(+)-Tiagabine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (+)-Tiagabine
• 英文别名: (3S)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-enyl]piperidin-1-ium-3-carboxylate
• 化学式: C₂₀H₂₅NO₂S₂
• 分子量: 375.556
• InChiKey: PBJUNZJWGZTSKL-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  97
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  双(3-甲基-2-噻吩基)甲酮 在 sodium hydroxide 、 氢溴酸 、 potassium carbonate 、 magnesium 、 potassium iodide 作用下， 以 乙醇 、 溶剂黄146 、 丙酮 为溶剂， 反应 51.5h， 生成 (+)-Tiagabine
  参考文献：
  名称：

  The synthesis of novel GABA uptake inhibitors. 1. Elucidation of the structure-activity studies leading to the choice of (R)-1-[4,4-bis(3-methyl-2-thienyl)-3-butenyl]-3-piperidinecarboxylic acid (Tiagabine) as an anticonvulsant drug candidate

  摘要：

  A series of different synthetic approaches to novel GABA uptake inhibitors are described, leading to examples which are derivatives of nipecotic acid and guvacine, substituted at nitrogen by 4,4-diaryl-3-butenyl or 2-(diphenylmethoxy)ethyl moieties. The in vitro value for inhibition of [H-3]-GABA uptake in rat synaptosomes was determined for each compound. It was found that the most potent examples are those having a substituent in an ''ortho'' position in one or both aromatic/heteroaromatic groups. The majority of the compounds described are structurally related to tiagabine, (R)-1-[4,4-bis(3-methyl-2-thienyl)-3-butenyl]-3-piperidinecarboxylic acid hydrochloride (NNC 05-0328) and some of the reasoning behind the selection of this compound as a drug candidate is summarized.

  DOI：

  10.1021/jm00064a005

文献信息

• Active agent delivery systems and methods for protecting and administering active agents
  申请人：Mickle Travis

  公开号：US20070232529A1

  公开（公告）日：2007-10-04

  The present invention relates to active agent delivery systems and more specifically to compositions that comprise amino acids, as single amino acids or peptides, covalently attached to active agents and methods for administering conjugated active agent compositions.

  本发明涉及活性物质输送系统，更具体地涉及包含氨基酸（作为单个氨基酸或肽）与活性物质共价连接的组合物以及用于给予共轭活性物质组合物的方法。
• ACTIVE AGENT DELIVERY SYSTEMS AND METHODS FOR PROTECTING AND ADMINISTERING ACTIVE AGENTS
  申请人：Mickle Travis

  公开号：US20090253792A1

  公开（公告）日：2009-10-08

  The present invention relates to active agent delivery systems and more specifically to compositions that comprise amino acids, as single amino acids or peptides, covalently attached to active agents and methods for administering conjugated active agent compositions.

  本发明涉及活性剂递送系统，更具体地涉及包含氨基酸（作为单个氨基酸或肽）与活性剂共价连接的组合物以及给予共轭活性剂组合物的方法。
• ACTIVE AGENT DELIVERY SYSTEMS AND METHODS FOR PROTECTING AND ADMINISTERING ACTIVE AGENTS
  申请人：Mickle Travis

  公开号：US20090306228A1

  公开（公告）日：2009-12-10

  The present invention relates to active agent delivery systems and more specifically to compositions that comprise amino acids, as single amino acids or peptides, covalently attached to active agents and methods for administering conjugated active agent compositions.

  本发明涉及活性剂递送系统，更具体地涉及包含氨基酸，作为单个氨基酸或肽，与活性剂共价结合的组合物以及用于给予共轭活性剂组合物的方法。
• Treatment of ADHD
  申请人：Gosforth Centre (Holdings) Pty Ltd

  公开号：EP2505197A1

  公开（公告）日：2012-10-03

  A method is described for treating attention deficit hyperactivity disorder (ADHD), by administering to the individual an anti-epileptic mood stabiliser at a dose which is sub-therapeutic for mood stabilisation, optionally in combination with a psychostimulant. Also described is a method of improving reading comprehension and/or fluency in an individual suffering from learning difficulties which method comprises administering to the individual an anti-epileptic mood stabiliser.

  本文描述了一种治疗注意力缺陷多动障碍（ADHD）的方法，即给患者服用抗癫痫情绪稳定剂，剂量为稳定情绪的次治疗剂量，可选择与精神兴奋剂联合使用。还描述了一种改善学习困难患者阅读理解和/或流畅性的方法，该方法包括给患者服用抗癫痫情绪稳定剂。
• TREATMENT OF ADHD
  申请人：Bird Philip

  公开号：US20100087422A1

  公开（公告）日：2010-04-08

  A method is described for treating attention deficit hyperactivity disorder (ADHD), by administering to the individual an anti-epileptic mood stabiliser at a dose which is sub-therapeutic for mood stabilisation, optionally in combination with a psychostimulant. Also described is a method of improving reading comprehension and/or fluency in an individual suffering from learning difficulties which method comprises administering to the individual an anti-epileptic mood stabiliser.