NO881121L - 5-substituerte kinolon- og naftyridonkarboksylsyrederivater. - Google Patents

5-substituerte kinolon- og naftyridonkarboksylsyrederivater.

Info

Publication number: NO881121L
Authority: NO; Norway
Prior art keywords: amino; oxo; methyl; dihydro; carbon atoms
Prior art date: 1987-04-02

Application number

NO881121A

Other languages

English (en)

Norwegian (no)

Other versions

NO881121D0 (no

Inventor

Uwe Petersen

Klaus Grohe

Michael Schriewer

Thomas Schenke

Ingo Haller

Karl Georg Metzger

Rainer Endermann

Hans-Joachim Zeiler

Original Assignee

Bayer Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1987-04-02

Filing date

1988-03-14

Publication date

1988-10-03

1988-03-14 Application filed by Bayer Ag filed Critical Bayer Ag

1988-03-14 Publication of NO881121D0 publication Critical patent/NO881121D0/no

1988-10-03 Publication of NO881121L publication Critical patent/NO881121L/no

Links

-1 5-SUBSTITUTED QUINOLON Chemical class 0.000 title claims abstract description 223
150000001732 carboxylic acid derivatives Chemical class 0.000 title claims abstract description 8
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 101
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 86
239000001257 hydrogen Substances 0.000 claims abstract description 86
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 71
125000000217 alkyl group Chemical group 0.000 claims abstract description 49
150000001875 compounds Chemical class 0.000 claims abstract description 42
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 37
239000011737 fluorine Substances 0.000 claims abstract description 37
229910052731 fluorine Inorganic materials 0.000 claims abstract description 37
239000000460 chlorine Substances 0.000 claims abstract description 34
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 32
229910052801 chlorine Inorganic materials 0.000 claims abstract description 32
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 23
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 17
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 16
125000003277 amino group Chemical group 0.000 claims abstract description 15
125000004122 cyclic group Chemical group 0.000 claims abstract description 13
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 13
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 13
229920002554 vinyl polymer Polymers 0.000 claims abstract description 13
238000002360 preparation method Methods 0.000 claims abstract description 11
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 9
238000000034 method Methods 0.000 claims abstract description 8
230000008569 process Effects 0.000 claims abstract description 3
150000002431 hydrogen Chemical class 0.000 claims description 70
239000002253 acid Substances 0.000 claims description 46
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 31
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 24
150000003839 salts Chemical class 0.000 claims description 23
125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 16
239000003513 alkali Substances 0.000 claims description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
150000001735 carboxylic acids Chemical class 0.000 claims description 15
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
229910052736 halogen Inorganic materials 0.000 claims description 14
150000002367 halogens Chemical class 0.000 claims description 14
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 13
239000004332 silver Substances 0.000 claims description 13
229910052709 silver Inorganic materials 0.000 claims description 13
125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 12
YCWRFIYBUQBHJI-UHFFFAOYSA-N 2-(4-aminophenyl)acetonitrile Chemical group NC1=CC=C(CC#N)C=C1 YCWRFIYBUQBHJI-UHFFFAOYSA-N 0.000 claims description 12
125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 12
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical class NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 12
125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 12
125000003282 alkyl amino group Chemical group 0.000 claims description 12
125000004414 alkyl thio group Chemical group 0.000 claims description 12
125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 12
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 12
125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims description 12
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 12
125000004663 dialkyl amino group Chemical group 0.000 claims description 11
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 11
125000000623 heterocyclic group Chemical group 0.000 claims description 11
150000004677 hydrates Chemical class 0.000 claims description 11
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 10
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
125000000033 alkoxyamino group Chemical group 0.000 claims description 9
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 8
150000007513 acids Chemical class 0.000 claims description 8
230000000844 anti-bacterial effect Effects 0.000 claims description 8
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
125000006310 cycloalkyl amino group Chemical group 0.000 claims description 8
125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 8
239000003814 drug Substances 0.000 claims description 8
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 claims description 7
241001465754 Metazoa Species 0.000 claims description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
QZGZNEIHSDIMDE-UHFFFAOYSA-N 1-cyclopropyl-5,6,8-trifluoro-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid Chemical compound C1CN(C)CCN1C1=C(F)C(F)=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F QZGZNEIHSDIMDE-UHFFFAOYSA-N 0.000 claims description 6
XNIVKSPSCYJKBL-UHFFFAOYSA-N 2h-1,2-benzoxazine-6-carboxylic acid Chemical compound O1NC=CC2=CC(C(=O)O)=CC=C21 XNIVKSPSCYJKBL-UHFFFAOYSA-N 0.000 claims description 6
MHFCVNDHFSOKMK-UHFFFAOYSA-N chembl146339 Chemical compound FC1=C(N)C(C(C(C(O)=O)=C2)=O)=C3N2C(C)COC3=C1N1CCN(C)CC1 MHFCVNDHFSOKMK-UHFFFAOYSA-N 0.000 claims description 6
YQCYCLNGTIRTCK-UHFFFAOYSA-N 5-amino-7-(3-aminopyrrolidin-1-yl)-1-ethyl-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound N1=C2N(CC)C=C(C(O)=O)C(=O)C2=C(N)C(F)=C1N1CCC(N)C1 YQCYCLNGTIRTCK-UHFFFAOYSA-N 0.000 claims description 5
XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 claims description 5
CRNDXEVHWDPJSJ-UHFFFAOYSA-N 5-amino-1-ethyl-6,8-difluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid Chemical compound FC1=C2N(CC)C=C(C(O)=O)C(=O)C2=C(N)C(F)=C1N1CCNCC1 CRNDXEVHWDPJSJ-UHFFFAOYSA-N 0.000 claims description 4
STSHUQRTDPMRHI-UHFFFAOYSA-N 5-amino-1-ethyl-6,8-difluoro-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=C2N(CC)C=C(C(O)=O)C(=O)C2=C(N)C(F)=C1N1CCN(C)CC1 STSHUQRTDPMRHI-UHFFFAOYSA-N 0.000 claims description 4
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
MLFYZWDFPVLMQQ-UHFFFAOYSA-N 5-amino-7-(3-aminopyrrolidin-1-yl)-1-ethyl-6-fluoro-4-oxo-1,8-naphthyridine-2-carboxylic acid Chemical compound N1=C2N(CC)C(C(O)=O)=CC(=O)C2=C(N)C(F)=C1N1CCC(N)C1 MLFYZWDFPVLMQQ-UHFFFAOYSA-N 0.000 claims description 3
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 3
BYQFEUWSBLIHPK-UHFFFAOYSA-N 1-cyclopropyl-5,6,8-trifluoro-4-oxo-7-[4-(3-oxobutyl)piperazin-1-yl]quinoline-3-carboxylic acid Chemical compound C1CN(CCC(=O)C)CCN1C1=C(F)C(F)=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F BYQFEUWSBLIHPK-UHFFFAOYSA-N 0.000 claims description 2
UVPAOMFBMNZWTA-UHFFFAOYSA-N 1-cyclopropyl-5,6,8-trifluoro-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid Chemical compound C1CNC(C)CN1C1=C(F)C(F)=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F UVPAOMFBMNZWTA-UHFFFAOYSA-N 0.000 claims description 2
GWVFYNAMXGQAPQ-UHFFFAOYSA-N 1-cyclopropyl-5,6,8-trifluoro-7-[4-(2-hydroxyethyl)piperazin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound C1CN(CCO)CCN1C1=C(F)C(F)=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F GWVFYNAMXGQAPQ-UHFFFAOYSA-N 0.000 claims description 2
AUVPRSZMNIKXQY-UHFFFAOYSA-N 1-cyclopropyl-5,6,8-trifluoro-7-imidazol-1-yl-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(F)C(N3C=NC=C3)=C(F)C(F)=C2C(=O)C(C(=O)O)=CN1C1CC1 AUVPRSZMNIKXQY-UHFFFAOYSA-N 0.000 claims description 2
YFKPOSDZURMCBA-UHFFFAOYSA-N 5-amino-1-cyclopropyl-6-fluoro-7-(3-hydroxypyrrolidin-1-yl)-4-oxoquinoline-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)C=2C(N)=C(F)C(N3CC(O)CC3)=CC=2N1C1CC1 YFKPOSDZURMCBA-UHFFFAOYSA-N 0.000 claims description 2
GMCYYXZTVSSTQW-UHFFFAOYSA-N 5-amino-7-(3-aminopyrrolidin-1-yl)-1-cyclopropyl-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(N)CCN1C1=C(F)C(N)=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F GMCYYXZTVSSTQW-UHFFFAOYSA-N 0.000 claims description 2
238000011282 treatment Methods 0.000 claims description 2
FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims 1
ZBRLJXNDTNUXJI-UHFFFAOYSA-N 1-cyclopropyl-5,6,8-trifluoro-4-oxo-7-[4-(2-oxopropyl)piperazin-1-yl]quinoline-3-carboxylic acid Chemical compound C1CN(CC(=O)C)CCN1C1=C(F)C(F)=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F ZBRLJXNDTNUXJI-UHFFFAOYSA-N 0.000 claims 1
QIPQASLPWJVQMH-UHFFFAOYSA-N 1-cyclopropyl-7-(3,5-dimethylpiperazin-4-ium-1-yl)-5,6,8-trifluoro-4-oxoquinoline-3-carboxylate Chemical compound C1C(C)NC(C)CN1C1=C(F)C(F)=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F QIPQASLPWJVQMH-UHFFFAOYSA-N 0.000 claims 1
SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 1
229940079593 drug Drugs 0.000 claims 1
235000013312 flour Nutrition 0.000 claims 1
229940126601 medicinal product Drugs 0.000 claims 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
150000003248 quinolines Chemical class 0.000 claims 1
150000007660 quinolones Chemical class 0.000 claims 1
230000001225 therapeutic effect Effects 0.000 claims 1
239000003242 anti bacterial agent Substances 0.000 abstract description 4
241000269627 Amphiuma means Species 0.000 abstract 3
125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
239000000546 pharmaceutical excipient Substances 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 62
238000002844 melting Methods 0.000 description 57
230000008018 melting Effects 0.000 description 56
238000000354 decomposition reaction Methods 0.000 description 45
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
235000019441 ethanol Nutrition 0.000 description 24
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 23
239000000203 mixture Substances 0.000 description 23
239000013543 active substance Substances 0.000 description 20
239000000243 solution Substances 0.000 description 16
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 15
239000000126 substance Substances 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
238000003776 cleavage reaction Methods 0.000 description 12
238000001816 cooling Methods 0.000 description 12
230000007017 scission Effects 0.000 description 12
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
208000015181 infectious disease Diseases 0.000 description 10
239000002244 precipitate Substances 0.000 description 10
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
238000003756 stirring Methods 0.000 description 8
229910021529 ammonia Inorganic materials 0.000 description 7
239000000843 powder Substances 0.000 description 7
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
239000000969 carrier Substances 0.000 description 6
239000000839 emulsion Substances 0.000 description 6
239000000825 pharmaceutical preparation Substances 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
238000010992 reflux Methods 0.000 description 6
239000000725 suspension Substances 0.000 description 6
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
239000002775 capsule Substances 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
201000010099 disease Diseases 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
238000009472 formulation Methods 0.000 description 5
239000003921 oil Substances 0.000 description 5
235000019198 oils Nutrition 0.000 description 5
239000007787 solid Substances 0.000 description 5
239000007858 starting material Substances 0.000 description 5
239000003826 tablet Substances 0.000 description 5
238000002560 therapeutic procedure Methods 0.000 description 5
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 5
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 4
KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
241000282412 Homo Species 0.000 description 4
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 4
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 4
206010039438 Salmonella Infections Diseases 0.000 description 4
229960003237 betaine Drugs 0.000 description 4
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
239000008298 dragée Substances 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
JFFLSJHTBZDAEP-UHFFFAOYSA-N ethyl 3-ethoxy-2-(2,3,4,5,6-pentafluorobenzoyl)prop-2-enoate Chemical compound CCOC=C(C(=O)OCC)C(=O)C1=C(F)C(F)=C(F)C(F)=C1F JFFLSJHTBZDAEP-UHFFFAOYSA-N 0.000 description 4
239000000499 gel Substances 0.000 description 4
239000008187 granular material Substances 0.000 description 4
239000005457 ice water Substances 0.000 description 4
229940098779 methanesulfonic acid Drugs 0.000 description 4
239000002674 ointment Substances 0.000 description 4
239000006187 pill Substances 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
239000000047 product Substances 0.000 description 4
125000006239 protecting group Chemical group 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
206010039447 salmonellosis Diseases 0.000 description 4
PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 4
239000007921 spray Substances 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
208000035143 Bacterial infection Diseases 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
201000004813 Bronchopneumonia Diseases 0.000 description 3
HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 3
206010012735 Diarrhoea Diseases 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
235000011114 ammonium hydroxide Nutrition 0.000 description 3
239000000440 bentonite Substances 0.000 description 3
235000012216 bentonite Nutrition 0.000 description 3
229910000278 bentonite Inorganic materials 0.000 description 3
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
230000037396 body weight Effects 0.000 description 3
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/10—Spiro-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Quinoline Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

NO881121A 1987-04-02 1988-03-14 5-substituerte kinolon- og naftyridonkarboksylsyrederivater. NO881121L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19873711193 DE3711193A1 (de)	1987-04-02	1987-04-02	5-substituierte chinolon- und naphthyridoncarbonsaeure-derivate

Publications (2)

Publication Number	Publication Date
NO881121D0 NO881121D0 (no)	1988-03-14
NO881121L true NO881121L (no)	1988-10-03

Family

ID=6324762

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO881121A NO881121L (no)	1987-04-02	1988-03-14	5-substituerte kinolon- og naftyridonkarboksylsyrederivater.

Country Status (14)

Country	Link
EP (1)	EP0284935A1 (fr)
JP (1)	JPS63258855A (fr)
KR (1)	KR880012593A (fr)
CN (1)	CN88101741A (fr)
AU (1)	AU1381188A (fr)
DD (1)	DD274029A5 (fr)
DE (1)	DE3711193A1 (fr)
DK (1)	DK180288A (fr)
FI (1)	FI881501A7 (fr)
HU (1)	HU201050B (fr)
IL (1)	IL85943A0 (fr)
NO (1)	NO881121L (fr)
PT (1)	PT87124B (fr)
ZA (1)	ZA882318B (fr)

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5563138A (en) *	1987-04-16	1996-10-08	Otsuka Pharmaceutical Company, Limited	Benzoheterocyclic compounds
JPS649992A (en) *	1987-06-30	1989-01-13	Dainippon Pharmaceutical Co	1,8-crosslinked quinolincarboxylic acid derivative, ester thereof and salt thereof
US4839355A (en) *	1987-09-09	1989-06-13	Sterling Drug Inc.	Tricyclic-pyridinylquinoline compounds, their preparation and use
US5164392A (en) *	1987-10-16	1992-11-17	Dainippon Pharmaceutical Co., Ltd.	Quinoline derivatives and antibacterial agent containing them
IL88003A (en) *	1987-10-16	1992-11-15	Dainippon Pharmaceutical Co	Quinoline derivatives,their preparation and pharmaceutical compositions containing them
JPH0228178A (ja) *	1988-04-23	1990-01-30	Toyama Chem Co Ltd	新規なピリドンカルボン酸誘導体およびその塩並びにそれらの製造法
AU609974B2 (en) *	1988-05-18	1991-05-09	Warner-Lambert Company	Improved process for the preparation of 5-amino-7- (substituted amino)-quinoline-3-carboxylic acids
JPH0674261B2 (ja) *	1988-06-21	1994-09-21	塩野義製薬株式会社	キノロンカルボン酸誘導体
AU5123690A (en) *	1989-03-13	1990-09-13	Bristol-Myers Squibb Company	5-substituted-1,4-dihydro-4-oxo-nephthyridine-3-carboxylate antibacterial agents
WO1990012799A1 (fr) *	1989-04-26	1990-11-01	The Upjohn Company	Agents de pyrido(1,2,3-de)-1,4-benzoxazinone a action antibacterienne
FI921475A7 (fi) *	1989-10-06	1992-04-03	Pfizer	1,4-dihydro-4-okso-3-kinoliinijohdannaisia selektiivisesti toksisina n isäkkään antibakteerisina aineina
US5385913A (en) *	1989-10-06	1995-01-31	Pfizer Inc.	1,4-dihydro-4-oxo-3-quinoline derivatives as selectively toxic mammalian antibacterial agents
KR100204987B1 (ko)	1990-04-18	1999-06-15	제이코버스 코넬리스 레이서	항미생물성 퀴놀로닐 락탐
DE4032560A1 (de) *	1990-10-13	1992-04-16	Bayer Ag	7-(2,7-diazabicyclo(3.3.0)octyl)-3-chinolon- und -naphtyridoncarbonsaeure-derivate
FR2681863B1 (fr) *	1991-09-27	1995-02-03	Rhone Dpc Europ	Solution de sparfloxacine sa preparation et sel la constituant.
WO1993013101A1 (fr) *	1991-12-27	1993-07-08	Yoshitomi Pharmaceutical Industries, Ltd.	Compose de pyridonecarboxylate, son utilisation pharmaceutique et compose spiro
US5646163A (en) *	1992-10-30	1997-07-08	The Procter & Gamble Company	Quinolone 5-(N-heterosubstituted amino) antimicrobials
TW252107B (fr) *	1993-08-27	1995-07-21	Hokuriku Pharmacetical Co Ltd
CA2210007A1 (fr) *	1995-01-24	1996-08-01	Yasuo Ito	Derives de l'acide quiloleine carboxylique
DE10108750A1 (de) *	2001-02-23	2002-09-05	Bayer Ag	Verbessertes Verfahren zur Herstellung von Fluorchinoloncarbonsäuren
WO2004024729A1 (fr) *	2002-09-10	2004-03-25	Pfizer Products Inc.	Composes diazabicycliques utilises dans le traitement de troubles associes au snc
CN100410249C (zh)	2003-09-10	2008-08-13	杏林制药株式会社	7-(4-取代-3-环丙基氨基甲基-1-吡咯烷基)喹诺酮羧酸衍生物
WO2005099688A2 (fr)	2004-04-07	2005-10-27	Takeda Pharmaceutical Company Limited	Composes cycliques
CA2688008A1 (fr)	2007-05-24	2008-11-27	Kyorin Pharmaceutical Co., Ltd.	Derive de la mutiline ayant une structure d'acide carboxylique a noyau aromatique heterocyclique en substituant a la position 14
CN105037388A (zh) *	2015-08-28	2015-11-11	安徽环球药业股份有限公司	一种安妥沙星的制备方法
CN106674254B (zh) *	2016-12-21	2019-03-15	广东省中医院	一类喹诺酮羧酸化合物及其中间体、制备方法以及应用

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS59137482A (ja) *	1983-01-26	1984-08-07	Otsuka Pharmaceut Co Ltd	ピロロ〔３，２，１，−ｉｊ〕キノリン−５−カルボン酸誘導体
IE58742B1 (en) *	1984-07-20	1993-11-05	Warner Lambert Co	Substituted-9-fluoro-3-methyl-7-oxo-2,3-dihydro-7h-pyrido[1,2,3-de] [1,4]benzoxauine-6-carboxylic acids; sibstituted-5-amino-6-6fluoro-4-oxo.1,4-dihydroquinoline-3 carboxylic acids; substituted-5-amino-6-fluoro-1,4-dihydro-4-oxo-1.8-naphthyridine-3-carboxylic acids; derivatives thereof; pharmaceutical compositions comprising the compounds; and processes for producing the compounds
US4657913A (en) *	1985-04-18	1987-04-14	Warner-Lambert Company	Trifluoro- quinoline -3- carboxylic acids and their use as anti-bacterial agents
AU594983B2 (en) *	1985-10-29	1990-03-22	Dainippon Pharmaceutical Co. Ltd.	Novel quinoline derivatives and processes for preparation thereof
US4977154A (en) *	1985-12-12	1990-12-11	Warner-Lambert Company	5-amino and 5-hydroxy-6-fluoroquinolones as antibacterial agents
EP0242789A3 (fr) *	1986-04-25	1990-09-05	Dainippon Pharmaceutical Co., Ltd.	Dérivés de quinoléine et procédés pour leur préparation

1987
- 1987-04-02 DE DE19873711193 patent/DE3711193A1/de not_active Withdrawn
1988
- 1988-03-14 NO NO881121A patent/NO881121L/no unknown
- 1988-03-21 EP EP88104452A patent/EP0284935A1/fr not_active Withdrawn
- 1988-03-28 AU AU13811/88A patent/AU1381188A/en not_active Abandoned
- 1988-03-29 DD DD88314159A patent/DD274029A5/de not_active IP Right Cessation
- 1988-03-30 FI FI881501A patent/FI881501A7/fi not_active Application Discontinuation
- 1988-03-30 PT PT87124A patent/PT87124B/pt not_active IP Right Cessation
- 1988-03-30 DK DK180288A patent/DK180288A/da not_active Application Discontinuation
- 1988-03-31 CN CN198888101741A patent/CN88101741A/zh active Pending
- 1988-03-31 IL IL85943A patent/IL85943A0/xx unknown
- 1988-03-31 ZA ZA882318A patent/ZA882318B/xx unknown
- 1988-03-31 KR KR1019880003588A patent/KR880012593A/ko not_active Withdrawn
- 1988-04-01 HU HU881619A patent/HU201050B/hu not_active IP Right Cessation
- 1988-04-01 JP JP63078298A patent/JPS63258855A/ja active Pending

Also Published As

Publication number	Publication date
CN88101741A (zh)	1988-11-16
FI881501A0 (fi)	1988-03-30
HU201050B (en)	1990-09-28
PT87124B (pt)	1992-07-31
PT87124A (pt)	1988-04-01
ZA882318B (en)	1988-10-04
KR880012593A (ko)	1988-11-28
DD274029A5 (de)	1989-12-06
FI881501A7 (fi)	1988-10-03
AU1381188A (en)	1988-10-06
HUT47098A (en)	1989-01-30
DK180288D0 (da)	1988-03-30
DE3711193A1 (de)	1988-10-13
JPS63258855A (ja)	1988-10-26
IL85943A0 (en)	1988-09-30
DK180288A (da)	1988-10-03
NO881121D0 (no)	1988-03-14
EP0284935A1 (fr)	1988-10-05

Publication	Publication Date	Title
NO881121L (no)	1988-10-03	5-substituerte kinolon- og naftyridonkarboksylsyrederivater.
CA1314544C (fr)	1993-03-16	Acides 8-cyano-1-cyclopropyl-4-oxo-1,4-dihydroquinoleine -3-carboxyliques; methode de preparation et agents antibacteriens a base de ces composes
JP3001848B2 (ja)	2000-01-24	置換された単環式または二環式ピロリジン誘導体
JP3046035B2 (ja)	2000-05-29	５―アルキルキノロンカルボン酸類
US4762831A (en)	1988-08-09	Antibacterial 1,8-bridged 4-quinolone-3-carboxylic acids
JPH07300416A (ja)	1995-11-14	抗菌性医薬
NZ230484A (en)	1991-06-25	Substituted antibacterial spiro heterocyclic compounds and pharmaceutical compositions
NO870126L (no)	1987-07-22	7-(azabicykloalkyl)-chinolonkarboksylsyre- og naftyridon-karboksylsyre-derivater.
HU195954B (en)	1988-08-29	Process for producing 1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-3-quinoline-carboxylic acid ester derivatives and pharmaceutics comprising the same
US5173484A (en)	1992-12-22	Quinolone- and naphthyridone carboxylic acid derivatives, process for their production, antibacterial compositions and feed additives containing them
US4806539A (en)	1989-02-21	1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acids and antibacterial agents containing them
JP2788043B2 (ja)	1998-08-20	キノロン−又はナフチリドンカルボン酸類
KR950007590B1 (ko)	1995-07-12	7-(1-피롤리디닐)-퀴놀론카르복실산 유도체의 제조 방법
JPH02290870A (ja)	1990-11-30	対掌体的に純粋な７‐（３‐アミノ‐１‐ピロリジニル）‐キノロン‐および‐ナフチリドンカルボン酸
US5190955A (en)	1993-03-02	Antibacterial 8-cyano-1-cyclopropyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids
KR890005200B1 (ko)	1989-12-18	7-(1-피롤리디닐)-퀴놀론카르복실산 유도체
JPH0348682A (ja)	1991-03-01	ピリドンカルボン酸化合物
AU649893B1 (en)	1994-06-02	Antibacterial agents
JP2523092B2 (ja)	1996-08-07	ベンゼン誘導体
IE19970856A1 (en)	2000-02-23	7-(1-Pyrrolidinyl)-3-quinolone and naphthyridone carboxylic acid derivatives, method for their preparation and for substituted mono- and bicyclic pyrrolidine intermediates, and their antibacterial and feed additive compositions
HU209300B (en)	1994-04-28	Method for producing quinolone-carboxylic acid derivatives and pharmaceutical preparatives containing these compounds
IE84193B1 (en)	2006-04-19	7-(1-Pyrrolidinyl)-3-quinolone and naphthyridone carboxylic acid derivatives, method for their preparation and for substituted mono- and bicyclic pyrrolidine intermediates, and their antibacterial and feed additive compositions