Hydroxybenzoate salts of metanicotine compounds

Details Hydroxybenzoate salts of metanicotine compounds Hydroxybenzoate salts of metanicotine compounds

C - Chemistry, Metallurgy

07

D

C07D 213/46 (2006.01) A61K 31/4406 (2006.01)

Patent

CA 2584586

Patients susceptible to or suffering from conditions and disorders, such as central nervous system disorders, are treated by administering to a patient in need thereof compositions that are hydroxybenzoate salts of E-metanicotine- type compounds. The formation of hydroxybenzoate salts of the E-metanicotine compounds is also useful in purifying the E-metanicotine compounds, as the hydroxybenzoate salts tend to crystallize out, leaving impurities such as Z- metanicotine compounds, and compounds where the double bond has migrated, in solution. If desired, the hydroxybenzoate salts can be converted to either the free base (the E-metanicotine) or to another pharmaceutically acceptable salt form. E-metanicotine-type compounds that include a five-membered heteroaryl ring linked to an olefinic linker, such as a penten-2-amine linker, which is linked to a terminal amine group, are also disclosed. Patients susceptible to or suffering from conditions and disorders, such as central nervous system disorders, can be treated by administering the compounds, pharmaceutical salts of the compounds, or pharmaceutical compositions including the compounds or their salts, to a patient in need thereof.

Selon l'invention, on traite des patients susceptibles de souffrir ou souffrant d'états et de troubles, par exemple du système nerveux central, en administrant à un patient qui en a besoin des compositions qui sont des sels hydroxybenzoates de composés du type E-métanicotine. La formation des sels hydroxybenzoates des composés E-métanicotine est utile également pour purifier les composés E-métanicotine, étant donné que les sels hydroxybenzoates tendent à se cristalliser, laissant en solution des impuretés telles que des composés Z-métanicotine et des composés dans lesquels la liaison double a migré. Les sels hydroxybenzoates peuvent, si désiré, être transformés en base libre (la E-métanicotine) ou en une autre forme de sel acceptable. L'invention se rapporte également aux composés du type E-métanicotine renfermant un noyau hétéroaryle à cinq chaînons lié à un groupe de liaison oléfinique, tel qu'un groupe de liaison pentène-2-amine, qui est lié à un groupe amine terminal. On peut traiter des patients susceptibles de souffrir ou souffrant d'états ou de troubles, par exemple du système nerveux central, en administrant à un patient qui en a besoin les composés, les sels pharmaceutiques des composés ou des compositions pharmaceutiques renfermant les composés précités ou leurs sels.

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