3-(1-Benzyl-piperidin-4-ylamino)-benzonitrile | 477179-13-8

• 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: 3-(1-Benzyl-piperidin-4-ylamino)-benzonitrile
• 英文别名: 3-(1-benzyl-piperidin-4-ylamino)-benznitrile；3-[(1-benzylpiperidin-4-yl)amino]benzonitrile
• CAS: 477179-13-8
• 化学式: C₁₉H₂₁N₃
• 分子量: 291.396
• InChiKey: SPRPLFPDVFHQFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  39.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(1-Benzyl-piperidin-4-ylamino)-benzonitrile 、 N,N-二乙基-4-溴苯甲酰胺 在 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 生成 4-(N-(1-benzylpiperidin-4-yl)-3-cyanoanilino)-N,N-diethylbenzamide
  参考文献：
  名称：

  Delta agonist hydroxy bioisosteres: The discovery of 3-((1-benzylpiperidin-4-yl){4-[(diethylamino)carbonyl]phenyl}amino)benzamide with improved delta agonist activity and in vitro metabolic stability

  摘要：

  We have investigated phenol replacements in a series of diaryl amino piperidine delta opioid agonists. From this study we have demonstrated that the hydroxy functional group can be replaced with a primary amide group, giving enhanced activity at the delta receptor, increased selectivity versus mu and kappa as well as improved in vitro metabolic stability. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.068
• 作为产物：
  描述：

  4-氨基-1-苄基哌啶 、 间溴苯甲腈 在 tris-(dibenzylideneacetone)dipalladium(0) 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 生成 3-(1-Benzyl-piperidin-4-ylamino)-benzonitrile
  参考文献：
  名称：

  Delta agonist hydroxy bioisosteres: The discovery of 3-((1-benzylpiperidin-4-yl){4-[(diethylamino)carbonyl]phenyl}amino)benzamide with improved delta agonist activity and in vitro metabolic stability

  摘要：

  We have investigated phenol replacements in a series of diaryl amino piperidine delta opioid agonists. From this study we have demonstrated that the hydroxy functional group can be replaced with a primary amide group, giving enhanced activity at the delta receptor, increased selectivity versus mu and kappa as well as improved in vitro metabolic stability. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.068

文献信息

• 4-(phenyl-(piperidin-4yl)-amino)-benzamide derivatives and their use for the treatment of pain, anxiety or gastrointestinal disorders
  申请人：——

  公开号：US20040142965A1

  公开（公告）日：2004-07-22

  Compounds of general formula I [Chemical formula should be inserted here. Please see paper copy] R 1 is selected from any one of phenyl, pyridinyl, thienyl, furanyl, imidazolyl, pyrrolyl, triazolyl, thiazolyl, and pyridine N-oxide; where each R 1 phenyl ring and R 1 heteroaromatic ring may optionally and independently be further substituted by 1, 2 or 3 substituents selected from straight and branched C 1 -C 6 alkyl, NO 2 , CF 3 , C 1 -C 6 alkoxy, chloro, fluoro, bromo, and iodo. The substitutions on the phenyl ring and on the heteroaromatic ring may take place in any position on said ring systems; are disclosed and claimed in the present application, as well as salts and pharmaceutical compositions comprising the novel compounds and their use in therapy, in particular in the management of pain, anxiety or functional gastrointestinal disorders.

  通式I的化合物 [化学式应在此处插入。请参见纸质副本]，其中R1从苯基、吡啶基、噻吩基、呋喃基、咪唑基、吡咯基、三唑基、噻唑基和吡啶N-氧化物中选择；其中每个R1苯环和R1杂环环可以选择且独立地进一步由选自直链和支链C1-C6烷基、NO2、CF3、C1-C6烷氧基、氯、氟、溴和碘的1、2或3个取代基取代。苯环和杂环环上的取代基可以在所述环系统上的任何位置发生；本申请中披露和声明了这些取代基，以及包括新化合物的盐和药物组成物以及它们在治疗中的使用，特别是在疼痛、焦虑或功能性胃肠疾病的管理中。
• 4-(PHENYL-(PIPERIDIN-4-YL)-AMINO)-BENZAMIDE DERIVATIVES AND THEIR USE FOR THE TREATMENT OF PAIN, ANXIETY OR GASTROINTESTINAL DISORDERS
  申请人：AstraZeneca AB

  公开号：EP1395556A1

  公开（公告）日：2004-03-10
• US7186733B2
  申请人：——

  公开号：US7186733B2

  公开（公告）日：2007-03-06
• [EN] 4-(PHENYL-(PIPERIDIN-4-YL)-AMINO)-BENZAMIDE DERIVATIVES AND THEIR USE FOR THE TREATMENT OF PAIN, ANXIETY OR GASTROINTESTINAL DISORDERS<br/>[FR] DERIVES DE 4-(PHENYL-(PIPERIDINE-4-YL)-AMINO)-BENZAMIDE ET LEUR UTILISATION DANS LE TRAITEMENT DE DOULEURS, DE L'ANXIETE OU DE TROUBLES GASTRO-INTESTINAUX
  申请人：ASTRAZENECA AB

  公开号：WO2002094784A1

  公开（公告）日：2002-11-28

  Compounds of general formula I[Chemical formula should be inserted here. Please see paper copy] R1 is selected from any one of phenyl, pyridinyl, thienyl, furanyl, imidazolyl, pyrrolyl, triazolyl, thiazolyl, and pyridine N-oxide; where each R1 phenyl ring and R1 heteroaromatic ring may optionally and independently be further substituted by 1, 2 or 3 substituents selected from straight and branched C1-C6alkyl, NO2, CF3, C1-C6alkoxy, chloro, fluoro, bromo, and iodo. The substitutions on the phenyl ring and on the heteroaromatic ring may take place in any position on said ring systems; are disclosed and claimed in the present application, as well as salts and pharmaceutical compositions comprisingthe novel compounds and their use in therapy, in particular in the management of pain, anxiety or functional gastrointestinal disorders.
• Delta agonist hydroxy bioisosteres: The discovery of 3-((1-benzylpiperidin-4-yl){4-[(diethylamino)carbonyl]phenyl}amino)benzamide with improved delta agonist activity and in vitro metabolic stability
  作者：Andrew M. Griffin、William Brown、Christopher Walpole、Martin Coupal、Lynda Adam、Mylene Gosselin、Dominic Salois、Pierre-Emmanuel Morin、Marie Roumi

  DOI：10.1016/j.bmcl.2009.09.068

  日期：2009.11

  We have investigated phenol replacements in a series of diaryl amino piperidine delta opioid agonists. From this study we have demonstrated that the hydroxy functional group can be replaced with a primary amide group, giving enhanced activity at the delta receptor, increased selectivity versus mu and kappa as well as improved in vitro metabolic stability. (C) 2009 Elsevier Ltd. All rights reserved.