Patent Abstract:
The present invention is directed to novel amide-containing compounds which have an improved solubility and a method of improving the solubility of amide-containing compounds. The amide-containing compounds include oxazolidinone compounds and the bioavailability of these oxazolidinone compounds is improved by improving the solubility thereof.

Full Description:
This application claims benefit of 60/304,808, filed Jul. 12, 2001. 
    
    
     FIELD OF THE INVENTION 
     The present invention is directed to amide-containing compounds having an improved water solubility and a method for improving the water-solubility of amide-containing compounds in general and, specifically, to oxazolidinone compounds having improved water solubility and a method of improving the water-solubility of oxazolidinone compounds. 
     BACKGROUND OF THE INVENTION 
     There are many compounds that contain amide groups which have desirable pharmacological activity. For example, oxazolidinone derivatives containing an amide group are known to exhibit a variety of biological activities. 
     Oxazolidinone derivatives have been shown to be inhibitors of monoamine oxidase-B, an enzyme implicated in Parkinson&#39;s disease. Ding et al.,  J. Med. Chem.  36:3606-3610 (1993). 
     Scientists have reported that certain oxazolidinone derivatives exhibit beneficial antibacterial effects. For instance, N-[3-[3-fluoro-4-(morpholin-4-yl)phenyl]2-oxooxazolidin-5(s)-ylmethyl] acetamide (below) has been reported to be useful for the treatment of bacterial infections. Lizondo et al.,  Drugs of the Future,  21:1116-1123 (1996). 
                        
 
     A ten step synthesis of oxazolidinone antibiotics has been described in U.S. Pat. No. 5,547,950. A four step synthesis of the antibacterial compound U-100592 also has been reported. Schauss et al.,  Tetrahedron Letters,  37:7937-7940 (1996). A five step preparation of enantiomerically pure cis- and trans-N-(propionyl)hexahydrobenzoxazolidin-2-ones further was reported in De Parrodi et al.,  Tetrahedron: Asymmetry,  8:1075-1082 (1997). 
     The synthesis of the oxazolidinone antibacterial agent shown below has been reported. Wang et al.,  Tetrahedron,  45:1323-1326 (1989). This oxazolidinone was made using a process that included the reaction of an aniline with glycidol to provide an amino alcohol, and the diethylcarbonate mediated cyclization of the amino alcohol to afford an oxazolidinone. 
                        
 
     The synthesis of oxazolidinone antibacterial agents, including the compound shown below has been reported. U.S. Pat. No. 4,705,799. The process used to make the compound shown below included a metal mediated reduction of a sulfonyl chloride to provide a sulfide. 
                        
 
     The synthesis of oxazolidinone antibacterial agents, including the pyridyl compound shown below has been reported. U.S. Pat. No. 4,948,801. The process used included an organometallic mediated coupling of an organotin compound and an aryl iodide. 
                        
 
     U.S. Pat. No. 5,652,238 discloses carboxylic and phosphate esters of substituted-hydroxyacetyl piperazine phenyl oxazolidinones. 
     U.S. Pat. No. 5,688,792 discloses substituted oxazine and thiazine oxazolidinone useful as antibacticals. 
     PCT International Publication WO 98/54161 discloses oxazolidinone antibacterial agents having a thiocarbonyl functionality. 
     U.S. Pat. No. 5,968,962 and PCT International Publication WO 99/29688 discloses phenyloxazolidinones having a C—C bond to 4-8 membered heterocyclic rings. 
     U.S. Pat. No. 5,952,324 discloses bicyclic oxazine and thiazine oxazolidinone useful as antibacticals. 
     PCT publications, WO 99/64416, WO 99/64417, and WO 00/21960 disclose oxazolidinone derivatives useful as antibacterial agents. 
     PCT Publication, WO 00/10566 discloses isoxazolinones useful as antibacterial agents. 
     U.S. Pat. No. 5,880,118 discloses substituted oxazine and thiazine oxazolidinone antimocrobials. 
     U.S. Pat. No. 6,968,962 discloses phenyloxazolidinones having a C—C bond to 4-8 membered heterocyclic rings. 
     U.S. Pat. No. 5,981,528 discloses antibiotic oxazolidinone derivatives. 
     U.S. patent application Ser. No. 60/236,595 discloses N-({(5S)-3-[4-(1,1-dioxido-4-thiomorpholinyl)-3,5-difluorophenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide. 
     PCT publications, WO 99/64416, WO 99/64417, and WO 00/21960 disclose isoxazolinone derivatives useful as antibacterial agents. 
     PCT publication, WO 00/10566 discloses isoxazolinones useful as antibacterial agents. 
     U.S. Pat. No. 5,164,510 discloses 5′-indolinyloxazolidin-2-ones of formula XI 
                        
 
which are useful as antibacterial agents.
 
     U.S. Pat. Nos. 5,036,092; 5,036,093; 5,039,690; 5,032,605 and 4,965,268 disclose aminomethyl oxazolidinyl aza cycloalkylbenzene derivatives useful as antibacterial agents. 
     U.S. Pat. Nos. 5,792,765 and 5,684,023 disclose substituted isoxazolinones useful as antibacterial agents. 
     International Publication No. WO 97/09328 discloses phenyloxazolidinones having a C—C bond to 4-8 membered heterocyclic rings useful as antimicrobial agents. 
     PCT International Publication WO 93/23384 discloses oxazolidinones containing a substituted diazine moiety and their use as antimicrobials. 
     PCT International Publication WO 95/07271 discloses substituted oxazine and thiazine oxazolidinones and their use as antimicrobials. 
     However, even though some amide-containing compounds have been shown to be extremely effective in the treatment of certain physiological disorders, some of these compounds have a low bioavailability due to their low water solubility and/or low permeability through biological barriers, such as the blood brain barrier and the intestinal barrier. 
     In order to increase the bioavailability of certain amines, peptides and peptidomimetics, prodrugs of these compounds, have been proposed. Zheng et al,  Tetrahedron Letters,  55:4237-4254 (1999), Wang et al,  Journal of Controlled Release,  65:245-251 (2000) and Wang et al,  Bioorganic  &amp;  Medicinal Chemistry,  6:417-426 (1998). These prodrugs derivatize certain polar functional groups transiently and bioreversably to mask undesirable physical chemical characteristics of the groups without permanently altering the pharmacological properties of the molecules and have been used very successfully in cases where the prodrug derivatization involves converting a carboxyl or a hydroxyl functional group into an ester which can be readily hydrolyzed in vivo either chemically or enzymatically. However, this strategy has not been successfully used in the case of an amide group due to the chemical stability thereof. 
     As such, there is a need for amide-containing compounds having an improved water-solubility and bioavailability and for methods for synthesizing these compounds. 
     SUMMARY OF THE INVENTION 
     The objects of the present invention are met by providing an oxazolidinone derivative of Formula (I) 
                        
     wherein J is O or S; 
                         
   R 210  is 
                         
   R 310 , R 410  and R 510  each independently are
       a) H,   b) C 1-4  alkyl,   c) halogen,   d) C 1-4  alkoxy,   e) hydroxy,   f) (CH 2 ) c OP(O)(OH) 2 ,   g) C 1-4  acyloxy, or   h) C 1-4  alkyl substituted by halogen, hydroxy, acyloxy, NR 1210 R 1310 , or alkoxy;   
       R 610 , R 710  and R 810  each independently are
       a) H,   b) CH 3 , or   c) C 2 H 5 ;   
       R 910  and R 1010  each independently are
       a) H,   b) CH 3 ,   c) C 2 H 5 , or   d) combine to form a C 3-5  cycloalkyl;   
       R 1110  is H or C 1-6  alkyl;   R 1210  and R 1310  each independently are
       a) H,   b) C 1-4  alkyl, or   c) combine to form a heterocyclic ring;   
       wherein a is 0 or 1, b is 0 or 1, and c is 0 or 1, with the proviso that when Q′ is 
                         
 
b is 0 and a+b is 0 or 1;
   R 1  is
       a) C 1-4  alkyl,   b) C 2-4  alkenyl,   c) OC 1-4  alkyl,   d) C 3-6  cycloalkyl,   e) C 1-4  alkyl substituted with 1-3F, 1-2Cl, CN, —COOC 1-4  alkyl or a C 3-6  cycloalkyl; or   f) H   
       A is 
                         
   R 4  is
       a) C 1-4  alkyl optionally substituted with one or more halos, OH, CN, NR 10 R 11 , or —CO 2 R 13 ,   b) C 2-4  alkenyl,   c) —NR 16 R 18 ,   d) —N 3 ,   e) —NHC(═O)R 7 ,   f) —NR 20 C(═O)R 7 ,   g) —N(R 1 ) 2 ,   h) —NR 16 R 19 , or   i) —NR 19 R 20 ,   
       R 5  and R 6  at each occurrence are the same or different and are
       a) C 1-2  alkyl, or   b) R 5  and R 6  taken together are —(CH 2 ) k —;   
       R 7  is C 1-4  alkyl optionally substituted with one or more halos;   R 10  and R 11  at each occurrence are the same or different and are
       a) H,   b) C 1-4  alkyl, or   c) C 3-8  cycloalkyl;   
       R 13  is
       a) H, or   b) C 1-4  alkyl;   
       R 14  and R 15  at each occurrence are the same or different and are
       a) C 1-4  alkyl, or   b) R 14  and R 15  taken together are —(CH) i —;   
       R 16  is
       a) H,   b) C 1-4  alkyl, or   c) C 3-8  cycloalkyl;   
       R 17  is
       a) C 1-4  alkyl, or   b) C 3-8  cycloalkyl;   
       R 18  is
       a) H,   b) C 1-4  alkyl,   c) C 2-4  alkenyl,   d) C 3-4  cycloalkyl,   e) —OR 13  or   f) —NR 21 R 22 ;   
       R 19  is
       a) Cl,   b) Br, or   c) I;   
       R 20  is a physiologically acceptable cation;   R 21  and R 22  at each occurrence are the same or different and are
       a) H,   b) C 1-4  alkyl, or   c) —NR 91 R 22  taken together are —(CH 2 ) m —;   
       wherein R 23  and R 24  at each occurrence are the same or different and are
       a) H,   b) F,   c) Cl,   d) C 1-2  alkyl,   e) CN   f) OH,   g) C 1-2  alkoxy,   h) nitro, or   i) amino;   
       Q is 
                         
       m) a diazinyl group optionally substituted with X and Y,   n) a triazinyl group optionally substituted with X and Y,   o) a quinolinyl group optionally substituted with X and Y,   p) a quinoxalinyl group optionally substituted with X and Y,   q) a naphthyridinyl group optionally substituted with X and Y, 
                         
                         
   
       Q and R 24  taken together are 
                         
   wherein Z 1  is
       a) —CH 2 —,   b) —CH(R 104 )—CH 2 —,   c) —C(O)—, or   d) —CH 2 CH 2 CH 2 —;   
       wherein Z 2  is
       a) —O 2 S—,   b) —O—,   c) —N(R 107 )—,   d) —OS—,   e) —S—, or   f) S(O)(NR 190 );   
       wherein Z 3  is
       a) —O 2 S—,   b) —O—,   c) —OS—,   d) —S—, or   e) S(O)(NR 190 )   
       wherein A 1  is
       a) H—, or   b) CH 3 ;   
       wherein A 2  is
       a) H—,   b) HO—,   c) CH 3 —,   d) CH 3 O—,   e) R 102 O—CH 2 —C(O)—NH—   f) R 103 O—C(O)—NH—,   g) (C 1 -C 2 )alkyl-O—C(O)—,   h) HO—CH 2 —,   i) CH 3 O—NH—,   j) (C 1 -C 3 )alkyl-O 2 C—   k) CH 3 —C(O)—,   l) CH 3 —C(O)—CH 2 —, 
                         
   
       A 1  and A 2  taken together are: 
                         
   wherein R 102  is
       a) H—,   b) CH 3 —,   c) phenyl-CH 2 —, or   d) CH 3 C(O)—;   
       wherein R 103  is
       a) (C 1 -C 3 )alkyl-, or   b) phenyl-;   
       wherein R 104  is
       a) H—, or   b) HO—;   
       wherein R 106  is
       a) CH 3 —C(O)—,   b) H—C(O)—,   c) Cl 2 CH—C(O)—,   d) HOCH 2 —C(O)—,   e) CH 3 SO 2 —, 
                         
   g) F2CHC(O)—, 
                         
   i) H 3 C—C(O)—O—CH 2 —C(O)—,   j) H—C(O)—O—CH 2 —C(O)—, 
                         
   l) HC≡C—CH 2 O—CH 2 —C(O)—, or   m) phenyl-CH 2 —O—CH 2 —C(O)—;   
       wherein R 107  is
       a) R 102 —C(R 110 )(R 111 )—C(O)—,   b) R 103 O—C(O)—   c) R 108 —C(O)—, 
                         
   f) H 3 C—C(O)—(CH 2 ) 2 —C(O)—,   g) R 109 —SO 2 —, 
                         
   i) HO—CH 2 —C(O)—,   j) R 116 —(CH 2 ) 2 —,   k) R 113 —C(O)—O—CH 2 —C(O)—,   l) (CH 3 ) 2 N—CH 2 —C(O)—NH—,   m) NC—CH 2 —,   n) F 2 —CH—CH 2 —, or   o) R 150 R 151 NSO 2      p) C(O)CR 180 R 180 R 181 OR 182 ,   q) C(O)CH 2 S(O) i CH 3 ,   r) C(O)CH 2 S(O)(NR 183 )CH 3 ,   s) C(S)R 184 ,   t) C(O)CH 2 OR 185 ,   u) C(O)(CH 2 )C(O)CH 3 ,   v) C(O)(CH 2 OH) 2 CH 3 ,   w) C(O)CH 2 CH 2 OR 189 , or   x) —CN;   
       wherein R 108  is
       a) H—,   b) (C 1 -C 4 )alkyl,   c) aryl —(CH 2 ) p ,   d) ClH 2 C—,   e) Cl 2 HC—,   f) FH 2 C—,   g) F 2 HC—,   h) (C 3 -C 6 )cycloalkyl, or   i) CNCH 2 —.   
       wherein R 109  is
       a) alkylC 1 -C 4 ,   b) —CH 2 Cl   c) —CH 2 CH═CH 2 ,   d) aryl, or   e) —CH 2 CN;   
       wherein R 110  and R 111  are independently
       a) H—,   b) CH 3 —; or   
       wherein R 112  is
       a) H—,   b) CH 3 O—CH 2 O—CH 2 —, or   c) HOCH 2 —;   
       wherein R 113  is
       a) CH 3 —,   b) HOCH 2 —,   c) (CH 3 ) 2 N-phenyl, or   d) (CH 3 ) 2 N—CH 2 —;   
       wherein R 114  is
       a) HO—,   b) CH 3 O—,   c) H 2 N—,   d) CH 3 O—C(O)—O—,   e) CH 3 —C(O)—O—CH 2 —C(O)O—,   f) phenyl-CH 2 —O—CH 2 —C(O)—O—,   g) HO—(CH 2 ) 2 —O—,   h) CH 3 O—CH 2 —O—(CH 2 ) 2 —O—, or   i) CH 3 O—CH 2 —O—;   
       wherein R 115  is
       a) H—, or   b) Cl—;   
       wherein R 116  is
       a) HO—   b) CH 3 O—, or   c) F;   
       wherein R 150  and R 151  are each H or alkyl C 1 -C 4  or R 150  and R 151  taken together with the nitrogen atom to which each is attached form a monocyclic heterocyclic ring having from 3 to 6 carbon atoms;   R 152  is
       a) H,   b) C 1-4 alkyl,   c) C 1-4 heteroalkyl,   d) (CH 2 ) i C(═O)OC 1-4 alkyl,   e) (CH 2 ) i C(═O)C 1-4 alkyl,   f) aryl, or   g) het 1 ;   
       R 153  and R 154  are independently
       a) H,   b) F,   c) C 1-4 alkyl,   d) C 3-6 cycloalkyl,   e) C 1-4 heteroalkyl,   f) aryl,   g) het 1 ,   h) OC 1-4 alkyl,   i) O(C═O)C 1-4 alkyl,   j) (C═O)OC 1-4 alkyl; or   k) R 153  and R 154  taken together are C 3-6 cycloalkyl;   
       R 155  is
       a) H,   b) F,   c) C 1-4 alkyl,   d) OC 1-4 alkyl,   e) SC 1-4 alkyl, or   f) NHC 1-4 alkyl;   
       R 156  is
       a) H,   b) C 1-4 alkyl,   c) OC 1-4 alkyl,   d) SC 1-4 alkyl, or   e) NHC 1-4 alkyl;   
       R 157  is
       a) —H,   b) —F,   c) —Cl,   d) —NH 2 ,   e) —OH,   f) —CN,   g) —C 1-4 alkyl,   h) —OC 1-4 alkyl,   i) —C 1-4 alkyl-W—C 1-4 alkyl,   j) —NHC 1-4 alkyl,   k) —(CH 2 ) i C 3-6 cycloalkyl,   l) —C(═O)C 1-4 alkyl,   m) —OC(═O)C 1-4 alkyl,   n) —C(═O)OC 1-4 alkyl,   o) —S(O) i C 1-4 alkyl, or   p) —C(═O)NHC 1-4 alkyl;   
       R 158  is
       a) —H,   b) —CH 3 ,   c) —F, or   d) —OH;   
       R 159  is
       a) —H,   b) —C 1-4 alkyl,   c) —C(═O)C 1-4 alkyl,   d) —C(═O)NHC 1-4 alkyl,   e) —OC(═O)C 1-4 alkyl,   f) —C(═O)OC 1-4 alkyl, or   g) —S(O) i C 1-4 alkyl, or   h) —C 1-4 alkyl-W 1 —C 1-4 alkyl;   
       R 160  is H, C 2-6  alkenyl, C 2-7 alkynyl, C 1-6  alkyl substituted with one or two of the following:
       a) F,   b) Cl,   c) CF 3 ,   d) —OH,   e) C 1-4 alkoxy,   f) —CH 2 C(═O)C 1-4 alkyl,   g) —OC(═O)N(R 161 ) 2 ,   h) C 1-4 alkyl S(O) n , (wherein n is 0, 1 or 2),   i) —CN,   j) carboxy,   k) —C 1-4 alkoxycarbonyl,   l) —C(═O)N(R 161 ) 2 ,   m) —N(R 161 )SO 2 C 1-4  alkyl,   n) —N(R 161 )C(═O)C 1-4  alkyl,   o) —N(R 161 )C(═O)N(R 4 ) 2 ,   p) —N(R 161 )C(═O)C 1-4  alkoxy,   q) aryl, or   r) Het 1 ;   
       R 161  is
       a) H, or   b) C 1-3  alkyl;   
       R 162  is
       a) H,   b) C 1-8  alkyl, optionally substituted with one to three F, Cl, OH, CN, NH 2 , OC(═O)C 1-4 alkyl, or OC 1-4  alkyl,   c) C 3-8  alkene, or   d) C(═O)NR 163 R 164 ;   
       R 163  and R 164  are independently
       a) H, or   b) C 1-8  alkyl, optionally substituted with one to three F, Cl, OH, CN, or NH 2 ;   
       R 165  is C 1-4  alkyl, optionally substituted with 1-3 R 168 ;   R 166  is
       a) C 1-8  alkyl, optionally substituted with 1-3 halo, CN, NO 2 , OH, SH or NH 2 ;   b) —C(═O)R 167  or   c) —C(═S)NHC 1-4  alkyl;   
       R 167  is
       a) H,   b) C 1-6  alkyl, optionally substituted with OH, C 1-4  alkoxy, NH 2 , SH or halo, or   c) —CH 2 OC(═O)C 1-4  alkyl;   
       R 168  is
       j) halo,   k) —CN,   l) —OH,   m) —SH,   n) —NH 2 ,   o) —OR 169 ,   p) —NHR 169 ,   q) —N(R 169 ) 2 , or   r) —S(═O) i R 169 ;   
       R 169  is
       g) C 1-6  alkyl,   h) —C(═O)C 1-4  alkyl,   i) —C(═O)O C 1-4  alkyl,   j) —C(═O)NH 2 ,   k) —C(═O)NH C 1-4  alkyl, or   l) —SO 2 C 1-4  alkyl;   with the proviso that where j is 0, Y 2  is —CH 2 —.   
       R 170  is
       a) H,   b) C 1-12  alkyl, optionally substituted with phenyl or CN, or   c) C 2-12  alkyl substituted with OH, SH, NH 2 , —OC 1-6  alkyl, —NHC 1-6  alkyl, —NHCOC 1-6  alkyl, —NHSO 2 C 1-6  alkyl, —S(O) i C 1-6  alkyl, or one to three halo;   
       R 172  is
       a) H,   b) C 1-8  alkyl,   c) aryl,   d) het 1 ,   e) C(═W)R 174 ,   f) C(═O)OR 175 , or   g) S(═O) i R 176 ;   
       R 173  is
       a) H, or   b) C 1-8  alkyl;   
       R 174  is
       a) H,   b) aryl,   c) het 1 ,   d) NR 177 R 178 , or   e) C 1-8  alkyl;   
       R 175  is
       a) C 1-8  alkyl,   b) aryl, or   c) het 1 ;   
       R 176  is
       a) aryl,   b) het 1 ,   c) NR 177 R 178 , or   d) C 1-8  alkyl;   
       R 177  and R 178  are independently
       a) H,   b) C 1-8  alkyl, or   c) aryl;   
       R 180  and R 181  taken together form C 3-5  cycloalkyl;   R 182  is H, CH 3  or C 1-4  alkanoyl;   R 183  is H, C 1-4  alkyl, C 1-4  alkanoyl, —C(═O)NH—C 1-4  alkyl or —CO 2 C 1-4  alkyl;   R 184  is C 1-4  alkyl, CH 2 OR 186 , S—C 1-4  alkyl, OC 1-4  alkyl, or NR 187 R 188 ;   R 185  is phenyl, —CO 2 —(CH 2 ) 2 —OCH 3 , —P(═O)(OH) 2 , —C(═O)—NR 187 R 186 , or —C(═O)—(CH 2 ) 2 —CO 2 H;   R 186  is H, phenyl, benzyl, CH 3  or C(═O)CH 3 ;   R 187  and R 188  are independently H or C 1-3  alkyl; or R 187  and R 188  taken together form a 5- or 6-membered saturated heterocycle, wherein said saturated heterocycle may further contain one or two additional hetero-atoms selected from a group consisting of O, S(O) n  or NR 182 ;   R 189  is H, CH 3  or benzyl;   R 190  is
       a) H,   b) C 1-4  alkyl,   c) C(═O)C 1-4  alkyl,   d) C(═O)OC 1-4  alkyl,   e) C(═O)NHR 191 , or   f) C(═S)NHR 191 ;   
       R 191  is H, C 1-4  alkyl, or phenyl;   at each occurrence, alkyl in R 190  and R 191  is optionally substituted with one or more halo, CN, NO 2 , phenyl, C 3-6  cycloalkyl, OR 192 , C(═O)R 192 , OC(═O)R 192 , C(═O)OR 192 , SC(═O) i R 192 , S(═O) i NR 192 R 192 , NR 192 R 192 , NR 192 SO 2 R 192 , NR 192 SO 2 R 192 R 192 , NR 192 C(═O)R 192 , C(═O)NR 192 R 192 , NR 192 R 192 , oxo or oxime;   R 192  is H, C 1-4  alkyl, or phenyl;
       at each occurrence, phenyl in R 191  and R 192  is optionally substituted with one or more halo, CN, NO 2 , phenyl, C 3-6  cycloalkyl, OR 192 , C(═O)R 192 , OC(═O)R 192 , C(═O)OR 192 , S(═O)R 196 , S(═O) i NR 192 R 192 , NR 192 SO 2 R 192 , NR 192 SO 2 NR 192 R 192 , NR 192 C(═O)R 192 , C(═O)NR 192 R 192 , or NR 192 R 192 ;   
       R 193  is selected from the group consisting of null, H, C 1 -C 4 alkyl, C 3 -C 5 cycloalkyl, C 1 -C 4 haloalkyl, and halophenyl;   R 194  is selected from the group consisting of H, alkyl, C 1 -C 2 alkoxy, halo, and haloalkoxy, or R 193  and R 194  can be taken together to form a 5- or 6-membered, optionally substituted, heteroalkyl or heteroaryl ring;   R 195  is H or F;   R 196  is selected from the group consisting of H, methyl, amino, and F;   R 197  is H, CH 3 , or F;   B is an unsaturated 4-atom linker having one nitrogen and three carbons;   M is
       a) H,   b) C 1-8  alkyl,   c) C 3-8  cycloalkyl,   d) —(CH 2 ) m OR 13 , or   e) —(CH 2 ) h —NR 21 R 22 ;   
       Z is
       a) O,   b) S, or   c) NM;   
       W is
       a) CH,   b) N, or   c) S or O when Z is NM;   
       Y is
       a) H,   b) F,   c) Cl,   d) Br,   e) C 1-3  alkyl, or   f) NO 2 ;   
       X is
       a) H,   b) —CN,   c) OR 27 ,   d) halo,   e) NO 2 ,   f) tetrazoyl,   g) —SH,   h) —S(═O) i R 4 ,   i) —S(═O) 2 —N═S(O) j R 5 R 6 ,   j) —SC(═O)R 7 ,   k) —C(═O)R 25 ,   l) —C(═O)NR 27 R 28 ,   m) —C(═NR 29 )R 25 ,   n) —C(R 25 )(R 28 )—OR 13 ,   o) —C(R 25 )(R 28 )—OC(═O)R 13 ,   p) —C(R 28 )(OR 13 )—(CH 2 ) h —NR 27 R 28 ,   q) —NR 27 R 28 ,   r) —N(R 27 )C(═O)R 7 ,   s) —N(R 27 )—S(═O) i R 7 ,   t) —C(OR 14 )(OR 15 )R 28 ,   u) —C(R 25 )(R 16 )—NR 27 R 26 , or   v) C 1-8  alkyl substituted with one or more halos, OH, ═O other than at alpha position, —S(═O) i R 17 , —NR 27 R 28 , C 2-5  alkenyl, C 2-5  alkynyl, or C 3-8  cycloalkyl;   
       X 1  is N or CR 158 ;   Y 1  is
       a) S(O) i ,   b) S(NR 159 ), or   c) S(NR 159 )(O);   
       W 1  is O or S;   X 2  is O or NR 162 ;   X 3  is S(O) i  or NR 166 ;   Y 2  is
       a) O   b) NH,   c) CH 2 , or   d) S(O) i ;   
       X 4  is
       a) O   b) NR 172 ,   c) S(O) i , or   d) S(O)(NR 173 ); and   
       Y 3  is CH or N;   R 4 , R 5 , R 6 , R 7 , R 13 , R 14 , R 15 , R 16 , and R 17  are the same as defined above;   R 25  is
       a) H,   b) C 1-8  alkyl optionally substituted with one or more halos, C 3-8  cycloalkyl, C 1-4  alkyl substituted with one or more of —S(═O) i R 17 , —OR 13 , or OC(═O)R 13 , NR 27 R 28 , or   c) C 2-5  alkenyl optionally substituted with CHO, or CO 2 R 13 ;   
       R 26  is
       a) R 28 , or   b) NR 27 NR 28 ;   
       R 27  and R 28  at each occurrence are the same or different and are
       a) H,   b) C 1-8  alkyl,   c) C 3-8  cycloalkyl,   d) —(CH 2 ) m OR 13 ,   e) —(CH 2 ) h —NR 21 R 22 , or   f) R 27  and R 28  taken together are —(CH 2 ) 2 O(CH 2 ) 2 —, —(CH 2 ) h CH(COR 7 )—, or —(CH 2 ) 2 N(CH 2 ) 2 (R 7 );   
       R 29  is
       a) —NR 27 R 28 ,   b) —OR 27 , or   c) —NHC(═O)R 28 ;   
       wherein R 30  is
       a) H,   b) C 1-8  alkyl optionally substituted with one or more halos, or   c) C 1-8  alkyl optionally substituted with one or more OH, or C 1-6  alkoxy;   
       wherein E is
       a) NR 39 ,   b) —S(═O) i ;   c) O, or   d) S(O)(NR 190 );   
       R 38  is
       a) H,   b) C 1-6  alkyl,   c) —(CH 2 ) q -aryl, or   d) halo;   
       R 39  is
       a) H,   b) C 1-6  alkyl optionally substituted with one or more OH, halo, or —CN,   c) —(CH 2 ) q -aryl,   d) —CO 2 R 40 ,   e) —COR 41 ,   f) —C(═O)—(CH 2 ) q —C(═O)R 40 ,   g) —S(═O) 2 —C 1-16  alkyl,   h) —S(═O) 2 —(CH 2 ) q -aryl, or   i) —(C═O) j -Het;   
       R 40  is
       a) H,   b) C 1-6  alkyl optionally substituted with one or more OH, halo, or —CN,   c) —(CH 2 ) q -aryl, or   d) —(CH 2 ) q —OR 42 ;   
       R 41  is
       a) C 1-6  alkyl optionally substituted with one or more OH, halo, or —CN,   b) —(CH 2 ) q -aryl, or   c) —(CH 2 ) q —OR 42 ;   
       R 42  is
       a) H,   b) C 1-6  alkyl,   c) —(CH 2 ) q -aryl, or   d) —C(═O)—C 1-6  alkyl;   
       aryl is
       a) phenyl,   b) pyridyl, or   c) napthyl; a to c optionally substituted with one or more halo, —CN, OH, SH, C 1-6  alkyl, C 1-6  alkoxy, or C 1-6  alkylthio;   
       h is 1, 2, or 3;   i is 0, 1, or 2;   j is 0 or 1, with the proviso that when j is 0, Y 2  is —CH 2 —;   k is 3, 4, or 5;   l is 2 or 3;   m is 4 or 5;   n is 0, 1, 2, 3, 4, or 5;   p is 0, 1, 2, 3, 4, or 5; with the proviso that n and p together are 1, 2, 3, 4, or 5;   q is 1, 2, 3, or 4;   u is 1 or 2;   w is 0, 1, 2, or 3;   x is 0, 1, 2, 3 or 4; and   y is 0, 1, 2, 3 or 4; with the proviso that x and y taken together are 3 or 4;   z is 1, 2, 3, 4 or 5, provided that i and z taken together are 2, 3, 4 or 5; and   G is 
                         
   

     The present invention also provides an oxazolidinone derivative of Formula (II) 
                        
 
wherein J, R 1 , G and A are as defined above.
 
     The present invention also is directed to an oxazolidinone derivative of formula (VIII) having an improved solubility, wherein R is —CH 2 -G-A and R 1 , G and A are as defined above. 
                        
 
     The present invention also is directed to a method of improving the solubility of an amide of Formula (III) 
                        
 
in which the compound of Formula (VIII) is prepared, wherein R is —CH 2 -G-A and R 1 , G and A are as defined above. 
                         
 
     The present invention also is directed to a method of improving the solubility of an amide of Formula (III) 
                        
 
in which the compound of Formula (XII) is prepared, wherein R is —CH 2 -G-A, with G, A, Q; R 310 , R 410 , R 510  and R 610  being as defined above. 
                         
 
     The present invention is also directed to an oxazolidinone derivative of formula (XIII) 
                        
 
wherein R is -G-A;
     J, G and A being as defined above;   R 1 ′ is
       a) H,   b) OH,   c) alkyl,   d) alkoxy,   e) alkenyl,   f) amino,   g) substituted alkyl,   h) substituted alkoxy,   i) substituted alkenyl, or   j) substituted amino, 
                         
   
       R 210  is 
                         
   R 310 , R 410  and R 510  each independently are
       a) H,   b) C 1-4  alkyl,   c) halogen,   d) C 1-4  alkoxy,   e) hydroxy,   f) (CH 2 ) c OP(O)(OH) 2 ,   g) C 1-4  acyloxy, or   h) C 1-4  alkyl substituted by halogen, hydroxy, acyloxy, NR 1210 R 1310 , or alkoxy; and   
       R 610  is
       a) H,   b) CH 3 , or   c) C 2 H 5 .   
       

     The present invention is also directed to a method of preparing an oxazolidinone derivative having an improved water solubility comprising the steps of providing an amide of formula (XVI) 
                        
 
reacting the amide with a compound of formula (XIV) 
                         
 
to form a compound of formula (XVII) 
                         
 
and removing the protecting groups to form a compound of formula (XVIII) 
                         
 
wherein R is -G-A and J, R′ 1 , G, A and Pr are as described above.
 
    
    
     DETAILED DESCRIPTION OF THE INVENTION 
     For the purpose of the present invention, the carbon content of various hydrocarbon containing moieties is indicated by a prefix designating the minimum and maximum number of carbon atoms in the moiety, i.e., the prefix C i-j  defines the number of carbon atoms present from the integer “i” to the integer “j”, inclusive. Thus, C 1-4  alkyl refers to alkyl of 1-4 carbon atoms, inclusive, or methyl, ethyl, propyl, butyl and isomeric forms thereof. 
     The terms “C 1-2  alkyl”, “C 1-3  alkyl”, “C 1-4  alkyl”, “C 1-5  alkyl”, “C 1-6  alkyl”, “C 1-8  alkyl”, and “C 1-16  alkyl” refer to an alkyl group having one to two, one to three, one to four, one to five, one to six, one to eight, or one to sixteen carbon atoms respectively such as, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl and their isomeric forms thereof. 
     The terms “C 2-4  alkenyl”, “C 2-5  alkenyl”, “C 2-8  alkenyl”, “C 2-14  alkenyl” and “C 2-16  alkenyl” refer to at least one double bond alkenyl group having two to four, two to five, two to eight, two to fourteen, or two to sixteen carbon atoms, respectively such as, for example, ethenyl, propenyl, butenyl, pentenyl, pentdienyl, hexenyl, hexdienyl, heptenyl, heptdienyl, octenyl, octdienyl, octatrienyl, nonenyl, nonedienyl, nonatrienyl, undecenyl, undecdienyl, dodecenyl, tridecenyl, tetradecenyl and their isomeric forms thereof. 
     The terms “C 2-5  alkynyl”, “C 2-8  alkynyl”, and “C 2-10  alkynyl” refer to at least one triple bond alkynyl group having two to five, two to eight, or two to ten carbon atoms respectively such as, for example, ethynyl, propynyl, butynyl, pentynyl, pentdiynyl, hexynyl, hexdiynyl, heptynyl, heptdiynyl, octynyl, octdiynyl, octatriynyl, nonynyl, nonediynyl, nonatriynyl and their isomeric forms thereof. 
     The terms “C 3-4  cycloalkyl”, “C 3-6  cycloalkyl”, “C 5-6  cycloalkyl”, and “C 3-8  cycloalkyl” refer to a cycloalkyl having three to four, three to six, five to six, or three to eight carbon atoms respectively such as, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and their isomeric forms thereof. 
     The terms “C 1-4  alkoxy”, “C 1-6  alkoxy”, and “C 1-8  alkoxy” refer to an alkyl group having one to four, one to six, or one to eight carbon atoms respectively attached to an oxygen atom such as, for example, methoxy, ethoxy, propyloxy, butyloxy, pentyloxy, hexyloxy, heptyloxy, or octyloxy and their isomeric forms thereof. 
     The terms “C 1-6  alkylamino”, and “C 1-8  alkylamino” refer to an alkyl group having one to six, or one to eight carbon atoms respectively attached to an amino moiety such as, for example, methylamino, ethylamino, propylamino, butylamino, pentylamino, hexylamino, heptylamino, or octoylamino and their isomeric forms thereof. 
     The terms “C 1-6  dialkylamino”, and “C 1-8  dialkylamino” refer to two alkyl groups having one to six, or one to eight carbon atoms respectively attached to an amino moiety such as, for example, dimethylamino, methylethylamino, diethylamino, dipropylamino, methypropylamino, ethylpropylamino, dibutylamino, dipentylamino, dihexylamino, methylhecylamino, diheptylamino, or dioctoylamino and their isomeric forms thereof. 
     The terms “C 1-3  acyl”, “C 1-4  acyl”, “C 1-5  acyl”, “C 1-6  acyl”, “C 1-8  acyl”, and “C 2-8  acyl” refer to a carbonyl group having an alkyl group of one to three, one to four, one to five, one to six, one to eight, or two to eight carbon atoms. 
     The terms “C 1-4  alkoxycarbonyl”, “C 1-6  alkoxycarbonyl”, and “C 1-8  alkoxycarbonyl” refer to an ester group having an alkyl group of one to four, one to six, or one to eight carbon atoms. 
     The term “C 1-8  alkyl phenyl” refers to an alkyl group having one to eight carbon atoms and isomeric forms thereof which is substituted with at least one phenyl radical. 
     The term “C 2-8  alkenyl phenyl” refers to a at least one double bond alkenyl group having one to eight carbon atoms and isomeric forms thereof which is substituted with at least one phenyl radical. 
     The term “C 1-8  alkyl pyridyl” refers to an alkyl group having one to eight carbon atoms and isomeric forms thereof which is substituted with at least one pyridyl radical. 
     The term “C 1-8  hydroxyl” refers to an alkyl group having one to eight carbon atoms and isomeric forms thereof attached to a hydroxy group. 
     The term “C 1-8  alkylsulfonyl” refers to an alkyl group having one to eight carbon atoms and isomeric forms thereof attached to a SO 2  moiety. 
     The term “C 1-6  alkylthio” refers to an alkyl group having one to six carbon atoms and isomeric forms thereof attached to a sulfur atom. 
     The term “Het” refers to 5 to 10 membered saturated, unsaturated or aromatic heterocyclic rings containing one or more oxygen, nitrogen, and sulfur forming such groups as, for example, pyridine, thiophene, furan, pyrazoline, pyrimidine, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 3-pyridazinyl, 4-pyridazinyl, 3-pyrazinyl, 2-quinolyl, 3-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 2-quinazolinyl, 4-quinazolinyl, 2-quinoxalinyl, 1-phthalazinyl, 4-oxo-2-imidazolyl, 2-imidazolyl, 4-imidazolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 4-oxo-2-oxazolyl, 5-oxazolyl, 4,5,-dihydrooxazole, 1,2,3-oxathiole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 3-isothiazole, 4-isothiazole, 5-isothiazole, 2-indolyl, 3-indolyl, 3-indazolyl, 2-benzoxazolyl, 2-benzothiazolyl, 2-benzimidazolyl, 2-benzofuranyl, 3-benzofuranyl, benzoisothiazole, benzisoxazole, 2-furanyl, 3-furanyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isopyrrolyl, 4-isopyrrolyl, 5-isopyrrolyl, 1,2,3,-oxathiazole-1-oxide, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 5-oxo-1,2,4-oxadiazol-3-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 3-oxo-1,2,4-thiadiazol-5-yl, 1,3,4-thiadiazol-5-yl, 2-oxo-1,3,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl, 1,2,4-triazol-5-yl, 1,2,3,4-tetrazol-5-yl, 5-oxazolyl, 1-pyrrolyl, 1-pyrazolyl, 1,2,3-triazol-1-yl, 1,2,4-triazol-1-yl, 1-tetrazolyl, 1-indolyl, 1-indazolyl, 2-isoindolyl, 7-oxo-2-isoindolyl, 1-purinyl, 3-isothiazolyl, 4-isothiazolyl and 5-isothiazolyl, 1,3,4,-oxadiazole, 4-oxo-2-thiazolinyl, or 5-methyl-1,3,4-thiadiazol-2-yl, thiazoledione, 1,2,3,4-thiatriazole, 1,2,4-dithiazolone. Each of these moieties may be substituted as appropriate. 
     The term het 1  at each occurrence is independently a C-linked 5- or 6-membered heterocyclic ring having 1 to 4 heteroatoms selected from the group consisting of oxygen, nitrogen, and sulfur within the ring. 
     The term het 2  at each occurrence is independently a N-linked 5- or 6-membered heterocyclic ring having 1 to 4 nitrogen and optionally having one oxygen or sulfur within the ring. 
     The term Het 1  is a 5- or 6-membered heteroaromatic moiety having 1-3 N, O or S atoms, optionally substituted with the following:
         a) F,   b) Cl,   c) C 1-3  alkoxy,   d) C 1-3  alkylthio, or   e) CN.       

     The term het 1  is a C-linked 5- or 6-membered saturated or unsaturated heterocyclic ring having 1, 2, or 3 heteroatoms selected from the group consisting of oxygen, sulfur, and nitrogen, which is optionally fused to a benzene ring. 
     The term halo refers to fluoro, chloro, bromo, or iodo. 
     The term Pr refers to a suitable phosphate protecting group, such as benzyl, alkyl, tert-butyl, etc. 
     The compounds of the present invention can be converted to their salts, where appropriate, according to conventional methods. 
     The term “pharmaceutically acceptable salts” refers to acid addition salts useful for administering the compounds of this invention and include hydrochloride, hydrobromide, hydroiodide, sulfate, phosphate, acetate, propionate, lactate, mesylate, maleate, malate, succinate, tartrate, citric acid, 2-hydroxyethyl sulfonate, fumarate and the like. These salts may be in hydrated form. 
     When Q is the structure of 
                        
 
the dotted line in the heterocyclic ring means that this bond can be either single or double. In the case where the dotted line is a double bond, the R 39  group will not be present.
 
     The compounds of this invention contain a chiral center at C5 of the isoxazoline ring, and as such there exist two enantiomers or a racemic mixture of both. This invention relates to both the enantiomers, as well as mixtures containing both the isomers. In addition, depending on substituents, additional chiral centers and other isomeric forms may be present in any of A or R 1  group, and this invention embraces all possible stereoisomers and geometric forms in these groups. 
     The compounds of this invention are useful for treatment of microbial infections in humans and other warm blooded animals, under both parenteral and oral administration. The inventive compounds have antibacterial activity against a number of human and veterinary pathogens including Gram-positive aerobic bacteria such as multiply-resistant staphylococci, streptococci and enterococci, Gram-negative organisms such as  H. influenzae  and  M. catarrhalis , anaerobic organisms such as  Bacteroides  spp. and  Clostridasppa, Mycobacterium tuberculosis, M. avium  and  M.  spp. and organisms such as  Mycoplasma  spp. 
     The pharmaceutical compositions of this invention may be prepared by combining the compounds of this invention with a solid or liquid pharmaceutically acceptable carrier and, optionally, with pharmaceutically acceptable adjuvants and excipients employing standard and conventional techniques. Solid form compositions include powders, tablets, dispersible granules, capsules, cachets and suppositories. A solid carrier can be at least one substance which may also function as a diluent, flavoring agent, solubilizer, lubricant, suspending agent, binder, tablet disintegrating agent, and encapsulating agent. Inert solid carriers include magnesium carbonate, magnesium stearate, talc, sugar, lactose, pectin, dextrin, starch, gelatin, cellulosic materials, low melting wax, cocoa butter, and the like. Liquid form compositions include solutions, suspensions and emulsions. For example, there may be provided solutions of the compounds of this invention dissolved in water and water-propylene glycol and water-polyethylene glycol systems, optionally containing suitable conventional coloring agents, flavoring agents, stabilizers and thickening agents. 
     Preferably, the pharmaceutical composition is provided employing conventional techniques in unit dosage form containing effective or appropriate amounts of the active component, that is, the compound according to this invention. 
     The quantity of active component, that is the compound according to this invention, in the pharmaceutical composition and unit dosage form thereof may be varied or adjusted widely depending upon the particular application, the potency of the particular compound, the desired concentration. Generally, the quantity of active component will range between 0.5% to 90% by weight of the composition. 
     In therapeutic use for treating, or combatting, bacterial infections in warm-blooded animals, the compounds or pharmaceutical compositions thereof will be administered orally, parenterally and/or topically at a dosage to obtain and maintain a concentration, that is, an amount, or blood-level of active component in the animal undergoing treatment which will be antibacterially effective. Generally, such antibacterially effective amount of dosage of active component will be in the range of about 0.1 to about 100, more preferably about 3.0 to about 50 mg/kg of body weight/day. It is to be understood that the dosages may vary depending upon the requirements of the patient, the severity of the bacterial infection being treated, and the particular compound being used. Also, it is to be understood that the initial dosage administered may be increased beyond the above upper level in order to rapidly achieve the desired blood-level or the initial dosage may be smaller than the optimum and the daily dosage may be progressively increased during the course of treatment depending on the particular situation. If desired, the daily dose may also be divided into multiple doses for administration, e.g., 2-4 four times per day. 
     When the compounds according to this invention are administered parenterally, i.e., by injection, for example, by intravenous injection or by other parenteral routes of administration. Pharmaceutical compositions for parenteral administration will generally contain a pharmaceutically acceptable amount of the compound or a soluble salt (acid addition salt or base salt) dissolved in a pharmaceutically acceptable liquid carrier such as, for example, water-for-injection and a buffer to provide a suitably buffered isotonic solution, for example, having a pH of about 3.5-6. Suitable buffering agents include, for example, trisodium orthophosphate, sodium bicarbonate, sodium citrate, N-methylglucamine, L(+)-lysine and L(+)-arginine to name but a few representative buffering agents. The compound of this invention generally will be dissolved in the carrier in an amount sufficient to provide a pharmaceutically acceptable injectable concentration in the range of about 1 mg/mL to about 400 mg/mL of solution. The resulting liquid pharmaceutical composition will be administered so as to obtain the above-mentioned antibacterially effective amount of dosage. The compounds according to this invention are advantageously administered orally in solid and liquid dosage forms. 
     As a topical treatment an effective amount of Formula I is admixed in a pharmaceutically acceptable gel or cream vehicle that can be applied to the patient&#39;s skin at the area of treatment. Preparation of such creams and gels is well known in the art and can include penetration enhancers. 
     The present invention improves the solubility and bioavailability of an amide of Formula III 
                        
 
by converting it into a prodrug of Formula (VIII). The general scheme for preparing the prodrug of Formula (VIII) is shown below in Schemes 1 and 2. 
                         
 
     In the above reaction scheme, the carboxylic acid derivative of Formula IV is prepared as described in M. G. Nicolaou, C.-S. Yuan and R. T. Borchardt,  J. Med. Chem.  1996, 61, 8636-8641. Condensation of the amine of Formula V with the carboxylic acid of IV is accomplished by methods known in the art for amide or peptide bond formation. Examples include 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 4-(dimethylamino)pyridine and solvents such as methylene chloride at reaction temperatures of 0 to 24° C., 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 1-hydroxybenzotriazole and solvents such as dimethylformamide at 0 to 24° C., and bis(2-oxo-3-oxazolidinyl)phosphinic chloride and triethylamine and solvents such as methylene chloride at 0 to 24° C. 
     In Step 2 of Scheme 1, the amide of VI undergoes an acylation reaction to give the compound of VII, wherein J is an oxygen atom. This reaction is conveniently carried out by allowing the compound of VI to react with an acid chloride in the presence of an efficient acid scavenger. Solvents such as methylene chloride, ethylene chloride or carbon tetrachloride at a temperature of from 24° C. to the reflux temperature of the solvent can be used. Acid scavengers such as 3 Å units molecular sieves, propylene oxide, 1,8-bis(dimethylamino)naphthalene and methyl trimethylsilylcarbamate are suitable for use in this reaction. In Step 3 of Scheme 1, the phosphate esters of Formula VII are deprotected. This can be carried out by hydrogenolysis at atmospheric pressure and ambient temperature with a palladium catalyst. Solvents such as tetrahydrofuran, diethylether, or 1,2-dimethoxyethane can be used for this reaction. 
     Alternatively, compounds of formula (VIII) can be prepared according to the following Scheme 2. In Scheme 2, P r  of formula (XIII) represents a suitable phosphate protecting group, such as benzyl, alkyl or tert-butyl. 
                        
 
     In Step 1, the acid (XIII) is converted to the acid chloride (XIV) with, for example, oxalyl chloride and dimethylformamide in a solvent, such as methylene chloride, at temperatures of from 0 to 30° C. In Step 2, the compound of formula (XIV) is allowed to react with the compound of formula (III) in a solvent, such as methylene chloride, ethylene chloride or acetonitrile, in the presence of an efficient acid scavenger, such as methyl trimethylsilylcarbamate, at the reflux temperature of the solvent. In Step 3, the phosphate protecting groups of the compound of formula (XV) is removed by methods known in the art. 
     Examples of amides containing oxazolidinone groups that can be used in the present invention are shown below. The preparation of the following amides of Examples 1-434 are shown in U.S. Pat. No. 6,362,189 B1, the disclosure of which is herein incorporated by reference thereto. 
     
       
         
               
               
             
           
               
                   
                 TABLE A 
               
               
                   
                   
               
             
             
               
                   
                 EXAMPLE 1: (S)-N-[[3-[3-Fluoro-4-(4-morpholinyl)phenyl]- 
               
               
                   
                 2-oxo-5-oxazolidinyl]methyl]thioacetamide (I) 
               
               
                   
                 EXAMPLE 2: (S)-N-[[3-[3-Fluoro-4-[4-(5-methyl-1,3,4- 
               
               
                   
                 thiadiazol-2-yl)-1-piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]thioacetamide (2) 
               
               
                   
                 EXAMPLE 3: (S)-N-[[3-[3-Fluoro-4-[2′,5′- 
               
               
                   
                 dioxospiro[piperidine-4,4′-imidazolidine]-1-yl]phenyl]- 
               
               
                   
                 2-oxo-5-oxazolidinyl]methyl]thioacetamide (3). 
               
               
                   
                 EXAMPLE 4: (S)-N-[[3-[3-Fluoro-4-(4- 
               
               
                   
                 morpholinyl)phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]thioacetamide (4). 
               
               
                   
                 EXAMPLE 5: (S)-cis-N-[[3-[3-Fluoro-4-(tetrahydro-1- 
               
               
                   
                 oxido-2H-thiopyran-4-yl)phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]ethanethioamide 
               
               
                   
                 EXAMPLE 6: (S)-trans-N-[[3-[3-Fluoro-4-(tetrahydro-1- 
               
               
                   
                 oxido-2H-thiopyran-4-yl)phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]ethanethioamide 
               
               
                   
                 EXAMPLE 7: (S)-N-[[3-[3-Fluoro-4-(tetrahydro-1,1- 
               
               
                   
                 dioxido-2H-thiopyran-4-yl)phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]ethanethioamide 
               
               
                   
                 EXAMPLE 8: (S)-N-[[3-[3-Fluoro-4-(4-morpholinyl)phenyl]- 
               
               
                   
                 2-oxo-5-oxazolidinyl]methyl]-thioformamide (7). 
               
               
                   
                 EXAMPLE 9: (S)-N-[[3-[3-Fluoro-4-(4-morpholinyl)phenyl]- 
               
               
                   
                 2-oxo-5-oxazolidinyl]methyl]thiopropion-amide (9). 
               
               
                   
                 EXAMPLE 10: (S)-N-[[3-[3-Fluoro-4-(4- 
               
               
                   
                 morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-2- 
               
               
                   
                 chlorothioacetamide (11). 
               
               
                   
                 EXAMPLE 11: (S)-N-[[3-[3-Fluoro-4-(4- 
               
               
                   
                 moropholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-α,α, 
               
               
                   
                 α-trifluorothioacetamide (13). 
               
               
                   
                 EXAMPLE 12: (S)-N-[[3-[3-Fluoro-4-(4- 
               
               
                   
                 morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-α- 
               
               
                   
                 fluorothioacetamide (15). 
               
               
                   
                 EXAMPLE 13: (S)-N-[[3-[3-Fluoro-4-(4- 
               
               
                   
                 morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-α,α- 
               
               
                   
                 difluorothioacetamide (17). 
               
               
                   
                 EXAMPLE 14: (S)-N-[[3-[3-Fluoro-4-(4- 
               
               
                   
                 morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-α- 
               
               
                   
                 cyanothioacetamide (19). 
               
               
                   
                 EXAMPLE 15: (S)-N-[[3-[3-Fluoro-4-(4- 
               
               
                   
                 morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-α,α- 
               
               
                   
                 dichlorothioacetamide (21). 
               
               
                   
                 EXAMPLE 16: (S)-N-[[3-[3-Fluoro-4-(4- 
               
               
                   
                 morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-α- 
               
               
                   
                 (methoxycarbonyl)thioacetamide (23). 
               
               
                   
                 EXAMPLE 17: (S)-N-[[3-[4-[1-[1,2,4]Triazolyl]phenyl]-2- 
               
               
                   
                 oxo-5-oxazolidinyl]methyl]thioacetamide (25). 
               
               
                   
                 EXAMPLE 18: (S)-N-[[3-[4-[1-[1,2,4]Triazolyl]phenyl]-2- 
               
               
                   
                 oxo-5-oxazolidinyl]methyl]thioacetamide (25). 
               
               
                   
                 EXAMPLE 19: (S)-N-[[3-[1-(Hydroxyacetyl)-5-indolinyl]-2- 
               
               
                   
                 oxo-5-oxazolidinyl]methyl]thioacetamide (28). 
               
               
                   
                 EXAMPLE 20: (S)-N-[[3-[3-Fluoro-4-[4-(hydroxyacetyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]thioacetamide (30). 
               
               
                   
                 EXAMPLE 21: (S)-N-[[3-[3-Fluoro-4-(4- 
               
               
                   
                 thiomorpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]thio- 
               
               
                   
                 acetamide (32). 
               
               
                   
                 EXAMPLE 22: (S)-N-[[3-[3-Fluoro-4-(4- 
               
               
                   
                 thiomorpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]thio- 
               
               
                   
                 acetamide, thiomorpholine S-oxide (34). 
               
               
                   
                 EXAMPLE 23: (S)-N-[[3-[3-Fluoro-4-(4- 
               
               
                   
                 thiomorpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]thio- 
               
               
                   
                 acetamide, thiomorpholine S, S-dioxide (36). 
               
               
                   
                 EXAMPLE 24: (S)-N-[[3-[3,5-Difluoro-4-[4- 
               
               
                   
                 (hydroxyacetyl)-1-piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]thioacetamide (38). 
               
               
                   
                   
               
             
          
         
       
     
     
       
         
               
             
               
               
               
             
           
               
                 TABLE B 
               
             
             
               
                   
               
               
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
             
          
           
               
                 Example 
                   
                   
               
               
                 No. 
                 Compound 
                 R, R′ 
               
               
                   
               
               
                 25 
                 (S)-N-[[3-[3-Fluoro-4-(4-morp 
                 R = H, R′ = 
               
               
                   
                 holinyl)- 
                 CH(CH 3 ) 2   
               
               
                   
                 phenyl]-2-oxo-5-oxazolidinyl] 
               
               
                   
                 methyl]-2- 
               
               
                   
                 methylpropanethioamide; mp 
               
               
                   
                 152-153°C. 
               
               
                   
                 (dec.); Anal. calcd for 
               
               
                   
                 C 18 H 24 FN 3 O 3 S: C, 
               
               
                   
                 56.67; H, 6.34; N, 11.02. 
               
               
                   
                 Found: C, 56.58; 
               
               
                   
                 H, 6.41; N, 10.81 
               
               
                 26 
                 (S)-N-[[3-[3-Fluoro-4-(4-morp holinyl)- phenyl]-2-oxo-5-oxazolidinyl] methyl]- cyclopropane-carbothioamide; mp 155-156° C.; Anal. calcd for C 18 H 22 FN 3 O 3 S: C, 56.98; H, 5.84; N, 11.07. Found: C, 56.98; H, 5.85; N, 10.97 
               
               
                 27 
                 (S)-N-[[3-[3,5-Difluoro-4-(4- 
                 R = F, R′ = CH 3   
               
               
                   
                 morpholinyl)- 
               
               
                   
                 phenyl]-2-oxo-5-oxazolidinyl] 
               
               
                   
                 methyl]thioacetamide 
               
               
                   
               
             
          
         
       
     
     
       
         
               
               
               
               
             
           
               
                 TABLE C 
               
               
                   
               
               
                   
                   
                   
                 Dithio 
               
               
                   
                   
                   
                 Compound 
               
               
                 Example 
                   
                   
                 (from 
               
               
                 No. 
                 Compound 
                 Amine 
                 Prepartion Z) 
               
               
                   
               
             
             
               
                 28 
                 (S)-N-[[3-[3-Fluoro-4- (4-thiomorpholinyl)- phenyl]-2-oxo-5- oxazolidinyl]methyl]- propanethioamide, thiomorphoilne S-oxide; mp 196-197° C.; Anal. calcd for C 17 H 22 FN 3 O 3 S 2 : C, 51.11; H, 5.55;  
               
               
                 #  N, 10.52; S, 16.05. Found: C, 50.99; H, 5.60; N, 10.55; S, 15.75 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Z (a) 
               
               
                 29 
                 S)-N-[[3-[3-Fluoro-4-(4- 
                 Same as 
                 Z (b) 
               
               
                   
                 thiomorpholinyl)- 
                 above 
               
               
                   
                 phenyl]-2-oxo-5 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethioamide, 
               
               
                   
                 thiomorpholine 
               
               
                   
                 S-oxide; mp 
               
               
                   
                 195-196° C.; 
               
               
                   
                 Anal. calcd for 
               
               
                   
                 C 18 H 24 FN 3 O 3 S 2 : C, 
               
               
                   
                 52.28; H, 5.85; 
               
               
                   
                 N, 10.16; 
               
               
                   
                 S, 15.51. Found: 
               
               
                   
                 C, 
               
               
                   
                 52.24; H, 5.97; 
               
               
                   
                 N, 10.16; 
               
               
                   
                 S, 15.28 
               
               
                 30 
                 (S)-N-[[3-[3-Fluoro-4- 
                 Same as 
                 Z (c) 
               
               
                   
                 (4-thiomorpholinyl)- 
                 above 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclopropanecarbothioamide, 
               
               
                   
                 thiomorpholine 
               
               
                   
                 S-oxide; mp 
               
               
                   
                 109-110° C.; 
               
               
                   
                 Anal. calcd for 
               
               
                   
                 C 18 H 22 FN 3 O 3 S 2 : C, 
               
               
                   
                 52.54; H, 5.39; 
               
               
                   
                 N, 10.21; 
               
               
                   
                 S, 15.58. Found: 
               
               
                   
                 C, 
               
               
                   
                 52.48; H, 5.51; 
               
               
                   
                 N, 10.28; 
               
               
                   
                 S, 15.29 
               
               
                 31 
                 (S)-N-[[3-[3-Fluoro-4- 
                 Same as 
                 Z (d) 
               
               
                   
                 (4-thiomorpholiny 
                 above 
               
               
                   
                 1)phenyl]-2-oxo-5 
               
               
                   
                 oxazolidinyl]methyl] 
               
               
                   
                 butanethioamide, 
               
               
                   
                 thiomorpholine 
               
               
                   
                 S-oxide 
               
               
                 32 
                 (S)-N-[[3-[3-Fluoro-4- 
                 Same as 
                 Z (e) 
               
               
                   
                 (4-thiomorpholinyl) 
                 above 
               
               
                   
                 phenyl]-2-oxo-5 
               
               
                   
                 oxazolidinyl]methyl]-3 
               
               
                   
                 methylbutanethioamide, 
               
               
                   
                 thiomorpholine 
               
               
                   
                 S-oxide 
               
               
                 33 
                 (S)-N-[[3-[3-Fluoro-4- 
                 Same as 
                 Z (f) 
               
               
                   
                 (4-thiomorpholinyl) 
                 above 
               
               
                   
                 phenyl]-2-oxo-5 
               
               
                   
                 oxazolidinyl]methyl]-2 
               
               
                   
                 methylbutanethioamide, 
               
               
                   
                 thiomorpholine 
               
               
                   
                 S-oxide 
               
               
                 34 
                 (S)-N-[[3-[3-Fluoro-4- 
                 Same as 
                 Z (g) 
               
               
                   
                 (4-thiomorpholinyl) 
                 above 
               
               
                   
                 phenyl]-2-oxo-5 
               
               
                   
                 oxazolidinyl]methyl] 
               
               
                   
                 3,3-dimethylbutanethio-amide, 
               
               
                   
                 thiomorpholine 
               
               
                   
                 S-oxide 
               
               
                 35 
                 (S)-N-[[3-[3-Fluoro-4- 
                 Same as 
                 Z (h) 
               
               
                   
                 (4-thiomorpholinyl) 
                 above 
               
               
                   
                 phenyl]-2-oxo-5 
               
               
                   
                 oxazolidinyl]methyl] 
               
               
                   
                 cyclobutanecarbothioamide, 
               
               
                   
                 thiomorpholine 
               
               
                   
                 S-oxide 
               
               
                 36 
                 (S)-N-[[3-[3-Fluoro-4- 
                 Same as 
                 Z (i) 
               
               
                   
                 (4-thiomorpholinyl) 
                 above 
               
               
                   
                 phenyl]-2-oxo-5 
               
               
                   
                 oxazolidinyl]methyl]-1- 
               
               
                   
                 cyclopentanecarbothio-amide, 
               
               
                   
                 thiomorpholine 
               
               
                   
                 S-oxide 
               
               
                 37 
                 (S)-N-[[3-[3-Fluoro-4- 
                 Same as above 
                 Z(j) 
               
               
                   
                 (4-thiomorpholinyl) 
               
               
                   
                 phenyl]-2-oxo-5 
               
               
                   
                 oxazolidinyl]methyl] 
               
               
                   
                 cyclohexanecarbothio-amide, 
               
               
                   
                 thiomorpholine 
               
               
                   
                 S-oxide 
               
               
                 38 
                 (S)-N-[(3-[3-Fluoro-4- 
                 Same as above 
                 Z (k) 
               
               
                   
                 (4-thiomorpholinyl)- 
               
               
                   
                 phenyl]-2-oxo-5 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 cyclopropylethanethio-amide, 
               
               
                   
                 thiomorpholine 
               
               
                   
                 S-oxide 
               
               
                 39 
                 (S)-N-[[3-[3-Fluoro-4- 
                 Same as above 
                 Z (l) 
               
               
                   
                 (4-thiomorpholinyl)- 
               
               
                   
                 phenyl]-2-oxo-5 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 cyclobutylethanethio-amide, 
               
               
                   
                 thiomorpholine 
               
               
                   
                 S-oxide 
               
               
                 40 
                 (S)-N-[[3-[3-Fluoro-4- 
                 Same as above 
                 Z (m) 
               
               
                   
                 (4-thiomorpholinyl)- 
               
               
                   
                 phenyl]-2-oxo-5 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 cyclopentylethanethio-amide, 
               
               
                   
                 thiomorpholine 
               
               
                   
                 S-oxide 
               
               
                 41 
                 (S)-N-[[3-[3-Fluoro-4- (4-thiomorpholinyl)- phenyl]-2-oxo-5 oxazolidinyl]methyl]- thioacetamide, thiomorpholine S-oxide 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Ethyl dithioacetate 
               
               
                 42 
                 (S)-N-[[3-[3-Fluoro-4- 
                 Same as above 
                 Z (a) 
               
               
                   
                 (4-thiomorpholinyl)- 
               
               
                   
                 phenyl]-2-oxo-5 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 propanethioamide, 
               
               
                   
                 thiomorpholine 
               
               
                   
                 S-oxide 
               
               
                 43 
                 (S)-N-[[3-[3-Difluoro- 
                 Same as 
                 Z (b) 
               
               
                   
                 4- 
                 above 
               
               
                   
                 (4-thiomorpholinyl)- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethio-amide, 
               
               
                   
                 thiomorpholine 
               
               
                   
                 S-oxide 
               
               
                 44 
                 (S)-N-[[3-[3-Difluoro- 
                 Same as 
                 Z (c) 
               
               
                   
                 4- 
                 above 
               
               
                   
                 (4-thiomorpholinyl)- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclopropanecarbothio-amide, 
               
               
                   
                 thiomorpholine 
               
               
                   
                 S-oxide 
               
               
                 45 
                 (S)-N-[[3-[4-(4 thiomorpholinyl)- phenyl]-2-oxo-5- oxazolidiny]methyl]- thioacetamide, thiomorpholine S-oxide 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Ethyl dithioacetate 
               
               
                 46 
                 (S)-N-[[3-[4-(4 
                 Same as 
                 Z (a) 
               
               
                   
                 thiomorpholinyl)- 
                 above 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 propanethioamide, 
               
               
                   
                 thiomorpholine 
               
               
                   
                 S-oxide 
               
               
                 47 
                 (S)-N-[[3-[4-(4 
                 Same as 
                 Z (b) 
               
               
                   
                 thiomorpholinyl)- 
                 above 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethio-amide, 
               
               
                   
                 thiomorpholine 
               
               
                   
                 S-oxide 
               
               
                 48 
                 (S)-N-[[3-[4-(4 
                 Same as 
                 Z (c) 
               
               
                   
                 thiomorpholinyl)- 
                 above 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclopropanecarbothio-amide, 
               
               
                   
                 thiomorpholine 
               
               
                   
                 S-oxide 
               
               
                 49 
                 (S)-N-[[3-[3,5- Difluoro-4-(4- hydroxyacetyl)-1- piperazinyl]pheny 1]-2-oxo-5- oxazolidinyl]- methyl]propanethioamide 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Z (a) 
               
               
                 50 
                 (S)-N-[[3-[3,5- 
                 Same as 
                 Z (b) 
               
               
                   
                 Difluoro-4-(4- 
                 above 
               
               
                   
                 hydroxyacetyl)-1- 
               
               
                   
                 piperazinyl]pheny-1]-2- 
               
               
                   
                 oxo-5- 
               
               
                   
                 oxazolidinyl]- 
               
               
                   
                 methyl]-2-methyl- 
               
               
                   
                 propanethioamide 
               
               
                 51 
                 (S)-N-[[3-[3,5- 
                 Same as 
                 Z (c) 
               
               
                   
                 Difluoro-4-(4- 
                 above 
               
               
                   
                 hydroxyacetyl)-1- 
               
               
                   
                 piperazinyl]pheny-1]-2- 
               
               
                   
                 oxo-5- 
               
               
                   
                 oxazolidinyl]- 
               
               
                   
                 methyl]cyclopropanethio-amide 
               
               
                 52 
                 (S)-N-[[3-[3-[4 (hydroxyacetyl)-1- piperazinyl]pheny 1]-2-oxo-5- oxazolidinyl]- methyl]propanethioamide 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Z (a) 
               
               
                 53 
                 (S)-N-[[3-[3-[4 
                 Same as 
                 Z (b) 
               
               
                   
                 (hydroxyacetyl)- 
                 above 
               
               
                   
                 1- 
               
               
                   
                 piperazinyl]pheny 
               
               
                   
                 1]-2- 
               
               
                   
                 oxo-5- 
               
               
                   
                 oxazolidinyl]- 
               
               
                   
                 methyl]-2-methyl- 
               
               
                   
                 propanethio-amide 
               
               
                 54 
                 (S)-N-[[3-[3-[4 
                 Same as 
                 Z (c) 
               
               
                   
                 (hydroxyacetyl)- 
                 above 
               
               
                   
                 1- 
               
               
                   
                 piperazinyl]pheny 
               
               
                   
                 1]-2- 
               
               
                   
                 oxo-5- 
               
               
                   
                 oxazolidinyl]- 
               
               
                   
                 methyl]cyclopropane- 
               
               
                   
                 carbothio-amide 
               
               
                   
               
             
          
         
       
     
     
       
         
               
               
               
               
             
           
               
                 TABLE D 
               
               
                   
               
               
                   
                   
                   
                 Dithio 
               
               
                   
                   
                   
                 Compound 
               
               
                 Example 
                   
                   
                 (from 
               
               
                 No. 
                 Compound 
                 Amine 
                 Preparation Z) 
               
               
                   
               
             
             
               
                 55 
                 (S)-N-[[3-[3- Fluoro-4- (4- thiomorpholinyl)- phenyl]-2-oxo-5- oxazolidinyl]meth yl]- propanethioamide, thiomorpholine S,S- dioxide 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Z (a) 
               
               
                 56 
                 (S)-N-[[3-[3- 
                 Same as 
                 Z (b) 
               
               
                   
                 Fluoro-4- 
                 above 
               
               
                   
                 (4- 
               
               
                   
                 thiomorpholinyl)- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]-2- 
               
               
                   
                 methylpropanethio 
               
               
                   
                 amide, 
               
               
                   
                 thiomorpholine 
               
               
                   
                 S,S-dioxide 
               
               
                 57 
                 (S)-N-[[3-[3- 
                 Same as 
                 Z (c) 
               
               
                   
                 Fluoro-4- 
                 above 
               
               
                   
                 (4- 
               
               
                   
                 thiomorpholinyl)- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]- 
               
               
                   
                 cyclopropanecarbo 
               
               
                   
                 thio- 
               
               
                   
                 amide, 
               
               
                   
                 thiomorpholine 
               
               
                   
                 S,S-dioxide 
               
               
                 58 
                 (S)-N-[[3-[3,5- Difluoro- 4-(4- thiomorpholinyl)- phenyl]-2-oxo-5- oxazolidinyl]- methyl]thioacetam ide, thiomorpholine S,S- dioxide 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                 59 
                 (S)-N-[[3-[3,5- 
                 Same as 
                 Z (a) 
               
               
                   
                 Difluoro- 
                 above 
               
               
                   
                 4-(4- 
               
               
                   
                 thiomorpholinyl)- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]- 
               
               
                   
                 propanethioamide, 
               
               
                   
                 thiomorpholine 
               
               
                   
                 S,S- 
               
               
                   
                 dioxide 
               
               
                 60 
                 (S)-N-[[3-[3,5- 
                 Same as 
                 Z (b) 
               
               
                   
                 Difluoro- 
                 above 
               
               
                   
                 4-(4- 
               
               
                   
                 thiomorpholinyl)- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]-2- 
               
               
                   
                 methylpropanethio 
               
               
                   
                 — 
               
               
                   
                 amide, 
               
               
                   
                 thiomorpholine 
               
               
                   
                 S,S-dioxide 
               
               
                 61 
                 (S)-N-[[3-[3,5- 
                 Same as 
                 Z (c) 
               
               
                   
                 Difluoro- 
                 above 
               
               
                   
                 4-(4- 
               
               
                   
                 thiomorpholinyl)- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl] 
               
               
                   
                 cyclopropanecarbo 
               
               
                   
                 thio- 
               
               
                   
                 amide, 
               
               
                   
                 thiomorpholine 
               
               
                   
                 S,S-dioxide 
               
               
                 62 
                 (S)-N-[[3-[4-(4- thio- morpholinyl)pheny 1]-2-oxo-5- oxazolidinyl]- methyl]thioacetam ide, thiomorpholine S,S-dioxide 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Ethyl dithioacetate 
               
               
                 63 
                 (S)-N-[[3-[4-(4- 
                 Same as 
                 Z (a) 
               
               
                   
                 thio- 
                 above 
               
               
                   
                 morpholinyl)pheny 
               
               
                   
                 1]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]- 
               
               
                   
                 methyl]propanethi 
               
               
                   
                 o- 
               
               
                   
                 amide, 
               
               
                   
                 thiomorpholine 
               
               
                   
                 S,S-dioxide 
               
               
                 64 
                 (S)-N-[[3-[4-(4- 
                 Same as 
                 Z (b) 
               
               
                   
                 thio- 
                 above 
               
               
                   
                 morpholinyl)pheny 
               
               
                   
                 1]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]- 
               
               
                   
                 methyl]-2-methyl- 
               
               
                   
                 propanethioamide, 
               
               
                   
                 thiomorpholine 
               
               
                   
                 S,S-dioxide 
               
               
                 65 
                 (S)-N-[[3-[4-(4- 
                 Same as 
                 Z (c) 
               
               
                   
                 thio- 
                 above 
               
               
                   
                 morpholinyl)pheny 
               
               
                   
                 1]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]- 
               
               
                   
                 methyl]cyclopropa 
               
               
                   
                 ne- 
               
               
                   
                 carbothioamide, 
               
               
                   
                 thiomorpholine 
               
               
                   
                 S,S-dioxide 
               
               
                   
               
             
          
         
       
     
     
       
         
               
               
               
               
             
           
               
                 TABLE E 
               
               
                   
               
               
                   
                   
                   
                 Dithio 
               
               
                   
                   
                   
                 Compound 
               
               
                 Example 
                   
                   
                 (from 
               
               
                 No. 
                 Compound 
                 Amine 
                 Preparation Z) 
               
               
                   
               
             
             
               
                 66 
                 (S)-N[[3-[3- Fluoro-4- (4- thiomorpholinyl)- phenyl]-2-oxo-5- oxazolidinyl]meth yl]- propanethioamide 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Z (a) 
               
               
                 67 
                 (S)-N-[[3-[3- 
                 Same as 
                 Z (b) 
               
               
                   
                 Fluoro-4- 
                 above 
               
               
                   
                 (4- 
               
               
                   
                 thiomorpholinyl)- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]-2- 
               
               
                   
                 methylpropanethio 
               
               
                   
                 amide 
               
               
                 68 
                 (S)-N-[[3-[3- 
                 Same as 
                 Z (c) 
               
               
                   
                 Fluoro-4- 
                 above 
               
               
                   
                 (4- 
               
               
                   
                 thiomorpholinyl)- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]- 
               
               
                   
                 cyclopropanecarbo 
               
               
                   
                 thio- 
               
               
                   
                 amide 
               
               
                 69 
                 (S)-N-[[3-[3- 
                 Same as 
                 Z (d) 
               
               
                   
                 Fluoro-4- 
                 above 
               
               
                   
                 (4- 
               
               
                   
                 thiomorpholinyl)- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl] 
               
               
                   
                 butanethioamide 
               
               
                 70 
                 (S)-N-[[3-[3- 
                 Same as 
                 Z (e) 
               
               
                   
                 Fluoro-4- 
                 above 
               
               
                   
                 (4- 
               
               
                   
                 thiomorpholinyl)- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]-3- 
               
               
                   
                 methylbutanethioa 
               
               
                   
                 mide 
               
               
                 71 
                 (S)-N-[[3-[3- 
                 Same as 
                 Z (f) 
               
               
                   
                 Fluoro-4- 
                 above 
               
               
                   
                 (4- 
               
               
                   
                 thiomorpholinyl)- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]-2- 
               
               
                   
                 methylbutanethioa 
               
               
                   
                 mide 
               
               
                 72 
                 (S)-N-[[3-[3- 
                 Same as 
                 Z (g) 
               
               
                   
                 Fluoro-4- 
                 above 
               
               
                   
                 (4- 
               
               
                   
                 thiomorpholinyl)- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]- 
               
               
                   
                 3,3- 
               
               
                   
                 dimenthylbutaneth 
               
               
                   
                 io- 
               
               
                   
                 amide 
               
               
                 73 
                 (S)-N-[[3-[3- 
                 Same as 
                 Z (h) 
               
               
                   
                 Fluoro-4- 
                 above 
               
               
                   
                 (4- 
               
               
                   
                 thiomorpholinyl)- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]- 
               
               
                   
                 cyclobutanecarbot 
               
               
                   
                 hio- 
               
               
                   
                 amide 
               
               
                 74 
                 (S)-N-[[3-[3- 
                 Same as 
                 Z (i) 
               
               
                   
                 Fluoro-4- 
                 above 
               
               
                   
                 (4- 
               
               
                   
                 thiomorpholinyl)- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]- 
               
               
                   
                 cyclopentanecarbo 
               
               
                   
                 thio- 
               
               
                   
                 amide 
               
               
                 75 
                 (S)-N-[[3-[3- 
                 Same as 
                 Z (j) 
               
               
                   
                 Fluoro-4- 
                 above 
               
               
                   
                 (4- 
               
               
                   
                 thiomorpholinyl)- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]- 
               
               
                   
                 cyclohexanecarbot 
               
               
                   
                 hio 
               
               
                   
                 amide 
               
               
                 76 
                 (S)-N-[[3-[3- 
                 Same as 
                 Z (k) 
               
               
                   
                 Fluoro-4- 
                 above 
               
               
                   
                 (4- 
               
               
                   
                 thiomorpholinyl)- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]-2- 
               
               
                   
                 cyclopropylethane 
               
               
                   
                 thio- 
               
               
                   
                 amide 
               
               
                 77 
                 (S)-N-[[3-[3- 
                 Same as 
                 Z (l) 
               
               
                   
                 Fluoro-4- 
                 above 
               
               
                   
                 (4- 
               
               
                   
                 thiomorpholinyl)- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]-2- 
               
               
                   
                 cyclobutylethanet 
               
               
                   
                 hio- 
               
               
                   
                 amide 
               
               
                 78 
                 (S)-N-[[3-[3- 
                 Same as 
                 Z (m) 
               
               
                   
                 Fluoro-4- 
                 above 
               
               
                   
                 (4- 
               
               
                   
                 thiomorpholinyl)- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]-2- 
               
               
                   
                 cyclopentylethane 
               
               
                   
                 thio- 
               
               
                   
                 amide 
               
               
                 79 
                 (S)-N-[[3-[3,5- Difluoro- 4-(4- thiomorpholinyl)- phenyl]-2-oxo-5- oxazolidinyl]meth yl] thioacetamide 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Ethyl dithioacetate 
               
               
                 80 
                 (S)-N-[[3-[3,5- 
                 Same as 
                 Z (a) 
               
               
                   
                 Difluoro- 
                 above 
               
               
                   
                 4-(4- 
               
               
                   
                 thiomorpholinyl)- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl] 
               
               
                   
                 propanethioamide 
               
               
                 81 
                 (S)-N-[[3-[3,5- 
                 Same as 
                 Z (b) 
               
               
                   
                 Difluoro- 
                 above 
               
               
                   
                 4-(4- 
               
               
                   
                 thiomorpholinyl)- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]-2- 
               
               
                   
                 methylpropanethio 
               
               
                   
                 amide 
               
               
                 82 
                 (S)-N-[[3-[3,5- 
                 Same as 
                 Z (c) 
               
               
                   
                 Difluoro- 
                 above 
               
               
                   
                 4-(4- 
               
               
                   
                 thiomorpholinyl)- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl] 
               
               
                   
                 cyclopropanecarbo 
               
               
                   
                 thio-amide 
               
               
                 83 
                 (S)-N-[[3-[4-(4- thio- morpholinyl)pheny 1]-2-oxo-5- oxazolidinyl]- methyl]thioacetam ide 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                 84 
                 (S)-N-[[3-[4-(4- 
                 Same as 
                 Z (a) 
               
               
                   
                 thio- 
                 above 
               
               
                   
                 morpholinyl)pheny 
               
               
                   
                 1]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]- 
               
               
                   
                 methyl]propanethi 
               
               
                   
                 o- 
               
               
                   
                 amide 
               
               
                 85 
                 (S)-N-[[3-[4-(4- 
                 Same as 
                 Z (b) 
               
               
                   
                 thio- 
                 above 
               
               
                   
                 morpholinyl)pheny 
               
               
                   
                 1]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]- 
               
               
                   
                 methyl]-2-methyl- 
               
               
                   
                 propanethioamide 
               
               
                 86 
                 (S)-N-[[3-[4-(4- 
                 Same as 
                 Z (c) 
               
               
                   
                 thio- 
                 above 
               
               
                   
                 morpholinyl)pheny 
               
               
                   
                 1]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]- 
               
               
                   
                 methyl]cyclopropa 
               
               
                   
                 ne- 
               
               
                   
                 carbothioamide 
               
               
                   
               
             
          
         
       
     
     EXAMPLE 87 
     (S)-N-[[3-[3-Fluoro-4-(4-thiomorpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-1-azetidinecarbothioamide, thiomorpholine S-oxide; Anal. Calcd for C 18 H 23 FN 4 O 3 S 2 , C, 50.69; H, 5.43; N, 13.14. Found: C, 50.79; H, 5.45; N, 12.82; mp 213-214° C. 
     EXAMPLE 88 
     (S)-N-[[3-[3-Fluoro-4-(4-thiomorpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-1-azetidinecarbothioamide 
     EXAMPLE 89 
     (S)-N-[[3-[3-Fluoro-4-[4-(hydroxyacetyl)-1-piperazinyl]phenyl-2-oxo-5-oxazolidinyl]methyl]propanethioamide 
     
       
         
               
             
               
               
               
             
           
               
                 TABLE F 
               
             
             
               
                   
               
               
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
             
          
           
               
                 Example No. 
                 Compound 
               
               
                   
               
               
                 90 
                 (S)-N-[[3-[3-Fluoro-4-[4-(hy 
                 R = CH(CH 3 ) 2   
               
               
                   
                 droxy- 
               
               
                   
                 acetyl)-1-piperazinyl]phenyl 
               
               
                   
                 ]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2-methy 
               
               
                   
                 lpropane-thioamide; Anal. 
               
               
                   
                 calcd for C 20 H 27 FN 4 O 4 S: C, 
               
               
                   
                 54.78; H, 6.21; N, 12.78; S, 
               
               
                   
                 7.21. Found: C, 54.67; H, 
               
               
                   
                 6.34; N, 12.41; 
               
               
                   
                 S, 7.15 
               
               
                 91 
                 (S)-N-[[3-[3-Fluoro-4-[4-( hydroxy- acetyl)-1-piperazinyl]phen yl]-2-oxo-5- oxazolidinyl]methyl]cyclop ropane-carbothioamide; mp 179-181° C.; Anal. calcd for C 20 H 25 FN 4 O 4 S: C, 55.03; H, 5.77; N, 12.84; 5, 7.34. Found: C, 55.15; H, 5.72; N, 12.76; 5, 7.09 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                 92 
                 (S)-N-[[3-[3-Fluoro-4-[4-( 
                 R = CH 2 —CH 2 —CH 3   
               
               
                   
                 hydroxy- 
               
               
                   
                 acetyl)-1-piperazinyl]phen 
               
               
                   
                 yl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]butane 
               
               
                   
                 thioamlde 
               
               
                 93 
                 (S)-N-[[3-[3-Fluoro-4-[4-( hydroxy- acetyl)-1-piperazinyl]phen yl]-2-oxo-5- oxazolidinyl]methyl]-3-met hylbutane- thioamide 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                 94 
                 (S)-N-[[3-[3-Fluoro-4-[4-( hydroxy- acetyl)-1-piperazinyl]phen yl]-2-oxo-5- oxazolidinyl]methyl]-2-met hylbutane thioamide 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                 95 
                 (S)-N-[[3-[3-Fluoro-4-[4-( 
                 R = CH 2 —C(CH 3 ) 3   
               
               
                   
                 hydroxy 
               
               
                   
                 acetyl)-1-piperazinyl]phen 
               
               
                   
                 yl]-2-oxo-5- oxazolidinyl 
               
               
                   
                 oxazolidinyl]methyl]-3,3-d 
               
               
                   
                 imethyl- 
               
               
                   
                 butanethioamide 
               
               
                 96 
                 (S)-N-[[3-[3-Fluoro-4-[4-( hydroxy- acetyl)-1-piperazinyl]phen yl]-2-oxo-5- oxazolidinyl]methyl]cyclob utane-carbothioamide 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                 97 
                 (S)-N-[[3-[3-Fluoro-4-[4-( hydroxy- acetyl)-1-piperazinyl]phen yl]-2-oxo-5- oxazolidinyl]methyl]cyclop entane- carbothioamide 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                 98 
                 (S)-N-[[3-[3-Fluoro-4-[4-( hydroxy- acetyl)-1-piperazinyl]phen yl]-2-oxo-5- oxazolidinyl]methyl]cycloh exane- carbothioamide 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                 99 
                 (S)-N-[[3-[3-Fluoro-4-[4-( hydroxy- acetyl)-1-piperazinyl]phen yl]-2-oxo-5- oxazolidinyl]methyl]-2-cyc lopropyl-ethanethioamide 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                 100  
                 (S)-N-[[3-[3-Fluoro-4-[4-(hy droxy- acetyl)-1-piperazinyl]phenyl ]-2-oxo-5- oxazolidinyl]methyl]-2-cyclo butyl ethanethioamide 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                 101  
                 (S)-N-[[3-[3-Fluoro-4-[4-(hy droxy- acetyl)-1-piperazinyl]phenyl ]-2-oxo-5- oxazolidinyl]methyl]-2-cyclo pentylethanethioamide 
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
             
          
         
       
     
     EXAMPLE 102 
     (S)-N-[[3-[3-Fluoro-4-[4-(hydroxyacetyl)-1-piperazinyl]phenyl]-2oxo-5-oxazolidinyl]methyl]-1-azetidinecarbothioamide 
     EXAMPLE 103 
     (S)-N-[[3-Fluoro-4-(4-acetyl-1-piperazinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]thioacetamide 
     
       
         
               
               
               
               
             
               
               
               
               
               
             
           
               
                 TABLE G 
               
               
                   
               
             
             
               
                   
                   
                   
                 Dithio 
               
               
                 Example No. 
                 Product 
                 Amine 
                 Compound 
               
               
                   
               
               
                 104 
                 (S)-N-[[3-[3-Fluoro-4-(4-acetyl-1- 
                 P-90 
                 Z (a) 
               
               
                   
                 piperazinyl)phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]propanethioamide; mp 
               
               
                   
                 161-162° C.; Anal. calcd for 
               
               
                   
                 C 19 H 25 FN 4 O 3 S: C, 55.87; H, 6.17; N, 
               
               
                   
                 13.72; S, 7.85. Found: C, 55.79; H, 
               
               
                   
                 6.26; N, 13.60; S, 7.71 
               
               
                 105 
                 (S)-N-[[3-[3-Fluoro-4-(4-acetyl-1- 
                 P-90 
                 Z (b) 
               
               
                   
                 piperazinyl)phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2-methylpropane- 
               
               
                   
                 thioamide 
               
               
                 106 
                 (S)-N-[[3-[3-Fluoro-4-(4-acetyl-1- 
                 P-90 
                 Z (c) 
               
               
                   
                 piperazinyl)phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]cyclopropanecarbo- 
               
               
                   
                 thioamide; mp 159-160° C.; Anal. calcd 
               
               
                   
                 for 
               
               
                   
                 C 20 H 25 FN 4 O 3 S: C, 57.13; H, 5.99; 
               
               
                   
                 N, 13.32; S, 7.62. Found: C, 57.05; 
               
               
                   
                 H, 6.01; N, 13.15; S, 7.45. 
               
               
                 107 
                 (S)-N-[[3-[3-Fluoro-4-(4-acetyl-1- 
                 P-90 
                 Z (d) 
               
               
                   
                 piperazinyl)phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]butanethioamide 
               
               
                 108 
                 (S)-N-[[3-[3-Fluoro-4-(4-acetyl-1- 
                 P-90 
                 Z (e) 
               
               
                   
                 piperazinyl)phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-3-methylbutanethioamide 
               
               
                 109 
                 (S)-N-[[3-[3-Fluoro-4-(4-acetyl-1- 
                 P-90 
                 Z (f) 
               
               
                   
                 piperazinyl)phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2-methylbutane-thioamide 
               
               
                 110 
                 (S)-N-[[3-[3-Fluoro-4-(4-acetyl-1- 
                 P-90 
                 Z (g) 
               
               
                   
                 piperazinyl)phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-3,3-dimethylbutane- 
               
               
                   
                 thioamide 
               
               
                 111 
                 (S)-N-[[3-[3-Fluoro-4-(4-acetyl-1- 
                 P-90 
                 Z (h) 
               
               
                   
                 piperazinyl)phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]cyclobutanecarbo-thioamide 
               
               
                 112 
                 (S)-N-[[3-[3-Fluoro-4-(4-acetyl-1- 
                 P-90 
                 Z (i) 
               
               
                   
                 piperazinyl)phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]cyclopentanecarbo- 
               
               
                   
                 thioamide 
               
               
                 113 
                 (S)-N-[[3-[3-Fluoro-4-(4-acetyl-1- 
                 P-90 
                 Z (j) 
               
               
                   
                 piperazinyl)phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]cyclohexanecarbo- 
               
               
                   
                 thioamide 
               
               
                 114 
                 (S)-N-[[3-[3-Fluoro-4-(4-acetyl-1- 
                 P-90 
                 Z (k) 
               
               
                   
                 piperazinyl)phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2-cyclopropylethane- 
               
               
                   
                 thioamide 
               
               
                 115 
                 (S)-N-[[3-[3-Fluoro-4-(4-acetyl-1- 
                 P-90 
                 Z (l) 
               
               
                   
                 piperazinyl)phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2-cyclobutylethane- 
               
               
                   
                 thioamide 
               
               
                 116 
                 (S)-N-[[3-[3-Fluoro-4-(4-acetyl-1- 
                 P-90 
                 Z (m) 
               
               
                   
                 piperazinyl)phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2-cyclopentylethane- 
               
               
                   
                 thioamide 
               
               
                 117 
                 (S)-N-[[3-[3,5-Difluoro-4-(4-acetyl- 
                 P-91 
                 Ethyl 
               
               
                   
                 1-piperazinyl)- 
                   
                 dithio- 
               
               
                   
                 phenyl]-2-oxo-5-oxazolidinyl]methyl] 
                   
                 acetate 
               
               
                   
                 thioacetamide 
               
               
                 118 
                 (S)-N-[[3-[3,5-Difluoro-4-(4-acetyl- 
                 P-91 
                 Z (a) 
               
               
                   
                 1-piperazinyl)- 
               
               
                   
                 phenyl]-2-oxo-5-oxazolidinyl]methyl] 
               
               
                   
                 propane-thioamide 
               
               
                 119 
                 (S)-N-[[3-[3,5-Difluoro-4-(4-acetyl- 
                 P-91 
                 Z (b) 
               
               
                   
                 1-piperazinyl)- 
               
               
                   
                 phenyl]-2-oxo-5-oxazolidinyl] 
               
               
                   
                 methyl]-2-methyl-propanethioamide 
               
               
                 120 
                 (S)-N-[[3-[3, 5-Difluoro-4-(4-acetyl- 
                 P-91 
                 Z (c) 
               
               
                   
                 1-piperazinyl)- 
               
               
                   
                 phenyl]-2-oxo-5-oxazolidinyl]methyl] 
               
               
                   
                 cycloproane- 
               
               
                   
                 carbothioamide 
               
               
                 121 
                 (S)-N-[[3-[4-(4-Acetyl-1- 
                 P-92 
                 Ethyl 
               
               
                   
                 piperazinyl)-2-oxo-5- 
                   
                 dithio- 
               
               
                   
                 oxazolidinyl]methyl]thioacetamide 
                   
                 acetate 
               
               
                 122 
                 (S)-N-[[3-[4-(4-Acetyl-1- 
                 P-92 
                 Z (a) 
               
               
                   
                 piperazinyl)-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]propanethioamide 
               
               
                 123 
                 (S)-N-[[3-[4-(4-Acetyl-1- 
                 P-92 
                 Z (b) 
               
               
                   
                 piperazinyl)-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethioamide 
               
               
                 124 
                 (S)-N-[[3-[4-(4-Acetyl-1- 
                 P-92 
                 Z (c) 
               
               
                   
                 piperazinyl)-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]cyclopropane- 
               
               
                   
                 carbothioamide 
               
               
                 125 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P-93 
                 Ethyl 
               
               
                   
                 (methoxyacetyl)-1- 
                   
                 dithio- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                   
                 acetate 
               
               
                   
                 oxazolidinyl]methyl]-thioacetamide 
               
               
                 126 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P-93 
                 Z (a) 
               
               
                   
                 (methoxyacetyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 propanethioamide 
               
               
                 127 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P-93 
                 Z (b) 
               
               
                   
                 (methoxyacetyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 propanethioamide 
               
               
                 128 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P-93 
                 Z (c) 
               
               
                   
                 (methoxyacetyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 methylpropanethioamide 
               
               
                 129 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P-93 
                 Z (d) 
               
               
                   
                 (methoxyacetyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 butanethioamide 
               
               
                 130 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P-93 
                 Z (e) 
               
               
                   
                 (methoxyacetyl)-1- 
               
               
                   
                 (methoxyacetyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-3- 
               
               
                   
                 methylbutanethioamide 
               
               
                 131 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P-93 
                 Z (f) 
               
               
                   
                 (methoxyacetyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylbutanethioamide 
               
               
                 132 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P-93 
                 Z (g) 
               
               
                   
                 (methoxyacetyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-3, 3- 
               
               
                   
                 dimethylbutanethioamide 
               
               
                 133 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P-93 
                 Z (h) 
               
               
                   
                 (methoxyacetyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclobutanecarbothioamide 
               
               
                 134 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P-93 
                 Z (i) 
               
               
                   
                 (methoxyacetyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclopentanecarbothioamide 
               
               
                 135 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P-93 
                 Z (j) 
               
               
                   
                 (methoxyacetyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclohexanecarbothioamide 
               
               
                 136 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P-93 
                 Z (k) 
               
               
                   
                 (methoxyacetyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 cyclopropylethanethioamide 
               
               
                 137 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P-93 
                 Z (l) 
               
               
                   
                 (methoxyacetyl)-1-piperazinyl] 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 cyclobutylethanethioamide 
               
               
                 138 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P-93 
                 Z (m) 
               
               
                   
                 (methoxyacetyl)-1-piperazinyl] 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 cyclopentylethanethioamide 
               
               
                 139 
                 (S)-N-[[3-[3,5-Difluoro-[4-[4- 
                 P-94 
                 Ethyl 
               
               
                   
                 (methoxyacetyl)-1- 
                   
                 dithio- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                   
                 acetate 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 thioacetamide 
               
               
                 140 
                 (S)-N-[[3-[3,5-Difluoro-[4-[4- 
                 P-94 
                 Z (a) 
               
               
                   
                 (methoxyacetyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-propanethioamide 
               
               
                 141 
                 (S)-N-[[3-[3, 5-Difluoro-[4-[4- 
                 P-94 
                 Z (b) 
               
               
                   
                 (methoxyacetyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethioamide 
               
               
                 142 
                 (S)-N-[[3-[3,5-Difluoro-[4-[4- 
                 P-94 
                 Z (c) 
               
               
                   
                 (methoxyacetyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclopropanecarbothioamide 
               
               
                 143 
                 (S)-N-[[3-[4-[4-(methoxyacetyl)-1- 
                 P-95 
                 Ethyl 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5-oxazolidinyl] 
                   
                 dithio- 
               
               
                   
                 methyl]thioacetamide 
                   
                 acetate 
               
               
                 144 
                 (S)-N-[[3-[4-[4-(methoxyacetyl)-1- 
                 P-95 
                 Z (a) 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5-oxazolidinyl] 
               
               
                   
                 methyl]propanethioamide 
               
               
                 145 
                 (S)-N-[[3-[4-[4-(methoxyacetyl)-1- 
                 P-95 
                 Z (b) 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5-oxazolidinyl] 
               
               
                   
                 methyl]-2-methylpropane-thioamide 
               
               
                 146 
                 (S)-N-[[3-[4-[4-(methoxyacetyl)-1- 
                 P-95 
                 Z (c) 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl] 
               
               
                   
                 cyclopropanecarbothioamide 
               
               
                 147 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P-96 
                 Ethyl 
               
               
                   
                 (cyanoacetyl)-1-piperazinyl]- 
                   
                 dithio- 
               
               
                   
                 phenyl]-2-oxo-5-oxazolidinyl]methyl] 
                   
                 acetate 
               
               
                   
                 thioacetamide 
               
               
                 148 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P-96 
                 Z (a) 
               
               
                   
                 (cyanoacetyl)-1-piperazinyl]- 
               
               
                   
                 phenyl]-2-oxo-5-oxazolidinyl]methyl] 
               
               
                   
                 propanethioamide 
               
               
                 149 
                 (S)-N-[[3-[3-Fluoro-4-[4-(cyanoacetyl)- 
                 P-96 
                 Z (a) 
               
               
                   
                 1-piperazinyl]- 
               
               
                   
                 phenyl]-2-oxo-5-oxazolidinyl]methyl]- 
               
               
                   
                 2-methyl-propanethioamide 
               
               
                 150 
                 (S)-N-[[3-[3-Fluoro-4-[4-(cyanoacetyl)- 
                 P-96 
                 Z (b) 
               
               
                   
                 1-piperazinyl]- 
               
               
                   
                 phenyl]-2-oxo-5-oxazolidinyl]methyl] 
               
               
                   
                 cyclopropane-carbothioamide 
               
               
                 151 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P-97 
                 Ethyl 
               
               
                   
                 (cyanoacetyl)-1- 
                   
                 dithio- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                   
                 acetate 
               
               
                   
                 oxazolidinyl]- 
               
               
                   
                 methyl]thioacetamide 
               
               
                 152 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P-97 
                 Z (a) 
               
               
                   
                 (cyanoacetyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]-methyl]propanethioamide 
               
               
                 153 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P-97 
                 Z (b) 
               
               
                   
                 (cyanoacetyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethioamide 
               
               
                 154 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P-97 
                 Z (c) 
               
               
                   
                 (cyanoacetyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]- 
               
               
                   
                 methyl]cyclopropanecarbothioamide 
               
               
                 155 
                 (S)-N-[[3-[4-[4-(Cyanoacetyl)-1- 
                 P-98 
                 Ethyl 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                   
                 dithio- 
               
               
                   
                 oxazolidinyl]mazinyl]phenyl]-2- 
                   
                 dithio- 
               
               
                   
                 oxo-5-oxazolidinyl]methyl] 
                   
                 acetate 
               
               
                   
                 thioacetamide 
               
               
                 156 
                 (S)-N-[[3-[4-[4-(Cyanoacetyl)-1- 
                 P-98 
                 Z (a) 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]propanethioamide 
               
               
                 157 
                 (S)-N-[[3-[4-[4-(Cyanoacetyl)-1- 
                 P-98 
                 Z (b) 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethioamide 
               
               
                 158 
                 (S)-N-[[3-[4-[4-(Cyanoacetyl)-1- 
                 P-98 
                 Z (c) 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl] 
               
               
                   
                 cycopropanecarbothioamide 
               
               
                 159 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P-99 
                 Ethyl 
               
               
                   
                 (acetoxyacetyl)-1- 
                   
                 dithio- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                   
                 acetate 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 thioacetamide 
               
               
                 160 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P-99 
                 Z (a) 
               
               
                   
                 (acetoxyacetyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-propanethioamide 
               
               
                 161 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P-99 
                 Z (b) 
               
               
                   
                 (acetoxyacetyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethioamide 
               
               
                 162 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P-99 
                 Z (c) 
               
               
                   
                 (acetoxyacetyl)-1-piperazinyl] 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclopropanecarbothioamide 
               
               
                 163 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P-99 
                 Z (d) 
               
               
                   
                 (acetoxyacetyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-butanethioamide 
               
               
                 164 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P-99 
                 Z (e) 
               
               
                   
                 (acetoxyacetyl)-1-piperazinyl]phenyl]- 
               
               
                   
                 2-oxo-5-oxazolidinyl]methyl]-3- 
               
               
                   
                 methylbutanethioamide 
               
               
                 165 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P-99 
                 Z (f) 
               
               
                   
                 (acetoxyacetyl)-1-piperazinyl]phenyl]- 
               
               
                   
                 2-oxo-5-oxazolidinyl]methyl]-2- 
               
               
                   
                 methylbutanethioamide 
               
               
                 166 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P-99 
                 Z (g) 
               
               
                   
                 (acetoxyacetyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-3,3- 
               
               
                   
                 dimethylbutanethioamide 
               
               
                 167 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P-99 
                 Z (h) 
               
               
                   
                 (acetoxyacetyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclobutanecarbothioamide 
               
               
                 168 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P-99 
                 Z (i) 
               
               
                   
                 (acetoxyacetyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclopentanecarbothioamide 
               
               
                 169 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P-99 
                 Z (j) 
               
               
                   
                 (acetoxyacetyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo- 
               
               
                   
                 5-oxazolidinyl]methyl]- 
               
               
                   
                 cyclohexanecarbothioamide 
               
               
                 170 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P-99 
                 Z (k) 
               
               
                   
                 (acetoxyacetyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 cyclopropylethanethioamide 
               
               
                 171 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P-99 
                 Z (l) 
               
               
                   
                 (acetoxyacetyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 cyclobutylethanethioamide 
               
               
                 172 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P-99 
                 Z (m) 
               
               
                   
                 (acetoxyacetyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 cyclopentylethanethioamide 
               
               
                 173 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P- 
                 Ethyl 
               
               
                   
                 (acetoxyacetyl)-1- 
                 100 
                 dithio- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                   
                 acetate 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 thioacetamide 
               
               
                 174 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P- 
                 Z (a) 
               
               
                   
                 (acetoxyacetyl)-1- 
                 100 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 propanethioamide 
               
               
                 175 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P- 
                 Z (b) 
               
               
                   
                 (acetoxyacetyl)-1- 
                 100 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethioamide 
               
               
                 176 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P- 
                 Z (c) 
               
               
                   
                 (acetoxyacetyl)-1- 
                 100 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclopropanecarbothioamide 
               
               
                 177 
                 (S)-N-[[3-[4-[4-(Acetoxyacetyl)-1- 
                 P- 
                 Ethyl 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                 100 
                 dithio- 
               
               
                   
                 oxazolidinyl]methyl]thioacetamide 
                   
                 acetate 
               
               
                 178 
                 (S)-N-[[3-[4-[4-(Acetoxyacetyl)-1- 
                 P- 
                 Z (a) 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                 101 
               
               
                   
                 oxazolidinyl]methyl]propanethioamide 
               
               
                 179 
                 (S)-N-[[3-[4-[4-(Acetoxyacetyl)-1- 
                 P- 
                 Z (b) 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                 101 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropane-thioamide 
               
               
                 180 
                 (S)-N-[[3-[4-[4-(Acetoxyacetyl)-1- 
                 P- 
                 Z (c) 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                 101 
               
               
                   
                 oxazolidinyl]methyl] 
               
               
                   
                 cyclopropanecarbo-thioamide 
               
               
                 181 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Ethyl 
               
               
                   
                 (benzyloxyacetyl)-1- 
                 102 
                 dithio- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                   
                 acetate 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 thioacetamide 
               
               
                 182 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (a) 
               
               
                   
                 (benzyloxyacetyl)-1- 
                 102 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-propanethioamide 
               
               
                 183 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (b) 
               
               
                   
                 (benzyloxyacetyl)-1- 
                 102 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethioamide 
               
               
                 184 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (c) 
               
               
                   
                 (benzyloxyacetyl)-1-piperazinyl] 
                 102 
               
               
                   
                 phenyl]-2-oxo-5-oxazolidinyl]methyl]- 
               
               
                   
                 cyclopropanecarbothioamide 
               
               
                 185 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P- 
                 Ethyl 
               
               
                   
                 (benzyloxyacetyl)-1- 
                 103 
                 dithio- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                   
                 acetate 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 thioacetamide 
               
               
                 186 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P- 
                 Z (a) 
               
               
                   
                 (benzyloxyacetyl)-1- 
                 103 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-propanethioamide 
               
               
                 187 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P- 
                 Z (b) 
               
               
                   
                 (benzyloxyacetyl)-1- 
                 103 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethioamide 
               
               
                 188 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P- 
                 Z (c) 
               
               
                   
                 (benzyloxyacetyl)-1- 
                 103 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclopropanecarbothioamide 
               
               
                 189 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Ethyl 
               
               
                   
                 (methoxycarbonyl)-1- 
                 105 
                 dithio- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                   
                 acetate 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 thioacetamide 
               
               
                 190 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (a) 
               
               
                   
                 (methoxycarbonyl)-1- 
                 105 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-propanethioamide 
               
               
                 191 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (b) 
               
               
                   
                 (methoxycarbonyl)-1- 
                 105 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethioamide 
               
               
                 192 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (c) 
               
               
                   
                 (methoxycarbonyl)-1- 
                 105 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclopropanecarbothioamide 
               
               
                 193 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (d) 
               
               
                   
                 (methoxycarbonyl)-1- 
                 105 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-butanethioamide 
               
               
                 194 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (e) 
               
               
                   
                 (methoxycarbonyl)-1- 
                 105 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-3- 
               
               
                   
                 methylbutanethioamide 
               
               
                 195 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (f) 
               
               
                   
                 (methoxycarbonyl)-1- 
                 105 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylbutanethioamide 
               
               
                 196 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (g) 
               
               
                   
                 (methoxycarbonyl)-1- 
                 105 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-3, 
               
               
                   
                 3-dimethylbutanethioamide 
               
               
                 197 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (h) 
               
               
                   
                 (methoxycarbonyl)-1- 
                 105 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclobutanecarbothioamide 
               
               
                 198 
                 (S)-N-[[ 3-[3-Fluoro-4-[4- 
                 P- 
                 Z (i) 
               
               
                   
                 (methoxycarbonyl)-1- 
                 105 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclopentanecarbothioamide 
               
               
                 199 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (j) 
               
               
                   
                 (methoxycarbonyl)-1- 
                 105 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclohexanecarbothioamide 
               
               
                 200 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (k) 
               
               
                   
                 (methoxycarbonyl)-1- 
                 105 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 cyclopropylethanethioamide 
               
               
                 201 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (l) 
               
               
                   
                 (methoxycarbonyl)-1- 
                 105 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 cyclobutylethanethioamide 
               
               
                 202 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (m) 
               
               
                   
                 (methoxycarbonyl)-1- 
                 105 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 cyclopentylethanethioamide 
               
               
                 203 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P- 
                 Ethyl 
               
               
                   
                 (methoxycarbonyl)-1- 
                 106 
                 dithio- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                   
                 acetate 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 thioacetamide 
               
               
                 204 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P- 
                 Z (a) 
               
               
                   
                 (methoxycarbonyl)-1- 
                 106 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 propanethioamide 
               
               
                 205 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P- 
                 Z (b) 
               
               
                   
                 (methoxycarbonyl)-1- 
                 106 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethioamide 
               
               
                 206 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P- 
                 Z (c) 
               
               
                   
                 (methoxycarbonyl)-1- 
                 106 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclopropanecarbothioamide 
               
               
                 207 
                 (S)-N-[[3-[4-[4- 
                 P- 
                 Ethyl 
               
               
                   
                 (methoxycarbonyl)-1- 
                 107 
                 dithio- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                   
                 acetate 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 thioacetamide 
               
               
                 208 
                 (S)-N-[[3-[4-[4- 
                 P- 
                 Z (a) 
               
               
                   
                 (methoxycarbonyl)-1- 
                 107 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 propanethioamide 
               
               
                 209 
                 (S)-N-[[3-[4-[4- 
                 P- 
                 Z (b) 
               
               
                   
                 (methoxycarbonyl)-1- 
                 107 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethioamide 
               
               
                 210 
                 (S)-N-[[3-[4-[4- 
                 P- 
                 Z (c) 
               
               
                   
                 (methoxycarbonyl)-1- 
                 107 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclopropanecarbothioamide 
               
               
                 211 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Ethyl 
               
               
                   
                 (methanesulfonyl)-1- 
                 108 
                 dithio- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                   
                 acetate 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 thioacetamide; mp 197-198° C.; Anal, 
               
               
                   
                 calcd for C 17 H 23 FN 4 O 4 S 2 : C, 47.43; H, 
               
               
                   
                 5.39; N, 13.01; S, 14.89. Found: C, 
               
               
                   
                 47.25; H, 5.40; N, 12.82; S, 14.56. 
               
               
                 212 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (a) 
               
               
                   
                 (methanesulfonyl)-1- 
                 108 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 propanethioamide; mp 
               
               
                   
                 207-208° C.; Anal. calcd for 
               
               
                   
                 C 18 H 25 FN 4 O 4 S 2 : C, 48.63; H, 5.67; N, 
               
               
                   
                 12.60; S, 14.42. Found: C, 48.51; H, 
               
               
                   
                 5.59; N, 12.52; S, 14.09. 
               
               
                 213 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (b) 
               
               
                   
                 (methanesulfonyl)-1- 
                 108 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethioamide; 
               
               
                   
                 mp 204-206° C.; Anal. calcd 
               
               
                   
                 for C 19 H 27 FN 4 O 4 S 2 : C, 49.76; H, 5.93; 
               
               
                   
                 N, 12.22; S, 13.98. Found: C, 49.63; 
               
               
                   
                 H, 5.92; N, 14.14; S, 13.91. 
               
               
                 214 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (a) 
               
               
                   
                 (methanesulfonyl)-1- 
                 108 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclopropanecarbothioamide; Anal. 
               
               
                   
                 calcd for C 19 H 25 FN 4 O 4 S 2 : C, 49.98; H, 
               
               
                   
                 5.52; N, 12.27; S, 14.04. Found: C, 
               
               
                   
                 49.42; H, 5.50; N, 12.08; S, 13.80. 
               
               
                 215 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P- 
                 Ethyl 
               
               
                   
                 (methanesulfonyl)-1- 
                 109 
                 dithio- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                   
                 acetate 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 thioacetamide 
               
               
                 216 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
               
               
                   
                 (methanesulfonyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 propanethioamide 
               
               
                 217 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
               
               
                   
                 (methanesulfonyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethioamide 
               
               
                 218 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
               
               
                   
                 (methanesulfonyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclopropanecarbothioamide 
               
               
                 219 
                 (S)-N-[[3-[4-[4- 
               
               
                   
                 (methanesulfonyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 thioacetamide 
               
               
                 220 
                 (S)-N-[[3-[4-[4- 
               
               
                   
                 (methanesulfonyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 propanethioamide 
               
               
                 221 
                 (S)-N-[[3-[4-[4- 
               
               
                   
                 (methanesulfonyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethioamide 
               
               
                 222 
                 (S)-N-[[3-[4-[4- 
               
               
                   
                 (methanesulfonyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclopropanecarbothioamide 
               
               
                 223 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
               
               
                   
                 (ethanesulfonyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 thioacetamide 
               
               
                 224 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
               
               
                   
                 (ethanesulfonyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 propanethioamide 
               
               
                 225 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
               
               
                   
                 (ethanesulfonyl)-1- 
                 111 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethioamide 
               
               
                 226 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
               
               
                   
                 (ethanesulfonyl)-1- 
                 111 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclopropanecarbothioamide 
               
               
                 227 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P- 
               
               
                   
                 (ethanesulfonyl)-1- 
                 112 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 thioacetamide 
               
               
                 228 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P- 
               
               
                   
                 (ethanesulfonyl)-1- 
                 112 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 propanethioamide 
               
               
                 229 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P- 
               
               
                   
                 (ethanesulfonyl)-1- 
                 112 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethioamide 
               
               
                 230 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P- 
               
               
                   
                 (ethanesulfonyl)-1- 
                 112 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclopropanecarbothioamide 
               
               
                 231 
                 (S)-N-[[3-[4-[4-(ethanesulfonyl)-1- 
                 P- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                 113 
               
               
                   
                 oxazolidinyl]methyl]thioacetamide 
               
               
                 232 
                 (S)-N-[[3-[4-[4-(ethanesulfonyl)-1- 
                 P- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                 113 
               
               
                   
                 oxazolidinyl]methyl]propanethioamide 
               
               
                 233 
                 (S)-N-[[3-[4-[4-(ethanesulfonyl)-1- 
                 P- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                 113 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropane-thioamide 
               
               
                 234 
                 (S)-N-[[3-[4-[4-(ethanesulfonyl)-1- 
                 P- 
                 Z (c) 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                 113 
               
               
                   
                 oxazolidinyl]methyl] 
               
               
                   
                 cyclopropanecarbothioamide 
               
               
                 235 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Ethyl 
               
               
                   
                 (chloromethanesulfonyl)-1- 
                 114 
                 dithio- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                   
                 acetate 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 thioacetamide 
               
               
                 236 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (a) 
               
               
                   
                 (chloromethanesulfonyl)-1- 
                 114 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-propanethioamide 
               
               
                 237 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (b) 
               
               
                   
                 (chloromethanesulfonyl)-1- 
                 114 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethioamide 
               
               
                 238 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (c) 
               
               
                   
                 (chloromethanesulfonyl)-1- 
                 114 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclopropanecarbothioamide 
               
               
                 239 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P- 
                 Ethyl 
               
               
                   
                 (chloromethanesulfonyl)- 
                 115 
                 dithio- 
               
               
                   
                 1-piperazinyl]phenyl]-2-oxo-5- 
                   
                 acetate 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 thioacetamide 
               
               
                 240 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P- 
                 Z (a) 
               
               
                   
                 (chloromethanesulfonyl)- 
                 115 
               
               
                   
                 1-piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]propanethioamide 
               
               
                 241 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P- 
                 Z (b) 
               
               
                   
                 (chloromethanesulfonyl)-1- 
                 115 
               
               
                   
                 piperazinyl]phenyl]- 
               
               
                   
                 2-oxo-5-oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethioamide 
               
               
                 242 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P- 
                 Z (c) 
               
               
                   
                 (chloromethanesulfonyl)-1- 
                 115 
               
               
                   
                 piperazinyl]phenyl]- 
               
               
                   
                 2-oxo-5-oxazolidinyl]methyl]- 
               
               
                   
                 cyclopropanecarbothioamide 
               
               
                 243 
                 (S)-N-[[3-[4-[4- 
                 P- 
                 Ethyl 
               
               
                   
                 (chloromethanesulfonyl)-1- 
                 116 
                 dithio- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                   
                 acetate 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 thioacetamide 
               
               
                 244 
                 (S)-N-[[3-[4-[4- 
                 P- 
                 Z (a) 
               
               
                   
                 (chloromethanesulfonyl)-1- 
                 116 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-propanethioamide 
               
               
                 245 
                 (S)-N-[[3-[4-[4- 
                 P- 
                 Z (b) 
               
               
                   
                 (chloromethanesulfonyl)-1- 
                 116 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethioamide 
               
               
                 246 
                 (S)-N-[[3-[4-[4- 
                 P- 
                 Z (c) 
               
               
                   
                 (chloromethanesulfonyl)-1- 
                 116 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclopropanecarbothioamide 
               
               
                 247 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Ethyl 
               
               
                   
                 (cyanomethane-sulfonyl)-1- 
                 117 
                 dithio- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                   
                 acetate 
               
               
                   
                 oxazolidinyl]methyl]thioacetamide 
               
               
                 248 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (a) 
               
               
                   
                 (cyanomethane-sulfonyl)-1- 
                 117 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-propanethioamide 
               
               
                 249 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (b) 
               
               
                   
                 (cyanomethane-sulfonyl)-1- 
                 117 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethioamide 
               
               
                 250 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (c) 
               
               
                   
                 (cyanomethane-sulfonyl)-1- 
                 117 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclopropanecarbothioamide 
               
               
                 251 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                   
                 Ethyl 
               
               
                   
                 (cyanomethane-sulfonyl)-1- 
                   
                 dithio- 
               
               
                   
                 piperazinyl]phenyl]-2 
                   
                 acetate 
               
               
                   
                 -oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]thioacetamide 
               
               
                 252 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P- 
                 Z (a) 
               
               
                   
                 (cyanomethane-sulfonyl)-1- 
                 118 
               
               
                   
                 piperazinyl]phenyl]- 
               
               
                   
                 2-oxo-5-oxazolidinyl]- 
               
               
                   
                 methyl]propanethioamide 
               
               
                 253 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P- 
                 Z (b) 
               
               
                   
                 (cyanomethane-sulfonyl)-1- 
                 118 
               
               
                   
                 piperazinyl]phenyl]- 
               
               
                   
                 2-oxo-5-oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethioamide 
               
               
                 254 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P- 
                 Z (c) 
               
               
                   
                 (cyanomethane-sulfonyl)-1- 
                 118 
               
               
                   
                 piperazinyl]phenyl]- 
               
               
                   
                 2-oxo-5-oxazolidinyl]methyl]- 
               
               
                   
                 cyclopropanecarbothioamide 
               
               
                 255 
                 (S)-N-[[3-[4-[4- 
                 P- 
                 Ethyl 
               
               
                   
                 (Cyanomethanesulfonyl)-1- 
                 119 
                 dithio- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                   
                 acetate 
               
               
                   
                 oxazolidinyl]methyl]thioacetamide 
               
               
                 256 
                 (S)-N-[[3-[4-[4- 
                 P- 
                 Z (a) 
               
               
                   
                 (Cyanomethanesulfonyl)-1- 
                 119 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl] 
               
               
                   
                 propanethioamide 
               
               
                 257 
                 (S)-N-[[3-[4-[4- 
                 P- 
                 Z (b) 
               
               
                   
                 (Cyanomethanesulfonyl)-1- 
                 119 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethioamide 
               
               
                 258 
                 (S)-N-[[3-[4-[4- 
                 P- 
                 Z (c) 
               
               
                   
                 (Cyanomethanesulfonyl)-1- 
                 119 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl] 
               
               
                   
                 cyclopropanecarbo 
               
               
                   
                 thioamide 
               
               
                 259 
                 (S)-N-[[3-[3-Fluoro-4-[4-(N- 
                 P- 
                 Ethyl 
               
               
                   
                 methylsulfamoyl)-1- 
                 120 
                 dithio- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                   
                 acetate 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 thioacetamide 
               
               
                 260 
                 (S)-N-[[3-[3-Fluoro-4-[4-(N- 
                 P- 
                 Z (a) 
               
               
                   
                 methylsulfamoyl)-1- 
                 120 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 propanethioamide 
               
               
                 261 
                 (S)-N-[[3-[3-Fluoro-4-[4-(N- 
                 P- 
                 Z (b) 
               
               
                   
                 methylsulfamoyl)-1- 
                 120 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethioamide 
               
               
                 262 
                 (S)-N-[[3-[3-Fluoro-4-[4-(N- 
                 P- 
                 Z (c) 
               
               
                   
                 methylsulfamoyl)-1- 
                 120 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclopropanecarbothioamide 
               
               
                 263 
                 (S)-N-[[3-[3,5-Difluoro-4-[4-(N- 
                 P- 
                 Ethyl 
               
               
                   
                 methylsulfamoyl)-1- 
                 121 
                 dithio- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                   
                 acetate 
               
               
                   
                 oxazolidinyl]methyl]thioacetamide 
               
               
                 264 
                 (S)-N-[[3-[3,5-Difluoro-4-[4-(N- 
                 P- 
                 Z (a) 
               
               
                   
                 methylsulfamoyl)-1- 
                 121 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 propanethioamide 
               
               
                 265 
                 (S)-N-[[3-[3,5-Difluoro-4-[4-(N- 
                 P- 
                 Z (b) 
               
               
                   
                 methylsulfamoyl)-1- 
                 121 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethioamide 
               
               
                 266 
                 (S)-N-[[3-[3,5-Difluoro-4-[4-(N- 
                 P- 
                 Z (c) 
               
               
                   
                 methylsulfamoyl)-1- 
                 121 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclopropanecarbothioamide 
               
               
                 267 
                 (S)-N-[[3-[4-[4-(N- 
                 P- 
                 Ethyl 
               
               
                   
                 methylsulfamoyl)-1- 
                 122 
                 dithio- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                   
                 acetate 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 thioacetamide 
               
               
                 268 
                 (S)-N-[[3-[4-[4-(N- 
                 P- 
                 Z (a) 
               
               
                   
                 methylsulfamoyl)-1- 
                 122 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 propanethioamide 
               
               
                 269 
                 (S)-N-[[3-[4-[4-(N- 
                 P- 
                 Z (b) 
               
               
                   
                 methylsulfamoyl)-1- 
                 122 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethioamide 
               
               
                 270 
                 (S)-N-[[3-[4-[4-(N- 
                 P- 
                 Z (c) 
               
               
                   
                 methylsulfamoyl)-1- 
                 122 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclopropanecarbothioamide 
               
               
                 271 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Ethyl 
               
               
                   
                 (N,N-dimethylsulfamoyl)-1- 
                 123 
                 dithio- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                   
                 acetate 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 thioacetamide 
               
               
                 272 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (a) 
               
               
                   
                 (N,N-dimethylsulfamoyl)-1- 
                 123 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 propanethioamide 
               
               
                 273 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (b) 
               
               
                   
                 (N,N-dimethylsulfamoyl)-1- 
                 123 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethioamide 
               
               
                 274 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (c) 
               
               
                   
                 (N,N-dimethylsulfamoyl)-1- 
                 123 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclopropanecarbothioamide 
               
               
                 275 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P- 
                 Ethyl 
               
               
                   
                 (N,N-dimethylsulfamoyl)-1- 
                 124 
                 dithio- 
               
               
                   
                 piperazinyl]phenyl]- 
                   
                 acetate 
               
               
                   
                 2-oxo-5-oxazolidinyl]methyl]- 
               
               
                   
                 thioacetamide 
               
               
                 276 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P- 
                 Z (a) 
               
               
                   
                 (N,N-dimethylsulfamoyl)-1- 
                 124 
               
               
                   
                 piperazinyl]phenyl]- 
               
               
                   
                 2-oxo-5-oxazolidinyl]methyl]- 
               
               
                   
                 propanethioamide 
               
               
                 277 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P- 
                 Z (b) 
               
               
                   
                 (N,N-dimethylsulfamoyl)-1- 
                 124 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethioamide 
               
               
                 278 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P- 
                 Z (c) 
               
               
                   
                 (N,N-dimethylsulfamoyl)-1- 
                 124 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclopropanecarbothioamide 
               
               
                 279 
                 (S)-N-[[3-[4-[4- 
                 P- 
                 Ethyl 
               
               
                   
                 (N,N-dimethylsulfamoyl)-1- 
                 125 
                 dithio- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                   
                 acetate 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 thioacetamide 
               
               
                 280 
                 (S)-N-[[3-[4-[4- 
                 P- 
                 Z (a) 
               
               
                   
                 (N,N-dimethylsulfamoyl)-1- 
                 125 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 propanethioamide 
               
               
                 281 
                 (S)-N-[[3-[4-[4- 
                 P- 
                 Z (b) 
               
               
                   
                 (N,N-dimethylsulfamoyl)-1- 
                 125 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethioamide 
               
               
                 282 
                 (S)-N-[[3-[4-[4- 
                 P- 
                 Z (c) 
               
               
                   
                 (N,N-dimethylsulfamoyl)-1- 
                 125 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclopropanecarbothioamide 
               
               
                 283 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Ethyl 
               
               
                   
                 (ethoxycarbonyl)-1- 
                 126 
                 dithio- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                   
                 acetate 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 thioacetamide 
               
               
                 284 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (a) 
               
               
                   
                 (ethoxycarbonyl)-1- 
                 126 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 propanethioamide 
               
               
                 285 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (b) 
               
               
                   
                 (ethoxycarbonyl)-1- 
                 126 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethioamide 
               
               
                 286 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (c) 
               
               
                   
                 (ethoxycarbonyl)-1- 
                 126 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclopropanecarbothioamide 
               
               
                 287 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (d) 
               
               
                   
                 (ethoxycarbonyl)-1- 
                 126 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 butanethioamide 
               
               
                 288 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (e) 
               
               
                   
                 (ethoxycarbonyl)-1- 
                 126 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-3- 
               
               
                   
                 methylbutanethioamide 
               
               
                 289 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (f) 
               
               
                   
                 (ethoxycarbonyl)-1- 
                 126 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylbutanethioamide 
               
               
                 290 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (g) 
               
               
                   
                 (ethoxycarbonyl)-1- 
                 126 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-3,3- 
               
               
                   
                 dimethylbutanethioamide 
               
               
                 291 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (h) 
               
               
                   
                 (ethoxycarbonyl)-1- 
                 126 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclobutanecarbothioamide 
               
               
                 292 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (i) 
               
               
                   
                 (ethoxycarbonyl)-1- 
                 126 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclopentanecarbothioamide 
               
               
                 293 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (j) 
               
               
                   
                 (ethoxycarbonyl)-1- 
                 126 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclohexanecarbothioamide 
               
               
                 294 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (k) 
               
               
                   
                 (ethoxycarbonyl)-1- 
                 126 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 cyclopropylethanethioamide 
               
               
                 295 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (l) 
               
               
                   
                 (ethoxycarbonyl)-1- 
                 126 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 cyclobutylethanethioamide 
               
               
                 296 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (m) 
               
               
                   
                 (ethoxycarbonyl)-1- 
                 126 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 cyclopentylethanethioamide 
               
               
                 297 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P- 
                 Ethyl 
               
               
                   
                 (ethoxycarbonyl)-1- 
                 127 
                 dithio- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                   
                 acetate 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 thioacetmide 
               
               
                 298 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P- 
                 Z (a) 
               
               
                   
                 (ethoxycarbonyl)-1- 
                 127 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 propanethioamide 
               
               
                 299 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P- 
                 Z (b) 
               
               
                   
                 (ethoxycarbonyl)-1- 
                 127 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethioamide 
               
               
                 300 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P- 
                 Z (c) 
               
               
                   
                 (ethoxycarbonyl)-1- 
                 127 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclopropanecarbothioamide 
               
               
                 301 
                 (S)-N-[[3-[4-[4- 
                 P- 
                 Ethyl 
               
               
                   
                 (ethoxycarbonyl)-1- 
                 127 
                 dithio- 
               
               
                   
                 piperazinyl]- 
                   
                 acetate 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl] 
               
               
                   
                 thioacetamide 
               
               
                 302 
                 (S)-N-[[3-[4-[4- 
                 P- 
                 Z (a) 
               
               
                   
                 (ethoxycarbonyl)-1- 
                 128 
               
               
                   
                 piperazinyl]- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 propanethioamide 
               
               
                 303 
                 (S)-N-[[3-[4-[4- 
                 P- 
                 Z (b) 
               
               
                   
                 (ethoxycarbonyl)-1- 
                 128 
               
               
                   
                 piperazinyl]- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 2-methylpropanethioamide 
               
               
                 304 
                 (S)-N-[[3-[4-[4- 
                 P- 
                 Z (c) 
               
               
                   
                 (ethoxycarbonyl)-1- 
                 128 
               
               
                   
                 piperazinyl]- 
               
               
                   
                 phenyl]-2-oxo-5-oxazolidinyl] 
               
               
                   
                 methyl]cyclopropane-carbothioamide 
               
               
                 305 
                 (S)-N-[[3-[3-Fluoro-4-(4- 
                 P- 
                 Ethyl 
               
               
                   
                 sulfamoyl-1-piperazinyl)- 
                 129 
                 dithio- 
               
               
                   
                 phenyl]-2-oxo-5-oxazolidinyl] 
                   
                 acetate 
               
               
                   
                 methyl]thioacetamide 
               
               
                 306 
                 (S)-N-[[3-[3-Fluoro-4-(4- 
                 P- 
                 Z (a) 
               
               
                   
                 sulfamoyl-1-piperazinyl)- 
                 129 
               
               
                   
                 phenyl]-2-oxo-5-oxazolidinyl] 
               
               
                   
                 methyl]-propanethioamide 
               
               
                 307 
                 (S)-N-[[3-[3-Fluoro-4-(4- 
                 P- 
                 Z (b) 
               
               
                   
                 sulfamoyl-1-piperazinyl)- 
                 129 
               
               
                   
                 phenyl]-2-oxo-5-oxazolidinyl] 
               
               
                   
                 methyl]-2-methylpropanethioamide 
               
               
                 308 
                 (S)-N-[[3-[3-Fluoro-4-(4- 
                 P- 
                 Z (c) 
               
               
                   
                 sulfamoyl-1-piperazinyl)- 
                 129 
               
               
                   
                 phenyl]-2-oxo-5-oxazolidinyl] 
               
               
                   
                 methyl]-cyclopropanecarbothioamide 
               
               
                 309 
                 (S)-N-[[3-[3-Fluoro-4-(4- 
                 P- 
                 Z (d) 
               
               
                   
                 sulfamoyl-1-piperazinyl)- 
                 129 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]butanethioamide 
               
               
                 310 
                 (S)-N-[[3-[3-Fluoro-4-(4-sulfamoyl-1- 
                 P- 
                 Z (e) 
               
               
                   
                 piperazinyl)phenyl]-2-oxo-5- 
                 129 
               
               
                   
                 oxazolidinyl]methyl]-3- 
               
               
                   
                 methylbutanethioamide 
               
               
                 311 
                 (S)-N-[[3-[3-Fluoro-4-(4- 
                 P- 
                 Z (f) 
               
               
                   
                 sulfamoyl-1-piperazinyl) 
                 129 
               
               
                   
                 phenyl]-2-oxo-5-oxazolidinyl] 
               
               
                   
                 methyl]-2-methylbutanethioamide 
               
               
                 312 
                 (S)-N-[[3-[3-Fluoro-4-(4- 
                 P- 
                 Z (g) 
               
               
                   
                 sulfamoyl-1-piperazinyl)phenyl]- 
                 129 
               
               
                   
                 2-oxo-5-oxazolidinyl]methyl]-3,3- 
               
               
                   
                 dimethylbutanethioamide 
               
               
                 313 
                 (S)-N-[[3-[3-Fluoro-4-(4- 
                 P- 
                 Z (g) 
               
               
                   
                 sulfamoyl-1-piperazinyl)phenyl]- 
                 129 
               
               
                   
                 2-oxo-5-oxazolidinyl] 
               
               
                   
                 methyl]cyclobutanecarbothioamide 
               
               
                 314 
                 (S)-N-[[3-[3-Fluoro-4-(4- 
                 P- 
                 Z (i) 
               
               
                   
                 sulfamoyl-1-piperazinyl)phenyl]- 
                 129 
               
               
                   
                 2-oxo-5-oxazolidinyl]methyl] 
               
               
                   
                 cyclopentanecarbothioamide 
               
               
                 315 
                 (S)-N-[[3-[3-Fluoro-4-(4- 
                 P- 
                 Z (j) 
               
               
                   
                 sulfamoyl-1-piperazinyl) 
                 129 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl] 
               
               
                   
                 cyclohexanecarbothioamide 
               
               
                 316 
                 (S)-N-[[3-[3-Fluoro-4-(4- 
                 P- 
                 Z (k) 
               
               
                   
                 sulfamoyl-1-piperazinyl) 
                 129 
               
               
                   
                 phenyl]-2-oxo-5-oxazolidinyl] 
               
               
                   
                 methyl]-2-cyclopropylethane- 
               
               
                   
                 thioamide 
               
               
                 317 
                 (S)-N-[[3-[3-Fluoro-4-(4- 
                 P- 
                 Z (l) 
               
               
                   
                 sulfamoyl-1-piperazinyl)phenyl]- 
                 129 
               
               
                   
                 2-oxo-5-oxazolidinyl] 
               
               
                   
                 methyl]-2-cyclobutylethane- 
               
               
                   
                 thioamide 
               
               
                 318 
                 (S)-N-[[3-[3-Fluoro-4-(4- 
                 P- 
                 Z (m) 
               
               
                   
                 sulfamoyl-1-piperazinyl)phenyl]- 
                 129 
               
               
                   
                 2-oxo-5-oxazolidinyl] 
               
               
                   
                 methyl]-2-cyclopentylethane- 
               
               
                   
                 thioamide 
               
               
                 319 
                 (S)-N-[[3-[3,5-Difluoro-4-(4- 
                 P- 
                 Ethyl 
               
               
                   
                 sulfamoyl-1-piperazinyl)phenyl]- 
                 130 
                 dithio- 
               
               
                   
                 2-oxo-5-oxazolidinyl] 
                   
                 acetate 
               
               
                   
                 methyl]thioacetamide 
               
               
                 320 
                 (S)-N-[[3-[3,5-Difluoro-4-(4- 
                 P- 
                 Z (a) 
               
               
                   
                 sulfamoyl-1-piperazinyl)phenyl]- 
                 130 
               
               
                   
                 2-oxo-5-oxazolidinyl] 
               
               
                   
                 methyl]propanethioamide 
               
               
                 321 
                 (S)-N-[[3-[3,5-Difluoro-4-(4- 
                 P- 
                 Z (b) 
               
               
                   
                 sulfamoyl-1-piperazinyl)phenyl]- 
                 130 
               
               
                   
                 2-oxo-5-oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethioamide 
               
               
                 322 
                 (S)-N-[[3-[3,5-Difluoro-4-(4- 
                 P- 
                 Z (c) 
               
               
                   
                 sulfamoyl-1-piperazinyl)phenyl]- 
                 130 
               
               
                   
                 2-oxo-5-oxazolidinyl]methyl] 
               
               
                   
                 cyclopropanecarbothioamide 
               
               
                 323 
                 (S)-N-[[3-[4-(4-sulfamoyl-1- 
                 P- 
                 Ethyl 
               
               
                   
                 piperazinyl)phenyl]-2-oxo-5- 
                 131 
                 dithio- 
               
               
                   
                 oxazolidinyl]methyl] 
                   
                 acetate 
               
               
                   
                 thioacetamide 
               
               
                 324 
                 (S)-N-[[3-[4-(4-sulfamoyl-1- 
                 P- 
                 Z (a) 
               
               
                   
                 piperazinyl)phenyl]-2-oxo-5- 
                 131 
               
               
                   
                 oxazolidinyl]methyl] 
               
               
                   
                 propanethioamide 
               
               
                 325 
                 (S)-N-[[3-[4-(4-sulfamoyl-1- 
                 P- 
                 Z (b) 
               
               
                   
                 piperazinyl)phenyl]-2-oxo-5- 
                 131 
               
               
                   
                 oxazolidinyl]methy 
               
               
                   
                 yl)phenyl]-2-oxo-5-oxazolidinyl] 
               
               
                   
                 methyl]-2-methylpropanethioamide 
               
               
                 326 
                 (S)-N-[[3-[4-(4-sulfamoyl-1- 
                 P- 
                 Z (c) 
               
               
                   
                 piperazinyl)phenyl]-2-oxo-5- 
                 131 
               
               
                   
                 oxazolidinyl]methyl] 
               
               
                   
                 cyclopropanecarbothioamide 
               
               
                 327 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Ethyl 
               
               
                   
                 (cyanomethyl)-1- 
                 132 
                 dithio- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                   
                 acetate 
               
               
                   
                 oxazolidinyl]methyl]thioacetamide 
               
               
                 328 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (a) 
               
               
                   
                 (cyanomethyl)-1- 
                 132 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5 
               
               
                   
                 oxazolidinyl]methyl] 
               
               
                   
                 propanethioamide 
               
               
                 329 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (b) 
               
               
                   
                 (cyanomethyl)-1- 
                 132 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethioamide 
               
               
                 330 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
                 P- 
                 Z (c) 
               
               
                   
                 (cyanomethyl)-1- 
                 132 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl] 
               
               
                   
                 cyclopropanecarbothioamide 
               
               
                 331 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P- 
                 Ethyl 
               
               
                   
                 (cyanomethyl)-1- 
                 133 
                 dithio- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                   
                 acetate 
               
               
                   
                 oxazolidinyl]methyl]thioacetamide 
               
               
                 332 
                 (S)-N-[[3-[3,5-Difluoro-4-[4-( 
                 P- 
                 Z (a) 
               
               
                   
                 cyanomethyl)-1- 
                 133 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]propanethioamide 
               
               
                 333 
                 (S)-N-[[3-[3,5-Difluoro-4-[4 
                 P- 
                 Z (b) 
               
               
                   
                 cyanomethyl)-1- 
                 133 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethioamide 
               
               
                 334 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P- 
                 Z (c) 
               
               
                   
                 (cyanomethyl)-1-piperazinyl] 
                 133 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclopropanecarbothioamide 
               
               
                 335 
                 (S)-N-[[3-[4-[4-(cyanomethyl)-1- 
                 P- 
                 Ethyl 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                 134 
                 dithio- 
               
               
                   
                 oxazolidinyl]methyl]thioacetamide 
                   
                 acetate 
               
               
                 336 
                 (S)-N-[[3-[4-[4-(cyanomethyl)-1- 
                 P- 
                 Z (a) 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                 134 
               
               
                   
                 oxazolidinyl]methyl]propanethioamide 
               
               
                 337 
                 (S)-N-[[3-[4-[4-(cyanomethyl)-1- 
                 P- 
                 Z (b) 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                 134 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethioamide 
               
               
                 338 
                 (S)-N-[[3-[4-[4-(cyanomethyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl] 
               
               
                   
                 cyclopropanecarbothioamide 
               
               
                 339 
                 (S)-N-[[3-[3-Fluoro-4-[4-(2- 
                 P- 
                 Ethyl 
               
               
                   
                 fluoroethyl)-1- 
                 135 
                 dithio- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                   
                 acetate 
               
               
                   
                 oxazolidinyl]methyl]thioacetamide 
               
               
                 340 
                 (S)-N-[[3-[3-Fluoro-4-[4-(2- 
                 P- 
                 Z (a) 
               
               
                   
                 fluoroethyl)-1- 
                 135 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]propanethioamide 
               
               
                 341 
                 (S)-N-[[3-[3-Fluoro-4-[4-(2- 
                 P- 
                 Z (b) 
               
               
                   
                 fluoroethyl)-1- 
                 135 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethioamide 
               
               
                 342 
                 (S)-N-[[3-[3-Fluoro-4-[4-(2- 
                 P- 
                 Z (c) 
               
               
                   
                 fluoroethyl)-1- 
                 135 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclopropanecarbothioamide 
               
               
                 343 
                 (S)-N-[[3-[3,5-Difluoro-4-[4-(2- 
                 P- 
                 Ethyl 
               
               
                   
                 fluoroethyl)-1- 
                 136 
                 dithio- 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                   
                 acetate 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 thioacetamide 
               
               
                 344 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P- 
                 Z (a) 
               
               
                   
                 (2-fluoroethyl)-1- 
                 136 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl] 
               
               
                   
                 propanethioamide 
               
               
                 345 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P- 
                 Z (b) 
               
               
                   
                 (2-fluoroethyl)-1- 
                 136 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethioamide 
               
               
                 346 
                 (S)-N-[[3-[3,5-Difluoro-4-[4- 
                 P- 
                 Z (c) 
               
               
                   
                 (2-fluoroethyl)-1- 
                 136 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 cyclopropanecarbothioamide 
               
               
                 347 
                 (S)-N-[[3-[4-[4-(2-fluoroethyl)-1- 
                 P- 
                 Ethyl 
               
               
                   
                 piperazinyl]phenyl]- 
                 137 
                 dithio- 
               
               
                   
                 2-oxo-5-oxazolidinyl]methyl] 
                   
                 acetate 
               
               
                   
                 thioacetamide 
               
               
                 348 
                 (S)-N-[[3-[4-[4-(2-fluoroethyl)-1- 
                 P- 
                 Z (a) 
               
               
                   
                 piperazinyl]phenyl]- 
                 137 
               
               
                   
                 2-oxo-5-oxazolidinyl]methyl] 
               
               
                   
                 propanethioamide 
               
               
                 349 
                 (S)-N-[[3-[4-[4-(2-fluoroethyl)-1- 
                 P- 
                 Z (b) 
               
               
                   
                 piperazinyl]phenyl]- 
                 137 
               
               
                   
                 2-oxo-5-oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethioamide 
               
               
                 350 
                 (S)-N-[[3-[4-[4-(2-fluoroethyl)-1- 
                 P- 
                 Z (c) 
               
               
                   
                 piperazinyl]phenyl]-2-oxo-5- 
                 137 
               
               
                   
                 oxazolidinyl]methyl] 
               
               
                   
                 cyclopropane-carbothioamide 
               
               
                 351 
                 (S)-N-[[3-[3-Fluoro-4-(4-formyl- 
                 P- 
                 Ethyl 
               
               
                   
                 1-piperazinyl)phenyl]-2-oxo-5- 
                 138 
                 dithio- 
               
               
                   
                 oxazolidinyl]methyl]thioacetamide; 
                   
                 acetate 
               
               
                   
                 Anal calcd for 
               
               
                   
                 C 17 H 21 FN 4 O 3 S: C, 53.67; H, 5.56; N, 
               
               
                   
                 14.73; S, 8.43. Found: C, 53.14; H, 
               
               
                   
                 5.42; N, 14.25; S, 8.18. 
               
               
                 352 
                 (S)-N-[[3-[3-Fluoro-4-(4-formyl- 
                 P- 
                 Z (a) 
               
               
                   
                 1-piperazinyl)phenyl]-2-oxo-5- 
                 138 
               
               
                   
                 oxazolidinyl]methyl] 
               
               
                   
                 propanethioamide; mp 
               
               
                   
                 166-167° C.; Anal. calcd for 
               
               
                   
                 C 18 H 23 FN 4 O 3 S: C, 54.81; 
               
               
                   
                 H, 5.88; N, 14.20; S, 8.13. Found: C, 
               
               
                   
                 54.83; H, 6.00; 
               
               
                   
                 N, 14.12; S, 7.96. 
               
               
                 353 
                 (S)-N-[[3-[3-Fluoro-4-(4-formyl- 
                 P- 
                 Z (b) 
               
               
                   
                 1-piperazinyl)phenyl]-2-oxo-5- 
                 138 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropane-thioamide; 
               
               
                   
                 mp 157-158° C.: Anal. calcd for 
               
               
                   
                 C 19 H 25 FN 4 O 3 S: C, 55.87, H, 6.17; N, 
               
               
                   
                 13.72; S, 7.85. Found: C, 55.67; H, 
               
               
                   
                 6.19; N, 13.50; S, 7.70. 
               
               
                 354 
                 (S)-N-[[3-[3-Fluoro-4-(4-formyl-1- 
                 P- 
                 Z (c) 
               
               
                   
                 piperazinyl)phenyl]-2-oxo-5- 
                 138 
               
               
                   
                 oxazolidinyl]methyl] 
               
               
                   
                 cyclopropane-carbothioamide; 
               
               
                   
                 mp 178-179° C.; Anal. calcd for 
               
               
                   
                 C 19 H 23 FN 4 O 3 S: C, 56.14; H, 5.70; N, 
               
               
                   
                 13.78; S, 7.89. Found: C, 56.13; H, 
               
               
                   
                 5.64; N, 13.64; S. 7.75. 
               
               
                 355 
                 (S)-N-[[3-[3,5-Difluro-4-(4- 
                 P- 
                 Ethyl 
               
               
                   
                 formyl-1-piperazinyl)- 
                 139 
                 dithio- 
               
               
                   
                 phenyl]-2-oxo-5- 
                   
                 acetate 
               
               
                   
                 oxazolidinyl]methyl] 
               
               
                   
                 thioacetamide 
               
               
                 356 
                 (S)-N-[[3-[3,5-Difluro-4-(4- 
                 P- 
                 Z (a) 
               
               
                   
                 formyl-1-piperazinyl)- 
                 139 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 propanethioamide 
               
               
                 357 
                 (S)-N-[[3-[3,5-Difluro-4-(4- 
                 P- 
                 Z (b) 
               
               
                   
                 formyl-1-piperazinyl)- 
                 139 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl]- 
               
               
                   
                 2-methyl-propanethioamide 
               
               
                 358 
                 (S)-N-[[3-[3,5-Difluro-4-(4- 
                 P- 
                 Z (c) 
               
               
                   
                 formyl-1-piperazinyl)- 
                 139 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methyl] 
               
               
                   
                 cyclo-propanecarbothioamide 
               
               
                 359 
                 (S)-N-[[3-[4-(4-formyl-1- 
                 P- 
                 Ethyl 
               
               
                   
                 piperazinyl)phenyl]-2-oxo-5- 
                 140 
                 dithio- 
               
               
                   
                 oxazolidinyl]methyl] 
                   
                 acetate 
               
               
                   
                 thioacetamide 
               
               
                 360 
                 (S)-N-[[3-[4-(4-formyl-1- 
                 P- 
                 Z (a) 
               
               
                   
                 piperazinyl)phenyl]-2-oxo-5- 
                 140 
               
               
                   
                 oxazolidinyl]methyl] 
               
               
                   
                 propanethioamide 
               
               
                 361 
                 (S)-N-[[3-[4-(4-formyl-1- 
                 P- 
                 Z (b) 
               
               
                   
                 piperazinyl)phenyl]-2-oxo-5- 
                 140 
               
               
                   
                 oxazolidinyl]methyl]-2- 
               
               
                   
                 methylpropanethioamide 
               
               
                 362 
                 (S)-N-[[3-[4-(4-formyl-1- 
                 P- 
                 Z (c) 
               
               
                   
                 piperazinyl)phenyl]-2-oxo-5- 
                 140 
               
               
                   
                 oxazolidinyl]methyl] 
               
               
                   
                 cyclopropane-carbothioamide 
               
               
                   
               
             
          
           
               
                   
                   
                 Isothiocyanate 
                   
                   
               
               
                 Example 
                   
                 Corresponding 
               
               
                 No. 
                 Product 
                 to Amine No. 
                 Amine 
               
               
                   
               
               
                 363 
                 (S)-N-[[3-[3-Fluoro-4-(4- 
               
               
                   
                 acetyl-1- 
               
               
                   
                 piperazinyl)phenyl]-2- 
               
               
                   
                 oxo-5-oxazolidinyl]- 
               
               
                   
                 methyl]-1- 
               
               
                   
                 azetidinecarbothioamide 
               
               
                 364 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
               
               
                   
                 (methoxyacetyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2- 
               
               
                   
                 oxo-5-oxazolidinyl] 
               
               
                   
                 methyl]-1- 
               
               
                   
                 azetidinecarbothioamide 
               
               
                 365 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
               
               
                   
                 (acetoxyacetyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2- 
               
               
                   
                 oxo-5-oxazolidinyl]- 
               
               
                   
                 methyl]-1- 
               
               
                   
                 azetidinecarbothioamide 
               
               
                 366 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
               
               
                   
                 (methoxycarbonyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2- 
               
               
                   
                 oxo-5-oxazolidinyl]- 
               
               
                   
                 methyl]-1- 
               
               
                   
                 azetidinecarbothioamide 
               
               
                 367 
                 (S)-N-[[3-[3-Fluoro-4-[4- 
               
               
                   
                 (ethoxycarbonyl)-1- 
               
               
                   
                 piperazinyl]phenyl]-2- 
               
               
                   
                 oxo-5-oxazolidinyl]- 
               
               
                   
                 methyl]-1- 
               
               
                   
                 azetidinecarbothioamide 
               
               
                 368 
                 (S)-N-[[3-[3-Fluoro-4- 
               
               
                   
                 (4-sulfamoyl-1- 
               
               
                   
                 piperazinyl)phenyl]-2- 
               
               
                   
                 oxo-5-oxazolidinyl]- 
               
               
                   
                 methyl]-1- 
               
               
                   
                 azetidinecarbothioamide 
               
               
                   
               
             
          
         
       
     
     EXAMPLE 369 
     (5S)-N-[[3-[3-Fluoro-4-(tetrahydro-1,4-thiazepin-4(5H)-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]thioacetamide, thiazepine S-oxide 
     
       
         
               
               
               
               
             
           
               
                 TABLE H 
               
               
                   
               
               
                   
                   
                   
                 Dithioester 
               
               
                 Example 
                   
                   
                 (from 
               
               
                 No. 
                 Compound 
                 Amine 
                 Preparation Z) 
               
               
                   
               
             
             
               
                 370 
                 (5S)-N-[[3-[3- Fluoro-4- (tetrahydro-1,4- thiazepin-4(5H)- yl))- phenyl]-2-oxo-5- oxazolidinyl]meth yl]- propanethioamide, thiazepine S- oxide 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Z (a) 
               
               
                 371 
                 S)-N-[[3-[3- 
                 Same as above 
                 Z (b) 
               
               
                   
                 Fluoro-4- 
               
               
                   
                 (tetrahydro-1,4- 
               
               
                   
                 thiazepin-4(5H)- 
               
               
                   
                 yl))- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]-2- 
               
               
                   
                 methylpropanethio 
               
               
                   
                 — 
               
               
                   
                 amide, thiazepine 
               
               
                   
                 S- 
               
               
                   
                 oxide. 
               
               
                 372 
                 (5S)-N-[[3-[3- 
                 Same as above 
                 Z (c) 
               
               
                   
                 Fluoro-4- 
               
               
                   
                 (tetrahydro-1,4- 
               
               
                   
                 thiazepin-4(5H)- 
               
               
                   
                 yl))- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]- 
               
               
                   
                 cyclopropanecarbo 
               
               
                   
                 thio- 
               
               
                   
                 amide, thiazepine 
               
               
                   
                 S- 
               
               
                   
                 oxide. 
               
               
                 373 
                 (5S)-N-[[3-[3- 
                 Same as above 
                 Z (d) 
               
               
                   
                 Fluoro-4- 
               
               
                   
                 (tetrahydro-1,4- 
               
               
                   
                 thiazepin-4(5H)- 
               
               
                   
                 yl))- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]- 
               
               
                   
                 butanethioamide, 
               
               
                   
                 thiazepine S- 
               
               
                   
                 oxide 
               
               
                 374 
                 (5S)-N-[[3-[3- 
                 Same as above 
                 Z (e) 
               
               
                   
                 Fluoro-4- 
               
               
                   
                 (tetrahydro-1,4- 
               
               
                   
                 thiazepin-4(5H)- 
               
               
                   
                 yl))- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methy 
               
               
                   
                 1]-3- 
               
               
                   
                 methylbutanethioam 
               
               
                   
                 ide, 
               
               
                   
                 thiazepine S-oxide 
               
               
                 375 
                 (5S)-N-[[3-[3- 
                 Same as above 
                 Z (f) 
               
               
                   
                 Fluoro-4- 
               
               
                   
                 (tetrahydro-1,4- 
               
               
                   
                 thiazepin-4(5H)- 
               
               
                   
                 yl))- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methy 
               
               
                   
                 1]-2- 
               
               
                   
                 methylbutanethioam 
               
               
                   
                 ide, 
               
               
                   
                 thiazepine S-oxide 
               
               
                 376 
                 (5S)-N-[[3-[3- 
                 Same as above 
                 Z (g) 
               
               
                   
                 Fluoro-4- 
               
               
                   
                 (tetrahydro-1,4- 
               
               
                   
                 thiazepin-4(5H)- 
               
               
                   
                 yl))- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methy 
               
               
                   
                 1]- 
               
               
                   
                 3,3- 
               
               
                   
                 dimethylbutanethio 
               
               
                   
                 — 
               
               
                   
                 amide, thiazepine 
               
               
                   
                 S- 
               
               
                   
                 oxide 
               
               
                 377 
                 (5S)-N-[[3-[3- 
                 Same as above 
                 Z (h) 
               
               
                   
                 Fluoro-4- 
               
               
                   
                 (tetrahydro-1,4- 
               
               
                   
                 thiazepin-4(5H)- 
               
               
                   
                 yl))- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methy 
               
               
                   
                 1]- 
               
               
                   
                 cyclobutanecarboth 
               
               
                   
                 io- 
               
               
                   
                 amide, thiazepine 
               
               
                   
                 S- 
               
               
                   
                 oxide 
               
               
                 378 
                 (5S)-N-[[3-[3- 
                 Same as above 
                 Z (i) 
               
               
                   
                 Fluoro-4- 
               
               
                   
                 (tetrahydro-1,4- 
               
               
                   
                 thiazepin-4(5H)- 
               
               
                   
                 yl))- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methy 
               
               
                   
                 1]-1- 
               
               
                   
                 cyclopentanecarbot 
               
               
                   
                 hio- 
               
               
                   
                 amide, thiazepine 
               
               
                 S- 
               
               
                   
                 oxide 
               
               
                 379 
                 (5S)-N-[[3-[3- 
                 Same as above 
                 Z (j) 
               
               
                   
                 Fluoro-4 - 
               
               
                   
                 (tetrahydro-1,4- 
               
               
                   
                 thiazepin-4(5H)- 
               
               
                   
                 yl))- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]- 
               
               
                   
                 cyclohexanecarbot 
               
               
                   
                 hio- 
               
               
                   
                 amide, thiazepine 
               
               
                 S- 
               
               
                   
                 oxide 
               
               
                 380 
                 (5S)-N-[[3-[3- 
                 Same as above 
                 Z (k) 
               
               
                   
                 Fluoro-4- 
               
               
                   
                 (tetrahydro-1,4- 
               
               
                   
                 thiazepin-4(5H)- 
               
               
                   
                 yl))- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]-2- 
               
               
                   
                 cyclopropylethane 
               
               
                   
                 thio- 
               
               
                   
                 amide, thiazepine 
               
               
                   
                 S- 
               
               
                   
                 oxide 
               
               
                 381 
                 (5S)-N-[[3-[3- 
               
               
                   
                 Fluoro-4- 
               
               
                   
                 (tetrahydro-1,4- 
               
               
                   
                 thiazepin-4(5H)- 
               
               
                   
                 yl))- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]-2- 
               
               
                   
                 cyclobutylethanet 
               
               
                   
                 hio- 
               
               
                   
                 amide, thiazepine 
               
               
                   
                 S- 
               
               
                   
                 oxide 
               
               
                 382 
                 (5S)-N-[[3-[3- 
               
               
                   
                 Fluoro-4- 
               
               
                   
                 (tetrahydro-1,4- 
               
               
                   
                 thiazepin-4(5H)- 
               
               
                   
                 yl))- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]-2- 
               
               
                   
                 cyclopentylethane 
               
               
                   
                 thio- 
               
               
                   
                 amide, thiazepine 
               
               
                   
                 S- 
               
               
                   
                 oxide 
               
               
                   
               
             
          
         
       
     
     EXAMPLE 383 
     (5S)-N-[[3-[3,5-Difluoro-4-(tetrahydro-1,4-thiazepin-4 (5H)-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]thioacetamide, thiazepine S-oxide 
     
       
         
               
               
               
               
             
           
               
                 TABLE I 
               
               
                   
               
               
                   
                   
                   
                 Dithioester 
               
               
                 Example 
                   
                   
                 (from 
               
               
                 No. 
                 Compound 
                 Amine 
                 Preparation Z) 
               
               
                   
               
             
             
               
                 384 
                 (5S)-N-[[3-[3,5- Difluoro-4- (tetrahydro- 1,4-thiazepin- 4(5H)-yl))- phenyl]-2-oxo-5- oxazolidinyl]meth yl]- propanethioamide, thiazepine S- oxide 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Z (a) 
               
               
                 385 
                 (5S)-N-[[3-[3,5- 
                 Same as above 
                 Z (b) 
               
               
                   
                 Difluoro-4- 
               
               
                   
                 (tetrahydro- 
               
               
                   
                 1,4-thiazepin- 
               
               
                   
                 4(5H)-yl))- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]-2- 
               
               
                   
                 methylpropanethio- 
               
               
                   
                 amide, thiazepine 
               
               
                   
                 S- 
               
               
                   
                 oxide 
               
               
                 386 
                 (5S)-N-[[3-[3,5- 
                 Same as above 
                 Z (c) 
               
               
                   
                 Difluoro-4- 
               
               
                   
                 (tetrahydro- 
               
               
                   
                 1,4-thiazepin- 
               
               
                   
                 4(5H)-yl))- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]- 
               
               
                   
                 cyclopropanecarbo 
               
               
                   
                 thio- 
               
               
                   
                 amide, thiazepine 
               
               
                   
                 S- 
               
               
                   
                 oxide 
               
               
                   
               
             
          
         
       
     
     EXAMPLE 387 
     (5S)-N-[[3-[4-(Tetrahydro-1,4-thiazepin-4(5H)-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]thioacetamide, thiazepine S-oxide. 
     
       
         
               
               
               
               
             
           
               
                 TABLE J 
               
               
                   
               
               
                   
                   
                   
                 Dithioester 
               
               
                 Example 
                   
                   
                 (from 
               
               
                 No. 
                 Compound 
                 Amine 
                 Preparation Z) 
               
               
                   
               
             
             
               
                 388 
                 (5S)-N-[[3-[4- (Tetrahydro-1,4- yl))- phenyl]-2-oxo-5- thiazepin-4(5H)- oxazolidinyl]meth yl]- propanethioamide, thiazepine S- oxide 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Z (a) 
               
               
                 389 
                 (5S)-N-[[3-[4- 
                 Same as above 
                 Z (b) 
               
               
                   
                 (Tetrahydro-1,4- 
               
               
                   
                 thiazepin-4(5H)- 
               
               
                   
                 yl))- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]-2- 
               
               
                   
                 methylpropanethio- 
               
               
                   
                 amide, thiazepine 
               
               
                   
                 S- 
               
               
                   
                 oxide 
               
               
                 390 
                 (5S)-N-[[3-[4- 
                 Same as above 
                 Z (c) 
               
               
                   
                 (Tetrahydro-1,4- 
               
               
                   
                 thiazepin-4(5H)- 
               
               
                   
                 yl))- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]- 
               
               
                   
                 cyclopropanecarbo 
               
               
                   
                 thio- 
               
               
                   
                 amide, thiazepine 
               
               
                   
                 S- 
               
               
                   
                 oxide 
               
               
                   
               
             
          
         
       
     
     EXAMPLE 391 
     (5S)-N-[[3-[3-Fluoro-4-(tetrahydro-1,4-thiazepin-4(5H)-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]thioacetamide, thiazepine S,S-dioxide 
     
       
         
               
               
               
               
             
           
               
                 TABLE K 
               
               
                   
               
               
                   
                   
                   
                 Dithioester 
               
               
                 Example 
                   
                   
                 (from 
               
               
                 No. 
                 Compound 
                 Amine 
                 Preparation Z) 
               
               
                   
               
             
             
               
                 392 
                 (5S)-N-[[3-[3- Fluoro-4- (4- thiomorpholinyl]- phenyl]-2-oxo-5- oxazolidinyl]met hyl] propanethioamide, thiazepine S,S- dioxide 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Z (a) 
               
               
                 393 
                 (5S)-N-E[3-[3- 
                 Same as above 
                 Z (b) 
               
               
                   
                 Fluoro-4- 
               
               
                   
                 (4- 
               
               
                   
                 thiomorpholinyl]- 
               
               
                   
                 phenly]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]met 
               
               
                   
                 hyl]-2- 
               
               
                   
                 methylpropanethi 
               
               
                   
                 o- 
               
               
                   
                 amide, 
               
               
                   
                 thiazepine S,S- 
               
               
                   
                 dioxide 
               
               
                 394 
                 (5S)-N-[[3-[3- 
                 Same as above 
                 Z (c) 
               
               
                   
                 Fluoro-4- 
               
               
                   
                 (4- 
               
               
                   
                 thiomorpholinyl]- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]met 
               
               
                   
                 hyl]- 
               
               
                   
                 cyclopropanecarb 
               
               
                   
                 othio- 
               
               
                   
                 amide, 
               
               
                   
                 thiazepine S,S- 
               
               
                   
                 dioxide 
               
               
                   
               
             
          
         
       
     
     EXAMPLE 395 
     (5S)-N-[[3-[3,5-Difluoro-4-(tetrahydro-1,4-thiazepin-4 (5H)-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]thioacetamide, thiazepine S,S-dioxide 
     
       
         
               
               
               
               
             
           
               
                 TABLE L 
               
               
                   
               
               
                   
                   
                   
                 Dithioester 
               
               
                 Example 
                   
                   
                 (from 
               
               
                 No. 
                 Compound 
                 Amine 
                 Preparation Z) 
               
               
                   
               
             
             
               
                 396 
                 (5S)-N-[[3-[3,5- Difluoro-4-(4- thiomorpholinyl]- phenyl]-2-oxo-5- oxazolidinyl]methy 1]- propanethioamide, thiazepine S,S- dioxide 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Z (a) 
               
               
                 397 
                 (5S)-N-[[3-[3,5- 
                 Same as above 
                 Z (b) 
               
               
                   
                 Difluoro-4-(4- 
               
               
                   
                 thiomorpholinyl]- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methy 
               
               
                   
                 l]-2- 
               
               
                   
                 methylpropanethio- 
               
               
                   
                 amide, thiazepine 
               
               
                   
                 S,S- 
               
               
                   
                 dioxide 
               
               
                 398 
                 (5S)-N-[[3-[3,5- 
                 Same as above 
                 Z (c) 
               
               
                   
                 Difluoro-4-(4- 
               
               
                   
                 thiomorpholinyl]- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methy 
               
               
                   
                 1]- 
               
               
                   
                 cyclopropanecarbot 
               
               
                   
                 hio- 
               
               
                   
                 amide, thiazepine 
               
               
                   
                 S,S- 
               
               
                   
                 dioxide 
               
               
                   
               
             
          
         
       
     
     EXAMPLE 399 
     (5S)-N-[[3-[4-(Tetrahydro-1,4-thiazepin-4(5H)-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]thioacetamide, thiazepine S,S-dioxide 
     
       
         
               
               
               
               
             
           
               
                 TABLE M 
               
               
                   
               
               
                   
                   
                   
                 Dithioester 
               
               
                 Example 
                   
                   
                 (From 
               
               
                 No. 
                 Compound 
                 Amine 
                 Preparation Z) 
               
               
                   
               
             
             
               
                 400 
                 (5S)-N-[[3-[4- (tetrahydro-1,4- thiazepin-4(5H)- yl))phenyl]-2-oxo- 5- ozolidinyl]- methyl]propanethio- amide, thiazepine S,S- dioxide 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Z (a) 
               
               
                 401 
                 (5S)-N-[[3-[4- 
                 Same as above 
                 Z (b) 
               
               
                   
                 (tetrahydro-1,4- 
               
               
                   
                 thiazepin-4(5H)- 
               
               
                   
                 yl))phenyl]-2-oxo- 
               
               
                   
                 5- 
               
               
                   
                 oxazolidinyl]methy 
               
               
                   
                 l]-2- 
               
               
                   
                 methylpropanethio- 
               
               
                   
                 amide, thiazepine 
               
               
                   
                 S,S- 
               
               
                   
                 dioxide 
               
               
                 402 
                 (5S)-N-[[3-[4- 
                 Same as above 
                 Z (c) 
               
               
                   
                 (tetrahydro-1,4- 
               
               
                   
                 thiazepin-4(5H)- 
               
               
                   
                 yl))phenyl]-2- 
               
               
                   
                 oxo-5- 
               
               
                   
                 oxazolidinyl]- 
               
               
                   
                 methyl]cyclopropa 
               
               
                   
                 ne- 
               
               
                   
                 carbothioamide, 
               
               
                   
                 thiazepine S,S- 
               
               
                   
                 dioxide 
               
               
                   
               
             
          
         
       
     
     EXAMPLE 403 
     (5S)-N-[[3-[3-Fluoro-4-(tetrahydro-1,4-thiazepin-4 (5H)-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]thioacetamide 
     
       
         
               
               
               
               
             
           
               
                 TABLE N 
               
               
                   
               
               
                   
                   
                   
                 Dithioester 
               
               
                 Example 
                   
                   
                 (From 
               
               
                 No. 
                 Compound 
                 Amine 
                 Preparation Z) 
               
               
                   
               
             
             
               
                 404 
                 (5S)-N-[[3-[3- Fluoro-4- (tetrahydro- 1,4- phenyl]-4(5H)- yl))- henY1J-2-oxo-5- oxazolidinyl]me thyl]- propanethio- amide 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Z (a) 
               
               
                 405 
                 (5S)-N-[[3-[3- 
                 Same as above 
                 Z (b) 
               
               
                   
                 Fluoro-4- 
               
               
                   
                 (tetrahydro-1,4- 
               
               
                   
                 thiazepin-4(5H)- 
               
               
                   
                 yl))- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]-2- 
               
               
                   
                 methylpropanethio 
               
               
                   
                 amide 
               
               
                 406 
                 (5S)-N-[[3-[3- 
                 Same as above 
                 Z (c) 
               
               
                   
                 Fluoro-4- 
               
               
                   
                 (tetrahydro-1,4- 
               
               
                   
                 thiazepin-4(5H)- 
               
               
                   
                 yl))- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]- 
               
               
                   
                 cyclopropanecarbo 
               
               
                   
                 thio- 
               
               
                   
                 amide 
               
               
                 407 
                 (5S)-N-[[3-[3- 
                 Same as above 
                 Z (d) 
               
               
                   
                 Fluoro-4- 
               
               
                   
                 (tetrahydro-1,4- 
               
               
                   
                 thiazepin-4(5H)- 
               
               
                   
                 yl))- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]- 
               
               
                   
                 butanethioamide 
               
               
                 408 
                 (5S)-N-[[3-[3- 
                 Same as above 
                 Z (e) 
               
               
                   
                 Fluoro-4- 
               
               
                   
                 (tetrahydro-1,4- 
               
               
                   
                 thiazepin-4(5H)- 
               
               
                   
                 yl))- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]-3- 
               
               
                   
                 methylbutanethioa 
               
               
                   
                 mide 
               
               
                 409 
                 (5S)-N-[[3-[3- 
                 Same as above 
                 Z (f) 
               
               
                   
                 Fluoro-4- 
               
               
                   
                 (tetrahydro-1,4- 
               
               
                   
                 thiazepin-4(5H)- 
               
               
                   
                 yl))- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]-2- 
               
               
                   
                 methylbutanethioa 
               
               
                   
                 mide 
               
               
                 410 
                 (5S)-N-[[3-[3- 
                 Same as above 
                 Z (g) 
               
               
                   
                 Fluoro-4- 
               
               
                   
                 (tetrahydro-1,4- 
               
               
                   
                 thiazepin-4(5H)- 
               
               
                   
                 yl))- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]- 
               
               
                   
                 3,3- 
               
               
                   
                 dimethylbutanethi 
               
               
                   
                 o- 
               
               
                   
                 amide 
               
               
                 411 
                 (5S)-N-[[3-[3- 
                 Same as above 
                 Z (h) 
               
               
                   
                 Fluoro-4- 
               
               
                   
                 (tetrahydro-1,4- 
               
               
                   
                 thiazepin-4(5H)- 
               
               
                   
                 yl))- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]- 
               
               
                   
                 cyclobutanecarbot 
               
               
                   
                 hio- 
               
               
                   
                 amide 
               
               
                 412 
                 (5S)-N-[[3-[3- 
                 Same as above 
                 Z (i) 
               
               
                   
                 Fluoro-4- 
               
               
                   
                 (tetrahydro-1, 4- 
               
               
                   
                 thiazepin-4(5H)- 
               
               
                   
                 yl))- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]- 
               
               
                   
                 cyclopentanecarbo 
               
               
                   
                 thio- 
               
               
                   
                 amide 
               
               
                 413 
                 (5S)-N-[[3-[3- 
                 Same as above 
                 Z (j) 
               
               
                   
                 Fluoro-4- 
               
               
                   
                 (tetrahydro-1,4- 
               
               
                   
                 thiazepin-4(5H)- 
               
               
                   
                 yl))- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]- 
               
               
                   
                 cyclohexanecarbot 
               
               
                   
                 hio- 
               
               
                   
                 amide 
               
               
                 414 
                 (5S)-N-[[3-[3-5 
                 Same as above 
                 Z (k) 
               
               
                   
                 Fluoro- 
               
               
                   
                 4-(tetrahydro 
               
               
                   
                 1,4- 
               
               
                   
                 thiazepin-4(5H)- 
               
               
                   
                 yl))- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]-2- 
               
               
                   
                 cyclopropylethane 
               
               
                   
                 thio- 
               
               
                   
                 amide 
               
               
                 415 
                 (5S)-N-[[3-[3- 
                 Same as above 
                 Z (l) 
               
               
                   
                 Fluoro-4- 
               
               
                   
                 (tetrahydro-1,4- 
               
               
                   
                 thiazepin-4(5H)- 
               
               
                   
                 yl))- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]-2- 
               
               
                   
                 cyclobutylethanet 
               
               
                   
                 hio- 
               
               
                   
                 amide 
               
               
                 416 
                 (5S)-N-[[3-[3- 
                 Same as above 
                 Z (m) 
               
               
                   
                 Fluoro-4- 
               
               
                   
                 (tetrahydro-1,4- 
               
               
                   
                 thiazepin-4(5H)- 
               
               
                   
                 yl))- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methy 
               
               
                   
                 1]-2- 
               
               
                   
                 cyclopentylethanet 
               
               
                   
                 hioam 
               
               
                   
                 ide 
               
               
                   
               
             
          
         
       
     
     EXAMPLE 417 
     (5S)-N-[[3-[3,5-Difluoro-4-(tetrahydro-1,4-thiazepin-4 (5H)-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]thioacetamide 
     
       
         
               
               
               
               
             
           
               
                 TABLE O 
               
               
                   
               
               
                   
                   
                   
                 Dithio Compound 
               
               
                 Example 
                   
                   
                 (from 
               
               
                 No. 
                 Compound 
                 Amine 
                 Preparation Z) 
               
               
                   
               
             
             
               
                 418 
                 (5S)-N-[[3-[3,5- Difluoro-4- (tetrahydro- 1,4-thiazepin- phenyl]-2-oxo-5- oxazolidinyl]methy 1]- propanethioamide 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Z (a) 
               
               
                 419 
                 (5S)-N-[[3-[3,5- 
                 Same as above 
                 Z (b) 
               
               
                   
                 Difluoro-4- 
               
               
                   
                 (tetrahydro- 
               
               
                   
                 1,4-thiazepin- 
               
               
                   
                 4(5H)-yl))- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methy 
               
               
                   
                 1]-2- 
               
               
                   
                 methylpropanethioa 
               
               
                   
                 mide 
               
               
                 420 
                 (5S)-N-[[3-[3,5- 
                 Same as above 
                 Z (c) 
               
               
                   
                 Difluoro-4- 
               
               
                   
                 (tetrahydro- 
               
               
                   
                 1,4-thiazepin- 
               
               
                   
                 4(5H)-yl))- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methy 
               
               
                   
                 l]- 
               
               
                   
                 cyclopropanecarbot 
               
               
                   
                 hio- 
               
               
                   
                 amide 
               
               
                   
               
             
          
         
       
     
     EXAMPLE 421 
     (5S)-N-[[3-[4-(Tetrahydro-1,4-thiazepin-4(5H)-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]thioacetamide 
     
       
         
               
               
               
               
             
           
               
                 TABLE P 
               
               
                   
               
               
                   
                   
                   
                 Dithio Compound 
               
               
                 Example 
                   
                   
                 (from 
               
               
                 No. 
                 Compound 
                 Amine 
                 Preparation Z) 
               
               
                   
               
             
             
               
                 422 
                 (5S)-N-[[3-[4- (Tetrahydro-1,4- thiazepin-4(5H)- yl))- phenyl]-2-oxo-5- oxazolidinyl]- methyl]propanethio- amide 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 Z (a) 
               
               
                 423 
                 (5S)-N-[[3-[4- 
                 Same as above 
                 Z (b) 
               
               
                   
                 (Tetrahydro-1,4- 
               
               
                   
                 thiazepin-4(5H)- 
               
               
                   
                 yl))- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]methy 
               
               
                   
                 l]-2- 
               
               
                   
                 methylpropanethioa 
               
               
                   
                 mide 
               
               
                 424 
                 (5S)-N-[[3-[4- 
                 Same as above 
                 Z (c) 
               
               
                   
                 (Tetrahydro-1,4- 
               
               
                   
                 thiazepin-4(5H)- 
               
               
                   
                 yl))- 
               
               
                   
                 phenyl]-2-oxo-5- 
               
               
                   
                 oxazolidinyl]- 
               
               
                   
                 methyl] 
               
               
                   
                 cyclopropane- 
               
               
                   
                 carbothioamide 
               
               
                 425 
                 (5S)-N-[[3-[3-Fluo 
               
               
                   
                 ro-4- 
               
               
                   
                 (tetrahydro-1,4- 
               
               
                   
                 thiazepin-4(5H)- 
               
               
                   
                 yl)phenyl]-2-oxo-5 
               
               
                   
                 — 
               
               
                   
                 oxazolidinyl]methy 
               
               
                   
                 1]-1- 
               
               
                   
                 azetidinecarbothio 
               
               
                   
                 amide, thiazepine 
               
               
                   
                 S-oxide 
               
               
                 426 
                 (5S)-N-[[3-[3-Fluo 
               
               
                   
                 ro-4- 
               
               
                   
                 (tetrahydro-1,4 
               
               
                   
                 thiazepin-4(5H)- 
               
               
                   
                 yl)phenyl]-2-oxo-5 
               
               
                   
                 oxazolidinyl]methy 
               
               
                   
                 l]-O- 
               
               
                   
                 methylthiocarbamat 
               
               
                   
                 e, thiazepine 
               
               
                   
                 S-oxide 
               
               
                 427 
                 (5S)-N-[[3-[3,5- 
               
               
                   
                 Difluoro-4- 
               
               
                   
                 (tetrahydro- 
               
               
                   
                 1,4-thiazepin- 
               
               
                   
                 4(5H)- 
               
               
                   
                 yl)phenyl]-2-oxo- 
               
               
                   
                 5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]-1- 
               
               
                   
                 azetidinecarbothi 
               
               
                   
                 oamide, 
               
               
                   
                 thiazepine 5- 
               
               
                   
                 oxide 
               
               
                 428 
                 (5S)-N-[[3-[4- 
               
               
                   
                 (Tetrahydro-1,4- 
               
               
                   
                 thiazepin-4(5H)- 
               
               
                   
                 yl)phenyl]-2-oxo- 
               
               
                   
                 5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]-1 
               
               
                   
                 azetidinecarbothi 
               
               
                   
                 oamide, 
               
               
                   
                 thiazepine 
               
               
                   
                 S-oxide 
               
               
                 429 
                 (5S)-N-[[3-[3-Flu 
               
               
                   
                 oro-4- 
               
               
                   
                 (tetrahydro-1,4 
               
               
                   
                 thiazepin-4(5H)- 
               
               
                   
                 yl)phenyl]-2-oxo- 
               
               
                   
                 5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]-1- 
               
               
                   
                 azetidinecarbothi 
               
               
                   
                 oamide, 
               
               
                   
                 thiazepine 
               
               
                   
                 S,S-dioxide 
               
               
                 430 
                 (5S)-N-[[3-[3,5- 
               
               
                   
                 Difluoro-4- 
               
               
                   
                 (tetrahydro- 
               
               
                   
                 1,4-thiazepin- 
               
               
                   
                 4(5H)- 
               
               
                   
                 yl)phenyl]-2-oxo- 
               
               
                   
                 5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]-1- 
               
               
                   
                 azetidinecarbothi 
               
               
                   
                 oamide, 
               
               
                   
                 thiazepine S,S- 
               
               
                   
                 dioxide 
               
               
                 431 
                 (5S)-N-[[3-[4- 
               
               
                   
                 (Tetrahydro-1,4- 
               
               
                   
                 thiazepin-4(5H)- 
               
               
                   
                 yl)phenyl]-2-oxo- 
               
               
                   
                 5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]-1- 
               
               
                   
                 azetidinecarbothi 
               
               
                   
                 oamide, 
               
               
                   
                 thiazepine S,S- 
               
               
                   
                 dioxide 
               
               
                 432 
                 (5S)-N-[[3-[3- 
               
               
                   
                 Fluoro-4- 
               
               
                   
                 (tetrahydro-1,4- 
               
               
                   
                 thiazepin-4(5H)- 
               
               
                   
                 yl)phenyl]-2-oxo- 
               
               
                   
                 5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]-1- 
               
               
                   
                 azetidinecarbothi 
               
               
                   
                 oamide 
               
               
                 433 
                 (5S)-N-[[3-[3,5- 
               
               
                   
                 Difluoro-4- 
               
               
                   
                 (tetrahydro- 
               
               
                   
                 1,4-thiazepin- 
               
               
                   
                 4(5H)- 
               
               
                   
                 yl)phenyl]-2- 
               
               
                   
                 oxo-5- 
               
               
                   
                 oxazolidinyl]met 
               
               
                   
                 hyl]-1- 
               
               
                   
                 azetidinecarboth 
               
               
                   
                 ioamide 
               
               
                 434 
                 (5S)-N-[[3-[4- 
               
               
                   
                 (Tetrahydro-1,4- 
               
               
                   
                 thiazepin-4(5H)- 
               
               
                   
                 yl)phenyl]-2-oxo- 
               
               
                   
                 5- 
               
               
                   
                 oxazolidinyl]meth 
               
               
                   
                 yl]-1- 
               
               
                   
                 azetidinecarbothi 
               
               
                   
                 oamide 
               
               
                   
               
             
          
         
       
     
     EXAMPLE 435 
     (5R)-(−)-3-[3-Fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinecarboxamide—Method A 
                                
Step 1: Preparation of (5R)-(−)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinecarboxylic acid
 
     A solution of benzyl 3-fluoro-4-(4-morpholinyl)phenylcarbamate ( J. Med. Chem.  1996, 39(3), 673-679, 2.50 g, 7.57 mmol) in dry tetrahydrofuran (37.8 mL) at −78° C. under nitrogen was treated with n-butyllithium (1.6M in hexanes, 4.82 mL, 7.72 mmol) dropwise and stirred at −78° C. for 30 minutes. The cooling bath was removed and the mixture was allowed to slowly warm to −40° C., at which point potassium (2R)-glycidate ( J. Org. Chem.  1992, 57(12), 3380-3387, 974 mg, 7.72 mmol) was added. After subsequent warming to ambient temperature, the resulting mixture was vigorously stirred for 2.75 days and then quenched with saturated aqueous ammonium chloride (20 mL), diluted with water (20 mL) and extracted with ethyl acetate (2×75 mL) to remove the remaining starting. The aqueous phase was adjusted to pH 2 with 1M aqueous hydrochloric acid, saturated with sodium chloride and extracted with methylene chloride (5×100 mL), and this combined organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. The product mixture was then chromatographed on a Flash 40M silica gel (90 g, 32-63 μm) cartridge, eluting with a gradient of acetonitrile/methylene chloride (10/90-40/60) containing 1% formic acid, and those fractions with an R f =0.15 by TLC (acetonitrile/methylene chloride, 50/50+1% formic acid) are pooled and concentrated to give the title compound,  1 H NMR (400 MHz, DMSO-d 6 ) δ 13.7 (bs, 1H), 7.48 (dd, 1H), 7.23 (m, 1H), 7.05 (t, 1H), 5.17 (dd, 1H), 4.30 (t, 1H), 4.06 (dd, 1H), 3.73 (m, 4H), 2.96 (m, 4H); MS (ESI+) for C 14 H 15 FN 2 O 5  m/z 311 (M+H) + ; [α] 25   D =−38° (c 0.94, DMSO). 
     Step 2: Preparation of (5R)-(−)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinecarboxamide 
     To a flame-dried flask containing (5R)-(−)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinecarboxylic acid (Step 1, 250 mg, 0.806 mmol) under nitrogen was added oxalyl chloride (4 mL) with stirring. The flask was capped with a drying tube, and the mixture was stirred at ambient temperature for 15 hours and then concentrated under reduced pressure to give the acid chloride intermediate [MS (ESI+) m/z 325 (M+H) +  observed for the methyl ester obtained by reaction of the acid chloride with methanol] which was used without further purification. This intermediate was then taken up in anhydrous tetrahydrofuran (8 mL) under nitrogen, cooled to 0° C., and ammonia (g) was bubbled in for 5 minutes. The resulting mixture was capped with a drying tube, stirred at ambient temperature for 1 hour, and then diluted with water (20 mL) and extracted with methanol/chloroform (10/90, 2×30 mL). The combined organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure, and the product mixture was recrystallized from ethyl acetate/hexane to give the title compound, mp 185-187° C. (decomp.); MS (ESI+) for C 14 H 16 FN 3 O 4  m/z 310 (M+H) + ; [α] 25   D =−23° (c 0.89, DMSO). 
     EXAMPLE 436 
     (5R)-(−)-3-[3-Fluoro-4-(4-morpholinyl)phenyl]-N-methyl-2-oxo-5-oxazolidinecarboxamide 
     
       
                 
         
             
             
         
      
     
     Following the general procedure of EXAMPLE 435, Step 2, and making non-critical variations but substituting methylamine for ammonia, the title compound was obtained, mp 182-183° C. (decomp.); MS (ESI+) for C 15 H 18 FN 3 O 4  m/z 324 (M+H) + ; [α] 25   D =−39° (c 0.92, DMSO). 
     EXAMPLE 437 
     (5R)-(−)-3-[3-Fluoro-4-(4-morpholinyl)phenyl]-N-allyl-2-oxo-5-oxazolidinecarboxamide 
     
       
                 
         
             
             
         
      
     
     To a flame-dried flask under nitrogen was added allylamine (0.60 mL, 8.05 mmol). The flask was cooled in an ice bath, and a solution of (5R)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinecarbonyl chloride (EXAMPLE 435, Step 2, 0.805 mmol theory) in anhydrous tetrahydrofuran (8.0 mL) was added. The resulting mixture was stirred under nitrogen for 2 hours, allowing the cooling bath to slowly expire, and was then diluted with water (10 mL) and extracted with methylene chloride (20 mL). The organic phase was washed with water (10 mL) and saline (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure, and the crude product was chromatographed on a Flash 40S silica gel (40 g, 32-63 μm) cartridge, eluting with a gradient of methanol/methylene chloride (0.5/99.5-2/98). Pooling and concentration of those fractions with an R f =0.44 by TLC (methanol/chloroform, 5/95) provides the title compound, mp 167-169° C.; MS (ESI+) for C 17 H 20 FN 3 O 4  m/z 350 (M+H) + ; [α] 25   D =−44° (c 0.94, DMSO). 
     EXAMPLE 438 
     (5R)-(−)-3-[3-Fluoro-4-(4-morpholinyl)phenyl]-N-propyl-2-oxo-5-oxazolidinecarboxamide 
     
       
                 
         
             
             
         
      
     
     Following the general procedure of EXAMPLE 437, and making non-critical variations but substituting propylamine for allylamine and triturating and filtering the final product from methanol/diethyl ether, the title compound was obtained, mp 165-167° C.; MS (ESI+) for C 17 H 22 FN 3 O 4  m/z 352 (M+H) + ; [α] 25   D =−43° (c 1.02, DMSO). 
     EXAMPLE 439 
     (5R)-(−)-3-[3-Fluoro-4-(4-morpholinyl)phenyl]-N-methoxy-2-oxo-5-oxazolidinecarboxamide 
     
       
                 
         
             
             
         
      
     
     A mixture of (5R)-(−)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinecarboxylic acid (EXAMPLE 1, Step 1, 150 mg, 0.483 mmol) and O-methylhydroxylamine hydrochloride (61 mg, 0.724 mmol) in tetrahydrofuran/water (1/1, 4.8 mL) was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (278 mg, 1.45 mmol), and the resulting mixture was stirred at ambient temperature for 30 minutes and was then diluted with water (10 mL) and extracted with ethyl acetate (2×20 mL). The combined organic phase was washed with water (10 mL) and saline (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure, and the crude product was chromatographed on a Flash 40S silica gel (40 g, 32-63 μm) cartridge, eluting with methanol/methylene chloride (2.5/97.5). Pooling and concentration of those fractions with an R f =0.53 by TLC (methanol/chloroform, 10/90) gives the title compound, mp 206-208° C. (decomp.); MS (ESI+) for C 15 H 18 FN 3 O 5  m/z 340 (M+H) + ; [α] 25   D =−56° (c 0.92, DMSO). 
     EXAMPLE 440 
     (5R)-(−)-3-[3-Fluoro-4-(4-morpholinyl)phenyl]-N-hydroxy-2-oxo-5-oxazolidinecarboxamide 
                                
Step 1: Preparation of (5R)-(−)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-N-benzyloxy-2-oxo-5-oxazolidinecarboxamide
 
     Following the general procedure of EXAMPLE 439, and making non-critical variations but substituting O-benzylhydroxylamine hydrochloride for O-methylhydroxylamine hydrochloride, the title compound was obtained, mp 191-193° C. (decomp.); MS (ESI+) for C 21 H 22 FN 3 O 5  m/z 416 (M+H) + ; [α] 25   D =−46° (c 0.93, DMSO). 
     Step 2: Preparation of (5R)-(−)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-N-hydroxy-2-oxo-5-oxazolidinecarboxamide 
     To a mixture of (5R)-(−)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-N-benzyloxy-2-oxo-5-oxazolidinecarboxamide (Step 1, 300 mg, 0.722 mmol) in methanol (28.8 mL) was added 5% palladium-on-carbon (77 mg) under nitrogen. The resulting mixture was degassed and stirred under a hydrogen atmosphere (balloon) for 1 hour. The catalyst was then removed by filtration through Celite, rinsing with methanol (60 mL), and the filtrate was concentrated under reduced pressure. Trituration of this residue with (5% methanol/methylene chloride)/diethyl ether gives the title compound, mp 141-143° C.; MS (ESI+) for C 14 H 16 FN 3 O 5  m/z 326 (M+H) + ; [α] 25   D =−70° (c 0.99, DMSO). 
     EXAMPLE 441 
     (5R)-(−)-3-[4-(3-Pyridyl)-3-fluorophenyl]-2-oxo-5-oxazolidinecarboxamide 
                                
Step 1: Preparation of (5R)-(−)-3-[3-fluoro-4-iodophenyl]-5-hydroxymethyl-2-oxazolidinone
 
     A solution of isobutyl 3-fluoro-4-iodophenylcarbamate ( Org. Process Res. Dev.  2001, 5(1), 80-83, 5.00 g, 14.83 mmol) in dry tetrahydrofuran (59 mL) at −78° C. under nitrogen was treated with lithium hexamethyldisilazide (1.0M in tetrahydrofuran, 15.6 mL, 15.57 mmol) dropwise and stirred at −78° C. for 45 minutes. Then, (R)-glycidyl butyrate (2.21 mL, 15.57 mmol) was added dropwise, and the resulting mixture was stirred at −78° C. for 1 hour and at ambient temperature for 2.75 days. The reaction mixture was then quenched with saturated aqueous ammonium chloride (20 mL), diluted with water (20 mL) and the layers are separated. The aqueous phase was extracted with ethyl acetate (25 mL), and the combined organic phase was washed with water (25 mL) and saline (25 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The product mixture was then chromatographed on a Flash 40M silica gel (90 g, 32-63 μm) cartridge, eluting with a gradient of methanol/methylene chloride (1/99-2/98), and those fractions with an R f =0.25 by TLC (methanol/chloroform, 5/95) are pooled and concentrated to give the title compound, mp 116-117° C.; MS (ESI+) for C 10 H 9 FINO 3  m/z 338 (M+H) + ; [α] 25   D =−41 (c 0.98, DMSO) 
     Step 2: Preparation of (−)-methyl (5R)-3-[3-fluoro-4-iodophenyl]-2-oxo-5-oxazolidinecarboxylate 
     A solution of (5R)-(−)-3-[3-fluoro-4-iodophenyl]-5-hydroxymethyl-2-oxazolidinone (Step 1, 7.61 g, 22.58 mmol) in acetone (150 mL) at −10° C. was treated with a mixture of CrO 3  (6.21 g, 62.1 mmol) in sulfuric acid (6M, 16.9 mL, 101 mmol) dropwise over 15 minutes. The resulting mixture was allowed to slowly warm to ambient temperature with vigorous stirring (slight exotherm to 35° C.) and was stirred for an additional 16 hours. The mixture was then treated with isopropanol (35 mL), diluted with saline (150 mL) and diethyl ether (150 mL), stirred until all solids are dissolved, and the layers are separated. The aqueous phase was extracted with diethyl ether (100 mL), and the combined organic phase was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the crude carboxylic acid intermediate which was taken up in methanol (225 mL) and treated with concentrated sulfuric acid (8 drops). The resulting homogeneous mixture was stirred at ambient temperature for 20 hours and was then concentrated under reduced pressure to give the crude methyl ester product which was chromatographed on two Flash 40M 90 g silica gel (32-63 μm) cartridges, eluting with a gradient of ethyl acetate/heptane (20/80-40/60). Pooling and concentration of those fractions with an R f =0.36 by TLC (ethyl acetate/hexane, 50/50) gives the title compound, mp 106-109° C.; MS (ESI+) for C 11 H 9 FINO 4  m/z 366 (M+H) + ; [α] 25   D =−30 (c 0.93, DMSO). 
     Step 3: Preparation of (5R)-(−)-3-[3-fluoro-4-iodophenyl]-2-oxo-5-oxazolidinecarboxamide 
     A solution of (−)-methyl (5R)-3-[3-fluoro-4-iodophenyl]-2-oxo-5-oxazolidinecarboxylate (Step 2, 6.23 g, 17.1 mmol) in acetonitrile (85 mL) was treated with concentrated ammonium hydroxide (85 mL), and the resulting mixture was stirred at ambient temperature for 1 hour. The mixture was then diluted with saline (100 mL) and extracted with methylene chloride (3×100 mL), and the combined organic phase was washed with saline (100 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was diluted with hot ethyl acetate (200 mL) and filtered to remove inorganic residue, and the filtrate was diluted with hexanes (300 mL). The resulting precipitate was isolated by filtration to give the title compound, mp 176-178° C.; MS (ESI+) for C 10 H 8 FIN 2 O 3  m/z 351 (M+H) + ; [α] 25   D =−19 (c 0.97, DMSO). 
     Step 4: Preparation of 3-(trimethylstannyl)pyridine 
     A mixture of hexamethylditin (654 mg, 1.99 mmol), 3-bromopyridine (300 mg, 1.90 mmol) and bis(triphenylphosphine)palladium(II) chloride (40 mg, 0.057 mmol) in 1,4-dioxane (9.5 ml) was degassed, heated up to 90° C. under nitrogen, stirred at this temperature for 2.5 hours and at ambient temperature overnight, and was then concentrated under reduced pressure. The product mixture was chromatographed on a Flash 40S 40 g silica gel (32-63 μm) cartridge, eluting with ethyl acetate/heptane (20/80), and those fractions with an R f =0.47 by TLC (ethyl acetate/hexane, 50/50) are pooled and concentrated to give the title compound (see  Chem. Pharm. Bull.  1982, 30(5), 1731-1737 for characterization). 
     Step 5: Preparation of (5R)-(−)-3-[4-(3-pyridyl)-3-fluorophenyl]-2-oxo-5-oxazolidinecarboxamide 
     A mixture of (5R)-(−)-3-[3-fluoro-4-iodophenyl]-2-oxo-5-oxazolidinecarboxamide (Step 3, 422 mg, 1.21 mmol), 3-(trimethylstannyl)pyridine (Step 4, 350 mg, 1.45 mmol), tris(dibenzylideneacetone)dipalladium(0) (22 mg, 0.0242 mmol), triphenylarsine (59 mg, 0.194 mmol) and copper(I) iodide (9 mg, 0.0484 mmol) in N-methyl-2-pyrrolidinone (4.8 mL) under nitrogen was degassed, heated up to 50° C. and stirred at this temperature for 2 days, during which additional tris(dibenzylideneacetone)dipalladium(0) (22 mg, 0.0242 mmol), triphenylarsine (59 mg, 0.194 mmol) and copper(I) iodide (9 mg, 0.0484 mmol) are added. The resulting mixture was diluted with water (15 mL) and extracted with methylene chloride (3×20 mL), and the combined organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting oil was diluted with ethyl acetate (25 mL) and extracted with aqueous hydrochloric acid (1M, 25 mL), and the aqueous phase was neutralized with sodium hydroxide (s), saturated with sodium chloride and extracted with methylene chloride (3×25 mL) containing a small amount of methanol. This combined organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure, and the residue was recrystallized from ethyl acetate/hexane to give the title compound, mp 240-242° C. (dec.); MS (ESI+) for C 15 H 12 FN 3 O 3  m/z 302 (M+H) + ; [α] 25   D =−25 (c 0.94, DMSO). 
     EXAMPLE 442 
     (5R)-(−)-3-[4-(4-Pyridyl)-3-fluorophenyl]-2-oxo-5-oxazolidinecarboxamide 
     
       
                 
         
             
             
         
      
     
     Following the general procedure of EXAMPLE 441, Step 5, and making non-critical variations but substituting 4-(trimethylstannyl)pyridine (U.S. Pat. No. 5,990,136, 23 Nov. 1999) for 3-(trimethylstannyl)pyridine, the title compound was obtained, mp 256-259° C. (dec.); MS (ESI+) for C 15 H 12 FN 3 O 3  m/z 302 (M+H) + ; [α] 25   D =−27 (c 0.94, DMSO). 
     EXAMPLE 443 
     (5R)-(−)-3-[4-(3,6-Dihydro-2H-pyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinecarboxamide 
                                
Step 1: Preparation of (5R)-3-[4-(trimethylstannyl)-3-fluorophenyl]-2-oxo-5-oxazolidinecarboxamide
 
     A mixture of (SR)-(−)-3-[3-fluoro-4-iodophenyl]-2-oxo-5-oxazolidinecarboxamide (EXAMPLE 441, Step 3, 3.50 g, 10.0 mmol), hexamethylditin (3.44 g, 10.5 mmol) and bis(triphenylphosphine)palladium(II) chloride (140 mg, 0.200 mmol) in 1,4-dioxane (50 mL) under nitrogen was degassed, heated up to 90° C. and stirred at 90° C. for 2 hours and at ambient temperature overnight. The resulting mixture was concentrated under reduced pressure to remove dioxane, diluted with methylene chloride (75 mL), washed with saline (25 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was chromatographed on a Flash 40M 90 g silica gel (32-63 μm) cartridge, eluting with a gradient of methanol/methylene chloride (1/99-2/98), and those fractions with an R f =0.26 by TLC (methanol/chloroform, 5/95) are pooled and concentrated to give the title compound,  1 H NMR (400 MHz, CDCl 3 ) δ 7.38 (m, 2H), 7.20 (m, 1H), 6.65 (s, 1H), 5.82 (s, 1H), 5.00 (dd, 1H), 4.26 (m, 2H), 0.35 (m, 9H). 
     Step 2: Preparation of (5R)-(−)-3-[4-(3,6-dihydro-2H-pyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidine-carboxamide 
     A mixture of 3,6-dihydro-2H-pyran-4-yl trifluoromethanesulfonic acid ester (U.S. Pat. No. 5,968,962, 19 Oct. 1999, 682 mg, 2.94 mmol), tris(dibenzylideneacetone)dipalladium(0) (54 mg, 0.0588 mmol) and triphenylarsine (144 mg, 0.470 mmol) in N-methyl-2-pyrrolidinone (14.7 mL) was degassed and stirred under nitrogen for 5 minutes. (5R)-3-[4-(trimethylstannyl)-3-fluorophenyl]-2-oxo-5-oxazolidinecarboxamide (Step 1, 1.14 g, 2.94 mmol) was then added, and the resulting mixture was stirred at ambient temperature for 5 days. The reaction mixture was then diluted with water (25 mL) and extracted with ethyl acetate (3×30 mL), and the combined organic phase was washed with water (3×30 mL) and saline (20 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crude product mixture was chromatographed on a Flash 40M 90 g silica gel (32-63 μm) cartridge, eluting with a gradient of methanol/methylene chloride (1/99-2.5/97.5), and those fractions with an R f =0.40 by TLC (methanol/chloroform, 2×5/95) are pooled and concentrated to give the title compound, mp 164-169° C.; MS (ESI−) for C 15 H 15 N 2 O 4 F m/z 305 (M−H) − ; [α] 25   D =−23 (c 0.96, DMSO). 
     EXAMPLE 444 
     (5R)-(−)-3-[4-(Tetrahydro-2H-pyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinecarboxamide 
     
       
                 
         
             
             
         
      
     
     A mixture of (5R)-(−)-3-[4-(3,6-dihydro-2H-pyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinecarboxamide (EXAMPLE 443, Step 2, 200 mg, 0.653 mmol) and 10% palladium-on-carbon (139 mg, 0.131 mmol) in methanol (26 mL) was shaken under a 40 psi hydrogen atmosphere on a Parr apparatus for 5 hours. The catalyst was then removed by filtration through a pad of Celite, and the filtrate was concentrated under reduced pressure and chromatographed on a Flash 40S 40 g silica gel (32-63 μm) cartridge, eluting with a gradient of methanol/methylene chloride (2/98-3/97). Pooling and concentration of those fractions with an R f =0.37 by TLC (methanol/chloroform, 2×5/95) gives the title compound, mp 153-156° C.; MS (ESI−) for C 15 H 17 N 2 O 4 F m/z 307 (M−H) − ; [α] 25   D =−21 (c 0.87, DMSO). 
     EXAMPLE 445 
     (5R)-3-[4-(3,6-Dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinecarboxamide S-oxide 
                                
Step 1: Preparation of (−)-methyl (5R)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinecarboxylate
 
     Following the general procedure of EXAMPLE 435, Step 1, and making non-critical variations but substituting isobutyl 4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenylcarbamate (WO 00/44741, Aug. 3, 2000) for benzyl 3-fluoro-4-(4-morpholinyl)phenylcarbamate, the crude (5R)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinecarboxylic acid intermediate was obtained and was used without further purification. This intermediate (540 mg crude) was taken up in methanol (16 mL), a drop of concentrated sulfuric acid was added, and the mixture was stirred at ambient temperature for 21 hours. Then, the reaction mixture was concentrated under reduced pressure and chromatographed on a Flash 40S 40 g silica gel (32-63 μm) cartridge, eluting with ethyl acetate/heptane (25/75). Pooling and concentration of those fractions with an R f =0.25 by TLC (ethyl acetate/hexs, 50/50) give the title compound, mp 106-110° C.; MS (ESI+) for C 16 H 16 NO 4 FS m/z 338 (M+H) + ; [α] 25   D =−36 (c 0.99, DMSO). 
     Step 2: Preparation of (5R)-(−)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinecarboxamide 
     Following the general procedure of EXAMPLE 441, Step 3, and making non-critical variations but substituting (−)-methyl (5R)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinecarboxylate (Step 1) for (−)-methyl (5R)-3-[3-fluoro-4-iodophenyl]-2-oxo-5-oxazolidinecarboxylate and purifying the product by recrystallization from methanol/diethyl ether, the title compound was obtained, mp 182-184° C. (dec.); MS (ESI−) for C 15 H 15 FN 2 O 3 S m/z 321 (M−H) − ; [α] 25   D =−24 (c 0.93, DMSO). 
     Step 3: Preparation of (5R)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinecarboxamide S-oxide 
     A mixture of (5R)-(−)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinecarboxamide (Step 2, 294 mg, 0.912 mmol) in methanol (18 mL) was treated with sodium periodate (205 mg, 0.958 mmol) in water (3.8 mL), and the mixture was stirred at ambient temperature for 44 hours. The resulting mixture was diluted with water (25 mL) and extracted with methylene chloride (5×30 mL), and the combined organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product mixture was triturated with acetone/diethyl ether and then filtered to give the title compound as a mixture of two diastereomers,  1 H NMR (400 MHz, DMSO-d 6 ) δ 7.87 (s, 1H), 7.63 (s, 1H), 7.52 (d, 1H), 7.39 (m, 2H), 5.83 (m, 1H), 5.04 (dd, 1H), 4.29 (t, 1H), 4.02 (dd, 1H), 3.65 (m, 1H), 3.39 (m, 1H), 3.10 (m, 1H), 2.92 (m, 2H), 2.54 (m, 1H); MS (ESI+) for C 15 H 15 FN 2 O 4 S m/z 339 (M+H) + . 
     EXAMPLE 446 
     (5R)-(−)-3-[4-(3,6-Dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinecarboxamide S,S-dioxide 
     
       
                 
         
             
             
         
      
     
     A solution of (5R)-(−)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinecarboxamide (EXAMPLE 445, Step 2, 209 mg, 0.648 mmol) in water/acetone (25/75, 13 mL) under nitrogen was treated with N-methylmorpholine N-oxide (190 mg, 1.62 mmol) and osmium tetroxide (2.5 wt % in tBuOH, 0.41 mL, 0.0324 mmol), and the mixture was stirred at ambient temperature for 43 hours. The reaction was then treated with ½-saturated aqueous sodium bisulfite (25 mL) and extracted with methylene chloride (3×25 mL), and the combined organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was chromatographed on a Flash 40S 40 g silica gel (32-63 m) cartridge, eluting with a gradient of methanol/methylene chloride (2.5/97.5-4/96), and those fractions with an R f =0.48 by TLC (methanol/chloroform, 10/90) are pooled and concentrated to give the title compound, mp 206-208° C.; MS (ESI−) for C 15 H 15 FN 2 O 5 S m/z 353 (M−H) − ; [α] 25   D =−20 (c 0.98, DMSO). 
     EXAMPLE 447 
     (5R)-(−)-3-[4-(Tetrahydro-2H-thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinecarboxamide S,S-dioxide 
     
       
                 
         
             
             
         
      
     
     A mixture of (5R)-(−)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinecarboxamide S,S-dioxide (EXAMPLE 446, 73 mg, 0.206 mmol) and 10% palladium-on-carbon (44 mg, 0.0412 mmol) in methanol (21 mL) was shaken under a 40 psi hydrogen atmosphere on a Parr apparatus for 16 hours. The catalyst was then removed by filtration through a pad of Celite, rinsing with methanol and tetrahydrofuran, and the filtrate was concentrated under reduced pressure and triturated with (5% methanol/methylene chloride)/diethyl ether. Filtration then provides the title compound, mp 229-231° C. (dec.); MS (ESI−) for C 15 H 17 FN 2 O 5 S m/z 355 (M−H) − ; [α] 25   D =−20 (c 0.83, DMSO). 
     EXAMPLE 448 
     (5R)-(−)-3-[3-Fluoro-4-[4-(hydroxyacetyl)-1-piperazinyl]phenyl]-2-oxo-5-oxazolidinecarboxamide 
                                
Step 1: Preparation of (−)-phenylmethyl 4-[4-[(5R)-5-(aminocarbonyl)-2-oxo-3-oxazolidinyl]-2-fluorophenyl]-1-piperazinecarboxylate
 
     Following the general procedure of EXAMPLE 435, Step 1, and making non-critical variations but substituting benzyl 4-(4-{[benzyloxycarbonyl]amino}-2-fluorophenyl)-1-piperazinecarboxylate ( J. Med. Chem.  1996, 39(3), 673-679) for benzyl 3-fluoro-4-(4-morpholinyl)phenylcarbamate, the crude 1-(phenylmethyl)-4-[4-[(5R)-5-carboxy-2-oxo-3-oxazolidinyl]-2-fluorophenyl]-1-piperazinecarboxylate intermediate was obtained [MS (ESI−) for C 22 H 22 N 3 O 6 F m/z 442 (M−H) − ] and was used without further purification. This intermediate (1.66 g crude) was taken up in methanol (75 mL), 4 drops of concentrated sulfuric acid are added, and the mixture was stirred at ambient-temperature for 19 hours. Then, the reaction mixture was concentrated under reduced pressure and chromatographed twice on a Flash 40M 90 g silica gel (32-63 μm) cartridge, eluting with a gradient of methanol/methylene chloride (1/99-2/98). Pooling and concentration of those fractions with an R f =0.64 by TLC (methanol/chloroform, 5/95) provides 740 mg of the phenylmethyl 4-[2-fluoro-4-[(5R)-5-(methoxycarbonyl)-2-oxo-3-oxazolidinyl]phenyl]-1-piperazinecarboxylate intermediate [MS (ESI+) for C 23 H 24 N 3 O 6 F m/z 458 (M+H) + ; 75-80% purity] which was used without further purification. This intermediate was taken up in 2M ammonia in methanol (13 mL), and the resulting mixture was stirred at ambient temperature for 3 hours and then concentrated under reduced pressure. The residue was chromatographed on a Flash 40M 90 g silica gel (32-63 μm) cartridge, eluting with a gradient of methanol/methylene chloride (1/99-3/97), and those fractions with an R f =0.20 by TLC (methanol/chloroform, 5/95) are pooled and concentrated to give the title compound, mp 172-175° C.; MS (ESI+) for C 22 H 23 N 4 O 5 F m/z 443 (M+H) + ; [α] 25   D =−17 (c 1.04, DMSO). 
     Step 2: Preparation of (5R)-3-[3-fluoro-4-[4-[(phenylmethoxy)acetyl]-1-piperazinyl]phenyl]-2-oxo-5-oxazolidinecarboxamide 
     A mixture of (−)-phenylmethyl 4-[4-[(5R)-5-(aminocarbonyl)-2-oxo-3-oxazolidinyl]-2-fluorophenyl]-1-piperazinecarboxylate (Step 1, 415 mg, 0.938 mmol) and 10% palladium-on-carbon (100 mg, 0.0938 mmol) in methanol (45 mL) was shaken under a 45 psi hydrogen atmosphere on a Parr apparatus for 4 hours. The catalyst was then removed by filtration through a pad of Celite, and the filtrate was concentrated under reduced pressure to give 290 mg (100%) of the (5R)-3-[(3-fluoro-4-piperazinyl)phenyl]-2-oxo-5-oxazolidinecarboxamide intermediate [MS (ESI+) for C 14 H 17 N 4 O 3 F m/z 309 (M+H) + ] which was used without further purification. A mixture of this intermediate (240 mg, 0.778 mmol) in methylene chloride (7.8 mL) under nitrogen was treated with triethylamine (163 μL, 1.17 mmol) followed by benzyloxyacetyl chloride (135 μL, 0.856 mmol), and the resulting homogeneous mixture was stirred at ambient temperature for 3 hours. The reaction mixture was then diluted with water (20 mL) and methylene chloride (20 mL), the layers are separated, and the organic phase was washed with saline (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product which was then chromatographed on a Flash 40M 90 g silica gel (32-63 μm) cartridge, eluting with methanol/methylene chloride (2.5/97.5). Pooling and concentration of those fractions with an R f =0.50 by TLC (methanol/chloroform, 10/90) provides the title compound,  1 H NMR (400 MHz, DMSO-d 6 ) δ 7.85 (s, 1H), 7.61 (s, 1H), 7.52 (dd, 1H), 7.36 (m, 4H), 7.31 (m, 1H), 7.24 (m, 1H), 7.06 (m, 1H), 5.01 (dd, 1H), 4.53 (s, 2H), 4.25 (m, 3H), 3.97 (dd, 1H), 3.58 (m, 4H), 2.96 (m, 4H); MS (ESI+) for C 23 H 25 FN 4 O 5  m/z 457 (M+H) + . 
     Step 3: Preparation of (5R)-(−)-3-[3-fluoro-4-[4-(hydroxyacetyl)-1-piperazinyl]phenyl]-2-oxo-5-oxazolidinecarboxamide 
     A mixture of (5R)-3-[3-fluoro-4-[4-[(phenylmethoxy)acetyl]-1-piperazinyl]phenyl]-2-oxo-5-oxazolidinecarboxamide (Step 2, 260 mg, 0.570 mmol) and 10% palladium-on-carbon (61 mg, 0.0570 mmol) in a mixture of methanol (5 mL) and EtOH (23 mL) was shaken under a 40 psi hydrogen atmosphere on a Parr apparatus for 22 hours. The catalyst was then removed by filtration through a pad of Celite, rinsing with tetrahydrofuran (200 mL), and the filtrate was concentrated under reduced pressure and triturated with methanol/diethyl ether. Filtration then provided the title compound, mp 232-235° C. (dec.); MS (ESI+) for C 16 H 19 FN 4 O 5  m/z 367 (M+H) + ; [α] 25   D =−20 (c 0.98, DMSO). 
     EXAMPLE 449 
     (5R)-(−)-3-[4-(Thiomorpholin-4-yl)-3,5-difluorophenyl]-2-oxo-5-oxazolidinecarboxamide S,S-dioxide 
                                
Step 1: Preparation of 4-(2,6-difluorophenyl)thiomorpholine 1,1-dioxide
 
     Aluminum chloride (310 g, 2.3 mol) was added to chlorobenzene (2.5 L) to give a cloudy green suspension. Vinyl sulfone (230 mL, 2.3 mol) was added via funnel, followed by 2,6-difluoroaniline (250 mL, 2.3 mol). The light brown solution was heated to 110° C. Upon completion of the reaction, the heat was removed and the black solution was self-cooled to 70° C. The reaction mixture was then quenched in methylene chloride (4 L) and ice water (5 L), the aqueous phase was extracted with methylene chloride (3 L, 2 L, 2 L, 2 L) and the combined organic layers are concentrated, rediluted with branched octane (3 L), and then cooled to 0° C. for 30 minutes. The solids are filtered and washed with branched octane (2×500 mL) and are then dissolved in methylene chloride (3 L) and loaded onto a SiO 2  plug (1.8 kg). The column was eluted with dichloromethane (16 L) until clear. The methylene chloride solution was concentrated, and the solids are dissolved in hot ethyl acetate (3 L) followed by the addition of hexanes (900 mL). The black solution was self-cooled to room temperature overnight, and the resulting light amber crystal needles are filtered and washed with hexanes (4×250 mL). The solids are dried under reduced pressure at 50° C. overnight to give the title compound,  1 H NMR (CDCl 3 ) (δ): 7.08 (m, 1H), 6.91 (m, 2H), 3.67 (m, 4H), 3.18 (m, 4H). 
     Step 2: Preparation of 4-(2,6-difluoro-4-nitrophenyl)thiomorpholine 1,1-dioxide 
     To a suspension of 4-(2,6-difluorophenyl)thiomorpholine 1,1-dioxide (Step 1, 300 g, 1.21 mol) in 3 L of acetic acid, nitric acid (255 mL, ca. 6 mol, fuming, 90%) was added over 30 minutes at ambient temperature. A yellow precipitate forms within minutes and increases over time. The reaction was kept at room temperature for 18 hours and was then poured into 6 L of water. After stirring for 2 hours, the yellow suspension was filtered. The precipitate was washed with water (1.5 L×3) and ethanol (0.5 L×2) and dried at 50° C. overnight to give the title compound,  1 H NMR (DMSO-d 6 ) (δ): 8.05 (m, 2H), 3.69 (m, 4H), 3.26 (m, 4H). 
     Step 3: Preparation of 4-(1,1-dioxido-4-thiomorpholinyl)-3,5-difluoroaniline 
     To an autoclave was added 4-(2,6-difluoro-4-nitrophenyl)thiomorpholine 1,1-dioxide (Step 2, 7.0 kg, 24 moles, 1.0 eq). Raney Nickel (1.4 kg) was activated and suspended in tetrahydrofuran (4 L), and the slurry was added to the autoclave followed by additional tetrahydrofuran (66 L). The mixture was heated at 40° C. under a 40 psi hydrogen atmosphere until the reaction was complete. The mixture was then filtered, and the filtrate was directly used in the next step. A small portion of the filtrate can be concentrated and recrystallized in isopropanol to give the title compound in pure form,  1 H NMR (DMSO-d 6 ) (δ): 6.17 (m, 2H), 5.35 (s, 2H), 3.32 (m, 4H), 3.15 (m, 4H). 
     Step 4: Preparation of isobutyl 4-(1,1-dioxido-4-thiomorpholinyl)-3,5-difluorophenylcarbamate 
     To a 400 L glass-lined reactor containing the 4-(1,1-dioxido-4-thiomorpholinyl)-3,5-difluoroaniline/tetrahydrofuran solutions (Step 3, 12.6 kg, 48 moles, 1.0 eq) was added 47% potassium carbonate solution (14.1 kg, 48 moles, 1.0 eq). The mixture was heated to approximately 45° C., and isobutyl chloroformate (7.2 kg, 53 moles, 1.1 eq) was added while maintaining a reaction temperature between 45° C. and 55° C. The reaction was stirred at 45°-55° C. Once deemed complete, the reaction was quenched by slowly adding water (45 L) over 15 minutes. The reaction mixture was cooled to 25° C. and the phases are separated. The tetrahydrofuran solution was swapped to an isopropanol (150 L)/water (50 L) suspension, and the slurry was slowly cooled to 5° C. The yellow slurry was then filtered and the cake washed with cold isopropanol (2×30 L). The yellow solids are dried with 60° C. nitrogen to give the title compound,  1 H NMR (CDCl 3 ) (δ): 7.02 (m, 2H), 6.81 (s, 1H), 3.95 (d, 2H), 3.60 (m, 4H), 3.17 (m, 4H), 1.97 (m, 1H), 0.94 (d, 6H). 
     Step 5: Preparation of (5R)-(−)-3-[4-(thiomorpholin-4-yl)-3,5-difluorophenyl]-2-oxo-5-oxazolidinecarboxamide S,S-dioxide 
     Following the general procedure of EXAMPLE 448, Step 1, and making non-critical variations but substituting isobutyl 4-(1,1-dioxido-4-thiomorpholinyl)-3,5-difluorophenylcarbamate (Step 4) for benzyl 4-(4-{[benzyloxycarbonyl]amino}-2-fluorophenyl)-1-piperazinecarboxylate and purifying the final product by trituration and filtration from (10% methanol/chloroform)/diethyl ether, the title compound was obtained, mp 245-248° C. (dec.); MS (ESI+) for C 14 H 15 F 2 N 3 O 5 S m/z 376 (M+H) + ; [δ] 25   D =−22 (c 1.00, DMSO). 
     EXAMPLE 450 
     (5R)-(−)-3-[3-Fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinecarboxamide—Method C 
                                
Step 1: Preparation of ethyl (5R)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinecarboxylate
 
     A solution of 3-fluoro-4-morpholinoaniline ( J. Med. Chem.  1996, 39(3), 673-679, 0.796 g, 4.0 mmol), ethyl 2(R)-epoxypropanoate (0.696 g, 6.0 mmol) and lithium triflate (0.97 g, 6.2 mmol) in acetonitrile (12 mL) was stirred at 50-60° C. overnight. Solvent and excess epoxide was removed under reduced pressure, and the crude amino alcohol was redissolved in dry acetonitrile (40 mL) and 1,1′-carbonyldiimidazole (1.46 g, 9.0 mmol) was added. The mixture was stirred at ambient temperature overnight, and then the solvent was removed under reduced pressure. The residue was partitioned between ethyl acetate (70 mL) and 3% aqueous citric acid (100 mL), the layers are separated, and the organic phase was washed with 3% aqueous citric acid (3×100 mL), water and saline, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The product mixture was then purified by silica gel chromatography, eluting with ethanol/methylene chloride (2/98), and the appropriate fractions are pooled and concentrated to give the title compound, MS (ESI+) for C 16 H 19 N 2 O 5 F m/z 339 (M+H) + . 
     Step 2: Preparation of (5R)-(−)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinecarboxamide 
     A mixture of of ethyl (5R)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinecarboxylate (Step 1, 0.22 g, 0.65 mmol) in 2M ammonia in methanol (5-6 mL) was heated in a closed vial at 60° C. for approximately 1 hour. The resulting mixture was cooled to ambient temperature and concentrated under reduced pressure, and the crude product was recrystallized from methanol to give the title compound, MS (ESI+) for C 14 H 16 N 3 O 4 F m/z 310 (M+H) + . 
     EXAMPLE 451 
     (5R)-(−)-3-[3,5-Difluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinecarboxamide 
                                
Step 1: Preparation of butyl (5R)-3-[3,5-difluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinecarboxylate
 
     A solution of 3,5-difluoro-4-(4-morpholinyl)aniline (See U.S. Pat. No. 5,688,792, 2.00 g, 9.34 mmol), butyl 2(R)-glycidate (2.02 g, 14.0 mmol) and lithium triflate (2.18 g, 14.0 mmol) in acetonitrile (37 mL) was stirred at 60° C. under N 2  for 48 hrs. Solvent was removed under reduced pressure, and the residue was taken up in MeOH/CH 2 Cl 2  (5/95, 100 mL), washed with water (2×25 mL) and saline (25 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was flushed through a Flash 40M 90 g silica gel cartridge with EtOAc/CH 2 Cl 2  (10/90), and the appropriate fractions were pooled and concentrated to give the amino alcohol intermediate [R t =0.10 by TLC, EtOAc/hexanes (25/75)] which was contaminated with residual starting material. This intermediate (2.5 g in two lots) was then dissolved in acetonitrile (total of 70 mL) and treated with 1,1′-carbonyldiimidazole (total of 1.69 g, 10.4 mmol, 1.5 equiv.), and the reaction mixtures were stirred at ambient temperature for 6 days and then concentrated under reduced pressure. The product mixtures were each taken up in CH 2 Cl 2  (50 mL), washed with 0.1M hydrochloric acid (2×20 mL) and saline (10 mL), dried over anhydrous sodium sulfate, concentrated under reduced pressure and chromatographed on a Flash 40M 90 g silica gel cartridge with EtOAc/CH 2 Cl 2  (5/95). Those fractions with an R f =0.16 by TLC (EtOAc/hexanes, 25/75) were pooled and concentrated to give the title compound, mp 99-100° C.; MS (ESI+) for C 18 H 22 N 2 O 5 F 2  m/z 385 (M+H) + . 
     Step 2: Preparation of (5R)-(−)-3-[3,5-difluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinecarboxamide 
     The butyl (SR)-3-[3,5-difluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinecarboxylate (Step 1, 350 mg, 0.910 mmol) was treated with 7N ammonia in methanol (9.1 mL) under N 2 , and the mixture was stirred at ambient temperature for 30 mins. The reaction mixture was then concentrated under reduced pressure, and the residue was recrystallized from EtOAc/hexanes to give the title compound, mp 181-183° C.; MS (ESI+) for C 14 H 15 N 3 O 4 F 2  m/z 328 (M+H) + ; [α] 25   D  −23 (c 0.94, DMSO). 
     EXAMPLE 452 
     (5R)-(−)-3-[4-(Thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxamide S,S-dioxide 
                                
Step 1: Preparation of butyl (5R)-3-[4-(thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate
 
     A solution of 4-(4-thiomorpholinyl)aniline (See  Med. Chem. Res.  1999, 9(3), 149-161, 2.60 g, 13.4 mmol), butyl 2(R)-glycidate (2.89 g, 20.1 mmol) and lithium triflate (3.13 g, 20.1 mmol) in acetonitrile (54 mL) was stirred at 60° C. under N 2  for 36 hrs. Solvent was removed under reduced pressure, and the residue was taken up in MeOH/CH 2 Cl 2  (5/95, 100 mL), washed with water (50 mL) and saline (20 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was flushed through a Flash 40M 90 g silica gel cartridge with EtOAc/CH 2 Cl 2  (15/85), and the appropriate fractions were pooled and concentrated to give the amino alcohol intermediate [R f =0.19 by TLC, EtOAc/hexanes (25/75)] which was contaminated with the dialkylated by-product. This intermediate (4.25 g) was then dissolved in acetonitrile (125 mL) and treated with 1,1′-carbonyldiimidazole (3.05 g, 18.8 mmol, 1.5 equiv.), and the reaction mixture was stirred at ambient temperature for approximately 3 days and then concentrated under reduced pressure. The product mixture was taken up in CH 2 Cl 2  (100 mL), washed with 0.1M hydrochloric acid (3×25 mL) and saline (25 mL), dried over anhydrous sodium sulfate, concentrated under reduced pressure and chromatographed on a Flash 40M 90 g silica gel cartridge with EtOAc/CH 2 Cl 2  (15/85). Those fractions with an R f =0.57 by TLC (EtOAc/hexanes, 50/50) were pooled and concentrated to give the title compound, mp 95.5-98° C.; MS (ESI+) for C 18 H 24 N 2 O 4 S m/z 365 (M+H) + . 
     Step 2: Preparation of butyl (5R)-3-[4-(thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate S,S-dioxide 
     A solution of butyl (5R)-3-[4-(thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate (Step 1, 600 mg, 1.65 mmol) in water/acetone (25/75, 32 mL) under N 2  was treated with N-methylmorpholine N-oxide (483 mg, 4.12 mmol) and osmium tetroxide (2.5 wt % in tBuOH, 1.03 mL, 0.0825 mmol), and the mixture was stirred at ambient temperature for 18 hrs. The reaction was then treated with ½-saturated aqueous sodium bisulfite (20 mL), diluted with water (20 mL) and extracted with CH 2 Cl 2  (2×50 mL). The combined organic phase was washed with saline (20 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure, and the product mixture was chromatographed on a Flash 40S 40 g silica gel cartridge with MeOH/CH 2 Cl 2  (1/99). Pooling and concentration of those fractions with an R f =0.5 by TLC (MeOH/CHCl 3 , 5/95) followed by recrystallization from EtOAc/hexanes gave the title compound, mp 100-102° C.; MS (ESI+) for C 18 H 24 N 2 O 6 S m/z 397 (M+H) + . 
     Step 3: Preparation of (5R)-(−)-3-[4-(thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxamide S,S-dioxide 
     The butyl (5R)-3-[4-(thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate S,S-dioxide (Step 2, 400 mg, 1.01 mmol) was treated with 7N ammonia in methanol (10.1 mL) under N 2 , and the mixture was stirred at ambient temperature for 25 mins. The resulting slurry was then diluted with diethyl ether (5 mL) and filtered to give the title compound, mp 226-228° C.; MS (ESI−) for C 14 H 17 N 3 O 5 S m/z 338 (M−H) − ; [α] 25   D  −22 (c 0.94, DMSO). 
     EXAMPLE 453 
     (5R)-(−)-3-[3-Fluoro-4-(thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxamide S,S-dioxide 
                                
Step 1: Preparation of butyl (5R)-3-[3-fluoro-4-(thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate
 
     Following the general procedure of EXAMPLE 452, Step 1, and making non-critical variations but substituting 3-fluoro-4-(4-thiomorpholinyl)aniline (See  J. Med. Chem.  1996, 39(3), 680-685) for 4-(4-thiomorpholinyl)aniline, the title compound was obtained, mp 128-130° C.; MS (ESI+) for C 18 H 23 N 2 O 4 ES m/z 383 (M+H) + . 
     Step 2: Preparation of butyl (5R)-3-[3-fluoro-4-(thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate S,S-dioxide 
     Following the general procedure of EXAMPLE 452, Step 2, and making non-critical variations but substituting butyl (5R)-3-[3-fluoro-4-(thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate (Step 1) for butyl (5R)-3-[4-(thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate, the title compound was obtained, mp 169-171° C. (dec.); MS (ESI+) for C 18 H 23 N 2 O 6 FS m/z 415 (M+H) + . 
     Step 3: Preparation of (5R)-(−)-3-[3-fluoro-4-(thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxamide S,S-dioxide 
     Following the general procedure of EXAMPLE 452, Step 3, and making non-critical variations but substituting butyl (5R)-3-[3-fluoro-4-(thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate S,S-dioxide (Step 2) for butyl (5R)-3-[4-(thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate S,S-dioxide, the title compound was obtained, mp 245-247° C. (dec.); MS (ESI+) for C 14 H 16 N 3 O 5 FS m/z 358 (M+H) + ; [α] 25   D  −22 (c 0.92, DMSO). 
     EXAMPLE 454 
     (5R)-(−)-3-[3-Fluoro-4-(thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxamide S-oxide 
                                
Step 1: Preparation of butyl (5R)-3-[3-fluoro-4-(thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate S-oxide
 
     A solution of sodium periodate (265 mg, 1.24 mmol) in water (5 mL) was treated with a slurry of butyl (5R)-3-[3-fluoro-4-(thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate (EXAMPLE 20, Step 1, 450 mg, 1.18 mmol) in methanol (24 mL), and the mixture was stirred at ambient temperature for 23 hrs. The resulting mixture was diluted with water (20 mL) and saline (20 mL) and extracted with CH 2 Cl 2  (2×40 mL), and the combined organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was chromatographed on a Flash 40S 40 g silica gel cartridge, eluting with a gradient of MeOH/CH 2 Cl 2  (1/99-2/98), and those fractions with an R f =0.37 by TLC (MeOH/CHCl 3 , 5/95) were pooled and concentrated and the residue recrystallized from EtOAc/hexanes to give the title compound, mp 128-129° C.; MS (ESI+) for C 18 H 23 N 2 O 5 FS m/z 399 (M+H) + . 
     Step 2: Preparation of (5R)-(−)-3-[3-fluoro-4-(thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxamide S-oxide 
     Following the general procedure of EXAMPLE 452, Step 3, and making non-critical variations, but substituting (SR)-3-[3-fluoro-4-(thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxamide S-oxide (Step 1) for butyl (5R)-3-[4-(thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate S,S-dioxide and purifying the product by trituration and filtration from hot acetonitrile, the title compound was obtained, mp 264-266° C. (dec.); MS (ESI+) for C 14 H 16 N 3 O 4 FS m/z 342 (M+H) + ; [α] 25   D  −22 (c 0.39, DMSO). 
     EXAMPLE 455 
     (5R)-(−)-3-[3,5-Difluoro-4-(thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxamide S-oxide 
                                
Step 1: Preparation of 4-(2,6-Difluoro-4-nitrophenyl)thiomorpholine
 
     A solution of 3,4,5-trifluoronitrobenzene (5.00 g, 28.24 mmol) in acetonitrile (60 mL) was cooled to 0° C. and treated with N,N-diisopropylethylamine (7.38 mL, 42.35 mmol) followed by thiomorpholine (2.98 mL, 29.65 mmol). The ice bath was removed and the reaction mixture stirred at room temperature under nitrogen for approximately 24 hrs, during which additional thiomorpholine (0.1 eq) was added. The solvent was removed under reduced pressure, and the residue was diluted with ethyl acetate, washed with 1N hydrochloric acid (until the washings were acidic), saturated aqueous sodium bicarbonate and saline, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound, mp 104-105° C. 
     Step 2: Preparation of 3,5-difluoro-4-(4-morpholinyl)aniline 
     A solution of 4-(2,6-difluoro-4-nitrophenyl)thiomorpholine (3.00 g, 11.5 mmol) in tetrahydrofuran (60 mL) was added to a Parr bottle containing a mixture of Raney nickel (1 g) in water (15 mL) under N 2 , and the reaction mixture was shaken on a Parr apparatus under a hydrogen atmosphere at 40 psi for 24 hrs. The catalyst was removed by filtration through Celite, rinsing with tetrahydrofuran and water, the filtrate was diluted with water (50 mL) and EtOAc (50 mL), and the layers were separated. The organic phase was washed with saline (25 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the resulting oil was chromatographed on a Flash 40M 90 g silica gel cartridge eluting with EtOAc/heptane (15/85). Pooling and concentration of those fractions with an Rt=0.19 by TLC (EtOAc/hexanes, 25/75) gave the title compound, mp 85-86° C.; MS (ESI+) for C 10 H 12 N 2 F 2 S m/z 231 (M+H) + . 
     Step 3: Preparation of butyl (5R)-3-[3,5-difluoro-4-(thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate 
     Following the general procedure of EXAMPLE 452, Step 1, and making non-critical variations but substituting 3,5-difluoro-4-(4-morpholinyl)aniline (Step 2) for 4-(4-thiomorpholinyl)aniline, the title compound was obtained, mp 102-103° C.; MS (ESI+) for C 18 H 22 N 2 O 4 F 2 S m/z 401 (M+H) + . 
     Step 4: Preparation of butyl (5R)-3-[3,5-difluoro-4-(thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate S-oxide 
     Following the general procedure of EXAMPLE 454, Step 1, and making non-critical variations but substituting butyl (5R)-3-[3,5-difluoro-4-(thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate (Step 3) for butyl (5R)-3-[4-(thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate, the title compound was obtained, mp 114-116° C.; MS (ESI+) for C 18 H 22 N 2 O 5 F 2 S m/z 417 (M+H) + . 
     Step 5: Preparation of (5R)-(−)-3-[3,5-Difluoro-4-(thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxamide S-oxide 
     Following the general procedure of EXAMPLE 452, Step 3, and making non-critical variations, but substituting (5R)-3-[3,5-difluoro-4-(thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxamide S-oxide (Step 4) for butyl (5R)-3-[4-(thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate S,S-dioxide, the title compound was obtained, mp 273-276° C. (dec.); MS (ESI+) for C 14 H 15 N 3 O 4 F 2 S m/z 360 (M+H) + ; [α] 25   D  −24 (c 0.96, DMSO). 
     EXAMPLE 456 
     (SR)-3-[3-Fluoro-4-(cis-tetrahydro-1-oxido-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxamide 
                                
Step 1: Preparation of 2-methylpropyl [3-fluoro-4-(tetrahydro-2H-thiopyran-4-yl)phenyl]carbamate
 
     A solution of 2-methylpropyl [3-fluoro-4-(tetrahydro-4-hydroxy-2H-thiopyran-4-yl)phenyl]carbamate (See  Org. Proc. Res. Dev.  2001, 5, 80-83, 4.00 g, 12.2 mmol) in trifluoroacetic acid (19 mL, 244 mmol) under N 2  was treated with triethylsilane (5.85 mL, 36.6 mmol) dropwise, stirred for 1 hr, and then added dropwise to saturated aqueous potassium carbonate (250 mL) with vigorous stirring. The mixture was extracted with diethyl ether (200 mL), and the organic phase was washed with water (2×50 mL) and saline (50 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Trituration and filtration from diethyl ether/hexanes or ethyl acetate/hexanes gave the title compound,  1 H NMR (CDCl 3 , 400 MHz) δ 7.26 (m, 1H), 7.11 (t, 1H), 6.97 (m, 1H), 6.59 (bs, 1H), 3.95 (d, 2H), 2.85 (m, 3H), 2.68 (m, 2H), 2.09 (m, 2H), 1.98 (m, 1H), 1.84 (m, 2H), 0.96 (d, 6H). 
     Step 2: Preparation of 3-fluoro-4-(tetrahydro-2H-thiopyran-4-yl)benzenamine 
     A mixture of 2-methylpropyl [3-fluoro-4-(tetrahydro-2H-thiopyran-4-yl)phenyl]carbamate (Step 1, 2.12 g, 6.81 mmol) in ethylene glycol (25 mL) was treated with aqueous potassium hydroxide (45%, 25.5 g, 204 mmol) with vigorous stirring, and the mixture was heated to 95° C. and stirred at this temperature for 18 hrs. The reaction was then cooled to ambient temperature and diluted with water (50 mL) and CH 2 Cl 2  (100 mL), the layers were separated, and the organic phase was washed with water (50 mL) and saline (20 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was chromatographed on a Flash 40M 90 g silica gel cartridge with a gradient of EtOAc/heptane (15/85-25/75), and those fractions with an R f =0.32 by TLC (EtOAc/hexanes, 25/75) were pooled and concentrated to give the title compound, mp 96-98° C.; MS (ESI+) for C 11 H 14 NFS m/z 212 (M+H) + . 
     Step 3: Preparation of butyl (5R)-3-[3-fluoro-4-(tetrahydro-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate 
     Following the general procedure of EXAMPLE 452, Step 1, and making non-critical variations but substituting 3-fluoro-4-(tetrahydro-2H-thiopyran-4-yl)benzenamine (Step 2) for 4-(4-thiomorpholinyl)aniline, the title compound was obtained, mp 98-100° C.; MS (ESI+) for C 19 H 24 NO 4 FS m/z 382 (M+H) + . 
     Step 4: Preparation of butyl (5R)-3-[3-fluoro-4-(cis-tetrahydro-1-oxido-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate 
     Following the general procedure of EXAMPLE 454, Step 1, and making non-critical variations but substituting butyl (5R)-3-[3-fluoro-4-(tetrahydro-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate (Step 3) for butyl (5R)-3-[4-(thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate, a mixture of the cis and trans sulfoxide products in approximately a 2:1 ratio was obtained. Subsequent purification by preparative HPLC (Chiralcel OD column, EtOH eluent) followed by recrystallization from EtOAc/hexanes provided the title compound, mp 142-145° C.; MS (ESI+) for C 19 H 24 NO 5 FS m/z 398 (M+H) + . 
     Step 5: Preparation of (5R)-3-[3-fluoro-4-(cis-tetrahydro-1-oxido-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxamide 
     Following the general procedure of EXAMPLE 452, Step 3, and making non-critical variations, but substituting butyl (SR)-3-[3-fluoro-4-(cis-tetrahydro-1-oxido-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate (Step 4) for butyl (5R)-3-[4-(thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate S,S-dioxide and purifying the product by trituration and filtration from hot methanol and acetonitrile, the title compound was obtained, mp 279-281° C. (dec.); MS (ESI+) for C 15 H 17 N 2 O 4 FS m/z 341 (M+H) + . 
     EXAMPLE 457 
     (5R)-3-[3-Fluoro-4-(trans-tetrahydro-1-oxido-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxamide 
                                
Step 1: Preparation of butyl (5R)-3-[3-fluoro-4-(trans-tetrahydro-1-oxido-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate
 
     Following the general procedure of EXAMPLE 454, Step 1, and making non-critical variations but substituting butyl (5R)-3-[3-fluoro-4-(tetrahydro-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate (EXAMPLE 23, Step 3) for butyl (5R)-3-[4-(thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate, a mixture of the cis and trans sulfoxide products in approximately a 2:1 ratio was obtained. Subsequent purification by preparative HPLC (Chiralcel OD column, EtOH eluent) followed by recrystallization from EtOAc/hexanes provided the title compound, mp 133-136° C.; MS (ESI+) for C 19 H 24 NO 5 FS m/z 398 (M+H) + . 
     Step 2: Preparation of (5R)-3-[3-fluoro-4-(trans-tetrahydro-1-oxido-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxamide 
     Following the general procedure of EXAMPLE 452, Step 3, and making non-critical variations, but substituting butyl (SR)-3-[3-fluoro-4-(trans-tetrahydro-1-oxido-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate (Step 1) for butyl (5R)-3-[4-(thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate S,S-dioxide, the title compound was obtained, mp 201-203° C.; MS (ESI+) for C 15 H 17 N 2 O 4 FS m/z 341 (M+H) + . 
     EXAMPLE 458 
     (5R)-(−)-3-[4-(tetrahydro-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxamide S,S-dioxide 
                                
Step 1: Preparation of 2-methylpropyl 4-bromophenylcarbamate
 
     A solution of 4-bromoaniline (10.0 g, 58.1 mmol) in tetrahydrofuran (230 mL) was treated with sodium bicarbonate (9.77 g, 116.2 mmol) and water (100 mL) followed by isobutyl chloroformate (8.3 mL, 63.9 mmol), and the mixture was stirred at ambient temperature for 2 hrs. The mixture was then diluted with water (100 mL) and EtOAc (100 mL), the layers were separated, and the organic phase was washed with water (50 mL) and saline (50 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Recrystallization of the resulting solid from EtOAc/hexanes provided the title compound, mp 95-96° C.; MS (ESI−) for C 11 H 14 NO 2 Br m/z 270 (M−H) − . 
     Step 2: Preparation of 2-methylpropyl [4-(tetrahydro-4-hydroxy-2H-thiopyran-4-yl)phenyl]carbamate 
     A solution of 2-methylpropyl 4-bromophenylcarbamate (Step 1, 10.0 g, 36.7 mmol) in anhydrous tetrahydrofuran (184 mL) at −78° C. under N 2  was treated n-butyllithium (1.6M in hexanes, 48.2 mL, 77.1 mmol) dropwise over 20 mins, and the mixture was stirred at −78° C. for 45 mins. The resulting slurry was then treated with a solution of tetrahydro-2H-thiopyran-4-one (4.48 g, 38.5 mmol) in anhydrous tetrahydrofuran (38 mL) dropwise over 5 mins to give an opaque mixture which was allowed to slowly warm to 0° C. with stirring over approximately 2.5 hrs. The mixture was then quenched by the slow addition of saturated aqueous ammonium chloride (75 mL), water (75 mL) was added, and the layers were separated. The organic phase was washed with water (50 mL) and saline (50 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the crude product was recrystallized from EtOAc/hexanes to give the title compound, mp 150-151° C.; MS (ESI−) for C 16 H 23 NO 3 S m/z 308 (M−H) − . 
     Step 3: Preparation of 2-methylpropyl [4-(tetrahydro-2H-thiopyran-4-yl)phenyl]carbamate 
     Following the general procedure of EXAMPLE 456, Step 1, and making non-critical variations but substituting 2-methylpropyl [4-(tetrahydro-4-hydroxy-2H-thiopyran-4-yl)phenyl]carbamate (Step 2) for 2-methylpropyl [3-fluoro-4-(tetrahydro-4-hydroxy-2H-thiopyran-4-yl)phenyl]carbamate and purifying the product by recrystallization from EtOAc/hexanes, the title compound was obtained, mp 126-128° C.; MS (ESI−) for C 16 H 23 NO 2 S m/z 292 (M−H) − . 
     Step 4: Preparation of 4-(tetrahydro-2H-thiopyran-4-yl)benzenamine 
     Following the general procedure of EXAMPLE 456, Step 2, and making non-critical variations but substituting 2-methylpropyl [4-(tetrahydro-2H-thiopyran-4-yl)phenyl]carbamate (Step 3) for 2-methylpropyl [3-fluoro-4-(tetrahydro-2H-thiopyran-4-yl)phenyl]carbamate, the title compound was obtained, mp 103-106° C.; MS (ESI+) for C 11 H 15 NS m/z 194 (M+H) + . 
     Step 5: Preparation of butyl (5R)-3-[4-(tetrahydro-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate 
     Following the general procedure of EXAMPLE 452, Step 1, and making non-critical variations but substituting 4-(tetrahydro-2H-thiopyran-4-yl)benzenamine (Step 4) for 4-(4-thiomorpholinyl)aniline, the title compound was obtained, mp 94-96° C.; MS (ESI+) for C 19 H 25 NO 4 s m/z 364 (M+H) + . 
     Step 6: Preparation of butyl (SR)-3-[4-(tetrahydro-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate S,S-dioxide 
     Following the general procedure of EXAMPLE 452, Step 2, and making non-critical variations but substituting butyl (5R)-3-[4-(tetrahydro-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate (Step 5) for butyl (5R)-3-[4-(thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate, the title compound was obtained, mp 176-179° C.; MS (ESI+) for C 19 H 25 NO 6 S m/z 396 (M+H) + . 
     Step 7: Preparation of (5R)-(−)-3-[4-(tetrahydro-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxamide S,S-dioxide 
     Following the general procedure of EXAMPLE 452, Step 3, and making non-critical variations, but substituting butyl (5R)-3-[4-(tetrahydro-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate S,S-dioxide (Step 6) for butyl (5R)-3-[4-(thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate S,S-dioxide, the title compound was obtained, mp 211-212° C.; MS (ESI−) for C 15 H 18 N 2 O 5 S m/z 337 (M−H) − ; [□] 25   D  −19 (c 0.95, DMSO) 
     EXAMPLE 459 
     (5R)-3-[4-(cis-tetrahydro-1-oxido-2H-thiopyran-4-yl)phenyl]-2-oxo-S-oxazolidinecarboxamide 
                                
Step 1: Preparation of butyl (5R)-3-[4-(cis-tetrahydro-1-oxido-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate
 
     Following the general procedure of EXAMPLE 459, Step 1, and making non-critical variations but substituting butyl (SR)-3-[4-(tetrahydro-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate (EXAMPLE 458, Step 5) for butyl (5R)-3-[4-(thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate, a mixture of the cis and trans sulfoxide products in approximately a 2:1 ratio was obtained. Subsequent purification by preparative HPLC (Chiralcel OD column, EtOH eluent) followed by recrystallization from EtOAc/hexanes provided the title compound, mp 127-130° C.; MS (ESI+) for C 19 H 25 NO 5 S m/z 380 (M+H) + . 
     Step 2: Preparation of (5R)-3-[4-(cis-tetrahydro-1-oxido-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxamide 
     Following the general procedure of EXAMPLE 452, Step 3, and making non-critical variations, but substituting butyl (5R)-3-[4-(cis-tetrahydro-1-oxido-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate (Step 1) for butyl (5R)-3-[4-(thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate S,S-dioxide, the title compound was obtained, mp 269-273° C. (dec.); MS (ESI−) for C 15 H 18 N 2 O 4 S m/z 321 (M−H) − . 
     EXAMPLE 460 
     (SR)-3-[4-(trans-tetrahydro-1-oxido-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxamide 
                                
Step 1: Preparation of butyl (5R)-3-[4-(trans-tetrahydro-1-oxido-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate
 
     Following the general procedure of EXAMPLE 454, Step 1, and making non-critical variations but substituting butyl (SR)-3-[4-(tetrahydro-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate (EXAMPLE 458, Step 5) for butyl (5R)-3-[4-(thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate, a mixture of the cis and trans sulfoxide products in approximately a 2:1 ratio was obtained. Subsequent purification by preparative HPLC (Chiralcel OD column, EtOH eluent) followed by recrystallization from EtOAc/hexanes provided the title compound, mp 115-117° C.; MS (ESI+) for C 19 H 25 NO 5 S m/z 380 (M+H) + . 
     Step 2: Preparation of (5R)-3-[4-(trans-tetrahydro-1-oxido-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxamide 
     Following the general procedure of EXAMPLE 452, Step 3, and making non-critical variations, but substituting butyl (5R)-3-[4-(trans-tetrahydro-1-oxido-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate (Step 1) for butyl (5R)-3-[4-(thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate S,S-dioxide, the title compound was obtained, mp 174-175° C.; MS (ESI−) for C 15 H 18 N 2 O 4 S m/z 321 (M−H) − . 
     EXAMPLE 461 
     (5R)-3-[4-(Tetrahydro-2H-thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinecarboxamide S,S-dioxide—Method B 
                                
Step 1: Preparation of 2-methylpropyl [4-(tetrahydro-1,1-dioxido-2H-thiopyran-4-yl)-3-fluorophenyl]carbamate
 
     Following the general procedure of EXAMPLE 452, Step 2, and making non-critical variations but substituting 2-methylpropyl [4-(tetrahydro-2H-thiopyran-4-yl)-3-fluorophenyl]carbamate (EXAMPLE 456, Step 1) for butyl (5R)-3-[4-(thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate, the title compound is obtained,  1 H NMR (CDCl 3 ) (δ) 7.36 (bd, 1H), 7.14 (t, 1H), 6.99 (m, 1H), 6.70 (bs, 1H), 3.95 (d, 2H), 3.14 (m, 4H), 3.07 (m, 1H), 2.38 (m, 2H), 2.18 (m, 2H), 1.95 (m,1H), 0.96 (d, 6H). 
     Step 2: Preparation of (5R)-3-[4-(tetrahydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-hydroxymethyl-2-oxazolidinone S,S-dioxide 
     A solution of 2-methylpropyl [4-(tetrahydro-1,1-dioxido-2H-thiopyran-4-yl)-3-fluorophenyl]carbamate (Step 1, 2.00 g, 5.82 mmol) in dry tetrahydrofuran at −78° C. under N 2  was treated with n-butyllithium (1.6M in hexanes, 3.82 mL, 6.11 mmol) dropwise and stirred at −78° C. for 45 mins. Then, (R)-glycidyl butyrate (0.86 mL, 6.11 mmol) was added dropwise, and the resulting mixture was stirred at −78° C. for 30 mins and at ambient temperature for 2.75 days. The reaction mixture was then quenched with saturated aqueous ammonium chloride (15 mL), diluted with water (15 mL) and EtOAc (25 mL), and the layers were separated. The organic phase was diluted with small amounts of methylene chloride, methanol and tetrahydrofuran in an attempt to dissolve a precipitate that had formed and was then washed with water (20 mL) and saline (20 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting solid was then diluted with hot methanol/EtOAc (1:5, 100 mL), followed by hexanes (150 mL), and filtered to give the title compound,  1 H NMR (DMSO) (δ) 7.51 (dd, 1H), 7.37 (t, 1H), 7.30 (m, 1H), 5.21 (t, 1H), 4.70 (m, 1H), 4.07 (t, 1H), 3.81 (dd, 1H), 3.65 (m, 1H), 3.55 (m, 1H), 3.37 (m, 2H), 3.20 (m, 1H), 3.10 (m, 2H), 2.15 (m, 2H), 2.03 (m, 2H). 
     Step 3: Preparation of methyl (5R)-3-[4-(tetrahydro-2H-thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinecarboxylate S,S-dioxide 
     A mixture of ruthenium(III) trichloride (29 mg, 0.139 mmol, 4 mol %), sodium periodate (3.21 g, 15.0 mmol), and sodium dihydrogen phosphate monohydrate (2.60 g, 18.8 mmol) in water/methylene chloride (10:1, 21 mL) was treated with a suspension of (5R)-3-[4-(tetrahydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-hydroxymethyl-2-oxazolidinone S,S-dioxide (Step 2, 1.20 g, 3.49 mmol) in acetonitrile (35 mL), and the resulting mixture was stirred at ambient temperature for 24 hrs and was then adjusted to pH 2 with aqueous hydrochloric acid (1M) and extracted with methylene chloride (3×100 mL). The combined organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure, and the residue was flushed through a Flash 40M 90 g silica gel cartridge with a gradient of CH 3 CN/CH 2 Cl 2  (20/80-40/60) containing 1% formic acid. Those fractions containing the carboxylic acid intermediate (920 mg total) were pooled and concentrated, and the white solid was dissolved in methanol (25 mL) and treated with 3 to 4 drops of concentrated sulfuric acid. The resulting mixture was stirred at ambient temperature for 4 hrs and was then concentrated under reduced pressure and chromatographed on a Flash 40S 40 g silica gel cartridge, eluting with a gradient of MeOH/CH 2 Cl 2  (1/99-2/98). Pooling and concentration of those fractions with an R f =0.53 by TLC (MeOH/CH 2 Cl 2 , 5/95) provided the title compound as an amorphous solid,  1 H NMR (CDCl 3 ) (δ) 7.50 (dd, 1H), 7.25 (t, 1H), 7.15 (m, 1H), 5.09 (dd, 1H), 4.27 (t, 1H), 4.13 (dd, 1H), 3.88 (s, 3H), 3.15 (m, 4H), 3.11 (m, 1H), 2.40 (m, 2H), 2.19 (m, 2H). 
     Step 4: Preparation of (SR)-3-[4-(tetrahydro-2H-thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinecarboxamide S,S-dioxide 
     Following the general procedure of EXAMPLE 452, Step 3, and making non-critical variations but substituting methyl (5R)-3-[4-(tetrahydro-2H-thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinecarboxylate S,S-dioxide (Step 3) for butyl (5R)-3-[4-(thiomorpholin-4-yl)phenyl]-2-oxo-5-oxazolidinecarboxylate S,S-dioxide and purifying the product by trituration and filtration from (5% MeOH/CH 2 Cl 2 )/Et 2 O, the title compound was obtained, mp 231-234° C. (dec.); MS (ESI−) for C 15 H 17 FN 2 O 5 S m/z 355 (M−H) − . 
     Additional Examples of amide-containing compounds that can be used in the present invention are disclosed below. 
     EXAMPLE 462 
     N-{3-[3-fluoro-4-(5-oxo-5,6-dihydro-4H-[1,3,4]thiadiazin-2-yl)-phenyl]-2-oxo-oxazolidin-5(S)-ylmethyl}-acetamide 
     EXAMPLE 463 
     N-{3-[3-fluoro-4-(6(S)-methyl-5-oxo-5,6-dihydro-4H-[1,3,4]thiadiazin-2-yl)-phenyl]-2-oxo-oxazolidin-5(S)-ylmethyl}-acetamide 
     EXAMPLE 464 
     N-{3-[3-fluoro-4-(6(R)-methyl-5-oxo-5,6-dihydro-4H-[1,3,4]thiadiazin-2-yl)-phenyl]-2-oxo-oxazolidin-5(S)-ylmethyl}-acetamide 
     EXAMPLE 465 
     N-{3-[3-fluoro-4-(5-oxo-5,6-dihydro-4H-[1,3,4]thiadiazin-2-yl)-phenyl]-2-oxo-oxazolidin-5 (S)-ylmethyl}-propionamide 
     EXAMPLE 466 
     cyclopropanecarboxylic acid {3-[3-fluoro-4-(5-oxo-5,6-dihydro-4H-[1,3,4]thiadiazin-2-yl)-phenyl]-2-oxo-oxazolidin-5(S)-ylmethyl}-amide 
     EXAMPLE 467 
     N-{3-[3-fluoro-4-(5-oxo-5,6-dihydro-4H-[1,3,4]thiadiazin-2-yl)-phenyl]-2-oxo-oxazolidin-5 (S)-ylmethyl}-thioacetamide 
     EXAMPLE 468 
     N-{3-[3-fluoro-4-(5-thioxo-5,6-dihydro-4H-[1,3,4]thiadiazin-2-yl)-phenyl]-2-oxo-oxazolidin-5 (S)-ylmethyl}-thioacetamide 
     EXAMPLE 469 
     N-{3-[3-fluoro-4-(5-oxo-5,6-dihydro-4H-[1,3,4]thiadiazin-2-yl)-phenyl]-2-oxo-oxazolidin-5 (S)-ylmethyl}-acetamide 
     EXAMPLE 470 
     N-{3-[3-fluoro-4-(5-oxo-5,6-dihydro-4H-[1,3,4]thiadiazin-2-yl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-3-(4-hydroxy-phenyl)-acrylamide 
     EXAMPLE 471 
     N-{3-[4-(6,6-dimethyl-5-oxo-5,6-dihydro-4H-[1,3,4]thiadiazin-2-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5(S)-ylmethyl}-acetamide 
     EXAMPLE 472 
     N-{3-[3-fluoro-4-(6-ethyl-5-oxo-5,6-dihydro-4H-[1,3,4]thiadiazin-2-yl)-phenyl]-2-oxo-oxazolidin-5(S)-ylmethyl}-acetamide 
     EXAMPLE 473 
     N-{3-[3-fluoro-4-(9-oxo-5-thia-7,8-diaza-spiro[3.5]non-6-en-6-yl)-phenyl]-2-oxo-oxazolidin-5(S)-ylmethyl}-acetamide 
     EXAMPLE 474 
     N-{3-[3-fluoro-4-(5-oxo-6-phenyl-5,6-dihydro-4H-[1,3,4]thiadiazin-2-yl)-phenyl]-2-oxo-oxazolidin-5(S)-ylmethyl}-acetamide 
     EXAMPLE 475 
     N-{3-[3-fluoro-4-(5-oxo-5,6-dihydro-4H-[1,3,4]thiadiazin-2-yl)-phenyl]-2-oxo-oxazolidin-5(S)-ylmethyl}-2-hydroxy-acetamide 
     EXAMPLE 476 
     N-{3-[3-fluoro-4-(5-oxo-5,6-dihydro-4H-[1,3,4]thiadiazin-2-yl)-phenyl]-2-oxo-oxazolidin-5(S)-ylmethyl}-3-oxo-butyramide 
     EXAMPLE 477 
     N-{3-[3-fluoro-4-(5-oxo-5,6-dihydro-4H-[1,3,4]thiadiazin-2-yl)-phenyl]-2-oxo-oxazolidin-5(S)-ylmethyl}-3-(4-fluoro-phenyl)-3-oxo-propionamide, 
     EXAMPLE 478 
     N-{3-[3-fluoro-4-(5-oxo-5,6-dihydro-4H-[1,3,4]thiadiazin-2-yl)-phenyl]-2-oxo-oxazolidin-5(S)-ylmethyl}-3-[4-(hydroxyimino-methyl)-phenyl]-acrylamide 
     EXAMPLE 479 
     N-{3-[3-fluoro-4-(5-oxo-5,6-dihydro-4H-[1,3,4]thiadiazin-2-yl)-phenyl]-2-oxo-oxazolidin-5(S)-ylmethyl}-3-[4-(methoxyimino-methyl)-phenyl]-acrylamide 
     EXAMPLE 480 
     N-{3-[4-(6,6-dimethyl-1,1,5-trioxo-1,4,5,6-tetrahydro-1 δ6 -[1,3,4]thiadiazin-2-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5(S)-ylmethyl}-acetamide 
     EXAMPLE 481 
     N-{3-[3-fluoro-4-(4-methyl-5-oxo-5,6-dihydro-4H-[1,3,4]thiadiazin-2-yl)-phenyl]-2-oxo-oxazolidin-5(S)-ylmethyl}-acetamide 
     EXAMPLE 482 
     N-{3-[3-fluoro-4-(5-oxo-6-propyl-5,6-dihydro-4H-[1,3,4]thiadiazin-2-yl)-phenyl]-2-oxo-oxazolidin-5(S)-ylmethyl}-acetamide 
     EXAMPLE 483 
     N-{3-[3-fluoro-4-(6-isopropyl-5-oxo-5,6-dihydro-4H-[1,3,4]thiadiazin-2-yl)-phenyl]-2-oxo-oxazolidin-5(S)-ylmethyl}-acetamide 
     EXAMPLE 484 
     N-{3-[3-fluoro-4-(6-fluoro-5-oxo-5,6-dihydro-4H-[1,3,4]thiadiazin-2-yl)-phenyl]-2-oxo-oxazolidin-5(S)-ylmethyl}-acetamide 
     EXAMPLE 485 
     N-{3-[3-fluoro-4-(6-hydroxymethyl-5-oxo-5,6-dihydro-4H-[1,3,4]thiadiazin-2-yl)-phenyl]-2-oxo-oxazolidin-5(S)-ylmethyl}-acetamide 
     EXAMPLE 486 
     N-{3-[3-fluoro-4-(6-(2-hydroxy-ethyl)-5-oxo-5,6-dihydro-4H-[1,3,4]thiadiazin-2-yl)-phenyl]-2-oxo-oxazolidin-5(S)-ylmethyl}-acetamide 
     EXAMPLE 487 
     N-(3-{3-fluoro-4-(6-(4-hydroxy-phenyl)-5-oxo-5,6-dihydro-4H-[1,3,4]thiadiazin-2-yl]-phenyl}-2-oxo-oxazolidin-5(S)-ylmethyl)-acetamide 
     EXAMPLE 488 
     N-{3-[4-(6,6-dimethyl-1,5-dioxo-1,4,5,6-tetrahydro-1 δ4 -[1,3,4]-thiadiazin-2-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5(S)-ylmethyl}-acetamide 
     EXAMPLE 489 
     N-[[(5S)-3-[4-(3,4-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]-2,2,2-trifluoroacetamide 
     EXAMPLE 490 
     N-[[(5S)-3-[4-(3,4-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 
     EXAMPLE 491 
     N-[[(5S)-3-[4-(3,4-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]ethanethioamide 
     EXAMPLE 492 
     N-[[(5S)-3-[4-(3,4-dihydro-1-oxido-2H-thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 
     EXAMPLE 493 
     N-[[(5S)-3-[4-(3,4-dihydro-1,1-dioxido-2H-thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 
     EXAMPLE 494 
     N-[[(5S)-3-[4-(3,4-dihydro-1-oxido-2H-thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]ethanethioamide, 
     EXAMPLE 495 
     N-[[(5S)-3-[4-(2,3-dihydro-1,1-dioxido-4H-1,4-thiazin-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 
     EXAMPLE 496 
     N-[[(5S)-3-[4-(2,3-dihydro-1,1-dioxido-4H-1,4-thiazin-4-yl)-3,5-difluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 
     EXAMPLE 497 
     N-[[(5S)-3-[4-(3,4-dihydro-1,1-dioxido-2H-thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]-2,2-difluoroacetamide 
     EXAMPLE 498 
     N-[[(5S)-3-[4-(3,4-dihydro-1,1-dioxido-2H-thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]-2,2-difluoroethanethioamide 
     EXAMPLE 499 
     2,2-Dichloro-N-[[(5S)-3-[4-(3,4-dihydro-1,1-dioxido-2H-thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 
     EXAMPLE 500 
     N-[[(5S)-3-[4-(3,4-dihydro-4-hydroxy-1,1-dioxido-2H-thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 
     EXAMPLE 501 
     N-[[(5S)-3-[3-Fluoro-4-(4-fluoro-3,4-dihydro-1,1-dioxido-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 
     EXAMPLE 502 
     N-[[(5S)-3-[4-(3,4-dihydro-1,1-dioxido-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 
     EXAMPLE 503 
     N-[[(5S)-3-[4-(3,4-dihydro-1,1-dioxido-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-2,2-difluoroacetamide, 
     EXAMPLE 504 
     2,2-dichloro-N-[[(5S)-3-[4-(3,4-dihydro-1,1-dioxido-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 
     EXAMPLE 505 
     [[(5S)-3-[4-(3,4-dihydro-1,1-dioxido-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-2,2-difluoroethanethioamide 
     EXAMPLE 506 
     N-[[(5S)-3-[4-(3,4-dihydro-1,1-dioxido-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]propionamide 
     EXAMPLE 507 
     N-[[(5S)-3-[4-(3,4-dihydro-1,1-dioxido-2H-thiopyran-4-yl)-3,5-difluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 
     EXAMPLE 508 
     N-[[(5S)-3-[4-(2,3-dihydro-1,1-dioxido-4H-1,4-thiazin-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]-2,2-difluoroethanethioamide 
     EXAMPLE 509 
     2,2-dichloro-N-[[(5S)-3-[4-(2,3-dihydro-1,1-dioxido-4H-1,4-thiazin-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 
     EXAMPLE 510 
     N-[[(5S)-3-[4-(2,3-dihydro-1,1-dioxido-4H-1,4-thiazin-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]-2,2-difluoroacetamide 
     EXAMPLE 511 
     N-[[(5S)-3-[4-(2,3-dihydro-1,1-dioxido-4H-1,4-thiazin-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-2,2-difluoroethanethioamide 
     EXAMPLE 512 
     2,2-dichloro-N-[[(5S)-3-[4-(2,3-dihydro-1,1-dioxido-4H-1,4-thiazin-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 
     EXAMPLE 513 
     N-[[(5S)-3-[4-(2,3-dihydro-111-dioxido-4H-1,4-thiazin-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-2,2-difluoroacetamide 
     EXAMPLE 514 
     N-[[(5S)-3-[4-(2,3-Dihydro-1,1-dioxido-4H-1,4-thiazin-4-yl)-3,5-difluorophenyl]-2-oxo-5-oxazolidinyl]methyl]-2,2-difluoroethanethioamide 
     EXAMPLE 515 
     2,2-dichloro-N-[[(5S)-3-[4-(2,3-dihydro-1,1-dioxido-4H-1,4-thiazin-4-yl)-3,5-difluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide, or 
     EXAMPLE 516 
     N-[[(5S)-3-[4-(2,3-dihydro-1,1-dioxido-4H-1,4-thiazin-4-yl)-3,5-difluorophenyl]-2-oxo-5-oxazolidinyl]methyl]-2,2-difluoroacetamide 
     EXAMPLE 517 
     N-[[(5S)-3-[4-(2,3-dihydro-1,1-dioxido-4H-1,4-thiazin-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 
     EXAMPLE 518 
     2,2-dichloro-N-[[(5S)-3-[4-(3,4-dihydro-1,1-dioxido-2H-thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 
     EXAMPLE 519 
     2,2-dichloro-N-[[(5S)-3-[4-(3,4-dihydro-1,1-dioxido-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 
     EXAMPLE 520 
     2,2-dichloro-N-[[(5S)-3-[4-(2,3-dihydro-1,1-dioxido-4H-1,4-thiazin-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 
     EXAMPLE 521 
     2,2-dichloro-N-[[(5S)-3-[4-(2,3-dihydro-1,1-dioxido-4H-1,4-thiazin-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 
     EXAMPLE 522 
     N-[[(5S)-3-[4-(2,3-dihydro-1,1-dioxido-4H-1,4-thiazin-4-yl)-3,5-difluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 
     EXAMPLE 523 
     N-[[(5S)-3-[4-(3,4-dihydro-1,1-dioxido-2H-thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]-2,2-difluoroacetamide 
     EXAMPLE 524 
     N-[[(5S)-3-[4-(3,4-dihydro-1,1-dioxido-2H-thiopyran-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]-2,2-difluoroethanethioamide 
     EXAMPLE 525 
     N-[[(5S)-3-[4-(3,4-dihydro-1,1-dioxido-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-2,2-difluoroacetamide 
     EXAMPLE 526 
     N-[[(5S)-3-[4-(2,3-dihydro-1,1-dioxido-4H-1,4-thiazin-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]-2,2-difluoroethanethioamide 
     EXAMPLE 527 
     N-[[(5S)-3-[4-(2,3-dihydro-1,1-dioxido-4H-1,4-thiazin-4-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]-2,2-difluoroacetamide 
     EXAMPLE 528 
     N-[[(5S)-3-[4-(2,3-dihydro-1,1-dioxido-4H-1,4-thiazin-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-2,2-difluoroethanethioamide, or 
     EXAMPLE 529 
     2,2-dichloro-N-[[(5S)-3-[4-(2,3-dihydro-1,1-dioxido-4H-1,4-thiazin-4-yl)-3,5-difluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide, 
     EXAMPLE 530 
     (S)-N-[[3-[3-fluoro-4-(1,2,3,4,6,7-hexahydro-5-oxo-1,4-diazepin-1-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 
     EXAMPLE 531 
     (S)-N-[[3-[3-fluoro-4-(1,2,3,4,6,7-hexahydro-5-oxo-1,4-diazepin-1-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]thioacetamide 
     EXAMPLE 532 
     (S)-N-[[3-[3-fluoro-4-(1,2,3,4,6,7-hexahydro-4-methyl-5-oxo-1,4-diazepin-1-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide, or 
     EXAMPLE 533 
     (S)-N-[[3-[3-fluoro-4-(1,2,3,4,6,7-hexahydro-4-methyl-5-oxo-1,4-diazepin-1-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]thioacetamide 
     EXAMPLE 534 
     N-[[(5S)-3-[3-fluoro-4-[tetrahydro-1,1-dioxido-2-(2-propenyl)-2H-1,2-thiazin-4-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 
     EXAMPLE 535 
     N-[[(5S)-3-[3-fluoro-4-(tetrahydro-1,1-dioxido-2H-1,2-thiazin-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 
     EXAMPLE 536 
     N-[[(5S)-3-[3-fluoro-4-(tetrahydro-1,1-dioxido-2H-1,2-thiazin-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]ethanethioamide 
     EXAMPLE 537 
     N-[[(5S)-3-[-fluoro-4-(tetrahydro-2-methyl-1,1-dioxido-2H-1,2-thiazin-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]ethanethioamide 
     EXAMPLE 538 
     N-[[(5S)-3-[4-(2,2-dioxido-1,2-oxathian-5-yl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]ethanethioamide, 
     EXAMPLE 539 
     N-[[(5S)-3-[4-(1,1-dioxido-4-isothiazolidinyl)-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]ethanethioamide, or 
     EXAMPLE 540 
     N-[[(5S)-3-[3-fluoro-4-(tetrahydro-2-methyl-1,1-dioxido-2H-1,2-thiazin-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 
     EXAMPLE 541 
     N-({(5S)-3-[(2R)-1-(2-fluoroethyl)-2-methyl-2,3-dihydro-1H-indol-5-yl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide 
     EXAMPLE 542 
     N-{[(5S)-3-((2R)-1-glycoloyl-2-methyl-2,3-dihydro-1H-indol-5-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide 
     EXAMPLE 543 
     N-({(5S)-3-[(2R)-1-glycoloyl-2-methyl-2,3-dihydro-1H-indol-5-yl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide 
     EXAMPLE 544 
     N-({(5S)-3-[(2R)-1-formyl-2-methyl-2,3-dihydro-1H-indol-5-yl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide 
     EXAMPLE 545 
     N-({(5S)-3-[(2R)-1-formyl-2-methyl-2,3-dihydro-1H-indol-5-yl]-2-oxo-1,3-oxazolidin-5-yl}methyl)propanamide 
     EXAMPLE 546 
     N-({(5S)-3-[(2R)-1-formyl-2-methyl-2,3-dihydro-1H-indol-5-yl]-2-oxo-1,3-oxazolidin-5-yl}methyl)ethanethioamide 
     EXAMPLE 547 
     N-({(5S)-3-[(2R)-1-(2-methoxyacetyl)-2-methyl-2,3-dihydro-1H-indol-5-yl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide 
     EXAMPLE 548 
     N-({(5S)-3-[(2R)-1-acetyl-2-methyl-2,3-dihydro-1H-indol-5-yl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide 
     EXAMPLE 549 
     N-[((5S)-3-{(2R)-2-methyl-1-[(methylamino)carbothioyl]-2,3-dihydro-1H-indol-5-yl}-2-oxo-1,3-oxazolidin-5-yl)methyl]acetamide 
     EXAMPLE 550 
     N-({(5S)-3-[(2R)-1-glycoloyl-2-methyl-2,3-dihydro-1H-indol-5-yl]-2-oxo-1,3-oxazolidin-5-yl}methyl)ethanethioamide 
     EXAMPLE 551 
     N-{[(5S)-3-[(2R)-1-formyl-2-methyl-1,2,3,4-tetrahydro-6-quinolinyl]-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide 
     EXAMPLE 552 
     N-{[(5S)-3-[(2R)-1-glycoloyl-2-methyl-1,2,3,4-tetrahydro-6-quinolinyl]-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide 
     EXAMPLE 553 
     N-({(5S)-3-[(2R)-1-formyl-2-methyl-1,2,3,4-tetrahydro-6-quinolinyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide 
     EXAMPLE 554 
     N-({(5S)-3-[(2R)-1-formyl-2-methyl-1,2,3,4-tetrahydro-6-quinolinyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)ethanethioamide 
     EXAMPLE 555 
     N-{[(5S)-3-[(3R) 4 -Formyl-3-methyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl]-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide 
     EXAMPLE 556 
     N-({(5S)-3-[(3R)-4-Formyl-3-methyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide 
     EXAMPLE 557 
     N-({(5S)-3-[(3R)-4-Formyl-3-methyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl]-2-oxo-1,3-oxazolidin-5-yl}methyl)ethanethioamide 
     EXAMPLE 558 
     N-({(5S)-3-[(2R) 2 -(fluoromethyl)-1-formyl-2,3-dihydro-1H-indol-5-yl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide 
     EXAMPLE 559 
     N-{[(5R)-3-(2(+)-methyl-2,3-dihydro-1-benzothien-5-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide, or 
     EXAMPLE 560 
     N-[[(5S)-3-[2-(1,1-dimethylethyl)-1-formyl-2,3-dihydro-1H-indol-5-yl]-2-oxo-5-oxazolidinyl]methyl]ethanethioamide 
     EXAMPLE 561 
     N-{[(5S)-3-(1-Methyl-2,2-dioxo-2,3-dihydro-1H-2,1-benzisothiazol-5-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide 
     EXAMPLE 562 
     N-({(5S)-3-[1-(2-Fluoroethyl)-2,2-dioxo-2,3-dihydro-1H-2,1-benzisothiazol-5-yl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide 
     EXAMPLE 563 
     N-({(5S)-3-[1-(2-Nitriloethyl)-2,2-dioxo-2,3-dihydro-1H-2,1-benzisothiazol-5-yl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide 
     EXAMPLE 564 
     N-({(5S)-3-[1-(2-Methoxyethyl)-2,2-dioxo-2,3-dihydro-1H-2,1-benzisothiazol-5-yl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide, or 
     EXAMPLE 565 
     N-({(5S)-3-[1-(2-Fluoroethyl)-2,2-dioxo-2,3-dihydro-1H-2,1-benzisothiazol-5-yl]-2-oxo-1,3-oxazolidin-5-yl}methyl)ethanethioamide 
     EXAMPLE 566 
     (−)-N-[[(5S)-3-[2-formyl-1,2,3,4-tetrahydro-6-isoquinolinyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 
     EXAMPLE 567 
     (−)-N-[[(5S)-3-[2-[(acetyloxy)acetyl]-1,2,3,4-tetrahydro-6-isoquinolinyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 
     EXAMPLE 568 
     (−)-N-[[(5S)-3-[2-[(hydroxy)acetyl]-1,2,3,4-tetrahydro-6-isoquinolinyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 
     EXAMPLE 569 
     (+)-N-[[(5S)-3-[2-formyl-1,2,3,4-tetrahydro-6-isoquinolinyl]-2-oxo-5-oxazolidinyl]methyl]ethanethioamide, or 
     EXAMPLE 570 
     (+)-N-[[(5S)-3-[2-[(hydroxy)acetyl]-1,2,3,4-tetrahydro-6-isoquinolinyl]-2-oxo-5-oxazolidinyl]methyl]ethanethioamide 
     EXAMPLE 571 
     (+)-N-[[(5S)-3-[2-formyl-1,2,3,4-tetrahydro-7-isoquinolinyl]-2-oxo-5-oxazolidinyl]methyl]ethanethioamide, or 
     EXAMPLE 572 
     (+)-N-[[(5S)-3-[2-[(hydroxy)acetyl]-1,2,3,4-tetrahydro-7-isoquinolinyl]-2-oxo-5-oxazolidinyl]methyl]ethanethioamide 
     EXAMPLE 573 
     (−)-N-[[(5S)-3-(3,4-dihydro-1H-2-benzopyran-6-yl)-2-oxo-5-oxazolidinyl]methyl]acetamide 
     EXAMPLE 574 
     (+)-N-[[(5S)-3-(3,4-dihydro-1H-2-benzopyran-6-yl)-2-oxo-5-oxazolidinyl]methyl]ethanethioamide 
     EXAMPLE 575 
     (−)-N-[[(5S)-3-(3,4-dihydro-1H-2-benzothiopyran-6-yl)-2-oxo-5-oxazolidinyl]methyl]acetamide 
     EXAMPLE 576 
     (+)-N-[[(5S)-3-(3,4-dihydro-1H-2-benzothiopyran-6-yl)-2-oxo-5-oxazolidinyl]methyl]ethanethioamide, or 
     EXAMPLE 577 
     (+)-N-[[(5S)-3-(3,4-dihydro-2,2-dioxido-1H-2-benzothiopyran-6-yl)-2-oxo-5-oxazolidinyl]methyl]ethanethioamide 
     EXAMPLE 578 
     (+)-N-[[(5S)-3-(3,4-dihydro-1H-2-benzopyran-7-yl)-2-oxo-5-oxazolidinyl]methyl]ethanethioamide 
     EXAMPLE 579 
     (−)-N-[[(5S)-3-(3,4-dihydro-1H-2-benzothiopyran-7-yl)-2-oxo-5-oxazolidinyl]methyl]acetamide 
     EXAMPLE 580 
     (+)-N-[[(5S)-3-(3,4-dihydro-1H-2-benzothiopyran-7-yl)-2-oxo-5-oxazolidinyl]methyl]ethanethioamide 
     EXAMPLE 581 
     (+)-N-[[(5S)-3-(3,4-dihydro-2,2-dioxido-1H-2-benzothiopyran-7-yl)-2-oxo-5-oxazolidinyl]methyl]ethanethioamide, or 
     EXAMPLE 582 
     N-[[(5S)-3-(3,4-dihydro-2-oxido-1H-2-benzothiopyran-7-yl)-2-oxo-5-oxazolidinyl]methyl]acetamide, 
     EXAMPLE 583 
     N-{[(5S)-3-(3-formyl-1,2,4,5-tetrahydro-1H-3-benzazepin-7-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide 
     EXAMPLE 584 
     N-{[(5S)-3-(3-glycoloyl-1,2,4,5-tetrahydro-1H-3-benzazepin-7-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide 
     EXAMPLE 585 
     N-{[(5S)-3-(3-glycoloyl-1,2,4,5-tetrahydro-1H-3-benzazepin-7-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl}ethanethioamide 
     EXAMPLE 586 
     N-{[(5S)-3-(3-acetyl-1,2,4,5-tetrahydro-1H-3-benzazepin-7-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide 
     EXAMPLE 587 
     N-{[(5S)-3-(3-benzoyl-1,2,4,5-tetrahydro-1H-3-benzazepin-7-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide 
     EXAMPLE 588 
     N-({(5S)-3-[3-(5-amino-1,3,4-thiadiazol-2-yl)-1,2,4,5-tetrahydro-1H-3-benzazepin-7-yl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide 
     EXAMPLE 589 
     N-({(5S)-3-[3-(methylsulfonyl)-1,2,4,5-tetrahydro-1H-3-benzazepin-7-yl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide 
     EXAMPLE 590 
     N-({(5S)-3-[3-(5-methylthio-1,3,4-thiadiazol-2-yl)-1,2,4,5-tetrahydro-1H-3-benzazepin-7-yl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide 
     EXAMPLE 591 
     N-({(5S)-3-[3-(5-methyl-1,3,4-thiadiazol-2-yl)-1,2,4,5-tetrahydro-1H-3-benzazepin-7-yl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide 
     EXAMPLE 592 
     N-[((5S)-3-{3-(phenyl)acetyl-1,2,4,5-tetrahydro-1H-3-benzazepin-7-yl}-2-oxo-1,3-oxazolidin-5-yl)methyl]acetamide 
     EXAMPLE 593 
     N-[((5S)-3-{3-[5-(formylamino)-1,3,4-thiadiazol-2-yl]-1,2,4,5-tetrahydro-1H-3-benzazepin-7-yl}-2-oxo-1,3-oxazolidin-5-yl)methyl]acetamide 
     EXAMPLE 594 
     N-[5-(7-{(5S)-5-[(acetylamino)methyl]-2-oxo-1,3-oxazolidin-3-yl}-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl)-1,3,4-thiadiazol-2-yl]-2-hydroxyacetamide 
     EXAMPLE 595 
     N-[((SS)-3-{3-[(4-iodophenyl)acetyl]-1,2,4,5-tetrahydro-1H-3-benzazepin-7-yl}-2-oxo-1,3-oxazolidin-5-yl)methyl]acetamide 
     EXAMPLE 596 
     N-[((5S)-3-{3-[(3-trifluoromethyl)phenyl)acetyl]-1,2,4,5-tetrahydro-1H-3-benzazepin-7-yl}-2-oxo-1,3-oxazolidin-5-yl)methyl]acetamide 
     EXAMPLE 597 
     N-[((5S)-3-{3-[(4-trifluoromethyl)phenyl)acetyl]-1,2,4,5-tetrahydro-1H-3-benzazepin-7-yl}-2-oxo-1,3-oxazolidin-5-yl)methyl]acetamide 
     EXAMPLE 598 
     N-({(5S)-2-oxo-3-[3-(5-oxopentanoyl)-1,2,4,5-tetrahydro-1H-3-benzazepin-7-yl]-1,3-oxazolidin-5-yl}methyl)acetamide 
     EXAMPLE 599 
     N-({(5S)-2-oxo-3-[3-(5-oxohexanoyl)-1,2,4,5-tetrahydro-1H-3-benzazepin-7-yl]-1,3-oxazolidin-5-yl}methyl)acetamide 
     EXAMPLE 600 
     N-[{(5S)-3-(2-formyl-1,3,4,5-tetrahydro-1H-2-benzazepin-7-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide 
     EXAMPLE 601 
     N-{[(5S)-3-(2-glycoloyl-1,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide 
     EXAMPLE 602 
     N-{[(5S)-3-(2-acetyl-1,3,4,5-tetrahydro-1H-2-benzazepin-7-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide 
     EXAMPLE 603 
     7-{(5S)-5-[(acetylamino)methyl]-2-oxo-1,3-oxazolidin-3-yl}-N-phenyl-1,3,4,5-tetrahydro-2H-2-benzazepine-2-carboxamide 
     EXAMPLE 604 
     N-{[(5S)-3-(1-formyl-2,3,4,5-tetrahydro-1H-1-benzazepin-7-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide 
     EXAMPLE 605 
     N-{[(SS)-3-(1-formyl-2,3,4,5-tetrahydro-1H-1-benzazepin-7-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl}ethanethioamide 
     EXAMPLE 606 
     N-[[(5S)-2-oxo-3-(1,2,4,5-tetrahydro-3-benzothiepin-7-yl)-5-oxazolidinyl]methyl]acetamide 
     EXAMPLE 607 
     N-[[(5S)-2-oxo-3-(1,2,4,5-tetrahydro-3,3-dioxido-3-benzothiepin-7-yl)-5-oxazolidinyl]methyl]acetamide 
     EXAMPLE 608 
     N-[[(5S)-2-oxo-3-(1,2,4,5-tetrahydro-3-benzothiepin-7-yl)-5-oxazolidinyl]methyl]ethanethioamide 
     EXAMPLE 609 
     N-[[(5S)-2-oxo-3-(1,2,4,5-tetrahydro-3,3-dioxido-3-benzothiepin-7-yl)-5-oxazolidinyl]methyl]ethanethioamide 
     EXAMPLE 610 
     N-({(5S)-3-[3-fluoro-4-(1-imino-1-oxido-1 λ4 ,4-thiazinan-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)ethanethioamide 
     EXAMPLE 611 
     N-({(5S)-3-[3-fluoro-4-(1-imino-1-oxido-1 λ4 ,4-thiazinan-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)propanecarbothioamide 
     EXAMPLE 612 
     N-({(5S)-3-[3-fluoro-4-(1-imino-1-oxido-1 λ4 ,4-thiazinan-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)cyclopropanecarbothioamide 
     EXAMPLE 613 
     N-({(5S)-3-[3-fluoro-4-(1-imino-1-oxidohexahydro-1 λ4 -thiopyran-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide (E)-isomer 
     EXAMPLE 614 
     N-({(5S)-3-[3-fluoro-4-(1-imino-1-oxidohexahydro-1 λ4 -thiopyran-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)ethanethioamide (E)-isomer 
     EXAMPLE 615 
     N-({(5S)-3-[3-fluoro-4-(1-imino-1-oxidohexahydro-1 λ4 -thiopyran-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)propanethioamide (E)-isomer 
     EXAMPLE 616 
     N-({(5S)-3-[3-fluoro-4-(1-imino-1-oxidohexahydro-1 λ4 -thiopyran-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)cyclopropanecarbothioamide (E)-isomer, 
     EXAMPLE 617 
     N-({(5S)-3-[3-fluoro-4-(1-imino-1-oxidohexahydro-1 λ4 -thiopyran-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide (Z)-isomer 
     EXAMPLE 618 
     N-({(5S)-3-[3-fluoro-4-(1-imino-1-oxidohexahydro-1 λ4 -thiopyran-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)ethanethioamide (Z)-isomer 
     EXAMPLE 619 
     N-({(5S)-3-[3-fluoro-4-(1-imino-1-oxidohexahydro-1 λ4 -thiopyran-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)propanethioamide (Z)-isomer 
     EXAMPLE 620 
     N-({(5S)-3-[3-fluoro-4-(1-imino-1-oxidohexahydro-1 λ4 -thiopyran-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)cyclopropanethioamide (Z)-isomer 
     EXAMPLE 621 
     N-({(5S)-3-[3-fluoro-4-[1-(acetylimino)-1-oxidohexahydro-1 λ4 -thiopyran-4-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide, Z-isomer 
     EXAMPLE 622 
     N-({(5S)-3-[3-fluoro-4-[1-(methylimino)-1-oxidohexahydro-1 λ4 -thiopyran-4-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)propanethioamide, Z-isomer 
     EXAMPLE 623 
     N-({(5S)-3-[3-fluoro-4-[1-(acetylimino)-1-oxidohexahydro-1 λ4 -thiopyran-4-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)propanethioamide, Z-isomer 
     EXAMPLE 624 
     N-({(5S)-3-[3-fluoro-4-[1-(ethylimino)-1-oxidohexahydro-1 λ4 -thiopyran-4-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)propanethioamide, Z-isomer, 
     EXAMPLE 625 
     N-({(5S)-3-[3-fluoro-4-[1-[(phenylmethyl)imino]-1-oxidohexahydro-1 λ4 -thiopyran-4-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)propanethioamide, Z-isomer 
     EXAMPLE 626 
     N-({(5S)-3-[3-fluoro-4-[1-[(3-phenylpropyl)imino]-1-oxidohexahydro-1 λ4 -thiopyran-4-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)propanethioamide, Z-isomer 
     EXAMPLE 627 
     N-({(5S)-3-[3-fluoro-4-(1-{([(methylamino)carbonyl]imino}-1-oxidohexahydro-1 λ4 -thiopyran-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)propanethioamide, Z-isomer 
     EXAMPLE 628 
     N-({(5S)-3-[3-fluoro-4-(1-[(methoxycarbonyl)imino]-1-oxidohexahydro-1 λ4 -thiopyran-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)propanethioamide, Z-isomer 
     EXAMPLE 629 
     N-({(5S)-3-[3-fluoro-4-(1-[[(ethoxycarbonyl)methyl]imino]-1-oxidohexahydro-1 λ4 -thiopyran-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)propanethioamide, Z-isomer 
     EXAMPLE 630 
     N-({(5S)-3-[3-fluoro-4-(1-{[[(4-nitrophenyl)amino]carbonyl]imino}-1-oxidohexahydro-1 λ4 -thiopyran-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)propanethioamide, Z-isomer 
     EXAMPLE 631 
     N-({(5S)-3-[3-fluoro-4-[1-[(aminocarbonyl)imino]-1-oxidohexahydro-1 λ4 -thiopyran-4-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)propanethioamide, Z-isomer 
     EXAMPLE 632 
     N-({(5S)-3-[3-fluoro-4-[1-[[(aminocarbonyl)methyl]imino]-1-oxidohexahydro-1 λ4 -thiopyran-4-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)propanethioamide, Z-isomer 
     EXAMPLE 633 
     N-({(5S)-3-[3-fluoro-4-[1-[(2-hydroxyethyl) imino]-1-oxidohexahydro-1 λ4 -thiopyran-4-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)propanethioamide, Z-isomer 
     EXAMPLE 634 
     N-[((5S)-3-{3-fluoro-4-[1-(methylimino)-1-oxido-1 λ4 ,4-thiazinan-4-yl]phenyl}-2-oxo-1,3-oxazolidin-5-yl)methyl]propanethioamide 
     EXAMPLE 635 
     N-[((5S)-3-{3-fluoro-4-[1-(methylimino)-1-oxido-1 λ4 ,4-thiazinan-4-yl]phenyl}-2-oxo-1,3-oxazolidin-5-yl) methyl]cyclopropanecarbothioamide 
     EXAMPLE 636 
     N-[((5S)-3-{3-fluoro-4-(1-[(methoxycarbonyl)imino]-1-oxido-1 λ4 ,4-thiazinan-4-yl)phenyl}-2-oxo-1,3-oxazolidin-5-yl)methyl]propanethioamide 
     EXAMPLE 637 
     N-[((5S)-3-{3-fluoro-4-(1-[(methoxycarbonyl)imino]-1-oxido-1 λ4 ,4-thiazinan-4-yl)phenyl}-2-oxo-1,3-oxazolidin-5-yl)methyl]cyclopropanecarbothioamide 
     EXAMPLE 638 
     N-({(5S)-3-[3-fluoro-4-[1-(methylimino)-1-oxidohexahydro-1 λ4 -thiopyran-4-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)cyclopropanecarbothioamide, Z-isomer 
     EXAMPLE 639 
     N-[((5S)-3-{3-fluoro-4-[1-[(methoxycarbonyl)imino]-1-oxidohexahydro-1-thiopyran-4-yl]phenyl}-2-oxo-1,3-oxazolidin-5-yl)methyl]cyclopropanecarbothioamide, Z-isomer 
     EXAMPLE 640 
     N-[((5S)-3-{3-fluoro-4-[1-(methylimino)-1-oxidohexahydro-1 λ4 -thiopyran-4-yl]phenyl}-2-oxo-1,3-oxazolidin-5-yl)methyl]cyclopropanecarbothioamide, E-isomer 
     EXAMPLE 641 
     N-[((5S)-3-{3-fluoro-4-[1-(methylimino)-1-oxidohexahydro-1 λ4 -thiopyran-4-yl]phenyl}-2-oxo-1,3-oxazolidin-5-yl)methyl]propanethioamide, E-isomer 
     EXAMPLE 642 
     N-[((5S)-3-{3-fluoro-4-[1-[[(phenylmethoxy)carbnonyl]imino]-1-oxidohexahydro-1 λ4 -thiopyran-4-yl]phenyl}-2-oxo-1,3-oxazolidin-5-yl)methyl]acetamide, Z-isomer 
     EXAMPLE 643 
     N-({(5S)-3-[3-Fluoro-4-(1-{[(benzylamino)carbonyl]imino}-1-oxidohexahydro-1 λ4 -thiopyran-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide, Z-isomer 
     EXAMPLE 644 
     N-{[(5S)-3-(3-fluoro-4-{4-[2-(methylsulfinyl)acetyl]-1-piperazinyl}phenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}propanethioamide 
     EXAMPLE 645 
     N-{[(5S)-3-(3-fluoro-4-{4-[2-(methylsulfanyl)acetyl]-1-piperazinyl}phenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}propanethioamide 
     EXAMPLE 646 
     N-{[(5S)-3-(3-fluoro-4-{4-[2-(methylsulfonyl)acetyl]-1-piperazinyl}phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl}propanethioamide 
     EXAMPLE 647 
     N-({(5S)-3-[4-(4-ethanethiolyl-1-piperazinyl)-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)propanethioamide 
     EXAMPLE 648 
     N-({(5S)-3-[4-(4-cyano-1-piperazinyl)-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)propanethioamide 
     EXAMPLE 649 
     N-({(5S)-3-(3-fluoro-4-{4-[2-(methylaminocarbonyloxy)acetyl]-1-piperazinyl}phenyl)-2-oxo-1,3-oxazolidin-5-yl}methyl)propanethioamide 
     EXAMPLE 650 
     N-({(5S)-3-(3-fluoro-4-{4-[2-[(2-methoxyethoxy)carbonyloxy]acetyl]-1-piperazinyl}phenyl)-2-oxo-1,3-oxazolidin-5-yl}methyl)propanethioamide 
     EXAMPLE 651 
     N-[((5S)-3-{3-fluoro-4-[4-((2S)-2-hydroxy-3-methoxypropanoyl)-1-piperazinyl]phenyl}-2-oxo-1,3-oxazolidin-5-yl)methyl]propanethioamide 
     EXAMPLE 652 
     N-[((5S)-3-{3-fluoro-4-[4-((2S)-2,3-dimethyoxypropanoyl)-1-piperazinyl]phenyl}-2-oxo-1,3-oxazolidin-5-yl)methyl]propanethioamide 
     EXAMPLE 653 
     N-[((5S)-3-{3-fluoro-4-[4-((2S)-3-hydroxy-2-methyoxypropanoyl)-1-piperazinyl]phenyl}-2-oxo-1,3-oxazolidin-5-yl)methyl]propanethioamide 
     EXAMPLE 654 
     N-({(5S)-3-[3-fluoro-4-(4-acetoacetyl-1-piperazinyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)propanethioamide 
     EXAMPLE 655 
     N-({(5S)-3-[3-fluoro-4-(4-pyruvoyl-1-piperazinyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)propanethioamide 
     EXAMPLE 656 
     N-({(5S)-3-[3-fluoro-4-[4-(3-hydroxypropanoyl)-1-piperazinyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl]propanethioamide 
     EXAMPLE 657 
     N-{[(5S)-3-(3-fluoro-4-{4-[(1-hydroxycyclopropyl)carbonyl]-1-piperazinyl}phenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}propanethioamide 
     EXAMPLE 658 
     N-[((5S)-3-{3-fluoro-4-[4-(2-phenoxyacetyl)-1-piperazinyl]phenyl}-2-oxo-1,3-oxazolidin-5-yl)methyl]propanethioamide 
     EXAMPLE 659 
     N-({(5S)-3-[3-fluoro-4-[4-((2S)-2,3-dihydroxypropanoyl)-1-piperazinyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)propanethioamide 
     EXAMPLE 660 
     N-({(5S)-3-[3-fluoro-4-[4-((2R)-2,3-dihydroxypropanoyl)-1-piperazinyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)propanethioamide 
     EXAMPLE 661 
     N-{[(5S)-3-(3-fluoro-4-{4-[3-hydroxy-2-(hydroxymethyl)-2-methylpropanoyl]-1-piperazinyl}phenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}propanethioamide 
     EXAMPLE 662 
     N-[((5S)-3-{3-fluoro-4-[4-((2S)-2-hydroxy-3-phenylpropanoyl)-1-piperazinyl]phenyl}-2-oxo-1,3-oxazolidin-5-yl)methyl]propanethioamide 
     EXAMPLE 663 
     N-[((5S)-3-{3-fluoro-4-[4-((2R)-2-hydroxy-3-phenylpropanoyl)-1-piperazinyl]phenyl}-2-oxo-1,3-oxazolidin-5-yl) methyl]propanethioamide 
     EXAMPLE 664 
     N-[((5S)-3-{3-fluoro-4-[4-((2R)-2-hydroxy-2-phenylacetyl)-1-piperazinyl]phenyl}-2-oxo-1,3-oxazolidin-5-yl)methyl]propanethioamide 
     EXAMPLE 665 
     N-[((5S)-3-{3-fluoro-4-[4-((2S)-2-acetoxy-2-phenylacetyl)-1-piperazinyl]phenyl}-2-oxo-1,3-oxazolidin-5-yl)methyl]propanethioamide 
     In order to more fully illustrate the nature of the invention and the manner of practicing the same, the following synthesis Example is presented. 
     SYNTHESIS EXAMPLE 
     2-{(3-[Acetyl({(5S)-3-[4-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-3-fluorophenyl]-2-oxo-1,3-oxazolidin 5-yl}methyl)amino]-1,1-dimethyl-3-oxopropyl}-3,5-dimethylphenyl Dihydrogen Phosphate. 
     Step 1. 
                        
 
A stirred mixture of 2 (0.57 g, 1.18 mmol) (M. G. Nicolaou, C. -S. Yuan and R. T. Borchardt,  J. Org. Chem.  1996, 61, 8636-8641), 3 (0.45 g, 1.19 mmol) (Case 6118.N CN1, Example 11, Step 1) and triethylamine (0.8 ml) in CH 2 Cl 2  (60 ml), under nitrogen was cooled in an ice bath and treated with bis (2-oxo-3-oxazolidinyl)phosphinic chloride (0.456 g, 1.79 mmol). It was kept in the ice bath for 45 min and at ambient temperature (24° C.) for 2 h 15 min and then concentrated in vacuo. The residue was mixed with EtOAc and washed with 5% aqueous citric acid and brine, dried (MgSO 4 ) and concentrated. Chromatography of the residue on silica gel with 2.5% MeOH—CH 2 Cl 2  gave 0.88 g of 4:  1 H NMR (300 MHz, CDCl 3 ) δ 1.61, 1.65 (s, s, 6H), 2.08 (s, 3H), 2.15 (m, 2H), 2.37 (m, 2H), 2.48 (s, 3H), 2.56 (m, 2H), 3.13 (m, 6H), 3.35 (m, 3H), 4.28 (m, 1H), 5.12 (m, 4H), 6.66 (s, 1H), 6.98 (s, 1H), 7.13 (m, 3H), 7.36 (m, 11H); MS (ESI) m/z 807 (M+H + ), 829 (M+Na + ).
 
     Step 2. 
                        
 
A stirred solution of 4 (0.85 g, 1.05 mmol) in methyl trimethylsilylcarbamate (3 ml), under nitrogen was treated, dropwise with acetyl chloride (0.25 ml, 3.5 mmol) and kept at ambient temperature (24° C.) for 3.5 h. It was then diluted with pentane to give a gum. The liquid was decanted and the residue was trituratred twice with pentane and once with Et 2 O to give a semisolid material that was chromatographed on silica gel with 30% EtOAc —CH 2 Cl 2 . The product amounted to 0.62 g of 5:  1 H NMR (300 MHz, CDCl 3 ) δ 1.55 (s, 3H), 1.62 (s, 3H), 2.16 (s, 3H), 2.20 (m, 1H), 2.23 (s, 3H), 2.42 (m, 2H), 2.57 (s, 3H), 3.17 (m, 5H), 3.52 (m, 5H), 3.87 (m, 2H), 4.61 (m, 1H), 5.05 (m, 4H), 6.79 (s, 1H), 6.98 (s, 1H), 7.11 (dd, 1H), 7.28 (m, 11H), 7.42 (dd, 1H); HRMS (FAB) calcd for C 44 H 51 FN 2 O 10 PS (M+H + ), 849.2986, found 849.2988.
 
     Step 3. 
                        
 
A mixture of 5 (0.62 g), 10% palladium-on-carbon catalyst (0.16 g) and THF (20 ml) was hydrogenated at atmospheric pressure for 80 min, filtered through celite and concentrated in vacuo. The resulting foam was triturated with Et 2 O to give 0.419 g of 1, a white powder: mp 116-124° C. (dec); MS (ESI) m/z 627 (M+H + ), 649 (M+Na + ); HRMS (FAB) calcd for C 28 H 37 FN 2 O 9 PS (M+H + ) 627.1941, found 627.1947.
 
     Although the present invention has been exemplified using oxazolidinone compounds, it is understood that any amide-containing compound can be made more water-soluble using the present invention. Moreover, although the foregoing invention has been described in some detail by way of illustration and example for purposes of clarity and understanding, it would be apparent to those skilled in the art that certain changes and modifications could be made without departing from the scope and spirit of the present invention. As such, the description and example should not be construed as limiting the scope of the invention.

Technology Classification (CPC): 2