KR920016437A - 피라닐 시아노구아니딘 유도체 - Google Patents

피라닐 시아노구아니딘 유도체 Download PDF

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KR920016437A
KR920016437A KR1019920002992A KR920002992A KR920016437A KR 920016437 A KR920016437 A KR 920016437A KR 1019920002992 A KR1019920002992 A KR 1019920002992A KR 920002992 A KR920002992 A KR 920002992A KR 920016437 A KR920016437 A KR 920016437A
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애트월 카네일
제이.그로버 게리
에스. 김 경
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니콜라스 피. 말라테스티닉
이이. 아르. 스퀴브 앤드 산즈, 인크
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Abstract

내용 없음

Description

피라닐 시아노구아니딘 유도체
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (34)

  1. 하기 일반식을 갖는 피라닐 시아노구아니딘 유도체 화합물.
    식 중, R1및 R7은 각각 독립적으로 수소, 시아노, 알콕시, 니트로, 할로 히드록시, 할로알킬, 벤질옥시이되, 단, R1및 R7중 적어도 하나는 수소가 아니고, R2는 수소, 히드록시 또는이고, R3및 R4는 각각 독립적으로 수소, 알킬 또는 아릴알킬이거나, 또는 R3및 R4는 이들이 결합된 탄소원자와 함께 5 내지 7원 카르보시클릭고리를 형성하고, R5는 H, 알킬, 할로알킬, 알케닐, 알키닐, 시크롤알킬, 아릴알킬, 시클로알킬알킬, -DN, -NO2, -COR, -COOR, -CONHR2, -CF3, S-알킬, -SO-알킬, -SO2알킬,,할로겐, 아미노, 치환 아미노, O-알킬, OCF2, OCH2CF3, -OCO알킬, -OCONR알킬, -NRCO알킬 및 NRCOO알킬, NRCONR2(상기 기들 중에서, R은 수소, 알킬, 할로알킬, 아릴, 아릴알킬, 시클로알킬, 또는 (시클로알킬)알킬기임)중에서 선택되고, R6는 H, 알킬, OH, O-알킬, 아미노, 치환 아미노, NHCOR(여기서, R은 상기한 바와 같음), CN, 및 NO2중에서 선택되고, R8은 수소, 알킬 중에서 선택되고, R9는 수소, 알킬, 알케닐, 아릴, 알릴알킬, 시클로알킬 또는 시클로알킬알킬중에서 선택되고, n은 1,2 또는 3이다.
  2. 제1항에 있어서, R1은 클로로 또는 플루오로이고, R2는 트란스-히드록시이고, R3및 R4는 각각 메틸이고, R5는 -CN 또는 -NO2이고, R6는 수소이고, R7은 수소이고, R8은 수소이고, R9는 수소인 화합물.
  3. 제1항에 있어서, 하기 일반식을 갖는 화합물.
    식 중, R1은 플루오로 또는 클로로이다.
  4. 제1항에 있어서, 화합물이 (트란스)-N"-시아노-N-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)-N'-(4-시아노 페닐)구아니딘인 화합물.
  5. 제1항에 있어서, 화합물이 (트란스)-N"-시아노-N-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)-N'-(4-메톡시 페닐)구아니딘인 화합물.
  6. 제1항에 있어서, 화합물이 (트란스)-N"-시아노-N-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)-N'-(4-니트로 페닐)구아니딘인 화합물.
  7. 제1항에 있어서, 화합물이 (트란스)-N-(4-클로로페닐)-N"-시아노-N-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)구아니딘인 화합물.
  8. 제1항에 있어서, 화합물이 (트란스)-N-(2-클로로페닐)-N"-시아노-N-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)구아니딘인 화합물.
  9. 제1항에 있어서, 화합물이 (트란스)-N-(3-클로로페닐)-N"-시아노-N-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)구아니딘인 화합물.
  10. 제1항에 있어서, 화합물이 (트란스)-N-(4-플루오로페닐)-N"-시아노-N-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)구아니딘인 화합물.
  11. 제1항에 있어서, 화합물이 (3S-트란스)-N"-시아노-N-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)-N'-(4-플루오로페닐)구아니딘인 화합물.
  12. 제1항에 있어서, 화합물이 (3S-트란스)-N-(4-클로로페닐)-N"-시아노-N'-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)구아니딘인 화합물.
  13. 제1항에 있어서, 화합물이 (3S-트란스)-N-(3-클로로페닐)-N"-시아노-N'-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)구아니딘인 화합물.
  14. 제1항에 있어서, 화합물이 트란스-N"-시아노-N-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)-N'-(4-(페닐 메톡시)페닐)구아니딘인 화합물.
  15. 제1항에 있어서, 화합물이 트란스-N"-시아노-N-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)-N'-(4-히드록시페닐)구아니딘인 화합물.
  16. 제1항에 있어서, 화합물이 (3S-트란스)-N-(3,4-디클로로페닐)-N"-시아노-N'-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)구아니딘인 화합물.
  17. 제1항에 있어서, 화합물이 (3S-트란스)-N"-시아노-N'-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)-N'-(4-트리플루오로메틸)페닐구아니딘인 화합물.
  18. 하기 일반식(Ⅱ)의 화합물을 카르보디이미드 존재하에 하기 일반식(Ⅲ)의 화합물과 커플링시키는 것으로 이루어지는 하기 일반식(Ⅰ)의 화합물의 제조방법.
    식 중, R1및 R7은 각각 독립적으로 수소, 시아노, 알콕시, 니트로, 할로 히드록시, 할로알킬, 벤질옥시이되, 단, R1및 R7중 적어도 하나는 수소가 아니고, R2는 수소, 히드록시 또는이고, R3및 R4는 각각 독립적으로 수소, 알킬 또는 아릴알킬이거나, 또는 R3및 R4는 이들이 결합된 탄소원자와 함께 5 내지 7원 카브보시클릭 고리를 형성하고, R5는 H, 알킬, 할로알킬, 알케닐, 알키닐, 시클로알킬, 아릴알킬, 시클로알킬알킬, -CN, -NO2, -COR, -COOR, -CONHR, -CONR2, -CF3, S-알킬, -SO-알킬, -SO2알킬,,할로겐, 아미노, 치환 아미노, O-알킬, OCF2, OCH2CF3, -OCO알킬, -OCONR알킬, -NRCO알킬 및 NRCOO알킬, NRCONR2(상기 기들 중에서, R은 수소, 알킬, 할로알킬, 아릴, 아릴알킬, 시클로알킬, 또는 (시클로알킬)알킬기임)중에서 선택되고, R6는 H, 알킬, -OH, O-알킬, 아미노, 치환 아미노, NHCOR(여기서, R은 상기한 바와 같음), CN, 및 NO2중에서 선택되고, R8은 수소, 알킬 중에서 선택되고, R9는 수소, 알킬, 알케닐, 아릴, 알릴알킬, 시클로알킬 또는 시클로알킬알킬중에서 선택되고, n은 1,2 또는 3이다.
  19. 제18항에 있어서, 상기 카르보디이미드가 하기 일반식을 갖는 방법.
    식중, X는 할로겐이고, Ra, Rb및 Rc는 독립적으로 알킬, 시클로알킬, 페닐, 페닐알킬, 시클로알킬알킬이거나, 또는 Ra 및 Rb가 N-원자와 함께 1-피롤리디닐, 1-피페리디닐, 4-모르폴리닐, 4-티오모르폴리닐, 4-알킬-1-피레라지닐 또는 4-페닐알킬-1-피페라지닐을 형성한다.
  20. 제18항에 있어서, 상기 카르보디이미드가 1-(3-디메틸아미노 프로필)-3-에틸-카르보디이미드 염산염인 방법.
  21. 제1항에 있어서, 화합물이 (3S-트란스)-N"-시아노-N-(6-시아노-3,4-디히드로-3-히드록시-2,2디메틸-2H-1-벤조피란-4-일)-N'-(4-니트로페닐)구아니딘인 화합물.
  22. 제1항에 있어서, 화합물이 (3S-트란스)-N-(3니트로페닐)-N"-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸2H-1-벤조피란-4-일)구아니딘인 화합물.
  23. 제1항에 있어서, 화합물이 (3S-트란스)-N-(3-트리플루오로메닐페닐)-N"-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)구아니딘인 화합물.
  24. 제1항에 있어서, 화합물이 (3S-트란스)-N'-시노아-N-6(-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)-N'-(3-메틸페닐)구아니딘인 화합물.
  25. 제1항에 있어서, 화합물이 (3S-트란스)-N"-N"-시아노-N'-(6-시아노-3,4-디히드로-3-히드록시-2,2-디메틸-2H-1-벤조피란-4-일)-N'-(4-메틸페닐)구아니딘인 화합물.
  26. 장기 보호량의 제1항의 화합물로 이루어진, 장기 외과 수술을 받는 포유동물의 허혈성 손상으로부터 장기를 보호하기 위한 제약 조성물.
  27. 제26항에 있어서, 상기 수술이 심폐의 보조관(bypass)수술인 조성물.
  28. 제26항에 있어서, 상기 수술이 장기 이식 수술인 조성물.
  29. 제28항에 있어서, 사기 수술이 심장 이식 수술인 조성물.
  30. 제26항에 있어서, 상기 화합물을 장기 기능을 보존, 보호 또는 유지하기 위하여 상기 수술에 사용되는 용액에 첨가한 조성물.
  31. 제30항에 있어서, 심장 보호량의 상기 화합물을 심폐의 보조관 또는 심장 이식 수술에 관련된 심장을 정지, 관류, 저장 및(또는)보호하는데 사용되는 심장마비(cadioplegic)용액에 첨가한 조성물.
  32. 제26항에 있어서, 상기 화합물을 상기 수술 이전 및(또는)도중 및(또는)이후에 장기 외과 수술을 받는 포유동물종에 투여하기 위한 조성물.
  33. 제28 또는 29항에 있어서, 상기 화합물을 상기 장기를 장기 기증자로부터 제거하기 이전 및(또는) 도중 및(또는) 이후에 장기 수용자에게 투여하기 위한 조성물.
  34. 심장 보호량의 제1항의 화합물 및 적당한 담체를 함유하는 심장 마비 용액.
    ※ 참고사항 : 최초출원 내용에 의하여 공개되는 것임.
KR1019920002992A 1991-02-27 1992-02-26 피라닐 시아노구아니딘 유도체 KR920016437A (ko)

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