KR20030042036A - 단백질 키나제 c 억제제로서의 인돌릴말레이미드 유도체 - Google Patents
단백질 키나제 c 억제제로서의 인돌릴말레이미드 유도체 Download PDFInfo
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Abstract
Description
Claims (11)
- 화학식 Ⅰ의 화합물 또는 그의 염:상기 식에서Ra는 H; C1-4알킬; 또는 OH, NH2, NHC1-4알킬 또는 N(디-C1-4알킬)2로 치환된 C1-4알킬이고;Rb는 H; 또는 C1-4알킬이며;R은 화학식 (a), (b), (c), (d), (e) 또는 (f)의 라디칼이고:여기서각각의 R1, R4, R7, R8, R11및 R14는 OH; SH; 헤테로사이클릭 잔기; NR16R17(여기서 각각의 R16및 R17은 독립적으로 H 또는 C1-4알킬이거나 R16과 R17은 그들이 결합된 질소 원자와 함께 헤테로사이클릭 잔기를 형성한다); 또는 화학식 α의 라디칼:-X-Rc-Y (α)(여기서 X는 직접 결합, O, S 또는 NR18이고, R18은 H 또는 C1-4알킬이며,Rc는 C1-4알킬렌 또는 하나의 CH2가 CRxRy(Rx와 Ry중 하나는 H이고 다른 하나는 CH3이거나, 각각의 Rx및 Ry는 CH3이거나 Rx와 Ry는 함께 -CH2-CH2-를 형성한다)에 의해 대체된 C1-4알킬렌이고,Y는 말단 탄소 원자에 결합하고 OH, 헤테로사이클릭 잔기 및 -NR19R20(여기서 각각의 R19및 R20은 독립적으로 H, C3-6사이클로알킬, C3-6사이클로알킬-C1-4알킬, 아릴-C1-4알킬 또는 말단 탄소 원자에서 OH로 임의로 치환된 C1-4알킬이거나, R19및 R20은 그들이 결합된 질소 원자와 함께 헤테로사이클릭 잔기를 형성한다)로부터 선택된다)이며;각각의 R2, R3, R5, R6, R9, R10, R12, R13, R15및 R'15는 독립적으로 H, 할로겐, C1-4알킬, CF3, OH, SH, NH2, C1-4알콕시, C1-4알킬티오, NHC1-4알킬, N(디-C1-4알킬)2또는 CN이고;E는 -N=이고 G는 -CH=이거나 E는 -CH=이고 G는 -N=이며;환 A는 임의로 치환된다.
- 제1항에 있어서, R1, R4, R7, R8, R11, R14또는 Y로서, 또는 N16R17또는 NR19R20에 의해 각각 형성된 헤테로사이클릭 잔기는 1 또는 2 개의 헤테로원자를 포함하고, 하나 이상의 환 탄소 원자 및/또는 존재하는 경우 하나의 환 질소 원자에서 임의로 치환되는 3 내지 8 원 포화, 불포화 또는 방향족 헤테로사이클릭 환인 화합물.
- 제2항에 있어서, R1, R4, R7, R8, R11, R14또는 Y로서의, 또는 NR16R17또는 NR19R20에 의해 각각 형성되는 헤테로사이클릭 잔기는 화학식 (γ)의 잔기인 화합물:상기 식에서환 D는 5, 6 또는 7 원 포화, 불포화, 또는 방향족 환이고;Xb는 -N-, -C= 또는 -CH-이며;Xc는 -N=,-NRf-,-CRf'= 또는 -CHRf'-(여기서 Rf는 환 질소 원자에 대한 치환체이고 C1-6알킬; 아실; C3-6사이클로알킬; C3-6사이클로알킬-C1-4알킬; 페닐; 페닐-C1-4알킬; 헤테로사이클릭 잔기; 및 화학식 (β)의 잔기:- R21-Y' (β)(여기서 R21은 C1-4알킬렌 또는 O에 의해 차단된 C2-4알킬이고,Y'는 OH, NH2, NH(C1-4알킬) 또는 N(C1-4알킬)2이다)로부터 선택되며,Rf'는 환 탄소 원자에 대한 치환체이고, C1-4알킬; C1-4알킬에 의해 임의로 추가 치환된 C3-6사이클로알킬;(여기서 p는 1, 2 또는 3이다); CF3; 할로겐; OH; NH2; -CH2-NH2; -CH2-OH; 피페리딘-1-일; 및 피롤리디닐로부터 선택된다)이며;C1과 C2간의 결합은 포화 또는 불포화이며;각각의 C1과 C2는 독립적으로 환 탄소 원자에 대해 상기 표시된 것들 중 선택된 1 또는 2 개의 치환체로 임의로 치환된 탄소 원자이고;C3와 Xb사이와 C1과 Xb사이의 선은 각각 5, 6 또는 7 원 환 D를 얻는데 요구되는 탄소 원자의 수를 나타낸다.
- 제3항에 있어서, D는 제3항에 특정된 바와 같이 임의로 C- 및/또는 N-치환된 피페라지닐 환인 화합물.
- 제1항 내지 제4항 중 어느 한 항에 있어서, R이 화학식 (d), (e) 또는 (f)의 라디칼인 화합물.
- 제1항에 있어서,3-(1,H-인돌-3-일)-4-[2-(4-메틸-피페라진-1-일)-퀴나졸린-4-일]-피롤-2,5-디온, 3-(1,H-1-메틸-인돌-3-일)-4-[2-(4,7-디아자-스피로[2.5]옥트-7-일)-퀴나졸린-4-일]-피롤-2,5-디온, 3-(1,H-인돌-3-일)-4-[2-(4-에틸-피페라진-1-일)-퀴나졸린-4-일]-피롤-2,5-디온, 3-(1,H-1-메틸-인돌-3-일)-4-[2-(4-에틸-피페라진-1-일)-6-클로로-퀴나졸린-4-일]-피롤-2,5-디온, 3-(1,H-7-메틸-인돌-3-일)-4-[2-(4-메틸-피페라진-1-일)-6-클로로-퀴나졸린-4-일]-피롤-2,5-디온, 3-(1,H-1-메틸-인돌-3-일)-4-[2-(3(S)-메틸-피페라진-1-일)-6-클로로-퀴나졸린-4-일]-피롤-2,5-디온, 3-(1,H-1-메틸-인돌-3-일)-4-[2-(3(R)-메틸-피페라진-1-일)-6-클로로-퀴나졸린-4-일]-피롤-2,5-디온 및 3-(1,H-인돌-3-일)-4-[3-(4-메틸-피페라진-1-일)-이소퀴놀린-1-일]-피롤-2,5-디온, 또는 그의 염으로부터 선택되는 화합물.
- a) 화학식 Ⅱ의 화합물을 화학식 Ⅲ의 화합물과 반응시키거나;b) 화학식 Ⅳ의 화합물을 화학식 Ⅴ의 화합물을 반응시키거나;c) 화학식 Ⅰ의 화합물에서 치환체 R1, R4, R7, R8, R11또는 R14를 또 다른 치환체 R1, R4, R7, R8, R11또는 R14로 전환시키고, 필요한 경우, 유리 형태로 얻어진 생성된 화학식 Ⅰ의 화합물을 염 형태로 전환시키거나 적절한 경우 반대로 행하는것을 포함하는 제1항에 따른 화학식 Ⅰ의 화합물의 제조방법:R-CH2-CO-NH2(Ⅲ)R-CO-CO-OCH3(Ⅴ)상기 식에서, Ra, Rb, 환 A, 및 R은 제1항에 정의된 바와 같다.
- 제1항에 있어서, 약제로서 사용하기 위한 화합물.
- 유리 형태 또는 약제학적으로 허용되는 염 형태의 제1항에 따른 화학식 Ⅰ의 화합물을 그를 위한 약제학적으로 허용되는 희석제 또는 담체와 함께 포함하는 약제학적 조성물.
- a) PKC 및 T-세포 활성화 및 증식 억제제 및 b) 면역억제제, 면역조절제, 항-염증, 항증식 또는 항당뇨 약물로부터 선택되는 적어도 하나의 제2 약제를 포함하는 배합물.
- 유효량의 제1항에 따른 화학식 Ⅰ의 화합물 또는 그의 약제학적으로 허용되는 염을 대상에게 투여하는 것을 포함하는, 치료를 필요로 하는 대상에서 T 림포사이트 및/또는 PKC 매개된 장애 또는 질환을 예방 또는 치료하는 방법.
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