KR940014355A - 퀴나졸린 유도체 - Google Patents

퀴나졸린 유도체 Download PDF

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KR940014355A
KR940014355A KR1019930027144A KR930027144A KR940014355A KR 940014355 A KR940014355 A KR 940014355A KR 1019930027144 A KR1019930027144 A KR 1019930027144A KR 930027144 A KR930027144 A KR 930027144A KR 940014355 A KR940014355 A KR 940014355A
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alkyl
amino
formula
alkoxy
alkylamino
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앤드류 존 바커
디어그 서더랜드 브라운
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수잔 제인 젠틀
체네카 리미티드
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Priority claimed from GB939310248A external-priority patent/GB9310248D0/en
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Publication of KR940014355A publication Critical patent/KR940014355A/ko

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    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
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    • C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
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    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • A—HUMAN NECESSITIES
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    • C07D239/72—Quinazolines; Hydrogenated quinazolines
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    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
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    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07—ORGANIC CHEMISTRY
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    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems

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Abstract

본원은 하기 구조식(Ⅰ)의 퀴나졸린유도체, 또는 그의 약학적으로 허용되는 염 ;
식중, m은 1,2 또는 3이고, 각각의 R1은 하이드록시, 아미노, 우레이도, 하이드록시아미노, 트리플루오로메톡시, (1-4C) 알킬, (1-4C)알콕시 및 (1-3C)알킬렌디옥시를 포함하며, Q는 1개 또는 2개의 질소헤테로 원자를 함유하며, 질소, 산소 및 황에서 선택된 추가의 헤테로 원자를 임의로 함유할 수 있는 9-또는 10-원 비사이클릭 헤테로사이클린 부분, 또는 Q는 헤테로사이클릭 또는 아릴부분이 할로게노, 하이드록시, 옥소, 아미노, 니트로, 카바모일, (1-4C) 알콕시 ; (1-4C) 알킬, (1-4C) 알킬아미노, 디-[(1-4C) 알킬]아미노 및 (2-4C) 알카노일아미도에서 선택된 1개 또는 2개의 치환체들을 임의로 함유할 수 있는 9- 또는 10-원 비사이클릭 아릴부분임.
당해 구조식(Ⅰ)의 퀴나졸린 유도체, 또는 그의 약학적으로 허용되는 염을 제조하는 방법 : 당해 구조식(Ⅰ)의 퀴노졸린 유도체, 또는 그의 약학적으로 허용되는 염을 함유하는 제약 조성물; 및 당해 구조식(I)이 퀴나졸린 유도체, 또는 그의 약학적으로 허용되는 염의 수용기 티로신 키나제 억제 특성을 암치료에 사용하는 방법에 관한다.

Description

퀴나졸린 유도체
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. 하기 구조식(Ⅰ)의 퀴나졸린 유도체 또는 그의 약학적으로 허용되는 염
    식중, m은 1,2 또는 3이며; 각각의 R1은 독립하여 하이드록시, 아미노 우레이도, 하이드록시아미노, 트리플루오로메톡시, (1-4C) 알킬, (1-4C)알콕시, (1-3C)알킬렌디옥시, (1-4C) 알킬아미노 디-[(1-4C) 알킬]아미노, 피롤리딘-1-일, 피페리디노, 모폴리노, 피페라진-1-일, 4-(1-4C) 알킬피폐라진-1-일, (1-4C) 알킬티오, 할로게노-(1-4C) 알킬, 하이드록시-(1-4C) 알킬, (2-4C) 알카노일옥시-(1-4C) 알킬, (1-4C) 알콕시-(1-4C) 알킬, 시아노-(1-4C) 아킬, 아미노-(1-4C) 알킬, (1-4C) 알킬아미노-(1-4C) 알킬, 디-[(1-4C) 알킬]아미노-(1-4C) 알킬, 피페리디노-(1-4C) 알킬 모폴리노-(1-4C) 알킬, 피페라진-1-일-(1-4C) 알킬, 4-(1-4C) 알킬 피페라진-1-일-1-4C) 알킬, 하이드록시-(2-4C) 알킬아미노-(1-4C) 알킬, (1-4C) 알콕시-(2-4C) 알킬아미노-(1-4C) 알킬, 할로게노-(2-4C) 알콕시, 하이드록시-(2-4C) 알콕시, (2-4C) 알카노일옥시-(2-4C) 알콕시, (1-4C) 알콕시-(2-4C) 알콕시, 아미노-(2-4C) 알콕시, (1-4C) 알킬아미노-(2-4C) 알콕시, 디-[(1-4C) 알킬]아미노-(2-4C) 알콕시, (2-4C) 알카노일옥시, 하이드록시-(2-4C) 알카노일옥시, (1-4C) 알콕시-(2-4C) 알카노일옥시, 페닐-(1-4C) 알콕시, 할로게노-(2-4C) 알킬아미노, (1-4C) 알킬아미노, 하이드록시-(2-4C) 알킬아미노, (2-4C) 알카노일옥시-(2-4C) 알킬아미노, (1-4C) 알콕시-(2-4C) 알킬아미노, 아미노-(2-4C) 알킬아미노, (1-4C) 알킬아미노, (2-4C) 알킬아미노, 디-[(1-4C) 알킬]아미노-(2-4C) 알킬아미노, (2-4C) 알카노일아미노, (1-4C) 알콕시카바보닐아미노, 벤즈아미도, 3-페닐우레이도, 할로게노-(2-4C) 알카노일아미노, 하이드록시-(2-4C) 알카노일아미노 또는 (1-4C) 알콕시-(2-4C) 알카노일아미노이고, 상술한 벤즈아미도 치환제 또는 R1치환체내 흑종의 페닐 그룹은, 임의로, 1개 또는 2개의 할로게노, (1-4C) 알킬 또는 (1-4C) 알콕시 치환체를 함유할 수 있음 ; Q는 1개 또는 2개의 질소헤테로 원자를 함유하고, 질소, 산소, 황에서 선택된 추가의 헤테로원자를 임의로 함유하는 9- 또는 10-원비사이틀릭 헤테로사이클릭 부분, 또는 그의 수소화된 유도체, 또는 Q는 헤테로사이클릭 또는 아릴 부분, 도는 수소화된 유도체가 할로게노, 하이드록시, 옥소, 아미노, 니트로, 카바모일, (1-4C) 알킬, (1-4C) 알콕시, (1-4C) 알킬아미노, 디-[(1-4C) 알킬]아미노 및 (2-4C) 알카노일아미노에서 선택된 1개 또는 2개의 치환체를 임의로 함유하는 9- 또는 10-원 비사이클릭 아릴부분, 또는 그의 수소화된 유도체임.
  2. 제 1 항에 있어서, R1이 추가로 수소, 할로게노 또는 니트로가 될 수 있고, Q에 위치하는 임의의 1개 또는 2개의 치환체가 추가로 카복시 및 (1-4C) 알콕시카보닐에서 선택될 수 있는 구조식(Ⅰ)의 퀴나졸린 유도체 또는 그의 약학적으로 허용되는 염[단, 4-(4-퀴나졸리닐아미노) 퀴나졸린을 제외함].
  3. 제 1 항 또는 제 2 항에 있어서, R1이 추가로 2-옥소 피롤리딘-1-일 또는 2-옥소피페리딘-1-일이 될 수 있고, Q에 위치하는 임의의 1개 또는 2개의 치환체가 추가로 시아노가될 수 있는 구조식(Ⅰ)의 퀴나졸린 임의의 1개 또는 그의 약학적으로 허용되는 염[단, 4-(4-퀴나졸리닐아미노) 퀴나졸린을 제외함].
  4. 제 1 항 또는 제 2 항에 있어서, , m은 1,2 또는 3이고, 각각의 R1이 독립하여 하이드록시, 아미노, 플루오로, 클로로, 니트로, 메틸, 에틸, 메톡시, 에톡시, 프로폭시, 이소프로폭시, 부톡시, 메틸렌디옥시, 에틸렌디옥시, 메틸아미노, 에틸아미노, 디메틸아미노, 디에틸아미노, 프로피온아미도 또는 2-클로로아세트아미도이며, Q가 플루오로, 클로로, 하이드록시, 아미노, 카복시, 메틸, 에틸, 메톡시, 에톡시, 메틸아미노, 디메틸아미노, 아세트아미도, 메톡시카보닐 및 에톡시카보닐에서 선택된 1개 또는 2개의 치환체들을 임의로 함유할 수 있는, 인돌일, 1H-벤즈이미다졸일, 1H-인다졸인, 벤족사졸일, 벤조티아졸일, 1H-벤조트리아졸일, 벤조[c]퓨라자닐, 벤조[c][2,1,3]티아디아졸릴, 퀴놀일, 이소퀴놀일, 시놀리닐, 퀴나졸리닐, 퀴녹살리닐, 인테닐, 인다닐, 나프틸 또는 1,2,3,4-테트라하이드로나프틸인 구조식(Ⅰ)의 퀴나졸린 유도체, 또는 그의 약학적으로 허용되는 염.
  5. 제 1항 또는 제 2 항에 있어서, (R1)m이 6-하이드록시, 7-하이드록시, 6,7-디하이드록시, 6-아미노, 7-아미노, 6-플루오로, 7-플루오로, 6-클로로, 7-클로로, 6-니트로, 6-메톡시, 7-메톡시, 6,7-디메톡시, 6,7-디에톡시, 6-하이드록시-7-메톡시, 6,7-메틸렌디옥시, 6,7-에틸렌디옥시, 6-메틸아미노, 7-메틸아미노, 6-에틸아미노, 6-디메틸아미노, 7-디메틸아미노, 6-디에틸아미노, 6-피롤리딘-1-일, 7-피롤리딘-1-일, 6-피페리디노, 7-피페리디노, 6-모폴리노, 7-모폴리노, 6-피페라진-1-일, 7-피페라진-1-일, 6-(4-메틸피페라진-1-일), 7-(4-메틸피페라진-1-일), 6-메틸티오, 7-메틸티오, 6-아미노-7-메톡시, 6-아미노-7-메틸아미노, 6-아세트아미도, 7-아세트아미도, 6-(2-클로로아세트아미도) 또는 7-(2-클로롤아세트아미도)이고, q가 플루오로, 클로로, 메틸, 에틸 및 메톡시에서 선택된 1개 또는 2개의 치환체들을 함유할 수 있는, 4-, 5- 또는 6-인돌일, 1H-벤즈이미다졸-4-일, 1H-벤즈이미다졸-5-일, 1H-벤즈이미다졸-6-일, 1H-인다졸-4-일, 1H-인다졸-5-일, 1H-인다졸-6-일, 1H-인다졸-7-일, 5-또는 6-벤조사졸일, 5-또는 6-벤조티아졸일, 1H-벤조트리아졸-4-일, 1H-벤조트리아졸-5-일, 1H-벤조트리아졸-6-일, 벤조[c][2,1,3]티아디아졸-4-일, 2-, 3-, 4-, 5-, 6-, 7- 또는 8-퀴놀일, 1-, 3-, 4-, 5-, 6-, 7- 또는 8-이소퀴놀일, 4-, 5-, 6-, 7- 또는 8-시놀리닐, 5-, 6-, 7- 또는 8-퀴나졸리닐 또는 2-, 5- 또는 6-퀴녹살리닐, 또는 Q가 플루오로, 클로로, 하이드록시, 카복시, 메틸, 메톡시 및 메톡시카보닐에서 선택된 1개 또는 2개의 치환체들을 임의로 함유할 수 있는, 4- 또는 5-인다닐, 1- 또는 2-나프틸, 1,2,3,4-테트라하이드로나프트-5-일 또는 1,2,3,4-테트라하이드로나프트-6-일인 구조식(Ⅰ)의 퀴나졸린 유도체, 또는 그의 약학적으로 허용되는 염.
  6. 제 1 항에 있어서, (R1)m이 6-아미노, 6,7-디메톡시, 6-피페리디노 또는 6-아세트아미도이고, Q가 5-인돌일, 1H-인다졸-5-일, 6-벤조티아졸일, 1H-벤조트리아졸-5-일, 벤조[c][2,1,3]티아디아졸-4-일, 5-퀴놀일, 6-퀴놀일, 8-퀴놀일, 5-이소쿠놀일 또는 5-퀴녹살리닐인 구조식(Ⅰ)의 퀴나졸린 유도체 또는 그의 약학적으로 허용되는 염.
  7. 6,7-디메톡시-4-(5-퀴놀아미노) 퀴나졸린, 6,7-디메톡시-4-(6-퀴놀일아미노) 퀴나졸린, 6,7-디메톡시-4-(5-이소퀴놀일아미노 퀴나졸린, 6,7-디메톡시-4-(5-인돌일아미노) 퀴나졸린, 6,7-디메톡시-4[(1H-인다졸-5-일)아미노]퀴나졸린, 4-(6-벤조티아졸일아미노)6,7-디메톡시퀴나졸린 및 4-[(벤조[c][2,1,3]티아디아졸-4-일)아미노]-6,7-디메톡시퀴나졸린에서 선택되는 구조식(Ⅰ)의 퀴나졸린 유도체 또는 그의 약학적으로 허용되는 산-부가염.
  8. (a) 하기 구조식(Ⅱ)을 지니는 퀴나졸린을 구조식 H2N-Q를 지니는 아민과 반응시키는 단계 ;
    식중, Z는 치환그룹 (b)R1이 니트로인 구조식(Ⅰ)의 퀴나졸린 유도체를 환원시켜, R1이 아미노기인 구조식(Ⅰ)의 화합물을 얻는 단계 ; (c)R1이 아미노인 구조식(Ⅰ)의 퀴나졸린 유도체를 아실화시켜, R1이 (2-4C) 알카노일아미노 또는 치환된 (2-4C) 알카노일아미노, 벤즈아미도, 우레이도 또는 3-페닐우레이도인 구조식(Ⅰ)의 화합물을 얻는 단계 ; (d) R1이적당한 하이드록시 또는 아미노인 구조식(Ⅰ)의 퀴나졸린 유도체를 알킬화시켜, R1이 (1-4C) 알콕시 또는 치환된 (1-4C) 알콕시 또는 R1이 (1-4C) 알킬아미노 또는 치환된 (1-4C) 알킬아미노인 구조식(Ⅰ)의 화합물을 얻는 단계 ; (e) R1이 치환 그룹을 지니는 (1-4C) 알킬 치환체인 구조식(Ⅰ)의 퀴나졸린 유도체를 적당한 아민, 알콜 또는 시아나이드와 반응시켜, R1이 아미노-, 옥시- 또는 시아노-치환된 (1-4C)알킬 치환체인 구조식(Ⅰ)의 화합물을 얻는 단계 ; (f) R1이 치환그룹인 구조식(Ⅰ)의 퀴나졸린 유도체를 적당한 아민 또는 티올과 반응시켜, R1이 아미노, (1-4C) 알킬아미노, 디-[(1-4C) 알킬]아미노, 피롤리딘-1-일, 피레리디노, 모폴리노, 피페라진-1-일, 4-(1-4C) 알킬피페라진-1-일 또는 (1-4C) 알킬티오인 구조식(Ⅰ)의 화합물을 얻는 단계 ; (g) R1이 할로겐 (2-4C) 알카노일아미노 그룹인 구조식(Ⅰ)의 퀴나졸린 유도체를 환화(cyclisation)시켜, R1이 2-옥시피롤리딘-1-일 또는 2-옥소피페리딘-1-일인 구조식(Ⅰ)의 화합물을 얻는 단계 ; 및 필요한 경우, 구조식(Ⅰ)을 지니는 퀴나졸린 유도체의 염을 전통적인 방법으로 구조식(Ⅰ)의 화합물과 적당한 산을 반응시켜 얻는 단계로 구성되는, 제 1 항 내지 제 7 항중 어느 한 항의 구조식(Ⅰ)의 퀴나졸린 유도체, 또는 그의 약학적으로 허용되는 염을 제조하는 방법.
  9. 제 1 항 내지 제 7 항중 어느 한 항의 구조식(Ⅰ)의 퀴나졸린 유도체 또는 그의 약학적으로 허용되는 염과 약학적으로 허용되는 희석제 또는 담체로 구성되는 약학적 조성물.
  10. 구조식(Ⅰ)의 퀴나졸린 유도체, 또는 그의 약학적으로 허용되는 염을 인간과 같은 온혈동물내에서 항암효과를 발휘하는 약제 제조에 사용되는 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019930027144A 1992-12-10 1993-12-10 퀴나졸린 유도체 KR940014355A (ko)

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