KR870002164A - 5-아미노-2,5-이치환된-4-하이드록시펜타노산 잔기를 함유하는 레닌 억제물의 제조방법 - Google Patents

5-아미노-2,5-이치환된-4-하이드록시펜타노산 잔기를 함유하는 레닌 억제물의 제조방법 Download PDF

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KR870002164A
KR870002164A KR1019860006535A KR860006535A KR870002164A KR 870002164 A KR870002164 A KR 870002164A KR 1019860006535 A KR1019860006535 A KR 1019860006535A KR 860006535 A KR860006535 A KR 860006535A KR 870002164 A KR870002164 A KR 870002164A
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싱 빈드라 제이스지트
폭스 클레인만 에드워드
루이스 로사리 로버트
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화이자 인코퍼레이티드
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Abstract

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Description

5-아미노-2,5-이치환된-4-하이드록시펜타노산 잔기를 함유하는 레닌억제물의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (13)

  1. 일반식
    의 화합물을 일반식 R-W4-(W5)n-OH에 화합물과 탈수 결합시키고 ; 이어서 히스티딘 질소상의 특징 t-부톡시카보닐그룹을 가수분해 비차단 및 특징 벤질옥시카보닐 보호된 질소 또는 비목적 벤질 에스테르 보호된 카복실산그룹을 가수분해 비차단시킴을 특징으로 하여 일반식(Ⅰ)의 폴리펩타이드 유도체 또는 약제학적으로 허용되는 그의 염을 제조하는 방법.
    상기식에서, n 및 m은 각각 1 또는 0이되 n과 m은 합이 적어도 1이고 : W는
    [여기에서, R5는 페닐, 1-나프틸, 4-하이드록시페톡, 4-메톡시페닐, 4-이미다졸릴 프로필 또는 이소프로필이다]이며 ; W1은
    [여기에서, R6는 -NH2,또는 -CH2NH2이다]이며 : n이 1인 경우, R은 수소, 분자량 500 미만인 아미노-보호아실, 프롤릴, 피로글루타밀, 또는 질소상에서 상기 아미노-보호 아실기로 보호되는 피로-글루타밀 또는 프롤릴이고 ; n이 0인 경우, R은 페녹시아세틸 또는 2-벤질-3-페닐프로피오닐이며 ; R1및 R2는 각각 독립적으로 수소, (C1-C6)알킬,(C4-C6)알케닐, 페닐, 나프틸, (C4-C7)사이클로알킬, (C4-C7)사이클로알케닐, (C7-C9)페닐알킬, (C11-C13)나프틸알킬, (C5-C10)(사이클로알킬)알킬, (C5-C10)(사이클로알케닐)알킬, 또는 방향족 환상에서 (C1-C3)알킬, (C1-C3)알콕시, 플루오로 또는 클로로로부터 선택한 동일한 또는 상이한 그룹으로 일-또는 이치환된 상기 그룹중 하나이고 ;
    (a) R3및 R4는 분리된어 각각 독립적으로 수소, (C1-C6)알킬, 페닐, 나프틸, (C4-C7)사이클로알킬, 아다만틸, (C7-C9)페닐알킬, (C11-C13)나프틸알킬, (C5-C10)(사이클로알킬)알킬 또는 아다만틸이거나 ; 또는 R3는 수소이고 R4는[여기에서, p 및 q는 각각 독립적으로 0 또는 1 내지 6의 정수이고 ; r은 0 또는 1이며; Q는 -CH2-, -CH=CH-, -O-, -NH-, -CHOH-, 또는 -CO-이고 ; Y는 메틸, 페닐, -COOR9,-CONR9R10,-CONHCOOCH2C6H5,NH2,-NHCOCH2C6H5,
    이며;R7,R8,R9및 R10은 각각 독립적으로 수소, (C1-C6)알킬, 페닐, (C4-C7) 사이클로알킬, (C7-C9)페닐알킬, (C5-C10)(사이클로알킬) 알킬, 또는 아다만틸이다]이거나 ; 또는
    (b) R3및 R4가 함께 질소에 부착하여 피롤, 인돌린, 이소인돌린, 피페리딘, 1,2,3,4-테트라 하이드로퀴놀린, 1,2,3,4-테트라하이드로이소퀴놀린, 피하이드로아제핀, 또는 모르폴린 환 시스템을 형성하고 ; W3는
    [여기에서, R14는 -NHCO2CH2CH2C6H5,또는 -CH2NHCO2CH2C6H5이다]이며; (a)(R12및 R13은 분리되어 각각 독립, 으로 수소, (C1-C6)알킬, 페닐, 나프틸, (C4-C7)사이클로알킬, (C7-C9)페닐알킬, (C11-C13)나프틸알킬, (C5-C10)(사이클로알킬)알킬, 또는 아다만틸이거나 ; 또는 R12는 수소이고 R13은[여기에서, p,q,r 및 Q은 상기 정의한 바와 같고 ; Y1은 메틸페닐, -COOR18, -CONR9R10, -CONHCOCCH2C6H5, -NHCOCH2C6H5,
    R7,R8,R9및 R10은 각각 독립적으로 상기 정의한 바와 같고 : R8은 수소 이외의 R7의 독립적인 값이다] 이거나 ; 또는 (b) R12및 R13이 함께 질소에 부착하여 피롤, 인돌린 이소인돌린, 피페리딘, 1,2,3,4-테트라-하이드로퀴놀린, 1,2,3,4-테트라하이드로이소퀴놀린, 피하이드로아제핀, 또는 모르폴린 환 시스템을 형성하고 ; W4및 W5는 각각 W 및 W1에 상응하나 이미다졸 질소상에 t-부톡시카보닐 그룹으로 차단된 히스티딘 잔기를 갖고 있다.
  2. 제1항에 있어서, n이 1이고 R이 t-부톡시카보닐인 방법.
  3. 제2항에 있어서, R1이 사이클로헥실메틸이고, R2, 2-메틸프로필 2-메틸-2-프로페닐, 벤질, 4-클로로벤질, 3-클로로벤질, 4-메틸벤질, 4-메톡시벤질, 3,4-디클로로벤질, 2-클로로벤질, 또는 사이클로헥실메틸인 방법.
  4. 제3항에 있어서, m이 0이고 W가 페닐-알라닐이며, W1이 히스티리딜인 방법.
  5. 제4항에 있어서, R2가 2-메틸프로필 또는 2-메틸-2-프로페닐이고, R3가 수소이며, R4가 수소, 메틸, 4-아미노부틸, 2-카복시에틸, 3-(에톡시카보닐)프로필 또는 3-(벤질옥시카보닐)프로필인방법.
  6. 제4항에 있어서, R2가 벤질, 4-클로로벤질, 4-메틸벤질, 4-메톡시벤질, 3,4-디클로로벤질, 3-클로로벤질 또는 2-클로로벤질이고, R3가 수소이며, R4가 메틸인 방법.
  7. 제4항에 있어서, R2가 사이클로헥실메틸이고, R3가 수소이며, R4가 메틸인 방법.
  8. 제2항에 있어서, m이 1이고, W가 페닐알라닐이며, W1이 히스티딜이고, W2가 리실이며, R1이 사이클로헥실메틸이고, R2가 2-메틸프로필인 방법.
  9. 제1항에 있어서, n이 0이고, m이 1이며, W가 히스티딜이고, W2가 리실이며, R1이 사이클로헥실-메틸이고, R2가 2-메틸프로필인 방법.
  10. 일반식
    의 화합물을 프롤린 메틸 에스테르의 제거와 함께 고리화시켜 일반식
    의 화합물을 제조하는 방법.
  11. 일반식(B)의 알데하이드를 반응 불활성 용매중에서[여기에서, R15는 (C1-C3)알킬이다]와 -50° 내지 -80℃로 반응시켜 주로 일반식(C)의 화합물을 형성시킴을 특징으로 하는 입체 선택적방법.
    상기식에서, R16은 (C1-C6)알킬,(C1-C6)알케닐, 페닐, 나프틸, (C4-C7)사이클로알킬, (C4-C7)사이클로알케닐, (C7-C9)페닐알킬, (C11-C13)나프틸알킬, (C5-C10)(사이클로알킬)알킬, 또는 방향족 활에서 (C1-C3)알킬, (C1-C3)알콕시, 플루오로 또는 클로로중에서 선택한 동일하거나 상이한 그룹으로 일-또는 이치환된 상기 그룹중의 하나이다.
  12. 제11항에 있어서, (a) 일반식 (c)의 화합물을 수소화시켜 일반식(D)의 화합물을 형성하고, (b) 일반식(D)의 화합물을 고리화시켜 일반식(E)의 화합물을 형성시키는 단계를 또한 포함하는 방법.
  13. 일반식
    의 락톤을 낮은 친핵성의 강한 염기 상당한 과량의 존재하에 일반식 R17X (여기에서, X는 클로로, 브로모 또는 요오도이다)의 유기 할라이드 실질적으로 1몰당량과 반응시켜 하기 일반식의 화합물을 제조하는 입체선택적 방법.
    상기식에서, R16은 (C1-C6)알킬, (C1-C6)알케닐, 페닐, 나프틸 (C4-C7)사이클로알킬, (C4-C7)사이클로알케닐 (C7-C9)페닐알킬,(C11-C13)나프탈알킬, (C5-C10)(사이클로알킬)알킬, 또는 방향족 환에서 (C1-C3)알킬, 알콕시, 플루오로 또는 클로로 등의 동일한 또는 상이한 치환체로 일-또는 이 치환된 상기 그룹중 하나이고; R17은 (C1-C6)(2-알케닐), (C4-C7)사이클로-2-알케닐), 벤질, 나프틸메틸, 또는 방향족 환에서 (C1-C3)알킬, (C1-C3)알콕시, 플루오로 또는 클로로등의 동일한 또는 상이한 치환체로 일-또는 이 치환된 상기 그룹중 하나이다.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019860006535A 1985-08-09 1986-08-08 5-아미노-2,5-이치환된-4-하이드록시펜타노산 잔기를 함유하는 레닌 억제물의 제조방법 KR890003603B1 (ko)

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US06/858,324 US4729985A (en) 1985-08-09 1986-04-30 Renin inhibitors containing 5-amino-2,5-disubstituted-4-hydroxypentanoic acid residues

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US4729985A (en) 1988-03-08
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DK379186A (da) 1987-04-01
EP0212903A3 (en) 1989-11-15
HUT41419A (en) 1987-04-28
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JPS6253952A (ja) 1987-03-09
NZ217127A (en) 1989-11-28
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DE3687380D1 (de) 1993-02-11
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PT83172A (en) 1986-09-01
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EG17971A (en) 1991-11-30
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YU142286A (en) 1988-10-31
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