Preparation and use of sulfated oligosaccharides
AssigneeThe Australian National University
InventorsChristopher Richard Parish, William Butler Cowden
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Abstract
Sulfated oligosaccharides, wherein the oligosaccharide has the general formula I: R.sub.1 --(R.sub.x).sub.n --R.sub.2 (I) wherein R.sub.1 and R.sub.2 and each R.sub.x represents a monosaccharide unit, all of which may be the same or different, adjacent monosaccharide units being linked by 1.fwdarw.2, 1.fwdarw.3, 1.fwdarw.4 and/or 1.fwdarw.6 glycosidic bonds and n is an integer of from 1 to 6, and use thereof as anti-angiogenic, anti-metastatic and/or anti-inflammatory agents.
Claims25
A sulfated oligosaccharide, wherein the oligosaccharide has the formula I:
- R.sub.1 --(R.sub.x).sub.n --R.sub.2 (I)
- wherein R.sub.1 and R.sub.2 and each R.sub.x represents a hexose monosaccharide unit, all of which may be the same or different, adjacent hexose monosaccharide units being linked by at least one bond selected from the group consisting of 1.fwdarw.2, 1.fwdarw.3, 1.fwdarw.4 and 1.fwdarw.6 glycosidic bonds, wherein at least 55% of the available hydroxyl groups on the hexose monosaccharide units are O-sulfated, and
- n is an integer of from 1 to 6;
- with the proviso that the oligosaccharide is not a compound comprising 1.fwdarw.4 linked glucose residues or a compound comprising a 1.fwdarw.2 linked fructose.
A method for the anti-angiogenic treatment of a warm-blooded animal patient in need of such treatment, which comprises administration to the patient of an effective amount of a sulfated oligosaccharide selected from the group consisting of oligosaccharides having the formula I:
- R.sub.1 --(R.sub.x).sub.n --R.sub.2 (I)
- wherein R.sub.1 and R.sub.2 and each R.sub.x represents a hexose monosaccharide unit, all of which may be the same or different, adjacent hexose monosaccharide units being linked by at least one bond selected from the group consisting of 1.fwdarw.2, 1.fwdarw.3, 1.fwdarw.4 and 1.fwdarw.6 glycosidic bonds, wherein al least 55% of the available hydroxyl groups on the hexose monosaccharide units are O-sulfated, and
- n is an integer of from 1 to 6;
- with the proviso that the oligosaccharide is not a compound comprising 1.fwdarw.4 linked glucose residues or a compound comprising a 1.fwdarw.2 linked fructose.
A pharmaceutical or veterinary composition for anti-angiogenic treatment, which comprises a sulfated oligosaccharide selected from the group consisting of oligosaccharides having the formula 1:
- R.sub.1 --(R.sub.x).sub.n --R.sub.2 (I)
- wherein R.sub.1 and R.sub.2 and each R.sub.x represents a hexose monosaccharide unit, all of which may be the same or different, adjacent hexose monosaccharide units being linked by at least one bond selected from the group consisting of 1.fwdarw.2, 1.fwdarw.3, 1.fwdarw.4 and 1.fwdarw.6 glycosidic bonds, wherein at least 55% of the available hydroxyl groups on the hexose monosaccharide units are O-sulfated, and
- n is an integer of from 1 to 6;
- with the proviso that the oligosaccharide is not a compound comprising 1.fwdarw.4 linked glucose residues or a compound comprising a 1.fwdarw.2 linked fructose, together with a pharmaceutically and veterinarily acceptable carrier or diluent therefor.
An oligosaccharide of the formula II:
- R.sub.y --(R.sub.y).sub.n --R.sub.y (II)
- wherein each R.sub.y group is the same and each represents a hexose monosaccharide unit, adjacent hexose monosaccharide units being linked by at least one bond selected from the group consisting of 1.fwdarw.3, 1.fwdarw.4 and 1.fwdarw.6 glycosidic bonds;
- and
- n is an integer of from 1 to 6 ;
- with the proviso that the oligosaccharide is not a compound comprising 1.fwdarw.4 linked glucose residues.
A method for the anti-metastatic treatment of a warm-blooded animal patient in need of such treatment, which comprises administration to the patient of an effective amount of a sulfated oligosaccharide selected from the group consisting of oligosaccharides having the formula I:
- R.sub.1 --(R.sub.x).sub.n --R.sub.2 (I)
- wherein R.sub.1 and R.sub.2 and each R.sub.x represents a hexose monosaccharide unit, all of which may be the same or different, adjacent hexose monosaccharide units being linked by at least one bond selected from the group consisting of 1.fwdarw.2, 1.fwdarw.3, 1.fwdarw.4 and 1.fwdarw.6 glycosidic bonds, wherein at least 55% of the available hydroxyl groups on the hexose monosaccharide units are O-sulfated, and
- n is an integer of from 1 to 6, with the proviso that the oligosaccharide is not a compound comprising 1.fwdarw.4 linked glucose residues or a compound comprising a 1.fwdarw.2 linked fructose.
A method for the anti-inflammatory treatment of a warm-blooded animal patient in need of such treatment, which comprises administration to the patient of an effective amount of a sulfated oligosaccharide selected from the group consisting of oligosaccharides having the formula I:
- R.sub.1 --(R.sub.x).sub.n --R.sub.2 (I)
- wherein R.sub.1 and R.sub.2 and each R.sub.x represents a hexose monosaccharide unit, all of which may be the same or different, adjacent hexose monosaccharide units being linked by at least one bond selected from the group consisting of 1.fwdarw.2, 1.fwdarw.3, 1.fwdarw.4 and 1.fwdarw.6 glycosidic bonds, wherein at least 55% of the available hydroxyl groups on the hexose monosaccharide units are O-sulfated, and
- n is an integer of from 1 to 6;
- with the proviso that the oligosaccharide is not a compound comprising 1.fwdarw.4 linked glucose residues or a compound comprising a 1.fwdarw.2 linked fructose.
A pharmaceutical or veterinary composition for anti-metastatic treatment, which comprises a sulfated oligosaccharide selected from the group consisting of oligosaccharides having the formula I:
- R.sub.1 --(R.sub.x).sub.n --R.sub.2 (I)
- wherein R.sub.1 and R.sub.2 and each R.sub.x represents a hexose monosaccharide unit, all of which may be the same or different, adjacent hexose monosaccharide units being linked by at least one bond selected from the group consisting of 1.fwdarw.2, 1.fwdarw.3, 1.fwdarw.4 and 1.fwdarw.6 glycosidic bonds, wherein at least 55% of the available hydroxyl groups on the hexose monosaccharide units are O-sulfated, and
- n is an integer of from 1 to 6;
- with the proviso that the oligosaccharide is not a compound comprising 1.fwdarw.4 linked glucose residues or a compound comprising a 1.fwdarw.2 linked fructose, together with a pharmaceutically and veterinarily acceptable carrier or diluent therefor.
A pharmaceutical or veterinary composition for anti-inflammatory treatment, which comprises a sulfated oligosaccharide selected from the group consisting of oligosaccharides having the formula I:
- R.sub.1 --(R.sub.x).sub.n --R.sub.2 (I)
- wherein R.sub.1 and R.sub.2 and each R.sub.x represents a hexose monosaccharide unit, all of which may be the same or different, adjacent hexose monosaccharide units being linked by at least one bond selected from the group consisting of 1.fwdarw.2, 1.fwdarw.3, 1.fwdarw.4 and 1.fwdarw.6 glycosidic bonds, wherein at least 55% of the available hydroxyl groups on the hexose monosaccharide units are O-sulfated, and
- n is an integer of from 1 to 6;
- with the proviso that the oligosaccharide is not a compound comprising 1.fwdarw.4 linked glucose residues or a compound comprising a 1.fwdarw.2 linked fructose, together with a pharmaceutically and veterinarily acceptable carrier or diluent therefor.
Dependencies are inferred from the claim text.