5-(4-Bromophenyl)-1-(2,4-dichlorophenyl)-4-ethylpyrazole-3-carboxylic Acid Chloride | 288104-80-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-Bromophenyl)-1-(2,4-dichlorophenyl)-4-ethylpyrazole-3-carboxylic Acid Chloride
• 英文别名: 5-(4-Bromophenyl)-1-(2,4-dichlorophenyl)-4-ethyl-1H-pyrazole-3-carbonyl chloride；5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethylpyrazole-3-carbonyl chloride
• CAS: 288104-80-3
• 化学式: C₁₈H₁₂BrCl₃N₂O
• 分子量: 458.569
• InChiKey: YLZWPTPVANYTAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(4-Bromophenyl)-1-(2,4-dichlorophenyl)-4-ethylpyrazole-3-carboxylic Acid Chloride 、 2-甲基-2-(甲氨基)丙酰胺 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 生成
  参考文献：
  名称：

  Discovery of 2-[5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-ethyl-1H-pyrazol-3-yl]-1,5,5-trimethyl-1,5-dihydro-imidazol-4-thione (BPR-890) via an Active Metabolite. A Novel, Potent and Selective Cannabinoid-1 Receptor Inverse Agonist with High Antiobesity Efficacy in DIO Mice

  摘要：

  By using the active metabolite 5 as an initial template, further structural modifications led to the identification of the titled compound 24 (BPR-890) as a highly potent CB I inverse agonist possessing an excellent CB2/1 selectivity and remarkable in vivo efficacy in diet-induced obese mice with a minimum effective dose as low as 0.03 mg/kg (po qd) at the end of the 30-day chronic study. Current SAR studies along with those of many existing rimonabant-mimicking molecules imply that around the pyrazole C3-position, a rigid and deep binding pocket should exist for CB1 receptor. In addition, relative to the conventional carboxamide carbonyl, serving as a key hydrogen-bond acceptor during ligand-CB1 receptor interaction, the corresponding polarizable thione carbonyl might play a more critical role in stabilizing the Asp366-Lys192 salt bridge in the proposed CB1-receptor homology model and inducing significant selectivity for CB1R over CB2R.

  DOI：

  10.1021/jm900471u
• 作为产物：
  描述：

  5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethyl-1H-pyrazole-3-carboxylic acid 以99的产率得到5-(4-Bromophenyl)-1-(2,4-dichlorophenyl)-4-ethylpyrazole-3-carboxylic Acid Chloride
  参考文献：
  名称：

  [EN] PYRAZOLECARBOXYLIC ACID DERIVATIVES, THEIR PREPARATION, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
  [FR] DERIVES D'ACIDE PYRAZOLECARBOXYLIQUE, LEUR PREPARATION, LES COMPOSITIONS PHARMACEUTIQUES EN CONTENANT

  摘要：

  Le N-pipéridino-5-(4-bromophényl)-1-(2,4-dichlorophényl)-4-éthylpyrazole-3-carboxamide, ainsi que ses sels et solvants, sont des antagonistes puissants des récepteurs cannabinoïdes CB1. Ils sont préparés en faisant réagir un dérivé fonctionnel de l'acide 5-(4-bromophényl)-1-(2,4-dichlorophényl)-4-éthylpyrazole-3-carboxylique avec de la 1-aminopipéridine, suivie éventuellement d'une salification.

  公开号：

  WO2000046209A1

文献信息

• Biphenyl-pyrazolecarboxamide compounds
  申请人：Tung Roger

  公开号：US20070066657A1

  公开（公告）日：2007-03-22

  The present invention relates to biphenyl-pyrazole compounds and in particular biphenyl-pyrazolecarboxamides. The invention further provides compositions comprising a compound of this invention and the use of such compositions in methods of treating diseases and conditions beneficially treated by antagonism or inverse agonism of the CB 1 receptor, such as obesity, smoking cessation, and normalization of blood lipid composition.

  本发明涉及联苯基吡唑化合物，特别是联苯基吡唑羧酰胺。该发明还提供了包含本发明化合物的组合物，以及利用这些组合物在治疗疾病和状况方面的方法，这些疾病和状况通过CB1受体的拮抗或逆作用有益治疗，如肥胖、戒烟和血脂组成的正常化。
• (1,5-DIPHENYL-1H-PYRAZOL-3-YL)OXADIAZOLE DERIVATIVES, PREPARATION METHOD THEREOF AND USE OF SAME IN THERAPEUTICS
  申请人：BARTH Francis

  公开号：US20080039510A1

  公开（公告）日：2008-02-14

  The invention relates to compounds having formula (I): Wherein R1, R2, R3 and R4 are as defined herein. The invention also relates to a method of preparing said compounds and to the application thereof in therapeutics.

  该发明涉及具有以下化学式（I）的化合物：其中R1、R2、R3和R4如本文所定义。该发明还涉及制备所述化合物的方法以及在治疗中的应用。
• Derivative of 5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethyl-N-(piperidine-1-yl)-1H-pyrazole-3-carboxamide, the preparation and therapeutic use thereof
  申请人：Miscoria Gilles

  公开号：US20060004055A1

  公开（公告）日：2006-01-05

  The invention relates to a derivative of 5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide of general formula (I): Preparation process and therapeutic use.

  本发明涉及通式(I)的5-(4-溴苯基)-1-(2,4-二氯苯基)-4-乙基-N-(哌啶-1-基)-1H-吡唑-3-羧酰胺的衍生物：制备方法和治疗用途。
• 吡唑甲酸类衍生物、其制备方法和含有它们的药物组合物
  申请人：赛诺菲-安万特

  公开号：CN1146544C

  公开（公告）日：2004-04-21

  本发明涉及是大麻素CB 1 受体强效拮抗剂的N-哌啶子基-5-(4-溴苯基)-1-(2，4-二氯苯基)-4-乙基吡唑-3-甲酰胺、其盐和溶剂化物。其制备方法包括令5-(4-溴苯基)-1-(2，4-二氯苯基)-4-乙基吡唑-3-甲酸的官能衍生物与1-氨基哌啶反应、随后选择性地成盐。
• Pyrazolecarboxylic acid derivatives, their preparation, pharmaceutical compositions containing them
  申请人：Sanofi-Synthelabo

  公开号：US06432984B1

  公开（公告）日：2002-08-13

  N-Piperidino-5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethylpyrazole-3-carboxamide and its salts and solvates are powerful antagonists of the CB1 cannabinoid receptors. They are prepared by reacting a functional derivative of 5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethylpyrazole-3-carboxylic acid with 1-aminopiperidine, optionally followed by salification.

  N-哌啶基-5-(4-溴苯基)-1-(2,4-二氯苯基)-4-乙基吡唑-3-羧酰胺及其盐和溶剂化合物是CB1大麻素受体的强效拮抗剂。它们是通过将5-(4-溴苯基)-1-(2,4-二氯苯基)-4-乙基吡唑-3-羧酸的官能衍生物与1-氨基哌啶反应制备的，可选择性地进行盐化反应。