Coatings for drug delivery devices

• US 8,883,186 B2
• Filed: 01/04/2013
• Issued: 11/11/2014
• Est. Priority Date: 11/12/2001
• Status: Expired due to Term

• Current Assignee: Advanced Cardiovascular Systems Incorporated
• Original Assignee: Advanced Cardiovascular Systems Incorporated
• Inventors: Pacetti, Stephen Dirk
• Primary Examiner(s): Westerberg, Nissa
• Assistant Examiner(s): YOUNG, MICAH PAUL
• Application Number:
  US13/734,858
• Publication Number:
  US 20130150460A1
• Time in Patent Office: 676 Days
• Field of Search: 424489-495, 424422-425
• US Class Current: 424/424
• CPC Class Codes: A61L 27/16 obtained by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: A61L 27/30 Inorganic materials
• CPC Class Codes: A61L 27/54 Biologically active materials, e.g. therapeutic substances A61L27/227 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 31/00 Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
• CPC Class Codes: C08L 29/02 Homopolymers or copolymers of unsaturated alcohols C08L29/14 takes precedence
• CPC Class Codes: C09D 129/04 Polyvinyl alcohol; Partially hydrolysed homopolymers or copolymers of esters of unsaturated alcohols with saturated carboxylic acids
• CPC Class Codes: C09D 129/06 Copolymers of allyl alcohol

Abstract

A polymer coating for medical devices based on a polyolefin derivative. A variety of polymers are described to make coatings for medical devices, particularly, for drug delivery stents. The polymers include homo-, co-, and terpolymers having at least one olefin-derived unit and at least one unit derived from vinyl alcohol, allyl alcohol and derivatives thereof.

Claims

1. A coating for a medical device, the coating comprising a polymer having a formula:

—

[CH₂—

CH(CH₃)]_p—

[CH₂—

CR³(OH)]_q—

[CH₂—

CH(CH₂OH)_y]_r—

,

wherein R³ is selected from a group consisting of a hydrogen atom and an alkyl group, wherein the coating contains a drug, and

p is an integer within a range of between about 30 and about 7,600;

q is an integer within a range of between about 30 and about 7,600;

r is an integer within a range of between 0 and about 7,600; and

y equals 1 if r equals at least 1.

2. The coating of claim 1, wherein the alkyl group is methyl.

3. The coating of claim 1, wherein the polymer absorbs not more than 5% of water by mass.

4. The coating of claim 1, wherein the polymer is soluble in an organic solvent.

5. The coating of claim 1, wherein the polymer has a tensile strength of not less than about 24 MPa (3,500 pounds per square inch).

6. The coating of claim 1, wherein the polymer has an ultimate elongation exceeding 30 percent.

7. A coating for a stent, the coating comprising a polymer having a formula:

—

[CH₂—

CH(CH₃)]_p—

[CH₂—

CR³(OH)]_q—

[CH₂—

CH(CH₂OH)_y]_r—

,

wherein R³ is selected from a group consisting of a hydrogen atom and an alkyl group;

p is an integer within a range of between about 30 and about 7,600;

q is an integer within a range of between about 30 and about 7,600;

r is an integer within a range of between 0 and about 7,600; and

y equals 1 if r equals at least 1.

8. The coating of claim 7, wherein the coating is a primer layer.

9. The coating of claim 7, wherein the coating is a rate release limiting membrane.

10. The coating of claim 7, wherein the alkyl group is methyl.

11. The coating of claim 7, wherein the polymer absorbs not more than 5% of water by mass.

12. The coating of claim 7, wherein the polymer is soluble in an organic solvent.

13. The coating of claim 7, wherein the polymer has a tensile strength of not less than about 24 MPa (3,500 pounds per square inch).

14. The coating of claim 7, wherein the polymer has an ultimate elongation exceeding 30 percent.

15. A coating for a medical device, the coating comprises a terpolymer which is a product of copolymerization of an olefin monomer and two different monounsaturated hydroxylated monomers, wherein the coating contains a drug;

wherein the two different monounsaturated hydroxylated monomers are selected from a group consisting of α

-methvinyl alcohol, allyl alcohol, methallyl alcohol, 1-hydroxy-2-methyl ethylene, 1-acetoxy-2-methyl propene, 3-butene-1-ol, 3-butene-2-ol, 2-butene-1-ol, 3-acetoxy-3-butene, and 4-acetoxy-3-butene.

16. The coating of claim 15, wherein the olefin comprises a C₂-C₈ straight chain or branched olefin.

17. The coating of claim 15, wherein the polymer absorbs not more than 5% of water by mass.

18. The coating of claim 15, wherein the polymer is soluble in an organic solvent.

19. The coating of claim 15, wherein the polymer has a tensile strength of not less than about 24 MPa (3,500 pounds per square inch).

20. The coating of claims 15, wherein the polymer has an ultimate elongation exceeding 30 percent.