Block copolymers of acrylates and methacrylates with fluoroalkenes

• US 9,446,173 B2
• Filed: 10/03/2014
• Issued: 09/20/2016
• Est. Priority Date: 11/14/2003
• Status: Expired due to Fees

• Current Assignee: Abbott Cardiovascular Systems Incorporated (Abbott Laboratories Incorporated)
• Original Assignee: Abbott Cardiovascular Systems Incorporated (Abbott Laboratories Incorporated)
• Inventors: Claude, Charles D.
• Primary Examiner(s): MULLIS, JEFFREY C
• Application Number:
  US14/505,918
• Publication Number:
  US 20150030652A1
• Time in Patent Office: 718 Days
• Field of Search: None
• US Class Current: 1/1
• CPC Class Codes: A61K 31/436 the heterocyclic ring system containing a six-membered ring having oxygen as a ring hetero atom, e.g. rapamycin
• 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: A61L 2300/416 Anti-neoplastic or anti-proliferative or anti-restenosis or anti-angiogenic agents, e.g. paclitaxel, sirolimus
• CPC Class Codes: A61L 2420/00 Materials or methods for coatings 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 31/10 Macromolecular materials
• CPC Class Codes: A61L 31/16 Biologically active materials, e.g. therapeutic substances A61L31/047 takes precedence
• CPC Class Codes: C08F 293/00 Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule on to polymers modified by introduction of unsaturated end groups C08F290/02
• CPC Class Codes: C08F 293/005 using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
• CPC Class Codes: C08L 2666/02 Organic macromolecular compounds, natural resins, waxes or and bituminous materials
• CPC Class Codes: C08L 53/00 Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
• CPC Class Codes: C09D 153/00 Coating compositions based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
• CPC Class Codes: Y10T 428/31855 Of addition polymer from unsaturated monomers
• CPC Class Codes: Y10T 428/31938 Polymer of monoethylenically unsaturated hydrocarbon

Abstract

A block copolymer comprising a fluorinated block and a non-fluorinated block and method of making the block copolymer are provided. Also provided herein are a coating on an implantable device comprising the block copolymer and method of using the implantable device.

Claims

1. A polymeric coating composition comprising:

a bioactive agent; and

a block copolymer which comprises end groups, a fluorinated block, and at least one non-fluorinated block;

wherein the fluorinated block comprises repeating units of the following structure;

2. The coating composition of claim 1, wherein the non-fluorinated block comprises one or more fluorinated pendant groups.

3. The coating composition of claim 2, wherein the fluorinated pendant group is —

CF₃.

4. The coating composition of claim 1, wherein the bioactive agent is tacrolimus, dexamethasone, rapamycin, everolimus, 40-O-(3-hydroxy)propyl-rapamycin, 40-O-[2-(2-hydroxy)ethoxy]ethyl-rapamycin, or 40-O-tetrazole-rapamycin.

5. An implantable device comprising the coating composition of claim 1.

6. The implantable device of claim 5, wherein the non-fluorinated block comprises one or more fluorinated pendant groups.

7. The implantable device of claim 6, wherein the fluorinated pendant group is —

CF₃.

8. The implantable device of claim 5, wherein the bioactive agent is tacrolimus, dexamethasone, rapamycin, everolimus, 40-O-(3-hydroxy)propyl-rapamycin, 40-O-[2-(2-hydroxy)ethoxy]ethyl-rapamycin, or 40-O-tetrazole-rapamycin.

9. The implantable device of claim 5, wherein the implantable device is a drug-eluting stent.

10. The implantable device of claim 9, wherein the drug-eluting stent is a self-expandable stent, balloon-expandable stent, or stent-graft.

11. The implantable device of claim 5, wherein the implantable device is a graft, artificial heart valve, cerebrospinal fluid shunt, pacemaker electrode, or endocardial lead.

12. The implantable device of claim 11, wherein the graft is an aortic graft.

13. A polymeric coating composition comprising:

a bioactive agent; and

a block copolymer which comprises end groups, a fluorinated block, and at least one non-fluorinated block;

wherein the fluorinated block comprises repeating units of the following structure;

14. The coating composition of claim 13, wherein the bioactive agent is tacrolimus, dexamethasone, rapamycin, everolimus, 40-O-(3-hydroxy)propyl-rapamycin, 40-O-[2-(2-hydroxy)ethoxy]ethyl-rapamycin, or 40-O-tetrazole-rapamycin.

15. An implantable device comprising the coating composition of claim 13.

16. The implantable device of claim 15, wherein the bioactive agent is tacrolimus, dexamethasone, rapamycin, everolimus, 40-O-(3-hydroxy)propyl-rapamycin, 40-O-[2-(2-hydroxy)ethoxy]ethyl-rapamycin, or 40-O-tetrazole-rapamycin.

17. The implantable device of claim 15, wherein the implantable device is a drug-eluting stent.

18. The implantable device of claim 17, wherein the drug-eluting stent is a self-expandable stent, balloon-expandable stent, or stent-graft.

19. The implantable device of claim 15, wherein the implantable device is a graft, artificial heart valve, cerebrospinal fluid shunt, pacemaker electrode, or endocardial lead.

20. The implantable device of claim 19, wherein the graft is an aortic graft.