4-(2,4-Dichlorophenyl)-piperidine | 756771-71-8

• 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: 4-(2,4-Dichlorophenyl)-piperidine
• 英文别名: 4-(2,4-Dichlorophenyl)piperidine
• CAS: 756771-71-8
• 化学式: C₁₁H₁₃Cl₂N
• mdl: MFCD05189930
• 分子量: 230.137
• InChiKey: KHZMXNYGPDDEAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(2,4-Dichlorophenyl)-piperidine 、 2-(吡啶-4-基甲氧基)乙酸 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 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 1-(4-(2,4-Dichlorophenyl)piperidin-1-yl)-2-(pyridin-4-ylmethoxy)ethanone
  参考文献：
  名称：

  4-Aryl piperazine and piperidine amides as novel mGluR5 positive allosteric modulators

  摘要：

  Positive allosteric modulation of metabotropic glutamate receptor 5 (mGluR5) is regarded as a potential novel treatment for schizophrenic patients. Herein we report the synthesis and SAR of 4-aryl piperazine and piperidine amides as potent mGluR5 positive allosteric modulators (PAMs). Several analogs have excellent activity and desired drug-like properties. Compound 2b was further characterized as a PAM using several in vitro experiments, and produced robust activity in several preclinical animal models. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.10.036
• 作为产物：
  描述：

  tert-butyl 4-(2,4-dichlorophenyl)-3,6-dihydro-2H-pyridine-1-carboxylate 在 platinum(IV) oxide 、 氢气 、 盐酸 作用下， 以 乙醇 、 1,4-二氧六环 为溶剂， 生成 4-(2,4-Dichlorophenyl)-piperidine
  参考文献：
  名称：

  4-Aryl piperazine and piperidine amides as novel mGluR5 positive allosteric modulators

  摘要：

  Positive allosteric modulation of metabotropic glutamate receptor 5 (mGluR5) is regarded as a potential novel treatment for schizophrenic patients. Herein we report the synthesis and SAR of 4-aryl piperazine and piperidine amides as potent mGluR5 positive allosteric modulators (PAMs). Several analogs have excellent activity and desired drug-like properties. Compound 2b was further characterized as a PAM using several in vitro experiments, and produced robust activity in several preclinical animal models. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.10.036

文献信息

• Constrained compounds as CGRP-receptor antagonists
  申请人：Chaturvedula V. Prasad

  公开号：US20060094707A1

  公开（公告）日：2006-05-04

  The invention encompasses constrained bicyclic and tricyclic CGRP-receptor antagonists, methods for identifying them, pharmaceutical compositions comprising them, and methods for their use in therapy for treatment of migraine and other headaches, neurogenic vasodilation, neurogenic inflammation, thermal injury, circulatory shock, flushing associated with menopause, airway inflammatory diseases, such as asthma and chronic obstructive pulmonary disease (COPD), and other conditions the treatment of which can be effected by the antagonism of CGRP-receptors.

  这项发明涵盖了受限的双环和三环CGRP受体拮抗剂，用于识别它们的方法，包含它们的药物组合物，以及它们在治疗偏头痛和其他头痛、神经源性血管舒张、神经源性炎症、热损伤、循环性休克、与绝经期相关的潮红、气道炎症性疾病（如哮喘和慢性阻塞性肺病（COPD））以及其他可以通过CGRP受体拮抗来治疗的疾病的治疗方法。
• Synthesis and SAR of calcitonin gene-related peptide (CGRP) antagonists containing substituted aryl-piperazines and piperidines
  作者：Rita L. Civiello、Xiaojun Han、Brett R. Beno、Prasad V. Chaturvedula、John J. Herbst、Cen Xu、Charles M. Conway、John E. Macor、Gene M. Dubowchik

  DOI：10.1016/j.bmcl.2016.01.026

  日期：2016.2

  improved oral bioavailability, metabolic stability, and pharmacokinetic properties, lower molecular weight, structurally simpler piperidine and piperazine analogs of BMS-694153 were prepared. Several were found to have nM binding affinity in vitro. The synthesis and SAR of these substituted piperidine and piperazine CGRP antagonists are discussed.

  降钙素基因相关肽（CGRP）是一种强力神经肽，与偏头痛的病理生理有关。在寻求具有改善的口服生物利用度，代谢稳定性和药代动力学性质的CGRP拮抗剂的过程中，制备了BMS-694153的较低分子量，结构更简单的哌啶和哌嗪类似物。发现一些在体外具有nM结合亲和力。讨论了这些取代的哌啶和哌嗪CGRP拮抗剂的合成和SAR。
• Disubstituted Phenylpiperidines as Modulators of Cortical Catecholaminergic Neurotransmission
  申请人：Sonesson Clas

  公开号：US20080269286A1

  公开（公告）日：2008-10-30

  The present invention relates to compounds of the formulae (4), (5) or (6), and their use in the treatment of central nervous system disorders.

  本发明涉及公式（4）、（5）或（6）的化合物及其在治疗中枢神经系统疾病中的应用。
• Constrained Compounds as CGRP-Receptor Antagonists
  申请人：Chaturvedula Prasad V.

  公开号：US20080287422A1

  公开（公告）日：2008-11-20

  The invention encompasses constrained bicyclic and tricyclic CGRP-receptor antagonists, methods for identifying them, pharmaceutical compositions comprising them, and methods for their use in therapy for treatment of migraine and other headaches, neurogenic vasodilation, neurogenic inflammation, thermal injury, circulatory shock, flushing associated with menopause, airway inflammatory diseases, such as asthma and chronic obstructive pulmonary disease (COPD), and other conditions the treatment of which can be effected by the antagonism of CGRP-receptors.

  该发明涵盖了受限的双环和三环CGRP受体拮抗剂，其识别方法，包含它们的药物组合物，以及将其用于治疗偏头痛和其他头痛，神经源性血管扩张，神经源性炎症，热伤害，循环性休克，与更年期有关的潮红，气道炎症性疾病（如哮喘和慢性阻塞性肺疾病（COPD））以及其他通过抗CGRP受体作用进行治疗的疾病的治疗方法。
• CONSTRAINED COMPOUNDS AS CGRP-RECEPTOR ANTAGONISTS
  申请人：Bristol-Myers Squibb Company

  公开号：EP1809633A1

  公开（公告）日：2007-07-25