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US 10,272,065 B2Granted
Gem-difluorinated C-glycoside compounds as anti-cancer agents
AssigneeBenoit & Côté
InventorSteve N. Slilaty
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Abstract
The present document describes a synthesis of a class of gem-difluorinated C-glycoside compounds derived from podophyllotoxin, which may be used, but not exclusively, in oncology for the treatment of cancer. More particularly, the podophyllotoxin gem-difluorinated C-glycoconjugated derivatives display improved conformational and chemical stability, and improved cytotoxicity exhibited against drug-resistant cancer cell lines.
Claims2
A method for preparing a compound of Formula I:
- or a pharmaceutically acceptable salt, hydrate or solvate thereof, comprising the steps of:
- 1) obtaining a compound of formula IV by epimerization and then substitution of an alcohol function in position 4 of podophyllotoxin or demethylated podophyllotoxin by an azido group subsequently reduced into an amine group
- wherein R5 is a methyl group;
- 2) obtaining a compound of Formula V
- wherein R1, R2, R3 are a hydrogen atom or a protective group for a hydroxyl,
- wherein R4 is a hydroxyl group or a protective group for a hydroxyl group, via the following reaction sequence:
- wherein R1, R2, R3, R4 are as defined in Formula V;
- and
- 3) coupling said compound of Formula IV with said compound of formula V.
6 more elements
Dependencies are inferred from the claim text.