KR960022445A - 제한된 9-시스-레티노이드 - Google Patents

제한된 9-시스-레티노이드 Download PDF

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KR960022445A
KR960022445A KR1019950072122A KR19950072122A KR960022445A KR 960022445 A KR960022445 A KR 960022445A KR 1019950072122 A KR1019950072122 A KR 1019950072122A KR 19950072122 A KR19950072122 A KR 19950072122A KR 960022445 A KR960022445 A KR 960022445A
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South Korea
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compound
methyl
formula
hydrogen
tetrahydro
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KR1019950072122A
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펭-링 큉
해롤드 번버그 게리
윌리암 엡스테인 조셉
매튜 길버트 아담
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이곤 이. 버그
아메리칸 시아나미드 캄파니
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Publication of KR960022445A publication Critical patent/KR960022445A/ko

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Abstract

본 발명은 관상 동맥 질환의 치료 및 예방에 유용하고 HDL 수준을 증가시켜 초기의 동맥 경화증을 보호하기 위한 신규한 9-시스-레티노산 유사체에 관한 것이다. 본 발명은 신규한 9-시스-레티노산 유사체를 제조하는 방법이 포함한다.

Description

제한된 9-시스-레티노이드
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (32)

  1. 일반식 (Ⅰ)의 화합물 및 약제학적으로 허용되는 염 및 에스테르.
    상기식에서, A, B 및 C는 CH, CH2, 산소 또는 황(여기서, 헤테로원자는 1개 이하가 존재한다)이고; D는 (CH)m(여기서, m은 0 내지 1의 정수이다) 또는 (CH)n(여기서, n은0 내지 2의 정수이다)이며, 점선(…)은 하나의 이중 결합만이 존재하는 겅우 a-b 위치에 위치하고, 다수의 이중 결합이 존재하는 경우 방향족 환을 생성하기 위해 공액 위치에 존재하는 이중 결합의 존재 또는 부재를 나타내고; R은 수소, 메틸, 에틸, t-부틸 또는 트리플루오로메틸이며; Ar은 일반식
    (여기서, R1, R2, R3및 R4는 수소, (C1-C3)알킬, (C1-C3)알콕시 또는 트리플루오로메틸이다)의 잔기, 일반식
    (여기서, R5는 수소, (C1-C3)알킬, 메톡시 또는 트리플루오로메틸이고, R6은 수소, 메틸 또는 에틸이다)의 잔기 또는 일반식
    (여기서, R6은 수소, 메틸 또는 에틸이고, R7은 수소, 메틸 또는 에틸이다)의 잔기이고; Y는 수소이며; X는 CH2OH, CHO, CO2H, CN, CH2CONH2또는 일반식(여기서, R8는 직쇄 또는 측쇄 (C1-C8)알킬이다) 또는 일반식(여기서, R9는 수소, 직쇄 또는 측쇄 C1-10)알킬, 글리코실, 2-메톡시에틸, 2-디멜틸아미노에틸, (1,2 또는 3)-피리딜 또는 (1,2 또는 3)-피리딜메틸이다)이거나, X와 Y는 함께 일반식.
    의 티아졸리딘디의 환을 형성한다.
  2. 일반식(Ⅰ)의 화합물 및 약제학적으로 허용되는 염 및 에스테르.
    상기식에서, A, B 및 C는 CH, CH2, 산소 또는 황(여기서, 헤테로원자는 1개 이하가 존재한다)이고; D는 (CH)m(여기서, m은 0 내지 1의 정수이다) 또는 (CH)n(여기서, n은0 내지 2의 정수이다)이며, 점선(…)은 하나의 이중 결합만이 존재하는 겅우 a-b 위치에 위치하고, 다수의 이중 결합이 존재하는 경우 방향족 환을 생성하기 위해 공액 위치에 존재하는 이중 결합의 존재 또는 부재를 나타내고; R은 수소, 메틸, 에틸, t-부틸 또는 트리플루오로메틸이며; Ar은 일반식
    (여기서, R1, R2, R3및 R4는 수소, (C1-C3)알킬, (C1-C3)알콕시 또는 트리플루오로메틸이다)의 잔기이고
    X는 CH2OH, CHO, CO2H, CN, CH2CONH2또는 일반식(여기서, R8는 직쇄 또는 측쇄 (C1-C8)알킬이다) 또는 일반식(여기서, R9는 수소, 직쇄 또는 측쇄 C1-10)알킬, 글리코실, 2-메톡시에틸, 2-디멜틸아미노에틸, (1,2 또는 3)-피리딜 또는 (1,2 또는 3)-피리딜메틸이다)의 잔기이며, Y는 수소이다.
  3. 일반식(Ⅰ)의 화합물 및 약제학적으로 허용되는 염 및 에스테르.
    상기식에서, A는 CH 또는 CH2이고, B 및 C는 CH, CH2, 산소 또는 황(여기서, 헤테로원자는 1개 이하가 존재한다)이며; D는 (CH)m(여기서 m은 0 내지 1의 정수이다) 또는 (CH2)n(여기서, n은 0 내지 2의 정수이다)이고; 점선(---)은 하나의 이중 결합만이 존재하는 경우 a-b 위치에 위치하고, 다수의 이중 결합이 존재하는 경우 방향족 환을 생성하기 위해 공액 위치에 존재하는 이중 결합의 존재 또는 부재를 나타내며; R은 수소, 메틸, 에틸, t-부틸 또는 트리플루오로메틸이고; Ar은 일반식
    (여기서, R5는 수소, (C1-C3)알킬, 메톡시 또는 트리플루오로메틸이고, R6은 수소, 메틸 또는 에틸이다)의 잔기이며 : X는 CH2OH, CHO, CO2H, CN, CH2CONH2또는 일반식(여기서, R8는 직쇄 또는 측쇄 (C1-C8)알킬이다) 또는 일반식(여기서, R9는 수소, 직쇄 또는 측쇄 C1-10)알킬, 글리코실, 2-메톡시에틸, 2-디멜틸아미노에틸, (1,2 또는 3)-피리딜 또는 (1,2 또는 3)-피리딜메틸이다)의 잔기이고, Y는 수소이다.
  4. 일반식 (Ⅰ)의 화합물 및 약제학적으로 허용되는 염 및 에스테르.
    상기식에서, A는 CH 또는 CH2이고; B 및 C는 CH, CH2산소 또는 황(여기서, 헤테로원자는 1개 이하가 존재한다)이며; D는 (CH)m(여기서, m은 0 내지 1의 정수이다) 또는 (CH2)n(여기서, n은0 내지 2의 정수이다)이고, 점선(…)은 하나의 이중 결합만이 존재하는 겅우 a-b 위치에 위치하고, 다수의 이중 결합이 존재하는 경우 방향족 환을 생성하기 위해 공액 위치에 존재하는 이중 결합의 존재 또는 부재를 나타내고; R은 수소, 메틸, 에틸, t-부틸 또는 트리플루오로메틸이며; Ar은 일반식
    (여기서, R6은 수소, 메틸 또는 에틸이고, R7은 수소, 메틸 또는 에틸이다)의 잔기이며; X는 CH2OH, CHO, CO2H, CN, CH2CONH2또는 일반식(여기서, R8는 직쇄 또는 측쇄 (C1-C8)알킬이다) 또는 일반식(여기서, R9는 수소, 직쇄 또는 측쇄 C1-10)알킬, 글리코실, 2-메톡시에틸, 2-디멜틸아미노에틸, (1,2 또는 3)-피리딜 또는 (1,2 또는 3)-피리딜메틸이다)의 잔기이고: Y는 수소이다.
  5. 제3항에 있어서, Z, E 및 E, E-3-메틸-5-[2-(5,6.,7,8-테트라하이드로-5,5,8,8-테트라메틸-2-나프탈레닐)-1-사이클로헥센-1-일]-2,4-펜타디에노산 에틸 에스테르인 화합물.
  6. 제3항에 있어서, E,E-3-메틸-5-[2-(5,6.,7,8-테트라하이드로-5,5,8,8-테트라메틸-2-나프탈레닐)-1-사이클로헥센-1-일]-2,4-펜타디에노산인 화합물.
  7. 제3항에 있어서, Z, E 및 E, E-3-메틸-5-[2-(5,6.,7,8-테트라하이드로-5,5,8,8-테트라메틸-2-나프탈레닐)-1-사이클로펜텐-1-일]-2,4-펜타디에노산 에틸 에스테르인 화합물.
  8. 제3항에 있어서, E, E-3-메틸-5-[2-(5,6.,7,8-테트라하이드로-5,5,8,8-테트라메틸-2-나프탈레닐)-1-사이클로펜텐-1-일]-2,4-펜타디에노산인 화합물.
  9. 제3항에 있어서, Z, E 및 E, E-3-메틸-5-[2-(3,5,5,8,8-펜타메틸-5,6,7,8-테트라하이드로-2-나프탈레닐)-1-사이클로헥센-1-일]-2,4-펜타디에노산 에틸 에스테르인 화합물
  10. 제3항에 있어서, E, E-3-메틸-5-[2-(3,5,5,8,8-펜타메틸-5,6,7,8-테트라하이드로-2-나프탈레닐)-1-사이클로헥센-1-일]-2,4-펜타디에노산인 화합물.
  11. 제3항에 있어서, Z, E 및 E, E-3-메틸-5-[2-(3,5,5,8,8-펜타메틸-5,6,7,8-테트라하이드로-2-나프탈레닐)-1-사이클로펜텐-1-일]-2,4-펜타디에노산 에틸 에스테르인 화합물
  12. 제3항에 있어서, E, E-3-메틸-5-[2-(3,5,5,8,8-펜타메틸-5,6,7,8-테트라하이드로-2-나프탈레닐)-1-사이클로펜텐-1-일]-2,4-펜타디에노산인 화합물.
  13. 제3항에 있어서, 3-메틸-5-[2-(5,6,7,8-테트라하이드로-3,5,5,8,8-펜타메틸-2-나프탈레닐)-페닐]-2,4-펜타디에노산인 화합물.
  14. 제3항에 있어서, (Z,E)-5-[3-[2-(5,6.,7,8-테트라하이드로-3,5,5,8,8-펜타메틸-2-나프탈레닐)-1-사이클로헥센-1-일]-2-프로페닐리덴-2,4-티아졸리딘디온인 화합물.
  15. 제3항에 있어서, 3-메틸-5-[2-(5,6.,7,8-테트라하이드로-3,5,5,8,8-테트라메틸-2-나프탈레닐)페닐]-2,4-펜타디에노산인 화합물.
  16. 제4항에 있어서, E,E-3-메틸-5-[2-(1,1,3,3-테트라메틸-1,3-디하이드로-5-이소벤조푸라닐)-1-사이클로펜트-1-일]-2, 4-펜타디에노산인 화합물.
  17. 치료학적 유효량의 제1항의 화합물 및 약제학적으로 허용되는 담체를 포함하는 포유동물의 관상 동맥 질환을 치료 및 예방하기 위한 약제학적 조성물.
  18. 치료학적 유효량의 제1항의 화합물 및 약제학적으로 허용되는 담체를 포함하는 포유동물의 플라스마 고밀도 지방단백질(HDL) 수준을 증가시키기 위한 약제학적 조성물.
  19. 치료학적 유효량의 제1항의 화합물 및 약제학적으로 허용되는 담체를 포함하는 포유동물의 아테롬성 동맥경화증을 치료 및 예방하기 위한 약제학적 조성물.
  20. 제17항에 있어서, 화합물이 E, E-3-메틸-5-[2-(3,5,5,8,8-펜타메틸-5,6,7,8-테트라하이드로-2-나프탈레닐)-1-사이클로펜텐-1-일]-2,4 -펜타디에노산인 조성물.
  21. 제17항에 있어서, 화합물이 E, E-3-메틸-5-[2-(5,6,7,8-테트라하이드로-5,5,8,8-테트라메틸-2-나프탈레닐)-1-사이클로헥센-1-일]-2,4 -펜타디에노산인 조성물.
  22. 제18항에 있어서, 화합물이 E, E-3-메틸-5-[2-(3,5,5,8,8-펜타메틸-5,6,7,8-테트라하이드로-2-나프탈레닐)-1-사이클로펜텐-1-일]-2,4 -펜타디에노산인 조성물.
  23. 제18항에 있어서, 화합물이 E, E-3-메틸-5-[2-(5,6,7,8-테트라하이드로-5,5,8,8-테트라메틸-2-나프탈레닐)-1-사이클로헥센-1-일]-2,4 -펜타디에노산인 조성물.
  24. 제19항에 있어서, 화합물이 E, E-3-메틸-5-[2-(3,5,5,8,8-펜타메틸-5,6,7,8-테트라하이드로-2-나프탈레닐)-1-사이클로펜텐-1-일]-2,4 -펜타디에노산인 조성물.
  25. 제19항에 있어서, 화합물이 E, E-3-메틸-5-[2-(5,6,7,8-테트라하이드로-5,5,8,8-테트라메틸-2-나프탈레닐)-1-사이클로헥센-1-일]-2,4 -펜타디에노산인 조성물.
  26. 치료학적 유효량의 제1항의 화합물 및 약제학적으로 허용되는 담체를 포함하는, 포유 동물에서 종양세표 분화의 유도에 의한 암을 치료하기 위한 약제학적 조성물.
  27. 제26항에 있어서, 화합물이 E, E-3-메틸-5-[2-(5,6,7,8-테트라하이드로-5,5,8,8-테트라메틸-2-나프탈레닐)-1-사이클로헥센-1-일]-2,4 -펜타디에노산인 조성물.
  28. 제26항에 있어서, 화합물이 E, E-3-메틸-5-[2-(5,6,7,8-테트라하이드로-5,5,8,8-테트라메틸-2-나프탈레닐)-1-사이클로펜텐-1-일]-2,4 -펜타디에노산인 조성물.
  29. 일반식 ArBr 또는 ArI(여기서, Ar은 제1항에 정의된 바와 같다)의 화합물을 불활성 용매중에서 -78℃ 내지 +30℃에서 알킬리튬과 반응시킨 다음 ZnCl2를 첨가하여 일반식 ArZnCL(여기서, Ar은 제1항에 정의된 바와 같다)의 화합물을 수득하고: ArZnCl을 팔라듐(O) 촉매의 조재하에 불활성 용매중에서 10℃내지 60℃에서 일반식(Ⅱ)의 화합물과 반응시켜 일반식(Ⅲ)의 화합물을 수득하며; 일반식(Ⅲ)의 화합물을 불활성 용매중에서 0℃ 내지 60℃에서 수소화 물 환원제와 반응시켜 일반식(Ⅳ)의 화합물을 수득하고; 일반식(Ⅳ)의 화합물을 삼치환된 포스핀 하이드로 브로마이드와 반응시켜 일반식(Ⅴ)의 화합물을 수득하며; 일반식(Ⅴ)의 화합물을 불활성 용매중에서 0℃에서 염기와 반응시킨 다음 일반식 O=C[여기서, R은 제1항에 정의된 바와 같고, X는 CO2R8(여기서, R8은 제1항에 정의된 바와 같다)이다]의 알데히드를 첨가하여 일반식(Ⅰ)의 화합물을 수득함을 특징으로 하여, 제1항에 따른 일반식(Ⅰ)의 화합물을 제조하는 방법.
    상기식에서, Ar, A, B, C, D, a,, b, R 및 점선(…)은 제1항에서 정의된 바와 같다.
  30. X가 -CO2H 또는 -CO2R8(여기서, R8은 제1항에 정의된 바와 같다)인 일반식(Ⅰ)의 화합물을 불활성 용매중에서 0℃ 내지 60℃에서 수소화물 환원제와 반응시켜 X가 - CH2OH인 일반식(Ⅰ)의 화합물을 수득하고; X가 -CH2OH인 일반식(Ⅰ)의 화합물을 산화제와 반응시켜 X가-CHO인 일반식(Ⅰ)의 화합물을 수득함을 특징으로 하여, X가 -CHO인 제1항에 따른 일반식(Ⅰ)의 화합물을 제조하는 방법.
    상기식에서, Ar, A, B, C, D, a,, b, R 및 점선(…)은 제1항에서 정의된 바와 같다
  31. X가 -CO2R8(여기서, R8은 제1항에 정의된 바와 같다)인 일반식(I)의 화합물을 가수분해 조건하에 30℃ 내지 100℃에서 염기와 반응시킨 다음 무기산으로 산성화시켜 X가 -CO2H인 일반식(Ⅰ)의 화합물을 수득하고; X가 -CH2OH인 일반식(Ⅰ)의 화합물을 불활성 용매중에서 0℃ 내지 25℃에서 활성화 시약과 반응시켜 중간 생성물을 수득하며; 중간 생성물에 일반식 R9NH2(여기서, R9는 제1항에 정의된 바와 같다)의 아민을 첨가하여 일반식(Ⅰ)의 화합물을 수득함을 특징으로 하여, X가 -C(O)-NHR9(여기서, R9는 제1항에 정의된 바와 같다)인 제1항에 따른 일반식(Ⅰ)의 화합물을 제조하는 방법.
    상기식에서, Ar, A, B, C, D, a,, b, R 및 점선(…)은 제1항에서 정의된 바와 같다
  32. 일반식(Ⅳ)의 화합물을 불활성 용매중에서 0℃ 내지 40℃에서 산화제와 반응시켜 일반식Ⅷ)의 화합물을 수득하고, 일반식(Ⅷ)의 화합물을 여기의 존재하에 불활성 용매중에서 일반식
    (여기서, R은 제1항에 정의된 바와 같다)의 일리드와 반응시켜 일반식(Ⅰ)의 화합물을 수득함을 특징으로 하여, X가 -CO2R8(여기서, R8은 제1항에 정의된 바와 같다)인 제1항에 따른 일반식(Ⅰ)의 화합물을 제조하는 방법.
    상기식에서, Ar, A, B, C, D, a,, b, R 및 Y는 제1항에서 정의된 바와 같다
    ※ 참고사항:최초출원 내용에 의하여 공개하는 것임.
KR1019950072122A 1994-12-19 1995-12-18 제한된 9-시스-레티노이드 KR960022445A (ko)

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US7655699B1 (en) 1992-04-22 2010-02-02 Eisai Inc. Compounds having selective activity for retinoid X receptors, and means for modulation of processes mediated by retinoid X receptors
US7115728B1 (en) 1995-01-30 2006-10-03 Ligand Pharmaceutical Incorporated Human peroxisome proliferator activated receptor γ
US5675033A (en) * 1995-06-06 1997-10-07 Allergan 2,4-pentadienoic acid derivatives having retinoid-like biological activity
EP1336600A3 (en) 1995-10-06 2004-07-07 Ligand Pharmaceuticals Incorporated Dimer-selective RXR modulators and methods for their use
FR2763588B1 (fr) * 1997-05-23 1999-07-09 Cird Galderma Composes triaromatiques, compositions les contenant et utilisations
WO1999005161A1 (en) 1997-07-25 1999-02-04 Ligand Pharmaceuticals Incorporated HUMAN PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA (PPARη) GENE REGULATORY SEQUENCES AND USES THEREFOR
EP1212322A2 (en) 1999-08-27 2002-06-12 Ligand Pharmaceuticals Incorporated 8-substituted-6-trifluoromethyl-9-pyrido[3,2-g]quinoline compounds as androgen receptor modulators
WO2001016139A1 (en) 1999-08-27 2001-03-08 Ligand Pharmaceuticals Incorporated Androgen receptor modulator compounds and methods
US6566372B1 (en) * 1999-08-27 2003-05-20 Ligand Pharmaceuticals Incorporated Bicyclic androgen and progesterone receptor modulator compounds and methods
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