Water soluble analogs and prodrugs of taxol

Publication Date
1995-05-02Filing Date
1992-10-16Inventor
Kingston, David G.
Liang, Jingyu
Metadata
Show full item recordAbstract
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.
Assignee
Virginia Tech Intellectual Properties, Inc.
Patent Number
5411984
Application Number
7963337
Primary/U.S. Class
514/449
Other/U.S. Class
549/510
549/511
CPC Class
C07D305/14
Patent Type
utility
Collections
- Virginia Tech Patents [545]