2-cyclopentyl-1, 2,3, 4-tetrahydroquinoline | 856703-29-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 2-cyclopentyl-1, 2,3, 4-tetrahydroquinoline
• 英文别名: 2-Cyclopentyl-1,2,3,4-tetrahydroquinoline
• CAS: 856703-29-2
• 化学式: C₁₄H₁₉N
• 分子量: 201.312
• InChiKey: JTGQILZPSLNYNY-UHFFFAOYSA-N

物化性质

• 沸点：
  336.1±12.0 °C(Predicted)
• 密度：
  1.034±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-cyclopentyl-1, 2,3, 4-tetrahydroquinoline 、 3-溴丙酮酸乙酯 以 四氢呋喃 为溶剂， 反应 15.0h， 生成 3-(3,4-二氢喹啉-1(2H)-基)-2-氧代丙酸乙酯
  参考文献：
  名称：

  [EN] TRICYCLIC 1-[(3-INDOL-3-YL)CARBONYL] PIPERAZINE DERIVATIVES AS CANNABINOID CB1 RECEPTOR AGONISTS
  [FR] DERIVES TRICYCLIQUES DE PIPERAZINE 1-[(3-INDOL-3-YL)CARBONYL] UTILES EN TANT QU'AGONISTES DU RECEPTEUR CANNABINOIDE CB1

  摘要：

  该发明涉及具有通式（I）的三环1-[(吲哚-3-基)羰基]哌嗪衍生物，其中X为CH2、O或S；R代表1-3个取自H、(C1-4)烷基、(C1-4)烷氧基和卤素的取代基；R1为(C5-8)环烷基；R2为H或(C1-4)烷基；R3、R3'、R4'、R4'、R5、R5'和R6'独立地为氢或(C1-4)烷基，可选地取代为(C1-4)烷氧基、OH或卤素；R6为氢或(C1-4)烷基，可选地取代为(C1-4)烷氧基、OH或卤素；或R6与R7一起形成一个含有O和S等进一步杂原子的4-7元饱和杂环；R7与R6一起形成一个含有O和S等进一步杂原子的4-7元饱和杂环；或R7为H、(C1-4)烷基或(C3-5)环烷基，烷基基团可选地取代为OH、卤素或(C1-4)烷氧基；或其药学上可接受的盐。该发明还涉及包含所述三环1-[(吲哚-3-基)羰基]哌嗪衍生物的药物组合物，并且涉及在治疗疼痛，如围手术疼痛、慢性疼痛、神经痛、癌症疼痛以及与多发性硬化相关的疼痛和痉挛中使用这些衍生物。

  公开号：

  WO2005058327A1
• 作为产物：
  描述：

  2-cyclopentylquinoline 在 nickel dichloride sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 2-cyclopentyl-1, 2,3, 4-tetrahydroquinoline
  参考文献：
  名称：

  [EN] TRICYCLIC 1-[(3-INDOL-3-YL)CARBONYL] PIPERAZINE DERIVATIVES AS CANNABINOID CB1 RECEPTOR AGONISTS
  [FR] DERIVES TRICYCLIQUES DE PIPERAZINE 1-[(3-INDOL-3-YL)CARBONYL] UTILES EN TANT QU'AGONISTES DU RECEPTEUR CANNABINOIDE CB1

  摘要：

  该发明涉及具有通式（I）的三环1-[(吲哚-3-基)羰基]哌嗪衍生物，其中X为CH2、O或S；R代表1-3个取自H、(C1-4)烷基、(C1-4)烷氧基和卤素的取代基；R1为(C5-8)环烷基；R2为H或(C1-4)烷基；R3、R3'、R4'、R4'、R5、R5'和R6'独立地为氢或(C1-4)烷基，可选地取代为(C1-4)烷氧基、OH或卤素；R6为氢或(C1-4)烷基，可选地取代为(C1-4)烷氧基、OH或卤素；或R6与R7一起形成一个含有O和S等进一步杂原子的4-7元饱和杂环；R7与R6一起形成一个含有O和S等进一步杂原子的4-7元饱和杂环；或R7为H、(C1-4)烷基或(C3-5)环烷基，烷基基团可选地取代为OH、卤素或(C1-4)烷氧基；或其药学上可接受的盐。该发明还涉及包含所述三环1-[(吲哚-3-基)羰基]哌嗪衍生物的药物组合物，并且涉及在治疗疼痛，如围手术疼痛、慢性疼痛、神经痛、癌症疼痛以及与多发性硬化相关的疼痛和痉挛中使用这些衍生物。

  公开号：

  WO2005058327A1

文献信息

• Cyclopropylindole derivatives
  申请人：Thurston David Edwin

  公开号：US06909006B1

  公开（公告）日：2005-06-21

  Compounds of formula (III) or (V), wherein is a solid support; L is a linking group or a single bond; T is a combinatorial unit; n is a positive integer, where if n is greater than 1, each T may be different: X is an electrophilic leaving group; Y is selected from NH-Prot, O-Prot, S-Prot, NO 2 , —NHOH. N 3 , NHR, NRR, N═NR, N(O)RR, NHSO 2 R, N═N═PhR, SR or SSR, where Prot represents a protecting group; A and B collectively represent a fused benzene or pyrrole ring (in either orientation), which is optionally substituted by up to respectively 4 or 2 groups independently selected from R, OH, OR, halo, nitro, amino, Me 3 Sn, CO 2 H, CO 2 R, R 1 is a nitrogen protecting group, where if Y includes a protecting group, these protecting groups are orthogonal and R 2 and R 7 are independently selected from H, R, OH, OR, halo, nitro, amino, Me 3 Sn, and other related compounds and collections of compounds.

  式（III）或（V）的化合物中，其中是固体支撑；L是连接基团或单键；T是组合单元；n是正整数，如果n大于1，则每个T可能不同：X是亲电离开基团；Y从NH-Prot、O-Prot、S-Prot、NO2、—NHOH、N3、NHR、NRR、N═NR、N（O）RR、NHSO2R、N═N═PhR、SR或SSR中选择，其中Prot代表保护基团；A和B共同代表一个融合的苯或吡咯环（在任何方向），可选地由最多分别从R、OH、OR、卤、硝基、氨基、Me3Sn、CO2H、CO2R中独立选择的4个或2个基团取代，R1是氮保护基团，如果Y包括保护基团，则这些保护基团是正交的，R2和R7分别独立选择自H、R、OH、OR、卤、硝基、氨基、Me3Sn和其他相关化合物和化合物集合。
• Tricyclic 1-[(indol-3-yl)carbonyl]piperazine derivatives as cannabinoid cb1 receptor agonists
  申请人：Adam-Worrall Julia

  公开号：US20070088025A1

  公开（公告）日：2007-04-19

  The invention relates to tricyclic 1-[(in-dol-3-yl)carbonyl]piperazine derivative having the general Formula (I) wherein X is CH 2 , O or S; R represents 1-3 substituents independently selected from H, (C 1-4 )alkyl, (C 1-4 )alkyloxy and halogen; R 1 is (C 5-8 )cycloalkyl; R 2 is H or (C 1-4 )alkyl; R 3 , R 3 ′, R 4 ′, R 4 ′, R 5 , R 5 ′ and R 6 ′ are independently hydrogen or (C 1-4 )-alkyl, optionally substituted with (C 1-4 )alkyloxy, OH or halogen; R 6 is hydrogen or (C 1-4 )alkyl, optionally substituted with (C 1-4 )alkyloxy, OH or halogen; or R 6 forms together with R 7 a 4-7 membered saturated heterocyclic ring, optionally containing a further heteroatom selected from O and S; R 7 forms together with R 6 a 4-7 membered saturated heterocydic ring, optionally containing a further heteroatom selected from O and S; or R 7 is H, (C 1-4 )alkyl or (C 3-5 )cycloalkyl, the alkyl groups being optionally substituted with OH, halogen or (C 1-4 )alkyloxy; or a pharmaceutically acceptable salt thereof. The invention also relates to pharmaceutical compositions comprising said tricyclic 1-[(indol-3-yl)carbonyl]piperazine derivatives, and to the use of these derivatives in the treatment of pain, such as peri-operative pain, chronic pain neuropathic pain, cancer pain, and pain and spasticity associated with multiple sclerosis.

  本发明涉及三环1-[(吲哚-3-基)羰基]哌嗪衍生物，其具有通式（I），其中X为CH2、O或S；R代表1-3个取自H、（C1-4）烷基、（C1-4）烷氧基和卤素的取代基；R1为（C5-8）环烷基；R2为H或（C1-4）烷基；R3、R3'、R4'、R4'、R5、R5'和R6'独立地为氢或（C1-4）烷基，可选地被（C1-4）烷氧基、OH或卤素取代；R6为氢或（C1-4）烷基，可选地被（C1-4）烷氧基、OH或卤素取代；或R6与R7形成4-7成员饱和杂环环，可选地包含进一步的选自O和S的杂原子；R7与R6a形成4-7成员饱和杂环环，可选地包含进一步的选自O和S的杂原子；或R7为H、（C1-4）烷基或（C3-5）环烷基，烷基基团可选地被OH、卤素或（C1-4）烷氧基取代；或其药学上可接受的盐。本发明还涉及含有上述三环1-[(吲哚-3-基)羰基]哌嗪衍生物的制药组合物，以及在治疗疼痛，如围手术期疼痛、慢性疼痛、神经病性疼痛、癌症疼痛和与多发性硬化症相关的疼痛和痉挛中使用这些衍生物的用途。
• Tricyclic 1-[(indol-3-yl)carbonyl]piperazine derivatives as cannabinoid CB1 receptor agonists
  申请人：N.V. Organon

  公开号：US07772227B2

  公开（公告）日：2010-08-10

  The invention relates to tricyclic 1-[(indol-3-yl)carbonyl]piperazine derivative having the general Formula (I) wherein X is CH2, O or S; R represents 1-3 substituents independently selected from H, (C1-4)alkyl, (C1-4)alkyloxy and halogen; R1 is (C5-8)cycloalkyl; R2 is H or (C1-4)alkyl; R3, R3′, R4′ R4′, R5, R5′ and R6′ are independently hydrogen or (C1-4)-alkyl, optionally substituted with (C1-4)alkyloxy, OH or halogen; R6 is hydrogen or (C1-4)alkyl, optionally substituted with (C1-4)alkyloxy, OH or halogen; or R6 forms together with R7 a 4-7 membered saturated heterocyclic ring, optionally containing a further heteroatom selected from O and S; R7 forms together with R6 a 4-7 membered saturated heterocyclic ring, optionally containing a further heteroatom selected from O and S; or R7 is H, (C1-4)alkyl or (C3-5)cycloalkyl, the alkyl groups being optionally substituted with OH, halogen or (C1-4)alkyloxy; or a pharmaceutically acceptable salt thereof. The invention also relates to pharmaceutical compositions comprising said tricyclic 1-[(indol-3-yl)carbonyl]piperazine derivatives, and to the use of these derivatives in the treatment of pain, such as peri-operative pain, chronic pain neuropathic pain, cancer pain, and pain and spasticity associated with multiple sclerosis.

  本发明涉及具有通式（I）的三环1-[(indol-3-yl)carbonyl]哌嗪衍生物，其中X为CH2、O或S；R代表1-3个取自H、(C1-4)烷基、(C1-4)烷氧基和卤素的取代基；R1为(C5-8)环烷基；R2为H或(C1-4)烷基；R3、R3′、R4′、R4′、R5、R5′和R6′独立地为氢或(C1-4)烷基，可选地取代(C1-4)烷氧基、OH或卤素；R6为氢或(C1-4)烷基，可选地取代(C1-4)烷氧基、OH或卤素；或R6与R7一起形成4-7成员饱和杂环环，可选地包含进一步从O和S选择的杂原子；R7与R6一起形成4-7成员饱和杂环环，可选地包含进一步从O和S选择的杂原子；或R7为H、(C1-4)烷基或(C3-5)环烷基，烷基基团可选地取代OH、卤素或(C1-4)烷氧基；或其药学上可接受的盐。本发明还涉及包含所述三环1-[(indol-3-yl)carbonyl]哌嗪衍生物的制药组合物，并且涉及使用这些衍生物治疗疼痛，例如围手术期疼痛、慢性疼痛、神经性疼痛、癌症疼痛以及与多发性硬化相关的疼痛和痉挛。
• TRICYCLIC 1-((3-INDOL-3-YL)CARBONYL)PIPERAZINE DERIVATIVES AS CANNABINOID CB1 RECEPTOR AGONISTS
  申请人：Akzo Nobel N.V.

  公开号：EP1696930A1

  公开（公告）日：2006-09-06
• US7772227B2
  申请人：——

  公开号：US7772227B2

  公开（公告）日：2010-08-10