Soluble implantable device comprising polyelectrolyte with hydrophobic counterions

• US 9,327,062 B2
• Filed: 02/17/2015
• Issued: 05/03/2016
• Est. Priority Date: 05/30/2008
• Status: Expired due to Fees

• Current Assignee: Abbott Cardiovascular Systems Incorporated (Abbott Laboratories Incorporated)
• Original Assignee: Abbott Cardiovascular Systems Incorporated (Abbott Laboratories Incorporated)
• Inventors: Hossainy, Syed F. A., Trollsas, O. Mikael, Kleiner, Lothar W.
• Primary Examiner(s): Wax, Robert A
• Assistant Examiner(s): HELM, CARALYNNE E
• Application Number:
  US14/624,063
• Publication Number:
  US 20150157771A1
• Time in Patent Office: 441 Days
• Field of Search: None
• US Class Current: 1/1
• 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 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 on the body structure of the implantable device, the biosoluble body structure comprising:

a complex comprising a polyelectrolyte and a counterion, the polyelectrolyte being poly(2-acrylamido-2-methyl-1-propane sulfonic acid) (PAMPS), sulfonated poly(ether ether ketone) (SPEEK), poly(acryloxyethyltrimethyl ammonium chloride), poly(methacryloxy(2-hydroxy)propyltrimethyl ammonium chloride), or a combination thereof;

wherein the implantable device is selected from the group consisting of stents, stent-grafts, catheters, grafts, pacemakers, defibrillators, leads for pacemakers, leads for defibrillators, electrodes for pacemakers, electrodes for defibrillators, artificial heart valves, anastomotic clips, arterial closure devices, patent foramen ovale closure devices, and cerebrospinal fluid shunts.

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 counterion is a hydrophobic counterion.

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

5. The implantable device of claim 2, wherein the bioactive agent is selected from the group consisting of 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.

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

7. The implantable device of claim 1, wherein the biosoluble body structure further comprises a biosoluble polymer selected from the group consisting of 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.

8. The implantable device of claim 2, wherein the bioactive agent is selected from the group consisting of paclitaxel, docetaxel, estradiol, 17-beta-estradiol, nitric oxide donors, super oxide dismutases, super oxide dismutases mimics, 4-amino-2,2,6,6-tetramethylpiperidine-1-oxyl (4-amino-TEMPO), biolimus, 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, 40-O-tetrazole-rapamycin, 40-epi-(N1-tetrazolyl)-rapamycin (ABT-578 ), γ

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

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

10. The implantable device of claim 1,

wherein the polyelectrolyte is poly(2-acrylamido-2-methyl-1-propane sulfonic acid) (PAMPS), sulfonated poly(ether ether ketone) (SPEEK), or a combination thereof.

11. The implantable device of claim 1, wherein the polyelectrolyte is poly(acryloxyethyltrimethyl ammonium chloride), poly(methacryloxy(2-hydroxy) -propyltrimethyl ammonium chloride), or a combination thereof.

12. A method of fabricating an implantable device, comprising

forming a biosoluble body structure comprising:

a complex comprising a polyelectrolyte and a counterion, the polyelectrolyte being poly(2-acrylamido-2-methyl-1-propane sulfonic acid) (PAMPS), sulfonated poly(ether ether ketone) (SPEEK), poly(acryloxyethyltrimethyl ammonium chloride), poly(methacryloxy(2-hydroxy)propyltrimethyl ammonium chloride, or a combination thereof;

wherein the implantable device is selected from the group consisting of stents, stent-grafts, catheters, grafts, pacemakers, defibrillators, leads for pacemakers, leads for defibrillators, electrodes for pacemakers, electrodes for defibrillators, artificial heart valves, anastomotic clips, arterial closure devices, patent foramen ovale closure devices, and cerebrospinal fluid shunts.

13. The method of claim 12, wherein the implantable device further comprises a bioactive agent.

14. The method of claim 12, wherein the counterion is a hydrophobic counterion.

15. The method of claim 12, wherein the complex has a high dissociation constant (pKa).

16. The method of claim 13, wherein the bioactive agent is selected from the group consisting of 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-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 method of claim 12, further comprising depositing a coating on the biosoluble body structure.

18. The method of claim 12, wherein the biosoluble body structure is a stent.

19. The method of claim 12, wherein the biosoluble body structure further comprises a biosoluble polymer selected from the group consisting of 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.

20. The method of claim 13, wherein the bioactive agent is selected from the group consisting of paclitaxel, docetaxel, estradiol, 17-beta-estradiol, nitric oxide donors, super oxide dismutases, super oxide dismutases mimics, 4-amino-2,2,6,6-tetramethylpiperidine-1-oxyl (4-amino-TEMPO), biolimus, 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, 40-O-tetrazole-rapamycin, 40-epi-(N1-tetrazolyl)-rapamycin (ABT-578 ), γ

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