Novel semi-synthetic glycopeptides as antibacterial agents

Details Novel semi-synthetic glycopeptides as antibacterial agents Novel semi-synthetic glycopeptides as antibacterial agents

C - Chemistry, Metallurgy

07

K

C07K 9/00 (2006.01) A61K 38/14 (2006.01) A61P 31/04 (2006.01)

Patent

CA 2710602

Semi-synthetic glycopeptides having antibacterial activity are described, in particular, the semi-synthetic glycopeptides described herein are made by chemical modification of a glycopeptide (Compound A, Compound B, Compound H or Compound C) or monosaccharide made by hydrolyzing the disaccharide moiety of the amino acid-4 of the parent glycopeptide in acidic medium to give the amino acid-4 monosaccharide; conversion of the monosaccharide to the amino-sugar derivative; acylation of the amino substituent on the amino acid-4 amino-substituted sugar moiety on these scaffolds with certain acyl groups; and conversion of the acid moiety on the macrocyclic ring of these scaffolds to certain substituted amides. Key reaction is the treatment of properly protected intermediate compound with isocyanate or carrying a Hofmann degradation of the primary amide of the 3rd amino acid asparagines with phenyl-bis-trifluoroacetate to give the primary amine. Also provided are methods for the 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.

L'invention concerne des glycopeptides semi-synthétiques ayant une activité antibactérienne. En particulier, les glycopeptides semi-synthétiques de la présente invention sont fabriqués par modification chimique d'un glycopeptide (composé A, composé B, composé H ou composé C) ou d'un monosaccharide fabriqué par hydrolyse de la fraction disaccharide de l'acide aminé-4 du glycopeptide parent dans un milieu acide pour donner le monosaccharide d'acide aminé-4; conversion du monosaccharide en dérivé de sucre aminé; acylation du substituant amino sur la fraction de sucre substitué par amino de l'acide aminé-4 sur ces échafaudages avec certains groupes acyles; et conversion de la fraction acide sur le cycle macrocyclique de ces échafaudages en certains amides substitués. La réaction clé est le traitement d'un composé intermédiaire correctement protégé avec un isocyanate ou la mise en uvre d'une dégradation d'Hofmann de l'amide primaire des asparagines du 3ème acide aminé avec du phényl-bis-trifluoroacétate pour donner l'amine primaire. L'invention concerne également des procédés pour la synthèse des composés, des compositions pharmaceutiques contenant les composés et des procédés d'utilisation des composés pour le traitement et/ou la prophylaxie de maladies, en particulier d'infections bactériennes.

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