EPI-589 | 1147883-03-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: EPI-589
• 英文别名: (R)-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide；(R)-2-Hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanamide；(2R)-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanamide
• CAS: 1147883-03-1
• 化学式: C₁₄H₁₉NO₄
• 分子量: 265.309
• InChiKey: BAANPNDZFYBQIB-CQSZACIVSA-N

物化性质

• 沸点：
  465.0±45.0 °C(Predicted)
• 密度：
  1.187±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  97.5
• 氢给体数：
  2
• 氢受体数：
  4

制备方法与用途

EPI-589 是一种醌衍生物，也是一种安全且具有良好耐受性的氧化还原酶抑制剂。它可用于肌萎缩性侧索硬化症的相关研究。

反应信息

• 作为产物：
  描述：

  (R)-(3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyranyl-2-yl)methylamine 在 iron(III) chloride hexahydrate 作用下， 以 水 为溶剂， 生成 EPI-589
  参考文献：
  名称：

  [EN] POLYMORPHIC AND AMORPHOUS FORMS OF (R)-2-HYDROXY-2-METHYL-4-(2,4,5-TRIMETHYL-3,6-DIOXOCYCLOHEXA-1,4-DIENYL)BUTANAMIDE
  [FR] FORMES POLYMORPHES ET AMORPHES DE (R)-2-HYDROXY-2-MÉTHYL-4-(2,4,5-TRIMÉTHYL-3,6-DIOXOCYCLOHEXA-1,4-DIÉNYLE)BUTANAMIDE

  摘要：

  本文披露了(R)-2-羟基-2-甲基-4-(2,4,5-三甲基-3,6-二氧杂环己-1,4-二烯基)丁酰胺的多形和非晶态的无水物、水合物和溶剂化物，以及使用这些组合物治疗或抑制氧化应激性疾病的方法，包括线粒体疾病、能量处理障碍、神经退行性疾病和衰老疾病。此外，本文还披露了制备这些多形和非晶态的方法。

  公开号：

  WO2016100579A1

文献信息

• 4-(p-QUINONYL)-2-HYDROXYBUTANAMIDE DERIVATIVES FOR TREATMENT OF MITOCHONDRIAL DISEASES
  申请人：Jankowski Orion D.

  公开号：US20090118257A1

  公开（公告）日：2009-05-07

  Methods of treating or suppressing mitochondrial diseases, such as Friedreich's ataxia (FRDA), Leber's Hereditary Optic Neuropathy (LHON), mitochondrial myopathy, encephalopathy, lactacidosis, and stroke (MELAS), Kearns-Sayre Syndrome (KSS), are disclosed, as well as compounds useful in the methods of the invention, such as 4-(p-quinolyl)-2-hydroxybutanamide derivatives. Methods and compounds useful in treating other disorders such as amyotrophic lateral sclerosis (ALS), Huntington's disease, Parkinson's disease, and pervasive developmental disorders such as autism are also disclosed. Energy biomarkers useful in assessing the metabolic state of a subject and the efficacy of treatment are also disclosed. Methods of modulating, normalizing, or enhancing energy biomarkers, as well as compounds useful for such methods, are also disclosed.

  揭示了治疗或抑制线粒体疾病的方法，例如弗里德雷希共济失调症（FRDA）、勒伯遗传性视神经病变（LHON）、线粒体肌病、脑病、乳酸中毒和中风（MELAS）、科恩斯-萨耶综合征（KSS），以及在本发明方法中有用的化合物，如4-(对喹啉基)-2-羟基丁酰胺衍生物。还揭示了用于治疗其他疾病的方法和化合物，如肌萎缩侧索硬化症（ALS）、亨廷顿病、帕金森病和广泛性发展障碍如自闭症。还揭示了用于评估受试者代谢状态和治疗疗效的能量生物标志物。还揭示了调节、规范或增强能量生物标志物的方法，以及用于这些方法的化合物。
• OPTICALLY RESOLVED TROLOX INTERMEDIATE AND METHOD FOR PRODUCING SAME
  申请人：Sumitomo Pharma Co., Ltd.

  公开号：EP4108658A1

  公开（公告）日：2022-12-28

  The present invention provides a method for chiral resolution of Trolox. The present disclosure relates to a method for producing a solid salt of a compound of formula I, wherein an amide-based solvent is added to a sample, which contains a compound of formula I, while being assumed to contain a compound of formula II, in the presence of an optical resolution agent: Formula I: (R)-6-hydroxy-2, 5, 7, 8-tetramethylchroman-2-carboxylic acid (hereinafter referred to R Trolox) Formula II: (S)-6-hydroxy-2, 5, 7, 8-tetramethylchroman-2-carboxylic acid (hereinafter referred to S Trolox).

  本发明提供了一种手性解析 Trolox 的方法。本发明涉及一种生产式 I 化合物固体盐的方法，其中在光学解析剂存在的情况下，向含有式 I 化合物的样品中加入酰胺基溶剂，同时假定样品中含有式 II 化合物： 式 I：(R)-6-羟基-2，5，7，8-四甲基苯并二氢吡喃-2-羧酸（以下简称 "R Trolox") 式 II：(S)-6-羟基-2，5，7，8-四甲基苯并二氢吡喃-2-羧酸（以下简称 S Trolox）。
• 4-(p-quinonyl)-2-hydroxybutanamide derivatives for treatment of mitochondrial diseases
  申请人：BioElectron Technology Corporation

  公开号：US10167251B2

  公开（公告）日：2019-01-01

  Methods of treating or suppressing mitochondrial diseases, such as Friedreich's ataxia (FRDA), Leber's Hereditary Optic Neuropathy (LHON), mitochondrial myopathy, encephalopathy, lactacidosis, and stroke (MELAS), Kearns-Sayre Syndrome (KSS), are disclosed, an well as compounds useful in the methods of the invention, such as 4-(p-quinolyl)-2-hydroxybutanamide derivatives. Methods and compounds useful in treating other disorders such as amyotrophic lateral sclerosis (ALS), Huntington's disease, Parkinson's disease and pervasive developmental disorders such as autism are also disclosed. Energy biomarkers useful in assessing the metabolic state of a subject and the efficacy of treatment are also disclosed. Methods of modulating, normalizing, or enhancing energy biomarkers, as well as compounds useful for such methods, are also disclosed.

  本发明公开了治疗或抑制线粒体疾病的方法，如弗里德雷氏共济失调（FRDA）、勒伯氏遗传性视神经病变（LHON）、线粒体肌病、脑病、乳酸中毒和中风（MELAS）、卡恩斯-赛尔综合征（KSS），以及用于本发明方法的化合物，如4-(对喹啉基)-2-羟基丁酰胺衍生物。本发明还公开了用于治疗其他疾病的方法和化合物，如肌萎缩性脊髓侧索硬化症（ALS）、亨廷顿氏病、帕金森氏病和广泛性发育障碍，如自闭症。还公开了有助于评估受试者代谢状态和治疗效果的能量生物标记物。还公开了调节、正常化或增强能量生物标志物的方法以及用于此类方法的化合物。
• Polymorphic and amorphous forms of (R)-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide
  申请人：BIOELECTRON TECHNOLOGY CORPORATION

  公开号：US10251847B2

  公开（公告）日：2019-04-09

  Disclosed herein are polymorphic and amorphous forms of anhydrate, hydrate, and solvates of (R)-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide and methods of using such compositions for treating or suppressing oxidative stress disorders, including mitochondrial disorders, impaired energy processing disorders, neurodegenerative diseases and diseases of aging. Further disclosed are methods of making such polymorphic and amorphous forms.

  本文公开了(R)-2-羟基-2-甲基-4-(2,4,5-三甲基-3,6-二氧代环己-1,4-二烯基)丁酰胺的无水物、水合物和溶质的多晶型和无定形形式，以及使用此类组合物治疗或抑制氧化应激紊乱（包括线粒体紊乱、能量处理受损紊乱、神经退行性疾病和衰老疾病）的方法。进一步公开了制造这种多晶型和无定形型的方法。
• 4-(P-quinonyl)-2-hydroxybutanamide derivatives for treatment of mitochondrial diseases
  申请人：PTC Therapeutics, Inc.

  公开号：US10968166B2

  公开（公告）日：2021-04-06

  Methods of treating or suppressing mitochondrial diseases, such as Friedreich's ataxia (FRDA), Leber's Hereditary Optic Neuropathy (LHON), mitochondrial myopathy, encephalopathy, lactacidosis, and stroke (MELAS), Kearns-Sayre Syndrome (KSS), are disclosed, as well as compounds useful in the methods of the invention, such as 4-(p-quinoly)-2-hydroxybutanamide derivatives. Methods and compounds useful in treating other disorders such as amyotrophic lateral sclerosis (ALS), Huntington's disease, Parkinson's disease, and pervasive developmental disorders such as autism are also disclosed. Energy biomarkers useful in assessing the metabolic state of a subject and the efficacy of treatment are also disclosed. Methods of modulating, normalizing, or enhancing energy biomarkers, as well as compounds useful for such methods, are also disclosed.

  本发明公开了治疗或抑制线粒体疾病的方法，如弗里德雷氏共济失调（FRDA）、勒伯氏遗传性视神经病变（LHON）、线粒体肌病、脑病、乳酸中毒和中风（MELAS）、卡恩斯-赛尔综合征（KSS），以及用于本发明方法的化合物，如4-（对-喹啉基）-2-羟基丁酰胺衍生物。本发明还公开了用于治疗其他疾病的方法和化合物，如肌萎缩性脊髓侧索硬化症（ALS）、亨廷顿氏病、帕金森氏病和广泛性发育障碍，如自闭症。还公开了有助于评估受试者代谢状态和治疗效果的能量生物标记物。还公开了调节、正常化或增强能量生物标志物的方法以及用于此类方法的化合物。