Epothilone derivatives and their synthesis and use

Details Epothilone derivatives and their synthesis and use Epothilone derivatives and their synthesis and use

C - Chemistry, Metallurgy

07

D

C07D 417/06 (2006.01) A61K 31/425 (2006.01) C07D 303/00 (2006.01) C07D 313/00 (2006.01) C07D 493/04 (2006.01)

Patent

CA 2334342

The invention relates to epothilone analog represented by formula (I) wherein (i) R2 is absent or oxygen; "a" can be either a single or double bond; "b" can be either absent or a single bond; and "c" can be either absent or a single bond, with the proviso that if R2 is oxygen then "b" and "c" are both a single bond and "a" is a single bond; if R2 is absent then "b" and "c" are absent and "a" is a double bond; and if "a" is a double bond, then R2, "b" and "c" are absent; R3 is a radical selected from the group consisting of hydrogen; lower alkyl; -CH=CH2; -CCH; -CH2F; -CH2Cl; -CH2-OH; -CH2-O-(C1-C6-alkyl); and -CH2-S- (C1-C6-alkyl); R4 and R5 are independently selected from hydrogen, methyl or a protecting group; and R1 is as defined in the specification, or a salt of a compound of formula (I) where a salt-forming group is present. A further aspect of the invention is related to the synthesis of epothilone E. These compounds have inter alia microtubuli depolymerisation inhibiting activity and are e.g. useful against proliferative diseases.

L'invention porte sur des analogues de l'épothilone de formule (I) dans laquelle: R¿2? est absent ou O; (a) peut être une liaison simple ou double; (b) peut être absent ou une liaison simple; et (c) peut être absent ou une liaison simple, sous réserve que si R¿2? est O, (b) et (c) soient chacun une liaison simple et (a) soit une liaison simple, que si R¿2? est absent, (b) et (c) soient absents, et (a) soit une double liaison, et que si (a) est une double liaison, R¿2?, (b) et (c) soient absents; R¿3? est un radical choisi parmi H, alkyle inférieur, -CH=CH¿2?, -C?CH, -CH¿2?F, -CH¿2?Cl, CH¿2?-OH, -CH¿2?-O-(C¿1?-C¿6? alkyle), et -CH¿2?-S-(C¿1?-C¿6? alkyle); R¿4? et R¿5? sont choisis indépendamment parmi H, méthyle et un groupe protecteur; et R¿1? est tel que défini dans la spécification. L'invention porte en outre sur un sel d'un composé de formule (I) dans lequel est présent un groupe formateur de sels, et sur la synthèse de l'épothilone E. Ces composés qui présentent notamment une activité inhibitrice de la dépolymérisation des microtubuli, s'avèrent par exemple utiles contre les maladies proliférantes.

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