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1. EP1874371 - ENDOPROSTHESES COMPRISING A POLYURETHANE BASED COATING

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Claims

1. An implantable endoprosthesis comprising:

a tubular member;

a coating on the tubular member comprising a polymeric material and a therapeutic agent,

characterized in that

the coating polymeric material releases the therapeutic agent, said polymeric material including the reaction product obtained by reacting a polyol, an isocyanate and a silsesquioxane having at least two pendent hydroxyl groups.


  2. The implantable endoprosthesis of claim 1, wherein the tubular member includes a polymeric material including a therapeutic agent dispersed.
  3. The implantable endoprosthesis of claim 1, wherein the coating includes between 1 percent by weight and 35 by weight therapeutic agent.
  4. The implantable endoprosthesis of claim 1, wherein the therapeutic agent inhibits restenosis.
  5. The implantable endoprosthesis of claim 4, wherein the therapeutic agent that inhibits restenosis comprises paclitaxel.
  6. The implantable endoprosthesis of claim 1, wherein the polymeric material fully releases its therapeutic agent in less than seven days in blood at body temperature.
  7. The implantable endoprosthesis of claim 1, wherein the polymeric material fully degrades in less than 365 days in blood at body temperature.
  8. The implantable endoprosthesis of claim 1, wherein the polyol is selected from the group consisting of be polyethylene glycol, polycaprolactone polyol, polycyclooctene polyol, trans-1,4 butadiene polyol, transisoprene polyol, polynorbornene polyol, polymethacrylate copolymer polyol, polycaprolactone-polylactide copolymer polyol, polycaprolactone-polyglycolide copolymer polyol, polycaprolactone-polylactide- polyglycolide copolymer polyol, polylactide polyol, polycaprolactone-poly(β-hydroxybutyric acid) copolymer polyol, poly(β-hydroxybutyric acid) polyol, and mixtures thereof.
  9. The implantable endoprosthesis of claim 1, wherein the polyol has only two pendent hydroxyl groups, and wherein the hydroxyl groups are disposed at ends of the polyol.
  10. The implantable endoprosthesis of claim 1, wherein the isocyanate comprises a diisocyanate.
  11. The implantable endoprosthesis of claim 10, wherein the diisocyanate is selected from the group consisting of 4,4'-diphenyl methylene diisocyanate, toluene-2,4-diisocyanate, toluene-2,6-diisocyanate, hexamethylene-1,6-diisocyanate, isophorone diisocyanate, and hydrogenated 4,4'-diphenylmethylene diisocyanate, and mixtures thereof.
  12. The implantable endoprosthesis of claim 1, wherein the silsesquioxane selected from the group consisting, 1-(2-trans-cyclohexanediol)ethyl-3,5,7,9,11,13,15-isobutylpentacyclo-[9.5.1.1 3,9.1 5,15.1 7,13] octasiloxane, 2-ethyl-2-[3-[[(heptaisobutylpentacyclo-[9.5.1.1 3,9.1 5,15.1 7,13]octasiloxanyl)oxy]dimethylsilyl]-propoxy]propane-1,3-diol, 1-(2,3-propanediol)propoxy-3,5,7,9,11,13,15-isobutylpentacyclo-[9.5.1.1 3,9.1 5,15.1 7,13]octasiloxane, 2-ethyl-2-[3-[[(heptaisobutylpentacyclo-[9.5.1.1 3,9.1 5,15.1 7,13]octasiloxanyl)oxy]dimethylsilyl]-propoxy]methyl]-1,3-propanediol, and mixtures thereof.
  13. The implantable endoprosthesis of claim 1, wherein a weight ratio of the polyol to the silsesquioxane is from 1:2 to 1:30.
  14. The implantable endoprosthesis of claim 1, wherein the coating has a thickness of between 3 micron and 50 micron before the implantable endoprosthesis is expanded.
  15. The implantable endoprosthesis of claim 1, wherein a coverage of the polymeric material on the tubular member is from 0.1 µg per square millimeter of surface area of the tubular member to 10 µg per square millimeter of surface area of the tubular member.
  16. The implantable endoprosthesis of claim 1, wherein the tubular member comprises a material selected from the group consisting of alloys, bioresorbable metals, metal oxides, bioresorbable polymers, and mixtures thereof.
  17. The implantable endoprosthesis of claim 1, wherein the polymeric material has an absolute molecular weight of greater than about 50,000.
  18. The implantable endoprosthesis of claim 1, wherein the polyol comprises polycaprolactone-polylactide copolymer, and the silsesquioxane comprises 2-ethyl-2-[3-[[(heptaisobutylpentacyclo-[9.5.1.1 3,9.1 5,15.1 7,13]octasiloxanyl)oxy]dimethylsilyl]-propoxy]methyl]-1,3-propanediol.
  19. The implantable endoprosthesis of claim 1, wherein the polyol has an absolute molecular weight of from 5,000 to 20,000.
  20. The implantable endoprosthesis of claim 1, wherein the polymeric material has a glass transition temperature of less than 100 °C.
  21. The implantable endoprosthesis of claim 1, wherein the polymeric material has a glass transition temperature of within about 10 °C of nominal human body temperature.
  22. The implantable endoprosthesis of claim 1, wherein the polymeric material has a storage modulus at 25 °C of less than 1,000 MPa.