Hydrophobic biologically absorbable coatings for drug delivery devices and methods for fabricating the same

• US 7,455,907 B2
• Filed: 04/11/2006
• Issued: 11/25/2008
• Est. Priority Date: 07/30/2003
• Status: Expired due to Fees

• Current Assignee: Advanced Cardiovascular Systems Incorporated
• Original Assignee: Advanced Cardiovascular Systems Incorporated
• Inventors: Pacetti, Stephen D., Hossainy, Syed F. A.
• Primary Examiner(s): ZACHARIA, RAMSEY E
• Application Number:
  US11/402,392
• Publication Number:
  US 20060182782A1
• Time in Patent Office: 959 Days
• Field of Search: 428/411.1, 428/480, 623/1.46, 623/1.49
• US Class Current: 428/411.1
• CPC Class Codes: A61L 31/10 Macromolecular materials
• CPC Class Codes: C08L 67/04 Polyesters derived from hydroxycarboxylic acids, e.g. lactones C08L67/06 takes precedence
• CPC Class Codes: Y10T 428/31504 Composite [nonstructural laminate]
• CPC Class Codes: Y10T 428/31786 Of polyester [e.g., alkyd, etc.]

Abstract

A polymer coating for medical devices based on polyorthoesters and methods for fabricating the coating are disclosed.

Claims

1. A medical article, comprising an implantable substrate having a coating deposited on the substrate, the coating comprising a polymer, the polymer being a product of co-polycondensation of a diketene acetal and a diol,

wherein the diol comprises, cycloaliphatic, aromatic, or organosilicon diols or blends or combinations thereof where the diketene acetal has a structure of formula (I) or the diol comprises cycloaliphatic, aromatic, or organosilicon diols or blends or combinations thereof where the diketene acetal has a structure of formula (II),

wherein the diketene acetal is selected from a group of compounds having formulae (I) or (II):

2. The article of claim 1, wherein the implantable substrate is a stent.

3. The article of claim 1, wherein the diketene acetal is selected from a group of compounds having formula (II)

4. The article of claim 1, wherein the diol is a cycloaliphatic diol selected from a group consisting of 1,2-cyclobutanediol, 1,3-cyclobutanediol, 1,2-cyclopentanediol, 1,3-cyclopentanediol, 1,2-cyclohexanediol, 1,3-cyclohexanediol, 1,2 cyclohexanediol, 1,3-cycloheptanediol, 1,4-cycloheptanediol, caprolactone diol, and mixtures thereof.

5. The article of claim 1, wherein the diol is an aromatic diol selected from a group consisting of, o-benzenedimethanol, m-benzenedimethanol, and mixtures thereof.

6. The article of claim 1, wherein the diol is an organosilicon diol comprising carbinol-terminated poly(dimethyl siloxane).

7. The article of claim 1, wherein a hydroxylated functional polymer compound is additionally included in the polycondensation process.

8. The article of claim 7, wherein the hydroxylated functional polymer compound comprises poly(alkylene glycols), hydroxylated poly(N-vinyl pyrrolidone), dextran, dextrin, hyaluronic acid, derivatives of hyaluronic acid, poly(2-hydroxyethyl methacrylate), hydroxy functional poly(styrene sulfonate), hydroxy functional phosphoryl choline methacrylate polymers, polymers with both hydroxyl and phosphoryl choline functionality, heparin, or mixtures thereof.

9. The article of claim 8, wherein the poly(alkylene glycols) are selected from a group consisting of poly(ethylene glycol), poly(propylene glycol), poly(tetramethylene glycol), and poly(ethylene oxide-co-propylene oxide).

10. A medical device, comprising a coating, the coating comprising a polymer including a unit having a formula:

11. A method for fabricating a coating for an implantable medical device, the method comprising applying a polymer onto the surface of the device, wherein the polymer comprises a product of co-polycondensation of a diketene acetal and a diol,

wherein the diol comprises, cycloaliphatic, aromatic, or organosilicon diols or blends or combinations thereof where the diketene acetal has a structure of formula (I) or the diol comprises cycloaliphatic, aromatic, or organosilicon diols or blends or combinations thereof where the diketene acetal has a structure of formula (II),

wherein the diketene acetal is selected from a group of compounds having formulae (I) or (II):

12. The method of claim 11, wherein the medical device is a stent.

13. The method of claim 11, wherein the diketene acetal is selected from a group of compounds having formula (II)

14. The method of claim 11, wherein the diol is a cycloaliphatic diol selected from a group consisting of 1,2-cyclobutanediol, 1,3-cyclobutanediol, 1,2-cyclopentanediol, 1,3-cyclopentanediol, 1,2-cyclohexanediol, 1,3-cyclohexanediol, 1,2-cycloheptanediol, 1,3-cycloheptanediol, 1,4-cycloheptanediol, caprolactone diol, and mixtures thereof.

15. The method of claim 11, wherein the diol is an aromatic diol selected from a group consisting of, o-benzenedimethanol, m-benzenedimethanol, and mixtures thereof.

16. The method of claim 11, wherein the diol is an organosilicon diol comprising carbinol-terminated poly(dimethyl siloxane).

17. The method of claim 11, wherein a hydroxylated functional polymer compound is additionally included in the polycondensation process.

18. The method of claim 17, wherein the hydroxylated functional polymer compound comprises poly(alkylene glycols), hydroxylated poly(N-vinyl pyrrolidone), dextran, dextrin, hyaluronic acid, derivatives of hyaluronic acid, poly(2-hydroxyethyl methacrylate), hydroxy functional poly(styrene sulfonate), hydroxy functional phosphoryl choline methacrylate polymers, polymers with both hydroxyl and phosphoryl choline functionality, heparin, or mixtures thereof.

19. The method of claim 18, wherein the poly(alkylene glycols) are selected from a group consisting of poly(ethylene glycol), poly(propylene glycol), poly(tetramethylene glycol), and poly(ethylene oxide-co-propylene oxide).