KR20010034269A - Hiv를 억제하는 피리미딘 유도체 - Google Patents
Hiv를 억제하는 피리미딘 유도체 Download PDFInfo
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- KR20010034269A KR20010034269A KR1020007007970A KR20007007970A KR20010034269A KR 20010034269 A KR20010034269 A KR 20010034269A KR 1020007007970 A KR1020007007970 A KR 1020007007970A KR 20007007970 A KR20007007970 A KR 20007007970A KR 20010034269 A KR20010034269 A KR 20010034269A
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Abstract
Description
Claims (24)
- HIV(인간 면역결핍 바이러스) 에 감염된 대상체(subject) 치료용 의약의 제조를 위한 하기 화학식 I 의 화합물, 그의 N-옥사이드, 약제학적으로 허용되는 부가 염 또는 입체화학적 이성체 형태의 용도:상기식에서,A 는 CH, CR4또는 N 이고;n 은 0, 1, 2, 3 또는 4 이며;Q 는 수소 또는 -NR1R2이고;R1및 R2는 각각 독립적으로 수소, 하이드록시, C1-12알킬, C1-12알킬옥시, C1-12알킬카보닐, C1-12알킬옥시카보닐, 아릴, 아미노, 모노- 또는 디(C1-12알킬)아미노, 모노- 또는 디(C1-12알킬)아미노카보닐로 구성된 군으로부터 선택되거나(여기에서, 상기 언급한 각각의 C1-12알킬기는 임의로 및 각각 개별적으로 하이드록시, C1-6알킬옥시, 하이드록시C1-6알킬옥시, 카복실, C1-6알킬옥시카보닐, 시아노, 아미노, 이미노, 아미노카보닐, 아미노카보닐아미노, 모노- 또는 디(C1-6알킬)아미노, 아릴 및 Het 로 구성된 군으로부터 각각 독립적으로 선택된 1 또는 2 개의 치환기로 치환될 수 있다);R1및 R2가 함께 피롤리디닐, 피페리디닐, 몰포리닐, 아지도 또는 모노- 또는 디(C1-12알킬)아미노C1-4알킬리덴을 형성할 수 있고;R3은 수소, 아릴, C1-6알킬카보닐, C1-6알킬, C1-6알킬옥시카보닐, C1-6알킬옥시카보닐로 치환된 C1-6알킬이며;R4는 각각 독립적으로 하이드록시, 할로, C1-6알킬, C1-6알킬옥시, 시아노, 아미노카보닐, 니트로, 아미노, 트리할로메틸, 트리할로메틸옥시, 또는 시아노 또는 아미노카보닐로 치환된 C1-6알킬이고;R5는 수소 또는 C1-4알킬이며;L 은 C1-10알킬, C3-10알케닐, C3-10알키닐, C3-7사이클로알킬, 또는 C3-7사이클로알킬, 인다닐, 인돌릴 및 페닐로 구성된 군으로부터 독립적으로 선택된 1 또는 2 개의 치환기로 치환된 C1-10알킬이거나(여기에서, 상기 페닐, 인다닐 및 인돌릴은 할로, 하이드록시, C1-6알킬, C1-6알킬옥시, 시아노, 아미노카보닐, C1-6알킬옥시카보닐, 포르밀, 니트로, 아미노, 트리할로메틸, 트리할로메틸옥시 및 C1-6알킬카보닐로 구성된 군으로부터 각각 독립적으로 선택된 1, 2, 3, 4 또는 가능한 경우 5 개의 치환기로 치환될 수 있다);L 은 -X1-R6또는 -X2-Alk-R7이고(여기에서,R6및 R7은 각각 독립적으로 페닐 또는 할로, 하이드록시, C1-6알킬, C1-6알킬옥시, C1-6알킬카보닐, C1-6알킬옥시카보닐, 포르밀, 시아노, 아미노카보닐, 니트로, 아미노, 트리할로메틸옥시 및 트리할로메틸로 구성된 군으로부터 각각 독립적으로 선택된 1, 2, 3, 4 또는 5 개의 치환기로 치환된 페닐이고;X1및 X2는 각각 독립적으로 -NR3-, -NH-NH-, -N=N-, -O-, -S-, -S(=O)- 또는 -S(=O)2- 이며;Alk 는 C1-4알칸디일이다);아릴은 페닐 또는 할로, C1-6알킬, C1-6알킬옥시, 시아노, 니트로 및 트리플루오로메틸로 구성된 군으로부터 각각 독립적으로 선택된 1, 2, 3, 4 또는 5 개의 치환기로 치환된 페닐이고;Het 는 지방족 또는 방향족 헤테로사이클 라디칼이며;상기 지방족 헤테로사이클 라디칼은 피롤리디닐, 피페리디닐, 호모피페리디닐, 피페라지닐, 몰포리닐, 테트라하이드로퓨라닐 및 테트라하이드로티에닐로 구성된 군으로부터 선택되고(여기에서, 상기 지방족 헤테로사이클 라디칼은 각각 옥소기로 임의로 치환될 수 있다);상기 방향족 헤테로사이클 라디칼은 피롤릴, 퓨라닐, 티에닐, 피리딜, 피리미디닐, 피라지닐 및 피리다지닐로 구성된 군으로부터 선택된다(여기에서, 상기 방향족 헤테로사이클 라디칼은 각각 하이드록시로 임의로 치환될 수 있다).
- 제 1 항에 있어서, n 이 최소한 1 이고, 적어도 하나의 R4가 시아노인 화합물의 용도.
- 제 1 항 또는 제 2 항에 있어서, 하기 화학식 I-1 의 화합물의 용도:
- 제 1 항 내지 제 3 항 중 어느 한 항에 있어서, 하기 화학식 I'-1 의 화합물의 용도:
- 하기 화학식 I' 의 화합물, 그의 N-옥사이드, 약제학적으로 허용되는 부가 염 또는 입체화학적 이성체 형태:상기식에서,L, Q, R3, R4, R5및 A 는 화학식 I 에서 정의한 바와 같고;R4'은 할로, C1-6알킬, 시아노, 아미노카보닐, 니트로, 트리할로메틸, 트리할로메틸옥시, 또는 시아노 또는 아미노카보닐로 치환된 C1-6알킬이고;n' 은 0, 1, 2 또는 3 이며;단, Q 및 L 은 아닐리노, 2,4,6-트리니트로-아닐리노, 3-메톡시아닐리노, 4-메톡시-아닐리노, 3,4-디메톡시-아닐리노, 3-클로로-4-플루오로-아닐리노, 4-시아노-아닐리노, 2-(C1-6알킬)-아닐리노, 4-(C1-6알킬)-아닐리노, 3-클로로-아닐리노, 4-브로모-아닐리노, 4-니트로-아닐리노 및 4-클로로-아닐리노가 아니다.
- 제 5 항에 있어서, 하기 화학식 I'-1 의 화합물:
- 제 6 항에 있어서, L 및 Q 가 아닐리노, 2,4,6-트리니트로-아닐리노, 4-(C1-6알킬)-아닐리노, 4-브로모-아닐리노, 4-니트로-아닐리노 및 4-클로로-아닐리노가 아닌 화합물.
- 제 6 항 또는 제 7 항에 있어서, R4'이 시아노, 아미노카보닐, 또는 시아노 또는 아미노카보닐로 치환된 C1-6알킬인 화합물.
- 제 5 항 내지 제 8 항 중 어느 한 항에 있어서, L 이 2,6-디클로로벤질이거나; L 이 -X1-R6이거나(여기에서, X1은 -NR3-, -S- 또는 -O- 이고, R6은 2,4,6-트리클로로페닐, 2,4,6-트리메틸-페닐, 2,4-디브로모-3,5-디클로로-페닐, 2,4-디브로모-6-플루오로-페닐, 2,4-디클로로-6-메틸-페닐, 2,6-디브로모-4-이소프로필-페닐, 2,6-디브로모-4-메틸페닐, 2,6-디브로모-4-프로프-1-일-페닐, 2,6-디클로로-4-시아노-페닐, 2,6-디클로로-4-트리플루오로메톡시-페닐, 2,6-디클로로-4-트리플루오로메틸-페닐, 2,6-디클로로-페닐, 2,6-디메틸-4-(1,1-디메틸에틸)-페닐, 2,6-디메틸-페닐, 2-브로모-4-플루오로-6-메틸-페닐, 2-브로모-6-클로로-4-플루오로-페닐, 4-브로모-2,6-디메틸-페닐, 4-클로로-2,6-디메틸-페닐, 4-시아노-2,6-디메틸-페닐이다); L 은 -X2-Alk-R7(여기에서, -X2-Alk- 는 -NH-CH2- 이고, R7은 페닐이다)인 화합물.
- 제 5 항 내지 제 9 항 중 어느 한 항에 있어서, Q 가 수소이고, L 이 -X1-R6이며(여기에서, X1은 -NH- 이고, R6은 2,4,6-트리메틸-페닐 또는 4-시아노-2,6-디메틸페닐이다), NR3(페닐 또는 피리딜로 임의로 치환된) 부위가 p-시아노-아닐리노를 나타내고, 피리미딘 환의 2번 위치에 존재하는 화합물.
- 제 5 항 내지 제 10 항 중 어느 한 항에 있어서, R4'이 할로, 시아노, 아미노카보닐 또는 시아노C1-6알킬이고; n 은 0 이며, A 는 CH 이고, R3는 수소이며; R5는 수소 또는 메틸이고; Q 는 수소 또는 NHR1이며; L 은 페닐, 2,4,6-트리클로로-페닐, 2,4,6-트리메틸-페닐, 2,4-디브로모-3,5-디클로로-페닐, 2,4-디브로모-6-플루오로-페닐, 2,4-디클로로-6-메틸-페닐, 2,6-디브로모-4-이소프로필-페닐, 2,6-디브로모-4-메틸-페닐, 2,6-디브로모-4-프로프-1-일-페닐, 2,6-디클로로-4-시아노-페닐, 2,6-디클로로-4-트리플루오로메톡시-페닐, 2,6-디클로로-4-트리플루오로메틸-페닐, 2,6-디클로로-페닐, 2,6-디메틸-4-(1,1-디메틸에틸)-페닐, 2,6-디메틸-페닐, 2-브로모-4-플루오로-6-메틸-페닐, 2-브로모-6-클로로-4-플루오로-페닐, 4-브로모-2,6-디메틸-페닐, 4-클로로-2,6-디메틸-페닐 또는 4-시아노-2,6-디메틸-페닐을 포함하는 화합물.
- 제 5 항에 있어서,4-[[4-아미노-6-[(2,6-디클로로페닐)메틸]-2-피리미디닐]아미노]벤조니트릴;6-[(2,6-디클로로페닐)메틸]-N2-(4-플루오로페닐)-2,4-피리미딘디아민;4-[[4-[(2,4-디클로로페닐)메틸]-6-[(4-하이드록시부틸)아미노]-2-피리미디닐]아미노]벤조니트릴;4-[[4-[(2,6-디클로로페닐)메틸]-6-[(3-하이드록시프로필)아미노]-2-피리미디닐]아미노]벤조니트릴;N-[2-[(4-시아노페닐)아미노]-6-[(2,6-디클로로페닐)메틸]-4-피리미디닐]-아세트아마이드;N-[2-[(4-시아노페닐)아미노]-6-[(2,6-디클로로페닐)메틸]-4-피리미디닐]-부탄아마이드;4-[[2-아미노-6-(2,6-디클로로펜옥시)-4-피리미디닐]아미노]벤조니트릴;4-[[4-[(2,6-디클로로페닐)메틸]-6-[(2-하이드록시-2-페닐에틸)아미노]-2-피리미디닐]아미노]벤조니트릴;4-[[4-[(2,6-디클로로페닐)메틸]-6-[(3-(2-옥소-1-피롤리디닐)프로필]아미노]-2-피리미디닐]아미노]벤조니트릴;4-[[4-[(2,6-디클로로페닐)메틸]-6-[[2-(2-하이드록시에톡시)에틸]아미노]-2-피리미디닐]아미노]벤조니트릴;4-[[4-[(2,6-디클로로페닐)메틸]-6-[(2,3-디하이드록시프로필)아미노]-2-피리미디닐]아미노]벤조니트릴;4-[[4-[(2,6-디클로로페닐)메틸]-6-(하이드록시아미노)-2-피리미디닐]아미노]벤조니트릴;4-[[4-[(2-시아노에틸)아미노]-6-[(2,6-디클로로페닐)메틸]-2-피리미디닐]아미노]벤조니트릴;4-[[4-[(2,6-디클로로페닐)메틸]-6-[[2-(1-피롤리디닐)에틸]아미노]-2-피리미디닐]아미노]벤조니트릴;4-[[4-아미노-6-[(2,6-디클로로페닐)메틸]-5-메틸-2-피리미디닐]아미노]벤조니트릴;N2-(4-브로모페닐)-6-[(2,6-디클로로페닐)메틸]-5-메틸-2,4-피리미딘디아민;4-[[4-[(2,4,6-트리메틸페닐)아미노]-2-피리미디닐]아미노]벤조니트릴;4-[[2-[(2,4,6-트리메틸페닐)아미노]-4-피리미디닐]아미노]벤조니트릴;4-[[4-[(2,6-디메틸페닐)아미노]-2-피리미디닐]아미노]벤조니트릴;4-[[4-(2,4,6-트리메틸펜옥시)-2-피리미디닐]아미노]벤조니트릴;4-[[4-[(2,6-디클로로페닐)티오]-2-피리미디닐]아미노]벤조니트릴;4-[[4-[[2,6-디브로모-4-(1-메틸에틸)페닐]아미노]-2-피리미디닐]아미노]벤조니트릴;4-[[4-[[2,6-디클로로-4-(트리플루오로메틸)페닐]아미노]-2-피리미디닐]아미노]벤조니트릴;4-[[4-[(2,4-디클로로-6-메틸페닐)아미노]-2-피리미디닐]아미노]벤조니트릴;4-[[2-[(시아노페닐)아미노]-4-피리미디닐]아미노]-3,5-디메틸벤조니트릴;4-[[4-[(2,4-디브로모-6-플루오로페닐)아미노]-2-피리미디닐]아미노]벤조니트릴;4-[[4-아미노-6-[(2,6-디클로로페닐)메틸]-5-메틸-2-피리미디닐]아미노]벤젠아세토니트릴;4-[[4-[메틸(2,4,6-트리메틸페닐)아미노]-2-피리미디닐]아미노]벤조니트릴;4-[[4-[(2,4,6-트리클로로페닐)아미노]-2-피리미디닐]아미노]벤조니트릴;4-[[4-[(2,4,6-트리메틸페닐)티오]-2-피리미디닐]아미노]벤조니트릴;4-[[4-[(2,4,6-트리메틸페닐)아미노-2-피리미디닐]아미노]벤조니트릴;4-[[4-아미노-6-(2,4,6-트리메틸페닐)아미노]-2-피리미디닐]아미노]벤조니트릴;4-[[2-아미노-6-(2,4,6-트리메틸페닐)아미노]-4-피리미디닐]아미노]벤조니트릴;4-[[4-(2-브로모-4-클로로-6-메틸펜옥시)-2-피리미디닐]아미노]벤조니트릴;4-[[4-[(4-클로로-2,6-디메틸페닐)아미노]-2-피리미디닐]아미노]벤조니트릴;3,5-디클로로-4-[[2-[(4-시아노페닐)아미노]-4-피리미디닐]아미노]벤조니트릴;4-[[4-[[2,6-디클로로-4-(트리플루오로메톡시)페닐]아미노]-2-피리미디닐]아미노]벤조니트릴;4-[[4-[(2,4-디브로모-3,6-디클로로페닐)아미노]-2-피리미디닐]아미노]벤조니트릴;4-[[4-[(2,6-디브로모-4-프로필페닐]아미노]-2-피리미디닐]아미노]벤조니트릴;4-[[4-[(2,4,6-트리메틸페닐)아미노]-2-피리미디닐]아미노]벤즈아마이드;4-[[4-[(4-(1,1-디메틸에틸)-2,6-디메틸페닐)아미노]-2-피리미디닐]아미노]벤조니트릴;4-[[2-[(4-시아노페닐)아미노]-4-피리미디닐]옥시]-3,5-디메틸벤조니트릴;4-[[4-[(4-클로로-2,6-디메틸페닐)아미노]-5-메틸-2-피리미디닐]아미노]벤조니트릴;4-[[2-[(4-시아노페닐)아미노]-5-메틸-4-피리미디닐]아미노]-3,5-디메틸벤조니트릴;4-[[4-[[4-(1,1-디메틸에틸)-2,6-디메틸페닐]아미노]-5-메틸-2-피리미디닐]아미노]벤조니트릴;4-[[4-[(4-브로모-2,6-디메틸페닐)아미노]-5-메틸-2-피리미디닐]아미노]벤조니트릴;4-[[5-메틸-4-[(2,4,6-트리메틸페닐)티오]-2-피리미디닐]아미노]벤조니트릴;4-[[4-[(2,6-디브로모-4-프로필페닐)아미노]-5-메틸-2-피리미디닐]아미노]벤조니트릴;4-[[4-[(2,4,6-트리메틸페닐)아미노]-2-피리미디닐]아미노]벤즈아마아드, N3-옥사이드;N2-(4-클로로페닐)-N4-(2,4,6-트리메틸페닐)-2,4-피리미딘디아민;4-[[4-[[2,6-디브로모-4-(1-메틸에틸)페닐]아미노]-5-메틸-2-피리미디닐]아미노]벤조니트릴;4-[[2-[(4-시아노페닐)아미노]-5-메틸-4-피리미디닐]아미노]-3,5-디메틸벤조니트릴;4-[[4-[(페닐메틸)아미노]-2-피리미디닐]아미노]벤조니트릴;그의 N-옥사이드, 약제학적으로 허용되는 부가 염 또는 입체화학적 이성체 형태인 화합물.
- 약제학적으로 허용되는 담체 및 치료학적 활성량의 제 5 항 내지 제 12 항 중 어느 한 항에 따른 화합물을 포함하는 약제학적 조성물.
- 치료학적 활성량의 제 5 항 내지 제 12 항 중 어느 한 항에 따른 화합물을 약제학적으로 허용되는 담체와 밀접하게 혼합시킴을 특징으로 하는, 제 13 항에 따른 약제학적 조성물을 제조하는 방법.
- a) 화학식 II-A 의 중간체를 임의로 용매 중에서 반응-불활성 대기 하에 임의로 산 존재 하에 화학식 III 의 아미노 유도체와 반응시키거나;b) 화학식 II-B 의 중간체를 임의로 용매 중에서 반응-불활성 대기 하에 임의로 산 존재 하에 화학식 VI 의 아미노 유도체와 반응시키거나;c) 중간체 H-X1-R6을 적합한 용매 중에서 임의로 적합한 산 또는 염기 존재 하에 화학식 II-C 의 중간체와 반응시켜 화학식 I'-C 로 나타내어지는, L 이 -X1-R6인 화학식 I' 의 화합물을 수득하거나;또는, 원하는 경우, 화학식 I' 의 화합물을 공지된 변환 반응에 따라 서로 전환시키거나, 추가로, 원하는 경우, 화학식 I' 의 화합물을 산으로 처리하여 치료학적 활성의 비-독성 산 부가 염으로 전환시키거나, 염기로 처리하여 치료학적 활성의 비-독성 염기 부가 염으로 전환시키거나, 반대로 산 부가 염 형태를 알칼리로 처리하여 유리 염기로 전환시키거나, 염기 부가 염 형태를 산으로 처리하여 유리산으로 전환시키고; 원하는 경우, 그의 입체화학적 이성체 형태 또는 N-옥사이드를 제조함을 특징으로 하는 제 5 항에 따른 화합물의 제조 방법:상기 반응식에서,Q, R3, R4, R4', R5, A, n' 및 L 은 제 5 항에서 정의된 바와 같고;W1은 적합한 이탈기이다.
- 제 5 항에 있어서, 의약으로서 사용하기 위한 화합물.
- 제 1 항에 따른 화학식 I 의 화합물과 다른 항레트로바이러스 화합물의 배합물.
- 제 5 항에 따른 화학식 I' 의 화합물과 다른 항레트로바이러스 화합물의 배합물.
- 제 17 항 또는 제 18 항에 있어서, 의약으로서 사용하기 위한 배합물.
- 항-HIV 치료에 있어서, 동시, 분리 또는 순차 사용을 위한 배합 제제로서 (a) 제 1 항에 따른 화학식 I 의 화합물 및 (b) 다른 항레트로바이러스 화합물을 포함하는 생성물.
- 항-HIV 치료에 있어서, 동시, 분리 또는 순차 사용을 위한 배합 제제로서 (a) 제 5 항에 따른 화학식 I' 의 화합물 및 (b) 다른 항레트로바이러스 화합물을 포함하는 생성물.
- 활성 성분으로서 (a) 제 1 항에 따른 화학식 I 의 화합물 및 (b) 다른 항레트로바이러스 화합물과 약제학적으로 허용되는 담체를 포함하는 약제학적 조성물.
- 활성 성분으로서 (a) 제 5 항에 따른 화학식 I' 의 화합물 및 (b) 다른 항레트로바이러스 화합물과 약제학적으로 허용되는 담체를 포함하는 약제학적 조성물.
- 하기 화학식 II'-B 의 화합물:[화학식 II'-B]상기식에서,R3, R4, R4', n', A 및 L 은 제 5 항에서 정의된 바와 같고,W1은 할로겐이다.
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KR1020067013365A KR100699514B1 (ko) | 1998-03-27 | 1999-03-24 | Hiv를 억제하는 피리미딘 유도체 |
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US7963298P | 1998-03-27 | 1998-03-27 | |
US60/079632 | 1998-03-27 | ||
EP98201587.7 | 1998-05-14 | ||
EP98201587A EP0945442A1 (en) | 1998-03-27 | 1998-05-14 | Trisubstituted pyrimidine derivatives |
EP98203948 | 1998-11-25 | ||
EP98203948.9 | 1998-11-25 |
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KR (1) | KR100643419B1 (ko) |
AR (1) | AR014785A1 (ko) |
BR (1) | BRPI9909191B8 (ko) |
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US20010011094A1 (en) | 2001-08-02 |
AR014785A1 (es) | 2001-03-28 |
US6197779B1 (en) | 2001-03-06 |
BRPI9909191B8 (pt) | 2021-07-06 |
ES2361146T3 (es) | 2011-06-14 |
BR9909191A (pt) | 2000-12-05 |
US20030083317A1 (en) | 2003-05-01 |
US8026248B2 (en) | 2011-09-27 |
DE69943247D1 (de) | 2011-04-14 |
US6440986B2 (en) | 2002-08-27 |
BRPI9909191B1 (pt) | 2018-04-03 |
US6903213B2 (en) | 2005-06-07 |
KR100643419B1 (ko) | 2006-11-10 |
US20050192305A1 (en) | 2005-09-01 |
US20050197354A1 (en) | 2005-09-08 |
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