KR940014394A - Novel pyridone carboxylic acid derivatives and preparation method thereof - Google Patents

Novel pyridone carboxylic acid derivatives and preparation method thereof Download PDF

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KR940014394A
KR940014394A KR1019930021035A KR930021035A KR940014394A KR 940014394 A KR940014394 A KR 940014394A KR 1019930021035 A KR1019930021035 A KR 1019930021035A KR 930021035 A KR930021035 A KR 930021035A KR 940014394 A KR940014394 A KR 940014394A
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compound
carboxylic acid
amino
azabicyclo
salt
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KR970007919B1 (en
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김진웅
조일환
이재목
이기호
김제학
정용환
안승호
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김정순
제일제당 주식회사
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    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/4375—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
    • 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

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  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

본 발명은 다음 일반식(Ⅰ)로 표시되는 피리돈 카르본산 화합물과 그의 염 및 이를 함유시켜서 된 항균제 조성물에 관한 것이다.The present invention relates to a pyridone carboxylic acid compound represented by the following general formula (I), a salt thereof and an antimicrobial composition containing the same.

상기 식(Ⅰ)에서, R1은 저급 알킬기, 할로겐 치환 저급 알킬기, 저급 알케닐기, 사이클로 알킬기 또는 치환되거나 치환되지 않은 페닐기를 의미하고, R2는 수소, 아미노기 또는 저급 알킬기를 의미하고, A는 질소 원자 또는 C-X(여기서 X는 수소, 할로겐 원자 또는 알콕시기를 의미함)를 의미하며, Z는 다음식으로 표시되는 기를 나타낸다.In formula (I), R 1 means lower alkyl group, halogen substituted lower alkyl group, lower alkenyl group, cycloalkyl group or substituted or unsubstituted phenyl group, R 2 means hydrogen, amino group or lower alkyl group, and A is A nitrogen atom or CX (where X means hydrogen, a halogen atom or an alkoxy group), and Z represents a group represented by the following formula.

(상기식에서, R3, R4는 수소 원자 또는 저급 알킬기를 의미하고, R5, R6는 수소, 히드록시, 알콕시, 아미노, 저급 알킬기로 치환된 아미노기를 의미하는데 둘중 하나는 수소를 의미한다.)Wherein R 3 and R 4 refer to a hydrogen atom or a lower alkyl group, and R 5 and R 6 refer to an amino group substituted with hydrogen, hydroxy, alkoxy, amino or a lower alkyl group, one of which means hydrogen .)

Description

신규한 피리돈 카르본산 유도체 및 그의 제조방법Novel pyridone carboxylic acid derivatives and preparation method thereof

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음As this is a public information case, the full text was not included.

Claims (54)

다음 일반식(Ⅰ)로 표시되는 피리돈 카르본산 유도체와 그의 에스테르 및 그의 염.The pyridone carboxylic acid derivative represented by the following general formula (I), its ester, and its salt. 상기 식(Ⅰ)에서 R1은 저급 알킬기, 할로겐 치환 저급 알킬기, 저급 알케닐기, 사이클로 알킬기 또는 치환되거나 치환되지 않은 페닐기를 의미하고, R2는 수소, 아미노기 또는 저급 알킬기를 의미하고, A는 질소 원자 또는 C-X(여기서 X는 수소, 할로겐 원자 또는 알콕시기를 의미함)를 의미하며, Z는 다음식으로 표시되는 기를 나타낸다.In formula (I), R 1 means lower alkyl group, halogen substituted lower alkyl group, lower alkenyl group, cycloalkyl group or substituted or unsubstituted phenyl group, R 2 means hydrogen, amino group or lower alkyl group, A is nitrogen A atom or CX (where X means hydrogen, a halogen atom or an alkoxy group), and Z represents a group represented by the following formula. (상기식에서, R3, R4는 수소 원자 또는 저급 알킬기를 의미하고, R5, R6는 수소, 히드록시, 알콕시, 아미노, 저급 알킬기로 치환된 아미노기를 의미하는데 둘중 하나는 수소를 의미한다).Wherein R 3 and R 4 refer to a hydrogen atom or a lower alkyl group, and R 5 and R 6 refer to an amino group substituted with hydrogen, hydroxy, alkoxy, amino or a lower alkyl group, one of which means hydrogen ). 제1항에 있어서, 화합물은 7-([1α, 5α, 6β]-6-아미노-1-메틸-3-아자비시클로[3.2.0]헵탄-3-일)-1-시클로프로필-6-플루오로-1, 4-디히드로-4-옥소퀴놀린-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is 7-([1α, 5α, 6β] -6-amino-1-methyl-3-azabicyclo [3.2.0] heptan-3-yl) -1-cyclopropyl-6- Pyridone carboxylic acid compound and its salt characterized by being fluoro-1 and 4-dihydro-4-oxoquinoline-3-carboxylic acid. 제1항에 있어서, 화합물은 7-([1α, 5α, 6β]-6-아미노-1-메틸-3-아자비시클로 [3.2.0]헵탄-3-일)-1-시클로프로필-6, 8-디플루오로-1, 4-디히드로-4-옥소퀴놀린-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is 7-([1α, 5α, 6β] -6-amino-1-methyl-3-azabicyclo [3.2.0] heptan-3-yl) -1-cyclopropyl-6, A pyridone carboxylic acid compound and salt thereof, characterized in that it is 8-difluoro-1, 4-dihydro-4-oxoquinoline-3-carboxylic acid. 제1항에 있어서, 화합물은 5-아미노-7-([1α, 5α, 6β]-6-아미노-1-메틸-3-아자비시클로 [3.2.0]헵탄-3-일)-1-시클로프로필-6, 8-디플루오로-1, 4-디히드로-4-옥소퀴놀린-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is 5-amino-7-([1α, 5α, 6β] -6-amino-1-methyl-3-azabicyclo [3.2.0] heptan-3-yl) -1-cyclo Pyridone carboxylic acid compound and its salt characterized by being propyl-6, 8-difluoro-1, 4-dihydro-4-oxoquinoline-3-carboxylic acid. 제1항에 있어서, 화합물은 7-([1α, 5α, 6β]-6-아미노-1-메틸-3-아자비시클로 [3.2.0]헵탄-3-일)-6, 8-디플루오로-1-(2, 4-디플루오로페닐)-1, 4-디히드로-4-옥소퀴놀린-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is 7-([1α, 5α, 6β] -6-amino-1-methyl-3-azabicyclo [3.2.0] heptan-3-yl) -6, 8-difluoro Pyridone carboxylic acid compound and its salt characterized by being -1- (2, 4-difluorophenyl) -1 and 4-dihydro-4-oxoquinoline-3-carboxylic acid. 제1항에 있어서, 화합물은 7-([1α, 5α, 6β]-6-아미노-1-메틸-3-아자비시클로 [3.2.0]헵탄-3-일)-1-시클로프로필-6, 8-디플루오로-5-메틸-1, 4-디히드로-4-옥소퀴놀린-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is 7-([1α, 5α, 6β] -6-amino-1-methyl-3-azabicyclo [3.2.0] heptan-3-yl) -1-cyclopropyl-6, A pyridone carboxylic acid compound and salt thereof, characterized in that it is 8-difluoro-5-methyl-1, 4-dihydro-4-oxoquinoline-3-carboxylic acid. 제1항에 있어서, 화합물은 7-([1α, 5α, 6β]-6-아미노-1-메틸-3-아자비시클로 [3.2.0]헵탄-3-일)-8-클로로-1-시클로프로필-6-플루오로-1, 4-디히드로-4-옥소퀴놀린-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is 7-([1α, 5α, 6β] -6-amino-1-methyl-3-azabicyclo [3.2.0] heptan-3-yl) -8-chloro-1-cyclo Pyridone carboxylic acid compound and its salt, characterized in that it is propyl-6-fluoro-1, 4-dihydro-4-oxoquinoline-3-carboxylic acid. 제1항에 있어서, 화합물은 7-([1α, 5α, 6β]-6-아미노-1-메틸-3-아자비시클로 [3.2.0]헵탄-3-일)-1-시클로프로필-6-플루오로-1, 4-디히드로-4-옥소-1, 8-나프티리딘-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is 7-([1α, 5α, 6β] -6-amino-1-methyl-3-azabicyclo [3.2.0] heptan-3-yl) -1-cyclopropyl-6- Pyridone carboxylic acid compound and salt thereof characterized by being fluoro-1, 4-dihydro-4-oxo-1, 8-naphthyridine-3-carboxylic acid. 제1항에 있어서, 화합물은 7-([1α, 5α, 6β]-6-아미노-1-메틸-3-아자비시클로 [3.2.0]헵탄-3-일)-1-(2, 4-디플루오로페닐)-6-플루오로-1, 4-디히드로-4-옥소-1, 8-나프티리딘-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is 7-([1α, 5α, 6β] -6-amino-1-methyl-3-azabicyclo [3.2.0] heptan-3-yl) -1- (2, 4- Difluorophenyl) -6-fluoro-1, 4-dihydro-4-oxo-1, 8-naphthyridine-3-carboxylic acid. A pyridone carboxylic acid compound and salt thereof. 제1항에 있어서, 화합물은 7-([1α, 5α, 6β]-6-아미노-1-메틸-3-아자비시클로 [3.2.0]헵탄-3-일)-6-플루오로-1-(4-플루오로페닐)1, 4-디히드로-4-옥소-1, 8-나프티리딘-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is 7-([1α, 5α, 6β] -6-amino-1-methyl-3-azabicyclo [3.2.0] heptan-3-yl) -6-fluoro-1- (4-fluorophenyl) 1, 4-dihydro-4-oxo-1, 8-naphthyridine-3-carboxylic acid. A pyridone carboxylic acid compound and salt thereof. 제1항에 있어서, 화합물은 7-([1α, 5α, 6β]-6-아미노-1-메틸-3-아자비시클로 [3.2.0]헵탄-3-일)-1-t-부틸-6-플루오로-1, 4-디히드로-4-옥소-1, 8-나프티리딘-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is 7-([1α, 5α, 6β] -6-amino-1-methyl-3-azabicyclo [3.2.0] heptan-3-yl) -1-t-butyl-6 -Pyrodon-1, 4-dihydro-4-oxo-1, 8-naphthyridine-3-carboxylic acid, and a salt thereof. 제1항에 있어서, 화합물은 7-([1α, 5α, 6β]-6-아미노-1-메틸-3-아자비시클로 [3.2.0]헵탄-3-일)-1-(2, 4-디플루오로페닐)-6-플루오로-5-메틸-1, 4-디히드로-4-옥소-1, 8-나프티리딘-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is 7-([1α, 5α, 6β] -6-amino-1-methyl-3-azabicyclo [3.2.0] heptan-3-yl) -1- (2, 4- Difluorophenyl) -6-fluoro-5-methyl-1, 4-dihydro-4-oxo-1, 8-naphthyridine-3-carboxylic acid and salts thereof . 제1항에 있어서, 화합물은 (＋)-7-([1α, 5α, 6β]-6-아미노-1-메틸-3-아자비시클로 [3.2.0]헵탄-3-일)-1-시클로프로필-6-플루오로-1, 4-디히드로-4-옥소-1, 8-나프티리딘-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is (+)-7-([1α, 5α, 6β] -6-amino-1-methyl-3-azabicyclo [3.2.0] heptan-3-yl) -1-cyclo Pyridone carboxylic acid compound and salt thereof characterized by being propyl-6-fluoro-1, 4-dihydro-4-oxo-1, 8-naphthyridine-3-carboxylic acid. 제1항에 있어서, 화합물은 (－)-7-([1α, 5α, 6β]-6-아미노-1-메틸-3-아자비시클로 [3.2.0]헵탄-3-일)-1-시클로프로필-6, 8-디플루오로-1, 4-디히드로-4-옥소퀴놀린-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is (-)-7-([1α, 5α, 6β] -6-amino-1-methyl-3-azabicyclo [3.2.0] heptan-3-yl) -1-cyclo Pyridone carboxylic acid compound and its salt characterized by being propyl-6, 8-difluoro-1, 4-dihydro-4-oxoquinoline-3-carboxylic acid. 제1항에 있어서, 화합물은 (＋)-7-([1α, 5α, 6β]-6-아미노-1-메틸-3-아자비시클로 [3.2.0]헵탄-3-일)-1-시클로프로필-6, 8-디플루오로-1, 4-디히드로-4-옥소퀴놀린-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is (+)-7-([1α, 5α, 6β] -6-amino-1-methyl-3-azabicyclo [3.2.0] heptan-3-yl) -1-cyclo Pyridone carboxylic acid compound and its salt characterized by being propyl-6, 8-difluoro-1, 4-dihydro-4-oxoquinoline-3-carboxylic acid. 제1항에 있어서, 화합물은 1-시클로프로필-6, 8-디플루오로-7-([1α, 5α, 6β]-6-히드록시-1-메틸-3-아자비시클로 [3.2.0]헵탄-3-일)-1, 4-디히드로-4-옥소퀴놀린-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is 1-cyclopropyl-6, 8-difluoro-7-([1α, 5α, 6β] -6-hydroxy-1-methyl-3-azabicyclo [3.2.0] Heptane-3-yl) -1, 4-dihydro-4-oxoquinoline-3-carboxylic acid, The pyridone carboxylic acid compound and its salt. 제1항에 있어서, 화합물은 1-시클로프로필-6-플루오로-7-([1α, 5α, 6β]-6-히드록시-1-메틸-3-아자비시클로 [3.2.0]헵탄-3-일)-1, 4-디히드로-4-옥소-1, 8-나프티리딘-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is 1-cyclopropyl-6-fluoro-7-([1α, 5α, 6β] -6-hydroxy-1-methyl-3-azabicyclo [3.2.0] heptan-3 -Yl) -1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, and a pyridone carboxylic acid compound and salt thereof. 제1항에 있어서, 화합물은 (－)-7-([1α, 5α, 6β]-6-아미노-1-메틸-3-아자비시클로 [3.2.0]헵탄-3-일)-1-시클로프로필-6, 8-디플루오로-5-메틸-1, 4-디히드로-4-옥소퀴놀린-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is (-)-7-([1α, 5α, 6β] -6-amino-1-methyl-3-azabicyclo [3.2.0] heptan-3-yl) -1-cyclo Pyridone carboxylic acid compound and salt thereof characterized by being propyl-6, 8-difluoro-5-methyl-1, 4-dihydro-4-oxoquinoline-3-carboxylic acid. 제1항에 있어서, 화합물은 (－)-5-아미노-7-([1α, 5α, 6β]-6-아미노-1-메틸-3-아자비시클로 [3.2.0]헵탄-3-일)-1-시클로프로필-6, 8-디플루오로-1, 4-디히드로-4-옥소퀴놀린-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is (−)-5-amino-7-([1α, 5α, 6β] -6-amino-1-methyl-3-azabicyclo [3.2.0] heptan-3-yl) 1-cyclopropyl-6, 8-difluoro-1, 4-dihydro-4-oxoquinoline-3-carboxylic acid. A pyridone carboxylic acid compound and salt thereof. 제1항에 있어서, 화합물은 (－)-7-([1α, 5α, 6β]-6-아미노-1-메틸-3-아자비시클로 [3.2.0]헵탄-3-일)-1-t-부틸-6-플루오로-1, 4-디히드로-4-옥소-1, 8-나프티리딘-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is (−)-7-([1α, 5α, 6β] -6-amino-1-methyl-3-azabicyclo [3.2.0] heptan-3-yl) -1-t Pyridone carboxylic acid compound and salt thereof characterized by -butyl-6-fluoro-1, 4-dihydro-4-oxo-1, 8-naphthyridine-3-carboxylic acid. 제1항에 있어서, 화합물은 (－)-7-([1α, 5α, 6β]-6-아미노-1-메틸-3-아자비시클로 [3.2.0]헵탄-3-일)-8-클로로-1-시클로프로필-6-플루오로-1, 4-디히드로-4-옥소퀴놀린-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is (-)-7-([1α, 5α, 6β] -6-amino-1-methyl-3-azabicyclo [3.2.0] heptan-3-yl) -8-chloro 1-cyclopropyl-6-fluoro-1, 4-dihydro-4-oxoquinoline-3-carboxylic acid, the pyridone carboxylic acid compound and its salt. 제1항에 있어서, 화합물은 (－)-7-([1α, 5α, 6β]-6-아미노-1-메틸-3-아자비시클로 [3.2.0]헵탄-3-일)-1-(2, 4-디플루오로페닐)-6-플루오로-1, 4-디히드로-4-옥소-1, 8-나프티리딘-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is selected from (−)-7-([1α, 5α, 6β] -6-amino-1-methyl-3-azabicyclo [3.2.0] heptan-3-yl) -1- ( 2,4-difluorophenyl) -6-fluoro-1, 4-dihydro-4-oxo-1, 8-naphthyridine-3-carboxylic acid, and a salt thereof . 제1항에 있어서, 화합물은 (－)-7-([1α, 5α, 6β]-6-아미노-1-메틸-3-아자비시클로 [3.2.0]헵탄-3-일)-6-플루오로-1-(4-플루오로페닐)-1, 4-디히드로-4-옥소-1, 8-나프티리딘-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is (-)-7-([1α, 5α, 6β] -6-amino-1-methyl-3-azabicyclo [3.2.0] heptan-3-yl) -6-fluoro Pyridone carboxylic acid compound and its salt characterized by being rho-1- (4-fluorophenyl) -1, 4-dihydro-4-oxo-1, 8-naphthyridine-3-carboxylic acid. 제1항에 있어서, 화합물은 7-([1α, 5α, 6β]-6-아미노-5-메틸-3-아자비시클로 [3.2.0]헵탄-3-일)-6, 8-디플루오로-1, 4-디히드로-4-옥소퀴놀린-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is 7-([1α, 5α, 6β] -6-amino-5-methyl-3-azabicyclo [3.2.0] heptan-3-yl) -6, 8-difluoro -1, 4-dihydro-4-oxoquinoline-3-carboxylic acid, and a pyridone carboxylic acid compound and its salt. 제1항에 있어서, 화합물은 7-([1α, 5α, 6β]-6-아미노-5-메틸-3-아자비시클로 [3.2.0]헵탄-3-일)-6-플루오로-1-(4-플루오로페닐)-1, 4-디히드로-4-옥소-1, 8-나프티리딘-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is 7-([1α, 5α, 6β] -6-amino-5-methyl-3-azabicyclo [3.2.0] heptan-3-yl) -6-fluoro-1- It is (4-fluorophenyl) -1, 4-dihydro-4-oxo-1, 8-naphthyridine-3-carboxylic acid, The pyridone carboxylic acid compound and its salt. 제1항에 있어서, 화합물은 8-클로로-1-시클로로프로필-7-([1α, 5α, 6β]-6-아미노-5-메틸-3-아자비시클로 [3.2.0]헵탄-3-일)-6-플루오로-1, 4-디히드로-4-옥소-3-퀴놀린카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is 8-chloro-1-cycloropropyl-7-([1α, 5α, 6β] -6-amino-5-methyl-3-azabicyclo [3.2.0] heptan-3- I) -6-fluoro-1, 4-dihydro-4-oxo-3-quinolinecarboxylic acid, and a pyridone carboxylic acid compound and its salt. 제1항에 있어서, 화합물은 7-([1α, 5α, 6β]-6-아미노-5-메틸-3-아자비시클로 [3.2.0]헵탄-3-일)-1-시클로프로필-6-플루오로-1, 4-디히드로-4-옥소-1, 8-나프티리딘-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is 7-([1α, 5α, 6β] -6-amino-5-methyl-3-azabicyclo [3.2.0] heptan-3-yl) -1-cyclopropyl-6- Pyridone carboxylic acid compound and salt thereof characterized by being fluoro-1, 4-dihydro-4-oxo-1, 8-naphthyridine-3-carboxylic acid. 제1항에 있어서, 화합물은 1-(2, 4)디플루오로페닐)-7-([1α, 5α, 6β]-6-아미노-5-메틸-3-아자비시클로 [3.2.0]헵탄-3-일)-6-플루오로-1, 4-디히드로-4-옥소-1, 8-나프티리딘-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is 1- (2, 4) difluorophenyl) -7-([1α, 5α, 6β] -6-amino-5-methyl-3-azabicyclo [3.2.0] heptane 3-yl) -6-fluoro-1, 4-dihydro-4-oxo-1, 8-naphthyridine-3-carboxylic acid. A pyridone carboxylic acid compound and salt thereof. 제1항에 있어서, 화합물은 (－)-7-([1α, 5α, 6β]-6-아미노-1-메틸-3-아자비시클로 [3.2.0]헵탄-3-일)-1-(2, 4-디플루오로페닐)-1, 4-디히드로-6-플루오로-5-메틸-4-옥소-1, 8-나프티리딘-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is selected from (−)-7-([1α, 5α, 6β] -6-amino-1-methyl-3-azabicyclo [3.2.0] heptan-3-yl) -1- ( 2,4-difluorophenyl) -1,4-dihydro-6-fluoro-5-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid Compounds and their salts. 제1항에 있어서, 화합물은 1-시클로프로필-7-([1α, 5α, 6β]-6-히드록시-3-아자비시클로 [3.2.0]헵탄-3-일)-6, 8-디플루오로-1, 4-디히드로-4-옥소-3-퀴놀린카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is 1-cyclopropyl-7-([1α, 5α, 6β] -6-hydroxy-3-azabicyclo [3.2.0] heptan-3-yl) -6, 8-di Pyridone carboxylic acid compound and its salt characterized by being fluoro-1 and 4-dihydro-4-oxo-3-quinolinecarboxylic acid. 제1항에 있어서, 화합물은 5-아미노-1-시클로프로필-7-([1α, 5α, 6β]-6-히드록시-3-아자비시클로 [3.2.0]헵탄-3-일]-6, 8-디플루오로-1, 4-디히드로-4-옥소-3-퀴놀린카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is 5-amino-1-cyclopropyl-7-([1α, 5α, 6β] -6-hydroxy-3-azabicyclo [3.2.0] heptan-3-yl] -6 And 8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, and a pyridone carboxylic acid compound and salt thereof. 제1항에 있어서, 화합물은 1-시클로프로필-7-([1α, 5α, 6β]-6-히드록시-3-아자비시클로 [3.2.0]헵탄-3-일)-6, 8-디플루오로-1, 4-디히드로-5-메틸-4-옥소-3-퀴놀린카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is 1-cyclopropyl-7-([1α, 5α, 6β] -6-hydroxy-3-azabicyclo [3.2.0] heptan-3-yl) -6, 8-di Pyridone carboxylic acid compound and its salt, characterized in that it is fluoro-1, 4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylic acid. 제1항에 있어서, 화합물은 1-시클로프로필-7-([1α, 5α, 6β]-6-아미노-3-아자비시클로 [3.2.0]헵탄-3-일)-6, 8-디플루오로-1, 4-디히드로-5-메틸-4-옥소-3-퀴놀린카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is 1-cyclopropyl-7-([1α, 5α, 6β] -6-amino-3-azabicyclo [3.2.0] heptan-3-yl) -6, 8-difluoro Ryo-1, 4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylic acid, It is a pyridone carboxylic acid compound and its salt. 제1항에 있어서, 화합물은 1-시클로프로필-7-([1α, 5α, 6β]-6-아미노-3-아자비시클로 [3.2.0]헵탄-3-일)-6, 8-디플루오로-1, 4-디히드로-4-옥소-3-퀴놀린카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is 1-cyclopropyl-7-([1α, 5α, 6β] -6-amino-3-azabicyclo [3.2.0] heptan-3-yl) -6, 8-difluoro Rho-1, 4-dihydro-4-oxo-3-quinolinecarboxylic acid, and a pyridone carboxylic acid compound and its salt. 제1항에 있어서, 화합물은 5-아미노-1-시클로프로필-7-([1α, 5α, 6β]-6-아미노-3-아자비시클로 [3.2.0]헵탄-3-일)-6, 8-디플루오로-1, 4-디히드로-4-옥소-3-퀴놀린카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is 5-amino-1-cyclopropyl-7-([1α, 5α, 6β] -6-amino-3-azabicyclo [3.2.0] heptan-3-yl) -6, A pyridone carboxylic acid compound and salt thereof characterized by being 8-difluoro-1 and 4-dihydro-4-oxo-3-quinolinecarboxylic acid. 제1항에 있어서, 화합물은 1-시클로프로필-7-([1α, 5α, 6β]-6-히드록시-3-아자비시클로 [3.2.0]헵탄-3-일)-6-플루오로-1, 4-디히드로-4-옥소-1, 8-나프티리딘-3-퀴놀린카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is 1-cyclopropyl-7-([1α, 5α, 6β] -6-hydroxy-3-azabicyclo [3.2.0] heptan-3-yl) -6-fluoro- 1, 4-dihydro-4-oxo-1, 8-naphthyridine-3-quinolinecarboxylic acid, and a pyridone carboxylic acid compound and its salt. 제1항에 있어서, 화합물은 1-시클로프로필-7-([1α, 5α, 6β]-6-아미노-3-아자비시클로 [3.2.0]헵탄-3-일)-6-플루오로-1, 4-디히드로-4-옥소-1, 8-나프티리딘-3-퀴놀린카복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is 1-cyclopropyl-7-([1α, 5α, 6β] -6-amino-3-azabicyclo [3.2.0] heptan-3-yl) -6-fluoro-1 And 4-dihydro-4-oxo-1, 8-naphthyridine-3-quinolinecarboxylic acid. The pyridone carboxylic acid compound and salt thereof. 제1항에 있어서, 화합물은 7-([1α, 5α, 6β]-6-아미노-3-아자비시클로 [3.2.0]헵탄-3-일)-1-디플루오로페닐)-1, 4-디히드로-6-플루오로-4-옥소-1, 8-나프티리딘-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is 7-([1α, 5α, 6β] -6-amino-3-azabicyclo [3.2.0] heptan-3-yl) -1-difluorophenyl) -1, 4 -Pyridone carboxylic acid compound and salt thereof characterized by -dihydro-6-fluoro-4-oxo-1, 8-naphthyridine-3-carboxylic acid. 제1항에 있어서, 화합물은 7-([1α, 5α, 6β]-6-아미노-3-아자비시클로 [3.2.0]헵탄-3-일)-1, 4디히드로-6-플루오로-1-(4-플루오로페닐)-4-옥소-1, 8-나프티리딘-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is 7-([1α, 5α, 6β] -6-amino-3-azabicyclo [3.2.0] heptan-3-yl) -1, 4dihydro-6-fluoro- 1- (4-fluorophenyl) -4-oxo-1,8-naphthyridine-3-carboxylic acid. A pyridone carboxylic acid compound and salt thereof. 제1항에 있어서, 화합물은 7-([1α, 5α, 6β]-6-아미노-3-아자비시클로 [3.2.0]헵탄-3-일)-8-클로로-1-시클로프로필-6-플루오로-1, 4-디히드로-4-옥소-3-퀴놀린카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is 7-([1α, 5α, 6β] -6-amino-3-azabicyclo [3.2.0] heptan-3-yl) -8-chloro-1-cyclopropyl-6- Pyridone carboxylic acid compound and its salt characterized by being fluoro-1 and 4-dihydro-4-oxo-3-quinolinecarboxylic acid. 제1항에 있어서, 화합물은 7-([1α, 5α, 6β]-6-아미노-3-아자비시클로 [3.2.0]헵탄-3-일)-1-(2, 4-디플루오로페닐)-1, 4-디히드로-6-플루오로-5-메틸-4-옥소-1, 8-나프티리딘-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is 7-([1α, 5α, 6β] -6-amino-3-azabicyclo [3.2.0] heptan-3-yl) -1- (2, 4-difluorophenyl ), 4-dihydro-6-fluoro-5-methyl-4-oxo-1, 8-naphthyridine-3-carboxylic acid. A pyridone carboxylic acid compound and salt thereof. 제1항에 있어서, 화합물은 (－)-7-([1α, 5α, 6β]-6-아미노-3-아자비시클로 [3.2.0]헵탄-3-일)-1-(2, 4-디플루오로페닐)-1, 4-디히드로-6-플루오로-4-옥소-1, 8-나프티리딘-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is (-)-7-([1α, 5α, 6β] -6-amino-3-azabicyclo [3.2.0] heptan-3-yl) -1- (2, 4- Difluorophenyl) -1, 4-dihydro-6-fluoro-4-oxo-1, 8-naphthyridine-3-carboxylic acid, The pyridone carboxylic acid compound and its salt. 제1항에 있어서, 화합물은 7-([1α, 5α, 6β]-6-아미노-1-메틸-아자비시클로 [3.2.0]헵탄-3-일)-1-(tert-부틸)-6-플루오로-1, 4-디히드로-4-옥소-1, 8-나프티리딘-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is 7-([1α, 5α, 6β] -6-amino-1-methyl-azabicyclo [3.2.0] heptan-3-yl) -1- (tert-butyl) -6 -Pyrodon-1, 4-dihydro-4-oxo-1, 8-naphthyridine-3-carboxylic acid, and a salt thereof. 제1항에 있어서, 화합물은 (－)-7-([1α, 5α, 6β]-6-아미노-3-아자비시클로 [3.2.0]헵탄-3-일)-1-시클로프로필-1, 4-디히드로-6-플루오로-5-메틸-1, 8-나프티리딘-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is selected from (−)-7-([1α, 5α, 6β] -6-amino-3-azabicyclo [3.2.0] heptan-3-yl) -1-cyclopropyl-1, Pyridone carboxylic acid compound and salt thereof characterized by 4-dihydro-6-fluoro-5-methyl-1, 8-naphthyridine-3-carboxylic acid. 제1항에 있어서, 화합물은 7-([1α, 5α, 6β]-6-아미노-1-메틸-3-아자비시클로 [3.2.0]헵탄-3-일)-1-시클로프로필-6-플루오로-8-메톡시-1, 4-디히드로-4-옥소퀴놀린-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is 7-([1α, 5α, 6β] -6-amino-1-methyl-3-azabicyclo [3.2.0] heptan-3-yl) -1-cyclopropyl-6- Pyridone carboxylic acid compound and its salt characterized by being fluoro-8-methoxy-1 and 4-dihydro-4-oxoquinoline-3-carboxylic acid. 제1항에 있어서, 화합물은 7-([1α, 5α, 6β]-6-아미노-1-메틸-3-아자비시클로 [3.2.0]헵탄-3-일)-1-시클로프로필-6-플루오로-1, 4-디히드로-4-옥소-1, 8-나프티리딘-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is 7-([1α, 5α, 6β] -6-amino-1-methyl-3-azabicyclo [3.2.0] heptan-3-yl) -1-cyclopropyl-6- Pyridone carboxylic acid compound and salt thereof characterized by being fluoro-1, 4-dihydro-4-oxo-1, 8-naphthyridine-3-carboxylic acid. 제1항에 있어서, 화합물은 8-클로로-1-시클로프로필-6-플루오로-7-([1α, 5α, 6β]-1-메틸-6-메틸아미노-3-아자비시클로 [3.2.0]헵탄-3-일)-1, 4-디히드로-4-옥소퀴놀린-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is 8-chloro-1-cyclopropyl-6-fluoro-7-([1α, 5α, 6β] -1-methyl-6-methylamino-3-azabicyclo [3.2.0 ] Heptan-3-yl) -1, 4-dihydro-4-oxoquinoline-3-carboxylic acid, and a pyridone carboxylic acid compound and its salt. 제1항에 있어서, 화합물은 1-시클로프로필-6, 8-디플루오로-7-([1α, 5α, 6β]-1-메틸-6-메틸아미노-3-아자비시클로 [3.2.0]헵탄-3-일)-1, 4-디히드로-4-옥소퀴놀린-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is 1-cyclopropyl-6, 8-difluoro-7-([1α, 5α, 6β] -1-methyl-6-methylamino-3-azabicyclo [3.2.0] Heptane-3-yl) -1, 4-dihydro-4-oxoquinoline-3-carboxylic acid, The pyridone carboxylic acid compound and its salt. 제1항에 있어서, 화합물은 1-시클로프로필-6-플루오로-7-([1α, 5α, 6β]-1-메틸-6-메틸아미노-3-아자비시클로 [3.2.0]헵탄-3-일)-1, 4-디히드로-4-옥소-1, 8-나프티리딘-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is 1-cyclopropyl-6-fluoro-7-([1α, 5α, 6β] -1-methyl-6-methylamino-3-azabicyclo [3.2.0] heptan-3 -Yl) -1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, and a pyridone carboxylic acid compound and salt thereof. 제1항에 있어서, 화합물은 7-([1α, 5α, 6β]-6-아미노-3-아자비시클로 [3.2.0]헵탄-3-일)-1-시클로프로필-6-플루오로-1, 4-디히드로-4-옥소-1, 8-나프티리딘-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is 7-([1α, 5α, 6β] -6-amino-3-azabicyclo [3.2.0] heptan-3-yl) -1-cyclopropyl-6-fluoro-1 And 4-dihydro-4-oxo-1, 8-naphthyridine-3-carboxylic acid. A pyridone carboxylic acid compound and salt thereof. 제1항에 있어서, 화합물은 7-([1α, 5α, 6β]-6-아미노-3-아자비시클로 [3.2.0]헵탄-3-일)-1-시클로프로필-6, 8-디플루오로-1, 4-디히드로-4-옥소퀴놀린-3-카르복실산인 것을 특징으로 하는 피리돈 카르본산 화합물과 그의 염.The compound of claim 1, wherein the compound is 7-([1α, 5α, 6β] -6-amino-3-azabicyclo [3.2.0] heptan-3-yl) -1-cyclopropyl-6, 8-difluoro Ryo-1, 4-dihydro-4-oxoquinoline-3-carboxylic acid, pyridone carboxylic acid compound and its salt. 다음 일반식(Ⅱ)로 표시되는 화합물과 다음 일반식(Ⅲ)으로 표시되는 화합물 또는 그의 산부가염과 불활성 유기용매 중에서 축합반응시키거나, R7이 저급 알킬인 경우 다음 일반식(Ⅱ)로 표시되는 화합물과 다음 일반식(Ⅲ)으로 표시되는 화합물 또는 그의 산부가염과 불활성 유기용매 중에서 축합반응시킨 후 가수분해시켜 다음 일반식(Ⅰ)로 표시되는 피리돈 카르본산 유도체를 제조하는 방법.Condensation reaction is carried out in a compound represented by the following general formula (II) and a compound represented by the following general formula (III) or an acid addition salt thereof and an inert organic solvent, or represented by the following general formula (II) when R 7 is lower alkyl. A method of preparing a pyridone carboxylic acid derivative represented by the following general formula (I) by condensation reaction of the compound represented by the following compound (III) or an acid addition salt thereof with an inert organic solvent and hydrolysis. 상기식에서, R1은 저급 알킬기, 할로겐 치환 저급 알킬기, 저급 알케닐기, 사이클로 알킬기 또는 치환되거나 치환되지 않은 페닐기를 의미하고, R2는 수소, 아미노기 또는 저급 알킬기를 의미하고, A는 질소원자 또는 C-X(여기서 X는 수소, 할로겐 원자 또는 알콕시기를 의미함)를 의미하며, R7은 수소 또는 저급 알킬기를 의미하며, Y는 할로겐 원자를 의미하며, Z는 다음식으로 표시되는 기를 나타낸다.Wherein R 1 means lower alkyl group, halogen substituted lower alkyl group, lower alkenyl group, cycloalkyl group or substituted or unsubstituted phenyl group, R 2 means hydrogen, amino group or lower alkyl group, A is nitrogen atom or CX (Where X means hydrogen, a halogen atom or an alkoxy group), R 7 means hydrogen or a lower alkyl group, Y means a halogen atom, and Z represents a group represented by the following formula. (여기서, R3, R4는 수소원자 또는 저급 알킬기를 의미하고, R5, R6는 수소, 히드록시, 알콕시, 아미노, 저급알킬기로 치환된 아미노기를 의미하는데 둘중 하나는 수소를 의미한다.)Wherein R 3 and R 4 refer to a hydrogen atom or a lower alkyl group, and R 5 and R 6 refer to an amino group substituted with hydrogen, hydroxy, alkoxy, amino or a lower alkyl group, one of which means hydrogen. ) 다음 일반식(Ⅰ)로 표시되는 피리돈 카르본산 유도체를 유효성분으로서 적어도 1종 이상 함유시켜서, 된 것임을 특징으로 하는 항균제 조성물.An antimicrobial composition comprising at least one pyridon carboxylic acid derivative represented by the following general formula (I) as an active ingredient. 상기식(Ⅰ)에서, R1은 저급 알킬기, 할로겐 치환 저급 알킬기, 저급 알케닐기, 사이클로 알킬기 또는 치환되거나 치환되지 않은 페닐기를 의미하고, R2는 수소, 아미노기 또는 저급 알킬기를 의미하고, A는 질소원자 또는 C-X(여기서 X는 수소, 할로겐 원자 또는 알콕시기를 의미함)를 의미하며, Z는 다음식으로 표시되는 기를 나타낸다.In formula (I), R 1 means lower alkyl group, halogen substituted lower alkyl group, lower alkenyl group, cycloalkyl group or substituted or unsubstituted phenyl group, R 2 means hydrogen, amino group or lower alkyl group, and A is A nitrogen atom or CX (where X means hydrogen, a halogen atom or an alkoxy group), and Z represents a group represented by the following formula. (여기서, R3, R4는 수소원자 또는 저급 알킬기를 의미하고, R5, R6는 수소, 히드록시, 알콕시, 아미노, 저급알킬기로 치환된 아미노기를 의미하는데 둘중 하나는 수소를 의미한다.)Wherein R 3 and R 4 refer to a hydrogen atom or a lower alkyl group, and R 5 and R 6 refer to an amino group substituted with hydrogen, hydroxy, alkoxy, amino or a lower alkyl group, one of which means hydrogen. ) 다음 일반식(Ⅲ)으로 표시되는 화합물.The compound represented by following General formula (III). 상기식(Ⅲ)에서, Z는 다음식으로 표시되는 기를 나타낸다.In the formula (III), Z represents a group represented by the following formula. (여기서, R3, R4는 수소원자 또는 저급 알킬기를 의미하고, R5, R6는 수소, 히드록시, 알콕시, 아미노, 저급알킬기로 치환된 아미노기를 의미하는데 둘중 하나는 수소를 의미한다.)(Wherein R 3 , R 4 means a hydrogen atom or a lower alkyl group, R 5 , R 6 means an amino group substituted with hydrogen, hydroxy, alkoxy, amino, lower alkyl group, one of which means hydrogen. ) ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
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