3-amino-6-chloro-5-(dimethylamino)-N-pyridin-2-yl-pyrazine-2-carboxamide | 37804-11-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3-amino-6-chloro-5-(dimethylamino)-N-pyridin-2-yl-pyrazine-2-carboxamide
• 英文别名: 3-amino-6-chloro-5-(dimethylamino)-N-pyridin-2-ylpyrazine-2-carboxamide
• CAS: 37804-11-8
• 化学式: C₁₂H₁₃ClN₆O
• 分子量: 292.728
• InChiKey: QUODWOZQRXAWHV-UHFFFAOYSA-N

物化性质

• 溶解度：
  在 DMSO 中溶解度为 100 mM

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  97
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-amino-6-chloro-5-(dimethylamino)-N-pyridin-2-yl-pyrazine-2-carboxamide 在 氢气 作用下， 生成 3-Amino-5-dimethylamino-pyrazine-2-carboxylic acid pyridin-2-ylamide
  参考文献：
  名称：

  Dipyridyl amides: potent metabotropic glutamate subtype 5 (mGlu5) receptor antagonists

  摘要：

  The mGlu5 receptor has been implicated in a number of CNS disorders. Herein, we report on the discovery, synthesis, and biological evaluation of dipyridyl amides as small molecules mGluR5 antagonists. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.11.078
• 作为产物：
  描述：

  2-氨基吡啶 、 3-氨基-6-氯-5-二甲氨基-吡嗪-2-羧酸 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 3-amino-6-chloro-5-(dimethylamino)-N-pyridin-2-yl-pyrazine-2-carboxamide
  参考文献：
  名称：

  Dipyridyl amides: potent metabotropic glutamate subtype 5 (mGlu5) receptor antagonists

  摘要：

  The mGlu5 receptor has been implicated in a number of CNS disorders. Herein, we report on the discovery, synthesis, and biological evaluation of dipyridyl amides as small molecules mGluR5 antagonists. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.11.078

文献信息

• [EN] BIPYRIDYL AMIDES AS MODULATORS OF METABOTROPIC GLUTAMATE RECEPTOR-5<br/>[FR] AMIDES BIPYRIDYLES EN TANT QUE MODULATEURS DU RÉCEPTEUR-5 MÉTABOTROPIQUE DU GLUTAMATE
  申请人：MERCK & CO INC

  公开号：WO2005079802A1

  公开（公告）日：2005-09-01

  The present invention is directed to novel amides such as those of Formula (I): (I) which are mGluR5 modulators useful in the treatment or prevention of diseases and conditions in which mGluR5 is involved, including but not limited to psychiatric and mood disorders such as schizophrenia, anxiety, depression, bipolar disorders, and panic, as well as in the treatment of pain, Parkinson’s disease, cognitive dysfunction, epilepsy, circadian rhythm and sleep disorders, such as shift-work induced sleep disorder and jet-lag, drug addiction, drug abuse, drug withdrawal, obesity and other diseases. The invention is also directed to pharmaceutical compositions comprising these compounds. This invention further provides a method of treatment of these disorders and conditions by the administration of an effective amount of these novel amides and/or compositions containing these compounds.

  本发明涉及新型酰胺，如式(I)所示的酰胺：(I)，这些酰胺是mGluR5调节剂，可用于治疗或预防涉及mGluR5的疾病和症状，包括但不限于精神疾病和情绪障碍，如精神分裂症、焦虑、抑郁、双相障碍和恐慌，以及用于治疗疼痛、帕金森病、认知功能障碍、癫痫、昼夜节律和睡眠障碍，如倒班工作引起的睡眠障碍和时差反应，药物成瘾、药物滥用、药物戒断、肥胖和其他疾病。本发明还涉及包含这些化合物的药物组合物。本发明进一步提供了通过给予这些新型酰胺和/或含有这些化合物的组合物的有效量来治疗这些疾病和症状的方法。
• Bipyridyl amides as modulators of metabotropic glutamate receptor-5
  申请人：Bonnefous Celine

  公开号：US20070149547A1

  公开（公告）日：2007-06-28

  The present invention is directed to novel amides such as those of Formula (I): (I) which are mGluR5 modulators useful in the treatment or prevention of diseases and conditions in which mGluR5 is involved, including but not limited to psychiatric and mood disorders such as schizophrenia, anxiety, depression, bipolar disorders, and panic, as well as in the treatment of pain, Parkinson's disease, cognitive dysfunction, epilepsy, circadian rhythm and sleep disorders, such as shift-work induced sleep disorder and jet-lag, drug addiction, drug abuse, drug withdrawal, obesity and other diseases. The invention is also directed to pharmaceutical compositions comprising these compounds. This invention further provides a method of treatment of these disorders and conditions by the administration of an effective amount of these novel amides and/or compositions containing these compounds.

  本发明涉及新型酰胺，例如公式（I）所示的酰胺：（I），它们是mGluR5调节剂，可用于治疗或预防包括但不限于精神和情绪障碍（如精神分裂症、焦虑、抑郁、双相障碍和惊恐）以及疼痛、帕金森病、认知功能障碍、癫痫、昼夜节律和睡眠障碍（如倒班工作引起的睡眠障碍和时差反应）、药物成瘾、药物滥用、药物戒断、肥胖症和其他疾病中涉及mGluR5的疾病和症状的治疗。本发明还涉及包含这些化合物的制药组合物。本发明还提供了通过给予这些新型酰胺和/或含有这些化合物的组合物的有效量来治疗这些疾病和症状的方法。
• BIPYRIDYL AMIDES AS MODULATORS OF METABOTROPIC GLUTAMATE RECEPTOR-5
  申请人：Merck & Co., Inc.

  公开号：EP1715867A1

  公开（公告）日：2006-11-02
• EP1715867A4
  申请人：——

  公开号：EP1715867A4

  公开（公告）日：2009-04-15
• Dipyridyl amides: potent metabotropic glutamate subtype 5 (mGlu5) receptor antagonists
  作者：Céline Bonnefous、Jean-Michel Vernier、John H. Hutchinson、Janice Chung、Grace Reyes-Manalo、Theodore Kamenecka

  DOI：10.1016/j.bmcl.2004.11.078

  日期：2005.2

  The mGlu5 receptor has been implicated in a number of CNS disorders. Herein, we report on the discovery, synthesis, and biological evaluation of dipyridyl amides as small molecules mGluR5 antagonists. (C) 2004 Elsevier Ltd. All rights reserved.