RU93058417A - Pyridone Carboxylic Acid Derivatives, Antimicrobial Agent - Google Patents
Pyridone Carboxylic Acid Derivatives, Antimicrobial AgentInfo
- Publication number
- RU93058417A RU93058417A RU93058417/04A RU93058417A RU93058417A RU 93058417 A RU93058417 A RU 93058417A RU 93058417/04 A RU93058417/04 A RU 93058417/04A RU 93058417 A RU93058417 A RU 93058417A RU 93058417 A RU93058417 A RU 93058417A
- Authority
- RU
- Russia
- Prior art keywords
- carboxylic acid
- mixture
- diastereomers
- acid derivatives
- pyridone carboxylic
- Prior art date
Links
- 239000004599 antimicrobial Substances 0.000 title claims 3
- UEYQJQVBUVAELZ-UHFFFAOYSA-N 2-Hydroxynicotinic acid Chemical class OC(=O)C1=CC=CN=C1O UEYQJQVBUVAELZ-UHFFFAOYSA-N 0.000 title claims 2
- 239000000203 mixture Substances 0.000 claims 3
- 210000002356 Skeleton Anatomy 0.000 claims 2
- 150000007660 quinolones Chemical class 0.000 claims 2
- 230000000845 anti-microbial Effects 0.000 claims 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 230000000704 physical effect Effects 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
Claims (1)
где R1 представляет метиловую группу, дифторметиловую группу и др.; R2 представляет насыщенную азотосодержащую гетероциклическую группу; А представляет С-Х3 или атом азота; каждый из Х1 и Х2 представляет атом галогена; Х3 и Z представляет атом водорода и др.Quinolone derivatives are known as synthetic antimicrobial agents having a skeleton of a fused pyridone carboxylic acid; also known are those which have substituents at various substituted positions of the named skeleton. In particular, if diastereomers exist, then there are 4 or more kinds of stereoisomers. A mixture of diastereomers is a mixture of isomers having different physical properties, and the use of such a mixture as a medicine is difficult. The present invention provides an antimicrobial 1- (1,2-cis-2-fluorocyclopropyl) -substituted quinolone derivative represented by the formula, which, although containing diastereomers, consists of a single stereoisomer
where R 1 represents a methyl group, a difluoromethyl group, and others; R 2 represents a saturated nitrogen-containing heterocyclic group; A represents CX 3 or a nitrogen atom; each of X 1 and X 2 represents a halogen atom; X 3 and Z represents a hydrogen atom, etc.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP22542591 | 1991-05-28 | ||
JP3-225425 | 1991-05-28 | ||
PCT/JP1992/000687 WO1992021659A1 (en) | 1991-05-28 | 1992-05-27 | Pyridonecarboxylic acid derivative |
Publications (2)
Publication Number | Publication Date |
---|---|
RU93058417A true RU93058417A (en) | 1996-12-27 |
RU2100351C1 RU2100351C1 (en) | 1997-12-27 |
Family
ID=16829173
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
RU93058417/04A RU2100351C1 (en) | 1991-05-28 | 1992-05-27 | Pyridone carboxylic acid derivatives and composition based on thereof |
Country Status (16)
Country | Link |
---|---|
US (1) | US5696132A (en) |
EP (1) | EP0593766B1 (en) |
JP (1) | JP3215500B2 (en) |
KR (1) | KR100232937B1 (en) |
AT (1) | ATE196135T1 (en) |
AU (1) | AU661999B2 (en) |
CA (1) | CA2110260C (en) |
DE (1) | DE69231422T2 (en) |
DK (1) | DK0593766T3 (en) |
ES (1) | ES2151488T3 (en) |
FI (1) | FI109201B (en) |
GR (1) | GR3034966T3 (en) |
NO (1) | NO180780C (en) |
RU (1) | RU2100351C1 (en) |
TW (1) | TW212179B (en) |
WO (1) | WO1992021659A1 (en) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3165742B2 (en) * | 1991-07-16 | 2001-05-14 | 中外製薬株式会社 | Method for producing quinolone carboxylic acid derivative |
NO304832B1 (en) * | 1992-05-27 | 1999-02-22 | Ube Industries | Aminokinolone derivatives and anti-HIV agents |
JP3268098B2 (en) * | 1992-12-25 | 2002-03-25 | 第一製薬株式会社 | Bicyclic cyclic amine derivative |
DE4339134A1 (en) * | 1993-11-16 | 1995-05-18 | Bayer Ag | 1- (2-fluorocyclopropyl) quinolone and naphthyridonecarboxylic acid derivatives |
DE4408212A1 (en) * | 1994-03-11 | 1995-09-14 | Bayer Ag | 5-vinyl and 5-ethynyl quinolone and naphthyridone carboxylic acids |
KR100389773B1 (en) * | 1995-02-02 | 2003-10-23 | 다이이찌 세이야꾸 가부시기가이샤 | The heterocyclic compound |
PT816355E (en) * | 1995-02-07 | 2003-09-30 | Daiichi Seiyaku Co | SPIRO-HETEROCYCLIC DERIVATIVES |
JP4040091B2 (en) * | 1995-11-22 | 2008-01-30 | 第一三共株式会社 | Substituted aminocycloalkylpyrrolidine derivatives |
US6121285A (en) * | 1995-11-22 | 2000-09-19 | Daiichi Pharmaceutical Co., Ltd. | Substituted aminocycloalkylpyrrolidine derivatives and cis-substituted aminocycloalkylpyrrolidine derivatives |
WO1998024781A1 (en) * | 1996-12-04 | 1998-06-11 | Daiichi Pharmaceutical Co., Ltd. | Substituted aminomethylpyrrolidine derivatives |
JPH1149698A (en) | 1997-07-31 | 1999-02-23 | Santen Pharmaceut Co Ltd | Water-based lactoferrin preparation with increased stability |
EP1757598A4 (en) | 2004-05-13 | 2010-07-21 | Daiichi Seiyaku Co | Substituted pyrrolidine derivative |
US7563805B2 (en) * | 2005-05-19 | 2009-07-21 | Daiichi Pharmaceutical Co., Ltd. | Tri-, tetra-substituted-3-aminopyrrolidine derivative |
US7977346B2 (en) | 2006-01-17 | 2011-07-12 | Guoqing Paul Chen | Spiro compounds and methods of use |
CN105330590B (en) * | 2015-10-15 | 2018-09-25 | 广州市朗启医药科技有限责任公司 | The preparation method of sitafloxacin five-membered ring side chain intermediate |
CN109942488A (en) * | 2019-04-04 | 2019-06-28 | 山东省联合农药工业有限公司 | A kind of quinoline carboxylic acid ester's compound and preparation method thereof and purposes |
Family Cites Families (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6028978A (en) * | 1983-07-27 | 1985-02-14 | Dainippon Pharmaceut Co Ltd | 1,8-naphthyridine derivative |
EP0191185B1 (en) * | 1984-12-14 | 1990-03-07 | Daiichi Seiyaku Co., Ltd. | Quinoline-carboxylic acid derivatives |
DE3509546A1 (en) * | 1985-03-16 | 1986-09-25 | Bayer Ag, 5090 Leverkusen | 7-AMINO-1- (SUBST.CYCLOPROPYL) -1,4-DIHYDRO-4-OXO-3-CHINOLINE CARBONIC ACIDS, METHOD FOR THE PRODUCTION THEREOF AND THE ANTIBACTERIAL AGENTS CONTAINING THEM |
DE3705621C2 (en) * | 1986-02-25 | 1997-01-09 | Otsuka Pharma Co Ltd | Heterocyclic substituted quinolonecarboxylic acid derivatives |
DE3702393A1 (en) * | 1987-01-28 | 1988-08-11 | Bayer Ag | 8-CYANO-1-CYCLOPROPYL-1,4-DIHYDRO-4-OXO- 3-CHINOLINE CARBONIC ACIDS, METHOD FOR THEIR PRODUCTION AND ANTIBACTERIAL AGENTS CONTAINING THEM |
US5563138A (en) * | 1987-04-16 | 1996-10-08 | Otsuka Pharmaceutical Company, Limited | Benzoheterocyclic compounds |
US4851418A (en) * | 1987-08-21 | 1989-07-25 | Warner-Lambert Company | Naphthyridine antibacterial agents containing an α-amino acid in the side chain of the 7-substituent |
US4920120A (en) * | 1988-01-25 | 1990-04-24 | Warner-Lambert Company | Antibacterial agents |
MY105136A (en) * | 1988-04-27 | 1994-08-30 | Daiichi Seiyaku Co | Optically active pyridonecarboxylic acid derivatives. |
DE3906365A1 (en) * | 1988-07-15 | 1990-01-18 | Bayer Ag | 7- (1-PYRROLIDINYL) -3-CHINOLONE AND NAPHTHYRIDONE CARBOXYLIC ACID DERIVATIVES, METHOD AND SUBSTITUTED (OXA) DIAZABICYCLOOCTANES AND NONANESE AS INTERMEDIATE PRODUCTS, AND ANTIBACTERIAL AGENTS AND FOOD ADDITIVES CONTAINING THEM |
US5057520A (en) * | 1989-03-24 | 1991-10-15 | Abbott Laboratories | 7-(peptidylpyrolidinyl)naphthyridine antibacterial compounds |
US5153203A (en) * | 1989-03-30 | 1992-10-06 | Wakunaga Seiyaku Kabushiki Kaisha | Quinolone derivatives and salts thereof, preparation processes thereof, and antibacterial agents containing the same |
US5252734A (en) * | 1989-04-03 | 1993-10-12 | Bayer Aktiengesellschaft | Antibacterial 5-alkylquinolonecarboxylic acids |
DE3910663A1 (en) * | 1989-04-03 | 1990-10-04 | Bayer Ag | 5-ALKYLCHINOLON CARBONIC ACIDS |
US5140033A (en) * | 1989-04-03 | 1992-08-18 | Bayer Aktiengesellschaft | Antibacterial 5-alkylquinolonecarboxylic acids |
DE3918544A1 (en) * | 1989-06-07 | 1990-12-13 | Bayer Ag | METHOD FOR PRODUCING 7- (3-AMINO AND 3-AMINO-METHYL-1-PYRROLIDINYL) -3-CHINOLONIC CARBONIC ACIDS AND -NAPHTHYRIDONE CARBONIC ACIDS |
MY109714A (en) * | 1990-10-18 | 1997-04-30 | Daiichi Seiyaku Co | Process for preparing 8-chloroquinolone derivatives |
US5072001A (en) * | 1990-11-30 | 1991-12-10 | Warner-Lambert Company | Certain optically active substituted 3-pyrraidine acetic acid derivatives useful as intermediates |
US5137892A (en) * | 1990-12-12 | 1992-08-11 | Abbott Laboratories | Quinoline, naphthyridine and pyridobenzoxazine derivatives |
-
1992
- 1992-05-27 WO PCT/JP1992/000687 patent/WO1992021659A1/en active IP Right Grant
- 1992-05-27 CA CA002110260A patent/CA2110260C/en not_active Expired - Fee Related
- 1992-05-27 ES ES92910698T patent/ES2151488T3/en not_active Expired - Lifetime
- 1992-05-27 RU RU93058417/04A patent/RU2100351C1/en not_active IP Right Cessation
- 1992-05-27 KR KR1019930703606A patent/KR100232937B1/en not_active IP Right Cessation
- 1992-05-27 AT AT92910698T patent/ATE196135T1/en not_active IP Right Cessation
- 1992-05-27 DE DE69231422T patent/DE69231422T2/en not_active Expired - Fee Related
- 1992-05-27 EP EP92910698A patent/EP0593766B1/en not_active Expired - Lifetime
- 1992-05-27 AU AU18872/92A patent/AU661999B2/en not_active Ceased
- 1992-05-27 DK DK92910698T patent/DK0593766T3/en active
- 1992-05-27 US US08/142,444 patent/US5696132A/en not_active Expired - Fee Related
- 1992-05-28 JP JP13650492A patent/JP3215500B2/en not_active Expired - Fee Related
- 1992-05-29 TW TW081104208A patent/TW212179B/zh active
-
1993
- 1993-11-25 FI FI935243A patent/FI109201B/en not_active IP Right Cessation
- 1993-11-26 NO NO934279A patent/NO180780C/en not_active IP Right Cessation
-
2000
- 2000-11-30 GR GR20000402669T patent/GR3034966T3/en not_active IP Right Cessation
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