KR900018099A - 3-피롤리디닐 티오 1-아자바이시클로[3.2.0]-헵트-2-엔-2-카르복실산 화합물 - Google Patents

3-피롤리디닐 티오 1-아자바이시클로[3.2.0]-헵트-2-엔-2-카르복실산 화합물 Download PDF

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KR900018099A
KR900018099A KR1019890006945A KR890006945A KR900018099A KR 900018099 A KR900018099 A KR 900018099A KR 1019890006945 A KR1019890006945 A KR 1019890006945A KR 890006945 A KR890006945 A KR 890006945A KR 900018099 A KR900018099 A KR 900018099A
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마사요시 무라다
히데오 츄츄미
게이지 마쯔다
고지 하도리
다가시 나가지마
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후지사와 도모기찌로
후지사와 야쿠힌 고오교오 가부시기가이샤
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Abstract

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Description

3-피롤리디닐티오-1-아자비시클로[3,2,0]-헵트-2-카르복실산 화합물
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Claims (14)

  1. 하기 식의 화합물과 그것의 약제학적 허용염.
    상기식에서, R1은 카르복시 또는 보호된 카르복시, R2는 히드록시(저급)알킬 또는 보호된 히드록시(저급)알킬, R3는 수소 또는 저급알킬, R4는 적절한 치환체(들)로 치환될수 있는 불포화 헤테로시클릭기, R5는 수소, 저급알칸이미도일 또는 이미노-보호성기이며, A는 저급알킬렌이다.
  2. 제1항에 있어서, R4는 1내지 4개 질소원자를 포함하는 불포화된 5또는 6-탄소원자 고리의 헤테로모노시클릭기, 1내지 2개 산소원자의 1내지 3개 질소원자를 포함하는 불포화된 5또는 6-탄소원자 고리의 헤테로모노시클릭기, 1내지 2개 산소원자의 1내지 3개 질소원자를 포함하는 불포화된 5또는 6-탄소원자 고리의 헤테로모노시클릭기, 또는 하나의 황원자를 포함하는 불포화된 5또는 6-탄소원자 고리의 헤테로모노시클릭기이며, 상기 헤테로시클릭기는, 옥소, 카르복시(저급)알킬, 보호된 카르복시(저급)알킬, 보호된 아미노, 저급 아릴 아미노, 우레이도(저급)알킬, 카르바모일, 카르바모일(저급)알킬, 저급알킬, 저급 알카노일(저급)알킬, 보호된 아미노(저급)알킬, 히드록시(저급)알킬, 보호된 히드록시(저급)알킬, 아지도(저급)알킬, 보킬과 아미노-보호성기로 부터 선택된 적합한 1 내지 3개 치환체로 치환될수 있는 화합물.
  3. 제2항에 있어서, R4가 피롤릴, 피롤리놀, 이미다졸릴, 이미다졸리닐, 피라졸릴, 피라졸리닐, 피리딜, 피리딜 N-옥시드, 피리디니오, 디히드로피리딜, 테트라히드로피리딜, 피리미디닐, 피리미디니오, 피라지닐, 피라지니오, 피리다지닐, 피리다지니오, 트리아지닐, 테트라히드로 트리아지닐, 트리아지니오, 트리아졸릴, 트리아졸리오, 테트라지닐, 테트라자니오, 테트라졸릴 또는 테트라졸리오이며, 그 헤테로시클릭시기는 옥소, 카르복시(저급)알킬, 카르보닐(저급)알킬, 저급 알카노일(저급)알킬과 아실로 부터 선택되는 1 내지 3개의 적합한 치환체들로 치환될 수 있는 화합물.
  4. 제3항에 있어서, R1이 카르복시이또는 에스테르화된 카르복시이며, R5가 수소, 저급 알칸이미도일 또는 아닐인 화합물.
  5. 제3항에 있어서, R1은 카르복시이고,저급 알케닐옥시카르보닐 또는 페닐(똔는 니트로페닐)(저급)알콕시 카르보닐, R2가 히드록시(저급)알킬,[페닐(저급 니트로페닐)(저급)알콕시]카르보닐옥시(저급)알킬 또는 [투라(저급)알킬실릴]옥시(저급)알킬이며, R4가 이미다졸릴, 피라졸릴 또는 이미다졸리닐이며, 상기 헤테로시클릭기는 옥소, 카르복시(저급)알킬, 저급 알케닐옥시카르보닐(저급)알킬, 페닐(또는 니트로 페닐)(저급)알콕시 카르보닐(저급)알킬, 카르바모일(저급)알킬, 저급 알카노일(저급)알킬, 저급 알케닐 옥시카르보닐 또는 페닐(또는 니트로페닐)(저급)알콕시 카르보닐이며, R5가 수소, 저급 알칸임도일, 저급 알케닐옥시카르보닐, 또는 페닐(또는 니트로페닐)(저급)알콕시카르보닐인 화합물.
  6. 제5항에 있어서, R1이 카르복시, R2가 히드록시(저급)알킬, R3가 저급 알킬, R4가 이미다졸릴, 피라졸릴, 이미다졸릴 또는 옥소 이미다졸리닐, R5가 수소 또는 저급 알칸이미도일이며, A가 저급 알킬렌인 화합물.
  7. 제6항에 있어서, R2는 히드록시(C1-C4)알킬, R3C1-C4알킬, R4가 이미다졸릴, 피라졸릴, 이미다졸린-1-일 또는 2-옥소이미다졸린-1-일, R5는 수소 또는 C1-C4알킨이미도일이며, A는 C1-C4알킬렌인 화합물.
  8. 제7항에 있어서, R2가 1-히드록시, R3는 메틸, R4가 이미다졸-1-일, 피라졸-1-일, 이미다졸린-1-일 또는 2-옥소이미다졸린-1-일, R5는 수소 또는 포름이미도일이며, A는 메틸렌인 화합물.
  9. 제7항에 있어서, (4R,5S,6S)-6-[(1R)-1-히드록시에틸]-3-[(2S,4S)-2-(이미다졸-1-일)메틸피롤리딘-4-일]티오-4-메틸-7-옥소-1-아자비시클로[3,2,0]헵트-2-엔-2-카르복실산, (4R,5S,6S)-6-[(1R)-1-히드록시에틸]-4-메틸-3-[(2S,4S)-2-(3-메틸-1-이미다졸리오)메틸피롤리딘-4-일]티오-4-메틸-7-옥소-1-아자비시클로[3,2,0]헵트-2-엔-2-카르복실레이트,(4R,5S,6S)-3-[(2S,4S)-2-(3-카르바모일메틸-1-이미다졸리오)메틸피롤리딘-4-일]티오-6-[(1R)-1-피드록시에틸]-4-메틸-7-옥소-1-아자비시클로[3,2,0]헵트-2-엔-2-카르복실레이트, (4R,5S,6S)-3-[(2S,4S)-2-(3-아세토닐-1-이미다졸리오)메틸피롤리딘-4-일]티오-6-[(1R)-1-피드록시에틸]-4-메틸-7-옥소-1-아자비시클로[3,2,0]헵트-2-엔-2-카르복실레이트, (4R,5S,6S)-3-[(2S,4S)-2-(3-카르바모일메틸-1-이미다졸리오)메틸피롤리딘-4-일]티오-6-[(1R)-1-피드록시에틸]-4-메틸-7-옥소-1-아자비시클로[3,2,0]헵트-2-엔-2-카르복산 아이오다이드이트, (4R,5S,6S)-6-[(1R)-1-히드록시에틸]-4-에틸-3-[(2S,4S)-2-(3-메틸-1-이미다졸리오)메틸피롤리딘-4-일]티오-7-옥소-1-아자비시클로[3,2,0]헵트-2-엔-2-카르복실산 아이오다이드, 이트, (4R,5S,6S)-6-[(1R)-1-히드록시에틸]-4-에틸-3-[(2S,4S)-2-(3-메틸-1-이미다졸리오)메틸피롤리딘-4-일]티오-7-옥소-1-아자비시클로[3,2,0]헵트-2-엔-2-카르복실산 클라이드 또는 (4R,5S,6S)-6-[(1R)-1-히드록시에틸]-4-틸-1-이미다졸리오)메틸피롤리딘-4-일]티오-7-옥소-1-아자비시클로[3,2,0]헵트-2-엔-2-카르복실산 클로라이드의 화합물.
  10. (a)하기식(Ⅱ)의 화합물 또는 그것의 옥소기에 반응성 있는 유도체 또는 그들의 염을 하기식(Ⅲ)의 화합물 또는 그것의 염과 반응시켜서, 하기식(Ⅰ)의 화합물 또는 그들의 염을 산출하며, (b)하기식(Ⅰ-a)의 화합물 또는 그들의 염을 Ra1상의 카르복시 보호성기 제거반응을 실시하여 하기식(Ⅰ-b)의 화합물 또는 그들의 염을 산출하고, (c)하기식(Ⅰ-c)의 화합물 또는 그들의 염을 Ra5의 이미노 보호성기 제거반응을 실시하여 하기식(Ⅰ-d)의 화합물 또는 그들의 염을 얻고, (d)하기식(Ⅰ-e)의 화합물 또는 그들의 염을 Ra2상의 히드록시 보호성기 제거반응을 실시 하여 하기식(Ⅰ-f)의 화합물 또는 그들의 염을 제조하며, (e)하기식(Ⅰ-f)의 화합물 또는 그들의 염을 식 R6-x로 표시되는 화합물과 반응시켜 하기식(Ⅰ-h)의 화합물 또는 그들의 염을 산출하고, (f)하기식(Ⅰ-d)의 화합물 또는 그들의 염을 저급 알칸 이미도일화제와 반응시켜 하기식(Ⅰ-i)의 화합물 또는 그들의 염을 산출하는 것으로 구서된 하기식(Ⅰ)의 화합물 또는 그들의 염의 제조방법.
    상기식에서 R1은 카르복시 또는 보호된 카르복시, R2는 히드록시(저급)알킬, R3는 수소 또는 저급알킬, R4는 적절한 치환테로 치환될수 있는 불포화된 헤테로 시클릭기, R5는 수소, 저급알칸 이미도일 또는 아미노 보호성기, A는 저급 아킬렌, Ra1은 보호된 카르복시, Ra5는 이미노-보호성기, Ra2는 보호된 히드록시(저급)아킬, Rb2는 히드록시(저급)알킬, Ra4는 적합한 치환체로 치환될수 있는 삼차 질소원자를 포함한 불포화된 헤테로시클릭기, R6은 카르복시와 아실로 구성되는 기로 임의로 치환된 저급알킬, X는 산잔기, Ra4는 적합한 치환체로 치환될수 있는, 사차 질소원자가 함유된 불포화된 헤테로시클릭기, Ra5는 저급 알칸이미도일이다.
  11. 활성성분으로 제1항의 화합물을 약제학적 허용 담체 또는 부형제와의 혼합물 상태로 함유하고 있는 약학적 조성물.
  12. 인체 또는 동물에, 감염성 질병의 치료를 위한 약제 제조시 제1항의 화합물을 사용하는 방법.
  13. 인체 또는 동물에 제1항의 화합물을 투여함으로써 감염성 질화를 치료하는 방법
  14. 항균제로서 제1항의 화합물을 사용하는 방법.
    ※ 참고사항 : 최초출원내용에 의하여 공개하는 것임.
KR1019890006945A 1988-05-23 1989-05-22 3-피롤리디닐 티오 1-아자바이시클로[3.2.0]-헵트-2-엔-2-카르복실산 화합물 KR900018099A (ko)

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