Stable salts of novel derivatives of 3,3-diphenylpropylamines

Details Stable salts of novel derivatives of 3,3-diphenylpropylamines Stable salts of novel derivatives of 3,3-diphenylpropylamines

C - Chemistry, Metallurgy

07

C

C07C 219/28 (2006.01) A61K 31/235 (2006.01) A61P 13/10 (2006.01) C07C 213/06 (2006.01) C07C 215/54 (2006.01) C07C 229/38 (2006.01)

Patent

CA 2389749

The present invention concerns highly pure, crystalline, stable compounds of novel derivatives of 3,3- diphenylpropylamines in the form of their salts, a method for the manufacture and highly pure, stable intermediate products. The method is in particular characterised by regio- and chemoselectivity and high yield. Salts of phenolic monoesters of 3,3-diphenylpropylamines are provided, that are particularly well-suited for use in pharmaceutical formulations. Preferred compounds are R-(+)-2-(3- diisopropylamino-1-phenyl-propyl)-4- hydroxymethylphenylisobutyrate ester hydrogen fumarate and R- (+)-2-(3-diisopropylamino-1-phenylpropyl)-4-hydroxy- methylphenylisobutyrate ester hydrochloride hydrate. Furthermore, stable, crystalline intermediate products that are essential for obtaining the abovementioned salts are provided. A preferred intermediate product is R-(-)-3-(3- diisopropylamino-phenyl-propyl)-4-hydroxy-benzoic acid methyl ester

La présente invention concerne des composés stables, cristallins, ultra-purs, de nouveaux dérivés de 3,3-diphénylpropylamines sous la forme de leurs sels, des procédés de fabrication de ces composés, ainsi que des produits intermédiaires stables ultra-purs. Ce procédé se caractérise en particulier par régiospécificité, sélectivité chimique, et un rendement élevé. Ledit procédé consiste à mettre en oeuvre des sels de monoesters phénoliques de 3,3-diphénylpropylamines, particulièrement adaptés à des formulations technico-pharmaceutiques. Les composés préférés sont l'hydrogénofumarate d'ester d'acide isobutyrique <i>R</i>-(+)-2-(3-diisopropylamino-1-phényl-propyl)-4-hydroxyméthylphényle, et l'hydrate de chlorure d'hydrogène d'ester d'acide isobutyrique <i>R</i>-(+)-2-(3-diisopropylamino-1-phényl-propyl)-4-hydroxyméthylphényle. Ledit procédé consiste également à mettre en oeuvre des produits intermédiaires stables, cristallins, nécessaires au procédé, pour l'obtention des sels cités plus haut. Un produit intermédiaire préféré est le méthylester d'acide benzoïque <i>R</i>-(-)-3-(3-Diisopropylamino-phényl-propyl)-4-hydroxy.

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