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KR890011853A - 치환된 피롤, 피라졸 및 트리아졸 안지오텐신ⅱ 길항제 - Google Patents

치환된 피롤, 피라졸 및 트리아졸 안지오텐신ⅱ 길항제 Download PDF

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KR890011853A
KR890011853A KR1019890000095A KR890000095A KR890011853A KR 890011853 A KR890011853 A KR 890011853A KR 1019890000095 A KR1019890000095 A KR 1019890000095A KR 890000095 A KR890000095 A KR 890000095A KR 890011853 A KR890011853 A KR 890011853A
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존 카리니 데이빗
조나스 비타우타스 던시아 존
제임스 웰스 그레고리
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제임스 제이 플라인
이.아이.듀퐁 드 네모아스 앤드 캄파니
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Abstract

내용 없음

Description

치환된 피롤, 피라졸 및 트리아졸 안지오텐신Ⅱ 길항제
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (51)

  1. 하기 일반식(Ⅰ)의 고혈압 치료 화합물 또는 이의 약제학적으로 적합한 염.
    상기식에서, X, Y 및 Z는 독립적으로 N 또는 CR2이고, 단 1) R2가 H가 아닌 경우, X, Y 또는 Z중 오직 하나만 CR2일수 있으며; 2) Z가 N인 경우, Y 및 X는 CR2가 아니거나; 또는 3) Y가 N인 경우, Z 및 X는 CR2가 아니고; 4) X 및 Y가 N인 경우, Z는 N이 아니며, 5) X가 N이고, Y 및 Z가 CR3인 경우, Y에 관하여 R2는 C3-4알킬 또는 C4알케닐이 아니고, Z에 관하여 R2는 H 또는 Cl이 아니며, R1은 (CH2)nOR4[여기서, n은 1이고 R4는 C1알킬이다]가 아니며 A는 탄소간 단일 결합이 아니고, R3는 CO2H가 아니며 R5는 H가 아니고; A 는 탄소간 단일결합, CO, O, NHCO또는 OCH2이며 ; R1은 탄소수 2 내지 6의 알킬, 탄소수 3 내지 6의 알케닐 또는 알키닐, 또는 (CH2)nOR4이고, 단 R1이 (CH2)nOR4인 경우 R2는 H, 탄소수 2내지 6의 알킬, 탄소수 3 내지 6의 알케닐 또는 알키닐이고; R2는 H, 탄소수 2내지 6의 알킬, 탄소수 3내지 6의 알케닐 또는 알키닐; -(CH2)nOR4;
    또는 (CH2)nSH이고; R4는 H 또는 탄소수 1 내지 4의 알킬이며; R5는 H, 할로겐, NO2, 메톡시 또는 탄소수 1 내지 4의 알킬이고, R6은 H, 탄소수 1 내지 6의 알킬; 탄소수 3 내지 6의 사이클로알킬, (CH2) mC6H5, OR7또는 NR8R9이며; R7은 H, 탄소수 1 내지 5의 알킬, 탄소수 3내지 6의 사이클로알킬, 페닐 또는 벤질이고; R8및 R9는 독립적으로 H, 탄소수 1 내지 4의 알킬, 페닐 또는 벤질이거나 NR8R9는 함께 결합되어 일반식의 환을 형성하며; Q는 NR10, O 또는 CH2이고; R10은 H, 탄소수 1 내지 4의 알킬 또는 페닐이고 ; R11은 탄소수 1 내지 6의 알킬, 탄소수 1 내지 6의 퍼플루오로알킬 또는 (CH2)pC6H5이고 ; R12는 H, 탄소수 1 내지 4의 알킬 또는 탄소수 1 내지 4의 아실이며 ; m은 0내지 6이고 ; n은 1 내지 6이며 ; p는 0내지 3이고 ; r은 0내지 1이며 ; t는 0내지 2이다.
  2. 제1항에 있어서, A가 탄소간 단일 결합 또는 NHCO이고 ; R1이 알킬, 탄소수 3 내지 5의 알케닐 또는 알키닐이며 ; R2가 H, 알킬 ; 탄소수 3 내지 5의 알케닐 또는
    이며 ; R4가 H 또는 CH3이고 ; R5가 H이며 ; R6이 H, 탄소수 1 내지 6의 알킬, OR7또는 NR8R9이고 ; R7이 탄소수 1 내지 6의 알킬이며 ; R8및 R9가 독립적으로 H, 탄소수 1 내지 4의 알킬이거나 또는 질소와 함께 결합하여환을 형성하며 ; R11이 CF3, 탄소수 1 내지 4의 알킬 또는 페닐이며 ; m이 0내지 3이고 n이 1내지 3인 화합물 또는 이의 약제학적으로 적합한 염.
  3. 제1항에 있어서, A가 탄소간 단일 결합이고, R1이 탄소수 3내지 5의 알킬 또는 알케닐 이거나 또는 CH2OR4이고, 단 R1이 CH2OR4인 경우 R2는 탄소수 3내지 5의 알킬 또는 알케닐이며 ; R2가 탄소수 3 내지 5의 알킬 또는 알케닐, CH2OR4,
    COR6,이고 ; R6이 H, OH 또는 탄소수 1 내지 4의 알킬이며 ; R7이 탄소수 1 내지 4의 알킬이 화합물 또는 이의 약제학적으로 적합한 염.
  4. 제1항에 있어서, 3-메톡시메틸-5-프로필-4-[(2'-(1H-테트라졸-5-일)비페닐-4-일)메틸]-1,2,4-트리아졸인 화합물 또는 이의 약제학적으로 적합한 염.
  5. 제1항에 있어서, 3-메톡시메틸-5-부틸-1-[(2'-카복시비페닐-4-일)메틸]피라졸인 화합물 또는 이의 약제학적으로 적합한 염.
  6. 제1항에 있어서, 5-부틸-1-[(2'-카복시비페닐-4-일)메틸]-1,2,3-트리아졸인 화합물 또는 이의 약제학적으로 적합한 염.
  7. 제1항에 있어서, 5-메톡시메틸-3-프로필-1-[(2'-카복시비페닐-4-일)메틸]피라졸인 화합물 또는 이의 약제학적으로 적합한 염.
  8. 제1항에 있어서, 3-카복시-5-n-프로필-1-[(2'-카복시비페닐-4-일)메틸]피라졸인 화합물 또는 이의 약제학적으로 적합한 염.
  9. 제1항에 있어서, 5-n-프로필-1-[(2'-카복시비페닐-4-일)메틸]피롤-2-카복실산인 화합물.
  10. 약제학적으로 적합한 담체 및 제1항 내지 제8항중 어느 한 항의 화합물을 함유하는 약제학적 조성물.
  11. 제1항 내지 제9항중 어느 한 항의 화합물을 동물의 혈압을 저하시키기에 유효한 양으로 동물에 투여함을 특징으로 하여, 온혈 동물의 고혈압을 치료하는 방법.
  12. 울혈증을 경감시키기 위해 심장의 혈액동력학적 부담을 보정하기에 유효한 양으로 제1항 내지 제9항 중 어느 한 항의 화합물을 동물에 투여함을 특징으로 하여, 온혈동물의 울혈성 심부전증(congestive heart failure)을 치료하는 방법.
  13. 일반식 (1) R'-C CH의 알킨을 하기 일반식 (3) 의 화합물과 반응시킴을 특징으로 하여, 헤테로사이클럭 환이 1,2,3-트리아졸인 제1항의 화합물을 제조하는 방법.
  14. 하기 일반식 (2) 의 1,2,3-트리아졸을 하기 일반식 (5) 의 화합물과 반응시킴을 특징으로 하여, 헤테로사이클릭 환이 1,2,3-트리아졸인 제1항의 화합물을 제조하는 방법.
    상기식에서, A는 단일 결합, 0 또는 CO이고 X는 할로겐이다.
  15. 하기 일반식(II) 의 화합물을 하기 일반식(13)의 화합물 또는 기타 아미드-결합 형성제와 반응시킴을 특징으로 하여, 헤테로사이클릭 환이 1,2,3-트리아졸이고, A가 NHCO인 제1항의 화합물을 제조하는 방법.
  16. 하기 일반식(II) 의 화합물을 하기 일반식 (12)의 화합물과 반응시킴을 특징으로 하여, 헤테로사이클릭 환이 1,2,3-트리아졸이며, A가 NHCO이고, R3이 CH2H인 제1항의 화합물을 제조하는 방법.
  17. 하기 일반식(20) 화합물의 프로톤을 제거하고 생성된 화합물을 하기 일반식 (21)의 화합물과 반응시킴을 특징으로 하여, 헤테로사이클릭 환이 1,2,3-트리아졸이고, A가 OCH2인 제1항의 화합물을 제조하는 방법.
    상기식에서 X는 할로겐이다.
  18. 하기 일반식(45) 의 화합물을 하기 일반식(46) 의 화합물과 반응시키거나 또는 하기 일반식 (51)의 하기 일반식(52) 의 화합물과 반응시킨후, 생성물을 하기 일반식(47) 의 화합물과 반응시킴을 특징으로 하여, 헤테로사이클릭 환이 1,2,4-트리아졸이고 A가 단일결합, 0또는 CO인 제1항의 화합물을 제조하는 방법.
  19. 하기 일반식(49)의 화합물을 하기 일반식 (47) 의 화합물과 반응시킴을 특징으로 하여, 헤테로사이클릭 환이 1,2,4-트리아졸이고 A가 단일결합, O 또는 CO인 제1항의 화합물을 제조하는 방법.
  20. 하기 일반식(50)의 화합물을 사이클로 축합시킴을 특징으로 하여, 헤테로사이클럭 환이 1,2,4-트리아졸이고 A가 단일 결합, O또는 CO인 제1항의 화합물을 제조하는 방법.
  21. 하기 일반식(54)의 화합물을 하기 일반식 (5)의 화합물과 반응시킴을 특징으로 하여, 헤테로사이클릭 환이 1,2,4-트리아졸이고 A가 단일결합, O또는 CO인 제1항의 화합물을 제조하는 방법.
    상기식에서, X는 할로겐이다.
  22. 하기 일반식(56)의 화합물을 하기 일반식(57)의 화합물과 반응시킴을 특징으로 하여, 헤테로사이클릭 환이 1,2,4-트리아졸이고 A가 단일결합, O또는 CO인 제1항의 화합물을 제조하는 방법.
  23. 하기 일반식(61)의 화합물을 하기 일반식 (13)의 화합물과 반응시킴을 특징으로 하여, 헤테로사이클릭 환이 1,2,4-트리아졸이고 A가 NHCO인 제1항의 화합물을 제조하는 방법.
  24. 하기 일반식(61)의 화합물을 하기 일반식 (12)의 화합물과 반응시킴을 특징으로 하여, 헤테로사이클릭 환이 1,2,4-트리아졸이고 A가 NHCO이고 R3이 CO2H인 제1항의 화합물을 제조하는 방법.
  25. 하기 일반식 (67)의 하기 일반식 (21)의 화합물과 반응시킴을 특징으로 하여, 헤테로사이클릭 환이 1,2,4-트리아졸이고 A가 OCH2인 제1항의 화합물을 제조하는 방법.
    상기식에서, X는 할로겐이다.
  26. 하기 일반식 (78)의 화합물을 하기 일반식(57)의 화합물과 반응시킴을 특징으로 하여, 헤테로사이클릭 환이 피라졸이고, A가 단일결합, O 또는 CO인 제1항의 화합물을 제조하는 방법.
  27. 하기 일반식(79)의 화합물을 하기 일반식(5)의 화합물과 반응시킴을 특징으로 하여, 헤테로사이클릭 환이 피라졸이고 A가 단일결합, O 또는 CO인 제1항의 화합물을 제조하는 방법.
    상기식에서, X는 할로겐이다.
  28. 하기 일반식(82)의 화합물을 하기 일반식(12) 또는(13)의 화합물과 반응시킴을 특징으로 하여 헤테로사이클릭 환이 피라졸이고 A가 NHCO인 제1항의 화합물을 제조하는 방법.
  29. 하기 일반식(86)의 화합물을 하기 일반식(21) 의 화합물과 반응시킴을 특징으로 하여, 헤테로사이클릭 환이 피라졸이고 A가 COH2인 제1항의 화합물을 제조하는 방법.
    상기식에서, X는 할로겐이다.
  30. 하기 일반식(99a)의 화합물을 하기 일반식 (5)의 화합물과 반응시킴을 특징으로 하여, 헤테로사이클릭 환이 1,2,4-피롤이고 A가 단일결합, O또는 CO인 제1항의 화합물을 제조하는 방법.
    상기식에서, X는 할로겐이다.
  31. 하기 일반식(98)의 화합물을 하기 일반식 (47)의 화합물과 반응시킴을 특징으로 하여, 헤테로사이클릭 환이 피롤이고 A가 단일결합, O또는 CO인 제1항의 화합물을 제조하는 방법.
  32. 하기 일반식(101)의 화합물을 하기 일반식(47) 의 화합물과 반응시킴을 특징으로 하여, 헤테로사이클릭 환이 피롤이고 A가 단일결합, O 또는 CO인 제1항의 화합물을 제조하는 방법.
  33. 하기 일반식 (105)의 화합물을 하기 일반식(47)의 화합물과 반응시킴을 특징으로 하여, 헤테로사이클릭 환이 피롤이고 A가 단일결합, O 또는 CO인 제1항이 화합물을 제조하는 방법.
  34. 하기 일반식 (119)의 화합물을 일반식(5)의 화합물과 반응시킨후 피롤 환상의 카보닐 그룹을 카보닐 그룹을 정교하게 R1및 R2로 전환시킴을 특징으로 하여, 헤테로사이클릭 환이 피롤이고 A가 단일결합, O 또는 CO인 제1항의 화합물을 제조하는 방법.
  35. R2가 CH2CN인 상응하는 화합물 (일반식127)을 가수분해시킴을 특징으로 하여, R2가 CH2CO2H인 제1항의 화합물 (일반식128)을 제조하는 방법.
  36. R2가 CH2CO2H인 제1항의 상응하는 화합물 (일반식128)을 환원시킴을 특징으로 하여, R2가 (CH2)2OH인 제1항의 화합물 (일반식 130)을 제조하는 방법.
  37. R2가 CH2CO2H인 제1항의 상응하는 화합물 (일반식128)을 알코올 R7OH와 반응시킴을 특징으로 하여, R2가 CH2CO2R7인 제1항의 화합물 (일반식129)을 제조하는 방법.
  38. R2가 CH2OH인 또는 (CH2)2OH인 제1항의 상응하는 화합물(일반식 125)(일반식 130)을 산무수물(R4CO)2O 또는 산 크로라이드 R4COCl과 반응시킴을 특징으로 하여 R2가 (CH2)OCOR4또는 (CH2)2OCOR4인 제1항의 화합물 (일반식131)을 제조하는 방법.
  39. R2가 CH2OH인 제1항의 상응하는 화합물 (일반식125)을 L이 할로겐, 메실레이트 또는 토실레이트인 화합물 R4L와 반응시킴을 특징으로 하여 R2가 CH2OR4인 제1항의 화합물 (일반식 132 )을 제조하는 방법.
  40. R2가 CH2Cl인 상응하는 화합물 (일반식126)을 M이 나트륨 또는 칼륨인 화합물 R4OM과 반응시킴을 특징으로 하여 R2가 CH2OR4인 제1항의 화합물 (일반식132)을 제조하는 방법.
  41. R2가 (CH2)mCO2H인 제1항의 상응하는 화합물 (일반식 128)을 일반식 R8R9NH의 화합물과 반응시킴을 특징으로 하여, R2가 -(CH2)mCONR8R9인 제1항의 화합물 (일반식 133)을 제조하는 방법.
  42. R2가 -(CH2)nNH2인 상응하는 화합물 (일반식 134)을 화합물 R11SO2Cl과 반응시킴을 특징으로 하여, R2가 -(CH2)nNSO2R11인 제1항의 화합물 (일반식 135)을 제조하는 방법.
  43. R2가 -(CH2)nNH2인 상응하는 화합물을 일반식 R11OCOCl 또는 R11OCO2R11의 화합물과 반응시킴을 특징으로 하여, R2가 -(CH2)nNHCO2R11인 제1항의 화합물(일반식 136)을 제조하는 방법.
  44. R2가 CH2Cl인 상응하는 화합물(일반식126)을 M이 나트륨 또는 칼륨인 화합물 R4SM과 반응시켜 설파이드 (일반식 137)을 수득한후, 임의로 산화시케 설폭사이드 또는 설폰(일반식 138)을 수득함을 특징으로 하여, R2가 -(CH2)nS9(C)tR4인 제1항의 화합물 (일반식 137,138)을 제조하는 방법.
  45. R2가 -(CH2)nOH인 제1항의 상응하는 화합물 (일반식139)을 플루오르화제와 반응시킴을 특징으로 하여, R2가 -(CH2)nF인 제1항의 화합물 (일반식140)을 제조하는 방법.
  46. R2가 -(CH2)nSCOCH3인 상응하는 화합물 (일반식141)을 가수분해시킴을 특징으로 하여 R2가 -(CH2)nSH인 제1항의 화합물 (일반식140)을 제조하는 방법.
  47. R2가 시아노메틸인 상응하는 화합물 (일반식127)을 나트륨아지드 및 염화암모늄과 반응 시키거나 또는 트리아킬틴 또는 트리아릴틴 아지드로 2,3-양극성 사이클로 부가반응시킴을 특징으로 하여 R2가 테트라졸릴메틸인 제1항의 화합물 (일반식 143)을 제조하는 방법.
  48. R2가 -CH2OH인 제1항의 상응하는 화합물 (일반식125)을 산화시킴을 특징으로 하여 R2가 -CHO인 제1항의 화합물 (일반식144)을 제조하는 방법.
  49. R2가 -CHO인 상응하는 화합물 (일반식144)을 쇄(chain) 연장반응시키거나 또는 R2가 CHOHCHRR'인 상응하는 화합물 (일반식145)을 탈수시킴을 특징으로 하여 R2가 알케닐인 제1항의 화합물 (일반식146)을 제조하는 방법.
  50. R1이 브로모알킬인 상응하는 화합물 (일반식148)을 염기와 접촉시킴을 특징으로 하여 R1이 알케닐인 제1항의 화합물 (일반식149)을 제조하는 방법.
  51. R1이 -CHO인 상응하는 화합물 (일반식150)을 쇄(chain) 연장반응시키거나 또는 일반식 RCH=PPh3의 화합물과 반응시킴을 특징으로 하여 R1이 알케닐인 제1항의 화합물 (일반식151)을 제조하는 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019890000095A 1988-01-07 1989-01-07 치환된 트리아졸 안지오텐신 ⅱ 길항제 KR910002823B1 (ko)

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HU906493D0 (en) 1991-04-29
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