KR930021633A - Novel azetidine derivatives of pyridonecarboxylic acid with antibacterial activity - Google Patents

Novel azetidine derivatives of pyridonecarboxylic acid with antibacterial activity Download PDF

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KR930021633A
KR930021633A KR1019930006389A KR930006389A KR930021633A KR 930021633 A KR930021633 A KR 930021633A KR 1019930006389 A KR1019930006389 A KR 1019930006389A KR 930006389 A KR930006389 A KR 930006389A KR 930021633 A KR930021633 A KR 930021633A
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amino
oxo
azetidinyl
dihydro
methyl
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조르디 꼬르베라-아르조나
조르디 프리골라-콘스탄샤
쥬앙 빠레스-꼬로미나스
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마뇨사스-바레라, 엔리께
라보라또리오스 델 독또르 에스떼버 쏘시에다 아노니마
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    • 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
    • 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
    • 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

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Abstract

이 발명은 1, 4-디히드로-4-옥소-3-퀴놀린 카르복시산, 4-옥소-1, 8-나프티리딘-3-카르복시산 및 2, 3-디히드로-7-옥소-7H-피리도[1, 2, 3-데][1, 4]벤족사진-6-카르복시산과 같은 피리돈카르복시산의 신규한 아제티딘 유도체, 이 화합물들의 치료학적으로 허용가능한 염, 그 제조방법 및 의약품으로서의 이들의 사용에 관한 것이다.This invention relates to 1, 4-dihydro-4-oxo-3-quinoline carboxylic acid, 4-oxo-1, 8-naphthyridine-3-carboxylic acid and 2, 3-dihydro-7-oxo-7H-pyrido [ Novel azetidine derivatives of pyridonecarboxylic acids, such as 1,2,3-dec] [1,4] benzoxazine-6-carboxylic acid, therapeutically acceptable salts of these compounds, methods for their preparation and their use as pharmaceuticals It is about.

Description

항균 활성을 갖는 피리돈카르복시산의 신규한 아제티딘 유도체Novel azetidine derivatives of pyridonecarboxylic acid with antibacterial activity

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is an open matter, no full text was included.

Claims (11)

일반식(Ⅰ)에 해당하는 이 발명의 주제 화합물.The subject compound of this invention corresponding to general formula (I). 상기 식에서, A는 질소원자 또는 대체적으로 수소원자가 붙어 있는 탄소원자(C-H), 또는 대체적으로 할로겐 원자가 붙어 있는 탄소원자(C-X)(이 경우에 X는 염소, 불소 또는 브롬 원자이다), 또는 대체적으로 히드록시 라디칼을 갖는 탄소원자(C-OH)이고, R₁은 저급 알킬 또는 시클로알킬 라디칼, 저급 할로알킬 라디칼, 아릴 라디칼 또는 특히 하나 또는 그보다 많은 불소원자(들)로 치환된 아릴 라디칼이고, R₂및 R₃는 수소원자, 저급 알킬 라디칼, 히드록시 라디칼, 아미노 라디칼, 아미노알킬 라디칼, 알킬아미노 라디칼, 디알킬아미노라디칼 3내지 6원 고리일 수 있는 질소 헤테로시클릭 라디칼, 알킬아미노알킬 라디칼, 알킬카르복사미도 라디칼(이 후자의 경우에 알킬 라디칼은 하나 또는 그보다 많은 할로겐으로 치환될 수 있다), 아릴설포닐옥시 라디칼, 알킬설 포닐옥시 라디칼, 카르복사미도 라디칼(이는 질소 또는 시아노 라디칼상에 치환되거나 치환되지 않을 수 있다)이고, R₄및 R5는 같거나 다를 수 있으며, 수소원자 또는 저급 알킬 라디칼이고, R6는 수소원자, 니트로 라디칼 또는 아미노 또는 치환 아미노 라디칼이고, R7은 히드록시 라디칼 또는 C₁∼C₄저급 알콕시 라디칼이고, A 및 R₁은 함께 C-CH₂-CH₂-CHR8- 또는 C-O-CH₂-CHR8-기로 나타나는 고리를 형성할 수 있으며, R8은 수소원자 또는 저급 알킬 라디칼이고, 이 후자의 경우에, “R” 또는 “S”배위를 갖는 또다른 치랄 중심이 있다.Wherein A is a carbon atom (CH) with a nitrogen atom or a hydrogen atom in general, or a carbon atom (CX) with a halogen atom in general (in this case X is a chlorine, fluorine or bromine atom), or substantially Is a carbon atom having a hydroxy radical (C-OH), R 'is a lower alkyl or cycloalkyl radical, a lower haloalkyl radical, an aryl radical or an aryl radical, in particular substituted with one or more fluorine atom (s), R2 and R3 is a hydrogen atom, a lower alkyl radical, a hydroxy radical, an amino radical, an aminoalkyl radical, an alkylamino radical, a nitrogen heterocyclic radical which may be a dialkylamino radical 3 to 6 membered ring, an alkylaminoalkyl radical, an alkylcarbox Unrefined radicals (in this latter alkyl radical may be substituted with one or more halogens), arylsulfonyloxy radicals, Kilseol sulfonyl and oxy radical, carboxamide not shown radical (which nitrogen or cyano can be optionally substituted on the radical) and, R₄ and R 5 may be the same or different, a hydrogen atom or a lower alkyl radical, R 6 is A hydrogen atom, a nitro radical or an amino or substituted amino radical, R 7 is a hydroxy radical or a C₁ to C₄ lower alkoxy radical, and A and R₁ together are C-CH₂-CH₂-CHR 8 -or CO-CH₂-CHR 8- It is possible to form a ring represented by a group, where R 8 is a hydrogen atom or a lower alkyl radical, in which case there is another chiral center having a “R” or “S” configuration. 제1항에 있어서, 아래 군으로부터 선택되는 일반식 (Ⅰ)에 해당되는 화합물들 : ·7-[(2S, 3R)-3-아미노-2-메틸-1-아제티디닐]-1-(2,4-디플루오로페닐)-6-플루오로-1, 4-디히드로-4-옥소-3-퀴놀린카르복시산, ·7-[(2S, 3R)-3-아미노-2-메틸-1-아제티디닐]-8-클로로-1-시클로프로필-6-플루오로-1, 4-디히드로-4-옥소-3-퀴놀린카르복시산, ·5-아미노-7-[(2S, 3R)-3-아미노-2-메틸-1-아제티디딜]-1-시클로프로필-6, 8-디플루오로-1, 4-디히드로-4-옥소-3-퀴놀린카르복시산, ·7-[(2S, 3R)-3-아미노-2-메틸-1-아제티디닐]-1-시클로프로필-6, 8-디플루오로-1, 4-디히드로-4-옥소-3-퀴놀린카르복시산, ·7-[(2S,3R)-3-아미노-2-메틸-1-아제티디닐]-8-클로로-1-(2, 4-디플루오로페닐)-6-플루오로-1, 4-디히드로-4-옥소-3-퀴놀린카르복시산, ·7-[3-아미노-3-메틸-1-아제티디닐]-8-클로로-1-시클로프로필-6-플루오로-1, 4-디히드로-4-옥소-3-퀴놀린카르복시산 p-톨루엔설폰산염, ·7-[(2RS, 3SR)-3-아미노-2-메틸-1-아제티디닐]-6, 8-디플루오로-1-에틸-1, 4-디히드로-4-옥소-3-퀴놀린카르복시산 p-톨루엔설폰산염, ·7-[(2RS,3SR)-3-아미노-2-메틸-1-아제티디닐]-1-(2, 4-디플루오로페닐)-6-플루오로-1, 4-디히드로-4-옥소-3-퀴놀린카르 복시산 p-톨루엔설폰산염, ·7-[(2S,3R)-3-아미노-2-메틸-1-아제티;디닐]-6, 8-디플루오로-1-에틸-1, 4-디히드로-4-옥소-3-퀴놀린카르복시산, ·7-[(2S,3R)-3-아미노-2-메틸-1-아제티디닐]-1-(2, 4-디플루오로페닐-6-플루오로-1, 4-디히드로-4-옥소-3-퀴놀린카르복시산, ·7-[(2S,3R)-3-아미노-2-메틸-1-아제티디닐]-1-(2, 4-디플루오로페닐-6-플루오로-1, 4-디히드로-4-옥소-1, 8-나프티리딘-3-카르복시산, ·7-[(2RS,3SR)-3-아미노-2-메틸-1-아제티디닐]-1-시클로프로필-6-플루오로-1, 4-디히드로-4-옥소-1, 8-나프티리딘-3-카르복시산 p-톨루엔설폰산염, ·7-[(2S,3R)-3-아미노-2-메틸-1-아제티디닐]-1-시클로프로필-6-플루오로-1, 4-디히드로-4-옥소-1, 8-나프티리딘-3-카르복시산 p-톨루엔설폰산염, ·7-(3-아미노-3-메틸-1-아제티디닐)-1-시클로프로필-6-플루오로-1, 4-디히드로-4-옥소-1, 8-나프티리딘-3-카르복시산 p-톨루엔설폰산염, ·1-시클로프로필-6-플루오로-7-(3-메틸-3-메틸아미노-1-아제티디닐)-1, 4-디히드로-4-옥소-1, 8-나프티리딘-3-카르복시산 p-톨루엔설폰산염, ·7-[(2R, 3S)-3-아미노-2-메틸-1-아제티디닐]-1-(2, 4-디플루오로페닐)-6-플루오로-1, 4-디히드로-4-옥소-1, 8-나프티리딘-3-카르복시산, ·7-[(2S,3R)-3-아미노-2-메틸-1-아제티디닐]-1-시클로프로필-6-플루오로-1, 4-디히드로-4-옥소-1, 8-나프티리딘-3-카르복시산 메탈설폰산염, ·7-[(2S,3R)-3-아미노-2-메틸-1-아제티디닐]-1-시클로프로필-6-플루오로-1, 4-디히드로-4-옥소-1, 8-나프티리딘-3-카르복시산 염산염, ·7-[(2S,3R)-3-아미노-2-메틸-1-아제티디닐]-6, 8-디플루오로-1-(2,4-디플루오로페닐)-1, 4-디히드로-4-옥소-3-퀴놀린카르복시산, ·7-[(2S,3R)-3-아미노-2-메틸-1-아제티디닐]-1-(2,4-디플루오로페닐)-6-플루오로-1, 4-디히드로-4-옥소-3-퀴놀린카르복시산 p-톨루엔설폰산염, ·7-[(2RS,3SR)-3-아미노-2-메틸-1-아제티디닐]-1-시클로프로필-6-플루오로-1, 4-디히드로-4-옥소-3-퀴놀린카르복시산 메탄설폰산염, ·5-아미노-7-(3-아미노-1-아제티디닐)-1-시클로프로필-6, 8-디플루오로-1, 4-디히드로-4-옥소-3-퀴놀린카르복시산, ·7-[(2S,3R)-3-아미노-2-메틸-1-아제티디닐]-1-(2,4-디플루오로페닐)-6-플루오로-1, 4-디히드로-4-옥소-3-퀴놀린카르복시산 염산염, ·7-[(2S,3R)-3-아미노-2-메틸-1-아제티디닐]-1-(2,4-디플루오로페닐)-6-플루오로-1, 4-디히드로-4-옥소-3-퀴놀린카르복시산 메탄설폰산염, ·7-(3-아미노-1-아제티디닐)-8-클로로-1-시클로프로필-6-플루오로-1, 4-디히드로-4-옥소-3-퀴놀린카르복시산, ·8-클로로-1-시클로프로필-6-플루오로-7-(3-메틸아미노-1-아제티디닐)-1, 4-디히드로-4-옥소-3-퀴놀린카르복시산, ·7-(3-아미노-1-아제티디닐)-8-클로로-1-(2,4-디플루오로페닐)-6-플루오로-1, 4-디히드로-4-옥소-3-퀴놀린카르복시산, ·8-클로로-1-(2,4-디플루오로페닐)-6-플루오로-7-(3-메틸-아미노-1-이제티디닐)-1, 4-디히드로-4-옥소-3-퀴놀린카르복시산, ·7-[(2R,3S)-3-아미노-2-메틸-1-아제티디닐]-8-클로로-1-시클로프로필-6-플루오로-1, 4-디히드로-4-옥소-3-퀴놀린카르복시산, ·5-아미노-7-(3-아미노-3-메틸-1-아제티디닐)-6, 8-디플루오로-1-(2,4-디플루오로페닐)-1, 4-디히드로-4-옥소-3-퀴놀린카르복시산, ·5-아미노-7-[(2R,3S)-3아미노-2-메틸-1-아제티디닐]-6, 8-디플루오로-1-(2,4-디플루오로페닐)-1, 4-디히드로-4-옥소-3-퀴놀린카르복시산, ·5-아미노-7-(3-아미노-1-아제티디닐)-6, 8-디플루오로-1-(2,4-디플루오로페닐)-1, 4-디히드로-4-옥소-3-퀴놀린카르복시산, ·5-아미노-7-(3-아미노-3-메틸-1-아제티디닐)-6, 8-디플루오로-1-에틸-1, 4-디히드로-4-옥소-3-퀴놀린카르복시산, ·5-아미노-7-[(2S,3R)-3-아미노-2-메틸-1-아제티디닐]-6, 8-디플루오로-1-에틸-1, 4-디히드로-4-옥소-3-퀴놀린카르복시산, ·5-아미노-7-(3-아미노-1-아제티디닐)-6, 8-디플루오로-1-에틸-1, 4-디히드로-4-옥소-3-퀴놀린 카르복시산.The compound according to claim 1, which corresponds to the general formula (I) selected from the following group: 7-[(2S, 3R) -3-amino-2-methyl-1-azetidinyl] -1- ( 2,4-difluorophenyl) -6-fluoro-1, 4-dihydro-4-oxo-3-quinolinecarboxylic acid, 7-[(2S, 3R) -3-amino-2-methyl-1 -Azetidinyl] -8-chloro-1-cyclopropyl-6-fluoro-1, 4-dihydro-4-oxo-3-quinolinecarboxylic acid, · 5-amino-7-[(2S, 3R)- 3-amino-2-methyl-1-azetidiyl] -1-cyclopropyl-6, 8-difluoro-1, 4-dihydro-4-oxo-3-quinolinecarboxylic acid, 7-[(2S , 3R) -3-amino-2-methyl-1-azetidinyl] -1-cyclopropyl-6, 8-difluoro-1, 4-dihydro-4-oxo-3-quinolinecarboxylic acid, -[(2S, 3R) -3-Amino-2-methyl-1-azetidinyl] -8-chloro-1- (2, 4-difluorophenyl) -6-fluoro-1, 4-di Hydro-4-oxo-3-quinolinecarboxylic acid, 7- [3-amino-3-methyl-1-azetidinyl] -8-chloro-1-cyclopropyl-6-fluoro-1, 4-dich Dro-4-oxo-3-quinolinecarboxylic acid p-toluenesulfonate, · 7-[(2RS, 3SR) -3-amino-2-methyl-1-azetidinyl] -6,8-difluoro-1 -Ethyl-1, 4-dihydro-4-oxo-3-quinolinecarboxylic acid p-toluenesulfonate, · 7-[(2RS, 3SR) -3-amino-2-methyl-1-azetidinyl] -1 -(2,4-difluorophenyl) -6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxic acid p-toluenesulfonic acid salt, 7-[(2S, 3R)- 3-amino-2-methyl-1-azeti; dinyl] -6, 8-difluoro-1-ethyl-1, 4-dihydro-4-oxo-3-quinolinecarboxylic acid, 7-[(2S , 3R) -3-amino-2-methyl-1-azetidinyl] -1- (2, 4-difluorophenyl-6-fluoro-1, 4-dihydro-4-oxo-3-quinoline Carboxylic acids, 7-[(2S, 3R) -3-amino-2-methyl-1-azetidinyl] -1- (2, 4-difluorophenyl-6-fluoro-1, 4-dihydro -4-oxo-1,8-naphthyridine-3-carboxylic acid, 7-[(2RS, 3SR) -3-amino-2-methyl-1-azetidinyl] -1-cyclopropyl-6-fluoro -1,4-dihydro-4-oxo-1, 8-naph Tyridine-3-carboxylic acid p-toluenesulfonate, 7-[(2S, 3R) -3-amino-2-methyl-1-azetidinyl] -1-cyclopropyl-6-fluoro-1, 4 -Dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid p-toluenesulfonate, 7- (3-amino-3-methyl-1-azetidinyl) -1-cyclopropyl-6- Fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid p-toluenesulfonate, 1-cyclopropyl-6-fluoro-7- (3-methyl-3- Methylamino-1-azetidinyl) -1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid p-toluenesulfonate, 7-[(2R, 3S) -3-amino -2-methyl-1-azetidinyl] -1- (2, 4-difluorophenyl) -6-fluoro-1, 4-dihydro-4-oxo-1, 8-naphthyridine-3- Carboxylic acid, 7-[(2S, 3R) -3-amino-2-methyl-1-azetidinyl] -1-cyclopropyl-6-fluoro-1, 4-dihydro-4-oxo-1, 8-naphthyridine-3-carboxylic acid metalsulfonic acid salt, 7-[(2S, 3R) -3-amino-2-methyl-1-azetidinyl] -1-cyclopropyl-6 -Fluoro-1, 4-dihydro-4-oxo-1, 8-naphthyridine-3-carboxylic acid hydrochloride, · 7-[(2S, 3R) -3-amino-2-methyl-1-azetidinyl ] -6, 8-difluoro-1- (2,4-difluorophenyl) -1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 7-[(2S, 3R) -3 -Amino-2-methyl-1-azetidinyl] -1- (2,4-difluorophenyl) -6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid p-toluene Sulfonate, 7-[(2RS, 3SR) -3-amino-2-methyl-1-azetidinyl] -1-cyclopropyl-6-fluoro-1, 4-dihydro-4-oxo-3 -Quinolinecarboxylic acid methanesulfonate, 5-amino-7- (3-amino-1-azetidinyl) -1-cyclopropyl-6, 8-difluoro-1, 4-dihydro-4-oxo- 3-quinolinecarboxylic acid, 7-[(2S, 3R) -3-amino-2-methyl-1-azetidinyl] -1- (2,4-difluorophenyl) -6-fluoro-1, 4-dihydro-4-oxo-3-quinolinecarboxylic acid hydrochloride, 7-[(2S, 3R) -3-amino-2-methyl-1-azetidinyl] -1- (2,4-difluoro Phenyl) -6-fluoro-1, 4-dihydro-4-oxo-3-quinolinecarboxylic acid methanesulfonate, 7- (3-amino-1-azetidinyl) -8-chloro-1-cyclopropyl-6-fluoro-1, 4- Dihydro-4-oxo-3-quinolinecarboxylic acid, 8-chloro-1-cyclopropyl-6-fluoro-7- (3-methylamino-1-azetidinyl) -1, 4-dihydro-4 Oxo-3-quinolinecarboxylic acid, 7- (3-amino-1-azetidinyl) -8-chloro-1- (2,4-difluorophenyl) -6-fluoro-1,4-di Hydro-4-oxo-3-quinolinecarboxylic acid, 8-chloro-1- (2,4-difluorophenyl) -6-fluoro-7- (3-methyl-amino-1-ezetidinyl)- 1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 7-[(2R, 3S) -3-amino-2-methyl-1-azetidinyl] -8-chloro-1-cyclopropyl- 6-fluoro-1, 4-dihydro-4-oxo-3-quinolinecarboxylic acid, 5-amino-7- (3-amino-3-methyl-1-azetidinyl) -6, 8-difluoro Rho-1- (2,4-difluorophenyl) -1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 5-amino-7-[(2R, 3 S) -3amino-2-methyl-1-azetidinyl] -6, 8-difluoro-1- (2,4-difluorophenyl) -1, 4-dihydro-4-oxo-3 -Quinolinecarboxylic acid, 5-amino-7- (3-amino-1-azetidinyl) -6, 8-difluoro-1- (2,4-difluorophenyl) -1, 4-dihydro 4-oxo-3-quinolinecarboxylic acid, 5-amino-7- (3-amino-3-methyl-1-azetidinyl) -6, 8-difluoro-1-ethyl-1, 4-di Hydro-4-oxo-3-quinolinecarboxylic acid, 5-amino-7-[(2S, 3R) -3-amino-2-methyl-1-azetidinyl] -6, 8-difluoro-1- Ethyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 5-amino-7- (3-amino-1-azetidinyl) -6,8-difluoro-1-ethyl-1 , 4-dihydro-4-oxo-3-quinoline carboxylic acid. 하기 일반식(Ⅱ)의 화합물을 하기 일반식(Ⅲ)의 아제티딘과 반응시키는 것을 특징으로 하는 제1항 및 제2항에 따른 화합물의 제조방법.A process for producing a compound according to claim 1 or 2, wherein the compound of formula (II) is reacted with azetidine of formula (III). 상기 식에서, A, R₁,R₂,R₃,R₄,R5,R6및 R7은 상기 정의한 바와 같고, Z는 할로겐 원자, 바람직하게는 염소 또는 불소이다.Wherein R, A, R₁, R₂, R₃, R₄, R 5, R 6 and R 7 is as defined above, Z is a halogen atom, preferably chlorine or fluorine. 의약품으로서, 특히 어떤 감염성 질병 치료를 위한 의약품으로서의 제1항 내지 제2항에 따른 일반식 (Ⅰ)의 유도체 및 이들의 치료학적으로 허용가능한 염.As a medicament, in particular as a medicament for the treatment of certain infectious diseases, derivatives of formula (I) according to claims 1 and 2 and therapeutically acceptable salts thereof. 제약학적으로 허용가능한 부형제에 첨가하여, 제1항 내지 제2항중 어느 한 항에 따른, 일반식 (Ⅰ)의 유도체 또는 그의 생리학적으로 허용가능한 염 적어도 하나를 포함하는 것을 특징으로 하는 제약 조성물.A pharmaceutical composition comprising, in addition to a pharmaceutically acceptable excipient, at least one derivative of formula (I) or a physiologically acceptable salt thereof according to any one of claims 1 to 2. 세균 감염 치료용 의약품 제조를 위한, 제1항 내지 제2항중 어느 한 항에 따른 일반식 (Ⅰ)의 유도체 및 이들의 생리학적으로 허용가능한 염의 사용.Use of a derivative of formula (I) according to any one of claims 1 to 2 and their physiologically acceptable salts for the manufacture of a medicament for the treatment of bacterial infections. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019930006389A 1992-04-16 1993-04-16 Novel azetidine derivatives of pyridonecarboxylic acid with antibacterial activity KR930021633A (en)

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