Methods and compositions for converting taxane amides to...

Details Methods and compositions for converting taxane amides to... Methods and compositions for converting taxane amides to...

C - Chemistry, Metallurgy

07

D

C07D 305/14 (2006.01)

Patent

CA 2495476

The invention relates to methods and compositions for converting taxane amides to paclitaxel or other taxanes. In one alternative embodiment, the present invention comprises; (i) selectively protecting at least one OH group of a taxane amide; (ii) contacting the taxane amide with a transition metal compound to reduce the amide; (iii) contacting the reduced amide with an agent capable of substantially removing the transition metal; (iv) contacting the reduced amide with a hydrolyzing amount of acid to form a taxane amine salt in solution; (v) adding a sufficient amount of solvent to solidify the amine salt; and (vi) converting the taxane amine salt into paclitaxel or other taxanes.

L'invention concerne des procédés et des compositions permettant de transformer des amides de taxane en paclitaxel ou en autres taxanes. Dans un mode de réalisation, le procédé comporte les étapes consistant à : (1) protéger sélectivement au moins un groupe OH d'un amide de taxane ; (2) mettre en contact l'amide de taxane avec un composé de métal de transition afin de réduire l'amide ; (2) mettre en contact l'amide réduit avec un agent pouvant éliminer sensiblement le métal de transition ; (4) mettre en contact l'amide réduit avec une quantité hydrolysante d'acide pour former un sel d'amine de taxane en solution ; (5) ajouter une quantité suffisante de solvant pour solidifier le sel d'amine ; et (6) transformer le sel d'amine de taxane en paclitaxel ou en autres taxanes.

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