Processes for preparation of taxanes and intermediates thereof

Details Processes for preparation of taxanes and intermediates thereof Processes for preparation of taxanes and intermediates thereof

C - Chemistry, Metallurgy

07

D

C07D 305/14 (2006.01)

Patent

CA 2723654

A paclitaxel intermediate of formula 1: wherein R1 is acetyl, R2 is tert-butyloxycarbonyl (BOC), R3 and R4 are phenyl and R5 is 1- ethoxyethyl, is provided. Also provided are processes for preparing taxane intermediates of formula 1 comprising reacting a compound of formula 2 with a compound of formula 3 wherein, R1, R2 and R5 are independently a hydroxyl protecting group; R3 is phenyl, substituted phenyl, a straight or branched alkyl containing 1 to 12 carbon atoms, alkenyl containing 2 to 12 carbon atoms, cycloalkyl containing 4 to 15 carbon atoms, cycloalkenyl or an R6-O- group in which R6 is: phenyl, substituted phenyl group, a C1-C8 straight or branched alkyl, a C2-C8 straight or branched alkenyl group, a C3-C8 straight or branched alkynyl, a C3-C7 cycloalkyl, C4-C7 cycloalkenyl, a C7-C11bicycloalkyl substituent, or a saturated or unsaturated nitrogen; and R4 is phenyl or a substituted phenyl group.

Cette invention concerne un intermédiaire de paclitaxel de formule 1, dans laquelle R1 est acétyle, R2 est tert-butyloxycarbonyle (BOC), R3 et R4 sont phényle et R5 est 1-éthoxyéthyle. Linvention concerne également des processus de préparation dintermédiaires de taxanes de formule 1 comprenant la mise en réaction dun composé de formule 2 avec un composé de formule 3, R1, R2 et R5 étant indépendamment un groupe protecteur hydroxyle, R3 étant phényle, phényle substitué, alkyle linéaire ou ramifié contenant de 1 à 12 atomes de carbone, alcényle contenant 2 à 12 atomes de carbone, cycloalkyle contenant 4 à 15 atomes de carbone, cycloalcényle ou un groupe R6-O- où R6 est phényle, groupe à substitution phényle, un alkyle en C1-C8 linéaire ou ramifié, un groupe alcényle en C2-C8 linéaire ou ramifié, un alcynyle en C3-C8 linéaire ou ramifié, un cycloalkyle en C3-C7, un cycloalcényle en C4-C7, un substituant bicycloalkyle en C7-C11 ou un azote saturé ou insaturé, et R4 étant phényle ou un groupe phényle substitué.

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