(7S)-7-[(5-fluoro-2-methyl-benzyl)oxy]-2-[(2R)-2-methylpiperazin-1-yl]-6,7-dihydro-5H-cyclopenta[b]pyridine

• 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: (7S)-7-[(5-fluoro-2-methyl-benzyl)oxy]-2-[(2R)-2-methylpiperazin-1-yl]-6,7-dihydro-5H-cyclopenta[b]pyridine
• 英文别名: (S)-7-(5-fluoro-2-methylbenzyloxy)-2-((R)-2-methylpiperazin-1-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine；(7S)-7-[(5-fluoro-2-methylphenyl)methoxy]-2-[(2R)-2-methylpiperazin-1-yl]-6,7-dihydro-5H-cyclopenta[b]pyridine
• 化学式: C₂₁H₂₆FN₃O
• 分子量: 355.455
• InChiKey: ZAZVLBZIEZHJFV-BEFAXECRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  37.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (7S)-7-[(5-fluoro-2-methyl-benzyl)oxy]-2-[(2R)-2-methylpiperazin-1-yl]-6,7-dihydro-5H-cyclopenta[b]pyridine 、 L-酒石酸 在 L-酒石酸 、 ice 、 乙醇 作用下， 以 异丙醇 为溶剂， 反应 74.0h， 以to give 90 mg of title compound as white crystals的产率得到(7S)-7-[(5-fluoro-2-methyl-benzyl)oxy]-2-[(2R)-2-methylpiperazin-1-yl]-6,7-dihydro-5H-cyclopenta[b]pyridine L-(+)-tartrate
  参考文献：
  名称：

  Tartrate Salt of (7S)-7-[(5-Fluoro-2-Methyl-Benzyl)oxy]-2-[(2R)-2-Methylpiperazin-1-YL]-6,7-Dihydro-5H-Cyclopenta[B]Pyridine

  摘要：

  本发明提供了公式（I）的酒石酸盐，公式I也被称为（7S）-7-[(5-氟-2-甲基苯基)氧基]-2-[(2R)-2-甲基哌嗪-1-基]-6,7-二氢-5H-环戊[b]吡啶。该酒石酸盐最好是结晶性的。本发明的公式I的酒石酸盐对于治疗与动物包括人类的5HT2c受体激活有关的疾病非常有用，例如治疗精神分裂症、认知缺陷包括与精神分裂症有关的认知缺陷、焦虑症、抑郁症、强迫症、癫痫、肥胖症、性功能障碍和尿失禁等。

  公开号：

  US20100004259A1
• 作为产物：
  描述：

  tert-butyl (R)-4-((S)-7-((5-fluoro-2-methylbenzyl)oxy)-6,7-dihydro-5H-cyclopenta[b]pyridin-2-yl)-3-methylpiperazine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (7S)-7-[(5-fluoro-2-methyl-benzyl)oxy]-2-[(2R)-2-methylpiperazin-1-yl]-6,7-dihydro-5H-cyclopenta[b]pyridine
  参考文献：
  名称：

  Design and synthesis of orally-active and selective azaindane 5HT2c agonist for the treatment of obesity

  摘要：

  Based on our original pyrazine hit, CP-0809101, novel conformationally-restricted 5HT2c receptor agonists with 2-piperazin-azaindane scaffold were designed. Synthesis and structure-activity relationship (SAR) studies are described with emphasis on optimization of the selectivity against 5HT2a and 5HT2b receptors with excellent 2c potency. Orally-active and selective compounds were identified with dose responsive in vivo efficacy in our pre-clinical food intake model. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.112

文献信息

• Cyclopentapyridine and tetrahydroquinoline derivatives
  申请人：Lefker A. Bruce

  公开号：US20060247254A1

  公开（公告）日：2006-11-02

  6,7-Dihydro-5H-cyclopenta[b]pyridine and 5,6,7,8-tetrahydroquinoline compounds of Formula (I), including salts, hydrates and solvates thereof, that act as 5-HT 2 receptor ligands and their uses in the treatment of diseases linked to the activation of 5-HT 2c receptors are described herein.

  本文介绍了公式(I)中的6,7-二氢-5H-环戊[b]吡啶和5,6,7,8-四氢喹啉化合物，包括其盐、水合物和溶剂化物，它们作为5-HT2受体配体，并且它们在治疗与5-HT2受体激活有关的疾病方面的用途。
• CONDENSED PYRIDINE DERIVATIVE AND USE THEREOF
  申请人：Matsumoto Takahiro

  公开号：US20100266504A1

  公开（公告）日：2010-10-21

  Provided are a condensed pyridine derivative having a serotonin 5-HT 2C receptor activation action, a prophylactic or therapeutic agent for a lower urinary tract symptom, obesity and/or organ prolapse and the like containing the condensed pyridine derivative, a screening method for a substance that increases leak point pressure upon a rise in the intravesical pressure or a prophylactic or therapeutic drug for stress urinary incontinence, a prophylactic or therapeutic drug for cystoceles or enteroceles, containing a substance that activates serotonin 5-HT 2C receptor, and a method of screening for a therapeutic drug for cystoceles or enteroceles, including increasing an intravesical pressure after bilateral transection of the hypogastric nerve and pudendal nerve of an animal, and measuring a closure response in the urethra, the rectum or the vagina observed at that time. A serotonin 5-HT 2c receptor activator containing a compound represented by the formula: wherein each symbol is as defined in the specification, or a salt thereof.

  提供了一种具有血清素5-HT2C受体激活作用的缩合吡啶衍生物，以及包含该缩合吡啶衍生物的预防或治疗下尿路症状、肥胖和/或器官脱垂等药物，以及增加膀胱内压力时增加泄漏点压力或预防或治疗压力性尿失禁的药物筛选方法，包含激活血清素5-HT2C受体的物质的预防或治疗膀胱脱垂或肠脱垂的药物，以及通过双侧切断动物的会阴神经和耻骨神经后增加膀胱内压力并测量尿道、直肠或阴道在此时观察到的闭合反应的膀胱脱垂或肠脱垂的治疗药物筛选方法。其中包含式的化合物的血清素5-HT2C受体激活剂：式中每个符号如规范中定义的那样，或其盐。
• WO2008/10073
  申请人：——

  公开号：——

  公开（公告）日：——
• CYCLOPENTAPYRIDINE AND TETRAHYDROQUINOLINE DERIVATIVES
  申请人：Pfizer Products Incorporated

  公开号：EP1869000A1

  公开（公告）日：2007-12-26
• TARTRATE SALT OF (7S)-7-[(5-FLUORO-2-METHYL-BENZYL)OXY]-2-[(2R)-2-METHYLPIPERAZIN-1-YL]-6,7-DIHYDRO-5H-CYCLOPENTA[B]PYRIDINE
  申请人：Pfizer Products Inc.

  公开号：EP2044029A1

  公开（公告）日：2009-04-08