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

C - Chemistry – Metallurgy – 07 – D

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Details

C07D 279/20 (2006.01) A61K 31/5415 (2006.01) A61P 25/28 (2006.01)

Patent

CA 2646163

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).

L'invention concerne, de manière générale, des composés de phénothiazine, et plus particulièrement, certains composés de phénothiazine soumis à une réduction stable, spécifiquement, certains composés de,7 diamino-10H-phénothiazine (DAPTZ) représentés par la formule (I): dans laquelle R1 et R9 sont indépendamment sélectionnés dans: -H; C1-4alkyle; C2-4alcényle et C1-4alkyle halogéné; chacun de R3NA et R3NB est indépendamment sélectionné dans: -H; C1-4alkyle; C2-4alcényle; et C1-4alkyle halogéné; chacun de R7NA et R7NB est indépendamment sélectionné dans: -H; C1-4alkyle; C2-4alcényle; et C1-4alkyle halogéné; et chacun de HX1 et HX2 représente indépendamment un acide protique; l'invention concernant en outre des sels, solvates et hydrates de qualité pharmaceutique correspondants. Ces composés sont utiles comme médicaments, par exemple, dans le traitement des tauopathies, notamment la maladie d'Alzheimer, ainsi que comme promédicaments pour les médicaments à base de thioninium oxydé correspondants (par exemple, le chlorure de méthythioninium chloride, MTC).

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