KR940005626A - 항생 화합물 - Google Patents

항생 화합물 Download PDF

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KR940005626A
KR940005626A KR1019930004664A KR930004664A KR940005626A KR 940005626 A KR940005626 A KR 940005626A KR 1019930004664 A KR1019930004664 A KR 1019930004664A KR 930004664 A KR930004664 A KR 930004664A KR 940005626 A KR940005626 A KR 940005626A
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methylcarbapenem
ylthio
hydroxyethyl
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프레데리끄 앙리 종
알렝 미쉘 베르뜨랑디
로날드 힐슨 벡 걸트
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수잔 제인 젠틀
제네카 리미티드
그레이엄 도날드 아놀드
제네카-파마 소시에떼아노님
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Abstract

본 발명은 하기 일반식(I)의 화합물 또는 이의 약학적으로 허용가능한 염 또는 이의 생체내 가수분해성 에스테르에 관한 것이다.
상기 식에서, R1은 1-히드록시에틸, 1-플루오로에틸 또는 히드록시메틸이고; R2는 수소 또는 Cl-4알킬이고; R3는 수소 또는 Cl-4알킬이고; P는 하기 일반식 (IA), (IB)또는 (IC)이며, 일반식(IB)에서의 나프틸기는 각 고리에서 결합되어 있는 카르바모일기의 질소에 결합될 수 있으며; Z는 카르복시, 설폰산, 설핀산, Cl-4알칸아 미도설포닐 (-SO2NHCOC1-3알킬), 벤즈아미도설포닐, Cl-4알킬설포닐카르바모일 (-CONHSO2Cl-4알킬), 페닐설포닐카르바모일, Cl-4알콕시카르바모일, 히드록시카르바모일, 설포아미노,Cl-4알칸설폰아미도, 시아노카르바모일, 시아노설파모일, 테트라졸-5-일, 3-히드록시이소옥사졸-4-일 및 3-히드록시이소옥사졸-5-일이며; P가 일반식(IA)또는 (IC)의 고리일때, Z는 카르복시가 아닐 경우에만 P는 임의로 치환된다. 또한, 본 발명의 화합물의 제조 방법, 이의 제조에서의 중간물질, 치료제로서의 이의 사용 및 이를 함유하는 약학적 조성물을 설명한다.

Description

항생 화합물
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. 하기 일반식(I)의 화합물 또는 이의 약학적으로 허용가능한 염 또는 이의 생체내 가수분해성 에스테르 :
    상기 식에서, R1은 1-히드록시에틸, 1-플루오로에틸 또는 히드록시메틸이고; R2는 수소 또는 Cl-4알킬이고; R3는 수소 또는 Cl-4알킬이고; P는 하기 일반식 (IA), (IB)또는 (IC)이며, 일반식(IB)에서의 나프틸기는 각 고리에서 결합되어 있는 카르바모일기의 질소에 결합될 수 있으며; Z는 카르복시, 설폰산, 설핀산, Cl-4알칸아 미도설포닐 (-SO2NHCOC1-3알킬), 벤즈아미도설포닐, Cl-4알킬설포닐카르바모일 (-CONHSO2Cl-4알킬), 페닐설포닐카르바모일, Cl-4알콕시카르바모일, 히드록시카르바모일, 설포아미노,Cl-4알칸설폰아미도, 시아노카르바모일, 시아노설파모일, 테트라졸-5-일, 3-히드록시이소옥사졸-4-일 및 3-히드록시이소옥사졸-5-일이며; P는 할로, 시아노, Cl-4알킬, 니트로, 히드록시, 카르복시, Cl-4알콕시, 트리플루오로메틸, Cl-4알콕시카르보닐, 아미노, Cl-4알킬아미노, 디-Cl-4알킬아미노, 설폰산, Cl-4알킬 S(O)n-(이때, n은 0-2이다), Cl-4알카노일아미노, Cl-4알카노일(Cl-4알킬)아미노, 카르바모일, Cl-4알킬카르바모일 및 디-Cl-4알킬카르바모일로부터 선택되는 하나 또는 두개의 치환체로 부가로 치환될 수 있으며; 단, p가 일반식(IA) 또는 (IC)의 고리이고, Z가 설폰산 또는Cl-4알칸설폰아미도일때, 상기 고리는 카르복시로 치환되지 않으며; P가 일반식(IA) 또는 (IC)의 고리일때, Z는 카르복시가 아니다;
  2. 제1항에 있어서, R1이 1-히드록시에틸이고, R2가 메틸인 화합물.
  3. 제1항 또는 제2항에 있어서, 하기 일반식(Ⅳ)인 화합물.
    상기 식에서, P, R3및 P상의 임의의 치환체는 제1항에서 정의된 바와같다.
  4. 제3항에 있어서, 고리 P상의 치환체 Z가 설폰산, 테트라졸-5-일, Cl-4알킬설포닐카르바모일 또는 시아노카르바모일인 화합물.
  5. 제3항에 있어서, 고리 P상의 임의의 치환체가 할로, 시아노, Cl-4알킬, 니트로, 히드록시, Cl-4알콕시, 카르바모일, 아미노 및 트리플루오로메틸로부터 선택된 화합물.
  6. 제1항에 있어서, 하기와 같은 화합물 및 이의 약학적으로 허용가능한 염 (1R, 5S, 6S, 8R. 2'S, 4'S)-2-(2-(3-설포페닐카르바모일)피롤리딘-4-일티오)-6- (1-히드록시에틸)-1-메틸카르바페넴-3-카르복실산; (1R, 5S, 6S, 8R, 2'S, 4'S)-2- (2-(3-메틸설포닐카르바모일페닐카르바모일)피롤리딘-4-일티오)-6-(1-히드톡시에틸)-1-메틸카르바페넴-3-카르복실산; (1R, 5S, 6S, 8R, 2'S, 4'S)-2-(2-(3-1H-테트라졸-5-일)페닐카르바모일)피롤리딘-4-일티오)-6-(1-히드록시에틸)-1-메틸카르바페넴-3-카르복실산; (1R, 5S, 6S, 8R, 2'S, 4'S)-2-(2-(2-히드록시-5-설포페닐카르바모일)피롤리딘-4-일티오)-6-(1-히드록시에틸)-1-메틸카르바페넴-3-카르복실산; (1R, 5S, 6S, 8R, 2'S, 4'S)-2-(2-(2-메록시-5-메틸--설포닐카르바모일)피롤리딘-4-일티오)-6-(1-히드록시에틸)-1-메틸카르바페넴-3-카르복실산; (1R, 5S, 6S, 8R, 2'S, 4'S)-2-(2-(3-페닐설포닐카르바모일페닐카르바모일)피롤리딘-4-일티오)-6-(1-히드록시에틸)-1-메틸카르바페넴-3-카르복실산, (1R, 5S, 6S, 8R, 2'S, 4'S)-2-(2-(2-메틸설포닐카르바모일-5-티에닐카르바모일)피롤리딘-4-일티오)-6-(1-히드록시에 틸)-1-메틸카르바페넴-3-카르복실산; (1R, 5S, 6S, 8R, 2'S, 4'S)-2-(2-(2-시아노카르바모일-5-티에닐카르바모일)피롤리딘-4-일티오)-6-(1-히드록시에틸)-1-메틸카르바페넴-3-카르복실산:(1R, 5S, 6S, 8R, 2'S, 4'S)-2-(2-(2-설포-5- 티에닐카르바모일)피롤리딘-4-일티오)-6-(1-히드록시에틸)-1-메틸카르바페넴-3-카르복실산;(1R, 5S, 6S, 8R, 2'S, 4'S)-2-(2-(1-카르복시-3-나프틸카르바모일)피롤리딘-4-일티오)-6-(1-히드록시에틸)-1-메틸카르바페넴-3-카르복실산; (1R, 5S, 6S, 8R, 2'S, 4'S)-2-(2-(2-카르복시-3-나프틸카르바모일)피롤리딘-4-일티오)-6-(1-히드록시에틸 )-1-메틸카르바페넴-3-카르복실산; (1R, 5S, 6S, 8R, 2'S, 4'S)-2-(2-(2-설포페닐카르바모일)피롤리딘-4-일티오)-6-(1-히드록시에틸)-1-메틸카르바페넴-3-카르복실산;또는 (1R, 5S, 6S, 8R, 2'S, 4'S)-(2-히드록시-4-설포-1-나프틸카르바모일)피롤리딘-4-일티오)-6-(1-히드록시에틸)-1-메틸카르바페넴-3-카르복실산.
  7. 제1항 내지 제6항중 어느 한 항에 따른 화합물 및 약제학적으로 허용가능한 담체를 포함하는 약학적 조성물.
  8. 하기 일반식(V)의 화합물을 탈보호시킨 후, 필요한 경우, (i)약학적으로 허용가능한 염을 형성시키고, (ii)이를 에스테르화시켜 생체내 가수분해성 에스테르를 형성시키는 것을 포함하는 화합물의 제조방법 :
    상기 식에서, R2는 제1항에서 정의된 바와같고; R10은 R3기(1항에서 정의된 바와같다) 또는 아미노 보호기이며; R13은 R1기(제1항에서 정의된 바와 같다), 보호된 히드록시메틸 또는 1-(보호된 히드록시)에틸기이며; R11은 수소 또는 카르복시 보호기이며; R12는 수소 또는 아미노 보호기이며; P1은 하기 일반식(ID), (IE) 또는 (IF)의 고리이며, 일반식(IE)에서의 나프틸기는 각 고리에서 결합되어 있는 카르바모일기의 질소에 결합될 수 있으며; R18은 Z기 또는 보호된 Z기이며, P1상의 임의의 치환체는 제1항에서 정의된 바와 같으며, 임의로 보호되며, 적어도 하나의 보호기가 존재한다 :
  9. 하기 (a)-(b)를 포함하고, 필요할 경우, (i)임의의 보호기의 제거; (ii)약학적으로 허용가능한 염의 형성; (iii)이를 에스테르화시킴으로써 생체내 가수분해성 에스테르를 형성시키는 제1항의 화합물 또는 제8항에서 정의된 바와같은 일반식(V)의 화합물의 제조방법: (a)하기 일반식(Ⅵ) 및 (Ⅶ)의 회합물을 반응시키거나; 또는 (b)하기 일반식(Ⅷ)화합물의 고리화 반응을 실시한다 :
    상기 식에서, P1, R2, R10, R11, R12및 R13은 제8항에서 정외된 바와같고; P1상의 임의의 치환체는 제8항에서 정의된 바와같고; L은 이탈기이며; R14, R15및 R16은 C1-6알콕시, 아릴옥시, 디-C1-6알킬아디노 및 디아릴아미노로부터 독립적으로 선택되며, R14-R16중의 임의의 두개는페닐렌디옥시를 나타내거나 또는 R14-R16중의 하나는 C1-4알킬, 아릴, 벤질 또는 페닐을 나타내며, 나머지 두개는 C1-4알킬, 트리플루오로메틸 또는 페닐을 나타내며 이때, 임의의 페닐기는 C1-3알킬 또는 C1-3알킬 또는 C1-3알콕시로 치환될 수 있으며; 임의의 작용기는 보호될 수 있다.
  10. 제8항의 일반식(Ⅳ)의 화합물, 제9항의 일반식(Ⅶ)또는 (Ⅷ)의 화합물 또는 하기 일반식(Ⅸ), (XⅡ) 또는 (XⅣ)의 화합물 :
    상기 식에서, P1, R2, R10-R13및 R17은 제8항에서 정의된 바와같고, R17은 보호기이다.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019930004664A 1992-03-26 1993-03-25 항생 화합물 KR100287040B1 (ko)

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HRP970281B1 (en) * 1996-05-28 2002-04-30 Merck & Co Inc Carbapenem antibiotic, composition and method of preparation
EP0923545A1 (en) 1996-08-17 1999-06-23 Zeneca Limited 3-mercaptopyrrolidines as farnesyl protein transferase inhibitors
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