WO1999016416A2 - Coated medical implants, method for producing them, and use of the same for preventing restenosis - Google Patents
Coated medical implants, method for producing them, and use of the same for preventing restenosis Download PDFInfo
- 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
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)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Materials Engineering (AREA)
- Biomedical Technology (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Materials For Medical Uses (AREA)
- Media Introduction/Drainage Providing Device (AREA)
Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2000513554A JP2001517543A (en) | 1997-09-29 | 1998-09-24 | Coated medical implant, method for manufacturing the same and use thereof for preventing restenosis |
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 |
EP98952617A EP1024842A2 (en) | 1997-09-29 | 1998-09-24 | Coated medical implants, method for producing them, and use of the same for preventing restenosis |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19744135.1 | 1997-09-29 | ||
DE19744135A DE19744135C1 (en) | 1997-09-29 | 1997-09-29 | Medical implants coated with epothilone |
Publications (2)
Publication Number | Publication Date |
---|---|
WO1999016416A2 true WO1999016416A2 (en) | 1999-04-08 |
WO1999016416A3 WO1999016416A3 (en) | 1999-08-05 |
Family
ID=7844759
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1998/006019 WO1999016416A2 (en) | 1997-09-29 | 1998-09-24 | Coated medical implants, method for producing them, and use of the same for preventing restenosis |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP1024842A2 (en) |
JP (1) | JP2001517543A (en) |
AU (1) | AU1025199A (en) |
DE (1) | DE19744135C1 (en) |
WO (1) | WO1999016416A2 (en) |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003078411A1 (en) | 2002-03-12 | 2003-09-25 | Bristol-Myers Squibb Company | C3-cyano epothilone derivatives |
WO2004052361A1 (en) * | 2002-12-09 | 2004-06-24 | Novartis Ag | Microtubule stabilisers for treating stenosis in stents |
EP1741715A1 (en) | 1998-06-22 | 2007-01-10 | Novartis AG | Epothilone derivatives and their synthesis and use |
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)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4579351B2 (en) | 1996-12-03 | 2010-11-10 | スローン−ケッタリング インスティトュート フォア キャンサー リサーチ | Synthesis of epothilone and its intermediates and analogs and uses thereof |
EP1180013B1 (en) | 1999-05-27 | 2006-03-08 | Biocompatibles UK Limited | Local drug delivery |
EP1179353A1 (en) * | 2000-08-11 | 2002-02-13 | B. Braun Melsungen Ag | Antithrombogenic implants with coating of polyphosphazenes and a pharmacologically active agent |
DE10107795B4 (en) * | 2001-02-13 | 2014-05-15 | Berlex Ag | Vascular support with a basic body, method for producing the vascular support, apparatus for coating the vascular support |
DE50210591D1 (en) | 2001-02-16 | 2007-09-13 | Abbott Lab Vascular Entpr Ltd | IMPLANTS WITH FK506 FOR RESTENOSIS TREATMENT AND PROPHYLAXIS |
EP1270026A1 (en) * | 2001-06-22 | 2003-01-02 | Erik Andersen | Stents comprising vitamin D analogues for restenosis inhibition |
DE10142881A1 (en) * | 2001-09-03 | 2003-04-03 | Jomed Gmbh | Implant containing combretastatin A-4, useful for inhibiting growth of muscle cells, particularly prevention of restenosis, especially a stent or stent-graft |
DE10231336A1 (en) * | 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 |
EP1506203B1 (en) | 2002-08-23 | 2007-01-03 | Sloan-Kettering Institute For Cancer Research | Synthesis of epothilones, intermediates thereto, analogues and uses thereof |
US20050038504A1 (en) * | 2003-01-22 | 2005-02-17 | Harry Halleriet | Kit for applying drug coating to a medical device in surgeon room |
EP2065054A1 (en) * | 2007-11-29 | 2009-06-03 | Bayer Schering Pharma Aktiengesellschaft | Combinations comprising a prostaglandin and uses thereof |
Citations (3)
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WO1997033552A1 (en) * | 1996-03-12 | 1997-09-18 | Pg-Txl Company, L.P. | Water soluble paclitaxel prodrugs |
WO1997045105A1 (en) * | 1996-05-24 | 1997-12-04 | Angiotech Pharmaceuticals, Inc. | Compositions and methods for treating or preventing diseases of body passageways |
US5716981A (en) * | 1993-07-19 | 1998-02-10 | Angiogenesis Technologies, Inc. | Anti-angiogenic compositions and methods of use |
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DE3524451A1 (en) * | 1985-07-09 | 1987-03-12 | Behringwerke Ag | Article for use in immunoassay coated with polymer |
US4758435A (en) * | 1986-08-11 | 1988-07-19 | American Cyanamid Company | Estradiol implant composition and method for preparation |
ATE86484T1 (en) * | 1987-08-08 | 1993-03-15 | Akzo Nv | CONTRACEPTIVE IMPLANT. |
US4846844A (en) * | 1987-08-31 | 1989-07-11 | Eli Lilly And Company | Antimicrobial coated implants |
CH683673A5 (en) * | 1991-10-01 | 1994-04-29 | Otsuka Pharma Co Ltd | Antithrombotic resin antithrombotic tubes, antithrombotic film and antithrombotic coating. |
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 |
KR101222904B1 (en) * | 1993-07-19 | 2013-01-17 | 안지오테크 파마슈티칼즈, 인코포레이티드 | Anti-angiogenic compositions, a stent coated with the anti-angiogenic compositions and a method for manufacturing the stent |
DE4334272C2 (en) * | 1993-10-07 | 1996-07-18 | Stemberger Axel Dr | Coating for biomaterial and its use |
-
1997
- 1997-09-29 DE DE19744135A patent/DE19744135C1/en not_active Expired - Lifetime
-
1998
- 1998-09-24 EP EP98952617A patent/EP1024842A2/en not_active Withdrawn
- 1998-09-24 WO PCT/EP1998/006019 patent/WO1999016416A2/en not_active Application Discontinuation
- 1998-09-24 JP JP2000513554A patent/JP2001517543A/en active Pending
- 1998-09-24 AU AU10251/99A patent/AU1025199A/en not_active Abandoned
Patent Citations (3)
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 (en) * | 1996-03-12 | 1997-09-18 | Pg-Txl Company, L.P. | Water soluble paclitaxel prodrugs |
WO1997045105A1 (en) * | 1996-05-24 | 1997-12-04 | Angiotech Pharmaceuticals, Inc. | Compositions and methods for treating or preventing diseases of body passageways |
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1741715A1 (en) | 1998-06-22 | 2007-01-10 | Novartis AG | Epothilone derivatives and their synthesis and use |
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 (en) | 2002-03-12 | 2003-09-25 | Bristol-Myers Squibb Company | C3-cyano epothilone derivatives |
WO2004052361A1 (en) * | 2002-12-09 | 2004-06-24 | Novartis Ag | Microtubule stabilisers for treating stenosis in 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 |
---|---|
EP1024842A2 (en) | 2000-08-09 |
DE19744135C1 (en) | 1999-03-25 |
WO1999016416A3 (en) | 1999-08-05 |
AU1025199A (en) | 1999-04-23 |
JP2001517543A (en) | 2001-10-09 |
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