(5-ethanesulfonyl-benzooxazol-2-yl)-[1-(3-ethoxy-4-methoxy-benzyl)-piperidin-4-yl]-amine | 909852-52-4

• 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: (5-ethanesulfonyl-benzooxazol-2-yl)-[1-(3-ethoxy-4-methoxy-benzyl)-piperidin-4-yl]-amine
• 英文别名: N-(1-(3-ethoxy-4-methoxybenzyl)piperidin-4-yl)-5-(ethylsulfonyl)benzo[d]oxazol-2-amine；N-[1-[(3-ethoxy-4-methoxyphenyl)methyl]piperidin-4-yl]-5-ethylsulfonyl-1,3-benzoxazol-2-amine
• CAS: 909852-52-4
• 化学式: C₂₄H₃₁N₃O₅S
• 分子量: 473.593
• InChiKey: KLQBJPKPQBLAOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (5-ethanesulfonyl-benzooxazol-2-yl)-piperidin-4-yl-amine dihydrobromide 、 3-乙氧基-4-甲氧基苯甲醛 在 sodium cyanoborohydride 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 乙醇 为溶剂， 反应 18.0h， 生成 (5-ethanesulfonyl-benzooxazol-2-yl)-[1-(3-ethoxy-4-methoxy-benzyl)-piperidin-4-yl]-amine
  参考文献：
  名称：

  Benzoxazole piperidines as selective and potent somatostatin receptor subtype 5 antagonists

  摘要：

  SAR studies of a recently described SST5R selective benzoxazole piperidine lead series are described with particular focus on the substitution pattern on the benzyl and benzoxazole side-chains. Introduction of a second meta substituent at the benzyl unit significantly lowers residual hH1 activity and insertion of substituents onto the benzoxazole periphery entirely removes remaining h5-HT(2B) activity. Compounds with single digit nM activity, functional antagonism and favorable physicochemical properties endowed with a good pharmacokinetic pro. le in rats are described which should become valuable tools for exploring the pharmacological role of the SST5 receptor in vivo. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.024

文献信息

• Benzothiazole, thiazolopyridine, benzooxazole and oxazolopyridine derivatives
  申请人：Binggeli Alfred

  公开号：US20060205718A1

  公开（公告）日：2006-09-14

  This invention is concerned with compounds of the formula wherein A, B 1 , B 2 , R 1 , R 2 and G are as defined in the description and claims, and pharmaceutically acceptable salts thereof. The invention further relates to pharmaceutical compositions containing such compounds, to a process for their preparation and to their use for the treatment and/or prevention of diseases which are associated with the modulation of SST receptors subtype 5.

  这项发明涉及以下式的化合物 其中A、B 1 、B 2 、R 1 、R 2 和G如描述和索赔中所定义，并其药学上可接受的盐。该发明还涉及含有这种化合物的药物组合物，以及用于制备它们的方法和它们用于治疗和/或预防与调节SST受体亚型5相关的疾病的用途。
• BENZOTHIAZOLE, THIAZOLOPYRIDINE, BENZOOXAZOLE AND OXAZOLOPYRIDINE DERIVATIVES AS ANTIDIABETIC COMPOUNDS
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1858901A1

  公开（公告）日：2007-11-28
• US7645753B2
  申请人：——

  公开号：US7645753B2

  公开（公告）日：2010-01-12
• [EN] BENZOTHIAZOLE, THIAZOLOPYRIDINE, BENZOOXAZOLE AND OXAZOLOPYRIDINE DERIVATIVES AS ANTIDIABETIC COMPOUNDS<br/>[FR] DERIVES DE BENZOTHIAZOLE, DE THIAZOLOPYRIDINE, DE BENZOOXAZOLE ET D'OXAZOLOPYRIDINE EN TANT QUE COMPOSES ANTIDIABETIQUES
  申请人：HOFFMANN LA ROCHE

  公开号：WO2006094682A1

  公开（公告）日：2006-09-14

  [EN] This invention is concerned with compounds of the formula (I) wherein A, B¹, B², R¹, R² and G are as defined in the description and claims, and pharmaceutically acceptable salts thereof. The invention further relates to pharmaceutical compositions containing such compounds, to a process for their preparation and to their use for the treatment and/or prevention of diseases which are associated with the modulation of SST receptors subtype 5.
  [FR] L'invention concerne des composés de formule (I), où A, B¹, B², R¹, R² et G sont tels que définis dans la description et dans les revendications, ainsi que leurs sels pharmaceutiquement acceptables. L'invention concerne également des compositions pharmaceutiques contenant de tels composés, leur procédé de fabrication, ainsi que leur utilisation pour le traitement et/ou la prévention de maladies associées à la modulation de récepteurs SST de sous-type 5.
• Benzoxazole piperidines as selective and potent somatostatin receptor subtype 5 antagonists
  作者：Rainer E. Martin、Peter Mohr、Hans Peter Maerki、Wolfgang Guba、Christoph Kuratli、Olivier Gavelle、Alfred Binggeli、Stefanie Bendels、Rubén Alvarez-Sánchez、André Alker、Liudmila Polonchuk、Andreas D. Christ

  DOI：10.1016/j.bmcl.2009.09.024

  日期：2009.11

  SAR studies of a recently described SST5R selective benzoxazole piperidine lead series are described with particular focus on the substitution pattern on the benzyl and benzoxazole side-chains. Introduction of a second meta substituent at the benzyl unit significantly lowers residual hH1 activity and insertion of substituents onto the benzoxazole periphery entirely removes remaining h5-HT(2B) activity. Compounds with single digit nM activity, functional antagonism and favorable physicochemical properties endowed with a good pharmacokinetic pro. le in rats are described which should become valuable tools for exploring the pharmacological role of the SST5 receptor in vivo. (c) 2009 Elsevier Ltd. All rights reserved.