POLYSULFONE BLOCK COPOLYMERS AS DRUG-ELUTING COATING MATERIAL

• US 20090238856A1
• Filed: 06/02/2009
• Published: 09/24/2009
• Est. Priority Date: 11/25/2003
• Status: Active Grant

• Current Assignee: Advanced Cardiovascular Systems Incorporated
• Original Assignee: Advanced Cardiovascular Systems Incorporated
• Inventors: Claude, Charles D., Ding, Ni, Yu, Yeung Siu
• Granted Patent: US 8,017,142 B2
• Time in Patent Office: Days
• US Class Current: 424/424
• CPC Class Codes: A61L 2300/606 Coatings
• 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 81/06 Polysulfones; Polyethersulfones

Abstract

A polymeric composition comprising a polysulfone polymer and an elastomeric polymer for use as a coating composition for coating an implantable device, such as a DES, and methods of making and using the implantable device are provided.

Claims

1. A method of forming an implantable device, comprising

forming a coating on the implantable device, the coating comprising a polymeric composition comprising a block copolymer comprising a polysulfone (A) and an elastomeric polymer (B), wherein the polysulfone and the elastomeric polymer form a conjugate by direct chemical bonding, and

wherein the elastomeric polymer is selected from the group consisting of polyisobutylene, polyperfluoroalkylene, polyhexafluoropentene, poly(butyl methacrylate), poly(lauryl methacrylate), polyalkylene oxide, polyalkylene oxide acrylate, and a combination thereof.

2. The method of claim 1, wherein the elastomeric polymer is selected from the group consisting of polyisobutylene, polyperfluoroalkylene, polyhexafluoropentene, poly(butyl methacrylate), poly(lauryl methacrylate), polyalkylene oxide acrylate, and a combination thereof.

3. The method of claim 1, wherein the block copolymer comprises at least one block of a polysulfone polymer (A) and at least one block of an elastomeric polymer (B) in a general formula selected from AB, ABA or BAB.

4. The method of claim 1 wherein the implantable device is a stent.

5. The method of claim 1, wherein the coating further comprises a bioactive agent.

6. The method of claim 5, wherein the bioactive agent is selected from the group consisting of tacrolimus, dexamethasone, rapamycin, Everolimus, 40-O-(3-hydroxy)propyl-rapamycin, 40-O-[2-(2-hydroxy)ethoxy]ethyl-rapamycin, and 40-O-tetrazole-rapamycin, sirolimus, sirolimus derivatives, paclitaxel, taxoids, estradiol, steroidal anti-inflammatory agents, antibiotics, nitric oxide donors, super oxide dismutases, super oxide dismutase mimics, 4-amino-2,2,6,6-tetramethylpiperidine- 1-oxyl (4-amino-TEMPO), and a combination thereof.

7. The method of claim 1, wherein the polysulfone and the elastomeric polymer form a conjugate comprising a block copolymer, wherein the block copolymer is selected from the group consisting of

wherein R₁ is selected from the group consisting of C1 to C10 alkyl, C2, C4 and C6 hydroxyalkyl, C1 to C6 fluoroalkyl, phenyl, substituted phenyl, polyethylene glycol, polyalkylene oxide, ethylene oxide and propylene oxide;

wherein R₂, R₄, R₅, R₇ and R₈ are independently selected from the group consisting of hydrogen, C1 to C6 alkyl, C2, C4 and C6 hydroxyalkyl, C1 to C6 fluoroalkyl, phenyl, substituted phenyl, carboxyl, amido, ester groups bearing a polyethylene glycol, and polyalkylene oxide;

wherein R₃ is selected from the group consisting of hydrogen, alkyl, cycloalkyl, phenyl, carboxyl, halo, amino, hydroxyl, amido, sulfido, and polyalkylene oxide;

wherein R₆ is a perfluoroalkyl group;

wherein R₄, R₅, and R₆ are selected such that the

 

block and the

 

are elastomeric; and

wherein n and m are independently positive integers.

8. The method of claim 7, wherein R₁ is butyl, isobutyl or isopropyl;

wherein R₂ is hydrogen or methyl;

wherein R₃ is hydrogen, halo, or methyl;

wherein R₄ and R₅ are independently hydrogen, methyl, ethyl, isopropyl, butyl, isobutyl, or phenyl;

wherein R₆ is CF₂CF₃, CF₂CF₂CF₃, perfluoroisopropyl, perfluorobutyl or perfluoroisobutyl; and

wherein R₇ and R₈ are independently methyl, ethyl, propyl, isopropyl, butyl, or isobutyl group.

9. The method of claim 7, wherein R₁ is butyl;

wherein R₂ is methyl;

wherein R₃ is hydrogen;

wherein R₄ or R₅ are methyl groups; and

wherein R₇ and R₈ are methyl groups.