2-[2-(aminomethyl)cyclohexyl]acetic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-[2-(aminomethyl)cyclohexyl]acetic acid
• 英文别名: 2-[2-(azaniumylmethyl)cyclohexyl]acetate
• 化学式: C₉H₁₇NO₂
• 分子量: 171.239
• InChiKey: VMTBKRPFIUIKPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  氯甲酸-9-芴基甲酯 、 2-[2-(aminomethyl)cyclohexyl]acetic acid 在 sodium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以26%的产率得到2-{2-[({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)methyl]cyclohexyl}acetic acid
  参考文献：
  名称：

  Discovery of Novel Nonpeptidic PAR2 Ligands

  摘要：

  Proteinase-activated receptor 2 (PAR2) is a class A G protein-coupled receptor whose activation has been associated with inflammatory diseases and cancer, thus representing a valuable therapeutic target. Pathophysiological roles of PAR2 are often characterized using peptidic PAR2 agonists. Peptidic ligands are frequently unstable in vivo and show poor bioavailability, and only a few approaches toward drug-like nonpeptidic PAR2 ligands have been described. The herein-described ligand 5a (IK187) is a nonpeptidic PAR2 agonist with submicromolar potency in a functional assay reflecting G protein activation. The ligand also showed substantial ss-arrestin recruitment. The development of the compound was guided by the crystal structure of PAR2, when the C-terminal end of peptidic agonists was replaced by a small molecule based on a disubstituted phenylene scaffold. IK187 shows preferable metabolic stability and may serve as a lead compound for the development of nonpeptidic drugs addressing PAR2.

  DOI：

  10.1021/acsmedchemlett.0c00154
• 作为产物：
  描述：

  2-氨基甲基苯乙酸 在 5wt.% Rh on activated alumina 、 氢气 作用下， 以 水 为溶剂， 100.0 ℃ 、1.8 MPa 条件下， 反应 24.0h， 以92%的产率得到2-[2-(aminomethyl)cyclohexyl]acetic acid
  参考文献：
  名称：

  Discovery of Novel Nonpeptidic PAR2 Ligands

  摘要：

  Proteinase-activated receptor 2 (PAR2) is a class A G protein-coupled receptor whose activation has been associated with inflammatory diseases and cancer, thus representing a valuable therapeutic target. Pathophysiological roles of PAR2 are often characterized using peptidic PAR2 agonists. Peptidic ligands are frequently unstable in vivo and show poor bioavailability, and only a few approaches toward drug-like nonpeptidic PAR2 ligands have been described. The herein-described ligand 5a (IK187) is a nonpeptidic PAR2 agonist with submicromolar potency in a functional assay reflecting G protein activation. The ligand also showed substantial ss-arrestin recruitment. The development of the compound was guided by the crystal structure of PAR2, when the C-terminal end of peptidic agonists was replaced by a small molecule based on a disubstituted phenylene scaffold. IK187 shows preferable metabolic stability and may serve as a lead compound for the development of nonpeptidic drugs addressing PAR2.

  DOI：

  10.1021/acsmedchemlett.0c00154

文献信息

• Neue Diphosphonsäurederivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel
  申请人：BOEHRINGER MANNHEIM GMBH

  公开号：EP0224751A1

  公开（公告）日：1987-06-10

  Die Erfindung betrifft Diphosphonsäurederivate der allge­meinen Formel I in der R₁, R₂ jeweils unabhängig voneinander oder auch gemeinsam Wasserstoff, niederes Acyl oder Alkyl, das durch Aryl substituiert sein kann, R₃, R₄ jeweils unabhängig voneinander oder gemeinsam Wasser­stoff, niederes Alkyl oder zusammen niederes Alkylen, R₅ Wasserstoff oder niederes Alkyl, X einen Valenzstrich oder niederes, geradkettiges oder ver­zweigtes Alkylen, Y einen Valenzstrich, niederes, geradkettiges oder verzweigtes, gegebenenfalls durch substituiertes Alkylen, Z Wasserstoff, Hydroxy oder gegebenenfalls durch Alkylgruppen substituiertes Amino und n = 1 - 3 bedeuten, sowie deren pharmakologisch unbedenkliche Salze, Verfahren zu ihrer Herstellung sowie Arzneimittel, die diese Verbin­dungen enthalten zur Behandlung von Calciumstoffwechsel­störungen.

  本发明涉及通式 I 的二膦酸衍生物 其中 R₁、R₂各自独立或同时为氢、低级酰基或烷基，可被芳基取代、 R₃、R₄各自独立或同时为氢、低级烷基或同时为低级亚烷基、 R₅ 氢或低级烷基、 X 是价基或低级直链或支链亚烷基、 Y 是价族、低级直链或支链亚烷基，可选被 取代的亚烷基、 Z 是氢、羟基或可选被烷基取代的氨基，以及 n = 1 - 3, 及其药理上可接受的盐、制备工艺和含有这些化合物的用于治疗钙代谢紊乱的药物。
• THERAPEUTIC AGENT OR PROPHYLACTIC AGENT FOR NEUROPATHIC PAIN
  申请人：Toray Industries, Inc.

  公开号：EP2599487A1

  公开（公告）日：2013-06-05

  An object of the present invention is to provide a therapeutic agent or a prophylactic agent for neuropathic pain, by which a synergistically-enhanced analgesic effect is obtained at a dose at which a calcium channel α2δ ligand does not produce any side effects as well as which agent does not produce any new side effects on the central nervous system. The present invention provides a therapeutic agent or a prophylactic agent for neuropathic pain comprising as effective ingredients a cyclohexane derivative, represented by the following formula, or a pharmaceutically acceptable salt thereof or a prodrug thereof, and a calcium channel α2δ ligand.

  本发明的目的是提供一种神经病理性疼痛的治疗剂或预防剂，通过这种治疗剂或预防剂，在钙通道α2δ配体不产生任何副作用以及该治疗剂不对中枢神经系统产生任何新的副作用的剂量下，可获得协同增强的镇痛效果。本发明提供了一种神经病理性疼痛的治疗剂或预防剂，其有效成分包括下式表示的环己烷衍生物或其药学上可接受的盐或其原药，以及钙通道α2δ配体。
• EP2599487B1
  申请人：——

  公开号：EP2599487B1

  公开（公告）日：2015-04-01
• TREATMENT OF ADHD
  申请人：Bird Philip

  公开号：US20100087422A1

  公开（公告）日：2010-04-08

  A method is described for treating attention deficit hyperactivity disorder (ADHD), by administering to the individual an anti-epileptic mood stabiliser at a dose which is sub-therapeutic for mood stabilisation, optionally in combination with a psychostimulant. Also described is a method of improving reading comprehension and/or fluency in an individual suffering from learning difficulties which method comprises administering to the individual an anti-epileptic mood stabiliser.
• METHODS OF TREATING OR PREVENTING NEUROPATHIC PAIN
  申请人：Toray Industreis, Inc.

  公开号：US20150105430A1

  公开（公告）日：2015-04-16

  A method treats or prevents neuropathic pain with a synergistically-enhanced analgesic effect at a dose at which a calcium channel α2δ ligand does not produce any side effects as well as which agent does not produce any new side effects on the central nervous system. The therapeutic agent or a prophylactic agent used in the method includes as effective ingredients a cyclohexane derivative or a pharmaceutically acceptable salt thereof or a prodrug thereof, and a calcium channel α2δ ligand.