2-(4-((1H-1,2,4-triazol-1-yl)methyl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl)-5-tert-butyl-1,3,4-thiadiazole | 1016555-30-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-((1H-1,2,4-triazol-1-yl)methyl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl)-5-tert-butyl-1,3,4-thiadiazole
• 英文别名: 2-tert-butyl-5-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-(1,2,4-triazol-1-ylmethyl)pyrazol-3-yl]-1,3,4-thiadiazole
• CAS: 1016555-30-8
• 化学式: C₂₄H₂₀Cl₃N₇S
• 分子量: 544.895
• InChiKey: LHMAHIKDKLBEPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-((1H-1,2,4-triazol-1-yl)methyl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N'-pivaloyl-1H-pyrazole-3-carbohydrazide 在 劳森试剂 作用下， 以 四氢呋喃 为溶剂， 反应 0.83h， 以68.8%的产率得到2-(4-((1H-1,2,4-triazol-1-yl)methyl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl)-5-tert-butyl-1,3,4-thiadiazole
  参考文献：
  名称：

  Discovery of 2-(4-((1H-1,2,4-triazol-1-yl)methyl)-5-(4-bromophenyl)-1-(2-chlorophenyl)-1H-pyrazol-3-yl)-5-tert-butyl-1,3,4-thiadiazole (GCC2680) as a potent, selective and orally efficacious cannabinoid-1 receptor antagonist

  摘要：

  Structure-activity relationship studies in a series of diarylpyrazolyl thiadiazoles identified cannabinoid-1 receptor antagonists with excellent potency and selectivity. Based on its exceptional in vivo efficacy in animal models and its favorable pharmacokinetic and toxicological profiles, 2-(4-((1H-1,2,4-triazol-1yl) methyl)-5-(4-bromophenyl)-1-(2-chlorophenyl)-1H-pyrazol-3-yl)-5-tert-butyl-1,3,4-thiadiazole (GCC2680) was selected as a preclinical candidate for the treatment of obesity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.07.013

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：Green Cross Corporation

  公开号：EP2097410A1

  公开（公告）日：2009-09-09
• US7875647B2
  申请人：——

  公开号：US7875647B2

  公开（公告）日：2011-01-25
• [EN] HETEROARYL-PYRAZOLE DERIVATIVES AS CANNABINOID CB1 RECEPTOR ANTAGONISTS<br/>[FR] DÉRIVÉS D'HÉTÉROARYL-PYRAZOLE UTILISÉS EN TANT QU'ANTAGONISTES DU RÉCEPTEUR CB1 DES CANNABINOÏDES
  申请人：GREEN CROSS CORP

  公开号：WO2008039023A1

  公开（公告）日：2008-04-03

  [EN] A heteroaryl-pyrazole compound of formula (I) or a pharmaceutically acceptable salt thereof is effective as a cannabinoid CB1 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.
  [FR] L'invention concerne un composé d'hétéroaryl-pyrazole représenté par la formule (I) ou un sel pharmaceutiquement acceptable de ce dernier efficace en tant qu'agoniste inverse ou antagoniste du récepteur CB1 des cannabinoïdes, qui est utile pour prévenir ou traiter l'obésité et les troubles métaboliques liés à l'obésité. La présente invention concerne également une méthode de préparation des composés d'hétéroaryl-pyrazole selon l'invention ou d'un sel pharmaceutiquement acceptable de ces derniers, une composition pharmaceutique les contenant, ainsi qu'une méthode de prévention ou de traitement de l'obésité et de troubles métaboliques liés à l'obésité.
• Discovery of 2-(4-((1H-1,2,4-triazol-1-yl)methyl)-5-(4-bromophenyl)-1-(2-chlorophenyl)-1H-pyrazol-3-yl)-5-tert-butyl-1,3,4-thiadiazole (GCC2680) as a potent, selective and orally efficacious cannabinoid-1 receptor antagonist
  作者：Jinhwa Lee、Hee Jeong Seo、Suk Ho Lee、Jeongmin Kim、Myung Eun Jung、Sung-Han Lee、Kwang-Seop Song、Junwon Lee、Suk Youn Kang、Min Ju Kim、Mi-Soon Kim、Eun-Jung Son、MinWoo Lee、Ho-Kyun Han

  DOI：10.1016/j.bmc.2010.07.013

  日期：2010.9

  Structure-activity relationship studies in a series of diarylpyrazolyl thiadiazoles identified cannabinoid-1 receptor antagonists with excellent potency and selectivity. Based on its exceptional in vivo efficacy in animal models and its favorable pharmacokinetic and toxicological profiles, 2-(4-((1H-1,2,4-triazol-1yl) methyl)-5-(4-bromophenyl)-1-(2-chlorophenyl)-1H-pyrazol-3-yl)-5-tert-butyl-1,3,4-thiadiazole (GCC2680) was selected as a preclinical candidate for the treatment of obesity. (C) 2010 Elsevier Ltd. All rights reserved.