C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
C07D 491/08 (2006.01) A61K 31/4162 (2006.01) A61P 35/00 (2006.01) C07D 491/18 (2006.01)
Patent
CA 2253912
The present invention relates to the preparation of taxane derivatives starting from 10-deacetyl/baccatine III, 14-hydroxy-10-deacetyl-baccatine III. 19-hydroxy-10-deacetyl- baccatine III and their esters at C13, reacting the respective 10-dehydro derivatives with hydrazine, hydroxylamine and derivatives thereof. The novel compounds are compounds of formula (1): Image wherein R1 and R2 are hydrogen atoms or R1 is hydrogen and R2 is a hydroxy, alkoxy or acyloxy group, or R1 and R2 together form a cyclic carbonate or a cyclic thiocarbonate group of formula Image R3 is hydrogen or hydroxy; R4 is hydrogen or an isoserine residue of formula (2) Image wherein R5 is a C1-C5 alkyl or C2-C5 alkenyl group or a phenyl residue, R6 has the same meanings as R5 or is a tert-butoxy group. The C13 esters of these molecules with substituted isoserine chains exert antitumor activity inhibiting cell proliferation of normal and resistant tumor cell lines and inducing apoptosis. These molecules due to their basic character can be administered upon salification in an aqueous medium without requiring the use of toxic surfactants.
L'invention concerne la préparation de dérivés de taxane, qui consiste à partir de 10-désacétyl-baccatine III, 14-hydroxy-10-désacétyl-baccatine III, 19-hydroxy-10-désacétyl-baccatine III et leurs esters au niveau de C13, à faire réagir les dérivés 10-déshydro respectifs avec de l'hydrazine, l'hydroxylamine, et des dérivés de celle-ci. Les nouveaux composés selon l'invention contiennent un groupe pyrazoline impliquant les atomes de carbone C7 et C9. Les esters C13 de ces molécules à chaînes isosérine substituée exercent une activité antitumorale inhibant la prolifération cellulaire de lignées de cellules normales et résistantes et induisant l'apoptose. Ces molécules, du fait de leur caractère de base, peuvent être administrées lors de la salification dans un milieu aqueux sans qu'il soit nécessaire d'utiliser des agents tensioactifs toxiques.
Indena S.p.a.
Kirby Eades Gale Baker
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