(+/-)-trans-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (+/-)-trans-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole
• 英文别名: trans-2,3,4,4a,5,9b-Hexahydro-1h-pyrido[4,3-b]indole；(4aR,9bR)-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole
• 化学式: C₁₁H₁₄N₂
• 分子量: 174.246
• InChiKey: BPPMRCNUQCVVFJ-GXSJLCMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-(2-氯乙基)-7-甲基-[1,3]噻唑并[3,2-a]嘧啶-5-酮 、 (+/-)-trans-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole 、 2-氨基-3-氯-1,4-萘醌 在 potassium iodide 、 sodium carbonate 作用下， 以 水 、 4-甲基-2-戊酮 为溶剂， 以1.5 g (28%)的产率得到(+/-)-trans-6-[2-(1,3,4,4a,5,9b-hexahydro-2H-pyrido[4,3-b]indol-2-yl)ethyl]-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one
  参考文献：
  名称：

  Hexahydro-pyrido(4,3-b)indole derivatives as antipsychotic drugs

  摘要：

  这项发明涉及公式##STR1##的化合物，其药学上可接受的加合盐和立体化异构体形式，其中Alk为C.sub.1-6烷二基；R.sup.1为氢、C.sub.1-6烷基、芳基或芳基C.sub.1-6烷基；R.sup.2、R.sup.3和R.sup.4分别独立选择自氢、卤素、羟基、硝基、氰基、C.sub.1-6烷基、C.sub.1-6烷氧基、三氟甲基、C.sub.1-6烷硫基、巯基、氨基、单烷基和二(烷基)氨基、羧基、C.sub.1-6烷氧羰基或C.sub.1-6烷基羰基；R.sup.5为氢、C.sub.1-6烷基、苯基或苯基C.sub.1-6烷基；R.sup.6为氢、C.sub.1-6烷基、C.sub.1-6烷氧基、C.sub.1-6烷硫基，或者公式--NR.sup.8 R.sup.9的基团，其中R.sup.8和R.sup.9分别独立选择自氢、C.sub.1-6烷基、苯基或苯基C.sub.1-6烷基；R.sup.7为氢或C.sub.1-6烷基；或R.sup.6和R.sup.7一起可能形成公式--R.sup.6 --R.sup.7 --的双价基团；具有中枢多巴胺和5-羟色胺拮抗活性；它们的制备、含有它们的组合物以及它们作为药物的用途。

  公开号：

  US06057325A1
• 作为产物：
  描述：

  (+/-)-trans-1,3,4,4a,5,9b-hexahydro-2-(phenylmethyl)-2H-pyrido[4,3-b]indole 生成 (+/-)-trans-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole
  参考文献：
  名称：

  Hexahydro-pyrido(4,3-b)indole derivatives as antipsychotic drugs

  摘要：

  这项发明涉及公式##STR1##的化合物，其药学上可接受的加合盐和立体化异构体形式，其中Alk为C.sub.1-6烷二基；R.sup.1为氢、C.sub.1-6烷基、芳基或芳基C.sub.1-6烷基；R.sup.2、R.sup.3和R.sup.4分别独立选择自氢、卤素、羟基、硝基、氰基、C.sub.1-6烷基、C.sub.1-6烷氧基、三氟甲基、C.sub.1-6烷硫基、巯基、氨基、单烷基和二(烷基)氨基、羧基、C.sub.1-6烷氧羰基或C.sub.1-6烷基羰基；R.sup.5为氢、C.sub.1-6烷基、苯基或苯基C.sub.1-6烷基；R.sup.6为氢、C.sub.1-6烷基、C.sub.1-6烷氧基、C.sub.1-6烷硫基，或者公式--NR.sup.8 R.sup.9的基团，其中R.sup.8和R.sup.9分别独立选择自氢、C.sub.1-6烷基、苯基或苯基C.sub.1-6烷基；R.sup.7为氢或C.sub.1-6烷基；或R.sup.6和R.sup.7一起可能形成公式--R.sup.6 --R.sup.7 --的双价基团；具有中枢多巴胺和5-羟色胺拮抗活性；它们的制备、含有它们的组合物以及它们作为药物的用途。

  公开号：

  US06057325A1

文献信息

• Optical Isomers of (+) and (-)-Trans-2,3,4,4A,5,9B-Hexahydro-2,8-Dimethyl-1H-Pyrido[4,3-B] Indole
  申请人：Salimov Ramiz Medzhidovich

  公开号：US20080262019A1

  公开（公告）日：2008-10-23

  The present invention represents novel optical isomers produced according the invention that are optic antipodes to each other having individual biological activity which can be used as active ingredients in pharmaceutical compositions with nootropic and sedative activity for treatment of different individual conditions of patients.

  本发明代表了根据本发明制备的新型光学异构体，它们是光学对映体，具有各自的生物活性，可以用作药物组合物的活性成分，具有脑功能增强和镇静作用，用于治疗患者的不同病况。
• Hexahydro-trans- and tetrahydropyridoindole neuroleptic agents
  申请人：PFIZER INC.

  公开号：EP0060610A1

  公开（公告）日：1982-09-22

  Derivatives of 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole and of (+)enantiomeric, mixtures of (+) and (-)-enantiomeric or (±)racemic 2,3,4,4a,5,9b-hexahydro-4a, 9b-trans-1H-pyrido[4,3-b]indole, substituted at the 5-position with an aryl group and at the 2-position with a carbonylaminoalkyl group or an aminoalkyl group, are neuroleptic agents useful in the treatment of certain psychoses and neuroses.

  2,3,4,5-四氢-1H-吡啶并[4,3-b]吲哚和(+)对映体的衍生物、(+)和(-)对映体的混合物或(±)外消旋2,3,4,4a,5,9b-六氢-4a,9b-反式-1H-吡啶并[4,3-b]吲哚的衍生物，在5位被芳基取代，在2位被羰基氨基烷基或氨基烷基取代，是治疗某些精神病和神经官能症的神经抑制剂。
• LIGANDS OF ALPHA-ADRENOCEPTORS AND OF DOPAMINE, HISTAMINE, IMIDAZOLINE AND SEROTONIN RECEPTORS AND THE USE THEREOF
  申请人：Alla Chem, LLC.

  公开号：EP2236511A2

  公开（公告）日：2010-10-06

  The invention relates to novel ligands the broad spectrum of biological activity of which includes simultaneously α-adrenoceptors, dopamine receptors, histamine receptors, imidazoline receptors and serotonin receptors, among them serotonin 5-HT7 receptors, which are compounds of general formula 1 in the form of free bases, geometrical isomers, racemic mixtures or individual optical isomers, pharmaceutically acceptable salts and/or hydrates, wherein: R1 is a substituent of amino group, selected from hydrogen, optionally substituted C1-C4 alkyl, acyl, heterocyclyl, alkoxycarbonyl, substituted sulfonyl; R2 is a substituent of cyclic system, selected from hydrogen, halogen, optionally substituted C1-C4 alkyl, CF3, CN, alkoxy, alkoxycarbonyl, carboxyl, heterocyclyl or substituted sulfonyl; Ar is optionally substituted aryl not necessarily annalated with heterocyclyl, or optionally substituted aromatic heterocyclyl; W is optionally substituted (CH2)m group, optionally substituted CH=CH group, optionally substituted CH2-CH=CH group, C≡C group, SO2 group; n = 1, 2; m = 1, 2, 3; solid line accompanied by dotted line, i.e. (---) may represent single or double bond. The invention also relates to active ingredients, pharmaceutical compositions comprising the said ligands as active ingredients; to novel medicaments useful for treatment of diseases and conditions of central nervous system (CNS) of humans and warm-blooded animals.

  本发明涉及新型配体，其广泛的生物活性同时包括α-肾上腺素受体、多巴胺受体、组胺受体、咪唑啉受体和血清素受体，其中包括血清素5-HT7受体，这些配体是通式1化合物，其形式为游离碱、几何异构体、外消旋混合物或单个光学异构体、药学上可接受的盐和/或水合物、 其中R1 是氨基的取代基，选自氢、任选取代的 C1-C4 烷基、酰基、杂环基、烷氧羰基、取代的磺酰基； R2 是环状体系的取代基，选自氢、卤素、任选取代的 C1-C4 烷基、CF3、CN、烷氧基、烷氧羰基、羧基、杂环基或取代的磺酰基；Ar 是任选取代的芳基，不一定是环状杂环基，或任选取代的芳香族杂环基； W 是任选取代的 (CH2)m 基团、任选取代的 CH=CH 基团、任选取代的 CH2-CH=CH 基团、C≡C 基团、SO2 基团；n = 1、2；m = 1、2、3；实线伴有虚线，即.即（---）可代表单键或双键。 本发明还涉及活性成分、包含上述配体作为活性成分的药物组合物；涉及用于治疗人类和温血动物中枢神经系统（CNS）疾病和病症的新型药物。
• HEXAHYDRO-PYRIDO(4,3-B)INDOLE DERIVATIVES AS ANTIPSYCHOTIC DRUGS
  申请人：JANSSEN PHARMACEUTICA N.V.

  公开号：EP0902684B1

  公开（公告）日：2003-04-09
• LIGANDS OF ALPHA-ADRENOCEPTORS, DOPAMINE, HISTAMINE, IMIDAZOLINE AND SEROTONIN RECEPTORS AND THEIR USE
  申请人：Ivashchenko Andrey Alexandrovich

  公开号：US20110039825A1

  公开（公告）日：2011-02-17

  The invention relates to novel ligands the broad spectrum of biological activity of which includes simultaneously α-adrenoceptors, dopamine receptors, histamine receptors, imidazoline receptors and serotonin receptors, among them serotonin 5-HT 7 receptors, which are compounds of general formula 1 in the form of free bases, geometrical isomers, racemic mixtures or individual optical isomers, pharmaceutically acceptable salts and/or hydrates, wherein: R1 is a substituent of amino group, selected from hydrogen, optionally substituted C 1 -C 4 alkyl, acyl, heterocyclyl, alkoxycarbonyl, substituted sulfonyl; R2 is a substituent of cyclic system, selected from hydrogen, halogen, optionally substituted C 1 -C 4 alkyl, CF 3 , CN, alkoxy, alkoxycarbonyl, carboxyl, heterocyclyl or substituted sulfonyl; Ar is optionally substituted aryl not necessarily annalated with heterocyclyl, or optionally substituted aromatic heterocyclyl; W is optionally substituted (CH 2 ) m group, optionally substituted CH═CH group, optionally substituted CH 2 —CH═CH group, C≡C group, SO 2 group; n=1, 2; m=1, 2, 3; solid line accompanied by dotted line, i.e. may represent single or double bond. The invention also relates to active ingredients, pharmaceutical compositions comprising the said ligands as active ingredients; to novel medicaments useful for treatment of diseases and conditions of central nervous system (CNS) of humans and warm-blooded animals.