COPOLYMERS HAVING ZWITTERIONIC MOIETIES AND DIHYDROXYPHENYL MOIETIES AND MEDICAL DEVICES COATED WITH THE COPOLYMERS

• US 20080139746A1
• Filed: 11/19/2007
• Published: 06/12/2008
• Est. Priority Date: 11/21/2006
• Status: Active Grant

• Current Assignee: Abbott Laboratories
• Original Assignee: Abbott Laboratories
• Inventors: Pacetti, Stephen
• Granted Patent: US 7,928,176 B2
• Time in Patent Office: Days
• US Class Current: 525/188
• 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

Copolymers are manufactured to include a zwitterionic monomer (e.g., methacryloyloxyethyl phosphorylcholine monomer), a dihydroxyphenyl derivatized monomer, and optionally one or more additional monomers. The dihydroxyphenyl derivatized monomer gives the copolymers excellent adhesion properties. Optional monomers include a cationic amino monomer, a hydrocarbon monomer, and/or a hydrophilic monomer. The copolymers are biocompatible and can be used with medical devices.

Claims

1. A biocompatible polymer having the formula,

2. A biocompatible polymer as in claim 1, wherein n+o+p+q+r=1.

3. A biocompatible polymer as in claim 1, wherein a 3,4-dihydroxyphenyl group is substituted with a 2,3-dihydroxyphenyl group.

4. A biocompatible polymer as in claim 1, in which the zwitterion group is selected from the group consisting of phosphorylcholine, phosphoryl ethanolamine, phosphatidyl ethanolamine, phosphoethanolamine, phosphatidyl serine, sulfobetaine and combinations thereof.

5. 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.

6. 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.

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

8. A medical device coating comprising the biocompatible polymer of claim 1.

9. A biocompatible polymer as in claim 1 having the formula,

10. A biocompatible polymer as in claim 9, in which R₆ is selected from the group consisting of phosphorylcholine, phosphoryl ethanolamine, phosphatidyl ethanolamine, phosphoethanolamine, phosphatidyl serine, sulfobetaine and combinations thereof.

11. A medical device coating comprising the biocompatible polymer of claim 9.

12. A biocompatible polymer as in claim 1 having the formula,

13. A biocompatible polymer as in claim 12, in which R₆ is selected from the group consisting of phosphorylcholine, phosphoryl ethanolamine, phosphatidyl ethanolamine, phosphoethanolamine, phosphatidyl serine, sulfobetaine and combinations thereof.

14. A medical device coating comprising the biocompatible polymer of claim 12.

15. A biocompatible polymer as in claim 1 having the formula,

16. A biocompatible polymer as in claim 14, in which R₆ is selected from the group consisting of phosphorylcholine, phosphoryl ethanolamine, phosphatidyl ethanolamine, phosphoethanolamine, phosphatidyl serine, sulfobetaine and combinations thereof.

17. A medical device coating comprising the biocompatible polymer of claim 15.

18. A biocompatible polymer as in claim 1, in which the molecular weight of the polymer is in a range from about 20 kDa to about 800 kDa.

19. A biocompatible polymer as in claim 1, in which the molecular weight of the polymer is in a range from about 2 kDa to about 200 kDa.

20. A biocompatible coating comprising the biocompatible polymer of claim 1 blended with a polymer selected from the group consisting of poly(vinyl pyrrolidinone), poly(n-butyl methacrylate), poly(n-butyl methacrylate) copolymers, methacrylate polymers, acrylate polymers, and/or a terpolymers of hexyl methacrylate, vinyl acetate, and vinyl pyrrolidinone.

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

22. A medical device as in claim 21, in which n+o+p+q+r=1.