Copolymers having zwitterionic moieties and dihydroxyphenyl moieties and medical devices coated with the copolymers

• US 7,928,176 B2
• Filed: 11/19/2007
• Issued: 04/19/2011
• 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:
  US11/942,695
• Publication Number:
  US 20080139746A1
• Time in Patent Office: 1,247 Days
• Field of Search: 526/277, 526/312, 526/320, 526/328.5
• US Class Current: 526/277
• 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 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 the polymer is substantially free of cross-linking.

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

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

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

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

11. A medical device coating comprising the biocompatible polymer of claim 10.

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

13. A medical device coating as in claim 11, 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, in which the molecular weight of the polymer is in a range from about 20 kDa to about 800 kDa.

16. 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.

17. 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.