Dry diazeniumdiolation methods for producing nitric oxide releasing medical devices

• US 8,158,187 B2
• Filed: 12/19/2008
• Issued: 04/17/2012
• Est. Priority Date: 12/19/2008
• Status: Expired due to Fees

• Current Assignee: Medtronic Vascular, Inc. (Medtronic Plc)
• Original Assignee: Medtronic Vascular, Inc. (Medtronic Plc)
• Inventors: Chen, Mingfei, Cheng, Peiwen, Udipi, Kishore
• Primary Examiner(s): Feely, Michael J
• Application Number:
  US12/340,089
• Publication Number:
  US 20100159119A1
• Time in Patent Office: 1,215 Days
• Field of Search: 427/2.1, 427/2.14, 427/2.24, 427/2.25, 427/2.26, 427/331, 427/333, 427/337, 427/372.2, 427/384, 427/398.4, 427/402, 427/407.1, 427/409, 427/2.21, 427/385.5
• US Class Current: 427/2.25
• CPC Class Codes: A61L 2300/114 Nitric oxide, i.e. NO
• 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 2300/608 having two or more layers
• CPC Class Codes: A61L 2300/61 containing two or more active agents in different layers
• CPC Class Codes: A61L 2420/02 Methods for coating 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 31/04 Antibacterial agents
• CPC Class Codes: A61P 9/00 Drugs for disorders of the cardiovascular system

Abstract

The methods of the present disclosure in a broad aspect provide for dry diazeniumdiolation procedures for producing nitric oxide releasing medical devices. These medical devices may alternatively have cap coats applied prior to dry diazeniumdiolation to produce nitric oxide releasing medical devices with cap coats.

Claims

1. A method of making a dry diazeniumdiolated polymer coated medical device comprising the steps of:

a) providing a medical device;

b) coating said medical device with a secondary amine functionalized polymer;

wherein said secondary amine functionalized polymer is a polymer represented by Formula I;

2. The method of claim 1, wherein said pressure is between about 0.1 atmospheres and about 35 atmospheres.

3. The method of claim 1, wherein said medical device is a metallic medical device.

4. The method of claim 3, wherein said metallic medical device comprises stainless steel, nitinol, tantalum, a nonmagnetic nickel-cobalt-chromium-molybdenum [MP35N] alloy, platinum, titanium, and a combination thereof.

5. The method of claim 1, further comprising coating said medical device with at least one bioactive agent.

6. The method of claim 5, wherein said bioactive agent is selected from the group consisting of an antisense agent, an antineoplastic agent, an antiproliferative agent, an antithrombogenic agent, an anticoagulant, an antiplatelet agent, an antibiotic, an anti-inflammatory agent, a steroid, a gene therapy agent, a therapeutic substance, an organic drug, a pharmaceutical compound, a recombinant DNA product, a recombinant RNA product, a collagen, a collagenic derivative, a protein, a protein analog, a saccharide, a saccharide derivative, and combinations thereof.

7. The method of claim 5, wherein said bioactive agent is zotarolimus.

8. The method of claim 1, wherein said medical device is selected from the group consisting of a vascular stent, stent graft, urethdral stent, biliary stent, catheter, suture, ocular device, heart valve, shunt, pacemaker, bone screw, bone anchor, protective plate, and prosthetic device.

9. The method of claim 1, wherein said medical device is a vascular stent.

10. A method of making a cap-coated dry diazeniumdiolated polymer coated medical device, comprising the steps of:

a) providing a medical device;

b) coating said medical device with a secondary amine functionalized polymer;

wherein said secondary amine functionalized polymer is a polymer represented by Formula I;

11. The method of claim 10, wherein said cap-coat polymer is selected from the group consisting of methacrylate polymer, acrylate polymer, block copolymer of styrene and isobutylene, and fluorinated polymer.

12. The method of claim 10, wherein said pressure is between about 0.1 atmospheres and about 35 atmospheres.

13. The method of claim 10, wherein said medical device is a metallic medical device.

14. The method of claim 13, wherein said metallic medical device comprises stainless steel, nitinol, tantalum, a nonmagnetic nickel-cobalt-chromium-molybdenum [MP35N] alloy, platinum, titanium, and a combination thereof.

15. The method of claim 10, wherein further comprising coating said medical device with at least one bioactive agent.

16. The method of claim 15, wherein said bioactive agent is selected from the group consisting of an antisense agent, an antineoplastic agent, an antiproliferative agent, an antithrombogenic agent, an anticoagulant, an antiplatelet agent, an antibiotic, an anti-inflammatory agent, a steroid, a gene therapy agent, a therapeutic substance, an organic drug, a pharmaceutical compound, a recombinant DNA product, a recombinant RNA product, a collagen, a collagenic derivative, a protein, a protein analog, a saccharide, a saccharide derivative, and combinations thereof.

17. The method of claim 15, wherein said bioactive agent is rapamycin or its derivatives.

18. The method of claim 10, wherein said medical device is selected from the group consisting of a vascular stent, stent graft, urethral stent, biliary stent, catheter, suture, ocular device, heart valve, shunt, pacemaker, bone screw, bone anchor, protective plate and prosthetic device.

19. The method of claim 10, wherein said medical device is a vascular stent.