(3S,4S)-1-Benzyl-4-(4-chloro-phenyl)-pyrrolidine-3-carboxylic acid | 1229236-26-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (3S,4S)-1-Benzyl-4-(4-chloro-phenyl)-pyrrolidine-3-carboxylic acid
• 英文别名: (3S,4S)-1-benzyl-4-(4-chlorophenyl)pyrrolidin-1-ium-3-carboxylate
• CAS: 1229236-26-3
• 化学式: C₁₈H₁₈ClNO₂
• 分子量: 315.799
• InChiKey: KFNFWUMLKQDFKI-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,4S)-1-Benzyl-4-(4-chloro-phenyl)-pyrrolidine-3-carboxylic acid 在 palladium on activated charcoal 三氯化铝 、 草酰氯 、 1-氯乙基氯甲酸酯 、 potassium tert-butylate 、 氢气 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 1,2-二氯乙烷 为溶剂， 生成 (3aR,8S,8aR)-6-Chloro-8-methyl-1,2,3,3a,8,8a-hexahydro-indeno[1,2-c]pyrrole
  参考文献：
  名称：

  The design and synthesis of a tricyclic single-nitrogen scaffold that serves as a 5-HT2C receptor agonist

  摘要：

  5-HT2C agonists have shown efficacy in limiting food consumption and thus may serve as an important drug class in combating obesity. We describe the design and synthesis of a novel tricyclic single-nitrogen scaffold that was used to produce 5-HT2C agonists. SAR was developed around this chemotype and compounds were identified that were potent (K-i < 15 nM) and selective relative to other 5-HT2 receptors. The most promising compound displayed a good pharmacokinetic profile in multiple animal species, and was efficacious in an acute feeding study in rats. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.070
• 作为产物：
  描述：

  1-Benzyl-4-(4-chloro-phenyl)-2,5-dihydro-1H-pyrrole-3-carboxylic acid 在 [Ru(OAc)2(R)-2-furyl-MeO-BIPHEP] 氢气 作用下， 以 甲醇 为溶剂， 60.0 ℃ 、4.0 MPa 条件下， 反应 24.0h， 以99%的产率得到(3S,4S)-1-Benzyl-4-(4-chloro-phenyl)-pyrrolidine-3-carboxylic acid
  参考文献：
  名称：

  PYRROLIDINE DERIVATIVES AS NK3 RECEPTOR ANTAGONISTS

  摘要：

  本发明涉及公式I的化合物，其中A、Ar、R、R2、R3、R4、p和o如规范和声明中定义的那样，或其药用活性盐。该化合物是高潜力的NK-3受体拮抗剂，用于治疗抑郁症、疼痛、精神病、帕金森病、精神分裂症、躁郁症、焦虑症和注意力缺陷多动障碍（ADHD）。

  公开号：

  US20100210659A1

文献信息

• PYRROLIDINE DERIVATIVES AS NK3 RECEPTOR ANTAGONISTS
  申请人：Knust Henner

  公开号：US20100210659A1

  公开（公告）日：2010-08-19

  The present invention relates to a compounds of formula I wherein A, Ar, R, R2, R3, R4, p, and o are as defined in the specification and claims or to a pharmaceutically active salt thereof. The present compounds are high potential NK-3 receptor antagonists for the treatment of depression, pain, psychosis, Parkinson's disease, schizophrenia, bipolar disorders, anxiety and attention deficit hyperactivity disorder (ADHD).

  本发明涉及公式I的化合物，其中A、Ar、R、R2、R3、R4、p和o如规范和声明中定义的那样，或其药用活性盐。该化合物是高潜力的NK-3受体拮抗剂，用于治疗抑郁症、疼痛、精神病、帕金森病、精神分裂症、躁郁症、焦虑症和注意力缺陷多动障碍（ADHD）。
• Pyrrolidine derivatives as NK3 receptor antagonists
  申请人：Hoffmann-La Roche Inc.

  公开号：US08318759B2

  公开（公告）日：2012-11-27

  The present invention relates to a compounds of formula I wherein A, Ar, R, R2, R3, R4, p, and o are as defined in the specification and claims or to a pharmaceutically active salt thereof. The present compounds are high potential NK-3 receptor antagonists for the treatment of depression, pain, psychosis, Parkinson's disease, schizophrenia, bipolar disorders, anxiety and attention deficit hyperactivity disorder (ADHD).

  本发明涉及式I的化合物，其中A、Ar、R、R2、R3、R4、p和o如规范和权利要求中所定义的，或其药物活性盐。本发明的化合物是高潜力的NK-3受体拮抗剂，用于治疗抑郁症、疼痛、精神病、帕金森病、精神分裂症、双相情感障碍、焦虑和注意力缺陷多动障碍（ADHD）。
• Process for the preparation of pyrollidine-3-carboxylic acids
  申请人：Hoffmann-La Roche Inc.

  公开号：US08344161B2

  公开（公告）日：2013-01-01

  The invention relates to a novel process for the preparation of (3S,4S)- or (3R,4R)-1-benzyl-4-(halogen-aryl)-pyrrolidine-3-carboxylic acids of formula I or salts thereof, wherein X and Y are each independently hydrogen or a halogen atom, with the proviso that at least one of X or Y is a halogen atom. The compounds of formula I are useful as starting materials or intermediates for the preparation of pharmaceutically active compounds, especially for compounds, which are useful for the treatment of central nervous system disorders.

  本发明涉及一种新型工艺，用于制备式I的(3S,4S)-或(3R,4R)-1-苯甲基-4-(卤代芳基)-吡咯烷-3-羧酸或其盐，其中X和Y各自独立地表示氢或卤素原子，但至少其中的一个是卤素原子。式I的化合物可用作制药活性化合物的起始物或中间体，特别是用于治疗中枢神经系统疾病的化合物。
• US8318759B2
  申请人：——

  公开号：US8318759B2

  公开（公告）日：2012-11-27
• US8344161B2
  申请人：——

  公开号：US8344161B2

  公开（公告）日：2013-01-01