BE1008260A6 - Amphiphile polyurethane charged with medicine which is coated onto vascularstents for the treatment of blood vessel constriction - Google Patents
Amphiphile polyurethane charged with medicine which is coated onto vascularstents for the treatment of blood vessel constriction Download PDFInfo
- Publication number
- BE1008260A6 BE1008260A6 BE9400383A BE9400383A BE1008260A6 BE 1008260 A6 BE1008260 A6 BE 1008260A6 BE 9400383 A BE9400383 A BE 9400383A BE 9400383 A BE9400383 A BE 9400383A BE 1008260 A6 BE1008260 A6 BE 1008260A6
- Authority
- BE
- Belgium
- Prior art keywords
- polyurethane
- amphiphile
- blood vessel
- treatment
- prostheses
- Prior art date
Links
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 15
- 239000004814 polyurethane Substances 0.000 title claims abstract description 15
- 210000004204 blood vessel Anatomy 0.000 title claims abstract description 13
- 239000003814 drug Substances 0.000 title abstract description 13
- OGQYPPBGSLZBEG-UHFFFAOYSA-N dimethyl(dioctadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC OGQYPPBGSLZBEG-UHFFFAOYSA-N 0.000 title abstract 3
- 238000000034 method Methods 0.000 claims abstract description 11
- 238000000576 coating method Methods 0.000 claims abstract description 6
- 239000011248 coating agent Substances 0.000 claims abstract description 5
- 208000031481 Pathologic Constriction Diseases 0.000 claims description 5
- 230000004044 response Effects 0.000 claims description 2
- 229940079593 drug Drugs 0.000 abstract description 11
- 238000006243 chemical reaction Methods 0.000 abstract description 4
- 229920000642 polymer Polymers 0.000 abstract description 4
- 238000002513 implantation Methods 0.000 abstract description 3
- 239000008280 blood Substances 0.000 abstract description 2
- 210000004369 blood Anatomy 0.000 abstract description 2
- 239000007943 implant Substances 0.000 abstract 1
- 239000002184 metal Substances 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 208000037803 restenosis Diseases 0.000 description 4
- 150000002009 diols Chemical class 0.000 description 3
- PUDHBTGHUJUUFI-SCTWWAJVSA-N (4r,7s,10s,13r,16s,19r)-10-(4-aminobutyl)-n-[(2s,3r)-1-amino-3-hydroxy-1-oxobutan-2-yl]-19-[[(2r)-2-amino-3-naphthalen-2-ylpropanoyl]amino]-16-[(4-hydroxyphenyl)methyl]-13-(1h-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-7-propan-2-yl-1,2-dithia-5,8,11,14,17-p Chemical compound C([C@H]1C(=O)N[C@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(N[C@@H](CSSC[C@@H](C(=O)N1)NC(=O)[C@H](N)CC=1C=C2C=CC=CC2=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(N)=O)=O)C(C)C)C1=CC=C(O)C=C1 PUDHBTGHUJUUFI-SCTWWAJVSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- 241000282887 Suidae Species 0.000 description 2
- 210000004351 coronary vessel Anatomy 0.000 description 2
- 229960002897 heparin Drugs 0.000 description 2
- 229920000669 heparin Polymers 0.000 description 2
- 229960002437 lanreotide Drugs 0.000 description 2
- 108010021336 lanreotide Proteins 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 230000002885 thrombogenetic effect Effects 0.000 description 2
- 230000001732 thrombotic effect Effects 0.000 description 2
- 230000002792 vascular Effects 0.000 description 2
- 239000005541 ACE inhibitor Substances 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 239000004970 Chain extender Substances 0.000 description 1
- 102000007625 Hirudins Human genes 0.000 description 1
- 108010007267 Hirudins Proteins 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- FQISKWAFAHGMGT-SGJOWKDISA-M Methylprednisolone sodium succinate Chemical compound [Na+].C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)COC(=O)CCC([O-])=O)CC[C@H]21 FQISKWAFAHGMGT-SGJOWKDISA-M 0.000 description 1
- 108010023197 Streptokinase Proteins 0.000 description 1
- 239000004433 Thermoplastic polyurethane Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 1
- 230000002927 anti-mitotic effect Effects 0.000 description 1
- 239000003080 antimitotic agent Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 238000002405 diagnostic procedure Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- WQPDUTSPKFMPDP-OUMQNGNKSA-N hirudin Chemical compound C([C@@H](C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC(OS(O)(=O)=O)=CC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]1NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H]2CSSC[C@@H](C(=O)N[C@@H](CCC(O)=O)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@H](C(=O)N[C@H](C(NCC(=O)N[C@@H](CCC(N)=O)C(=O)NCC(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)N2)=O)CSSC1)C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]1NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=2C=CC(O)=CC=2)NC(=O)[C@@H](NC(=O)[C@@H](N)C(C)C)C(C)C)[C@@H](C)O)CSSC1)C(C)C)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 WQPDUTSPKFMPDP-OUMQNGNKSA-N 0.000 description 1
- 229940006607 hirudin Drugs 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 206010020718 hyperplasia Diseases 0.000 description 1
- 230000003463 hyperproliferative effect Effects 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000028709 inflammatory response Effects 0.000 description 1
- 229960004584 methylprednisolone Drugs 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229960005202 streptokinase Drugs 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/14—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
- A61L31/16—Biologically active materials, e.g. therapeutic substances
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/416—Anti-neoplastic or anti-proliferative or anti-restenosis or anti-angiogenic agents, e.g. paclitaxel, sirolimus
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/42—Anti-thrombotic agents, anticoagulants, anti-platelet agents
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Media Introduction/Drainage Providing Device (AREA)
- Materials For Medical Uses (AREA)
Abstract
The process of coating endovascular prostheses with medicinally chargedamphiphile polyurethane has been successful in significantly improving thebiocompatibility and the blood compatibility of endovascular prostheses.When these amphiphile polyurethane are implanted into the human or animaltissue or blood vessels, they remain stable and do not trigger aninflammatory reaction. Moreover, it is possible to incorporate medicines inthese polymers, which have a slow release function after implantation, atthe location of the implant. This system can further reduce thethrombogenicity of the prostheses coated with amphiphile polyurethane andcan inhibit the rejection reaction to the prostheses.
Description
AMFIFIELE POLYURETHANEN OPGELADEN MET MEDICIJNEN GECOAT OPVASCULAIRE STENTS TER BEHANDELING VAN BLOEDVATVERNAUWINGEN.
BESCHRIJVING
Behandeling van bloedvatvernauwingen door middel van een balloncatheter is een populaire methode. Vorig jaar werden op deze manier in ons land meer dan 6000 patienten met coronaire bloedvatvernauwingen behandeld. Probleem van deze behandelingsmethode is enerzijds het gevaar dat tijdens het opblazen van de ballon een scheur ontstaat waardoor het bloedvat kan dichtvallen en alzo een akuut myocardinfarkt kan veroorzaken, anderzijds is het goed gedocumenteerd dat deze behandelingsmethode gepaard gaat met een frequente teruggroei(restenose) van de bloedvatvernauwing binnen de 6 maand na de behandeling. Om deze problemen optelossen werden enerzijds medicijnen uitgetest om de teruggroei van de vernauwing te voorkomen en anderzijds nieuwe behandelingsmethoden ontwikkeld.
Een van die nieuwe behandelingsmethoden bestaat erin een metalen intravasculaire prothese (stent) ter hoogte van de vernauwing te plaatsen. Deze methode is zeer efficient voor het behandelen van vaatscheuren die kunnen ontstaan tijdens de ballondilatatie maar deze metalen ondersteuningen zijn op zichzelf ook trombogeen en kunnen aanleiding geven tot een trombotische occlusie van het bloedvat. Anderzijds bleek dat door het implanteren van een metalen prothese in een bloedvat het lichaam kan reageren met een afweerreactie waardoor terug bloedvatvernauwingen (restenose) kunnen ontstaan binnen de 6 maand na implantatie van de prothese. Vervolgens heeft men geprobeerd polymeer prothesen te maken maar ook deze gaven dezelfde problemen.
Door het bedekken (coaten) van deze endovasculaire prothesen met amfifiele polyurethanen zijn wij erin geslaagd zowel het probleem van de trombotische occlusies als het probleem van de reactieve hyperproliferatieve response die aanleiding geeft tot restenose op belangrijke wijze te beperken. Deze polyurethanen worden gesynthetiseerd vertrekkend van amfifiele polyester-diolen op basis van ethyleeno:<ide en propyleenoxide. Door reactie met een diosocyanaat en een ketenverlenger (butaandiol) wordt finaal een thermoplastisch polyurethaan bekomen. Door de geschikte keuze van a) het polyesterdiol, meer bepaald de verhouding ethyleenoxide/propyleenoxide, en b) het moleculair gewicht van het diol kan de bio- en bloedcompatibiliteit worden beinvloed.
Deze polyurethanen hebben de eigenschap, wanneer ingeplant in menselijke of dierlijke weefsels of in menselijke of dierlijke bloedvaten, stabiel te blijven en quasi geen inflammatoire reactie uit te lokken.
Deze polyurethanen bleken in onze dierexperimenten dan ook uitermate geschikt als coating van endovasculaire prothesen.
Verder is het mogelijk om medicijnen aan deze polyurethanen te binden. Deze medicijnen hebben tot doel de trombogeniciteit van de prothesen nog verder te verminderen
(heparine, hirudine, streptokinase, tpa e.a.) en de afstotingsreactie tegen de prothese nog verder te inhiberen
(ACE remmers, corticoiden, angiopeptine, antimitotica e.a.). Geneesmiddel beladen coatings worden aangebracht door de
<EMI ID=1.1>
het medicijn in de polymeeroplossing. Tijdens de polymerisatie worden de geneesmuiddelen als het ware gevangen in het polymeernetwerk.
Bij proefondervindelijk onderzoek in vitro, waarbij we medicijnopgeladen polyurethaan gecoate stents incubeerden in een fysiologische bufferoplossing hebben wij kunnen aantonen dat het medicijn langzaam losgelaten werd gedurende verschillende dagen. Bij deze opstelling gebruikten we angiopeptine, methylprednisolone en heparine. Het grote voordeel van het gebruik van amfifiele polyurethanen is dat ze zowel met hydrofobe als hydrofiele medicijnen kunnen opgeladen worden.
Proefondervindelijk onderzoek bij varkens toonde aan dat door het inplanteren van een medicijnopgeladen polyurethaan gecoate stent het mogelijk is om hoge bloedvatwand weefselconcentraties te bekomen gedurende tenminste 10 dagen. De plasmaconcentraties waren verwaarloosbaar laag. We konden dus aantonen dat met deze methode een selectieve toediening van het medicijn tehoogte van het targetorgaan kan bekomen worden. Men kan dus verwachten dat met deze methode de systemische bijwerkingen van de gebruikte medicijnen belangrijk zullen afnemen.
Proefondervindelijk onderzoek bij varkens toonde aan dat inplantatie van medicijn opgeladen polyurethaan gecoatte stents in coronaire bloedvaten significant minder trombogene occlusies vertoonden in vergelijking met niet gecoatte metalen stents. Verder kon aangetoond worden dat de medicijnopgeladen polyurethaan gecoatte stent significant minder neointimale hyperplasie (restenose) vertoonden in vergelijking met niet gecoatte metalen stents.
TOEPASSINGSMOGELIJKHEDEN VAN HET SYSTEEM
1. Behandeling van bloedvatvernauwingen bij mens en dier.
2. Behandeling van complicaties ontstaan tijdens andere
behandelingsmethoden van bloedvatvernauwingen.
3. Behandeling van complicaties ontstaan tijdens
diagnostische procedures voor het opsporen van cardiale en vaataandoeningen.
4. Coating van prothesen, draden, en catheters ingebracht
voor medische doeleinden.
AMPHI-FILE POLYURETHANS CHARGED WITH MEDICINES COATED VASCULAR STENTS FOR TREATING VESSEL STRENGTHS.
DESCRIPTION
Treatment of blood vessel strictures by means of a balloon catheter is a popular method. Last year, more than 6,000 patients with coronary artery strictures were treated in this way in our country. The problem of this treatment method is on the one hand the danger that during the inflation of the balloon a rupture occurs which can cause the blood vessel to close and thus cause an acute myocardial market, on the other hand, it is well documented that this treatment method is accompanied by a frequent regrowth (restenosis) of the blood vessel constriction within 6 months after treatment. To solve these problems, medicines were tested on the one hand to prevent the regrowth of the narrowing and on the other hand new treatment methods were developed.
One of these new treatment methods is to place a metal intravascular prosthesis (stent) at the level of the narrowing. This method is very efficient in treating vascular tears that may develop during balloon dilatation, but these metal supports are also thrombogenic in themselves and may lead to thrombotic occlusion of the blood vessel. On the other hand, it has been found that by implanting a metal prosthesis in a blood vessel, the body can react with an immune response, which can lead to blood vessel constrictions (restenosis) within 6 months after implantation of the prosthesis. Subsequently, attempts were made to make polymer prostheses, but these also presented the same problems.
By covering (coating) these endovascular prostheses with amphiphilic polyurethanes, we have succeeded in significantly limiting both the problem of thrombotic occlusions and the problem of the reactive hyperproliferative response that gives rise to restenosis. These polyurethanes are synthesized starting from amphiphilic polyester diols based on ethylene oxide and propylene oxide. A thermoplastic polyurethane is finally obtained by reaction with a diosocyanate and a chain extender (butanediol). By the suitable choice of a) the polyester diol, in particular the ratio of ethylene oxide / propylene oxide, and b) the molecular weight of the diol, the bio and blood compatibility can be influenced.
These polyurethanes have the property, when implanted in human or animal tissues or in human or animal blood vessels, to remain stable and to elicit virtually no inflammatory response.
In our animal experiments, these polyurethanes were therefore extremely suitable as a coating for endovascular prostheses.
It is also possible to bind medicines to these polyurethanes. These drugs aim to further reduce the thrombogenicity of the prostheses
(heparin, hirudin, streptokinase, tpa and others) and to further inhibit the rejection reaction against the prosthesis
(ACE inhibitors, corticoids, angiopeptin, antimitotics, etc.). Drug loaded coatings are applied by the
<EMI ID = 1.1>
the drug in the polymer solution. During the polymerization, the drug components are, as it were, trapped in the polymer network.
In vitro experimentation, in which we incubated drug-charged polyurethane-coated stents in a physiological buffer solution, we demonstrated that the drug was slowly released over several days. In this setup, we used angiopeptin, methylprednisolone and heparin. The major advantage of using amphiphilic polyurethanes is that they can be charged with both hydrophobic and hydrophilic drugs.
Experimental studies in pigs showed that by implanting a drug-charged polyurethane coated stent it is possible to obtain high blood vessel wall tissue concentrations for at least 10 days. Plasma concentrations were negligibly low. We were therefore able to demonstrate that with this method a selective administration of the drug can be achieved at the height of the target organ. It can therefore be expected that with this method the systemic side effects of the drugs used will decrease significantly.
Experimental studies in pigs showed that implantation of drug-charged polyurethane coated stents into coronary arteries showed significantly fewer thrombogenic occlusions compared to uncoated metal stents. Furthermore, it could be shown that the drug-charged polyurethane coated stent exhibited significantly less neointimal hyperplasia (restenosis) compared to uncoated metal stents.
SCOPE OF APPLICATION OF THE SYSTEM
1. Treatment of blood vessel strictures in humans and animals.
2. Treatment of complications arising during others
treatment methods of blood vessel strictures.
3. Treatment of complications arising during
diagnostic procedures for detecting cardiovascular disease.
4. Coating of prostheses, wires, and catheters inserted
for medical purposes.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE9400383A BE1008260A6 (en) | 1994-04-14 | 1994-04-14 | Amphiphile polyurethane charged with medicine which is coated onto vascularstents for the treatment of blood vessel constriction |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE9400383A BE1008260A6 (en) | 1994-04-14 | 1994-04-14 | Amphiphile polyurethane charged with medicine which is coated onto vascularstents for the treatment of blood vessel constriction |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE1008260A6 true BE1008260A6 (en) | 1996-02-27 |
Family
ID=3888095
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE9400383A BE1008260A6 (en) | 1994-04-14 | 1994-04-14 | Amphiphile polyurethane charged with medicine which is coated onto vascularstents for the treatment of blood vessel constriction |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE1008260A6 (en) |
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|---|---|---|---|---|
| WO2010095044A3 (en) * | 2009-02-21 | 2010-11-04 | Sofradim Production | Medical device with degradation-retarding coating |
| US8648144B2 (en) | 2009-02-21 | 2014-02-11 | Sofradim Production | Crosslinked fibers and method of making same by extrusion |
| US8795331B2 (en) | 2010-03-25 | 2014-08-05 | Covidien Lp | Medical devices incorporating functional adhesives |
| US8865857B2 (en) | 2010-07-01 | 2014-10-21 | Sofradim Production | Medical device with predefined activated cellular integration |
| US8956603B2 (en) | 2009-02-21 | 2015-02-17 | Sofradim Production | Amphiphilic compounds and self-assembling compositions made therefrom |
| US8968818B2 (en) | 2009-02-21 | 2015-03-03 | Covidien Lp | Medical devices having activated surfaces |
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| US9510810B2 (en) | 2009-02-21 | 2016-12-06 | Sofradim Production | Medical devices incorporating functional adhesives |
| US9523159B2 (en) | 2009-02-21 | 2016-12-20 | Covidien Lp | Crosslinked fibers and method of making same using UV radiation |
| US9555154B2 (en) | 2009-02-21 | 2017-01-31 | Covidien Lp | Medical devices having activated surfaces |
| US9775928B2 (en) | 2013-06-18 | 2017-10-03 | Covidien Lp | Adhesive barbed filament |
| US9987297B2 (en) | 2010-07-27 | 2018-06-05 | Sofradim Production | Polymeric fibers having tissue reactive members |
-
1994
- 1994-04-14 BE BE9400383A patent/BE1008260A6/en not_active IP Right Cessation
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| US9517291B2 (en) | 2009-02-21 | 2016-12-13 | Covidien Lp | Medical devices having activated surfaces |
| US9523159B2 (en) | 2009-02-21 | 2016-12-20 | Covidien Lp | Crosslinked fibers and method of making same using UV radiation |
| US9272074B2 (en) | 2010-03-25 | 2016-03-01 | Sofradim Production | Surgical fasteners and methods for sealing wounds |
| US9554782B2 (en) | 2010-03-25 | 2017-01-31 | Covidien Lp | Medical devices incorporating functional adhesives |
| US10143471B2 (en) | 2010-03-25 | 2018-12-04 | Sofradim Production | Surgical fasteners and methods for sealing wounds |
| US8795331B2 (en) | 2010-03-25 | 2014-08-05 | Covidien Lp | Medical devices incorporating functional adhesives |
| US9247931B2 (en) | 2010-06-29 | 2016-02-02 | Covidien Lp | Microwave-powered reactor and method for in situ forming implants |
| US8865857B2 (en) | 2010-07-01 | 2014-10-21 | Sofradim Production | Medical device with predefined activated cellular integration |
| US9987297B2 (en) | 2010-07-27 | 2018-06-05 | Sofradim Production | Polymeric fibers having tissue reactive members |
| US9775928B2 (en) | 2013-06-18 | 2017-10-03 | Covidien Lp | Adhesive barbed filament |
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| Date | Code | Title | Description |
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| RE | Patent lapsed |
Owner name: D.S.B. N.V. Effective date: 19960430 |