Medical device coatings

• US 9,737,644 B2
• Filed: 09/22/2015
• Issued: 08/22/2017
• Est. Priority Date: 08/25/2010
• Status: Active Grant

• Current Assignee: Medtronic Incorporated (Medtronic Plc)
• Original Assignee: TYRX, INC. (Medtronic Plc)
• Inventors: Pulapura, Satish, Ge, Qing
• Primary Examiner(s): Chung, Susannah
• Assistant Examiner(s): Butcher, Robert T
• Application Number:
  US14/861,597
• Publication Number:
  US 20160008521A1
• Time in Patent Office: 700 Days
• Field of Search: None
• CPC Class Codes: A61K 31/155 Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
• CPC Class Codes: A61K 31/496 Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
• CPC Class Codes: A61K 31/65 Tetracyclines
• CPC Class Codes: A61K 33/38 Silver; Compounds thereof
• CPC Class Codes: A61L 2300/204 with nitrogen-containing functional groups, e.g. aminoxides, nitriles, guanidines
• CPC Class Codes: A61L 2300/216 with other specific functional groups, e.g. aldehydes, ketones, phenols, quaternary phosphonium groups
• CPC Class Codes: A61L 2300/404 Biocides, antimicrobial agents, antiseptic agents
• CPC Class Codes: A61L 2300/606 Coatings
• CPC Class Codes: A61L 2420/06 Coatings containing a mixture of two or more compounds
• 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 1/02 Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
• CPC Class Codes: A61P 17/02 for treating wounds, ulcers, burns, scars, keloids, or the like
• CPC Class Codes: A61P 23/00 Anaesthetics
• CPC Class Codes: A61P 25/00 Drugs for disorders of the nervous system
• CPC Class Codes: A61P 27/02 Ophthalmic agents
• 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 31/00 Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
• CPC Class Codes: A61P 31/04 Antibacterial agents
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: A61P 43/00 : Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: A61P 7/02 : Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
• CPC Class Codes: A61P 7/04 : Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
• CPC Class Codes: A61P 9/00 : Drugs for disorders of the cardiovascular system
• CPC Class Codes: C08L 67/02 : Polyesters derived from dicarboxylic acids and dihydroxy compounds C08L67/06 takes precedence
• CPC Class Codes: C08L 71/02 : Polyalkylene oxides
• CPC Class Codes: C09D 171/02 : Polyalkylene oxides
• CPC Class Codes: C09D 5/14 : Paints containing biocides, e.g. fungicides, insecticides or pesticides C09D5/16 takes precedence
• CPC Class Codes: Y02A 50/30 : Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
• CPC Class Codes: Y10T 428/265 : 1 mil or less
• CPC Class Codes: Y10T 428/31678 : Of metal

Abstract

The present invention relates to coatings comprising polyethylene glycol and at least one polyphenolic polymer. In particular, the polyphenolic polymer could be selected from the group consisting of tyrosine-derived polyarylates, linear polyesteramides, dihydroxybenzoate polymers, and resorcinol-derived polymers. The coating of the present invention may also include a drug, such as an antibiotic. The coatings of the present invention are suitable for use as coatings for medical devices, such as orthopedic pins or stents.

Claims

1. A medical device comprising a coating comprising at least one drug, polyethylene glycol and a polyphenolic polymer, the polyphenolic polymer comprising a linear polyesteramide, the coating comprising about 20% to about 70% of the at least one drug, based on a combined weight of the at least one drug, the polyethylene glycol and the polyphenolic polymer, the polyethylene glycol comprising about 3% to about 16% of the combined weight.

2. The medical device of claim 1, wherein the linear polyesteramide comprises monomer units having the formula:

3. The medical device of claim 1, wherein the polyethylene glycol is selected from the group consisting of PEG-3350, PEG-1000, and PEG-400, the polyphenolic polymer comprising about 20% to about 75% of the combined weight.

4. The medical device of claim 1, wherein the at least one drug comprises rifampin and minocycline.

5. The medical device of claim 1, wherein the medical device is comprised of a material selected from the group consisting of a metal, an organic material, a natural or synthetic polymer or copolymer, and a material of biological origin.

6. The medical device of claim 1, wherein a thickness of the coating is 10 μ

m.

7. The medical device of claim 1, wherein the at least one drug comprises an antimicrobial agent.

8. The medical device of claim 7, wherein at least about 30% to about 50% of the antimicrobial agent, based on the combined weight, is eluted from the coating after about 24 hours.

9. The medical device of claim 7, wherein at least about 80% of the antimicrobial agent is eluted from the coating within about 3 days.

10. The medical device of claim 1, wherein the medical device is an orthopedic fixation device.

11. The medical device of claim 1, wherein the orthopedic fixation device is a screw, tack rod, pin, or plate.

12. The medical device of claim 1, wherein the medical device is a mesh, pouch, or covering.

13. The medical device of claim 1, wherein the medical device is a dressing used in negative pressure wound therapy.

14. The medical device of claim 1, wherein the medical device comprises a material selected from metals, organic natural or synthetic polymers, and materials from a biological origin, wherein the metals include stainless steel and titanium, the organic natural or synthetic polymers include polyethylene, polylactic acid, polyglycolic acid and cellulose, and the material from the biological origin includes porcine heart valves.

15. The medical device of claim 1, wherein the medical device is configured for use for structural reinforcement for muscle flaps, to provide vascular integrity for ligament repair/replacement or for organ support/positioning/repositioning.

16. The medical device of claim 1, wherein the medical device is configured for use in reconstruction procedures involving soft tissue including orthopaedic graft support or stabilization.

17. The medical device of claim 1, wherein the medical device is configured for use in bone fractures.

18. The medical device of claim 1, wherein the medical device comprises a deformable substrate, and the coating is configured to biodegrade such that the coating stiffens or changes a shape of the medical device as the coating biodegrades.

19. The medical device of claim 1, wherein the medical device is selected from a group consisting of implantable access systems, neurostimulators, spinal cord stimulators, breast implants, biopsy devices and patches for delivery of therapeutic agent to intact skin and broken skin.