N-(piperidin-1-yl)-4,5-di-(4-methylphenyl)-1-methylimidazole-2-carboxamide | 489446-84-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-(piperidin-1-yl)-4,5-di-(4-methylphenyl)-1-methylimidazole-2-carboxamide
• 英文别名: 1-methyl-N-(piperidin-1-yl)-4,5-dip-tolyl-1H-imidazole-2-carboxamide；1-methyl-4,5-bis(4-methylphenyl)-N-piperidin-1-ylimidazole-2-carboxamide
• CAS: 489446-84-6
• 化学式: C₂₄H₂₈N₄O
• 分子量: 388.513
• InChiKey: WOPRDVHBRJFDQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,5-di-(4-methylphenyl)-1-methylimidazole-2-carboxylic acid 、 N-(piperidin-1-yl)-4,5-di-(4-methylphenyl)-1-methylimidazole-2-carboxamide 在 甲胺 作用下， 以 四氢呋喃 为溶剂， 生成 N-methyl-4,5-di-(4-methylphenyl)-1-methylimidazole-2-carboxamide
  参考文献：
  名称：

  Substituted imidazoles as cannabinoid receptor modulators

  摘要：

  本发明涉及将这些新型化合物用于选择性拮抗Cannabinoid-1（CB1）受体。因此，本发明的化合物可用作治疗精神病、记忆障碍、认知障碍、偏头痛、神经病、神经炎症性疾病（包括多发性硬化症和吉兰-巴雷综合征）、病毒性脑炎、脑血管意外和头部创伤的炎症后遗症、焦虑症、压力、癫痫、帕金森病和精神分裂症的精神药物。这些化合物还可用于治疗物质滥用障碍，特别是阿片类药物、酒精和尼古丁。这些化合物还可用于治疗与过度食物摄入及相关并发症相关的肥胖或进食障碍。同时还声明了结构式（I）的新型化合物。

  公开号：

  US20030114495A1
• 作为产物：
  描述：

  2-Chloro-4,5-di-(4-methylphenyl)-1-methylimidazole 在 palladium on activated charcoal 正丁基锂 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， -70.0~20.0 ℃ 、344.74 kPa 条件下， 反应 1.5h， 生成 N-(piperidin-1-yl)-4,5-di-(4-methylphenyl)-1-methylimidazole-2-carboxamide
  参考文献：
  名称：

  Synthesis and activity of 4,5-diarylimidazoles as human CB1 receptor inverse agonists

  摘要：

  Structure-activity relationship studies directed toward the optimization of 4,5-diarylimidazole-2-carboxamide analogs as human CBI receptor inverse agonists resulted in the discovery of the two amide derivatives 24a and b (hCB1 IC50 = 6.1 and 4.0 nM) which also demonstrated efficacy in overnight feeding studies in the rat for reduction in both food intake and overall body weight. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.078

文献信息

• Diaryl Ether Derivatives and Uses Thereof
  申请人：Ruggeri B. Roger

  公开号：US20080070887A1

  公开（公告）日：2008-03-20

  Compounds of Formula (I) that act as antagonists at the mu, kappa and/or delta opioid receptors and therefore useful in the treatment of diseases, conditions and/or disorders that benefit from such antagonism in animals are described herein. where R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are described herein.

  本文描述了具有化学式（I）的化合物，这些化合物在mu、kappa和/或delta阿片受体上起拮抗作用，因此在动物治疗受益于这种拮抗作用的疾病、状况和/或障碍方面具有用处。其中R1、R2、R3、R4、R5和R6如下描述。
• [EN] METHOD OF TREATMENT OR PREVENTION OF OBESITY<br/>[FR] METHODE DE TRAITEMENT OU DE PREVENTION DE L'OBESITE
  申请人：MERCK & CO INC

  公开号：WO2003075660A1

  公开（公告）日：2003-09-18

  The present invention relates to a method of treating or preventing obesity (or suppressing the appetite) in a human patient by antagonizing CB1 receptors and inhibiting the enzyme 11β-HSD1 in an amount that is effective to treat or prevent obesity. Compounds useful in the present invention have an ion channel activity level greater than about 2 µM. Preferably the compound is a dual selective inhibitor, selectively antagonizing CB1 receptors and selectively inhibiting the enzyme 11β-HSD1.

  本发明涉及一种通过拮抗CB1受体并抑制11β-HSD1酶的方法来治疗或预防人类患者的肥胖症（或抑制食欲）。在治疗或预防肥胖症方面，本发明中有用的化合物具有大于约2µM的离子通道活性水平。最好的情况是，该化合物是一种双重选择性抑制剂，选择性地拮抗CB1受体并选择性地抑制11β-HSD1酶。
• Method of treatment or prevention of obesity
  申请人：Fong M Tung

  公开号：US20050171161A1

  公开（公告）日：2005-08-04

  The present invention relates to a method of treating or preventing obesity (or suppressing the appetite) in a human patient by antagonizing CB1 receptors and inhibiting the enzyme 11β-HSD1 in an amount that is effective to treat or prevent obesity. Compounds useful in the present invention have an ion channel activity level greater than about 2 μM. Preferably the compound is a dual selective inhibitor, selectively antagonizing CB1 receptors and selectively inhibiting the enzyme 11β-HSD1

  本发明涉及一种通过拮抗CB1受体和抑制11β-HSD1酶以有效治疗或预防肥胖（或抑制食欲）的方法。本发明中有用的化合物具有大于约2μM的离子通道活性水平。最好的化合物是双重选择性抑制剂，可以选择性地拮抗CB1受体和选择性地抑制酶11β-HSD1。
• Diaryl, Dipyridinyl and Aryl-Pyridinyl Derivatives and Uses Thereof
  申请人：Ruggeri Roger B.

  公开号：US20080167371A1

  公开（公告）日：2008-07-10

  Compounds of Formula (I) that act as antagonists at the mu, kappa and/or delta opioid receptors and therefore useful in the treatment of diseases, conditions and/or disorders that benefit from such antagonism in animals are described herein. where R, R 1 , R 2a , R 2b , R 3 , R 4 , V, R 6 , R 7 , R 8 , R 9 , W and X are described herein.

  本文描述了化学式（I）的化合物，它们作为mu、kappa和/或delta阿片受体拮抗剂，因此对于需要这种拮抗作用的动物的疾病、状况和/或障碍的治疗是有用的。其中R、R1、R2a、R2b、R3、R4、V、R6、R7、R8、R9、W和X的描述在此处给出。
• Pyrimido [4,5-D] Azepine Derivatives As 5-HT2C Agonists
  申请人：Andrews Mark

  公开号：US20100113422A1

  公开（公告）日：2010-05-06

  The present invention provides a compound of formula (I): or a pharmaceutically acceptable salt thereof wherein the variables R 1 , R 2 , R 3a , R 3b , R 3b , R 3d , and R 100 are as defined herein. The invention is also directed to pharmaceutical compositions comprising the compounds of formula (I) and methods of treating a 5-HT 2c receptor-mediated disorders with a compound of formula (I) or a pharmaceutical composition comprising a compound of formula (I).

  本发明提供了式（I）的化合物：或其药学上可接受的盐，其中变量R1、R2、R3a、R3b、R3b、R3d和R100如本文所定义。本发明还涉及包括式（I）化合物的制药组合物，以及使用式（I）的化合物或包括式（I）的制药组合物治疗5-HT2c受体介导的疾病的方法。