WO1999016416A2 - Implants medicaux revetus, leur procede de preparation et leur utilisation pour la prevention de restenoses - Google Patents

Implants medicaux revetus, leur procede de preparation et leur utilisation pour la prevention de restenoses Download PDF

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Publication number
WO1999016416A2
WO1999016416A2 PCT/EP1998/006019 EP9806019W WO9916416A2 WO 1999016416 A2 WO1999016416 A2 WO 1999016416A2 EP 9806019 W EP9806019 W EP 9806019W WO 9916416 A2 WO9916416 A2 WO 9916416A2
Authority
WO
WIPO (PCT)
Prior art keywords
polymer
medical implants
stent
epothilone
active ingredient
Prior art date
Application number
PCT/EP1998/006019
Other languages
German (de)
English (en)
Other versions
WO1999016416A3 (fr
Inventor
Werner Krause
Original Assignee
Schering Ag
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 Schering Ag filed Critical Schering Ag
Priority to EP98952617A priority Critical patent/EP1024842A2/fr
Priority to AU10251/99A priority patent/AU1025199A/en
Priority to JP2000513554A priority patent/JP2001517543A/ja
Publication of WO1999016416A2 publication Critical patent/WO1999016416A2/fr
Publication of WO1999016416A3 publication Critical patent/WO1999016416A3/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C09D175/08—Polyurethanes from polyethers
    • 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
    • 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
    • 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

Definitions

  • the invention relates to agents for the production of coated, drug-delivering medical implants, e.g. Stents, the implants prepared in this way, processes for their preparation and their use for restenosis prophylaxis.
  • coated, drug-delivering medical implants e.g. Stents
  • Implants especially stents, are state of the art (Pschyrembel, clinical dictionary 257th edition, publisher W. de Gruyter). Stents are self-expanding endoprostheses that keep the gait open
  • Enable structures in human or animal bodies e.g. vascular, esophageal, tracheal, bile duct stent. They are used as a palliative measure for narrowing due to occlusion (eg atherosclerosis) or external pressure (eg for tumors).
  • Radioactive stents are used, for example, after vascular surgery or interventional radiological interventions (eg balloon angioplasty) for prophylaxis of restenosis.
  • a stent is known from international patent application WO 94/13268, which gradually releases an active substance in the body.
  • a polymer composition is known from US Pat. No. 5,599,552 which can gel in the body. In solid form, it represents an implant that can gradually release an active ingredient.
  • the object of the present invention is therefore to provide medical implants which are better tolerated than conventional medical implants.
  • the surface of the medical implants is coated with a polymer into which at least one active ingredient based on the epothilone base, e.g. Epothilon A or B or a derivative of epothilone, as well as possibly other active substances, e.g. thrombosis-preventing substances and / or estrogens and / or corticosteroids are incorporated.
  • Epothilone and its synthesis are known from the literature (Höfle et al., Angew. Chem. 108: 1 671 -3 (1 996), Schinzer et al., Angew. Chem. 1 09: 543-4 (1997)).
  • the active substance epothilone can also be applied directly to the medical implant without a polymer.
  • the device according to the invention thus consists of the medical implant, possibly of a polymer on the surface of the implant and at least one active ingredient from the class of the epothilones.
  • the invention also relates to devices, substances, solutions and containers for the coating of implants according to the invention, for example in the form of a kit. Such kits can be used by the physician on site for the coating of selected implants.
  • the commercially available implants can be used as the base body, for the stents e.g. a Wiktor stent, a Strecker stent or a Palmaz-Schatz stent.
  • suitable polymers are polyurethanes, polylactides, mixed polylactide glycolides or other polymers described in the literature.
  • the implants according to the invention - described with the aid of stents - can be produced by way of example as follows:
  • An uncoated stent is first coated with a polymer (e.g. a polyurethane, obtainable from the reaction of an amphiphilic polyether, diphenyimethane-4-4'-diisocyanate and butanediol).
  • a polymer e.g. a polyurethane, obtainable from the reaction of an amphiphilic polyether, diphenyimethane-4-4'-diisocyanate and butanediol.
  • a solvent e.g. chloroform
  • Active ingredient epothilone
  • the same solvent for example chloroform or ethyl acetate
  • Another active ingredient can be applied to epothilone derivative.
  • active ingredients are antithrombotic drugs, e.g. Iloprost, estrogens such as ethinyl estradiol or corticoids such as Dexamethasone, Fluocortolon, Difluorcortolon or their esters.
  • An uncoated stent can first be coated with a polymer (e.g. a polyurethane, obtainable from the reaction of an amphiphilic polyether, diphenylmethane-4-4'-diisocyanate and butanediol). This polymer is modified so that it is on the surface
  • Cyclodextrin carries.
  • the polymer is dissolved in a solvent (e.g. chloroform) and the stent is immersed in the polymer solution. After the stent has been removed from the polymer solution, it is dried in a drying chamber at room temperature.
  • the "activation" of the stent now takes place by immersing the modified stent in an aqueous solution of epothilone. The active ingredient is incorporated into the cyclodextrin. The stent is now ready for use.
  • the implants according to the invention achieve the task described in the introduction.
  • the implants according to the invention are physiologically well tolerated.
  • the particular advantage of the implants according to the invention is that the physician can select a stent according to his needs on site and then activate the selected stent by the described method.
  • the few substances and solutions required for this can be delivered prepared accordingly, so that the corresponding medical practitioner only has to immerse the uncoated stent in the given order in the individual solutions.
  • the invention thus also relates to those substances, solutions and preparations (kits) and containers prepared for the method according to the invention.
  • the polymer used is polyurethane, which can be obtained as a chain extender by reacting an amphiphilic polyether, diphenylmethane-4,4'-diisocyanate and butanediol.
  • the stents are coated by immersing them in a 5% chloroform solution of the polymer. Then they are allowed to dry in a clean room drying chamber at room temperature. The average layer thickness is 20 ⁇ m.
  • Epothilon A is coated by immersing the polymer-coated stent in an aqueous solution of Epothilon A (0.5 mg / ml). After drying, the stent is ready for use.
  • the coating of the stent with the polymer and the subsequent coating with epothilone A is carried out as described in Example 1. However, the stent is now alternately immersed in a solution with the polymer and - after drying - in an aqueous solution of Epothilon A. This creates a multi-layer structure. The amount of active ingredient incorporated can be controlled via the number of epothilone-containing layers. The stent is implanted after the last drying cycle.
  • the coating is carried out as described in Example 2. However, the stent is now alternately immersed in a solution with the polymer and - each after drying - in an aqueous solution of epothilone A or lloprost or a solution of an estrogen derivative or corticoid in chloroform.
  • the order of the coating materials can be varied. This creates a multi-layer structure. The amount of active ingredient incorporated can be controlled via the number of the respective layers.
  • the stent is implanted after the last drying cycle.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Surgery (AREA)
  • Vascular Medicine (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Biomedical Technology (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Materials For Medical Uses (AREA)
  • Media Introduction/Drainage Providing Device (AREA)

Abstract

L'invention concerne des agents pour la préparation d'implants médicaux revêtus libérant des principes actifs, par exemple des extenseurs, les implants ainsi préparés, leur procédé de préparation et leur utilisation pour la prévention de resténoses.
PCT/EP1998/006019 1997-09-29 1998-09-24 Implants medicaux revetus, leur procede de preparation et leur utilisation pour la prevention de restenoses WO1999016416A2 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP98952617A EP1024842A2 (fr) 1997-09-29 1998-09-24 Implants medicaux revetus, leur procede de preparation et leur utilisation pour la prevention de restenoses
AU10251/99A AU1025199A (en) 1997-09-29 1998-09-24 Coated medical implants, method for producing them, and use of the same for preventing restenosis
JP2000513554A JP2001517543A (ja) 1997-09-29 1998-09-24 被覆医療用インプラント、その製造方法及びその再狭窄予防のための使用

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19744135A DE19744135C1 (de) 1997-09-29 1997-09-29 Beschichtete medizinische Implantate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Restenoseprophylaxe
DE19744135.1 1997-09-29

Publications (2)

Publication Number Publication Date
WO1999016416A2 true WO1999016416A2 (fr) 1999-04-08
WO1999016416A3 WO1999016416A3 (fr) 1999-08-05

Family

ID=7844759

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1998/006019 WO1999016416A2 (fr) 1997-09-29 1998-09-24 Implants medicaux revetus, leur procede de preparation et leur utilisation pour la prevention de restenoses

Country Status (5)

Country Link
EP (1) EP1024842A2 (fr)
JP (1) JP2001517543A (fr)
AU (1) AU1025199A (fr)
DE (1) DE19744135C1 (fr)
WO (1) WO1999016416A2 (fr)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003078411A1 (fr) 2002-03-12 2003-09-25 Bristol-Myers Squibb Company Derives de c3-cyano epothilone
WO2004052361A1 (fr) * 2002-12-09 2004-06-24 Novartis Ag Stabilisateurs de microtubules utilises dans le traitement de la stenose dans des stents
EP1741715A1 (fr) 1998-06-22 2007-01-10 Novartis AG Dérivés de l'epothilone, leur synthèse et leur utilisation
US7265199B2 (en) 2000-04-11 2007-09-04 Celonova Biosciences Germany Gmbh Poly-tri-fluoro-ethoxypolyphosphazene coverings and films
US7922764B2 (en) 2006-10-10 2011-04-12 Celonova Bioscience, Inc. Bioprosthetic heart valve with polyphosphazene
US7932031B2 (en) 2004-11-30 2011-04-26 Bristol-Myers Squibb Company Methods for determining sensitivity to microtubule-stabilizing agents comprising ixabepilone by measuring the level of estrogen receptor 1
US8007821B2 (en) 2001-01-11 2011-08-30 Celonova Biosciences Germany Gmbh Substrates containing polyphosphazene as matrices and substrates containing polyphosphazene with microstructured surface
US8101275B2 (en) 2001-08-17 2012-01-24 Celonova Biosciences, Inc. Device based on nitinol, a process for its production, and its use
US8318235B2 (en) 2003-01-22 2012-11-27 Cordis Corporation Method for applying drug coating to a medical device in surgeon room
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
US9107850B2 (en) 2004-10-25 2015-08-18 Celonova Biosciences, Inc. Color-coded and sized loadable polymeric particles for therapeutic and/or diagnostic applications and methods of preparing and using the same
US9114162B2 (en) 2004-10-25 2015-08-25 Celonova Biosciences, Inc. Loadable polymeric particles for enhanced imaging in clinical applications and methods of preparing and using the same
US10973770B2 (en) 2004-10-25 2021-04-13 Varian Medical Systems, Inc. Color-coded and sized loadable polymeric particles for therapeutic and/or diagnostic applications and methods of preparing and using the same

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE69734362T2 (de) 1996-12-03 2006-07-20 Sloan-Kettering Institute For Cancer Research Synthese von epothilonen, zwischenprodukte dazu, analoga und verwendungen davon
EP1180013B1 (fr) 1999-05-27 2006-03-08 Biocompatibles UK Limited Administration de medicament localisee
EP1179353A1 (fr) * 2000-08-11 2002-02-13 B. Braun Melsungen Ag Implants antithrombotiques avec un revêtement de polyphosphazène et d'un agent actif
DE10107795B4 (de) * 2001-02-13 2014-05-15 Berlex Ag Gefäßstütze mit einem Grundkörper, Verfahren zur Herstellung der Gefäßstütze, Vorrichtung zur Beschichtung der Gefäßstütze
KR100994543B1 (ko) * 2001-02-16 2010-11-16 아스텔라스세이야쿠 가부시키가이샤 Ｆｋ506을 포함하는 이식편
EP1270026A1 (fr) * 2001-06-22 2003-01-02 Erik Andersen Stents comprenant des analogues de vitamine D pour éviter les resténoses
DE10142881A1 (de) * 2001-09-03 2003-04-03 Jomed Gmbh Implantate mit Combretastatin A-4 (CA4)
DE10231336A1 (de) * 2002-07-11 2004-01-22 Bayer Ag Stents
US7649006B2 (en) 2002-08-23 2010-01-19 Sloan-Kettering Institute For Cancer Research Synthesis of epothilones, intermediates thereto and analogues thereof
ES2281692T3 (es) 2002-08-23 2007-10-01 Sloan-Kettering Institute For Cancer Research Sintesis de epotilones, sus intermediarios, sus analogos y sus usos.
US20050038504A1 (en) * 2003-01-22 2005-02-17 Harry Halleriet Kit for applying drug coating to a medical device in surgeon room
EP2065054A1 (fr) * 2007-11-29 2009-06-03 Bayer Schering Pharma Aktiengesellschaft Combinaisons comprenant une prostaglandine et leurs utilisations

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WO1997033552A1 (fr) * 1996-03-12 1997-09-18 Pg-Txl Company, L.P. Bioprecurseurs de paclitaxel solubles dans l'eau
WO1997045105A1 (fr) * 1996-05-24 1997-12-04 Angiotech Pharmaceuticals, Inc. Compositions et methodes pour traiter ou prevenir des maladies des voies corporelles
US5716981A (en) * 1993-07-19 1998-02-10 Angiogenesis Technologies, Inc. Anti-angiogenic compositions and methods of use

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US4846844A (en) * 1987-08-31 1989-07-11 Eli Lilly And Company Antimicrobial coated implants
GB2266892B (en) * 1991-10-01 1996-04-17 Otsuka Pharma Co Ltd Antithrombotic resin, antithrombotic tube, antithrombotic film and antithrombotic coat
US5599352A (en) * 1992-03-19 1997-02-04 Medtronic, Inc. Method of making a drug eluting stent
US5342348A (en) * 1992-12-04 1994-08-30 Kaplan Aaron V Method and device for treating and enlarging body lumens
NZ533467A (en) * 1993-07-19 2006-02-24 Angiotech Pharm Inc Anti-angiogenic compositions and methods of use
DE4334272C2 (de) * 1993-10-07 1996-07-18 Stemberger Axel Dr Beschichtung für Biomaterial und seine Verwendung

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5716981A (en) * 1993-07-19 1998-02-10 Angiogenesis Technologies, Inc. Anti-angiogenic compositions and methods of use
WO1997033552A1 (fr) * 1996-03-12 1997-09-18 Pg-Txl Company, L.P. Bioprecurseurs de paclitaxel solubles dans l'eau
WO1997045105A1 (fr) * 1996-05-24 1997-12-04 Angiotech Pharmaceuticals, Inc. Compositions et methodes pour traiter ou prevenir des maladies des voies corporelles

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1741715A1 (fr) 1998-06-22 2007-01-10 Novartis AG Dérivés de l'epothilone, leur synthèse et leur utilisation
US7265199B2 (en) 2000-04-11 2007-09-04 Celonova Biosciences Germany Gmbh Poly-tri-fluoro-ethoxypolyphosphazene coverings and films
US8007821B2 (en) 2001-01-11 2011-08-30 Celonova Biosciences Germany Gmbh Substrates containing polyphosphazene as matrices and substrates containing polyphosphazene with microstructured surface
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
US8101275B2 (en) 2001-08-17 2012-01-24 Celonova Biosciences, Inc. Device based on nitinol, a process for its production, and its use
WO2003078411A1 (fr) 2002-03-12 2003-09-25 Bristol-Myers Squibb Company Derives de c3-cyano epothilone
WO2004052361A1 (fr) * 2002-12-09 2004-06-24 Novartis Ag Stabilisateurs de microtubules utilises dans le traitement de la stenose dans des stents
US8318235B2 (en) 2003-01-22 2012-11-27 Cordis Corporation Method for applying drug coating to a medical device in surgeon room
US9107850B2 (en) 2004-10-25 2015-08-18 Celonova Biosciences, Inc. Color-coded and sized loadable polymeric particles for therapeutic and/or diagnostic applications and methods of preparing and using the same
US9114162B2 (en) 2004-10-25 2015-08-25 Celonova Biosciences, Inc. Loadable polymeric particles for enhanced imaging in clinical applications and methods of preparing and using the same
US9597419B2 (en) 2004-10-25 2017-03-21 Boston Scientific Limited Loadable polymeric particles for enhanced imaging in clinical applications and methods of preparing and using the same
US10973770B2 (en) 2004-10-25 2021-04-13 Varian Medical Systems, Inc. Color-coded and sized loadable polymeric particles for therapeutic and/or diagnostic applications and methods of preparing and using the same
US7932031B2 (en) 2004-11-30 2011-04-26 Bristol-Myers Squibb Company Methods for determining sensitivity to microtubule-stabilizing agents comprising ixabepilone by measuring the level of estrogen receptor 1
US7922764B2 (en) 2006-10-10 2011-04-12 Celonova Bioscience, Inc. Bioprosthetic heart valve with polyphosphazene

Also Published As

Publication number Publication date
AU1025199A (en) 1999-04-23
JP2001517543A (ja) 2001-10-09
WO1999016416A3 (fr) 1999-08-05
DE19744135C1 (de) 1999-03-25
EP1024842A2 (fr) 2000-08-09

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