AMINO ACID MIMETIC COPOLYMERS AND MEDICAL DEVICES COATED WITH THE COPOLYMERS

• US 20080125514A1
• Filed: 11/19/2007
• Published: 05/29/2008
• Est. Priority Date: 11/21/2006
• Status: Active Grant

• Current Assignee: Abbott Laboratories Incorporated
• Original Assignee: Abbott Laboratories Incorporated
• Inventors: Pacetti, Stephen
• Granted Patent: US 7,928,177 B2
• Time in Patent Office: Days
• US Class Current: 523/113
• CPC Class Codes: A61L 2300/00 Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
• 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 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 31/10 Macromolecular materials
• CPC Class Codes: A61L 31/16 Biologically active materials, e.g. therapeutic substances A61L31/047 takes precedence
• CPC Class Codes: A61P 29/00 Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: A61P 37/08 Antiallergic agents antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14
• CPC Class Codes: A61P 7/02 Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
• CPC Class Codes: C08L 27/18 Homopolymers or copolymers or tetrafluoroethene

Abstract

Biocompatible polymers are manufactured to include an amino acid mimetic monomer and one or more hydrophobic acrylate monomers. The amino acid mimetic monomers are selected to mimic the side chain of the amino acids asparagine or glutamine. The amino acid mimetic monomer can be a methacryloyl or acryloyl derivative of 2-hydroxyacetamide, 3-hydroxypropionamide, alaninamide, lactamide, or glycinamide. These amide functional groups offer the advantage of moderate hydrophilicity with little chemical reactivity. The amino acid mimetic monomer can be copolymerized with one or more hydrophobic acrylate monomers to obtain desired coating properties.

Claims

1. A biocompatible polymer comprising:

2. A biocompatible polymer as in claim 1, in which the amino acid mimetic group is selected from the group consisting of acetamide, propionamide, alaninamide, lactamide, glycinamide, or a combination thereof.

3. A biocompatible polymer as in claim 1, in which the hydrophobic group is selected from the group consisting of a methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, 2-ethyl-hexyl, n-hexyl, cyclohexyl, n-hexyl, isobornyl, or trimethylcyclohexyl, and combinations thereof.

4. A biocompatible polymer as in claim 1, in which the glass transition temperature of the polymer when hydrated is in a range from about −

30°

C. to about 37°

C.

5. A biocompatible polymer as in claim 1, in which the glass transition temperature of the polymer when dry is in a range from about −

30°

C. to about 100°

C.

6. A biocompatible polymer as in claim 1, in which R₁ and R₂ are methyl groups.

7. A biocompatible polymer as in claim 1 having a chemical formula of

8. A biocompatible polymer as in claim 1 having a chemical formula of

9. A biocompatible polymer as in claim 1 having a chemical formula of

10. A biocompatible polymer as in claim 1 having a chemical formula of

11. A biocompatible polymer as in claim 1 having a chemical formula of

12. A biocompatible polymer as in claim 1, in which the number average molecular weight is in a range from about 20K to about 800K.

13. A biocompatible polymer as in claim 1, in which the number average molecular weight is in a range from about 100K to about 600K.

14. A biocompatible polymer as in claim 1, in which the number average molecular weight is in a range from about 2K to about 200K.

15. A biocompatible polymer as in claim 1, in which the polymer is substantially free of cross-linking.

16. An implant device coating comprising the biocompatible polymer of any of claims 1, 7, 8, 9, 10, or 11.

17. A medical device comprising a supporting structure having a coating associated therewith, the coating comprising a polymer having the formula,

18. A medical device as in claim 17, in which the amino acid mimetic group is selected from the group consisting of acetamide, propionamide, alaninamide, lactamide, glycinamide, or a combination thereof.

19. A medical device as in claim 17, in which the hydrophobic group is selected from the group consisting of a methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, 2-ethyl-hexyl, n-hexyl, cyclohexyl, n-hexyl, isobornyl, or trimethylcyclohexyl, and combinations thereof.

20. A medical device as in claim 17, in which R₁ and R₂ are methyl groups.