Polymer films

• US 9,408,916 B2
• Filed: 09/19/2014
• Issued: 08/09/2016
• Est. Priority Date: 09/19/2013
• Status: Active Grant

• Current Assignee: Microvention Incorporated (Terumo Corporation)
• Original Assignee: Microvention Incorporated (Terumo Corporation)
• Inventors: Cruise, Gregory M., Hincapie, Gloria, Harris, Clayton, Wu, Yue
• Primary Examiner(s): Sample, David
• Assistant Examiner(s): POLLEY, CHRISTOPHER M
• Application Number:
  US14/491,813
• Publication Number:
  US 20150079328A1
• Time in Patent Office: 690 Days
• US Class Current: 1/1
• CPC Class Codes: A61K 47/32 Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers , poly(meth)acrylates, or polyvinyl pyrrolidone
• 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: A61L 31/048 obtained by reactions only involving carbon-to-carbon unsaturated bonds A61L31/041 takes precedence
• CPC Class Codes: A61L 31/148 Materials at least partially resorbable by the body
• CPC Class Codes: A61L 31/16 Biologically active materials, e.g. therapeutic substances A61L31/047 takes precedence
• CPC Class Codes: B32B 2439/80 Medical packaging
• CPC Class Codes: B65B 3/003 Filling medical containers such as ampoules, vials, syringes or the like
• CPC Class Codes: C08F 120/56 Acrylamide; Methacrylamide
• CPC Class Codes: C08F 220/06 Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
• CPC Class Codes: C08F 220/20 of polyhydric alcohols or phenols , e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
• CPC Class Codes: C08F 220/56 Acrylamide; Methacrylamide
• CPC Class Codes: C08F 222/102 of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
• CPC Class Codes: C08F 222/385 Monomers containing two or more (meth)acrylamide groups, e.g. N,N'-methylenebisacrylamide
• CPC Class Codes: C08J 2333/14 of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
• CPC Class Codes: C08J 2333/26 Homopolymers or copolymers of acrylamide or methacrylamide
• CPC Class Codes: C08J 5/18 Manufacture of films or sheets
• CPC Class Codes: Y10T 428/1341 Contains vapor or gas barrier, polymer derived from vinyl chloride or vinylidene chloride, or polymer containing a vinyl alcohol unit
• CPC Class Codes: Y10T 428/21 Circular sheet or circular blank

Abstract

Biodegradable, cross-linked polymer films and methods of making the same are described. The polymer films can be used for preventing adhesions following surgery and/or delivering therapeutic agents.

Claims

1. A polymer film comprising:

at least one monomer including at least one functional group; and

at least one crosslinker selected from bis-glycidyl amino alcohol, bi-functionalized methacryloyl-Ala-Pro-Gly-Leu-AEE-methacrylate,

2. The polymer film of claim 1, wherein the polymer film has a shape selected from a circle, square, rectangle, triangle, ellipse, or pentagon.

3. The polymer film of claim 1, wherein the at least one functional group is acrylate, acrylamide, methacrylate, or methacrylamide.

4. The polymer film of claim 1, wherein the at least one monomer includes an ionizable functional group.

5. The polymer film of claim 4, wherein the ionizable functional group is basic.

6. The polymer film of claim 4, wherein the ionizable functional group is acidic.

7. The polymer film of claim 1, wherein the at least one crosslinker includes at least two functional groups.

8. The polymer film of claim 1, wherein the crosslinker includes at least one linkage susceptible to degradation through hydrolysis or enzymatic action.

9. The polymer film of claim 8, wherein the at least one linkage is an ester, a thioester, a carbonate, a carbamate, a peptide cleavable by matrix metalloproteinases, a peptide cleavable by matrix collagenase, a peptide cleavable by matrix elastase, a peptide cleavable by matrix cathepsin, or a combination thereof.

10. The polymer film of claim 9, including a second crosslinker including a second linkage selected from an ester, a thioester, a carbonate, a carbamate, a peptide cleavable by matrix metalloproteinases, a peptide cleavable by matrix collagenases, a peptide cleavable by matrix elastases, and a peptide cleavable by matrix cathepsins.

11. The polymer film of claim 1, wherein the polymer film is substantially degraded within about 6 months of implantation.

12. The polymer film of claim 1, wherein the polymer film is substantially degraded within about 1 month of implantation.

13. The polymer film of claim 1, wherein the at least one monomer is acrylamide and the at least one crosslinker is bis-glycidyl amino alcohol.

14. The polymer film of claim 1, wherein the at least one monomer is acrylamide and the at least one crosslinker is bi-functionalized methacryloyl-Ala-Pro-Gly-Leu-AEE-methacrylate.

15. A method of making a polymer film comprising:

reacting a prepolymer solution including at least one monomer including at least one functional group, at least one crosslinker susceptible to degradation, and an initiator; and

forming the polymer film, wherein the polymer film has a thickness between about 40 μ

m and about 1,200 μ

m,

wherein the at least one crosslinker is selected from bis-glycidyl amino alcohol, bi-functionalized methacryloyl-Ala-Pro-Gly-Leu-AEE-methacrylate,

16. The method of claim 15, wherein the film is formed between two plates including at least one spacer.

17. The method of claim 15, wherein the initiator is N,N,N′

,N′

-tetramethylethylenediamine.

18. The method of claim 15, wherein the polymer film has a shape selected from a circle, square, rectangle, triangle, ellipse, or pentagon.

19. The method of claim 15, wherein the at least one functional group is acrylate, acrylamide, methacrylate, or methacrylamide.

20. The method of claim 15, wherein the polymer film is biodegradable.

21. The method of claim 20, wherein the polymer film is substantially degraded within about 1 month of implantation.

22. The method of claim 20, wherein the at least one monomer is acrylamide and the at least one crosslinker is bis-glycidyl amino alcohol.

23. The method of claim 20, wherein the at least one monomer is acrylamide and the at least one crosslinker is bi-functionalized methacryloyl-Ala-Pro-Gly-Leu-AEE-methacrylate.