Amino acid mimetic copolymers and medical devices coated with the copolymers

• US 8,048,975 B2
• Filed: 03/10/2011
• Issued: 11/01/2011
• Est. Priority Date: 11/21/2006
• Status: Expired due to Fees

• Current Assignee: Abbott Laboratories
• Original Assignee: Abbott Laboratories
• Inventors: Pacetti, Stephen
• Primary Examiner(s): Lipman; Bernard
• Application Number:
  US13/045,465
• Publication Number:
  US 20110160391A1
• Time in Patent Office: 236 Days
• Field of Search: 526/304, 526/306, 526/307.7, 526/312, 526/319, 526/328.5
• US Class Current: 526/304
• 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 medical device comprising a supporting structure having a coating associated therewith, the coating comprising a polymer having the formula,

2. The implant device coating as in claim 1, in which the amino acid mimetic group is selected from the group consisting of acetamide, propionamide, alaninamide, lactamide, and glycinamide.

3. The medical device 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. The medical device as in claim 1, in which R₁ and R₂ are methyl groups.

5. The medical device 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.

6. The medical device 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.

7. The medical device as in claim 1, in which the polymer having a chemical formula of

8. The medical device as in claim 1, in which the polymer having a chemical formula of

9. The medical device as in claim 1, wherein the polymer having a chemical formula of

10. The medical device as in claim 1, in which the polymer having a chemical formula of

11. The medical device as in claim 1, in which the polymer having a chemical formula of

12. The medical device as in claim 1, in which the number average molecular weight of the polymer is in a range from about 20K to about 800K.

13. The medical device as in claim 1, in which the number average molecular weight of the polymer is in a range from about 100K to about 600K.

14. The medical device as in claim 1, in which the number average molecular weight of the polymer is in a range from about 2K to about 200K.

15. The medical device as in claim 1, in which the polymer is substantially free of cross-linking.