WO2000032238A1 - Stent having drug crystals thereon - Google Patents
Stent having drug crystals thereon Download PDFInfo
- Publication number
- WO2000032238A1 WO2000032238A1 PCT/US1999/027279 US9927279W WO0032238A1 WO 2000032238 A1 WO2000032238 A1 WO 2000032238A1 US 9927279 W US9927279 W US 9927279W WO 0032238 A1 WO0032238 A1 WO 0032238A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- medical device
- therapeutic agent
- coating
- polymer
- crystals
- Prior art date
Links
Classifications
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6957—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being a device or a kit, e.g. stents or microdevices
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
-
- 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
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/416—Anti-neoplastic or anti-proliferative or anti-restenosis or anti-angiogenic agents, e.g. paclitaxel, sirolimus
-
- 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
- A61L2300/602—Type of release, e.g. controlled, sustained, slow
- A61L2300/604—Biodegradation
-
- 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
- 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
- A61L2300/63—Crystals
Definitions
- the present invention relates to the localized delivery of therapeutic agents, and more particularly to the localized delivery of crystalline therapeutic agents to target locations within a body.
- systemic administration of drug agents treats the body as a whole even though the disease to be treated may be localized.
- systemic administration may not be desirable because the drug agents often have unwanted effects on parts of the body that are not intended to be treated, or because treatment of the diseased part of the body requires a high concentration of drug agent that may not be achievable by systemic administration.
- U.S. Patent No. 5,304,121 which is incorporated herein by reference, discloses a method of delivering water-soluble drugs to tissue at desired locations of a body lumen wall. The method generally includes the steps of impregnating a hydrogel polymer on a balloon catheter with an aqueous drug solution, inserting the catheter into a blood vessel to a desired location, and expanding the catheter balloon against the surrounding tissue to allow the release of the drug.
- One potential drawback to conventional localized drug administration is the uncontrolled rapidity at which the drug or drug solution is released from the delivery device. It is often desired, if not necessary, to control and/or lengthen the time period over which the drug is released. For example, it might be advantageous to lengthen the release time from seconds to minutes, or from minutes to hours, days, or even weeks. Exceptionally long release times as long as several months are often desired, for example, where the drug is released from an implanted device such as a stent. Moreover, it is often desired to control the release rate of the drug over prolonged periods of time.
- the present invention provides a medical device for insertion into a mammalian body, wherein the medical device has a therapeutic agent applied to at least a portion of a surface thereof, and the therapeutic agent is in a crystalline form.
- the present invention provides a method of delivering a therapeutic agent to a target location within a mammalian body.
- the method comprises the steps of placing crystals of the therapeutic agent on at least a portion of a surface of a medical device, and delivering the medical device to the target location.
- One advantage of the present invention is that it retards the release of therapeutic agents from a localized drug delivery system.
- Another advantage of the present invention is that it provides for a controlled release rate of therapeutic agents from a localized drug delivery system.
- Balloon catheter refers to a tubular instrument with a balloon or multiple balloons that can be inflated or deflated without removal after insertion into the body.
- Biodegradable refers to a substance that can be substantially chemically degraded or decomposed by exposure to bodily tissue or fluids.
- Biostable refers to a substance that is not substantially chemically degraded or decomposed by exposure to bodily tissue or fluids.
- Crystal refers to a solid of regular shape and, for a given material, characteristic angles, wherein the individual atoms or molecules within the crystal take up regular positions with respect to one another.
- Crystalstallization refers to the process whereby a material assumes a crystalline form when a vapor or liquid becomes solidified, or a solute precipitates from solution under proper conditions.
- Drug and “therapeutic agent” are used interchangeably to refer to any substance used in the prevention, diagnosis, alleviation, treatment or cure of disease.
- Stepsis refers to a stricture of any bodily canal.
- Stent refers to any tubular structure used to maintain or support a bodily orifice or cavity.
- Fig. 1 is a scanning electron microphotograph of medical device having crystals of therapeutic agent thereon.
- Fig. 2 is a scanning electron microphotograph of medical device having a layer of therapeutic agent crystals thereon.
- Fig. 3 is a graph showing the release profiles of paclitaxel from coated stents, for paclitaxel in both crystalline and non-crystalline form.
- the present invention makes use of crystals of therapeutic agents to retard the release of the therapeutic agent when delivered to a target location within a mammalian body. Moreover, the release of the therapeutic agent in its crystalline form is controlled in that the therapeutic agent is released at a characteristic rate or release profile over time.
- the present invention provides a medical device for insertion into a mammalian body, wherein the medical device has a therapeutic agent applied to at least a portion of a surface thereof, and the therapeutic agent is in the form of crystals.
- the therapeutic agent used in the present invention includes, for example, any pharmaceutically active material that can be crystallized.
- Such therapeutic agents may include biologically active solutes such as anti-thrombogenic agents such as heparin, heparin derivatives, urokinase, PPACK (dextrophenylalanine proline arginine chloromethylketone), rapamycin, probucol, and verapimil; angiogenic and anti-angiogenic agents; anti-proliferative agents such as enoxaprin, angiopeptin, or monoclonal antibodies capable of blocking smooth muscle cell proliferation, hirudin, and acetylsalicylic acid; anti-inflammatory agents such as dexamethasone, prednisolo ⁇ e, corticosterone, budesonide, estrogen, sulfasalazine, and mesalamine; antineoplastic/ antiproliferative/ anti-mitotic agents such as paclitaxel, 5-fluorouracil
- Preferred therapeutic agents for use in the present invention are paclitaxel and derivatives thereof.
- the therapeutic agent is placed on a medical device for insertion into the body to a target location.
- the medical device used in the present invention is any insertable or implantable device including, for example, stents, balloon catheters, blood clot filters, vascular grafts, stent grafts, aneurysm filling coils, intralumenal paving systems, etc., as are known in the art.
- a preferred medical device for use with the present invention is an implantable device such as a stent, for which the present invention allows for the continued release of therapeutic agents therefrom for extended time periods of up to several months.
- the therapeutic agent is applied to the medical device, for example, such that isolated, individual crystals 101 exist on the surface of the medical device 102.
- the therapeutic agent is applied to the medical device such that a layer 201 of crystals exists on at least a portion of the medical device 202.
- the crystals of the therapeutic agent are optionally placed within or over a polymer coating, which at least partially coats the medical device as described further herein.
- the crystals of the therapeutic agent are applied to the medical device by any suitable method.
- the crystals are formed by the following steps: i) placing a therapeutic agent, while in a non-crystalline form, into solution with a polymer in which the therapeutic agent is substantially soluble; ii) applying the solution onto at least a portion of a medical device as a coating; iii) drying the coating to form a dry coating wherein the therapeutic agent is dispersed in the polymer; iv) exposing the coated medical device to a non-solvent (i.e., a material in which the therapeutic agent is relatively insoluble); and v) allowing the therapeutic agent to diffuse out of the coating to the interface between the coating and the non-solvent, whereupon the therapeutic agent crystallizes on the surface of the coating.
- a non-solvent i.e., a material in which the therapeutic agent is relatively insoluble
- the non-solvent penetrates the coating such that the therapeutic agent crystallizes within the coating.
- the polymer coating comprises any polymeric material in which the therapeutic agent is substantially soluble.
- the polymer is, for example, hydrophilic, hydrophobic, and/or biodegradable.
- the polymer is selected from the group consisting of polycarboxylic acids, cellulosic polymers, gelatin, polyvinylpyrrolidone, maleic anhydride polymers, polyamides, polyvinyl alcohols, polyethylene oxides, glycosaminoglycans, polysaccharides, polyesters, polyurethanes, silicones, polyorthoesters, polyanhydrides, polycarbonates, polypropylenes, polylactic acids, polyglycolic acids, polycaprolactones, polyhydroxybutyrate valerates, polyacrylamides, polyethers, and mixtures and copolymers thereof.
- Coatings from polymer dispersions such as polyurethane dispersions (BAYHYDROL, etc.) and acrylic latex dispersions are also within the scope of the present invention.
- a preferred polymer for use in the polymer coating of the present invention is polyurethane.
- the crystals are formed by the following steps: i) forming a miscible solution comprising the therapeutic agent, a solvent and a non-solvent, wherein the therapeutic agent is substantially soluble in the solvent and substantially insoluble in the non- solvent, and wherein the solvent is miscible in, and more volatile than, the non-solvent; ii) applying the solution onto a medical device as a coating; and iii) allowing at least a portion of the solvent to evaporate from the coating, whereupon the therapeutic agent forms into crystals on the surface of the medical device.
- the therapeutic agent is applied to the medical device, while in solution or otherwise, by any suitable method.
- Preferred methods include spraying the device with the therapeutic agent or solution, and dipping the device into the therapeutic agent or solution.
- the thickness of the therapeutic agent, together with any polymer is in the range of from 1 to about 50 microns. The thickness of such a coating is not, however, a critical feature of the present invention so long as a sufficient amount of therapeutic agent to provide a sustained or controlled release over a suitable or desired time period is provided.
- the medical device is optionally at least partially coated with a polymer precoat for enhanced adhesion of the therapeutic agent.
- the polymer precoat should have a low solubility for the therapeutic agent.
- Preferred precoat materials include polycarboxylic acids, cellulosic polymers, gelatin, polyvinylpyrrolidone, maleic anhydride polymers, polyamides, polyvinyl alcohols, polyethylene oxides, glycosaminoglycans, polysaccharides, polyesters, polyurethanes, silicones, polyorthoesters, polyanhydrides, polycarbonates, polypropylenes, polylactic acids, polyglycolic acids, polycaprolactones, polyhydroxybutyrate valerates, polyacrylamides, polyethers, and mixtures and copolymers thereof.
- the crystals of the therapeutic agent are optionally coated with a polymer topcoat for physical protection of the crystals, and/or as a barrier to premature release of the therapeutic agent, and/or to further retard or control the release rate of the therapeutic agent.
- the topcoat may be either biodegradable or biostable. If the topcoat is biodegradable, the therapeutic agent is substantially released after the decomposition of the topcoat. If the topcoat is biostable, the therapeutic agent is substantially released by diffusion through the topcoat.
- Preferred biodegradable materials for the topcoat include polymers such as poly(L-lactic acid), poly(DL-lactic acid), polycaprolactone, poly(hydroxy butyrate), polyglycolide, poly(dioxanone), poly(hydroxy valerate), polyorthoester; copolymers such as poly (lactide-co- glycolide), polyhydroxy(butyrate-co-valerate), polyglycolide-co-trimethylene carbonate; polyanhydrides; polyphosphoester; polyphosphoester-urethane; polyamino acids; polycyanoacrylates; biomolecules such as fibrin, fibrinogen, cellulose, starch, collagen and hyaluronic acid; and mixtures thereof.
- polymers such as poly(L-lactic acid), poly(DL-lactic acid), polycaprolactone, poly(hydroxy butyrate), polyglycolide, poly(dioxanone), poly(hydroxy valerate), polyorthoester; copolymers such as poly (lactide
- Preferred biostable materials for the topcoat include polymers such as polyurethane, silicones, polyesters, polyolefins, polyamides, polycaprolactam, polyimide, polyvinyl chloride, polyvinyl methyl ether, polyvinyl alcohol, acrylic polymers and copolymers, polyacrylonitrile, polystyrene copolymers of vinyl monomers with olefins (such as styrene acrylonitrile copolymers, ethylene methyl methacrylate copolymers, ethylene vinyl acetate), polyethers, rayons, cellulosics (such as cellulose acetate, cellulose nitrate, cellulose propionate, etc.), parylene and derivatives thereof; and mixtures and copolymers thereof.
- polymers such as polyurethane, silicones, polyesters, polyolefins, polyamides, polycaprolactam, polyimide, polyvinyl chloride, polyvinyl methyl ether,
- the precoat and topcoat materials are applied by any suitable method such as, for example, spraying, dipping, and vapor deposition such as plasma deposition, physical vapor deposition, chemical vapor deposition, ion bombardment, ion-beam sputter deposition, ion-beam assisted deposition, and sputtering.
- spraying dipping
- vapor deposition such as plasma deposition, physical vapor deposition, chemical vapor deposition, ion bombardment, ion-beam sputter deposition, ion-beam assisted deposition, and sputtering.
- Example 1 Formation of Paclitaxel Crystals from Coated Stents by Exposure to a Non-solvent Paclitaxel (TAXOL ® ) was placed into solution by mixing about 0.19 milligrams of polyurethane, about 0.10 milligrams reagent paclitaxel, and about 27.15 milligrams of 99.9% ACS HPLC-grade chloroform stabilized with ethanol. The mixture was mixed with a magnetic stirrer for about one hour to form a solution consisting of about 1.0% solids and having a polyurethane-to-paclitaxel ratio of about 65-to-35.
- TAXOL ® Non-solvent Paclitaxel
- the paclitaxel solution was sprayed onto 9 millimeter NIR ® (Medinol, Tel Aviv, Israel) stents with a Badger Air Brush model 350 sprayer at a pressure of about 19 psi for about 1 minute. The distance between the stents and the spray nozzle was about 2.5 inches. A uniform coating of approximately 13 microns was obtained. The coating was dried for about 30 minutes at about 65°C to remove solvent, followed by thorough drying for about 3 hours at 70°C under vacuum.
- 9 millimeter NIR ® Medinol, Tel Aviv, Israel
- Paclitaxel crystals were formed on some of the stents by exposure to about 5 milliliters of distilled water for about 1.5 days while stirring at room temperature. The stents were thereafter removed from water and air dried. Scanning electron microscopy was used to confirm the presence of paclitaxel crystals on the surface of the coated stents. The crystals were up to approximately 200 microns in length.
- Stents coated with paclitaxel in both crystalline and non- crystalline form were made in accordance with Example 1.
- the in-vitro release of paclitaxel from these stents was measured as a function of time. As shown in Fig. 3, the paclitaxel in crystalline form was released at a slower rate than the paclitaxel dispersed in the polyurethane coating on the coated stents.
- Topcoats are applied to the coated stents described in Example 1.
- the topcoats comprise either poly(lactide-co-caprolactone) in solution with 99.9% ACS HPLC-grade chloroform stabilized with ethanol, or polyvinyl alcohol in solution with deionized water.
- Topcoat solutions are applied to coated stents by spraying with a Badger Air Brush model 350 sprayer at a pressure of about 19 psi for about 10 seconds.
- the distance between the stents and the spray nozzle is about 2.5 inches.
- a uniform coating of approximately 1 to 2 microns is obtained.
- Paclitaxel is placed in solution with acetonitrile, a solvent. Water, a non-solvent, is added in an amount that does not result in precipitation of the paclitaxel from the acetonitrile / water mixture.
- the mixture of paclitaxel, acetonitrile and water is sprayed onto a NIR ® (Medinol, Tel Aviv, Israel) stent with a Badger Air Brush model 350 sprayer at a pressure of about 19 psi for about 1 minute.
- the distance between the stents and the spray nozzle is about 2.5 inches.
- a uniform coating of approximately 13 microns is obtained. As the acetonitrile evaporates from the coating, paclitaxel crystals form.
- the present invention provides for the controlled, localized delivery of therapeutic agents to target locations within a mammalian body.
- the invention makes use of crystals of such therapeutic agents to retard and/or control the rate of release.
Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU18212/00A AU1821200A (en) | 1998-12-03 | 1999-11-17 | Stent having drug crystals thereon |
EP99961692A EP1135165A1 (en) | 1998-12-03 | 1999-11-17 | Stent having drug crystals thereon |
CA002353606A CA2353606A1 (en) | 1998-12-03 | 1999-11-17 | Stent having drug crystals thereon |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US20425598A | 1998-12-03 | 1998-12-03 | |
US09/204,255 | 1998-12-03 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2000032238A1 true WO2000032238A1 (en) | 2000-06-08 |
WO2000032238A9 WO2000032238A9 (en) | 2000-12-07 |
Family
ID=22757217
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1999/027279 WO2000032238A1 (en) | 1998-12-03 | 1999-11-17 | Stent having drug crystals thereon |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP1135165A1 (en) |
AU (1) | AU1821200A (en) |
CA (1) | CA2353606A1 (en) |
WO (1) | WO2000032238A1 (en) |
Cited By (61)
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WO2002068000A2 (en) * | 2000-11-16 | 2002-09-06 | Microspherix Llc | Polymeric imagable brachytherapy seed |
EP1392751A1 (en) * | 2001-05-07 | 2004-03-03 | Cornell Research Foundation, Inc. | Biodegradable copolymers linked to segment with a plurality of functional groups |
US6746661B2 (en) | 2000-11-16 | 2004-06-08 | Microspherix Llc | Brachytherapy seed |
US7265199B2 (en) | 2000-04-11 | 2007-09-04 | Celonova Biosciences Germany Gmbh | Poly-tri-fluoro-ethoxypolyphosphazene coverings and films |
EP1857127A1 (en) | 2002-09-20 | 2007-11-21 | Bayer Schering Pharma Aktiengesellschaft | Bolloon catheter for Paclitaxel-release |
WO2008089730A2 (en) * | 2007-01-22 | 2008-07-31 | Eurocor Gmbh | Method for loading structured surfaces |
WO2007106441A3 (en) * | 2006-03-10 | 2008-08-07 | Cook Inc | Taxane coatings for implantable medical devices |
WO2009055306A2 (en) * | 2007-10-23 | 2009-04-30 | Abbott Cardiovascular Systems Inc. | Coating designs for the tailored release of dual drugs from polymeric coatings |
US7638159B2 (en) * | 2006-09-12 | 2009-12-29 | Boston Scientific Scimed, Inc. | Liquid masking for selective coating of a stent |
US7750041B2 (en) * | 2001-03-26 | 2010-07-06 | Bayer Schering Pharma Aktiengesellschaft | Preparation for the prophylaxis of restenosis |
WO2010086863A2 (en) | 2009-02-02 | 2010-08-05 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Crystalline drug-containing coatings |
US7776310B2 (en) | 2000-11-16 | 2010-08-17 | Microspherix Llc | Flexible and/or elastic brachytherapy seed or strand |
WO2009158276A3 (en) * | 2008-06-25 | 2010-11-25 | Boston Scientific Scimed, Inc. | Medical devices containing therapeutic agents |
US7875284B2 (en) | 2006-03-10 | 2011-01-25 | Cook Incorporated | Methods of manufacturing and modifying taxane coatings for implantable medical devices |
WO2011008393A3 (en) * | 2009-07-17 | 2011-03-24 | Boston Scientific Scimed, Inc. | Nucleation of drug delivery balloons to provide improved crystal size and density |
EP2324866A2 (en) | 2002-07-12 | 2011-05-25 | Cook Incorporated | Angioplasty balloons drug-coated in an expanded condition |
WO2011061295A1 (en) | 2009-11-19 | 2011-05-26 | Blue Medical Devices Bv | Narrow profile composition-releasing expandable medical balloon catheter |
WO2011005421A3 (en) * | 2009-07-10 | 2011-06-30 | Boston Scientific Scimed, Inc. | Use of nanocrystals for a drug delivery balloon |
US8101275B2 (en) | 2001-08-17 | 2012-01-24 | Celonova Biosciences, Inc. | Device based on nitinol, a process for its production, and its use |
JP2012514510A (en) * | 2009-01-09 | 2012-06-28 | インバテック テクノロジー センター ゲゼルシャフト ミット ベシュレンクテル ハフツング | Drug eluting medical device |
US8753709B2 (en) | 2004-03-22 | 2014-06-17 | Abbott Cardiovascular Systems Inc. | Methods of forming coatings with a crystalline or partially crystalline drug for implantable medical devices |
US8802184B2 (en) | 2007-05-30 | 2014-08-12 | Abbott Cardiovascular Systems Inc. | Medical devices containing biobeneficial particles |
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EP1810665B1 (en) | 2005-12-29 | 2015-03-04 | Cordis Corporation | Polymeric compositions comprising therapeutic agents in crystalline phases, and methods of forming the same |
AU2011256902B2 (en) * | 2005-07-15 | 2015-03-12 | Micell Technologies, Inc. | Polymer coatings containing drug powder of controlled morphology |
US9056152B2 (en) | 2011-08-25 | 2015-06-16 | Boston Scientific Scimed, Inc. | Medical device with crystalline drug coating |
US9080146B2 (en) | 2001-01-11 | 2015-07-14 | Celonova Biosciences, Inc. | Substrates containing polyphosphazene as matrices and substrates containing polyphosphazene with a micro-structured surface |
US20150196489A1 (en) * | 2013-12-18 | 2015-07-16 | Massachusetts Institute Of Technology | Polymer matrices for controlling crystallization |
WO2015181826A1 (en) | 2014-05-27 | 2015-12-03 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Crystalline coating and release of bioactive agents |
US9415142B2 (en) | 2006-04-26 | 2016-08-16 | Micell Technologies, Inc. | Coatings containing multiple drugs |
US9433516B2 (en) | 2007-04-17 | 2016-09-06 | Micell Technologies, Inc. | Stents having controlled elution |
US9486431B2 (en) | 2008-07-17 | 2016-11-08 | Micell Technologies, Inc. | Drug delivery medical device |
US9510856B2 (en) | 2008-07-17 | 2016-12-06 | Micell Technologies, Inc. | Drug delivery medical device |
JP2017500949A (en) * | 2013-09-10 | 2017-01-12 | リューベン,アレクサンダー | Vascular endoprosthesis coating |
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Also Published As
Publication number | Publication date |
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EP1135165A1 (en) | 2001-09-26 |
AU1821200A (en) | 2000-06-19 |
CA2353606A1 (en) | 2000-06-08 |
WO2000032238A9 (en) | 2000-12-07 |
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