Triterpenoid 2-deoxy Glycosides, Method of Preparation Thereof and Use Thereof as Medicaments

Triterpenoid 2-deoxy glycosides of general formula Ia

• wherein:
• each of “a” and “b” is a double (d) or a single (s) bond;
• R2 is selected from the group comprising COOH, COOCH2C6H5, COO(CH2)nCH3,
• wherein n=0-10, and CH2OR2a;
• R3 is CH3 or CHO;
• R4 is CH3 or CH2;
• X1 is CHOR1 or C═O;
• X2, X3 are independently CH2 or C═O;
• R1 is selected from the group comprising acetyl, 2-deoxy-α-D-galactopyranosyl, 3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl, 2-deoxy-α-D-glucopyranosyl, 3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl, 4,6-di-O-acetyl-3-brom-2,3-dideoxy-α-D-glucopyranosyl, 4-(2′,3′,4′,6′-tetra-O-acetyl-β-D-galactopyranosyl)-3,6-di-O-acetyl-2-deoxy-α-D-glucopyranosyl, 4-(β-D-galactopyranosyl)-2-deoxy-α-D-glucopyranosyl, 4-(2′,3′,4′,6′-tetra-O-acetyl-α-D-glucopyranosyl)-3,6-di-O-acetyl-2-deoxy-α-D-glucopyranosyl, 4-(α-D-glucopyranosyl)-2-deoxy-α-D-glucopyranosyl, 4-(2′,3′,4′,6′-tetra-O-acetyl-β-D-galactopyranosyl)-6-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl, 4-(β-D-galactopyranosyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl, 4-(2′,3′,4′,6′-tetra-O-acetyl-α-D-glucopyranosyl)-6-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl, 4-(α-D-glucopyranosyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl, 3,4-di-O-acetyl-2-deoxy-α-L-rhamnosyl, 2-deoxy-α-L-rhamnosyl, 4-O-acetyl-2,3-dideoxy-3-brom-α-L-rhamnosyl, 4-O-acetyl-2,3,6-trideoxy-α-L-erythro-hex-2-enopyranosyl, 2,3,6-trideoxy-α-L-erythro-hex-2-enopyranosyl and hydrogen;
• R2a is selected from the group comprising 2-deoxy-α-D-galactopyranosyl, 3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl, 2-deoxy-α-D-glucopyranosyl, 3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl, 4,6-di-O-acetyl-3-brom-2,3-dideoxy-α-D-glucopyranosyl, 4-(2′,3′,4′,6′-tetra-O-acetyl-β-D-galactopyranosyl)-3,6-di-O-acetyl-2-deoxy-α-D-glucopyranosyl, 4-(β-D-galactopyranosyl)-2-deoxy-α-D-glucopyranosyl, 4-(2′,3′,4′,6′-tetra-O-acetyl-α-D-glucopyranosyl)-3,6-di-O-acetyl-2-deoxy-α-D-glucopyranosyl, 4-(α-D-glucopyranosyl)-2-deoxy-α-D-glucopyranosyl, 4-(2′,3′,4′,6′-tetra-O-acetyl-β-D-galactopyranosyl)-6-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl, 4-(β-D-galactopyranosyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl, 4-(2′,3′,4′,6′-tetra-O-acetyl-α-D-glucopyranosyl)-6-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl, 4-(α-D-glucopyranosyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl, 3,4-di-O-acetyl-2-deoxy-α-L-rhamnosyl, 2-deoxy-α-L-rhamnosyl, 4-O-acetyl-2,3-dideoxy-3-brom-α-L-rhamnosyl, 4-O-acetyl-2,3,6-trideoxy-α-L-erythro-hex-2-enopyranosyl, 2,3,6-trideoxy-α-L-erythro-hex-2-enopyranosyl and hydrogen;
• provided that:
• when “a” is a single bond (s), “b” is a double bond (d), and when “b” is a single bond (s), “a” is a double bond (d);
• when “a” is a single bond, R4 is CH3, and when “a” is a double bond, R4 is CH2;
• when X2 is C═O and X3 is CH2, “a” is a single bond (s) and “b” is a double bond (d);
• when X2 is C═O and X3 is C═O, “a” is a single bond (s) and “b” is a double bond (d);
• at least one of X1 and R2 comprises 2-deoxy glycosyl
• when R2 is COO(CH2)nCH3, wherein n=0 or 1, R1 is not 2-deoxy-α-D-galactopyranosyl, 3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl, 2-deoxy-α-D-glucopyranosyl, 3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl.