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3,7-diamino-10h-phenothiazine salts and their use

A kind of use, alkyl technology, applied in 3 fields, can solve malaria-related death, significant drug resistance and other problems

Active Publication Date: 2009-06-17
WISTA LAB LTD
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  • Summary
  • 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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  • 3,7-diamino-10h-phenothiazine salts and their use
  • 3,7-diamino-10h-phenothiazine salts and their use
  • 3,7-diamino-10h-phenothiazine salts and their use

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Embodiment

[0466] As described below, the following syntheses are for illustrative purposes only and do not limit the scope of the present invention.

[0467] chemical synthesis

[0468] synthesis 1

[0469] 3-nitro-10H-phenothiazine

[0470]

[0471] Add sodium nitrite (20.00g, 210mmol) 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 title mono-nitro compound (15 g, ~50%) as a brown solid; v max (KBr) / cm -1 : 3328(NH), 3278(NH), 3229...

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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; 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 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 [0002] 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 tauopathy, such as Alzheimer's disease, and also as corresponding sulfoxonium drugs (e.g. methylsulfonium chloride, MTC) prodrug. Background technique [0003] In order to more fully describe and fully disclose this invention and the state of the art related to this invention, this application ref...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D279/20A61K31/5415A61P25/28
CPCC09B21/00C07D279/22C07D279/20A61K31/5415A61P1/16A61P13/08A61P13/12A61P25/00A61P25/14A61P25/16A61P25/20A61P25/28A61P29/00A61P31/04A61P31/12A61P31/14A61P31/18A61P33/00A61P33/02A61P33/06A61P35/00A61P43/00A61P7/06A61P9/00A61P3/10Y02A50/30
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
Owner WISTA LAB LTD