2-(3-chloro-phenylamino)-4-trifluoromethyl-pyrimidine-5-carboxylic acid N-(3-methoxybenzyl)amide

• 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: 2-(3-chloro-phenylamino)-4-trifluoromethyl-pyrimidine-5-carboxylic acid N-(3-methoxybenzyl)amide
• 英文别名: 2-(3-chloroanilino)-N-[(3-methoxyphenyl)methyl]-4-(trifluoromethyl)pyrimidine-5-carboxamide
• 化学式: C₂₀H₁₆ClF₃N₄O₂
• 分子量: 436.821
• InChiKey: AKRADNLOOALELB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  76.1
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  benzyl 2-(3-chlorophenylamino)-4-trifluoromethyl-pyrimidine-5-carboxylate 在 N-乙基吗啉 、 氢氧化钾 、 1-羟基苯并三唑一水物 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 2-(3-chloro-phenylamino)-4-trifluoromethyl-pyrimidine-5-carboxylic acid N-(3-methoxybenzyl)amide
  参考文献：
  名称：

  Discovery of 2-[(2,4-Dichlorophenyl)amino]-N-[(tetrahydro- 2H-pyran-4-yl)methyl]-4-(trifluoromethyl)- 5-pyrimidinecarboxamide, a Selective CB2 Receptor Agonist for the Treatment of Inflammatory Pain

  摘要：

  Selective CB2 receptor agonists are promising potential therapeutic agents for the treatment of inflammatory and neuropathic pain. A focused screen identified a pyrimidine ester as a partial agonist at the CB2 receptor with micromolar potency. Subsequent lead optimization identified 35, GW842166X, as the optimal compound in the series. 35 has an oral ED50 of 0.1 mg/kg in the rat FCA model of inflammatory pain and was selected as a clinical candidate for this indication.

  DOI：

  10.1021/jm061195+

文献信息

• Pyrimidine derivatives as CB2 cannabinoid receptor modulators
  申请人：GLAXO GROUP LIMITED

  公开号：EP1736470A2

  公开（公告）日：2006-12-27

  The present invention relates to novel pyrimidine 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.

  本发明涉及新型嘧啶衍生物、含有这些化合物的药物组合物及其在治疗疾病（尤其是疼痛）中的用途，这些疾病是由大麻素受体活性的增加或降低直接或间接引起的。
• Discovery of 2-[(2,4-Dichlorophenyl)amino]-<i>N</i>-[(tetrahydro- 2<i>H</i>-pyran-4-yl)methyl]-4-(trifluoromethyl)- 5-pyrimidinecarboxamide, a Selective CB2 Receptor Agonist for the Treatment of Inflammatory Pain
  作者：Gerard M. P. Giblin、Celestine T. O'Shaughnessy、Alan Naylor、William L. Mitchell、Andrew J. Eatherton、Brian P. Slingsby、D. Anthony Rawlings、Paul Goldsmith、Andrew J. Brown、Carl P. Haslam、Nick M. Clayton、Alex W. Wilson、Iain P. Chessell、Andrew R. Wittington、Richard Green

  DOI：10.1021/jm061195+

  日期：2007.5.1

  Selective CB2 receptor agonists are promising potential therapeutic agents for the treatment of inflammatory and neuropathic pain. A focused screen identified a pyrimidine ester as a partial agonist at the CB2 receptor with micromolar potency. Subsequent lead optimization identified 35, GW842166X, as the optimal compound in the series. 35 has an oral ED50 of 0.1 mg/kg in the rat FCA model of inflammatory pain and was selected as a clinical candidate for this indication.