New sulphated oligosaccharide derivatives

FIELD: medicine, pharmaceutics.

SUBSTANCE: present invention refers to new compounds of general formula I [X]n-Y-ZR1R2, wherein the radicals are specified in the description, effective as heparan sulphate-binding protein inhibitors. The invention also refers to a pharmaceutical or veterinary composition having heparan sulphate-binding protein inhibitory activity for preventing or treating a disorder in a mammal, and to the use of these compounds and compositions for antiangiogenic, antimetastatic, anti-inflammatory, antimicrobial, anticoagulant and/or antithrombotic therapy in a mammal.

EFFECT: preparing the new compounds of general formula I [X]n-Y-ZR1R2, wherein the radicals are specified in the description, effective as the heparan sulphate binding protein inhibitors.

10 cl, 31 ex, 11 tbl, 40 dwg

 

The text descriptions are given in facsimile form.

1. The compound of General formula:

in which
each of X and Y represents a monosaccharide unit, and in which each hydroxyl group is not involved in a glycosidic bonds, independently substituted by a group of SO3M or N, where M is any pharmaceutically acceptable cation;
X and Y are any D - or L-hexose;
Y is in the shape of a closed or open loop;
Z represents O, N or S, or their higher oxidation States, or the relationship, and is linked to the anomeric carbon atom when Y is regenerating monosaccharide;
R1is a linker selected from the group consisting of C1-6of alkyl, C1-6alkylamino,1-6allylthiourea, triazolyl and thiazolyl substituted one the second or two With 1-6alkyl groups, or represents a bond;
R2is a lipophilic group selected from the group consisting of cholesteryl; cholestanol; kolata; desoxycholate, where each hydroxyl group is independently substituted by H, SO3M or1-6the alkyl, where M is as defined above; glycyrrhetinic; linear C9-16of alkyl; C9-16of alkyl, substituted triazolyl-C6-10by aryl; C8-16of alkyl, substituted C1-8by alkyl; C1-6alkylamino,1-6alkylamino, substituted C1-6by alkyl; and (C1-6alkylamides12-24of alkyl;
n is an integer from 0 to 6;
the degree of sulfation of each compound is in the range from 70 to 100% of the total number of hydroxyl groups, and
if R1represents a bond, R2is not glycyrrhetic acid or its derivatives;
if n is 3-6, a R1represents a bond, and X and Y are α(1→4)-linked glucose, R2not a C12-C18 linear alkyl group;
if n is 3-5, a R1represents a bond, and X and Y are β(1→3)-linked glucose, R2not a C9-C12 linear alkyl group or cholesterole group;
if n=0 and Z=O, R1is not C1-6alkylamino, and R2is not linear With9-16by alkyl; and
if n=0 is Z=O, Y = glucopyranose and R1represents a bond, R2is not cholesterola.

2. The compound according to claim 1, in which R2represents cholestanol.

3. The compound according to claim 1, in which R2represents propellered.

4. The compound according to any one of claims 1 to 3, in which R1represents methyl[1,2,3]-triazole-1-ilen linker.

5. A compound selected from the group consisting of 3β-cholestanol 2,3,4,6-Tetra-O-matriculant-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-matriculant-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-matriculant-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-matriculant-β-D-glucopyranoside (compound 65), 4-(cholestan-3-intoximeter)[1,2,3]triazole-1-yl 2,3,4,6-Tetra-O-matriculant-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-matriculant-α-D-glyukopiranozil-(1→4)-1-deoxy-2,3,6-tri-O-matriculant-β-D-glucopyranoside (compound 70), 4-(cholestan-3β-intoximeter)[1,2,3]triazole-1-yl 2,3,4,6-Tetra-O-matriculant-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-matriculant-α-D-glyukopiranozil-(1→4)-1-deoxy-2,3,6-tri-O-matriculant-β-D-glucopyranoside (compound 76), 3β-cholestanol 2,3,4,6-Tetra-O-matriculant-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-matriculant-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-matriculant-β-D-glucopyranoside (compound 87), Dementieva salt 3-stearamidopropyl 2,3,4,6-Tetra-O-sulfo-α-D-glyukopiranozil-(1→4)-23,6-three-O-sulfo-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-sulfo-β-D-glucopyranoside (compound 123), treecontrol salt 3-stearamidopropyl 2,3,4,6-Tetra-O-sulfo-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-sulfo-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-sulfo-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-sulfo-β-D-glucopyranoside (compound 128), 3-{4-(cholestan-3β-intoximeter)-[1,2,3]triazole-1-yl}propyl 2,3,4,6-Tetra-O-matriculant-α-D-mannopyranosyl-(1→3)-2,4,6-tri-O-matriculant-α-D-mannopyranosyl-(1→2)-3,4,6-tri-O-matriculant-α-D-mannopyranoside (compound 48), 3-{4-(cholestan-3β-intoximeter)[1,2,3]triazole-1-yl}propyl 2,3,4,6-Tetra-O-matriculant-α-D-mannopyranosyl-(1→3)-2,4,6-tri-O-matriculant-α-D-mannopyranosyl-(1→3)-3,4,6-tri-O-matriculant-α-D-mannopyranoside (compound 60), heptanethiol salt of 4-(cholestan-3β-intoximeter)[1,2,3]triazole-1-yl 2,3,4,6-Tetra-O-sulfo-β-D-galactopyranosyl-(1→4)-2,3,6-tri-O-sulfo-β-D-glucopyranoside (compound 93), heptanethiol salt of 4-(cholestan-3β-intoximeter)[1,2,3]triazole-1-yl 2,3,4,6-Tetra-O-sulfo-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-sulfo-β-D-glucopyranoside (compound 97), Dementieva salt of 2-(cholestan-3-yloxy)acetamido 2,3,4,6-Tetra-O-sulfo-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-sulfo-α-D-glyukopiranozil-(1→4)-2,3,6 three-O-sulfo-β-O-glucopyranoside (compound 134), Dementieva salt of 1-[(cholestan-3-yloxy)propyl]-3-[2,3,4,6-Tetra-O-sulfo-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-sulfo-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-sulfo-β-D-glucopyranosid]thiourea (compounds is their 139) and N-(2,3,4,6-Tetra-O-matriculant-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-matriculant-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-matriculant-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-matriculant-β-D-glyukopiranozil)-4-((3R,10S,12S,13R)-3-O-matriculant-12-O-acetyl-10,13-dimethylhexanoic-1H-cyclopent[a]phenanthrene-17-yl)pentanone (compound 83).

6. Pharmaceutical or veterinary composition having inhibitory activity against heparin-sulfate-binding proteins, for the prevention or treatment of a mammal disorder resulting from angiogenesis, metastasis, inflammation, coagulation/thrombosis, high level of triglycerides in the blood, microbial infection and/or cardiovascular disease, which contains an effective amount of at least one compound according to claim 1 or 5, together with a pharmaceutically or veterinary acceptable carrier or diluent, at least one of the specified connection.

7. Applying an effective amount of a compound according to claim 1 or 5 to obtain drugs for the prevention or treatment of the subject is a mammal disorder resulting from angiogenesis, metastasis, inflammation, coagulation/thrombosis, high level of triglycerides in the blood, microbial infection and/or cardiovascular disease, where the drug has an inhibitory activity against heparin-sulfate-binding proteins.

8. The use according to claim 7, in which the compound is chosen from the group consisting of 3β-cholestanol 2,3,4,6-Tetra-O-matriculant-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-matriculant-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-nutrisol is oneto-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-matriculant-β-D-glucopyranoside (compound 65), 4-(cholestan-3-intoximeter)[1,2,3]triazole-1-yl 2,3,4,6-Tetra-O-matriculant-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-matriculant-α-D-glyukopiranozil-(1→4)-1-deoxy-2,3,6-tri-O-matriculant-β-D-glucopyranoside (compound 70), 4-(cholestan-3β-intoximeter)[1,2,3]triazole-1-yl 2,3,4,6-Tetra-O-matriculant-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-matriculant-α-D-glyukopiranozil-(1→4)-1-deoxy-2,3,6-tri-O-matriculant-β-D-glucopyranoside (compound 76), 3β-cholestanol 2,3,4,6-Tetra-O-matriculant-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-matriculant-α-D-glyukopiranozil-(1→4)-2,3,6-three-O-matriculant-β-D-glucopyranoside (compound 87), Dementieva salt 3-stearamidopropyl 2,3,4,6-Tetra-O-sulfo-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-sulfo-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-sulfo-β-D-glucopyranoside (compound 123) and treecontrol salt 3-stearamidopropyl 2,3,4,6-Tetra-O-sulfo-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-sulfo-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-sulfo-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-sulfo-β-D-glucopyranoside (compound 128).

9. The method of prevention or treatment of the subject is a mammal disorder resulting from angiogenesis, metastasis, inflammation, coagulation/thrombosis, high level of triglycerides in the blood, microbial infection and/or cardiovascular disease, which includes the introduction of this subject effetive the number, at least one compound according to claim 1 or 5, or the composition containing at least one specified compound, where the compound has inhibitory activity against heparin-sulfate-binding proteins.

10. The method according to claim 9, in which the compound is chosen from the group consisting of 3β-cholestanol 2,3,4,6-Tetra-O-matriculant-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-matriculant-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-matriculant-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-matriculant-β-D-glucopyranoside (compound 65), 4-(cholestan-3-intoximeter)[1,2,3]triazole-1-yl 2,3,4,6-Tetra-O-matriculant-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-matriculant-α-D-glyukopiranozil-(1→4)-1-deoxy-2,3,6-tri-O-matriculant-β-D-glucopyranoside (compound 70), 4-(cholestan-3β-intoximeter)[1,2,3]triazole-1-yl 2,3,4,6-Tetra-O-matriculant-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-matriculant-α-D-glyukopiranozil-(1→4)-1-deoxy-2,3,6-tri-O-matriculant-β-D-glucopyranoside (compound 76), 3β-cholestanol 2,3,4,6-Tetra-O-matriculant-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-matriculant-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-matriculant-β-D-glucopyranoside (compound 87), Dementieva salt 3-stearamidopropyl 2,3,4,6-Tetra-O-sulfo-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-sulfo-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-sulfo-β-D-glucopyranoside (compound 123) and treecontrol sale-stearamidopropyl 2,3,4,6-Tetra-O-sulfo-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-sulfo-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-sulfo-α-D-glyukopiranozil-(1→4)-2,3,6-tri-O-sulfo-β-D-glucopyranoside (compound 128).



 

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23 cl, 7 ex, 2 tbl, 8 dwg

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