5-fluoro-2-[(4-(pyridin-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: 5-fluoro-2-[(4-(pyridin-2-yl)piperazin-1-yl)methyl]-1H-benzimidazole
• 英文别名: 6-Fluoro-2-(4-pyridin-2-yl-piperazin-1-ylmethyl)-1H-benzoimidazole；6-fluoro-2-[(4-pyridin-2-ylpiperazin-1-yl)methyl]-1H-benzimidazole
• 化学式: C₁₇H₁₈FN₅
• 分子量: 311.362
• InChiKey: ZSKFERSPBICNGI-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：

  4-氟-1,2-苯二胺 在 盐酸 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 5-fluoro-2-[(4-(pyridin-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：US20030008878A1

  公开（公告）日：2003-01-09

  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）的化合物的组合物用于治疗性功能障碍。
• 2-(4-aryl or heteroaryl-piperazin-1-ylmethyl)-1H-indole derivatives interacting with the dopamine D4 receptor
  申请人：Pfizer Inc.

  公开号：US20030100757A1

  公开（公告）日：2003-05-29

  A compound of the formula 1 wherein a, T, V, X, Y, Z, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are as defined above, their pharmaceutically acceptable salts and pharmaceutical compositions containing such compounds or their salts.

  该化合物的公式为1，其中a、T、V、X、Y、Z、R1、R2、R3、R4、R5、R6、R7、R8和R9如上所定义，其药学上可接受的盐和含有这种化合物或其盐的制药组合物。
• Dopamine D4 ligands for the treatment of novelty-seeking disorders
  申请人：——

  公开号：US20020049209A1

  公开（公告）日：2002-04-25

  The present invention provides a method of treating or preventing a novelty-seeking disorder such as pathological gambling, attention deficit disorder with hyperactivity disorder, substance addiction, drug addiction, alcohol addiction and sex addiction. using a compound which is a dopamine D4 receptor ligand, or a pharmaceutically acceptable salt thereof.

  本发明提供了一种治疗或预防新奇寻求障碍，如病理性赌博、注意力缺陷多动障碍、物质成瘾、药物成瘾、酒精成瘾和性成瘾的方法。所使用的化合物是多巴胺D4受体配体或其药学上可接受的盐。
• [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。