Novel reaction conditions for the cleavage of silyl ethers...

C - Chemistry – Metallurgy – 07 – D

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C07D 305/14 (2006.01)

Patent

CA 2373819

Novel reaction conditions for the cleavage of silyl ethers from silyl protected taxane precursors to afford paclitaxel and paclitaxel analogues in high yield and quality are described. Paclitaxel is prepared from a taxane precursor by treating the taxane precursor with a strong acid such as trifluoroacetic acid in a solvent such as aqueous acetic acid, such that the amount and number of side reactions and taxane impurities are significantly minimized. Also described are the crystallization methods for the isolation of paclitaxel in either of the two crystal forms A or B. Paclitaxel and paclitaxel analogues are anti-cancer agents.

L'invention concerne de nouvelles conditions de réaction destinées au clivage des silyl-éthers à partir de précurseurs protégés de taxane visant la fabrication de paclitaxel et d'analogues de paclitaxel. Paclitaxel est préparé à partir d'un précurseur de taxane par le traitement de ce dernier avec un acide fort tel que l'acide triacétique dans un solvant tel qu'un acide acétique aqueux, de manière à réduire fortement l'ampleur et le nombre de réactions secondaires et d'impuretés de taxane. L'invention concerne également des procédés de cristallisation destinés à l'isolation du paclitaxel dans l'une des formes cristallines, A ou B. Le paclitaxel et les analogues de paclitaxel sont des agents anticancéreux.

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