5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carbohydrazide | 443141-90-0

• 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)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carbohydrazide
• 英文别名: 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1 H-pyrazole-3-carboxylic acid hydrazide；5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-pyrazole-3-carbohydrazide；5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carbohydrazide
• CAS: 443141-90-0
• 化学式: C₁₇H₁₃Cl₃N₄O
• 分子量: 395.675
• InChiKey: JTJORYHEPQPVJK-UHFFFAOYSA-N

物化性质

• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  72.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carbohydrazide 、 三甲基乙酸 在 N-甲基吗啉 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以87%的产率得到5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-N'-(2,2-dimethylpropanoyl)-4-methyl-1H-pyrazole-3-carbohydrazide
  参考文献：
  名称：

  Pentacycle derivatives as cannabinoid CB1 receptor ligands

  摘要：

  Cannabinoid CB-1 receptors have been the focus of extensive studies since the first clinical results of rimonabant (SR141716) for the treatment of obesity and obesity-related metabolic disorders were reported in 2001. To further evaluate the properties of CB receptors, we have designed and efficiently prepared a series of pentacycle derivatives. Five of the new compounds which displayed high in vitro rCB1 binding affinities were assayed for binding to hCB2 receptor. Noticeably, 2-(5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-(5-methyl- 1,3,4-thiadiazol-2-yl)-1H-pyrazol-3-yl)-5-(1-(trifluoromethyl) cyclopropyl)-1,3,4-oxadiazole (16l) demonstrated good binding affinity and decent selectivity for rCB1 receptor (IC50 = 1.72 nM, hCB2/rCB1 = 142). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.015
• 作为产物：
  描述：

  5-(4-氯苯基)-1-(2,4-二氯苯基)-4-甲基-1H-吡唑-3-羧酸乙酯 以97的产率得到5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carbohydrazide
  参考文献：
  名称：

  Method for preparing N-piperidino-1,5-diphenylpyrazole-3-carboxamide and derivatives

  摘要：

  本发明涉及一种制备N-哌啶基-1,5-二苯基吡唑-3-羧酰胺及其衍生物的方法。

  公开号：

  EP1947090A1

文献信息

• Synthesis and Structure−Activity Relationships of Amide and Hydrazide Analogues of the Cannabinoid CB₁ Receptor Antagonist <i>N</i>-(Piperidinyl)- 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1<i>H</i>-pyrazole-3-carboxamide (SR141716)
  作者：Ma. Elena Y. Francisco、Herbert H. Seltzman、Anne F. Gilliam、René A. Mitchell、Sharyl L. Rider、Roger G. Pertwee、Lesley A. Stevenson、Brian F. Thomas

  DOI：10.1021/jm010498v

  日期：2002.6.1

  (SAR) of the aminopiperidine region. The structural modifications include the substitution of alkyl hydrazines, amines, and hydroxyalkylamines of varying lengths for the aminopiperidinyl moiety. Proximity and steric requirements at the aminopiperidine region were probed by the synthesis of analogues that substitute alkyl hydrazines of increasing chain length and branching. The corresponding amide analogues

  合成了联芳基吡唑N-（哌啶基）-5-（4-氯苯基）-1-（2,4-二氯苯基）-4-甲基-1H-吡唑-3-甲酰胺（SR141716; 5）的类似物以研究氨基哌啶区的构效关系（SAR）。结构修饰包括用不同长度的烷基肼，胺和羟烷基胺取代氨基哌啶基部分。通过取代链长和支链增加的烷基肼的类似物的合成，探讨了氨基哌啶区域的邻近性和空间要求。将相应的酰胺类似物与酰肼进行比较，以确定第二种氮对受体结合亲和力的影响。N-环己基酰胺14代表直接亚甲基，用于氮取代5，降低了杂原子相互作用的可能性，而吗啉代类似物15增加了额外杂原子相互作用的可能性。合成了一系列链长增加的羟烷基酰胺，以研究其他受体氢结合位点的存在。在使用大麻素激动剂[（3）H]（1R，3R，4R）-3- [2-羟基-4-（1,1-二甲基庚基）苯基] -4-（3-羟丙基）环己-1的置换分析中-ol（CP 55 940; 2）或拮抗剂[（3）H] 5
• (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。
• [EN] PROCESS FOR THE PREPARATION OF RIMONABANT<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION DE RIMONABANT
  申请人：MAPRIMED S A

  公开号：WO2009109222A1

  公开（公告）日：2009-09-11

  The present invention relates to a new process for the preparation of Rimonabant through the formation of an intermediate compound of formula (VII). The invention further relates to a process for the preparation of the compound of formula (VII).

  本发明涉及一种通过形成公式（VII）的中间化合物制备Rimonabant的新工艺。本发明还涉及一种制备公式（VII）化合物的工艺。
• METHOD FOR THE PREPARATION OF N-PIPERIDINO-1, 5-DIPHENYLPYRAZOLE-3-CARBOXAMIDE DERIVATIVES
  申请人：VAYRON Philippe

  公开号：US20080119653A1

  公开（公告）日：2008-05-22

  A process for the preparation of for the preparation of N-piperidino-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxamide and of its salts, wherein 1,5-dibromopentane is reacted with a compound of formula (IIIa) in the presence of Na 2 CO 3 in acetonitrile heated at reflux.

  一种制备N-哌啶基-5-(4-氯苯基)-1-(2,4-二氯苯基)-4-甲基吡唑-3-羧酰胺及其盐的方法，其中1,5-二溴戊烷在乙腈中与式（IIIa）的化合物在Na2CO3存在下加热回流反应。
• Method for the preparation of N-piperidino-1, 5-diphenylpyrazole-3-carboxamide derivatives
  申请人：Sanofi-Aventis

  公开号：US07462632B2

  公开（公告）日：2008-12-09

  A process for the preparation of for the preparation of N-piperidino-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxamide and of its salts, wherein 1,5-dibromopentane is reacted with a compound of formula (IIIa) in the presence of Na2CO3 in acetonitrile heated at reflux.

  一种制备N-哌啶基-5-(4-氯苯基)-1-(2,4-二氯苯基)-4-甲基吡唑-3-羧酰胺及其盐的方法，其中在乙腈中以回流加热的条件下，将1,5-二溴戊烷与式（IIIa）的化合物在Na2CO3的存在下反应。