(1S,5S)-1-[5-(trifluoromethyl)-2-pyridinyl]-3-azabicyclo[3.1.0]hexane | 927439-51-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1S,5S)-1-[5-(trifluoromethyl)-2-pyridinyl]-3-azabicyclo[3.1.0]hexane
• 英文别名: (1S,5S)-1-[5-(trifluoromethyl)pyridin-2-yl]-3-azabicyclo[3.1.0]hexane
• CAS: 927439-51-8
• 化学式: C₁₁H₁₁F₃N₂
• 分子量: 228.217
• InChiKey: WJKHDCRPNISRMI-PSASIEDQSA-N

物化性质

• 沸点：
  289.9±35.0 °C(Predicted)
• 密度：
  1.348±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-(phenylmethyl)-1-[5-(trifluoromethyl)-2-pyridinyl]-3-azabicyclo[3.1.0]hexane 在 palladium 10% on activated carbon 盐酸 、 氢气 、 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 反应 20.0h， 以81%的产率得到(1S,5S)-1-[5-(trifluoromethyl)-2-pyridinyl]-3-azabicyclo[3.1.0]hexane
  参考文献：
  名称：

  [EN] AZABICYCLO (3.1.0) HEXANE DERIVATIVES USEFUL AS MODULATORS OF DOPAMINE D3 RECEPTORS
  [FR] DERIVES AZABICYCLO (3.1.0) HEXANE UTILES COMME MODULATEURS DES RECEPTEURS D3 DE LA DOPAMINE

  摘要：

  本发明涉及公式(I)的新化合物或其药学上可接受的盐，其中G选自以下组成的一组：苯基、吡啶基、苯并噻唑基、吲哚基；p是一个从0到5的整数；R1独立地选自以下组成的一组：卤素、羟基、氰基、C1-4烷基、卤代C1-4烷基、C1-4烷氧基、卤代C1-4烷氧基、C1-4烷酰基；或对应于一个R5基团；R2是氢或C1-4烷基；R3是C1-4烷基；R4是氢，或苯基、杂环基、5-或6-成员杂芳基，或8-到11-成员双环基，其中任何一个基团可以选择地被来自以下组成的1、2、3或4个取代基所取代：卤素、氰基、C1-4烷基、卤代C1-4烷基、C1-4烷氧基、C1-4烷酰基；R5是选自以下组成的基团：异噁唑基、-CH2-N-吡咯基、1,1-二氧化-2-异噻唑啉基、噻吩基、噻唑基、吡啶基、2-吡咯烷基，这样的基团可以选择地被一个或两个取代基所取代，所述取代基选自：卤素、氰基、C1-4烷基、卤代C1-4烷基、C1-4烷氧基、C1-4烷酰基；当R1是氯且p为1时，该R1不位于与分子其余部分的连接键的邻位；当R1对应于R5时，p为1；它们的制备方法，用于这些方法的中间体，含有它们的药物组合物以及它们作为多巴胺D3受体调节剂在治疗中的用途，例如用于治疗药物依赖或作为抗精神病药物。

  公开号：

  WO2005080382A1

文献信息

• 3-(1,2,4-TRIAZOL-3YLALKYL) AZABRICLO (3.1.0) HEXANE DERIVATIVES AS MODULATORS OF DOPAMINE D3 RECEPTORS
  申请人：Bonanomi Giorgio

  公开号：US20090124629A1

  公开（公告）日：2009-05-14

  The present invention relates to novel compounds of formula (I) or pharmaceutically acceptable salt thereof: wherein G is selected from a group consisting of: phenyl, pyridyl, benzothiazolyl and indazolyl; p is an integer ranging from 0 to 5; R 1 is independently selected from a group consisting of: halogen, hydroxy, cyano, C 1-4 alkyl, haloC 1-4 alkyl, C 1-4 alkoxy, haloC 1-4 alkoxy, C 1-4 alkanoyl and SF 5 ; or corresponds to a group R 5 ; each R 2 is independently hydrogen, fluorine or C 1-4 alkyl; n is 2, 3, 4, or 5; R 3 is C 1-4 alkyl; R 4 is hydrogen, or a C 1-4 alkyl group, a benzyl group, a phenyl group, a heterocyclyl group, a 5- or 6-membered heteroaromatic group, or a 8- to 11-membered bicyclic group, any of which groups is optionally substituted by 1, 2, 3 or 4 substituents selected from the group consisting of: halogen, cyano, C 1-4 alkyl, haloC 1-4 alkyl, C 1-4 alkoxy, haloC 1-4 alkoxy, C 1-4 alkanoyl and SF 5 ;or R 4 is a —SR 6 group; R 5 is selected from a group consisting of: isoxazolyl, —CH 2 —N-pyrrolyl, 1,1-dioxido- 2-isothiazolidinyl, thienyl, thiazolyl, pyridyl and 2-pyrrolidinonyl, and such a group is optionally substituted by one or two substituents selected from a group consisting of: halogen, cyano, C 1-4 alkyl, haloC 1-4 alkyl, C 1-4 alkoxy and C 1-4 alkanoyl; R 6 is C 1-4 alkyl or —CH 2 C 3-4 cycloalkyl; and when R 1 is chlorine and p is 1, such R 1 is not present in the ortho position with respect to the linking bond to the rest of the molecule; and when R 1 corresponds to R 5 , p is 1. processes for their preparation, intermediates used in these processes, pharmaceutical compositions containing them and their use in therapy, as modulators of dopamine D 3 receptors, e.g. to treat drug dependency, as antipsychotic agents, to treat obsessive compulsive spectrum disorders, premature ejaculation or cognition impairment.

  本发明涉及以下式（I）的新化合物或其药学上可接受的盐：其中G选自以下组：苯基，吡啶基，苯并噻唑基和吲唑基；p为0至5的整数；R1独立选自以下组：卤素，羟基，氰基，C1-4烷基，卤代C1-4烷基，C1-4烷氧基，卤代C1-4烷氧基，C1-4酰基和SF5；或对应于R5基团；每个R2独立地为氢，氟或C1-4烷基；n为2、3、4或5；R3为C1-4烷基；R4为氢，或C1-4烷基，苄基，苯基，杂环基，5-或6-成员杂芳基，或8-至11-成员双环基团，其中任何一个基团可以选择地由1、2、3或4个来自以下组的取代基取代：卤素，氰基，C1-4烷基，卤代C1-4烷基，C1-4烷氧基，卤代C1-4烷氧基，C1-4酰基和SF5；或R4为-SR6基团；R5选自以下组：异噁唑基，-CH2-N-吡咯基，1,1-二氧化-2-异噻唑烷基，噻唑基，吡啶基和2-吡咯烷基，并且此类基团可以选择地由1或2个来自以下组的取代基取代：卤素，氰基，C1-4烷基，卤代C1-4烷基，C1-4烷氧基和C1-4酰基；R6为C1-4烷基或- C3-4环烷基；当R1为氯且p为1时，此类R1不在与分子的其余部分的连接键的正交位置上存在；当R1对应于R5时，p为1。本发明还涉及制备这些化合物的方法，用于这些方法的中间体，包含它们的药物组合物以及它们作为多巴胺D3受体调节剂的用途，例如用于治疗药物依赖，作为抗精神病药物，用于治疗强迫症谱系障碍，早泄或认知障碍。
• Use of Azabicyclo Hexane Derivatives
  申请人：Hamprecht Dieter

  公开号：US20090036461A1

  公开（公告）日：2009-02-05

  The present invention provides a new use of a compound of formula (I) or a pharmaceutically acceptable salt or solvate salt thereof: wherein: G is selected from a group consisting of: phenyl, pyridyl, benzothiazolyl, indazolyl; p is an integer ranging from 0 to 5; R 1 is independently selected from a group consisting of: halogen, hydroxyl, cyano, C 1-4 alkyl, haloC 1-4 alkyl, C 1-4 alkoxy, haloC 1-4 alkoxy, C 1-4 alkanoyl; or corresponds to a group R 5 ; R 2 is hydrogen or C 1-4 alkyl; R 3 I s C 1-4 alkyl; R 4 is hydrogen, or a phenyl group, a heterocyclyl group, a 5- or 6-membered heteroaromatic group, or a 8- to 11-membered bicyclic group, any of which groups is optionally substituted by 1, 2, 3 or 4 substituents selected from the group consisting of: halogen, cyano, C 1-4 alkyl, haloC 1-4 alkyl, C 1-4 alkoxy, C 1-4 alkanoyl; R 5 is a moiety selected from the group consisting of: isoxazolyl, —CH 2 —N-pyrrolyl, 1,1-dioxido-2-isothiazolidinyl, thienyl, thiazolyl, pyridyl, 2-pyrrolidinonyl, and such a group is optionally substituted by one or two substituents selected from: halogen, cyano, C 1-4 alkyl, haloC 1-4 alkyl, C 1-4 alkoxy, C 1-4 alkanoyl; and when R 1 is chlorine and p is 1, such R 1 is not present in the ortho position with respect to the linking bond to the rest of the molecule; and when R 1 corresponds to R 5 , p is 1; in the manufacture of a medicament for the treatment of a somatoform disorder such as body dysmorphic disorder or hyperchondriasis, bulimia nervosa, anorexia nervosa, binge eating, paraphilia and nonparaphilic sexual addictions, Sydeham's chorea, torticollis, autism, a movement disorder including Tourette's syndrome; and in the manufacture of a medicament for the treatment of premature ejaculation.

  本发明提供了化合物(I)或其药学上可接受的盐或溶剂盐的新用途：其中：G选择自苯基、吡啶基、苯并噻唑基、吲哚基的群组;p为0至5的整数；R1独立地选择自卤素、羟基、氰基、C1-4烷基、卤代C1-4烷基、C1-4烷氧基、卤代C1-4烷氧基、C1-4酰基；或对应于R5基团；R2为氢或C1-4烷基；R3为C1-4烷基；R4为氢、苯基、杂环基、5-或6-成员杂芳基、或8-至11-成员双环基中的任何一种，其中任何一种基团均可选地被1、2、3或4个来自卤素、氰基、C1-4烷基、卤代C1-4烷基、C1-4烷氧基、C1-4酰基的取代基所取代；R5为从异恶唑基、—CH2—N-吡咯基、1,1-二氧化-2-异噻唑烷基、噻唑基、吡啶基、2-吡咯烷酰基中选择的基团，并且此类基团可选地被1或2个来自卤素、氰基、C1-4烷基、卤代C1-4烷基、C1-4烷氧基、C1-4酰基的取代基所取代；当R1为氯且p为1时，此类R1不位于与分子其余部分的连接键的正交位置；当R1对应于R5时，p为1；用于制造治疗躯体形式障碍（如身体畸形障碍或健忘症）、暴食症、厌食症、暴饮暴食、性变态和非性变态性瘾症、辛德汉舞蹈病、斜颈、自闭症、包括图雷特综合症在内的运动障碍的药物；以及用于制造治疗早泄的药物。
• Azabicyclo (3.1.0.) hexane derivatives useful as modulators of dopamine d3 receptors
  申请人：Arista Luca

  公开号：US20070142438A1

  公开（公告）日：2007-06-21

  The present invention relates to novel compounds of formula (I) or a pharmaceutically acceptable salt thereof: 1. wherein G is selected from a group consisting of: phenyl, pyridyl, benzothiazolyl, indazolyl; p is an integer ranging from 0 to 5; R 1 is independently selected from a group consisting of: halogen, hydroxy, cyano, C 1-4 alkyl, haloC 1-4 alkyl, C 1-4 alkoxy, halo 1-4 alkoxy, C 1-4 alkanoyl; or corresponds to a group R 5 ; R 2 is hydrogen or C 1-4 alkyl; R 3 is C 1-4 alkyl; R 4 is hydrogen, or a phenyl group, a heterocyclyl group, a 5- or 6-membered heteroaromatic group, or a 8- to 11-membered bicyclic group, any of which groups is optionally substituted by 1, 2, 3 or 4 substituents selected from the group consisting of: halogen, cyano, C 1-4 alkyl, haloC 1-4 alkyl, C 1-4 alkoxy, C 1-4 alkanoyl; R 5 is a moiety selected from the group consisting of: isoxazolyl, —CH 2 —N-pyrrolyl, 1,1-dioxido-2-isothiazolidinyl, thienyl, thiazolyl, pyridyl, 2-pyrrolidinonyl, and such a group is optionally substituted by one or two substituents selected from: halogen, cyano, C 1-4 alkyl, halo 1-4 alkyl, C 1-4 alkoxy, C 1-4 alkanoyl; and when R 1 is chlorine and p is 1, such R 1 is not present in the ortho position with respect to the linking bond to the rest of the molecule; and when R 1 corresponds to R 5 , p is 1; or a salt thereof which are useful as modulators of dopamine D 3 receptors, e.g. to treat drug dependency or as antipsychotic agents.

  本发明涉及公式（I）的新化合物或其药学上可接受的盐：1.其中G选自以下组中的一组：苯基，吡啶基，苯并噻唑基，吲哚基；p为0至5的整数；R1独立地选自以下组中的一组：卤素，羟基，氰基，C1-4烷基，卤代C1-4烷基，C1-4烷氧基，卤代1-4烷氧基，C1-4酰基；或对应于R5基团；R2为氢或C1-4烷基；R3为C1-4烷基；R4为氢，苯基，杂环基，5-或6-成员杂芳基，或8-至11-成员双环基中的一种，其中任何一种基团均可选择性地被1、2、3或4个来自以下组的取代基所取代：卤素，氰基，C1-4烷基，卤代C1-4烷基，C1-4烷氧基，C1-4酰基；R5是从以下组中选择的一部分：异噁唑基，-CH2-N-吡咯基，1,1-二氧化-2-异硫氮基，噻唑基，噻唑基，吡啶基，2-吡咯烷基，这样的基团可以选择地被一个或两个取代基所取代：卤素，氰基，C1-4烷基，卤代1-4烷基，C1-4烷氧基，C1-4酰基；当R1为氯且p为1时，该R1不位于与分子的其余部分的连接键的邻位上；当R1对应于R5时，p为1；或其盐，它们可用作多巴胺D3受体的调节剂，例如用于治疗药物依赖或作为抗精神病药物。
• Azabicyclo (3.1.0) Hexane Derivatives Useful As Modulators Of Dopamine D3 Receptors
  申请人：Arista Luca

  公开号：US20100160336A1

  公开（公告）日：2010-06-24

  The present invention relates to novel compounds of formula (I) or a pharmaceutically acceptable salt thereof: wherein G is selected from a group consisting of: phenyl, pyridyl, benzothiazolyl, indazolyl; p is an integer ranging from 0 to 5; R 1 is independently selected from a group consisting of: halogen, hydroxy, cyano, C 1-4 alkyl, haloC 1-4 alkyl, C 1-4 alkoxy, haloC 1-4 alkoxy, C 1-4 alkanoyl; or corresponds to a group R 5 ; R 2 is hydrogen or C 1-4 alkyl; R 3 is C 1-4 alkyl; R 4 is hydrogen, or a phenyl group, a heterocyclyl group, a 5- or 6-membered heteroaromatic group, or a 8- to 11-membered bicyclic group, any of which groups is optionally substituted by 1, 2, 3 or 4 substituents selected from the group consisting of: halogen, cyano, C 1-4 alkyl, haloC 1-4 alkyl, C 1-4 alkoxy, C 1-4 alkanoyl; R 5 is a moiety selected from the group consisting of: isoxazolyl, —CH 2 —N-pyrrolyl, 1,1-dioxido-2-isothiazolidinyl, thienyl, thiazolyl, pyridyl, 2-pyrrolidinonyl, and such a group is optionally substituted by one or two substituents selected from: halogen, cyano, C 1-4 alkyl, haloC 1-4 alkyl, C 1-4 alkoxy, C 1-4 alkanoyl; and when R 1 is chlorine and p is 1, such R 1 is not present in the ortho position with respect to the linking bond to the rest of the molecule; and when R 1 corresponds to R 5 , p is 1; processes for their preparation, intermediates used in these processes, pharmaceutical compositions containing them and their use in therapy, as modulators of dopamine D 3 receptors, e.g. to treat drug dependency or as antipsychotic agents.

  本发明涉及式（I）的新化合物或其药学上可接受的盐： 其中， G选自以下组：苯基，吡啶基，苯并噻唑基，吲唑基； p为0至5的整数； R1独立地选自以下组：卤素，羟基，氰基，C1-4烷基，卤代C1-4烷基，C1-4烷氧基，卤代C1-4烷氧基，C1-4酰基；或对应于R5基团； R2为氢或C1-4烷基； R3为C1-4烷基； R4为氢，苯基，杂环基，5-或6-成员杂芳基，或8-至11-成员双环基中的任意一种，其中任一基团均可选地被1、2、3或4个来自以下组的取代基所取代：卤素，氰基，C1-4烷基，卤代C1-4烷基，C1-4烷氧基，C1-4酰基； R5为以下组中选出的基团：异恶唑基，-CH2-N-吡咯基，1,1-二氧化-2-异噻唑啉基，噻唑基，噻唑啉基，吡啶基，2-吡咯烷酰基，该基团可选地被1或2个来自以下组的取代基所取代：卤素，氰基，C1-4烷基，卤代C1-4烷基，C1-4烷氧基，C1-4酰基； 当R1为氯且p为1时，该R1不在与分子的其余部分的连接键的正交位置上；当R1对应于R5时，p为1； 本发明还涉及制备这些化合物的方法、用于这些方法的中间体、含有它们的制药组合物以及其作为多巴胺D3受体调节剂的用途，例如用于治疗药物依赖或作为抗精神病药物。
• USE OF AZABICYCLO HEXANE DERIVATIVES
  申请人：HAMPRECHT Dieter

  公开号：US20120196910A1

  公开（公告）日：2012-08-02

  The present invention provides a new use of a compound of formula (I) or a pharmaceutically acceptable salt or solvate salt thereof: for the treatment of a somatoform disorder such as body dysmorphic disorder or hyperchondriasis, bulimia nervosa, anorexia nervosa, binge eating, paraphilia and nonparaphilic sexual addictions, Sydeham's chorea, torticollis, autism, a movement disorder including Tourette's syndrome.

  本发明提供了化合物(I)或其药学上可接受的盐或溶剂盐的一种新用途：用于治疗躯体形式障碍，如身体畸形障碍或疑病症，暴食症，厌食症，暴食症，性偏执症和非性偏执性性成瘾，辛德汉舞蹈症，斜颈，自闭症，包括图雷特综合征在内的运动障碍。