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US 5,412,123 AGranted
Anthraquinone and anthracene derivatives as inhibitors of the cell-adhesion molecules of the immune system
AssigneeGlycomed Incorporated
InventorsNarasinga Rao, Peng C. Tang, John H. Musser
Life of this patent
Estimating the term…
Abstract
Derivatives of anthraquinone and anthracene are synthesized and formulated into pharmaceutical formulations. When the formulations are administered the derivatives act as ligands binding to an interrupting the biological chain of events associated with selectin receptors in the human body.
Claims17
A compound comprising the following structural formula I:
- ##STR38## R1=OH, O-alkyl wherein the alkyl contains 1 to 6 carbon atoms, or O-linker wherein the linker group is an alkyl containing 1 to 12 carbon atoms or a heteroalkyl containing 1 to 12 atoms which contains heteroatoms selected from the group consisting of S, N and O;
- R2=R--COOH, or CH.sub.2 --O--CO.sub.2 H, CH.sub.2 O--R--CO.sub.2 H, OCH.sub.2 CO.sub.2 H, O--R--O--SO.sub.3, O--R--O--PO.sub.3, or O--R--CO.sub.2 H wherein R is an alkyl containing 1 to 6 carbon atoms;
- R3=H, an alkyl containing 1 to 6 carbon atoms or a heteroalkyl containing 1 to 6 atoms with the heteroatom being selected from the group consisting of N, S and O;
- R4 OH, or O--R' wherein R' is an alkyl containing 1 to 6 carbon atoms or a heteroalkyl containing 1 to 6 atoms with the heteroatom being selected from the group consisting of S and N;
- R5=--(CH.sub.2).sub.n -- wherein n is an integer of from 1 to 12 and the --(CH.sub.2).sub.n -- group may be further attached to a heteroatom selected from the group consisting of N, S and O;
- and
- R6=Hexose or a hexNAc, or a disaccharide linked by either .alpha.- or .beta.-linkage to R5 through an --O-- linker or a linking group which includes as a base atom chain comprised of atoms selected from the group consisting of C, N and S, and
- pharmaceutically acceptable salts and multivalent derivatives of a compound of formula I.
5 more elements
A method of treating an animal for inflammation comprising administering to an animal in need thereof a therapeutically effective amount of a compound having the following structural formula I:
- ##STR39## R1=OH, O-alkyl wherein the alkyl contains 1 to 6 carbon atoms, or O-linker wherein the linker group is an alkyl containing 1 to 12 carbon atoms or a heteroalkyl containing 1 to 12 atoms which contains heteroatoms selected from the group consisting of S, N and O;
- R2=R--COOH, or CH.sub.2 --O--CO.sub.2 H, CH.sub.2 O--R--CO.sub.2 H, OCH.sub.2 CO.sub.2 H, O--R--O--SO.sub.3, O--R--O--PO.sub.3, or O--R--CO.sub.2 H wherein R is an alkyl containing 1 to 6 carbon atoms;
- R3=H, an alkyl containing 1 to 6 carbon atoms or a heteroalkyl containing 1 to 6 atoms with the heteroatom being selected from the group consisting of N, S and O;
- R4=OH, or O--R' wherein R' is an alkyl containing 1 to 6 carbon atoms or a heteroalkyl containing 1 to 6 atoms with the heteroatom being selected from the group consisting of S and N;
- R5=--(CH.sub.2).sub.n -- wherein n is an integer of from 1 to 12 and the --(CH.sub.2).sub.n -- group may be further attached to a heteroatom selected from the group consisting of N, S and O;
- and
- R6=Hexose or a hexNAc, or a disaccharide linked by either .alpha.- or .beta.-linkage to R5 through an --O-- linker or a linking group which includes as a base atom chain comprised of atoms selected from the group consisting of C, N and S, and
- pharmaceutically acceptable salts and multivalent derivatives of a compound of formula I.
5 more elements
An assay test material for determining the presence of ELAM-1 in a sample comprising:
- a substrate the surface of which has bound thereto
- a ligand comprising the formula:
- ##STR40## R1=OH, O-alkyl wherein the alkyl contains 1 to 6 carbon atoms, or O-linker wherein the linker group is an alkyl containing 1 to 12 carbon atoms or a heteroalkyl containing 1 to 12 atoms which contains heteroatoms selected from the group consisting of S, N and O;
- R2=R--COOH, or CH.sub.2 --O--CO.sub.2 H, CH.sub.2 O--R--CO.sub.2 H, OCH.sub.2 CO.sub.2 H, O--R--O--SO.sub.3, O--R--O--PO.sub.3, or O--R--CO.sub.2 H wherein R is an alkyl containing 1 to 6 carbon atoms;
- R3=H, an alkyl containing 1 to 6 carbon atoms or a heteroalkyl containing 1 to 6 atoms with the heteroatom being selected from the group consisting of N, S and O;
- R4=OH, or O--R' wherein R' is an alkyl containing 1 to 6 carbon atoms or a heteroalkyl containing 1 to 6 atoms with the heteroatom being selected from the group consisting of S and N;
- R5=--(CH.sub.2).sub.n -- wherein n is an integer of from 1 to 12 and the --(CH.sub.2).sub.n -- group may be further attached to a heteroatom selected from the group consisting of N, S and O;
- and
- R6=Hexose or a hexNAc, or a disaccharide linked by either .alpha.- or .beta.-linkage to R5 through an --O-- linker or a linking group which includes as a base atom chain comprised of atoms selected from the group consisting of C, N and S, and
- pharmaceutically acceptable salts and multivalent derivatives of a compound of formula I.
7 more elements
Dependencies are inferred from the claim text.