Carbon coating on an implantable device

• US 8,128,688 B2
• Filed: 06/19/2007
• Issued: 03/06/2012
• Est. Priority Date: 06/27/2006
• Status: Expired due to Fees

• Current Assignee: Abbott Cardiovascular Systems Incorporated (Abbott Laboratories Incorporated)
• Original Assignee: Abbott Cardiovascular Systems Incorporated (Abbott Laboratories Incorporated)
• Inventors: Ding, Ni, Michal, Gene, Pacetti, Stephen D.
• Primary Examiner(s): Isabella, David
• Assistant Examiner(s): Swaminathan, Seema
• Application Number:
  US11/820,560
• Publication Number:
  US 20070298354A1
• Time in Patent Office: 1,722 Days
• Field of Search: 623/1.11, 623/1.15, 623/1.46, 623/1.42
• US Class Current: 623/1.42
• CPC Class Codes: A61L 2300/606 Coatings
• CPC Class Codes: A61L 31/084 Carbon; Graphite
• CPC Class Codes: A61L 31/16 Biologically active materials, e.g. therapeutic substances A61L31/047 takes precedence

Abstract

A carbon coating on a stent having a bioactive agent covalently attached thereto and methods of making the same are described. The covalent attachment may be achieved via a photo-reactive chemical or a thermo-reactive chemical. In some embodiments, the carbon coating includes a diamond-like material. The bioactive agent may be heparin or superoxide dismutase enzyme or a mimetic thereof.

Claims

1. An implantable device comprising a carbon coating and a bioactive agent attached thereto;

wherein the bioactive agent is covalently attached to a photo-reactive chemical (PRC) which is in turn covalently attached directly to the carbon coating;

wherein the carbon coating comprises covalently linked carbon (C), hydrogen (H), silicon (Si), and oxygen (O) atoms; and

wherein the carbon coating comprises a diamond-like material.

2. The implantable device of claim 1, wherein the bioactive agent is attached to the PRC via at least one reactive group.

3. The implantable device of claim 1, wherein the PRC is a compound in the benzophenone family or a compound in the azide family.

4. The implantable device of claim 3, wherein the PRC is selected from the group consisting of benzophenone tetracarboxylic dianhydride, benzoylbenzoic acid, benzoyl benzoyl chloride, 4-benzoylbenzoic acid N-hydroxysuccinimide ester, benzoyl benzoyl amine, substituted phenyl azide and substituted acyl azide.

5. The implantable device of claim 1, wherein the bioactive agent is selected from the group consisting of superoxide dismutase (SOD), super oxide dismutase mimetics (SODm), heparin, polyethylene glycol/oxide, synthetic peptides or natural proteins, nitric oxide donor molecules, and combinations thereof.

6. The implantable device of claim 1, wherein the implantable device is a stent.

7. A method of treating or preventing a disorder, comprising implanting in a human being an implantable device according to claim 1, wherein the disorder is selected from the group consisting of atherosclerosis, thrombosis, restenosis, hemorrhage, vascular dissection or perforation, vascular aneurysm, vulnerable plaque, chronic total occlusion, claudication, anastomotic proliferation for vein and artificial grafts, bile duct obstruction, ureter obstruction, tumor obstruction, and combinations thereof.

8. A method of treating or preventing a disorder, comprising implanting in a human being an implantable device according to claim 5, wherein the disorder is selected from the group consisting of atherosclerosis, thrombosis, restenosis, hemorrhage, vascular dissection or perforation, vascular aneurysm, vulnerable plaque, chronic total occlusion, claudication, anastomotic proliferation for vein and artificial grafts, bile duct obstruction, ureter obstruction, tumor obstruction, and combinations thereof.

9. An implantable device comprising a carbon coating and a bioactive agent attached thereto,

wherein the bioactive agent is covalently attached to a photo-reactive chemical (PRC) or a thermo-reactive chemical (TRC), which is in turn covalently attached directly to the carbon coating, and

wherein the carbon coating is a diamond-like carbon coating containing only the elements carbon (C) and hydrogen (H).

10. The implantable device of claim 9, wherein the device is made from bioabsorbable polymers, biostable polymers, a metallic material, or an alloy.

11. The implantable device of claim 9, wherein the bioactive agent is attached to the PRC or the TRC via at least one reactive group.

12. The implantable device of claim 9, wherein the PRC is a compound in the benzophenone family or a compound in the azide family.

13. The implantable device of claim 12, wherein the PRC is selected from the group consisting of benzophenone tetracarboxylic dianhydride, benzoylbenzoic acid, benzoyl benzoyl chloride, 4-benzoylbenzoic acid N-hydroxysuccinimide ester, benzoyl benzoyl amine, substituted phenyl azide, and substituted acyl azide.

14. The implantable device of claim 9, wherein the TRC is selected from the group consisting of acyl peroxide, alkyl peroxide, hydroperoxide, perester, azo compounds, disulfides, and combinations thereof.

15. The implantable device of claim 9, wherein the TRC is selected from the group consisting of acetyl or benzoyl peroxides, cumyl peroxide, t-butyl peroxide, t-butyl hydroperoxide, cumyl hydroperoxide, t-butyl perbenzoate, and azobisisobutylonitrile (AIBN).

16. The implantable device of claim 9, wherein the carbon coating further comprises a metal and/or a ceramic.

17. The implantable device of claim 9, wherein the bioactive agent is selected from the group consisting of superoxide dismutase (SOD), super oxide dismutase mimetics (SODm), heparin, polyethylene glycol/oxide, polyethylene glycol/oxide derivative, sodium hyaluronate and its derivatives, sialic acid, synthetic peptides or natural proteins, synthetic or natural polysaccharides, aloe derived pectin (DelSite Inc.), recombinant human gelatin (Fibrogen), nitric oxide donor molecules, and combinations thereof.

18. The implantable device of claim 9, wherein the bioactive agent is selected from the group consisting of paclitaxel, docetaxel, estradiol, 4-amino-2,2,6,6-tetramethylpiperidine-1-oxyl (4-amino-TEMPO), tacrolimus, dexamethasone, rapamycin, rapamycin derivatives, 40-O-(2-hydroxy) ethyl-rapamycin (everolimus), 40-O-(3-hydroxy)propyl-rapamycin, 40-O-[2-(2-hydroxy) ethoxy]ethyl-rapamycin, 40-O-tetrazole-rapamycin, 40-epi-(N1-tetrazolyl)-rapamycin (ABT-578), clobetasol, pimecrolimus, imatinib mesylate, midostaurin, prodrugs thereof, co-drugs thereof, pegylated drugs thereof, and combinations thereof.

19. The implantable device of claim 9, wherein the implantable device is a stent.

20. The implantable device of claim 9, wherein the implantable device is a bioabsorbable stent.