US5008253A
Expired / Lapsed
US
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Sulfoamino derivatives of chondroitin sulfates of dermatan sulfate and of hyaluronic acid and their pharmacological properties
Assignee: Crinos Industria Farmacobiologica SpA
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Filing: 1989-05-02
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Granted: 1991-04-16
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Expires: 2009-05-02
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 of 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 compounds of the present invention find use in the therapy of arteriosclerosis.
Inventors
- 👤 Benito Casu
- 👤 Giangiacomo Torri
- 👤 Annamaria Naggi
- 👤 Marisa Mantovani
- 👤 Rodolfo Pescador
- 👤 Roberto Porta
- 👤 Giuseppe Prino
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 14:57
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
63 words
Synthetic sulfoamino derivatives of glycosaminoglycans selected from the group consisting of chondroitin sulfates A and C, their mixtures, dermatan sulfate and chondroitin sulfate B, the dimeric units of which have the following formula: ##STR6## wherein R represents OH, SO 3 - , R 1 represents H, SO 3 - , Y represents H, COO - , and X represents H, COO - .
Claim 2
Dependent Claim
63 words
Synthetic sulfoamino derivatives of glycosaminoglycans selected from the group consisting of chondroitin sulfates A and C, their mixtures, dermatan sulfate and chondroitin sulfate B, the dimeric units of which have the following formula: ##STR6## wherein R represents OH, SO 3 - , R 1 represents H, SO 3 - , Y represents H, COO - , and X represents H, COO - .
Claim 3
Dependent Claim
16 words
Synthetic sulfoamino derivatives of the hyaluronic acid, the dimeric units of which have the formula: ##STR7##
Claim 4
Dependent Claim
16 words
Synthetic sulfoamino derivatives of the hyaluronic acid, the dimeric units of which have the formula: ##STR7##
Claim 5
Dependent Claim
42 words
Synthetic derivatives according to claims 1 or 2, characterized by the 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 × 10.sup.3
______________________________________
Claim 6
Dependent Claim
34 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 × 10.sup.3
______________________________________
Claim 7
Dependent Claim
74 words
A process for the preparation of the derivatives according to claim 1 or 2, characterized in that a first N-deacetylation step in carried out by heating the starting glycosaminoglycan 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
24 words
A process according to claim 5, characterized in that said sulfating agent is selected from the group consisting of triethylamine-sulfuric anhydride and chlorosulfonic 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 is brought to the level required for the next N-sulfation step.
Claim 10
Dependent Claim
20 words
A process according to claim 5, characterized in that before said N-deacetylation step a preliminary depolymerization step is carried out.
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
17 words
Pharmaceutical composition, comprising, a glycosaminoglycan derivative according to claims 1 or 2, together with pharmaceutically acceptable excipients.
Claim 13
Dependent Claim
10 words
Pharmaceutical compostion according to claim 10, having lipaemia 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)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1994-04-15 | 1994-10-15 | 1995-04-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1998-04-15 | 1998-10-15 | 1999-04-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2002-04-15 | 2002-10-15 | 2003-04-16 | $7700.00 | Window Closed / Lapsed |