Method for deacetylation of biopolymers

Patent metadata

Field	Value
Publication number	US-11254792-B2
Application number	US-201616066746-A
Country	US
Kind code	B2
Filing date	Dec 28, 2016
Priority date	Dec 29, 2015
Publication date	Feb 22, 2022
Grant date	Feb 22, 2022

Abstract

A method for at least partial deacetylation of a biopolymer comprising acetyl groups, including: a1) providing a biopolymer including acetyl groups; a2) reacting the biopolymer including acetyl groups with hydroxylamine (NH2OH) or a salt thereof at a temperature of 100° C. or less for 2-200 hours to form an at least partially deacetylated biopolymer; and a3) recovering the at least partially deacetylated biopolymer.

First claim

The invention claimed is:

1. A method of preparing a hydrogel product comprising crosslinked glycosaminoglycan molecules, the method comprising:
(a) obtaining a solution comprising an at least partially deacetylated glycosaminoglycan with a degree of acetylation between 50% and 99% and a second glycosaminoglycan, wherein the second glycosaminoglycan is different from the at least partially deacetylated glycosaminoglycan;
(b) activating carboxyl groups on the at least partially deacetylated glycosaminoglycan and/or the second glycosaminoglycan with a coupling agent, to form activated glycosaminoglycans;
(c) crosslinking the activated glycosaminoglycans via two different crosslinkers solely with amide bonds to provide crosslinked glycosaminoglycans; and
(d) acylating residual amine groups of the crosslinked glycosaminoglycans obtained in (c) to form acylated crosslinked glycosaminoglycans; and
(e) subjecting the crosslinked glycosaminoglycans provided in (c) or (d) to alkaline treatment to hydrolyze ester crosslinks formed as byproducts during the amide crosslinking in (c),
wherein the first and second glycosaminoglycans are not the two different crosslinkers, and wherein the two different crosslinkers are carbohydrate-based crosslinkers.

2. The method according to claim 1 , wherein the second glycosaminoglycan is at least partially deacetylated.

3. The method according to claim 1 , wherein the second glycosaminoglycan is not deacetylated.

4. The method according to claim 1 , wherein the glycosaminoglycans are selected from hyaluronic acid, chondroitin, chondroitin sulphate, heparin sulphate, heparosan, heparin, dermatan sulphate, and keratin sulphate.

5. The method according to claim 1 , wherein the at least partially deacetylated glycosaminoglycan and/or the second glycosaminoglycan is hyaluronic acid.

6. The method according to claim 1 , wherein the at least partially deacetylated glycosaminoglycan and the second glycosaminoglycan are hyaluronic acids.

7. The method according to claim 1 , wherein (b) and (c) occur simultaneously.

8. The method according to claim 1 , wherein (b) occurs prior to (c).

9. The method according to claim 1 , wherein the hydrogel product comprises a portion of glycosaminoglycans which are not crosslinked.

10. The method according to claim 9 , wherein the crosslinked glycosaminoglycan molecules comprise at least 80% by weight of the hydrogel product.

11. The method according to claim 1 , wherein the at least partially deacetylated glycosaminoglycan has a degree of acetylation between 93% and 99%.

12. The method according to claim 1 , wherein the second glycosaminoglycan obtained in a) is not altered or modified by addition or removal of functional groups.

13. The method according to claim 1 , wherein at least one of the two different crosslinkers is diaminotrehalose.

Assignees

• Galderma Holding SA

Inventors

• Olsson Johan
• Harris Craig Steven

Classifications

• C08B37/0069 Primary

  Chondroitin-4-sulfate, i.e. chondroitin sulfate A; Dermatan sulfate, i.e. chondroitin sulfate B or beta-heparin; Chondroitin-6-sulfate, i.e. chondroitin sulfate C; Derivatives thereof · CPC title

• A61K2800/10

  General cosmetic use · CPC title

• A61Q19/00

  Preparations for care of the skin · CPC title

• A61K8/042

  Gels · CPC title

• A61K8/735

  Mucopolysaccharides, e.g. hyaluronic acid; Derivatives thereof · CPC title