3-butyl-1-{1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]piperidin-4-yl}urea | 1408075-47-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-butyl-1-{1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]piperidin-4-yl}urea
• 英文别名: N-Butyl-Na(2)-[1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]-4-piperidinyl]urea；1-butyl-3-[1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)purin-6-yl]piperidin-4-yl]urea
• CAS: 1408075-47-7
• 化学式: C₂₇H₂₉Cl₂N₇O
• 分子量: 538.48
• InChiKey: FZKJYQKVIPMHPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  88
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  6-chloro-8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purine 在 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 3-butyl-1-{1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]piperidin-4-yl}urea
  参考文献：
  名称：

  Diphenyl Purine Derivatives as Peripherally Selective Cannabinoid Receptor 1 Antagonists

  摘要：

  Cannabinoid receptor 1 (CB1) antagonists are potentially useful for the treatment of several diseases. However, clinical development of several CB1 antagonists was halted due to central nervous system (CNS)-related side effects including depression and suicidal ideation in some users. Recently, studies have indicated that selective regulation of CB1 receptors in the periphery is a viable strategy for treating several important disorder. Past efforts to develop peripherally selective antagonists of CB1 have largely targeted rimonabant, an inverse agonist of CB1. Reported here are out efforts toward developing a peripherally selective CB1 antagonist based on the otenabant scaffold. Even though otenabant penetrates the CNS, it is unique among CB1 antagonists that have been clinically tested because it has properties that are normally associated with peripherally selective compounds. Our efforts have resulted in an orally absorbed compound that is a potent and selective CB1 antagonist with limited penetration into the CNS.

  DOI：

  10.1021/jm301181r

文献信息

• [EN] PERIPHERALLY RESTRICTED DIPHENYL PURINE DERIVATIVES<br/>[FR] DÉRIVÉS DE DIPHÉNYLE PURINE RESTREINTS DE MANIÈRE PÉRIPHÉRIQUE
  申请人：RES TRIANGLE INST

  公开号：WO2013123335A1

  公开（公告）日：2013-08-22

  The invention provides compounds capable of acting as antagonists at cannabanoid receptors according to the following formula: Such compounds may be used to treat conditions for which the cannabinoid receptor system has been implicated, such as obesity, liver disease, diabetes, pain, and inflammation.

  该发明提供了能够作为大麻素受体拮抗剂的化合物，其化学式如下：这些化合物可用于治疗与大麻素受体系统有关的疾病，如肥胖、肝病、糖尿病、疼痛和炎症。
• PERIPHERALLY RESTRICTED DIPHENYL PURINE DERIVATIVES
  申请人：RESEARCH TRIANGLE INSTITUTE

  公开号：US20150031689A1

  公开（公告）日：2015-01-29

  The invention provides compounds capable of acting as antagonists at cannabanoid receptors according to the following formula: Such compounds may be used to treat conditions for which the cannabinoid receptor system has been implicated, such as obesity, liver disease, diabetes, pain, and inflammation.

  该发明提供了能够作为大麻素受体拮抗剂的化合物，其化学式如下：这些化合物可用于治疗大麻素受体系统被涉及的疾病，如肥胖症、肝病、糖尿病、疼痛和炎症等。
• US9187480B2
  申请人：——

  公开号：US9187480B2

  公开（公告）日：2015-11-17
• US9458160B2
  申请人：——

  公开号：US9458160B2

  公开（公告）日：2016-10-04
• Diphenyl Purine Derivatives as Peripherally Selective Cannabinoid Receptor 1 Antagonists
  作者：Alan Fulp、Katherine Bortoff、Yanan Zhang、Herbert Seltzman、James Mathews、Rodney Snyder、Tim Fennell、Rangan Maitra

  DOI：10.1021/jm301181r

  日期：2012.11.26

  Cannabinoid receptor 1 (CB1) antagonists are potentially useful for the treatment of several diseases. However, clinical development of several CB1 antagonists was halted due to central nervous system (CNS)-related side effects including depression and suicidal ideation in some users. Recently, studies have indicated that selective regulation of CB1 receptors in the periphery is a viable strategy for treating several important disorder. Past efforts to develop peripherally selective antagonists of CB1 have largely targeted rimonabant, an inverse agonist of CB1. Reported here are out efforts toward developing a peripherally selective CB1 antagonist based on the otenabant scaffold. Even though otenabant penetrates the CNS, it is unique among CB1 antagonists that have been clinically tested because it has properties that are normally associated with peripherally selective compounds. Our efforts have resulted in an orally absorbed compound that is a potent and selective CB1 antagonist with limited penetration into the CNS.