POLYMERS CONTAINING SILOXANE MONOMERS

• US 20080262606A1
• Filed: 06/09/2008
• Published: 10/23/2008
• Est. Priority Date: 07/30/2004
• Status: Active Grant

• Current Assignee: Abbott Cardiovascular Systems Incorporated (Abbott Laboratories)
• Original Assignee: Abbott Cardiovascular Systems Incorporated (Abbott Laboratories)
• Inventors: Pacetti, Stephen D., Ding, Ni
• Granted Patent: US 9,580,558 B2
• Time in Patent Office: Days
• US Class Current: 623/1.42
• CPC Class Codes: A61L 2300/00 Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
• 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: C08G 77/442 containing vinyl polymer sequences
• CPC Class Codes: C08L 83/04 Polysiloxanes

Abstract

A polymer of siloxanes as flexibility monomers and strength monomers is provided. It is also provided a polymer blend that contains a polymer formed of siloxane monomers and strength monomers and another biocompatible polymer. The biocompatible polymer or polymer blend described herein and optionally a bioactive agent can form a coating on an implantable device such as a drug-delivery stent. The implantable device can be used for treating or preventing 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 biocompatible polymer comprising siloxane monomers that impart flexibility to the polymer and monomers that impart mechanical strength to the polymer, wherein the polymer has_the structure of formula I:

wherein m and n are independently positive integers,

wherein X is an absence, or a linking group, and

wherein A is a biobeneficial moiety,

wherein the siloxane monomer is derived from a compound having the formula of

where R₁ and R₂ are independently H, F, Cl, Br, I, C1-C10 alkyl, C3-C10 cycloalkyl, substituted C1-C10 alkyl, haloalkyl, fluoroalkyl, chloroalkyl, bromoalkyl, iodoalkyl, phenyl, substituted phenyl, alkoxyphenyl, halophenyl and alkylphenyl, aryl, or substituted aryl, alkoxyaryl, haloaryl and alkylaryl, and Z₁ and Z₂ are independently absence or oxygen (O).

2. The biocompatible polymer of claim 1, wherein the biobeneficial moiety is poly(ethylene glycol).

3. The biocompatible polymer of claim 1, wherein R₁ and R₂ are independently fluoroalkyl groups.

4. The biocompatible polymer of claim 1 wherein the strength monomer is selected from the group consisting of ethylene, propylene, vinylidene fluoride, hexafluoropropene, tetrafluoroethylene, chlorotrifluoroethylene, vinyl fluoride, and hydropentafluoropropene, high T_g methacrylates, methyl methacrylate, ethyl methacrylate, n-propyl methacrylate, t-butyl methacrylate, styrene, methyl styrene, hydroxyl ethyl acrylate, 4-methoxyphenyl acrylate, t-butyl acrylate, o-tolyl acrylate, hydroxyl ethyl methacrylate, isotactic cyclohexyl methacrylate, cyclohexyl methacrylate, cyclohexyl acrylate, isopropyl methacrylate, 3,3-dimethylbutyl methacrylate, ethyl fluoromethacrylate and combinations thereof.

5. An implantable device having a biocompatible coating thereon, wherein the biocompatible coating comprises the biocompatible polymer of claim 1.

6. An implantable device having a biocompatible coating thereon, wherein the biocompatible coating comprises the biocompatible polymer of claim 2.

7. An implantable device having a biocompatible coating thereon, wherein the biocompatible coating comprises the biocompatible polymer of claim 3.

8. An implantable device having a biocompatible coating thereon, wherein the biocompatible coating comprises the biocompatible polymer of claim 4.

9. The implantable device of claim 5 which is a drug-delivery stent, wherein the coating further comprises a bioactive agent.

10. The implantable device of claim 6 which is a drug-delivery stent, wherein the coating further comprises a bioactive agent.

11. The implantable device of claim 7 which is a drug-delivery stent, wherein the coating further comprises a bioactive agent.

12. The implantable device of claim 8 which is a drug-delivery stent, wherein the coating further comprises a bioactive agent.

13. The drug-delivery stent of claim 9, wherein the bioactive agent is selected from the group consisting of paclitaxel, docetaxel, estradiol, nitric oxide donors, super oxide dismutases, super oxide dismutases mimics, 4-amino-2,2,6,6-tetramethylpiperidine-1-oxyl (4-amino-TEMPO), tacrolimus, dexamethasone, rapamycin, rapamycin derivatives, 40-O-(2-hydroxy)ethyl-rapamycin (everolimus), 40-O-(3-hydroxy)propyl-rapamycin, 40-O-[2-(2-hydroxy)ethoxy]ethyl-rapamycin, and 40-O-tetrazole-rapamycin, ABT-578, clobetasol, progenitor cell capturing antibody, prohealing drugs, prodrugs thereof, co-drugs thereof, and a combination thereof.

14. The drug-delivery stent of claim 10, wherein the bioactive agent is selected from the group consisting of paclitaxel, docetaxel, estradiol, nitric oxide donors, super oxide dismutases, super oxide dismutases mimics, 4-amino-2,2,6,6-tetramethylpiperidine-1-oxyl (4-amino-TEMPO), tacrolimus, dexamethasone, rapamycin, rapamycin derivatives, 40-O-(2-hydroxy)ethyl-rapamycin (everolimus), 40-O-(3-hydroxy)propyl-rapamycin, 40-O-[2-(2-hydroxy)ethoxy]ethyl-rapamycin, and 40-O-tetrazole-rapamycin, ABT-578, clobetasol, progenitor cell capturing antibody, prohealing drugs, prodrugs thereof, co-drugs thereof, and a combination thereof.

15. The drug-delivery stent of claim 11, wherein the bioactive agent is selected from the group consisting of paclitaxel, docetaxel, estradiol, nitric oxide donors, super oxide dismutases, super oxide dismutases mimics, 4-amino-2,2,6,6-tetramethylpiperidine-1-oxyl (4-amino-TEMPO), tacrolimus, dexamethasone, rapamycin, rapamycin derivatives, 40-O-(2-hydroxy)ethyl-rapamycin (everolimus), 40-O-(3-hydroxy)propyl-rapamycin, 40-O-[2-(2-hydroxy)ethoxy]ethyl-rapamycin, and 40-O-tetrazole-rapamycin, ABT-578, clobetasol, progenitor cell capturing antibody, prohealing drugs, prodrugs thereof, co-drugs thereof, and a combination thereof.

16. The drug-delivery stent of claim 12, wherein the bioactive agent is selected from the group consisting of paclitaxel, docetaxel, estradiol, nitric oxide donors, super oxide dismutases, super oxide dismutases mimics, 4-amino-2,2,6,6-tetramethylpiperidine-1-oxyl (4-amino-TEMPO), tacrolimus, dexamethasone, rapamycin, rapamycin derivatives, 40-O-(2-hydroxy)ethyl-rapamycin (everolimus), 40-O-(3-hydroxy)propyl-rapamycin, 40-O-[2-(2-hydroxy)ethoxy]ethyl-rapamycin, and 40-O-tetrazole-rapamycin, ABT-578, clobetasol, progenitor cell capturing antibody, prohealing drugs, prodrugs thereof, co-drugs thereof, and a combination thereof.