Sulfated oligosaccharide derivatives
AssigneeProgen Industries Ltd
InventorsVito Ferro, Jon Fairweather, Tomislav Karoli, Ligong Liu
Life of this patent
Estimating the term…
Abstract
The invention relates to compounds which are polysulfated oligosaccharide derivatives having activity as inhibitors of heparan sulfate-binding proteins and inhibitors of the enzyme heparanase; methods for the preparation of the compounds; compositions comprising the compounds, and use of the compounds and compositions thereof for the antiangiogenic, antimetastatic, anti-inflammatory, antimicrobial, anticoagulant and/or antithrombotic treatment, lowering of blood triglyceride levels and inhibition of cardiovascular disease of a mammalian subject.
Claims17
A compound of the general formula:
- X—[Y]n-Z-UR1
- wherein:
- X, Y and Z are each a monosaccharide unit with a group UR bonded via a single or multiple bond to each non-linking carbon of X, Y and Z, except carbon-1 of monosaccharide Z which bears UR1 bonded via a single or multiple bond;
- n is an integer having a value of 0-6;
- each U is independently C, N, S or O or their higher oxidation states, including CO, COO, NO, NO2, S(O), S(O)O;
- each R is independently SO3M or H, where M is any pharmaceutically acceptable cation or is any alkyl, aryl, acyl, aroyl, alkyl sulfonyl, aryl sulfonyl, PEG, a PEG derivative, H or the group
- where independently in each AB group, A is O or NH, and B is H, or M where M is as defined above, or al alkyl, aryl or any other suitable group;
- R1 is SO3M, H, alkyl, aryl, acyl, aroyl, alkyl sulfonyl, aryl sulfonyl, PEG or a PEG derivative, or R1 together with U is N3 or a substituted triazole or derivative, or a substituted tetrazole or derivative, or a substituted aryl or derivative, or a substituted heteroaryl or derivative;
- with the provisos that:
- at least one of UR1 or UR is not OSO3M, NSO3M, OH or OPO3M2, and
- at least 50% of the R groups are SO3M.
A compound of the general formula:
- wherein:
- n is an integer having a value of 0-6;
- U is C, No S or O or their higher oxidation states, including CO, COO, NO, NO2, S(O), S(O)O;
- each R is independently SO3M or H4, where M is any pharmaceutically acceptable cation or is any alkyl, aryl, acyl, aroyl, alkyl sulfonyl, aryl sulfonyl, PEG, a PEG derivative, H or the group
- where independently in each AB group, A is O or NH, and B is H, or M where M is as defined above, or an alkyl aryl or any other suitable group;
- R1 is SO3M, H, alkyl, aryl, acyl, aroyl, alkyl sulfonyl, aryl sulfonyl, PEG or a PEG derivative, or R1 together with U is N3 or a substituted triazole or derivative, or a substituted tetrazole or derivative, or a substituted aryl or derivative, or a substituted heteroaryl or derivative;
- with the provisos that:
- when U is O or N, at least one of R1 or K is not SO3M, H or PO3M2, and
- at least 50% of the R groups are SO3M.
The composition according to claim 9 which further includes a pharmaceutically or veterinarially acceptable excipient, buffer, stabiliser, isotonicising agent, preservative or antioxidant.
The use according to claim 12, wherein said mammalian subject is a human subject.
The method according to claim 14 wherein said mammalian subject is a human subject.
Dependencies are inferred from the claim text.