Derivatized poly(ester amide) as a biobeneficial coating

• US 8,609,123 B2
• Filed: 11/29/2004
• Issued: 12/17/2013
• Est. Priority Date: 11/29/2004
• Status: Expired due to Fees

• Current Assignee: Advanced Cardiovascular Systems Incorporated
• Original Assignee: Advanced Cardiovascular Systems Incorporated
• Inventors: Hossainy, Syed Faiyaz Ahmed, Pacetti, Stephen Dirk
• Primary Examiner(s): Heyer, Dennis
• Application Number:
  US10/999,391
• Publication Number:
  US 20060115513A1
• Time in Patent Office: 3,305 Days
• Field of Search: None
• US Class Current: 424/423
• CPC Class Codes: A61L 2300/608 having two or more layers
• 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: C08L 77/12 Polyester-amides

Abstract

A derivatized poly(ester amide) (D-PEA) and coatings and medical devices formed therefrom are provided. The coatings and medical devices may optionally include a biobeneficial material and/or a biocompatible polymer and/or a bioactive agent. The medical devices can be implanted in a patient to treat, prevent, or ameliorate a disorder such as 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, or combinations thereof.

Claims

1. A coating on a medical device comprising a layer comprising a derivatized poly(ester amide)(D-PEA),

the D-PEA being derivatized with a biobeneficial moiety selected from the group consisting of poly(vinyl pyrrolidone), poly(styrene sulfonate), poly(hydroxypropyl methacrylamide), hyaluronic acid, fibrin, albumin, elastin, dextran, and combinations thereof;

wherein the D-PEA is further derivatized with a nitric oxide preserver moiety.

2. The coating of claim 1, wherein the biobeneficial moiety is poly(vinyl pyrrolidone).

3. The coating of claim 1, wherein the biobeneficial moiety is poly(styrene sulfonate).

4. The coating of claim 1, further comprising a bioactive agent.

5. The coating of claim 4, wherein the bioactive agent is selected from the group consisting of paclitaxel, docetaxel, estradiol, nitric oxide donors, super oxide dismutases, 4-amino-2,2,6,6-tetramethylpiperidine-1-oxyl (4-amino-TEMPO), tacrolimus, dexamethasone, rapamycin, 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, ABT-578, clobetasol, progenitor cell capturing antibody, and combinations thereof.

6. The coating of claim 1, wherein the layer of D-PEA is coated on top of a drug matrix.

7. The coating of claim 6, wherein the drug matrix comprises a D-PEA.

8. The coating of claim 1, wherein the medical device is a stent.

9. The coating of claim 6, wherein the medical device is a stent.

10. The coating of claim 6, wherein the medical device is a metallic stent with channels, pores, perforations and/or depots.

11. The coating of claim 6, wherein the medical device is a metallic stent formed of a material comprising magnesium, stainless steel, cobalt-chromium alloy or nitinol.

17. A stent comprising a coating according to claim 1.

18. The coating of claim 1, wherein the biobeneficial moiety is poly(hydroxypropyl methacrylamide).

19. The coating of claim 1, wherein the biobeneficial moiety is hyaluronic acid.

20. The coating of claim 1, wherein the biobeneficial moiety is fibrin.

21. The coating of claim 1, wherein the biobeneficial moiety is albumin.

22. The coating of claim 1, wherein the biobeneficial moiety is elastin.

23. The coating of claim 1, wherein the biobeneficial moiety is dextran.

12. A medical device formed of a material comprising a derivatized poly(ester amide) (D-PEA),

the D-PEA being derivatized with a biobeneficial moiety selected from the group consisting of poly(vinyl pyrrolidone), poly(styrene sulfonate), poly(hydroxypropyl methacrylamide), hyaluronic acid, fibrin, albumin, elastin, dextran, and combinations thereof;

where the D-PEA is further derivatized with a nitric oxide preserver moiety.

13. The medical device of claim 12, wherein the D-PEA is included in a coating layer for the device.

14. The medical device of claim 12, wherein the biobeneficial moiety is poly(vinyl pyrrolidone).

15. The medical device of claim 12, further comprising a bioactive agent.

16. The medical device of claim 12 which is a stent.