5-(4-chlorophenyl)-N-cyclopropyl-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide | 1020810-09-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-chlorophenyl)-N-cyclopropyl-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide
• 英文别名: 5-(4-chlorophenyl)-N-cyclopropyl-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxamide
• CAS: 1020810-09-6
• 化学式: C₂₀H₁₆Cl₃N₃O
• 分子量: 420.726
• InChiKey: BBPROFMXODYTFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(4-chlorophenyl)-N-cyclopropyl-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide 在 五氯化磷 、 迭氮酸 作用下， 以 甲苯 为溶剂， 反应 0.17h， 生成 5-[5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazol-3-yl]-1-cyclopropyltetrazole
  参考文献：
  名称：

  Tetrazole-biarylpyrazole derivatives as cannabinoid CB1 receptor antagonists

  摘要：

  Cannabinoid CB1 receptors have been the focus of extensive studies since the first clinical results of rimonabant (SR141716) for the treatment of obesity and related metabolic disorders were reported in 2001. To further evaluate the properties of CB receptors, we have designed a new series of tetrazole-biarylpyrazoles. The various analogues were efficiently prepared and bioassayed for binding to cannabinoid CB1 receptor. Six of the new compounds which displayed high in vitro CB1 binding affinities were assayed for binding to CB2 receptor. Noticeably, cyclopentyl-tetrazole (9a) demonstrated good binding affinity and selectivity for CB1 receptor (IC50 = 11.6 nM and CB2/CB1 = 366). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.02.061
• 作为产物：
  描述：

  4-(4-氯苯基)-3-甲基-2,4-二氧代丁酸乙酯 在 diisopropylethylamine 、 水 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 24.0h， 生成 5-(4-chlorophenyl)-N-cyclopropyl-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide
  参考文献：
  名称：

  [EN] SUBSTITUTED PYRAZOLE COMPOUNDS AS CB1 RECEPTOR ANTAGONISTS AND USES THEREOF
  [FR] COMPOSÉS PYRAZOLE SUBSTITUÉS COMME ANTAGONISTES DU RÉCEPTEUR CB1 ET LEURS UTILISATIONS

  摘要：

  本发明涉及公式1的化合物，或其同位素形式、立体异构体、互变异构体、药学上可接受的盐、溶剂合物、多型体、前药、S-氧化物或N-氧化物，以及它们的制备方法。该发明还涉及含有这些化合物的药物组合物；以及公式1的化合物和含有这些化合物的药物组合物在治疗由大麻素1（CB1）受体介导的疾病或障碍中的用途。

  公开号：

  WO2015162452A1

文献信息

• Heteroaryl-Pyrazole Derivatives as Cannabinoid CB1 Receptor Antagonists
  申请人：LEE Jinhwa

  公开号：US20080081812A1

  公开（公告）日：2008-04-03

  A heteroaryl-pyrazole compound of formula (I) or a pharmaceutically acceptable salt thereof is effective as a cannabinoid CB 1 receptor inverse agonist or antagonist, which is useful for preventing or treating obesity and obesity-related metabolic disorders. The present invention also provides a method for preparing the inventive heteroaryl-pyrasole compounds or a pharmaceutically acceptable salt thereof, a pharmaceutical composition containing same, and a method for preventing or treating obesity and obesity-related metabolic disorders.

  一种异芳基-吡唑化合物，其公式为(I)或其药用可接受盐，可作为大麻素CB1受体的反向激动剂或拮抗剂，用于预防或治疗肥胖及其相关代谢紊乱。本发明还提供了制备本发明的异芳基-吡唑化合物或其药用可接受盐的方法，包含该化合物的药物组合物，以及用于预防或治疗肥胖及其相关代谢紊乱的方法。
• Heteroaryl-pyrazole derivatives as cannabinoid CB1 receptor antagonists
  申请人：Lee Jinhwa

  公开号：US20080081815A1

  公开（公告）日：2008-04-03

  A novel heteroaryl-pyrazole compound of formula (I) or a pharmaceutically acceptable salt thereof is effective as a cannabinoid CB 1 receptor inverse agonist or antagonist, which is useful for preventing or treating obesity and obesity-related metabolic disorders. The prevention also provide a method for preparing same, a pharmaceutical composition containing same, and a method for preventing or treating obesity and obesity-related metabolic disorders.

  化合物I式的新型杂环基吡唑化合物或其药学上可接受的盐，作为大麻素CB1受体的反向激动剂或拮抗剂，对于预防或治疗肥胖症和肥胖相关代谢紊乱是有效的。该预防还提供了一种制备方法、包含该化合物的制药组合物以及预防或治疗肥胖症和肥胖相关代谢紊乱的方法。
• US7875647B2
  申请人：——

  公开号：US7875647B2

  公开（公告）日：2011-01-25
• [EN] SUBSTITUTED PYRAZOLE COMPOUNDS AS CB1 RECEPTOR ANTAGONISTS AND USES THEREOF<br/>[FR] COMPOSÉS PYRAZOLE SUBSTITUÉS COMME ANTAGONISTES DU RÉCEPTEUR CB1 ET LEURS UTILISATIONS
  申请人：PIRAMAL ENTPR LTD

  公开号：WO2015162452A1

  公开（公告）日：2015-10-29

  The present invention relates to compounds of formula 1, or isotopic forms, stereoisomers, tautomers, pharmaceutically acceptable salts, solvates, polymorphs, prodrugs, S-oxides or N-oxides thereof, and processes for their preparation. The invention further relates to pharmaceutical compositions containing the compounds; and use of the compounds of formula 1 and the pharmaceutical compositions comprising the compounds in the treatment of diseases or disorders mediated by cannabinoid 1 (CB1) receptors.

  本发明涉及公式1的化合物，或其同位素形式、立体异构体、互变异构体、药学上可接受的盐、溶剂合物、多型体、前药、S-氧化物或N-氧化物，以及它们的制备方法。该发明还涉及含有这些化合物的药物组合物；以及公式1的化合物和含有这些化合物的药物组合物在治疗由大麻素1（CB1）受体介导的疾病或障碍中的用途。
• Tetrazole-biarylpyrazole derivatives as cannabinoid CB1 receptor antagonists
  作者：Suk Youn Kang、Sung-Han Lee、Hee Jeong Seo、Myung Eun Jung、Kwangwoo Ahn、Jeongmin Kim、Jinhwa Lee

  DOI：10.1016/j.bmcl.2008.02.061

  日期：2008.4

  Cannabinoid CB1 receptors have been the focus of extensive studies since the first clinical results of rimonabant (SR141716) for the treatment of obesity and related metabolic disorders were reported in 2001. To further evaluate the properties of CB receptors, we have designed a new series of tetrazole-biarylpyrazoles. The various analogues were efficiently prepared and bioassayed for binding to cannabinoid CB1 receptor. Six of the new compounds which displayed high in vitro CB1 binding affinities were assayed for binding to CB2 receptor. Noticeably, cyclopentyl-tetrazole (9a) demonstrated good binding affinity and selectivity for CB1 receptor (IC50 = 11.6 nM and CB2/CB1 = 366). (C) 2008 Elsevier Ltd. All rights reserved.