Synthesis of taxol enhancers

Details Synthesis of taxol enhancers Synthesis of taxol enhancers

C - Chemistry, Metallurgy

07

C

C07C 327/56 (2006.01) C07D 209/42 (2006.01) C07D 209/44 (2006.01) C07D 213/77 (2006.01) C07D 213/83 (2006.01) C07D 261/18 (2006.01) C07D 307/54 (2006.01) C07D 333/38 (2006.01)

Patent

CA 2453415

Disclosed is a method of preparing a thiohydrazide compound a formula (II) from a hydrazide starting compound of formula (I). The method comprises reacting the starting compound of formula (I) with a thionylating reagent. The thiohydrazide of formula (II) can be reacted with compounds of the formula Z- C(O)-Y-C(O)-z or HO-C(O)-Y-C(O)-OH and a carboxylic acid activating agent to produce compound of formula III which enhance the anti-cancer activity of taxol and analogs thereof. The variables R1, R2,R5, R10, Y and Z are as defined in the claims.

L'invention concerne un procédé de préparation d'un composé de thiohydrazide de formule (II), à partir d'un composé de base d'hydrazide de formule (I). Ce procédé consiste à faire réagir le composé de base de formule (I) avec un réactif de thionylation. Le thiohydrazide de formule (II) peut être soumis à une réaction avec des composés de formule Z-C(O)-Y-C(O)-Z ou HO-C(O)-Y-C(O)-OH et un agent activant d'acide carboxylique, de sorte à produire des composés de formule (III) qui amplifient l'activité anticancéreuse du Taxol et de ses analogues. Les variables R¿1?, R¿2?, R¿5?, R¿10?, Y et Z sont telles que définies dans les revendications.

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