1-(4-Chlorophenyl)-2-(2,4-dichlorophenyl)-5-iodo-N-(piperidin-1-yl)-1H-imidazole-4-carboxamide | 505074-61-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-Chlorophenyl)-2-(2,4-dichlorophenyl)-5-iodo-N-(piperidin-1-yl)-1H-imidazole-4-carboxamide
• 英文别名: 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-iodo-N-piperidin-1-ylimidazole-4-carboxamide
• CAS: 505074-61-3
• 化学式: C₂₁H₁₈Cl₃IN₄O
• 分子量: 575.664
• InChiKey: MCLDRTREOJASMB-UHFFFAOYSA-N

物化性质

• 熔点：
  192-201 °C (decomp)
• 密度：
  1.74±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-iodo-1H-imidazole-4-carboxylic acid 、 1-氨基哌啶 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 16.0h， 生成 1-(4-Chlorophenyl)-2-(2,4-dichlorophenyl)-5-iodo-N-(piperidin-1-yl)-1H-imidazole-4-carboxamide
  参考文献：
  名称：

  Probing the cannabinoid CB1/CB2 receptor subtype selectivity limits of 1,2-diarylimidazole-4-carboxamides by fine-tuning their 5-substitution pattern

  摘要：

  The cannabinoid CB1/CB2 receptor subtype selectivity in the 1,2-diarylimidazole-4-carboxamide series was boosted by fine-tuning its 5-substitution pattern. The presence of the 5-methylsulfonyl group in 11 led to a greater than similar to 840-fold CB1/CB2 subtype selectivity. The compounds 10, 18 and 19 were found more active than rimonabant (1) in a CB1-mediated rodent hypotension model after oral administration. Our findings suggest a limited brain exposure of the P-glycoprotein substrates 11, 12 and 21. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.03.068

文献信息

• 1 H-imidazole derivatives having CB1 agonistic, CB1 partial agonistic or CB1-antagonistic activity
  申请人：Kruse G. Cornelis

  公开号：US20050054679A1

  公开（公告）日：2005-03-10

  The present invention relates to a group of novel 1H-imidazole derivatives, to methods for the preparation of these compounds, and to pharmaceutical compositions containing one or more of these compounds as an active component. These 1H-imidazole derivatives are potent cannabinoid-CB 1 receptor agonists, partial agonists or antagonists, useful for the treatment of psychiatric and neurological disorders, as well as and other diseases involving cannabinoid neurotransmission. The compounds have the general formula (I) wherein R and R 1 -R 4 have the meanings given in the specification.

  本发明涉及一组新颖的1H-咪唑衍生物，以及制备这些化合物的方法和含有这些化合物中的一个或多个作为活性成分的药物组合物。这些1H-咪唑衍生物是有效的大麻素-CB1受体激动剂、部分激动剂或拮抗剂，可用于治疗精神疾病和神经系统疾病，以及其他涉及大麻素神经传递的疾病。这些化合物具有通式（I），其中R和R1-R4的含义如规范中所述。
• 1H-imidazole derivatives having cb1 agonistic, cb1 partial agonistic or cb1 antagonistic activity
  申请人：——

  公开号：US20040235854A1

  公开（公告）日：2004-11-25

  The present invention relates to a group of novel 1H-imidazole derivatives, to methods for the preparation of these compounds, and to pharmaceutical compositions containing one or more of these compounds as an active component. These 1H-imidazole derivatives are potent cannabinoid-CB1 receptor agonists, partial agonists or antagonists, useful for the treatment of psychiatric and neurological disorders, as well as and other diseases involving cannabinoid neurotransmission. The compounds have the general formula (I) wherein R and R1-R4 have the meanings given in the specification. 1

  本发明涉及一组新型1H-咪唑衍生物，以及制备这些化合物的方法和含有这些化合物作为活性成分的药物组合物。这些1H-咪唑衍生物是有效的大麻素-CB1受体激动剂、部分激动剂或拮抗剂，可用于治疗精神和神经系统疾病，以及其他涉及大麻素神经递质的疾病。这些化合物的一般式为(I)，其中R和R1-R4在规范中给出了它们的含义。
• 1H-IMIDAZOLE DERIVATIVE HAVING CB1, AGONISTIC, CB1 PARTIAL AGONISTIC OR CB1 ANTAGNISTIC ACTIVITY
  申请人：KRUSE Cornelis G.

  公开号：US20090181949A1

  公开（公告）日：2009-07-16

  The present invention relates to a group of novel 1H-imidazole derivatives, to methods for the preparation of these compounds, and to pharmaceutical compositions containing one or more of these compounds as an active component. These 1H-imidazole derivatives are potent cannabinoid-CB1 receptor agonists, partial agonists or antagonists, useful for the treatment of psychiatric and neurological disorders, as well as and other diseases involving cannabinoid neurotransmission. The compounds have the general formula (I) wherein R and R1-R4 have the meanings given in the specification.

  本发明涉及一组新型1H-咪唑衍生物，以及制备这些化合物的方法和含有这些化合物作为活性成分的药物组合物。这些1H-咪唑衍生物是有效的大麻素-CB1受体激动剂、部分激动剂或拮抗剂，可用于治疗精神和神经疾病，以及其他涉及大麻素神经传递的疾病。这些化合物的一般式为(I)，其中R和R1-R4在说明书中有所描述。
• 1H-IMIDAZOLE DERIVATIVES HAVING CB1 AGONISTIC, CB1 PARTIAL AGONISTIC OR CB1- ANTAGONISTIC ACTIVITY
  申请人：Solvay Pharmaceuticals B.V.

  公开号：EP1438296B1

  公开（公告）日：2008-11-26
• US7109216B2
  申请人：——

  公开号：US7109216B2

  公开（公告）日：2006-09-19