8-methyl-5-(2-(6-methylpyridin-3-yl)ethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole | 23224-24-0

• 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: 8-methyl-5-(2-(6-methylpyridin-3-yl)ethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole
• 英文别名: 2-desmethyl-Dimebon；8-methyl-5-[2-(6-methyl-pyridin-3-yl)-ethyl]-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole；1,3,4,5-Tetrahydro-8-methyl-5-<2-(6-methyl-3-pyridyl)-athyl>-2H-pyrido<4,3-b>indol；8-methyl-5-[2-(6-methylpyridin-3-yl)ethyl]-1,2,3,4-tetrahydropyrido[4,3-b]indole
• CAS: 23224-24-0
• 化学式: C₂₀H₂₃N₃
• 分子量: 305.423
• InChiKey: JCPPGNFHTRTYGX-UHFFFAOYSA-N

物化性质

• 熔点：
  93-95 °C
• 沸点：
  522.4±50.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  29.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  丙烯腈 、 8-methyl-5-(2-(6-methylpyridin-3-yl)ethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole 在 ammonium cerium (IV) nitrate 、 碳酸氢钠 作用下， 以 水 为溶剂， 反应 2.17h， 以61.43%的产率得到3-(8-methyl-5-(2-(6-methylpyridin-3-yl)ethyl)-3,4-dihydro-1H-pyrido[4,3-b]indol-2(5H)-yl)propanenitrile
  参考文献：
  名称：

  [EN] PYRIDO [4,3-B] INDOLES AND METHODS OF USE
  [FR] PYRIDO[4,3-B]INDOLES ET PROCÉDÉS D'UTILISATION

  摘要：

  公开号：

  WO2010127177A8
• 作为产物：
  描述：

  2-benzyl-8-methyl-5-(2-(6-methylpyridin-3-yl)ethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole 在 palladium 10% on activated carbon 、 甲酸铵 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以80%的产率得到8-methyl-5-(2-(6-methylpyridin-3-yl)ethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole
  参考文献：
  名称：

  [11C]Dimebon, radiosynthesis and lipophilicity of a new potential PET agent for imaging of Alzheimer’s disease and Huntington’s disease

  摘要：

  [C-11] Dimebon (2-[C-11]methyl-8-methyl-5-(2-(6-methylpyridin-3-yl)ethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole), a new potential PET agent for imaging of Alzheimer's disease and Huntington's disease, was prepared by N-[C-11] methylation of desmethyl-Domebon precursor with [C-11]CH3OTf and purified with a semi-preparative HPLC method in 30-40% decay corrected radiochemical yield and 222-296 GBq/mu mol specific activity at EOB. The measured lipophilicity coefficient (Log P) value of [C-11] Dimebon was 2.53. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.02.094

文献信息

• [EN] NEW TETRACYCLIC COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS TÉTRACYCLIQUES
  申请人：MEDIVATION TECHNOLOGIES INC

  公开号：WO2009055828A1

  公开（公告）日：2009-04-30

  This disclosure relates to new tetracyclic compounds that may be used to modulate a histamine receptor in an individual. The compounds in one embodiment are tetracyclic [4,3- b]indoles. Pharmaceutical compositions comprising the compounds are also provided, as are methods of using the compounds in a variety of therapeutic applications, including the treatment of a cognitive disorder, psychotic disorder, neurotransmitter-mediated disorder and/or a neuronal disorder.

  这项披露涉及可能用于调节个体组织胺受体的新四环化合物。在一个实施例中，这些化合物是四环[4,3- b]吲哚类化合物。此外还提供了包含这些化合物的药物组合物，以及使用这些化合物进行各种治疗应用的方法，包括治疗认知障碍、精神障碍、神经递质介导的障碍和/或神经元障碍。
• PYRIDOINDOLE MODULATORS OF NMDA RECEPTOR AND ACETYLCHOLINESTERASE
  申请人：Gant Thomas G.

  公开号：US20100125085A1

  公开（公告）日：2010-05-20

  The present invention relates to new pyridoindole modulators of NMDA receptors, AMPA receptors, and/or L-type calcium channels, and/or inhibitors of acetylcholinesterase, pharmaceutical compositions thereof, and methods of use thereof.

  本发明涉及新的吡啶吲哚调节NMDA受体、AMPA受体和/或L型钙通道，和/或抑制乙酰胆碱酯酶的药物组合物，以及其使用方法。
• SUBSTITUTED 2,3,4,5-TETRAHYDRO-1H-PYRIDO[4,3-B]INDOLES, METHODS FOR USE THEREOF
  申请人：Ivachtchenko Alexandre Vasilievich

  公开号：US20190233409A1

  公开（公告）日：2019-08-01

  The present invention relates to compound of the formula 1.2, or a pharmaceutically acceptable salt, or hydrate thereof wherein R 1 is C 1 -C 5 alkyl; R 2 , is independently hydrogen, halogen, C 1 -C 3 alkyl, CF 3 , OCF 3 or OCH 3 ; i is 1, 2,3, or 4; Ar is unsubstituted phenyl or substituted phenyl substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, a substituted amino group or trifluoromethyl; or Ar is a substituted or unsubstituted 6-membered aromatic heterocycle one or, with two nitrogen atoms in the heterocycle; excluding the compounds of the formulas A1-A4 The invention relates to the novel chemical compounds, methods for their preparation and use as antagonists of 5-HT 6 receptors, simultaneously regulating homeostasis of calcium ions in cells. The invention relates to the novel annelated azaheterocycles—2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoles, to methods for their preparation, to pharmaceutical compositions, including these compounds as active substances, and to methods of treatment and profylaxis of various diseases.

  本发明涉及公式1.2的化合物，或其药学上可接受的盐或水合物，其中R1为C1-C5烷基；R2独立地为氢、卤素、C1-C3烷基、CF3、OCF3或OCH3；i为1、2、3或4；Ar为未取代的苯基或取代的苯基，取代基为卤素、C1-C6烷基、C1-C6烷氧基、取代氨基或三氟甲基；或Ar为取代或未取代的6元芳杂环之一，其中异杂环中含有两个氮原子；但不包括A1-A4式的化合物。本发明涉及新的化学化合物、其制备方法以及作为5-HT6受体拮抗剂的用途，同时调节细胞内钙离子的稳态。本发明涉及新的螺合的氮杂环-2,3,4,5-四氢-1H-吡啶[4,3-b]吲哚化合物，以及其制备方法、包括这些化合物作为活性物质的制药组合物，以及各种疾病的治疗和预防方法。
• SUSTITUTED 2,3,4,5-TETRAHYDRO-1H-PYRIDO[4,3-B]INDOLES, METHODS FOR USE THEREOF
  申请人：Alla Chem, LLC

  公开号：US20130217703A1

  公开（公告）日：2013-08-22

  The present invention relates to a method of antagonizing a 5-HT 6 serotonin receptor and simultaneously regulating Ca +2 ion homeostasis in a cell, comprising administering to the cell a compound of formula 1, or a pharmaceutically acceptable salt thereof, wherein: R 1 is a C 1 -C 5 alkyl; R 2 i is independently hydrogen, halogen, a C 1 -C 3 alkyl, CF 3 , OCF 3 or OCH 3 ; i is 1, 2, 3 or 4; Ar is an unsubstituted phenyl or a substituted phenyl substituted with halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, substituted amino group or trifluoromethyl; or Ar is a substituted or unsubstituted 6-membered aromatic heterocycle with one or two nitrogen atoms in the heterocycle; and W is an ethylene group —CH 2 —CH 2 —, ethenyl group —CH═CH—, or ethynyl group —C≡C—. The invention also relates to new compounds selected from the group of compounds of the general formula 1, method for their preparation, pharmaceutical compositions and method for treating a cognitive disorder or neurodegenerative disease, or obesity in a subject in need thereof comprising administering an effective dose to the subject of a compound of formula 1 according to claim 1 , or a pharmaceutically acceptable salt thereof.

  本发明涉及一种拮抗5-HT6 5-羟色胺受体和同时调节细胞内Ca+2离子稳态的方法，包括向细胞中投与式1的化合物或其药学上可接受的盐，其中：R1是C1-C5烷基；R2独立地是氢、卤素、C1-C3烷基、CF3、OCF3或OCH3；i为1、2、3或4；Ar是未取代的苯基或取代的苯基，其被卤素、C1-C6烷基、C1-C6烷氧基、取代的氨基团或三氟甲基取代；或Ar是带有一个或两个氮原子的取代或未取代的6元芳香杂环；W是乙烯基—CH2—CH2—、乙烯基—CH═CH—或乙炔基—C≡C—。本发明还涉及从式1的化合物组中选择的新化合物、其制备方法、制备药物组合物的方法以及治疗认知障碍或神经退行性疾病或肥胖症的方法，包括向需要治疗的受体中投与式1的化合物或其药学上可接受的盐的有效剂量。
• Tetracyclic compounds
  申请人：HUNG David T.

  公开号：US20090239854A1

  公开（公告）日：2009-09-24

  This disclosure relates to new tetracyclic compounds that may be used to modulate a histamine receptor in an individual. The compounds in one embodiment are tetracyclic [4,3-b]indoles. Pharmaceutical compositions comprising the compounds are also provided, as are methods of using the compounds in a variety of therapeutic applications, including the treatment of a cognitive disorder, psychotic disorder, neurotransmitter-mediated disorder and/or a neuronal disorder.

  本公开涉及新的四环化合物，可用于调节个体中的组胺受体。在一种实施例中，该化合物为四环[4,3-b]吲哚。还提供了包含该化合物的药物组合物，以及使用该化合物进行各种治疗应用的方法，包括治疗认知障碍、精神障碍、神经递质介导的障碍和/或神经元障碍。