Hydrophobic cross-linked gels for bioabsorbable drug carrier coatings

• US 9,220,820 B2
• Filed: 07/16/2013
• Issued: 12/29/2015
• Est. Priority Date: 10/15/2005
• Status: Active Grant

• Current Assignee: Atrium Medical Corporation (Getinge AB)
• Original Assignee: Atrium Medical Corporation (Getinge AB)
• Inventors: Faucher, Keith M., Tang, Hui, Rogers, Lisa, Ferraro, Joseph, Martakos, Paul, Herweck, Steven A., Karwoski, Theodore
• Primary Examiner(s): Fisher, Abigail
• Assistant Examiner(s): KASSA, JESSICA M
• Application Number:
  US13/943,489
• Publication Number:
  US 20140010949A1
• Time in Patent Office: 896 Days
• US Class Current: 1/1
• CPC Class Codes: A61L 2300/41 Anti-inflammatory agents, e.g. NSAIDs
• 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 2300/802 Additives, excipients, e.g. cyclodextrins, fatty acids, surfactants
• CPC Class Codes: A61L 29/08 Materials for coatings
• CPC Class Codes: A61L 29/16 Biologically active materials, e.g. therapeutic substances A61L29/048 takes precedence
• CPC Class Codes: A61L 31/08 Materials for coatings
• 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 7/02 Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
• CPC Class Codes: A61P 9/00 Drugs for disorders of the cardiovascular system
• CPC Class Codes: B05D 3/0254 After-treatment

Abstract

Coatings for medical devices, methods of making the coatings, and methods of using them are described.

Claims

1. A method of preparing a coated medical device, the method comprising:

combining fish oil with vitamin E and one or more therapeutic agents to form a combined fish oil-vitamin E-therapeutic agents material, wherein the fish oil comprises two or more omega-3 fatty acids;

applying the combined fish oil-vitamin E-therapeutic agents material to a medical device; and

heat curing the combined fish oil-vitamin E-therapeutic agents material to cross-link the two or more omega-3 fatty acids directly to each other by one or more of ester bonds and lactone bonds, thereby forming the coated medical device.

2. The method of claim 1, further comprising a step of partially curing the fish oil prior to the step of combining the fish oil with the vitamin E by heat curing to a lesser amount of crosslinking.

3. The method of claim 1, wherein the combined fish oil-vitamin E-therapeutic agents material is heat cured at about 200°

F. for at least about twenty four hours.

4. The method of claim 1, wherein the one or more therapeutic agents comprise an anti-proliferative agent.

5. The method of claim 1, wherein the one or more therapeutic agents comprise an anti-inflammatory agent.

6. The method of claim 1, wherein the two or more omega-3 fatty acids are selected from the group consisting of eicosapentaenoic acid (EPA), docosahexanoic acid (DHA) and alpha-linolenic acid (ALA).

7. The method of claim 1, further comprising a step of sterilizing the coated medical device.

8. The method of claim 7, wherein the step of sterilizing is selected from the group consisting of ethylene oxide, gamma radiation, E beam, steam, gas plasma, or vaporized hydrogen peroxide sterilization.

9. The method of claim 1, wherein the medical device is selected from the group consisting of a stent, a catheter balloon and a surgical mesh.

10. A method of preparing a bioabsorbable coating or film, the method comprising:

partially heat curing fish oil to cross-link two or more fatty acids contained therein directly to each other by ester bonds to form a partially cured fish oil;

combining the partially cured fish oil with a therapeutic agent to form a combined fish oil-therapeutic agent material; and

heat curing the combined fish oil-therapeutic agent material to cross-link the two or more fatty acids directly to each other by ester bonds, thereby forming the bioabsorbable coating or film.

11. The method of claim 10, wherein the combined fish oil-therapeutic agent material is heat cured at about 200°

F. for at least about twenty four hours.

12. The method of claim 10, wherein the bioabsorbable coating or film hydrolyzes in vivo, into substantially non-inflammatory compounds.

13. The method of claim 10, wherein the fish oil is partially heat cured at about 200°

F.

14. The method of claim 10, wherein the fish oil is partially heat cured at about 150°

F.

15. The method of claim 10, wherein the combined fish oil-therapeutic agent material is heat cured for at least about twenty four hours.

16. The method of claim 10, wherein the therapeutic agent is an anti-proliferative agent.

17. The method of claim 10, wherein the therapeutic agent is an anti-inflammatory agent.

18. The method of claim 10, wherein the therapeutic agent is an anti-infective agent.

19. The method of claim 10, further comprising steps of providing vitamin E and combining the vitamin E with the partially cured fish oil prior to heat curing the combined fish oil-therapeutic agent material.

20. The method of claim 10, further comprising steps of providing an anti-oxidant and combining the anti-oxidant with the partially cured fish oil prior to heat curing the combined fish oil-therapeutic agent material.

21. The method of claim 10, wherein the two or more fatty acids are omega-3 fatty acids.

22. The method of claim 21, wherein the omega-3 fatty acids are selected from the group consisting of eicosapentaenoic acid (EPA), docosahexanoic acid (DHA) and alpha-linolenic acid (ALA).

23. The method of claim 10, further comprising a step of sterilizing the bioabsorbable coating.

24. The method of claim 23, wherein the step of sterilizing is selected from the group consisting of ethylene oxide, gamma radiation, E beam, steam, gas plasma, or vaporized hydrogen peroxide sterilization.

25. The method of claim 10, further comprising a step of applying the combined fish oil-therapeutic agent material to a medical device prior to heat curing the combined fish oil-therapeutic agent material.

26. The method of claim 10, further comprising a step of applying the bioabsorbable coating to the medical device.

27. A method of preparing a coated medical device, the method comprising:

partially curing fish oil to cross-link two or more fatty acids contained therein directly to each other by one or more of ester bonds and lactone bonds so as to form a partially cured fish oil;

combining the partially cured fish oil with a therapeutic agent to form a combined partially cured fish oil-therapeutic agent material;

applying the combined partially cured fish oil-therapeutic agent material to a medical device; and

heat curing the combined partially cured fish oil-therapeutic agent material to further cross-link two or more of the fatty acids directly to each other by one or more of ester bonds and lactone bonds, and thereby forming the coated medical device.

28. The method of claim 27, wherein the combined partially cured fish oil-therapeutic agent material is heat cured at about 200°

F. for at least about twenty four hours.

29. The method of claim 27, wherein the fish oil is partially heat cured at about 200°

F.

30. The method of claim 27, wherein the fish oil is partially heat cured at about 150°

F.

31. The method of claim 27, wherein the combined partially cured fish oil-therapeutic agent material is heat cured for at least about twenty four hours.

32. The method of claim 27, wherein the therapeutic agent is an anti-proliferative agent.

33. The method of claim 27, wherein the therapeutic agent is an anti-inflammatory agent.

34. The method of claim 27, wherein the therapeutic agent is an anti-infective agent.

35. The method of claim 27, further comprising steps of providing vitamin E and combining the vitamin E with the partially cured fish oil prior to the step of combining the partially cured fish oil with the therapeutic agent.

36. The method of claim 27, wherein the two or more fatty acids are omega-3 fatty acids.

37. The method of claim 36, wherein the two or more fatty acids are selected from the group consisting of eicosapentaenoic acid (EPA), docosahexanoic acid (DHA) and alpha-linolenic acid (ALA).

38. The method of claim 27, further comprising a step of sterilizing the coated medical device.

39. The method of claim 38, wherein the step of sterilizing is selected from the group consisting of ethylene oxide, gamma radiation, E beam, steam, gas plasma, or vaporized hydrogen peroxide sterilization.

40. The method of claim 27, wherein the medical device is selected from the group consisting of a stent, a catheter balloon and a surgical mesh.

41. The method of claim 27, further comprising steps of providing an anti-oxidant and combining the anti-oxidant with the partially cured fish oil prior to heat curing the combined partially cured fish oil-therapeutic agent material.