WO2008064058A2 - Use of a terpolymer of tetrafluoroethylene, hexafluoropropylene, and vinylidene fluoride in drug eluting coatings - Google Patents

Use of a terpolymer of tetrafluoroethylene, hexafluoropropylene, and vinylidene fluoride in drug eluting coatings Download PDF

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WO2008064058A2
WO2008064058A2 PCT/US2007/084779 US2007084779W WO2008064058A2 WO 2008064058 A2 WO2008064058 A2 WO 2008064058A2 US 2007084779 W US2007084779 W US 2007084779W WO 2008064058 A2 WO2008064058 A2 WO 2008064058A2
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medical device
range
coating
polymer
thv
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PCT/US2007/084779
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English (en)
French (fr)
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WO2008064058A3 (en
WO2008064058A9 (en
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Stephen Pacetti
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Abbott Laboratories
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Priority to JP2009537353A priority Critical patent/JP5557373B2/ja
Priority to EP07868765A priority patent/EP2097119A4/en
Publication of WO2008064058A2 publication Critical patent/WO2008064058A2/en
Publication of WO2008064058A9 publication Critical patent/WO2008064058A9/en
Publication of WO2008064058A3 publication Critical patent/WO2008064058A3/en

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L27/54—Biologically active materials, e.g. therapeutic substances
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/28—Materials for coating prostheses
    • A61L27/34—Macromolecular materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
    • A61L29/08—Materials for coatings
    • A61L29/085—Macromolecular materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
    • A61L29/14—Materials characterised by their function or physical properties, e.g. lubricating compositions
    • A61L29/16—Biologically active materials, e.g. therapeutic substances
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/08—Materials for coatings
    • A61L31/10—Macromolecular materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/14—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L31/16—Biologically active materials, e.g. therapeutic substances
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices

Definitions

  • 60/866,804 entitled “Zwitterionic Copolymers, Method of Making and Use on Medical Devices" (Attorney Docket No. 16497.64), co-pending United States Provisional Patent Application No. 60/866805, entitled “Zwitterionic Terpolymers, Method of Making and Use on Medical Devices" (Attorney Docket No. 16497.65), co-pending United States Provisional Patent Application No. 60/866,798, entitled "Amino Acid Mimetic Copolymers and Medical Devices Coated with the Copolymers" (Attorney Docket No. 16497.70), co-pending United States Provisional Patent Application No.
  • 60/866,797 entitled “Methods for Manufacturing Amino Acid Mimetic Copolymers and Use of Same” (Attorney Docket No. 16497.71), co-pending United States Provisional Patent Application No. 60/866,796, entitled “Copolymers Having l-Methyl-2-Methoxyethyl Moieties” (Attorney Docket No. 16497.72), and co-pending United States Provisional Patent Application No. 60/866,792, entitled “Methods for Manufacturing Copolymers Having l-methyl-2-Methoxyethyl Moieties and Use of Same” (Attorney Docket No. 16497.73), each of which was filed November 21, 2006, and each of which is hereby incorporated by reference in their entirety.
  • Embodiments of the invention relate to polymer coated implantable medical devices. More particularly, embodiments of the invention relate to implantable medical devices coated with terpolymers of tetrafluroethylene(TFE), hexafluropropylene (HFP), and vinylidene fluoride (VDF).
  • TFE tetrafluroethylene
  • HFP hexafluropropylene
  • VDF vinylidene fluoride
  • Implantable intravascular stents are commonly used in many medical procedures to treat disorders of the circulatory system. Although these devices work well mechanically, chronic issues of restenosis and, to a lesser extent, thrombosis remain. These biologically derived issues are currently being addressed using pharmacological therapies, including the use of drug eluting polymer coatings on stents.
  • Polymeric coatings used on implantable medical devices for drug delivery typically serve two purposes. First, the polymer holds the drug on the device such that it is presented to the lesion. Secondly, the polymer controls the release rate of the drug from the coating to maintain an efficacious tissue concentration for the duration of time required to yield the clinically desired result.
  • the materials used in coating implantable vascular stents should satisfy additional criteria including: adhesion to the implant (e.g. adhesion to stent struts) to prevent delamination; adequate elongation to accommodate implant deformation without buckling or cracking; sufficient hardness to withstand crimping operations without excessive damage; sterilizability; biocompatibility including hemocompatibility and chronic vascular tissue compatibility; in the case of durable or permanent coatings, the polymer needs to be sufficiently biostable to avoid biocompatibility concerns; processability (e.g. production of stent coatings that are microns thick); reproducible and feasible polymer synthesis; and an adequately defined regulatory path.
  • adhesion to the implant e.g. adhesion to stent struts
  • adequate elongation to accommodate implant deformation without buckling or cracking
  • sufficient hardness to withstand crimping operations without excessive damage sterilizability
  • biocompatibility including hemocompatibility and chronic vascular tissue compatibility
  • processability e.g.
  • fluoropolymers One class of polymers extensively used in implantable medical devices is fluoropolymers.
  • One common example is poly(tetrafluoroethylene) (Teflon®) which is used in vascular grafts and soft tissue implants.
  • Fluoropolymers possess many properties that render them useful for coatings on implantable devices. For example, fluoropolymers have excellent biostability, good blood compatibility, and low water absorption, which enables low drug permeability for good drug release control.
  • fluoropolymers have excellent biostability, good blood compatibility, and low water absorption, which enables low drug permeability for good drug release control.
  • One problem with existing fluoropolymers used to coat implantable medical devices is their high degree of crystallinity . The high crystallinity of the polymers makes the polymers difficult to process and apply to a medical device.
  • THV poly(tetrafluoroethylene-co-hexafluoropropylene-co-vinylidene fluoride)
  • the THV polymer has the following chemical formula.
  • n is in a range from 0.005 to 0.85
  • m is in a range from 0.005 to 0.85
  • o is in a range from 0.005 to a 0.99.
  • THV Coating the implantable medical devices with THV is advantageous for several reasons.
  • One advantage of THV is its elasticity. THV has superior elongation properties compared to many fluoropolymers and other hydrophobic polymers used on medical devices. Good polymer elongation is beneficial for avoiding polymer cracking during application of the polymer and use of the device.
  • Another advantage is that THV includes some tetrafluoroethylene monomer. Poly(tetrafluoroethylene) is one of the most chemically resistant, stable, and lubricious polymers available. To the extent that the TFE monomer is present at the surface, a coating of THV can be more lubricious and inert compared to other coatings.
  • THV is its processability .
  • THV is soluble in several organic solvents. Consequently, THV can be applied to the implantable device using solvent based techniques including, but not limited to, spraying, dip coating, roll coating, spin coating, direct application by brush or needle, inkjet printing, or the like.
  • Solvent-based application techniques are useful for applying a thin, even coating, which can be advantageous for controlled drug delivery.
  • the THV polymers can be applied to a medical device using non-solvent techniques including powder coating.
  • non-solvent techniques including powder coating.
  • Figure IA illustrates a stent coated with a THV terpolymer according to one embodiment of the invention.
  • Figure IB is a cross-section of a strut of the stent of Figure IA.
  • Embodiments of the invention relate to implantable medical devices coated with terpolymers of tetrafluoroethylene, hexafluoropropylene, and vinylidene fluoride
  • THV THV
  • the implantable medical devices coated with THV provide superior performance and improved manufacturability compared to existing implantable medical devices coated with fluoropolymers.
  • the THV polymer has the following chemical formula.
  • n is in a range from about 0.005 to about 0.85
  • m is in a range from about 0.005 to about 0.85
  • o is in a range from about 0.005 to about 0.99.
  • the monomers shown in the chemical formula above and other chemical formulas herein can be in any order within the copolymer molecule and the monomer linkages shown in the chemical formulas only represent that the monomers are part of the same copolymer molecule.
  • the polymeric molecules can include monomers other than those shown in the chemical formulas.
  • the THV coating on the implantable medical devices of the invention are advantageously biocompatible.
  • the THV polymer includes only fluorinated monomers that have been shown to be biocompatible when used as a homopolymer and/or copolymer on medical devices.
  • poly(tetrafluoroethylene) has been used on vascular grafts and poly(vinylindene fluoride) and poly(vinylidene flouride-co- hexafluoropropylene) have been used in implantable sutures.
  • Another feature of the THV polymer is that it can be soluble in an organic solvent. This feature is in contrast to most polymers that include tetrafluoroethylene monomers, which are typically insoluble in organic solvents.
  • Solvent insoluble fluoropolymers include poly(tetrafluoroethylene-co-hexafluoropropylene), poly(tetrafluoroethylene-co-ethylene), and poly(tetrafluoroethylene-co- chlorotrifluoro ethylene. These polymers are insoluble in organic solvents, in large part because of the crystallinity of the TFE monomer.
  • the THV used in embodiments of the invention can be solvent soluble because of the hexafluoropropylene and vinylidene fluoride monomers.
  • poly(vinylidene fluoride) is solvent soluble due to the high dipolar moment of the CF 2 group.
  • the hexafluoropropylene monomer leads to an amorphous polymer due to its atactic structure. Consequently, hexafluoropropylene and vinylidene fluoride monomers inhibit crystallization of the tetrafluoroethylene.
  • the THV monomer can include less than 75 mole % of tetrafluoroethylene monomer and in an alternative embodiment less than 50 mol %.
  • Table 1 The physical properties of various commercially available THV polymers (available from Dyneon) are shown in Table 1.
  • the physical properties of the Dyneon THV polymers in Table 1 illustrate various properties that make THV suitable for use on implantable medical devices, particularly for drug eluting stents.
  • Table 1 also includes poly(n-butyl methacrylate) (PMBA), which is currently being used on drug eluting stents such as Xience VTM and CYPHERTM.
  • PMBA poly(n-butyl methacrylate)
  • the ultimate elongations for THV are high and show that the THV polymers can plastically deform without cracking.
  • the THV polymer has an elongation in a range from about 50% to about 800%, alternatively in a range from about 100% to about 700%. In yet another alternative embodiment, the elongation is in a range from about 300% to about 800% and alternatively in a range from about 400 % to about 700%.
  • the THV polymers In contrast to PBMA, the THV polymers have a melting point. The existence of a melting point indicates that the THV polymers have some crystallinity, but not so much as to prevent solubility. A small amount of crystallinity is advantageous because it gives the polymer strength.
  • the THV polymers can be synthesized by a free radical process using either suspension or emulsion polymerization.
  • Typical initiators are peroxide and azo compounds, organic soluble peroxides being used advantageously for suspension polymerization.
  • the reaction is performed in an autoclave due to the gaseous nature of the monomers and water is the most common dispersed phase.
  • the polymerization is a single-step reaction with minimal purification required as the gaseous monomers escape once the reactor is vented to the atmosphere.
  • Examples of THV polymers suitable for use in embodiments of the invention are commercially available from Dyneon, LLC
  • the polymerization reaction can be controlled to produce the copolymers of the invention with a desired molecular weight.
  • the number average molecular weight of the copolymer is in the range from about 2OK to about 800K, in another embodiment, the number average molecular weight is in a range from about
  • the implant devices of embodiments of the invention can be coated with THV using solvent and non-solvent based techniques.
  • suitable techniques for applying the coating to the medical device include spraying, dip coating, roll coating, spin coating, powder coating, inkjet printing, and direct application by brush or needle.
  • the copolymers can be applied directly to the surface of the implant device, or they can be applied over a primer or other coating material.
  • the THV polymers can be used alone as a coating or can be combined with other polymers or agents to form a polymer coating.
  • the THV polymers can be used as a base coat, top coat, or other coating layer and can be used with or without a primer coating.
  • the polymer coatings are applied to a medical device using a solvent-based technique.
  • the polymer can be dissolved in the solvent to form a solution, which can be more easily applied to the medical device using one or more of the above mentioned techniques or another technique. Thereafter substantially all or a portion of the solvent can be removed to yield the polymer coating on a surface of the medical device.
  • suitable solvents include, but are not limited to, dimethylacetamide (DMAC), dimethylformamide (DMF), tetrahydrofuran (THF), dimethylsulfoxide (DMSO), cyclohexanone, xylene, toluene, acetone, z-propanol, methyl ethyl ketone, propylene glycol monomethyl ether, methyl t-butyl ketone, methyl isobutyl ketone, ethyl acetate, n-butyl acetate, n-butanol, ethanol, methanol, chloroform, trichloroethylene, 1,1,1- trichloreoethane, methylene chloride, cyclohexane, and dioxane.
  • DMAC dimethylacetamide
  • DMF dimethylformamide
  • THF tetrahydrofuran
  • DMSO dimethylsulfoxide
  • cyclohexanone
  • Solvent mixtures can be used as well.
  • Representative examples of the mixtures include, but are not limited to, DMAC and acetone (50:50 w/w); tetrahydrofuran and DMAC (80:20, 50:50, or 20:80 w/w); and acetone and cyclohexanone (80:20, 50:50, or 20:80 w/w).
  • Examples of suitable implantable devices that can be coated with the copolymers of the invention include coronary stents, peripheral stents, catheters, arteriovenous grafts, by-pass grafts, pacemaker and defibrillator leads, anastomotic clips, arterial closure devices, patent foramen ovale closure devices, and drug delivery balloons.
  • the copolymers are particularly suitable for permanently implanted medical devices.
  • the implantable device can be made of any suitable biocompatible materials, including biostable and bioabsorbable materials.
  • suitable biocompatible metallic materials include, but are not limited to, stainless steel, tantalum, titanium alloys (including nitinol), and cobalt alloys (including cobalt-chromium-nickel and cobalt- chromium-tungsten alloys).
  • Suitable nonmetallic biocompatible materials include, but are not limited to, polyamides, fluoropolymers, polyolef ⁇ ns (i.e. polypropylene, polyethylene etc.), nonabsorbable polyesters (i.e. polyethylene terephthalate), and bioabsorbable aliphatic polyesters (i.e. homopolymers and copolymers of lactic acid, glycolic acid, lactide, glycolide, para-dioxanone, trimethylene carbonate, ⁇ - caprolactone, and the like, and combinations of these).
  • the THV polymer is particularly useful as a coating for stents due to its biocompatibility, elongation, mechanical strength, and controlled drug release.
  • the THV polymer coated stents can be self-expanding or balloon expandable.
  • the stents can be composed of wire structures, flat perforated structures that are subsequently rolled to form tubular structures, or cylindrical structures that are woven, wrapped, drilled, etched or cut.
  • FIG. 1A shows a stent 10 coated with a THV polymer according to one embodiment of the invention.
  • Stent 10 includes a generally tubular body 12 with a lumen.
  • the struts of body 12 e.g. strut 14
  • Figure IB illustrates a cross-section of the stent of Figure IA coated with a THV polymer coating 16 according to an embodiment of the invention.
  • the THV polymer coating 16 can be conformal as in Figure IB. Alternatively, the coating can be ablumenal, luminal, or any combination thereof. Because the THV polymers of the have improved elongation properties compared to existing fluoropolymers, coating 16 can expand as the stent expands during use without cracking.
  • a bioactive agent is associated with the coated medical devices.
  • the bioactive agent can be associated with a base coat, top coat, mixed with the THV polymers, and/or be incorporated or otherwise applied to a supporting structure of the medical device.
  • the bioactive agents can be any moiety capable of contributing to a therapeutic effect, a prophylactic effect, both a therapeutic and prophylactic effect, or other biologically active effect in a mammal.
  • the agent can also have diagnostic properties.
  • the bioactive agents include, but are not limited to, small molecules, nucleotides, oligonucleotides, polynucleotides, amino acids, oligopeptides, polypeptides, and proteins.
  • the bioactive agent inhibits the activity of vascular smooth muscle cells.
  • the bioactive agent controls migration or proliferation of smooth muscle cells to inhibit restenosis.
  • Bioactive agents include, but are not limited to, antiproliferatives, antineoplastics, antimitotics, anti-inflammatories, antiplatelets, anticoagulants, antifibrins, antithrombins, antibiotics, antiallergics, antioxidants, and any prodrugs, metabolites, analogs, homologues, congeners, derivatives, salts and combinations thereof. It is to be appreciated that one skilled in the art should recognize that some of the groups, subgroups, and individual bioactive agents may not be used in some embodiments of the invention.
  • Antiproliferatives include, for example, actinomycin D, actinomycin IV, actinomycin I 1 , actinomycin X 1 , actinomycin C 1 , dactinomycin (COSMEGEN ® , Merck & Co., Inc.), imatinib mesylate, and any prodrugs, metabolites, analogs, homologues, congeners, derivatives, salts and combinations thereof.
  • Antineoplastics or antimitotics include, for example, paclitaxel (TAXOL ® , Bristol-Myers Squibb Co.), docetaxel (TAXOTERE ® , Aventis S.A.), midostaurin, methotrexate, azathioprine, vincristine, vinblastine, fluorouracil, doxorubicin hydrochloride (ADRIAMYCIN ® , Pfizer, Inc.) and mitomycin (MUTAMYCIN ® , Bristol-Myers Squibb Co.), midostaurin, and any prodrugs, metabolites, analogs, homologues, congeners, derivatives, salts and combinations thereof.
  • paclitaxel TAXOL ® , Bristol-Myers Squibb Co.
  • TXOTERE ® docetaxel
  • midostaurin methotrexate
  • azathioprine vincristine, vinblastine
  • Antiplatelets, anticoagulants, antifibrin, and antithrombins include, for example, sodium heparin, low molecular weight heparins, heparinoids, hirudin, argatroban, forskolin, vapiprost, prostacyclin and prostacyclin analogues, dextran, D-phe-pro-arg- chloromethylketone (synthetic antithrombin), dipyridamole, glycoprotein Ilb/IIIa platelet membrane receptor antagonist antibody, recombinant hirudin, and thrombin inhibitors (ANGIOMAX ® , Biogen, Inc.), and any prodrugs, metabolites, analogs, homologues, congeners, derivatives, salts and combinations thereof.
  • Cytostatic or antiproliferative agents include, for example, angiopeptin, angiotensin converting enzyme inhibitors including captopril (CAPOTEN ® and CAPOZIDE ® , Bristol-Myers Squibb Co.), cilazapril or lisinopril (PRJNIVIL ® and PRINZIDE ® , Merck & Co., Inc.); calcium channel blockers including nifedipine; colchicines; fibroblast growth factor (FGF) antagonists, fish oil (omega 3-fatty acid); histamine antagonists; lovastatin (MEVACOR ® , Merck & Co., Inc.); monoclonal antibodies including, but not limited to, antibodies specific for Platelet-Derived Growth Factor (PDGF) receptors; nitroprusside; phosphodiesterase inhibitors; prostaglandin inhibitors; suramin; serotonin blockers; steroids; thioprotease inhibitors; PDGF antagonist
  • Antiallergic agents include, but are not limited to, pemirolast potassium (ALAMAST ® , Santen, Inc.), and any prodrugs, metabolites, analogs, homologues, congeners, derivatives, salts and combinations thereof.
  • Other bioactive agents useful in embodiments of the invention include, but are not limited to, free radical scavengers; nitric oxide donors; rapamycin; methyl rapamycin; 42-Epi-(tetrazoylyl)rapamycin (ABT-578); 40-O-(2-hydroxy)ethyl- rapamycin (everolimus); tacrolimus; pimecrolimus; 40-O-(3 -hydroxy )propyl- rapamycin; 40-O-[2-(2-hydroxy)ethoxy]ethyl-rapamycin; tetrazole including rapamycin analogs including those described in U.S.
  • Free radical scavengers include, but are not limited to, 2,2',6,6'-tetramethyl-l- piperinyloxy, free radical (TEMPO); 4-amino-2,2',6,6'-tetramethyl-l-piperinyloxy, free radical (4-amino-TEMPO); 4-hydroxy-2,2',6,6'-tetramethyl-piperidene-l-oxy, free radical (TEMPOL), 2,2',3,4,5,5'-hexamethyl-3-imidazolinium-l-yloxy methyl sulfate, free radical; 16-doxyl-stearic acid, free radical; superoxide dismutase mimic (SODm) and any analogs, homologues, congeners, derivatives, salts and combinations thereof.
  • TEMPO free radical
  • 4-amino-2,2',6,6'-tetramethyl-l-piperinyloxy, free radical (4-amino-TEMPO)
  • Nitric oxide donors include, but are not limited to, S-nitrosothiols, nitrites, N-oxo-N- nitrosamines, substrates of nitric oxide synthase, diazenium diolates including spermine diazenium diolate and any analogs, homologues, congeners, derivatives, salts and combinations thereof.
  • the medical devices of the invention can be used in any vascular, non- vascular, or tubular structure in the body.
  • a coated stent can be used in, but is not limited to use in, neurological, carotid, coronary, aorta, renal, biliary, ureter, iliac, femoral, and popliteal vessels. IV. EXAMPLES
  • Example 1 The following are specific examples of methods for using THV polymer on a coated implantable device.
  • Example 1 The following are specific examples of methods for using THV polymer on a coated implantable device.
  • Example 1 describes a method for manufacturing a coated stent using THV 220A available from Dyneon of Oakdale, Minnesota.
  • a primer coating is applied to the stent.
  • a primer solution including between about 0.1 mass % and about 15 mass %, (e.g., about 2.0 mass %) of poly(n-butyl methacrylate) (PBMA) and the balance, a solvent mixture of acetone and cyclohexanone (having about 70 mass % of acetone and about 30 mass % of cyclohexanone) is prepared.
  • PBMA poly(n-butyl methacrylate)
  • the solution is applied onto a stent to form a primer layer.
  • a spray apparatus e.g., Sono-Tek MicroMist spray nozzle, manufactured by Sono-Tek Corporation of Milton, New York
  • the spray apparatus is an ultrasonic atomizer with a gas entrainment stream.
  • a syringe pump is used to supply the coating solution to the nozzle.
  • the composition is atomized by ultrasonic energy and applied to the stent surfaces.
  • a useful nozzle to stent distance is about 20 mm to about 40 mm at an ultrasonic power of about one watt to about two watts.
  • the stent is optionally rotated about its longitudinal axis, at a speed of 100 to about 600 rpm, for example, about 400 rpm.
  • the stent is also linearly moved along the same axis during the application.
  • the primer solution is applied to a 15 mm Triplex, N stent (available from Abbott Vascular Corporation) in a series of 20-second passes, to deposit, for example, 20 ⁇ g of coating per spray pass. Between the spray passes, the stent is allowed to dry for about 10 seconds to about 30 seconds at ambient temperature. Four spray passes can be applied, followed by baking the primer layer at about 80 0 C for about 1 hour. As a result, a primer layer can be formed having a solids content of about 80 ⁇ g.
  • Solids means the amount of the dry residue deposited on the stent after all volatile organic compounds (e.g., the solvent) have been removed.
  • a THV 220A solution is prepared.
  • the solution is prepared by dissolving between about 0.1 mass % and about 15 mass %, (e.g., about 2.0 mass %) of the THV 220A in a solvent.
  • the solvent can be a mixture of about 50 mass % acetone and about 50 mass % dimethylacetamide.
  • the copolymer solution is applied to a stent.
  • Twenty spray passes are performed with a coating application of 10 ug per pass, with a drying time between passes of 10 seconds, followed by baking the copolymer layer at about 60 0 C for about 1 hour, to form a layer having a solids content between about 30 ⁇ g and 750 ⁇ g, (e.g., about 225 ⁇ g).
  • Example 2 describes a method for manufacturing a drug eluting stent according to one embodiment of the invention.
  • the medical device is manufactured using the same method as in Example 1, except that instead of the THV 220A solution, a polymer-drug solution is prepared and applied using the following formula.
  • a drug-including formulation is prepared that includes:
  • the therapeutic agent is ABT-578 (available from Abbott Vascular Corp. of Chicago, Illinois); and
  • the drug-including formulation is applied to the stent in a manner similar to the application of the copolymer solution in Example 1.
  • the process results in the formation of a drug-polymer reservoir layer having a solids content between about 30 ⁇ g and 750 ⁇ g, (e.g., about 225 ⁇ g), and a drug content of between about 10 ⁇ g and about 250 ⁇ g, (e.g., about 75 ⁇ g).
PCT/US2007/084779 2006-11-21 2007-11-15 Use of a terpolymer of tetrafluoroethylene, hexafluoropropylene, and vinylidene fluoride in drug eluting coatings WO2008064058A2 (en)

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US8658749B2 (en) 2014-02-25
US7928176B2 (en) 2011-04-19
US8202956B2 (en) 2012-06-19
US20080124450A1 (en) 2008-05-29
US7910678B2 (en) 2011-03-22
US20080125560A1 (en) 2008-05-29
US7622537B2 (en) 2009-11-24
US7781551B2 (en) 2010-08-24
US8846839B2 (en) 2014-09-30
US20120157602A1 (en) 2012-06-21
US20110166250A1 (en) 2011-07-07
EP2097119A2 (en) 2009-09-09
JP2010509998A (ja) 2010-04-02
US20080139746A1 (en) 2008-06-12
US8101156B2 (en) 2012-01-24
JP5557373B2 (ja) 2014-07-23
US20100022663A1 (en) 2010-01-28
US7928177B2 (en) 2011-04-19
US20080147178A1 (en) 2008-06-19
US8063151B2 (en) 2011-11-22
WO2008064058A3 (en) 2008-12-24
US20100183798A1 (en) 2010-07-22
US20110160391A1 (en) 2011-06-30
EP2097119A4 (en) 2012-10-17
US20110160382A1 (en) 2011-06-30
US8197880B2 (en) 2012-06-12
US20110160331A1 (en) 2011-06-30
US8399584B2 (en) 2013-03-19
US8048975B2 (en) 2011-11-01
US8071705B2 (en) 2011-12-06
US20080153923A1 (en) 2008-06-26
WO2008064058A9 (en) 2008-10-30
US20110160417A1 (en) 2011-06-30
US20080146696A1 (en) 2008-06-19
US20080125514A1 (en) 2008-05-29
US8569435B2 (en) 2013-10-29

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