3-乙炔基-5-[(2S)-1-甲基-2-吡咯烷基]吡啶马来酸盐 | 192231-16-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 3-乙炔基-5-[(2S)-1-甲基-2-吡咯烷基]吡啶马来酸盐
• 英文名称: 3-Ethynyl-5-((S)-1-methyl-pyrrolidin-2-yl)-pyridine; compound with (Z)-but-2-enedioic acid
• 英文别名: Altinicline maleate；(Z)-but-2-enedioic acid;3-ethynyl-5-[(2S)-1-methylpyrrolidin-2-yl]pyridine
• CAS: 192231-16-6
• 化学式: C₄H₄O₄*C₁₂H₁₄N₂
• 分子量: 302.33
• InChiKey: BCPPKHPWLRPWBJ-OURKGEEVSA-N

物化性质

• 熔点：
  152.5-153.5 °C
• 溶解度：
  水中溶解度为 100 mM，DMSO 溶解度为 50 mM

计算性质

• 辛醇/水分配系数(LogP)：
  -3.13
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  98.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-乙炔基尼古丁 以93的产率得到3-乙炔基-5-[(2S)-1-甲基-2-吡咯烷基]吡啶马来酸盐
  参考文献：
  名称：

  J. Med. Chem. 1996, 39, 3235-3237

  摘要：

  DOI：

文献信息

• NOVEL COMPOUND AND MEDICAL USE THEREOF
  申请人：Kokubo Masaya

  公开号：US20130245074A1

  公开（公告）日：2013-09-19

  Provided is a levodopa prodrug that overcomes the problems attributed to the blood kinetics of levodopa such as large number of doses and the incidence of side effects due to frequent dosing. (2S)-2-Amino-3-(3,4-bis((2-(benzoyloxy)-2-methylpropanoyl)oxy)phenyl)propanoic acid, a salt thereof, or a solvate thereof is a levodopa prodrug, and provides a flat blood concentration-time profile of levodopa through oral administration, and therefore is useful as a preventive and/or therapeutic agent for Parkinson's disease and/or Parkinson's syndrome that overcomes the problems associated with pharmaceutical preparations of levodopa.

  提供了一种左多巴前药，它克服了左多巴的血液动力学问题，例如需要大量剂量和频繁给药导致的副作用。其化学名为(2S)-2-氨基-3-(3,4-双((2-(苯甲酰氧基)-2-甲基丙酰氧)苯基)丙酸，其盐或溶剂化合物是左多巴前药，通过口服给药提供了左多巴平稳的血药浓度时间曲线，因此可用作克服左多巴药物制剂相关问题的帕金森病和/或帕金森综合征的预防和/或治疗药物。
• A Practical and Efficient Synthesis of the Selective Neuronal Acetylcholine-Gated Ion Channel Agonist (<i>S</i>)-(−)-5-Ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine Maleate (SIB-1508Y)
  作者：Leo S. Bleicher、Nicholas D. P. Cosford、Audrey Herbaut、J. Stuart McCallum、Ian A. McDonald

  DOI：10.1021/jo971572d

  日期：1998.2.1

  An efficient, high-yielding synthetic procedure for the preparation of the novel neuronal acetylcholine-gated ion channel agonist (S)-(-)-5-ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine maleate [(S)-2, SIB-1508Y] is described. The key steps in the process include the lithium bis(trimethylsilyl)amide-mediated acylation of N-vinylpyrrolidinone with ethyl 5-bromonicotinate, a high-yielding sodium borohydride reduction of imine 5, and a new heteroaryl-alkyne cross-coupling protocol for the introduction of the ethyne moiety in (S)-2. The preparation of enantiomerically pure (S)-2 was accomplished via a combination of enantioselective reduction of imine 5 and crystallization of enantiomerically enriched 5-bromo-3-(1-methyl-2-pyrrolidinyl)pyridine (7) as the dibenzoyl-L-tartaric acid salt.
• US8748485B2
  申请人：——

  公开号：US8748485B2

  公开（公告）日：2014-06-10
• US8703816B2
  申请人：——

  公开号：US8703816B2

  公开（公告）日：2014-04-22