Triterpene saponins, methods of synthesis, and uses thereof

Details Triterpene saponins, methods of synthesis, and uses thereof Triterpene saponins, methods of synthesis, and uses thereof

C - Chemistry, Metallurgy

07

H

C07H 15/24 (2006.01) A61K 31/704 (2006.01) A61P 37/04 (2006.01)

Patent

CA 2720771

The present invention relates to triterpene glycoside saponin-derived adjuvants, syntheses thereof, intermediates thereto, and uses thereof. QS-7 is a potent immuno-adjuvant that is significantly less toxic than QS-21, a related saponin that is currently the favored adjuvant in anticancer and antiviral vaccines. Tedious isolation and purification protocols have hindered the clinical development of QS-7. A novel semi-synthetic method is provided wherein a hydrolyzed prosapogenin mixture is used to synthesize QS-7, QS-21, and related analogs, greatly facilitating access to QS- 7 and QS-21 analogs for preclinical and clinical evaluation.

La présente invention concerne des adjuvants dérivés de saponine de triterpène glycoside, des synthèses de ceux-ci, des intermédiaires à ceux-ci et leurs utilisations. QS-7 est un immuno-adjuvant puissant qui est nettement moins toxique que QS-21, une saponine apparentée qui est couramment l'adjuvant préféré dans des vaccins anticancéreux et antiviraux. Des protocoles d'isolation et de purification fastidieux ont gêné le développement clinique de QS-7. Un nouveau procédé semi-synthétique est décrit, un mélange de prosapogénine hydrolysée étant utilisé pour synthétiser QS-7, QS-21, et des analogues apparentés, facilitant grandement l'accès à des analogues de QS-7 et QS-21 pour une évaluation pré-clinique et clinique.

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