4-[N-(1-benzyl-piperidin-4-yl)-amino]-N,N-diethyl benzamide | 209902-02-3

• 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: 4-[N-(1-benzyl-piperidin-4-yl)-amino]-N,N-diethyl benzamide
• 英文别名: 4-(1-Benzyl-piperidin-4-ylamino)-N,N-diethyl-benzamide；4-[(1-benzylpiperidin-4-yl)amino]-N,N-diethylbenzamide
• CAS: 209902-02-3
• 化学式: C₂₃H₃₁N₃O
• 分子量: 365.519
• InChiKey: LSSMSUXPIUTNMG-UHFFFAOYSA-N

物化性质

• 沸点：
  535.4±50.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  35.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[N-(1-benzyl-piperidin-4-yl)-amino]-N,N-diethyl benzamide 、 1,3-二溴苯 在 tris-(dibenzylideneacetone)dipalladium(0) 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 以68%的产率得到4-((1-benzylpiperidin-4-yl)(3-bromophenyl)amino)-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 、 N,N-二乙基-4-溴苯甲酰胺 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， 以77%的产率得到4-[N-(1-benzyl-piperidin-4-yl)-amino]-N,N-diethyl benzamide
  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

• Compounds with analgesic effect
  申请人：Astra Pharma Inc.

  公开号：US06153626A1

  公开（公告）日：2000-11-28

  Compounds of general formula (I) ##STR1## wherein m is 0 or 1, and n is 1 or 2; are disclosed and claimed in the present application, as well as their pharmaceutically acceptable salts, pharmaceutical compositions comprising the novel compounds and their use in therapy, in particular in the management of pain.

  通式（I）的化合物 ##STR1## 中，其中m为0或1，n为1或2；在本申请中被披露并声明，以及它们的药学上可接受的盐，包括新化合物的制药组合物以及它们在治疗中的应用，特别是在疼痛管理中的应用。
• 4-(Phenyl-(piperidin-4-yl)-amino)-benzamide derivatives and their use for the treatment of pain, anxiety or gastrointestinal disorders
  申请人：——

  公开号：US20040235897A1

  公开（公告）日：2004-11-25

  Compounds of general formula I 1 R 1 is selected from any one of phenyl, pyridinyl, pyrrolyl, thienyl, furanyl, imidazolyl, triazolyl, 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 their pharmaceutically acceptable salts and pharmaceutical compositions comprising the novel compounds and their use in therapy, in particular in the management of pain, anxiety and functional gastrointestinal disorders.

  通式I1R1的化合物选择自苯基、吡啶基、吡咯基、噻吩基、呋喃基、咪唑基、三唑基和吡啶N-氧化物中的任意一种；其中每个R1苯环和R1杂环环可以选择性地且独立地进一步由1、2或3个取代基组成，所述取代基选择自直链和支链C1-C6烷基、NO2、CF3、C1-C6烷氧基、氯、氟、溴和碘。苯环和杂环环上的取代作用可以在所述环系统的任何位置发生；本申请公开并要求其药学上可接受的盐和含有新化合物的药物组合物以及它们在治疗中的使用，特别是在疼痛、焦虑和功能性胃肠障碍的管理中。
• 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：US07226933B2

  公开（公告）日：2007-06-05

  Compounds of general formula I R1 is selected from any one of phenyl, pyridinyl, pyrrolyl, thienyl, furanyl, imidazolyl, triazolyl, 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 their pharmaceutically acceptable salts and pharmaceutical compositions comprising the novel compounds and their use in therapy, in particular in the management of pain, anxiety and functional gastrointestinal disorders.

  通式为IR1的化合物可从苯基、吡啶基、吡咯基、噻吩基、呋喃基、咪唑基、三唑基和吡啶N-氧化物中选择；其中，每个R1苯环和R1杂环环上的取代基可以选择性地独立地进一步取代为1、2或3个取代基，所选的取代基包括直链和支链C1-C6烷基、NO2、CF3、C1-C6烷氧基、氯、氟、溴和碘。苯环和杂环环上的取代作用可以在所述环系统的任何位置发生；本申请公开和声明了这些化合物及其药学上可接受的盐和包含这些新化合物的制药组合物，并且它们在治疗中的使用，特别是在疼痛、焦虑和功能性胃肠疾病的管理中。
• Piperidin-4-yl amines with analgesic effect
  申请人：AstraZeneca AB

  公开号：EP1428821A1

  公开（公告）日：2004-06-16

  Compounds of general formula (I) wherein m is 0 or 1, and n is 1 or 2; are disclosed and claimed in the present application, as well as their pharmaceutically acceptable salts, pharmaceutical compositions comprising the novel compounds and their use in therapy, in particular in the management of pain.

  通式(I)化合物 其中 m 为 0 或 1，n 为 1 或 2； 以及它们的药学上可接受的盐、包含这些新型化合物的药物组合物和它们在治疗中的用途，特别是在疼痛治疗中的用途。
• Novel compounds with analgesic effect
  申请人：Astra Pharma Inc.

  公开号：US20030055045A1

  公开（公告）日：2003-03-20

  Compounds of general formula (I) 1 wherein m is 0 or 1, and n is 1 or 2; are disclosed and claimed in the present application, as well as their pharmaceutically acceptable salts, pharmaceutical compositions comprising the novel compounds and their use in therapy, in particular in the management of pain.

  本申请公开了通式(I)1（其中m为0或1，n为1或2）的化合物及其药学上可接受的盐、包含这些新型化合物的药物组合物以及它们在治疗中的用途，特别是在疼痛治疗中的用途。