CA2538669A1 - Medicated stent having multi-layer polymer coating - Google Patents
Medicated stent having multi-layer polymer coating Download PDFInfo
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- CA2538669A1 CA2538669A1 CA002538669A CA2538669A CA2538669A1 CA 2538669 A1 CA2538669 A1 CA 2538669A1 CA 002538669 A CA002538669 A CA 002538669A CA 2538669 A CA2538669 A CA 2538669A CA 2538669 A1 CA2538669 A1 CA 2538669A1
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- stent
- polymer
- copolymer
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- polymers
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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
- 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
- A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
- A61F2/00—Filters implantable into blood vessels; Prostheses, i.e. artificial substitutes or replacements for parts of the body; Appliances for connecting them with the body; Devices providing patency to, or preventing collapsing of, tubular structures of the body, e.g. stents
- A61F2/02—Prostheses implantable into the body
- A61F2/04—Hollow or tubular parts of organs, e.g. bladders, tracheae, bronchi or bile ducts
- A61F2/06—Blood vessels
- A61F2/07—Stent-grafts
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
- A61F2/00—Filters implantable into blood vessels; Prostheses, i.e. artificial substitutes or replacements for parts of the body; Appliances for connecting them with the body; Devices providing patency to, or preventing collapsing of, tubular structures of the body, e.g. stents
- A61F2/82—Devices providing patency to, or preventing collapsing of, tubular structures of the body, e.g. stents
-
- 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
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/22—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing macromolecular materials
- A61L15/225—Mixtures of macromolecular compounds
-
- 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
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/42—Use of materials characterised by their function or physical properties
- A61L15/425—Porous materials, e.g. foams or sponges
-
- 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
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/42—Use of materials characterised by their function or physical properties
- A61L15/62—Compostable, hydrosoluble or hydrodegradable 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
- A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
- A61F2/00—Filters implantable into blood vessels; Prostheses, i.e. artificial substitutes or replacements for parts of the body; Appliances for connecting them with the body; Devices providing patency to, or preventing collapsing of, tubular structures of the body, e.g. stents
- A61F2/02—Prostheses implantable into the body
- A61F2/04—Hollow or tubular parts of organs, e.g. bladders, tracheae, bronchi or bile ducts
- A61F2/06—Blood vessels
- A61F2/07—Stent-grafts
- A61F2002/072—Encapsulated stents, e.g. wire or whole stent embedded in lining
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
- A61F2250/00—Special features of prostheses classified in groups A61F2/00 - A61F2/26 or A61F2/82 or A61F9/00 or A61F11/00 or subgroups thereof
- A61F2250/0058—Additional features; Implant or prostheses properties not otherwise provided for
- A61F2250/0067—Means for introducing or releasing pharmaceutical products into the body
-
- 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
- A61L2420/00—Materials or methods for coatings medical devices
- A61L2420/08—Coatings comprising two or more layers
Abstract
This invention relates to stents having tacrolimus and/or everolimus containing medicated multi-layer hybrid polymer coatings, useful for the treatment of stenosed vasculature or other body passages.
Claims (45)
1. A stent having a coating comprising:
(a) a primer layer comprising a plurality of polymers comprising an anchoring polymer, and (b) a drug reservoir layer comprising a polymeric matrix of a plurality of polymers, comprising a drug stabilizing polymer and a toughening polymer, and an active agent comprising tacrolimus and/or everolimus integrated in the polymeric matrix, the polymeric matrix protecting and stabilizing the active agent(s) during sterilization and storage, the coating having sufficient adhesion and flexibility to remain intact upon insertion and stent expansion in a subject and releasing efficacious amounts of the active agent at the site of stent expansion.
(a) a primer layer comprising a plurality of polymers comprising an anchoring polymer, and (b) a drug reservoir layer comprising a polymeric matrix of a plurality of polymers, comprising a drug stabilizing polymer and a toughening polymer, and an active agent comprising tacrolimus and/or everolimus integrated in the polymeric matrix, the polymeric matrix protecting and stabilizing the active agent(s) during sterilization and storage, the coating having sufficient adhesion and flexibility to remain intact upon insertion and stent expansion in a subject and releasing efficacious amounts of the active agent at the site of stent expansion.
2. The stent of claim 1, further comprising an intermediate layer between the primer layer and the drug release layer, comprising a polymer composition distinct from the primer layer and drug reservoir layer.
3. The stent of claim 1, further comprising one or more image enhancing material(s) in one of the layers, or in a separate layer(s), that is capable of enhancing visibility in ultra sound, magnetic resonance imaging, and/or X ray imaging.
4. The stent of claim 1, wherein the primer layer and/or the drug reservoir layer is a single layer.
5. The stent of claim 1, wherein the anchoring polymers have functional groups, selected from amides, carboxyl, hydroxyl, amine, imine, amide, imide, sulfoxyl, sulfonyl, and combinations.
6. The stent of claim 1, wherein the primer layer further comprises one or more cross-linking and/or cross-linkable polymers selected from epoxy resins, melamine resins, phenolics, and isocyanate polymers.
7. The stent of claim 1, wherein the primer layer further comprises one or more of polyvinylpyrrolidone/vinyl acetate copolymer (PVP/VA), olefin acrylic acid copolymer, polyethylene glycol, polyethylene oxide, and polyvinylpyridine polymers and copolymers.
8. The stent of claim 1, wherein the stabilizing polymer is a cellulose ester, a cellulose ether, an acrylic polymer and/or an acrylic copolymer.
9. The stent of claim 1, wherein the toughening polymer is a polyurethane.
10. The stent of claim 1 wherein the drug reservoir layer further includes a relatively hydrophilic polymer selected from the group consisting of hydroxyethyl methacrylate (HEMA), copolymers of HEMA with acrylate, copolymers of HEMA with polymethylmethacrylate (PMMA), polyvinyl pyrrolidone, polyvinylpyrrolidone/vinyl acetate copolymers (PVP/VA), polyethylene glycols, and polyethylene oxides.
11. The stent of claim 1 comprising more than one active agent.
12. The stent of claim 1 in which the primer layer comprises one or more polymer;
selected from the group consisting of acrylate polymer/copolymer, acrylate carboxyl and/or hydroxyl copolymer, olefin acrylic acid copolymer, ethylene acrylic acid copolymer, polyamide polymers/copolymers polyimide polymers/copolyners, and/or polyether sulfones.
selected from the group consisting of acrylate polymer/copolymer, acrylate carboxyl and/or hydroxyl copolymer, olefin acrylic acid copolymer, ethylene acrylic acid copolymer, polyamide polymers/copolymers polyimide polymers/copolyners, and/or polyether sulfones.
13. The stent of claim 1 in which the primer layer comprises one or more polymer selected from the group consisting of ethylene vinylacetate copolymer, acrylate polymer/copolymer, acrylate carboxyl and/or hydroxyl copolymer, olefin acrylic acid copolymer, ethylene acrylic acid copolymer, polyamide polymers/copolymers polyimide polymers/copolymers, and/or polyether sulfones.
14. The stent of claim 2, wherein the intermediate layer comprises one or more polymers selected from the group consisting of acrylate polymer/copolymer, acrylate carboxyl and/or hydroxyl polymer/copolymer, polyvinylpyrrolidone/vinyl acetate copolymer (PVP/VA), polyurethane, silicone urethane polymer, polycarbonate urethane polymer, polyvinylbutyral, and/or epoxy polymers.
15. The stent of claim 1, wherein the primer and/or drug reservoir layer comprises one or more polymer selected from the group consisting of polyurethane, polycarbonate urethane polymer, and silicone urethane polymer.
16. The stent of claim 1 comprising one or more polymers having a flexural modulus greater that 1000 psi and elongation at break greater than 200%.
17. The stent of claim 1 having a drug reservoir layer comprising a polymer selected from acrylate polymer/copolymer, acrylate hydroxyl and/or carboxyl copolymer, polyvinyl pyrrolidone (PVP), polyvinylpyrrolidone/vinyl acetate copolymer (PVP/VA), cellulose ester, polyurethane, polycarbonate-urethane polymer, silicone-urethane polymer, epoxy polymer, polyethylene glycol and/or polyethylene oxide.
18. The stent of claim 1 having a drug reservoir layer comprising one or more polyurethanes, and one or more cellulose ester polymers.
19. The stent of claim 1 having a drug reservoir layer comprising one or more polymers selected from acrylate polymer/copolymer, acrylate polymer/copolymer containing carboxyl and/or hydroxyl groups, cellulose nitrate and/or other cellulose ester.
20. The stent of claim 1 wherein the active agent comprises an anti-restenotic agent effective at a stented site.
21. The stent of claim 1 having a total coating thickness between about 0.3 and about 30 microns.
22. The stent of claim 1 the primer layer having a thickness between about 0.01 and about 5 microns, and the drug reservoir layer having a thickness of between about 0.1 and about 10 microns.
23. The stent of claim 2 the intermediate layer having a thickness between about 0.1 and about 15 microns.
24. The stent of claim 1, further comprising an active agent selected from one or more of anti-thrombogenic agents, anti-inflammatory agents, antineoplastic agents, anti-proliferative agents, cytostatic agents, cytotoxic agents, antimicrobial agents, anti-restenotic agents, anti-platelet agents, and anti-coagulant agents.
25. The stent of claim 1, further comprising an active agent selected from one or more of anti-fibrin and fibrinolytic agents, anti-platelet agents, prostacyclins (and analogues), glycoprotein IIb/IIIa agents, thromboxane inhibitors, anti-thrombin and anti-coagulant agents, anti-mitotic, antiproliferative and cytostatic agents, antiangiogenic and angiostatic agents, ACE inhibitors, growth factor antagonists, antioxidants, vitamins, calcium channel blockers, fish oil (omega 3-fatty acid), phosphodiesterase inhibitors, nitric acid donor, Somatostatin analogues, immunosuppressive agents, antiinflamatory agents, antimicrobials, radionuclides including alpha, beta and gamma emitting isotopes, COX-2 inhibitors, endothelial promoters, kinase inhibitors, epidermal growth factor kinase inhibitors, tyrosine kinase inhibitors, MAP
kinase inhibitors, and protein transferase inhibitors.
kinase inhibitors, and protein transferase inhibitors.
26. The stent of claim 1, further comprising an active agent selected from one or more of plasmin, streptokinase, single chain urokinase, urokinase, t-PA
(tissue type plasminogen activator), aminocaproic acid, aspirin, monoclonal antibodies, peptides, ReoPro, Cilastagel, eptifibatide, tirofiban, ticlopidine, Vapiprost, dipyridamole, forskolin, angiopeptin, argatroban, dextan, heparin, LMW heparin, heparin complexes, Enoxaparin, Dalteparin, hirudin, recombinant hirudin, anti-thrombin, synthetic antithrombins, thrombin inhibitors, Warfarin, other coumarins, vincristine, vinblastine, paclitaxel and its analogues, methotrexate, cisplatin, fluorouracil, rapamycin, azathioprine, cyclophosphamide, mycophenolic acid, corticosteroids, colchicine, nitroprusside, paclitaxel, angiostatin and endostatin; genetic materials, oligonucleotides, Cilazapril, Lisinopril, Captopril, VEGF, FGF, Probucol, Tocopherol, nifedipine, dipyridamole, Molsidomine, angiopeptin, prednisolone, glucocorticoid, dexamethasone, rifamycin, Re-188, Re-186, I-125, Y-90 celecoxib, Vioxx, dipyridamole, and theophylline.
(tissue type plasminogen activator), aminocaproic acid, aspirin, monoclonal antibodies, peptides, ReoPro, Cilastagel, eptifibatide, tirofiban, ticlopidine, Vapiprost, dipyridamole, forskolin, angiopeptin, argatroban, dextan, heparin, LMW heparin, heparin complexes, Enoxaparin, Dalteparin, hirudin, recombinant hirudin, anti-thrombin, synthetic antithrombins, thrombin inhibitors, Warfarin, other coumarins, vincristine, vinblastine, paclitaxel and its analogues, methotrexate, cisplatin, fluorouracil, rapamycin, azathioprine, cyclophosphamide, mycophenolic acid, corticosteroids, colchicine, nitroprusside, paclitaxel, angiostatin and endostatin; genetic materials, oligonucleotides, Cilazapril, Lisinopril, Captopril, VEGF, FGF, Probucol, Tocopherol, nifedipine, dipyridamole, Molsidomine, angiopeptin, prednisolone, glucocorticoid, dexamethasone, rifamycin, Re-188, Re-186, I-125, Y-90 celecoxib, Vioxx, dipyridamole, and theophylline.
27. The stent of claim 1 wherein the primer layer comprises one or more of acrylate/carboxyl polymer, epoxy polymer, polyvinylpyrrolidone vinylacetate copolymer (PVP/VA).
28. The stent of claim 1 wherein the primer layer comprises one or more of ethylene acrylic acid copolymer (EAA), epoxy polymer, and polycarbonate urethane.
29. The stent of claim 2 wherein the intermediate layer comprises polycarbonate polyurethane.
30. The stent of claim 1 wherein the drug reservoir layer comprises one or more of acrylate/carboxyl polymer, epoxy polymer, and polyvinylpyrrolidone vinylacetate copolymer (PVP/VA).
31. The stent of claim 1 wherein the drug release layer comprises nitrocellulose.
32. The stent of claim 1 wherein the drug release layer comprises nitrocellulose and one or more of polytetramethylene ether glycol urethane, polycarbonate-urethane, silicone-urethane polymer, polyethylene glycol, polymethylmethacrylate-2-hydroxyethylmethacrylate copolymer, polyethylmethacrylate-2-hydroxyethylmethacrylate copolymer, polypropylmethacrylate-2-hydroxyethylmethacrylate copolymer, polybutylmethacrylate-2-hydroxyethylmethacrylate copolymer, Polymethylacrylate-hydroxyethylmethacrylate copolymer, polyethylacrylate-2-hydroxyethylmethacrylate copolymer, polypropylacrylate-2-hydroxymethacrylate copolymer, polybutylacrylate-2-hydroxyethylmethacrylate copolymer, copolymermethylvinylether maleicanhydride copolymer, and poly (2-hydroxyethyl methacrylate).
33. The stent of claim 1, wherein the drug release layer comprises an ionic heparin complex, and at least one other bioactive agent that is not anti-thrombogenic.
34. The stent of claim 1, further comprising active agents, wherein one of the agents is an ionic complex of heparin, and at least one more agent is present that is selected from the group consisting of an anti-angiogenic factor, an immunosuppressing agent, an antimicrobial agent, an anti-inflammatory agent, an anti-restenotic agent and combinations.
35. The stent of claim 1, further comprising heparin together with at least one anti-restenotic drug selected from the group consisting of paclitaxel, rapamycin and combinations.
36. The stent of claim 1, further comprising an active agent selected from the group consisting of paclitaxel, heparin complexes, rifamycin, methotrexate, and combinations.
37. The stent of claim 1, further comprising benzalkonium heparinate and paclitaxel.
38. The stent of claim 1, wherein the primer layer comprises an ethylene acrylic acid copolymer and an epoxy polymer.
39. The stent of claim 38, wherein the ethylene acrylic acid copolymer is one or more of PRIMACOR 5989 and 5990.
40. The stent of claim 38, wherein the epoxy is one or more of EPOTUF 38-505, EPOTUF 37-618, and EPON 1001.
41. The stent of claim 1, wherein the drug reservoir layer comprises a polyurethane and a cellulose nitrate.
42. The stent of claim 41, wherein the polyurethane is polytetramethylene ether glycol urethane and/or polycarbonate urethane.
43. The stent of claim 41 wherein the polyurethane is selected from the group consisting of Chronoflex AR, Chronoflex AL, Chronoflex C and Bionate 80A.
44. The stent of claim 41 wherein the polyurethane is Chronoflex AR.
45. The stent of claim 1, wherein the primer layer comprises an ethylene acrylic acid copolymer and an epoxy polymer and the drug reservoir layer comprises a polyurethane and a cellulose ester.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/662,877 US7771468B2 (en) | 2001-03-16 | 2003-09-16 | Medicated stent having multi-layer polymer coating |
US10/662,877 | 2003-09-16 | ||
PCT/US2004/030354 WO2005030094A1 (en) | 2003-09-16 | 2004-09-16 | Medicated stent having multi-layer polymer coating |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2538669A1 true CA2538669A1 (en) | 2005-04-07 |
CA2538669C CA2538669C (en) | 2010-11-30 |
Family
ID=34393334
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA2538669A Expired - Fee Related CA2538669C (en) | 2003-09-16 | 2004-09-16 | Medicated stent having multi-layer polymer coating |
Country Status (5)
Country | Link |
---|---|
US (3) | US7771468B2 (en) |
EP (1) | EP1680047A4 (en) |
JP (1) | JP2007505704A (en) |
CA (1) | CA2538669C (en) |
WO (1) | WO2005030094A1 (en) |
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- 2003-09-16 US US10/662,877 patent/US7771468B2/en not_active Expired - Fee Related
-
2004
- 2004-09-16 EP EP04784270A patent/EP1680047A4/en not_active Withdrawn
- 2004-09-16 WO PCT/US2004/030354 patent/WO2005030094A1/en active Application Filing
- 2004-09-16 JP JP2006527022A patent/JP2007505704A/en active Pending
- 2004-09-16 CA CA2538669A patent/CA2538669C/en not_active Expired - Fee Related
-
2010
- 2010-07-01 US US12/828,512 patent/US8287590B2/en not_active Expired - Fee Related
-
2012
- 2012-10-15 US US13/651,828 patent/US20130253636A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
US8287590B2 (en) | 2012-10-16 |
CA2538669C (en) | 2010-11-30 |
US7771468B2 (en) | 2010-08-10 |
US20040117007A1 (en) | 2004-06-17 |
US20130253636A1 (en) | 2013-09-26 |
JP2007505704A (en) | 2007-03-15 |
US20100331967A1 (en) | 2010-12-30 |
EP1680047A4 (en) | 2011-07-27 |
EP1680047A1 (en) | 2006-07-19 |
WO2005030094A1 (en) | 2005-04-07 |
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