KR850007255A - 약제학상 유용한 디하이드로피리디닐 디카복실레이트 아마이드 및 에스테르 - Google Patents

약제학상 유용한 디하이드로피리디닐 디카복실레이트 아마이드 및 에스테르 Download PDF

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KR850007255A
KR850007255A KR1019850002382A KR850002382A KR850007255A KR 850007255 A KR850007255 A KR 850007255A KR 1019850002382 A KR1019850002382 A KR 1019850002382A KR 850002382 A KR850002382 A KR 850002382A KR 850007255 A KR850007255 A KR 850007255A
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piperazinyl
nitrophenyl
dimethyl
dihydro
compound
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에스. 포인덱스터(외 1) 그레이엄
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이삭 쟈크브스키
브리스톨 마이어스 캄파니
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Abstract

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Description

약제학상 유용한 디하이드로피리디닐 디카복실레이트 아마이드 및 에스테르
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (71)

  1. R2와 R6가 저급알킬, 하이드록시알킬, 알콕시알킬, 알킬아미노알킬, 혹은 디알킬아미노알킬로부터 독립적으로 선택되고; R4가 5-7탄소의 사이클로알킬, 7-9탄소원자의 바이사이클로알케닐, 헤타릴(푸라닐, 인돌릴, 메틸티오피리딜, 디에닐, 벤즈옥사디아졸릴 및 벤조티아디아졸릴로 구성); 아릴(페닐, 나프틸 혹은 독립적으로 아세토아미노, 저급알킬, 저급알콕시, 시아노, 할로겐, 하이드록실, 니트로, 티리플루오로메틸, 트리를루오로메틸-슬포닐 혹은 메틸슬로포닐일 수 있는 치환제를 갖는 치환 페닐로 구성)이고; R5가 R2이거나이며; X는 O이거나 NH이며; Y는 C2 내지 C5알킬렌사슬, 알킬렌옥시알킬렌, 티오알킬렌, 혹은 알킬렌아미노알킬렌사슬이며; Z는 저급알킬, 저급알콕시, 시아노, 할로 및 트리플오로메틸 중에서 선택된 하나 혹은 그 이상의 치환체 그룹으로 치환되거나 치환되지 않을 수 있는페닐피리디닐 혹은 피리미디닐인 일반식 XXI의 화합물과 이 물질의 약제상 허용 가능한 산부가염.
  3. X가 NH인 청구범위 제1항의 화합물.
  4. R5가인 청구범위 제1항의 화합물.
  5. R2와 R6가 저급알킬이고, R4가 니트로페닐이며, R5가 저급알킬이거나이고 X가 0이나 NH이며; Y가 C2-C4알킬렌 사슬이고, Z가 치환페닐인 청구범위 제1항의 화합물.
  6. R2와 R6가 메틸이고, R4가 3-니트로페닐, R5가 메틸, X가 O, Y가 C2나 C3알킬렌사슬이며, Z가 2-메톡시페닐환인 청구범위 제1항의 화합물.
  7. [3-[4-[(2-피리미디닐)-4-피페라지닐]프로필]메틸 1,4-디하이트로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트인 청구범위 제1항의 화합물.
  8. [3-[4-(3-시아노-2-피리디닐)-1-피페라지닐]프로필]메틸-1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트인 청구범위 제1항의 화합물.
  9. [3-[[3-[4-(2-메톡시-페닐)-1-피페라지닐]프로필]아미노]프로필]메틸 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트인 청구범위 제1항의 화합물.
  10. [2-[2-[4-(2-메톡시페닐)-1-피페라지닐]에톡시]에틸]메틸 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트인 청구범위 제1항의 화합물.
  11. [2-[2-[4-(2-메톡시페닐)-1-피페라지닐]에톡시]에틸] 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트인 청구범위 제1항의 화합물.
  12. [2-메톡시에틸)[3-[4-(2-메톡시페닐)-1-피페라지닐]프로필] 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트인 청구범위 제1항의 화합물.
  13. 메틸 1,4-디하이드로-5-[[[3-[4-(2-메톡시페닐)-1-피페라지닐]프로필]아미노]카보닐]-2,6-디메틸-4-(3-니트로페닐)-3-피리딘디카복실레이트인 청구범위 제2항의 화합물.
  14. 메틸 1,4-디하이드로-5-[[[2-[4-(2-메톡시페닐)-1-피페라지닐]에틸]아미노]카보닐]-2,6-디메틸-4-(3-니트로페닐)-3-피리딘디카복실레이트인 청구범위 제2항의 화합물.
  15. 비스-[3-[4-(2-메톡시페닐)-1-피페라지닐]프로필] 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트인 청구범위 제3항의 화합물.
  16. 비스-[3-[11-(2-피리미디닐)-4-피페라지닐]프로필] 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트인 청구범위 제3항의 화합물.
  17. [3-[4-(2-메톡시페닐)-1-피페라지닐]프로필]메틸 1,4-디하이드로-2,6-디메틸-4-(2-니트로페닐)-3,5-피리딘디카복실레이트인 청구범위 제4항의 화합물.
  18. [2-[4-페닐-1-피페라지닐)에틸]메틸 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트인 청구범위 제4항의 화합물.
  19. 4-[4-[(2메톡시페닐)-1-피페라지닐]부틸]메틸 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트인 청구범위 제4항의 화합물.
  20. [3-[4-[3-(트리플루오로메틸)페닐]-1-피페라지닐]프로필]메틸 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트인 청구범위 제4항의 화합물.
  21. 에틸 [3-[4-[2-(메톡시 페닐)-1-피페라지닐]프로필] 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트인 청구범위 제4항의 화합물.
  22. [3-[4-(3-(클로로페닐)-1-피페라지닐]프로필]메틸 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트인 청구범위 제4항의 화합물.
  23. [3-[4-(2-(메톡시페닐-1-피페라지닐]프로필]메틸 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트인 청구범위 제5항의 화합물.
  24. 2-[4-(2-(메톡시페닐-1-피페라지닐)메틸 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트인 청구범위 제5항의 화합물.
  25. [3-[4-(4-플루오로페닐)-1-피페라지닐]프로필]메틸 디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트인 청구범위 제4항의 화합물.
  26. 비스 [3-[4-(4-플루오로페닐)-피페라지닐]프로필] 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트인 청구범위 제3항의 화합물.
  27. 메틸 [3-[4-(2-트리플루오로메틸)페닐]-1-피페라지닐]프로필] 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트인 청구범위 제4항의 화합물.
  28. 메틸 [3-[4-(2-메틸 페닐)-1-피페라지닐]프로필] 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트인 청구범위 제4항의 화합물.
  29. 비스 [3-[4-(2-메틸 페닐)-1-피페라지닐]프로필] 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트인 청구범위 제3항의 화합물.
  30. [2-(N,N-디메탈아미노)-에틸] [3-[4-(2-메톡시페닐)-1-피페라지닐]프로필 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트인 청구범위 제1항의 화합물.
  31. 치료상의 잇점이 현관확장으로 부터 일어나는 조건을 갖춘 포유동물에 청구범위 제1항에서 청구된 바와 같은 화합물의 비독성이면서도 효과적인 혈관 확장작용을 하는 투여량을 투여하는 것으로 구성되는, 포유동물 숙주에서 혈관확장효과를 일으키게 하는 방법.
  32. 청구범위 제1항에서 청구된 화합물을 비독성이면서 효과적인 항고혈압성을 지닌 투여량으로 고혈압증이 있는 포유동물 숙주에 투여하는 것으로 구성되는, 고혈압억제 방법.
  33. 저혈성 발명의 포유동물 숙주 대상체에 청구범위 제1항에서 청구된 화합물의 비독성이면서 항저혈성 투여량을 투여하는 것으로 구성되는 저혈 억제 방법.
  34. 치료적 잇점이 혈소판 기능 억제에서 일어나는 조건을 갖춘 포유동물에 청구범위 제1항에서 청구된 환합물의 비독성이면서 효과적인 혈소판 기능 억제 투여량을 투여하는 것으로 구성되는 혈소판 기능 억제 방법.
  35. 약 5 내지 약 50mg의 청구범위 제1항에서 청구된 화합물을 약제상 허용 가능하고 비독성인 불활성 담체와 혼합시킨 것으로 구성되는, 앙기나, 고혈압 혹은 저혈과 같은 심장혈관병을 치료하는 약제상조성물.
  36. [2-[[2-[4-(2-메톡시-페닐)-1-피페라지닐]에틸]티오]에틸]메틸 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트인 청구범위 제1항의 화합물.
  37. [5-[4-(2-메톡시페닐)-1-피페라지닐]펜틸]메틸 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트인 청구범위 제1항의 화합물.
  38. 생성물이 다음 화합물중 어떤 것임을 특징으로 하는 방법. 2-[4-(2-메톡시페닐)-1-피페라지닐]에틸]메틸 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘 디카복실레이트 디하이드로클로라이드하이드레이트, [2-(4-페닐-1-피페라지닐)에틸]메틸 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트, [3-[4-(2-메톡시페닐)-1-피페라지닐)프로필]메틸 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트, 메틸 1,4-디하이드로-5-[[[2-(4-(2-메톡시페닐)-1-피페라지닐)]에틸]아미노]카보닐-2,6-디메틸-4-(3-니트로페닐)-3-피리딘카복실레이트, 메틸 1,4-디하이드로-5-[[[3-[4-(2-메톡시페닐)-1-피페라지닐]프로필]아미노]카보닐]-2,6-디메틸-4-(3-니트로페닐)-3-피리딘 카복실레이트, 비스-[3-[4-(2-메톡시페닐)-피페라지닐]프로필] 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트디하이드로클로라이드, 4-[4-[(2-메톡시페닐)-1-피페라지닐]부틸]메틸 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐) 3,5-피리딘디카복실레이트 디하이드로클로라이드, [3-[1-(2-피리디닐)-4-피페라지닐]프로필]메틸 1,4 -디하이드로-2,6-디메틸-4-(3-니트로페닐) 2,5-피리딘디카복실레이트 하이드로클로라이드 아세토니트릴솔베이트, 비스 [3-[1-(2-피리미디닐)-4-피페라지닐] 프로필] 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트하이드로클로라이드, [3-[4-(3-시아노-2-피리디닐)-1-피페라지닐]프로필]메틸 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트하이드로클로라이드, [3-[4-[3-(트리플루오로메틸)페닐]-1-피페라지닐]프로필]메틸 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트하이드로클로라이드, 에틸 [3-[4-(2-메톡시페닐)-1-피페라지닐]프로필] 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트하이드로클로라이드하이드레이트, [3-[[3-[4-(2-메톡시페닐)-1-피페라지닐]프로필]아미노]-프로필]메틸 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트디하이드로클로라이드하이드레이트, [2-[2-[4-(2-메톡시페닐)-1-피페라지닐]에톡시]에틸]메틸 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트하이드로클로라이드하이드레이트, 비스 [2-[2-[4-(2-에톡시페닐)-1-피페라지닐]에톡시]에틸] 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트 테트라하이드로 클로라이로 모노하이드레이트, (2-메톡시 에틸)[3-[4-(2-메톡시페닐)-1-피페라지닐]-프로필] 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트모노하이드레이트, [3-[4-(2-메톡시페닐)-1-피페라지닐]프로필]메틸 1,4-디하이드로-2,6-디메틸-4-(2-니트로페닐) 3,5-피리딘디카복실레이트모노하이드로클로라이드헤미하이드레이트, [3-[4-(3-클로로페닐)-1-피페라지닐)프로필]메틸 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트모노하이드로클로라이드, [3-[4-(4-플루오로페닐)-1-피페라지닐]프로필]메틸디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트, 비스 [3-[4-(4-플루오로페닐)피페라지닐]프로필] 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트, 메틸 [3-[4-(2-트리플루오로메틸)페닐-1-피페라지닐]-프로필] 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트, 메틸 [3-[4-(2-메틸페닐)-1-피페라지닐]프로필] 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트, 비스[3-[4-(2-메틸페닐)-1-피페라지닐]프로필]1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트, [2-(N,N-디메틸아미노)에틸][3-[4-(2-메톡시페닐)-1-피페라지닐]프로필] 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)3,5-피리딘디카복실레이트트리하이드로클로라이드, [2-[[2-[4-(2-메톡시페닐)-1-피페라지닐]에틸]티오]에틸]메틸 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트, [5-[4-(2-메톡시페닐)-1-피페라지닐]페닐]메틸 1,4-디하이드로-2,6-디메틸-4-(3-니트로페닐)-3,5-피리딘디카복실레이트클로로메탄솔베이트.
  39. 화합물이 약제 가능하고 고혈압치료와, 저혈 장애치료 및 어떤 혈소판의 기능을 억제하는데 유용한 것을 특징으로 하는 청구범위 제1항에 따른 화합물.
  40. 청구범위 제1항에 따른 화합물의 투여량이 포유동물의 체중에 대하여 약 1 내지 약 20mg/kg 범위 이내인 것으로 구성되는 포유동물에 경구 투여용으로 적합한 단위 투여형태인 약제상 조성물.
  41. 청구범위 제1항에 따른 화합물의 투여량이 포유동물의 체중에 대하여 약 0.05 내지 약 1mg/kg의 범위 이내인 것으로 구성되는 포유동물에 비경구 투여용으로 적합한 단위 투여 형태인 약제상 조성물.
  42. 청구범위 제1항에 따른 화합물의 투여량이 약 5 내지 약 50mg의 범위내이며, 이 투여량을 하루에 1 내지 3번 투여하는 것으로 구성되는, 포유동물에 경구 투여용으로 적합한 단위 투여량 형태인 약제상 조성물.
  43. 조성물이 약 10 내지 약 20mg 범위이내의 투여량을 함유하는 청구범위 제41항에 따른 조성물.
  44. 다음 그룹으로부터 선택된 공정으로 구성된 R2와 R6가 저급알킬, 하이드록시알킬, 알콕시알킬알킬, 아미노알킬, 혹은 디알킬아미노알킬로부터 독립적으로 선택되고; R4가 5-7탄소의 사이클로알킬, 7-9 탄소원자의 비이사이클로알케닐, 헤타릴(푸라닐, 인돌릴, 메틸티오피리딜, 디에닐, 벤즈옥사디아졸릴 및 밴조티아디아졸릴로 구성); 아릴(페닐, 나프틸 혹은 독립적으로 아세토아미노, 저급알킬, 저급알콕시, 시아노, 할로겐, 하이드록실, 니트로, 트리플루오로메틸, 트리플루오로메틸-술포닐 혹은 메틸슬포닐일 수 있는 치환체를 갖는 치환페닐로 구성)이고; R5가 R2이거나이며; X는 O이거나 NH이며; Y는 C2내지 C5알킬렌사슬, 알킬렌옥시알킬렌, 알킬렌티오알킬렌, 혹은 알킬렌아미노알킬렌사슬이며; Z는 저급알킬, 저급알콕시, 시아노, 할로 및 트리플루오로메틸중에서 선택된 하나 혹은 그 이상의 치환체 그룹으로 치환되거나 치환되지 않을 수 있는 페닐, 피리디닐 혹은 피리미디닐인, 일반식 XXI의 화합물과 이 물질의 약제상 허용 가능한 산부가염을 제조하는 방법.
  46. 가) 일반식Ⅱc
  47. 의 피페라지닐 알카노일 아세테이트 화합물을 변형된 Hantzsch 축합조건(암모늄 아세테이트/에타놀)하에 일반식 Ⅲb
  49. 의 3-옥소알카노에이트 화합물로 처리하여 X가 산소인 일반식 XXI의 화합물을 얻고;
  50. 나) 1) V가 C2-C5알킬렌사슬이고 W가 할로겐이며, 바람직하기는 염소인 일반식 Ⅱb
  52. 의 할로알킬 알킬노일 아세테이트를 변형된 Hnatzsch 축합조건(암모늄 아세테이트/에타놀)하에 일반식 Ⅲb의 3-옥소알카노에이트 화합물과 반응시켜서 일반식 ⅤⅡd의 중간체 생성물.
  54. 을 얻어서,
  55. 2) 그 중간체 생성물 ⅤⅡd를 U가 수소, 하이드록시알킬렌, 슬포하이드로 알킬렌 혹은 아미노알킬아민인 피페라진 중간체 ⅤⅢd
  57. 와 반응시켜서 X가 산소인 일반식 XXI의 생성물을 얻고;
  58. 다) 1) 일반식 XI의 1,3-디카보닐피페라진화합물
  60. 을 노베나켈(Knovenagel) 조건(벤젠중의 피페리딘과 초산)하에 일반식 X′의 적합한 알데히드
  61. R4-CHO X′
  62. 와 반응시켜서 일반식 Ⅲa
  64. 의 중간체 카브옥사미드 화합물을 얻어서,
  65. 2) 그 중간체 화합물 Ⅲa를 일반식 IVb의 엔아민 화합물
  67. 과 반응시켜서 X가 NH인 일반식 XXI의 생성물을 얻고;
  68. 라) 3- 및 5-피리딘환 위치에 대청을 갖는 일반식 XXI화합물이 필요하면, 일반식 IVa의 엔아민 피페라진 중간체 화합물을 Hantzsch 축합조건하에 일반식 X′의 적합한 알데히드
  70. 과 반응시켜서 XXI 생성물을 얻는 것.
  71. ※참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019850002382A 1984-04-11 1985-04-09 약제학상 유용한 디하이드로피리디닐디카르복실레이트 아마이드 및 에스테르의 제조방법 KR920005742B1 (ko)

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US06/693,426 US4755512A (en) 1984-04-11 1985-01-22 Pharmaceutically useful dihydropyridinyldicarboxylate amides and esters incorporating arylpiperazinylalkyl moities
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