Isolation and purification of paclitaxel and cephalomannine

Details Isolation and purification of paclitaxel and cephalomannine Isolation and purification of paclitaxel and cephalomannine

C - Chemistry, Metallurgy

07

D

C07D 305/14 (2006.01)

Patent

CA 2210972

A novel process for extraction, isolation and separation of taxanes, particularly paclitaxel, from natural sources such as bark, needles and twigs from Taxus species, tissue cultures, and fungi is described, wherein the taxanes are separated from the crude extracts by partitioning between polar and nonpolar solvents, precipitation in nonpolar solutions, reacting the mixture by halogenation of unsaturated taxane derivatives, followed by chromatographically separating and crystallizing taxanes from a mixture of polar and nonpolar solvents; more particularly, the process of halogenation of unsaturated side chain taxane derivatives, particularly cephalomannine in presence of paclitaxel, is described, wherein bromine is preferably added to the double bond of unsaturated taxanes leaving paclitaxel unchanged, with paclitaxel being easily separated from the mixture including the less polar halogenated taxane derivatives.

Description d'un procédé nouveau pour l'extraction, l'isolement et la séparation des taxanes, en particulier du paclitaxel, de sources naturelles comme l'écorce, les aiguilles et les brindilles des espèces de Taxus, de cultures de tissus et de champignons. Au cours du procédé, les taxanes sont séparées d'extraits bruts par partage entre solvants polaires et non polaires, précipitation dans les solutions non polaires, réaction du mélange par halogénation des dérivés de taxanes insaturés, puis séparation par chromatographie et cristallisation des taxanes d'un mélange de solvants polaires et non polaires; description plus particulièrement du procédé d'halogénation des dérivés de taxanes à chaîne latérale insaturée, particulièrement la céphalomannine en présence de paclitaxel, au cours duquel de la bromine est de préférence ajoutée au double lien de taxanes insaturées en laissant le paclitaxel inchangé, ce dernier étant facile à séparer du mélange comprenant les dérivés de taxanes halogénés moins polaires.

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