Method of synthesizing a paclitaxel derivative
OwnerJames Leslie Douglas, Brian Francis Kaller +1inventors
InventorsJames Leslie Douglas, Brian Francis Kaller, Lynda M. Moran
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Abstract
A process for synthesizing paclitaxel derivative compounds useful for the treatment of cancer, comprises protecting the hydroxyl group at C-2′ position of a paclitaxel compound by reacting the same with a protecting group reagent to provide a protecting group (PG) at the C-2′ position, converting the hydroxyl group at C-7 position of the paclitaxel compound to a methylthiomethyl ether, and deprotecting the C-2′ position hydroxyl group through the removal of the protecting group reagent, thus yielding the final desired paclitaxel derivative product.
Claims16
A process for synthesizing a 7-O-methylthiomethyl paclitaxel of formula (1)
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- comprising the steps of:
- (a) reacting paclitaxel with a protecting group reagent selected from the group consisting of trialkylsilyl halides and dialkylalkoxysilyl halides with the proviso that triethylsilyl chloride is excluded, to provide a C-2′ protected paclitaxel of formula (2) having a protecting group, PG, in the C-2′ position;
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- (b) reacting the C-2′ protected paclitaxel of formula (2) with a methylthiomethylation reagent to form a C-2′ protected, 7-O-methylthiomethyl paclitaxel of formula (3);
- and
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- (c) removing the protecting group PG to form the 7-O-methylthiomethyl paclitaxel of formula (1).
Dependencies are inferred from the claim text.