WO2000002599A1 - Stent metallique biocompatible a revetement d'hydroxymethacrylate - Google Patents

Stent metallique biocompatible a revetement d'hydroxymethacrylate Download PDF

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Publication number
WO2000002599A1
WO2000002599A1 PCT/IL1999/000376 IL9900376W WO0002599A1 WO 2000002599 A1 WO2000002599 A1 WO 2000002599A1 IL 9900376 W IL9900376 W IL 9900376W WO 0002599 A1 WO0002599 A1 WO 0002599A1
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WO
WIPO (PCT)
Prior art keywords
poly
methacrylate
stent
polymerization
coating
Prior art date
Application number
PCT/IL1999/000376
Other languages
English (en)
Inventor
Itzhak Binderman
Original Assignee
Advanced Biocompatible Coatings Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Advanced Biocompatible Coatings Inc. filed Critical Advanced Biocompatible Coatings Inc.
Priority to AU46452/99A priority Critical patent/AU4645299A/en
Publication of WO2000002599A1 publication Critical patent/WO2000002599A1/fr

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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
    • A61L31/08—Materials for coatings
    • A61L31/10—Macromolecular materials

Definitions

  • the present invention relates to the application of a coating of a poly-hydroxymethacrylate derivative to improve the biocompatibility of metal stents intended for implantation or insertion. More specifically, the present invention relates to the coating of metallic stents with effective amounts of a coating of a poly-hydroxymethacrylate derivative which will drastically increase the thromboresistance of the stent, as well as prevent any significant deposit of protein, or the occurrence of mineral encrustation, and thereby achieve inhibition of restenosis.
  • the present invention is based on a different approach. Instead of coating the stent with polyurethane or any of the other polymers cited above, according to the present invention, a coating of a poly-hydroxy methacrylate derivative is applied to a metallic stent which results in a highly biocompatible and thromboresistant coating for said stents.
  • a hemo-compatible, restenosis-inhibiting metallic stent comprising a coating of a poly-hydroxy methacrylate derivative.
  • poly-hydroxy methacrylate derivative is intended to nclude hydroxy, alkoxy, and dihydroxy, i.e. glycol derivatives. More specifically, the present invention provides a hemo-compatible, restenosis-inhibiting metallic stent, comprising a coating of a poly-hydroxy methacrylate derivative selected from the group consisting of poly-hydroxyethylmethacrylate (PHEMA), poly (hydroxyethoxyethyl methacrylate) (PHEEMA), poly (hydroxydiethoxyethyl methacrylate) (PHDEEMA), poly (methoxyethyi methacrylate) (PMEMA), poly (methoxyethoxyethyl methacrylate) PMEEMA, poly (methoxydiethoxyethyl methacrylate) (PMDEEMA), poly (ethylene glycol dimethacrylate) (PEGDMA), and mixtures thereof.
  • PHEMA poly-hydroxyethylmethacrylate
  • PHEEMA poly (hydroxyethoxyethyl methacryl
  • a hydroxymethacrylate derivative selected from the group consisting of 2-hydroxyethyl-methacrylate; hydroxyethoxyethyl methacrylate, hydroxydiethoxyethyl methacrylate, methoxyethyi methacrylate, methoxyethoxyethyl methacrylate, methoxydiethoxyethyl methacrylate, ethylene glycol dimethacrylate and mixtures thereof;
  • polystyrene resin poly(hydroxyethoxyethyl methacrylate)
  • PHEEMA poly(hydroxyethoxyethyl methacrylate)
  • PHDEEMA poly(hydroxydiethoxyethyl methacrylate)
  • PMEMA poly (methoxyethyi methacrylate)
  • PMEEMA poly (methoxydiethoxyethyl methacrylate)
  • PEGDMA poly (ethylene glycol dimethacrylate)
  • the present invention also provides a process for producing hemo-compatible bioactive restenosis inhibiting metallic stents, comprising the steps of: a) coating a metallic stent with a liquid which contains poly-hydroxyethylmethacrylate in liquid form; b) cleaning the stent to extract any remaining residues; and c) drying the same.
  • the present invention does not aim at mimicking the cell-membrane directly. Rather, the aimed-for biocompatibility is achieved by applying a coating of a poly-hydroxymethacrylate to the metallic surface of a stent.
  • Current uses of 2-hydroxyethyl-methacrylate (hereinafter referred to as HEMA) or its polymer (hereinafter referred to as PHEMA) include adhesives, artificial nails, lacquers, cosmetic compositions, UV-inks and soft lens applications. Surfaces of plastic devices are modified with PHEMA. Furthermore, it is also used as an anti-adhesive to prevent cell attachment in cell cultures, and as an inducer of trabecular bone in dental implants. As such, its non-toxicity and usefulness in medical and biological applications is well-documented.
  • poly-HEMA is used as a biocompatigenic coating for metal stents.
  • This PHEMA coating renders the stents biocompatible by covering the metallic surface with a uniformly distributed layer of strongly polar and hence hydrophilic groups.
  • acrylic-type polymers which are poly-hydroxymethacrylate derivatives and which are similar in general structure to PHEMA:
  • poly (hydroxyethoxyethyl methacrylate) PHEEMA
  • poly (hydroxydiethoxyethyl methacrylate) PHDEEMA
  • poly (methoxyethyi methacrylate) PMEMA
  • poly (methoxyethoxyethyl methacrylate) PMEEMA poly (methoxydiethoxyethyl methacrylate) (PMDEEMA)
  • PEGDMA poly (ethylene glycol dimethacrylate)
  • the polymerization of the HEMA takes place directly on the metallic surface of the stent.
  • the HEMA is polymerized partly before it comes to the surface of the stent.
  • the polymers described in said patent include bioabsorbable polymers such as poly(lactic acid), poly(lactide-co-glycolide) and poly(hydroxbutyrate-co-valerate) and biostable polymers such as polyurethanes, silicones, polyesters, vinyl homopolymers and copolymers, acrylate homopolymers and copolymers, polyethers and cellulosics, however said patent does not teach or suggest the specific use of a coating of a polyhydroxymethacrylate derivative to a stent in the substantial absence of a therapeutic component in order to provide restenosis-inhibiting properties to said stent and the only acrylate polymer mentioned in said patent is an ethylene-methyl methacrylate copolymer, listed as one among tens of other named polymers.
  • bioabsorbable polymers such as poly(lactic acid), poly(lactide-co-glycolide) and poly(hydroxbutyrate-co-valerate)
  • PHEMA biocompatigenic nature of PHEMA.
  • PHEMA strongly hydrophilic nature of the outside layer of PHEMA attracts a dense water-coat, thus preventing blood-corpuscles to come into direct contact with the stent, an event that normally triggers the thrombogenic reaction (see, e.g., Binderman, I., et al., Grafts of HTR Polymer versus Kiel Bone in Experimental Long Bone Defects in Rats, ASTM, PA 19103).
  • polar PHEMA coating attracts the polar moiety on circulating phospholipids which then precipitate under the form of a lipid bilayer.
  • biocompatibility would again be a consequence of mimicking the thromboresistance of cell-membranes. If this latter hypothesis turns out to be correct, it underscores the possibility of self-assembly and hence self-repair of the very factor that induces biocompatibility. This is an extremely desirable property for a stent, especially in locations where there are considerable shear forces due to strong blood-circulation, such as heart and main arteries. In addition, PHEMA coated stents prevent adverse cell reaction of the injured site, cell growth, and restenosis.
  • the present invention enables the prevention or minimization of restenosis that is evident in some cases with the introduction of metallic stents, by providing hemo-compatible bioactive restenosis-inhibiting metallic stents.
  • HEMA 2-Hydroxyethyl methacrylate
  • PHEMA poly-HEMA
  • PHEMA 2-Hydroxyethyl methacrylate
  • PHEMA poly-HEMA
  • the stents can be made of stainless steel, Ti-based alloys, shape memory alloys or any other metal, eventually in combination with synthetic or biological materials.
  • the stents are coated with the hydrophilic HEMA-monomer, which is then polymerized by using dielectric heating, UV light, electron-beam radiation, gamma-radiation, ozone initiation, X-rays, lasers, visible light, thermal cure or any other means.
  • said polymerization can be initiated by at least one of photopolymerization, ionic-polymerization, and chemical-polymerization.
  • the stent After the polymerization procedure, the stent is placed in hot or boiling liquid, e.g. water to remove the remaining monomers.
  • hot or boiling liquid e.g. water
  • Such stents find applications in e.g. vascular, endo-esophageal and urological stents, as well as for coronary artery bypass surgery or the repair of aneurysms, etc. .
  • a stock solution is prepared by dissolving the 2-hydroxyethyl methacrylate (HEMA), formula C 6 H w 0 3 , CAS Number 868-77-9, in ethanol.
  • HEMA 2-hydroxyethyl methacrylate
  • Other possible solvents are dimethyl sulfoxide (DMSO), propanol, glycerol, ethylene glycol, cyclohexanol, toluene and dimethyl formamide (DMF). It is preferable to use the HEMA in an as pure as possible form, typically better than 98.4%.
  • Typical solutions are made by dissolving 120 mg HEMA in 1 ml 95% ethanol. The dissolving process is helped by shaking the solution and a storage at e.g. 37°C for 12 hrs.
  • a separation of undissolved material can be reached by centrifuging at e.g. 2500 rpm for 30 min. Further dilution with ethanol can be used to produce coatings of various thickness. Polymerization is lightly inhibited by trace amounts of an inhibitor such as the methyl ether of hydroquinone (MEHQ). MEHQ should be present in a concentration within the range of 150 to 300 ppm, preferably 200 ppm.
  • MEHQ methyl ether of hydroquinone
  • the HEMA can be modified by the addition of a cross linking agent such as triethyleneglycol dimethacrylate, which comprises between about 0.1 and 6% of the HEMA, preferably 5%. Alternatively, tetraethylenglycol dimethacrylate, diethyleneglycol dimethacrylate and monoethyleneglycol dimethacrylate can be used. A combination of these diesters can also be used.
  • the stents After wetting the stents with the described solution, they can be air dried in a e.g. sterile environment (sterile lamina flow hood), or when inhibitors are applied, the polymerization can take place by means of a dielectric furnace, UV light or controlled temperature chamber.
  • the heating provides sufficient free radical activity to overcome the effect of the inhibitor, resulting in polymerization of the coating.
  • the heating step is, e.g. about 1.5 minutes in duration in a dielectric furnace when the upper electrode is positioned about 5 mm above the stent.
  • the stent In order to remove any remaining HEMA monomer and/or traces of the inhibitor after the polymerization step, the stent is boiled in water for about 2 to 3 minutes after cooling down.
  • the stents can be dried at a slightly higher temperature.
  • 2-hydroxyethyl methacrylate can be applied directly to the stent or with the help of a primer such as silanes.
  • the surface modification by selective alkaline hydrolysis was studied. It was found that the thickness of the modified layer can be influenced by the reaction temperature, NaOH concentrations and reaction time.
  • the scope of the invention includes the coating with a poly-hydroxymethacrylate derivative of all metallic surfaces of stents of all types, as well for only metallic stents and for the coating of stents formed from the combination of metal with synthetic or biologic tissues.
  • a stock solution is prepared by dissolving 120 mg 2-hydroxyethyl methacrylate (HEMA), formula C 6 H 10 O 3 , CAS Number 868-77-9, in 1 ml 95% ethanol. It is preferable to use the HEMA in an as pure as possible form, typically better than 98.4%.
  • HEMA 2-hydroxyethyl methacrylate
  • the dissolving process is helped by shaking the solution for 1 hr. and storing at 37 °C for 12 hr.
  • Palmaz-Schatz stent and a Wiktor stent were used in this particular example. Other stents have been used in other tests.
  • the stents were thoroughly cleaned using laboratory detergents, and washed in warm water.
  • the stents were left to air dry in a sterile environment (sterile lamina flow hood).
  • the stents were then wetted with the solution by dipping them in the solution to the point where their entire surface was submerged in the liquid.
  • the stents were left to air dry in a sterile environment (sterile lamina flow hood).
  • Steps 8-10 were repeated 4 times in order to get the appropriate coating thickness.
  • the stents were moved to a UV light chamber and radiated for an additional 10 min. The stents were then placed in the chamber in a way that all sides of the stent were no more than 3 cm away from each lamp.
  • the stent was boiled in water for about 2 to 3 minutes after cooling down.
  • the stents were then placed on an angioplasty balloon and were inflated to 85% of their range.
  • the stents were weighed and examined under a scanning microscope to determine the uniformity of the coat and its attachment to the stent surface.
  • a stock solution was prepared by dissolving 120 mg poly-hydroxyethyl methacrylate (PHEMA) IN 1 ML 95% ethanol. It is preferable to use the PHEMA in an as pure as possible form, typically better than 98.4%.
  • PHEMA poly-hydroxyethyl methacrylate
  • Palmaz-Schatz stent and a Wiktor stent were used in this particular example. Other stents have been used in other tests.
  • the stents were thoroughly cleaned using laboratory detergents and washed in warm water.
  • the stents were left to air dry in a sterile environment (sterile lamina flow hood).
  • the stents were then wetted with the solution by dipping them in the solution to the point where their entire surface was submerged in the liquid. 8. Using a specially designed lever, the stents were lifted out of the solution at a rate of 1 mm/sec. This facilitated the uniformity of the coat.
  • the stents were left to air dry in a sterile environment (sterile lamina flow hood) for 15 min.
  • Steps 7-9 were repeated 4 times in order to obtain the appropriate coating thickness.
  • the stent was boiled in water for about 2 to 3 minutes.
  • the stents were then placed on an angioplasty balloon and were inflated to 85% of their range.
  • the stents were weighed and examined under a scanning microscope to determine the uniformity of the coat and its attachment to the stent surface.

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  • Health & Medical Sciences (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Surgery (AREA)
  • Vascular Medicine (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Materials For Medical Uses (AREA)

Abstract

L'invention concerne un stent métallique hémocompatible, inhibant la resténose, comprenant un revêtement de polyhydroxyméthacrylate sélectionné dans le groupe comprenant le polyhydroxyéthyl méthacrylate (PHEMA), le poly(hydroxyéthoxyéthyl méthycrylate) (PHEEMA), le poly(hydroxydiéthoxyéthyl méthacrylate) (PHDEEMA), le poly(méthoxyéthyl méthacrylate) (PMEMA), le poly(méthoxyéthoxyéthyl méthacrylate) (PMEEMA), le poly(méthoxydiéthoxyéthyl méthacrylate) (PMDEEMA), le poly(éthylèneglycol diméthacrylate) (PEGDMA), ainsi que des mélanges de ces composés.
PCT/IL1999/000376 1998-07-08 1999-07-08 Stent metallique biocompatible a revetement d'hydroxymethacrylate WO2000002599A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU46452/99A AU4645299A (en) 1998-07-08 1999-07-08 Biocompatible metallic stents with hydroxy methacrylate coating

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US11212598A 1998-07-08 1998-07-08
US09/112,125 1998-07-08

Publications (1)

Publication Number Publication Date
WO2000002599A1 true WO2000002599A1 (fr) 2000-01-20

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WO (1) WO2000002599A1 (fr)

Cited By (40)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002024249A2 (fr) * 2000-09-22 2002-03-28 Koole Levinas H Procede servant a immobiliser poly(hema) sur des extenseurs
US6503954B1 (en) 2000-03-31 2003-01-07 Advanced Cardiovascular Systems, Inc. Biocompatible carrier containing actinomycin D and a method of forming the same
US6540776B2 (en) 2000-12-28 2003-04-01 Advanced Cardiovascular Systems, Inc. Sheath for a prosthesis and methods of forming the same
WO2004009145A1 (fr) * 2002-07-19 2004-01-29 Advanced Cardiovascular Systems, Inc. Polymeres purifies pour revetements de dispositifs medicaux implantables
US6713119B2 (en) 1999-09-03 2004-03-30 Advanced Cardiovascular Systems, Inc. Biocompatible coating for a prosthesis and a method of forming the same
US6716444B1 (en) 2000-09-28 2004-04-06 Advanced Cardiovascular Systems, Inc. Barriers for polymer-coated implantable medical devices and methods for making the same
US6749626B1 (en) 2000-03-31 2004-06-15 Advanced Cardiovascular Systems, Inc. Actinomycin D for the treatment of vascular disease
US6753071B1 (en) 2001-09-27 2004-06-22 Advanced Cardiovascular Systems, Inc. Rate-reducing membrane for release of an agent
US6759054B2 (en) 1999-09-03 2004-07-06 Advanced Cardiovascular Systems, Inc. Ethylene vinyl alcohol composition and coating
US6790228B2 (en) 1999-12-23 2004-09-14 Advanced Cardiovascular Systems, Inc. Coating for implantable devices and a method of forming the same
US6818247B1 (en) 2000-03-31 2004-11-16 Advanced Cardiovascular Systems, Inc. Ethylene vinyl alcohol-dimethyl acetamide composition and a method of coating a stent
US6908624B2 (en) 1999-12-23 2005-06-21 Advanced Cardiovascular Systems, Inc. Coating for implantable devices and a method of forming the same
US7022372B1 (en) 2002-11-12 2006-04-04 Advanced Cardiovascular Systems, Inc. Compositions for coating implantable medical devices
EP1748806A1 (fr) * 2004-03-31 2007-02-07 Advanced Cardiovascular Systems, Inc. Compositions de polyacrylate biocompatibles pour applications medicales
WO2006102418A3 (fr) * 2005-03-24 2007-04-19 Advanced Cardiovascular System Dispositifs implantables constitues de polymeres de methacrylate ou d'acrylate non salissants
US7504125B1 (en) 2001-04-27 2009-03-17 Advanced Cardiovascular Systems, Inc. System and method for coating implantable devices
US7651695B2 (en) 2001-05-18 2010-01-26 Advanced Cardiovascular Systems, Inc. Medicated stents for the treatment of vascular disease
US7732535B2 (en) 2002-09-05 2010-06-08 Advanced Cardiovascular Systems, Inc. Coating for controlled release of drugs from implantable medical devices
US8211489B2 (en) 2007-12-19 2012-07-03 Abbott Cardiovascular Systems, Inc. Methods for applying an application material to an implantable device
US8361538B2 (en) 2007-12-19 2013-01-29 Abbott Laboratories Methods for applying an application material to an implantable device
US8689729B2 (en) 2003-05-15 2014-04-08 Abbott Cardiovascular Systems Inc. Apparatus for coating stents
EP2720039A1 (fr) * 2011-06-13 2014-04-16 Hitachi Chemical Company, Ltd. Agent pour l'amélioration de l'adhésivité de cellules cancéreuses
US8871883B2 (en) 2002-12-11 2014-10-28 Abbott Cardiovascular Systems Inc. Biocompatible coating for implantable medical devices
US8961588B2 (en) 2002-03-27 2015-02-24 Advanced Cardiovascular Systems, Inc. Method of coating a stent with a release polymer for 40-O-(2-hydroxy)ethyl-rapamycin
US9028859B2 (en) 2006-07-07 2015-05-12 Advanced Cardiovascular Systems, Inc. Phase-separated block copolymer coatings for implantable medical devices
US9056155B1 (en) 2007-05-29 2015-06-16 Abbott Cardiovascular Systems Inc. Coatings having an elastic primer layer
US9067000B2 (en) 2004-10-27 2015-06-30 Abbott Cardiovascular Systems Inc. End-capped poly(ester amide) copolymers
US9084671B2 (en) 2002-06-21 2015-07-21 Advanced Cardiovascular Systems, Inc. Methods of forming a micronized peptide coated stent
US9101697B2 (en) 2004-04-30 2015-08-11 Abbott Cardiovascular Systems Inc. Hyaluronic acid based copolymers
US9114198B2 (en) 2003-11-19 2015-08-25 Advanced Cardiovascular Systems, Inc. Biologically beneficial coatings for implantable devices containing fluorinated polymers and methods for fabricating the same
USRE45744E1 (en) 2003-12-01 2015-10-13 Abbott Cardiovascular Systems Inc. Temperature controlled crimping
US9175162B2 (en) 2003-05-08 2015-11-03 Advanced Cardiovascular Systems, Inc. Methods for forming stent coatings comprising hydrophilic additives
US9339592B2 (en) 2004-12-22 2016-05-17 Abbott Cardiovascular Systems Inc. Polymers of fluorinated monomers and hydrocarbon monomers
US9364498B2 (en) 2004-06-18 2016-06-14 Abbott Cardiovascular Systems Inc. Heparin prodrugs and drug delivery stents formed therefrom
US9381279B2 (en) 2005-03-24 2016-07-05 Abbott Cardiovascular Systems Inc. Implantable devices formed on non-fouling methacrylate or acrylate polymers
US9561309B2 (en) 2004-05-27 2017-02-07 Advanced Cardiovascular Systems, Inc. Antifouling heparin coatings
US9561351B2 (en) 2006-05-31 2017-02-07 Advanced Cardiovascular Systems, Inc. Drug delivery spiral coil construct
US9580558B2 (en) 2004-07-30 2017-02-28 Abbott Cardiovascular Systems Inc. Polymers containing siloxane monomers
US10064982B2 (en) 2001-06-27 2018-09-04 Abbott Cardiovascular Systems Inc. PDLLA stent coating
US10076591B2 (en) 2010-03-31 2018-09-18 Abbott Cardiovascular Systems Inc. Absorbable coating for implantable device

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Publication number Priority date Publication date Assignee Title
EP0574880A1 (fr) * 1992-06-15 1993-12-22 United States Surgical Corporation Procédé de traitement d'une matière d'implantation bioabsorbable
WO1996025897A2 (fr) * 1995-02-22 1996-08-29 Menlo Care, Inc. Prothese endovasculaire a treillis dilatable revetu
CA2226129A1 (fr) * 1997-01-03 1998-07-03 Huls Aktiengesellschaft Polymeres ayant des proprietes bacteriophobes et, facultativement, d'inhibition de la proliferation cellulaire

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0574880A1 (fr) * 1992-06-15 1993-12-22 United States Surgical Corporation Procédé de traitement d'une matière d'implantation bioabsorbable
WO1996025897A2 (fr) * 1995-02-22 1996-08-29 Menlo Care, Inc. Prothese endovasculaire a treillis dilatable revetu
CA2226129A1 (fr) * 1997-01-03 1998-07-03 Huls Aktiengesellschaft Polymeres ayant des proprietes bacteriophobes et, facultativement, d'inhibition de la proliferation cellulaire

Cited By (51)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6713119B2 (en) 1999-09-03 2004-03-30 Advanced Cardiovascular Systems, Inc. Biocompatible coating for a prosthesis and a method of forming the same
US6759054B2 (en) 1999-09-03 2004-07-06 Advanced Cardiovascular Systems, Inc. Ethylene vinyl alcohol composition and coating
US6908624B2 (en) 1999-12-23 2005-06-21 Advanced Cardiovascular Systems, Inc. Coating for implantable devices and a method of forming the same
US6790228B2 (en) 1999-12-23 2004-09-14 Advanced Cardiovascular Systems, Inc. Coating for implantable devices and a method of forming the same
US6818247B1 (en) 2000-03-31 2004-11-16 Advanced Cardiovascular Systems, Inc. Ethylene vinyl alcohol-dimethyl acetamide composition and a method of coating a stent
US6503954B1 (en) 2000-03-31 2003-01-07 Advanced Cardiovascular Systems, Inc. Biocompatible carrier containing actinomycin D and a method of forming the same
US6749626B1 (en) 2000-03-31 2004-06-15 Advanced Cardiovascular Systems, Inc. Actinomycin D for the treatment of vascular disease
WO2002024249A3 (fr) * 2000-09-22 2002-08-01 Levinas H Koole Procede servant a immobiliser poly(hema) sur des extenseurs
WO2002024249A2 (fr) * 2000-09-22 2002-03-28 Koole Levinas H Procede servant a immobiliser poly(hema) sur des extenseurs
US6716444B1 (en) 2000-09-28 2004-04-06 Advanced Cardiovascular Systems, Inc. Barriers for polymer-coated implantable medical devices and methods for making the same
US6540776B2 (en) 2000-12-28 2003-04-01 Advanced Cardiovascular Systems, Inc. Sheath for a prosthesis and methods of forming the same
US8007858B2 (en) 2001-04-27 2011-08-30 Advanced Cardiovascular Systems, Inc. System and method for coating implantable devices
US7504125B1 (en) 2001-04-27 2009-03-17 Advanced Cardiovascular Systems, Inc. System and method for coating implantable devices
US7651695B2 (en) 2001-05-18 2010-01-26 Advanced Cardiovascular Systems, Inc. Medicated stents for the treatment of vascular disease
US10064982B2 (en) 2001-06-27 2018-09-04 Abbott Cardiovascular Systems Inc. PDLLA stent coating
US6753071B1 (en) 2001-09-27 2004-06-22 Advanced Cardiovascular Systems, Inc. Rate-reducing membrane for release of an agent
US8961588B2 (en) 2002-03-27 2015-02-24 Advanced Cardiovascular Systems, Inc. Method of coating a stent with a release polymer for 40-O-(2-hydroxy)ethyl-rapamycin
US9084671B2 (en) 2002-06-21 2015-07-21 Advanced Cardiovascular Systems, Inc. Methods of forming a micronized peptide coated stent
US7491233B1 (en) * 2002-07-19 2009-02-17 Advanced Cardiovascular Systems Inc. Purified polymers for coatings of implantable medical devices
JP2005533556A (ja) * 2002-07-19 2005-11-10 アドヴァンスド カーディオヴァスキュラー システムズ， インコーポレイテッド 植え込み可能な医療器具の被覆のための精製されたポリマー
WO2004009145A1 (fr) * 2002-07-19 2004-01-29 Advanced Cardiovascular Systems, Inc. Polymeres purifies pour revetements de dispositifs medicaux implantables
US7732535B2 (en) 2002-09-05 2010-06-08 Advanced Cardiovascular Systems, Inc. Coating for controlled release of drugs from implantable medical devices
US7022372B1 (en) 2002-11-12 2006-04-04 Advanced Cardiovascular Systems, Inc. Compositions for coating implantable medical devices
US8871236B2 (en) 2002-12-11 2014-10-28 Abbott Cardiovascular Systems Inc. Biocompatible polyacrylate compositions for medical applications
US8871883B2 (en) 2002-12-11 2014-10-28 Abbott Cardiovascular Systems Inc. Biocompatible coating for implantable medical devices
US8986726B2 (en) 2002-12-11 2015-03-24 Abbott Cardiovascular Systems Inc. Biocompatible polyacrylate compositions for medical applications
US9175162B2 (en) 2003-05-08 2015-11-03 Advanced Cardiovascular Systems, Inc. Methods for forming stent coatings comprising hydrophilic additives
US8689729B2 (en) 2003-05-15 2014-04-08 Abbott Cardiovascular Systems Inc. Apparatus for coating stents
US9114198B2 (en) 2003-11-19 2015-08-25 Advanced Cardiovascular Systems, Inc. Biologically beneficial coatings for implantable devices containing fluorinated polymers and methods for fabricating the same
USRE45744E1 (en) 2003-12-01 2015-10-13 Abbott Cardiovascular Systems Inc. Temperature controlled crimping
EP1748806A1 (fr) * 2004-03-31 2007-02-07 Advanced Cardiovascular Systems, Inc. Compositions de polyacrylate biocompatibles pour applications medicales
EP1748806B1 (fr) * 2004-03-31 2017-04-19 Abbott Cardiovascular Systems Inc. Compositions de polyacrylate biocompatibles pour applications médicales
US9101697B2 (en) 2004-04-30 2015-08-11 Abbott Cardiovascular Systems Inc. Hyaluronic acid based copolymers
US9561309B2 (en) 2004-05-27 2017-02-07 Advanced Cardiovascular Systems, Inc. Antifouling heparin coatings
US9375445B2 (en) 2004-06-18 2016-06-28 Abbott Cardiovascular Systems Inc. Heparin prodrugs and drug delivery stents formed therefrom
US9364498B2 (en) 2004-06-18 2016-06-14 Abbott Cardiovascular Systems Inc. Heparin prodrugs and drug delivery stents formed therefrom
US9580558B2 (en) 2004-07-30 2017-02-28 Abbott Cardiovascular Systems Inc. Polymers containing siloxane monomers
US9067000B2 (en) 2004-10-27 2015-06-30 Abbott Cardiovascular Systems Inc. End-capped poly(ester amide) copolymers
US9339592B2 (en) 2004-12-22 2016-05-17 Abbott Cardiovascular Systems Inc. Polymers of fluorinated monomers and hydrocarbon monomers
WO2006102418A3 (fr) * 2005-03-24 2007-04-19 Advanced Cardiovascular System Dispositifs implantables constitues de polymeres de methacrylate ou d'acrylate non salissants
US9381279B2 (en) 2005-03-24 2016-07-05 Abbott Cardiovascular Systems Inc. Implantable devices formed on non-fouling methacrylate or acrylate polymers
US8932615B2 (en) 2005-03-24 2015-01-13 Abbott Cardiovascular Systems Inc. Implantable devices formed on non-fouling methacrylate or acrylate polymers
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