1-(4-chlorophenyl)-5-(2,4-dichlorophenyl)-N-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-1H-1,2,4-triazole-3-carboxamide

• 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)-5-(2,4-dichlorophenyl)-N-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-1H-1,2,4-triazole-3-carboxamide
• 英文别名: N-(3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl)-1-(4-chlorophenyl)-5-(2,4-dichlorophenyl)-1,2,4-triazole-3-carboxamide
• 化学式: C₂₂H₂₀Cl₃N₅O
• 分子量: 476.793
• InChiKey: IQBDRJGQTWPMPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  63
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(4-chlorophenyl)-5-(2,4-dichlorophenyl)-1H-1,2,4-triazole-3-carboxylic acid 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 1-(4-chlorophenyl)-5-(2,4-dichlorophenyl)-N-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-1H-1,2,4-triazole-3-carboxamide
  参考文献：
  名称：

  与SR141716相关的有效咪唑和三唑CB1受体拮抗剂。

  摘要：

  合成了与SR141716相关的二芳基咪唑甲酰胺和二芳基三唑甲酰胺，并测试了与人CB（1）受体的结合。适当取代的咪唑对临床候选者具有相当的效力，而类似的三唑则不那么有效，因为在唑环上不存在其他取代基。

  DOI：

  10.1016/j.bmcl.2003.12.068

文献信息

• [EN] 1H-1,2,4-TRIAZOLE-3-CARBOXAMIDE DERIVATIVES AS CANNABINOID-CB1 RECEPTOR LIGANDS<br/>[FR] DERIVES DE 1H-1,2,4-TRIAZOLE-3-CARBOXAMIDE AYANT UNE ACTIVITE AGONISTE PARTIELLE, AGONISTE OU ANTAGONISTE INVERSE DU RECEPTEUR DE CANNABINOIDES-CB1
  申请人：SOLVAY PHARM BV

  公开号：WO2004026301A1

  公开（公告）日：2004-04-01

  The present invention relates to a group of 1H-1,2,4-triazole-3-carboxamide derivatives, to methods for the preparation of these compounds, and to pharmaceutical compositions containing at least one of these compounds as an active ingredient. These 1H-1,2,4-triazole-3-carboxamide derivatives are potent cannabinoid-CB1 receptor agonists, partial agonists, inverse agonists or antagonists, useful for the treatment of disorders involving cannabinoid neurotransmission. The compounds have the general formula (I), wherein R and R1-R3 have the meanings given in the specification.

  本发明涉及一组1H-1,2,4-三唑-3-羧酰胺衍生物，以及制备这些化合物的方法和含有至少其中一种化合物作为活性成分的药物组合物。这些1H-1,2,4-三唑-3-羧酰胺衍生物是有效的大麻素-CB1受体激动剂、部分激动剂、反向激动剂或拮抗剂，可用于治疗涉及大麻素神经递质的疾病。这些化合物具有通式(I)，其中R和R1-R3在说明书中给出。
• Novel medical uses of compounds showing CB1-antagonistic activity and combination treatment involving said compounds
  申请人：Antel Jochen

  公开号：US20050124660A1

  公开（公告）日：2005-06-09

  The present invention relates to a novel medical use of compounds with CB 1 -receptor activity selected from the group of 4,5-dihydro-1H-pyrazole derivatives, 1H-Imidazole derivatives, thiazole derivatives and/or 1H-1,2,4-triazole-3-carboxamide derivatives, as each defined in the specification, or of a prodrug thereof, a tautomer thereof or a salt thereof, in the manufacture of medicaments for the treatment and/or prophylaxis of CB 1 receptor related diseases in juvenile patients and/or for the treatment and/or prophylaxis of drug induced obesity in juvenile, as well as in adolescent, patients. Furthermore, the invention pertains to the use of said compounds with CB 1 -receptor activity in combination with lipase inhibitors. Said compounds are particularly suitable in combination with lipase inhibitors in the manufacture of medicaments for the treatment and/or prophylaxis of obesity in adolescent or in juvenile patients and/or for the treatment and/or prophylaxis of drug induced obesity in juvenile as well as in adolescent patients. Preferred lipase inhibitors are orlistat, panclicins, ATL-962 and/or lipstatin.

  本发明涉及一种新型医用化合物，该化合物具有CB1受体活性，所述化合物选自4,5-二氢-1H-吡唑衍生物、1H-咪唑衍生物、噻唑衍生物和/或1H-1,2,4-三唑-3-羧酰胺衍生物，如规范中所定义，或其前药、互变异构体或盐，用于制造治疗和/或预防CB1受体相关疾病的药物，适用于青少年患者，以及用于治疗和/或预防青少年和/或成年患者的药物诱导肥胖症。此外，本发明涉及将具有CB1受体活性的化合物与脂肪酶抑制剂结合使用。这些化合物与脂肪酶抑制剂结合使用特别适用于制造用于治疗和/或预防青少年或儿童患者的肥胖症的药物，以及用于治疗和/或预防青少年和/或成年患者的药物诱导肥胖症。优选的脂肪酶抑制剂是奥利司他、泛克立汀、ATL-962和/或脂肪酸盐酶抑制剂。
• 1H-1,2,4-triazole-3-carboxamide derivatives having cannabinoid-CB1 receptor agonistic, partial agonistic, inverse agonistic or antagonistic activity
  申请人：——

  公开号：US20040106614A1

  公开（公告）日：2004-06-03

  The present invention relates to a group of 1H-1,2,4-triazole-3-carboxamide derivatives, to methods for the preparation of these compounds, and to pharmaceutical compositions containing at least one of these compounds as an active ingredient. These 1H-1,2,4-triazole-3-carboxamide derivatives are potent cannabinoid-CB 1 receptor agonists, partial agonists, inverse agonists or antagonists, useful for the treatment of disorders involving cannabinoid neurotransmission. The compounds have the general formula (I) 1 wherein R and R 1 -R 3 have the meanings given in the specification.

  本发明涉及1H-1,2,4-三唑-3-羧酰胺衍生物的一组，涉及制备这些化合物的方法，以及含有至少一种这些化合物作为活性成分的制药组合物。这些1H-1,2,4-三唑-3-羧酰胺衍生物是有效的大麻素-CB1受体激动剂、部分激动剂、反向激动剂或拮抗剂，可用于治疗涉及大麻素神经递质的疾病。这些化合物具有通式（I）1，其中R和R1-R3的含义如说明书中所述。
• 1H-1,2,4-TRIAZOLE-3-CARBOXAMIDE DERIVATIVES AS CANNABINOID-CB sb 1 /sb RECEPTOR LIGANDS
  申请人：Solvay Pharmaceuticals B.V.

  公开号：EP1542678A1

  公开（公告）日：2005-06-22
• US7319110B2
  申请人：——

  公开号：US7319110B2

  公开（公告）日：2008-01-15