Semi-synthetic desmethyl-vancomycin-based glycopeptides with...

A - Human Necessities – 61 – K

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A61K 38/04 (2006.01) A61K 38/14 (2006.01) C07K 7/50 (2006.01) C07K 7/54 (2006.01)

Patent

CA 2599297

Semi-synthetic glycopeptides that have antibacterial activity are based on modifications of the desmethyl- vancomycin scaffold, in particular, acylation of the amino substituent on the amino-substituted sugar moiety on this scaffold with certain acyl groups; and/or conversion of the acid moiety on the macrocyclic ring of this scaffolds to certain substituted amides. In addition, compounds of the invention include desmethyl- vancomycin scaffolds on which the acid moiety on the macrocyclic ring is converted to certain substituted amides and the amino substituent on the amino-substituted sugar moiety is alkylated with certain alkyl groups. Also provided are methods for synthesis of the compounds, pharmaceutical compositions containing the compounds, and methods of use of the compounds for the treatment and/or prophylaxis of diseases, especially bacterial infections.

Des glycopeptides semi-synthétiques à action antibactérienne sont obtenus par modification de l'échafaudage du desméthyle-vancomycine, en particulier, par acylation du substituant aminique sur la fraction de sucre aminosubstituée sur cet échafaudage par certains groupes acyle; et/ou par conversion de la fraction acide sur le noyau macrocyclique de cet échafaudage par certains amides substitués. De plus, les composés de l'invention contiennent des échafaudages de desméthyle-vancomycine sur lesquels la fraction acide sur le noyau macrocyclique est convertie en certains amides substitués et le substituant aminique sur la fraction aminosubstituée est alkylé par certains groupes alkyle. Par ailleurs, l'invention concerne des procédés de synthèse de ces composés, des compositions pharmaceutiques qui contiennent ces composés ainsi que des procédés d'utilisation de ces composés dans le traitement et/ou la prophylaxie de maladies, en particulier les infections bactériennes.

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