3-(R)-methylgababutin | 223426-17-3

• 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: 3-(R)-methylgababutin
• 英文别名: ((1R,3R)-1-aminomethyl-3-methyl-cyclopentyl)-acetic acid；2-((1R,3R)-1-(aminomethyl)-3-methylcyclopentyl)acetic acid；2-[(1R,3R)-1-(aminomethyl)-3-methylcyclopentyl]acetic acid
• CAS: 223426-17-3
• 化学式: C₉H₁₇NO₂
• 分子量: 171.239
• InChiKey: HYVKVSAZCPKHDV-VXNVDRBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  [(1R,3R)-1-(methoxycarbonylamino-methyl)-3-methyl-cyclopentyl]-acetic acid methyl ester 在 盐酸 、 水 作用下， 以 1,4-二氧六环 为溶剂， 以85%的产率得到3-(R)-methylgababutin
  参考文献：
  名称：

  Synthesis and in vivo evaluation of 3-substituted gababutins

  摘要：

  A range of 3-alkylated five-membered ring derivatives of Gabapentin were synthesized and several were found to have good levels of potency against the alpha 2 delta calcium subunit of a voltage-gated calcium channel. Two compounds were pro. led in in vivo models of pain and anxiety. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.089

文献信息

• Novel method for the stereoselective synthesis of cyclic amino acids
  申请人：Bryans Stephen Justin

  公开号：US20060084825A1

  公开（公告）日：2006-04-20

  The instant invention is a route to stereospecific 3-substituted 5-membered ring isomers of Formula (A). The final products are useful as agents in the treatment of epilepsy, faintness attacks, hypokinesia, cranial disorders, neurodegenerative disorders, depression, anxiety, panic, pain, neuropathological disorders, gastrointestinal disorders such as irritable bowel syndrome (IBS), inflammation especially arthritis, sleep disorders, premenstrual syndrome, and hot flashes. The invention provides novel routes to synthesize stereoselectively analogs of gabapentin (Neurontin™) of Formulas (I), (II), (III), and (IV) wherein R is C 1 -C 10 alkyl or C 3 -C 10 cycloalkyl and pharmaceutically acceptable salts thereof.

  该即时发明是一种合成Formula（A）的立体特异性3-取代5-成员环异构体的途径。最终产品可用作治疗癫痫、昏厥发作、运动减少、颅内疾病、神经退行性疾病、抑郁症、焦虑症、恐慌、疼痛、神经病理性疾病、肠道疾病（如肠易激综合征）、炎症尤其是关节炎、睡眠障碍、经前综合征和潮热的药剂。该发明提供了合成Gabapentin（Neurontin™）的立体选择性类似物的新途径，其化学式为（I）、（II）、（III）和（IV），其中R为C1-C10烷基或C3-C10环烷基及其药学上可接受的盐。
• Method for the stereoselective synthesis of cyclic amino acids
  申请人：——

  公开号：US20030069438A1

  公开（公告）日：2003-04-10

  1 The instant invention is a route to stereospecific 3-substituted 5-membered ring isomers of Formula (A). The final products are useful as agents in the treatment of epilepsy, faintness attacks, hypokinesia, cranial disorders, neurodegenerative disorders, depression, anxiety, panic, pain, neuropathological disorders, gastrointestinal disorders such as irritable bowel syndrome (IBS), inflammation especially arthritis, sleep disorders, premenstrual syndrome, and hot flashes. The invention provides novel routes to synthesize stereoselectively analogs of gabapentin (Neurontin™) of Formulas (I), (II), (III) and (IV) wherein R is C 1 -C 10 alkyl or C 3 -C 10 cycloalkyl and pharmaceutically acceptable salts thereof.

  该发明是一种合成具有立体选择性的Formula (A)中的3-取代5-成员环异构体的途径。最终产物可用作治疗癫痫、晕厥、运动减退、颅内疾病、神经退行性疾病、抑郁症、焦虑症、惊恐症、疼痛、神经病理性疾病、肠道疾病如肠易激综合征（IBS）、炎症特别是关节炎、睡眠障碍、经前综合症和潮热的药物。该发明提供了新的途径，以立体选择性地合成Formula (I)、(II)、(III)和(IV)中的gabapentin（Neurontin™）的类似物，其中R为C1-C10烷基或C3-C10环烷基和其药学上可接受的盐。
• Combinations of an alpha-2-delta ligand with a selective inhibitor of cyclooxygenase-2
  申请人：——

  公开号：US20030199567A1

  公开（公告）日：2003-10-23

  The invention relates to a combination, comprising a selective inhibitor of COX-2, or a pharmaceutically acceptable salt thereof, and an Alpha-2-delta ligand, or a pharmaceutically acceptable salt thereof, and valdecoxib. Examples of selective inhibitors of COX-2 include valdecoxib, rofecoxib, and celecoxib. Examples of Alpha-2-delta ligands include gabapentin, pregabalin, (3S,4S)-( 1 -Aminomethyl-3,4-dimethyl-cyclopentyl)-acetic acid, and 3-(1-aminomethyl-cyclohexylmethyl)-4H-[1,2,4]oxadiazol-5-one hydrochloride. The combinations are useful for treating certain diseases including cartilage damage, inflammation, pain, and arthritis.

  本发明涉及一种组合物，包括COX-2的选择性抑制剂或其药学上可接受的盐，以及Alpha-2-delta配体或其药学上可接受的盐和瓦尔德考昔。 COX-2的选择性抑制剂的例子包括瓦尔德考昔，罗非昔布和塞来昔布。 Alpha-2-delta配体的例子包括加巴喷丁，普拉巴林，（3S，4S）-（1-氨甲基-3,4-二甲基-环戊基）-乙酸和3-（1-氨甲基-环己基甲基）-4H-[1,2,4]噁二唑-5-酮盐酸盐。该组合物可用于治疗某些疾病，包括软骨损伤，炎症，疼痛和关节炎。
• Cyclic amino acids and derivatives thereof useful as pharmaceutical agents
  申请人：——

  公开号：US20030220397A1

  公开（公告）日：2003-11-27

  The invention is a novel series of cyclic amino acids which are useful in the treatment of epilepsy, faintness attacks, neurodegenerative disorders, depression, anxiety, panic, pain, neuropathological disorders, gastrointestinal disorders such as irritable bowel syndrome (IBS), and inflammation, especially arthritis. A pharmaceutical composition containing a compound of the invention as well as methods of preparing the compounds and novel intermediates useful in the preparation of the final compounds are included.

  这项发明是一系列新型的环状氨基酸，可用于治疗癫痫、晕厥发作、神经退行性疾病、抑郁症、焦虑症、惊恐症、疼痛、神经病理性疾病、肠道功能紊乱综合症（IBS）和炎症，特别是关节炎。包含一种该发明化合物的药物组合物以及制备该化合物的方法和制备最终化合物有用的新型中间体。
• Gabapentin analogues for fibromy algia and concomitant disorders
  申请人：——

  公开号：US20040180959A1

  公开（公告）日：2004-09-16

  This invention provides new uses for compounds of formula 1 or a pharmaceutically acceptable salt thereof for the treatment of fibromyalgia and other disorders.

  该发明提供了公式1化合物或其药学上可接受的盐的新用途，用于治疗纤维肌痛和其他疾病。