ANTIBACTERIAL QUINOLONE COMPOUNDS

Abstract: A quinolone compound of formula (I) as defined herein having antibacteria properties, pharmaceutical compositions containing the quinoline compound and method for treating bacterial infections in animals including humans.

Description: ANTIBACTERIAL QUIN0L0NE COMPOUNDS Background of the Invention The present invention relates to new quinolone compounds useful as antibacterial agents. Various quinolone type structures are known for their antibacterial properties, however new antibacterials are continually sought especially those which exhibit both gram positive and gram negative activity. Information Disclosure International Application Number PCT US87/02556 (International Publication Number WO 88/02627) discloses naphthyridine- and quino¬ line-carboxylic acids having a 1-tertiary-alkyl substituent, composi¬ tions containing them, and their use in treating bacterial infections in warm-blooded animals and man. 1-tertiar -alkyl substituents dis¬ closed include 1,1-dimethylethyl, 1,1-dimethylpropyl, 1-methyl-l- phenylethyl, 1-phenylcyclopropyl, 2-methyl-l-phenylcyclopropyl, 1- methylcyclopropyl, 1,2-dime hylcyclopropyl, 1-methylcyclobutyl, 1- methylethenyl and 1-adamantyl. There are disclosed numerous N- heterocyclic ring substitutents in the 7-position including piper- azinyl, piperidinyl, 3-amino-l-pyrrolidinyl, 3-aminoalkyl-l-pyrrolid- inyl, 2-aminoalkyl-morpholin-4-yl, 2-aminoalkyl-thimorpholin-4-yl, and diazabicycloalkyl groups containing 7-9 atoms in the diazobicyc- loalkyl ring system. Also disclosed are amines and intermediates used in the preparation of the naphthyridine- and quinoline-carboxylic acids. International Application Number PCT US87/02556 (International Publication Number WO 88/02627) describes additional background references including: R. Albrecht, Progress in Drug Research, 21:9-104 (1977); Egawa, et al., J. Med. Chem. 27:1543-1548 (1984); M.P. Wentland and J.B. Cornett, Annual Reports in Medicinal Chemistry, 20:145-154 (1985); U.S. Patent 3,590,036, 4,146,719, 4,284,629, 4,341,784, 4,352,803, 4,359,578, 4,556,658, 4,559,341, 4,559,342, 4,563,448, 4,571,396, 4,578,473, and 4,705,788; German Offen. DE 3142854; GB A 2,160,519 and GB A 937,183; EP 0, 132,845, EP 0,134,165, EP 0,153,163, EP 0,166,939, and EP 0,167,763; Spanish Patent 8504767; and South African Patent Application Publication No. 853954. At the 28th ICAAC (Interscience Conference on Antimicrobial Agents and Chemotherapy) held October 23-26, 1988 in Los Angeles, CA, the antibacterial activity of 7-(lR,4R-2,5-diazabicyclo-[2,2,l]- heptan-2-yl)-6-fluoro-l-t-butyl-l,4-dihydro-4-oxo-l,8-naphthyridine- 3-carboxylic acid (BMY 40062) was disclosed in poster abstracts (#962 and #963) . The synthesis and structure-activity relationships of related quinoline and naphthyridine carboxylic acids incorporating 1-tertiary- lkyl substituents is described by D. Bouzard, et al., in J. Med. Chem. 32:537-542 (1989). The synthesis and structure-activity relationships of various 1- aryl-6-fluoroquinolone, l-aryl-6-fluoronaphthyridine and l-aryl-6,8- difluoroquinolone antibacterial agents is described by D.T. Chu, et al., in J. Med. Chem. 28:1558-1564 (1985); J. Med. Chem. 29:2363- 2369 (1986); and J. Med Chem. 30:504-509 (1987). The synthesis of a variety of 1- and 2-substituted bicyclo- [l.l.l]pentanes is described by K.B. Wiberg and V.Z. Williams in J. Org. Chem., 35:369-373 (1970). The synthesis of a variety of 1,3-disubstituted bicyclo[1.1.1]- pentanes is described by D.E. Applequist, et al. , in J. Org. Chem. 47:4985-4995 (1982). Various quinolone-carboxylic acids are disclosed in U.S. Patent 4,563,448 for combating plant-pathogenic bacteria. Other quinolone acids suitable for treating bacteria infection are disclosed in U.S. Patent 4,559,342 and in German Patent DE 3,615,303. In one aspect the present compounds, Formula IA also exhibit antibacteria proper¬ ties but unlike the disclosed compounds possess a unique substituent on the piperazinyl ring. The preparation of various piperazinyl and 3-amino-l-pyr- rolidinyl naphthyridine derivatives, including 2-(4-(l-cyclopropyl-3- carboxy-6-fluoro-1,4-dihydro-4-oxo-7-quinolinyl)-1-piperazinyl)-2- butanedioic acid, 2-(4-(l-cyclopropyl-3-carboxyethyl-6-fluoro-1,4- dihydro-4-oxo-7-quinolinyl)-1-piperazinyl)-2-butanedioic acid, dimethyl ester, 2-(4-(l-ethyl-3-carboxy-6-fluoro-l,4-dihydro-4-oxo-7- quinolin l)-1-piperazinyl)-2-butanedioic acid, and 2-(4-(l-ethyl-3- carboxyethyl-6-fluoro-l,4-dihydro-4-oxo-7-quinolinyl)-1-piperazinyl)- 2-butanedioic acid, dimethyl ester are disclosed in Japanese publica- tion 62-207258 (Chem. Abst. 108(15) :131600s) and Great Britain Patent Application 87-GB-002508. Summary of the Invention The present invention is directed toward new compounds, generi- cally represented by Formula I, useful as antibacterials or in the preparation of antibacterial compositions. Formula I is defined where X is nitrogen, a carbon substituted with a hydrogen, hydroxyl, cyano, nitro, halogen C1-C4 alkyl or an amine; R3 is H, halogen, amine or hydroxyl; Y is 1) alkyl, C2-C1 Q cycloaklyl or heterocycloalkyl, phenyl or substituted phenyl wherein the substituent is one or more of 0 - C o alkyl, halogen, hydroxyl, hydrogen or a combination thereof, or C2-C alkylene wherein each carbon may be substituted with a fluori- ne; 2) -C(R j^ 3)2C=CR^ where R^3 is independently hydrogen, methyl, halogen substituted methyl or joined to form a cyclopropyl and R 4 is hydrogen, fluorine, chlorine, bromine, C -Cg alkyl or phenyl; or 3) bicyclo (1.1.1) pent-1-yl which can be substituted at C-3 with C -Cg alkyl, C -Cg alkoxy, fluoro, bromo, chloro, nitro, amino, hydroxy, COOH, C00 Cι-Cg alkyl) and phenyl optionally substituted with one or two C -C4 alkyl, C^-C alkoxy, halo, trifluromethyl, C2- Cg dialkylamino, C -C3 alkylthio or nitro; Z is nitrogen, or a fluorine substituted carbon; wherein R^ is hydrogen or hydroxyl; wherein R7 is selcted from the Formula A'- H' ; wherein R^ is independently selected from H, C3-C cycloalkyl, C5-C cycloalkenyl, -Q-N(R 10 )-C(R 9 )H-CH 2 -C(R 8 )O, -Q-N(R 10 )-C(R 9 )-CH(R 12 )- C(Rg)0, Rg is hydrogen, hydroxyl, amine, C1-C4 alkoxy or aryloxy,- SH, C -Cg thioalkyl or thioaryl; R9 is C1-C4 alkyl, Cg-C j ^ aryl, alkylaryl, heteroaryl, -(CH2) n -Cθ2-(CH2) m - χι, Rχι is hydrogen, hydroxyl, methyl alkyloxy, aryloxy or an amine, n is 0-4 and m is 0- 4; R^o i s hydrogen, -(CH3) Q C2-C4 alkyl, Cg-C^ ar yl > alkylaryl, heteroaryl, or acetyl, where o is 0 or 1; Q is (CH2) q where q is 0-2, CH-CH3 or C(CH3)2 and Cχ-Cg alkyl optionally substituted with 1, 2 or 3 hydroxy, fluoro, chloro, amino, C -C4 alkylamino, trifluoroacetyl- amino and phenyl; A, B, C, and D are independently selected from H, amino, hydroxy, halogen, C -C4 alkyl optionally substituted with 1, 2 or 3 hydroxy, fluoro, chloro, amino, C2-C alkylene, ethynyl, C -C4 alkylamino, trifluoroacetylamino, C3-Cg cycloalkyl, C^-C g alkoxy- methyl, phenoxymethyl, C -C3 alkyl aminomethyl, C1-C3 dialkyl aminomethyl, Cg-C ] ^ aryl, substituted aryl, heteroaryl or substituted heteroaryl containing at least one 0, N or S and phenyl; and phar¬ maceutically acceptable acid addition and base salts thereof. In one aspect, the compound of the present invention is as shown in Formula IA or therapeutically acceptable salts wherein: R^ is hydrogen or hydroxyl; Y is C -C^ Q alkyls, C3-C Q cycloalkyl or heterocycloalkyl, a phenyl, or a substituted phenyl wherein the substituent on the phenyl group is one or more of C -C j f j alkyl, halogen, hydroxyl, hydrogen or a combination thereof, or C2-C alkylene wherein each carbon atom may be substituted with fluorine; R3 is hydrogen, halogen, amine or hydroxyl; A, B, C, D are independently hydrogen, hydroxyl, halogen, C1-C4 alkyl, ethenyl, ethynyl, 03-05 cycloalkyl, fluoromethyl, difluoro- methyl, difluoroethyl, trifluoromethyl, hydroxymethyl, C -C^g alkoxy methyl, phenoxymethyl, C -C3 alkyl aminomethyl, C -C3 dialkyl aminomethyl, C -C 2 aryl, substituted aryl, heteroaryl or substituted heteroaryl containing at least one 0, N or S; Rg is hydrogen, hydroxyl, amine, C -C4 alkoxy or aryloxy, -SH, C -Cg thiσalkyl or thioaryl; R9 is C -C4 alkyl, Cg-C 2 aryl, alkylaryl, heteroaryl, -(CH2) n - C02-(CH2 m -Rιχ, wherein R- ^ is hydrogen, hydroxyl, methyl alkyloxy, aryloxy or an amine, n is 0-4 and m is 0-4; R θ i- s hydrogen, - CH3) 0 C2-C4 alkyl, C -C 2 aryl, alkylaryl, heteroaryl, or acetyl, where o is 0 or 1; R^2 *- s hydrogen CN, halogen, or R9; Z is nitrogen or carbon substituted by fluorine; X is nitrogen, a carbon substituted with hydrogen, hydroxyl, cyano, nitro, halogen, C -C4 alkyl, or an amine; and Q is (CH 2 ) q where q is 0-2, CH-CH3 or C(CH3) 2 . The dotted bonds indicate that the carbon atom having the A group can be bonded to either the nitrogen to form Formula IA2 or the carbon atom having the D group to form Formula IA^. When the structure is as depicted in Formula IA a then R o is -(CH3) 0 where o is 0 and preferably, Q is (CH2) q where q is 0. Preferred compounds of the Formula IA structure can include 2- [4-(l-Cyclopropyl-3-carboxy-6,8-difluoro-l,4-dihydro-4-oxo-7-quinoli- nyl)-1-piperazinyl]2-butenedioic acid, dimethyl ester; 2-[4-(l-Ethyl- 3-carboxy-6-fluoro-l,4-dihydro-4-oxo-7-quinolinyl)-l-piperizinyl]2- butenedioic acid, dimethyl ester; 2-[4-(l-Cyclopropyl-3-carboxy- 5,6, 8-trifluoro-l,4-dihydro-4-oxo-7-quinolinyl)-1-piperazinyl]2- butenedioic acid, dimethyl ester; 2-[4-(l-Cyclopropyl-3-carboxy-6- fluoro-1,4-dihydro-4-oxo-7-quinolinyl)-1-piperazinyl]2-butenedioic acid, dimethyl ester; and (E)-2-(N-(3-carboxy-l-cyclopropyl-6,8- difluoro-1,4-dihydro-4-oxo-7-quinolinyl)-l-(3-aminopyrrolinyl))-2- butenedioic acid, 1, -dimethyl ester. In another aspect, the present invention is as shown in Formula IB which are novel -oxo-naphthyridine- and 4-oxo-quinoline-3- carboxylic acids derivatives having a l-bicyclo[l.l.l]pent-l-yl substituent, to compositions containing the same, and their use in treating bacterial infections in warm-blooded animals and man. Also disclosed are novel amines and intermediates used in the preparation of the same. In yet another aspect, the subject invention is novel naph¬ thyridine- and quinoline-carboxylic acids derivatives having a propargyl moiety (RC=C-CR'2") at the Y position according to Formula I, as structurally depicted in Formula IC and to compositions containing the same. In another aspect, the present invention is a pharmaceutical composition containing an antibacterially effective amount of a compound or therapeutically acceptable salts thereof according to Formula I in admixture with a pharmaceutical carrier. The composi¬ tion can contain from about 0.5 to about 90% by weight of such compound. The composition can be present in unit dose form of tab¬ lets, pills, dragees, capsules, ampules or suppositories. In yet another aspect, the present invention is method for treating bacterial infection in animals including humans which comprises administering an antibacterially effective amount of a compound or therapeutically acceptable salts thereof according to Formula I. In the method the compound can be administered orally or parenterally. Detailed Description of Invention The present invention relates to quinolone compounds and anti¬ bacterial agents containing these compounds. The quinolone compounds are structurally represented by Formula I, shown on the Formula Sheet, and includes therapeutically acceptable salts thereof. Formula I is further broken down into Formula IA, IB and IC where each structure encompasses a similar heterocyclic ring structure each with a particular Y substituent. For instance, Formula IA has a group of alkyl, alkylene, cycloalkyl, heterocycloalkyl phenyl and substituted phenyls at the Y position, Formula IB has a bicyclo (1.1.1) pent-1-yl substituent at the Y position and Formula IC has a propargyl substituent at the Y position. Formula IA Formula IA is defined wherein R^ is hydrogen or hydroxyl; Y is G 1" G 10 alkyls, C- -CIQ cycloalkyl or heterocycloalkyl, a phenyl, or a substituted phenyl wherein the substituent on the phenyl group is one or more of alkyl, halogen, hydroxyl, hydrogen or a combination thereof, or C2-C4 alkylene wherein each carbon atom may be sub¬ stituted with fluorine (known substituents for the Y group are described by Domagala et al., J. Med. Chem., H, 991 (1988) herein incorporated by reference) ; R3 is hydrogen, halogen, amine or hydroxyl; A, B, C, D are independently hydrogen, hydroxyl, halogen, c l" c 4 alkyl, ethenyl, ethynyl, C3~Cg cycloalkyl, fluoromethyl, difluoromethyl, difluoroethyl, trifluoromethyl, hydroxymethyl, Cχ-C g alkoxy methyl, phenoxy-methyl, C -C3 alkyl aminomethyl, C -C3 dialkyl aminomethyl, Cg-C j ^ aryl, substituted aryl, heteroaryl or sub¬ stituted heteroaryl; Rg is hydrogen, hydroxyl, amine, C -C alkoxy or aryloxy, -SH, C -Cg thioalkyl or thioaryl; Rg is C -C4 alkyl, C -C 2 aryl, alkylaryl, heteroaryl, -(CH2) n -C02-(CH2) m -Rχι, wherein R^ is hydrogen, hydroxyl, methyl alkyloxy, aryloxy or an amine, n is 0-4 and m is 0-4; R ø is hydrogen, -(CH3) 0 C2-C4 alkyl, Cg-Cχ2 aryl, alkylaryl, heteroaryl, or acetyl, where o is 0 or 1; R 2 is hydrogen CN, halogen, or R9; Z is nitrogen or carbon substituted by fluorine; X is nitrogen, a carbon substituted with hydrogen, hydroxyl, cyano, nitro, halogen, C -C4 alkyl, or an amine; and Q is (CH2) q where q is 0-2, CH-CH3 or C(CH 3 ) 2 . The dotted bonds indicate that the carbon atom having the A group can be bonded to either the nitrogen to form Formula IAa or the carbon atom having the D group to form Formula IAb. When the struct¬ ure is as depicted in Formula IAa then R-JQ is -(CH3) Q where o is 0 and preferably, Q is (CH2) q where q is 0. Preferred quinolone compounds of Formula IAa are where R^ is hydroxy, Y is cyclopropane or ethyl, R3 is hydrogen or fluorine, Z and X are carbon or fluorine substituted carbon, A, B, C and D are hydrogen, Rg is methoxyl, R9 is a carbomethoxyl ester so as to form either the dimethylester of maleic or fumaric acid and R-^Q ^ S " (CH3) 0 .where o is 0. Preferred quinolone compounds of Formula IAb are when R^ is hydroxyl and Y is cyclopropyl and R3, A, B, C, D and RX are hydrogen, Rg is O-CH3, R9 is C(0)0CH 3 , Z and X are C(F) and Q is (CH2) q where q " Is zero. Examples of "C -C Q alkyl" are one to ten carbon atoms such as methyl, ethyl, propyl, butyl, etc. and isomerlc forms thereof. The "C2-C4 alkylenes" are ethylene, propylene and 1 or 2-butylene and iso eric forms thereof. Examples of "C3-C10 cycloalkyl" are cyclo¬ propyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. and "heterocyclo- alkyl"are cycloalkyl ring which contain at least one heteroatom such as oxygen, sulfur or nitrogen. Examples of "C _C 2 aryl" are compounds such as phenyl, α- naphthyl, /9-naphthyl, m-methylphenyl, p-trifluoromethylphenyl and the like. The aryl groups can also be substituted with one to 3 hydroxy, C -C3 alkoxy, C -C3 alkyl, trifluoromethyl, fluoro, chloro or bromo groups. Examples of "alkylaryl" are alkyl chains of one to eight carbon atoms and isomeric forms thereof which are substituted with aryl groups of 6 to 12 carbon atoms. Examples of "heteroaryls" are 6 to 12 carbon atom aryls which contain at least one heteroatom such as nitrogen, sulfur and oxygen. An "amine" is meant to include primary, secondary and tertiary amines. "Halogen" is meant to include F, Cl, Br and I. "Therapeut¬ ically acceptable salts" are those compounds of Formula I wherein a carboxyl group is substituted with a counter ion such as Li, Na, K, Ca or other acceptable counter ions for carboxylic acids. A generic scheme for the preparation of the Formula IAa quinol¬ one compounds is illustrated in Scheme 1, below. The scheme shows two alternative routes to arrive at the compound represented by formula IAa. Starting material "a" is converted to an enol-ether "b" which is treated with a primary amine to yield "c" which is treated with a base to yield "d" which is reacted with piperazine to yield "e" which is treated with dimethyl acetylene dicarboxalate to yield "f" which is hydrolyzed to yield "I". Alternatively, "d" is hydroly- zed to "h" which is treated with piperazine to yield "i" which is treated with di ethylacetylene dicarboxalate to yield "IAa". A generic scheme for the preparation of the Formula IAb quinol¬ one compounds is illustrated in Scheme 2, below. The chemistry is described by Domagala et al. , J. Med. Chem., 31, 991 (1988). The compounds according to the invention have good actions against Gram-positive and Gram- egative bacteria, particularly against enterobacteriaceae. The effectiveness of the subject compounds on bacteria were obtained by performing a dip disk assay. The antibacterial activity of the compounds was determined by the disk-diffusion method. Paper disks (12.7 mm) were loaded with 0.05 ml of drug solution prepared at a concentration of 0.1 cg/ml; the disks were allowed to air dry. They were then applied to the surface of microorganism-seeded agar assay trays, which contained the bacterial strain Pseudomonas aeruginosa UC 95 (PA), Escherichia coli UC 51 (EC), Klebsiella pneumoniae UC 57 (KP) , or Staphylococcus aureus UC 80 (SA) . The assay trays were incubated overnight under aerobic condition to allow for the growth of the organisms. Zones of growth inhibition due to the action of the antibiotic were then measured to the nearest milli¬ meter. The results show that compounds 1-4, all of Formula IAa, cor¬ responding to Examples 1-4, below, have potent gram negative and positive activity as compared to the commercially available antibac- teria Ciprofloxacin, from Miles Pharm. Div. , West Haven, CT. The effectiveness of additional compounds 5-9, (5-7 are Formula IAa compounds and 8 and 9 are Formula IAb compounds) on bacteria were obtained by performing a dip disk assay as described above. The antibacterial activity of the compounds was determined by the disk- diffusion method where the disks were loaded with 0.05 ml of drug solution prepared at a concentration of 1.0 mcg/ml; the disks were allowed to air dry. (Growth Inhibition at 1.0 mcg/ml for) Compound EC PA SA KP 5 24 27 27 28 6 7 8 9 Compound 10 corresponding to Formula IAb and as described in Example 10 was compared to a control of ciprofloxacin as shown below. Concentration in up/ml Organism Staphylococcus Aureus Staphylococcus Aureus Staphylococcus Aureus Staphylococcus Aureus Staphylococcus Epidermidis Staphylococcus Faecalis Staphylococcus Pneumoniae Staphylococcus Pyogenes Acinetobacter Calcoaceticus Citrobacter Freundii Enterobacter Cloacae Escherichia Coli Escherichia Coli Escherichia Coli Escherichia Coli Klebsiella Pneumoniae Proteus Penneri Pseudomonas Aeruginosa Pseudomonas Aeruginosa Pseudomonas Aeruginosa Serratia Marcescens The data shows that compound 10, Example 10, had gram negative and positive activity greatly increased over that of ciprofloxacin. Formula IB Formula IB is defined wherein X is selected from N, CH, CF, CC1, CBr, and CCH 3 ; wherein R3 is selected from H, F and NH2; wherein R is selected from H, C -Cg alkyl, C -Cg alkoxy, fluoro, bromo, chloro, nitro, amino, hydroxy, COOH, C00(C -Cg alkyl) and phenyl optionally substituted with one or two C^-C alkyl, C^-C3 alkoxy, halo, trifluoromethyl, C^-C dialkylamino, C1-C3 alkylthio or nitro; wherein R 7 is selected from Formula A', B' , C , D' , E' , F' , G' and H' (see GENERAL FORMULA sheet) wherein R^ is independently selected from H, C3-C5 cycloalkyl, C5-C5 cycloalkenyl, -Q-N(R g)- C(R 9 )H-CH 2 -C(Rg)0 (see GENERAL FORMULA sheet), -Q-N(R 10 )-C(R 9 )-CH- C(Rg)0 and C^-Cg alkyl optionally substituted with 1, 2 or 3 hydroxy, fluoro, chloro, amino, C1-C4 alkylamino, trifluoroacetylamino and phenyl; wherein A, B, C, and D are independently selected from H, amino, hydroxy, fluoro, chloro, C -C4 alkyl optionally substituted with 1, 2 or 3 hydroxy, fluoro, chloro, amino, C2-C4 alkylene, C -C4 alkylamino, trifluoroacetylamino and phenyl; and wherein n, when present, is selected from the integers 0, 1, 2, and 3; Rg is hydrogen or methyl; R9 is C1-C4 alkyl or -(CH2) m -Cθ2-(CH2)p-Rχ3, wherein R 3 is hydrogen, methyl or an amine, m is 0-4 and p is 0-4; R jfj i hydroxy, amine, C -C alkoxy or aryloxy; and Q is (CH 2 ) q where q is 0-2, CH-CH3 or C(CH 3 ) 2 ; pharmaceutically acceptable acid addition and base salts thereof. R is preferably hydrogen. R3 is preferably hydrogen or NH2. X is preferably CH, CF and N. R is preferably 1-piperazinyl, 4-methyl-l-piperazinyl, 3- methyl-1-piperazinyl, 3,5-dimethyl-1-piperazinyl, 2,5-diazabicyclo [2,2,l]heptan-2-yl, 3-amino-l-pyrrolidinyl, 3-amino-4-methyl-l- pyrrolidinyl, 3-hydroxy-1-pyrrolidinyl and 3-(ethylamino)methyl-l- pyrrolidinyl. R o is preferably hydrogen. R9 is preferably a carbomethoxy ester and Rg is methoxy so as to form either the dimethyl ester of succinic, maleic and/or fuπtaric acid. Examples of "C^-C4 alkyl" are one to four carbon atoms such as methyl, ethyl, propyl, butyl and isomeric forms thereof. Examples of "C -Cg alkoxy" Include methoxy, ethoxy, propoxy, butoxy, heptoxy and isomeric forms thereof. Examples of "C3-C cycloalkyl" are cyclopropyl, cyclobutyl, eye- lopentyl and cyclohexyl. Examples of "C5-C5 cycloalkenyl" include cyclopenten-3-yl and cyclohexen-3-yl. Examples of Formula IB compounds of this invention include: l-(bicyclo[l.l.l]pent-l-yl)-6,8-difluoro-l,4-dihydro-4-oxo-7-(l- piperazinyl)-3-quinolinecarboxylic acid (Cpd #1) ; 1- (bicyclo[l.l.l]pent-l-yl)-l,4-dihydro-6-fluoro-4-oxo-7-(l- piperazinyl)-3-quinolinecarboxylic acid (Cpd #2); l-(bicyclo[1.1.l]pent-l-yl)-l,4-dihydro-6-fluoro-7-(1-piperazin¬ yl)-4-oxo-3-quinolinecarboxylic acid, methane sulfonate; 7- [4-(cyclopenten-3-yl)-1-piperazinyl]-1-(bicyclo[1.1.1]pent-1- yl)-1,4-dihydro-6-fluoro-4-oxo-3-quinolinecarboxylic acid, hydro- chloride; 7- (8-methyl-3,8-diazabicyclo[3.2.1]octan-3-yl)-l-(bicyclo- [1.1.l]pent-l-yl)-1,4-dihydro-6-fluoro-4-oxo-3-quinolinecarboxylic acid, hydrochloride; 7- [3-phenyl-1-piperazinyl] -1- (bicyclo[l.1.1]pent-1-yl)-1,4- dihydro-6-fluoro-4-oxo-3-quinolinecarboxylic acid, methanesulfonate; 1- (bicyclo[l.l.l]pent-l-yl)-l,4-dihydro-6-fluoro-7-(4-methyl-l- piperazinyl)-4-oxo-3-quinolinecarboxylic acid, hydrochloride; 7-(2,5-diazabicyclo[2.2.2]octan-2-yl)-l-(bicyclo[l.l.l]pent-l- yl)-l,4-dihydro-6-fluoro-4-oxo-3-quinolinecarboxylic acid; 7-(lS,4S-2,5-diazabicyclo[2.2.1]heptan-2-yl)-l-(bicyclo[l.l.l]- pent-l-yl)-l,4-dihydro-6-fluoro-4-oxo-3-quinolinecarboxylic acid; 7- (3- (aminomethyl)-l-pyrrolidinyl)-l-(bicyclo[1.1.1]pent-l-yl)- l,4-dihydro-6-fluoro-4-oxo-3-quinolinecarboxylic acid; 7- (3- (ethylamino)methyl-1-pyrrolidinyl-1-(bicyclo[1.1.1]pent-1- y1)-1,4-dihydro-6-fluoro-4-oxo-3-quinolinecarboxylic acid; 7- (3-methyl-1-piperazinyl)-1-(bicyclo[1.1.1]pent-l-yl)-1,4-di¬ hydro-6-fluoro-4-oxo-3-quinolinecarboxylic acid; 7- (3 ,5-dimethyl-1-piperazinyl)-1-(bicyclo[1.1.1]pent-l-yl)-1,4- dihydro-6-fluoro-4-oxo-3-quinolinecarboxylic acid; 7- (4- (dimethylamino) -1-piperazinyl) -1- (bicyclo[1.1.1]pent-1- yl)-l,4-dihydro-6-fluoro-4-oxo-3-quinolinecarboxylic acid; 7-(4-(1,1-dimethylethyl)-1-piperazinyl)-1-(bicyclo[1.1.1]pent-1- yl)-l,4-dihydro-6-fluoro-4-oxo-3-quinolinecarboxylic acid; 7-(3-(ethylamino)methyl-1-pyrrolidinyl)-1-(bicyclo[1.1.1]pent-1- 1)-1,4-dihydro-6,8-difluoro-4-oxo-3-quinolinecarboxylic acid; 7- (3-amino-1-pyrrolidinyl) -1- (bicyclo[1.1.1]pent-1-yl)-1,4- dihydror6-fluoro-4-oxo-3-quinolinecarboxylic acid, hydrochloride; 7-(3-hydroxy-l-pyrrolidinyl)-l-(bicyclo[l.l.l]pent-l-yl)-l,4- dihydro-6-fluoro-4-oxo-3-quinolinecarboxylic acid; 7-(3-amino-1-pyrrolidinyl)-1-(bicyclo[1.1.1]pent-1-yl)-1,4- dihydro-6-fluoro-4-oxo-3-quinolinecarboxylic acid; 7- (3-amino-4-methyl-pyrrolidin-l-yl)-l-(bicyclo[1.1.l]pent-l- yl)-l,4-dihydro-6-fluoro-4-oxo-3-quinolinecarboxylic acid; 7-(3-hydroxy-l-pyrrolidinyl)-l-(bicyclo[l.l.l]pent-l-yl)-l,4- dlhydro-6,8-difluoro-4-oxo-3-quinolinecarboxylic acid (Cpd #3); 7-(3-amino-4-methyl-pyrrolidin-l-yl)-l-(bicyclo[1.1.l]pent-l- yl)-1,4-dihydro-6,8-difluoro-4-oxo-3-quinolinecarboxylic acid; 7- (3-hydroxy-3-methylpyrrolidin-1-yl)-1-(bicyclo[1.1.l]pent-l- yl)-l,4-dihydro-6-fluoro-4-oxo-l,8-naphthyridine-3-carboxylic acid; 7-(3-amino-3-methylpyrrolidin-1-yl)-1-(bicyclo[1.1.1]pent-1-yl)- 1,4-dihydro-6-fluoro-4-oxo-l,8-naphthyridine-3-carboxylic acid; 7-(3-hydroxy-3-phenylpyrrolidin-1-yl)-1-(bicyclo[1.1.1]pent-l- y1)-1,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid; 7-(3-amino-3-phenylpyrrolidin-l-yl)-1-(bicyclo[l.l.l]pent-l-yl)- 1,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid; 7-(3,5-dimethyl-l-piperazinyl)-l-(bicyclo[l.l.l]pent-l-yl)-l,4- dihydro-6-fluoro-4-oxo-l,8-naphthyridine-3-carboxylic acid; 7-(3-hydroxy-l-pyrrolidinyl)-l-(bicyclo[l.l.l]pent-l-yl)-l,4- dihydro-6-fluoro-4-oxo-l,8-naphthyridine-3-carboxylic acid (Cpd #91); 7-(1-piperazinyl)-1-(bicyclo[1.1.1]pent-1-yl)-1,4-dihydro-6- fluoro-4-oxo-l,8-naphthyridine-3-carboxylic acid (Cpd #4) ; 7-(3-methyl-l-piperazinyl)-l-(bicyclo[l.l.l]pent-l-yl)-l,4-di- hydro-6-fluoro-4-oxo-l,8-naphthyridine-3-carboxylic acid; 7- (4 -methyl -1-piperazinyl) -1- (bicyclo [1.1.1] pent -1-yl) -1,4- dihydro-6,8-difluoro-4-oxo-3-quinolinecarboxylic acid (Cpd #99); 7-(lS,4S-2,5-diazabicyclo[2.2.1]heptan-2-yl)-l-(bicyclo- [1.1.1] pent- 1-yl) - 1,4- dihydro-6- fluoro -4 -oxo-l,8-naphthyridine-3- carboxylic acid; 7 -(2,5 -diazabicyclo [2.2.2] octan-2-yl)-l- (bicyclo [1.1. l]pent-l- yl)-l, 4-dihydro- 6 -fluoro-4-oxo-l, 8 -naphthyridine-3 -carboxylic acid; 7- (4-(cyclopenten-3-yl)-l-piperazinyl)-l-(bicyclo[l.l.l]pent-l- yl ) - 1 , 4 - dihydro - 6 - fluoro - 4 - oxo -1,8- naphthyridine - 3 - carboxylic acid ; 7- (3- (ethylamino)methyl-l-pyrrolidinyl) -1- (bicyclo [1.1.1] pent- 1- yl) -l,4-dihydro-6-fluoro-4-oxo-l, 8 -naphthyridine- 3 -carboxylic acid; 7.- (3-methyl-1-piperazinyl) -1-(bicyclo[1.1.1]pent-1-yl)-1,4 dihydro-6-fluoro- -oxo-1,8-naphthyridine-3-carboxylic acid; 7-(3,4-dimethyl-l-piperazinyl)-l-(bicyclo[l.l.l]pent-l-yl)-l,4 dihydro-6-fluoro-4-oxo-l,8-naphthyridine-3-carboxylic acid; 7- (3-phenyl-l-piperazinyl)-l-(bicyclo[l.l.l]pent-l-yl)-l,4 dihydro-6-fluoro-4-oxo-l,8-naphthyridine-3-carboxylic acid, methane- sulfonate; 7-(lR,4R-2,5-diazabicyclo[2.2.1]heptan-2-yl)-l-(bicyclo- [1.1.1]pent-1-yl)-1,4-dihydro-6-fluoro-4-oxo-l,8-naphthyridine-3- carboxylic acid; 7- (8-methyl-3,8-diazabicyclo[3.2.1]octan-3-yl)-l- (bicyclo- [1.1.1]pent-1-yl)-1,4-dihydro-6-fluoro-4-oxo-l,8-naphthyridine-3- carboxylic acid, methanesulfonate salt; 7- (3,8-diazabicyclo[3.2.1]octan-3-yl)-l-(bicyclo[1.1.l]pent-l- yl)-1, -dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid, methanesulfonate; 7- (2-aminomethyl-morpholin-4-yl)-l-(bicyclo[1.1.1]pent-1-yl)- l,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid; 7-((S)-3-amino-l-pyrrolidinyl)-l-(bicyclo[l.l.l]pent-l-yl)-l,4- dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid; 7- (3-amino-4-methy1-pyrrolidin-1-yl)-1-(bicyclo[1.1.1]pent-l- yl)-l,4-dihydro-6-fluoro-4-oxo-l,8-naphthyridine-3-carboxylic acid; 7- (trans-3-amino-4-methyl-pyrrolidin-l-yl)-l-(bicyclo[l.l.l]- pent-1-yl) -l,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxyli acid; 7- (cis-3-amino-4-methyl-pyrrolidin-l-yl)-l-(bicyclo[1.1.1]pent- 1-yl)-1,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid; and preferably 7- (3-amino-1-pyrrolidinyl) -1- (bicyclo[1.1.1]pent-1-yl)-1,4- dihydro-6-fluoro-4-oxo-l,8-naphthyridine-3-carboxylic acid (Cpd #36) ; and 7- (3-amino-1-pyrrolidinyl) -1- (bic clofl.1.1]pent-1-yl)-1,4- dihydro-6,8-difluoro-4-oxo-3-quinolinecarboxylic acid (Cpd #84); and more preferably 7- (3-amino-1-pyrrolidinyl) -1-(bicyclofl.1.1]pent-1-yl)-1,4- dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid (Cpd #36). The compounds of Formula IB according to this invention may be provided as pharmaceutically acceptable acid addition and base salts wherein. the anion or cation, respectively, does not contribute sig¬ nificantly to the toxicity of the salt and which salts are compatible with the standard and conventional pharmaceutically acceptable carriers and other conventional adjuvants and excipients customarily employed in producing pharmaceutical compositions adapted for oral or parenteral administration. The acid addition salts are formed by conventional techniques involving reaction of compounds of Formula I with mineral acids such as, for example, hydrochloric acid, hydrobro- mic acid, phosphoric acid, and sulfuric acid, and with organic carb- oxyllc and sulfonic acids such as, for example, aspartic acid, glut- amic acid, galacturonic acid, gluconic acid, acetic acid, citric acid, aleic acid, succinic acid, benzole acid, tartaric acid, ascorbic acid, methanesulfonic acid, ethanesulfonic acid, 2-hydroxy- ethanesulfonic acid, p-toluenesulfonic acid, and the like. The compounds of Formula IB with R3 - H or F are readily prepared as depicted in Schemes 13 and 14. For example, reaction of an appropriate 1-amino-bicyclo[l.l.l]pentane hydrochloride with an appropriate nicotinyl-(X-N) or benzoyl- (X-CH, CF, CC1, CBr, CCH3) acetate 3 in a suitable solvent such as methylene chloride and in the presence of a suitable base such as diisopropylethylamine affords the novel enamino keto esters 4. The preparation of the requisite nicotinyl- and benzoyl-acetates .3 is described, for example, by D.T.W. chu, et al., in J. Med. Chem. 28:1558-1564 (1985); J. Med. Chem. 29:2363-2369 (1986); and J. Med. Chem. 30:504-509 (1987). The enamino keto esters 4 are then cyclized to the corresponding novel naphthyridine- or quinoline-esters 5. in an suitable aprotic solvent such as tetrahydrofuran and in the presence of a suitable base such as sodium hydride. Naphthyridine- or quinoline-esters 5, can be converted to the targeted antibacterial agents of Formula I by two different routes. In the first of these, esters 5 , are treated with an appropriate heterocyclic amine in a suitable solvent such as acetonitrile in the presence of a suitable base such as diisopropyle¬ thylamine or DBU (l,8-diazabicyclo[5.4.0]undec-7-ene) to provide the penultimate naphthyridine- or quinoline-esters 6.. Esters 6. can be converted to the corresponding acids of Formula I (R5=H,F by treating them, for example, with aqueous sodium hydroxide. Alterna¬ tively, a second route to compounds of Formula I involves the saponification of esters 5_ with, for example, aqueous sodium hydroxi- de, to- rovide the penultimate naphthyridine- or quinoline-carboxylic acids 2- The compounds 2 are then reacted with an appropriate heterocyclic amine in a suitable solvent such as pyridine, which acts as its own base, or in an aprotic solvent such as DMSO (dimethylsul- foxide) in the presence of a suitable added base such as diisopropyl¬ ethylamine, to afford the targeted naphthyridine- or quinoline¬ carboxylic acids of Formula I (R3~H,F). A number of synthetic routes are available to prepare compounds of Formula IB with R3-NH2. Representative procedures utilized to prepare similar 5-aminoquinolinecarboxylic acids are described by J.M. Domagala, et al. , in J. Med. Chem. 31:506-509 (1988); and in EP 0,221,463. For example, quinolone esters 5, (R5-F) can be reacted with an appropriate protected amine such as benzylamine in a suitable solvent such as acetonitrile and in the presence of a suitable base such as potassium carbonate to provide quinoline esters 5_ (R5-NHCH2- Ph) . Catalytic hydrogenolysis in a suitable solvent system such as acetic acid/ethanol and in the presence of a suitable catalyst such as palladium black, then affords the corresponding quinoline esters 5. (R3-NH2) . Application of the synthetic protocols described above for Schemes 13 and 14 then provides the targeted naphthyridine- and quinoline-carboxylic acids of Formula I (R5-NH2) . Formula IC The present invention also provides new naphthyridine- and quinoline-carboxylic acids of Formula I (see GENERAL FORMULA sheet) . In Formula IC, X is N, CH, CF, CC1, CBr, or CCH3 and R3 is H, F or NH2. The R23 groups are independently hydrogen, methyl, a methyl substituted with one or more halogens (fluorine, cholorine, bromine or iodide, preferably, fluorine) such as, for example, -CH2F or are joined to form a cyclopropyl. R24 is hydrogen, fluorine, chlorine, bromine, C -Cg alkyl, or phenyl. R 7 is as defined above for Formula I or selected from various piperazinyl and pyrrolidinyl structures as depicted in Formula J' , K' , L' , M' , N' , 0', P' , Q' and R' (see GENERAL FORMULA sheet) wherein R2 is independently selected from hydrogen, C -Cg alkyl optionally substituted with one or more hydroxy, fluoro, chloro, amino, C -C4 alkylamino, trifluoroacetyl¬ amino and phenyl groups and R27 is hydrogen, hydroxyl or a C -Cg alkyl optionally substituted with one or more hydroxy, or halogens (fluorine, chlorine, bromine or iodide, preferably, fluorine). Typically in Formula IC, R7 can be 1-piperazinyl (Formula J'), 4- methyl-1-piperazinyl (Formula K'), 3-methyl-l-piperazinyl (Formula L'), 3,5-dimethyl-l-piperazinyl (Formula M'), 2,5-diazabicyclo [2.2.1]hept-2-yl (Formula N'), 3-hydroxy-1-pyrrolidinyl (Formula 0' where Rg is hydrogen), 3-amino-1-pyrrolidinyl (Formula P' where Rg is hydrogen), 3-amino-4-methyl-l-pyrrolidinyl (Formula Q'), 4-amino- methyl-3-hydroxy-l-pyrrolidinyl (Formula R' where R£g is hydrogen and R27 is hydroxyl) and 3-(ethylamino)methyl-l-pyrrolidinyl (Formula R' where R26 is ethyl and R27 is hydrogen) . Examples of "C -Cg alkyl" are one to six carbon atoms such as methyl, ethyl, propyl, butyl, etc. and isomeric forms thereof. Examples of Formula IC compounds of this invention include: (+, -)-6, 8-difluoro-l,4-dihydro-l-(l,l-dimethyl-2-propynyl)-4-oxo-7- (1-piperazinyl)-3-quinolinecarboxylic acid methanesulfonate; (+,-)- 6,8-difluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-l-(2-propynyl)-3- quinolinecarboxylic acid methanesulfonate; (+,-)-7-(3-amino-l- pyrrolidinyl)-1,4-dihydro-1- (1,l-dimethyl-2-propynyl)-6-fluoro-4- oxo-l,8-naphthyridine-3-carboxylic acid methanesulfonate; (+,-)-7- (amlno-l-pyrrolidinyl) -6,8-difluoro-l,4-dihydro-l-(l,l-dimethyl-2- propynyl)-4-oxo-3-quinolinecarboxylic acid; or (+,-)-7-(amino-l-pyr- rolidinyl)-6,8-difluoro-l,4-dihydro-4-oxo-l-(2-propynyl)-3-quinoline- carboxylic acid. The compounds of Formula I according to this invention may be provided as pharmaceutically acceptable acid addition and base salts wherein the anion or cation, respectively, does not contribute sig¬ nificantly to the toxicity of the salt and which salts are compatible with the standard and conventional pharmaceutically acceptable carriers and other conventional adjuvants and excipients customarily employed in producing pharmaceutical compositions adapted for oral or parenteral administration. The acid addition salts are formed by conventional techniques involving reaction of compounds of Formula I with mineral acids such as, for example, hydrochloric acid, hydrobro- mic acid, phosphoric acid, and sulfuric acid, and with organic carb¬ oxylic and sulfonic acids such as, for example, aspartic acid, glut- amic acid, galacturonic acid, gluconic acid, acetic acid, citric acid, maleic acid, succinic acid, benzoic acid, tartaric acid, ascorbic acid, methanesulfonic acid, ethanesulfonic acid, 2-hydroxy- ethanesulfonic acid, p-toluenesulfonic acid, and the like. In. one method, the compounds of Formula IC can be prepared according to the general reaction Scheme 16, below. In this scheme the first step involves the coupling of a propargyl moiety with a vinyl ether 1 to form compound 2, followed by base induced cycliza- tion to produce the quinolone 3. When the quinolone 3 is reacted with heterocycles such as piperidine or trifluoroacetamidopyr- rolidine, under the normal conditions (heating at reflux temperature in acetonitrile overnight) it produces the N-l dealkylated compound 4 with a heterocycle substituted at C-7. In a preferred synthesis, the coupling reaction of heterocycle was achieved in dimethylsulfoxide solvent in the presence of potassium dibasic phosphate buffer. Compound 4 is then hydrolyzed to the final product 5 by running the reaction at room temperature. In another aspect, as is mentioned above, this invention is a pharmaceutical composition comprising an antibacterially effective amount of a compound of Formula IC above. In still another aspect, this invention is a method of combat¬ ting bacterial infection in warm-blooded animals comprising adminis¬ tering to said animals an antibacterially effective amount of a com- pound of Formula IC or of a pharmaceutical composition thereof. Pharmaceutically acceptable base salts are formed by conven¬ tional techniques involving reaction of the compounds of Formula IC with alkali (Na,K) and alkaline earth (Ca, Ba, Zn, Mn) metal bases, more preferably with alkali metal bases such as, for example, dilute solutions of sodium hydroxide and potassium carbonate. Also, pharma¬ ceutically acceptable base salts are formed by conventional tech¬ niques involving reaction with amines such as, for example, triethyl- amine, dibenzylamine, triethanolamine, ethanolamine, N,N' -dibenzyl- ethylenediamine, procaine and equivalent amines. The antibacterial activity of the compounds of Formula IC was determined by using standard testing procedures such as the deter¬ mination of minimum inhibitory concentration (MIC) by agar dilution as described in "Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically" (MFT) published January 1983 by the National Committee for Clinical Laboratory Standards, 771 East Lancaster Avenue, Villanova, PA 19084, USA. Briefly, MIC values are determined in unsupplemented Mueller Hinton Agar (MHA) . The com¬ pounds tested are diluted serially into molten MHA at 47°C. The agar is poured into petri dishes and allowed to harden. The various bacteria used for testing are grown overnight on MHA at 35"C and transferred to Trypticase soy broth (TSB) until a turbidity of 0.5 McFarland standard is obtained. The bacteria are diluted one to 20 in TSB and inoculated on the plates (1 μl using a Steers replicator) . The plates are incubated at 35 β C for 20 hours and the MIC is read to be the lowest concentration of drug that completely inhibits visible growth of the bacteria. Ciprofloxacin was used as a control and the results of the compounds of the subject invention are shown in Table CI where A is (+. -)-6,8-difluoro-l,4-dihydro-l-(l,l-dimethyl-2-propynyl)-4-oxo-7- (l-piperazinyl)-3-quinolinecarboxylic acid methanesulfonate, B is (+, -)-7-(amino-1-pyrrolidinyl)-6,8-difluoro-1,4-dihydro-1- (1,1- dimethyl-2-propynyl)-4-oxo-3-quinolinecarboxylic acid, C is (+,-)- 6,8-difluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1-(2-propynyl)-3- quinolinecarboxylic acid methanesulfonate, D is (+,-)-7-(amino-l-pyr- rolidinyl)-6,8-difluoro-l,4-dihydro-4-oxo-l-(2-propynyl)-3-quinoline- carboxylic acid, and E is (+,-)-7-(3-amino-l-pyrrolidinyl)-l,4- dihydro-1-(1,1-dimethyl-2-propynyl)-6-fluoro-4-oxo-l,8-naphthyridine- 3-carboxylic acid methanesulfonate. It is to be understood that the formulas herein representing the various compounds according to the Invention are intended to embrace all optical isomers, as well as racemic mixtures thereof, within the scope of the given formulas unless otherwise indicated. In another aspect, as is mentioned above, this invention is a pharmaceutical composition comprising an antibacterially effective amount of a compound of Formula I above. In still another aspect, this invention is a method of combat¬ ting bacterial infection in warm-blooded animals comprising adminis- tering to said animals an antibacterially effective amount of a com¬ pound of Formula I or of a pharmaceutical composition thereof. Pharmaceutically acceptable base salts are formed by conven¬ tional techniques involving reaction of the compounds of Formula I with alkali (Na,K) and alkaline earth (Ca, Ba, Zn, Mn) metal bases, more preferably with alkali metal bases such as, for example, dilute solutions of sodium hydroxide and potassium carbonate. Also, pharma¬ ceutically acceptable base salts are formed by conventional tech¬ niques involving reaction with amines such as, for example, triethyl- amine, .dibenzylamine, triethanolamine, ethanolamine, N,N' -dibenzyl- ethylenediamine, procaine and equivalent amines. The pharmaceutical compositions of this invention may be pre¬ pared by combining the compounds of Formula I of this invention with a solid or liquid pharmaceutically acceptable carrier and, option¬ ally, with pharmaceutically acceptable adjuvants and excipients employing standard and conventional techniques. Solid form composi¬ tions 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 disintegrat¬ ing 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 appropriate amounts of the active component, that is, the compound of Formula I according to this invention. The quantity of active component, that is the compound of Form¬ ula I according to this invention, in the pharmaceutical composition and unit dosage form thereof may be varied or adjusted widely depend¬ ing 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. The compounds according to the invention have a potent and broad antimicrobial efficacy. These properties make it possible to use them as chemotherapeutic active compounds in medicine and as sub- stances for preserving inorganic and organic materials, in particular organic materials of all types, for example polymers, lubricants, dyes, fibers, leather, paper and wood, foodstuffs and water. The compounds according to the invention are active against Gram-negative and Gram-positive bacteria and bacterioid microorgan¬ isms. Thus, diseases caused by these pathogens can be treated. The compounds according to the invention are particularly active against bacteria and bacterioid microorganisms. Thus, they are part- icularly well suited for the chemotherapy of local and systemic In¬ fections caused by these pathogens in medicine. For example, local and/or systemic diseases caused by the fol¬ lowing pathogens or by mixtures of the following pathogens can be treated and/or prevented: Micrococcaceae, such as staphylococci, for example Staphylococcus aureua, Staph. Epidermidis, (Staph. — Staphyl¬ ococcus); Lactobacteriaceae, such as streptococci, for example Strep¬ tococcus pyogenes, a- and ?-haemolytic streptococci, non (7-) hae o- lytic streptococci, enterococci and Diplococcus pneumoniae (pneumo- cocci) (Str. — Streptococcus); Enterobacteriaceae, such as encherich- iae bacteria of the coli group; encherichia bacteria, for example Escherichia coli, enterobacter bacteria, for example aerogenes, E. cloacae, Klebsiella bacteria, for example K. pneumoniae, serratin, for example Serratia marcescens (E. — Enterobacter) (K. — Klebsi¬ ella) , proteae bacteria of the proteus groups; proteus, for example Proteus vulgaris, Pr. morganii, Pr. rettgeri and Pr. mirabilis (Pr. - Proteus) ; pseudomonadaceae, such as pseudomonas bacteria, for example Pseudomonas aeruginosa (PS. — Pseudomonas); bacteroidaceae, such as bacteroides bacteria, for example Bacteroides fragilis (B. — Bacter- oides) ; mycoplasma, for example Mycoplasma pneumonia. The present invention includes pharmaceutical preparations which in addition to non-toxic, inert pharmaceutically suitable excepients contain one or more compounds according to the invention or which consist of one or more active compounds according to the invention, and processes for the production of these preparations. The present invention also includes pharmaceutical preparations in dosage units. This means that the preparations are in the form of individual parts, for example tablets, dragees, capsules, pills, sup¬ positories and ampoules, of which the content of active substance corresponds to a fraction or a multiple of an individual dose. An individual dose preferably contains the amount of active compound which is given in one administration and which usually corresponds to a whole, a half or a third or a quarter of a daily dose. By non-toxic, inert pharmaceutically suitable excipients there are solid, semi-solid or liquid diluents, fillers and formulatio auxiliaries of all kinds. Preferred pharmaceutical preparations ar tablets, dragees, capsules, pills, granules, suppositories, solu tions, suspensions and emulsions, pastes, ointments, gels, creams, lotions, powders and sprays. Tablets, dragees, capsules, pills and granules can contain th active compound or compounds alongside the customary excipients suc as (a) fillers and extenders, for example starches, lactose, sucrose, glucose, mannitol and silica, (b) binders, for example carboxymeth l- cellulose, alginates, gelatine and polyvinylpyrrolidone, (c) humec- tants, for example glycerine, (d) disintegrating agents, for exampl agar-agar, calcium carbonate and sodium carbonate, (e) solution re- tarders, for example paraffin, and (f) absorption accelerators, fo example quaternary ammonium compound (g) wetting agents, for exampl cetyl alcohol or glycerine monostearate, (h) adsorbents, for exampl kaolin and bentonite, and (i) lubricants, for example talc, calciu stearate and magnesium stearate and solid polyethylene glycols, o mixtures of the substances listed under (a) to (i) . The tablets, dragees, capsules, pills and granules can be pro- vided with the customary coatings and shells, optionally containin opacifying agents, and can also be of such composition that the release the active compound or compounds only, or preferentially, i a certain part of the intestinal tract, optionally in a delaye manner, examples of embedding compositions which can be used bein polymeric substances and waxes. The active compound or compounds, optionally together with on or more of the above mentioned excipients, can also be in a micro- encapsulated form. Suppositories can contain, in addition to the active compound o compounds, the customary water-soluble or water-insoluble excipients, for example polyethylene glycols, fats, for example cacao fat, and higher esters (for example C 4-alcohol with C g-fatty acid) or mix¬ tures of these substances. Ointments, pastes, creams and gels can contain the customary excipients in addition to the active compound or compounds, for example animal and vegetable fats, waxes, paraffins, starch, traga- canth, cellulose derivatives, polyethylene glycols, silicones, ben- tonites, silica, talc and zinc oxide or mixtures of these substances. Powders and sprays can contain the customary excipients in addition to the active compound or compounds, for example lactose, talc, silica, aluminum hydroxide, calcium silicate and polyamide powders or mixtures of these substances. Sprays can additionally contain the customary propellents, for example chlorofluorohydro- carbons. Solutions and emulsions can contain the customary excipients in addition to the active compound or compounds, such as solvents, solu- bilising agents and emulsifiers, for example water, ethyl alcohol, isopropyl alcohol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1,3-butylene glycol, dimethyIfor- mamide, oils, especially cottonseed oil, groundnut oil, maize germ oil, olive oil, castor oil and sesame oil, glycerine, glycerine- formal, tetrahydrofurfuryl alcohol, polyethylene glycols and fatty acid esters of sorbitan, or mixtures of these substances. For parenteral administration, the solutions and emulsions can be in a sterile form which is isotonic with blood. Suspensions can contain the customary excipients in addition to the active compound or compounds, such as liquid diluents, for exam- pie water, ethyl alcohol or propylene glycol, suspending agents, for example ethoxylated isostearyl alcohols, polyoxyethylene sorbitol esters and sorbitan esters, microcrystalline cellulose, aluminium metahydroxide, bentonite, agar-agar and tragacanth or mixtures of these substances. The formulation forms mentioned can also contain dyestuffs, preservatives and additives which improve the odour and flavour, for example peppermint oil and eucalyptus oil, and sweeteners, for exam¬ ple saccharin. The therapeutically active compounds should preferably be pre- sent in the above mentioned pharmaceutical preparations in a concen¬ tration of about 0.1 to 99.5, preferably of about 0.5 to 95, percent by weight of the total mixture. The above mentioned pharmaceutical preparations can also contain other pharmaceutical active compounds in addition to the active com- pounds according to the invention. The above mentioned pharmaceutical preparations are manufactured in the usual manner according to known methods, such as by mixing the active compound ^>r compounds with the excipient or excipients. The active compounds or the pharmaceutical preparations can be administered locally, orally, parenterally, intraperitoneally and/or rectally, preferably orally or parenterally, such as intravenously or intramuscularly. In general, it has proved advantageous in medicine to administer the active compound or compounds in total amounts of about 0.5 to about 50, preferably 1 to 30, especially preferably 1-20 mg/kg of body weight, orally or parenterally, every 24 hours, optionally in the form of several individual administrations, in order to achieve the desired results. An individual administration contains the active compound or the active compounds preferably in amounts of about 1 to about 250, especially of 3 to 60, mg/kg of body weight. However, it can be necessary to deviate from the dosages mentioned and in particular to do so as a function of the nature and body weight of the subject to be treated, the nature and the severity of the illness, the nature of the preparation and of the administration of the medicine, and the time or interval over which the administra¬ tion takes place. Thus it can suffice in some cases to manage with less than the above mentioned amount of active compound whilst in other cases the above mentioned amount of active compound must be exceeded. The particular required optimum dosage and the type of administration of the active compounds can easily be decided by anyone skilled in the art, on the basis of his expert knowledge. The new compounds can be utilized as feedstuff. Example 1 Preparation of 2- [4-(l-Cyclopropyl-3-carboxy-6,8-di- fluoro-1,4-dihydro-4-oxo-7-quinolinyl)-1-piperazin¬ yl]2-butenedioic acid, dimethyl ester. The preparation of this compound is illustrated in Scheme 3, below. The starting material "A" is disclosed in J. Med. Chem., 31(5), 991-1001, by Domagala, et al. This ester (1.64 g, 5.27 mmol) dissolved in 120 ml of DMF and 590 mg, (6.84 mmol) of piperazine was added with stirring overnight at 55° C. The mixture was allowed to cool to 23° C, filtered and washed with ethyl alcohol to yield 594 mg of a white powder "B". The amino ester B (500 mg, 1.32 mmol) was dissolved in 20 ml of chloroform and 163 μl_ (1.32 mmol of dimethyl acetylene dicarboxylate was added. The product C was then obtained by evaporating off the solvent. Product C (250 mg, 0.48 mmol) was dissolved in 2.0 ml of THF and 1.0 ml (2.0 mmol) of potassium hydroxide and stirred at 23 β C for 24 hours. The THF was then removed by vacuum and the residue dissolved in 25 ml of water and washed with 25 ml of ethyl acetate. The acid- ity was adjusted to pH 6 and a white participate formed. The parti¬ cipate D was filtered, air dried and washed with ethyl alcohol to yield 180 mg of the subject product In 81% yield. Example 2 Preparation of 2-[4-(l-Ethyl-3-carboxy-6-fluoro-l,4- dihydro-4-oxo-7-quinolinyl)-l-piperizinyl]2-butene- dioic acid, dimethyl ester. The preparation of this compound is Illustrated in Scheme 4, below. The starting material A is disclosed in J. Chem. Soc, 1664 (1967) by Bartett, R.K. and Humphrey, L.R. The starting material A (1 g, 37 mmol) was admixed with 14 ml of pyridine and 1.58 g (18.5 mmol) of piperazine at 60" C for about 4 hours. The solvent was removed under nitrogen and the product B recrystallized from ethyl alcohol. The piperazine product B yield was 72%, 0.85 g, melting point 195-201" C. Product B (0.4 g, 1.25 mmol) was admixed with 10 ml. of DMF and 154 λ (1.25 mmol) of acetylene dicarboxylate at room temperature for about 2 hours. The solvent was then evaporated under nitrogen and the residue recrystallized from DMF and ethyl alcohol. The product C was dried in an oven at 60" C to obtain 265 mg, 235-239" C melting point, in 46% yield. Example 3 Preparation of 2-[4-(l-Cyclopropyl-3-carboxy-6-fluoro- 1,4-dihydro-4-oxo-7-quinolinyl)-1-piperazinyl]2-but¬ enedioic acid, dimethyl ester. The preparation of this compound is illustrated in Scheme 5, below. The starting material A is disclosed in Chemical Abstracts 106:201748f. The starting material A (500 mg, 1.45 mmol) was dissolved in 10 ml chloroform and added to 178 μ ~ (1.45 mmol) dimethylacetylene dicarboxylate. The mixture was stirred overnight at room temperature and then chromatographed over 150 g of silica dioxide and flushed with chloroform and ethyl alcohol (96:4). The product B was recry¬ stallized in ethyl acetate to yield 727 mg of white solid. The ester product B (200 mg, 0.41 mmol) was added to 1 ml of THF, 2 ml of 2N potassium hydroxide and stirred at 30° C for about 4 hours.. After all material had dissolved the THF was evaporated an the remaining mixture was diluted with 10 ml of water. The pH wa adjusted to 7 and a white participate formed. The participate wa filtered and dried to yield 141 mg of a white solid product C, melt- ing point 225-226" C. 73% yield. Example 4 Preparation of 2-[4-(3-carboxy-l-cyclopropyl-6,8- difluoro-l,4-dihydro-4-oxo-7-quinolinyl)--1-piperazin¬ yl]-2-pentenedioic acid-(E)-l,5-dimethyl ester. The preparation of this compound is illustrated in Scheme 6, below. The amino acid (A, 350 mg, 1.0 mmol) was dissolved in DM (6.0 mL) and 3-chloro-l,5-pentenedioic acid dimethyl ester (193 mg, 1.0 mmol) was added. The reaction was stirred overnight at 50°C, then DBU (2 equivalents) was added. The reaction immediately turne red. The reaction was stirred for 1 hour, then the solvent was removed under a stream of dry N2 gas. The residue was chromatograph- ed (flash Siθ2, 100 g) , eluting with methylene chloride / methanol / acetic acid (90 : 10 : 0.5), to give the product as a pale orange solid (167 mg, 33 %) . MP - 158-61°C, dec. Example 5 Preparation of 2-[4-(5-amino-3-carboxy-l-cyclopropyl- 6 , 8-difluoro-l , 4-dihydro-4-oxo-7-quinolinyl) -1- piperazinyl]-2-butenedioic acid, (E)-l,4-dimethyl ester. The preparation of this compound is illustrated in Scheme 7, below. The starting material A is disclosed in J. Med. Chem., 30, p. 2285 (1987) by L. Mitscher, et al. The starting material A (27.46 g, 97.4 mmol) was admixed with 41 ml of acetic anhydride and 17.4 g (117.4 mmol) triethylor- thoformate and refluxed for about 3 hours. The mixture was evapora¬ ted at 60°C and azeotroped with toluene three times to yield 32.98 g of product B. The enol ether B (12 g, 35.5 mmol) was added to 2.05 g, 36 mmol of cyclopropylamine in 50 ml of methylene chloride and stirred at room temperature. This mixture was evaporated under vacuum and the product added to 600 g silica gel packed and eluted with methyl- ene chloride. Approximately 11.43 g of the product C was obtained in a 92% yield and had a melting point of 88-92°C. The ena ine C (10 g, 27 mmol) was stirred in 185 ml of THF at 0°C and 1.14 g of a 60% oil dispersion of sodium hydride was added.- The mixture was evaporated under vacuum, transferred to a separation funnel, extracted three times with chloroform and dried over magnesium sulfate. This procedure yielded 10.6 g of product which was recrystallized from ethyl acetate to give 8.28 g of product D, melting point 166-169°C, in 88% yield. The tetrafluoro ester D (6.0 g, 18.7 mmol) was admixed to 2.75 g potassium carbonate and 2.0 g (18.7 mmol) of benzylamine in 200 ml acetonitrile and refluxed for 3 hours. The solid was filtered off, the filtrate evaporated and the residue added to 700 g of silica gel packed and eluted with 3% methanol/methylene chloride. This procedure afforded 4.15 g of E in 55% yield, melting point 130-133°C. The benzylamine E (1.85 g, 4.45 mmol) was dissolved in 17 ml ethanol and 11 ml acetic acid with 10% palladium on carbon (0.28 g) and shaked for 1.5 hours under 12 pounds hydrogen pressure. The mixture was filtered rinsing with chloroform. The filtrate was evaporated and the residue triturated with ethanol to give 1.23 g of the product F in 85% yield, melting point 228-232°C. A mixture of trifluoro ester F (0.5 g, 1.53 mmol) and 0.65 g of piperazine (7.65 mmol) in 25 ml of acetonitrile was refluxed for 1 day. The mixture was evaporated under vacuum and the residue added to 50 g of silica gel packed with 5% methanol/methylene chloride. Elution with 5-15% methanol/ methylene chloride afforded 0.54 g (90% yield) of product which was recrystallized from ethyl acetate/- methylene chloride, melting point 209-219°C. Ester G (0.24 g, 0.62 mmol) was stirred for 1 day in 6 ml of tetrahydrofuran and 3 ml of 2 N aqueous potassium hydroxide. The tetrahydrofuran was evaporated off under vacuum and the resulting aqueous layer was neutralized with 2N hydrochloric acid. The product was filtered off and washed with water, ethanol, and ether to afford 0.11 g (49% yield) of product H, melting point 228-235°C. Product I was prepared as B in example 2. The amino acid H (0.17 g) was converted to 64 mg (27% yield) of I after silica gel chromatography (0.5% acetic acid, 10% methanol/methylene chloride) and recrystallization from methanol/methylene chloride. mp 171- 186°C. Example 6 Preparation of 2-[4-(3-carboxy-l-cyclobutyl-6,8- difluoro-1,4-dihydro-4-oxo-7-quinolinyl)-1-piperazin¬ yl] -2-butenedioic acid (E)-1,4-dimethyl ester. The preparation of this compound is illustrated in Scheme 8, below. The starting material A is disclosed in J. Med. Chem. 31, p. 991 (1988) by J.M. Domagala et al. Piperazine was added to A as in Example 5. Refluxing A (2.0 g) with piperazine in acetonitrile for 2 days followed by column chromatography afforded 2.03 g (84% yield) of B which was recrystall¬ ized from Et0Ac/CH 2 Cl (mp 188-192°C). Ester B (0.5 g) was refluxed in 36 ml of 6N hydrochloric acid for 7 hours. Evaporation of the solvent under nitrogen and recrystallization of the residue from ethanol afforded 0.296 g (64%) of product C, mp 310-328°C. Product D was prepared as B in example 2. The amino acid C (0.27 g) was converted to 0.214 g (57% yield) of D after recrystal¬ lization from ethanol (mp 215-221°C). Example 7 Preparation of 2-[4-(3-carboxy-l-benzene(4-fluoro)- 6, 8-difluoro-l, 4-dihydro-4-oxo-7-quinolinyl) -1- piperazinyl]-2-butenedioic acid, (E)-1,4-dimethyl ester. The preparation of this compound is illustrated in Scheme 9, below. The starting material A is disclosed in J. Med. Chem. 30, p. 504 (1987) by D.T.W. Chu et al. Product B was prepared as B in example 2. The amino acid A (0.4 g) was converted to 0.35 g (64% yield) of B after recrystalliza¬ tion from dimethyl formamide/ethanol (mp 244-251°C). Example 8 Preparation of 2-[4-(3-carboxy-l-benzene(2,4-difluo- ro)-1,4-dihydro-4-oxo-7-quinolinyl)-1- (3-aminopyr- rolidinyl)] -2-butenedioic acid, (E)-1,4-dimethyl ester. The preparation of this compound is illustrated in Scheme 10, below. The starting material A is disclosed in J. Med. Chem. 30, p. 504 (1987) by D.T.W. Chu et al. Product B was prepared as B in example 2. The amino acid A (0.23 g) was converted to 85 mg (27% yield) of B after chromatography over 80g silanized silica gel packed and eluted with chloroform and recrystallization from methylene chloride/hexane (mp 176-182°C). Example 9 Preparation of 2-[4-(3-carboxy-l-cyclopropyl-6,8- difluoro-1,4-dihydro-4-oxo-7-quinolinyl)-l-(3-amino- pyrrolidinyl)] -3-butenoic acid-(E)-l-methyl ester. The preparation of this compound is illustrated in Scheme 11. The preparation of the starting material A is described as "B" in example 10, scheme 2. The amino acid A (200 mg, 0.57 mmol) was dissolved in DMF (1.0 mL) and heated to 150°C for 4 h with methylacetoacetate (108 uL, 1.0 mmol). The mixture was then cooled and DMF removed under a stream of dry nitrogen. The residue was extracted with methylene chloride and concentrated, then chro atographed over silanized silica gel, eluting with 3 % ethanol in methylene chloride, giving the product B (159 mg, 63 %) as a pale yellow powder. MP - 189-91°C, dec. Example 10 Preparation of 2-[4-(3-carboxy-l-cyclopropyl-6,8- difluoro-1,4-dihydro-4-oxo-7-quinolinyl)-l-(3-amino- pyrrolidinyl)]-2-butenedioic acid-(E)-1,4-dimethyl ester. The preparation of this compound is illustrated in Scheme 2. The trifluoro ester (described as A in Scheme 3, 18.0 g, 57.8 mmol) was admixed with 3-acetamidopyrrolidine (7.41 g, 57.8 mmol) in acetonitrile (100 mL) . Triethyl amine (8.22 mL, 59 mmol) was added and the mixture stirred at 57°C for 24 h. The solvent was removed and the residue dissolved in methylene chloride and washed with water, then concentrated and chromatographed over flash silica gel eluting with 5 % ethanol In methylene chloride to give the product A (15.4 g, 64 %) as a white solid. MP - 132-5°C. The product A (2.0 g, 4.8 mmol) was then dissolved in 2 N K0H (14 mL) and heated to reflux for 6 h, then neutralized under heating with acetic acid. On cooling the mixture was filtered and the filtrate discarded. The product was then dissolved in 2.5 % acetic acid in water (2.5 mL / 100 mL) and filtered thru a medium frit. The filtrate was made to pH 10 with 50 % sodium hydroxide and neutralized with acetic acid to give a white powder which was filtered and washed with methanol and ether to give B as a white powder (809 mg, 48 %) . The product B (400 mg, 1.2 mmol) was dissolved in a mixture of chloroform (3.0 mL) and DMF (0.5 mL) and dimethylacetylenedicarboxy- late (141 uL, 1.2 mmol) was added. the mixture was stirred for 24 h at 23°C, then the solvent was removed under a stream of dry nitrogen gas and the residue was chromatographed over silanized silica gel, eluting with chloroform to give the product C (354 mg, 63 %) as an off white solid. MP - 173-5°C, dec. Example 11 Preparation of 2-[4-(l-Cyclopropyl-3-carboxy-5,6,8- trifluoro-1,4-dihydro-4-oxo-7-quinolinyl)-1-piperazin¬ yl]2-butenedioic acid, dimethyl ester. The preparation of this compound is illustrated in Scheme 13, below, and the starting material A is disclosed in Scheme 7. The tetrafluoro ester A (0.44 g) was admixed with 5 ml of pyridine and 0.12 g of piperazine for about 1 day. The pyridine wa then evaporated off under nitrogen and the residue chromatographe over silica gel (5-10% methanol/methylene chloride) to afford 0.166 (31% yield) of the product B which was recrystallized from methylene chloride/hexane. mp 227"C. The product C was prepared as C in example 1. The amino ester B (0.23 g, 0.58 mmol) was converted to 0.21 g (67% yield) of C after chromatography over 20 g silica gel packed and eluted with 3% methanol/methylene chloride and recrystallization fro ethanol/ethyl acetate (mp 224-7"C). The ester C (0.15 g) was admixed with 5 ml of methylene chloride and 100 mg of potassium trimethylsilanolate at room tempera¬ ture for about two days. Column chromatography over 20 g of silica gel packed and eluted with 0.5% acetic acid, 10% methanol in methyl¬ ene chloride followed by recrystallization from ethanol afforded 60 mg (41% yield) of product D, mp 215-223"C. The ester D (2 g, 6.08 mmol) was refluxed in 6N (150 ml) hydro¬ chloric acid for about seven hours and evaporated at 70" C. The residue was recrystallized from ethyl alcohol to yield 0.59 g of product E, melting point 169-177"C. The tetrafluoro acid E (0.4 g, 1.33 mmol) was admixed with 5.5 ml of pyridine and 0.42 g (4.8 mmol) of piperazine and heated to 60° C for about 1.5 hours. The pyridine was then evaporated off under nitrogen and the product recrystallized from ethyl alcohol with ethyl acetate to yield 0.34 g of product F, melting point 230-238°C, in 70% yield. The piperazine compound F (0.2 g, 0.54 mmol) with 5 ml of DMF was added to 66 μL (0.54 mmol) of acetylene dicarboxylate and stirred at room temperature for about 2 hours. The solvent was removed under nitrogen, the residue recrystallized from ethylalcohol and dried in vacuum at 60°C to yield the product F, .202 mg, melting point 170- 180°C, in 70% yield. Example 12 Preparation of l-(bicyclo[l.l.l]pent-l-yl)-6,8- difluoro-1,4-dihydro-4-oxo-7-(l-piperazinyl)-3- quinolinecarboxylic acid (Cpd #1) Part A: A 50 ml one-neck round bottom flask Is equipped with a magnetic stirring bar condenser and gas inlet. To this flask is added ethyl 2,3,4,5-tetrafluorobenzoyl acetate (2.8 g, 10.6 mmol) along with acetic anhydride (6.5 g, 63.6 mmol) and triethyl orthoformate (2.4 g, 15.9 mmol). After stirring, within a few minutes the mixture is com- pletely dissolved to give a clear solution. This mixture is refluxed for 3 hours (oil bath at about 140*C) . The condenser is periodically removed to allow EtOAc to evaporate as It is formed. At this time the TLC shows a new product present. The volatiles are removed under reduced pressure and the contents of the flask are further concen- trated to a constant mass at high vacuum (.4 mmHg) . 1 H nmr shows a mixture of the desired cis and trans product. 3.1 g of an orange oil is obtained which is stored under nitrogen in the freezer until needed. Part B: 1-Amino-bicyclo[l.l.l]pentane hydrochloride (250 mg, 2.09 mmol) is placed into a 50 ml round bottom flask equipped with a magnetic stirring bar and gas inlet. Then 10 ml of CH2CI2 is added. Next the enol ether obtained above (670 mg, 2.09 mmol), dissolved in 2 ml of CH2CI2 is added, and the mixture is cooled to 0"C with an ice bath. Next a solution of Hunig's base (270 mg, 2.09 mmol) in 3 ml of CH 2 Cl2 is added and the mixture is allowed to stir for one hour at 0"C. The reaction mixture is allowed to stir an additional hour at room tem¬ perature. TLC of the mixture at this time shows complete consumption of starting material. The reaction mixture is concentrated to leave behind an orange waxy solid. The mixture is chromatographed on sil¬ ica gel. Elution with 5:1 hexane/EtOAc gives 470 mg of the enamino keto ester as a light yellow gummy solid. Part C: In a flame dried 35 ml flask equipped with a pressure equalizing addition funnel, magnetic stirring bar, and gas inlet is placed NaH (40 mg, 0.560 mmol) as a 50% oil suspension. Next 5 ml of dry THF is added and the whole is cooled to 0°C with an ice bath. Next the enamino keto ester obtained above (100 mg, 0.280 mmol) dissolved in 20 ml of dry THF is added dropwise via the addition funnel. After the addition is complete the reaction mixture is heated in an oil bath at 50"C for 15 minutes. TLC at this time shows complete con¬ sumption of starting material. The reaction mixture is cooled to 0°C and treated with 0.5 ml of HOAc to consume any unreacted NaH. The mixture is then concentrated in vacuum to give a yellow gummy solid. After further drying at .4 mHg for one hour a light yellow solid results. The crude material is chromatographed on silica gel (elution 400 ml CHC1 3 followed by 500 ml 5% MeOH/CHCl 3 ) to give 1- (bicyclo[1.1.1]pent-l-yl-l,4-dihydro-6,7,8-trifluoro-4-oxo-3-quinol¬ ine carboxylic acid ethyl ester as a white solid (68 mg, mp-176- 178°C)). Part D: A 25 ml flame dried round bottom flask is equipped with a reflux condenser, magnetic stirring bar, and gas inlet. The system is purged with nitrogen and the trifluoroquinolone obtained above (150 mg, 0.445 mmol) is added along with 10 ml dry CH3CN. Then piperazine (191 mg, 2.22 mmol) is added. The resultant red solution is brought to reflux. As reflux begins the solution becomes yellow. The mix- ture is left to reflux overnight. The reaction mixture is concen¬ trated and triturated with ether to leave a pale peach colored solid. This gives a 140 mg sample (mp-185-187"C) which is pure by -*-H nmr and 100 mg of a pink solid which has a mixture of materials. The pure material is pushed to the next step. Part E: The ester obtained above (90 mg, 0.223 mmol) is suspended in 1 ml of water and 1.2 ml IN aqueous NaOH is added. The suspension is refluxed for one hour. The solution is cooled and adjusted to pH near 7.5 with IN HC1. The precipitate is filtered and washed with water and dried in vacuo to give 55 mg of Compound No. 1 (mp-=225- 226°C). Example 13 Preparation of l-(bicyclo[l.l.l]pent-l-yl)-6- fluoro-4-oxo-7- (1-piperazinyl) -3-quinolinecar¬ boxylic acid (Cpd #2) Part A: A 250 ml flame dried round bottom flask is equipped with a pressure equalizing addition funnel, magnetic stirring bar, and gas inlet. The flask is charged with a 50% sodium hydride-in-oil suspen- sion (3..74 g, 78.0 mmol) along with 20 ml of dry THF. The slurry of NaH is cooled to 0"C with an ice bath and a solution of 2,4-dichloro- 5-fluoroacetophenone (7.8 g, 37.6 mmol) in 100 ml of diethylcarbonate (100 ml) is added slowly (dropwise) to the slurry of NaH. After the addition is complete the mixture Is stirred at room temperature until gas evolution ceases (30 minutes) . The deep red-orange solution is then heated to 80"C for 1.5 hours. The reaction mixture is poured into an ice-cold water (250 ml) solution containing acetic acid (8 ml). The mixture is extracted (3 X 150 ml) with ether, dried over Na2S04, and concentrated to an orange oil. The oil is distilled at high vacuum (1 mmHg 133-135"C). 7.9 g of ethyl 2,4-dichloro-5- fluorobenzoylacetate is obtained as a light yellow oil. Part B: Into a 25 ml flask equipped with a magnetic stirring bar and reflux condenser is placed the benzoylacetate obtained above (2.0 g, 7.17 mmol) along with acetic anhydride (4.75 g, 46.6 mmol) and tri- ethyl orthoformate (1.6 g, 10.8 mmol). The solution is heated at 130°C for 2.5 hours with frequent removal of the condenser to remove ethyl acetate as it forms during the reaction. The solution is con- centrated under reduced pressure to constant weight. Part C: Into a 50 ml flask equipped with a magnetic stirring bar and gas inlet is placed the enol ether obtained above (840 mg, 2.50 mmol) and l-amino-bicyclo[l.l.l]-pentane hydrochloride (300 mg, 2.50 mmol) in 15 ml of CH2CI2. This solution is cooled to 0°C and Hunig's base (323 mg, 2.50 mmol) is added. The mixture is stirred until room temperature is reached. The reaction mixture is concentrated to a solid material. TLC shows starting material to be consumed. The mixture is chromatographed on silica gel (MPLC) eluting hexane/ethyl acetate (7:1). 720 mg of the enamino keto ester is obtained as a yellow viscous oil. Part D: Into a 100 ml flame dried flask equipped with a pressure equalizing addition funnel, magnetic stirring bar, and gas inlet was placed NaH (169 mg 50% oil suspension, 3.52 mmol) along with 10 ml of dry THF. The slurry was cooled to 0°C and a solution of the enamino keto ester obtained above (630 mg, 1.76 mmol) dissolved in 35 ml of dry THF was added dropwise via the additional funnel. After the addition was complete the mixture was heated at 80"C for 3 hours. The mixture was then cooled to 0"C and acidified with 2 ml of glacial acetic acid. Concentration to dryness, followed by chromatography on silica gel (eluted with CHCI3, moving to 5% MeOH/CHCl 3 ) gave 470 mg of 1-(bicyclo[1.1.1]pent-1-yl)-1,4-dihydro-6-fluoro-7-chloro-4-oxo- quinoline-3-carboxylic acid ethyl ester (m.p.-223-225"C). Part E: The quinolone ester obtained in the previous step (349 mg, 1.04 mmol) is slurried in 3 ml of H2O. Next 5 ml of IN NaOH is added and the mixture is brought to reflux. After one hour reflux, TLC shows starting material to be consumed and a low Rf material forms. The mixture is cooled to 0°C and acidified to pH 7. The solids are filtered, washed with water, cold ethanol, and ether. Drying under vacuum gives 290 mg of an off-white solid (mp>250"C). Part F: The quinolone acid obtained above (120 mg, .390 mmol) is slurried in 3 ml of pyridine and piperazine (134 mg, 1.56 mmol) is added. The mixture is brought to reflux and stirred under nitrogen at this temperature for 18 hours. At this time water is added to give a solution which is extracted (4 X 50 ml) with chloroform. Reverse phase TLC (elution with 4:1 MeOH/0.05 M BU4NHSO4) shows UV active material of extracts different than starting material. The chloroform layer is dried and concentrated to give 116 mg of an off- white solid. Recrystallization from 5:1 Et2θ/CH2Cl2 gives 75 mg of Compound No. 2 (mp-233-235°C) . Following the general procedure of Examples 1 and 2, and making non-critical variations, except starting with the appropriate naphthyridine- or quinoline-esters .5 or the corresponding acids 1_ and introducing the appropriate heterocyclic amine (R7) , the compounds described in Table I can be prepared. The compounds according to the invention have good actions against Gram-positive and Gram-negative bacteria. The effectiveness of the subject compounds on some bacteria were obtained by performing a dipped disk assay. The antibacterial activ- ity of the compounds is determined by the disk-diffusion method. Paper disks (12.7 mm) were loaded with 0.10 ml of drug solution pre¬ pared at a concentration of 1 and 0.1 mcg/ml; the disks were allowed to air dry. They were then applied to the surface of microorganism- seeded 'agar assay trays, which contained the bacterial strain Pseudo¬ monas aeruginosa UC 95 (PA) , Escherichia coli UC 51 (EC) or Staphylo¬ coccus aureus UC 80 (SA) . The assay trays were incubated overnigjht under aerobic condition to allow for the growth of the organisms. Zones of growth inhibition due to the action of the antibiotic were then measured to the nearest millimeter. (Growth Inhibition Zone, in mm) Compound Cipro Cipro The results show that compounds 1 and 2, corresponding to Examples 1-2, above, have potent gram negative and positive activity as compared to the commercially available antibacterial Ciprofloxacin ("Cipro"), from Miles Pharm. Div. , West Haven, CT. Compounds of this invention can also be tested for in vitro antimicrobial activity using standard testing procedures such as the determination of minimum inhibitory concentration (MIC) by agar dilu¬ tion as described in "Methods for Dilution Antimicrobial Susceptibil- ity Tests for Bacteria That Grow Aerobically" (MFT) published January 1983 by the National Committee for Clinical Laboratory Standards, 771 East Lancaster Avenue, Villanova, PA 19084, USA. Briefly, MIC values are determined in unsupplemented Mueller Hinton Agar (MHA) . The compounds tested are diluted serially into molten MHA at 47°C. The agar is poured Into petri dishes and allowed to harden. The various bacteria used for testing are grown overnight on MHA at 35°C and transferred to Trypticase soy broth (TSB) until a turbidity of 0.5 McFarland standard is obtained. The bacteria are diluted one to 20 in TSB and inoculated on the plates (1 μl using a Steers replicator) . The plates are incubated at 35°C for 20 hours and the MIC is read to be the lowest concentration of drug that completely inhibits visible growth of the bacteria. The MIC test results of selected of Formula B compounds of this invention are found in Tables B2-B9. The compounds according to the invention have a potent and broad antimicrobial efficacy. These properties make it possible to use them as chemotherapeutic active compounds in medicine and as sub¬ stances for preserving inorganic and organic materials, in particular organic materials of all types, for example polymers, lubricants, dyes, fibres, leather, paper and wood, foodstuffs and water. The compounds according to the invention are active against Gram-negative and Gram-positive bacteria and bacterioid microorgan¬ isms. Thus, diseases caused by these pathogens can be treated. The compounds according to the invention are particularly active against bacteria and bacterioid microorganisms. Thus, they are par¬ ticularly well suited for the chemotherapy of local and systemic infections caused by these pathogens in medicine. For example, local and/or systemic diseases caused by the fol- lowing pathogens or by mixtures of the following pathogens can be treated and/or prevented: Micrococcaceae, such as staphylococci, for example Staphylococcus aureus, Staph. Epidermidis, (Staph. - Staphyl¬ ococcus); Lactobacteriaceae, such as streptococci, for example Strep¬ tococcus pyogenes, a- and /3-haemolytic streptococci, non (7-) haemo- lytic streptococci, enterococci and Diplococcus pneumoniae (pneumo- cocci) (Str. - Streptococcus); Enterobacteriaceae, such as encherich- iae bacteria of the coli group; encherichia bacteria, for example Escherichia coli, enterobacter bacteria, for example, E. aerogenes, E. cloacae, Klebsiella bacteria, for example K. pneumoniae, serratin, for example Serratia marcescens (E. — Enterobacter) (K. - Klebsi¬ ella) , proteae bacteria of the proteus groups; proteus, for example Proteus vulgaris, Pr. morganii, Pr. rettgeri and Pr. mirabilis (Pr. - Proteus); pseudomonadaceae, such as pseudomonas bacteria, for example Pseudomonas aeruginosa (PS. - Pseudomonas); bacteroidaceae, such as bacteroides bacteria, for example Bacteroides fragilis (B. — Bacter¬ oides); mycoplasma, for example Mycoplasma pneumonia. Example 14 (+, -)-7- (3-amino-1-pyrrolidinyl)-1,4-dihydro-l-(1,1- dimethyl-2-propynyl)-6-fluoro-4-oxo-l,8-naphthyridine- 3-carboxylic acid methanesulfonate The preparation of this compound is structurally depicted in Scheme 17, below. To a solution of pyridine enolether 6 (620 mg, 1.8 mM) in ethanol (5 ml) at room temperature dimethylpropargyl amine (0.6 ml, dried over MgS04) was added with stirring. The reaction mixture was concentrated in vacuo after 3.5 hours. This coupled intermediate 7 was used directly for the next cyclization step. It was dissolved in THF (10 ml) and cooled in an ice bath. NaH (100 mg of 50% NaH dispersed in oil) was added and the mixture was stirred at 0"C for 2 hours and for 2 hours at room temperature. The desired product was precipitated out of the reaction mixture which was filtered, washed with H2O and Et2 ~ 0 and dried to obtain the first crop of 8 (310 mg). The filtrate was washed with EtOAc and the organic layer was taken, dried over MgSU4 and concentrated in vacuo . The residue was tritu¬ rated with ether to obtain the 2nd crop of 8 (55 mg) . Total 365 mg (1.1 mM), yield 61%; mp 229-231"C (decomp.). A heterogeneous mixture of the naphthridine ester 8 (168 mg, 0.5 mM) , 3-N-trifluoroacetyl aminopyrrolidine hydrochloride salt (120 mg, 0.55 mM) and K2HPO (220 mg) in DMSO was stirred at room temperature for 2 days. The desired trifluoroacetylaminopyrolidine coupled product 9 was precipitated out of the reaction mixture and the solid was filtered, washed with H2O and EtOAc and dried to obtain the pure product 9 (225 mg, 4.7 mM) in 94% yield; mp 268-270 β C (decomp.). IH NMR (dg-DMSO) δ 9.7 (s, IH) , 9.1 (s, IH) , 7.89 (d, J-13 Hz, IH) , 4.5 (broad multiplet, IH) , 4.21 (q,J-7 Hz, 2H) , 3.7-4.1 (m, 5H including one single at 3.8 for C«C-H) , 2.0-2.3 (m, 8H including one singlet at 2.12 for 6H), 1.27 (t, J-7 Hz, 3H) ; IR (mineral oil) 1695, 1630, 1444 cm "1 ; HRMS (m/z) 482.1569 (calcd for C 22 H22 F 4 N 4°4482.1577). Naphthridine ester 9 (650 mg, 1.35 mM) was dissolved in DMSO (20 ml) containing aq. NaOH (240 mg of 50% NaOH in 3 ml H2O by heating briefly at 75°C) . The mixture was allowed to cool to room tempera¬ ture over 1 hour and then left at room temperature overnight. The DMSO was removed in vacuo and the residue was dissolved in 15 ml of H2O whose pH was 9.8 at this point. The pH of the solution was adjusted to 7 by use of IN HC1. The carboxylic acid product was precipitated out of the solution which was filtered, washed with H2O and dried to obtain 360 mg of solid which was found to be the acid 10 with trifluoroacetyl group of the pyrrolidine ring intact. The filtrate solution was concentrated again in vacuo and the residue was redissolved in H2O (5 ml) . The pH of the solution was readjusted to 7 to induce the additional solid precipitation. The solid precipi¬ tate was filtered, washed with H2O followed by Et2θ and dried to obtain 135 mg of solid. Two batches of solid (360 mg and 135 mg) were subjected into a hydrolysis reaction condition separately. A mixture of 360 mg solid, 150 mg of 50% NaOH, 15 ml of H2O and 5 ml of methanol was heated at reflux temperature for 2 hours. The pH of the solution was adjusted to 7 by use of IN HC1 and the solid precipitate was filtered, washed with H2O and Et2θ. After drying 260 mg of the completely hydrolyzed product, 11 was obtained. By following the same procedure with 135 mg of the other batch of solid, 100 mg of the desired product II was obtained; total 360 mg (1 mM) , yield 74%. To the hydrolysis product 11 (360 mg) in DMSO (20 ml) at 75"C which was still a heterogeneous mixture, methanesulfonic acid (110 mg in 3 ml of PrOH) was added dropwise at 75"C. Upon addition of the acid the mixture became a homogeneous solution instantaneously. The solution was cooled to room temperature and at this point no solid precipitation was observed. Therefore, most of DMSO was removed in vacuo and THF (10 ml) was added to the residue with stirring. The desired solid product was precipitated, filtered, washed with Et2θ and dried to obtain 395 mg of methanesulfonic acid salt 12; mp 245- 250° (decomp.). X H NMR (D 2 0) S 8.97 (s, IH) , 7.62 (d, J-13Hz, IH) , 4.0-4.35 (m, 5H) , 3.26 (s, IH) , 2.78 (s, 3H) , 2.2-2.6 (m, 2H) , 2.1 (s, 6H); IR (mineral oil) 3268 (broad), 1722, 1703, 1633, 1600 cm -1 ; HRMS (FAB, M + H) 359.1535 (calcd for C 18 H 2 oN4θ3F 359.1519). Example 15 Preparation of (E)-2-(4-(3-carboxy-l-(l,l-dimethyl- propargyl) -6-fluoro-1,4-dihydro-4-oxo-7- (1,8-naph¬ thyridine) ) -1- (N-3-aminopyrrolidinyl)))-2-butnedioic acid, dimethyl ester Dimethyl acetylenedicarboxylate (25 μl, 0.2 mmol) was added to a solution of the amino acid (55 mg, 0.145 mmol) in DMF (2.5 ml). After stirring at 50 β C for 6.5 h, the solvent was evaporated off under a stream of nitrogen. The residue was flash chromatographed (5 g CC-4 silica gel, 2% MeOH/CH 2 Cl 2 , 4 ml fractions), to afford 44 mg of product (60%, fractions 6-10). An analytical sample was recrys¬ tallized from EtOAc/hexane. mp 110-4°C; Example 16 Preparation of E-2-(4-(3-carbosy-l-(bicyclo(1.1.1.)- pent-1-yl) -6-fluoro-1,4-dihydro-4-oxo-7- (1,8-naph¬ thyridine) ) -1- (N- (3-aminopyrrolidinyl)))-2-butenoic acid, dimethyl ester Dimethyl acetylenedicarboxylate (71 mg) was added to a DMF (3 mL) suspension of the amino acid (165 mg) and the resulting reaction stirred at 55"C for 2 hours. The reaction was cooled to room temperature and the DMF removed under a stream of N2. The resulting solid was dissolved in CH2CI2 and filtered. The filtrate was evaporated and the resulting product recrystallized from isopropyl alcohol/ether to yield 152 mg of a white solid. MP 157-61"C. FORMJLA SHEET FORHJLA SHEET - Continued C-Rg I 0I FORMULAS (continued) H Formula IB 20 Formula IBa FORMULAS (continued) Formula IC ^24 HN N- Formula J' \_ Formula 0' HO Formula 1 Formula P' Formula Q' or Formula R 1 Formula N' FORMULAS (continued) Compound No. 1 m.p. 225-226'C 15 Compound No. 2 m.p. 233-235°C 30 Compound No. 3 m.p. 232-233°C Compound No. 4 mp >250 β C FORMULAS (continued) Compound No. 84 m.p. 222-223 # C 25 Compound No. 36 m.p. 275"C dec Compound No. 91 m.p. >300"C Compound No. 99 m.p. 264-265°C FORMULAS (continued) R - Formula A' wherein W is NR 2 , S or 0, R 2 -0 H' 55 < SCHEME 1 15 30 35 SCHEME 1 (continued) 15 - SCHEME 2 (continued ) 10 C0 2 CH 3 C0 2 CH 3 SCHEME 3 SCHEME 4 SCHEME 5 MeO SCHEME 6 25 CO„CH 2 3 SCHEME 7 - Continued SCHEME 8 SCHEME 9 SCHEME 10 30 SCHEME 11 - - SCHEME 12 20 SCHEME 12 - Continued CH.O ^ C SCHEME 13 ,1.2,3 1.2.3 (Rg S F or CI) SCHEME 14 Step 5 ~ SCHEME 15 ■ acid SCHEME 16 SCHEME 17 HCOCF. R - -C(CH 3 ) 2 C-CH Formula B -&7- 1-piperazinyl 1-piperazinyl 3-hydroxy-1-pyrrolidinyl 1-piperazinyl 3-phenyl-1-piperazinyl 3-amino-3-methylpyrrolidin-1-yl 4-methyl-1-piperazinyl 2,5-diazabicyclo[2.2.2]octan-2-yl lS,4S-2,5-diazabicyclo[2.2.1]heptan-2-yl 3-aminomethy1-1-pyrro1idiny1 3-(ethylamino)methyl-1-pyrrolidinyl 3-methyl-1-piperazinyl 3,5-dimethyl-l-piperazinyl 4-dimethylamino-l-piperazinyl lR,4R-2,5-diazabicyclo[2.2.l]heptan-2-yl 4-(1,1-dimethylethyl)-1-piperazinyl 3-(ethylamino)methyl-l-pyrrolidinyl 1R,4R-2,5-diazabicyclo[2.2.l]heptan-2-yl 3-amino-l-pyrrolidinyl 8-methyl-3,8-diazabicyclo[3.2.1]octan-3-yl 3-methyl-1-piperazinyl IS,4S-2,5-diazabicyclo[2.2.l]heptan-2-yl 2,5-diazabicyclo[2.2.2]octan-2-yl 4-(cyclopenten-3-yl)-1-piperazinyl 3-aminomethyl-1-pyrrolidinyl 3-(ethylamino)methyl-1-pyrrolidinyl 3-methyl-l-piperazinyl TABLE BI (continued) Cpd # S 7 28 N 3 , 4- dime thy 1 - 1 - p iper az in 1 29 N 3 - phenyl - 1 - p iper az iny 1 30 N 1R, 4R- 2 , 5-diazabicyclo [2.2.1 } hep tan- 2 -yl 31 N 1R , 4R- 5 -methyl - 2 , 5 -diazabicyclo [ 2.2. l]hep- tan-2-yl 32 N 8-methyl-3,8-diazabicyclo[3.2.1]octan-3-yl 33 N 3,8-diazabicyclo[3.2.1]octan-3-yl 34 N 2-aminomethyl-morpholin-4-yl 35 N 3-amino-3-methylpyrrolidin-1-yl 36 N 3-amino-1-pyrrolidinyl (racemate) 37 N 3-fluoromethyl-piperazin-4-yl 38 N 3-aminomethyl-piperazin-4-yl 39 CH 3-fluoromethyl-piperazin-4-yl 40 N 1,4-diazabicyclo[3.2.l]oct-4-yl 41 N 3,8-diazabicyclo[3.2.1]oct-8-yl 42 N 3-amino-4-methyl-l-pyrrolidinyl (cis and trans mixture) 43 N 4-aminomethyl-3-hydroxy-1-pyrrolidinyl 44 CH 4-aminomethyl-3-hydroxy-1-pyrrolidinyl 45 N (R)-3-amino-l-pyrrolidinyl 46 N (S)-3-amino-1-pyrrolidinyl 47 N cis-3-amino-4-methyl-1-pyrrolidinyl 48 N trans-3-amino-4-methyl-1-pyrrolidinyl 49 N 3-aminomethyl-4-fluoro-1-pyrrolidinyl (cis and trans) 50 N 3-aminomethyl-4-fluoro-1-pyrrolidin l (cis) 51 N 3-aminomethyl-4-fluoro-1-pyrrolidinyl (trans) 52 N 3-amino-4-fluoro-l-pyrrolidinyl (cis and trans) 53 N 3-amino-4-fluoro-1-pyrrolidinyl (cis) 54 N 3-amino-4-fluoro-1-pyrrolidinyl (trans) 55 N 3-meth lamino-1-pyrrolidinyl 56 N 3-ethylamino-1-pyrrolidinyl 57 N 3-dimethylamino-1-pyrrolidinyl 58 N 3-(R)-(4-methylpiperazin-l-yl)-1-pyrrolidinyl 59 N 3-(R)-N' ,N' -dimethylhydrazino-pyrrolidin-1-yl TABLE BI (continued) E 7 3-(iminomethyl)amino-1-pyrrolidinyl 3-imino-1-pyrrolidinyl 3-(aminoiminomethyl)amino-1-pyrrolidinyl 2-methyl-4-amino-l-pyrrolidinyl (cis and trans 2-methyl-4-amino-1-pyrrolidinyl (cis) 2-methyl-4-amino-l-pyrrolidinyl (trans) 3-hydroxyamino-1-pyrrolidinyl 3-hydroxyimino-1-pyrrolidinyl 3-(N-cyano)amino-1-pyrrolidinyl 2,6-diazabicyclo[3.2.0]heptan-6-yl 2-methyl-2,6-diazabicyclo[3.2.0]heptan-6-yl 3-(R)-amino-4-(R)-ethyl-1-pyrrolidinyl 3-(R)-amino-4-(S)-ethyl-1-pyrrolidinyl 3-(S)-amino-4-(R)-ethyl-1-pyrrolidinyl 3-(S)-amino-4-(S)-ethyl-1-pyrrolidinyl 2-(R)-methyl-3-(R)-amino-1-pyrrolidinyl 2-(R)-methyl-3-(S)-amino-1-pyrrolidinyl 2-(S)-methyl-3-(R)-amino-1-pyrro1idinyl 2-(S)-methyl-3-(S)-amino-1-pyrrolidinyl 3-(R)-amino-4-(R)-phenyl-1-pyrrolidinyl 3-(R)-amino-4-(S)-phenyl-1-pyrrolidinyl 3-(S)-amino-4-(R)-phenyl-1-pyrrolidinyl 3-(S)-amino-4-(S)-phenyl-1-pyrrolidinyl 4-(cyclopenten-3-yl)-1-piperazinyl 3-amino-1-pyrrolidinyl (racemate) 3-amino-4-methyl-pyrrolidin-l-yl 3-hydroxy-1-pyrrolidinyl 3-amino-4-methyl-pyrrolidin-l-yl 3,5-dimethyl-1-piperazinyl 3-hydroxy-3-phenylpyrrolidin-1-yl 3-amino-3-phenylpyrrolidin-1- l 3-hydroxy-1-pyrrolidinyl (racemate) 3-hydroxy-3-methylpyrrolidin-1-yl 3-(2-butenedioic acid, dimethyl ester)amino- 1-pyrrolidinyl TABLE BI (continued) Cpd # S 7 94 CH 4-(2-butenedioic acid, dimethyl ester)-1- piperazinyl 95 CH 3-(2-butanedioic acid)amino-l-pyrrolidinyl 96 CH 3-(2-butanedioic acid)-1-piperazinyl 97 CH 3-(2-butanedioic acid, dimethyl ester)amino- 1-pyrrolidinyl 98 CH 3-(2-butanedioic acid, dimethyl ester)-1- piperazin l 99 CF 4-methyl-1-piperazinyl TABLE B2 MIC Medium MHA Control Ciprofloxacin MINIMUM INHIBITORY CONCENTRATION (meg τ>er mil Organism Name Staphylococcus aureus Staphylococcus aureus Staphylococcus aureus Staphylococcus aureus Staphylococcus aureus Staphylococcus epidermidis Streptococcus faecalis Streptococcus pneumoniae Streptococcus pyogenes Acinetobacter calcoaceticus Citerobacter freundii Enterobacter cloacae Escherichia coli Escherichia coli Escherichia coli Escherichia coli Klebsiella pneumoniae Proteus penneri Pseudomonas aeruginosa Pseudomonas aeruginosa Pseudomonas aeruginosa Serratia marcescens Cultures numbered less than 30000 are from the Upjohn culture collec¬ tion (UC) ; cultures numbered 30000 or greater are non-UC cultures. TABLE B3 MIC Medium MHA Control Ciprofloxacin MINIMUM INHIBITORY CONCENTRATION (meg per ml") Organism Name Cult No. Compound No. 2 Cipro Staphylococcus aureus 6685 0.5 0.25 Staphylococcus aureus 9213 1 1 Staphylococcus aureus 9218 1 0.5 Staphylococcus aureus 9271 1 0.5 Staphylococcus epidermidis 30031 0.5 0.125 Streptococcus faecalis 9217 4 0.5 Streptococcus pneumoniae 41 4 0.5 Streptococcus pyogenes 152 2 0.25 Acinetobacter calcoaceticus 12170 0.5 0.25 Citerobacter freundii 3507 0.06 <0.008 Enterobacter cloacae 9382 0.125 0.015 Escherichia coli 6674 0.125 0.015 Escherichia coli 9952 0.125 0.015 Escherichia coli 9451 0.125 0.015 Escherichia coli 9855 0.125 0.015 Klebsiella pneumoniae 12081 0.25 0.03 Proteus penneri 9679 0.5 0.03 Pseudomonas aeruginosa 6676 4 0.5 Pseudomonas aeruginosa 9191 2 0.25 Pseudomonas aeruginosa 12120 1 0.125 Serratia marcescens 6888 0.5 0.06 Cultures numbered less than 30000 are from the Upjohn culture collec¬ tion (UC) ; cultures numbered 30000 or greater are non-UC cultures. TABLE B4 MIC Medium MHA Control Ciprofloxacin Organism Name Staphylococcus aureus Staphylococcus aureus Staphylococcus aureus Staphylococcus aureus Staphylococcus epidermidis Streptococcus faecalis Streptococcus pneumoniae Streptococcus pyogenes Acinetobacter calcoaceticus Citerobacter freundii Enterobacter cloacae Escherichia coli Escherichia coli Escherichia coli Escherichia coli Klebsiella pneumoniae Proteus penneri Pseudomonas aeruginosa Pseudomonas aeruginosa Pseudomonas aeruginosa Serratia marcescens Cultures numbered less than 30000 are from the Upjohn culture collec¬ tion (UC) ; cultures numbered 30000 or greater are non-UC cultures. TABLE B5 MIC Medium MHA Control Ciprofloxacin MINIMUM INHIBITORY Organism Name Staphylococcus aureus Staphylococcus aureus Staphylococcus aureus Staphylococcus aureus Staphylococcus epidermidis Streptococcus faecalis Streptococcus pneumoniae Streptococcus pyogenes Acinetobacter calcoaceticus Citerobacter freundii Enterobacter cloacae Escherichia coli Escherichia coli Escherichia coli Escherichia coli Klebsiella pneumoniae Proteus penneri Pseudomonas aeruginosa Pseudomonas aeruginosa Pseudomonas aeruginosa Serratia marcescens Cultures numbered less than 30000 are from the Upjohn culture collec¬ tion (UC) ; cultures numbered 30000 or greater are non-UC cultures. TABLE B6 IC Medium MHA Control Ciprofloxacin MINIMUM INHIBITORY CONCENTRATION (meg per ml) Organism Name Cult No. Compound No. 99 Cipro Staphylococcus aureus 6685 0.5 0.125 Staphylococcus aureus 9213 0.5 0.5 Staphylococcus aureus 9218 0.5 0.25 Staphylococcus aureus 9271 0.5 0.5 Staphylococcus epidermidis 30031 0.5 0.125 Streptococcus faecalis 9217 4 0.5 Streptococcus pneumoniae 41 2 0.25 Streptococcus pyogenes 152 2 0.125 Acinetobacter calcoaceticus 12170 0.125 0.125 Citerobacter freundii 3507 0.25 <0.008 Enterobacter cloacae 9382 0.25 0.015 Escherichia coli 6674 0.25 0.015 Escherichia coli 9952 0.125 <0.008 Escherichia coli 9451 0.255 0.015 Escherichia coli 9855 0.25 0.015 Klebsiella pneumoniae 12081 0.5 0.03 Proteus penneri 9679 2 0.015 Pseudomonas aeruginosa 6676 4 0.5 Pseudomonas aeruginosa 9191 4 0.125 Pseudomonas aeruginosa 12120 2 0.125 Serratia marcescens 6888 1 0.06 Cultures numbered less than 30000 are from the Upjohn culture collec¬ tion (UC) ; cultures numbered 30000 or greater are non-UC cultures. TABLE B7 MIC Medium MHA Control Ciprofloxacin MINIMUM INHIBITORY Organism Name Staphylococcus aureus Staphylococcus aureus Staphylococcus aureus Staphylococcus aureus Staphylococcus epidermidis Streptococcus faecalis Streptococcus pneumoniae Streptococcus pyogenes Acinetobacter calcoaceticus Citerobacter freundii Enterobacter cloacae Escherichia coli Escherichia coli Escherichia coli Escherichia coli Klebsiella pneumoniae Proteus penneri Pseudomonas aeruginosa Pseudomonas aeruginosa Pseudomonas aeruginosa Serratia marcescens Cultures numbered less than 30000 are from the Upjohn culture collec¬ tion (UC) ; cultures numbered 30000 or greater are non-UC cultures. TABLE B8 MIC Medium MHA Control Ciprofloxacin Organism Name Staphylococcus aureus Staphylococcus aureus Staphylococcus aureus Staphylococcus aureus Staphylococcus epidermidis Streptococcus faecalis Streptococcus pneumoniae Streptococcus pyogenes Acinetobacter calcoaceticus Citerobacter freundii Enterobacter cloacae Escherichia coli Escherichia coli Escherichia coli Escherichia coli Klebsiella pneumoniae Proteus penneri Pseudomonas aeruginosa Pseudomonas aeruginosa Pseudomonas aeruginosa Serratia marcescens Cultures numbered less than 30000 are from the Upjohn culture collec¬ tion (UC) ; cultures numbered 30000 or greater are non-UC cultures. TABLE B9 MIC Medium MHA Control Ciprofloxacin MINIMUM INHIBITORY CONCENTRATION (meg per ml) Organism Name Cult No. Compound No. 84 Cipro Staphylococcus aureus 6685 0.06 0.25 Staphylococcus aureus 9213 0.125 1 Staphylococcus aureus 9218 0.125 0.5 Staphylococcus aureus 9271 0.125 0.5 Staphylococcus epidermidis 30031 0.125 0.125 Streptococcus faecalis 9217 0.5 0.5 Streptococcus pneumoniae 41 0.5 0.5 Streptococcus pyogenes 152 0.25 0.25 Acinetobacter calcoaceticus 12170 0.125 0.25 Citerobacter freundii 3507 0.36 <0.008 Enterobacter cloacae 9382 0.06 0.015 Escherichia coli 6674 0.03 0.015 Escherichia coli 9952 0.03 0.015 Escherichia coli 9451 0.06 0.015 Escherichia coli 9855 0.06 0.03 Klebsiella pneumoniae 12081 0.06 0.03 Proteus penneri 9679 0.25 0.03 Pseudomonas aeruginosa 6676 1 0.5 Pseudomonas aeruginosa 9191 0.5 0.125 Pseudomonas aeruginosa 12120 0.5 0.125 Serratia marcescens 6888 0.125 0.06 Cultures numbered less than 30000 are from the Upjohn culture collec¬ tion (UC) ; cultures numbered 30000 or greater are non-UC cultures.

Claims: CLAIMS 1. A compound of Formula I wherein X is nitrogen, a carbon substituted with a hydrogen hydroxyl, cyano, nitro, halogen Cχ-C4 alkyl or an amine; R3 is H, halogen, amine or hydroxyl; Y is 1) C -C o alkyl, C -C o cycloaklyl or heterocycloalkyl phenyl or substituted phenyl wherein the substituent is one o more of C^-Cχø alkyl, halogen, hydroxyl, hydrogen or a combination thereof, or C -C4 alkylene wherein each carbon ma be substituted with a fluorine; 2) -C(R 3) C«CR 4 where R 3 is independently hydrogen methyl, halogen substituted methyl or joined to form a cyclopro pyl and R^4 is hydrogen, fluorine, chlorine, bromine, Cχ-Cg alky or phenyl; or 3) bicyclo (1.1.1) pent-1-yl which can be substituted at C- with Cχ-Cg alkyl, C -Cg alkoxy, fluoro, bromo, chloro, nitro amino, hydroxy, COOH, C00(C^-Cg alkyl) and phenyl optionall substituted with one or two C -C alkyl, C -C β alkoxy, halo trifluromethyl, C -Cg dialkylamino, C -C3 alk lthio or nitro; Z is nitrogen, or a fluorine substituted carbon; is hydrogen or hydroxyl; Formula A' Formula B' Formula C R 2 2 N- wherein W is NR 2 , S or 0, Formula D' Formula E' Formula F' IM / " CHΛ j .-, N- Formula G' and Formula H' R 2 is independently selected from H, C3-C5 cycloalkyl, C5-C5 cycloalkenyl, -Q-N(R 10 )-C(R 9 )H-CH2-C(R 8 )0, -Q-N(R 10 )-C(R 9 )-CH(R 12 )- C(Rg)0 wherein R3 is hydrogen, hydroxyl, amine, C- ^ -C^ alkoxy or aryloxy, -SH, C^-C thioalkyl or thioaryl, R9 is C1-C alkyl, C -Cι 2 aryl, alkylaryl, heteroaryl, -(CH 2 ) n -C0 2 -(CH 2 ) m -R ι, B-n is hydrogen, hydroxyl, methyl alkyloxy, aryloxy or an amine, n is 0-4 and m is 0- 4, R 10 is hydrogen, -(CH ) 0> C -C4 alkyl, Cg-C j ^ aryl, alkylaryl, heteroaryl, or acetyl, where o is 0 or 1; Q is (CH 2 ) q where q is 0-2, CH-CH3, C(CH 3 ) 2 or C x -C 6 alkyl optionally substituted with 1, 2 or 3 hydroxy, fluoro, chloro, amino, C -C4 alkylamino, trifluoroacetylamino and phenyl; A, B, C, and D are independently selected from H, amino, hydroxy, halogen, C -C4 alkyl optionally substituted with 1, 2 or 3 hydroxy, fluoro, chloro, amino, C2-C4 alkylene, ethynyl, C -C alkylamino, trifluoroacetylamino, C3-C cycloalkyl, C _- C _S alkoxy- methyl, phenoxymethyl, C -C3 alkyl aminomethyl, C -C3 dialkyl aminomethyl, C -C j ^ aryl, substituted aryl, heteroaryl or substituted heteroaryl containing at least one 0, N or S and phenyl; and pharmaceutically acceptable acid addition and base salts thereof. 2. The compound of Claim 1 which is structurally represented by the formula (IA) : and therapeutically acceptable salts thereof wherein ^ is hydrogen or hydroxyl; Y is C -C o alkyls, C3-C Q cycloalkyl or heterocycloalkyl, a phenyl, -or a substituted phenyl wherein the substituent on the phenyl group is one or more of C^-C^Q alkyl, halogen, hydroxyl, hydrogen or a combination thereof, or C -C alkylene wherein each carbon atom may be substituted with fluorine; R3 is hydrogen, halogen, amine or hydroxyl; A, B, C, D are independently hydrogen, hydroxyl, halogen, C -C4 alkyl, ethenyl, ethynyl, C3-C5 cycloalkyl, fluoromethyl, difluoro¬ methyl, difluoroethyl, trifluoromethyl, hydroxymethyl, C^-C^g alkoxy methyl, phenoxymethyl, C -C3 alkyl aminomethyl, C -C3 dialkyl aminomethyl, Cg-C^ aryl, substituted aryl, heteroaryl or substituted heteroaryl containing at least one 0, N or S; Rg is hydrogen, hydroxyl, amine, C1-C4 alkoxy or aryloxy, -SH, C -Cg thioalkyl or thioaryl; Ro is C1-C4 alkyl, Cg-C 2 aryl, alkylaryl, heteroaryl, -(CH ) n - Cθ2-(CH 2 ) m -R , wherein Rχι is hydrogen, hydroxyl, methyl alkyloxy, aryloxy or an amine, n is 0-4 and m is 0-4; R^0 ^ s hydrogen, -(CH3) 0 C2-C4 alkyl, Cg-C 2 aryl, alkylaryl, heteroaryl, or acetyl, where o is 0 or 1; R 2 is hydrogen CN, halogen, or R9; Z is nitrogen or a fluorine substituted carbon; X is nitrogen, a carbon substituted with hydrogen, hydroxyl, cyano, nitro, halogen, C -C4 alkyl, or an amine; and Q is (CH 2 ) q where q is 0-2, CH-CH3 or C(CH 3 ) 2 . 3. The compound of Claim 2 wherein Z is a fluorine substituted carbon atom. 4. The compound of Claim 3 wherein X is a fluorine substituted car¬ bon atom. 5. The compound of Claim 4 wherein R3 is fluorine. 6. The compound of Claim 2 wherein Z is a fluorine substituted car¬ bon and X is a carbon. 7. The compound of Claim 2 wherein Rg is methoxy and Rg is a carbomethoxy group. 8. The' compound of Claim 2 wherein the carbon atom having the A group is bond to the nitrogen atom having the R^ group, R^Q →- S -(CH3) 0 where o is 0, and X is (CH 2 )q where q is 0. 9. The compound of Claim 8 which is a) 2- [4- (l-Cyclopropyl-3-carboxy-6,8-difluoro-l,4-dihydro-4- oxo-7-quinolinyl)-1-piperazinyl]2-butenedioic acid, dimethyl ester; b) 2- [4- (l-Ethyl-3-carboxy-6-fluoro-l,4-dihydro-4-oxo-7- quinolinyl)-l-piperizinyl]2-butenedioic acid, dimethyl ester; c) 2- [4- (l-Cyclopropyl-3-carboxy-5,6,8-trifluoro-l,4-dihydro- 4-oxo-7-quinolinyl)-1-piperazinyl]2-butenedioic acid, di¬ methyl ester; d) 2- [4- (l-Cyclopropyl-3-carboxy-6-fluoro-l,4-dihydro-4-oxo-7- quinolinyl)-1-piperazinyl]2-butenedioic acid, dimethyl ester; e) 2- [4- (3-carboxy-l-cyclopropyl-6,8-difluoro-l,4-dihydro-4- oxo-7-quinolinyl)--1-piperazinyl] -2-pentenedioic acid-(E)- 1,5-dimethyl ester; f) 2- [4-(5-amino-3-carboxy-l-cyclopropyl-6, 8-difluoro-1,4- dihydro-4-oxo-7-quino1iny1)-l-piperaziny1] -2-butenedioic acid, (E)-l,4-dimethyl ester; g) 2- [4-(3-carboxy-l-cyclobutyl-6,8-difluoro-l,4-dihydro-4-oxo- 7-quinolinyl)-1-piperazinyl] -2-butenedioic acid (E)-1,4- dimethyl ester; or h) 2 - [ 4- (3-carboxy- 1-benzene(4-fluoro) -6 , 8-difluoro-l ,4- dihydro-4-oxo-7-quinoliny1) -1-piperaziny1] -2-butenedioic acid, (E)-1,4-dimethyl ester. 10. The compound of Claim 2 wherein the carbon atom having the A group is bond to the carbon atom having the D group. 11. The compound of Claim 10 which is a) (E)-2-(N-(3-carboxy-1-cyclopropyl-6,8-difluoro-l,4- dihydro - 4 - oxo - 7 - quinolinyl) - 1- (3 -aminopyrrolinyl) ) - 2 - butenedioic acid, 1,4-dimethyl ester; b) 2- [4- (3-carboxy-l-benzene(2 ,4-difluoro) -l ,4-dihydro-4-oxo-7- quinolinyl) - 1 - ( 3 - aminopyrrolidinyl) ] - 2 -butenedioic acid , (E) - 1,4-dimethyl ester; or c) 2- [4- (3-carboxy- 1-cyclopropyl- 6, 8 -dif luoro -1,4 -dihydro -4- oxo-7-quinolinyl) -1- (3-aminopyrrolidinyl) ] -3-butenoic acid- (E)-l-methyl ester. 12. The compound of Claim 1 structurally represented by the Formula IB wherein X is selected from N, CH, CF, CC1, CBr, and CCH3; wherein R3 is selected from H, F and NH 2 ; wherein R is selected from H, C -C° alkyl, C -Cg alkoxy, fluoro, bromo, chloro, nitro, amino, hydroxy, COOH, C0O(C -Cg alkyl) and phenyl optionally substituted with one or two C -C4 alkyl, C-L-C3 alkoxy, halo, trifluromethyl, C 2 -Cg dialkylamino, C -C3 alk lthio or nitro; wherein R 7 is selected from Formula A' - Formula B' Formula C wherein W is NR 2 , S or 0, Formula D' Formula E' Formula F' Formula G' and Formula H' wherein R 2 is independently selected from H, C3-Cg cycloalkyl, C5-C cycloalkenyl, -Z-N(R 10 )-C(R 11 )H-CH 2 -C(R 12 )0, -Z-N(R 10 )-C(R n )-CH- C(R 2 )0. and C^-Cg alkyl optionally substituted with 1, 2 or 3 hydroxy, fluoro, chloro, amino, C^-C4 alkylamino, trifluoroacetyl- amino and phenyl; wherein A, B, C, and D are independently selected from H, amino, hydroxy, fluoro, chloro, C1-C alkyl optionally sub¬ stituted with 1, 2 or 3 hydroxy, fluoro, chloro, amino, C 2 -C4 alkyl¬ ene, C1-C alkylamino, trifluoroacetylamino and phenyl; and wherein n, when present, is selected from the integers 0, 1, 2, and 3; and pharmaceutically acceptable acid addition and base salts thereof. 13. A compound according to Claim 12 wherein R is hydrogen. 14. A compound according to Claim 12 wherein R7 is selected from 1- piperazinyl, 4-methyl-l-piperazinyl, 3-methyl-l-piperazinyl, 3,5- dimethyl-1-piperazinyl, 2,5-diazabicyclo [2,2,l]heptan-2-yl, 3-amino- 1-pyrrolidinyl, 3-amino-4-methyl-l-pyrrolidinyl, 4-aminomethyl-3- hydroxy-1-pyrrolidinyl and 3-(ethylamino)methyl-l-pyrrolidinyl. 15. A compound according to Claim 12 selected from 1- (bicyclo[1.1.l]pent-l-yl)-6,8-difluoro-l,4-dihydro-4-oxo-7-(l- piperazinyl)-3-quinolinecarboxylic acid; 1- (bicyclo[1.1.1]pent-1-yl)-1,4-dihydro-6-fluoro-4-oxo-7-(l- piperazinyl)-3-quinolinecarboxylic acid; 1- (bicyclo[1.1.l]pent-l-yl)-l,4-dihydro-6-fluoro-7-(1-piperazin¬ yl)-4-oxo-3-quinolinecarboxylic acid, methane sulfonate; 7- [4-(cyclopenten-3-yl)-1-piperazinyl]-1-(bicyclo[1.1.l]pent-l- yl)-1,4-dihydro-6-fluoro-4-oxo-3-quinolinecarboxylic acid, hydro¬ chloride; 7- (8-methyl-3,8-diazabicyclo[3.2.1]octan-3-yl)-1- (bicyclo- [1.1.1]pent-1-yl)-1,4-dihydro-6-fluoro-4-oxo-3-quinolinecarboxylic acid, hydrochloride; 7- [3-phenyl-1-piperazinyl] -1-(bicyclo[1.1.1]pent-1-yl) -1,4- dihydro-6-fluoro-4-oxo-3-quinolinecarboxylic acid, methanesulfonate; 1- (bicyclo[1.1.l]pent-l-yl)-1,4-dihydro-6-fluoro-7-(4-methy11- piperazinyl)-4-oxo-3-quinolinecarboxylic acid, hydrochloride; 7-(2,5-diazabicyclo[2.2.2]octan-2-yl)-l-(bicyclo[l.l.l]pent-l- yl)-l,4-dihydro-6-fluoro-4-oxo-3-quinolinecarboxylic acid; 7-(IS,4S-2,5-diazabicyclo[2.2.l]heptan-2-yl)-l-(bicyclo[1.1.1]- pent-l-yl)-l,4-dihydro-6-fluoro-4-oxo-3-quinolinecarboxylic acid; 7-(3-(aminomethyl) -1-pyrrolidinyl)-1-(bicyclo[1.1.l]pent-l-yl)- l,4-dihydro-6-fluoro-4-oxo-3-quinolinecarboxylic acid; 7- ("3-(ethylamino)methyl-1-pyrrolidinyl-1-(bicyclo[1.1.l]pent-l- yl)-l,4-dihydro-6-fluoro-4-oxo-3-quinolinecarboxylic acid; 7- (3-methyl-l-piperazinyl)-l-(bicyclo[l.l.l]pent-l-yl)-l,4-di¬ hydro-6-fluoro-4-oxo-3-quinolinecarboxylic acid; 7- (3,5-dimethyl-1-piperazinyl)-1-(bicyclo[1.1.l]pent-l-yl)-1,4- dihydro-6-fluoro-4-oxo-3-quinolinecarboxylic acid; 7- (4-(dimethylamino)-1-piperazinyl)-1-(bicyclo[1.1.l]pent-l-yl)- l,4-dihydro-6-fluoro-4-oxo-3-quinolinecarboxylic acid; 7-(4-(l,l-dimethylethyl)-l-piperazinyl)-l-(bicyclo[l.l.l]pent-l- yl)-1,4-dihydro-6-fluoro-4-oxo-3-quinolinecarboxylic acid; 7- (3-(ethylamino)methyl-1-pyrrolidinyl)-1-(bicyclo[1.1.l]pent-l- yl)-1,4-dihydro-6,8-difluoro-4-oxo-3-quinolinecarboxylic acid; 7- (3-amino-l-pyrrolidinyl) -1- (bicyclo[l.1.1]pent-1-yl) -1,4- dihydro-6-fluoro-4-oxo-3-quinolinecarboxylic acid, hydrochloride; 7- (3-hydrox -1-pyrrolidinyl) -1- (bicyclo[1.1.1]pent-1-yl)-1,4- dihydro-6-fluoro-4-oxo-3-quinolinecarboxylic acid; 7- (3-amino-1-pyrrolidinyl) -1- (bicyclo[1.1.1]pent-1-yl) -1,4- dihydro-6-fluoro-4-oxo-3-quinolinecarboxylic acid; 7- (3-amino-4-methyl-pyrrolidin-l-yl) -1- (bicyclo[l.l.l]pent-l- yl)-l,4-dihydro-6-fluoro-4-oxo-3-quinolinecarboxylic acid; 7- (3-hydroxy-l-pyrrolidinyl) -1-(bicyclo[l.l.l]pent-l-yl)-l,4- dihydro-6,8-difluoro-4-oxo-3-quinolinecarboxylic acid; 7- (3-amino-l-pyrrolidinyl) -1- (bicyclo[1.1.1]pent-1-yl) -1,4- dihydro-6,8-difluoro-4-oxo-3-quinolinecarboxylic acid; 7- (3-amino-4-methyl-pyrrolidin-l-yl) -1- (bicyclo[1.1.l]pent-l- yl)-1,4-dihydro-6,8-difluoro-4-oxo-3-quinolinecarboxylic acid; 7- (3-hydrox -3-methylpyrrolidin-1-yl)-1-(bicyclo[1.1.1]pent-1- yl)-l,4-dihydro-6-fluoro-4-oxo-l,8-naphthyridine-3-carboxylic acid; 7- (3-amino-3-methylpyrrolidin-l-yl)-1-(bicyclo[1.1.1]pent-1-yl)- 1,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid; 7- (3-hydroxy-3-phenylpyrrolidin-1-yl)-1-(bicyclo[1.1.1]pent-1- yl)-l,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid; 7- (3-amino-3-phenylpyrrolidin-1-yl)-1-(bicyclo[1.1.1]pent-1-yl)- 1,4-dihydro-6-fluoro-4-oxo-l,8-naphthyridine-3-carboxylic acid; 7- (3,5-dimethyl-1-piperazinyl)-1-(bicyclo[1.1.l]pent-l-yl)-1,4- dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid; 7- (3-hydroxy-l-pyrrolidinyl) -1- (bicyclo[l.l.l]pent-l-yl)-l,4- dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid; 7- (1-piperazinyl) -1- (bicyclofl.l. l]pent-l-yl) -1, 4-dihydro-6- f luoro-4-oxo-l , 8-naphthyridine-3-carboxylic acid; 7-(3-methyl-l-piperazinyl)-l-(bicyclo[l.l.l]pent-l-yl)-l,4-di- hydro-6 -fluoro- 4-oxo-l, 8 -naphthyridine- 3 -carboxylic acid; 7-(lS,4S-2,5-diazabicyclo[2.2.1]he tan-2-yl)-l-(bicyclo- [l.l.l]pent-l-yl)-l, 4-dihydro- 6-fluoro-4-oxo-l,8-naphthyridine-3- carboxylic acid; 7- (2, 5 -diazabicyclo [2.2.2 ]octan-2-yl)-l- (bicyclo[l.l. l]pent-l- yl) -1 ,4-dihydro-6-f luoro-4-oxo-l , 8 -naphthyridine- 3 -carboxylic acid; 7- (4- (cyclopenten-3-yl) -1-piperazinyl) -1- (bicyclo [1.1. l]pent-l- yl ) - 1 , 4 - dihydro - 6 - fluoro - 4- oxo -1,8 -naphthyridine - 3 - carboxylic acid ; 7 - (3 - (ethylamino)methyl-l-pyrrolidinyl) -1- (bicyclo [1.1. l]pent-l- yl)-l, 4-dihydro- 6-fluoro-4-oxo-l,8-naphthyridine-3-carboxylic acid; 7- (3 -methyl -1-piperazinyl) -1- (bicyclo [1.1.1] pent -1-yl) -1,4- dihydro- 6 -fluoro- 4-oxo-l , 8 -naphthyridine- 3 -carboxylic acid; 7- (3 ,4-dimethyl -1-piperazinyl) -1- (bicyclo [1.1.1] pent-1-yl) -1,4- dihydro - 6 - fluoro - 4 - oxo -1,8 -naphthyridine - 3 - carboxylic acid ; 7- (3 -phenyl -1-piperazinyl) -1- (bicyclo [1.1.1] pent- 1-yl) -1,4- dihydro- 6- fluoro -4-oxo-l, 8 -naphthyridine- 3 -carboxylic acid, methane¬ sulf onate ; 7 -(1R.4R- 2, 5 -diazab icyclo [2. .1] hep tan- 2-yl)-l- (bicyclo - [1.1.1] pent- 1-yl ) - 1 , 4- dihydro- 6 - fluoro -4-oxo-l , 8 -naphthyridine- 3- carboxylic acid; 7 - ( 8 -me thy 1 -3,8- diazab icyclo [3.2.1] octan- 3 - l ) - 1 - (b icyclo - [1.1.1] pent- 1-yl) - 1,4- dihydro- 6- fluoro -4-oxo-l, 8 -naphthyridine- 3- carboxylic acid, methanesulf onate salt; 7 -(3, 8 -diazabicyclo [3.2.1] octan-3-yl)-l- (bicyclo [1.1. l]pent-l- yl)-l,4-dihydro-6-fluoro-4-oxo-l, 8 -naphthyridine- 3 -carboxylic acid, methanesulf onate ; 7- (2 -aminomethyl -morpholin-4-yl) -1- (bicyclo [1.1. l]pent-l-yl)- 1 , 4-dihydro-6-f luoro-4-oxo-l , 8-naphthyridine-3-carboxylic acid; 7- (3-amino-l-pyrrolidinyl) -1- (bicyclo [1.1.1] pent- 1-yl) -1,4- dihydro-6-f luoro- 4-oxo-l, 8 -naphthyridine- 3 -carboxylic acid; 7- ((S) - 3- amino -1-pyrrolidinyl) -1- (bicyclo [1.1. l]pent-l-yl) -1,4- dihydro-6-fluoro-4-oxo-l, 8 -naphthyridine- 3 -carboxylic acid; 7- (3-amino-4-methyl-pyrrolidin-l-yl) -1- (bicyclo[l.l.l]pent-l- yl) -1 , 4-dihydro - 6 - fluoro -4 -oxo- 1 , 8 -naphthyridine-3 -carboxylic acid; 7- (trans-3-amino-4-methyl-pyrrolidin-l-yl) -1- (bicyclo [1.1. l]pent- 1-yl) -1, 4-dihydro- 6 -fluoro-4-oxo-l,8-naphthyridine-3-carboxylic acid 7 -(cis -3 -amino-4 -methyl-pyrrolidin-l-yl)-l- (bicyclo [1.1. ljpent l-yl)-l,4-dihydro-6-fluoro-4-όxo-l,8-naphthyridine-3-carboxylic acid 7- (4 -methyl- 1-piperazinyl) -1- (bicyclo [1.1.1 ]pent-l-yl) -1, dihydro- 6, 8 -dif luoro-4-oxo- 3 -quinolinecarboxylic acid (Cpd #99). 16. The compound of Claim 1 structurally represented by the Formul IC and pharmaceutically acceptable acid addition and base salt thereof, wherein X is N, CH, CF, CC1, CBr, or CCH 3 ; R3 is H, F or NH 2 ; R 2 3 are independently hydrogen, methyl, halogen substitute methyl or joined to form a cyclopropyl; R 2 4 is hydrogen, fluorine, chlorine, bromine, C -Cg alkyl, o phenyl; wherein R7 is Formula J' , ■ - H 3 CN N- Formula K' Formula L' Formula M' Formula N' Formula 0' Formula P' H 3 C N- Formula Q' or H 3 Formula R' wherein R 2 g is independently selected from H, C3-C cycloalkyl, Cg-C cycloalkenyl, and C -Cg alkyl optionally substituted with 1, 2 or hydroxy, fluoro, chloro, amino, C1-C alkylamino, trifluoroacetyl amino and phenyl and R 2 y is hydrogen, hydroxyl or a C^-C alky optionally substituted with one or more hydroxy, or halogens. 17. The compound of Claim 16 where X is CF. 18. The compound of Claim 16 where R3, R 2 3 and R 2 are hydrogen. 19. The compound of Claim 16 where R5 is 1-piperazinyl, 4-methyl-l piperazinyl, 3-methyl-1-piperazinyl, 3,5-dimethyl-1-piperazinyl, 2,5 diazabicyclo [2.2.1]hept-2-yl, 3-amino-l-pyrrolidinyl, 3-amino-4 methyl-1-pyrrolidinyl, 4-aminomethyl-3-hydroxy-l-pyrrolidinyl and 3 (ethylamino)meth l-1-pyrrolidinyl. 20. The compound of Claim 16 where R7 is Formula P' and R g i hydrogen. 21. The compound of Claim 16 which is: a) (+, -)-6,8-difluoro-l,4-dihydro-l-(1,1-dimethyl-2-propyny- l)-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid methane¬ sulfonate, D ) (+, -)-6,8-difluoro-l,4-dihydro-4-oxo-7-(1-piperazinyl)- 1-(2-propynyl)-3-quinolinecarboxylic acid methanesulfonate, c) (+,-)-7-(3-amino-1-pyrrolidinyl)-1,4-dihydro-1-(1,1- dimethyl-2-ρropynyl) -6-fluoro-4-oxo-l,8-naphthyridine-3-carboxyli acid methanesulfonate, d) (+, -)-7-(amino-1-pyrrolidinyl)-6,8-difluoro-1,4-dihydro- 1-(l,l-dimethyl-2-propynyl)-4-oxo-3-quinolinecarboxylic acid, or e) (+ ι -)-7-(amino-1-pyrrolidinyl)-6,8-difluoro-l,4-dihydro- 4-oxo-l-(2-propynyl)-3-quinolinecarboxylic acid. 22. A pharmaceutical composition comprising a pharmaceuticall acceptable carrier and an antibacterially effective amount of a compound of Formula I according to Claim 1 in admixture with a pharmaceutical carrier. 23. ' Use of a compound of Formula I according to Claim 1 for prepara¬ tion of a medicament for combatting bacterial infection in warm¬ blooded animals comprising administering to said animals an antibac¬ terially effective amount of a compound of Formula I.

Inventors: BARBACHYN MICHAEL R, BISAHA SHARON N, GAMMILL RONALD B, JUDGE THOMAS M, KIM KYOUNG S, TIMKO JOSEPH M, BARBACHYN, MICHAEL, R., BISAHA, SHARON, N., GAMMILL, RONALD, B., JUDGE, THOMAS, M., KIM, KYOUNG, S., TIMKO, JOSEPH, M.
Applicants: UPJOHN CO, THE UPJOHN COMPANY
Application year: 1989
Main classification: C07D401
IPC codes: A61K31, C07D215, C07D401, C07D413, C07D417, C07D471, C07D487, C07D519