SEMISYNTHETIC METHOD OF PRODUCING 10-DEACETYL-N-DEBENZOYLPACLITAXEL Russian patent published in 2010 - IPC C07D305/14 A61K31/337 A61P35/00 

Abstract RU 2384578 C2

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing 10-deacetyl-N-debenzoyl-paclitaxel (I) , involving the following stages: a) reacting 2-(2,4-dimethoxyphenyl)-3-(2-nitrobenzene sulfenyl)-4(S)-phenyl-5(R)-oxazolidine carboxylic acid (V) with 10-deacetyl-7,10-bis-trichloroacetyl baccatin III (VI) to obtain 10-deacetyl-7,10-bis-trichloroacetyl baccatin(III)-13-yl ether 2-(2,4-dimethoxyphenyl)-3-(2-nitrobenzene sulfenyl)-4(S)-phenyl-5-(R)-oxazolidine carboxylic acid (VII) , b) hydrolysis of trichloroacetyl groups in positions 7 and 10 of the compound of formula (VII) to obtain 10-deacetylbaccatin(III)-13-yl ether 2-(2,4-dimethoxyphenyl)-3-(2-nitrobenzene sulfenyl)-4(S)-phenyl-5(R)-oxazolidine carboxylic acid (VIII) , c) treatment of the compound of formula (VIII) with acid to obtain 10-deacetyl-N-debenzoylpaclitaxel (I). This compound is a synthon used in making taxanes with anti-tumour activity. The invention also relates to a method of producing docetaxel from the said compound of formula (I).

EFFECT: improved method.

10 cl, 2 dwg, 5 ex

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RU 2 384 578 C2

Authors

Gabetta Bruno

Gambini Andrea

Bombardelli Ehtsio

Fontana Gabriele

Dates

2010-03-20Published

2005-10-07Filed