2-{[4-(3-fluoropyridin-2-yl)piperazin-1-yl]methyl}-1H-benzimidazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 2-{[4-(3-fluoropyridin-2-yl)piperazin-1-yl]methyl}-1H-benzimidazole
• 英文别名: 2-{[4-(3-fluoropyridin-2-yl)piperazin-1-yl]methyl}-H1-benzimidazole；2-[[4-(3-fluoropyridin-2-yl)piperazin-1-yl]methyl]-1H-benzimidazole
• 化学式: C₁₇H₁₈FN₅
• 分子量: 311.362
• InChiKey: DIIMPNOBUZSQDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  48
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-氟吡啶 在 三乙烯二胺 、 正丁基锂 、 caesium carbonate 作用下， 以 乙醚 、 正己烷 、 N,N-二甲基甲酰胺 、 正丁醇 为溶剂， 反应 76.25h， 生成 2-{[4-(3-fluoropyridin-2-yl)piperazin-1-yl]methyl}-1H-benzimidazole
  参考文献：
  名称：

  Discovery of 2-(4-Pyridin-2-ylpiperazin-1-ylmethyl)-1H-benzimidazole (ABT-724), a Dopaminergic Agent with a Novel Mode of Action for the Potential Treatment of Erectile Dysfunction

  摘要：

  A new class of agents with potential utility for the treatment of erectile dysfunction has been discovered, guided by the hypothesis that selective D-4 agonists are erectogenic but devoid of the side effects typically associated with dopaminergic agents. The lead agent 2-(4-pyridin-2-ylpiperazin-1-ylmethyl)-1H-benzimidazole (1, ABT-724) was discovered by optimization of a series of benzimidazole arylpiperazines. This highly selective D-4 agonist was found to be very potent and efficacious in vivo, eliciting penile erections in rats at a dose of 0.03 mumol/kg, with a positive response rate of 77% erectile incidence. Even at high doses, it was devoid of side effects in animal models of central nervous system behaviors, emesis, or nausea. The structure-activity relationship of the parent benzimidazole series leading to 1 is described, with the detailed in vitro and in vivo profiles described. Distinctive structural features were discovered that are associated with D-4 selective agonism in this series of analogues.

  DOI：

  10.1021/jm030505a

文献信息

• Benzimidazoles that are useful in treating sexual dysfunction
  申请人：——

  公开号：US20020169166A1

  公开（公告）日：2002-11-14

  The present invention relates to the use of compounds of formula (I) 1 for the treatment of sexual dysfunction and to compositions containing compounds of formula (I) for the treatment of sexual dysfunction.

  本发明涉及使用式(I)的化合物治疗性功能障碍，以及含有式(I)化合物的组合物用于治疗性功能障碍。
• [EN] BENZIMIDAZOLES THAT ARE USEFUL IN TREATING SEXUAL DYSFUNCTION<br/>[FR] BENZIMIDAZOLES UTILES DANS LE TRAITEMENT DE TROUBLES SEXUELS
  申请人：ABBOTT LAB

  公开号：WO2002088093A1

  公开（公告）日：2002-11-07

  The present invention relates to the use of compounds of formula (I) for the treatment of sexual dysfunction and to compositions containing compounds of formula (I) for the treatment of sexual dysfunction.

  本发明涉及使用式(I)化合物治疗性功能障碍，以及含有式(I)化合物的组合物治疗性功能障碍。
• [EN] BENZIMIDAZOLE-DERIVATIVES FOR THE TREATMENT OF SEXUAL DYSFUNCTION<br/>[FR] DERIVES DE BENZIMIDAZOLE UTILISES POUR TRAITER UN DYSFONCTIONNEMENT SEXUEL
  申请人：ABBOTT LAB

  公开号：WO2003076431A1

  公开（公告）日：2003-09-18

  The present invention relates to the use of compounds of formula (I) for the treatment of sexual dysfunction and to compositions containing compounds of formula (I) for the treatment of sexual dysfunction.

  本发明涉及使用式(I)的化合物治疗性功能障碍，以及含有式(I)的化合物的组合物治疗性功能障碍。
• Benzimidazoles that are useful in treating male sexual dysfunction
  申请人：Abbott Laboratories

  公开号：US07022728B2

  公开（公告）日：2006-04-04

  The present invention relates to the use of compounds of formula (I) for the treatment of sexual dysfunction and to compositions containing compounds of formula (I) for the treatment of sexual dysfunction.

  本发明涉及使用式(I)化合物治疗性功能障碍以及含有式(I)化合物的组合物治疗性功能障碍。
• BENZIMIDAZOLES THAT ARE USEFUL IN TREATING SEXUAL DYSFUNCTION
  申请人：ABBOTT LABORATORIES

  公开号：EP1373220A1

  公开（公告）日：2004-01-02