EP0340628A2
Expired / Lapsed
EP
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Sulfoamino derivatives of chondroitin sulfates, of dermaten sulfate and of hyaluronic acid and their pharmacological properties
Assignee: Crinos Industria Farmacobiologica SpA
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Filing: 1989-04-27
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Granted: —
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Expires: 2009-04-27
Abstract
Abstract Novel derivatives are disclosed as obtained from chondroitin sulfate, dermatan sulfate and hyaluronic acid, having a molar ratio between sulfate groups and carboxylic groups like that of heparin and furthermore characterized by possessing, as the heparin, the sulfoamino group at the carbon atom at the 6 position hexosamine. The novel compounds show a very remarkable clearing activity in comparison with the starting mucopolysaccharides, this activity being similar and for some derivatives comparable with that of heparin. Moreover, differently from what normally happens upon sulfating the sulfomucopolysaccharides, the anticoagulating activity of the novel compounds is negligible or anyhow very reduced. the compound of the present invention find use in the therapy of arteriosclerosis.
Inventors
- 👤 Benitu Casu
- 👤 Giangiacomo Torri
- 👤 Annamaria Naggi
- 👤 Marisa Mantovani
- 👤 Rodolfo Pescador
- 👤 Roberto Porta
- 👤 Giuseppe Prino
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-23 17:39
CPC Classifications
C; C07; C07H; C07H5/00; C07H5/04; C07H5/06; C08; C08B; C08B37/00; C08B37/006; C08B37/0063; C08B37/0069; A; A61; A61P; A61P7/00; A61P7/02; C08B37/0072
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
54 words
Synthetic sulfoamino derivatives of glycosaminoglycans selected in the group comprising chondroitin sulfates A and C, their mixtures, dermatan sulfate and chondroitin sulfate B, the dimeric units of which have the following formula: wherein R represents OH, SO 3 , R, represents H, SO 3 , Y represents H, COO-, and X represents H, COO-.
Claim 2
Dependent Claim
54 words
Synthetic sulfoamino derivatives of glycosaminoglycans selected in the group comprising chondroitin sulfates A and C, their mixtures, dermatan sulfate and chondroitin sulfate B, the dimeric units of which have the following formula: wherein R represents OH, SO 3 , R, represents H, SO 3 , Y represents H, COO-, and X represents H, COO-.
Claim 3
Dependent Claim
15 words
Synthetic sulfoamino derivatives of the hyaluronic acid, the dimeric units of which have the formula:
Claim 4
Dependent Claim
15 words
Synthetic sulfoamino derivatives of the hyaluronic acid, the dimeric units of which have the formula:
Claim 5
Dependent Claim
40 words
Synthetic derivatives according to claims 1 and 2, characterized by following chemical parameters calculated on dry basis and referred to the corresponding sodium salt: sulfonic sulfur 8,0-12% sulfate/carboxylic groups 1,5-2,3 residual N-acetyl groups <3% molecular weight 2,3-30 x 10 3
Claim 6
Dependent Claim
35 words
Synthetic derivatives according to claim 3, characterized in that said parameters are included in the following ranges: sulfonic sulfur 9,5-11,4% sulfate / carboxylic groups 1,8-2,1 residual N-acetyl groups <1% molecular weight 3-15 x 10 3
Claim 7
Dependent Claim
72 words
A process for the preparation of the derivatives of claim 1 and 2, characterized in that a first deacetylation step in carried out by heating the starting glycosaminoglycane to the temperature of 105°C with an excess of hydrazine sulfate and anhydrous hydrazine for a time not greater than 6 hours and a subsequent step of selective N-sulfation is carried out in aqueous medium at pH 9 with an excess of sulfating agent.
Claim 8
Dependent Claim
20 words
A process according to claim 5, characterized in that said sulfating agent is selected among triethylamine-sulfuric anhydride and clorosulfonic acid.
Claim 9
Dependent Claim
37 words
A process according to claim 5, characterized in that said N-deacetylation reaction is carried out in a number of steps until the content of acetyl groups in brought to the level required for the next N-sulfation step.
Claim 10
Dependent Claim
26 words
A process according to claim 5, characterized in that before said N-deacetylation step a preliminary depolymerization step is carried out in a per se known manner.
Claim 11
Dependent Claim
19 words
A process according to claim 8, characterized in that said depolymerization step is carried out before the N-sulfation step.
Claim 12
Dependent Claim
23 words
Pharmaceutical composition, characterized by containig, as the active ingredient, a giycosaminoglycan derivative according to claims 1 and 2, together with the usual excipients.
Claim 13
Dependent Claim
9 words
Pharmaceutical compostion according to claim 10, having clearing activity.
Claim 14
Dependent Claim
21 words
Pharmaceutical composition according to claim 10, characterized in that said active ingredient is contained in a unitary dose of 1-500 mg.
References Cited (Backward Citations)
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