ethyl 4-(4-benzylpiperazin-1-yl)cyclohexanecarboxylate | 1088710-04-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 4-(4-benzylpiperazin-1-yl)cyclohexanecarboxylate
• 英文别名: ethyl 4-(4-benzylpiperazin-1-yl)cyclohexane-1-carboxylate
• CAS: 1088710-04-6
• 化学式: C₂₀H₃₀N₂O₂
• 分子量: 330.47
• InChiKey: FIPJTZLOPKPOCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 4-(4-benzylpiperazin-1-yl)cyclohexanecarboxylate 在 sodium hydroxide 、 水 、 三氟乙酸 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 48.0h， 生成 4-(4-benzylpiperazin-1-yl)cyclohexanecarboxylic acid
  参考文献：
  名称：

  WO2008/145681

  摘要：

  公开号：
• 作为产物：
  描述：

  N,N-双(2-氯乙基)苯甲胺 、 ethyl cis-4-aminocyclohexanecarboxylate hydrochloride 在 碳酸氢钠 作用下， 以 乙醇 为溶剂， 以68%的产率得到ethyl 4-(4-benzylpiperazin-1-yl)cyclohexanecarboxylate
  参考文献：
  名称：

  Discovery of a Novel 5-HT₃ Antagonist/5-HT_1A Agonist 3-Amino-5,6,7,8-tetrahydro-2-{4-[4-(quinolin-2-yl)piperazin-1-yl]butyl}quinazolin-4(3H)-one (TZB-30878) as an Orally Bioavailable Agent for Irritable Bowel Syndrome

  摘要：

  We have prepared a series of quinazolinone derivatives linked with piperazinylquinoline for the treatment of irritable bowel syndrome (IBS). Using pharmacophore analysis, we designed and synthesized compounds which bind to both serotonin receptor subtype 1A (5-HT1A) and subtype 3 (5-HT3). Quinazolinone derivatives with a sulfur atom in the linker showed high affinity in in vitro assays, but low in vivo activity. Focusing on the linker to improve the pharmacokinetic profile, the sulfur atom in the linker was replaced with a methylene group. Further optimization led to the discovery of compound 17m (TZB-30878) (J. Pharmacol. Exp. Ther. 2007, 322, 1315-1323, Patent WO2005082887 (A1), 2005), a novel 5-HT1A agonist/5-HT3 antagonist in the 3-aminoquinazolinone series. In in vivo functional assays, 17m dose dependently inhibited the Bezold-Jarisch reflex and induced 5-HT1A-mediated behaviors, and in an IBS animal model, 17m significantly inhibited stress-induced defecation. Pretreatment by WAY-100635 (5-HT1A antagonist) significantly attenuated but did not abolish the inhibitory effects of 17m. These results suggested that 17m exerted inhibitory effects via both 5-HT1A agonistic and 5-HT3 antagonistic activities and that 17m would be useful as a therapeutic agent for IBS.

  DOI：

  10.1021/jm1002292

文献信息

• CCR2 Receptor Antagonists and Uses Thereof
  申请人：Ebel Heiner

  公开号：US20100204209A1

  公开（公告）日：2010-08-12

  The present invention relates to novel antagonists for CCR2 (CC chemokine receptor 2) and their use for providing medicaments for treating conditions and diseases, especially pulmonary diseases like asthma and COPD.

  本发明涉及新型CCR2（CC趋化因子受体2）拮抗剂及其用于提供治疗疾病和病症的药物，特别是用于治疗肺部疾病，如哮喘和COPD。
• CCR2 receptor antagonists and uses thereof
  申请人：Ebel Heiner

  公开号：US08653262B2

  公开（公告）日：2014-02-18

  The present invention relates to novel antagonists for CCR2 (CC chemokine receptor 2) and their use for providing medicaments for treating conditions and diseases, especially pulmonary diseases like asthma and COPD.

  本发明涉及新的CCR2（CC趋化因子受体2）拮抗剂及其用途，用于提供治疗疾病和病症的药物，特别是用于治疗肺部疾病，如哮喘和COPD。
• CCR2 RECEPTOR ANTAGONISTS AND USES THEREOF
  申请人：Boehringer Ingelheim International GmbH

  公开号：EP2155689A2

  公开（公告）日：2010-02-24
• US8653262B2
  申请人：——

  公开号：US8653262B2

  公开（公告）日：2014-02-18
• [EN] CCR2 RECEPTOR ANTAGONISTS AND USES THEREOF<br/>[FR] ANTAGONISTES DES RÉCEPTEURS CCR2 ET UTILISATIONS DE CEUX-CI
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2008145681A2

  公开（公告）日：2008-12-04

  [EN] The present invention relates to novel antagonists for CCR2 (CC chemokine receptor 2) and their use for providing medicaments for treating conditions and diseases, especially pulmonarydiseases like asthma and COPD.
  [FR] L'invention concerne de nouveaux antagonistes de CCR2 (récepteur 2 des chimiokines CC) et leur utilisation pour produire des médicaments destinés à traiter des états pathologiques et des maladies, notamment des maladies pulmonaires telles que l'asthme et la bronchopneumopathie chronique obstructive.