7-chloro-3-(4-{[N-ethyl-N-(2-hydroxyethyl)amino]methyl}-[1,3]-thiazol-2-yl)-1-(tetrahydropyran-4-yl)methyl-1H-indole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 7-chloro-3-(4-{[N-ethyl-N-(2-hydroxyethyl)amino]methyl}-[1,3]-thiazol-2-yl)-1-(tetrahydropyran-4-yl)methyl-1H-indole
• 英文别名: 2-[[2-[7-Chloro-1-(oxan-4-ylmethyl)indol-3-yl]-1,3-thiazol-4-yl]methyl-ethylamino]ethanol
• 化学式: C₂₂H₂₈ClN₃O₂S
• 分子量: 434.002
• InChiKey: UKOAAEWZHAWVNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  78.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  7-氯吲哚 在 tetraphosphorus decasulfide 、 草酰氯 、 氨 、 水 、 sodium hydride 、 potassium carbonate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 6.67h， 生成 7-chloro-3-(4-{[N-ethyl-N-(2-hydroxyethyl)amino]methyl}-[1,3]-thiazol-2-yl)-1-(tetrahydropyran-4-yl)methyl-1H-indole
  参考文献：
  名称：

  设计，合成和（吲哚-3-基）杂环衍生物作为CB1受体激动剂的结构活性关系。发现临床候选者

  摘要：

  我们报告了一种新型的吲哚-3-杂环CB1受体激动剂的结构-活性关系（SAR）的扩展。从强力但难溶的铅开始，1，采取了一种合理的方法来平衡溶解度，hERG活性和效价，同时在小鼠甩尾试验中保持所需的长效作用。这导致了化合物38的发现，该化合物成功地进入了临床开发阶段。

  DOI：

  10.1016/j.bmcl.2011.02.023

文献信息

• (Indol-3-yl) heterocycle derivatives as a agonists of the cannabinoid cb1 receptor
  申请人：Adam-Worrall Julia

  公开号：US20070142446A1

  公开（公告）日：2007-06-21

  Disclosed herein are indole derivatives of the formula (I) wherein each of the substitutents is given the definition as set forth in the specification and claims. Also disclosed are pharmaceutical compositions containing the indole derivatives and use of the derivatives for the treatment of pain.

  本文揭示了公式(I)的吲哚衍生物，其中每个取代基的定义如规范和要求所述。还揭示了含有这些吲哚衍生物的药物组合物，并且这些衍生物可用于治疗疼痛。
• (INDOL-3-YL)-HETEROCYCLE DERIVATIVES AS AGONISTS OF THE CANNABINOID CB1 RECEPTOR
  申请人：N.V. Organon

  公开号：EP1725232B1

  公开（公告）日：2008-01-23
• USE OF TOPICAL FORMULATIONS OF CANNABINOIDS IN THE TREATMENT OF EPIDERMOLYSIS BULLOSA AND RELATED CONNECTIVE TISSUE DISORDERS
  申请人：INMED PHARMACEUTICALS INC.

  公开号：US20190142788A1

  公开（公告）日：2019-05-16

  Mutations in keratin genes or the genes that regulate keratin expression can result in epithelial cells lacking sufficient structural integrity. The resulting disruption of connective tissue gives rise to inherited disorders such epidermolysis bullosa. It has been found that various cannabinoids (including mixtures of cannabidiols and cannabinol) upregulate expression of various keratins such that loss of function in other keratin genes may be compensated for. By way of this upregulation, these cannabinoids can be used to treat epidermolysis bullosa and other connective tissue disorders arising from intermediate filament dysfunction.
• TOPICAL FORMULATIONS OF CANNABINOIDS AND USE THEREOF IN THE TREATMENT OF PAIN
  申请人：INMED PHARMACEUTICALS INC.

  公开号：US20200289458A1

  公开（公告）日：2020-09-17

  Pharmaceutical compositions comprising one or more cannabinoids and a pharmaceutically acceptable carrier are disclosed. The compositions are in a form suitable for topical administration, and are useful in the treatment of pain. The cannabinoids suitable for use include cannabidiols, cannabinols, and various other naturally occurring and synthetic cannabinoids. The compositions may also further include anti-inflammatory agents, steroids, or terpenoids. In preferred embodiments, the cannabinoids incorporated in the compositions are cannabidiol (CBD) and cannabinol (CBN) while the carriers are selected from the group consisting of Labrasol™, Transcutol™, lecithin, lysolecithin, isopropyl palmitate, and isopropyl myristate.
• US7700634B2
  申请人：——

  公开号：US7700634B2

  公开（公告）日：2010-04-20