KR960704900A - 시그마 및/또는 5에이취티1에이 (5ht1a) 수용기에 대한 활성을 가진 테트라히드로피리딘-(또는 4-히드록시피레리딘) 알킬아졸 (tetrahydropyridine-(or 4-hydroxypiperidine)alkylazoles having an affinity for sigma and/or 5ht1a receptors) - Google Patents

시그마 및/또는 5에이취티1에이 (5ht1a) 수용기에 대한 활성을 가진 테트라히드로피리딘-(또는 4-히드록시피레리딘) 알킬아졸 (tetrahydropyridine-(or 4-hydroxypiperidine)alkylazoles having an affinity for sigma and/or 5ht1a receptors) Download PDF

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KR960704900A
KR960704900A KR1019960701606A KR19960701606A KR960704900A KR 960704900 A KR960704900 A KR 960704900A KR 1019960701606 A KR1019960701606 A KR 1019960701606A KR 19960701606 A KR19960701606 A KR 19960701606A KR 960704900 A KR960704900 A KR 960704900A
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butyl
tetrahydropyridinyl
phenyl
hydroxy
piperidinyl
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메르세-비달 라몬
프라골라-콘스탄사 조르디
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호세 마리아 라폴스 페러
라 보라토리오스 델 디알. 에스테베, 에스. 아.
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Abstract

본 발명은 불안증, 정신병, 간질, 경련, 운동기능 장애, 건망증, 뇌혈관 질환 또는 노인성 치매의 치료에 사용되는 약제로서 하기 일반식(I)의 화합물을 제공한다.

Description

시그마 및/또는 5에이취티1에이 (5HT1A) 수용기에 대한 활성을 가진 테트라히드로피리딘-(또는 4-히드록시피레리딘) 알킬아졸 (TETRAHYDROPYRIDINE-(OR 4-HYDROXYPIPERIDINE)ALKYLAZOLES HAVING AN AFFINITY FOR SIGMA AND/OR 5HT1A RECEPTORS)
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (5)

  1. 하기 일반식(I)의 화합물 및 그 생리적 허용염;
    상기 식에서, R1, R2및 R3은 동일하거나 상이하며, 각각 수소 원자, 할로겐 원자, 선형 또는 분지형 알킬라디칼, 퍼플루오로알킬 라디칼, 아릴 또는 치환된 아릴 라디칼 또는 알콕시 라디칼을 의미하며, 또한, 두 개의 인접한 라디칼은 방향족 또는 포화 고리를 이룰 수 있으며, A는 탄소 원자를 의미하고 점선은 추가의 결합을 의미하거나, 아니면 A는 히드록실기에 연결된 탄소 원자(C-OH)를 의미하고 점선은 추가의 결합이 없음을 의미하고, n은 2내지 6의 번위의 값이며, 4가 바람직하고, Z1는질소 원자 또는 C-R4로나타낼 수 있는치환된 탄소 원자를 의미하고, Z2는 질소 원자 또는 C-R5로 나타낼 수 있는 치환된 탄소 원자를 의미하고 Z4는 질소 원자 또는 C-R7로 나타낼 수 있는 치환된 탄소 원자를 의미하고, R4, R5, R6및 R7은 동일하거나 상이하며, 각각 수소 원자, 할로겐 원자, 선형 또는 분지형 알킬 라디칼, 히드록시 라디칼, 알콕시 라디칼, 카르복실 라디칼, 카르복스아미드 라디칼, 알킬 카르복실레이트 라디칼 또는 아릴 또는 치환된 아릴 라디칼을 의미하거나, 아니면 두 개의 인접한 라디칼이 방향족 고리일 수도 있고 아닐 수도 있는 또다른 고리의 일부를 이룰 수 있다.
  2. 제1항에 있어서, 하기군에서 선택되는 일반식(I)의 화합물; 1,4-클로로-1-〔4-(4-히드록시-4-페닐-1-피페리디닐)부틸〕-1H-피라졸, 2. 4,5-클로로-1-〔4-(4-히드록시-4-페닐-1-피페리디닐)부틸〕-2-메틸-1H-이미다졸, 3. 1-〔4-(4-히드록시-4-페닐-1-피페리디닐)부틸〕-1H-벤즈이미다졸, 4. 1-〔4-(4-히드록시-4-페닐-1-피페리디닐)부틸〕-1H-1,2,4-트리아졸, 5. 4-클로로-1-〔4-(4-클로로페닐)-4-히드록시-4-페닐-1-피페리디닐)부틸〕-1H-피라졸 , 6. 4,5-디클로로-1-〔4-(4-히드록시-4-(4-클로로페닐-1-피페리디닐)부틸〕-2-메틸-1H-이미다졸, 7. 4-클로로-1-〔4-(4-히드록시-4-(3-트리플루오로메틸페닐)-1-피페리디닐)부틸〕-1H-피라졸, 8. 4,5-디클로로-1-〔4-(4-히드록시-4-(3-트리프루오로메틸페닐)-1-피페리디닐)부틸〕-2-메틸-1H-이미다졸, 9. 4,5-디클로로-1-〔4-〔4-(4-플루오로페닐)-4-히드록시-1-피페리디닐〕부틸〕-2-메틸-1H-이미다졸, 10. 1-〔4-〔4-(4-히드록시-4-페닐-1-피페리디닐〕부틸〕인돌, 11. 4,5-디클로로-1-{4-〔4-히드록시-4-(4-메틸페닐)-1-피페리디닐)부틸〕-2-메메틸-1A-이미다졸틸-1H-피라졸, 12. 1-〔4-(4-히드록시-4-페닐)-1-피페리디닐〕부틸}-1H-피라졸, 13. 1-〔4-(4-히드록시-4-페닐-1-피페리디닐)부틸〕-1H-인다졸, 14. 2-〔4-(4-히드록시-4-페닐-1-피페리디닐)부틸〕-1H-인다졸, 15. 4-클로로-1-{4-〔4-(4-히드록시-4-(4-메틸페닐)-1-피페리디닐)부틸〕-1H-피라졸, 16. 4-클로로-1-〔4-(4-히드록시-4-(40메톡시페닐-1-피페리디닐)부틸〕-1H-피라졸, 17. 1-〔4-(4-히드록시-4-페닐-1-피페리디닐)부틸〕-2-페닐-1H-이미다졸, 18. 1-〔4-(4-히드록시-4-(4-메틸페닐)-1-피페리디닐)부틸〕-1H-벤즈이미다졸, 19. 4,5-디페닐-1-〔4-(4-히드록시-4-페닐-1-피페리디닐)부틸〕-1H-이미다졸, 20. 4-클로로-1-{4-〔4-히드록시-4-(1-나프틸)-1-피페리디닐〕부틸}-1H-피라졸, 21. 4-클로로-1-{4-〔4-히드록시-4-(2-나프틸)-1-피페리디닐)부틸〕-1H-피라졸, 22. 4-클로로-1-{4-〔4-페닐-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-1H-피라졸, 23. 1-{4-〔4-페닐-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-1H-벤즈이미다졸, 24. 1-{4-〔4-페닐-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-1H-1,2,4-트리아졸, 25. 4-클로로-1-{4-〔4-(4-클로로페닐)-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-1H-피라졸, 26. 4,5-디클로로-1-{4-〔4-(4-클로로페닐)-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-2-메틸-1H-이미다졸, 27. 4-클로로-1-{4-〔4-(3-트리플루오로메틸페닐)-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-1H-피라졸, 28. 4,5-디클로로-2-메틸-1-{4-〔4-(3-트리플루오로메틸페닐)-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-1H-이니다졸, 29. 4-클로로-1-{4-〔4-(4-플루오로페닐)-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-1H-피라졸, 30. 4,5-디클로로-1-{4-〔4-(4-플루오로페닐)-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-2-메틸-1H-이미다졸, 31. 4,5-디클로로-1-{4-〔4-페닐-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-2-메틸-1H-이미다졸, 32. 4,5-디클로로-1-{4-〔4-페닐-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-2-메틸-1H-이미다졸 염산염, 33. 4,5-디클로로-1-{4-〔4-페닐-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-2-메틸-1H-이미다졸 이염산염, 34. 1-{4-〔4-(4-플루오로페닐)-1-(1,2,3,6-테트라히드로피리디닐)부틸〕인돌, 35. 1-{4-〔4-(4-플루오로페닐)-1-(1,2,3,6-테트라히드로피리디닐)부틸〕인돌, 36. 4,5-디클로로-2-메틸-1-{4-〔4-(4-메틸페닐)-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-1H-이미다졸, 37. 1-{4-〔4-페닐-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-1H-피라졸, 38. 1-{4-〔4-페닐-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-1H-인다졸, 39. 2-{4-〔4-페닐-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-2H-인다졸, 40. 4-클로로-1-{4-〔4-(4-메틸페닐)-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-1H-피라졸, 41. 4-클로로-1-{4-〔4-(4-메톡시페닐)-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-1H-피라졸, 42. 4-클로로-1-{4-〔4-페닐-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-1H-피라졸, 43. 4,5-디클로로-1-{4-〔4-(4-메톡시페닐)-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-2-메틸-1H-이미다졸, 44. 2-페닐-1-{4-〔4-(4-메톡시페닐)-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-1H-이미다졸, 45. 1-{4-〔4-(4-메틸페닐)-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-1H-벤즈이미다졸, 46. R4, R5, R6 및 R7가 또다른 방향족 또는 비방향족 고리를 형성하지 않는 4,5-디페닐-1-{4-〔4-페닐-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-1H-이미다졸, 47. 4-클로로-1-{4-〔4-(1-나프틸)-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-1H-피라졸, 48. 4-클로로-1-{4-〔4-(2-나프틸)-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-1H-피라졸, 49. 1-{2-〔4-(4-플루오로페닐)-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-1H-벤즈이미다졸, 50. 1-{4-〔4-페닐〕-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-1H-벤즈이미다졸 염산염, 51. 1-{4-〔4-(4-플루오로페닐)-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-1H-벤즈이미다졸, 52. 1-{4-〔4-(4-플루오로페닐)-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-1H-벤즈이미다졸 염산염, 53. 4,5-디클로로-2-메틸-1-{4-〔4-(3-트리플루오로메틸페닐)-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-1H-벤즈이미다졸 염산염, 54. 4-클로로-1-{4-〔4-(4-플루오로페닐)-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-1H-피라졸 염산염, 55. 1-{4-〔4-(4-페닐)-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-1H-인다졸 염산염, 56. 4,5-디클로로-1-{4-〔4-(4-플루오로페닐)-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-2-메틸-1H-이미다졸 염산염, 57. 4-(4-클로로페닐)-1-{4-〔4-페닐-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-1H-피라졸 염산염, 58. 4-(4-클로로페닐)-1-{4-〔4-페닐-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-1H-피라졸, 59. 1-{4-〔4-(4-플루오로페닐)-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-1H-트리아졸염산염, 60. 1-{4-〔4-(4-플루오로페닐)-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-1H-트리아졸, 61. 1-{4-〔4-(4-플루오로페닐)-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-2-메틸-1H-벤즈이미다졸, 62. 1-{4-〔4-(4-플루오로페닐)-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-1H-인다졸, 63. 2-{4-〔4-(4-플루오로페닐)-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-2H-인다졸, 64. 2-{4-〔4-(4-플루오로페닐)-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-2H-벤즈트리아조 염산염, 65. 2-{4-〔4-(4-플루오로페닐)-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-2H-벤즈트리아졸, 66. 1-{4-〔4-(4-플루오로페닐)-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-1H-벤즈트리아졸 염산염, 67. 1-{4-〔4-(4-플루오로페닐)-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-1H-벤즈트리아졸, 68. 4-클로로-1-{4-〔4-(4-플루오로페닐)-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-1H-피라졸염산염, 69. 1-{4-〔4-페닐-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-1H-피라졸 염산염, 70. 1-{4-〔4-페닐-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-1H-트리아졸 염산염, 71. 1-{4-〔4-페닐-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-1H-이미다졸 염산염, 72. 1-{4-〔4-페닐-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-1H-피롤 염산염, 73. 1-{4-〔4-페닐-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-1H-피롤, 74. 4-(4-클로로)-1-{4-〔4-히드록시-4-페닐-1-피페리디닐)부틸〕-1H-피라졸, 75. 1-{4-〔4-(4-플루오로페닐)-4-히드록시-1-피페리디닐)부틸〕-1H-피라졸, 76. 4-(4-클로로)-1-{4-〔4-히드록시-4-(3-트리플루오로메틸페닐)-1-피페리디닐)부틸〕-1H-피라졸, 77. 1-{4-〔4-(4-플루오로페닐)-4-히드록시-1-피페리디닐)부틸〕-1H-피라졸, 78. 2-{4-〔4-(4-플루오로페닐)-4-히드록시-1-피페리디닐)부틸〕-2H-인다졸, 79. 2-{4-〔4-(4-플루오로페닐)-4-히드록시-1-피페리디닐)부틸〕-2H-벤즈트리아졸, 80. 1-{4-〔4-(4-플루오로페닐)-4-히드록시-1-피페리디닐)부틸〕-2H-벤즈트리아졸, 81. 3-클로로-1-{4-〔4-페닐-1-피페리디닐)부틸〕-2H-벤즈트리아졸, 82. 3-클로로-1-{4-〔4-페닐-1-(1,2,3,6-테트라히드로피리디닐)부틸〕-1H-인다졸 염산염.
  3. 하기 반응중 하나 이상을 실시하여, 제1항 또는 제2항에 따른 일반식(I)의 화합물을 제조하는 방법; (1). 하기 일반식(II)의 스피란 유도체와 하기 일반식(III)의 질소함유 헤테로고리 화합물과의 반응;
    상기 식들에서, R1, R2, R3, A, Z1, Z2, Z3및 R6는 상기 정의와 동일하며, m은 0 내지 4의 범위를 갖는 값이며, X는 클로로, 브로모, 메실옥시 또는 토실옥시와 같은 이탈기를 의미한다. (2). 하기 일반식(Ⅳ)의 유도체, 하기 일반식(Ⅴ)의 알킬화제 및 일반식(Ⅲ)의 질소함유 헤테로고리 화합물 사이의 동시적인 "1회(one pot)"반응;
    상기 식들에서, R1, R2, R3, A, X, n, Z1, Z2, Z4및 R6는 상기 정의와 동일하다. (3). 알킬화 조건하에서 일반식(Ⅳ)의 아민과 하기 일반식(Ⅵ)의 유도체의 반응;
    상기 식들에서, R1, R2, R3, A, X, n, Z1, Z2, Z|4및 R6는 상기 정의와 동일하다. (4). 알킬화 조건하에서 일반식(Ⅶ)의 화합물과 일반식(Ⅲ)의 질소 함유 헤테로고리 화합물의 반응;
    상기 식들에서, R1, R2, R3, n, X, A, Z1, Z2, Z|4및 R6는 상기 정의와 동일하다. (5). 일반식(I)의 화합물의 탈수;
    상기 식들에서, R1, R2, R3, n, X, A, Z1, Z2, Z|4및 R6는 상기 정의와 동일하며, A는 히드록실기에 연결된 탄소 원자(C-OH)를 의미하며, 점선은 임의의 추가 결합이 없음을 의미한다. (6). 하기 일반식(Ⅷ)의 화합물에 페닐리튬 또는 페닐마그네슘 브로마이드 같은 유기금속 시약의 첨가;
    상기 식에서, n, Z1, Z2, Z4및 R6는 상기 정의와 동일하다. (7). 하기 일반식(Ⅸ) 화합물의 환원;
    상기 식에서, R1, R2, R3, A, n, Z1, Z2, Z4및 R6는 상기 정의와 동일하다.
  4. 제1항 또는 제2항에 있어서, 약제로서, 구체적으로 불안증, 정신병, 간질, 경련, 운동기능 장애, 건망증, 뇌혈관 질환 또는 노인성 치매의 치료 활성을 가진 약제로서의 용도를 가진 일반식(I)의 화합물 및 그 생리적 허용염.
  5. 약학적 허용 부형제 외에도, 제1항 또는 제2항에 따른 하나 이상의 일반식(I)의 화합물 또는 하나 이상의 그 생리적 허용염을 함유하는 약학 조성물.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019960701606A 1994-07-29 1995-07-26 시그마및/또는5에이취티1에이수용체에대한친화성을가진테트라히드로피리딘알킬아졸또는4-히드록시피페리딘알킬아졸 KR100389785B1 (ko)

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