Soluble implantable device comprising polyelectrolyte with hydrophobic counterions

• US 8,986,728 B2
• Filed: 07/09/2012
• Issued: 03/24/2015
• Est. Priority Date: 05/30/2008
• Status: Active Grant

• Current Assignee: Abbott Cardiovascular Systems Incorporated (Abbott Laboratories Incorporated)
• Original Assignee: Abbott Cardiovascular Systems Incorporated (Abbott Laboratories Incorporated)
• Inventors: Hossainy, Syed F. A., Trollsas, Mikael O., Kleiner, Lothar W.
• Primary Examiner(s): Switzer, Juliet
• Assistant Examiner(s): HELM, CARALYNNE E
• Application Number:
  US13/544,749
• Publication Number:
  US 20120276185A1
• Time in Patent Office: 988 Days
• Field of Search: None
• US Class Current: 424/426
• CPC Class Codes: A61F 2/82 Devices providing patency to, or preventing collapsing of, tubular structures of the body, e.g. stents stent-grafts for tubular structures of the body other than blood vessels A61F2/04; stent-grafts for blood vessels A61F2/07; instruments specially adapted for placement or removal of stents or stent-grafts A61F2/95; for closing wounds, or holding wounds closed A61B17/04 - A61B17/115; dilators A61M29/00
• CPC Class Codes: A61L 2300/602 Type of release, e.g. controlled, sustained, slow
• CPC Class Codes: A61L 27/34 Macromolecular materials
• CPC Class Codes: A61L 27/58 Materials at least partially resorbable by the body
• CPC Class Codes: A61L 29/085 Macromolecular materials
• CPC Class Codes: A61L 29/148 Materials at least partially resorbable by the body
• CPC Class Codes: A61L 31/048 obtained by reactions only involving carbon-to-carbon unsaturated bonds A61L31/041 takes precedence
• CPC Class Codes: A61L 31/06 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds A61L31/041 takes precedence
• CPC Class Codes: A61L 31/10 Macromolecular materials
• CPC Class Codes: A61L 31/148 Materials at least partially resorbable by the body
• CPC Class Codes: A61L 31/16 Biologically active materials, e.g. therapeutic substances A61L31/047 takes precedence
• CPC Class Codes: C08L 1/286 substituted with acid radicals, e.g. carboxymethyl cellulose [CMC] C08L1/282 takes precedence
• CPC Class Codes: C08L 5/08 Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
• CPC Class Codes: C08L 89/00 Compositions of proteins; Compositions of derivatives thereof foodstuff preparations A23J3/00
• CPC Class Codes: C09D 101/286 substituted with acid radicals C09D101/282 takes precedence
• CPC Class Codes: C09D 105/08 Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
• CPC Class Codes: C09D 189/00 Coating compositions based on proteins; Coating compositions based on derivatives thereof foodstuff preparations A23J3/00

Abstract

The present invention provides an implantable device having a biosoluble coating or a biosoluble body structure comprising a polyelectrolyte and a counterion and the methods of making and using the same.

Claims

1. An implantable device, comprising a biosoluble body structure and optionally comprising a coating deposited upon the body structure of the implantable device, the biosoluble body structure or comprising:

a complex comprising a polyelectrolyte and a counterion, the counterion being p-propylbenzenesulfonate.

2. The implantable device of claim 1, wherein the biosoluble body structure further comprises a bioactive agent.

3. The implantable device of claim 1, wherein the optional coating is present.

4. The implantable device of claim 1, wherein the complex has a high dissociation constant (pKa).

5. The implantable device of claim 1, wherein the biosoluble body structure further comprises a biosoluble polymer selected from poly(ethylene glycol) (PEG), poly(lactide-co-glycolide)-co-poly(ethylene glycol) (PLGA-PEG) block copolymers, other PEG copolymers, poly(vinyl alcohol) (PVA), hyaluronic acid, hydroxyl cellulose, carboxymethylcellulose (CMC), polysaccharides, phosphoryl choline containing polymers, chitosan, collagen, and combinations thereof.

6. The implantable device of claim 2, wherein the bioactive agent is selected from paclitaxel, docetaxel, estradiol, 17-beta-estradiol, nitric oxide donors, super oxide dismutases, 4-amino-2,2,6,6-tetramethylpiperidine-1-oxyl (4-amino-TEMPO), biolimus, tacrolimus, dexamethasone, rapamycin, 40-O-(2-hydroxy)ethyl-rapamycin (everolimus), 40-O-(3-hydroxy)propyl-rapamycin, 40-O-[2-(2-hydroxy)ethoxy]ethyl-rapamycin, 40-O-tetrazole-rapamycin, 40-epi-(N1-tetrazolyl)-rapamycin (ABT-578), γ

-hiridun, clobetasol, pimecrolimus, imatinib mesylate, midostaurin, fenofibrate, and combinations thereof.

7. The implantable device of claim 1, wherein the body structure of the implantable device is a stent.

13. A method of treating a medical condition in a blood vessel of a patient comprising implanting in the blood vessel of the patient an implantable device according to claim 1.

14. A method of treating a medical condition in a blood vessel of a patient comprising implanting in the blood vessel of the patient an implantable device according to claim 6.

15. The implantable device of claim 3, wherein the optional coating comprises a bioactive agent, which may be the same as or different from, any bioactive agent of the biosoluble body structure, if present.

16. The implantable device of claim 15, wherein the bioactive agent of the coating is selected from paclitaxel, docetaxel, estradiol, 17-beta-estradiol, nitric oxide donors, super oxide dismutases, 4-amino-2,2,6,6-tetramethylpiperidine-1-oxyl (4-amino-TEMPO), biolimus, tacrolimus, dexamethasone, rapamycin, 40-O-(2-hydroxy)ethyl-rapamycin (everolimus), 40-O-(3-hydroxy)propyl-rapamycin, 40-O-[2-(2-hydroxy)ethoxy]ethyl-rapamycin, 40-O-tetrazole-rapamycin, 40-epi-(N1-tetrazolyl)-rapamycin (ABT-578), γ

-hiridun, clobetasol, pimecrolimus, imatinib mesylate, midostaurin, fenofibrate, and combinations thereof.

17. The implantable device of claim 5, wherein the biosoluble polymer is selected from poly(ethylene glycol) (PEG), poly(lactide-co-glycolide)-co-poly(ethylene glycol) (PLGA-PEG) block copolymers, poly(vinyl alcohol) (PVA), hyaluronic acid, hydroxyl cellulose, carboxymethylcellulose (CMC), chitosan, collagen, and combinations thereof.

19. The implantable device of claim 6, wherein the bioactive agent is selected from biolimus, tacrolimus, rapamycin, 40-O-(2-hydroxy)ethyl-rapamycin (everolimus), 40-O-(3-hydroxy)propyl-rapamycin, 40-O-[2-(2-hydroxy)ethoxy]ethyl-rapamycin, 40-O-tetrazole-rapamycin, 40-epi-(N1-tetrazolyl)-rapamycin (ABT-578), and combinations thereof.

8. An implantable device, comprising a biosoluble body structure formed of a material that is sparingly soluble in an aqueous medium,

the biosoluble body structure comprising:

a complex comprising a polyelectrolyte and a counterion, the counterion being p-propylbenzenesulfonate.

9. A method of fabricating an implantable device, comprising

forming a biosoluble body structure comprising:

a complex comprising a polyelectrolyte and a counterion, the counterion being p-propylbenzenesulfonate.

10. The method of claim 9, wherein the body structure further comprises a bioactive agent.

11. The method of claim 9, wherein the biosoluble body structure further comprises a biosoluble polymer selected from poly(ethylene glycol) (PEG), poly(lactide-co-glycolide)-co-poly(ethylene glycol) (PLGA-PEG) block copolymers, other PEG copolymers, poly(vinyl alcohol) (PVA), hyaluronic acid, hydroxyl cellulose, carboxymethylcellulose (CMC), polysaccharides, phosphoryl choline containing polymers, chitosan, collagen, and combinations thereof.

12. The method of claim 10, wherein the bioactive agent is selected from paclitaxel, docetaxel, estradiol, 17-beta-estradiol, nitric oxide donors, super oxide dismutases, 4-amino-2,2,6,6-tetramethylpiperidine-1-oxyl (4-amino-TEMPO), biolimus, tacrolimus, dexamethasone, rapamycin, 40-O-(2-hydroxy)ethyl-rapamycin (everolimus), 40-O-(3-hydroxy)propyl-rapamycin, 40-O-[2-(2-hydroxy)ethoxy]ethyl-rapamycin, 40-O-tetrazole-rapamycin, 40-epi-(N1-tetrazolyl)-rapamycin (ABT-578), γ

-hiridun, clobetasol, pimecrolimus, imatinib mesylate, midostaurin, fenofibrate, and combinations thereof.

18. The method of claim 11, wherein the biosoluble polymer is selected from poly(ethylene glycol) (PEG), poly(lactide-co-glycolide)-co-poly(ethylene glycol) (PLGA-PEG) block copolymers, poly(vinyl alcohol) (PVA), hyaluronic acid, hydroxyl cellulose, carboxymethylcellulose (CMC), chitosan, collagen, and combinations thereof.

20. The method of claim 12, wherein the bioactive agent is selected from biolimus, tacrolimus, rapamycin, 40-O-(2-hydroxy)ethyl-rapamycin (everolimus), 40-O-(3-hydroxy)propyl-rapamycin, 40-O-[2-(2-hydroxy)ethoxy]ethyl-rapamycin, 40-O-tetrazole-rapamycin, 40-epi-(N1-tetrazolyl)-rapamycin (ABT-578), and combinations thereof.

21. A method of fabricating an implantable device, comprising

forming a biosoluble body structure comprising:

a complex comprising a polyelectrolyte and a counterion, the counterion being selected from the group consisting of p-propylbenzenesulfonate, nonyl acid, and combinations thereof;

wherein the body structure further comprises a bioactive agent, the bioactive agent being selected from paclitaxel, docetaxel, estradiol, 17-beta-estradiol, nitric oxide donors, super oxide dismutases, 4-amino-2,2,6,6-tetramethylpiperidine-1-oxyl (4-amino-TEMPO), biolimus, tacrolimus, dexamethasone, rapamycin, 40-O-(2-hydroxy)ethyl-rapamycin (everolimus), 40-0-(3-hydroxy)propyl-rapamycin, 40-O-[2-(2-hydroxy)ethoxy]ethyl-rapamycin, 40-O-tetrazole-rapamycin, 40-epi-(N1-tetrazolyl)-rapamycin (ABT-578), 7-hiridun, clobetasol, pimecrolimus, imatinib mesylate, midostaurin, fenofibrate, and combinations thereof.

22. The method of claim 21, wherein the biosoluble body structure further comprises a biosoluble polymer selected from poly(ethylene glycol) (PEG), poly(lactide-co-glycolide)-co-poly(ethylene glycol) (PLGA-PEG) block copolymers, other PEG copolymers, poly(vinyl alcohol) (PVA), hyaluronic acid, hydroxyl cellulose, carboxymethylcellulose (CMC), polysaccharides, phosphoryl choline containing polymers, chitosan, collagen, and combinations thereof.

23. The method of claim 22, wherein the biosoluble polymer is selected from poly(ethylene glycol) (PEG), poly(lactide-co-glycolide)-co-poly(ethylene glycol) (PLGA-PEG) block copolymers, poly(vinyl alcohol) (PVA), hyaluronic acid, hydroxyl cellulose, carboxymethylcellulose (CMC), chitosan, collagen, and combinations thereof.

24. The method of claim 21, wherein the bioactive agent is selected from biolimus, tacrolimus, rapamycin, 40-O-(2-hydroxy)ethyl-rapamycin (everolimus), 40-O-(3-hydroxy)propyl-rapamycin, 40-O-[2-(2-hydroxy)ethoxy]ethyl-rapamycin, 40-O-tetrazole-rapamycin, 40-epi-(N1-tetrazolyl)-rapamycin (ABT-578), and combinations thereof.