KR870011100A - 1.5-디아릴-3-치환된-피라졸 및 그의 합성방법 - Google Patents

1.5-디아릴-3-치환된-피라졸 및 그의 합성방법 Download PDF

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KR870011100A
KR870011100A KR870005383A KR870005383A KR870011100A KR 870011100 A KR870011100 A KR 870011100A KR 870005383 A KR870005383 A KR 870005383A KR 870005383 A KR870005383 A KR 870005383A KR 870011100 A KR870011100 A KR 870011100A
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lower alkyl
methoxyphenyl
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폴 와취터 미카엘
폴 페로 미카엘
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벤자민 에프 람버트
오르토 파마슈티칼 코포레이션
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Abstract

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Description

1.5-디아릴-3-치환된-피라졸 및 그의 합성방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (30)

  1. 하기 일반식의 화합물 및 약제학적으로 허용되는 그의 염.
    상기식에서 R1, R2, R3및 R4는 동일하거나 상이하며, 독립적으로 수소, 저급알킬, 저급 알콕시, 페닐, 할로, 하이드록시, 저급 알킬설포닐, 저급알킬티오, 니트로, 트리플루오로메틸, ω-트리플루오로메틸, 저급 알콕시, 아미노, 아세트아미도, 카복시, 알킬하이드록삼산으로 이루어진 그룹 중에서 선택되거나, R1, R2,또는 R3, R4가 이들이 부착된 페닐그룹과함께 나프틸 또는 치환된 나프틸 그룹을 형성하고; R은 탄소수 2내지 16의 포화 또는 불포화된 직쇄 탄화수소이며; Y는 수소, 브로모, 클로로 또는 저급 알킬이고; X는 카복시, 하이드록시, 아세톡시, 알카노일옥시, 저급알콕시, 저급 알킬 카보닐, 옥시미노, 시아노, 아미노, C(O)-R5및 -C(O)C(O)-R5로 이루어진 그룹중에서 선택되며; R5는 수소, 알킬, 저급 알콕시 및 NR6R7로 이루어진 그룹중에서 선택되고, R6및R7은 동일하거나 상이하며 수소 및 저급 알킬로 이루어진 그룹중에서 선택되거나 R6또는R7은 수소, 저급알킬, 저급 알콕시, 하이드록시, 아실옥시, 벤질옥시, 2-하이드록시 저급 알킬, 저급 알킬 카복시, 페닐, 치환된 페닐, 피리딜, 타이졸릴, 디하이드로 타이졸릴, 5-테트라졸릴, -OCO(CH2)nCOR9[여기에서, R9는 -OH-ONa, 디알킬 아미노(예, 디에틸아미노)및 모폴리노이고, n은 2또는 3이다]; -OCOR10[여기에서, R10은 -CH2NR11R12｛여기에서, R11및R12는 알킬(예,메틸), 사이클로알킬(예, 사이클로헥실)이거나, 함께는 헤테로사이틀릭 환(예, N-메틸피페라지노)이다｝,-CH2Cl, -CH2O-저급알킬 또는 t-부틸, -CH-저급알킬-CO2-Q｛여기에서, Q는 저급알킬 또는 -H, 아실(예, 아세틸, 프로피오닐 또는 부티릴)이다｝이다]; -NR8OH[여기에서, R8은 수소, -CO-저급알킬, -CO-t-부틸, -COC7H15,-CO-페닐, SO2-저급알킬 및 -COCONHOH이다]; -NHR13[여기에서, R13은 수소, -CO-저급알킬, -CO-t-부틸, -COC7H15, -CO-페닐, SO2-저급알킬-COCO2-저급알킬, -COCONHOH, -COCO2H, -COCO2H, COCON(저급알킬)OH, 및 PO(O-저급알킬)2이다[;-C(R14)=NNH-2-티아졸리노,-CH(OH)R14및 -C(O)R14[여기에서,R14는 수소,저급알킬,페닐 및 t-부틸이다];-C(=NOH)NH2및 -C(=NH)N(OH)-저급알킬, ω-알카노에이트 및 O-NR8R9[여기에서, R8및 R9는 동일하거나 상이하며 수소, 저급알킬, 페닐 및 치환된 페닐로 이루어진 그룹중에서 선택된다]로 이루어진 그룹중에서 선택되며;단,(a)Y가 브로모 또는 클로로인 경우, X는 -COOH,CH2OH또는 -C(O)-R5[여기에서, R5는 NR6R7이고, 이때 R6는 -OH이며 R7은 저급알킬이다]이고; (b)(i)R-X가 (CH2)3CO2H또는 (CH2)2CO(O)NHOH이고 (ii)R3및 R4가 4-메톡시, 3-메톡시-4-하이드록시, 2-하이드록시 및 수소인 경우, R1및 R2중 적어도 하나는 수소 이외의 것이며; (c)R-X가 함께 탄소-탄소 결합에 의해 서로 결합된 3개의 포화된 탄소원자를 함유하는 경우, R1및 R2중 적어도 하나, 또는 R3및R4중 적어도 하나는 수소 이외의 것이다.
  2. 제1항에 있어서, R2및R4가 수소이고, R1및 R2이 할로, 트리플루오로메틸, 저급알킬 및 저급알콕시로 이루어진 그룹중에서 선택되는 화합물.
  3. 제2항에 있어서, R이 포화되는 직쇄이고 탄소-탄소 결합에 의해 서로 결합된 3개의 탄소원자를 함유하는 화합물.
  4. 제3항에 있어서, X가 하이드록시, 카복시, 약제학적으로 허용되는 양이온의 카복실레이트염, C(O)-NR6R7[여기에서, R6및 R7은 수소, 하이드록시, 메틸, t-부ㅣㄹ, 2-하이드록시에틸 및 카복시메틸로 이루어진 그룹중에서 선택된다]로 이루어진 그룹중에서 선택되는 화합물.
  5. 제2항에 있어서, R이 불포화되고 2내지 16개의 탄소원자를 함유하는 화합물.
  6. 제5항에 있어서, X가 카복실인 화합물 또는 그의 염.
  7. 하기 일반식의 화합물.
    상기식에서, R1및 R3는 할로, 트리플루오로메틸, 메틸 및 메톡시로 이루어진 그룹중에서 선택된다.
  8. 하기 일반식의 화합물.
    상기식에서, R1및 R3는 할로, 트리플루오로메틸, 메틸 및 메톡시로 이루어진 그룹중에서 선택되고, X는 카복시 및 C(O)-R5[여기에서, R5는 N(CH3)OH, N(t-C4H9)OH, NHOH, ONH(CH3)및 ONH(t-C4H9)로 이루어진 그룹중에서 선택된다]로 이루어진 그룹중에서 선택된다.
  9. 제1항에 있어서, 3-[5-(4-클로로페닐)-1-(4-메톡시페닐)-3-피라졸릴]-N-하이드록시-N-메틸프로판 아마이드인 화합물.
  10. 제1항에 있어서, 5-[(4-클로로페닐)-3-(3-하이드록시프로필)-1-(4-메톡시페닐)피라졸인 화합물.
  11. 제1항에 있어서, 5-[(4-트루플루오로메틸페닐)-3-(3-하이드록시프로필)-1-(4-메톡시페닐)피라졸인 화합물.
  12. 제1항에 있어서, 1-(4-브로모피닐)-5-(4-클로로페닐)-3-(3-하이드록시프로필)피라졸인 화합물.
  13. 제1항에 있어서, 나트륨8-[5-(4-클로로페닐)-1-(4-메톡시페닐)-3-피라졸릴]-5(Z)-옥테노에이트인 화합물.
  14. 제1항에 있어서, 나트륨3-[5-(4-클로로페닐)-1-(4-메톡시페닐)-3-피라졸릴]프로파노에이트인 화합물.
  15. 제1항에 있어서, 3-[5-(4-클로로페페)-1-(4-메톡시페닐)-3-피라졸릴]-N-3급-부틸-N-하이드록시 프로판아마이드인 화합물.
  16. 제1항에 있어서, N-카복시메틸-3-[5-(4-클로로페닐)-1-(4-메톡시페닐)-3-피라졸릴]-프로판아마이드인 화합물.
  17. 제1항에 있어서, N-카복시메틸-3-[5-(4-클로로페닐)-1-(4-메톡시페닐)-3-피라졸릴]프로판아마이드, 3-[5-(4-클로로페닐-1-(4-메톡시페닐)-3-피라졸릴]-N-하이드록시-N-이소프로필프로판아마이드, 3-[5-(4-클로로페닐-1-(4-메톡시페닐)-3-피라졸릴]-N-사이클로헥실-N-하이드록시프로판아마이드 및 3-[5-(4-클로로페닐-1-(4-메톡시페닐)-3-피라졸릴]-N-에틸-하이드록시프로판아마이드로 이루어진 그룹중에서 선택되는 화합물.
  18. 제1항에 있어서, 3-[5-(4-클로로페닐-1-(4-메톡시페닐)-3-피라졸릴]-N-하이드록시-N-페닐프로판아마이드, 3-[5-(4-클로로페닐-1-(4-메톡시페닐)-3-피라졸릴]프로필아민, 3-[5-(4-클로로페닐-1-(4-메톡시페닐)-3-피라졸릴]프로판알, 5-(4-클로로페닐-3-(3-옥시미노-프로필)-1-(4-메톡시페닐)피라졸릴 및3-(3-하이드록시프로필)-1-(4-메틸옥시페닐)-5-(4-톨릴)피라졸릴로 이루어진 그룹중에서 선택되는 화합물.
  19. 약제학적으로 허용되는 담체중에 분산된 활성성분으로서 제1항에 따른 치환된 피라졸 화합물의 유효량을 함유하는 국소, 경구, 비경구 및 에어로졸 두여용의 약제학적 조성물.
  20. 제19항에 있어서, 조성물이 포유류에 유입될 경우 치환된 피라졸 화합물이 조성물에 존재하는 양으로 사이클로옥시게네이스 및 리폭시게네이스 경로를 억제할 수 있느 약제학적 조성물.
  21. 제19항에 따른 약제학적 조성물을 포유류에게 투여하여 염증반응을 나타내는 포유류의 염증을 경감시키는 방법.
  22. 제19항에 따른 약제학적 조성물을 포유류에게 투여하여 건선 또는 다른 피부병을 포함한 피부의 염증상태를 치료하는 방법.
  23. 약제학적으로 허용되는 담체중에 분산된 활성성분으로 제1항에 따른 치환된 피라졸 화합물의 심근부전증에 대한 유효량을 함유하는 약제학적 조성물을 포유류에게 투여하여 앙기나, 혈관경련, 경색을 포함한 심근부전증을 치료하는 방법.
  24. 제19항에 따른 약제학적 조성물을 포유류에게 투여하여 천식 및 알레르기성 과민성 질환을 치료하는 방법.
  25. 아릴하이드라진을 알킬쇄의 탄소수가 적어도 4인 1-아릴-(오메가-치환된)-알킬-1,3-디온과 반응시키되, 상기 반응을 상기 반응조건에 대해 실질적으로 불활성인 용매중에서 수행하고, 상기 오메가-치환체는 상기 반응조건에 대해 실질적으로 불활성이며, 상기 아릴그룹은 동일하거나 상이하고 일-또는이-치환된 페닐이며, 여기에서 페닐치환체는 수소,저급알킬, 저급알콕시, 페닐, 할로, 하이드록시, 저급알킬설포닐, 저급알킬티오, 니트로, 트리플루오로메틸, 오메가-트리플루오로메틸 저급알콕시, 나프틸 및 치환된 나프닐로 이루어진 그룹중에서 선택됨을 특징으로하여, 제1항의 1,5-디아릴-3-(오메가-치환된 저급알킬)-피라졸을 합성하는 방법.
  26. 제1항에 있어서, 3-[1-(4-메톡시페닐)-5-(4-메틸페닐)-3-피라졸릴]-N-하이드록시-N-메틸프로판아마이드인 화합물.
  27. 제1항에 있어서, 3-[1-(4-메톡시페닐)-5-(4-메틸페닐)-3-피라졸릴]-N-석시닐옥시프로판아미드인 화합물.
  28. 제1항에 있어서, 3-[5-(4-클로로페닐)-1-(4-메톡시페닐)-3-피라졸릴]-N′-N′-디메틸글리시닐옥시-N-메틸프로판아마이드인 화합물.
  29. 제1항에 있어서, N-[3-5-(4-클로로페닐)-1-(4-메톡시페닐)-3-피라졸릴]프로필]-N,N′-디하이드록시-옥사마이드인 화합물.
  30. 제1항에 있어서, N-아세틸-N-아세톡시[5-(4-클로로페닐)-1-(4-메톡시페닐)-3-피라졸릴]프로판아마이드인 화합물.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019870005383A 1986-05-29 1987-05-29 1,5-디아릴-3-치환된-피라졸, 이의 합성방법 및 이를 포함하는 약제학적 조성물 KR960007163B1 (ko)

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US07/042,661 US4826868A (en) 1986-05-29 1987-04-29 1,5-Diaryl-3-substituted pyrazoles pharmaceutical compositions and use

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