Water soluble derivatives of taxol

Details Water soluble derivatives of taxol Water soluble derivatives of taxol

C - Chemistry, Metallurgy

07

D

C07D 305/14 (2006.01)

Patent

CA 2080393

ABSTRACT SulFonated 2'-acryloyltaxol and sulfonated 2'-O-acyl acid taxol derivatives are synthesized which have improved water solubility and stability while maintaining bio-activlty. In particular, 2'-[(3-sulfo-1-oxopropyl)oxy]taxol sodium salt is synthesized by reacting taxol with acrylic acid, and subsequently reacting the 2'-acryloyltaxol with bisulfite in a Michael reaction. 2'-([4-((2-sulfoethyl)amino)-1,4-dioxo- butyl]oxy)taxolsodium salt and 2'-([4-((3-sulfopropyl)amino)- 1,4-dioxobutyl]oxy)taxol sodium salt are synthesized by reacting 2'-succinyltaxol with the tetrabutylammonium salts of taurine and 3-aminopropyl sulfonic acid, respectively, and subsequently exchanging the ammonium with sodium. Glycol derivatives of 2'-0-acyl acid taxols with improved water solubility are synthesized by reaction of a glycol with 2'-0- acyl acid taxol.

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