Articles including natural biodegradable polysaccharides and uses thereof

• US 8,241,656 B2
• Filed: 11/11/2005
• Issued: 08/14/2012
• Est. Priority Date: 09/21/2005
• Status: Expired due to Fees

• Current Assignee: Nc Surmodics
• Original Assignee: Surmodics Incorporated
• Inventors: Chudzik, Stephen J., Swan, Dale G., Burkstrand, Michael J.
• Primary Examiner(s): Singh, Anoop
• Assistant Examiner(s): FALKOWITZ, ANNA R
• Application Number:
  US11/271,237
• Publication Number:
  US 20070065482A1
• Time in Patent Office: 2,468 Days
• Field of Search: 424/423, 424/427, 424/426, 424/133.1
• US Class Current: 424/426
• CPC Class Codes: A61K 47/34 Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers A61K47/10 takes precedence
• CPC Class Codes: A61K 9/0024 Solid, semi-solid or solidifying implants, which are implanted or injected in body tissue compositions for intravenous administration, normal injectable solutions or dispersions for, e.g. subcutaneous administration A61K9/0019; brain implants A61K9/0085; (coated) prostheses, catheters or stents A61L
• CPC Class Codes: A61K 9/0051 Ocular inserts, ocular implants
• CPC Class Codes: A61K 9/2027 obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
• CPC Class Codes: A61K 9/205 Polysaccharides, e.g. alginate, gums; Cyclodextrin
• CPC Class Codes: A61L 2300/232 Monosaccharides, disaccharides, polysaccharides, lipopolysaccharides
• CPC Class Codes: A61L 2300/252 Polypeptides, proteins, e.g. glycoproteins, lipoproteins, cytokines
• CPC Class Codes: A61L 2300/258 Genetic materials, DNA, RNA, genes, vectors, e.g. plasmids
• CPC Class Codes: A61L 2300/604 Biodegradation
• CPC Class Codes: A61L 2300/606 Coatings
• CPC Class Codes: A61L 2420/02 Methods for coating medical devices
• CPC Class Codes: A61L 27/20 Polysaccharides
• CPC Class Codes: A61L 27/34 Macromolecular materials
• CPC Class Codes: A61L 27/54 Biologically active materials, e.g. therapeutic substances A61L27/227 takes precedence
• CPC Class Codes: A61L 27/58 Materials at least partially resorbable by the body
• CPC Class Codes: A61L 29/085 Macromolecular materials
• CPC Class Codes: A61L 29/16 Biologically active materials, e.g. therapeutic substances A61L29/048 takes precedence
• CPC Class Codes: A61L 31/042 Polysaccharides
• CPC Class Codes: A61L 31/10 Macromolecular materials
• CPC Class Codes: A61L 31/16 Biologically active materials, e.g. therapeutic substances A61L31/047 takes precedence
• CPC Class Codes: A61P 43/00 : Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: B05D 1/36 : Successively applying liquids or other fluent materials, e.g. without intermediate treatment
• CPC Class Codes: B05D 7/52 : Two layers
• CPC Class Codes: C08B 31/006 : Crosslinking of derivatives of starch
• CPC Class Codes: C08B 31/04 : of organic acids , e.g. alkenyl-succinated starch
• CPC Class Codes: C08B 33/02 : Esters
• CPC Class Codes: C08B 33/04 : Ethers
• CPC Class Codes: C08L 3/02 : Starch; Degradation products thereof, e.g. dextrin
• CPC Class Codes: C08L 3/12 : Amylose; Amylopectin; Degradation products thereof
• CPC Class Codes: C09D 103/02 : Starch; Degradation products thereof, e.g. dextrin
• CPC Class Codes: C09D 103/18 : Ethers

Abstract

Medical articles having a body member including natural biodegradable polysaccharides are described. The body member is formed from a plurality of natural biodegradable polysaccharides having pendent coupling groups. The body member can also include a bioactive agent which can be released to provide a therapeutic effect to a patient.

Claims

1. A medical implant comprising a biodegradable body member comprising a matrix of crosslinked polymers, wherein the matrix is formed from a composition comprising polymers having a molecular weight of 500,000 Da or less and comprising

repeating glucopyranose units comprising hydroxyl groups present on 2, 3, and 6 position carbons, wherein the glucopyranose units are joined by α

-1,4 linkages,

pendent polymerizable groups, and

an ester group present between the pendent polymerizable group and the glucopyranose unit, wherein the ester group is formed from esterification of a hydroxyl group selected from the hydroxyl groups present on the 2, 3, and 6 position carbons of the glucopyranose unit which comprises the formula;

2. The medical implant of claim 1 wherein polymers comprising repeating glucopyranose units have a molecular weight in the range of 500 Da to 500,000 Da.

3. The medical implant of claim 2 wherein the polymers comprising repeating glucopyranose units have a molecular weight in the range of 1000 Da to 10,000 Da.

4. The medical implant of claim 1 wherein the polymers comprising repeating glucopyranose units are selected from the group consisting of amylose and maltodextrin.

5. The medical implant of claim 1 wherein the polymerizable groups are present on the polymer in an amount of 0.7 mmoles or less of pendent polymerizable groups per milligram poly(glucopyranose) polymer.

6. The medical implant of claim 1 wherein the polymerizable groups are selected from vinyl groups, acrylate groups, methacrylate groups, ethacrylate groups, 2-phenyl acrylate groups, acrylamide groups, methacrylamide groups, itaconate groups, and styrene groups.

7. The medical implant of claim 1 wherein the composition comprises a photoinitiator comprising two or more photoreactive groups.

8. The medical implant of claim 1 wherein the composition comprises a redox pair.

9. The medical implant of claim 1 wherein the matrix further comprises a bioactive agent.

10. The medical implant of claim 9 wherein the bioactive agent is selected from the group comprising polypeptides, nucleic acids, and polysaccharides.

11. The medical implant of claim 10 wherein the bioactive agent has a molecular weight of 10,000 Da or greater.

12. The medical implant of claim 1 having a dry mass of 2.5 g or less.

13. The medical implant of claim 1 wherein the body member comprises a cross section having a circular shape.

14. The medical implant of claim 1 adapted for placement into at least one portion of the eye.

15. The medical implant of claim 14 fabricated to have an intravitreal lifetime of 24 hours or less.

16. The medical implant of claim 14 fabricated to have an intravitreal lifetime of one month or less.

17. The medical implant of claim 1 wherein the composition comprises the polymers at a concentration in the range of 200 mg/mL to 2000 mg/mL.

18. The medical implant of claim 1 wherein the body member is formed by a method comprising steps of:

(i) disposing in a mold the composition comprising (a) the polymers comprising repeating glucopyranose units, (b) an initiator, and (c) a bioactive agent; and

(ii) activating the initiator to cause polymerization of the polymers and matrix formation.

19. The medical implant of claim 17 where the composition comprises the polymers at a concentration in the range of 300 mg/mL to 1500 mg/mL.

20. The medical implant of claim 19 where the composition comprises the polymers at a concentration in the range of 500 mg/mL to 1500 mg/mL.

21. The medical implant of claim 20 where the composition comprises the polymers at a concentration in the range of 600 mg/mL to 1500 mg/mL.

23. The medical implant of claim 1 wherein the ester group is formed by reaction of a compound including a polymerizable group and an isocyante group, wherein a hydroxyl group selected from the hydroxyl groups present on the 2, 3, and 6 position carbons of the glucopyranose unit react with the isocyante group to form the ester group, which is in the form of a carbamate group.

24. The medical implant of claim 23 wherein the compound including the polymerizable group and the isocyante group has the following structure:

22. An ocular implant comprising a biodegradable body member comprising a matrix comprising crosslinked polymers, wherein the matrix is formed from a composition comprising polymers having a molecular weight of 500,000 Da or less and comprising

repeating glucopyranose units comprising hydroxyl groups present on 2, 3, and 6 position carbons, wherein the glucopyranose units are joined by α

-1,4 linkages

pendent polymerizable groups, and

an ester group present between the pendent polymerizable group and the glucopyranose unit, wherein the ester group is formed from esterification of a hydroxyl group selected from the hydroxyl groups present on the 2, 3, and 6 position carbons of the glucopyranose unit which comprises the formula;

25. A medical implant comprising a biodegradable body member comprising a matrix of polymers, wherein the matrix is formed from a composition comprising polymers having a molecular weight of 500,000 Da or less and comprising repeating glucopyranose units comprising hydroxyl groups present on 2, 3, and 6 position carbons, wherein the glucopyranose units are joined by α

-1,4 linkages, and pendent polymerizable groups, and an ester group present between the pendent polymerizable group and the glucopyranose unit which comprises the formula;