(+)-(3aS,4R,7aS)-4-hydroxy-4-(m-tolylethynyl)-octahydro-indole-1-carboxylic acid methyl ester | 1636881-77-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: (+)-(3aS,4R,7aS)-4-hydroxy-4-(m-tolylethynyl)-octahydro-indole-1-carboxylic acid methyl ester
• 英文别名: (3aS,4R,7aS)-4-hydroxy-4-m-tolylethynyl-octahydro-indole-1-carboxylic acid methyl ester；methyl (3aS,4R,7aS)-4-hydroxy-4-[2-(3-methylphenyl)ethynyl]-3,3a,5,6,7,7a-hexahydro-2H-indole-1-carboxylate
• CAS: 1636881-77-0
• 化学式: C₁₉H₂₃NO₃
• 分子量: 313.397
• InChiKey: ZFPZEYHRWGMJCV-LNLFQRSKSA-N

物化性质

• 沸点：
  476.3±45.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-(3aS,4R,7aS)-4-hydroxy-4-(m-tolylethynyl)-octahydro-indole-1-carboxylic acid methyl ester 、 2-(2-甲氧基乙氧基)乙酸 以to yield (3aR,4S,7aR)-4-[2-(2-methoxy-ethoxy)-acetoxy]-4-m-tolylethynyl-octahydro-indole-1-carboxylic acid methyl ester的产率得到(3aR,4S,7aR)4-[2-(2-methoxy-ethoxy)-acetoxy]-4-m-tolylethynyl-octahydro-indole-1-carboxylic acid methyl ester
  参考文献：
  名称：

  4-Tolyl-ethynyl-octahydro-indole-1-ester derivatives

  摘要：

  该发明涉及化合物(I)的公式，其中取代基如规范中所定义；以自由形式或盐形式存在；其制备方法，其用作药物以及包含它们的药物。

  公开号：

  US20130303538A1
• 作为产物：
  描述：

  (-)-(3aR,4S,7aR)-4-hydroxy-4-(m-tolylethynyl)-octahydro-indole hydrochloride 在 三乙胺 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 、 三氟乙酸 为溶剂， 生成 (3aR,4S,7aR)-八氢-4-羟基-4-[2-(3-甲基苯基)乙炔基]-1H-吲哚-1-羧酸甲酯 、 (+)-(3aS,4R,7aS)-4-hydroxy-4-(m-tolylethynyl)-octahydro-indole-1-carboxylic acid methyl ester
  参考文献：
  名称：

  AFQ056/mavoglurant, a novel clinically effective mGluR5 antagonist: Identification, SAR and pharmacological characterization

  摘要：

  Here we describe the identification, structure-activity relationship and the initial pharmacological characterization of AFQ056/mavoglurant, a structurally novel, non-competitive mGlu5 receptor antagonist. AFQ056/mavoglurant was identified by chemical derivatization of a lead compound discovered in a HTS campaign. In vitro, AFQ056/mavoglurant had an IC50 of 30 nM in a functional assay with human mGluR5 and was selective over the other mGluR subtypes, iGluRs and a panel of 238 CNS relevant receptors, transporter or enzymes. In vivo, AFQ056/mavoglurant showed an improved pharmacokinetic profile in rat and efficacy in the stress-induced hyperthermia test in mice as compared to the prototypic mGluR5 antagonist MPEP. The efficacy of AFQ056/mavoglurant in humans has been assessed in L-dopa induced dyskinesia in Parkinson's disease and Fragile X syndrome in proof of principle clinical studies. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.09.033

文献信息

• [EN] 4-TOLYL-ETHYNYL-OCTAHYDRO-INDOLE-1-ESTER DERIVATIVES<br/>[FR] DÉRIVÉS DE 4-TOLYL-ÉTHYNYL-OCTAHYDRO-INDOLE-1-ESTER
  申请人：NOVARTIS AG

  公开号：WO2012101058A1

  公开（公告）日：2012-08-02

  The invention relates to compounds of the formula (I) in which the substituents are as defined in the specification; in free form or in salt form; to their preparation, to their use as medicament and to medicaments comprising them.

  该发明涉及以下式（I）的化合物，其中取代基如规范中定义；以自由形式或盐形式存在；其制备方法，作为药物的用途以及包含它们的药物。
• 4-tolyl-ethynyl-octahydro-indole-1-ester derivatives
  申请人：Nozulak Joachim

  公开号：US09067881B2

  公开（公告）日：2015-06-30

  The invention relates to compounds of the formula (I) in which the substituents are as defined in the specification; in free form or in salt form; to their preparation, to their use as medicament and to medicaments comprising them.

  该发明涉及公式（I）中取代基的化合物，其中取代基如规范中定义的；以自由形式或盐形式存在；它们的制备，它们作为药物的用途以及包含它们的药物。
• 4-TOLYL-ETHYNYL-OCTAHYDRO-INDOLE-1-ESTER DERIVATIVES
  申请人：Novartis AG

  公开号：EP2668159A1

  公开（公告）日：2013-12-04
• US9067881B2
  申请人：——

  公开号：US9067881B2

  公开（公告）日：2015-06-30