tert-butyl 4-[(RS)-(4-chlorophenyl)(cyano)methyl]piperidine-1-carboxylate | 1207438-47-8

• 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: tert-butyl 4-[(RS)-(4-chlorophenyl)(cyano)methyl]piperidine-1-carboxylate
• 英文别名: tert-butyl 4-((4-chlorophenyl)(cyano)methyl)piperidine-1-carboxylate；tert-Butyl 4-((4-chlorophenyl)(cyano)methyl)piperidine-1-carboxylate；tert-butyl 4-[(4-chlorophenyl)-cyanomethyl]piperidine-1-carboxylate
• CAS: 1207438-47-8
• 化学式: C₁₈H₂₃ClN₂O₂
• 分子量: 334.846
• InChiKey: DNNWAVYYUHAHTI-UHFFFAOYSA-N

物化性质

• 沸点：
  453.6±20.0 °C(Predicted)
• 密度：
  1.172±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 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：
  53.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-[(RS)-(4-chlorophenyl)(cyano)methyl]piperidine-1-carboxylate 在 甲醇 、 sodium tetrahydroborate 、 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 tert-butyl 4-[(1RS)-1-(4-chlorophenyl)-2-hydroxyethyl]piperidine-1-carboxylate
  参考文献：
  名称：

  [EN] SULFONYL PIPERIDINE DERIVATIVES AND THEIR USE FOR TREATING PROKINETICIN MEDIATED DISEASES
  [FR] DÉRIVÉS DE SULFONYLPIPÉRIDINE ET LEUR UTILISATION POUR LE TRAITEMENT DE MALADIES MÉDIÉES PAR UNE PROKINÉTICINE

  摘要：

  本发明提供了以下式（I）的化合物及其药学上可接受的盐：（I）其中m、n、W、X、Y、Z、R1、R2、R3和R4如规范中定义，用于治疗或预防由前动力素介导的疾病或状况，如精神疾病和神经病状。

  公开号：

  WO2013179024A1
• 作为产物：
  描述：

  对氯苯乙腈 在 sodium tetrahydroborate 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.5h， 生成 tert-butyl 4-[(RS)-(4-chlorophenyl)(cyano)methyl]piperidine-1-carboxylate
  参考文献：
  名称：

  Novel triple reuptake inhibitors with low risk of CAD associated liabilities: Design, synthesis and biological activities of 4-[(1S)-1-(3,4-dichlorophenyl)-2-methoxyethyl]piperidine and related compounds

  摘要：

  A novel triple reuptake inhibitor with low potential of liabilities associated with cationic amphiphilic drug (CAD) was identified following an analysis of existing drugs. Low molecular weight (MW < ca. 300), low aromatic ring count (number = 1) and reduced lipophilicity (ClogP < 3.5) were hypothesized to be key factors to avoid the CAD associated liabilities (CYP2D6 inhibition, hERG inhibition and phospholipidosis). Based on the hypothesis, a series of piperidine compounds was designed with consideration of the common characteristic features of CNS drugs. Optimization of the side chain by adjusting overall lipophilicity suggested that incorporation of a methoxymethyl group could provide compounds with a balance of both potent reuptake inhibition and low liability potential. Compound (S)-3a showed a potent antidepressant-like effect in the mice tail suspension test (MED = 10 mg/kg, p.o.), proportional monoamine transporter occupancies and enhancement of monoamine concentrations in mouse prefrontal cortex. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.025

文献信息

• THERAPEUTIC COMPOUNDS
  申请人：Takeda Pharmaceutical Company Limited

  公开号：US20130324576A1

  公开（公告）日：2013-12-05

  The present invention provides compounds of formula (I) and pharmaceutically acceptable salts thereof in which m, n, W, X, Y, Z, R, R 1 , R 2 , R 3 and R 4 are as defined in the specification, for use in therapy.

  本发明提供了式(I)的化合物及其药学上可接受的盐，其中m、n、W、X、Y、Z、R、R1、R2、R3和R4如规范中定义，用于治疗。
• [EN] SULFONYL PIPERIDINE DERIVATIVES AND THEIR USE FOR TREATING PROKINETICIN MEDIATED DISEASES<br/>[FR] DÉRIVÉS DE SULFONYLPIPÉRIDINE ET LEUR UTILISATION POUR LE TRAITEMENT DE MALADIES MÉDIÉES PAR UNE PROKINÉTICINE
  申请人：TAKEDA PHARMACEUTICAL

  公开号：WO2013179024A1

  公开（公告）日：2013-12-05

  The present invention provides compounds of formula (I) and pharmaceutically acceptable salts thereof : (I) in which m, n, W, X, Y, Z, R1, R2, R3 and R4 are as defined in the specification, for use in the treatment or prevention of a diseases o conition mediated by a prokineticin, such as psychiatric and neurological conitions.

  本发明提供了以下式（I）的化合物及其药学上可接受的盐：（I）其中m、n、W、X、Y、Z、R1、R2、R3和R4如规范中定义，用于治疗或预防由前动力素介导的疾病或状况，如精神疾病和神经病状。
• SULFONYL PIPERIDINE DERIVATIVES AND THEIR USE FOR TREATING PROKINETICIN MEDIATED DISEASES
  申请人：TAKEDA PHARMACEUTICAL COMPANY LIMITED

  公开号：US20150111922A1

  公开（公告）日：2015-04-23

  The present invention provides compounds of formula (I) and pharmaceutically acceptable salts thereof: (I) in which m, n, W, X, Y, Z, R 1 , R 2 , R 3 and R 4 are as defined in the specification, for use in the treatment or prevention of a diseases o conition mediated by a prokineticin, such as psychiatric and neurological conditions.

  本发明提供了公式（I）的化合物及其药学上可接受的盐：（I）其中m、n、W、X、Y、Z、R1、R2、R3和R4如规范中所定义，用于治疗或预防由前动力素介导的疾病或情况，例如精神和神经疾病。
• Sulfonyl piperidine derivatives and their use for treating prokineticin mediated diseases
  申请人：TAKEDA PHARMACEUTICAL COMPANY LIMITED

  公开号：US10167273B2

  公开（公告）日：2019-01-01

  The present invention provides compounds of formula (I) and pharmaceutically acceptable salts thereof in which q, R11, R12, R13 and R14 are as defined in the specification, for use in therapy.

  本发明提供了式 (I) 化合物及其药学上可接受的盐类 其中 q、R11、R12、R13 和 R14 如说明书中所定义，用于治疗。
• US9475795B2
  申请人：——

  公开号：US9475795B2

  公开（公告）日：2016-10-25