Biologically absorbable coatings for implantable devices based on poly(ester amides) and methods for fabricating the same

• US 7,220,816 B2
• Filed: 12/16/2003
• Issued: 05/22/2007
• Est. Priority Date: 12/16/2003
• Status: Expired due to Fees

• Current Assignee: Advanced Cardiovascular Systems Incorporated
• Original Assignee: Advanced Cardiovascular Systems Incorporated
• Inventors: Pacetti, Stephen D., DesNoyer, Jessica R.
• Primary Examiner(s): Boykin; Terressa
• Application Number:
  US10/738,704
• Publication Number:
  US 20050131201A1
• Time in Patent Office: 1,253 Days
• Field of Search: 427/2.25, 427/2.28, 427/207.1, 427/322, 623/1.15, 623/1.46, 623/1.49, 428/423.1, 428/474.4, 428/478.2, 528/289, 528/290, 528/291, 528/292, 528/335, 424/423
• US Class Current: 528/272
• CPC Class Codes: A61L 31/10 Macromolecular materials
• CPC Class Codes: C08L 77/12 Polyester-amides
• CPC Class Codes: Y10T 428/31725 Of polyamide
• CPC Class Codes: Y10T 428/31768 Natural source-type polyamide [e.g., casein, gelatin, etc.]

Abstract

Coatings for an implantable medical devices such as stents and methods of fabricating thereof are disclosed. The coatings comprise a biologically absorbable poly(ester amide), which is a polymeric product of a reaction between a diol-diamine and a dicarboxylic acid.

Claims

1. A medical article comprising an implantable substrate having a coating, the coating including a polymeric product of a reaction between a diol-diamine and a dicarboxylic acid,

wherein the diol-diamine comprises a unit derived from a diol and

wherein the polymeric product comprises a copolymer of a formula

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

3. The medical article of claim 1, wherein the diol-diamine is a product of condensation of two molecules of an amino acid or a mixture of two amino acids and one molecule of the diol.

4. The medical article of claim 3, wherein the amino acid comprises a substance having the formula H₂N—

CHR—

COOH, wherein R is selected from a group consisting of hydrogen, methyl, iso-propyl, sec-butyl, iso-butyl, benzyl, methyl mercaptoethyl, methylene amide, and ethylene amide.

5. The medical article of claim 3, wherein the amino acid is selected from a group consisting of glycine, alanine, valine, isoleucine, leucine, phenyl alanine, methionine, asparagine, glutamine, proline, and mixtures thereof.

6. The medical article of claim 1, wherein the diol comprises a substance having the formula HO—

(CH₂)_x—

OH, wherein x is an integer having a value between 2 and 16.

7. The medical article of claim 1, wherein the diol is selected from a group consisting of ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butane diol, 1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, 1,11-undecanediol, and 1,12-dodecanediol, and mixtures thereof.

8. The medical article of claim 1, wherein the dicarboxylic acid comprises a substance having the formula HOOC—

(CH₂)_y—

COOH, wherein y is an integer having a value between 0 and 16.

9. The medical article of claim 1, wherein the dicarboxylic acid is selected from a group consisting of oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, undecanedioic acid, dodecanedioic acid, brassylic acid, tetradecanedioic acid, pentadecanedioic acid, thapsic acid, and mixtures thereof.

10. A medical article comprising an implantable substrate having a coating, the coating including a copolymer having a formula

23. The medical article of claim 10, wherein the implantable substrate is a stent.

11. A medical article comprising an implantable substrate having a coating, the coating including a copolymer having a formula

12. A method for fabricating a medical article, the method including:

(a) synthesizing a copolymer; and

(b) forming a coating comprising the copolymer on at least a portion of an implantable substrate, the synthesizing of the copolymer including reacting a diol-diamine with a dicarboxylic acid,

wherein the diol-diamine comprises a unit derived from a diol.

13. The method of claim 12, wherein the implantable substrate is a stent.

14. The method of claim 12, wherein the diol-diamine is a product of condensation of two molecules of an amino acid or a mixture of two amino acids and one molecule of the diol.

15. The method of claim 14, wherein the amino acid comprises a substance having the formula H₂N—

CHR—

COOH, wherein R is selected from a group consisting of hydrogen, methyl, iso-propyl, sec-butyl, iso-butyl, benzyl, methyl mercaptoethyl, methylene amide, and ethylene amide.

16. The method of claim 14, wherein the amino acid is selected from a group consisting of glycine, alanine, valine, isoleucine, leucine, phenyl alanine, methionine, asparagine, glutamine, proline, and mixtures thereof.

17. The method of claim 12, wherein the diol comprises a substance having the formula HO—

(CH₂)_x—

OH, wherein x is an integer having a value between 2 and 16.

18. The method of claim 12, wherein the dicarboxylic acid comprises a substance having the formula HOOC—

(CH₂)_y—

COOH, wherein y is an integer having a value between 0 and 16.

19. The method of claim 12, wherein the dicarboxylic acid is selected from a group consisting of oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, undecanedioic acid, dodecanedioic acid, brassylic acid, tetradecanedioic acid, pentadecanedioic acid, thapsic acid, and mixtures thereof.

24. The method of claim 12, wherein the diol is selected from a group consisting of ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butane diol, 1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, 1,11-undecanediol, and 1,12-dodecanediol, and mixtures thereof.

20. A method for fabricating a medical article, the method including:

(a) synthesizing a copolymer; and

(b) forming a coating comprising the copolymer on at least a portion of an implantable substrate, wherein the copolymer has a formula

21. The method of claim 20, wherein the implantable substrate is a stent.

22. A method for fabricating a medical article, the method including:

(a) synthesizing a copolymer; and

(b) forming a coating comprising the copolymer on at least a portion of an implantable substrate, wherein the copolymer has a formula

25. A method for fabricating a medical article, the method including:

forming a coating comprising a copolymer on at least a portion of an implantable substrate, the copolymer being a product of a reaction between a diol-diamine and a dicarboxylic acid,

wherein the diol-diamine comprises a unit derived from a diol and

wherein the polymeric product comprises a copolymer of a formula

26. A method for fabricating a medical article, the method including:

forming a coating comprising a copolymer on at least a portion of an implantable substrate, wherein the copolymer has a formula

27. A method for fabricating a medical article, the method including:

forming a coating comprising a copolymer on at least a portion of an implantable substrate, wherein the copolymer has a formula