KR960000878A - 신규 인간 면역 결핍 바이러스(hiv)프로테아제 억제 화합물 및 그의 제조방법 - Google Patents

신규 인간 면역 결핍 바이러스(hiv)프로테아제 억제 화합물 및 그의 제조방법 Download PDF

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KR960000878A
KR960000878A KR1019940013423A KR19940013423A KR960000878A KR 960000878 A KR960000878 A KR 960000878A KR 1019940013423 A KR1019940013423 A KR 1019940013423A KR 19940013423 A KR19940013423 A KR 19940013423A KR 960000878 A KR960000878 A KR 960000878A
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phenyl
methyl
hexanoyl
methanesulfonyl
amide
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KR0125117B1 (ko
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고종성
최낙현
박지효
윤흥식
김성천
최호일
손영찬
이창선
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성재갑
주식회사 엘지화학
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Priority to US08/473,877 priority patent/US5696134A/en
Priority to EP95108908A priority patent/EP0687675A3/en
Priority to JP7172733A priority patent/JP2987313B2/ja
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Abstract

본 발명은 하기 일반식(I)로 표시되는 인간 면역 결핍 바이러스(HIV)의 중식을 억제하는 신규 HIV 프로테아제 억제 화합물 및 그의 제조방법, 및 상기 화합물을 유효성분으로 함유하는, HIV 감염으로 발생되는 후천성면역 결핍증의 치료 또는 예방을 위한 조성물에 관한 것이다.
상기식에서, A, B, R1,R3, 및 R4는 명세서 중에서 정의한 바와 같다.

Description

신규 인간 면역 결핍 바이러스(HIV) 프로테아제 억제 화합물 및 그의 제조방법.
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (6)

  1. 하기 일반식(I)의 시스-에폭사이드 구조를 갖는 화합물 및 그의 약제학적으로 허용되는 염, 수화물 또는 용매화물 :
    상기식에서, R1및 R2는 각각 독립적으로 수소원자 및 저급 중에서 선택되고, R3는 저급알킬, 방향족라디칼로 치환된 알킬, 아릴 및 탄소수 3내지 8의 사이클릭 알킬중에서 선택되고, R4는 C1-C4알킬이고, n은 0.1또느 2이고, A는 하기 일반식(Ⅱ)의 그룹이고,
    (상기식에서, X는 -CO-, -COCO-, -SO2- 또느 CS이며, Y는 -O-, -NH또는 -NCH3-이고, m은 0또는 1이고, R5는 수소, 저급알킬, 사이클릭 알킬, 아릴, 아릴아킬, 아릴옥시알킬, 아미노알킬, 알킬아미노알킬, 사이클릭아미노알킬, 알콕시알킬, 폴리알콕시알킬, 헤테로사이클, 헤테로사이클릭알킬, 아릴티오알킬, 아릴설포닐알킬, 헤테로사이클릭티오알킬, 헤테로사이클릭설포닐알킬, 사이클로알콕시알킬, 사이클로알킬티오알킬, 헤테로사이클릭옥시알킬 및 사이클로알킬설포닐알킬로 이루어진 그룹중에서 선택된다), B는 하기 일반식(Ⅲ)의 그룹이다 :
    (상기식에서, Z는 O, OH또는 -NCH3-이고, R6및 R7은 각각 독립적으로 저급 알킬, 방향족 라디칼로 치환된 저급 알킬, 탄소수 3내지 8의 사이클릭 알킬로 치환된 저급 알킬 및 방향족 라디칼중에서 선택된다).
  2. 제1항에 있어서, R1및 R2가 각각 독립적으로 수소, 메틸 또는 에틸이고, R3가 이소부틸, 사이클로펜틸메틸, 사이클로헥실메틸 또는 벤질이며, R4가 수소, 메틸 또는 에틸이고, R5가 사이클로헥실메틸, 벤질, 퀴놀리닐, 테트라하이드로 퀴놀리닐, 이소퀴놀리닐, 인돌릴, 피리딜, 피리딜메틸, 이소퀴놀리닐옥시메틸, 나프톡시메틸, 테트라하이드로피라닐, 벤조피라닐, 티아졸릴메틸 또는 티아졸릴이며, R6및 R7이 각각 독립적으로 이소프로필, 이소부틸, 이소펜틸, 벤질, 사이클로프로필, 사이클로부틸, 사이클로펜틸, 사이클로프로필메틸 또는 페닐인 화합물.
  3. 제1항에 있어서, {(5S)-[N-(2-퀴놀린 키보닐)-(-메탄설포닐)-L-알라닌일]아미노}-(4R,3S)-에폭시-6-페닐-헥사노일]-(2S)-[(1-페닐-3-메틸)부틸]아미드, {(5S)-[N-(2-퀴놀린 카보닐)-(-메탄설포닐)-L-알라닌일}아미노]-(4R,3S)-에폭시-6-페닐-헥사노일]-(2S)-[(1-페닐-2-메틸)프로필]아미드, {(5S)-[N-(2-퀴놀린 카보닐)-(-메탄설포닐)-L-알라닌일]아미노}-(4R,3S)-에폭시-6-페닐-헥사노일]-[디(이소프로필)메틸]아미드, {(5S)-[N-벤질옥시카보닐-(-메탄설포닐)-L-발리닐]아미노}-(4R,3S)-에폭시-6-페닐-헥사노일]-(2S)-[(1-페닐-3-메틸)-부틸]아미드, {(5S)-[N-벤질옥시카보닐-(-메탄설포닐)-L-발리닐]아미노}-(4R,3S)-에폭시-6-페닐-헥사노일]-(2S)-[(1-페닐-2-메틸)-프로필]아미드, {(5S)-[N-벤질옥시카보닐-(-메탄설포닐)-L-발리닐]아미노}-(4R,3S)-에폭시-6-페닐-헥사노일]-(디(이소프로필)메틸]아미드, {(5S)-[N-2-퀴놀린카보닐)-(-메탄설포닐)-L-발리닐]아미노}-(4R,3S)-에폭시-6-페닐-헥사노일]-(2S)-[(1-페닐-3-메틸)-부틸]아미드, {(5S)-[N-(2-퀴놀린카보닐)-(-메탄설포닐)-L-발리닐]아미노}-(4R,3S)-에폭시-6-페닐-헥사노일]-(2S)-[(1-페닐-2-메틸)-프로필]아미드, {(5S)-[N-(2-퀴놀린카보닐)-(-메탄설포닐)-L-발리닐]아미노}-(4R,3S)-에폭시-6-페닐-헥사노일]-[디(이소프로필)메틸]아미드, {(5S)-[N-(2-피리일메톡시)카보닐-(-메탄설포닐)-L-발리닐]아미노}-(4R,3S)-에폭시-6-페닐-헥사노일](2S)-[(1-페닐-3-메틸)-부틸]아미드, {(5S)-[N-(2-피리딜메톡시)카보닐-(-메탄설포닐)-L-발리닐]아미노}-(4R,3S)-에폭시-6-페닐-헥사노일]-(2S)-[(1-페닐-3-메틸)-프로필]아미드, {(5S)-[N-(2-피리일메톡시)카보닐-(-메탄설포닐)-L-발리닐]아미노}-(4R,3S)-에폭시-6-페닐-헥사노일]-[디(이소프로필)메틸]아미드, {(5S)-[N-(3-피리딜메톡시)카보닐-(-메탄설포닐)-L-발리닐]아미노}-(4R,3S)-에폭시-6-페닐-헥사노일]-(2S)-[(1-페닐-3-메틸)-부틸]아미드, {(5S)-[N-(3-피리딜메톡시)카보닐-(-메탄설포닐)-L-발리닐]아미노}-(4R,3S)-에폭시-6-페닐-헥사노일]-(2S)-[(1-페닐-3-메틸)-프로필]아미드, {(5S)-[N-(3-피리딜메톡시)카보닐-(-메탄설포닐)-L-발리닐]아미노}-(4R,3S)-에폭시-6-페닐-헥사노일]-[디(이소프로필)메틸]아미드, {(5S)-[N-(4-피리딜메톡시)카보닐-(-메탄설포닐)-L-발리닐]아미노}-(4R,3S)-에폭시-6-페닐-헥사노일]-(2S)-[(1-페닐-3-메틸)-부틸]아미드, {(5S)-[N-(3-피리딜메톡시)카보닐-(-메탄설포닐)-L-발리닐]아미노}-(4R,3S)-에폭시-6-페닐-헥사노일]-(2S)-[(1-페닐-3-메틸)-프로필]아미드, {(5S)-[N-(3-피리딜메톡시)카보닐-(-메탄설포닐)-L-발리닐]아미노}-(4R,3S)-에폭시-6-페닐-헥사노일]-[디(이소프로필)메틸]아미드, {(5S)-[N-(1-피놀리딘)아세틸-(-메탄설포닐)-L-발리닐]아미노}-(4R,3S)-에폭시-6-페닐-헥사노일]-(2S)-[(1-페닐-3-메틸)-부틸]아미드, {(5S)-[N-(1-피놀리딘)아세틸-(-메탄설포닐)-L-발리닐]아미노}-(4R,3S)-에폭시-6-페닐-헥사노일]-(2S)-[(1-페닐-2-메틸)-프로필]아미드,{(5S)-[N-(1-피놀리딘)아세틸-(-메탄설포닐)-L-발리닐]아미노}-(4R,3S)-에폭시-6-페닐-헥사노일]-[디(이소프로필)메틸]아미드, {(5S)-[N-아세틸)-(-메탄설포닐)-L-발리닐]아미노)-(4R,3S)-에폭시-6-페닐-헥사노일]-(2S)-[(1-페닐-3-메틸)-부틸]아미드, {(5S)-[N-아세틸)-(-메탄설포닐)-L-발리닐]아미노)-(4R,3S)-에폭시-6-페닐-헥사노일]-(2S)-[(1-페닐-2-메틸)-프로필]아미드, {(5S)-[N-아세틸)-(-메탄설포닐)-L-발리닐]아미노)-(4R,3S)-에폭시-6-페닐-헥사노일]-[디(이소프로필)메틸]아미드, {(5S)-[N-(4-옥소-4H-1-벤조피란-2-카보닐-(-메탄설포닐)-L-발리닐]아미노}-(4R,3S)-에폭시-6-페닐-헥사노일]-(2S)-[(1-페닐-3-메틸)-부틸]아미드, {(5S)-[N-(4-옥소-4H-1-벤조피란-2-카보닐-(-메탄설포닐)-L-발리닐]아미노}-(4R,3S)-에폭시-6-페닐-헥사노일]-(2S)-[(1-페닐-3-메틸)-프로필]아미드, {(5S)-[N-(4-옥소-4H-1-벤조피란-2-카보닐-(-메탄설포닐)-L-발리닐]아미노}-(4R,3S)-에폭시-6-페닐-헥사노일]-[디(이소프로필)메틸]아미드, {(5S)-[N(5-이소퀴놀리닐옥시)아세틸-(-메탄설포닐)-L-발리닐]아미노}-(4R,3S)-에폭시-6-페닐-헥사노일]-[디(이소프로필)메틸]아미드, {(5S)-[N(5-이소퀴놀리닐옥시)아세틸-(-메탄설포닐)-L-발리닐]아미노}-(4R,3S)-에폭시-6-페닐-헥사노일]-(2S)-[(1-페닐-3-메틸)-메틸]아미드, 및 {(5S)-[N(5-이소퀴놀리닐옥시)아세틸-(-메탄설포닐)-L-발리닐]아미노}-(4R,3S)-에폭시-6-페닐-헥사노일]-(2S)-[(1-페닐-3-메틸)-프로필]아미드, 및 그의 약제학적으로 허용가능한 염, 수화물 또는 용매화물.
  4. 하기 일반식(가)의 화합물을 하기 일반식(나)의 화합물과 커플링 반응시킨 후 산화시켜 하기 일반식(다) 화합물을 얻고 : 이 일반식(다)의 화합물로부터 벤질옥시카보닐 보호그룹을 제거한 뒤, 하기 일반식(마) 화합물과 커플링 반응시킨 후 산화시켜 하기 일반식(바)로 부터 벤질옥시카보닐 보호 그룹을 제거한 후 하기 일반식(아) 또는 (자)의 화합물과 커플링 반응시킴을 포함하는, 제1항의 일반식(I)의 화합물의 제조 방법.
    상기식에서, A, B, R1, R2, R3및 R4는 제1항에서 정의한 바와 같다.
  5. 하기 일반식(차)의 화합물을 -78℃에서 칼륨 헥사메틸디실라잔(KHMDS)의 존재하에, 하기 일반식(카)의 화합물과 반응시켜 하기 일반식(타)의 화합물을 수득한 다음, 이를 산촉매 존재하에, t-부탄을중에서 응매의 환류온도로 가열하여 하기 일반식(가)화합물을 제조하는 방법 :
    상기식에서, X는 할로겐 원자, 예를 들면 Br 또는 1이고, R3는 제1항에서 정의한 바와 같다.
  6. 제1항에 따른 화합물의 치료 효과량과 약제학적으로 허용가능한 담체, 분산제, 수화제, 불활성 회석제, 부형제 및 윤활제중에서 선택된 1종 이상의 보조제를 함유하는 인간 면역 결핍 바이러스 감염의 치료 또는 예방을 위한 조성물.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임
KR1019940013423A 1993-11-30 1994-06-15 항 에이즈(aids)효과를 갖는 신규한 인간 면역 결핍 바이러스(hiv)프로테아제 억제 화합물 및 그의 제조방법 KR0125117B1 (ko)

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US08/473,877 US5696134A (en) 1993-11-30 1995-06-07 Irreversible HIV protease inhibitors, intermediates, compositions and processes for the preparation thereof
EP95108908A EP0687675A3 (en) 1994-06-15 1995-06-09 Irreversible HIV protease inhibitors, intermediates, compositions and processes for their preparation
JP7172733A JP2987313B2 (ja) 1994-06-15 1995-06-15 不可逆的なヒト免疫不全ウイルス（ｈｉｖ）プロテアーゼ阻害剤、中間体、組成物およびその製造方法

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EP0812839A1 (en) * 1994-12-08 1997-12-17 LG Chemical Limited Irreversible HIV protease inhibitors, compositions containing same and process for the preparation thereof
EP0812857A1 (en) * 1994-12-08 1997-12-17 LG Chemical Limited Irreversible HIV protease inhibitors, compositions containing same and process for the preparation thereof
US6037157A (en) 1995-06-29 2000-03-14 Abbott Laboratories Method for improving pharmacokinetics
KR970062034A (ko) * 1996-02-22 1997-09-12 성재갑 사람면역결핍 바이러스 1형의 단백질 분해효소 억제제에 대해 내성을 갖는 돌연변이 단백질 분해효소
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WO2017040963A1 (en) 2015-09-03 2017-03-09 Forma Therapeutics, Inc. [6,6] fused bicyclic hdac8 inhibitors
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EP0361341A3 (en) 1988-09-28 1991-07-03 Miles Inc. Therapeutics for aids based on inhibitors of hiv protease
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