US20090062909A1 - Stent with polymer coating containing amorphous rapamycin - Google Patents

Stent with polymer coating containing amorphous rapamycin Download PDF

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Publication number
US20090062909A1
US20090062909A1 US11/995,685 US99568506A US2009062909A1 US 20090062909 A1 US20090062909 A1 US 20090062909A1 US 99568506 A US99568506 A US 99568506A US 2009062909 A1 US2009062909 A1 US 2009062909A1
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United States
Prior art keywords
rapamycin
stent
coating
polymer coating
peva
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Abandoned
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US11/995,685
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English (en)
Inventor
Doug Taylor
James DeYoung
Jim McCain
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MiCell Technologies Inc
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MiCell Technologies Inc
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Application filed by MiCell Technologies Inc filed Critical MiCell Technologies Inc
Priority to US11/995,685 priority Critical patent/US20090062909A1/en
Assigned to MICELL TECHNOLOGIES, INC. reassignment MICELL TECHNOLOGIES, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: TAYLOR, DOUG, DEYOUNG, JAMES, MCCLAIN, JIM
Publication of US20090062909A1 publication Critical patent/US20090062909A1/en
Abandoned legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F2/00—Filters implantable into blood vessels; Prostheses, i.e. artificial substitutes or replacements for parts of the body; Appliances for connecting them with the body; Devices providing patency to, or preventing collapsing of, tubular structures of the body, e.g. stents
    • A61F2/82—Devices providing patency to, or preventing collapsing of, tubular structures of the body, e.g. stents
    • A61F2/86—Stents in a form characterised by the wire-like elements; Stents in the form characterised by a net-like or mesh-like structure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F2/00—Filters implantable into blood vessels; Prostheses, i.e. artificial substitutes or replacements for parts of the body; Appliances for connecting them with the body; Devices providing patency to, or preventing collapsing of, tubular structures of the body, e.g. stents
    • A61F2/02—Prostheses implantable into the body
    • A61F2/04—Hollow or tubular parts of organs, e.g. bladders, tracheae, bronchi or bile ducts
    • A61F2/06—Blood vessels
    • A61F2/07—Stent-grafts
    • 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
    • A61L31/02—Inorganic materials
    • A61L31/022—Metals or alloys
    • 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
    • A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F2/00—Filters implantable into blood vessels; Prostheses, i.e. artificial substitutes or replacements for parts of the body; Appliances for connecting them with the body; Devices providing patency to, or preventing collapsing of, tubular structures of the body, e.g. stents
    • A61F2/82—Devices providing patency to, or preventing collapsing of, tubular structures of the body, e.g. stents
    • A61F2002/821—Ostial stents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F2240/00—Manufacturing or designing of prostheses classified in groups A61F2/00 - A61F2/26 or A61F2/82 or A61F9/00 or A61F11/00 or subgroups thereof
    • A61F2240/001—Designing or manufacturing processes
    • A61F2240/002—Designing or making customized prostheses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F2250/00—Special features of prostheses classified in groups A61F2/00 - A61F2/26 or A61F2/82 or A61F9/00 or A61F11/00 or subgroups thereof
    • A61F2250/0058—Additional features; Implant or prostheses properties not otherwise provided for
    • A61F2250/0067—Means for introducing or releasing pharmaceutical products into the body
    • 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
    • A61L2300/20—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials
    • A61L2300/216—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials with other specific functional groups, e.g. aldehydes, ketones, phenols, quaternary phosphonium groups
    • 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
    • A61L2300/60—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a special physical form
    • A61L2300/606—Coatings
    • 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
    • A61L2420/00—Materials or methods for coatings medical devices
    • A61L2420/08—Coatings comprising two or more layers

Definitions

  • DES drug eluting stents
  • Such localized delivery of these agents avoids the problems of systemic administration, which may be accompanied by unwanted effects on other parts of the body, or because administration to the afflicted body part requires a high concentration of pharmaceutical or biological agent that may not be achievable by systemic administration.
  • the coating may provide for controlled release, including long-term or sustained release, of a pharmaceutical or biological agent.
  • biomedical implants may be coated with materials to provide beneficial surface properties, such as enhanced biocompatibility or lubriciousness.
  • the present invention provides a coated coronary stent comprising: a stainless steel sent framework coated with a primer layer of Parylene C; and a rapamycin-polymer coating having substantially uniform thickness disposed on the stent framework, wherein the rapamycin-polymer coating comprises polybutyl methacrylate (PBMA), polyethylene-co-vinyl acetate (PEVA) and rapamycin, wherein substantially all of the rapamycin in the coating is in amorphous form and substantially uniformly dispersed within the rapamycin-polymer coating.
  • PBMA polybutyl methacrylate
  • PEVA polyethylene-co-vinyl acetate
  • rapamycin rapamycin
  • the invention provides coated stents, wherein rapamycin is in the form of particles having an average diameter from 2 nm to 500 nm.
  • the invention provides coated stents, wherein the rapamycin-polymer coating has a thickness of about 1 to about 30 microns.
  • the coating is preferably substantially free of solvent residue.
  • the invention provides a coated stent, wherein the rapamycin-polymer coating is sintered in dense carbon dioxide at a temperature of about 40 C to about 60 C, whereby bulk properties and adhesion of the coating to the stent are improved without altering the quality of the rapamycin, PBMA or PEVA.
  • the rapamycin-polymer coating covers substantially the entire surface of the stent framework and/or the rapamycin-polymer coating is substantially free of aggregated particles.
  • the invention provides a stent coated with a polymer and rapamycin comprising: a stainless steel stent framework coated with a primer layer of Parylene C; and a rapamycin-polymer coating disposed on the stent framework, wherein the rapamycin-polymer coating comprises PBMA, PEVA; and rapamycin substantially uniformly dispersed within the rapamycin-polymer coating, wherein substantially all of rapamycin in the coating is in amorphous form, wherein disposing the coating is carried out by a spray coating process whereby rapamycin spray particles are formed by rapid expansion of a supercritical or near critical fluid mixture, and the rapamycin spray particles and the stent framework are oppositely charged so that the spray particles are electrostatically attracted to the stent framework.
  • the spray coating process is carried out under RESS condition.
  • the supercritical or near critical fluid mixture preferably comprises PBMA, PEVA and rapamycin dissolved in dimethylether, chlorofluorocarbon, hydrofluorocarbon, carbon dioxide or mixtures thereof.
  • FIG. 1 Rapid Expansion of Supercritical Solutions (RESS) process equipment see C. Domingo et al, Journal of Supercritical Fluids 10, 39-55 (1997)
  • FIG. 2 Infrared spectra of each component and the spray coating mixture. Individual peaks for each component are labeled.
  • FIG. 3 Stents coated (top panel) and sintered under different conditions (lower two panels) with rapamycin, PEVA and PBMA. All stent surfaces are coated
  • FIG. 4 Infrared spectra with all components coated, before and after sintering. The spectra indicate that no damage is done to the coating during the sintering process.
  • FIG. 5 XRD for RESS sprayed and as received rapamycin.
  • the RESS sprayed rapamycin does not show any diffraction peaks indicating the RESS sprayed material is in amorphous form
  • Compressed fluid refers to a fluid of appreciable density (e.g., >0.2 g/cc) that is a gas at standard temperature and pressure.
  • Supercritical fluid refers to a compressed fluid under conditions wherein the temperature is at least 80% of the critical temperature of the fluid and the pressure is at least 50% of the critical pressure of the fluid.
  • substances that demonstrate supercritical or near critical behavior suitable for the present invention include, but are not limited to carbon dioxide, isobutylene, ammonia, water, methanol, ethanol, ethane, propane, butane, pentane, dimethyl ether, xenon, sulfur hexafluoride, halogenated and partially halogenated materials such as chlorofluorocarbons, hydrochlorofluoro carbons, hydrofluorocarbons, perfluorocarbons (such as perfluoromethane and perfluoropropane, chloroform, trichloro-fluoromethane, dichloro-difluoromethane, dichloro-tetrafluoroethane) and mixtures thereof.
  • chlorofluorocarbons such as chlorofluorocarbons, hydrochlorofluoro carbons, hydrofluorocarbons, perfluorocarbons (such as perfluoromethane and perfluoropropane, chloroform, trich
  • “Sintering” as used herein refers to the process by which the polymer or polymers form continuous coating by treatment of the coated substrate with a densified gas, compressed fluid, compressed gas, near critical fluid or supercritical fluid that is a non-solvent for both the polymer and the pharmaceutical agent and biological agents, but an agent that induces formation of continuous domains of polymer.
  • a densified gas, compressed fluid, compressed gas, near critical fluid or supercritical fluid that is a non-solvent for both the polymer and the pharmaceutical agent and biological agents, but an agent that induces formation of continuous domains of polymer.
  • Rapid Expansion of Supercritical Solutions involves the dissolution of a polymer into a compressed fluid, typically a supercritical fluid, followed by rapid expansion into a chamber at lower pressure, typically near atmospheric conditions.
  • the atmosphere of the chamber is maintained in an electrically neutral state by maintaining an isolating “cloud” of gas in the chamber. Carbon dioxide or other appropriate gas is employed to prevent electrical charge is transferred from the substrate to the surrounding environment.
  • Electrostatic capture refers to the collection of the spray-produced particles upon a substrate that has a different electrostatic potential than the sprayed particles.
  • the substrate is at an attractive electronic potential with respect to the particles exiting, which results in the capture of the particles upon the substrate. i.e. the substrate and particles are oppositely charged, and the particles transport through the fluid medium of the capture vessel onto the surface of the substrate is enhanced via electrostatic attraction. This may be achieved by charging the particles and grounding the substrate or conversely charging the substrate and grounding the particles, or by some other process, which would be easily envisaged by one of skill in the art of electrostatic capture.
  • Open vessel refers to a vessel open to the outside atmosphere, and thus at substantially the same temperature and pressure as the outside atmosphere.
  • “Closed vessel” as used herein refers to a vessel sealed from the outside atmosphere, and thus may be at significantly different temperatures and pressures to the outside atmosphere. Rapamycin is an immunosuppressive lactam macrolide that is produced by Streptomyces hygroscopicus , and having the structure depicted in Formula:
  • the present invention provides a coated coronary stent comprising: a stainless steel sent framework coated with a primer layer of Parylene C; and a rapamycin-polymer coating having substantially uniform thickness disposed on the stent framework, wherein the rapamycin-polymer coating comprises polybutyl methacrylate (PBMA), polyethylene-co-vinyl acetate (PEVA) and rapamycin, wherein substantially all of the rapamycin in the coating is in amorphous form and substantially uniformly dispersed within the rapamycin-polymer coating.
  • PBMA polybutyl methacrylate
  • PEVA polyethylene-co-vinyl acetate
  • the PBMA, PEVA and rapamycin are present in a ratio of about 1:1:1.
  • the invention provides coated stents, wherein rapamycin is in the form of particles having an average diameter from 2 nm to 500 nm.
  • the invention provides coated stents, wherein the rapamycin-polymer coating has a thickness of about 1 to about 30 microns.
  • the coating is preferably substantially free of solvent residue.
  • the invention provides a coated stent, wherein the rapamycin-polymer coating is sintered in dense carbon dioxide at a temperature of about 40 C to about 60 C, whereby bulk properties and adhesion of the coating to the stent are improved without altering the quality of the rapamycin, PBMA or PEVA.
  • the rapamycin-polymer coating covers substantially the entire surface of the stent framework.
  • the invention encompasses embodiments wherein the rapamycin-polymer coating is substantially free of aggregated particles.
  • the invention also provides a stent coated with a polymer and rapamycin comprising: a stainless steel stent framework coated with a primer layer of Parylene C; and a rapamycin-polymer polymer coating disposed on the stent framework, wherein the rapamycin-polymer coating comprises PBMA, PEVA; and rapamycin substantially uniformly dispersed within the rapamycin-polymer coating, wherein substantially all of rapamycin in the coating is in amorphous form, wherein disposing the coating is carried out by a spray coating process whereby rapamycin spray particles are formed by rapid expansion of a supercritical or near critical fluid mixture, and the rapamycin spray particles and the stent framework are oppositely charged so that the spray particles are electrostatically attracted to the stent framework.
  • the spray coating process is carried out under RESS condition.
  • the supercritical or near critical fluid mixture preferably comprises PBMA, PEVA and rapamycin dissolved in dimethylether, chlorofluorocarbon, hydrofluorocarbon, carbon dioxide or mixtures thereof.
  • FIG. 1 The RESS process equipment used in the present studies is depicted in FIG. 1 . This is a common design for a RESS apparatus see C. Domingo et al, Journal of Supercritical Fluids 10, 39-55 (1997).
  • a solution containing rapamycin that is saturated in a solvent or supersaturated in a solvent is sprayed at a flow rate sufficient to achieve flow into a chamber of known volume pressurized above ambient pressure and containing a coronary stent.
  • the system temperature is held constant or allowed to vary so that any number of points in the phase diagrams of the solution or mixture or any of its individual components can be mapped in pressure-temperature, volume-pressure or pressure-volume space constituting liquid, gas or supercritical CO 2 conditions.
  • CO 2 in any single phase or combination of phases flows through the chamber at a mass flow rate of 5 gm/min to some multiple of this flow rate.
  • the solute and solvent flow that is a solution of the therapeutic compound and suitable solvent for the chosen solute or solutes cease but CO 2 flow continues for an additional period of time maintaining constant pressure during this period. After this time period, the pressure is dropped to atmospheric pressure.
  • the particles are attracted to the stent by charging the substrate oppositely to that of the sprayed particle charge by applying a voltage that is greater than 5000 V but less than the ionization potential of the most easily ionized component of the mixture.
  • the particles may also traverse an electromagnetic field such that the field is used to guide the particle to a target.
  • the individual bands used for compositional analysis were determined by spray coating Si wafer chips with each component separately.
  • the coating thickness was determined gravimetrically and calculated from the density of the materials. It was assumed that the layer is fully dense. The thickness can be controlled by varying the spray time.
  • the coating In the as sprayed state, the coating lacks strong adhesion to the substrate. Sintering the coated substrate (see FIG. 3 ) dramatically improves coating adhesion while leaving the components unaltered as the infrared spectra shown in FIG. 4 confirm.
  • the coating is sintered in a supercritical carbon dioxide environment allowing mild sintering conditions to be used with temperature below 80 C.
  • FIG. 4 shows Infrared spectra with all components coated, before and after sintering.
  • the spectra indicate that no damage is done to the coating during the sintering process.
  • the spectra demonstrate that the sintering process does not adversely impact the coating since no new stretches appear in the after sintering spectrum.
  • FIG. 5 shows XRD data taken for an authentic rapamycin sample (as received rapamycin) and RESS sprayed rapamycin.
  • the RESS sprayed rapamycin does not show any diffraction peaks indicating the RESS sprayed material is in amorphous form. In other words, the RESS sprayed rapamycin lacks any crystallinity as indicated by the absence of diffraction peaks in the XRD.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Vascular Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Biomedical Technology (AREA)
  • Epidemiology (AREA)
  • Surgery (AREA)
  • Transplantation (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Cardiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Pulmonology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Inorganic Chemistry (AREA)
  • Materials For Medical Uses (AREA)
  • Media Introduction/Drainage Providing Device (AREA)
US11/995,685 2005-07-15 2006-07-14 Stent with polymer coating containing amorphous rapamycin Abandoned US20090062909A1 (en)

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US11/995,685 US20090062909A1 (en) 2005-07-15 2006-07-14 Stent with polymer coating containing amorphous rapamycin

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US69965005P 2005-07-15 2005-07-15
US76533906P 2006-02-03 2006-02-03
US11/995,685 US20090062909A1 (en) 2005-07-15 2006-07-14 Stent with polymer coating containing amorphous rapamycin
PCT/US2006/027322 WO2007011708A2 (fr) 2005-07-15 2006-07-14 Stent a revetement polymere renfermant de la rapamycine amorphe

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Cited By (30)

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US20080095919A1 (en) * 2006-10-23 2008-04-24 Mcclain James B Holder For Electrically Charging A Substrate During Coating
US20090123515A1 (en) * 2005-07-15 2009-05-14 Doug Taylor Polymer coatings containing drug powder of controlled morphology
US20090186069A1 (en) * 2006-04-26 2009-07-23 Micell Technologies, Inc. Coatings Containing Multiple Drugs
US20090292351A1 (en) * 2008-04-17 2009-11-26 Micell Technologies, Inc. Stents having bioabsorbable layers
US20100015200A1 (en) * 2008-07-17 2010-01-21 Micell Technologies, Inc. Drug Delivery Medical Device
US20100030261A1 (en) * 2006-10-02 2010-02-04 Micell Technologies, Inc. Surgical Sutures Having Increased Strength
US20100063580A1 (en) * 2007-01-08 2010-03-11 Mcclain James B Stents having biodegradable layers
US20100211164A1 (en) * 2007-04-17 2010-08-19 Mcclain James B Stents having biodegradable layers
US20100228348A1 (en) * 2007-05-25 2010-09-09 Micell Technologies, Inc. Polymer Films for Medical Device Coating
US20100239635A1 (en) * 2009-03-23 2010-09-23 Micell Technologies, Inc. Drug delivery medical device
US20100241220A1 (en) * 2009-03-23 2010-09-23 Mcclain James B Peripheral Stents Having Layers
US20100256746A1 (en) * 2009-03-23 2010-10-07 Micell Technologies, Inc. Biodegradable polymers
US20100256748A1 (en) * 2009-04-01 2010-10-07 Micell Technologies, Inc. Coated stents
US20100272778A1 (en) * 2007-04-17 2010-10-28 Micell Technologies, Inc. Stents having controlled elution
US20100298928A1 (en) * 2007-10-19 2010-11-25 Micell Technologies, Inc. Drug Coated Stents
US20110159069A1 (en) * 2008-12-26 2011-06-30 Shaw Wendy J Medical Implants and Methods of Making Medical Implants
US20110190864A1 (en) * 2010-02-02 2011-08-04 Micell Technologies, Inc. Stent and stent delivery system with improved deliverability
US20110238161A1 (en) * 2010-03-26 2011-09-29 Battelle Memorial Institute System and method for enhanced electrostatic deposition and surface coatings
WO2011130448A1 (fr) * 2010-04-16 2011-10-20 Micell Technologies, Inc. Endoprothèses vasculaires ayant une élution contrôlée
US9510856B2 (en) 2008-07-17 2016-12-06 Micell Technologies, Inc. Drug delivery medical device
US9636309B2 (en) 2010-09-09 2017-05-02 Micell Technologies, Inc. Macrolide dosage forms
US10117972B2 (en) 2011-07-15 2018-11-06 Micell Technologies, Inc. Drug delivery medical device
US10188772B2 (en) 2011-10-18 2019-01-29 Micell Technologies, Inc. Drug delivery medical device
US10232092B2 (en) 2010-04-22 2019-03-19 Micell Technologies, Inc. Stents and other devices having extracellular matrix coating
US10272606B2 (en) 2013-05-15 2019-04-30 Micell Technologies, Inc. Bioabsorbable biomedical implants
US10464100B2 (en) 2011-05-31 2019-11-05 Micell Technologies, Inc. System and process for formation of a time-released, drug-eluting transferable coating
US10835396B2 (en) 2005-07-15 2020-11-17 Micell Technologies, Inc. Stent with polymer coating containing amorphous rapamycin
US11039943B2 (en) 2013-03-12 2021-06-22 Micell Technologies, Inc. Bioabsorbable biomedical implants
US11426494B2 (en) 2007-01-08 2022-08-30 MT Acquisition Holdings LLC Stents having biodegradable layers
US11904118B2 (en) 2010-07-16 2024-02-20 Micell Medtech Inc. Drug delivery medical device

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