2,3-dihydro-1H-indole-3-carboxylic acid methyl-(1-methyl-piperidin-4-yl)-amide | 583815-02-5

• 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: 2,3-dihydro-1H-indole-3-carboxylic acid methyl-(1-methyl-piperidin-4-yl)-amide
• 英文别名: N-methyl-N-(1-methylpiperidin-4-yl)-2,3-dihydro-1H-indole-3-carboxamide
• CAS: 583815-02-5
• 化学式: C₁₆H₂₃N₃O
• 分子量: 273.378
• InChiKey: UHUQUFUTYMONIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  35.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3-dihydro-1H-indole-3-carboxylic acid methyl-(1-methyl-piperidin-4-yl)-amide 、 苯并[1,2,5]噻二唑-4-磺酰氯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 1-(2,1,3-benzothiadiazol-4-ylsulfonyl)-N-methyl-N-(1-methylpiperidin-4-yl)-2,3-dihydroindole-3-carboxamide
  参考文献：
  名称：

  The discovery and SAR of indoline-3-carboxamides—A new series of 5-HT6 antagonists

  摘要：

  Antagonists of the 5-HT6 receptor have been shown to improve cognitive function in a wide range of animal models and as such may prove to be attractive agents for the symptomatic treatment of cognitive disorders such as Alzheimer's disease ( AD) and schizophrenia. We report herein the identification and SAR around N-(2-aminoalkyl)-1-(arylsulfonyl)indoline-3-carboxamides-a novel chemotype of 5-HT6 antagonists. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.04.085
• 作为产物：
  描述：

  1-甲基-4-(甲氨基)哌啶 、 吲哚啉-3-羧酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以58%的产率得到2,3-dihydro-1H-indole-3-carboxylic acid methyl-(1-methyl-piperidin-4-yl)-amide
  参考文献：
  名称：

  The discovery and SAR of indoline-3-carboxamides—A new series of 5-HT6 antagonists

  摘要：

  Antagonists of the 5-HT6 receptor have been shown to improve cognitive function in a wide range of animal models and as such may prove to be attractive agents for the symptomatic treatment of cognitive disorders such as Alzheimer's disease ( AD) and schizophrenia. We report herein the identification and SAR around N-(2-aminoalkyl)-1-(arylsulfonyl)indoline-3-carboxamides-a novel chemotype of 5-HT6 antagonists. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.04.085

文献信息

• 1-arylsulfonyl-3-substituted indole and indoline derivatives useful in the treatment of central nervous system disorders
  申请人：Spinks Daniel

  公开号：US20050154023A1

  公开（公告）日：2005-07-14

  The present invention relates to 1-arylsulfonyl-3-substituted indole or indoline derivatives having the general formula I wherein the dotted line represents an optional bond; n is 0 or 1; m is 0-5 and Ar, R 6 -R 11 , are defined in the description. The invention further relates to pharmaceutical compositions comprising said derivatives, and to the use of these 1-arylsulfonyl-3-substituted indole or indoline derivatives in the treatment of central nervous disorders such as psychosis, schizophrenia, manic depressions, depressions, neurological disorders, cognitive enhancement, Parkinson's disease, amyotrophic lateral sclerosis, Alzheimer's disease and Huntington's disease.

  本发明涉及具有一般式I的1-芳基磺酰基-3-取代吲哚或吲哚啉衍生物，其中虚线表示可选键；n为0或1；m为0-5，而Ar、R6-R11在说明中定义。本发明还涉及包含所述衍生物的制药组合物，并且涉及使用这些1-芳基磺酰基-3-取代吲哚或吲哚啉衍生物治疗中枢神经系统疾病，如精神病、精神分裂症、躁郁症、抑郁症、神经系统疾病、认知增强、帕金森病、肌萎缩性侧索硬化症、阿尔茨海默病和亨廷顿病。
• 1-ARYLSULFONYL-3-SUBSTITUED INDOLE AND INDOLINE DERIVATES USEFUL IN THE TREATMENT OF CENTRAL NERVOUS SYSTEM DISORDERS
  申请人：N.V. Organon

  公开号：EP1476151B1

  公开（公告）日：2008-07-16
• US7838518B2
  申请人：——

  公开号：US7838518B2

  公开（公告）日：2010-11-23
• [EN] 1-ARYLSULFONYL-3-SUBSTITUTED INDOLE AND INDOLINE DERIVATIVES USEFUL IN THE TREATMENT OF CENTRAL NERVOUS SYSTEM DISORDERS<br/>[FR] DERIVES D'INDOLE ET D'INDOLINE 1-ARYLSULFONYL-3-SUBSTITUES UTILES DANS LE TRAITEMENT DE TROUBLES DU SYSTEME NERVEUX CENTRAL
  申请人：AKZO NOBEL NV

  公开号：WO2003068220A1

  公开（公告）日：2003-08-21

  The present invention relates to 1- arylsulfonyl-3 substituted indoline derivatives having the general formula (I) (I) wherein the dotted line represents an optional bond, n is 0 or 1, m is 0-5 and Ar, R6-R11 are as defined in the description. The invention further relates to pharmaceutical compositions comprising the said derivatives, and to the use of these 1- arylsulfonyl-3- substituted indole or indoline derivatives in the treatment of central nervous disorders such as psychosis, schizophrenia, manic depressions, depressions, neurological disorders, cognitive enhancement, Parkinson' s disease, amyotrophic lateral sclerosis, Alzheimer' s disease and Huntington' s disease.