KR940701397A - 불안해소 효과를 갖는 피페리딘 유도체 - Google Patents
불안해소 효과를 갖는 피페리딘 유도체Info
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Abstract
하기의 일반 구조식(I)을 갖는 피페리딘 화합물들은 시그마 수용체 활성도가 강하다:
상기 식(I)에서 R1은 a) 적어도 2개의 스페이서 기(spacer group)를 통해 피페리딜 N-원자에 연결되어 있는 알킬기, 알케닐기, 시클로알킬기, 시클로알케닐기, 페닐기, 시클로알킬알킬기, 시클로알케닐알킬기, 페닐알킬 또는 디페닐알킬기로 이루어지는 기 이 든지 혹은;
상기 식(I)에서, X는 CH10, O, S, SO, SO2또는 NR10이다.
한편, 상기 식(I)에서, (i) Z1과 Z2가 서로 연결되어 있을 때는 Z1이 CH2, O 또는 S이고; Z2및 Z3는 독립적으로 (CH2)n(여기서, n는 0 또는 1), 또는 S이든지, 혹은 Z1과 Z2는 둘다 -CH=CH-기를 의미할 수도 있든지; 또는 Z3가 (CH2)n(여기서, n=0)일 때에, Z1과 Z2는 둘다 3개의 2가기(二價基)를 의미할 수도 있고; 또는 ii) R1이 상기 b)에 정의된 기라면, Z1과 Z2는 또한 결합되어 있지 않을 수도 있는데, 이 경우에 Z1은 치환기이고, Z2는 수소이고, Z3는 (CH2)n(여기서, n=0)이다.
더욱이, 이 화합물들은 동물 모델에서, 불안 해소 효과가 있음이 나타났다. 따라서, 이 화합물들은 불안, 정신병, 간질, 운동장애, 운동신경장애, 건망증, 뇌혈관질환, 알쯔하이머타입의 노인성 치매, 또는 파킨슨병 치료용의 약품으로 유용하게 쓰인다.
Description
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Claims (13)
- 불안, 정신병, 간질, 운동장애, 운동신경장애, 건망증, 뇌혈관질환, 알쯔하이머 타입의 노인성 치매, 또는 파킨슨병 치료용의 약제 제조용으로 쓰기 위한 하기의 일반 구조식 I을 갖는 피페리딘 화합물 또는 이 화합물의 산 부가염 혹은 프로-드러그의 사용.[상기식에서, R1은 a) -D-B-A-R기(基)이고, 여기서 B는 분기쇄 또는 직쇄로 연결되어 있을 수 있고, 선택적으로 히드록시로 치환될 수 있고, 2 내지 24개의 탄소원자를 가지는 지방족 카르복시산으로 에스테르화되어질 수도 있는 알킬렌, 알케닐렌 및 알키닐렌 중에서 선택되는 19개 까지의 스페이서그룹(spacer group)이고; A는 O, S, SO, SO2및(여기서, W는 0 또는 S이고 점선은 선택적 결합을 표시)로부터 선택되는 하나의 ‘결합’ 또는 2가(價)의 기이고; R은 알킬, 알케닐, 시클로알킬, 시클로알케닐, 페닐, 시클로알킬 알킬, 시클로알케닐알킬, 페닐알킬, 디페닐알킬, 한 두개 히드록시기로 대체되어 있으며 2 내지 24개의 탄소원자를 가지는 지방족 카르복시산으로 선택적으로 에스테르화 되어 있을 수도 있는 알킬기, 그리고 페닐고리에 한개 이상의 치환기가 선택적으로 치환되어 있는 페닐기; 그리고 D는 CR8R9(여기서 R8및 R9는 아래에 R4내지 R7에 대해 정의된 치환된 또는 시클로알킬렌기로부터 독립적으로 선택); b) 상기 I식에서 R1은 하기의 일반 구조식 II을 갖는 기이다:상기식에서, X는 CHR10, O, S, SO, SO2또는 NR10인데, 여기서 R10은 수소, 저급 알킬 또는 알케닐, 시클로알킬 또는 시클로알킬알킬, 시클로알케닐 또는 시클로알케닐알킬, 아실, 아미노알킬, 모노- 또는 디알킬아미노알킬, 술포닐 또는 아릴알킬 또는 할로겐·저급알킬·저급알콕시·히드록시·트리플루오로메틸·시아노 중에서 독립적으로 선택되는 한개 이상의 치환기로 선택적으로 치환되는 페닐이든지, 혹은 R10은 헤테로 방향족 기중에서 바람직하게는 2-티에닐, 3-티에닐, 2-푸라닐, 3-푸라닐, 2-티아조릴, 2-옥사조릴, 2-이미다조릴, 2-피리딜, 3-피리딜, 또는 4-피리딜이고; 한두개의 점선은 ‘결합’을 표시할 수도 있고; Y로 부터 나오는 점선이 ‘결합’을 의미할 때는 Y가 N 또는 CH이고; 상기의 점선이 ‘결합’을 의미하지 않을 때는 Y가 CH2, NH, C=0 또는 C=S이고; RaRbRcRd는 수소, 할로겐, 저급알킬, 저급알콕시, 히드록시, 저급알킬티오, 저급 알킬술포닐, 저급 알킬- 또는 디알킬-아미노, 시아노, 트리플루오로메틸, 또는 트리플루오로메틸티오이고; U는 CH2, O 또는 S이고; 또는 U로부터 나오는 점선들 중의 하나가 ‘결합’을 가리킬때는 U는 CH이고; U와 Q1또는 U와 Q2사이의 결합이 삼중결합일 수도 있는데, 이 경우에는 U가 “C”이고; Q1은 한 결합, 알킬렌 또는 알케닐렌으로부터 선택되고 Q2는 적어도 두 개의 C원자, 알케닐렌 또는 Q2′ D기(여기서 Q2′는 Q2에 대한 정의와 같고, D는 위에 정의되어 있다)를 갖는 알킬렌이고, Q1및 Q2는 둘다 2 내지 20개의 탄소원자를 가지고, 2 내지 24개의 탄소원자를 가지는 지방족 카르복시산으로 선택적으로 에스테르화된 한개 이상의 히드록시기로 선택적으로 치환된 것이고; R2및 R3은 독립적으로 수소, 저급알킬이든지, 또는 서로 연결되어 에틸렌 또는 프로필렌 다리를 형성할 수 있고; R4, R5, R6, R7은 독립적으로 수소, 할로겐, 저급알킬, 저급알콕시, 히드록시, 저급알킬티오, 저급알킬- 또는 디알킬아미노, 시아노, 트리플루오로메틸, 또는 트리플루오로메틸티오이고; i) Z1및 Z2가 같이 연결되어 있을 경우에, Z2는 CH2, O, 또는 S이고; Z2및 Z3은 독립적으로 (CH2)n(여기서, n은 0 또는 1), O 또는 S인데, 단 조건은 Z2가 S 또는 O일 때 Z1이 O가 아닐 수도 있고, 또한 Z2와 Z3둘다 (CH2)n(여기서, n=0)이 아닐수도 있다는 것이고; 또는 Z1및 Z2는 함께 -CH=CH-기를 나타낼 수도 있고; 또는 Z3가 (CH2)n(여기서, n=0)일때, Z1및 Z2는 선택적으로 하나의 불포화 결합을 포함하고, 또한 선택적으로 하나의 O- 또는 S-헤테로 원자를 포함하는 3개의 2가의 기를 나타낼 수도 있든지; 또는 ii) R1이 상기 b)에 정의된 바의 기이라면, Z1및 Z2는 또한 연결되어 있지 않을수 있는데, 이 경우 Z1은 R4, R5, R6, R7에 대해 정의된 바의 기이고, Z2는 수소이고, Z3은 (CH2)n(여기서, n=0)이고; Z1, Z2, Z3이 상기 i)에 정의된 바의 것이고 (여기서, Z3은 n 이 0인 (CH2)n), 또 Z1및 Z2가 모두 선택적으로 하나의 불포화 결합을 포함하는 2 또는 3개의 2가의 탄화수소 기를 나타내고, 또한 R1이 상기 a)에 정의된 바의 기이라는 조건하에서는, 상기 D-B-A-R기는 페닐, -C1-3-알킬, 저급알킬 또는 저급알케닐이 아닐수도 있다.]
- 제1항에 있어서, 사용된 리반식 I의 화합물이, Z1및 Z2가 함께 결합되어 있고, Z1, Z2및 Z3중 적어도 하나는 O 또는 S인 화합물인 것을 특징으로 하는 피페리딘 화합물의 이용.
- 제2항에 있어서, 사용된 일반식 I의 화합물이 Z3은 n이 0인 (CH2)n이고, Z2는 “O” 또는 “S”이고, Z1은 CH2이거나 Z1과 Z2는 함께 CH2-O-CH2인 화합물인 것을 특징으로 하는 피페리딘 화합물의 이용.
- 제2항에 있어서, 사용된 일반식 I의 화합물이 Z1은 CH2, Z2가 O이고 Z3가 CH2인 것; 또는 Z3이 O이고 Z1-Z2가 CH=CH인 것; 또는 Z1은 O, Z3가 O이고 Z2는 n이 0인 (CH2)n인 화합물인 것을 특징으로 하는 피페리딘 화합물의 이용.
- 제1항에 있어서, 사용된 화합물이, Z1과 Z2가 함께 결합되어 있지 않고 Z3은 n=0 (CH2)n인 화합물인 것을 특징으로 하는 피페리딘 화합물의 이용.
- 제1항에 있어서, 사용된 일반식 I의 화합물이 1′-(3-아다만틸옥시-1-프로필) 스피로[3H-2-벤조피란-3,4′-피페리딘]; 1′-[4-(1-벤질-3-인돌일)-1-부틸]-스피로[이소벤조푸란-1(3H), 4′-피페리딘]; 1′-(3-(3-페닐이미다졸리딘-2-온-1-일)-1-프로필)스피로[이소벤조푸란-1(3H), 4′-피페리딘]; 1′-[4-[1-(4-플루오로페닐]-3-인돌일]-1-부틸]-스피로[이소벤조푸란-1(3H), 4′피페리딘]; 1,4-디히드로-1′-[4-[1-[(4-플루오로페닐)-3-인돌일]-1-부틸] 스피로[3H-2-벤조피란-3,4′-피페리딘]; 1′-[4-(1-p-톨루엔술폰일-3-인돌일)-1-부틸]스피로[이소벤조푸란-1(3H), 4′피페리딘]; 1′-[4-[5-플루오로-1-(4-플루오로페닐)-3-인돌일]-1-부틸] 스피로[이소벤조푸란-1(3H), 4′-피페리딘]; 6-플루오로-1′-[4-[1-(4-플루오로페닐)-3-인돌일]-1-부틸]스피로[이소벤조푸란-1-(3H), 4′-피페리딘]; 1′-[4-[1-(4-메틸페닐)-3-인돌일]-1-부틸] 스피로[1H-2-벤조피란-4(3H), 4′-피페리딘]; 1-(4-플루오로페닐)-3-[4-(4-(4-플루오로페닐)-1-피페리딜)-1-부틸]인돌; 1′-[4-1-(2-티아졸일)-3-인돌일]-1-부틸] 스피로[이소벤조푸란-1(3H), 4′-피페리딘]; 1′-[3-(5-플루오로벤조푸란-3-일)-1-프로필]스피로[이소벤조푸란-1(3H), 4′-피페리딘]; 1′-[3-(5-플루오로벤조푸란-3-일-부틸]스피로[이소벤조푸란-1(3H), 4′-피페리딘]; 1′-[4-[1-(4-플루오로페닐)-5-트리플루오로메틸인다졸-3-일]-1-부틸]스피로[이소벤조푸란-1(3H), 4′-피페리딘]; 4-플루오로페닐-3-[4-(4-(4-플루오로페닐)-1-피페리딘일)-1-부틸]-5-트리플루오로메틸-인다졸; 1′-(4-(1,2-벤즈이속사졸-3-일)-1-부틸)스피로[이소벤조푸란-1(3H), 4′-피페리딘]; 및 1′-[3-(벤조[b]티오펜-3-일티오)-1-프로필]스피로[이소벤조푸란-1(3H), 4′-피페리딘]; 로 구성된 군으로 부터 선택되는 것인 것을 특징으로 하는 피페리딘 화합물의 이용.
- 제1항에 규정된 일반식 I화합물이 R1이 상기 b)에서 정의한 바와같은 식 II의 기이고, Z1, Z2및 Z3가 상기 ii)에서 정의한 바와같고, X는 NH, Y는 CH이며, Y로 부터의 점선이 하나의 결합인 경우, -Q1-U-Q2는 탄소수가 5보다 적은 알킬이 아닐수 있고; R1이 Z3은 O, Z1은 CH2, Z2는 (CH2)n(여기서 n=0), X는 O, Y는 N인 앞서정의한 식 II의 기이고, Y로 부터의 점선은 하나의 결합을 나타내고, -Q1-U-Q2가 -(CH2)3인 경우, Rc는 플루오로가 아닐 수 있고; Z3은 O, Z2및 Z1은 모두 CH2이고 D-B-A-R은 선택적으로 치환된 펜에틸인 경우, R6은 메톡시가 아닐수 있으며; 그리고 Z1이 O, Z2및 Z3가 모두 CH2인 경우, D-B-A-R은 펜에틸, 또는 선택적으로 히드록시 치환된 헥실 또는 헵틸이 아닐 수 있는 것을 특징으로 하는 피페리딘 화합물 또는 이것의 산부가염 또는 프로-드러그.
- 제7항에 있어서, Z1및 Z2가 함께 결합된 경우 Z1, Z2및 Z3중 적어도 하나는 O 또는 S인 것을 특징으로 하는 피페리딘 화합물 또는 이것의 산부가염 또는 프로-드러그.
- 제8항에 있어서, 일반식 I의 화합물이 Z3은 n이 0인 (CH2)n이고, Z2는 “O” 또는 “S”이며 Z1은 CH2이거나 Z1및 Z2가 함께 CH2-O-CH2인 화합물인 것을 특징으로 하는 피페리딘 화합물 또는 이것의 산부가염 또는 프로-드러그.
- 제8항에 있어서, 일반식 I의 화합물이 Z1은 CH2, Z2는 O이고 Z3은 CH2인 것; Z3은 O이고 Z1-Z2는 CH=CH인것; 또는 Z1은 O, Z3은 O이며 Z2는 n=0인 (CH2)n인 화합물인 것을 특징으로 하는 피페리딘 화합물 또는 이것의 산부가염 또는 프로-드러그.
- 제7항에 있어서, 일반식 I의 화합물이 Z1및 Z2가 함께 결합되어 있지 않고 Z3은 n이 0인 (CH2)n인 화합물인 것을 특징으로 하는 피페리딘 화합물 또는 이것의 산부가염 또는 프로-드러그.
- 제7항에 있어서, 상기 화합물이 1′-(3-아다만틸옥시-1-프로필) 스피로[3H-2-벤조피란-3,4′-피페리딘); 1′-[4-(1-벤질-3-인돌일)-1-부틸]-스피로[이소벤조푸란-1(3H), 4′-피페리딘]; 1′-(3-(3-페닐이미다졸리딘-2-온-1-일)-1-프로필) 스피로[이소벤조푸란-1(3H), 4′-피페리딘]; 1′-[4-[-1-(4-플루오로페닐)-3-인돌일)-1-부틸]-스피로[3H-2-벤조피란-3,4′-피페리딘]; 1′-[4-[1-P-톨루엔술폰일-3-인돌일)-1-부틸]-스피로[이소벤조푸란-1(3H), 4′-피페리딘]; 1,4-디히드로-1′-[4-[1-(4-플루오로페닐)-3-인돌일]-1-부틸] 스피로[이소벤조푸란-1(3H), 4′-피페리딘]; 1′-[4-(1-p-톨루엔술폰일-3-인돌일)-1-부틸) 스피로[이소벤조푸란-1(3H), 4′-피페리딘]; 1′-[4-[5-플루오로-1-(4-플루오로페닐)-3-인돌일]-1-부틸] 스피로[이소벤조푸란-1(3H), 4′-피페리딘]; 6-플루오로-1′-[4-[1-(4-플루오로페닐)-3-인돌일]-1-부틸] 스피로[이소벤조푸란-1(3H), 4′-피페리딘]; 1′-[4-[1-(4-메틸페닐)-3-인돌일]-1-부틸] 스피로[1H-2-벤조푸란-1(3H), 4′-피페리딘]; 1-(4-플루오로페닐)-3-[4-(4-(4-플루오로페닐)-1-피페리딜)-1-부틸]인돌; 1′-[4-(1-(2-티아졸일)-3-인돌일]-1-부틸] 스피로[이소벤조푸란-1(3H), 4′-피페리딘]; 1′-[3-(5-플루오로벤조푸란-3-일)-1-프로필] 스피로[이소벤조푸란-1(3H), 4′-피페리딘]; 1′-[4-(5-플루오로벤조푸란-3-일)-1-부틸] 스피로[이소벤조푸란-1(3H), 4′-피페리딘]; 1′-[4-[1-(4-플루오로페닐)-5-트리풀루오로메틸인다졸-3-일]-1-부틸] 스피로[이소벤조푸란-1(3H), 4′-피페리딘]; 4-플루오로페닐-3-[4-(4-(4-플루오로페닐)-1-피페리딘일)-1-부틸]-5-트리플루오로메틸-인다졸; 1′-(4-(1,2-벤즈이속사졸-3-일)-1-부틸)스피로[이소벤조푸란-1(3H), 4′-피페리딘]; 및 1′-[3-(벤조[b] 티오펜-3-일티오)-1-프로필] 스피로[이소벤조푸란-1(3H), 4′-피페리딘]; 로 구성된 군으로 부터 선택되는 것인 것을 특징으로 하는 피페리딘 화합물 또는 이것의 산분가염 또는 프로-드러그.
- 하나 이상의 약제학적으로 허용되는 담체 또는 희석제와 함께 제6항에 따른 적어도 하나의 피페리딘 화합물 또는 이것의 약제학적으로 허용되는 산부가염 또는 프로-드러그로 구성된 것을 특징으로 하는 약제학적 조성물.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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DK1131/91 | 1991-06-13 | ||
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DK15792A DK15792D0 (da) | 1992-02-10 | 1992-02-10 | Spirocyclic compounds |
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- 1993-12-10 FI FI935558A patent/FI108137B/fi active
- 1993-12-13 US US08/166,647 patent/US5665725A/en not_active Expired - Lifetime
-
1995
- 1995-03-30 HU HU95P/P00094P patent/HU210869A9/hu unknown
- 1995-06-07 US US08/478,563 patent/US5807871A/en not_active Expired - Fee Related
- 1995-06-07 US US08/486,510 patent/US6031099A/en not_active Expired - Fee Related
-
1998
- 1998-05-06 JP JP13918398A patent/JP3203230B2/ja not_active Expired - Fee Related
- 1998-05-06 JP JP10139146A patent/JPH111475A/ja active Pending
- 1998-08-12 HK HK98109879A patent/HK1009272A1/xx not_active IP Right Cessation
-
1999
- 1999-09-07 US US09/391,290 patent/US6207677B1/en not_active Expired - Fee Related
- 1999-09-16 NO NO19994488A patent/NO310275B1/no not_active IP Right Cessation
- 1999-09-16 NO NO994487A patent/NO994487D0/no not_active Application Discontinuation
- 1999-10-04 FI FI992135A patent/FI112480B/fi active
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