Synthetic lipid-a analogs and uses thereof

Details Synthetic lipid-a analogs and uses thereof Synthetic lipid-a analogs and uses thereof

C - Chemistry, Metallurgy

07

H

C07H 13/06 (2006.01) A61K 39/39 (2006.01) A61P 35/00 (2006.01)

Patent

CA 2396744

New synthetic Lipid-A analogs based on monosaccharide (1) and disaccharide (2) derivatives were designed and prepared in the present invention. Both structures (1) and (2) incorporate novel lipid structures (3) and (4) that are not found in nature. Also, novel disaccharide Lipid-A structures (2) that incorporate novel contingents of uniform lipids and where R1, R4 and R5 are the same substitution group of structure (III) were synthesized. Liposome formulations containing totally synthetic components such as synthetic Lipid-A and synthetic lipopeptide derived from tumor-associated MUC1 mucin are described along with their therapeutic utility. Comparative test results of immunostimulating properties and toxicity of Lipid-A analogs (1) and (2) are included.

La présente invention concerne la conception et la préparation de nouveaux analogues de lipide-A de synthèse basés sur des dérivés de monosaccharide (1) et de disaccharide (2). Ces deux structures (1) et (2) comprennent de nouvelles structures lipidiques (3) et (4) qui ne peuvent être trouvées dans la nature. L'invention concerne également la synthèse de nouvelles structures (2) de lipide-A de disaccharide renfermant de nouveaux contingents de lipides uniformes, dans lesquelles R¿1?, R¿4? et R¿5? représentent le même groupe de substitution de structure (III). L'invention concerne, en outre, des formulations de liposomes contenant des composants entièrement synthétiques, tels que des lipides-A synthétiques et des lipopeptides dérivés de la mucine MUC1 associée aux tumeurs, leur utilisation thérapeutique, ainsi que des résultats de tests comparatifs des propriétés immo-stimulatrices et de la toxicité des analogues de Lipide-A (1) et (2).

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