Preparation method of 3,7-diamino-10H-phenothiazine compounds

一种吩噻嗪、二氨基的技术，应用在3,7-二氨基-10H-吩噻嗪化合物领域，能够解决疟疾-相关死亡、耐药性显著等问题

Active Publication Date: 2014-10-29
WISTA LAB LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, drug resistance is a major factor and is especially pronounced for Plasmodium falciparum, the major parasite species responsible for almost all malaria-related deaths

Method used

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  • Preparation method of 3,7-diamino-10H-phenothiazine compounds
  • Preparation method of 3,7-diamino-10H-phenothiazine compounds
  • Preparation method of 3,7-diamino-10H-phenothiazine compounds

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Embodiment

[0541] As described below, the following syntheses are for illustrative purposes only and do not limit the scope of the present invention.

[0542] chemical synthesis

[0543] synthesis 1

[0544] 3-nitro-10H-phenothiazine

[0545]

[0546] Sodium nitrite (20.00g, 210mmol) was added to 10H-phenothiazine (20.00g, 50mmol), chloroform (100cm 3 ) and acetic acid (20cm 3 ), the resulting mixture was stirred at room temperature for 1 hour. Acetic acid was then added to the mixture (20 cm 3 ), and stirred for another 18 hours. The resulting suspension was filtered and washed separately with acetic acid, ethanol, water and finally ethanol to give a purple / brown solid. The residue was dissolved in hot DMF, cooled and filtered to afford the dinitro compound as a purple solid. The DMF solution was concentrated and the precipitate was washed with water and methanol to afford the titled mono-nitro compound (15 g, ~50%) as a brown solid; v max (KBr) / cm -1 :3328(NH),3278(NH),...

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Abstract

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).

Description

[0001] This application is a Chinese invention patent application (application date is March 28, 2007, application number is 200780020349.X (PCT application number is: PCT / GB2007 / 001103), and the invention name is "3,7-diamino-10H- Phenothiazine salts and their use") divisional application. [0002] This application is related to US Patent Application 60 / 786,690, filed March 29, 2006; the contents of US Patent Application 60 / 786,690 are hereby incorporated by reference in their entirety. technical field [0003] The present invention relates generally to the field of phenothiazine compounds; more particularly to certain stably reduced phenothiazine compounds, and in particular to certain 3,7-diamino-10H-phenothiazine (DAPTZ) compounds such as N, N,N',N'-tetramethyl-10H-phenothiazine-3,7-diamine bis(hydrochloride) compound and N,N,N',N'-tetramethyl-10H-phenothiazine- 3,7-Diamine bis(hydroiodic acid) compound. These compounds are used as drugs, e.g. for the treatment of tauopa...

Claims

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Application Information

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Patent Type & AuthorityApplications(China)
IPC IPC(8): C07D279/20A61K31/5415A61P25/28A61P35/00A61P31/12A61P31/04A61P31/14A61P31/18A61P33/06A61P33/02
CPCC07D279/22C09B21/00C07D279/20A61K31/5415A61P1/16A61P13/08A61P13/12A61P25/00A61P25/14A61P25/16A61P25/20A61P25/28A61P29/00A61P31/04A61P31/12A61P31/14A61P31/18A61P33/00A61P33/02A61P33/06A61P35/00A61P43/00A61P7/06A61P9/00A61P3/10Y02A50/30
Inventor克劳德.M.维希克珍妮特.E.里卡德查尔斯.R.哈林顿戴维.霍斯利约翰.M.D.斯托雷科林.马歇尔詹姆斯.P.辛克莱托马斯.C.巴德利
OwnerWISTA LAB LTD