US20040253467A1 - Device based on nitinol with a polyphosphazene coating - Google Patents
Device based on nitinol with a polyphosphazene coating Download PDFInfo
- Publication number
- US20040253467A1 US20040253467A1 US10/486,809 US48680904A US2004253467A1 US 20040253467 A1 US20040253467 A1 US 20040253467A1 US 48680904 A US48680904 A US 48680904A US 2004253467 A1 US2004253467 A1 US 2004253467A1
- Authority
- US
- United States
- Prior art keywords
- nitinol
- catheter
- polymer
- vascular
- substrate based
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
- 0 [1*]P([4*])(C)=NP([2*])([5*])=NP([3*])([6*])=NC Chemical compound [1*]P([4*])(C)=NP([2*])([5*])=NP([3*])([6*])=NC 0.000 description 2
Classifications
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- 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
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/02—Inorganic materials
- A61L27/04—Metals or alloys
- A61L27/06—Titanium or titanium alloys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/02—Inorganic materials
- A61L31/022—Metals or alloys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/08—Materials for coatings
- A61L31/10—Macromolecular materials
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/3154—Of fluorinated addition polymer from unsaturated monomers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31678—Of metal
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31725—Of polyamide
Definitions
- the present invention relates to a device, comprising a substrate based essentially on nitinol and, arranged thereon at least partially, a covering or a coating based on at least one polyphosphazene derivative having the general formula (I), a process for its production, and the use of the device as an artificial implant, vascular or nonvascular stent, catheter, thrombolectomy or embolectomy catheter, fragmentation spindle or catheter, guide wire, filter, vascular connector, hernia patch, oral, dental or throat implant or urether.
- nitinol is an intermetallic compound, mainly consisting of the metals nickel and titanium. After earlier deformation at a low temperature, nitinol has the peculiarity of assuming its original shape again after heating to a high temperature. This property is also known as “thermal shape memory”. Moreover, nitinol has a second functional property, the “mechanical shape memory” or alternatively super-elasticity. The latter property in particular, the ability to tolerate elastic extensions up to 8% completely reversibly, has led to a large number of applications as implants and components for interventional treatment methods, such as, for example, stents, stent grafts, vascular connectors, filters, capture baskets and guide wires.
- interventional treatment methods such as, for example, stents, stent grafts, vascular connectors, filters, capture baskets and guide wires.
- stents and filters are customarily brought to the position of the vessel at which they open up to the original shape.
- the nitinol component is compressed in the cold at extensions up to approximately 8%.
- endovascular stents having a defined diameter are first processed, then compressed in the cold and brought to the position of the vessel at which they are to be placed by means of insertion instruments.
- the previously compressed stent opens up to its original shape due to the body heat and/or due to its elastic ability and supports the surrounding vessel. Owing to the shape which is already fixed during manufacture, an overextension of the vessel can be avoided.
- the material nitinol per se has a very good body compatibility.
- various techniques were developed in order to seal the surface of an implant essentially manufactured from nitinol, such as, for example, a stent, and to provide it with a leakproof, nickel-impermeable layer. These processes of chemical aftertreatment customarily lead to a leakproof layer of titanium dioxide, through which nickel can hardly escape. These processes are known, inter alia, as electropolishing and are customary in different variants.
- oxidic layers do not inevitably worsen the physical compatibility of implants, they yield a surface which only allows a low hemocompatibility to be expected and thus makes necessary the use of vitamin K antagonists, and other anticoagulants, such as acetyl-salicylic acid. This represents an additional stress for the affected patients.
- a form of surface improvement to be additionally used would thus be desirable, such as, for example, a coating which makes leakproof the properties of a surface which is produced by electropolishing or in another way and is impermeable to metal ions, in particular nickel ions, with respect to the hemo- and biocompatibility and also further improves other properties, such as, in particular, the glidability, without damaging the leakproofness and isolating properties of such a surface.
- a surface obtained in such a way is also only temperature-stable within limits and becomes brittle in the cold, which in the specific case of the coating of nitinol leads at least to hairline cracks, at which thrombi can form. Moreover, the adhesion of such a coating is not particularly good. This becomes brittle during the cold treatment which is necessary and as a result of this detaches very easily, which in particular in the case of implants in endovascular systems can have considerable health sequelae. In the case of other materials, elastic properties which are important in virtually all cases for a coating of the type mentioned are only achieved by the addition of plasticizers. Plasticizers, however, decrease the blood and physical compatibility considerably.
- plasticizers can additionally lead to inflammatory reactions, reactions of the immune and anticoagulation system and thus to stress for the patients.
- the majority of plastics and plastic mixtures “plasticized” in such a way become brittle in the cold and and lose their elasticity. As a result, in the case of such materials the danger is always present that on renewed expansion cracks form or the layer detaches.
- the present invention is thus based on the object of making available a device based on nitinol suitable as an artificial implant, which is to be distinguished by high physical compatibility and a very good hemo-compatibility. Additionally, a device of this type should withstand the considerable temperature variations and mechanical stresses, such as, for example, elastic extensions of up to approximately 8%, which occur during the processing and use of the material nitinol, without a worsening of the property profile of the device, such as, for example, detachment or crack formation. This should in particular be achieved without the use of a plasticizer, since otherwise the physical compatibility of such an implant would be considerably decreased.
- a device comprising a substrate based essentially on nitinol and, arranged thereon at least partially, a covering or a coating based on at least one polymer having the following general formula (I),
- radicals R 1 to R 6 are identical or different and are an alkoxy, alkyl-sulfonyl, dialkylamino or aryloxy radical or a hetero-cycloalkyl or heteroaryl radical having nitrogen as a hetero atom.
- a further subject of the present invention is the use of the device according to the invention as an artificial implant, vascular or nonvascular stent, catheter, thrombolectomy or embolectomy catheter, fragmentation spindle or catheter, filter, vascular connector, hernia patch, oral, dental or throat implant, guide wire or urether, preferably as a vascular or nonvascular stent or as an oral, dental or throat implant.
- the device according to the invention exhibits a high physical compatibility and a very good hemocompatibility. Moreover, the device according to the invention shows essentially no adsorption of macrophages or colonization of bacteria.
- the polyphosphazene having the above formula (I) specifically selected in the context of the present invention for the coating of the substrate based on nitinol withstands in a particularly advantageous manner the in some cases extreme temperature variations and mechanical stresses in the course of the processing of the nitinol substrate without becoming brittle, detaching or tearing.
- the specifically selected polyphosphazene having the above formula (I) As a result of the specifically selected polyphosphazene having the above formula (I), the surface properties of nitinol are permanently improved, since the specifically selected poly-phosphazene derivative according to the general formula (I) is degraded neither hydrolytically nor enzymatically.
- the specifically selected polyphosphazene having the above formula (I) is elastic over a very wide temperature range, in particular at temperatures below the freezing point, without the use of plasticizers.
- the degree of polymerization of the polymer according to the above formula (I) used for the coating of the nitinol substrate is 2 to ⁇ .
- At least one of the radicals R 1 to R 6 in the polymer used is an alkoxy radical which is substituted by at least one fluorine atom.
- alkyl radicals in the alkoxy, alkylsulfonyl and dialkylamino radicals are, for example, straight- or branched-chain alkyl radicals having 1 to 20 carbon atoms, where the alkyl radicals can be substituted, for example, by at least one halogen atom, such as a fluorine atom.
- alkoxy radicals are methoxy, ethoxy, propoxy and butoxy groups, which can preferably be substituted by at least one fluorine atom.
- the 2,2,2-trifluoroethoxy group is particularly preferred.
- alkylsulfonyl radicals are methyl-, ethyl-, propyl- and butylsulfonyl groups.
- dialkylamino radicals are dimethyl-, diethyl-, dipropyl- and dibutylamino groups.
- the aryl radical in the aryloxy radical is, for example, an aryl unit having one or more aromatic ring systems, where the aryl radical can be substituted, for example, by at least one alkyl radical defined above.
- aryloxy radicals are phenoxy and naphthoxy groups and derivatives thereof.
- the heterocycloalkyl radical is, for example, a ring systems containing 3 to 7 atoms, where at least one ring atom is a nitrogen atom.
- the heterocycloalkyl radical can be substituted, for example, by at least one alkyl radical defined above.
- Examples of heterocycloalkyl radicals are piperidinyl, piperazinyl, pyrrolidinyl and morpholinyl groups and derivatives thereof.
- the heteroaryl radical is, for example, a compound having one or more aromatic ring systems, where at least one ring atom is a nitrogen atom.
- the heteroaryl radical can be substituted, for example, by at least one alkyl radical defined above. Examples of heteroaryl radicals are pyrrolyl, pyridinyl, pyridinolyl, isoquinolyl and quinolyl groups, and derivatives thereof.
- the polymer is poly[bis(trifluoroethoxy)phosphazene].
- the polymer can also be a poly[bis(trifluoroethoxy)-phosphazene] labelled by 32 P, 33 P or As or Sb isotopes.
- the polymeric compound poly[bis(trifluoroethoxy)phosphazene] shows a good antithrombogenic action (cf. Tur, Investigations on the thrombus resistance of poly[bis(trifluoroethoxy)-phosphazene] and Hollemann Wiberg, “Stickstoff-informationen des Phosphors” [Nitrogen compounds of phosphorus], Textbook of inorganic chemistry, 666-669, 91st-100th edition, Walter de Gruyter Verlag, 1985, and Tur, Vinogradova, inter alia “Entwicklungstendenzen bei polymeranalogen redesignen von Polyphosphazen” [Development tendencies in polymer-analogous reactions of polyphosphazene], Acta Polymerica 39, 424-429, no.
- the devices according to the invention on the one hand have excellent mechanical and body-compatible properties and on the other hand a high resistance against inflammation-promoting organisms, such as, for example, macrophages.
- a high resistance against inflammation-promoting organisms such as, for example, macrophages.
- the substrate based on nitinol can be partially coated with a covering based on at least one polymer having the general formula (I).
- the substrate is based on nitinol coated completely with a covering based on at least one polymer having the general formula (I).
- the nitinol substrate, which coated thereon has a covering of the polyphosphazene polymer according to the formula (I), is present in the form of an at least partially pierced or perforated tube, such as is customary, for example, in the case of an endovascular implant, such as a stent.
- the covering of at least one polyphosphazene polymer according to the formula (I) according to the present invention arranged or deposited on the nitinol substrate can further comprise one or more pharmaceutically active compounds, such as, for example, cytotoxic compounds, such as rapamycin, taxol, doxorubicin, platinum derivatives, 5-fluoracyl or antiinflammatory active compounds such as diclofenac or acetylsalicylic acid or other active compounds in a corresponding pharmaceutical preparation, preferably having delayed release or quantitatively controlled release over a relatively long period.
- cytotoxic compounds such as rapamycin, taxol, doxorubicin, platinum derivatives, 5-fluoracyl or antiinflammatory active compounds such as diclofenac or acetylsalicylic acid or other active compounds in a corresponding pharmaceutical preparation, preferably having delayed release or quantitatively controlled release over a relatively long period.
- the covering of the device according to the invention has, for example, a thickness of approximately 1 nm to approximately 100 ⁇ m, preferably to approximately 500 nm and particularly preferably to approximately 100 nm.
- a layer which contains an adhesion promoter i.e. adjacent to the coating based on at least one polymer having the general formula (I) is arranged an adhesion promoter layer.
- the adhesion promoter or spacer preferably contains a polar end group.
- a polar end group examples of these are hydroxyl, carboxylate, aldehyde, amino or nitro groups.
- end groups based on an alkoxy, alkylsulfonyl, dialkylamino or aryloxy radical or a heterocycloalkyl or heteroaryl radical having nitrogen as a heteroatom can also be present, where these radicals can also be differently substituted, for example by halogen atoms, in particular fluorine.
- the adhesion promoter can be, for example, an organosilicon compound, preferably an amino-terminated silane or a compound based on an aminosilane, an amino-terminated alkene, a nitro-terminated alkene, a nitro-terminated silane or an alkylphosphonic acid.
- an organosilicon compound preferably an amino-terminated silane or a compound based on an aminosilane, an amino-terminated alkene, a nitro-terminated alkene, a nitro-terminated silane or an alkylphosphonic acid.
- amino-propyltrimethoxysilane and aminopropyltriethoxysilane are particularly preferred.
- the adhesion promoter in particular improves the adhesion of the covering to the surface of the nitinol substrate by coupling of the adhesion promoter to the nitinol surface, for example by means of ionic and/or covalent bonds, and further coupling to the described polymer of the formula (I) of the covering, for example by means of ionic and/or covalent bonds.
- a further subject of the present invention relates to the production of the device according to the invention, comprising the steps:
- step (c) optionally hydroxylation of the surface treated in step (b) and application of an adhesion promoter
- the substrate based on nitinol can be made available in step (a), for example, in the form of an at least partially pierced or perforated tube.
- the substrate essentially comprises nitinol as the material forming the substrate.
- the substrate based on nitinol can in the course of this already be subjected to an electropolishing or other treatment for the production of a surface which is leakproof and impermeable to nickel ions.
- step (b) of the process according to the invention a plasma treatment of the nitinol surface takes place, the plasma preferably being an air or oxygen plasma.
- the plasma treatment By means of the plasma treatment, an ultrathin, leakproof TiO 2 layer is produced on the substrate based essentially on nitinol.
- Other plasma gases such as, for example, argon can also be employed.
- the plasma gases employed can further optionally contain one or more additives customary in such a process step, such as, for example, allyl, vinylbenzene, etc.
- an activation and cleaning of the nitinol surface by means of the plasma treatment takes place, whereby a complete and uniform oxidation and activation of the surface is brought about.
- step (c) a hydroxylation of the nitinol surface, for example by water, is optionally carried out and an adhesion promoter, preferably amino-propyltrimethoxysilane (APTMS) or aminopropyltriethoxy-silane, is applied to the surface and crosslinked.
- an adhesion promoter preferably amino-propyltrimethoxysilane (APTMS) or aminopropyltriethoxy-silane
- a solution which contains at least one compound of the general formula (I) in a concentration of 0.1 to 99% by weight is then applied to this surface in step (d), customarily by spraying or dipping.
- solvents ethyl acetate, acetone, THF, toluene or xylenes can be used here.
- the choice of the solvents or solvent mixtures is not restricted to the solvents mentioned.
- the evaporation of the solvent can proceed without further measures. Customarily, the concentration of the solvent vapor above the substrate, the pressure and the temperature is controlled. At the beginning of the first drying phase, an atmosphere saturated with the solvent vapor is customarily established above the coated substrate, the concentration of the solvent vapor subsequently being slowly reduced over a number of hours.
- the temperature can vary here from ⁇ 30° C. to +90° C.
- the pressure can run through a ramp from normal pressure to water jet vacuum (20 torr). After the first drying phase, the coated substrate is then dried further for a certain time in an oil pump vacuum (0.1 torr).
- the device coated with the dried polymer of the compound (I) based on nitinol can then be directly further used after appropriate sterilization and further processed in the cold, i.e. compressed.
- various layer thicknesses of from 0.1 nm to 300 ⁇ m or thicker, preferably in the range from 500 nm to 30 ⁇ m, and particularly preferably around 100 nm, can be produced.
- the structuring of the polymer coating is subject to no specific restriction.
- structures of the order of magnitude of nanometers, micrometers or even larger or smaller, preferably in the range from 10 nm to 100 ⁇ m, can be produced.
- all structures can be produced and used which can be generated photolithographically or using electron beams, X-rays or laser beams or by means of other techniques.
- a microstructuring of the coating can also be obtained by means of direct “writing” on a film produced beforehand based on at least one polyphosphazene derivative according to the above formula (I) by means of laser beams, electron beams or X-rays or else by “melt structuring”, where a thin wire is brought to the melting temperature of the polymer, which then melts the desired structure into the coating by direct contact.
- a structuring of this type in that structures are imprinted in the film which particularly favorably arrange the flow behavior of liquids (e.g. sharkskin or lotus effect).
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- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Inorganic Chemistry (AREA)
- Vascular Medicine (AREA)
- Surgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Transplantation (AREA)
- Medicinal Chemistry (AREA)
- Dermatology (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Materials For Medical Uses (AREA)
- Prostheses (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/725,709 US8101275B2 (en) | 2001-08-17 | 2007-03-19 | Device based on nitinol, a process for its production, and its use |
US13/356,639 US8313841B2 (en) | 2001-08-17 | 2012-01-23 | Device based on nitinol, a process for its production, and its use |
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10140522 | 2001-08-17 | ||
DE10140522.7 | 2001-08-17 | ||
DE10202467.7 | 2002-01-23 | ||
DE2002102467 DE10202467A1 (de) | 2002-01-23 | 2002-01-23 | Vorrichtung auf Basis von Nitinol, ein Verfahren zu dessen Herstellung sowie dessen Verwendung |
PCT/EP2002/009017 WO2003015719A1 (de) | 2001-08-17 | 2002-08-12 | Vorrichtung auf basis von nitinol mit polyphosphazenüberzug |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/725,709 Continuation US8101275B2 (en) | 2001-01-11 | 2007-03-19 | Device based on nitinol, a process for its production, and its use |
Publications (1)
Publication Number | Publication Date |
---|---|
US20040253467A1 true US20040253467A1 (en) | 2004-12-16 |
Family
ID=26009956
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/486,809 Abandoned US20040253467A1 (en) | 2001-08-17 | 2002-08-12 | Device based on nitinol with a polyphosphazene coating |
US11/725,709 Expired - Fee Related US8101275B2 (en) | 2001-01-11 | 2007-03-19 | Device based on nitinol, a process for its production, and its use |
US13/356,639 Expired - Lifetime US8313841B2 (en) | 2001-08-17 | 2012-01-23 | Device based on nitinol, a process for its production, and its use |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/725,709 Expired - Fee Related US8101275B2 (en) | 2001-01-11 | 2007-03-19 | Device based on nitinol, a process for its production, and its use |
US13/356,639 Expired - Lifetime US8313841B2 (en) | 2001-08-17 | 2012-01-23 | Device based on nitinol, a process for its production, and its use |
Country Status (9)
Country | Link |
---|---|
US (3) | US20040253467A1 (de) |
EP (1) | EP1432380B1 (de) |
AT (1) | ATE340551T1 (de) |
CA (1) | CA2457018C (de) |
DE (1) | DE50208282D1 (de) |
DK (1) | DK1432380T3 (de) |
ES (1) | ES2272807T3 (de) |
PT (1) | PT1432380E (de) |
WO (1) | WO2003015719A1 (de) |
Cited By (7)
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US20060068363A1 (en) * | 2003-03-26 | 2006-03-30 | Polyzenix Gmbh | Coated dental implants |
US20080095816A1 (en) * | 2006-10-10 | 2008-04-24 | Celonova Biosciences, Inc. | Compositions and Devices Comprising Silicone and Specific Polyphosphazenes |
US20080138377A1 (en) * | 2002-07-05 | 2008-06-12 | Celonova Biosciences, Inc. | Vasodilator Eluting Luminal Stent Devices With A Specific Polyphosphazene Coating and Methods for Their Manufacture and Use |
EP2167131A1 (de) * | 2007-07-09 | 2010-03-31 | Apogee Technology, Inc. | Beschichtungsformulierungen mit polyphosphazen-polyelektrolyten und biologischen wirkstoffen und mit solchen formulierungen beschichtete unebenheiten |
EP2173431A1 (de) * | 2007-07-09 | 2010-04-14 | Apogee Technology, Inc. | Immunstimulierende polyphosphazen-verbindungen zur intradermalen immunisierung |
US20100312331A1 (en) * | 2007-05-15 | 2010-12-09 | Chameleon Biosurfaces Limited | Polymer coatings on medical devices |
US11043390B2 (en) * | 2017-07-31 | 2021-06-22 | Centre National De La Recherche Scientifique | Mask for protecting a semiconductor material for localized etching applications |
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Publication number | Priority date | Publication date | Assignee | Title |
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DE10100961B4 (de) | 2001-01-11 | 2005-08-04 | Polyzenix Gmbh | Körperverträglicher Werkstoff und mit diesem Werkstoff beschichtetes Substrat für die Züchtung von Zellen und künstlichen aus Zellen aufgebauten oder gewachsenen organischen Implantaten |
US20210299056A9 (en) | 2004-10-25 | 2021-09-30 | Varian Medical Systems, Inc. | Color-Coded Polymeric Particles of Predetermined Size for Therapeutic and/or Diagnostic Applications and Related Methods |
WO2009054851A1 (en) * | 2007-10-24 | 2009-04-30 | Celonova Biosciences, Inc. | Specific polyphosphazene-containing three-dimensional bone support implants and mehods for their use |
EP2252218A4 (de) * | 2008-02-11 | 2012-06-06 | Celonova Biosciences Inc | Gewebebefestigungsartikel und vorrichtungen und relevante verfahren |
US9833240B2 (en) | 2008-02-18 | 2017-12-05 | Covidien Lp | Lock bar spring and clip for implant deployment device |
US8758373B2 (en) | 2008-02-18 | 2014-06-24 | Covidien Lp | Means and method for reversibly connecting a patch to a patch deployment device |
US9398944B2 (en) | 2008-02-18 | 2016-07-26 | Covidien Lp | Lock bar spring and clip for implant deployment device |
US8317808B2 (en) | 2008-02-18 | 2012-11-27 | Covidien Lp | Device and method for rolling and inserting a prosthetic patch into a body cavity |
US9034002B2 (en) | 2008-02-18 | 2015-05-19 | Covidien Lp | Lock bar spring and clip for implant deployment device |
US9044235B2 (en) | 2008-02-18 | 2015-06-02 | Covidien Lp | Magnetic clip for implant deployment device |
US9393093B2 (en) | 2008-02-18 | 2016-07-19 | Covidien Lp | Clip for implant deployment device |
US9393002B2 (en) | 2008-02-18 | 2016-07-19 | Covidien Lp | Clip for implant deployment device |
EP2247245B1 (de) | 2008-02-18 | 2017-06-28 | Covidien LP | Vorrichtung zur ablage und befestigung eines pflasters auf biologischem gewebe |
US8808314B2 (en) | 2008-02-18 | 2014-08-19 | Covidien Lp | Device and method for deploying and attaching an implant to a biological tissue |
US9301826B2 (en) | 2008-02-18 | 2016-04-05 | Covidien Lp | Lock bar spring and clip for implant deployment device |
WO2009105761A2 (en) * | 2008-02-22 | 2009-08-27 | Celonova Biosciences, Inc. | Multi-functional wound dressing matrices and related methods |
CA2730547C (en) | 2008-10-20 | 2013-08-06 | Polytouch Medical Ltd. | A device for attaching a patch to a biological tissue |
WO2011021083A1 (en) | 2009-08-17 | 2011-02-24 | PolyTouch Medical, Inc. | Articulating patch deployment device and method of use |
EP2467066B1 (de) | 2009-08-17 | 2019-03-27 | Covidien LP | Mittel zur aufhebbaren verbindung eines implantats mit einer einsatzvorrichtung |
US20140094861A1 (en) * | 2012-10-01 | 2014-04-03 | Smith & Nephew, Inc. | Surgical locator |
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- 2002-08-12 ES ES02794780T patent/ES2272807T3/es not_active Expired - Lifetime
- 2002-08-12 DK DK02794780T patent/DK1432380T3/da active
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- 2002-08-12 PT PT02794780T patent/PT1432380E/pt unknown
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2007
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US8343212B2 (en) | 2007-05-15 | 2013-01-01 | Biotectix, LLC | Polymer coatings on medical devices |
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Also Published As
Publication number | Publication date |
---|---|
WO2003015719A1 (de) | 2003-02-27 |
DK1432380T3 (da) | 2007-01-15 |
EP1432380B1 (de) | 2006-09-27 |
PT1432380E (pt) | 2007-01-31 |
ES2272807T3 (es) | 2007-05-01 |
US20070184277A1 (en) | 2007-08-09 |
CA2457018C (en) | 2010-12-14 |
US8101275B2 (en) | 2012-01-24 |
EP1432380A1 (de) | 2004-06-30 |
DE50208282D1 (de) | 2006-11-09 |
ATE340551T1 (de) | 2006-10-15 |
US20120118436A1 (en) | 2012-05-17 |
CA2457018A1 (en) | 2003-02-27 |
US8313841B2 (en) | 2012-11-20 |
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