1-(tert-butoxycarbonyl)-3-(3-methylphenyl)piperidine-4-carboxylic acid | 916420-77-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1-(tert-butoxycarbonyl)-3-(3-methylphenyl)piperidine-4-carboxylic acid
• 英文别名: 3-(3-methylphenyl)-1-[(2-methylpropan-2-yl)oxycarbonyl]piperidine-4-carboxylic acid
• CAS: 916420-77-4
• 化学式: C₁₈H₂₅NO₄
• 分子量: 319.401
• InChiKey: GYECPDXWCPUNQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(tert-butoxycarbonyl)-3-(3-methylphenyl)piperidine-4-carboxylic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 tert-butyl (3RS,4RS)-4-([3,5-bis(trifluoromethyl)benzyl](methyl)carbamoyl)-3-(3-methylphenyl)piperidine-1-carboxylate
  参考文献：
  名称：

  Novel 3-phenylpiperidine-4-carboxamides as highly potent and orally long-acting neurokinin-1 receptor antagonists with reduced CYP3A induction

  摘要：

  The synthesis and biological evaluation of a series of novel 3-phenylpiperidine-4-carboxamide derivatives are described. These compounds are generated by hybridization of the substructures from two types of tachykinin NK1 receptor antagonists. Compound 42 showed high metabolic stability and excellent efficacy in the guinea-pig GR-73637-induced locomotive activity assay at 1 and 24 h after oral administration. It also exhibited good pharmacokinetic profiles in four animal species, and a low potential in a pregnane X receptor induction assay. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.048
• 作为产物：
  描述：

  M-TOLYLMAGNESIUM BROMIDE 在 copper(l) iodide 、 1-氯乙基氯甲酸酯 、 水 、 potassium hydroxide 作用下， 以 乙醚 、 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 19.0h， 生成 1-(tert-butoxycarbonyl)-3-(3-methylphenyl)piperidine-4-carboxylic acid
  参考文献：
  名称：

  Novel 3-phenylpiperidine-4-carboxamides as highly potent and orally long-acting neurokinin-1 receptor antagonists with reduced CYP3A induction

  摘要：

  The synthesis and biological evaluation of a series of novel 3-phenylpiperidine-4-carboxamide derivatives are described. These compounds are generated by hybridization of the substructures from two types of tachykinin NK1 receptor antagonists. Compound 42 showed high metabolic stability and excellent efficacy in the guinea-pig GR-73637-induced locomotive activity assay at 1 and 24 h after oral administration. It also exhibited good pharmacokinetic profiles in four animal species, and a low potential in a pregnane X receptor induction assay. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.048

文献信息

• Piperidine derivative and use thereof
  申请人：Shirai Junya

  公开号：US20080275085A1

  公开（公告）日：2008-11-06

  The present invention provides a novel piperidine derivative and a tachykinin receptor antagonist containing same, as well as a compound represented by the formula: wherein R 1 is carbamoylmethyl, methylsulfonylethylcarbonyl and the like; R 2 is methyl or cyclopropyl; R 3 is a hydrogen atom or methyl; R 4 is a chlorine atom or trifluoromethyl; R 5 is a chlorine atom or trifluoromethyl; and a group represented by the formula: is a group represented by the formula: wherein R 6 is a hydrogen atom, methyl, ethyl or isopropyl; R 7 is a hydrogen atom, methyl or a chlorine atom; and R 8 is a hydrogen atom, a fluorine atom, a chlorine atom or methyl; or 3-methylthiophen-2-yl, and a salt thereof.

  本发明提供了一种新颖的哌啶衍生物和含有该衍生物的催吐肽受体拮抗剂，以及由下式表示的化合物： 其中R1为羰胺甲基、甲磺酰乙基羰基等；R2为甲基或环丙基；R3为氢原子或甲基；R4为氯原子或三氟甲基；R5为氯原子或三氟甲基；以及由下式表示的基团： 是由下式表示的基团： 其中R6为氢原子、甲基、乙基或异丙基；R7为氢原子、甲基或氯原子；R8为氢原子、氟原子、氯原子或甲基；或3-甲基噻吩-2-基，并且其盐。
• [EN] PIPERIDINE DERIVATIVE AND USE THEREOF<br/>[FR] DÉRIVÉ DE PIPERIDINE ET SON UTILISATION
  申请人：TAKEDA PHARMACEUTICAL

  公开号：WO2008133344A2

  公开（公告）日：2008-11-06

  [EN] The present invention provides a novel piperidine derivative and a tachykinin receptor antagonist containing same, as well as a compound represented by the formula (I) wherein R1 is carbamoylmethyl, methylsulfonylethylcarbonyl and the like; R2 is methyl or cyclopropyl; R3 is a hydrogen atom or methyl; R4 is a chlorine atom or trifluoromethyl; R5 is a chlorine atom or trifluoromethyl; and a group represented by the formula (II) is a group represented by the formula (III) wherein R6 is a hydrogen atom, methyl, ethyl or isopropyl; R7 is a hydrogen atom, methyl or a chlorine atom; and R8 is a hydrogen atom, a fluorine atom, a chlorine atom or methyl; or 3-methylthiophen-2-yl, and a salt thereof.
  [FR] La présente invention concerne un nouveau dérivé de piperidine et un antagoniste du récepteur tachykinine comprenant celui-ci, ainsi qu'un composé représenté par la formule (I), dans laquelle R1 représente carbamoylméthyle, méthylsulfonyléthylcarbonyle et similaire, R2 représente méthyle ou cyclopropyle; R3 représente un atome d'hydrogène ou méthyle, R4 représente un atome de chlore ou trifluorométhyle, R5 représente un atome de chlore ou trifluorométhyle, et un groupe représenté par la formule (II) constitue un groupe représenté par la formule (III), où R6 représente un atome d'hydrogène, méthyle, éthyle ou isopropyle, R7 représente un atome d'hydrogène, méthyle ou un atome de chlore, et R8 représente un atome d'hydrogène, un atome de fluor, un atome de chlore ou méthyle ou 3-méthylthiophèn-e2-yl, et un sel de ceux-ci.