6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-carboxamide | 53101-53-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-carboxamide
• 英文别名: 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxamide；6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carboxamide
• CAS: 53101-53-4
• 化学式: C₁₄H₁₉NO₃
• 分子量: 249.31
• InChiKey: BVYZEFLWUAIZRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-carboxamide 、 硝酸铈铵 以yielded 157 mg of 2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide as a yellow solid的产率得到2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide
  参考文献：
  名称：

  4-(p-QUINONYL)-2-HYDROXYBUTANAMIDE DERIVATIVES FOR TREATMENT OF MITOCHONDRIAL DISEASES

  摘要：

  本发明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-赛尔综合症（KSS），以及在该发明中有用的化合物，例如4-（对苯二酚基）-2-羟基丁酰胺衍生物。本发明还揭示了用于治疗其他疾病的方法和化合物，例如肌萎缩性侧索硬化症（ALS），亨廷顿病，帕金森病以及广泛性发育障碍，例如自闭症。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。本发明还揭示了调节、规范或增强能量生物标志物的方法，以及用于此类方法的化合物。

  公开号：

  US20120122934A1
• 作为产物：
  描述：

  奎诺二甲基丙烯酸酯 在 氨 作用下， 生成 6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-carboxamide
  参考文献：
  名称：

  [EN] COMPOUNDS FOR PROTECTION OF CELLS
  [FR] COMPOSÉS POUR LA PROTECTION DES CELLULES

  摘要：

  这项发明涉及具有结构式（I）的化合物。其中，R1和R2分别从C1-C6烷基组中选择，最好是甲基、乙基、丙基或异丙基；R3从CH2NHR9、C(=0)YR10、-CH20H组中选择；公式（II）。

  公开号：

  WO2014098586A1

文献信息

• [EN] 6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMAN-COMPOUNDS FOR THE TREATMENT OF CHRONIC OBSTRUCTIVE AIRWAY DISEASES<br/>[FR] COMPOSÉS 6-HYDROXY-2,5,7,8-TETRAMÉTHYLCHROMAN- POUR LE TRAITEMENT DE MALADIES OBSTRUCTIVES CHRONIQUES DES VOIES RESPIRATOIRES
  申请人：SULFATEQ BV

  公开号：WO2015193365A1

  公开（公告）日：2015-12-23

  The present invention relates to compounds for the treatment of chronic obstructive airway diseases such as chronic obstructive pulmonary disease (COPD) or asthma or bronchiectasis. The present invention further relates to drug delivery devices suitable to be used in the treatment of chronic obstructive airway diseases such as a nebulizer comprising the present compounds. Specifically, the present invention relates to (6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)(piperazin-1-yl)methanone or N,6-dihydroxy-2,5,7,8-tetramethylchroman-2-carboxamide or a pharmaceutically acceptable salt or base thereof for use in the treatment of chronic obstructive airway diseases, preferably chronic obstructive pulmonary disease (COPD) or asthma or bronchiectasis, more preferably chronic obstructive pulmonary disease (COPD).

  本发明涉及用于治疗慢性阻塞性气道疾病，如慢性阻塞性肺病（COPD）或哮喘或支气管扩张症的化合物。本发明还涉及适用于治疗慢性阻塞性气道疾病的药物给药装置，例如包含本发明化合物的雾化器。具体地，本发明涉及用于治疗慢性阻塞性气道疾病，尤其是慢性阻塞性肺病（COPD）或哮喘或支气管扩张症的（6-羟基-2,5,7,8-四甲基色素-2-基）（哌嗪-1-基）甲酮或N,6-二羟基-2,5,7,8-四甲基色素-2-甲酰胺或其药用可接受的盐或碱。
• [EN] COMPOUND FOR THE PROPHYLAXIS OR TREATMENT OF ORGAN DAMAGE<br/>[FR] COMPOSÉ POUR LA PROPHYLAXIE OU LE TRAITEMENT DE LÉSION D'ORGANE
  申请人：SULFATEQ BV

  公开号：WO2016188766A1

  公开（公告）日：2016-12-01

  The present invention relates to compounds for prophylaxis or treatment of organ damage by restoring endothelial function and/or inhibiting reactive oxygen species production and especially to compounds for prophylaxis or treatment of diabetic kidney damage. Specifically, the present invention relates to 6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)(piperazin-1-yl)methanone or N,6-dihydroxy-2,5,7,8-tetramethylchroman-2-carboxamide or a pharmaceutically acceptable salt or base thereof for use in the prophylaxis or treatment of organ damage by restoring endothelial function and/or inhibiting reactive oxygen species production and especially diabetic kidney organ damage.

  本发明涉及用于预防或治疗器官损伤的化合物，通过恢复内皮功能和/或抑制活性氧产生，特别是用于预防或治疗糖尿病肾损伤的化合物。具体而言，本发明涉及6-羟基-2,5,7,8-四甲基色烯-2-基)(哌嗪-1-基)甲酮或N,6-二羟基-2,5,7,8-四甲基色烯-2-羧酰胺或其药用可接受的盐或碱，用于通过恢复内皮功能和/或抑制活性氧产生，特别是糖尿病肾器官损伤的预防或治疗。
• [EN] POLYMORPHIC AND AMORPHOUS FORMS OF (R)-2-HYDROXY-2-METHYL-4-(2,4,5-TRIMETHYL-3,6-DIOXOCYCLOHEXA-1,4-DIENYL)BUTANAMIDE<br/>[FR] FORMES POLYMORPHES ET AMORPHES DE (R)-2-HYDROXY-2-MÉTHYL-4-(2,4,5-TRIMÉTHYL-3,6-DIOXOCYCLOHEXA-1,4-DIÉNYLE)BUTANAMIDE
  申请人：EDISON PHARMACEUTICALS INC

  公开号：WO2016100579A1

  公开（公告）日：2016-06-23

  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。
• Hydroquinone derivative and pharmaceutical use thereof
  申请人：Japan Energy Corporation

  公开号：US05821247A1

  公开（公告）日：1998-10-13

  Disclosed is a hydroquinone derivative or a pharmaceutically acceptable salt thereof, the hydroquinone derivative being represented by formula (I): ##STR1## wherein R.sup.1 is a phenyl group which is unsubstituted or substituted with a substituent or substituents each independently selected from the group consisting of a halogen atom, a C1-4 alkyl group and a C1-4 alkoxy group; R.sup.2 is a hydrogen atom or a C1-4 alkyl group; each of R.sup.3 and R.sup.4 is independently a hydrogen atom or a C1-4 alkyl group; R.sup.5 is a hydrogen atom or a C1-4 alkyl group; each of R.sup.6, R.sup.7 and R.sup.8 is independently a hydrogen atom or a C1-4 alkyl group; P is a hydroxyl group; Q is a hydroxyl group, a C1-4 alkoxy group, a C1-18 acyloxy group or an oxo group; P may form together with Q an ether bond; R is a hydroxyl group, a C1-4 alkoxy group, a C1-18 acyloxy group or an oxo group, provided that when one of said Q and said R is an oxo group, the other is also an oxo group; X is a single bond, an --NR.sup.10 --group or a --CH.sub.2 --NR.sup.10 --group in which R.sup.10 is a hydrogen atom or a C1-4 alkyl group; Y is a methylene group or a carbonyl group; and dotted bonds in a six membered ring represent that said six membered ring has the maximum number of double bonds.

  本发明涉及一种羟基苯醌衍生物或其药学上可接受的盐，该羟基苯醌衍生物由公式（I）表示：##STR1##其中，R.sup.1是苯基，其未取代或被取代为取自卤原子、C1-4烷基和C1-4烷氧基的各自独立的取代基；R.sup.2是氢原子或C1-4烷基；R.sup.3和R.sup.4各自独立地是氢原子或C1-4烷基；R.sup.5是氢原子或C1-4烷基；R.sup.6，R.sup.7和R.sup.8各自独立地是氢原子或C1-4烷基；P是羟基；Q是羟基、C1-4烷氧基、C1-18酰氧基或氧代基；P可以与Q共同形成醚键；R是羟基、C1-4烷氧基、C1-18酰氧基或氧代基，但当Q和R中的一个为氧代基时，另一个也为氧代基；X是单键、--NR.sup.10--基团或--CH.sub.2--NR.sup.10--基团，其中R.sup.10是氢原子或C1-4烷基；Y是亚甲基基团或羰基基团；六元环中的点状键表示该六元环具有最大数量的双键。
• 4-(p-quinonyl)-2-hydroxybutanamide derivatives for treatment of mitochondrial diseases
  申请人：Edison Pharmaceuticals, Inc.

  公开号：US07968746B2

  公开（公告）日：2011-06-28

  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.

  本发明公开了治疗或抑制线粒体疾病的方法，如弗里德赫氏共济失调症（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）、基恩斯-塞尔综合症（KSS），以及在本发明方法中有用的化合物，如4-(p-喹啉基)-2-羟基丁酰胺衍生物。本发明还公开了治疗其他疾病，如肌萎缩性侧索硬化症（ALS）、亨廷顿病、帕金森病和广泛性发育障碍，如自闭症的方法和化合物。本发明还公开了用于评估受试者代谢状态和治疗效果的能量生物标志物。本发明还公开了调节、规范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。