KR910000658A - 이미다졸릴- 알케노산 - Google Patents

이미다졸릴- 알케노산 Download PDF

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KR910000658A
KR910000658A KR1019900008739A KR900008739A KR910000658A KR 910000658 A KR910000658 A KR 910000658A KR 1019900008739 A KR1019900008739 A KR 1019900008739A KR 900008739 A KR900008739 A KR 900008739A KR 910000658 A KR910000658 A KR 910000658A
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methyl
compound
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thienyl
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알란 핀켈스타인 조셉
와인스톡 조셉
맥쿨로치 키이난 리챠드
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스튜아트 알. 슈터
스미스클라인 비참 코포레이션
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Abstract

내용 없음

Description

이미다졸릴-알케노산
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (17)

  1. 일반식(Ⅰ)의 화합물 또는 약제학적으로 허용되는 염.
  3. R1은 비치환되거나, Cl, Br, F, I C1-C4알킬, 니트로, CO2R7, 테트라졸-5-일, C1-C4알콕시, 하이드록시, SC1-C4알킬, SO2NHR7, SO3H, CONR7R7, CN, SO2C1-C4알킬 및 CnF2n+1(여기에서 n은 1내지 3이다)중에서 선택된 하나 내지 3개의 치환체에 의해 치환된, 페닐, 비페닐, 나프틸, 또는 아다만틸 메틸이고: R2는 비치환되거나, C1-C4알킬, 니트로, Cl, Br, F, I, 하이드록실, C1-C4알콕시, NR7R7, CO2R7, CN 및 CONR7R7중에서 선택된 1 내지 3개의 치환체에 의해 치환된, C2-C10알킬, C3-C10알케닐, C3-C10알키닐, C3-C6사이클로알킬 또는 (CH2)0-8페닐이며: X는 단일결합, S 또는 O이고: R3은 수소, Cl, Br, F, I, CHO, 하이드록시메틸, COOR7, CONR7R7, NO2, 또 CnF2n+1(여기에서 n은 1내지 3이다)이며: R4및 R5는 독립적으로 수소, C1-C6알킬, 티에닐-Y-, 피라졸릴-Y-, 이미다졸릴-Y-, 티아졸리-Y-, 푸릴-Y-, 피롤릴-Y, 티아졸릴-Y-, 옥사졸릴-Y-, 이속사졸릴-Y-, 피리딜-Y- 또는 테트라졸릴-Y-이고, 단 R4및 R5는 모두 수소 및 C1-C4알킬 중에서 선택되어서는 안되며, 헤테로 사이클릭 환은 각각 비치환되거나, C1-C4알킬, C1-C4알콕시, Cl, Br, F, I, NR7R7, CO2R7, SO2NHR7, SO3H 또는 CONR7R|7에 의해 치환되어야 하고: Y는 단일결합, S, O 또는 직쇄 또는 측쇄이거나 페닐 또는 벤질로 임의 치환된 C1-C6알킬이며, 여기에서 아릴그룹은 각각 비치환되거나 할로, NO2, CF3, C1-C4알킬, C1-C4알콕시, CN, 또는 CO2R7에 의해 치환되고, R6는 -Z-COOR8또는 -Z-CONR7R7이며: Z는 단일결합: 비닐: -CH2-O-CH2-: C1-C4알킬, 페닐, 벤질, 티에닐메틸 또는 푸릴메틸이다)이고: R7는 각각 독립적으로 수소, C1-C4알킬, 또는 (CH2)m페닐(여기에서 m은 0내지 4이다)이며: R8은 수소, C1-C6알킬, 또는 2-디(C|1-C4알킬)아미노-2-옥소에틸이다.
  4. 제1항에 있어서, R1이 비치환되거나, 클로로, 플루오로, 트리플루오로메틸, 니트로, 메틸, 메톡시, 하이드록시, 설파이드, 시아노, 카복시, 카보-C1-C4알콕시, 카바모일 및 테트라졸-5-일 중에서 선택된 하나 내지 3개의 치환체에 의해 치환된 페닐이고: X가 단일결합이며; R2가 C2-C8알킬이고: R3가 수소, 클로로, 플루오로 또는 트리플루오로 메틸이며: R4가 수소, 또는 C1-C4알킬이고: R5가 각각 메틸 또는 메톡시에의해 임의로 치환된 티에틸메틸, 푸릴메틸, 이미다졸릴메틸 또는 피리딜메틸이며: R6가 COOH, COOC1-C2알킬, CONH2인 화합물.
  5. 제1항 또는 제2항에 있어서, E(트랜스)이성체인 화합물.
  6. 제1항에 있어서, (E)-3-[2-n-부틸-1-{(4-카복시페닐)메틸}-1H-이미다졸-5-일]-2-(2-티에닐)메틸-2-프로페논산 또는 이의 약제학적으로 허용되는 염.
  7. 제1항에 있어서, (E)-3-[2-n-부틸-1-{(4-카복시-3-클로로페닐)메틸}-1H-이미다졸-5-일]-2-(2-티에닐)메틸-2-프로페논산 또는 이의 약제학적으로 허용되는 염.
  8. 제1항에 있어서, (E)-3-[2-n-부틸-1-{(2-클로로페닐)메틸}-1H-이미다졸-5-일]-2-(2-티에닐)메틸-2-프로페논산, (E)-3-[2-n-부틸-1-{(4-카복시-2-클로로페닐)메틸}-1H-이미다졸-5-일]-2-(2-티에닐)메틸-2-프로페논산, (E)-3-[2-n-부틸-1-{(4-카복메톡시 페닐)메틸}-1H-이미다졸-5-일]-2-(2-티에닐)메틸-2-프로페논산, (E)-3-[2-n-헥실-1-{(4-카복시 페닐)메틸}-1H-이미다졸-5-일]-2-(2-티에닐)메틸-2-프로페논산, (E)-3-[2-n-프로필-1-{(4-카복시페닐)메틸}-1H-이미다졸-5-일]-2-(2-티에닐)메틸-2-프로페논산, (E)-3-[2-n-부틸-1-{(2-니트로페닐)메틸}-1H-이미다졸-5-일]-2-(2-티에닐)메틸-2-프로페논산, (E)-3-[2-n-부틸-1-{(2-클로로페닐)메틸}-1H-이미다졸-5-일]-2-(2-푸릴)메틸-2-프로페논산, (E)-3-[2-n-부틸-1-{(2-클로로페닐)메틸}-1H-이미다졸-5-일]-2-(4-이미다졸릴)메틸-2-프로페논산, (E)-3-[2-n-부틸-1-{(2-클로로페닐)메틸}-1H-이미다졸-5-일]-2-(3-티에닐)메틸-2-프로페논산, (E)-3-[2-n-부틸-1-{(2-클로로페닐)메틸}-1H-이미다졸-5-일]-2-(5-메틸-2-티에닐)메틸-2-프로페논산, (E)-3-[2-n-부틸-1-{(2-시아노페닐)메틸}-1H-이미다졸-5-일]-2-(2-티에닐)메틸-2-프로페논산, (E)-3-[2-n-부틸-1-{(4-메톡시-3-메틸페닐)메틸}-1H-이미다졸-5-일]-2-(2-티에닐)메틸-2-프로페논산, (E)-3-[2-n-부틸-1-{(2-클로로페닐)메틸}-1H-이미다졸-5-일]-2-(4-피리딜)메틸-2-프로페논산, (E)-3-[2-n-부틸-1-{(2-클로로페닐)메틸}-1H-이미다졸-5-일]-2-(5-메톡시-2-티에닐)메틸-2-프로페논산, (E)-3-[2-n-부틸-1-{(2,3-디클로로페닐)메틸}-1H-이미다졸-5-일]-2-(2-티에닐)메틸-2-프로페논산, 또는 (E)-3-[2-n-부틸-1-{(2-트리플루오로메틸페닐)메틸}-1H-이미다졸-5-일]-2-(2-티에닐)메틸-2-프로페논산: 또는 이의 약제학적으로 허용되는 염.
  9. 제1항 내지 제6항중 어느 한항에 따르는 화합물 및 이의 약제학적으로 허용되는 담체를 함유하는 약제학적 조성물.
  10. a)일반식(Ⅱ)의 화합물을 염기의 존재하에서 (C1-C4알콕시)2P(O)CH(R5)COOC1-C6알킬(여기에서 R5는 제1항에서 정의한 바와 같다)과 반응시키거나, b)일반식(Ⅲ)의 화합물을 일반식(Ⅳ)의 화합물과 반응시키거나, c)일반식(Ⅱ)의 화합물을 염기의 존재하에서 일반식(Ⅴ)의 화합물과 반응시키거나, d)일반식(Ⅳ)의 화합물을 염기와 반응시키거나, c)일반식(Ⅱ)의 화합물을 아세트산 무수물 중에서 염기의 존재하에 적절한 헤테로 사이클릭 아세트산과 반응시킨후: (i)상기와 같이 제조된 일반식(Ⅰ)의 에스테르 화합물을 환원시키고, 이어서, C1-C6알킬 할로아세테이트와 반응시켜 Z가 -CH2-O-CH2- 인 일반식(Ⅰ)의 화합물을 생성시키거나, (ⅱ)상기와 같이 제조된 일반식(Ⅰ)의 에스테르 화합물을 가수분해시키고, 이어서 아미노생성시약의 존재하에서 적절히 치환된 아미노산과 반응시켜 Z가 -C(O)NHCHR9-이고 R9이 수소, C1-C4알킬, 페닐, 벤질, 티에닐 메틸, 또는 푸릴메틸인 일반식(Ⅰ)의 화합물을 생성시키거나, (ⅲ)상기와 같이 제조된 일반식(Ⅰ)의 에스테르 화합물을 환원시키고, 이어서 C1-C6알킬과 반응시킨후 포스핀 리간드의 존재하에서 일산화탄소와 반응시켜 Z가 메틸렌그룹인 일반식(Ⅰ)의 화합물을 생성시키거나, (ⅳ)Z가 케틸렌그룹인 상기와 같이 제조된 일반식(Ⅰ)의 에스테르 화합물을 리튬 디알킬아미드와 반응시키고, 이어서 알킬화제와 반응시켜 Z가 C1-C4알킬, 벤질, 티에닐 메틸 또는 푸릴메틸에 의해 치환된 메틸렌그룹인 일반식(Ⅰ)의 화합물을 생성시킨후: 필요한 경우 (i)R1그룹이 C1-C4알콕시에 의해 치환된 일반식(Ⅰ)의 화합물을 탈보호시켜 R1그룹이 하이드록시에 의해 치환된 일반식(Ⅰ)의 화합물을 생성시키거나, (ⅱ)R1그룹이 CO2C1-C|4알킬에 의해 치환된 일반식(Ⅰ)의 화합물을 가수분해시켜 R1그룹이 카복시에 의해 치환된 일반식(Ⅰ)의 화합물을 생성시키거나, (ⅲ)R1그룹이 카복시에 의해 치환된 일반식(Ⅰ)의 화합물을 할로겐화제로 처리하고, 이어서 암모니아와 반응시켜 1급 아미드로 전환시키고, 옥살릴클로라이드/디케틸포름아미드로 탈수시키고, 아지드와 반응시켜, R1그룹이 테트라졸-5-일 그룹에 의해 치환된 일반식(Ⅰ)의 화합물을 생성시키거나, (ⅳ)R6가 -Z-COOC1-C6알킬인 일반식(Ⅰ)의 화합물을 가수분해시켜 R6가 -Z-COOH인 일반식(Ⅰ)의 화합물을 생성시키거나, (ⅴ)R6가 -Z-COOH인 일반식(Ⅰ)의 화합물을 할로겐화제로 처리하고, 이어서 적절히 치환된 아민과 반응시켜 R6가 -Z-CONR7R7이고 R7가 수소, C1-C4알킬 또는 (CH2)0-4페닐인 일반식(Ⅰ)의 화합물을 생성시킨후: 임의로 약제학적으로 허용되는 염을 형성시킴을 특징으로 하여, 제1항에서 정의한 일반식(Ⅰ)의 화합물 또는 이의 약제학적으로 허용되는 염을 제조하는 방법.
  12. 상기식에서, R2,R3,R4,R5및 X는 제1항에서 정의한 바와 같고:R|1′는 제1항에서 정의한 R1이며, 단 R1′그룹상의 치환체는 테트라졸-5-일, OH, 또는 CO2H를 포함해서는 안되고: W는 Cl, Br, F, I, C1-C4알킬, 니트로, CO2C1-C|4알킬, C1-C4알콕시, SCC1-C4알킬, CN, SO2C1-C4알킬, SO2NHR|7, NHSO2C1-C4알킬 또는 CnF2n+1이며, 여기에서 n은 1 내지 3이고, p는 0 내지 3이며, R7은 수소, C1-C4알킬 또는 (CH2)0-4페닐이고: R11은 COCH3또는 SO2CH3이다.
  13. 안지오텐신Ⅱ수용체 길항작용이 한 인자인 질병을 치료하기 위한 약제를 제조하는데 있어서 제1항에서 정의한 일반식(Ⅰ)의 화합물 또는 이의 약제학적으로 허용되는 염의 용도.
  14. 고혈압증을 치료하기 위한 약제를 제조하는데 있어서, 제1항에서 정의한 일반식(Ⅰ)의 화합물 또는이의 약제학적으로 허용되는 염의 용도.
  15. 울형성 심부전증을 치료하기 위한 약제를 제조하는데 있어서, 제1항에서 정의한 일반식(Ⅰ)의 화합물 또는 이의 약제학적으로 허용되는 염의 용도.
  16. 신장병을 치료하기 위한 약제를 제조하는데 있어서 제1항에서 정의한 일반식(Ⅰ)의 화합물 또는 이의 약제학적으로 허용되는 염의 용도.
  17. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019900008739A 1989-06-14 1990-06-14 이미다졸릴-알켄산 및 이의 제조방법 및 약제학적 조성물 KR0165837B1 (ko)

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PL165609B1 (pl) 1995-01-31
ATE250587T1 (de) 2003-10-15
KR0165837B1 (ko) 1999-02-18
IE902140A1 (en) 1991-01-02
EP0403159B1 (en) 2000-03-01
IL94698A (en) 1994-07-31
DE69034103T2 (de) 2004-07-15
CN1079649A (zh) 1993-12-22
HU903847D0 (en) 1990-11-28
DE69033469T2 (de) 2000-09-07
EP0955294A2 (en) 1999-11-10
FI902970A0 (fi) 1990-06-13
HK1012384A1 (en) 1999-07-30
GR3033452T3 (en) 2000-09-29
CN1048159C (zh) 2000-01-12
DK0403159T3 (da) 2000-08-14
PT94377A (pt) 1991-03-20
CA2018438A1 (en) 1990-12-14
PL285591A1 (en) 1991-03-25
PH27592A (en) 1993-08-31
NL300006I1 (nl) 2000-07-03
EP0955294A3 (en) 2000-04-19
NZ233997A (en) 1991-04-26
DE10075018I1 (de) 2000-09-21
EP0403159A2 (en) 1990-12-19
HK1025315A1 (en) 2000-11-10
NO175977B (no) 1994-10-03
EP0403159A3 (en) 1991-12-27
DK0955294T3 (da) 2004-02-02
ATE190051T1 (de) 2000-03-15
IL94698A0 (en) 1991-04-15
DE10075018I2 (de) 2001-08-09
CN1027504C (zh) 1995-01-25
EP0955294B1 (en) 2003-09-24
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CY2232B1 (en) 2003-04-18
ES2142789T3 (es) 2000-05-01
HU208537B (en) 1993-11-29
NO902632L (no) 1990-12-17
DE69034103D1 (de) 2003-10-30
IE902140L (en) 1990-12-14
CA2018438C (en) 2000-08-08
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JPH0768223B2 (ja) 1995-07-26
ES2207091T3 (es) 2004-05-16
AU5690190A (en) 1991-01-10
AU633322B2 (en) 1993-01-28
JPH03115278A (ja) 1991-05-16
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FI102610B1 (fi) 1999-01-15
CN1048038A (zh) 1990-12-26
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PT94377B (pt) 1997-02-28
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