dimethyl-(2-{3-[(S)-1-(2-fluoro-pyridin-3-yl)-ethyl]-benzo[b]thiophen-2-yl}-ethyl)-amine | 873693-83-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: dimethyl-(2-{3-[(S)-1-(2-fluoro-pyridin-3-yl)-ethyl]-benzo[b]thiophen-2-yl}-ethyl)-amine
• 英文别名: NBI-4 (non-labeled)；2-[3-[(1S)-1-(2-fluoropyridin-3-yl)ethyl]-1-benzothiophen-2-yl]-N,N-dimethylethanamine
• CAS: 873693-83-5
• 化学式: C₁₉H₂₁FN₂S
• 分子量: 328.454
• InChiKey: KLFVGKSTNOVPOR-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  44.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  dimethyl-(2-{3-[1-(2-fluoro-pyridin-3-yl)-ethyl]-benzo[b]thiophen-2-yl}-ethyl)-amine 在 chiral HPLC 作用下， 生成 dimethyl-(2-{3-[(R)-1-(2-fluoro-pyridin-3-yl)-ethyl]-benzo[b]thiophen-2-yl}-ethyl)-amine 、 dimethyl-(2-{3-[(S)-1-(2-fluoro-pyridin-3-yl)-ethyl]-benzo[b]thiophen-2-yl}-ethyl)-amine
  参考文献：
  名称：

  Novel benzothiophene H1-antihistamines for the treatment of insomnia

  摘要：

  SAR of lead benzothiophene H-1-antihistamine 2 was explored to identify backup candidates with suitable pharmacokinetic profiles for an insomnia program. Several potent and selective H-1-antihistamines with a range of projected half-lives in humans were identified. Compound 16d had a suitable human half-life as demonstrated in a human microdose study, but variability in pharmacokinetic profile, attributed to metabolic clearance, prevented further development of this compound. Compound 28b demonstrated lower predicted clearance in preclinical studies, and may represent a more suitable backup compound. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.134

文献信息

• Sleep inducing compounds and methods relating thereto
  申请人：Beaton Graham

  公开号：US20060014797A1

  公开（公告）日：2006-01-19

  Compounds having the following structure (I): including stereoisomers, prodrugs, and pharmaceutically acceptable salts, esters and solvates thereof, wherein R 1 , R 2 , R 3a , R 3b , L 1 , L 2 and n are as defined herein. Such compounds generally function as H 1 receptor ligands, and thus have utility as sleep inducing agents. Pharmaceutical compositions containing a compound of structure (I), as well as methods relating to the use thereof, are also disclosed.

  具有以下结构（I）的化合物，包括立体异构体、前药、以及其药用可接受的盐、酯和溶剂合物，其中R1、R2、R3a、R3b、L1、L2和n如本文所定义。这些化合物通常作为H1受体配体发挥作用，因此具有作为催眠药的用途。还披露了含有结构（I）化合物的药物组合物，以及与其使用相关的方法。
• US7393865B2
  申请人：——

  公开号：US7393865B2

  公开（公告）日：2008-07-01
• [EN] SLEEP-INDUCING COMPOUNDS AND METHODS RELATED THERETO<br/>[FR] COMPOSES SOMNIFERES ET PROCEDES ASSOCIES
  申请人：NEUROCRINE BIOSCIENCES INC

  公开号：WO2006019497A2

  公开（公告）日：2006-02-23

  Compounds having the following structure (I): including stereoisomers, prodrugs, and pharmaceutically acceptable salts, esters and solvates thereof, wherein R1, R2, R3a, R3b, L1, L2 and n are as defined herein. Such compounds generally function as H1 receptor ligands, and thus have utility as sleep inducing agents. Pharmaceutical compositions containing a compound of structure (I), as well as methods relating to the use thereof, are also disclosed.
• Novel benzothiophene H1-antihistamines for the treatment of insomnia
  作者：Wilna J. Moree、Florence Jovic、Timothy Coon、Jinghua Yu、Bin-Feng Li、Fabio C. Tucci、Dragan Marinkovic、Raymond S. Gross、Siobhan Malany、Margaret J. Bradbury、Lisa M. Hernandez、Zhihong O’Brien、Jianyun Wen、Hua Wang、Samuel R.J. Hoare、Robert E. Petroski、Aida Sacaan、Ajay Madan、Paul D. Crowe、Graham Beaton

  DOI：10.1016/j.bmcl.2010.01.134

  日期：2010.4

  SAR of lead benzothiophene H-1-antihistamine 2 was explored to identify backup candidates with suitable pharmacokinetic profiles for an insomnia program. Several potent and selective H-1-antihistamines with a range of projected half-lives in humans were identified. Compound 16d had a suitable human half-life as demonstrated in a human microdose study, but variability in pharmacokinetic profile, attributed to metabolic clearance, prevented further development of this compound. Compound 28b demonstrated lower predicted clearance in preclinical studies, and may represent a more suitable backup compound. (C) 2010 Elsevier Ltd. All rights reserved.