1-(7-chloro-1,3-dimethyl-1H-pyrrolo[2,3-c]pyridine-4-yl)-1-morpholin-4-yl-methanone | 871819-49-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: 1-(7-chloro-1,3-dimethyl-1H-pyrrolo[2,3-c]pyridine-4-yl)-1-morpholin-4-yl-methanone
• 英文别名: (7-chloro-1,3-dimethylpyrrolo[2,3-c]pyridin-4-yl)-morpholin-4-ylmethanone
• CAS: 871819-49-7
• 化学式: C₁₄H₁₆ClN₃O₂
• 分子量: 293.753
• InChiKey: OZIYZQHFCUZHRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(7-chloro-1,3-dimethyl-1H-pyrrolo[2,3-c]pyridine-4-yl)-1-morpholin-4-yl-methanone 、 3,5-二氟苯胺 反应 0.5h， 以to give 1-[7-(3,5-difluoro-phenylamino)-1,3-dimethyl-1H-pyrrolo[2,3-c]pyridin-4-yl]-1-morpholin-4-yl-methanone (33 mg)的产率得到1-[7-(3,5-difluoro-phenylamino)-1,3-dimethyl-1H-pyrrolo[2,3-c]pyridin-4-yl]-1-morpholin-4-yl-methanone
  参考文献：
  名称：

  Pyrrolopyridine Derivatives

  摘要：

  本发明涉及新型吡咯吡啶衍生物、含有这些化合物的药物组合物及其在治疗疾病，特别是疼痛方面的用途，这些疾病直接或间接地由大麻素受体活性的增加或减少引起。

  公开号：

  US20070219229A1
• 作为产物：
  描述：

  吗啉 、 7-chloro-1,3-dimethyl-1H-pyrrolo[2,3-c]pyridine-4-carboxylic acid 在 N-乙基吗啉 、 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以463 mg的产率得到1-(7-chloro-1,3-dimethyl-1H-pyrrolo[2,3-c]pyridine-4-yl)-1-morpholin-4-yl-methanone
  参考文献：
  名称：

  Discovery of 1-[4-(3-Chlorophenylamino)-1-methyl-1H-pyrrolo[3,2-c]pyridin-7-yl]-1-morpholin-4-ylmethanone (GSK554418A), a Brain Penetrant 5-Azaindole CB₂ Agonist for the Treatment of Chronic Pain

  摘要：

  We report the synthesis and SAR of a series of novel azaindole CB2 agonists. 6-Azaindole 18 showed activity in an acute pain model but was inactive in a chronic model. 18 is a Pgp substrate with low brain penetration. The template was redesigned, and the resulting 5-azaindole 36 was a potent CB2 agonist with high CNS penetration. This compound was efficacious in the acute model and the chronic joint pain model.

  DOI：

  10.1021/jm9009857

文献信息

• [EN] PYRROLOPYRIDINE DERIVATIVES<br/>[FR] DERIVES DE PYRROLOPYRIDINE
  申请人：GLAXO GROUP LTD

  公开号：WO2005121140A1

  公开（公告）日：2005-12-22

  The present invention relates to novel pyrrolopyridine derivatives, pharmaceutical compositions containing these compounds and their use in the treatment of diseases, particularly pain, which diseases are caused directly or indirectly by an increase or decrease in activity of the cannabinoid receptor.

  这项发明涉及新型吡咯吡啶衍生物，含有这些化合物的药物组合物以及它们在治疗疾病，特别是疼痛方面的用途，这些疾病直接或间接地由大麻素受体活性的增加或减少引起。
• Pyrrolopyridine Derivatives
  申请人：Eatherton John Andrew

  公开号：US20070219229A1

  公开（公告）日：2007-09-20

  The present invention relates to novel pyrrolopyridine derivatives, pharmaceutical compositions containing these compounds and their use in the treatment of diseases, particularly pain, which diseases are caused directly or indirectly by an increase or decrease in activity of the cannabinoid receptor.

  本发明涉及新型吡咯吡啶衍生物、含有这些化合物的药物组合物及其在治疗疾病，特别是疼痛方面的用途，这些疾病直接或间接地由大麻素受体活性的增加或减少引起。
• PYRROLOPYRIDINE DERIVATIVES
  申请人：GLAXO GROUP LIMITED

  公开号：EP1753764A1

  公开（公告）日：2007-02-21
• US7589206B2
  申请人：——

  公开号：US7589206B2

  公开（公告）日：2009-09-15
• Discovery of 1-[4-(3-Chlorophenylamino)-1-methyl-1<i>H</i>-pyrrolo[3,2-<i>c</i>]pyridin-7-yl]-1-morpholin-4-ylmethanone (GSK554418A), a Brain Penetrant 5-Azaindole CB₂ Agonist for the Treatment of Chronic Pain
  作者：Gerard M. P. Giblin、Andrew Billinton、Michael Briggs、Andrew J. Brown、Iain P. Chessell、Nick M. Clayton、Andrew J. Eatherton、Paul Goldsmith、Carl Haslam、Matthew R. Johnson、William L. Mitchell、Alan Naylor、Alcide Perboni、Brian P. Slingsby、Alex W. Wilson

  DOI：10.1021/jm9009857

  日期：2009.10.8

  We report the synthesis and SAR of a series of novel azaindole CB2 agonists. 6-Azaindole 18 showed activity in an acute pain model but was inactive in a chronic model. 18 is a Pgp substrate with low brain penetration. The template was redesigned, and the resulting 5-azaindole 36 was a potent CB2 agonist with high CNS penetration. This compound was efficacious in the acute model and the chronic joint pain model.