Selective process for the deacylation and deacetylation of taxol and taxanes
AssigneeHauser, Inc.
InventorsQun Y. Zheng, Lynn G. Darbie, Christopher K. Murray
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Abstract
The present invention relates to a highly selective method for the deacetylation and deacylation of taxol and taxanes compounds. Specifically, the present invention relates to a one step process wherein acyl groups located at the carbon 2', 10, and 7 positions of taxol and other taxane compounds may be selectively removed.
Claims28
A process for selectively removing acyl group(s) located at the C-2', C-7, and/or C-10 position(s) of a taxane compound comprising the steps of:
- dissolving the taxane compound in a quantity of solvent whereby a taxane solution is produced;
- adding a peroxide to said taxane solution;
- adding a base to said taxane solution containing said peroxide whereby a reaction mixture is produced;
- and
- stirring said reaction mixture.
A process for selectively removing acyl group(s) located at the C-2', C-7 and/or C-10 position(s) of a taxane compound comprising the steps of:
- dissolving the taxane compound in tetrahydrofuran whereby a taxane solution is produced;
- adding hydrogen peroxide to said taxane solution;
- adding a base to said taxane solution containing hydrogen peroxide whereby a reaction mixture is produced;
- and
- stirring said reaction mixture.
A process for the selective deacylation of a taxane compound having acyl group(s) located at the C-2', C-7 and/or C-10 position(s) comprising the steps of:
- dissolving the taxane compound in a solvent whereby a taxane solution is produced;
- adding approximately 0.05 ml of a peroxide per mg of the taxane in said taxane solution to said taxane solution;
- adding NaHCO.sub.3 to said taxane solution containing said peroxide whereby a reaction mixture is produced;
- and
- stirring said reaction mixture for a period of time sufficient to remove the desired acyl group(s) positioned at the C-2', C-7 and/or C-10 position(s) of said taxane compound.
Dependencies are inferred from the claim text.