3-Phenyl-3-pyridin-4-ylpiperidin-2-one | 945936-58-3

• 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: 3-Phenyl-3-pyridin-4-ylpiperidin-2-one
• CAS: 945936-58-3
• 化学式: C₁₆H₁₆N₂O
• 分子量: 252.316
• InChiKey: INRKOCUXDXQYEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Phenyl-3-pyridin-4-ylpiperidin-2-one 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 以80%的产率得到3-Phenyl-3-piperidin-4-ylpiperidin-2-one
  参考文献：
  名称：

  Synthesis and structure–activity relationship of benzetimide derivatives as human CXCR3 antagonists

  摘要：

  The synthesis and evaluation of benzetimide derivatives showing potent CXCR3 antagonism are described. Optimization of the screening hits led to the identification of more potent CXCR3 antagonists devoid of anti-cholinergic activity and identification of the key pharmacophore moieties of the series. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.07.115
• 作为产物：
  描述：

  Ethyl 4-cyano-2-phenyl-2-pyridin-4-ylbutanoate 在 镍 氢气 作用下， 以 四氢呋喃 为溶剂， 生成 3-Phenyl-3-pyridin-4-ylpiperidin-2-one
  参考文献：
  名称：

  WO2007/90826

  摘要：

  公开号：

文献信息

• WO2007/90826
  申请人：——

  公开号：——

  公开（公告）日：——
• Piperidine Derivatives as Cxcr3 Receptor Antagonists
  申请人：Coesemans Erwin

  公开号：US20090030039A1

  公开（公告）日：2009-01-29

  The present invention relates to a compound of formula (I) a N-oxide thereof, a pharmaceutically acceptable salt thereof, a stereochemically isomeric form thereof or a solvate thereof, wherein X represents N or CH; Y and Z each independently represent C(═O) or CH 2 provided that at least one of Y and Z represents C(═O); R 1 represents CH(R 4 )-aryl or CH(R 4 )-heteroaryl; R 2 represents aryl 2 or heteroaryl; R 3 represents hydrogen; C 1-4 alkylcarbonyl; C 1-6 alkyl optionally substituted with C 1-6 alkyloxy, C 1-6 alkylthio, C 1-6 alkyloxycarbonyl or aryl 1 ; provided that when Y and Z each represent C(═O), X represents CH, R 3 represents hydrogen, R 4 represents hydrogen, and R 2 represents unsubstituted pyridyl or phenyl optionally substituted with one halo or with one C 1-4 alkyloxy or with one or two C 1-4 alkyl, then aryl in the definition of R 1 is other than phenyl substituted with one halo or with one or two C 1-4 alkyl; and provided that when Y and Z each represent C(═O), X represents CH, R 3 represents hydrogen, and R 2 represents unsubstituted pyridyl or phenyl optionally substituted with one halo or with one C 1-4 alkyloxy or with one or two C 1-4 alkyl, then heteroaryl in the definition of R 1 is other than unsubstituted thienyl or unsubstituted pyridyl. The present invention also relates to the use of a compound of formula (I) for the manufacture of a medicament for preventing or treating a disease mediated through activation of the CXCR3 receptor; to processes for preparing the compounds of formula (I) and pharmaceutical compositions comprising them.
• [EN] PIPERIDINE DERIVATIVES AS CXCR3 RECEPTOR ANTAGONISTS<br/>[FR] DERIVES DE PIPERIDINE EN TANT QU'ANTAGONISTES DU RECEPTEUR CXCR3
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2007090826A1

  公开（公告）日：2007-08-16

  [EN] The present invention relates to a compound of formula (I), aN-oxide thereof, a pharmaceutically acceptable salt thereof, a stereochemically isomeric form thereof or a solvate thereof, wherein X represents N or CH; Y and Z each independently represent C(=O) or CH₂ provided that at least one of Y and Z represents C(=O); R¹ represents CH(R⁴)-aryl or CH(R⁴)-heteroaryl; R² represents aryl² or heteroaryl; R³ represents hydrogen; C_1-4alkylcarbonyl; C_1-6alkyl optionally substituted with C_1-6alkyloxy, C_1-6alkylthio, C_1-6alkyloxycarbonyl or aryl¹ ; provided that when Y and Z each represent C(=O), X represents CH, R³ represents hydrogen, R⁴ represents hydrogen, and R² represents unsubstituted pyridyl or phenyl optionally substituted with one halo or with one C_1-4alkyloxy or with one or two C_1-4alkyl, then aryl in the definition of R¹ is other than phenyl substituted with one halo or with one or two C_1-4alkyl; and provided that when Y and Z each represent C(=O), X represents CH, R³ represents hydrogen, and R² represents unsubstituted pyridyl or phenyl optionally substituted with one halo or with one C_1-4alkyloxy or with one or two C_1-4alkyl, then heteroaryl in the definit ion of R¹ is other than unsubstituted thienyl or unsubstituted pyridyl. The present invention also relates to the use of a compound of formula (I) for the manufacture of a medicament for preventing or treating a disease mediated through activation of the CXCR3 receptor; to processes for preparing the compounds of formula (I) and pharmaceutical compositions comprising them.
  [FR] La présente invention concerne un composé de formule (I), un de ses N-oxyde, un de ses sels pharmaceutiquement acceptable, une de ses formes stéréochimiquement isomérique ou un de ses solvates, X représentant N ou CH ; Y et Z représentant chacun indépendamment C(=O) or CH₂, au moins un élément parmi Y et Z représentant C(=O) ; R¹ représentant CH(R⁴)-aryle ou CH(R⁴)-hétéroaryle ; R² représentant aryle ou hétéroaryle ; R³ représentant l'hydrogène ; C_1-4alkylcarbonyle ; C_1-6alkyle éventuellement substitué par C_1-6alkyloxy, C_1-6alkylthio, C_1-6alkyloxycarbonyle ou aryle ; à condition que lorsque Y et Z représentent chacun C(=O), X représente CH, R³ représente l'hydrogène, R⁴ représente l'hydrogène, et R² représente un pyridyle non substitué ou un phényle éventuellement substitué par un halo ou un C_1-4alkyloxy ou un ou deux C_1-4alkyle, aryle dans la définition de R¹ étant autre qu'un phényle substitué par un halo ou un ou deux C_1-4alkyle ; et à condition que lorsque Y et Z représentent chacun C(=O), X représente CH, R³ représente l'hydrogène, et R² représente un pyridyle non substitué ou un phényle éventuellement substitué par un halo ou par un C_1-4alkyloxy ou par un ou deux C_1-4alkyle, un hétéroaryle dans la définition de R¹ étant autre qu'un thiényle non substitué ou un pyridyle non substitué. La présente invention concerne également l'utilisation d'un composé de formule (I) pour la fabrication d'un médicament pour la prévention ou le traitement d'une maladie induite par l'activation du récepteur CXCR3 ; des procédés de préparation des composés de formule (I) et des compositions pharmaceutiques les comprenant.
• Synthesis and structure–activity relationship of benzetimide derivatives as human CXCR3 antagonists
  作者：Jean-Pierre Bongartz、Mieke Buntinx、Erwin Coesemans、Bart Hermans、Guy Van Lommen、Jean Van Wauwe

  DOI：10.1016/j.bmcl.2008.07.115

  日期：2008.11

  The synthesis and evaluation of benzetimide derivatives showing potent CXCR3 antagonism are described. Optimization of the screening hits led to the identification of more potent CXCR3 antagonists devoid of anti-cholinergic activity and identification of the key pharmacophore moieties of the series. (c) 2008 Elsevier Ltd. All rights reserved.