KR970701183A - 4-헤테로사이클릴-치환된 퀴나졸릴 유도체, 이들의 제조 방법 및 항암제로서의 용도(4-heterocyclyl-substituted quinazoline derivatives, processes for their preparation and their use as anti-cancer agents) - Google Patents

4-헤테로사이클릴-치환된 퀴나졸릴 유도체, 이들의 제조 방법 및 항암제로서의 용도(4-heterocyclyl-substituted quinazoline derivatives, processes for their preparation and their use as anti-cancer agents)

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KR970701183A
KR970701183A KR1019960704612A KR19960704612A KR970701183A KR 970701183 A KR970701183 A KR 970701183A KR 1019960704612 A KR1019960704612 A KR 1019960704612A KR 19960704612 A KR19960704612 A KR 19960704612A KR 970701183 A KR970701183 A KR 970701183A
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alkoxy
alkyl
hydroxy
mono
alkylamino
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리 디 아놀드
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스피겔 알렌 제이
화이자 인코포레이티드
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Abstract

본 발명은 Z가 하기 화학식(2), 화학식(3), 화학식(4) 또는 화학식(5) (이때, X는 메틸렌, 티오, -N(H)- 또는 옥시이고; Y는 산소 또는 황원자를 혼입할 수 있는 5 또는 6원 방향족 또는 부분적으로 포화된 고리를 완결하고; T는 메틸렌, -N(H)-, 티오 또는 옥시이다); 또는 Z가 하기 화학식(6) (이때, D는 포화탄소, 산소 또는 티오일 수 있다); 또는 Z가 화학식(7) (이때, A는 7 내지 9원의 단일 불포화 단일 이자 고리를 완결하고, R1, R2, R3, m, n, p 및 q는 명세서에서 정의된 바와 같다)인 하기 화학식(1)의 특정한 4-아미노퀴나 졸린 및 그의 약학적으로 허용가능한 염 및 이성질체에 관한 것이다. 화학식(1)의 화합물은 과다중식 질병 치료에 유용하며, 특히 항암제로서 유용하다.

Description

4-헤테로사이클릴-치환된 퀴나졸릴 유도체, 이들의 제조방법 및 항암제로서의 용도(4-HETEROCYCLYL-SUBSTITUTED QUINAZOLINE DERIVATIVES PROCESSES FOR THEIR PREPARATION AND THEIR USE AS ANTI-CANCER AGENTS)
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (25)

  1. 하기 A, B 또는 C인 화학식(1)의 화합물 및 그의 약학적으로 허용가능한 염 및 입체이성질체;
    A:Z가 화학식(2), 화학식(3), 화학식(4) 또는 화학식(5)이고,
    상기 식에서, X는 메틸렌, 티오, -N(H)- 또는 옥시이고, Y는 산소 또는 황 원자를 혼입할 수 있는 5원 또는 6원 방향족 또는 부분적 포화고리를 완결하고; T는 메틸렌, -N(H)-, 티오 또는 옥시이고;
    B:Z가 하기 화학식(6)이고
    상기 식에서, D는 포화탄소, 옥시 또는 티오일 수 있고; 또는 Z가 하기 화학식(7)이고
    상기 식에서, A는 7 내지 9원의 단일 불포화 모노-아자 고리를 완결하고; R1은 각각 독립적으로 a. 트리플루오로메틸, 할로, 니트로, 하이드록시, 아미노, 시아노, 시아노, (C1-C4)알킬, (C1-C4)알콕시, (C1-C|4)알콕시카보닐, (C1-C4)알카노일옥시, (C1-C4)알카노일아미노, 카복시, 페녹시, 벤조일옥시, 카바모일, 모노 -N- 또는 디-N-N-디-(C1-C4)알킬카바모일, 모노-N- 또는 디-N,N-(C1-C4)알킬아미노, 모노-N- 또는 디-N-N-(하이드록시, (C2-C4)알킬)아미노, 모노-N- 또는 디-N-N-((C1-C4)알콕시(C2-C4)알킬)아미노, 아닐리노, 필롤리딘-1-일, 피페리딘-1-일, 모르폴리노, 피레라진-1-일, 4-(C2-C4)알킬피페라진-1-일, (C1-C4)알킬티오, 페닐리오 또는 (C1-C4)알킬상에서 치환된 상기 기들; b. 하이드록시(C2-C4)알콕시(C1-C4)알킬, (C1-C4)알콕시-(C2-C4)알콕시-(C1-C4)알킬, 하이드록시(C2-C4)알킬티오-(C1-C|4)알킬, (C1-C4)알콕시-(C2-C4)알킬티오-(C1-C4)알킬, 하이드록시아미노, 벤조일아미노, 모노-N- 또는 디-N,N-(C1-C4)알킬카바모일메틸아미노, 카바모일메틸아미노, (C1-C4)알콕시카보닐아미노, (C1-C4)알카노일아미노, 카복시메틸아미노, (C1-C4)알콕시카보닐메틸아미노, (C1-C|4)알콕시아미노, (C2-C4)알카노일옥시아미노, 페닐(C1-C4)알킬아미노, (C1-C4)알킬설포닐아미노, 벤젠설폰아미도, 3-페닐우레이도, 2-옥소피롤리딘-1-일, 2,5-디옥소피롤리딘-1-일, 우레이도, (C1-C4)알콕시(C1-C4)알킬카보닐아미노, (C1-C4)알킬설피닐, (C1-C4)아킬설포닐, (C1-C4)알콕시(C2-C4)알킬티오, 모노, 디- 또는 트리플루오로메틸옥시, (C1-C4)알킬렌디옥시, 벤질옥시 아지도, 구아니디노, 아미노카보닐, 모노 -N- 또는 디-N,N-(C1-C4)알킬아미노카보닐, 페닐(C1-C4)알콕시, 카복시메톡시, (C1-C4)알콕시카보닐메톡시, 카바모일메톡시, 모노 -N- 또는 디-N,N-(C1-C4)알킬카바모일메톡시, 모노 -N- 또는 디-N,N-(하이드록시(C2-C4)알킬)키복사미도, 모노-N- 또는 디-N,N-(C1-C4)알킬카바모일메톡시, 모노 -N- 또는 디-N,N-(하이드록시(C2-C4)알킬)키복사미도, 모노-N- 또는 디-N,N-((C1-C4)알콕시(C2-C4)알킬)카복사미도 또는 비스((C1-C4)알칸설포닐)아미도; 또는 c, (C2-C4)알콕시, (C2-C4)알킬티오, (C2-C4)알카노일옥시, (C2-C4)알킬아미노, (C1-C4)알킬(C1-C4)알킬렌디옥시 또는 (C2-C4)알카노일아미노이고; 이들 각각의기는 아미노, 할로, 하이드록시, (C2-C4)알카노일옥시, (C1-C4)알콕시, 모노-N- 또는 디-N,N-(C1-C4)알킬아미노, 모노 -N- 또는 디-N,N-(하이드록시(C2-C|4)알킬)아미노, 모노-N- 또는 디-N,N-((C1-C4)알콕시(C2-C4)알킬)아미노, (C1-C4)알카노일아미노, 페녹시, 아닐리노, 이미다졸-1-일, 페닐티오, 피페리디노, 모르폴리노, 피페라진-1-일, 4-(C1-C4)알킬피페라진-1-일, 카복시, (C1-C4)알콕시카보닐, 카바모일, 모노 -N- 또는 디-N,N-(C1-C4)알킬카바모일, 카복사미도, 모노 -N- 또는 디-N,N-(C1-C4)알킬카복사미도 또는 모노 -N- 또는 디-N,N-(하이드록시(C2-C4)알킬)카복사미도로 치환되고; 이때 R1치환체에서의 임의의 페닐이 할로, 니트로, 트리플루오로메틸, 하이드록시, (C1-C4)알콕시 또는 (C1-C4)알킬로 선택적으로 단일 또는 이치환되고 상기 (C1-C4)알킬렌디옥시는 퀴나졸린 잔기의 양 말단에서 열결되고; 각 경우의 R2는 독립적으로 모노-, 디- 또는 트리-플루오로메틸, 할로, 니트로, 하이드록시, 아미노, 아지도, 이소티오시아노, (C1-C4)알킬, 페닐, 티에닐, (C1-C4)알콕시, 벤질옥시, 페녹시, (C2-C6)알케닐, (C2-C6)알키닐, (C1-C4)알킬렌디옥시, 시아노, 벤조일아미노, 크리플루오로메틸카보닐아미노, (C1-C4)알카노일아미노, (C1-C4)알카노일, N-모노- 또는 N,N-디-(C1-C4)알킬아미노, (C1-C4)알킬설포닐아미노, 트리플루오로메틸설포닐아미노, (C1-C4)알킬티오, (C1-C4)알킬설피닐 또는 (C1-C4)알킬설포닐, 피롤-1-일, 피페리딘-1-일 또는 피롤리딘-1-일이고, 상기 페닐, 벤질옥시, 페녹시 및 벤조일아미노는 할로, 니트로, 틀리플루오로메틸, 하이드록시 또는 (C1-C4)알킬로 선택적으로 단일 치환되고 상기 (C1-C4)알킬렌디옥시는 벤젠 잔기상의 인접한 탄소에 양말단에서 연결되고; 각각의 경우에 R3는 독립적으로 하이드록시, 아미노, 모노 -N- 또는 디-N,N-(C1-C4)알킬아미노, 설포 또는 (C1-C4)알콕시이고(단, 상기 기는 옥시, 티오 또는 -N-에 인접하 고리 탄소에 연결되어 있지 않는다), 또는 각각의 경우에 R3은 독립적으로 카복시, 하이드록시 (C1-C4)알킬, (C1-C4)알콕시(C|1-C4)알킬, 아미노(C1-C4)알킬, 모노 -N- 또는 디-N,N-(C1-C4)알킬아미노(C1-C4)알킬, 모르폴리노(C1-C4)알킬, 4-(C1-C4)알킬-피페라진-1-일(C1-C4)알킬, 카복시(C1-C|4)알킬, (C1-C4)알콕시카보닐, 설포(C1-C4)알킬 또는 (C1-C4)알킬이고; 이때 m은 0 내지 3이고; n은 0 내지 4이고; p는 0,1 또는 2이고; q는 0,1 또는 2이고; 단, 4-(3,4-디하이드-2H-퀴놀린-1-일)-퀴나졸린은 포함되지 않는다.
  2. 제1항에 있어서, Z가
    이고; 각각의 경우, R1은 각각 독립적으로 하이드록시, (C1-C4)알콕시, 하이드록시(C2-C4)알콕시, 아미노(C2-C4)알킬, 아미노(C2-C|4)알콕시, (C1-C4)알콕시(C2-C4)알콕시, (C1-C4)알킬렌디옥시, 하이드록시(C1-C4)알킬(C1-C4)알킬렌디옥시, (C1-C4)알콕시(C1-C4)알킬, (C1-C4)알킬렌디옥시, 모노-N- 또는 디-N,N-(C|1-C4)알킬아미노(C2-C4)알콕시, 3- 또는 4-(C1-C4)알콕시-(2-하이드록시)-(C3-C4)알콕시, 카복시(C1-C4)알콕시, (C1-C4)알콕시(C1-C4)알카노일옥시,니트로, 하이드록시아미노, 아미노, 모노-N- 또는 디-N,N-(C1-C4)알킬아미노, (C1-C4)알카노일아미노, 하이드록시(C2-C4)알킬아미노, (C1-C4)알콕시(C2-C4)알킬아미노, (C1-C4)알킬설폰아미노, 모르폴리노, (C1-C4)알킬-피페라진-1-일, 비스(C1-C4)알칸설폰아미도, 디(C1-C4)알킬아미노(C|2-C4)알킬아미노, (C1-C4)알킬아미노(C2-C4)알킬아미노, 이미다졸-1-일, 피페리딘-1-일, 피롤리딘-1-일, (C1-C4)알콕시(C1-C4)알킬카보닐아미노, N-(C1-C4)알킬-N-(C1-C4)알카노일-아미노, 카복시, (C1-C4)알콕시카보닐, (C1-C4)알콕시카보닐(C|1-C4)알콕시, 아미도, 모노-N- 또는 디-N,N-(C1-C4)알킬아미노카보닐, 모노-N- 또는 디-N,N-(하이드록시(C2-C4)알킬)아미노카보닐, (C1-C4)알킬, 하이드록시(C1-C4)알킬, 모노-N- 또는 디-N,N-((C1-C4)알콕시(C1-C4)알킬)아미노(C1-C4)알킬, 모노-N- 또는 디-N,N-(C1-C4)알킬아미노(C1-C4)알킬, (C1-C4)알카노일아미노(C1-C4)알킬, (C1-C4)알콕시(C2-C4)알콕시(C1-C4)알킬, (C1-C4)알킬티오, (C1-C4)알콕시(C2-C4)알킬티오 또는 하이드록시(C2-C4)알킬티오이고; 각각의 경우 R2가 독립적으로 니트로, 할로, (C1-C4)알킬, 피롤-1-일, 하이드록실,아미노, 모노-N- 또는 디-N,N-(C1-C4)알킬아미노, 아미노(C1-C4)알킬, 아지도, 에테닐, 에티닐, (C1-C4)알킬렌디옥시, 페닐 또는 (C1-C4)알킬티오이고; 각각의 경우 R3는 독립적으로 하이드록시(C1-C4)알킬, (C1-C4)알킬, 아미노(C1-C4)알킬, (C1-C4)카복시(C1-C4)알킬 또는 모노-N- 또는 디-N,N-(C1-C4)알킬아미노(C1-C4)알킬; m은 0,1 또는 2이고; p가 0 또는 1 이고; n은 0,1,2 또는 3인 화합물.
  3. 제2항에 있어서, Z가이고 각각의 경우 R1이 6 및/또는 7의 위치에서 독립적으로 치환되는 화합물; 상기 식에서, X가 -N(H)-이다.
  4. 제2항에 있어서, Z가또는이고 각각의 경우 R1이 6 및/또는 7의 위치에서 독립적으로 치환되는 화합물
  5. 제2항에 있어서, Z가이고 ; n이 1,2 또는 3이고; m이 1 또는 2이고; 각각의 경우 R1이 독립적으로 6 및/또는 7의 위치에서 치환되고 (C1-C4)알킬, (C1-C4)알콕시, 하이드록시(C2-C4)알콕시, (C1-C|4)알콕시(C2-C4)알콕시. 카복시(C1-C4)알콕시, (C1-C4)알콕시카보닐(C1-C|4)알콕시, 이미다졸-1-일-(C2-C4)알콕시, 모르폴리노(C2-C4)알콕시, 4-(C1-C4)알킬피페라진-1-일(C|1-C4)알콕시, (C1-C4)알콕시-2-하이드록시(C3-C4)알콕시,아미노, (C1-C4)알킬아미노, 디-N,N-알킬아미노, (C1-C4)알카노일아미노, (C1-C4)알킬설포닐아미도, 모르폴리노(C1-C|4)알킬피페라진-1-일, 모노-N- 또는 디-N,N-(C1-C4)알킬아미노(C2-C4)알킬아미노이고; 각각의 경우 R2가 독립적으로 4-하이드록시, 4아미노, 5-플루오로, 5-하이드록시, 5-아미노, 6-할로, 6-메틸, 6-에테닐, 6-에티닐, 6-니트로 또는 7-메틸인 화합물.
  6. 제5항에 있어서, 각각의 경우 R2가 독립적으로 할로, 니트로, 하이드록시 또는 메틸이고, R1이 (C1-C4)알콕시 또는 (C1-C4)알킬이고, m이 2이고, n이 1 또는 2인 화합물.
  7. 제5항에 있어서, m이 2이고, R1이 6-메톡시이고, R1이 7-메톡시이고, n이 2이고, R2가 5-플루오로이고, R2가 6-브로모인 화합물.
  8. 제5항에 있어서, m이 2이고, R1이 6-(2-메톡시에톡시)이고, R1이7-(2-메톡시에톡시)이고, n이 1이고, R2가 6-클로로인 화합물.
  9. 제5항에 있어서, m이 2이고, R1이 6-메톡시이고, R1이 7-(2-하이드록시에톡시)이고, n이 1이고, R2가 6-클로로인 화합물.
  10. 제5항에 있어서, m이 1이고, R1이 6-아미노이고, n이 1이고, R2가 6-클로로인 화합물.
  11. 제5항에 있어서, m이 2이고, R1이 6-메톡시이고, R1이 7-(3-하이드록시프로폭시)이고, n이 1이고, R2가 6-클로로인 화합물.
  12. 제5항에 있어서, m이 2이고, R1이 7-(2-이미다졸-1-일-에톡시)이고, R1이 6- 메톡시이고, n이 1이고, R2가 6-클로로인 화합물.
  13. 제5항에 있어서, m이 2이고, R1이 6-메톡시이고, R1이 7-메톡시이고, n이 1이고, R2가 6-클로로인 화합물.
  14. 제5항에 있어서, m이 2이고, R1이 6-메톡시이고, R1이 7-(2-메톡시-에톡시)이고, n이 1이고, R2가 5-플루오로이고, R2가 6-브로모인 화합물.
  15. 제5항에 있어서, m이 2이고, R1이 6-메톡시이고, R1이 7-메톡시이고, n이 2이고, R2가 5-아미노이고, R2가 6-클로로인 화합물.
  16. 제5항에 있어서, m이 2이고, R1이 6-메톡시이고, R1이 7-(2-하이드록시-3-메톡시)프로폭시이고, n이 1이고, R2가 6-클로로인 화합물.
  17. 제1항에 있어서, Z가이고; B가 6원 고리가 점선 부분에서 0,1 또는 2개의 이중결합을 갖고, n이 0 내지 2이고, 각각의 경우, R2가 독립적으로 할로, 하이드록시 또는 (C1-C4)알킬이고, m이 0,1 또는 2이고, 각각의 경우, R|1이 6 및/또는 7의 위치에서 독립적으로 치환되고 하이드록시, (C1-C4)알콕시, 하이드록시(C2-C4)알콕시, 아미노(C2-C4)알콕시, (C1-C|4)알콕시(C2-C4)알콕시, (C1-C4)알킬렌디옥시, 하이드록시(C1-C4)알킬(C1-C4)알킬렌디옥시, (C1-C4)알콕시(C1-C4)알킬(C1-C4)알킬렌디옥시, 모노-N- 또는 디-N,N-(C1-C4)알킬아미노(C2-C4)알콕시, 3- 또는 4-(C1-C4)알콕시-(2-하이드록시)-(C3-C4)알콕시, 카복시(C1-C4)알콕시, 모르폴리노(C2-C4)알콕시, 이미다졸-1-일(C2-C4)알콕시, 4(C1-C4)알킬피페라진-1-일-(C|2-C4)알콕시, C1-C4)알콕시C1-C4)알카노일옥시, 니트로, 하이드록시아미노, 아미노, 모노-N- 또는 디-N,N-(C1-C4)알킬아미노, (C1-C4)알카노일아미노, 하이드록시(C|2-C4)알킬아미노, (C1-C4)알콕시(C2-C4)알킬아미노, (C1-C4)알킬설폰아미도, 모르폴리노, (C1-C4)알킬-피페라진-1-일, 비스(C1-C4)알칸설폰아미도, 디-N,N-(C1-C4)알킬아미노(C|2-C4)알킬아미노, (C1-C4)알킬아미노(C2-C4)알킬아미노, 피페리딘-1-일, 이미다졸-1-일, 피롤리딘-1-일, (C1-C4)알콕시(C1-C4)알킬카보닐아미도, N-(C1-C|4)알킬-N-(C1-C4)알카노일-아미노, 카복시, (C1-C4)알콕시카보닐, (C1-C4)알콕시카보닐(C1-C4)알콕시,아미도, 모노-N- 또는 디-N,N-(C1-C4)알킬아미노카보닐, 모노-N- 또는 디-N,N-(하이드록시(C2-C|4)알킬)아미노카보닐, (C1-C4)알킬, 하이드록시(C1-C4)알킬, 모노-N- 또는 디-N,N-(C1-C4)알콕시(C1-C4)알킬아미노(C1-C4)알킬, 모노-N- 또는 디-N,N-(C|1-C4)알킬아미노(C1-C4)알킬, (C1-C4)알카노일아미노(C1-C4)알킬, (C1-C4)알콕시(C2-C4)알콕시(C1-C4)알킬, (C1-C4)알킬티오, (C1-C4)알콕시(C2-C4)알킬티오 또는 하이드록시(C2-C4)알킬티오인 화합물.
  18. 제1항에 있어서, Z가이고; D가 포화탄소이고, n이 0,1 내지 2이고, R2가 각각의 경우 독립적으로 할로, 하이드록시, 아미노, 니트로 트리풀루오로메틸, 에테닐 또는 (C1-C4)알킬이고, m이 0,1 또는 2이고, R1이 각각의 경우, 6 및/또는 7의 위치에서 독립적으로 치환되고 하이드록시, (C1-C4)알콕시, 하이드록시(C2-C4)알콕시, 아미노(C2-C4)알킬, 아미노(C2-C|4)알콕시, (C1-C4)알콕시(C2-C4)알콕시, (C1-C4)알킬렌디옥시, 하이드록시(C1-C4)알킬(C1-C4)알킬렌디옥시, (C1-C4)알콕시(C1-C4)알킬(C1-C4)알킬렌디옥시, 모노-N- 또는 디-N,N-(C|1-C4)알킬아미노(C2-C4)알콕시, 3- 또는 4-(C1-C4)알콕시-(2-하이드록시)-(C3-C4)알콕시, 카복시(C1-C4)알콕시, 모르폴리노(C2-C4)알콕시, 이미다졸-1-일(C2-C4)알콕시, 4(C1-C4)알킬피페라진-1-일-(C2-C4)알콕시, (C1-C4)알콕시(C1-C4)알카노일옥시, 니트로, 하이드록시아미노, 아미노, 모노-N- 또는 디-N,N-(C1-C4)알킬아미노, (C1-C4)알카노일아미노, 하이드록시(C2-C4)알킬아미노, (C1-C4)알콕시(C2-C|4)알킬아미노, (C1-C4)알킬설폰아미도, 모르폴리노, (C1-C4)알킬-피페라진-1-일, 비스(C1-C4)알칸설폰아미도, 디-N,N-(C1-C4)알킬아미노(C2-C4)알킬아미노, (C1-C4)알킬아미노(C2-C4)알킬아미노, 피페리딘-1-일, 이미다졸-1-일, 피롤리딘-1-일, (C1-C4)알콕시(C1-C4)알킬카보닐아미도, N-(C1-C4)알킬-N-(C1-C4)알카노일-아미노, 카복시, (C1-C4)알콕시카보닐, (C1-C4)알콕시카보닐(C1-C4)알콕시,아미도, 모노-N- 또는 디-N,N-(C1-C4)알킬아미노카보닐, 모노-N- 또는 디-N,N-(하이드록시(C2-C4)알킬)아미노카보닐, (C1-C4)알킬, 하이드록시(C1-C4)알킬, 모노-N- 또는 디-N,N-(C1-C4)알콕시(C1-C4)알킬아미노(C|1-C4)알킬, 모노-N- 또는 디-N,N-(C1-C4)알킬아미노(C1-C4)알킬, (C1-C4)알카노일아미노(C1-C4)알킬, (C1-C4)알콕시(C2-C4)알콕시(C1-C4)알킬, (C1-C4)알킬티오, (C1-C4)알콕시(C2-C4)알킬티오 또는 하이드록시(C2-C4)알킬티오인 화합물.
  19. 제18항에 있어서, R2가 각각의 경우 독립적으로 할로, 니트로, 하이드록시, (C1-C4)알킬 또는 트리플루오로메틸이고, R1이 (C1-C4)알콕시, (C1-C4)알킬렌디옥시 또는 알킬이고, m이 2이고, n이 1 또는 2인 화합물.
  20. 과다중식 질병 치료량의 제1항의 화합물을 과다중식 질병의 치료가 필요한 포유동물에 투여함을 포함하는 과다중식 질병의 치료방법.
  21. 제20항에 있어서, 과다중식 질병이 암인 방법.
  22. 제21항에 있어서, 질병이 뇌암, 폐암, 인상세포암, 방광암, 위장암, 췌장암, 간암, 신장암, 결장직장암, 유방암, 두암, 경부감, 식도암, 부인과암 또는 갑상선암인 방법.
  23. 제20항에 있어서, 과다중식 질병이 암이 아닌 방법.
  24. 제23항에 있어서, 암이 아닌 과다중식 질병이 건선 또는 양성 전립선 과형성증인 방법.
  25. 과다중식 질병 치료량의 제1항의 화합물 및 약학적으로 허용가능한 담체를 포함하는, 포유동물에서 과다중식 질병을 치료하기 위한 약학 조성물.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019960704612A 1994-02-23 1995-01-27 4-헤테로사이클릴-치환된 퀴나졸린 유도체, 이들의 제조 방법 및항암제로서의 용도 KR100225721B1 (ko)

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