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US 6,294,521 B1Granted
Phosphosugars and phosphosugar-containing compounds having anti-inflammatory activity
AssigneeThe Australian National University
InventorWilliam Butler Cowden
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Abstract
D-mannoside-6-phosphate compounds having anti-inflammatory activity are disclosed, and use thereof in treating inflammatory diseases, particularly cell-mediated inflammatory diseases.
Claims17
A phosphosugar compound selected from:
- a. D-mannose-6-phosphate derivatives of the Formula I:
- wherein the D-mannose-6-phosphate residue is in either the α-configuration or the β-configuration;
- and wherein X is selected from the group consisting of unsubstituted straight or branched chain alkyl, substituted straight or branched chain alkyl, unsubstituted straight or branched chain alkenyl, substituted straight or branched chain alkenyl, unsubstituted straight or branched chain alkynyl, substituted straight or branched chain alkynyl, unsubstituted cycloalkyl, substituted cycloalkyl, unsubstituted aryl, substituted aryl, unsubstituted heteroaryl, substituted heteroaryl, unsubstituted aralkyl, substituted aralkyl, unsubstituted heteroaralkyl, substituted heteroaralkyl, polyether, monosaccharide, disaccharide and trisaccharide groups;
- and wherein each —OR group, which may be the same or different, is —OH or an ester group;
- with the proviso that X does not represent methyl, butyl or hexadecyl when the —OR groups all represent —OH;
- b. D-mannose-6-phosphate derivatives of the Formula IA:
- wherein the D-mannose-6-phosphate residues are in either the α-configuration or the β-configuration;
- wherein each —OR group is as defined above;
- and wherein W is a linker moiety between the residues, said linker moiety being selected from the group consisting of:
- (i) —(CH2)n—, in which n is an integer of from 2 to 20;
- (ii) —Z—, in which Z is selected from the group consisting of a substituted aryl or heteroaryl linker moiety and an unsubstituted aryl or heteroaryl linker moiety;
- and
- (iii ) —(CH2)n—YZY—(CH2)n, in which n is an integer of from 1 to 10, Y is selected from the group consisting of O, NH, S, CO, CH2, COO and CONH, and Z is selected from the group consisting of a substituted aryl or heteroaryl linker moiety and an unsubstituted aryl or heteroaryl linker moiety;
- and
- c. pharmaceutically acceptable salts thereof.
12 more elements
A method of treatment of cell-mediated inflammation in a human or non-human mammalian patient in need of such treatment, which comprises administration to the patient of an effective amount of at least one phosphosugar compound selected from:
- a. D-mannose-6-phosphate derivatives of the Formula I:
- wherein the D-mannose-6-phosphate residue is in either the α-configuration or the β-configuration;
- and wherein X is selected from the group consisting of unsubstituted straight or branched chain alkyl, substituted straight or branched chain alkyl, unsubstituted straight or branched chain alkenyl, substituted straight or branched chain alkenyl, unsubstituted straight or branched chain alkynyl, substituted straight or branched chain alkynyl, unsubstituted cycloalkyl, substituted cycloalkyl, unsubstituted aryl, substituted aryl, unsubstituted heteroaryl, substituted heteroaryl, unsubstituted aralkyl, substituted aralkyl, unsubstituted heteroaralkyl, substituted heteroaralkyl, polyether, monosaccharide, disaccharide and trisaccharide groups;
- and wherein each —OR group, which may be the same or different, is —OH or an ester group;
- b. D-mannose-6-phosphate derivatives of the Formula IA:
- wherein the D-mannose-6-phosphate residues are in either the α-configuration or the β-configuration;
- wherein each —OR group is as defined above;
- and wherein W is a linker moiety between the residues;
- and
- c. pharmaceutically acceptable salts thereof.
7 more elements
Dependencies are inferred from the claim text.