Anticancer taxanes such as paclitaxel, docetaxel and their...

Details Anticancer taxanes such as paclitaxel, docetaxel and their... Anticancer taxanes such as paclitaxel, docetaxel and their...

2005-05-31

2005-05-31

Owens, Amelia A. (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C549S511000

Reexamination Certificate

active

06900342

ABSTRACT:
A process for the preparation of taxanes comprisingwherein R is a tert. butoxycarbonyl or benzoyl group; PMP is p-methoxyphenyl group; G1is acetyl group; G2is haloacetyl group comprisinga) protecting the C-7 hydroxyl group of 10-deacetylbaccatin III with haloacetyl chlorides and then acetylating the C-10 hydroxyl group with acetyl chloride to obtain a protected 10-deacetylbaccatin III (1);b) subjecting the protected 10-deacetylbaccatin III (1) to coupling with an oxazolidine-5-caboxylic acid of formula 2wherein R is tert. butoxycarbonyl or benzoyl; PMP is p-methoxyphenyl group in the presence of a condensation agent and an activating agent to obtain C-13 esters of formula 3;c) treating the coupled products 3 with weak acidic medium to open the oxazolidine ring to obtain intermediates of formula 4;wherein R is a tert. butoxycarbonyl or benzoyl group; G1is acetyl group; G2is haloacetyl groupd) subjecting the intermediates of compound 4 to selective deprotection of haloacyl group in the presence of acetyl group under mild alkaline condition at −20 to +40° C. for 6-24 h in the presence of ammonia or aliphatic amine or aromatic amines or their combination to obtain paclitaxel or docetaxel.

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