1-(3,7-dinitrophenothiazin-10-yl)-ethanone | 1628-79-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: 1-(3,7-dinitrophenothiazin-10-yl)-ethanone
• 英文别名: 10-Acetyl-3,7-dinitro-phenothiazin；10-acetyl-3,7-dinitro-10H-phenothiazine；1-(3,11-dinitrophenothiazin-10-yl)ethanone；3,7-dinitro-10-acetyl-phenothiazine；1-(3,7-Dinitro-10h-phenothiazin-10-yl)ethanone；1-(3,7-dinitrophenothiazin-10-yl)ethanone
• CAS: 1628-79-1
• 化学式: C₁₄H₉N₃O₅S
• 分子量: 331.309
• InChiKey: VUWDHXCPXJCIJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  137
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(3,7-dinitrophenothiazin-10-yl)-ethanone 在 镍 硝酸 、 一水合肼 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 2.0h， 生成 10-acetyl-5-oxo-5,10-dihydro-5λ⁴-phenothiazine-3,7-diamine
  参考文献：
  名称：

  吩噻嗪系列的合成

  摘要：

  DOI：

  10.1007/bf00475284
• 作为产物：
  描述：

  10H-苯并噻嗪,3-硝基- 在 吡啶 、 溶剂黄146 、 sodium nitrite 作用下， 以 氯仿 为溶剂， 反应 18.0h， 生成 1-(3,7-dinitrophenothiazin-10-yl)-ethanone
  参考文献：
  名称：

  WO2007/110627

  摘要：

  公开号：

文献信息

• Therapeutic use of diaminophenothiazines
  申请人：Wischik Claude Michel

  公开号：US09149481B2

  公开（公告）日：2015-10-06

  The present invention relates generally to methods and materials for use in the treatment or prophylaxis of diseases, for example cognitive disorders, using diaminophenothiazines. In particular it relates to treatments having optimised pharmacokinetic properties, and dosage forms are intended to improve the relative cognitive or CNS benefits of the diaminophenothiazines, for instance compared to haematological effects.

  本发明一般涉及用于治疗或预防疾病的方法和材料，例如认知障碍，使用二氨基苯噻嗪。具体而言，它涉及具有优化药代动力学性质的治疗方法，以及旨在改善二氨基苯噻嗪相对认知或中枢神经系统益处的剂型，例如与造血影响相比。
• [EN] METHOD FOR PREPARATION OF 3,7-BIS-(DIMETHYLAMINO)-PHENOTHIAZIN-5-IUM CHLORIDE OR BROMIDE<br/>[FR] PROCÉDÉ DE PRÉPARATION DE CHLORURE OU BROMURE DE 3,7-BIS-(DIMÉTHYLAMINO)-PHÉNOTHIAZIN-5-IUM
  申请人：MIKROCHEM SPOL S R O

  公开号：WO2018167185A1

  公开（公告）日：2018-09-20

  The present invention relates to: a process for preparing 3,7-bis-(dimethylamino)-phenothiazin-5- ium bromide or chloride; a method of converting 3,7-bis-(dimethylamino)-phenothiazin-5-ium bromide to 3,7-bis-(dimethylamino)-phenothiazin-5-ium chloride; and the purification of 7-bis- (dimethylamino)-phenothiazin-5-ium chloride by crystallization from aqueous solution of hydrochloric acid, leading to a pharmaceutically acceptable 3,7-bis-(dimethylamino)-phenothiazin- 5-ium chloride (methylthioninium chloride, methylene blue, MTC) of formula I below reported.

  本发明涉及：制备3,7-双-(二甲氨基)-苯并噻嗪-5- 唑溴化物或氯化物的方法；将3,7-双-(二甲氨基)-苯并噻嗪-5-唑溴化物转化为3,7-双-(二甲氨基)-苯并噻嗪-5-唑氯化物的方法；以及通过从盐酸水溶液中结晶纯化7-双-(二甲氨基)-苯并噻嗪-5-唑氯化物，得到药用可接受的3,7-双-(二甲氨基)-苯并噻嗪-5-唑氯化物（甲硫鸟苷氯化物，亚甲基蓝，MTC）的方法。
• 3,7-DIAMINO-10H-PHENOTHIAZINE SALTS AND THEIR USE
  申请人：Wischik Claude Michel

  公开号：US20090054419A1

  公开（公告）日：2009-02-26

  This invention pertains generally to the field of phenothiazine compounds, and more particularly to certain stably reduced phenothiazine compounds, specifically, certain 3,7 diamino-10H-phenothiazine (DAPTZ) compounds of the following formula wherein: each of R 1 and R 9 is independently selected from: —H; C 1-4 alkyl; C 2-4 alkenyl; and halogenated C 1-4 alkyl; each of R 3NA and R 3NB is independently selected from: —H; C 1-4 alkyl; C 2-4 alkenyl; and halogenated C 1-4 alkyl; each of R 7NA and R 7NB is independently selected from: —H; C 1-4 alkyl; C 2-4 alkenyl; and halogenated C 1-4 alkyl; each of HX 1 and HX 2 is independently a protic acid; and pharmaceutically acceptable salts, solvates, and hydrates thereof. These compounds are useful as drugs, for example, in the treatment of tauopathies, such as Alzheimer's disease, and also as prodrugs for the corresponding oxidized thioninium drugs (for example, methythioninium chloride, MTC).

  本发明涉及苯并噻嗪化合物领域，更具体地涉及某些稳定还原的苯并噻嗪化合物，具体而言，涉及以下式子的某些3,7-二氨基-10H-苯并噻嗪(DAPTZ)化合物：其中：R1和R9各自独立地选自：—H；C1-4烷基；C2-4烯基；和卤代C1-4烷基；R3NA和R3NB各自独立地选自：—H；C1-4烷基；C2-4烯基；和卤代C1-4烷基；R7NA和R7NB各自独立地选自：—H；C1-4烷基；C2-4烯基；和卤代C1-4烷基；HX1和HX2各自独立地为质子酸；以及其药学上可接受的盐、溶剂化合物和水合物。这些化合物在药物方面具有用途，例如在治疗tau蛋白病中，如阿尔茨海默病，并且作为相应氧化噻唑铵药物（例如甲基噻唑铵盐，MTC）的前药。
• Methods of synthesis and/or purification of diaminophenothiazinium compounds
  申请人：WisTa Laboratories Ltd.

  公开号：US07956183B2

  公开（公告）日：2011-06-07

  A method for the synthesis of a diaminophenothiazinium compound of the following formula: comprising (a) purifying a corresponding reduced compound which is N-acylated at the heterocyclic nitrogen; (b) deacylating the purified compound to provide the corresponding reduced compound; and (c) oxidizing the reduced compound to provide the diaminophenothiazinium compound. Optional purification may performed, for example, after deacylating and after oxidizing. The method provides high purity diaminophenothiazinium compounds which are suitable for pharmaceutical and related therapeutic uses. Such uses include inactivating pathogens, the treatment of the infectious diseases, and for the treatment of diseases of protein aggregation, such as tauopathies, including Alzheimer's disease.

  一种合成以下式子的二氨基苯并噻吩化合物的方法：包括(a)纯化相应的还原化合物，该化合物在杂环氮上被N-酰化；(b)脱酰化纯化后的化合物，以得到相应的还原化合物；(c)氧化还原化合物，以得到二氨基苯并噻吩化合物。可选地，在脱酰化和氧化后进行纯化。该方法提供高纯度的二氨基苯并噻吩化合物，适用于制药和相关治疗用途。这些用途包括灭活病原体，治疗传染病，以及治疗蛋白聚集性疾病，如tau病变，包括阿尔茨海默病。
• 3,7-diamino-10H-phenothiazine salts and their use
  申请人：Wista Laboratories Ltd.

  公开号：US07888350B2

  公开（公告）日：2011-02-15

  This invention pertains generally to the field of phenothiazine compounds, and more particularly to certain stably reduced phenothiazine compounds, specifically, certain 3,7 diamino-10H-phenothiazine (DAPTZ) compounds of the following formula wherein: each of R1 and R9 is independently selected from: —H; C1-4alkyl; C2-4alkenyl; and halogenated C1-4alkyl; each of R3NA and R3NB is independently selected from: —H; C1-4alkyl; C2-4alkenyl; and halogenated C1-4alkyl; each of R7NA and R7NB is independently selected from: —H; C1-4alkyl; C2-4alkenyl; and halogenated C1-4alkyl; each of HX1 and HX2 is independently a protic acid; and pharmaceutically acceptable salts, solvates, and hydrates thereof. These compounds are useful as drugs, for example, in the treatment of tauopathies, such as Alzheimer's disease, and also as prodrugs for the corresponding oxidized thioninium drugs (for example, methythioninium chloride, MTC).

  本发明涉及苯并噻嗪化合物领域，更具体地涉及某些稳定还原的苯并噻嗪化合物，具体来说，涉及以下公式的某些3,7-二氨基-10H-苯并噻嗪（DAPTZ）化合物： 其中，R1和R9各自独立选择自：—H；C1-4烷基；C2-4烯基；和卤代C1-4烷基；R3NA和R3NB各自独立选择自：—H；C1-4烷基；C2-4烯基；和卤代C1-4烷基；R7NA和R7NB各自独立选择自：—H；C1-4烷基；C2-4烯基；和卤代C1-4烷基；HX1和HX2各自独立为质子酸；以及其药学上可接受的盐、溶剂和水合物。这些化合物可用作药物，例如，用于治疗tau病理，如阿尔茨海默病，同时也可作为相应氧化硫铵药物（例如甲硫铵盐，MTC）的前药。