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KR840007001A - 이미다조[1,5-a] 피리딘 유도체의 제조방법 - Google Patents

이미다조[1,5-a] 피리딘 유도체의 제조방법 Download PDF

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KR840007001A
KR840007001A KR1019830006030A KR830006030A KR840007001A KR 840007001 A KR840007001 A KR 840007001A KR 1019830006030 A KR1019830006030 A KR 1019830006030A KR 830006030 A KR830006030 A KR 830006030A KR 840007001 A KR840007001 A KR 840007001A
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phenylene
alkylene
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제이. 브라운 레슬리
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아놀드 자일러, 에른스트 알테르
시바-가이기 에이지
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Abstract

내용 없음

Description

이미다조〔1,5-a〕피리딘 유도체의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (7)

  1. a) 일반식(Ⅳ)의 화합물을 폐환시켜 일반식(Ⅰa)의 화합물을 수득하고, 생성된 c′가 c가 아닌 화합물을 일반식(Ⅰ)화합물로 전환시키거나,
    b) A가 에테닐렌 또는 저급알킬로 치환된 에테닐렌을 나타내는 일반식(Ⅰ)의 화합물을 제조하기 위해 일반식(Ⅶ)화합물을 일반식(Ⅷ)의 화합물과 축합시키고, 생성된 c′가 c가 아닌 화합물을 일반식(Ⅰ)의 화합물로 전환시키거나,
    c) A가 직접결합을 나타내고 B가 저급 알킬렌페닐렌 저급알킬렌, 저급알킬렌페닐렌, 저급알킬렌-(티오 또는 옥시)-저급알킬렌, 저급알킬렌-(티오 또는 옥시)-페닐렌, 저급알킬렌페닐렌-저급알케닐렌 또는 저급알키디 에닐렌을 나타내는 일반식(Ⅰ)의 화합물을 제조하기 위해, 일반식 (Ⅸ)의 화합물을 일반식(Ⅹ)의 반응성 기능유도체와 축합시키고, 생성된 일반식(Ⅰb)의 화합물(c′는 c가 아님)을 일반식(Ⅰ)의 화합물로 전환시키거나,
    d) B가 저급알킬렌-(티오 또는 옥시)-페닐렌, 페닐렌-(티오 또는 옥시)-저급알킬렌 또는 저급알킬렌-(티오 또는 옥시)-저급알킬렌을 나타내는 일반식(Ⅰ)의 화합물을 제조하기 위해, B가 저급알킬렌 또는 페닐렌을 나타내고 c′가 반응성의 기능적으로 변형된 하이드록시 메틸을 나타내는 일반식(Ⅰa)에 상응하는 중간체를 저급알칸티올 또는 저급알칸티올과 또는 c 또는 c′에 의해 적절히 치환된 페놀 또는 티오페놀과 축합시키고 생성된 c′가 c가 아닌 화합물을 일반식(Ⅰ)의 화합물로 전환시키고, 경우에 따라 생성된 일반식(Ⅰ)의 화합물을 본 발명의 다른 화합물로 전환시키고/시키거나, 경우에 따라 생성된 유리화합물을 염으로 또는 생성된 염을 유리화합물 또는 다른 염으로 전환시키고, 경우에 따라 생성된 이성체 또는 라세메이트의 혼합물을 단일이성체 또는 라세메이트로 분할하며, 경우에 따라 생성된 라세메이트를 광학적 대장체로 분할함을 특징으로 하여 일반식(Ⅰ)의 이미다조〔1, 5-a〕 피리딘 유도체, 그의 5, 6, 7, 8-테트라하이드로 유도체 또는 그의 염을 제조하는 방법.
    상기식에서
    R1은 수소, 할로겐, 저급알킬, 저급알콕시, 하이드록시 또는 아릴-저급알콕시(이때 아릴은 페닐, 또는 저급알콕시, 저급알킬, 할로겐 또는 트리플루오로-메틸로 일 또는 이 치환된 페닐을 나타냄)이고 ;
    R2는 수소, 할로겐, 또는 저급알킬을 나타내며 ;
    C는 카복시, 저급알콕시카보닐, 비치환된 또는 일 또는 이-(저급알킬)치환된 카바모일, 시아노, 포르밀 하이드록시메틸, 5-테트라졸릴, 4, 5-디히드로-2-옥사졸릴, 저급알킬로 치환된 4, 5-디하이드로-2-옥사졸릴 또는 하이드록시카바모일을 나타내고 ;
    a) A는 에테닐렌(비닐렌) 또는 저급알킬로 치환된 에테닐렌(비닐렌)을 나타내고,
    B는 탄소수 1내지 12의 알킬렌, 탄소수 각기 2내지 12의 알키닐렌 또는 알케닐렌, 페닐렌-저급알킬렌, 페닐렌, 저급알케닐렌페닐렌, 페닐렌-(티오 또는 옥시)-저급알킬렌을 나타내거나 ;
    b) A는 직접결합을 나타내고
    B는 저급알킬렌-페닐렌, 페닐렌 저급알킬렌, 페닐렌, 저급알킬렌-(티오 또는 옥시)-저급알킬렌, 저급알킬렌-(티오 또는 옥시)-페닐렌, 페닐렌-(티오 또는 옥시)-저급알킬렌, 페닐렌 저급알케닐렌, 저급알킬렌페닐렌 저급알케닐렌 또는 탄소수 5내지 12의 알카디에닐렌을 나타내며,
    R2′ 및 R2″는 수소 또는 저급알킬을 나타내고 ; 일반식(Ⅳ) 및 (Ⅰa)중 C′는 카복시, 저급알콕시카보닐, 비치환된 또는 일-또는 이-(저급알킬)치한된 카바모일, 시아노, 하이드록시메틸, 저급알카노일옥시메틸, 에테르화된 하이드록시메틸, 할로메틸, 5-테트라졸릴, 4, 5-디하이드로-2-옥사졸릴, 저급알킬로 치환된 4, 5-디하이드로-2옥사졸릴, 하이드록시카바모일, 할로, 저급알킬렌 옥시디메틸을 나타내고 ;
    R3는 수소 또는 저급알킬을 나타내며 ;
    R4는 수소 또는 저급알킬을 나타내며 ;
    R5는 디-저급알킬포스포노 또는 트리아릴포스포라닐을 나타내며 ;
    일반식(Ⅷ)중 C′는 카복시, 저급알콕시카보닐, 카바모일, 일- 또는 이-(저급알킬)치환된 카바모일, 시아노, 할로메틸, 저급 알카노일옥시메틸, 에테르화된 하이드록시메틸, 5-테트라졸릴, 4, 5-디하이드로-2-옥사졸릴, 저급알킬로 치환된 4, 5-디하이드로-2-옥사졸릴, 또는 하이드록시카바모일을 나타내고 ;
    M은 알카리금속이고 ;
    일반식(Ⅸ)중 R1및 R2는 수소 또는 저급알킬을 나타내고 ;
    B′는 저급 알킬렌페닐렌 저급알킬렌, 저급알킬렌페닐렌, 저급알킬렌-(티오 또는 옥시)-저급알킬렌, 저급알킬렌-(티오 또는 옥시)-페닐렌, 저급알킬렌 페닐렌저급알케닐렌, 또는 저급알카디에닐렌을 나타내며 ;
    일반식(Ⅹ) 및 (Ⅰb)중 C′는 카복시, 트리알콕시메틸, 비치환된 또는 일 -또는 이-(저급알킬) 치환된 카바모일, 시아노, 저급알카노일옥시메틸, 에테르화 하이드록시메틸, 할로메틸 4, 5-디하이드로-2-옥사졸릴 또는 저급알킬로 치환된 4, 5-디하이드로-2-옥사졸릴, 5-테트라졸릴 또는 하이드록시카바모일을 나타낸다.
  2. 제1항에 있어서, R1이 수소, 할로겐, 저급알킬, 저급알콕시, 하이드록시, 페닐-저급알콕시 또는 페닐 환상에서 저급알콕시, 저급알킬 또는 할로겐으로 일- 또는 이 치환된 페닐-저급 알콕시이며 ; R2는 수소, 할로겐 또는 저급알킬을 나타내고 ; A는 에테닐렌 또는 저급알킬로 치환된 에테닐렌을 나타내며 ; B는 탄소수 1내지 12의 알킬렌, 각기 탄소수 2내지 12의 알키닐렌 또는 알케닐렌, 페닐렌-저급알킬렌, 페닐렌-저급알케닐렌, 페닐렌, 페닐렌(티오 또는 옥시)-저급알킬렌을 나타내고 ; C는 카복시, 저급알콕시카보닐, 비치환된 또는 일- 또는 이-(저급알킬) 치환된 카바모일, 시아노, 하이드록시메틸, 포르밀, 5-테트라졸릴, 4, 5-디하이드로-2-옥사졸릴, 저급알킬로 치환된 4, 5-디하이드로 -2-옥사졸릴 또는 하이드록시 카바모일을 나타내는 일반식(Ⅰ)의 화합물 또는 그의 염을 제조하는 방법.
  3. 제1항에 있어서, R1이 수소, 할로겐, 저급알킬, 저급알콕시, 하이드록시 또는 아릴-저급알콕시(이때 아릴은 페닐, 또는 저급알콕시, 저급알킬, 할로겐 또는 트리플루오로메틸로 일- 또는 이- 치환된 페닐임)이며 ; R2는 수소, 할로겐, 또는 저급알킬을 나타내고 ; C는 카복시, 저급 알콕시카보닐, 비치환된 또는 일- 또는 이-(저급알킬) 치환된 카바모일, 시아노, 하이드록시메틸, 포르밀, 5-테트라졸릴, 4,5-디하이드로-2-옥사졸릴, 저급알킬로 치환된 4, 5-디하이드로-2-옥사졸릴 또는 하이드록시카바모일을 나타내며 ; A는 직접결합을 나타내고 ; B는 저급알킬렌페닐 저급알킬렌, 저급 알킬렌페닐렌, 페닐렌저급알킬렌, 페닐렌, 저급알킬렌-(티오 또는 옥시)-저급알킬렌, 저급알킬렌-(티오 또는 옥시)-페닐렌, 페닐렌-(티오 또는 옥시)-저급알킬렌, 페닐렌 저급알케닐렌, 저급알킬렌페닐렌 저급알케닐렌 또는 탄소수 5내지 12의 알카디에닐렌인 일반식(Ⅰ)의 화합물, 그의 5, 6, 7, 8-테트라하이드로 유도체 또는 그의 염을 제조하는 방법.
  4. 제1항에 있어서, 5-(4-카복시부티-1, 3-디에닐)-이미다조〔1,5-a〕 피리딘 또는 그의 염을 제조하는 방법.
  5. 제1항에 있어서, 5-〔p-(2-카복시프로프-1-에닐)페닐〕이미다조〔1,5-a〕 피리딘 또는 그의 염을 제조하는 방법.
  6. 제1항에 있어서, 5-(9-카복시노나-6,8-디에닐) 이미다조〔1,5-a〕 피리딘 또는 그의 염을 제조하는 방법.
  7. 일반식(Ⅰ)의 상응하는 이미다조〔1,5-a〕 피리딘 화합물을 수소로 환원시킴을 특징으로 하여 제1항에서 정의된 5, 6, 7, 8-테트라하이드로이미다조〔1,5-a〕 피리딘 또는 그의 염을 제조하는 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019830006030A 1982-12-21 1983-12-20 이미다조[1,5-a]피리딘 유도체의 제조방법 Expired KR910000440B1 (ko)

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US06/451,902 US4588732A (en) 1982-12-21 1982-12-21 Certain imidazo(1,5-a)pyridine derivatives and their use as thromboxane synthetase inhibitors
US451902 1982-12-21

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US4728645A (en) * 1982-12-21 1988-03-01 Ciba-Geigy Corporation Substituted imidazo[1,5-A]pyridine derivatives and other substituted bicyclic derivatives, useful as aromatase inhibitors
US4889861A (en) * 1982-12-21 1989-12-26 Ciba-Geigy Corp. Substituted imidazo[1,5-a]pyridine derivatives and other substituted bicyclic derivatives and their use as aromatase inhibitors
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US5057521A (en) * 1988-10-26 1991-10-15 Ciba-Geigy Corporation Use of bicyclic imidazole compounds for the treatment of hyperaldosteronism
US5716964A (en) * 1989-12-04 1998-02-10 G.D. Searle & Co. Tetrazolyl substituted imidazo 1,2-a!pyridinylalkyl compounds for treatment of neurotoxic injury
IE904346A1 (en) * 1989-12-04 1991-06-05 Searle & Co IMIDAZO[1,2-a]PYRIDINYLALKYL COMPOUNDS FOR TREATMENT OF¹NEUROTOXIC INJURY
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MTP1076B (en) * 1990-01-12 1991-09-30 Ciba Geigy Ag Hemihydrate
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US5468757A (en) * 1994-01-31 1995-11-21 Eli Lilly And Company 6-azaindole thromboxane synthase inhibitors
EP1565463B1 (en) * 2002-11-18 2008-06-11 Novartis AG Imidazo[1,5a] pyridine derivatives and methods for treating aldosterone mediated diseases

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JPS6050190B2 (ja) * 1978-05-02 1985-11-07 小野薬品工業株式会社 イミダゾ−ル誘導体
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NZ206652A (en) 1986-11-12
PH23147A (en) 1989-05-11
KR910000440B1 (ko) 1991-01-25
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GR81356B (ko) 1984-12-11
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IL70485A (en) 1987-02-27
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US4588732A (en) 1986-05-13
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EP0114573A1 (de) 1984-08-01
JPH047348B2 (ko) 1992-02-10
ATE33651T1 (de) 1988-05-15
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