US 7,605,278 B2 · Methods and compositions for converting taxane amides to paclitaxel or other taxanes

Abstract

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.

Claims36

Dependent claims

A method for forming a taxane or precursor or analog thereof from a raw material, the raw material comprising a compound represented by the formula below:

wherein, R2 is H, Ac or a protecting group;
R3 is H, xylosyl or protecting group;
R4 is H or protecting group;
RN is H or an alkyl group;
and
X=deprotonated sulfuric acid or deprotonated sulfur containing acid;
deprotonated nitric acid or other nitrogen containing acid;
deprotonated carboxylic acid, except trifluoro acetic acid;
deprotonated phosphoric acid or any phosphorus containing acid;
deprotonated tartaric acid;
deprotonated p-toluene sulfonic acid;
or deprotonated picric acid;
and
wherein said taxane or precursor or derivative thereof is in a solid, purified form;
the method comprising benzoylating the raw material with a benzoylation solution comprising a benzoylating agent and a buffer such that the pH of the benzoylation solution is about 4 to about 6.

12 more elements

Dependencies are inferred from the claim text.

Methods and compositions for converting taxane amides to paclitaxel or other taxanes

Life of this patent

Methods and compositions for converting taxane amides to paclitaxel or other taxanes

Life of this patent

Abstract

Claims36