KR960704838A - 디플루오로 스타톤 항바이러스성 유사체 (Difluoro statone antiviral analogs) - Google Patents

디플루오로 스타톤 항바이러스성 유사체 (Difluoro statone antiviral analogs)

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KR960704838A
KR960704838A KR1019960701172A KR19960701172A KR960704838A KR 960704838 A KR960704838 A KR 960704838A KR 1019960701172 A KR1019960701172 A KR 1019960701172A KR 19960701172 A KR19960701172 A KR 19960701172A KR 960704838 A KR960704838 A KR 960704838A
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alkyl
alkylene
benzyl
phenyl
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반 도르쎌라 비비안
쉬를렝 다니엘
타르뉘 셀린느
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스티븐 엘. 네스빗
메렐 파마슈티칼즈 인코포레이티드
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Abstract

본 발명은 신규의 스타톤 항바이러스성 유사체, 이의 제조방법 및 이의 제조에 유용한 중간체, 및 항바이러스 제제로서의 이의 용도에 관한 것이다.

Description

디플루오로 스타톤 항바이러스성 유사체(Difluoro statone antiviral analogs)
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (30)

  1. 일반식(I)의 화합물, 및 이의 입체이성질체, 수화물, 동배체 및 약제학적으로 허용되는 염.
    상기 식에서 P1은 C1-6알킬렌{여기서, T´는 [(O)´b- W´-R´]이고, T´은 [(O)´b- W´-R´]이거나, H이다(여기서, 각각의 W 및 W´는 독립적으로 C1-6알킬렌이거나 존재하지 않으며, 단 W가 R의 질소원자에 직접 결합되는 경우, W는 C2-6알킬렌이고, W´가 R´의 질소원자에 직접 결합되는 경우, W는 C2-6알킬렌이다)}이고; P2는 C1-6알킬, 사이클로펜틸, 하이드록시 C1-6알킬, 페닐, 벤질 또는 3-테트라하이드로푸릴이고; R 및 R´는 각각 독립적으로 C2-6알케닐렌, 피페라지닐, 치환된 피페라지닐, 피페리딜, 몰폴리닐, 피리딜, 피라지닐 또는 피리미디닐 〔여기서, 치환된 피페라지닐은 이의 하나의 질소 원자가 CHO, C(O)NHR4, C1-4알킬 또는 CO2R4에 의해 치환돈 피페라지닐이다〕이며; R1은 벤질옥시, C1-6알콕시, C1-6알킬, 페닐, 벤질, 펜에틸, 플로오레닐메틸렌옥시, 2-퀴놀리닐, PDL,,NHSO2R4, N(R4) (벤질) 또는 N(R4)(PDL)이며; PDL은 -(CH2)a-2, 3- 또는 4-피리딜, 또는 p-치환된 벤질옥시[여기서, 치환체는 니트로, OH, 아미노, C1-6알콕시. 하이드록시 C1-6알킬렌 또는 할로게노이다]이며; R3는 C2-6, C1-6알콕시. 하이드록시 C1-6알킬 또는 OH이고; R4는 H, C1-6알킬, 페닐 또는 벤질이고; R5는H, C1-6알킬, OH, C1-6알콕시, -(CH2)d (V)e, CH2Si(CH3)2(R3), (CH2)d
    -(C1-6알킬렌)-OR4또는 -CH(Y)(Z) 〔여기서, Y는 C1-6하이드록시 알킬렌, C1-6알킬 또는 (CH2)e-C6H4-(V)e이고, Z는 CHO, CO2R4, CO2NHR4또는 (CH2)e-OR4이며, V는 OR4또는 하이드록시 C1-6알킬렌이다〕이고; R6은 R5에 대해 정의한 바와 같으나, 단 R5가 H이고 R5및 R6이 이들이 부착되어 있는 질소원자와 함께 다음 일반식의 헤테로사이클릭 잔기
    를 형성하는 경우, R6은 H 이외의 것이며; R7은 CH2OR4, C(O)NHR4또는 CHO이고; R8은 (H, OH) 또는 =O이며; a는 0,1,2 또는 3이며; b 및 b´는 각각 독립적으로 0 또는 1이고; d 및 d´는 각각 독립적으로 1 또는 2이며; e 및 e´는 각각 독립적으로 0,1 또는 2이고; x는 0 또는 1이다.
  2. 제1항에 있어서, x가 1인 화합물.
  3. 제2항에 있어서, P1이 C1-3알킬렌인 화합물.
  4. 제1항에 있어서 b가 1인 화합물.
  5. 제1항에 있어서, T´가 수소인 화합물.
  6. 제1항에 있어서, b가 1이고 W가 C1-3알킬렌이며 R이 몰폴리닐이고 T´가 수소인 화합물.
  7. 제1항에 있어서, b가 1이고 W가 C1-3알킬렌이며 R이 피리딜이고 T´가 수소인 화합물.
  8. 제1항에 있어서, b가 1이고 W가 C1-3알킬렌이며 R이 에테닐이고 T´가 수소인 화합물.
  9. 제1항에 있어서, W가 C1-2알킬렌인 화합물.
  10. 제1항에 있어서, P2가 C1-6알킬인 화합물.
  11. 제1항에 있어서, P2가 C1-3알킬인 화합물.
  12. 제1항에 있어서, R1이 벤질옥시인 화합물.
  13. 제1항에 있어서, R1이 PDL인 화합물.
  14. 제1항에 있어서, R5가 H이고 R6이 벤질인 화합물.
  15. 제1항에 있어서, R5가 H이고 R6이 CH(Y)(Z)〔여기서, Y는 C1-3알킬이고, Z는 -(CH2)e─OR4이다(여기서, e는 1이고, R4는 벤질 또는 C1-3알킬이다)〕인 화합물.
  16. 제1항에 있어서, 4-(N-벤질옥시카보닐-L-발릴)아미노-2,2-디플루오로-3-옥소 -5-[4-(옥소-4-펜테닐)페닐]-N-벤질 펜탄아미드인 화합물.
  17. 제1항에 있어서, 4-(N-벤질옥시카보닐-L-발릴)아미노-2,2-디플루오로-3-옥소 -5-〔4-2-{N-몰폴리닐}에틸옥시)페닐〕-N-벤질 펜탄아미드인 화합물.
  18. 제1항에 있어서, N-(4-벤질옥시카보닐-L-발릴)아미노-2,2-디플루오로-3-옥소 -5-〔4-({2-피리딜}메틸옥시)페닐〕-N-벤질 펜탄아미드인 화합물.
  19. 제1항에 있어서, N-〔3-(3-피리딜)프로파노일〕-4-(L-발릴)아미노-2,2-디플루오로-3-옥소-5-〔4-(2-{N-몰폴리닐}에틸옥시)페닐〕-N-벤질 펜탄아미드인 화합물.
  20. 제1항에 있어서, N-〔3-(3-피리딜)프로파노일〕-4-(L-발릴)아미노-2,2-디플루오로-3-옥소-5-〔4-({2-피리딜)}메틸옥시)페닐〕N-벤질 펜탄아미드인 화합물.
  21. 제1항에 있어서, N-(4-벤질옥시카보닐-L-발릴)아미노-2,2-디플루오로-1,3-디옥소-5-〔(4-{2-N-몰폴리닐}에틸옥시)페닐-펜틸〕-O-메틸-D-발리놀인 화합물.
  22. 제1항에 있어서, N-〔4-(N-벤질옥시카보닐-L-발릴)아미노-2,2-디플루오로-1,3-디옥소-5-〔(4-{2-N-몰폴리닐}에틸옥시)페닐-펜틸〕-O-메틸-D-발리놀인 화합물.
  23. 약제학적 활성 화합물로서 사용하기 위한, 제1항에 따르는 화합물.
  24. HIV 감염의 치료에 사용하기 위한, 제1항에 따르는 화합물.
  25. 임의로 약제학적으로 허용되는 담체와 배합하여, 제1항에 따르는 화합물을 포함하는 약제학적 조성물.
  26. 제7항에 있어서, HIV 감염을 치료하기 위한 약제학적 조성물.
  27. HIV 감염 치료용 약제학적 조성물을 제조하기 위한, 임의로 약제학적으로 허용되는 담체와 배합하는 제1항에 따르는 화합물의 용도.
  28. 다음 일반식(Ⅱ)의 화합물을 사용하는 단계, 이 화합물을 산화시키는 단계 및 이로써 생성된 산화 화합물을 임의로 약제학적으로 허용되는 이의 염으로 전환시키는 단계를 포함하는, 일반식(I)의 화합물, 및 이의 수화물, 동배체 및 약제학적으로 허용되는 염의 제조방법.
    상기 식에서 P1는 C1-6알킬렌{여기서, T는〔(O)b-W-R〕이고, T'는 〔(O)b-W'-R'〕이거나, H이다(여기서, 각각의 W 및 W´는 독립적으로 C1-6알킬렌이거나 존재하지 않으며,단 W가 R의 질소원자에 직접 결합되는 경우, W는 C2-6알킬렌이다)}이고; P2는 C1-6알킬, 사이클로펜틸, 하이드록시 C1-6알킬, 페닐, 벤질 또는 3-테트라하이드로푸릴이고; R 및 R´는 각각 독립적으로 C2-6알케닐렌, 피페라지닐, 치환된 피페라지닐, 피페리딜, 몰폴리닐, 피리딜, 피라지닐 또는 피리미디닐 〔여기서, 치환된 피페라지닐은 이의 하나의 질소 원자가 CHO, C(O)NHR4, C1-4알킬 또는 CO2R4에 의해 치환된 피페라지닐이다〕이며; R1은 벤질옥시, C1-6알콕시, C1-6알킬, 페닐, 벤질, 펜에틸, 플루오레닐메틸렌옥시, 2-퀴놀리닐, NHSO2R4, N(R4) (벤질) 또는 N(R4)(PDL)이며; PDL은 -(CH2)a-2, 3- 또는 4-피리딜, 또는 p-치환된 벤질옥시〔여기서, 치환체는 니트로, OH, 아미노, C1-6알콕시, 하이드록시 C1-6알킬렌 또는 할로게노이다〕이며; R3는 C2-6알케닐, C1-6알콕시. 하이드록시 C1-6알킬 또는 OH이고; R4 H, C1-6알킬, 페닐 또는 벤질이고; R5는H, C1-6알킬, OH, C1-6알콕시, -(CH2)d (V)e, CH2Si(CH3)2(R3), (CH2)d (C1-6알킬렌)-OR4또는 -CH(Y)(Z) 〔여기서, Y는 C1-6하이드록시 알킬렌, C1-6알킬 또는 (CH2)e-C6H4-(V)e이고, Z는 CHO, CO2R4, CO2NHR4또는 (CH2)e-OR4이며, V는 OR4또는 하이드록시 C1-6알킬렌이다〕이고; R6은 R5에 대해 정의한 바와 같으나, 단 R5가 H이고 R5및 R6이 이들이 부착되어 있는 질소원자와 함께 다음 일반식의 헤테로사이클릭 잔기
    를 형성하는 경우, R6은 H이외의 것이며; R7은 CH2OR4, C(O)NHR4또는 CHO이고; R8은 (H, OH) 또는 =O이며; a는 0,1,2 또는 3이며; b 및 b´는 각각 독립넉으로 0 또는 1이고; d 및 d´는 각각 독립적으로 1 또는 2이며; e 및 e´는 각각 독립적으로 0,1 또는 2이고; x는 0 또는 1이다.
  29. 제12항에 있어서, 산화 단계에서 데스 마틴(Dess Martin)산화를 이용하는 방법.
  30. 제12항에 있어서, 산화 단계에서 스웨론(Swern) 산화를 이용하는 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019960701172A 1993-09-09 1994-08-10 디플루오로 스타톤 항바이러스성 유사체 KR100308839B1 (ko)

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