KR20020012590A - 베타2-아드레날린성 촉진제 - Google Patents
베타2-아드레날린성 촉진제 Download PDFInfo
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Abstract
Description
Claims (16)
- 유리, 염 또는 용매화물 형태의 하기 화학식 I의 화합물.<화학식 I>식 중,Ar은 하기 화학식 II의 기이고,<화학식 II>R1은 수소, 히드록시 또는 알콕시이고,R2및 R3은 각각 독립적으로 수소 또는 알킬이고,R4, R5, R6및 R7은 각각 독립적으로 수소, 할로겐, 시아노, 히드록시, 알콕시, 아릴, 알킬, 1개 이상의 할로겐 원자 또는 1개 이상의 히드록시 또는 알콕시기로 치환된 알킬, 1개 이상의 헤테로 원자로 단속된 알킬, 알케닐, 트리알킬실릴,카르복시, 알콕시카르보닐 또는 -CONR11R12(여기서, R11및 R12는 각각 독립적으로 수소 또는 알킬임)이거나, R4와 R5, R5와 R6또는 R6과 R7은 이들이 결합한 탄소 원자와 함께 카르보시클릭 또는 헤테로시클릭 고리를 나타내고,R8은 할로겐, -OR13, -CH2OR13또는 -NHR13{여기서, R13은 수소, 알킬, 1개 이상의 헤테로원자로 단속된 알킬, -COR14(여기서, R14는 수소, -N(R15)R16, 알킬 또는 1개 이상의 헤테로원자로 단속된 알킬, 또는 아릴이고, R15및 R16은 각각 독립적으로 수소, 알킬 또는 1개 이상의 헤테로원자로 단속된 알킬임)이거나, R13은 -C(=NH)R17, -SOR17또는 -SO2R17(여기서, R17은 알킬 또는 1개 이상의 헤테로원자로 단속된 알킬임)임}이고,R9는 수소이거나, R8은 -NHR18(여기서, -NHR18과 R9는 이들이 결합한 탄소 원자와 함께 5원 또는 6원 헤테로사이클을 나타냄)이고,R10은 -OR19또는 -NHR19{여기서, R19는 수소, 알킬, 1개 이상의 헤테로원자로 단속된 알킬 또는 -COR20(여기서, R20은 -N(R21)R22, 알킬 또는 1개 이상의 헤테로원자로 단속된 알킬, 또는 아릴이고, R21및 R22는 각각 독립적으로 수소, 알킬 또는 1개 이상의 헤테로원자로 단속된 알킬임)임}이고,X는 할로겐, 할로메틸 또는 알킬이고,Y는 탄소 또는 질소이고,n은 1 또는 2이고,p는 Y가 질소인 경우 0이고, Y가 탄소인 경우 1이고,q 및 r은 각각 0 또는 1이고, q+r의 합은 1 또는 2이며,별표*로 표시된 탄소 원자는 R1이 히드록시 또는 알콕시인 경우 R 또는 S 배위, 또는 이들의 혼합물을 갖는다.
- 제1항에 있어서, Ar이Y는 탄소이고,R8은 -NHR18이며, -NHR18과 R9는 함께R23이 알킬렌, 알케닐렌 또는 알킬렌옥시기인 화학식 -NH-CO-R23의 기,R24가 알킬렌옥시기인 화학식 -NH-SO2-R24의 기,R25가 알킬렌 또는 알케닐렌기이고, R26이 알킬인 화학식 -NH-R25(COOR26)-의 기이거나, 또는화학식 -NH-CO-NH- 또는 -NH-CO-S-의 기를 나타내고,R10은 -OR19(여기서, R19는 제1항에 정의된 바와 같음)이고,X는 알킬이고,p는 1, q는 1이고, r은 0 또는 1인 화학식 II의 기인 화합물.
- 제2항에 있어서, Ar이 하기 화학식 III, IV, V, VI 또는 VII의 기인 화합물.<화학식 III><화학식 IV><화학식 V><화학식 VI><화학식 VII>식 중, R29, R30및 R31은 각각 독립적으로 수소 또는 C1-C4-알킬이고,Z는 -O-, -NH- 또는 -S-이다.
- 제1항에 있어서, Ar이 하기 화학식 IIIa의 기인 화합물.<화학식 IIIa>식 중, R29, R30및 R31은 각각 독립적으로 수소 또는 C1-C4-알킬이다.
- 제1항에 있어서, Ar이 Y는 탄소이고, R8은 -CH2OR13(여기서, R13은 수소, C1-C4-알킬 또는 C1-C4-알콕시-C1-C4-알킬임)이고, R9는 수소이고, R10은 -OR19(여기서, R19는 수소, C1-C4-알킬 또는 C1-C4-알콕시-C1-C4-알킬임)이거나, R10은 -NHR19[여기서, R19는 수소, C1-C4-알킬 또는 -COR20{여기서, R20은 C1-C4-알킬, C6-C10-아릴 또는 -N(R21)R22(여기서, R21및 R22는 각각 독립적으로 수소 또는 C1-C4-알킬임)임}임]이고, p 및 q는 각각 1이고, r은 0인 화학식 II의 기이거나; 또는 Y는 질소이고, R8은 -CH2OR13(여기서, R13은 수소, C1-C4-알킬 또는 C1-C4-알콕시-C1-C4-알킬임)이고, R10은 -OR19(여기서, R19는 수소, C1-C4-알킬 또는 C1-C4-알콕시-C1-C4-알킬임)이고, p 및 r은 0이고, q는 1인 화학식 II의 기인 화합물.
- 제5항에 있어서, Ar이 하기 화학식 XII, XIII 또는 XIV의 기인 화합물.<화학식XII><화학식 XIII><화학식 XIV>
- 제1항에 있어서, Ar이 Y는 탄소이고, R8이 -NHR13{여기서, R13은 수소, C1-C10알킬, 1 내지 3개의 헤테로원자로 단속된 C1-C10알킬, -COR14(여기서, R14는 수소, C1-C10-알킬 또는 1 내지 3개의 헤테로원자로 단속된 C1-C10-알킬임)이거나, R13이 -C(=NH)R17, -SOR17또는 -SO2R17(여기서, R17은 C1-C10-알킬 또는 1 내지 3개의 헤테로원자로 단속된 C1-C10-알킬임)이고, R9는 수소이고, R10은 -OR18(여기서, R18은 수소, C1-C4-알킬 또는 C1-C4-알콕시-C1-C4알킬임)임}이고, p 및 q는 각각 1이고, r은 0인 화학식 II의 기인 화합물.
- 제7항에 있어서, Ar이 하기 화학식 XV의 기인 화합물.<화학식 XV>
- 제1항 내지 제8항 중 어느 한 항에 있어서, R4, R5, R6및 R7이 각각 수소이거나 이들이 결합한 벤젠 고리가 대칭적으로 치환된 화합물.
- 제1항에 있어서, Ar이 화학식 III, IV, V, XII 또는 XV의 기이고, R1은 히드록시이고, R2및 R3은 수소이며, R4와 R7은 동일하고 각각 수소, C1-C4-알킬 또는 C1-C4-알콕시이고, R5와 R6은 동일하고 각각 수소, C1-C4-알킬, C1-C4-알콕시 또는 C1-C4-알콕시-C1-C4-알킬이거나, R5와 R6은 함께 -(CH2)4- 또는 -O(CH2)2O-를 나타내는 유리, 염 또는 용매화물 형태의 화합물.
- 제10항에 있어서, 별표*로 표시된 화학식 I의 탄소 원자가 R 배위를 갖는 화합물.
- 유리, 염 또는 용매화물 형태의 하기 화학식 I의 화합물.<화학식 I>식 중, (A) Ar은 하기 화학식 III의 기이고,<화학식 III>(여기서, R29, R30및 R31은 각각 H이고, R1은 OH이고, R2및 R3은 각각 H임)(i) n은 1이고, R4및 R7은 각각 CH3O-이고, R5및 R6은 각각 H이거나;(ii) n은 1이고, R4및 R7은 각각 H이고, R5및 R6은 각각 CH3CH2-이거나;(iii) n은 1이고, R4및 R7은 각각 H이고, R5및 R6은 각각 CH3-이거나;(iv) n은 1이고, R4및 R7은 각각 CH3CH2-이고, R5및 R6은 각각 H이거나;(v) n은 1이고, R4및 R7은 각각 H이고, R5및 R6은 함께 -(CH2)4-를 나타내거나;(vi) n은 1이고, R4및 R7은 각각 H이고, R5및 R6은 함께 -O(CH2)2O-를 나타내거나;(vii) n은 1이고, R4및 R7은 각각 H이고, R5및 R6은 각각 CH3(CH2)3-이거나;(viii) n은 1이고, R4및 R7은 각각 H이고, R5및 R6은 각각 CH3(CH2)2-이거나;(ix) n은 2이고, R4, R5, R6및 R7은 각각 H이거나;(x) n은 1이고, R4및 R7은 각각 H이고, R5및 R6은 각각 CH3OCH2-이거나; 또는(B) Ar은 하기 화학식 XV의 기이고,<화학식 XV>(여기서, R13은 H임)R1은 OH이고, R2및 R3은 각각 H이고, R4및 R7은 각각 H이고, R5및 R6은 각각 H이며, n은 1이거나; 또는(C) 8-히드록시-5-[1-히드록시-2-(인단-2-일아미노)-에틸]-1H-퀴놀린-2-온, 5-[2-(5,6-디메톡시-인단-2-일아미노)-1-히드록시-에틸]-8-히드록시-1H-퀴놀린-2-온, 5-[2-(5,6-디에틸-인단-2-일아미노)-1-히드록시-에틸]-8-히드록시-3-메틸-1H-퀴놀린-2-온, 5-[2-(5,6-디에틸-인단-2-일아미노)-1-히드록시-에틸]-8-메톡시메톡시-6-메틸-1H-퀴놀린-2-온, 5-[2-(5,6-디에틸-인단-2-일아미노)-1-히드록시-에틸]-8-히드록시-6-메틸-1H-퀴놀린-2-온, 8-히드록시-5-[2-(5,6-디에틸-인단-2-일아미노)-1-히드록시-에틸]-3,4-디히드로-1H-퀴놀린-2-온, N-{2-히드록시-5-[(R)-1-히드록시-2-(2,5,6-트리메틸-인단-2-일아미노)-에틸]-페닐}-포름아미드, 5-[(R)-2-(5,6-디에틸 -2-메틸-인단-2-일아미노)-1-히드록시-에틸]-8-히드록시-1H-퀴놀린-2-온, (S)-5-[2-(4,7-디에틸-인단-2-일아미노)-1-히드록시-에틸]-1H-퀴놀린-2-온 염산염, 5-[(R)-1-히드록시-2-(6,7,8,9-테트라히드로-5H-벤조시클로헵텐-7-일아미노)-에틸]-1H-퀴놀린-2-온 염산염, (R)-5-[2-(5,6-디에틸-인단-2-일아미노)-1-히드록시-에틸] -1H-퀴놀린-2-온 염산염, N-{5-[(R)-2-(5,6-디에틸-인단-2-일아미노)-1-히드록시-에틸]-2-히드록시-페닐}-포름아미드, 4-[(R)-2-(5,6-디에틸-인단-2-일아미노)-1-히드록시-에틸]-2-디메틸아미노-페놀 염산염, 4-[(R)-2-(5,6-디에틸-인단-2-일아미노)-1-히드록시-에틸]-2-메틸아미노-페놀 염산염, N-{5-[2-(5,6-디에틸-인단-2-일아미노)-1-히드록시-에틸]-2-히드록시-페닐}-메탄술폰아미드 염산염), (R)-8-히드록시-5-[(S)-1-히드록시-2-(4,5,6,7-테트라메틸-인단-2-일아미노)-에틸]-1H-퀴놀린-2-온, 8-히드록시-5-[(R)-1-히드록시-2-(2-메틸-인단-2-일아미노)-에틸]-1H-퀴놀린-2-온, 5-[2-(5,6-디에틸-인단-2-일아미노)-에틸]-8-히드록시-1H-퀴놀린-2-온, 8-히드록시-5-[(R)-1-히드록시-2-(2-메틸-2,3,5,6,7,8-헥사히드로-1H-시클로펜타[b]나프탈렌-2-일아미노)-에틸]-1H-퀴놀린-2-온, 5-[(S)-2-(2,3,5,6,7,8-헥사히드로-1H-시클로펜타[b]나프탈렌-2-일아미노)-1-히드록시-에틸]-8-히드록시-1H-퀴놀린-2-온, N-{2-히드록시-5-[(R)-1-히드록시-2-(2-메틸-인단-2-일아미노)-에틸]-페닐}-메탄술폰아미드), 에탄술폰산 {2-히드록시-5-[(R)-1-히드록시-2-(2-메틸-인단-2-일아미노)-에틸]-페닐}-아미드, 프로판-1-술폰산 {2-히드록시-5-[(R)-1-히드록시-2-(2-메틸-인단-2-일아미노)-에틸]-페닐}-아미드, N-{5-[2-(2-에틸-인단-2-일아미노)-1-히드록시-에틸]-2-히드록시-페닐}-메탄술폰아미드 또는 N-{2-히드록시-5-[(R)-1-히드록시-2-(2,5,6-트리메틸-인단-2-일아미노)-에틸]-페닐}-메탄술폰아미드로부터 선택된 화합물이다.
- 제1항 내지 제12항 중 어느 한 항에 따른 화합물을 임의로 제약상 허용되는 담체와 함께 포함하는 제약 조성물.
- β2-아드레날린성 수용체의 활성화에 의해 예방되거나 경감되는 질병 치료용 의약을 제조하기 위한 제1항 내지 제12항 중 어느 한 항에 따른 화합물의 용도.
- 폐쇄성 또는 염증성 기도 질환 치료용 의약을 제조하기 위한 제1항 내지 제12항 중 어느 한 항에 따른 화합물의 용도.
- (a) R1이 히드록시인 화합물을 제조하기 위해 (i) 하기 화학식 XVI의 화합물을 하기 화학식 XVII의 화합물과 반응시키거나, (ii) 하기 화학식 XVIII의 화합물을 환원시켜서 케토기를 -CH(OH)-로 전환시키거나;(b) R1이 수소인 화합물을 제조하기 위해 R1이 히드록시인 화학식 I의 상응하는 화합물을 환원시키거나; 또는(c) R1이 알콕시인 화학식 I의 화합물을 제조하기 위해 (i) R1이 히드록시인 화학식 I의 상응하는 화합물을 O-알킬화시키거나 (ii) R1대신에 이탈 부분을 갖는 상응하는 화합물을 R1이 알콕시인 화학식 R1H의 알코올과 반응시키고;경우에 따라서는 보호된 형태의 화학식 I의 생성된 화합물을 비보호된 형태의 상응하는 화합물로 전환시키고;유리, 염 또는 용매화물 형태의 화학식 I의 생성된 화합물을 회수하는 것을 포함하는 유리, 염 또는 용매화물 형태의 화학식 I의 화합물의 제조 방법.<화학식 XVI><화학식 XVII><화학식 XVIII>식 중, Ar1은 제1항에서 정의한 바와 같은 Ar이거나 그의 보호된 형태이고, R2, R3, R4, R5, R6, R7및 n은 제1항에서 정의한 바와 같고, R32는 수소 또는 아민 보호기이다.
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