KR960704892A - 3-Pyrrolidinylthio-carbapenem derivatives and their bactericidal activity (3-PYRROLIDINYLTHIO-CARBAPENEM DERIVATIVES AND THEIR ANTIMICROBIAL ACTIVITY) - Google Patents

3-Pyrrolidinylthio-carbapenem derivatives and their bactericidal activity (3-PYRROLIDINYLTHIO-CARBAPENEM DERIVATIVES AND THEIR ANTIMICROBIAL ACTIVITY)

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KR960704892A
KR960704892A KR1019960701945A KR19960701945A KR960704892A KR 960704892 A KR960704892 A KR 960704892A KR 1019960701945 A KR1019960701945 A KR 1019960701945A KR 19960701945 A KR19960701945 A KR 19960701945A KR 960704892 A KR960704892 A KR 960704892A
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methyl
hydroxymethyl
dimethyl
pyridinio
imidazolio
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KR100444563B1 (en
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마사요시 무라타
히데오 츠츠미
게이지 마츠다
고지 하토리
다카시 나카지마
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후지야마 아키라
후지사와 야쿠힝 고교 가부시키가이샤
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Abstract

본 발명은 살균제로 유용한 하기 일반식(I)의 화합물 및 이것의 약학적 허용염에 관한 것이다:The present invention relates to compounds of the general formula (I) and pharmaceutically acceptable salts thereof useful as fungicides:

상기 식에서, R1은 카르복시 등이고, R2는 하이드록시(저급)알킬 등이며, R3은 수소 또는 저급 알킬이고 R4는 2(또는 3)-메틸피리딘-4-일메틸 등이며, 및 R5는 수소 또는 이미노-보호기이다.Wherein R 1 is carboxy or the like, R 2 is hydroxy (lower) alkyl or the like, R 3 is hydrogen or lower alkyl and R 4 is 2 (or 3) -methylpyridin-4-ylmethyl or the like, and R 5 is hydrogen or an imino-protecting group.

Description

3-피롤로디닐티오-카르바페넴 유도체류 및 이것의 살균활성(3-PYRROLIDINYLTHIO-CARBAPENEM DERIVATIVES AND THEIR ANTIMICROBIAL ACTIVITY)3-Pyrrolidinylthio-carbapenem derivatives and their bactericidal activity (3-PYRROLIDINYLTHIO-CARBAPENEM DERIVATIVES AND THEIR ANTIMICROBIAL ACTIVITY)

내용없음No content

Claims (9)

하기 일반식(I)의 화합물 또는 이것의 약학적 허용염:A compound of formula (I) or a pharmaceutically acceptable salt thereof: 상기 식에서, R1은 카르복시, COO-또는 보호된 카르복시이고, R2는 하이드록시(저급)알킬 또는 보호된 하이드록시(저급)알킬이며, R3은 수소 또는 저급 알킬이고, R4는 2(또는 3)-메틸피리딘-4-일메틸, 2-시아노피리딘-4-일메틸, 2-카르바모일피리딘-4-일메틸, [1,2 (또는 1,3)-디메틸-4-피리디니오]메틸, (1-메틸-2-시아노-4-피리디니오)메틸, (1-메틸-2-카르바모일-4-피리디니오)메틸, [1-(2-보호된 하이드록시에틸)-4-피리디니오]메틸, [1-(2-하이드록시에틸)-4-피리디니오]메틸, [1-(2-카르바모일메틸)-4-피리디니오]메틸, [2-(하이드록시메틸)피리딘-4-일]메틸, [2-(하이드록시메틸)-1-메틸-4-피리디니오]메틸, 2-(이미다졸-1-일)프로필, 2-(1-메틸이미다졸-5-일)에틸, 2-(1,3-디메틸-4-이미다졸리오)에틸, 2-(3-디메틸-1-이미다졸리오)프로필, [1-메틸-2-(하이드록시메틸)이미다졸-5-일]메틸, (1-메틸-2-카르바모일이미다졸-5-일)메틸, [1,3-디메틸-2-(하이드록시메틸)-4-이미다졸리오]메틸, (1,3-디메틸-2-카르바모일-4-이미다졸리오)메틸, 2-(1-카르바모일메틸-3-메틸-4-이미다졸리오)에틸, [3-메틸-1-(2-하이드록시에틸)-4-이미다졸리오]메틸, [3-메틸-1-(카르바모일메틸)-4-이미다졸리오]메틸, [1-메틸-4-(하이드록시메틸-피라졸-5-일]메틸, [1-메틸-5-(하이드록시메틸)피라졸-3-일]메틸, [2-메틸-1-(카르바모일메틸)-3-피라졸리오]메틸, [1-(2-하이드록시메틸)피라졸-4-일]메틸, [2-메틸-1-(2-하이드록시에틸)-3-피라졸리오]메틸, [1,2-디메틸-4-(하이드록시메틸)-3-피라졸리오]메틸, [1,2-디메틸-5-(하이드록시메틸)-3-피라졸리오]메틸, [1-메틸-5-(하이드록시메틸)피라졸-4-일]메틸, [1,2-디메틸-3-(하이드록시메틸)-4-피라졸리오]메틸, [1-메틸-2-(카르바모일메틸)-4-피라졸리오]메틸, [1-메틸-2-(2-하이드록시메틸)-4-피라졸리오]메틸, 2-[2-(보호된 이미노)-3-메틸이미다졸린-1-일]에틸, 2-(2-이미노-3-메틸이미다졸린-1-일)에틸, (1-메틸-1,2,3-트리아졸-5-일)메틸, [1,3-디메틸-4-(1,2,3-트리아졸리오)]메틸 또는 6-(피라졸리디노[1,2-a]피라졸리오)메틸이며, 및 R5는 수소 또는 이미노-보호기이다.Wherein R 1 is carboxy, COO - or protected carboxy, R 2 is hydroxy (lower) alkyl or protected hydroxy (lower) alkyl, R 3 is hydrogen or lower alkyl and R4 is 2 (or 3) -methylpyridin-4-ylmethyl, 2-cyanopyridin-4-ylmethyl, 2-carbamoylpyridin-4-ylmethyl, [1,2 (or 1,3) -dimethyl-4-pyri Dini] methyl, (1-methyl-2-cyano-4-pyridinio) methyl, (1-methyl-2-carbamoyl-4-pyridinio) methyl, [1- (2-protected Hydroxyethyl) -4-pyridinio] methyl, [1- (2-hydroxyethyl) -4-pyridinio] methyl, [1- (2-carbamoylmethyl) -4-pyridinio] Methyl, [2- (hydroxymethyl) pyridin-4-yl] methyl, [2- (hydroxymethyl) -1-methyl-4-pyridinio] methyl, 2- (imidazol-1-yl) propyl , 2- (1-methylimidazol-5-yl) ethyl, 2- (1,3-dimethyl-4-imidazolio) ethyl, 2- (3-dimethyl-1-imidazolio) propyl , [1-methyl-2- (hydroxymethyl) imidazol-5-yl] Methyl, (1-methyl-2-carbamoylimidazol-5-yl) methyl, [1,3-dimethyl-2- (hydroxymethyl) -4-imidazolio] methyl, (1,3 -Dimethyl-2-carbamoyl-4-imidazolio) methyl, 2- (1-carbamoylmethyl-3-methyl-4-imidazolio) ethyl, [3-methyl-1- (2 -Hydroxyethyl) -4-imidazolio] methyl, [3-methyl-1- (carbamoylmethyl) -4-imidazolio] methyl, [1-methyl-4- (hydroxymethyl- Pyrazol-5-yl] methyl, [1-methyl-5- (hydroxymethyl) pyrazol-3-yl] methyl, [2-methyl-1- (carbamoylmethyl) -3-pyrazoloio] Methyl, [1- (2-hydroxymethyl) pyrazol-4-yl] methyl, [2-methyl-1- (2-hydroxyethyl) -3-pyrazolo] methyl, [1,2-dimethyl -4- (hydroxymethyl) -3-pyrazolo] methyl, [1,2-dimethyl-5- (hydroxymethyl) -3-pyrazolo] methyl, [1-methyl-5- (hydroxy Methyl) pyrazol-4-yl] methyl, [1,2-dimethyl-3- (hydroxymethyl) -4-pyrazolio] methyl, [1-methyl-2- (carbamoylmethyl) -4- Pirazolio ] Methyl, [1-methyl-2- (2-hydroxymethyl) -4-pyrazolio] methyl, 2- [2- (protected imino) -3-methylimidazolin-1-yl] ethyl , 2- (2-imino-3-methylimidazolin-1-yl) ethyl, (1-methyl-1,2,3-triazol-5-yl) methyl, [1,3-dimethyl-4 -(1,2,3-triaziolio) methyl or 6- (pyrazolidino [1,2-a] pyrazolo) methyl and R 5 is hydrogen or an imino-protecting group. 제1항에 있어서, R1이 카르복시, COO- 또는 에스테르화된 카르복시이고, R2가 하이드록시(저급)알킬, 아실옥시(저급)알킬 또는 트리(저급)알킬실릴옥시(저급)알킬이며, R4가 2(또는 3)-메틸피리딘-4-일메틸, 2-시아노피리딘-4-일메틸, 2-카르바모일피리딘-4-일메틸, [1,2 (또는 1,3)-디메틸-4-피리디니오]메틸, (1-메틸-2-시아노-4-피리디니오)메틸, (1-메틸-2-카르바모일-4-피리디니오)메틸, [1-(2-보호된 하이드록시에틸)-4-피리디니오]메틸 (상기 보호된 하이드록시는 아실옥시 또는 트리(저급)알킬실릴옥시임), [1-(2-하이드록시에틸)-4-피리디니오]메틸, [1-(2-카르바모일메틸)-4-피리디니오]메틸, [2-(하이드록시메틸)피리딘-4-일]메틸, [2-(하이드록시메틸)-1-메틸-4-피리디니오]메틸, 2-(이미다졸-1-일)프로필, 2-(1-메틸이미다졸-5-일)에틸, 2-(1,3-디메틸-4-이미다졸리오)에틸, 2-(3-디메틸-1-이미다졸리오)프로필, [1-메틸-2-(하이드록시메틸)이미다졸-5-일]메틸, (1-메틸-2-카르바모일이미다졸-5-일)메틸, [1,3-디메틸-2-(하이드록시메틸)-4-이미다졸리오]메틸, (1,3-디메틸-2-카르바모일-4-이미다졸리오)메틸, 2-(1-카르바모일메틸-3-메틸-4-이미다졸리오)에틸, [3-메틸-1-(2-하이드록시에틸)-4-이미다졸리오]메틸, [3-메틸-1-(카르바모일메틸)-4-이미다졸리오]메틸, [1-메틸-4-(하이드록시메틸-피라졸-5-일]메틸, [1-메틸-5-(하이드록시메틸)피라졸-3-일]메틸, [2-메틸-1-(카르바모일메틸)-3-피라졸리오]메틸, [1-(2-하이드록시메틸)피라졸-4-일]메틸, [2-메틸-1-(2-하이드록시에틸)-3-피라졸리오]메틸, [1,2-디메틸-4-(하이드록시메틸)-3-피라졸리오]메틸, [1,2-디메틸-5-(하이드록시메틸)-3-피라졸리오]메틸, [1-메틸-5-(하이드록시메틸)피라졸-4-일]메틸, [1,2-디메틸-3-(하이드록시메틸)-4-피라졸리오]메틸, [1-메틸-2-(카르바모일메틸)-4-피라졸리오]메틸, [1-메틸-2-(2-하이드록시메틸)-4-피라졸리오]메틸, 2-[2-(보호된 이미노)-3-메틸이미다졸린-1-일]에틸, 2-(2-이미노-3-메틸이미다졸린-1-일)에틸, (1-메틸-1,2,3-트리아졸-5-일)메틸, [1,3-디메틸-4-(1,2,3-트리아졸리오)]메틸 또는 6-(피라졸리디노[1,2-a]피라졸리오)메틸이며, 및 R5가 수소 또는 에스테르화된 카르복시인 화합물.The compound of claim 1, wherein R 1 is carboxy, COO- or esterified carboxy, R 2 is hydroxy (lower) alkyl, acyloxy (lower) alkyl or tri (lower) alkylsilyloxy (lower) alkyl, R4 is 2 (or 3) -methylpyridin-4-ylmethyl, 2-cyanopyridin-4-ylmethyl, 2-carbamoylpyridin-4-ylmethyl, [1,2 (or 1,3)- Dimethyl-4-pyridinio] methyl, (1-methyl-2-cyano-4-pyridinio) methyl, (1-methyl-2-carbamoyl-4-pyridinio) methyl, [1- (2-protected hydroxyethyl) -4-pyridinio] methyl (the protected hydroxy is acyloxy or tri (lower) alkylsilyloxy), [1- (2-hydroxyethyl) -4- Pyridinio] methyl, [1- (2-carbamoylmethyl) -4-pyridinio] methyl, [2- (hydroxymethyl) pyridin-4-yl] methyl, [2- (hydroxymethyl) -1-methyl-4-pyridinio] methyl, 2- (imidazol-1-yl) propyl, 2- (1-methylimidazol-5-yl) ethyl, 2- (1,3-dimethyl- 4-imidazolio) ethyl, 2- ( 3-dimethyl-1-imidazolio) propyl, [1-methyl-2- (hydroxymethyl) imidazol-5-yl] methyl, (1-methyl-2-carbamoylimidazole-5- Yl) methyl, [1,3-dimethyl-2- (hydroxymethyl) -4-imidazolio] methyl, (1,3-dimethyl-2-carbamoyl-4-imidazolio) methyl, 2- (1-carbamoylmethyl-3-methyl-4-imidazolio) ethyl, [3-methyl-1- (2-hydroxyethyl) -4-imidazolio] methyl, [3- Methyl-1- (carbamoylmethyl) -4-imidazolio] methyl, [1-methyl-4- (hydroxymethyl-pyrazol-5-yl] methyl, [1-methyl-5- (hydr Oxymethyl) pyrazol-3-yl] methyl, [2-methyl-1- (carbamoylmethyl) -3-pyrazolio] methyl, [1- (2-hydroxymethyl) pyrazol-4-yl ] Methyl, [2-methyl-1- (2-hydroxyethyl) -3-pyrazolo] methyl, [1,2-dimethyl-4- (hydroxymethyl) -3-pyrazolo] methyl, [ 1,2-dimethyl-5- (hydroxymethyl) -3-pyrazolo] methyl, [1-methyl-5- (hydroxymethyl) pyrazol-4-yl] methyl, [1,2-dimethyl- 3- (lower Hydroxymethyl) -4-pyrazolo] methyl, [1-methyl-2- (carbamoylmethyl) -4-pyrazoloio] methyl, [1-methyl-2- (2-hydroxymethyl)- 4-pyrazolio] methyl, 2- [2- (protected imino) -3-methylimidazolin-1-yl] ethyl, 2- (2-imino-3-methylimidazoline-1- Il) ethyl, (1-methyl-1,2,3-triazol-5-yl) methyl, [1,3-dimethyl-4- (1,2,3-triaziolio)] methyl or 6- ( Pyrazolidino [1,2-a] pyrazolio) methyl, and R5 is hydrogen or esterified carboxy. 제2항에 있어서, R1이 카르복시, COO- 또는 에스테르화된 카르복시이고, R2가 하이드록시(저급)에틸이며, R4가 2(또는 3)-메틸피리딘-4-일메틸, 2-시아노피리딘-4-일메틸, 2-카르바모일피리딘-4-일메틸, [1,2 (또는 1,3)-디메틸-4-피리디니오]메틸, (1-메틸-2-시아노-4-피리디니오)메틸, (1-메틸-2-카르바모일-4-피리디니오)메틸, [1-(2- 하이드록시에틸)-4-피리디니오]메틸 ,[1-(카르바모일메틸)-4-피리디니오]메틸,[2-(하이드록시메틸)피리딘-4-일]메틸, [2-(하이드록시메틸]-1-메틸-4-피리디니오]메틸, 2-(이미다졸-1-1일)프로필, 2-(1-메틸이미다졸-5-일)에틸, 2-(1,3-디메틸-4-이미다졸리오)에틸, 2-(3-메틸-1-이미다졸리오)프로필,[1-메틸-2-[하이드록시메틸]이미다졸-5-일]메틸, (1-메틸-2-카르바모일이미다졸-5-일)메틸, [1,3-디메틸-2-2(하이드록시메틸)-4-이미다졸리오]메릴, (1,3-디메릴-2-카르바모일-4-이미다졸리오)메틸, 2-(1-카르바모일메틸-3-메틸-4-이미다졸리오)에틸,[3-메틸-1-(2-하이드록시메틸)-4-이미다졸리오]메틸, [3-메틸-1-(카라바모일메틸)-4-이미다졸리오]메틸,[1-메틸-4-(하이들고시메틸)파라졸-5-일]메틸,[1-메틸-5-(하이드록시메틸)피라졸-3-일]메틸, [2-메틸-1-(카르바모일메틸)-3-피라졸리오]메틸, [1-(2-하이드록시에틸)피라졸-4-일]메틸, [2-메틸-1-(2-하이드록시메틸)-3-피라졸리오]메틸, [1,2-디메틸-4-(하이드록시메틸)-3-피라졸리오]메틸,[1,2-디메틸-5-(하이드록시메틸)-4-피라졸리오]메틸, [1-메틸-2-(카르바모일메틸)-4-피라졸리오]메틸, [1-메틸-2-(2 -하이드록시메틸)-4-피라졸리오]메틸, 2-[2-이미노-3-메틸-4-이미다졸린-1-일)에틸, (1-메틸-1H-1,2,3-트리아졸-5-일)메틸, [1,3-디메틸-4-(1H-1,2,3-트리아졸리오)]메틸 또는 6-(피라졸리디노[1,2-a]피라졸리오)메틸이며, 및 R5가 수소인 화합물.The compound of claim 2, wherein R 1 is carboxy, COO- or esterified carboxy, R 2 is hydroxy (lower) ethyl, R 4 is 2 (or 3) -methylpyridin-4-ylmethyl, 2- Cyanopyridin-4-ylmethyl, 2-carbamoylpyridin-4-ylmethyl, [1,2 (or 1,3) -dimethyl-4-pyridinio] methyl, (1-methyl-2-cya No-4-pyridinio) methyl, (1-methyl-2-carbamoyl-4-pyridinio) methyl, [1- (2-hydroxyethyl) -4-pyridinio] methyl, [1 -(Carbamoylmethyl) -4-pyridinio] methyl, [2- (hydroxymethyl) pyridin-4-yl] methyl, [2- (hydroxymethyl] -1-methyl-4-pyridinio ] Methyl, 2- (imidazol-1-1yl) propyl, 2- (1-methylimidazol-5-yl) ethyl, 2- (1,3-dimethyl-4-imidazolio) ethyl, 2- (3-methyl-1-imidazolio) propyl, [1-methyl-2- [hydroxymethyl] imidazol-5-yl] methyl, (1-methyl-2-carbamoylimidazole -5-yl) methyl, [1,3-dimethyl-2-2 (hydroxymethyl) -4-imidazolio] meryl, (1,3-dimethic 2-carbamoyl-4-imidazolio) methyl, 2- (1-carbamoylmethyl-3-methyl-4-imidazolio) ethyl, [3-methyl-1- (2-hydro Roxymethyl) -4-imidazolio] methyl, [3-methyl-1- (carbamoylmethyl) -4-imidazolio] methyl, [1-methyl-4- (hydigomethylmethyl) parasol -5-yl] methyl, [1-methyl-5- (hydroxymethyl) pyrazol-3-yl] methyl, [2-methyl-1- (carbamoylmethyl) -3-pyrazolio] methyl, [1- (2-hydroxyethyl) pyrazol-4-yl] methyl, [2-methyl-1- (2-hydroxymethyl) -3-pyrazolo] methyl, [1,2-dimethyl-4 -(Hydroxymethyl) -3-pyrazolio] methyl, [1,2-dimethyl-5- (hydroxymethyl) -4-pyrazolo] methyl, [1-methyl-2- (carbamoylmethyl ) -4-pyrazolio] methyl, [1-methyl-2- (2-hydroxymethyl) -4-pyrazolio] methyl, 2- [2-imino-3-methyl-4-imidazoline -1-yl) ethyl, (1-methyl-1H-1,2,3-triazol-5-yl) methyl, [1,3-dimethyl-4- (1H-1,2,3-triaziolio )] Methyl or 6- (pyrazolidino [1,2-a] pyrazole O) it is methyl, and R 5 is a hydrogen. (a) 하기 일반식(II)의 화합물 또는 이것의 옥소기에서의 반응성 유도체 또는 이것의 염을 하기 일반식(Ⅲ)의 화합물 또는 이것의 염과 반응시켜 하기 일반식(I)의 화합물 또는 이것의 염을 수득하거나; (b) 하기 일반식(I-a)의 화합물 또는 이것의 염으로부터 Ra1의 카르복시-보호기를 제거 반응시켜 하기 일반식(I-b)의 화합물 또는 이것의 염을 수득하거나; (c) 하기 일반식(I-c)의 화합물 또는 이것의 염으로부터 Ra5의 이미노-보호기를 제거 반응시켜 하기 일반식(I-d)의 화합물 또는 이것의 염을 수득하거나; (d) 하기 일반식(I-e)의 화합물 또는 이것의 염을 하기 일반식(Ⅳ)의 화합물과 반응시켜 하기 일반식(I-f)의 화합물 또는 이것의 염을 수득하거나; (e) 하기 일반식(I-g)의 화합물로부터 Rb4의 하이드록시-보호기를 제거반응시켜 하기 일반식(I-h)의 화합물 또는 이것의 염을 수득하거나; (f) 하기 일반식(I-i)의 화합물 또는 이것의 염을 산무수물과 반응시켜 하기 일반식(I-j)의 화합물 또는 이것의 염을 수득하거나; 또는 (g) 하기 일반식(I-k)의 화합물 또는 이것의 염으로부터 Ra2의 하이드록시-보호기를 제거 반응시켜 하기 일반식(I-l)의 화합물 또는 이것의 염을 수득하여, 하기 일반식(I)의 화합물 또는 이것의 염을 제조하는 방법:(a) A compound of the following general formula (I) or a compound of formula (II) or a reactive derivative thereof or an salt thereof in an oxo group thereof by reacting with a compound of the following general formula (III) or a salt thereof To obtain a salt of; (b) removing the carboxy-protecting group of Ra 1 from the compound of formula (Ia) or a salt thereof to obtain a compound of formula (Ib) or a salt thereof; (c) removing the imino-protecting group of Ra 5 from the compound of formula (Ic) or a salt thereof to obtain a compound of formula (Id) or a salt thereof; (d) reacting a compound of formula (Ie) or a salt thereof with a compound of formula (IV) to yield a compound of formula (If) or a salt thereof; (e) removing the hydroxy-protecting group of Rb 4 from the compound of formula (Ig) to obtain a compound of formula (Ih) or a salt thereof; (f) reacting a compound of formula (Ii) or a salt thereof with an acid anhydride to yield a compound of formula (Ij) or a salt thereof; Or (g) removing the hydroxy-protecting group of Ra 2 from the compound of the following general formula (Ik) or a salt thereof to obtain a compound of the following general formula (Il) or a salt thereof, and the following general formula (I) Process for the preparation of compounds of or salts thereof: 상기 식에서, R1, R2, R3, R4및 R5는 각각 제1항에서 정의한 바와 같고, Ra1은 보호된 카르복시이며, Ra2는 보호된 하이드록시(저급)알킬이고, Rb2는 하이드록시(저급)알킬이며, Ra4는 2(또는 3)-메틸피리딘-4-일메틸, 2-시아노피리딘-4-일메틸, 2-카르바모일피리딘-4-일메틸, [1,2 (또는 1,3)-디메틸-4-피리디니오]메틸, (1-메틸-2-시아노-4-피리디니오)메틸, (1-메틸-2-카르바모일-4-피리디니오)메틸, [1-(2-보호된 하이드록시에틸)-4-피리디니오]메틸 (상기 보호된 하이드록시는 아실옥시 또는 트리(저급)알킬실릴옥시임), [1-(2-하이드록시에틸)-4-피리디니오]메틸, [1-(2-카르바모일메틸)-4-피리디니오]메틸, [2-(하이드록시메틸)피리딘-4-일]메틸, [2-(하이드록시메틸)-1-메틸-4-피리디니오]메틸, 2-(이미다졸-1-일)프로필, 2-(1-메틸이미다졸-5-일)에틸, 2-(1,3-디메틸-4-이미다졸리오)에틸, 2-(3-디메틸-1-이미다졸리오)프로필, [1-메틸-2-(하이드록시메틸)이미다졸-5-일]메틸, (1-메틸-2-카르바모일이미다졸-5-일)메틸, [1,3-디메틸-2-(하이드록시메틸)-4-이미다졸리오]메틸, (1,3-디메틸-2-카르바모일-4-이미다졸리오)메틸, 2-(1-카르바모일메틸-3-메틸-4-이미다졸리오)에틸, [3-메틸-1-(2-하이드록시에틸)-4-이미다졸리오]메틸, [3-메틸-1-(카르바모일메틸)-4-이미다졸리오]메틸, [1-메틸-4-(하이드록시메틸-피라졸-5-일]메틸, [1-메틸-5-(하이드록시메틸)피라졸-3-일]메틸, [2-메틸-1-(카르바모일메틸)-3-피라졸리오]메틸, [1-(2-하이드록시메틸)피라졸-4-일]메틸, [2-메틸-1-(2-하이드록시에틸)-3-피라졸리오]메틸, [1,2-디메틸-4-(하이드록시메틸)-3-피라졸리오]메틸, [1,2-디메틸-5-(하이드록시메틸)-3-피라졸리오]메틸, [1,2-디메틸-3-(하이드록시메틸)-4-피라졸리오]메틸, [1-메틸-2-(카르바모일메틸)-4-피라졸리오]메틸, [1-메틸-2-(2-하이드록시메틸)-4-피라졸리오]메틸 또는 [1,3-디메틸-4-{1H-1,2,3-트리아졸리오)]메틸이며, Rb4는 [1-(2-보호된 하이드록시에틸)-4-피리디니오]메틸 또는 2-(2-보호된 이미노-3-메틸이미다졸린-1-일)에틸이고, Rc4는 [1-(2-하이드록시에틸)-4-피리디니오]메틸 또는 2-(2-이미노-3-메틸이미다졸린-1-일)에틸이며, Ra5는 이미노-보호기이고, R6은 메틸, 카르바모일메틸, 2-하이드록시에틸 또는 2-보호된 하이드록시에틸이며, 및 X-는 산 잔기이다.Wherein R 1 , R 2 , R 3 , R 4 and R 5 are each as defined in claim 1 , Ra 1 is a protected carboxy, Ra 2 is a protected hydroxy (lower) alkyl, Rb 2 Is hydroxy (lower) alkyl, Ra 4 is 2 (or 3) -methylpyridin-4-ylmethyl, 2-cyanopyridin-4-ylmethyl, 2-carbamoylpyridin-4-ylmethyl, [ 1,2 (or 1,3) -dimethyl-4-pyridinio] methyl, (1-methyl-2-cyano-4-pyridinio) methyl, (1-methyl-2-carbamoyl-4 -Pyridinio) methyl, [1- (2-protected hydroxyethyl) -4-pyridinio] methyl (where the protected hydroxy is acyloxy or tri (lower) alkylsilyloxy), [1- (2-hydroxyethyl) -4-pyridinio] methyl, [1- (2-carbamoylmethyl) -4-pyridinio] methyl, [2- (hydroxymethyl) pyridin-4-yl] Methyl, [2- (hydroxymethyl) -1-methyl-4-pyridinio] methyl, 2- (imidazol-1-yl) propyl, 2- (1-methylimidazol-5-yl) ethyl , 2- (1,3-dimethyl-4-imida Lio) ethyl, 2- (3-dimethyl-1-imidazolio) propyl, [1-methyl-2- (hydroxymethyl) imidazol-5-yl] methyl, (1-methyl-2-carba Moylimidazol-5-yl) methyl, [1,3-dimethyl-2- (hydroxymethyl) -4-imidazolio] methyl, (1,3-dimethyl-2-carbamoyl-4- Imidazolio) methyl, 2- (1-carbamoylmethyl-3-methyl-4-imidazolio) ethyl, [3-methyl-1- (2-hydroxyethyl) -4-imidazoli O] methyl, [3-methyl-1- (carbamoylmethyl) -4-imidazolio] methyl, [1-methyl-4- (hydroxymethyl-pyrazol-5-yl] methyl, [1 -Methyl-5- (hydroxymethyl) pyrazol-3-yl] methyl, [2-methyl-1- (carbamoylmethyl) -3-pyrazoloio] methyl, [1- (2-hydroxymethyl ) Pyrazol-4-yl] methyl, [2-methyl-1- (2-hydroxyethyl) -3-pyrazolio] methyl, [1,2-dimethyl-4- (hydroxymethyl) -3- Pyrazolio] methyl, [1,2-dimethyl-5- (hydroxymethyl) -3-pyrazolio] methyl, [1,2-dimethyl-3- (hydroxymethyl) -4-pyrazolorio] Methyl, [1-methyl-2- (carbamoylmethyl) -4-pyrazolio] methyl, [1-methyl-2- (2-hydroxymethyl) -4-pyrazolo] methyl or [1, 3-dimethyl-4- {1H-1,2,3-triazio)] methyl and Rb4 is [1- (2-protected hydroxyethyl) -4-pyridinio] methyl or 2- (2 Protected imino-3-methylimidazolin-1-yl) ethyl and Rc4 is [1- (2-hydroxyethyl) -4-pyridinio] methyl or 2- (2-imino-3 -Methylimidazolin-1-yl) ethyl, Ra 5 is an imino-protecting group, R 6 is methyl, carbamoylmethyl, 2-hydroxyethyl or 2-protected hydroxyethyl, and X- Is an acid residue. 활성 성분으로서 제1항의 화합물을 약학적 허용담체 또는 부형제와의 혼합물 형태로 포함하는 약학조성물.A pharmaceutical composition comprising the compound of claim 1 as an active ingredient in the form of a mixture with a pharmaceutically acceptable carrier or excipient. 감염성 질환의 치료용 약제의 제조에 제1항의 화합물을 사용하는 방법.A method of using the compound of claim 1 in the manufacture of a medicament for the treatment of an infectious disease. 제1항의 화합물을 인체 또는 동물에게 투여하는 것을 포함하는 감염성 질환의 치료방법.A method of treating an infectious disease comprising administering a compound of claim 1 to a human or animal. 제1항의 화합물을 살균제로 사용하는 방법.A method of using the compound of claim 1 as a fungicide. 약제로 사용하기 위한 제1항의 화합물.The compound of claim 1 for use as a medicament. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019960071945A 1993-10-08 1996-04-08 2-axis actuator and optical disk device KR100444563B1 (en)

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JP1995-354198 1995-12-27

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KR100473365B1 (en) * 2002-10-18 2005-03-10 주식회사 하원제약 1b-methylcarbapenem derivative having pyrrolidine derivative with oxadiazole moiety and method for preparation of the same

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