(S)-3-(3-methoxyphenoxy)pyrrolidine | 931409-73-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-3-(3-methoxyphenoxy)pyrrolidine
• 英文别名: (3S)-3-(3-methoxyphenoxy)pyrrolidine；Pyrrolidine, 3-(3-methoxyphenoxy)-, (3S)-
• CAS: 931409-73-3
• 化学式: C₁₁H₁₅NO₂
• mdl: MFCD08688087
• 分子量: 193.246
• InChiKey: XEJBWNVKUCYHJV-NSHDSACASA-N

物化性质

• 沸点：
  307.4±32.0 °C(Predicted)
• 密度：
  1.084±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-3-(3-methoxyphenoxy)pyrrolidine 、 4-cyano-4,4-diphenylbutanoic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以100%的产率得到5-oxo-5-[(3S)-3-phenoxypyrrolidin-1-yl]-2,2-diphenylpentanenitrile
  参考文献：
  名称：

  Inhalation by Design: Novel Tertiary Amine Muscarinic M₃ Receptor Antagonists with Slow Off-Rate Binding Kinetics for Inhaled Once-Daily Treatment of Chronic Obstructive Pulmonary Disease

  摘要：

  A novel tertiary amine series of potent muscarinic M-3 receptor antagonists are described that exhibit potential as inhaled long-acting bronchodilators for the treatment of chronic obstructive pulmonary disease. Geminal dimethyl functionality present in this series of compounds confers very long dissociative half-life (slow off-rate) from the M-3 receptor that mediates very long-lasting smooth muscle relaxation in guinea pig tracheal strips. Optimization of pharmacokinetic properties was achieved by combining rapid oxidative clearance with targeted introduction of a phenolic moiety to secure rapid glucuronidation. Together, these attributes minimize systemic exposure following inhalation, mitigate potential drug-drug interactions, and reduce systemically mediated adverse events. Compound 47 (PP-3635659) is identified as a Phase II clinical candidate from this series with in vivo duration of action studies confirming its potential for once-daily use in humans.

  DOI：

  10.1021/jm200884j
• 作为产物：
  描述：

  tert-butyl (3S)-3-(3-methoxyphenoxy)pyrrolidine-1-carboxylate 在 盐酸 、 氨 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 3.0h， 以85%的产率得到(S)-3-(3-methoxyphenoxy)pyrrolidine
  参考文献：
  名称：

  WO2007/34325

  摘要：

  公开号：

文献信息

• Carboxamide derivatives as muscarinic receptor antagonists
  申请人：Glossop Alan Paul

  公开号：US20070105831A1

  公开（公告）日：2007-05-10

  The invention relates to compounds of formula processes and intermediates for their preparation, their use as muscarinic antagonists and pharmaceutical composition containing them.

  本发明涉及具有下列公式的化合物、其制备方法和中间体，以及包含它们的抗胆碱能药物组合物。
• Carboxamide Derivatives As Muscarinic Receptor Antagonists
  申请人：Glossop Paul Alan

  公开号：US20100029720A1

  公开（公告）日：2010-02-04

  The invention relates to compounds of formula processes and intermediates for their preparation, their use as muscarinic antagonists and pharmaceutical composition containing them.

  本发明涉及具有以下式的化合物，以及制备它们的过程和中间体，它们作为毒蕈碱受体拮抗剂的用途和包含它们的制药组合物。
• CARBOXAMIDE DERIVATIVES AS MUSCARINIC RECEPTOR ANTAGONISTS
  申请人：Pfizer Limited

  公开号：EP1928821B1

  公开（公告）日：2009-01-07
• US7772223B2
  申请人：——

  公开号：US7772223B2

  公开（公告）日：2010-08-10
• US8268881B2
  申请人：——

  公开号：US8268881B2

  公开（公告）日：2012-09-18