Abstract:
The present invention relates to new cephalosporin compounds of the formula (I), particularly 3-position of cephem rings thereof substituted with new thione compounds and pharmaceutically acceptable salts thereof, which have broad antibacterial activities against both Gram-positive and Gram-negative bacteria, and the said compounds can be prepared by reacting the compounds of the formula (II) with the new thione compounds of the formula (III). ##STR1## wherein R 1  is a C 1-4  alkyl(preferably methyl or ethyl), C 3-4  alkenyl(preferably allyl), C 3-4  alkynyl (preferably propargyl) group or --C(R a ) (R b )CO 2  H(preferably --C(CH 3 ) 2  CO 2  H or --CH 2  CO 2  H), wherein R 1  and R b , same or different, are a hydrogen atom or a C 1-4  alkyl group; 
     R 2  is a C 1-4  alkyl(preferably methyl or ethyl), C 3-4  alkenyl(preferably allyl), C 3-4  cycloalkyl(preferably cyclopropyl) group or carboxyalkyl(preferably --CH 2  CO 2  H) group; 
     R 3  is a 5- or 6-membered heterocyclic compound-containing 1 or 2 nitrogen atom(s) (preferably piperazine, alkylpiperazine-substituted with C 1-4  alkyl at N-- or 2-position of piperazine, imidazole-substituted or unsubstituted with C 1-4  alkyl); R 4  is hydrogen or a carboxylic acid.

Description:
This application is a 35 USC §371 of PCT/KR93/0005, filed Jan. 16, 1993. 
    
    
     This application is a 35 USC §371 of PCT/KR93/0005, filed Jan. 16, 1993. 
     FIELD OF THE INVENTION 
     The present invention relates to new cephalosporin compounds of the formula (I), particularly 3-position of cephem rings substituted with new thione compounds and pharmaceutically acceptable salts thereof, which have broad antibacterial activities against both Gram-positive and Gram-negative bacteria. 
     SUMMARY OF THE INVENTION 
     An objective of the present invention is to provide new antibiotic cephalosporin compounds of the formula(I) or pharmaceutically acceptable salts thereof ##STR2## wherein R 1  is a C 1-4  alkyl (preferably ethyl or ethyl), C 3-4  alkenyl(preferably allyl), C 3-4  alkynyl (preferably propargyl) group or --C(R a )(R b )CO 2  H(preferably --C(CH 3 ) 2  CO 2  H or --CH 2  CO 2  H), wherein R a  and R b , same or different, are a hydrogen atom or a C 1-4  alkyl group; 
     R 2  is a C 1-4  alkyl (preferably methyl or ethyl), C 3-4  alkenyl (preferably allyl), C 3-4  cycloalkyl (preferably cyclopropyl)group or carboxyalkyl (preferably --CH 2  CO 2  H)group; 
     R 3  is a 5- or 6-membered heterocyclic compounds-containing 1 or 2 nitrogen atom(s) (preferably piperazine, alkylpiperazine-substituted with C 1-4  alkyl at N-- or 2-position of piperazine, imidazole-substituted or unsubstituted with C 1-4  alkyl); 
     R 4  is hydrogen or a carboxylic acid. 
     DETAILED DESCRIPTION OF THE INVENTION 
     The compounds of the formula(I) can be prepared by reacting the compounds of the formular(II) with the new thione compounds of the formular (III), as follows: ##STR3## wherein R 1  is a methyl, allyl, propargyl group or --C(CH 3 ) 2  CO 2  H; 
     R 2 ,R 3  and R 4  are the same as defined above. 
     In the preparation of the objective compounds(I), the compounds of the formula(III) are used preferably in an amount of from 1 to 2 equivalent(s) based on 1 equivalent of the compounds of the formula(II). The reaction for introducing the compounds(lII) into the 3-position of compound(II) to prepare compounds(I) is carried out in the presence of a solvent such as water, N,N-dimethylformamide, dimethylsulfoxide, or a mixed agueous solvent of water. An appropriate water-miscible solvent is acetonitrile or acetone. 
     Also, the reaction may be carried out at 40° C. to 100° C., preferably 60° C. to 80° C. 
     To stabilize reaction products and their intermediates, one or more salts selected from the group consisting of sodium iodide and potassium iodide can be used as stabilizing agents. 
     On the other hand, the separation and purification of the compounds(I) can be carried out using a known method such as recrystallization, column chromatography over silica gel or ion-exchange chromatography. 
     The new thione compounds of the formula(III) can be prepared from quinolone compounds which prepared by known method, as follows: ##STR4## wherein R 2  is a methyl cyclopropyl, ethyl or allyl group; 
     R 4  is hydrogen; 
     R 3  is the same as defined above. 
     The compounds of the formula(IV) can be prepared by reacting quinolone compounds, sodium borohydride with p-toluenesulfonic acid in the polar solvent, preferably alcohol. 
     The compounds of the formula(V) can be prepared by reacting the compounds of the formular(IV) with p-chloranil in the polar solvent, preferably 1,4-dioxane at 50° C. to 100° C. 
     Also, the compounds of the formula(VI) can be prepared by reacting the compounds of the formular(V) with phosphorus pentasulfide in the polar solvent, preferably acetonitrile, and the new thione compounds of the formula(III) can be prepared by substitution of 5- or 6-membered heterocyclic compounds-containing 1 or 2 nitrogen atom(s)(preferably piperazine, alkylpiperazine-substituted with C 1-4  alkyl at N-- or 2-position of piperazine, imidazole-substituted or unsubstituted with C 1-4  alkyl) at the 7-position of compounds(VI). 
     In case R 4  is a carboxylic acid, the compounds of the formula(III) can be prepared from the compounds of the formula(VII) which prepared by known method, as follows: ##STR5## wherein R 2  is a cyclopropyl; 
     R 4  is a carboxylic acid; 
     R 3  is the same as defined above. 
     The compounds of the formula(VIII) can be prepared by reacting with the compounds of the formular(VII) and phosphorus pentasulfide in the polar solvent, preferably acetonitrile. 
     The compounds of the formula(IX) can be prepared by hydrolysis of the compounds(VIII). 
     Also, the compounds of the formula(III) can be prepared by substitution of 5-or 6-membered heterocyclic compounds-containing 1 or 2 nitrogen atom(s) (preferably piperazine, alkylpiperazine-substituted with C 1-4  alkyl at N-- or 2-position of piperazine, imidazole-substituted or unsubstituted with C 1-4  alkyl) at the 7-position of compounds(IX). 
     The new thione compounds of the formula(III) are shown in Table 1. 
     
                       TABLE 1______________________________________New Thione Compounds ##STR6##Compound No.      R.sub.2    R.sub.3       R.sub.4______________________________________III-1      Methyl     Piperazine    HIII-2      Methyl     N-Methylpiperazine                               HIII-3      Methyl     1-Ethylpiperazine                               HIII-4      Methyl     2-Methylpiperazine                               HIII-5      Methyl     Imidazole     HIII-6      Methyl     4-Methylimidazole                               HIII-7      Cyclopropyl                 Piperazine    HIII-8      Cyclopropyl                 N-Methylpiperazine                               HIII-9      Cyclopropyl                 1-Ethylpiperazine                               HIII-10     Cyclopropyl                 2-Methylpiperazine                               HIII-11     Cyclopropyl                 Imidazole     HIII-12     Cyclopropyl                 4-Methylimidazole                               HIII-13     Cyclopropyl                 1-Ethylpiperazine                               COOHIII-14     Cyclopropyl                 2-Methylpiperazine                               COOHIII-15     Ethyl      Piperazine    HIII-16     Ethyl      N-Methylpiperazine                               HIII-16     Ethyl      N-Methylpiperazine                               HIII-17     Ethyl      1-Ethylpiperazine                               HIII-18     Ethyl      2-Methylpiperazine                               HIII-19     Allyl      Piperazine    HIII-20     Allyl      N-Methylpiperazine                               HIII-21     Allyl      1-Ethylpiperazine                               HIII-22     Allyl      2-Methylpiperazine                               H______________________________________ 
    
     The new cephalosporin compounds of the formula(I) are shown in Table 2. 
     
                                           TABLE 2__________________________________________________________________________New Cephalosporin Compounds ##STR7##Compound No.   R.sub.1  R.sub.2 R.sub.3    R.sub.4__________________________________________________________________________I-1     CH.sub.3 Methyl  Piperazine HI-2     CH.sub.3 Methyl  N-Methylpiperazine                               HI-3     CH.sub.3 Methyl  1-Ethylpiperazine                               HI-4     CH.sub.3 Methyl  2-Methylpiperazine                               HI-5     CH.sub.3 Cyclopropyl                    Piperazine HI-6     CH.sub.3 Cyclopropyl                    N-Methylpiperazine                               HI-7     CH.sub.3 Cyclopropyl                    1-Ethylpiperazine                               HI-8     CH.sub.3 Cyclopropyl                    2-Methylpiperazine                               HI-9     CH.sub.3 Ethyl   Piperazine HI-10    CH.sub.3 Ethyl   N-Methylpiperazine                               HI-11    CH.sub.3 Ethyl   1-Ethylpiperazine                               HI-12    CH.sub.3 Ethyl   2-Methylpiperazine                               HI-13    CH.sub.3 Allyl   Piperazine HI-14    CH.sub.3 Allyl   N-Methylpiperazine                               HI-15    CH.sub.3 Allyl   1-Ethylpiperazine                               HI-16    CH.sub.3 Allyl   2-Methylpiperazine                               HI-17    CH.sub.3 Methyl  Imidazole  HI-18    CH.sub.3 Methyl  4-Methylimidazole                               HI-19    CH.sub.3 Cyclopropyl                    Imidazole  HI-20    CH.sub.3 Cyclopropyl                    4-Methylimidazole                               HI-21    CH.sub.2 CHCH.sub.2            Methyl  Piperazine HI-22    CH.sub.2 CHCH.sub.2            Methyl  N-Methylpiperazine                               HI-23    CH.sub.2 CHCH.sub.2            Methyl  1-Ethylpiperazine                               HI-24    CH.sub.2 CHCH.sub.2            Methyl  2-Methylpiperazine                               HI-25    CH.sub.2 CHCH.sub.2            Cyclopropyl                    Piperazine HI-26    CH.sub.2 CHCH.sub.2            Cyclopropyl                    N-Methylpiperizine                               HI-27    CH.sub.2 CHCH.sub.2            Cyclopropyl                    1-Ethylpiperazine                               HI-28    CH.sub.2 CHCH.sub.2            Cyclopropyl                    2-Methylpiperazine                               HI-29    CH.sub.2 CHCH.sub.2            Ethyl   Piperazine HI-30    CH.sub.2 CHCH.sub.2            Ethyl   N-Methylpiperazine                               HI-31    CH.sub.2 CHCH.sub.2            Ethyl   1-Ethylpiperazine                               HI-32    CH.sub.2 CHCH.sub.2            Ethyl   2-Methylpiperazine                               HI-33    CH.sub.2 CHCH.sub.2            Allyl   Piperazine HI-34    CH.sub.2 CHCH.sub.2            Allyl   N-Methylpiperazine                               HI-35    CH.sub.2 CHCH.sub.2            Allyl   1-Ethylpiperazine                               HI-36    CH.sub.2 CHCH.sub.2            Allyl   2-Methylpiperazine                               HI-37    CH.sub.2 CCH            Methyl  Piperazine HI-38    CH.sub.2 CCH            Methyl  N-Methylpiperazine                               HI-39    CH.sub.2 CCH            Methyl  1-Ethylpiperazine                               HI-40    CH.sub.2 CCH            Methyl  2-Methylpiperazine                               HI-41    CH.sub.2 CCH            Cyclopropyl                    Piperazine HI-42    CH.sub.2 CCH            Cyclopropyl                    N-Methylpiperazine                               HI-43    CH.sub.2 CCH            Cyclopropyl                    1-Ethylpiperazine                               HI-44    CH.sub.2 CCH            Cyclopropyl                    2-Methylpiperazine                               HI-45    CH.sub.2 CCH            Ethyl   Piperazine HI-46    CH.sub.2 CCH            Ethyl   N-Methylpiperazine                               HI-47    CH.sub.2 CCH            Ethyl   1-Ethylpiperazine                               HI-48    CH.sub.2 CCH            Ethyl   2-Methylpiperazine                               HI-49    CH.sub.2 CCH            Allyl   Piperazine HI-50    CH.sub.2 CCH            Allyl   N-Methylpiperazine                               HI-51    CH.sub.2 CCH            Allyl   1-Ethylpiperazine                               HI-52    CH.sub.2 CCH            Allyl   2-Methylpiperazine                               HI-53    C(CH.sub.3).sub.2 CO.sub.2 H            Methyl  Piperazine HI-54    C(CH.sub.3).sub.2 CO.sub.2 H            Methyl  N-Methylpiperazine                               HI-55    C(CH.sub.3).sub.2 CO.sub.2 H            Methyl  1-Ethylpiperazine                               HI-56    C(CH.sub.3).sub.2 CO.sub.2 H            Methyl  2-Methylpiperazine                               HI-57    C(CH.sub.3).sub.2 CO.sub.2 H            Cyclopropyl                    Piperazine HI-58    C(CH.sub.3).sub.2 CO.sub.2 H            Cyclopropyl                    N-Methylpiperazine                               HI-59    C(CH.sub.3).sub.2 CO.sub.2 H            Cyclopropyl                    1-Ethylpiperazine                               HI-60    C(CH.sub.3).sub.2 CO.sub.2 H            Cyclopropyl                    2-Methylpiperazine                               HI-61    C(CH.sub.3).sub.2 CO.sub.2 H            Ethyl   1-Ethylpiperazine                               HI-62    C(CH.sub.3).sub.2 CO.sub.2 H            Ethyl   2-Methylpiperazine                               HI-63    C(CH.sub.3).sub.2 CO.sub.2 H            Allyl   1-Ethylpiperazine                               HI-64    C(CH.sub.3).sub.2 CO.sub.2 H            Allyl   2-Methylpiperazine                               HI-65    C(CH.sub.3).sub.2 CO.sub.2 H            Methyl  Imidazole  HI-66    C(CH.sub.3).sub.2 CO.sub.2 H            Methyl  4-Methylimidazole                               HI-67    C(CH.sub.3).sub.2 CO.sub.2 H            Cyclopropyl                    Imidazole  HI-68    C(CH.sub.3).sub.2 CO.sub.2 H            Cyclopropyl                    4-Methylimidazole                               HI-69    CH.sub.3 Cyclopropyl                    1-Ethylpiperazine                               CO.sub.2 HI-70    CH.sub.3 Cyclopropyl                    2-Methylpiperazine                               CO.sub.2 HI-71    C(CH.sub.3).sub.2 CO.sub.2 H            Cyclopropyl                    1-Ethylpiperazine                               CO.sub.2 HI-72    C(CH.sub.3).sub.2 CO.sub.2 H            Cyclopropyl                    2-Methylpiperazine                               CO.sub.2 H__________________________________________________________________________ 
    
    
    
     The present invention is described in detail by the following Preparations and Examples: 
     Preparation 1 
     Preparation of 1-methyl-6,7-difluoro-1,4-dihydro-4-thioquinoline 
     A. Preparation of 1-methyl-6,7-difluro-1,2,3,4-tetrahydro-4-oxoquinoline 
     1-Methyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline carboxylic acid(7 g) was added to methyl alcohol(800 ml), and stirred at 0° C. After sodium borohydride(4.3 g) and p-toluene sulfonic acid(cat.amount) were added thereto, the reaction mixture was refuluxed for an hour, and the organic solvent was removed under reduced pressure. To the residue was added chloroform(500 ml), and it was washed twice with water (200 ml). The separated organic layer was dehydrated, and concentrated. The residue was solidified with pet. ether, and dried to give the bright-yellow-above-indicated compound(3.6 g). 
     m.p.: 65°-67.5° C. 
     Yield: 77% 
     NMR: δ(CDCl 3 ) 2.65(t,2H), 2.90(s,3H), 3.40(t,2H), 6.40(dd,1H), 7.78(m,1H) 
     B. Preparation of 1-methyl-6.7-difluoro-1,4-dihydro-4-oxoquinoline 
     1-Methyl-6,7-difluoro-1,2,3,4-tetrahydro-4-oxoquinoline(3.19 g) was added to 1,4-dioxane(90 ml). After p-chloranil(7.5 g) was added thereto, the reaction mixture was stirred at 80° C. After 24 hours, the organic solvent was removed under reduced pressure. To the residue was added chloroform(100 ml), and it was washed with 1N-sodium hydroxide solution and water. The separated organic layer was dehydrated, and concentrated. The residue was solidified with pentane, and dried to give the white above-indicated compound(1.6 g). 
     m.p.: 173.5°-175.5° C. 
     Yield: 52% 
     NMR: δ(CDCl 3 ) 3.75(s,3H), 6.20(d,1H), 7.20(ad,1H), 7.50(d,1H), 8.20(dd,1H) 
     C.Preparation of 1-methyl-6,7-difluoro-1,4-dihydro-4-thioquinoline 
     1-Methyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline(1.6 g), phosphorus pentasulfide (5.3 g), and sodium bicarbonate(4.0 g) were added to acetonitrile(50 ml), and stirred at 60° C. for 4 hours, cooled to room temperature. The precipitates were filtered, and dried to give the yellow above-indicated compound(1.36 g). 
     m.p.: 198°-200° C. 
     Yield: 77% 
     NMR: δ(CDCl 3 ) 3.90(s,3H), 7,30(d,1H), 7.55-7.85(m,2H), 8.50-8.85(dd,1H) 
     Preparation 2 
     Preparation of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-thioquinoline 
     A. Preparation of 1-cyclopropyl-6,7-difluoro-1,2,3,4-tetrahydro-4-oxoquinoline 
     1-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline carboxylic acid(20 g) and sodium borohydride(11.5 g) were reacted in the same method as described in Preparation 1-A to give the yellow above-indicated compound(12 g). 
     m.p.: 77.8°-80.4° C. 
     Yield: 86% 
     NMR: δ(CDCl 3 ) 0.65-1.05(m,4H), 2.20-2.40(m,1H), 2.60(t,2H), 3.50(t,2H), 7.05(dd,1H), 7.70(dd,1H) 
     B. Preparation of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline 
     1-Cyclopropyl-6,7-difluoro-1,2,3,4-tetrahydro-4-oxoquinoline(10 g) and p-chloranil (22 g) were reacted in the same method as described in Preparation 1-B to give the white above-indicated compound(8.6 g). 
     m.p.: 169.6°-172° C. 
     Yield: 87% 
     NMR: δ(CDCl 3 ) 0.95-1.40(m,4H), 3.20-3.45(m,1H), 6.15(d,1H), 7.50-7.80(m,2H), 8.10(dd,1H) 
     C. Preparation of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-thioquinoline 
     1-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline(4.8 g) and phosphorus pentasulfide(14.6 g) were reacted in the same method as described in preparation 1-C to give the yellow above-indicated compound(4.98). 
     m.p.: 178°-177° C. 
     Yield: 94% 
     NMR: δ(CDCl 3 ) 0.90-1.45(m,4H), 3.25-3.60(m,1H), 7.20-7.50(m,2), 7.60-7.92(dd,1H), 8.55-8.85(dd,1H) 
     Preparation 3: 
     Preparation of 1-ethyl,-6,7-difluoro-1,4-dihydro-4-thioquinoline 
     A. Preparation of 1-ethyl-6,7-difluoro-1,2,3,4-tetrahydro-4-oxoquinoline 
     1-Ethyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline carboxylic acid(20 g) and sodium borohydride(12 g) were reacted in the same method as described in Preparation 1-A to give the bright-yellow above-indicated compound(11 g). 
     m.p.: 82°-84° C. 
     Yield: 80% 
     NMR: δ(CDCl 3 ) 1.15(t,3H), 2.70(t,2H), 3.40(q,2H), 3.50(t,2H), 6.50(dd,1H), 7.65(dd,1H) 
     B. Preparation of 1-ethyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline 
     1-Ethyl-6,7-difluoro-1,2,3,4-tetrahydro-5-oxoquinoline(10 g) and p-chloranil (23 g) were reacted in the same method as described in Preparation 1-B to give the white above-indicated compound(6.7 g). 
     m.p.: 176°-178° C. 
     Yield: 68% 
     NMR: δ(CDCl 3 ) 1.20(t,3H), 4.10(q,2H), 6.20(d,1H), 7.70-8.05(m,2H), 8.20(dd,1H) 
     C. Preparation of ethyl-6,7-difluoro-1,4-dihydro-4-thioquinoline 
     1-Ethyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline(6.7 g) and phosphorus pentasulfide(21 g) were reacted in the same method as described in Preparation 1-C to give the yellow above-indicated compound(4.4 g). 
     m.p.: 174°-176° C. 
     Yield: 60% 
     NMR: δ(CDCl 3 ) 1.40(t,3H), 4.40(q,2H), 7.30(d,1H), 7.95(d,1H), 8.15(dd,1H), 8.65(dd,1H) 
     Preparation 4: 
     Preparation of 1-allyl-6,7-difluoro-1,4-dihydro-4-thioquinoline 
     A. Preparation of 1-allyl-6,7-difluoro-1,2,3,4-tetrahydro-4-oxoquinoline 
     1-Allyl-6,7-difluoro-1,4-dihydro-4-oxoquiniline carboxylic acid(25 g) and sodium borohydride(14.2 g) were reacted in the same method as described in Preparsation 1-A to give the bright-yellow above-indicated compound(14 g). 
     m.p.: 57°-59° C. 
     Yield: 80% 
     NMR: δ(CDCl 3 ) 2.70(t,2H), 3.55(t,2H), 3.95(d,2H), 5.25(dd,2H), 5.75-5.90(m,1H), 6.50(dd,1H), 7.65(dd,1H), 
     B. Preparation of 1-allyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline 
     1-Allyl-6,7-difluoro-1,2,3,4-tetrahydro-4-oxoquinoline(13.3 g) and p-chloranil (29.3 g) were reacted in the same method as described in Preparation 1-B to give the white above-indicated compound(12.3 g). 
     m.p.: 172°-174° C. 
     Yield: 93% 
     NMR: δ(CDCl 3 ) 4.70(d,2H), 5.18(d,1H), 5.38(d,1H), 5.95-6.10(m,1H), 6.28(d,1H), 7.25(dd,1H), 7.55(d,1H), 8.25(dd,1H) 
     C. Preparation of 1-allyl-6,7-difluoro-1,4-dihydro-4-thioquinoline 
     1-Allyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline(12 g) and phosphorus pentasulfide(36 g) were reacted in the same method as described in Preparation 1-C to give the yellow above-indicated compound(10 g). 
     m.p.: 160°-163° C. (dec.) 
     Yield: 77% 
     NMR: δ(CDCl 3 ) 5.05(d,2H), 5.15(d,1H), 5.25(d,1H), 5,98-6.10(m,1H), 7.35(d,1H), 7.95-8.05(m,2H), 8.65(dd,1H) 
     Preparation 5: 
     Preparation of 1-methyl-6-fluoro-7-piperazinyl-1,4-dihydro-4-thioquinoline 
     1-Methyl-6,7-difluoro-1,4-dihydro-4-thioquinoline(1.2 g) and piperazine (1.4 g) were added to pyridine(7 ml), and stirred at 130° C. for an hour. The organic solvent was removed under reduced pressure. To the residue was added chloroform(50 ml), and it was washed with water. The separated organic layer was dehydrated, and concentrated. The residue was solidified with water, and dried to give the yellow above-indicated compound(0.9 g). 
     m.p.: 255° C. 
     Yield: 54% 
     NMR: δ(DMSO-d 6 ) 2.60-3.10(m,8H), 3.90(s,3H), 7.10-7.65(m,3H), 8.40(d,1H) 
     Preparation 6: 
     Preparation of 1-methyl-6-fluoro-7-(N-methylpiperazinyl)-1,4-dihydro-4-thioquinoline 
     1-Methyl-6,7-difluoro-1,4-thioquinoline(1.2 g) and N-methylpiperazine(1.9 ml) were reacted in the same method as described in Preparation 5 to give the yellow above-indicated compound(1.1 g). 
     m.p.: 226°-228° C.(dec.) 
     Yield: 63% 
     NMR: δ(DMSO-d 6 ) 2.38(s,3H), 2.60(t,4H), 3.30(t,4H), 3.75(s,3H), 6.58(d,1H), 7.05(m,2H), 8.40(d,1H) 
     Preparation 7: 
     Preparation of 1-methyl-6-fluoro-7-(1-ethylpiperazinyl)-1,4-dihydro-4-thioquinoline 
     1-Methyl-6,7-difluoro-1,4-thioquinoline(6 g) and 1-ethylpiparazine(9.5 g) were reacted in the same method as described in Preparation 5 to give the yellow above-indicated compound(4.2 g). 
     m.p.: 214°-216° C.(dec.) 
     Yield: 54% 
     NMR: δ(DMSO-d 6 ) 1.15(t,3H), 2.30-2.80(m,6H), 3.30(t,4H), 3.80(s,3H), 6.60(d,1H), 7.05-7.25(m,2H), 8.50(d,1H) 
     Preparation 8: 
     Preparation of 1-methyl-6-fluoro-7-(2-methylpiperazinyl)-1,4-dihydro-4-thioquinoline 
     1-Methyl-6,7-difluoro-1,4-thioquinoline(4.9 g) and 2-methylpiperazine(6.8 g) were reacted in the same method as described in Preparation 5 to give the yellow above-indicated compound(4.0 g). 
     m.p.: 177°-179° C. 
     Yield: 56% 
     NMR: δ(DMSO-d 6 ) 1.70(s,3H), 2.70-3.30(m,3H), 3.40-3.70(m,4H), 3.90(s,3H), 6.65(d,1H), 7.05-7.30(m,2H), 8.50(d,1H) 
     Preparation 9: 
     Preparation of 1-methyl-6-fluoro-7-imidazolyl-1,4-dihydro-4-thioquinoline 
     1-Methyl-6,7-difluoro-1,4-thioquinoline(2 g) and imidazole(1.9 g) were added to pyridine(20 ml), and stirred at 130° C. for 5 hours. The organic solvent was removed under reduced pressure. The residue was solidified with water, and dried to give the yellow above-indicated compound(1.3 g). 
     m.p.: 255°-257° C.(dec.) 
     Yield: 51% 
     NMR: δ(DMSO-d 6 ) 3.90(s,3H), 7.15-7.25(m,2H),7.70-8.40(m,4H), 8.50(d,1H) 
     Preparation 10: 
     Preparation of 1-methyl-6-fluoro-7-(4-methylimidazolyl)-1,4-dihydro-4-thioquinoline 
     1-Methyl-6,7-difluoro-1,4-thioquinoline(2 g) and 4-methylimidazole(2.3 g) were reacted in the same method as described in Preparation 9 to give the yellow above-indicated compound(1.4 g). 
     m.p.: 278°-280° C.(dec.) 
     Yield: 52% 
     NMR: δ(DMSO-d 6 ) 2.40(s,3H), 3.90(s,3H), 6.90-8.35(m,5H), 8.60(d,1H) 
     Preparation 11: 
     Preparation of 1-cyclopropyl-6-fluoro-7-piperazinyl-1,4-dihydro-4-thioquinoline 
     1-Cyclopropyl-6,7-difluoro-1,4-thioquinoline(1.5 g) and piperazine(1.64 g) were reacted in the same method as described in Preparation 9 to give the yellow above-indicated compound(1.1 g). 
     m.p.: 205°-208.3° C. 
     Yield: 55% 
     NMR: δ(DMSO-d 6 ) 0.90-1.40(m,4H), 2.65-3.60(m,9H), 7.05-7.70(m,3H), 8.40(d,1H) 
     Preparation 12: 
     Preparation of 1-cyclopropyl-6-fluoro-7-(N-methylpiperazinyl)-1,4-dihydro-4-thioquinoline 
     1-Cyclopropyl-6,7-difluoro-1,4-thioquinoline(1.5 g) and N-methylpiperazine (2.1 ml) were reacted in the same method as described in Preparation 9 to give the yellow above-indicated compound(1.1 g). 
     m.p.: 181.5°-183.7° C. 
     Yield: 52% 
     NMR: δ(DMSO-d 6 ) 0.95-1.40(m,4H),2.38(s,3H), 2.62(t,4H), 3.30(t,4H). 3.40-3.62(m,1H), 7.00-7.40(m,3H), 8.40(d,1H). 
     Preparation 13: 
     Preparation of 1-cyclopropyl-6-fluoro-7-(1-ethylpiperazinyl)-1,4-dihydro-4-thioquinoline 
     1-Cyclopropyl-6,7-difluoro-1,4-thioquinoline (5 g) and 1-ethylpiperazine 7.3 g) were reacted in the same method as described in Preparation 9 to give the yellow above-indicated compound(4.0 g). 
     m.p.: 178°-180° C. 
     Yield: 54% 
     NMR: δ(DMSO-d 6 ) 0.95-1.40(m,4H),2.30-2.75(m,6H), 3.30(t,4H), 3.40-3.60(m,1H), 7.05-7.40(dd,3H), 8.45 (d,1H), 
     Preparation 14: 
     Preparation of 1-cyclopropyl-6-fluoro-7-(2-methylpiperazinyl)-1,4-dihydro-4-thioquinoline 
     1-Cyclopropyl6,7-difluoro-1,4-thioquinoline(5 g) and 2-methylpiperazine(6.4 g) were reacted in the same method as described in Preparation 9 to give the yellow above-indicated compound(4.8 g). 
     m.p.: 132°-132° C.(dec.) 
     Yield: 89% 
     NMR: δ(DMSO-d 6 ) 0.90-1.40(m,7H),2.40-3.75(m,8H), 7.10-7.38(dd,3H), 8.50(d,1H) 
     Preparation 15: 
     Preparation of 1-cyclopropyl-6-fluoro-7-imidazolyl-1,4-dihydro-4-thioquinoline 
     1-Cyclopropyl-6,7-difluoro-1,4-thioquinoline(5 g) and imidazole(4.3 g) were reacted in the same method as described in Preparation 9 to give the yellow above-indicated compound(2.8 g). 
     m.p.: 205°-207° C.(dec.) 
     Yield: 45% 
     NMR: δ(DMSO-d 6 ) 1.10-1.20(m,2H), 1.28-1.38(m,2H), 3.65-3.85(m,1H), 7.25(dd,2H), 7.80(s,1H), 7.95(dd,1H), 8.25(dd1H), 8.35(d,1H), 8.55(d,1H) 
     Preparation 16: 
     Preparation of 1-cyclopropyl-6-fluoro-7-(4-methylimidazolyl)-1,4-dihydro-4-thioquinoline 
     1-Cyclopropyl-6,7-difluoro-1,4-thioquinoline(2.5 g) and 4-methylpiperazine(2.6 g) were reacted in the same method as described in Preparation 9 to give the yellow above-indicated compound(1.9 g). 
     m.p.: 242°-244° C.(dec.) 
     Yield: 58% 
     NMR: δ(DMSO-d 6 ) 1.00-1.35(m,4H), 2.45(s,3H), 3.72-3.85(m,1H), 6.90(s,1H), 7.25-8.35(m,4H), 8.60(d,1H) 
     Preparation 17: 
     Preparation of 1-cyclopropyl-6-fluoro-7-(1-ethylpiperazinyl)-1,4-dihydro-4-thioquinoline-3-carboxylic acid 
     1-Cyclopropyl-6,7-difluoro-1,4-thioquinoline-3-carboxylic acide(1.8 g) and 1-ethylpiperazine(2.2 g) were reacted in the same method as described in Preparation 9 to give the yellow above-indicated compound(1.5 g). 
     m.p.: 232°-234° C.(dec.) 
     Yield: 60% 
     NMR: δ(DMSO-d 6 ) 1.20(t,3H), 1.40(m,2H), 2.75-3.40(m,6H), 3.60(m,4H), 7.40(d,1H), 8.40(d,1H), 8.85(s,1H) 
     Preparation 18: 
     Preparation of 1-cyclopropyl-6-fluoro-7-(2-methylpiperazinyl)-1,4-dihydro-4-thioquinoline-3-carboxylic acid 
     1-Cyclopropyl-6,7-difluoro-1,4-thioquinoline-3-carboxylic acid(2 g) and 2-methylpiperazine(2.2 g) were reacted in the same method as described in Preparation 9 to give the yellow above-indicated compound(1.3 g). 
     m.p.: 240°-242° C.(dec.) 
     Yield: 45% 
     NMR: δ(DMSO-d 6 ) 1.20-1.45(m,4H), 1.70(s,3H), 2.75-3.30(m,4H), 3.45-3.75(m,4H), 7.40(d,1H), 8.45(d,1H), 8.80(s,1H) 
     Preparation 19: 
     Preparation of 1-ethyl-6-fluoro-7-piperazinyl-1,4-dihydro-4-thioquinoline 
     1-Ethyl-6,7-difluoro-1,4-thioquinoline(1 g) and piperazine(1.15 g) were reacted in the same method as described in Preparation 9 to give the yellow above-indicated compound(1.2 g). 
     m.p.: 106°-108° C. 
     Yield: 89% 
     NMR: δ(DMSO-d 6 ) 1.40(t,3H), 2.60-3.45(m,8H), 4.40(q,2H), 7.05-7.85(m,3H), 8.40(d,1H) 
     Preparation 20: 
     Preparation or 1-ethyl-6-fluoro-7-(N-methylpiperazinyl)-1,4-dihydro-4-thioquinoline 
     1-Ethyl-6,7-difluoro-1,4-thioquinoline(1 g) and N-methylpiperazine (1.33 g) were reacted in the same method as described in Preparation 9 to give the yellow above-indicated compound(1.1 g). 
     m.p.: 184°-186° C.(dec.) 
     Yield: 77% 
     NMR: δ(DMSO-d 6 ) 1.40(t,3H), 2.28(s,3H),2.48-2.55(m,4H), 3.25-3.35(m,4H), 4.42(q,2H), 7.05(d,1H), 7.15(d,1H), 7.88(d,1H), 8.40(d,1H) 
     Preparation 21: 
     Preparation of 1-ethyl-6-fluoro-7-(1-ethylpiperazinyl)-1,4-dihydro-4-thioquinoline 
     1-Ethyl-6,7-difluoro-1,4-thioquinoline(1 g) and 1-ethylpiperazine(1.52 g) were reacted in the same method as described in Preparation 9 to give the yellow above-indicated compound(1.23 g). 
     m.p.: 159°-161° C. 
     Yield: 82% 
     NMR: δ(DMSO-d 6 ) 1.20(t,3H), 1.40(t,3H), 2.40-3.50(m,8H), 3.80(q,2H), 4.40(q,2H), 7.05-7.20(m,2H), 7.85(d,1H), 8.45(d,1H) 
     Preparation 22: 
     Preparation of 1-ethyl-6-fluoro-7-(2-methylpiperazinyl)-1,4-dihydro-4-thioquinoline 
     1-Ethyl-6,7-difluoro-1,4-thioquinoline(1 g) and 2-methylpiperazine(1.33 g) were reacted in the same method as described in Preparation 9 to give the yellow above-indicated compound(1.25 g). 
     m.p.: 125°-127° C.(dec.) 
     Yield: 87% 
     NMR: δ(DMSO-d 6 ) 1.15(d,3H), 1.40(t,3H), 2.40-3.60(m,7H), 4.40(q,2H), 7.05-7.40(m,3H), 8.45(d,1H) 
     Preparation 23: 
     Preparation of 1-allyl-6-fluoro-7-piperazinyl-1,4-dihydro-4-thioquinoline 
     1-Allyl-6,7-difluoro-1,4-thioquinoline(2 g) and piperazine(2.2 g) were reacted in the same method as described in Preparation 9 to give the yellow above-indicated compound(2.3 g). 
     m.p.: 93°-95° C. 
     Yield: 86% 
     NMR: δ(DMSO-d 6 ) 2.64-3.40(m,8H), 5.10(d,2H), 5.15-6.20(m,3H), 7.05-7.90(m,3H), 8.40(d,1H) 
     Preparation 24: 
     Preparation of 1-allyl-6-fluoro-7-(N-methylpiperazinyl)-1,4-dihydro-4-thioquinoline 
     1-Allyl-6,7-difluoro-1,4-thioquinoline(2 g) and N-methylpiperazine(2.5 g) were reacted in the same method as described in Preparation 9 to give the yellow above-indicated compound(2.3 g). 
     m.p.: 145°-147° C. 
     Yield: 82% 
     NMR: δ(DMSO-d 6 ) 2.25(s,3H), 2.60-3.30(m,8H), 5.10(d,2H), 5.30-6.05(m,3H), 7.10-7.80(m,3H), 8.40(d,1H) 
     Preparation 25: 
     Preparation of 1-allyl-6-fluoro-7-(1-ethylpiperazinyl)-1,4-dihydro-4-thioquinoline 
     1-Allyl-6,7-difluoro-1,4-thioquinoline(2 g) and 2-ethylpiperazine(2.9 g) were reacted in the same method as described in Preparation 9 to give the yellow above-indicated compound(2.35 g). 
     m.p.: 118°-120° C. 
     Yield: 80% 
     NMR: δ(DMSO-d 6 ) 1.15(t,3H), 2.30-3.30(m,10H), 5.05(d,2H), 5.20-6.20(m,3H), 7.05-7.80(m,3H), 8.40(d,1H) 
     Preparation 26: 
     Preparation of 1-allyl-6-fluoro-7-(2-methylpiperazinyl)-1,4-dihydro-4-thioquinoline 
     1-Allyl-6,7-difluoro-1,4-thioquinoline(2 g) and 2-methylpiperazine(2.5 g) were reacted in the same method as described in Preparation 9 to give the yellow above-indicated compound(1.9 g). 
     m.p.: 162°-164° C. 
     Yield: 68% 
     NMR: δ(DMSO-d 6 ) 1.05(d,3H), 2.40-3.50(m,7H), 5.05(d,2H), 5.20(d,1H),5.30(d,1H), 5.98-6.12(m,1H), 7.00(d,1H), 7.18(d,1H), 7.85 (d,1H), 8.38(d,1H) 
     EXAMPLE 1 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamide]-3-(1-methyl-6-fluoro-7-piperazinylquinolinium-4-yl)thiomethyl-3-cephem-4-carboxylate 
     To a solution of 3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino) acetamido]-3-cephem-4-carboxylic acid(0.73 g) suspended in 1:1(V/V) mixture of acetonitrile/water(30 ml) were added 1-methyl-6-fluoro-7-piperazinyl-1,4-dihydro-4-thioquinoline(0.5 g) and sodium iodide(2.4 g). The reaction mixture was heated to 60° C. for 5 hours. 
     The organic solvent was removed under reduced pressure. The residue was added acetone. The precipitates were filtered, and dried to give the above-indicated compound(0.6 g). 
     IR: (KBr, cm -1 ) 1762(β-lactam) 
     NMR: δ(DMSO-d 6 ) 3.00-3.70(m,10H), 3.85(s,3H), 3.90(s,3H), 4.30(s,2H), 5.05(d,1H), 5.65(dd,1H), 6.75(s,1H), 6.90-7.50(m,4H), 7.75(d,1H), 8.30(d,1H), 9.20-9.60(m,1H) 
     EXAMPLE 2 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-[1-methyl-6-fluoro-7-(N-methylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-cephem-4-carboxylic acid(0.7 g) and 1-methyl-6-fluoro-7-(N-methylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.5 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.61 g). 
     IR: (KBr, cm -1 ) 1760(β-lactam) 
     NMR: δ(DMSO-d 6 ) 2.38(s,3H), 3.20-3.70(m,10H), 3.80(s,3H), 3.90(s,3H), 4.25(s,2H), 4.95(d,1H), 5.50(dd,1H), 6.60(s,1H),6.80-7.40(m,4H),7.70(d,1H), 8.70(d,1H), 9.40-9.65(m,1H) 
     EXAMPLE 3 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-[1-methyl-6-fluoro-7-(1-ethylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-cephem-4-carboxylic acid(0.67 g) and 1-methyl-6-fluoro-7-(1-ethylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.5 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.53 g). 
     IR: (KBr, cm -1 ) 1760(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.00(t,3H), 2.40(q,2H), 2.80-3.70(m,10H), 3.80(s,3H), 3.95(s,3H), 4.30(s,2H), 4.95(d,1H), 5.50(dd,1H), 6.65(s,1H), 6.80-7.30(m,4H), 7.90(d,1H), 8.40(d,1H), 9.30(d,1H) 
     EXAMPLE 4 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-(1-methyl-6-fluoro-7-(2-methyl)piperazinylquinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-cephem-4-carboxylic acid(0.7 g) and 1-methyl-6-fluoro-7-(2-methylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.5 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.57 g). 
     IR: (KBr, cm -1 ) 1760(β-lactam) 
     NMR: δ(DMSO- 6 ) 1.70(s,3H), 2.75-3.70(m,9H), 3.70(s,3H), 3.85(s,3H), 4.40(s,2H), 5.00(d,1H), 5.50(dd,1H), 6.60(s,1H), 6.90-7.30(m,4H), 7.80(d,1H), 9.40(d,1H) 
     EXAMPLE 5 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-(1-cyclopropyl-6-fluoro-7-piperazinylquinolinium-4-yl)thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-cephem-4-carboxylic acid(0.68 g) and 1-cyclopropyl-6-fluoro-7-piperazinyl-1,4-dihydro-4-thioquinoline(0.5 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.53 g). 
     IR: (KBr,cm -1 ) 1760(β-lactam) 
     NMR: δ(DMSO-d 6 ) 0.95-1.40(m,4H), 2.95-3.60(m,1H), 3.85(s,3H), 4.20(s.e.,2H), 4.95(d,1H), 5.50(dd,1H), 6.60-7.30(m,5H), 7.70(d,1H), 8.20(d,1H), 9.30-9.50(m,1H), 
     EXAMPLE 6 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-[1-cyclopropyl-6-fluoro-7-(N-methylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z) -2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-cephem-4-carboxylic acid(0.65 g) and 1-cyclopropyl-6-fluoro-7-(N-methylpiperazinyl) -1,4-dihydro-4-thioquinoline(0.5 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.52 g). 
     IR: (KBr,cm -1 ) 1760(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.00-1.45(m,4H), 2.30(s,3H), 3.10-3.80(m,11H), 3.90(s,3H), 4.00-4.40(s.e.,2H), 4.95(d,1H), 5.50(dd,1H), 6.70(s,1H), 6.95-7.30(m,4H), 7.70(d,1H), 8.45(d,1H), 9.42(d,1H) 
     EXAMPLE 7 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-3-[1-cyclopropyl-6-fluoro-7-(1-ethylpiperazinyl)quinolinium-4-yl]-thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-cephem-4-carboxylic acid(0.63 g) and 1-cyclopropyl-6-fluoro-7-(1-ethylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.5 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.57 g). 
     IR: (KBr, cm -1 ) 1760(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.00-1.40(m,7H), 2.45(q,2H), 3.00-3.80(m,11H), 3.90(s,3H), 4.40(s,2H), 4.95(d,1H), 5.45(dd,1H), 6.65(s,1H), 6.90-7.35(m,4H), 7.70(d,1H), 8.45(s,1H), 9.40 (d,1H) 
     EXAMPLE 8 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-[1-cyclopropyl-6-fluoro-7-(2-methylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-cephem-4-carboxylic acid(0.65 g) and 1-cyclopropyl-6-fluoro-7-(2-methylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.5 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.61 g). 
     IR: (KBr,cm -1 ) 1760(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.00-1.35(m,4H), 1.74(s,3H), 2.70-3.75(m,10H), 3.90(s,3H), 4.40(s,2H), 5.00(d,1H), 5.50(dd,1H), 6.65(s,1H), 6.90-7.30(m,4H), 7.70(d,1H), 8.40(d,1H), 9.40(d,1H) 
     EXAMPLE 9 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-(1-ethyl-6-fluoro-7-piperazinylquinolinum-4-yl)thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-cephem-4-carboxylic acid(0.3 g) and 1-ethyl-6-fluoro-7-piperazinyl-1,4-dihydro-4-thioquinoine(0.21 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.24 g). 
     IR: (KBr,cm -1 ) 1760(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.45(t,3H), 2.65-3.60(m,10H), 3.90(s,3H), 4.10(q,2H), 4.40(s,2H), 5.00(d,1H), 5.50(dd,1H), 6.60(s,1H), 6.85-7.20(m,4H), 7.75(d,1H), 8.40(d,1H), 9.45 (d,1H) 
     EXAMPLE 10 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-(1-ethyl-6-fluoro-7-(N-methylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-cephem-4-carboxylic acid(0.3 g) and 1-ethyl-6-fluoro-7-(N-methylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.22 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.25 g). 
     IR: (KBr,cm -1 ) 1760(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.40(t,3H), 2.45(s,3H), 2.65(t,4H), 3.30-3.60(m,6H), 3.90(s,3H), 4.10(q,2H), 4.40(s,2H), 5.05(d,1H), 5.50(dd,1H), 6.65(s,1H), 7.05-7.40(m,4H), 7.45(d,1H), 8.45(d,1H), 9.40(d,1H) 
     EXAMPLE 11 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-[1-ethyl-6-fluoro-7-(1-ethylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylat 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-cephem-4-carboxylic acid(0.3 g) and 1-ethyl-6-fluoro-7-(1-ethylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.23 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.26 g). 
     IR: (KBr,cm -1 ) 1760(β-lactam). 
     NMR: δ(DMSO-d 6 ) 1.20(t,3H), 1.40(t,3H), 2.30-2.85(m,6H), 3.30-3.85 (m,6H), 3.85(s,3H), 4.10(q,2H), 4.40(s,2H), 4.95(d,1H), 5.50(dd,1H), 6.65(s,1H), 6.80-7.15(m,4H), 7.25(d,1H), 8.45(d,1H), 9.40(d,1H) 
     EXAMPLE 12 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-[1-ethyl-6-fluoro-7-(2-methylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-cephem-4-carboxylic acid(0.3 g) and 1-ethyl-6-fluoro-7-(2-methylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.22 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.26 g). 
     IR: (KBr,cm -1 ) 1760(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.40(t,3H), 1.70(s,3H), 2.65-3.25(m,3H), 3.45-3.75(m,6H), 3.90(s,3H), 4.10(q,2H), 4.45(s,2H), 5.00(d,1H), 5.50(dd,1H), 6.65(s,1H), 6.70-7.30(m,4H), 7.40(d,1H), 8.45(d,1H), 9.40(d,1H) 
     EXAMPLE 13 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-(1-allyl-6-fluoro-7-piperazinylquinolinium-4-yl)thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-cephem-4-carboxylic acid(0.3 g) and 1-allyl-6-fluoro-7-piperazinyl-1,4-dihydro-4-thioquinoline(0.2 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.23 g). 
     IR: (KBr,cm -1 ) 1760(β-lactam) 
     NMR: δ(DMSO-d 6 ) 2.65-3.60 (m,10H), 3.90(s,3H), 4.40-4.50(m,4H), 4.95(d,1H), 5.20(d,2H), 5.45(dd,1H), 6.10-6.25(m,1H), 6.65 (s,1H), 6.90-7.45(m,4H), 7.75(d,1H), 8.40(d,1H), 9.40(d,1H) 
     EXAMPLE 14 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-[1-allyl-6-fluoro-7-(N-methylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-cephem-4-carboxylic acid(0.3 g) and 1-allyl-6-fluoro-7-(N-methylpiperazinyl )-1,4-dihydro-4-thioquinoline(0.2 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.25 g). 
     IR: (KBr,cm -1 ) 1760(β-lactam) 
     NMR: δ(DMSO-d 6 ) 2.40(s,3H), 2.65-3.60(m,10H), 3.90(s,3H), 4.40-4.50(m,4H), 7.55(d,1H), 8.40(d,1H), 9.45(d,1H) 
     EXAMPLE 15 
     Synthesis of 7-[(Z)-2(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-[1-allyl-6-fluoro-7-(1-ethylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-cephem-4-carboxylic acid(0.3 g) and 1-allyl-6-fluoro-7-(1-ethylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.22 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.24 g). 
     IR: (KBr,cm -1 ) 1760(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.20(t,3H), 2.35-2.70(m,6H), 3.30-3.65(m,6H). 3.95(s,3H), 4.35-4.50(m,4H), 4.95-5.05(m,3H), 5.45(dd,1H), 5.95-6.05(m,1H), 6.65(s,1H), 6.70-7.25(m,4H), 7.30(d,1H), 8.40(d,1H), 9.40(d,1H) 
     EXAMPLE 16 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-[1-allyl-6-fluoro-7-(2-methylpiperazinyl)quinolinium-4-yl]thiomethyl 3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-cephem-4-carboxylic acid(0.3g) and 1-allyl-6-fluoro-7-(2-methylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.2 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.26 g). 
     IR: (KBr,cm -1 ) 1760(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.70(s,3H), 2.70-3.20(m,3H), 3.45-3.70(m,6H), 3.90(s,3H) 4.40-4.50(m,4H), 5.00(d,1H), 5.10(d,2H), 5.45(dd,1H), 6.00-6.10(m,1H), 6.65(s,1H), 6.70-7.30(s,4H), 7.35(d,1H), 8.50(d,1H), 9.40(d,1H) 
     Example 17 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-(1-methyl-6-fluoro-7-imidazolylquinolinium-4-yl)thiomethyl-3-cephem-4-carboxylate 
     To a solution of 3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-cephem-4-carboxylic acid(0.8 g) suspended in 1:1(V/V) mixture of acetonitrile/water(40 ml) were added 1-methyl-6-fluoro-7-imidazolyl-1,4-dihydro-4-thioquinoine(0.51 g) and sodium iodide(2.6 g). The reaction mixture was heated to 60° C. for 5 hours. The organic solvent was removed under reduced pressure. The residue was added acetone. The precipitates were filtered, and chromatographed over silica gel. Elution with a 4:1(V/V) mixture of acetonitrile/water gave the above-indicated compound(0.65 g). 
     IR: (KBr,cm -1 ) 1761(β-lactam) 
     NMR: δ(DMSO-d 6 ) 3.55(s,2H), 3.85(s,3H), 3.95(s,3H), 4.40(s,2H), 4.95(d,1H), 5.50(dd,1H), 6.65(s,1H), 6.70(d,1H), 6.80-7.40(m,6H), 7.85(s,1H), 8.50(d,1H), 9.40(d,1H) 
     EXAMPLE 18 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-[1-methyl-6-fluoro-7-(4-methylimidazolyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-cephem-4-carboxylic acid(0.45 g) and 1-methyl-6-fluoro-7-(4-methylimidazolyl)-1,4-dihydro-4-thioquinoline(0.3 g) were reacted in the same manner as described in Example 17 to give the above-indicated compound(0.38 g). 
     IR: (KBr,cm -1 ) 1762(β-lactam) 
     NMR: δ(DMSO-d 6 ) 2.40(s,3H), 3.50(s,2H), 3.80(s,3H), 3.90(s,3H) 4.40(s,2H), 5.00(d,1H), 5.50(dd,1H), 6.60-6.85(m,3H), 7.05-7.60(m,5H), 8.50(d,1H), 9.40(d,1H) 
     EXAMPLE 19 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamide]-3-(1-cyclopropyl-6-fluoro-7-imidazolylquinolinium-4-yl)thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamide]-3-cephem-4-carboxylic acid(0.8 g) and 1-cyclopropyl-6-fluoro-7-imidazolyl-1,4-dihydro-4-thioquinoline(0.55 g) were reacted in the same manner as described in Example 17 to give the above-indicated compound(0.66 g). 
     IR: (KBr,cm -1 ) 1762(β-lactam) 
     NMR: δ(DMSO-d 6 ) 0.95-1.40(m,4H), 3.40-3.65(m,3H), 3.90(s,3H), 4.40(s,2H), 4.95(d,1H), 5.50(dd,1H), 6.65(s,1H), 6.85-7.35(m,6H) 7.40(d,1H), 7.85(s,1H), 8.50(d,1H), 9.40(d,1H) 
     EXAMPLE 20 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-[1-cyclopropyl-6-fluoro-7-(4-methylimidazolyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-cephem-4-carboxylic acid(0.8 g) and 1-cyclopropyl-6-fluoro-7-(4-methylimidazolyl) -1,4-dihydro-4-thioquinoline(0.58 g) were reacted in the same manner as described in Example 17 to give the above-indicated compound(0.67 g). 
     IR: (KBr,cm -1 ) 1761(β-lactam) 
     NMR: δ(DMSO-d 6 ) 0.90-1.40(m,4H), 2.45(s,3H), 3.45-3.60(m,3H), 3.90(s,3H), 4.40(s,2H), 5.00(d,1H), 5.50(dd,1H), 6.65(s,1H), 6.90-7.50(m,6H), 7.65(s,1H), 8.45(d,1H), 9.40(d,1H) 
     EXAMPLE 21 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(allyloxyimino)acetamido]-3-(1-methyl-6-fluoro-7-piperazinylquinolinium-4-yl)thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(allyloxyimino)acetamido]-3-cephem-4-carboxylic acid(0.4 g) and 1-methyl-6-fluoro-7-piperazinyl-1,4-dihydro-4-thioquinoline(0.26 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.34 g). 
     IR: (KBr,cm -1 ) 1762(β-lactam) 
     NMR: δ(DMSO-d 6 ) 2.65-3.10(m,8H), 3.58(s,2H), 3.90(s,3H), 4.40(s,2H), 5.05-5.80(m,4H), 5.85-6.15(m,3H), 6.85(s,1H), 6.95-7.30(m,4H), 7.65(d,1H), 8.40(d,1H), 9.40(d,1H), 
     EXAMPLE 22 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(allyloxyimino) acetamido]-3-[1-methyl-6-fluoro-7-(N-methylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(allyloxyimino)acetamido]-3-cephem-4-carboxylic acid(0.4 g) and 1-methyl-6-fluoro-7-(N-methylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.27 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.33 g). 
     IR: (KBr,cm -1 ) 1760(β-lactam) 
     NMR: δ(DMSO-d 6 ) 2.40(s,3H), 2.60-3.65(m,10H), 3.80(s,3H), 4.40(s,2H), 5.00-6.10(m,7H), 6.55-7.05(m,4H), 8.40(d,1H), 9.45(d,1H) 
     EXAMPLE 23 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(allyloxyimino) acetamido]-3-[1-methyl-6-fluoro-7-(1-ethylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(allyloxyimino)acetamido]-3-cephem-4-carboxylic acid(0.4 g) and 1-methyl-6-fluoro-7-(1-ethylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.28 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.33 g). 
     IR: (KBr,cm -1 ) 1761(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.20(t,3H), 2.35-2.80(m,6H), 3.30-3.60(m,6H), 3.80(s,3H), 4.45(s,2H), 5.05-5.90(m,6H), 6.10-6.70(m,3H), 7.05-7.25 (m,2H), 8.50(d,1H), 9.45(d,1H), 
     EXAMPLE 24 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(allyloxyimino)acetamido]-3-[1-methyl-6-fluoro-7-(2-methylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(allyloxyimino)acetamido]-3-cephem-4-carboxylic acid(0.4 g) and 1-methyl-6-fluoro-7-(2-methylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.27 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.34 g). 
     IR: (KBr,cm -1 ) 1762(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.70(s,3H), 2.70-3.75(m,9H), 3.85(s,3H), 4.45(s,2H), 5.00-5.80(m,6H), 5.95-6.65(m,3H), 7.05-7.30(m,2H), 8.50(d,1H), 9.40(d,1H) 
     EXAMPLE 25 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(allyloxyimino)acetamido]-3-(1-cyclopropyl-6-fluoro-7-piperazinylquinolinium-4-yl)thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(allyloxyimino)acetamido]-3-cephem-4-carboxylic acid(0.3 g) and 1-cyclopropyl-6-fluoro-7-piperazinyl-1,4-dihydro-4-thioquinoline(0.2 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.25 g). 
     IR: (KBr,cm -1 ) 1760(β-lactam) 
     NMR: δ(DMSO-d 6 ) 0.85-1.40(m,4H), 2.80-3.90(m,11H), 4.30-4.80(m,4H), 4.90-5.30(m,3H), 6.90-7.56(m,5H), 7.70(d,1H), 8.20(d,1H), 9.20-9.50(m,1H) 
     EXAMPLE 26 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(allyloxyimino)acetamido]-3-[1-cyclopropyl-6-fluoro-7-(N-methylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(allyloxyimino)acetamido]-3-cephem-4-carboxylic acid(0.3 g) and 1-cyclopropyl-6-fluoro-7-(N-methylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.22 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.34 g). 
     IR: (KBr,cm -1 ) 1761(β-lactam) 
     NMR: δ(DMSO-d 6 ) 0.95-1.40(m,4H), 2.35(s,3H), 3.00-3.70(m,11H), 4.42-4.80(m,3H), 5.00-5.40(m,3H), 5.70-6.00(m,3H), 6.00(s,1H),6.95-7.40(m,4H),7.70(d,1H), 8.20(d,1H), 9.40(d,1H) 
     EXAMPLE 27 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(allyloxyimino)acetamido]-3-[1-cyclopropyl-6-fluoro-7-(1-ethylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(allyloxyimino)acetamido]-3-cephem-4-carboxylic acid(0.3 g) and 1-cyclopropyl-6-fluoro-7-(1-ethylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.23 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.24 g). 
     IR: (KBr,cm -1 ) 1761(β-lactam) 
     NMR: δ(DMSO-d 6 ) 0.90-1.40(m,7H), 2.45-3.55(m,13H), 4.42-4.90(m,3H), 5.05-5.50(m,3H), 5.65-6.10(m,3H),8.50(s,1H), 6.90-7.30(m,4H) 7.45(d,1H), 8.45(d,1H), 9.45(d,1H) 
     EXAMPLE 28 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(allyloxyimino)acetamido]-3-[1-cyclopropyl-6-fluoro-7-(2-methylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(allyloxyimino)acetamido]-3-cephem-4-carboxylic acid(0.3 g) and 1-cyclopropyl-6-fluoro-7-(2-methylpiperazinyl)-4-dihydro-4-thioquinoline(0.22 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.23 g). 
     IR: (KBr,cm -1 ) 1762(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.00-1.40(m,4H), 1.70(s,3H),2.90-3.75(m,19H), 4.45-4.95(m,3H), 5.00-5.45(m,3H), 5.70-6.15(m,3H), 6.60(s,1H), 6.80-7.25(m,4H), 7.40(d,1H), 8.50(d,1H), 9.45(d,1H) 
     EXAMPLE 29 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(allyloxyimino)acetamido]-3-(1-ethyl-6-fluoro-7-piperazinylquinolinium-4-yl)thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(allyloxyimino)acetamido]-3-cephem-4-carboxylic acid(0.15 g) and 1-ethyl-6-fluoro-7-piperazinyl-1,4-dihydro-4-thioquinoline(0.1 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.11 g). 
     IR: (KBr,cm -1 ) 1760(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.45(t,3H), 2.65-3.55(m,10H), 4.10 (q,2H), 4.45-5.40(m,6H), 5.75-6.20(m,3H), 6.60(s,1H), 6.90-7.55 (m,4H), 7.70(d,1H), 8.40(d,1H), 9.40(d,1H), 
     EXAMPLE 30 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(allyloxyimino)acetamido]-3-[1-ethyl-6-fluoro-7-(N-methylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(allyloxyimino)acetamido]-3-cephem-4-carboxylic acid(0.15 g) and 1-ethyl-6-fluoro-7-(N-methylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.1 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.11 g). 
     IR: (KBr,cm -1 ) 1760(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.40(t,3H), 2.40(s,3H), 2.60-3.60(m,10H), 4.10(q,2H), 4.40-5.55(m,6H), 5.80-6.25(m,3H), 6.65(s,1H), 6.90-7.35(m,4H), 7.40(d,1H), 8.45(d,1H), 9.45(d,1H), 
     EXAMPLE 31 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(allyloxyimino)acetamido]-3-[1-ethyl-6-fluoro-7-(1-ethylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(allyloxyimino)acetamido]-3-cephem-4-carboxylic acid(0.15 g) and 1-ethyl-6-fluoro-7-(1-ethylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.11 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.12 g). 
     IR: (KBr,cm -1 ) 1760(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.20(t,3H), 1.40(t,3H), 2.50-3.55(m,12H), 4.10(q,2H), 4.40-4.85(m,3H), 4.95-5.50(m,3H), 5.80-6.15(m,3H), 6.60(s,1H),6.75-7.20(m,4H), 7.30(d,1H), 8.45(d,1H), 9.40(d,1H) 
     EXAMPLE 32 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(allyloxyimino)acetamido]-3-[1-ethyl-6-fluoro-7-(2-methylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(allyloxyimino)acetamido]-3-cephem-4-carboxylic acid(0.15 g) and 1-ethyl-6-fluoro-7-(2-methylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.1 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.12 g). 
     IR: (KBr,cm -1 ) 1761(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.40(t,3H), 1.70(s,3H), 2.65-3.70(m,9H), 4.10(q,2H), 4.45-4.90(m,3H), 5.00-5.65(m,3H), 5.90-6.20(m,3H), 6.60-6.70(m,2H), 6.90-7.25(m,3H), 7.40(d,1H), 8.45(d,1H), 9.40(d,1H) 
     EXAMPLE 33 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(allyloxyimino)acetamido]-3-(1-allyl-6-fluoro-7-piperazinylquinolinium-4-yl)thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(allyloxyimino)acetamido]-3-cephem-4-carboxylic acid(0.15 g) and 1-allyl-6-fluoro-7-piperazinyl-1,4-dihydro-4-thioquinoline(0.1 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.12 g). 
     IR: (KBr,cm -1 ) 1760(β-lactam) 
     NMR: δ(DMSO-d 6 ) 2.65-3.65(m,10H), 4.40-4.50(m,4H), 4.95-6.20(m,10H), 6.65(s,1H), 6.90-7.50(m,4H), 7.75(d,1H), 8.40(d,1H), 9.45(d,1H) 
     EXAMPLE 34 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(allyloxyimino)acetamido]-3-[1-allyl-6-fluoro-7-(N-methylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z) -2-(2-aminothiazol-4-yl)-2-(allyloxyimino)acetamido]-3-cephem-4-carboxylic acid(0.15 g) and 1-allyl-6-fluoro-7-(N-methylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.1 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.11 g). 
     IR: (KBr,cm -1 ) 1758(β-lactam) 
     NMR: δ(DMSO-d 6 ) 2.40(s,3H), 2.70-3.55(m,10H), 4.45-4.55(m,4H), 4.95-5.45(m,6H), 5.50-6.15(m,4H), 6.60(s,1H), 6.85-7.50(m,4H), 7.55(d,1H), 8.40(d,1H), 9.40(d,1H) 
     EXAMPLE 35 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(allyloxyimino)acetamido]-3-[1-allyl-6-fluoro-7-(1-ethylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(allyloxyimino)acetamido]-3-cephem-4-carboxylic acid(0.15 g) and 1-allyl-6-fluoro-7-(1-ethylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.11 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.12 g). 
     IR: (KBr,cm -1 ) 1759(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.15(t,3H), 2.40-3.50(m,12H),4.40(m,4H), 4.95-5.60(m,6H), 5.75-6.15(m,4H), 6.60-6.70(m,2H), 6.90-7.15(m,3H), 7.30(d,1H), 8.40(d,1H), 9.40(d,1H), 
     EXAMPLE 36 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(allyloxyimino)acetamido]-3-[1-allyl-6-fluoro-7-(2-methylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(allyloxyimino)acetamido]-3-cephem-4-carboxylic acid(0.15 g) and 1-allyl-6-fluoro-7-(2-methylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.1 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.11 g). 
     IR: (KBr,cm -1 ) 1758(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.70(s,3H), 2.70-3.75 (m,9H), 4.45 (m,4H) 4.80-5.45(m,6H), 5.70-6.15(m,4H), 6.65(m,2H), 6.85-7.30(m,3H), 7.35(d,1H), 8.50(d,1H), 9.45(d,1H) 
     EXAMPLE 37 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(propargyloxyimino)acetamido]-3-(1-methyl-6-fluoro-7-piperazinylquinolinium-4-yl)thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(propargyloxyimino)acetamido]-3-cephem-4-carboxylic acid(0.4 g) and 1-methyl-6-fluoro-7-piperazinyl-1,4-dihydro-4-thioquinoline(0.26 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.33 g). 
     IR: (KBr,cm -1 ) 1759(β-lactam) 
     NMR: δ(DMSO-d 6 ) 2.60-3.50(m,9H), 3.65(s,2H), 3.90(s,3H), 4.45(s,2H), 4.75(s,2H), 5.05(d,1H), 5.55(dd,1H), 6.65(s,1H), 6.80`7.50(m,4H), 7.65(d,1H), 8.40(d,1H), 9.45(d,1H) 
     EXAMPLE 38 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(propargyloxyimino) acetamido]-3-[1-methyl-6-fluoro-7-(N-methylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(propargyloxyimino)acetamido]-3-cephem-4-carboxylic acid(0.4 g) and 1-methyl-6-fluoro-7-(N-methylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.27 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.34 g). 
     IR: (KBr,cm -1 ) 1760(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.70(s,3H), 2.70-3.75 (m,9H), 4.45(m,4H), 4.80-5.45(m,6H), 5.70-6.15(m,4H), 6.65 (m,2H), 6.85-7.30(m,3H), 7.35(d,1H), 8.50(d,1H), 9.45(d,1H) 
     EXAMPLE 39 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(propargyloxyimino) acetamido]-3-[1-methyl-6-fluoro-7-(1-ethylpiperazinyl)quinolinium-4-yl]-thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(propargyloxyimino)acetamido]--3-cephem-4-carboxylic acid(0.4 g) and 1-methyl-6-fluoro-7-(1-ethylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.29 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.36 g). 
     IR: (KBr,cm -1 ) 1760(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.15(t,3H), 2.40-3.50(m,11H), 3.60(s,2H), 3.80(s,3H), 4.40(s,2H), 4.80(s,2H), 5.05(d,1H), 5.50(dd,1H), 6.60(m,2H), 6.75-7.20(m,3H), 7.25(d,1H), 8.50(d,1H), 9.45(d,1H) 
     EXAMPLE 40 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(propargyloxyimino) acetamido]-3-[1-methyl-6-fluoro-7-(2-methylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(propargyloxyimino)acetamido]-3-cephem-4-carboxylic acid(0.4 g) and 1-methyl-6-fluoro-7-(2-methylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.27 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.35 g). 
     IR: (KBr,cm -1 ) 1759(β-lactam) 
     NMR: (DMSO-d 6 ) 1.70(s,3H), 2.70-3.70(m,10H), 3.85(s,3H), 4.45(s,2H), 4.80(s,2H), 5.00(d,1H), 5.50(dd,1H), 6.65(m,2H), 6.85-7.20(m,3H), 7.30(d,1H), 8.50(d,1H), 9.45(d,1H) 
     EXAMPLE 41 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(propargyloxyimino) acetamido]-3-(1-cyclopropyl-6-fluoro-7-piperazinylquinolinium-4-yl)thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(propargyloxyimino)acetamido]-3-cephem-4-carboxylic acid(0.4 g) and 1-cyclopropyl-6-fluoro-7-piperazinyl-1,4-dihydro-4-thioquinoline(0.28 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.33 g). 
     IR: (KBr,cm -1 ) 1758(β-lactam) 
     NMR: δ(DMSO-d 6 ) 0.90-1.40(m,4H), 2.60-3.40(m,10H), 3.60(s,2H), 4.45(s,2H), 4.75(s,2H), 5.05(d,1H), 5.55(dd,1H), 6.60(s,1H), 6.80-7.40(m,4H), 7.70(d,1H), 8.40(d,1H), 9.45(d,1H) 
     EXAMPLE 42 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(propargyloxyimino) acetamido]-3-[1-cyclopropyl-6-fluoro-7-(N-methylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(propargyloxyimino)acetamido]-3-cephem-4-carboxylic acid(0.4 g) and 1-cyclopropyl-6-fluoro-7-(N-methylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.29 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.32 g). 
     IR: (KBr,cm -1 ) 1760(β-lactam) 
     NMR: δ(DMSO-d 6 ) 0.95-1.40(m,4H), 2.35(s,3H), 2.65-3.60(m,12H), 4.40(s,2H), 4.70(s,2H), 4.95(d,1H), 5.50(dd,1H), 6.65 (s,1H), 6.85-7.30(m,4H), 7.40(d,1H), 8.40(d,1H), 9.40(d,1H) 
     EXAMPLE 43 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(propargyloxyimino) acetamido]-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z) -2-(2-aminothiazol-4-yl)-2-(propargyloxyimino) acetamido]-3-cephem-4-carboxylic acid(0.4 g) and 1-cyclopropyl-6-fluoro-7-(1-ethylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.3 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.32 g). 
     IR: (KBr,cm -1 ) 1759(β-lactam) 
     NMR: δ(DMSO-d 6 ) 0.90-1.40(m,7H), 2.30-3.60(m,14H), 4.45(s,2H), 4.70(s,2H), 4.95 (d,1H), 5.55(dd,1H), 6.60(s,1H), 6.90-7.35(m,4H), 7.40(d,1H), 8.45(d,1H), 9.40(d,1H) 
     EXAMPLE 44 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(propargyloxyimino) acetamido]-3-[1-cyclopropyl-6-fluoro-7-(2-methylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7- [(Z)-2-(2-aminothiazol-4-yl)-2-(propargyloxyimino)acetamido]-3-cephem-4-carboxylic acid(0.4 g) and 1-cyclopropyl-6-fluoro-7-(2-methylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.29 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.33 g). 
     IR: (KBr,cm -1 ) 1759(β-lactam) 
     NMR: δ(DMSO-d 6 ) 0.95-1.40(m,4H), 1.70(s,3H), 2.70-3.75(m,11H), 4.40(s,2H), 4.75(s,2H), 5.05(d,1H), 5.45(dd,1H), 6.65(s,1H), 6.85-7.30(m,4H), 7.40(d,1H), 8.50(d,1H), 9.45(d,1H) 
     EXAMPLE 45 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(propargyloxyimino) acetamido]-3-(1-ethyl-6-fluoro-7-piperazinylquinolinium-4-yl)thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(propargyloxyimino)acetamido]-3-cephem-4-carboxylic acid(0.5 g) and 1-ethyl-6-fluoro-7-piperazinyl-1,4-dihydro-4-thioquinoline(0.33 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.40 g). 
     IR: (KBr,cm -1 ) 1760(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.40(t,3H), 2.60-3.50(m,11H), 4.10-4.70(m,6H), 5.00(d,1H), 5.50(dd,1H), 6.65(s,1H), 6.90-7.50(m,4H), 7.70(d,1H), 8.40(d,1H), 9.40(d,1H) 
     EXAMPLE 46 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(propargyloxyimino)acetamido]-3-[1-ethyl-6-fluoro-7-(N-methylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(propargyloxyimino)acetamido]-3-cephem-4-carboxylic acid(0.5 g) and 1-ethyl-6-fluoro-7-(N-methylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.35 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.39 g). 
     IR: (KBr,cm -1 ) 1760(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.40(t,3H), 2.40(s,3H), 2.65-3.55(m,11H), 4.10-4.75(m,6H), 4.95(d,1H), 5.50(dd,1H), 6.65(s,1H), 6.85-7.30(m,4H), 7.40(d,1H), 8.45(d,1H), 9.45(d,1H) 
     EXAMPLE 47 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(propargyloxyimino)acetamido]-3-[1-ethyl-6-fluoro-7-(1-ethylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(propargyloxyimino)acetamido]-3-cephem-4-carboxylic acid(0.5 g) and 1-ethyl-6-fluoro-7-(1-ethylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.37 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.45 g). 
     IR: (KBr,cm -1 ) 1760(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.20(t,3H), 1.40(t,3H), 2.30-3.60(m,13H), 4.10-4.40(m,4H), 4.80(s,2H), 5.00(d,1H), 5.45(dd,1H), 6.70(m,2H), 6.85-7.20(m,3H), 7.25(d,1H), 8.45(d,1H), 9.45(d,1H) 
     EXAMPLE 48 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(propargyloxyimino) acetamido]-3-[1-ethyl-6-fluoro-7-(2-methylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(propargyloxyimino)acetamido]-3-cephem-4-carboxylic acid(0.5 g) and 1-ethyl-6-fluoro-7-(2-methylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.35 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.40 g). 
     IR: (KBr,cm -1 ) 1760(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.40(t,3H), 1.70(s,3H), 2.65-3.70(m,10H), 4.10-4.80(m,6H), 5.00(d,1H), 5.60(dd,1H), 6.65(m,2H), 6.85-7.30(m,3H), 7.35(d,1H), 8.45(d,1H), 9.40(d,1H) 
     EXAMPLE 49 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(propargyloxyimino) acetamido]-3-(1-allyl -6-fluoro-7-piperazinylquinolinium-4-yl)thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(propargyloxyimino)acetamido]-3-cephem-4-carboxylic acid(0.5 g) and 1-allyl-6-fluoro-7-piperazinyl-1,4-dihydro-4-thioquinoline(0.31 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.41 g). 
     IR: (KBr,cm -1 ) 1758(β-lactam) 
     NMR: δ(DMSO-d 6 ) 2.65-3.60(m,11H), 4.40-4.80(m,6H), 5.00-5.25(m,3H), 5.65(dd,1H), 6.05-6.20(m,1H), 6.65(s,1H), 6.85-7.40(m,4H), 7.80(d,1H), 8.40(d,1H), 9.45(d,1H) 
     EXAMPLE 50 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(propargyloxyimino)acetamido]-3-[1-allyl-6-fluoro-7-(N-methylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(propargyloxyimino)acetamido]-3-cephem-4-carboxylic acid(0.5 g) and 1-allyl-6-fluoro-7-(N-methylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.34 g) were reacted in the same manner as described in Example. 1 to give the above-indicated compound(0.42 g). 
     IR: (KBr,cm -1 ) 1759(β-lactam) 
     NMR: δ(DMSO-d 6 ) 2.40(s,3H), 2.65-3.55(m,11H), 4.45-4.70(m,6H), 5.00(m,3H), 5.60(dd,1H), 5.90-6.05(m,1H), 6.60(s,1H), 6.80-7.40(m,1H), 7.55(d,1H), 8.40(d,1H), 9.45(d,1H) 
     EXAMPLE 51 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(propargyloxyimino) acetamido]-3-[1-allyl-6-fluoro-7-(1-ethylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(propargyloxyimino)acetamido]-3-cephem-4-carboxylic acid(0.5 g) and 1-allyl-6-fluoro-7-(1-ethylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.35 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.40 g). 
     IR: (KBr,cm -1 ) 1760(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.20(t,3H), 2.30-3.55(m,13H), 4.40-4.80(m,6H), 4.95(m,3H), 5.60(dd,1H), 5.95-6.10(m,1H), 6.65(m,2H), 6.80-7.20(m,3H), 7.30(d,1H), 8.40(d,1H), 9.45(d,1H) 
     EXAMPLE 52 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(propargyloxyimino) acetamido]-3-[1-allyl-6-fluoro-7-(2-methylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(propargyloxyimino)acetamido]-3-cephem-4-carboxylic acid(0.5 g) and 1-allyl-6-fluoro-7-(2-methylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.34 g) were reacted in the same manner as described in Example 1 to give the above-indicated compound(0.38 g). 
     IR: (KBr,cm -1 ) 1759(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.70(s,3H), 2.70-3.75(m,10H), 4.40-4.75(m,6H), 5.00(d,1H), 5.10(d,2H). 5.55(dd,1H), 6.60(m,1H), 6.60(m,2H), 6.80-7.25(m,3H), 7.40(d,1H), 8.50(d,1H), 9.45(d,1H) 
     EXAMPLE 53 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-(1-ethyl-6-fluoro-7-piperazinylquinolinium-4-yl)thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-cephem-4-carboxylic acid(0.4 g) and 1-methyl-6-fluoro-7-piperazinyl-1,4-dihydro-4-thioquinoline(0.24 g) were reacted in the same manner as described in Example 17 to give the above-indicated compound(0.29 g). 
     IR: (KBr,cm -1 ) 1763(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.45(d,6H), 2.60-3.55(m,10H), 3.90(s,3H), 4.40(s,2H), 5.00(d,1H), 5.65(dd,1H), 6.70(s,1H), 7.00-7.40(m,4H), 7.65(d,1H), 8.40(d,1H), 9.25(d,1H) 
     EXAMPLE 54 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-[1-methyl-6-fluoro-7-(N-methylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-cephem-4-carboxylic acid(0.4 g) and 1-methyl-6-fluoro-7-(N-methylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.25 g) were reacted in the same manner as described in Example 17 to give the above-indicated compound(0.29 g). 
     IR: (KBr,cm -1 ) 1763(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.38(s,3H), 1.42(s,3H), 2.30(s,3H), 2.70-3.60(m,10H), 3.95(s,3H), 4.40(s,2H), 5.06(d,1H), 5.65(dd,1H), 6.70(s,1H), 7.05(d,1H), 7.15(m,2H), 7.35(d,1H), 7.85(d,1H), 8.40(d,1H), 9.10(d,1H) 
     EXAMPLE 55 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-[1-methyl-6-fluoro-7-(1-ethylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-cephem-4-carboxylic acid(0.4 g) and 1-methyl-6-fluoro-7-(1-ethylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.26 g) were reacted in the same manner as described in Example 17 to give the above-indicated compound(0.31 g). 
     IR: (KBr,cm -1 ) 1761 (β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.20(t,3H), 1.40(s,6H), 2.30-2.85(m,6H), 3.20-3.55(m,6H), 3.95(s,3H), 4.40(s,2H), 5.10(d,1H), 5.65(dd,1H), 6.70(s,1H), 6.80(d,1H), 6.90-7.30(m,3H), 7.35(d,1H), 8.50(d,1H), 9.30(d,1H) 
     EXAMPLE 56 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-[1-methyl-6-fluoro-7-(2-methylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-cephem-4-carboxylic acid(0.4 g) and 1-methyl-6-fluoro-7-(2-methylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.25 g) were reacted in the same manner as described in Example 17 to give the above-indicated compound(0.30 g). 
     IR: (KBr,cm -1 ) 1762(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.45(s,6H), 1.70(s,3H),2.70-3.70(m,9H), 3.90(s,3H), 4.40(s,2H), 5.10(d,1H), 5.65(dd,1H), 6.70(m,2H), 6.80-7.20(m,3H), 7.40(d,1H), 8.50(d,1H), 9.25(d,1H) 
     EXAMPLE 57 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-(1-cyclopropyl-6-fluoro-7-piperazinylquinolinium-4-yl)thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-cephem-4-carboxylic acid(0.8 g) and 1-cyclopropyl-6-fluoro-7-piperazinyl-1,4-dihydro-4-thioquinoline(0.54 g) were reacted in the same manner as described in Example 17 to give the above-indicated compound(0.67 g). 
     IR: (KBr,cm -1 ) 1763(β-lactam) 
     NMR: δ(DMSO-d 6 ) 0.90-1.45(m,10H), 2.70-3.55 (m,11H), 4.40(s,2H), 5.05(d,1H), 5.65(dd,1H), 6.70(s,1H), 6.90-7.50(m,4H), 7.70(d,1H), 8.40(d,1H), 9.30(d,1H) 
     EXAMPLE 58 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-[1-cyclopropyl-6-fluoro-7-(N-methylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-cephem-4-carboxylic acid(0.8 g) and 1-cyclopropyl-6-fluoro-7-(N-methylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.56 g) were reacted in the same manner as described in Example 17 to give the above-indicated compound(0.66 g). 
     IR: (KBr,cm -1 ) 1763(β-lactam) 
     NMR: δ(DMSO-d 6 ) 0.95-1.50(m,10H), 2.40(s,3H), 2.60-3.55(m,11H), 4.40(s,2H), 5.10(d,1H), 5.65(dd,1H), 6.70(s,1H), 6.85-7.30(m,4H), 7.40(d,1H), 8.40(d,1H), 9.20(d,1H) 
     EXAMPLE 59 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-[1-cyclopropyl-6-fluoro-7-(1-ethylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-cephem-4-carboxylic acid(0.8 g) and 1-cyclopropyl-6-fluoro-7-(1-ethylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.58 g) were reacted in the same manner as described in Example 17 to give the above-indicated compound(0.68 g). 
     IR: (KBr, cm -1 ) 1762(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.00-1.50(m,13H), 2.40-2.65(m,6H), 3.30-3.60(m,7H), 4.25(s.e., 2H), 5.00(d,1H), 5.65(dd,1H), 6.70(s,1H), 7.10(d,1H), 7.50(d,1H), 7.75(d,1H), 7.85(d,1H), 8.10(d,1H), 8.35(d,1H), 8.90(d,1H) 
     EXAMPLE 60 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-[1-cyclopropyl-6-fluoro-7-(2-methylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-cephem-4-carboxylic acid(0.8 g) and 1-cyclopropyl-6-fluoro-7-(2-methylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.56 g) were reacted in the same manner as described in Example 17 to give the above-indicated compound(0.64 g). 
     IR: (KBr,cm -1 ) 1762(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.00-1.45(m,10H), 1.70(s,3H), 2.70-3.70(m,10H), 4.25(s,2H), 5.00(d,1H), 5.60(dd,1H), 6.70(s,1H), 6.85-7.30(m,4H), 7.50(d,1H), 8.50(d,1H), 9.20(d,1H) 
     EXAMPLE 61 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-[1-ethyl-6-fluoro-7-(1-ethylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-cephem-4-carboxylic acid(0.8 g) and 1-ethyl-6-fluoro-7-(1-ethylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.53 g) were reacted in the same manner as described in Example 17 to give the above-indicated compound(0.67 g). 
     IR: (KBr,cm -1 ) 1763(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.20(t,3H), 1.40(t,3H), 1.45(s,6H), 2.50-3.55(m,12H), 4.10-4.45(m,4H), 5.00(d,1H), 5.65(dd,1H), 6.70(s,1H), 6.80-7.20(m,4H), 7.40(d,1H), 8.45(d,1H), 9.20(d,1H) 
     EXAMPLE 62 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-[1-ethyl-6-fluoro-7-(2-methylpiperazinyl)quinolinium-4-yl]thiomethyl]-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-cephem-4-carboxylic acid(0.8 g) and 1-ethyl-6-fluoro-7-(2-methylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.51 g) were reacted in the same manner as described in Example 17 to give the above-indicated compound(0.65 g). 
     IR: (KBr,cm -1 ) 1762(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.40(t,3H), 1.45(s,6H), 1.70(s,3H), 2.65-3.50(m,9H) 4.15-4.35(m,4H), 5.00(d,1H), 5.65(dd,1H), 6.70(m,2H), 6.85-7.30(m,3H), 7.50(d,1H), 8.45(d,1H), 9.30(d,1H) 
     EXAMPLE 63 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-[1-allyl-6-fluoro-7-(1-ethylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-cephem-4-carboxylic acid(0.8 g) and 1-allyl-6-fluoro-7-(1-ethylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.51 g) were reacted in the same manner as described in Example 17 to give the above-indicated compound(0.66 g). 
     IR: (KBr,cm -1 ) 1763(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.20(t,3H), 1.40(s,6H), 2.50-3.50(m,12H), 4.40-4.55(m,4H), 4.95-5.10(m,3H), 5.70-6.00(m,2H), 6.70(m,2H), 6.80-7.30(m,3H), 7.55(d,1H), 8.40(d,1H), 9.25(d,1H) 
     EXAMPLE 64 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-[1-allyl-6-fluoro-7-(2-methylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-cephem-4-carboxylic acid(0.8 g) and 1-allyl-6-fluoro-7-(2-methylpiperazinyl)-1,4-dihydro-4-thioquinoline(0.49 g) were reacted in the same manner as described in Example 17 to give the above-indicated compound(0.63 g). 
     IR: (KBr,cm -1 ) 1763(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.40(s,6H), 1.70(s,3H), 2.70-3.75(m,9H), 4.45(m,4H), 5.00-5.10(m,3H), 5.65(dd,1H), 6.05(m,1), 6.65(m,2H), 6.90-7.30(m,3H), 7.45(d,1H), 8.50(d,1H), 9.45(d,1H) 
     EXAMPLE 65 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-(1-ethyl-6-fluoro-7-imidazolylquinolinium-4-yl)thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-cephem-4-carboxylic acid(0.4 g) and 1-methyl-6-fluoro-7-imidazolyl-1,4-dihydro-4-thioquinoline(0.22 g) were reacted in the same manner as described in Example 17 to give the above-indicated compound(0.31 g). 
     IR: (KBr,cm -1 ) 1760(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.50(s,6H), 3.65(s,2H), 3.90(s,3H), 4.45(s,2H), 5.00(d,1H), 5.65(dd,1H), 6.65(d,1H), 6.70(s,1H), 6.85-7.40(m,6H), 7.85(s,1H), 8.50(d,1H), 9.40(d,1H) 
     EXAMPLE 66 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-[1-methyl-6-fluoro-7-(4-methylimidazolyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-cephem-4-carboxylic acid(0.4 g) and 1-methyl-6-fluoro-7-(4-methylimidazolyl-1,4-dihydro-4-thioquinoline(0.23 g) were reacted in the same manner as described in Example 17 to give the above-indicated compound(0.33 g). 
     IR: (KBr,cm -1 ) 1761(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.50(s,6H), 2.40(s,3H), 3.65(s,2H), 3.95(s,3H), 4.45(s,2H), 5.05(d,1H), 5.70(dd,1H), 6.60-6.85(m,3H), 6.90-7.40(m,4H), 7.60(d,1H), 8.50(d,1H), 9.30(d,1H) 
     EXAMPLE 67 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-(1-cyclopropyl-6-fluoro-7-imidazolylquinolinium-4-yl)thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-cephem-4-carboxylic acid(0.3 g) and 1-cyclopropyl-6-fluoro-7-imidazolyl-1,4-dihydro-4-thioquinoline(0.18 g) were reacted in the same manner as described in Example 17 to give the above-indicated compound(0.24 g). 
     IR: (KBr,cm -1 ) 1760(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.00-1.45(m,10H), 3.50-3.65(m,3H), 4.45(s,2H), 5.10(d,1H), 5.70(dd,1H), 6.70(s,1H), 6.90-7.40(m,7H), 7.85(s,1H), 8.50(d,1H), 9.35(d,1H) 
     EXAMPLE 68 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-[1-cyclopropyl-6-fluoro-7-(4-methylimidazolyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-cephem-4-carboxylic acid(0.3 g) and 1-cyclopropyl-6-fluoro-7-(4-methylimidazolyl)-1,4-dihydro-4-thioquinoline(0.19 g) were reacted in the same manner as described in Example 17 to give the above-indicated compound(0.23 g). 
     IR: (KBr,cm -1 ) 1761(β-lactam) 
     NMR: δ(DMSO-d 6 ) 0.95-1.45(m,10H), 2.45(s,3H), 3.45-3.60(m,3H), 4.50(s,2H), 5.10(d,1H), 5.70 (dd,1H), 6.70 (s,1H), 6.90 (s,1H), 6.95-7.60 (m,6H ), 8.45(d,1H), 9.30(d,1H) 
     EXAMPLE 69 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-[1-cyclopropyl-3-carboxylicacid-6-fluoro-7-(1-ethylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-cephem-4-carboxylic acid (0.7 g) and 1-cyclopropyl-6-fluoro-7-(1-ethylpiperazinyl)-1,4-dihydro-4-thioquinoline-3-carboxylic acid(0.63 g) were reacted in the same manner as described in Example 17 to give the above-indicated compound(0.59 g). 
     IR: (KBr,cm -1 ) 1761(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.00-1.40(m,7H), 2.75-3.70(m,13H), 3.90(s,3H), 4.40(s,2H), 5.00(d,1H), 5.50(dd,1H), 6.65(s,1H), 7.40(d,1H), 8.40(d,1H), 8.85(s,1H), 9.50(d,1H) 
     EXAMPLE 70 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-[1-cyclopropyl-1-3-carboxylicacid-6-fluoro-7-(2-methylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-cephem-4-carboxylic acid(0.6 g) and 1-cyclopropyl-6-fluoro-7-(2-methylpiperazinyl)-1,4-dihydro-4-thioquinoline-3-carboxylic acid(0.52 g) were reacted in the same manner as described in Example 17 to give the above-indicated compound(0.52 g). 
     IR: (KBr,cm -1 ) 1760(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.10-1.45(m,4H), 1.70(s,3H), 2.75-3.70(m,10H), 3.90(s,3H), 4.40(s,2H), 5.05(d,1H), 5.50(dd,1H), 6.65(s,1H), 7.40(d,1H), 8.45(d,1H), 8.75(s,1H), 9.50(d,1H) 
     EXAMPLE 71 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-[1-cyclopropyl-3-carboxylicacid-6-fluoro-7-(1-ethylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-cephem-4-carboxylic acid (0.4 g) and 1-cyclopropyl-6-fluoro-7-(1-ethylpiperazinyl)-1,4-dihydro-4-thioquinoline-4-carboxylic acid(0.31 g) were reacted in the same manner as described in Example 17 to give the above-indicated compound(0.34 g). 
     IR: (KBr,cm -1 ) 1760(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.00-1.50(m,13H), 2.75-3.60(m,13H), 4.50(s,2H), 5.10(d,1H), 5.70(dd,1H), 6.70(s,1H), 6.95-7.40(m,3H), 8.40(d,1H), 8.80(s,1H), 9.55(d,1H) 
     EXAMPLE 72 
     Synthesis of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-[1-cyclopropyl-3-carboxylicacid-6-fluoro-7-(2-methylpiperazinyl)quinolinium-4-yl]thiomethyl-3-cephem-4-carboxylate 
     3-acetoxymethyl-7-[(Z)-2-(2-aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-cephem-4-carboxylic acid(0.4 g) and 1-cyclopropyl-6-fluoro-7-(2-methylpiperazinyl)-1,4-dihydro-4-thioquinoline-3-carboxylic acid(0.3 g) were reacted in the same manner as described Example 17 to give the above-indicated compound(0.32 g). 
     IR: (KBr,cm -1 ) 1760(β-lactam) 
     NMR: δ(DMSO-d 6 ) 1.10-1.45(m,10H), 1.70(s,3H),2.75-3.60(m,10H) 4.50(s,2H), 5.10(d,1H), 5.70(dd,1H), 6.70(s,1H), 6.90-7.35(m,3H), 8.50(d,1H), 8.85(s,1H), 9.50(d,1H) 
     In order to illustrate the usefulness of the invented compounds, the minimal inhibitory concentrations-(MIC) thereof against standard strains were determined and compared with Cefotaxime, a known compound. 
     Also, the in vitro antibacterial activity was determined by a two-fold dilution method as described below: 
     That is, the two-fold serial dilutions of the compound were made and dispersed in Muller Hinton Broth medium. Standard test strain which had the 10 6  CFU per ml was inoculated on the medium, and was incubated at 37° C. for 18 to 20 hours. The results of the MIC tests are shown in Table 3. 
     
                                           TABLE 3__________________________________________________________________________Antibacterial Activity (MIC, μg/ml)Strains Bacillus       Staphylococcus              Staphylococcus                     Streptococcus                            Pseudomonas                                   Esherichia                                          KlebsiellaCompound subtilis       aureus epidermidis                     faecalis                            aeurginosa                                   coli   pneumoniaeNo.   ATCC 6633       ATCC 65389              ATCC 12228                     ATCC 10541                            NCTC 10490                                   ATCC 25922                                          ATCC 10031__________________________________________________________________________I-1   0.2   0.2    0.1    0.05   1.56   0.78   0.2I-2   0.39  1.56   0.78   0.39   3.13   12.5   0.39I-3   0.2   0.05   0.1    0.025  0.78   0.78   0.1I-4   0.1   0.1    0.2    0.05   0.78   0.78   0.1I-5   0.39  1.56   0.78   0.39   3.13   12.5   0.1I-6   0.39  0.39   0.39   0.2    1.56   12.5   0.1I-7   0.2   0.39   0.2    0.05   0.39   0.78   0.05I-8   0.2   0.39   0.2    0.2    0.39   0.78   0.05I-9   0.1   0.2    0.2    0.1    3.13   1.56   0.78I-10  0.39  0.39   1.56   1.56   6.25   12.5   0.78I-11  0.1   0.1    0.2    0.05   1.56   1.56   0.39I-12  0.1   0.1    0.2    0.025  1.56   1.56   0.39I-13  0.39  1.56   1.56   0.78   1.56   3.13   0.78I-14  0.1   0.78   0.39   0.2    3.13   3.13   1.56I-15  0.1   0.2    0.78   0.39   1.56   1.56   0.39I-16  0.2   0.2    0.39   0.78   1.56   1.56   0.39I-18  0.1   0.2    0.2    0.2    1.56   --     --I-20  0.2   0.78   0.39   0.2    1.56   1.56   0.1I-21  0.39  0.2    0.1    0.025  6.25   3.13   0.1I-22  0.39  0.2    0.1    0.013  3.13   6.25   0.39I-23  0.2   0.1    0.1    0.2    1.56   1.56   0.2I-24  0.2   0.1    0.1    0.1    0.78   1.56   0.2I-25  0.2   0.78   0.78   0.2    0.39   6.25   0.39I-26  0.1   0.39   1.56   0.2    0.39   6.25   0.2I-27  0.2   0.2    0.2    0.2    0.78   --     0.39I-28  0.39  0.2    0.2    0.2    1.56   --     0.78I-29  0.39  0.78   0.78   0.39   3.13   1.56   0.39I-30  0.39  1.56   0.78   0.39   6.25   3.13   0.78I-31  0.2   0.39   0.78   0.39   0.78   0.78   0.39I-32  0.39  0.39   0.78   0.39   1.56   0.78   0.39I-33  0.78  0.78   1.56   0.39   3.13   3.13   1.56I-34  0.78  1.56   1.56   0.78   6.25   3.13   1.56I-35  0.39  0.78   0.78   0.39   0.78   1.56   0.78I-36  0.39  0.78   1.56   0.39   1.56   1.56   0.78I-37  0.2   0.39   0.78   0.2    0.2    --     0.78I-38  0.78  0.78   0.39   0.2    0.78   --     3.13I-39  0.2   0.39   0.2    0.2    0.2    --     0.78I-40  0.2   0.39   0.1    0.2    0.2    --     0.78I-41  0.2   0.78   0.78   0.39   3.13   3.13   6.25I-42  0.2   0.78   0.78   0.39   3.13   3.13   3.13I-43  0.1   0.1    0.1    0.05   0.78   1.56   0.78I-44  0.05  0.39   0.2    0.2    1.56   1.56   0.78I-45  0.1   0.2    0.78   0.39   1.56   3.13   0.78I-46  0.78  0.78   0.39   0.2    6.25   12.5   6.25I-47  0.2   0.2    0.78   0.1    1.56   6.25   1.56I-48  0.1   0.39   0.78   0.39   1.56   3.13   1.56I-49  0.39  1.56   1.56   0.78   1.56   1.56   1.56I-50  0.78  3.13   3.13   1.56   3.13   3.13   3.13I-51  0.78  3.13   1.56   1.56   1.56   0.78   0.78I-52  0.39  3.13   1.56   0.78   1.56   0.78   1.56I-53  0.39  3.13   1.56   0.39   1.56   --     1.56I-54  0.78  6.25   3.13   1.56   3.13   6.25   3.13I-55  0.2   1.56   0.78   0.2    0.39   0.78   0.39I-56  0.2   0.78   0.78   0.39   0.78   0.39   0.39I-57  0.78  6.25   6.25   1.56   0.78   0.78   0.39I-59  0.39  0.78   1.56   0.78   0.78   0.78   0.39I-61  3.13  1.56   1.56   0.39   1.56   3.13   3.13I-64  1.56  3.13   1.56   0.39   3.13   1.56   1.56I-65  0.39  1.56   1.56   0.39   1.56   --     1.56I-68  0.78  1.56   1.56   0.2    0.78   1.56   0.78CTX   0.2   0.78   0.78   0.39   1.56   0.78   0.39__________________________________________________________________________ *CTX: Cefotaxime