3-chloro-N-(6-methylpyridin-3-yl)-5-(1-propyl-1H-benzo[d]imidazol-2-yl)pyridin-2-amine | 1072929-21-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 3-chloro-N-(6-methylpyridin-3-yl)-5-(1-propyl-1H-benzo[d]imidazol-2-yl)pyridin-2-amine
• 英文别名: [3-chloro-5-(1-propyl-1H-benzoimidazol-2-yl)-pyridin-2-yl]-(6-methyl-pyridin-3-yl)-amine；3-chloro-N-(6-methylpyridin-3-yl)-5-(1-propylbenzimidazol-2-yl)pyridin-2-amine
• CAS: 1072929-21-5
• 化学式: C₂₁H₂₀ClN₅
• 分子量: 377.876
• InChiKey: WEGQZOQLVXNSEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5,6-二氯烟酸甲酯 在 tris-(dibenzylideneacetone)dipalladium(0) 、 水 、 potassium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium hydroxide 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 32.0h， 生成 3-chloro-N-(6-methylpyridin-3-yl)-5-(1-propyl-1H-benzo[d]imidazol-2-yl)pyridin-2-amine
  参考文献：
  名称：

  Benzimidazoles as Potent and Orally Active mGlu5 Receptor Antagonists with an Improved PK Profile

  摘要：

  A focused chemical optimization effort of a compound 1 based on metabolite elucidation is described, resulting in 15i, a highly potent and selective mGlu5 receptor antagonist with an improved pharmacokinetic profile compared to 1. Characterization of 15i in vivo in the fear potentiated startle (FPS) paradigm revealed a robust reduction of conditioned fear behavior. This effect nicely correlates with the rat brain pharmacokinetics.

  DOI：

  10.1021/ml100215b

文献信息

• Organic compounds
  申请人：Glatthar Ralf

  公开号：US20090105266A1

  公开（公告）日：2009-04-23

  The present invention relates to novel benzimidazole derivatives, their preparation, their use as pharmaceuticals and pharmaceutical compositions containing them, wherein the compounds have the formula (I): in which the substitutents are as defined in claim 1 and salts, solvates, hydrates and N-oxides thereof.

  本发明涉及新型苯并咪唑衍生物，其制备，其用作药物以及含有它们的药物组合物，其中化合物具有以下结构式（I）： 其中取代基如权利要求1中所定义，并且其盐、溶剂合物、水合物和N-氧化物。
• NICOTINIC ACID DERIVATIVES AS MODULATORS OF METABOTROPIC GLUTAMATE RECEPTOR-5
  申请人：Novartis AG

  公开号：EP2146969A1

  公开（公告）日：2010-01-27
• [EN] NICOTINIC ACID DERIVATIVES AS MODULATORS OF METABOTROPIC GLUTAMATE RECEPTOR-5<br/>[FR] COMPOSÉS ORGANIQUES
  申请人：NOVARTIS AG

  公开号：WO2008128968A1

  公开（公告）日：2008-10-30

  [EN] The present invention relates to novel benzimidazole derivatives, their preparation, their use as pharmaceuticals and pharmaceutical compositions containing them, wherein the compounds have the Formula (I): in which the substitutents are as defined in claim 1 and and salts, solvates, hydrates and N- oxides thereof.
  [FR] La présente invention concerne de nouveaux dévirés de benzimidazole, leur préparation, leur utilisation en tant que produits pharmaceutiques et des compositions pharmaceutiques les contenant, les composés étant de formule (I) : dans laquelle les substituants sont tels que définis dans la revendication 1 et les sels, solvates, hydrates et N-oxydes de ceux-ci.
• Benzimidazoles as Potent and Orally Active mGlu5 Receptor Antagonists with an Improved PK Profile
  作者：David Carcache、Ivo Vranesic、Joachim Blanz、Sandrine Desrayaud、Markus Fendt、Ralf Glatthar

  DOI：10.1021/ml100215b

  日期：2011.1.13

  A focused chemical optimization effort of a compound 1 based on metabolite elucidation is described, resulting in 15i, a highly potent and selective mGlu5 receptor antagonist with an improved pharmacokinetic profile compared to 1. Characterization of 15i in vivo in the fear potentiated startle (FPS) paradigm revealed a robust reduction of conditioned fear behavior. This effect nicely correlates with the rat brain pharmacokinetics.