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US 6,388,060 B1Granted
Process for the sulfation of uronic acid-containing polysaccharides
AssigneeVascular Therapeutics Inc.
InventorsSteven Y. C. Guo, Edward H. Conrad
Life of this patent
Estimating the term…
Abstract
This present invention provides methods of sulfating uronic acid-containing polysaccharides. High levels of sulfation can be obtained using the methods of the present invention.
Claims19
A process for sulfating a uronic acid-containing polysaccharide, said process comprising:
- a) conversion of said uronic acid-containing polysaccharide to an amine salt of said uronic acid-containing polysaccharide;
- b) treating said amine salt of said uronic acid-containing polysaccharide, dissolved in an aprotic solvent, with sulfuric acid to form a first solution and addition of N,N′ carbodiimide to said first solution to form a second solution;
- c) adjusting the pH of said second solution to a pH above 12 for a period of time ranging from about 30 minutes to about 60 minutes and, thereafter, adjusting the pH of said second solution to a pH of about 7;
- and
- d) contacting said second solution with a sulfating agent to form said sulfated uronic acid-containing polysaccharide.
2 more elements
A process for sulfating dermatan sulfate, said process comprising:
- a) converting said dermatan sulfate to an amine salt of dermatan sulfate;
- b) treating said amine salt of dermatan sulfate with sulfuric acid to form a first solution and addition of an N,N′ carbodiimide to form a second solution;
- c) adjusting the pH of said second solution to a pH above 12 for a period of time ranging from about 30 minutes to about 60 minutes and, thereafter, adjusting the pH of said second solution to a pH of about 7;
- and
- d) contacting said second solution with a sulfating agent to form oversulfated dermatan sulfate.
2 more elements
A process for sulfating heparin, said process comprising:
- a) converting said heparin to an amine salt of heparin;
- b) treating said amine salt of heparin with sulfuric acid to form a first solution and addition of an N,N′ carbodiimide to said first solution to form a second solution;
- c) adjusting the pH of said second solution to a pH above 12 for a period of time ranging from about 30 minutes to about 60 minutes and, thereafter, adjusting the pH of said second solution to a pH of about 7;
- and
- d) contacting said second solution with a sulfating agent to form sulfated heparin.
2 more elements
A process for sulfating dermatan sulfate or chondroitin sulfate, said process comprising:
- (a) converting said dermatan sulfate, or chondroitin sulfate to an amine salt of dermatan sulfate, or an amine salt of chondroitin sulfate;
- (b) treating said amine salt of dermatan sulfate or chondroitin sulfate, dissolved in an aprotic solvent, with sulfuric acid to form a first solution and adding N,N′ carbodiimide, to said first solution to form a second solution to initiate and maintain a sulfating reaction for a period of time from about 1 hour to about 3 hours;
- and (c) treating said second solution with base in an aqueous solution at pH above 13 for a period of time ranging from about 30 minutes to about 60 minutes and, thereafter, adjusting the pH of said second solution to a pH of about 7.
A process for sulfating heparin, said process comprising:
- (a) converting said heparin to an amine salt of heparin;
- (b) treating said amine salt of heparin, dissolved in an aprotic solvent, with sulfuric acid to form a first solution and adding N,N′ carbodiimide, to said first solution to form a second solution to initiate and maintain a sulfating reaction for a period of time from about 1 hour to about 3 hours;
- (c) treating said second solution with base in an aqueous solution at a pH above 13 for a period of time ranging from about 30 minutes to about 60 minutes and, thereafter, adjusting the pH of said second solution to a pH of about 7;
- and
- (d) contacting said second solution with a sulfating agent to form sulfated heparin.
2 more elements
A process for sulfating heparan sulfate, said process comprising:
- (a) converting said heparan sulfate to an amine salt of heparin sulfate;
- (b) treating said amine salt of heparan sulfate, dissolved in an aprotic solvent, with sulfuric acid to form a first solution and adding N,N′ carbodiimide, to said first solution to form a second solution to initiate and maintain a sulfating reaction for a period of time from about 1 hour to about 3 hours;
- (c) treating said second solution with base in an aqueous solution at a pH above 13 for a period of time ranging from about 30 minutes to about 60 minutes and, thereafter, adjusting the pH of said second solution to a pH of about 7;
- and
- (d) contacting said second solution with a sulfating agent to form sulfated heparan sulfate.
2 more elements
A process for sulfating alginic acid and hyaluronic acid, said process comprising:
- (a) converting said alginic acid or hyaluronic acid to an amine salt of alginiate, or an amine salt of hyaluronate;
- (b) treating said amine salt of alginate or hyaluronate, dissolved in aprotic solvent, with sulfuric acid to form a first solution and adding N,N′ carbodiimide to said first solution to form a second solution to initiate and maintain a sulfating reaction for a period of time from about 1 hour to about 3 hours;
- and
- (c) treating said second solution with base in an aqueous solution at a pH above 13 for a period of time ranging from about 30 minutes to about 60 minutes and, thereafter, adjusting the pH of said second solution to a pH of about 7.
1 more element
A process for sulfating a uronic acid-containing polysaccharide, said process comprising:
- (a) converting said uronic acid-containing polysaccharide to an amine salt of said uronic acid-containing polysaccharide;
- (b) treating said amine salt of said uronic acid-containing polysaccharide, dissolved in an aprotic solvent, with sulfuric acid to form a first solution and adding N,N′ carbodiimide to said first solution to form a second solution;
- and
- (c) adjusting the pH of said second solution to a pH above 12 for a period of time ranging from about 30 minutes to about 60 minutes and, thereafter, adjusting the pH of said second solution to a pH of about 6 to about 8.
1 more element
Dependencies are inferred from the claim text.