Virginia Tech Intellectual Properties Inc

Jingyu Liang

David G Kingston

Substituted 2'-benzoyl and 2', 7-dibenzoyl taxol derivatives are synthesized which have improved water solubility and stability while maintaining bioactivity. In a preferred embodiment, taxol 2',7-di(sodium 1,2-benzenedicarboxylate) is synthesized by reacting taxol with phthalic anhydride, and subsequently neutralizing the resulting acid by an ion exchange resin. Taxol 2'-(sodium 1,4-benzenedicarboxylate) is prepared by reacting the monobenzyl ester of 1,4-benzene dicarboxylic acid with taxol in the presence of dicyclohexyl carbodiimide and dimethylaminopyridine, hydrogenolysing the resulting ester to remove the benzyl group, and neutralizing with ion exchange resin. Other taxol prodrugs are prepared by modifications of these routes. In a preferred embodiment, the compounds prepared have improved water-solubility as compared with taxol and demonstrate activity in the M109 mouse bioassay system.

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Nanjing, China

Jingyu Liang