CA2519503C - Drug delivery from a polymer coating on a medical device - Google Patents
Drug delivery from a polymer coating on a medical device Download PDFInfo
- Publication number
- CA2519503C CA2519503C CA2519503A CA2519503A CA2519503C CA 2519503 C CA2519503 C CA 2519503C CA 2519503 A CA2519503 A CA 2519503A CA 2519503 A CA2519503 A CA 2519503A CA 2519503 C CA2519503 C CA 2519503C
- Authority
- CA
- Canada
- Prior art keywords
- coating
- monomer unit
- copolymer
- layer
- methacrylate
- 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.)
- Expired - Lifetime
Links
- 238000000576 coating method Methods 0.000 title claims abstract description 200
- 239000011248 coating agent Substances 0.000 title claims abstract description 186
- 229920000642 polymer Polymers 0.000 title claims description 201
- 238000012377 drug delivery Methods 0.000 title description 4
- 239000000178 monomer Substances 0.000 claims abstract description 389
- 229920001577 copolymer Polymers 0.000 claims abstract description 248
- 230000009477 glass transition Effects 0.000 claims abstract description 146
- 238000000034 method Methods 0.000 claims abstract description 68
- 239000000203 mixture Substances 0.000 claims abstract description 68
- 229920001519 homopolymer Polymers 0.000 claims abstract description 66
- 239000003814 drug Substances 0.000 claims description 112
- 229940124597 therapeutic agent Drugs 0.000 claims description 100
- 229920000669 heparin Polymers 0.000 claims description 49
- 125000000524 functional group Chemical group 0.000 claims description 48
- 229960002897 heparin Drugs 0.000 claims description 46
- -1 poly (isocyanatoethyl Chemical group 0.000 claims description 45
- 229960001592 paclitaxel Drugs 0.000 claims description 42
- 229930012538 Paclitaxel Natural products 0.000 claims description 41
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- 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 claims description 39
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- 239000002904 solvent Substances 0.000 claims description 29
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 22
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 21
- 239000002202 Polyethylene glycol Substances 0.000 claims description 21
- 229920001223 polyethylene glycol Polymers 0.000 claims description 21
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 16
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 9
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- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 8
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 claims description 8
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
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- AJXBTRZGLDTSST-UHFFFAOYSA-N amino 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)ON AJXBTRZGLDTSST-UHFFFAOYSA-N 0.000 claims description 4
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- 230000004044 response Effects 0.000 claims description 4
- 125000001174 sulfone group Chemical group 0.000 claims description 4
- QRIMLDXJAPZHJE-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CO QRIMLDXJAPZHJE-UHFFFAOYSA-N 0.000 claims description 3
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 3
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 3
- 150000001241 acetals Chemical class 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 3
- 150000001266 acyl halides Chemical class 0.000 claims description 3
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- 150000001345 alkine derivatives Chemical class 0.000 claims description 3
- 150000001361 allenes Chemical class 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
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- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 3
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 claims description 3
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical class B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 3
- 229910000085 borane Inorganic materials 0.000 claims description 3
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
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- 239000004005 microsphere Substances 0.000 claims description 3
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- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 3
- 229920000570 polyether Polymers 0.000 claims description 3
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- 150000003567 thiocyanates Chemical class 0.000 claims description 3
- RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical class SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 claims description 3
- 150000003573 thiols Chemical class 0.000 claims description 3
- YXMISKNUHHOXFT-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) prop-2-enoate Chemical compound C=CC(=O)ON1C(=O)CCC1=O YXMISKNUHHOXFT-UHFFFAOYSA-N 0.000 claims description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 claims description 2
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 2
- 108010035532 Collagen Proteins 0.000 claims description 2
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- 102000016942 Elastin Human genes 0.000 claims description 2
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 claims description 2
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- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 2
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- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 claims description 2
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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
- Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
- Y10T428/24942—Structurally defined web or sheet [e.g., overall dimension, etc.] including components having same physical characteristic in differing degree
- Y10T428/2495—Thickness [relative or absolute]
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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]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/31909—Next to second addition polymer from unsaturated monomers
- Y10T428/31928—Ester, halide or nitrile of addition polymer
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Vascular Medicine (AREA)
- Animal Behavior & Ethology (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
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Applications Claiming Priority (3)
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| US45133303P | 2003-02-28 | 2003-02-28 | |
| US60/451,333 | 2003-02-28 | ||
| PCT/IB2004/000534 WO2004075943A1 (en) | 2003-02-28 | 2004-03-01 | Polymeric network system for medical devices and methods of use |
Publications (2)
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| CA2519503A1 CA2519503A1 (en) | 2004-09-10 |
| CA2519503C true CA2519503C (en) | 2015-04-28 |
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Families Citing this family (93)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999055396A1 (en) | 1998-04-27 | 1999-11-04 | Surmodics, Inc. | Bioactive agent release coating |
| US20020188037A1 (en) * | 1999-04-15 | 2002-12-12 | Chudzik Stephen J. | Method and system for providing bioactive agent release coating |
| US7097850B2 (en) | 2002-06-18 | 2006-08-29 | Surmodics, Inc. | Bioactive agent release coating and controlled humidity method |
| US20040111144A1 (en) * | 2002-12-06 | 2004-06-10 | Lawin Laurie R. | Barriers for polymeric coatings |
| US7776926B1 (en) | 2002-12-11 | 2010-08-17 | Advanced Cardiovascular Systems, Inc. | Biocompatible coating for implantable medical devices |
| US7758880B2 (en) | 2002-12-11 | 2010-07-20 | Advanced Cardiovascular Systems, Inc. | Biocompatible polyacrylate compositions for medical applications |
| JP4791349B2 (ja) | 2003-02-28 | 2011-10-12 | バイオインターラクションズ リミテッド | 医療機器のためのポリマーネットワークシステム及び使用方法 |
| US20150005180A9 (en) * | 2003-09-19 | 2015-01-01 | Kazuhiko Ishihara | Biochip |
| AU2004281178A1 (en) * | 2003-10-15 | 2005-04-28 | Tyco Healthcare Group, Lp | Method of joining materials |
| US7550444B2 (en) | 2004-03-26 | 2009-06-23 | Surmodics, Inc. | Composition and method for preparing biocompatible surfaces |
| JP2007530173A (ja) | 2004-03-26 | 2007-11-01 | サーモディクス，インコーポレイティド | 生体適合性表面のための方法およびシステム |
| JP2007532187A (ja) | 2004-04-06 | 2007-11-15 | サーモディクス，インコーポレイティド | 生物活性物質のためのコーティング組成物 |
| WO2005115490A2 (en) * | 2004-05-25 | 2005-12-08 | Surmodics, Inc. | Natural biodegradable polysaccharide coatings for meical articles |
| US20060088571A1 (en) * | 2004-10-21 | 2006-04-27 | Medtronic Vascular, Inc. | Biocompatible and hemocompatible polymer compositions |
| US7919110B2 (en) * | 2005-01-25 | 2011-04-05 | Boston Scientific Scimed, Inc. | Medical device drug release regions containing non-covalently bound polymers |
| US8075906B2 (en) | 2005-02-01 | 2011-12-13 | Boston Scientific Scimed, Inc. | Medical devices having polymeric regions with copolymers containing hydrocarbon and heteroatom-containing monomeric species |
| US20060171980A1 (en) * | 2005-02-01 | 2006-08-03 | Helmus Michael N | Implantable or insertable medical devices having optimal surface energy |
| US7517914B2 (en) * | 2005-04-04 | 2009-04-14 | Boston Scientificscimed, Inc. | Controlled degradation materials for therapeutic agent delivery |
| US7591841B2 (en) * | 2005-12-16 | 2009-09-22 | Advanced Cardiovascular Systems, Inc. | Implantable devices for accelerated healing |
| US20070155907A1 (en) * | 2005-12-30 | 2007-07-05 | Zhao Jonathon Z | Biologically active block copolymers |
| US11039942B2 (en) * | 2006-06-13 | 2021-06-22 | Sino Medical Sciences Technology Inc. | Drug eluting stent and method of use of the same for enabling restoration of functional endothelial cell layers |
| US10188826B2 (en) * | 2006-09-29 | 2019-01-29 | Covidien Lp | Catheters including antimicrobial sleeve and methods of making catheters |
| WO2008076383A2 (en) * | 2006-12-18 | 2008-06-26 | Med Institute Inc. | Stent graft with releasable therapeutic agent |
| US8241567B2 (en) * | 2007-04-20 | 2012-08-14 | Becton, Dickinson And Company | Hydrogel compositions |
| US8133553B2 (en) | 2007-06-18 | 2012-03-13 | Zimmer, Inc. | Process for forming a ceramic layer |
| US8309521B2 (en) | 2007-06-19 | 2012-11-13 | Zimmer, Inc. | Spacer with a coating thereon for use with an implant device |
| US8608049B2 (en) | 2007-10-10 | 2013-12-17 | Zimmer, Inc. | Method for bonding a tantalum structure to a cobalt-alloy substrate |
| AU2009204183A1 (en) * | 2008-01-09 | 2009-07-16 | Innovative Health Technologies, Llc | Implant pellets and methods for performing bone augmentation and preservation |
| DE102008006654A1 (de) * | 2008-01-30 | 2009-08-06 | Biotronik Vi Patent Ag | Implantat mit einem Grundkörper aus einer biokorrodierbaren Legierung |
| EP2249892B1 (fr) * | 2008-02-21 | 2017-11-15 | Hexacath | Dispositif medical implantable avec une couche de protection/retention d'un agent actif ou medicament, notamment hydrosoluble |
| US8034396B2 (en) * | 2008-04-01 | 2011-10-11 | Tyco Healthcare Group Lp | Bioadhesive composition formed using click chemistry |
| DK2268332T3 (da) * | 2008-04-09 | 2019-05-06 | Aachen Scient International Pte Ltd | Fremgangsmåde til produktion af en bioaktiv overflade på en endoprostese eller på ballonen af et ballonkateter |
| US20090264478A1 (en) * | 2008-04-18 | 2009-10-22 | Warsaw Orthopedic, Inc. | Sulfasalazine formulations in a biodegradable polymer carrier |
| GB0816783D0 (en) * | 2008-09-15 | 2008-10-22 | Carmeda Ab | Immobilised biological entities |
| US8049061B2 (en) | 2008-09-25 | 2011-11-01 | Abbott Cardiovascular Systems, Inc. | Expandable member formed of a fibrous matrix having hydrogel polymer for intraluminal drug delivery |
| US8226603B2 (en) | 2008-09-25 | 2012-07-24 | Abbott Cardiovascular Systems Inc. | Expandable member having a covering formed of a fibrous matrix for intraluminal drug delivery |
| US8076529B2 (en) | 2008-09-26 | 2011-12-13 | Abbott Cardiovascular Systems, Inc. | Expandable member formed of a fibrous matrix for intraluminal drug delivery |
| CA2753162A1 (en) | 2009-02-21 | 2010-08-26 | Sofradim Production | Amphiphilic compounds and self-assembling compositions made therefrom |
| EP2398850B1 (en) | 2009-02-21 | 2018-08-22 | Sofradim Production | Medical devices with an activated coating |
| WO2010096654A1 (en) | 2009-02-21 | 2010-08-26 | Tyco Healthcare Group Lp | Medical devices having activated surfaces |
| US8969473B2 (en) | 2009-02-21 | 2015-03-03 | Sofradim Production | Compounds and medical devices activated with solvophobic linkers |
| CA2753171A1 (en) | 2009-02-21 | 2010-08-26 | Sofradim Production | Crosslinked fibers and method of making same using uv radiation |
| WO2010095047A2 (en) | 2009-02-21 | 2010-08-26 | Sofradim Production | Apparatus and method of reacting polymers passing through metal ion chelated resin matrix to produce injectable medical devices |
| AU2010215196B2 (en) | 2009-02-21 | 2015-04-16 | Covidien Lp | Crosslinked fibers and method of making same by extrusion |
| US8968733B2 (en) * | 2009-02-21 | 2015-03-03 | Sofradim Production | Functionalized surgical adhesives |
| US8663689B2 (en) * | 2009-02-21 | 2014-03-04 | Sofradim Production | Functionalized adhesive medical gel |
| US8535477B2 (en) * | 2009-02-21 | 2013-09-17 | Sofradim Production | Medical devices incorporating functional adhesives |
| EP2398584A2 (en) | 2009-02-21 | 2011-12-28 | Sofradim Production | Apparatus and method of reaching polymers by exposure to uv radiation to produce injectable medical devices |
| US8877170B2 (en) * | 2009-02-21 | 2014-11-04 | Sofradim Production | Medical device with inflammatory response-reducing coating |
| US8512728B2 (en) | 2009-02-21 | 2013-08-20 | Sofradim Production | Method of forming a medical device on biological tissue |
| AU2010215931A1 (en) | 2009-02-21 | 2011-10-13 | Covidien Lp | Medical devices having activated surfaces |
| CN102933658A (zh) | 2009-12-18 | 2013-02-13 | 界面生物公司 | 从自组装涂层局部递送药物 |
| EP2338534A2 (de) * | 2009-12-21 | 2011-06-29 | Biotronik VI Patent AG | Medizinisches Implantat, Beschichtungsverfahren sowie Implantationsverfahren |
| GB201004101D0 (en) | 2010-03-12 | 2010-04-28 | Carmeda Ab | Immobilised biological entities |
| WO2011119536A1 (en) | 2010-03-22 | 2011-09-29 | Abbott Cardiovascular Systems Inc. | Stent delivery system having a fibrous matrix covering with improved stent retention |
| US9272074B2 (en) | 2010-03-25 | 2016-03-01 | Sofradim Production | Surgical fasteners and methods for sealing wounds |
| US8795331B2 (en) | 2010-03-25 | 2014-08-05 | Covidien Lp | Medical devices incorporating functional adhesives |
| CA2794450A1 (en) * | 2010-03-25 | 2011-09-29 | Tyco Healthcare Group Lp | Chemical knots for sutures |
| AU2011233663B2 (en) * | 2010-04-03 | 2016-04-14 | Praful Doshi | Medical devices including medicaments and methods of making and using same |
| US10413506B2 (en) | 2010-04-03 | 2019-09-17 | Praful Doshi | Medical devices including medicaments and methods of making and using same including enhancing comfort, enhancing drug penetration, and treatment of myopia |
| AU2011276443A1 (en) | 2010-06-29 | 2013-01-31 | Covidien Lp | Microwave-powered reactor and method for in situ forming implants |
| WO2012001532A2 (en) | 2010-07-01 | 2012-01-05 | Sofradim Production | Medical device with predefined activated cellular integration |
| WO2012014080A2 (en) | 2010-07-27 | 2012-02-02 | Sofradim Production | Polymeric fibers having tissue reactive members |
| US8480227B2 (en) | 2010-07-30 | 2013-07-09 | Novartis Ag | Silicone hydrogel lenses with water-rich surfaces |
| US11786455B2 (en) | 2011-05-10 | 2023-10-17 | Itochu Chemical Frontier Corporation | Non-aqueous patch |
| ES3034911T3 (en) | 2011-05-10 | 2025-08-26 | Itochu Chemical Frontier Corp | Non-aqueous patch |
| JP5856153B2 (ja) | 2011-05-10 | 2016-02-09 | 伊藤忠ケミカルフロンティア株式会社 | 非水性貼付剤 |
| SI2823815T1 (sl) | 2011-09-27 | 2018-09-28 | Itochu Chemical Frontier Corporation | Ne-vodni obliž |
| HUE029018T2 (en) | 2011-10-12 | 2017-02-28 | Novartis Ag | A method for producing UV absorbing contact lenses by coating |
| KR101201984B1 (ko) * | 2012-02-28 | 2012-11-15 | 주식회사 제네웰 | 창상 봉합용 조직접착제 및 그 제조방법 |
| CA2867766C (en) * | 2012-03-27 | 2018-08-07 | F. Hoffmann-La Roche Ag | Improved spacer membrane for an enzymatic in-vivo sensor |
| HUE031702T2 (en) | 2012-12-17 | 2017-07-28 | Novartis Ag | A method for producing improved UV absorbing ophthalmic lenses |
| JP6454325B2 (ja) * | 2013-04-26 | 2019-01-16 | バイオインタラクションズ・リミテッドＢｉｏＩｎｔｅｒａｃｔｉｏｎｓ Ｌｔｄ | 生物活性被覆 |
| USRE49528E1 (en) * | 2013-04-26 | 2023-05-16 | Biointeractions Ltd. | Bioactive coatings |
| US9775928B2 (en) | 2013-06-18 | 2017-10-03 | Covidien Lp | Adhesive barbed filament |
| HUE038809T2 (hu) | 2013-12-17 | 2018-11-28 | Novartis Ag | Térhálósított hidrofíl bevonattal ellátott szilikon hidrogél lencse |
| JP2016005533A (ja) * | 2014-05-30 | 2016-01-14 | 株式会社日本ステントテクノロジー | ステント |
| US20160015852A1 (en) * | 2014-07-15 | 2016-01-21 | Industrial Technology Research Institute | Composite material |
| MY183678A (en) | 2014-08-26 | 2021-03-08 | Alcon Inc | Method for applying stable coating on silicone hydrogel contact lenses |
| CN104610516B (zh) * | 2015-01-12 | 2018-05-18 | 西北大学 | 含磷酰胆碱和聚乙二醇的功能聚合物及其抗污涂层的构建方法 |
| US20160346219A1 (en) | 2015-06-01 | 2016-12-01 | Autotelic Llc | Phospholipid-coated therapeutic agent nanoparticles and related methods |
| JP6805488B2 (ja) | 2015-12-02 | 2020-12-23 | 国立大学法人山形大学 | 医療用具用重合体用単量体組成物、及び、医療用具用重合体 |
| KR102604468B1 (ko) | 2015-12-15 | 2023-11-22 | 알콘 인코포레이티드 | 실리콘 하이드로겔 콘택트 렌즈 상에 안정한 코팅을 적용하기 위한 방법 |
| US11150219B2 (en) | 2016-08-03 | 2021-10-19 | Basf Se | Bio-recognition elements |
| CN117492228A (zh) | 2017-12-13 | 2024-02-02 | 爱尔康公司 | 周抛和月抛水梯度接触镜片 |
| JP2021531061A (ja) | 2018-05-22 | 2021-11-18 | インターフェース バイオロジクス，インコーポレーテッド | 薬物を脈管壁に送達するための組成物及び方法 |
| CN109096431B (zh) * | 2018-08-21 | 2020-11-27 | 湖南工业大学 | 一种纳米发电机与自驱动传感器用聚丙烯酸丁酯-聚甲基丙烯酸丁酯共聚物及其制备方法 |
| JP7603447B2 (ja) * | 2019-01-09 | 2024-12-20 | 株式会社日本触媒 | 防汚剤、防汚塗膜及び防汚塗膜付き基材 |
| CN121648353A (zh) * | 2019-03-19 | 2026-03-13 | 杰美特涂层科技(厦门)有限公司 | 一种包含共价键合的肝素涂层的医疗装置的制备方法 |
| AU2020302924A1 (en) | 2019-06-27 | 2022-02-17 | Layerbio, Inc. | Ocular device delivery methods and systems |
| CN113072669B (zh) * | 2020-01-03 | 2022-02-18 | 万华化学集团股份有限公司 | 核-壳结构的丙烯酸酯类可溶胀流变改性剂及其制备方法 |
| CN117159811A (zh) * | 2022-01-30 | 2023-12-05 | 苏州浩微生物医疗科技有限公司 | 一种表面处理组合物、医疗器械及其制备方法 |
| CN115970070B (zh) * | 2022-12-26 | 2023-08-18 | 上海发微医用材料有限公司 | 含亲水聚合物的涂层体系及双层涂层体系、亲水涂层和应用 |
Family Cites Families (63)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US150549A (en) * | 1874-05-05 | e wing | ||
| US2353A (en) * | 1841-11-12 | i s p e t t i t s m i t h | ||
| US1937475A (en) * | 1930-09-24 | 1933-11-28 | Peter S Legge | Abrading apparatus |
| US6387379B1 (en) * | 1987-04-10 | 2002-05-14 | University Of Florida | Biofunctional surface modified ocular implants, surgical instruments, medical devices, prostheses, contact lenses and the like |
| CA2027921C (en) * | 1989-10-19 | 1997-12-09 | Nobuo Nakabayashi | Bone cement composition, cured product thereof, implant material and process for the preparation of the same |
| JP2751938B2 (ja) * | 1989-10-19 | 1998-05-18 | 宣男 中林 | 骨セメント組成物および硬化体 |
| US5843089A (en) * | 1990-12-28 | 1998-12-01 | Boston Scientific Corporation | Stent lining |
| EP0623150A4 (en) | 1992-11-19 | 1999-08-25 | Univ Case Western Reserve | Nonthrombogenic implant surfaces. |
| WO1994021308A1 (en) * | 1993-03-18 | 1994-09-29 | Cedars-Sinai Medical Center | Drug incorporating and releasing polymeric coating for bioprosthesis |
| US5464650A (en) * | 1993-04-26 | 1995-11-07 | Medtronic, Inc. | Intravascular stent and method |
| US5637113A (en) * | 1994-12-13 | 1997-06-10 | Advanced Cardiovascular Systems, Inc. | Polymer film for wrapping a stent structure |
| US6231600B1 (en) * | 1995-02-22 | 2001-05-15 | Scimed Life Systems, Inc. | Stents with hybrid coating for medical devices |
| US5607475A (en) * | 1995-08-22 | 1997-03-04 | Medtronic, Inc. | Biocompatible medical article and method |
| GB9608882D0 (en) | 1996-04-30 | 1996-07-03 | Luthra Ajay K | Non-thrombogenic and anti-thrombogenic polymers |
| US5980972A (en) | 1996-12-20 | 1999-11-09 | Schneider (Usa) Inc | Method of applying drug-release coatings |
| JP2002515932A (ja) | 1997-04-18 | 2002-05-28 | カリフォルニア インスティチュート オブ テクノロジー | 多機能性ポリマー性組織コーティング |
| US6273913B1 (en) | 1997-04-18 | 2001-08-14 | Cordis Corporation | Modified stent useful for delivery of drugs along stent strut |
| GB9714650D0 (en) * | 1997-07-11 | 1997-09-17 | Strakan Ltd | Block copolymer |
| IL122153A (en) | 1997-11-10 | 2005-03-20 | Alomone Labs Ltd | Biocompatible polymeric coating material |
| US6224625B1 (en) * | 1997-10-27 | 2001-05-01 | Iowa-India Investments Company Limited | Low profile highly expandable stent |
| US6221425B1 (en) | 1998-01-30 | 2001-04-24 | Advanced Cardiovascular Systems, Inc. | Lubricious hydrophilic coating for an intracorporeal medical device |
| US6007833A (en) | 1998-03-19 | 1999-12-28 | Surmodics, Inc. | Crosslinkable macromers bearing initiator groups |
| WO1999055396A1 (en) * | 1998-04-27 | 1999-11-04 | Surmodics, Inc. | Bioactive agent release coating |
| FR2785812B1 (fr) * | 1998-11-16 | 2002-11-29 | Commissariat Energie Atomique | Protheses bioactives, notamment a proprietes immunosuppressives, antistenose et antithrombose, et leur fabrication |
| US6734256B1 (en) * | 1998-12-29 | 2004-05-11 | 3M Innovative Properties Company | Block copolymer hot-melt processable adhesives, methods of their preparation, and articles therefrom |
| JP2002534461A (ja) * | 1999-01-12 | 2002-10-15 | クアナム メディカル コーポレイション | 水不溶性のパクリタキセル誘導体の投与のための組成物および方法 |
| US6530950B1 (en) * | 1999-01-12 | 2003-03-11 | Quanam Medical Corporation | Intraluminal stent having coaxial polymer member |
| WO2000041738A1 (en) * | 1999-01-12 | 2000-07-20 | Quanam Medical Corporation | Polymer compositions for intraluminal stent |
| ATE226837T1 (de) * | 1999-01-12 | 2002-11-15 | Quanam Medical Corp | Polymerzusammensetzung für intraluminalen stent |
| US6340465B1 (en) | 1999-04-12 | 2002-01-22 | Edwards Lifesciences Corp. | Lubricious coatings for medical devices |
| GB2349644A (en) | 1999-05-01 | 2000-11-08 | Biointeractions Ltd | Infection resistant polymers, methods for their preparation, and their uses |
| US6287379B1 (en) * | 1999-06-10 | 2001-09-11 | Jack Khalifeh | Apparatus and method for disposing rubber waste material during the manufacturing of products which are heated in a rotary kiln |
| US6258121B1 (en) | 1999-07-02 | 2001-07-10 | Scimed Life Systems, Inc. | Stent coating |
| US6503556B2 (en) * | 2000-12-28 | 2003-01-07 | Advanced Cardiovascular Systems, Inc. | Methods of forming a coating for a prosthesis |
| US6713119B2 (en) * | 1999-09-03 | 2004-03-30 | Advanced Cardiovascular Systems, Inc. | Biocompatible coating for a prosthesis and a method of forming the same |
| US6251136B1 (en) * | 1999-12-08 | 2001-06-26 | Advanced Cardiovascular Systems, Inc. | Method of layering a three-coated stent using pharmacological and polymeric agents |
| JP5460939B2 (ja) | 2000-03-13 | 2014-04-02 | バイオコンパティブルズ ユーケー リミテッド | ヒドロゲル生物医学用製品 |
| US6776796B2 (en) | 2000-05-12 | 2004-08-17 | Cordis Corportation | Antiinflammatory drug and delivery device |
| US7682648B1 (en) | 2000-05-31 | 2010-03-23 | Advanced Cardiovascular Systems, Inc. | Methods for forming polymeric coatings on stents |
| US6673385B1 (en) * | 2000-05-31 | 2004-01-06 | Advanced Cardiovascular Systems, Inc. | Methods for polymeric coatings stents |
| CA2424029C (en) * | 2000-09-29 | 2008-01-29 | Cordis Corporation | Coated medical devices |
| US6545097B2 (en) * | 2000-12-12 | 2003-04-08 | Scimed Life Systems, Inc. | Drug delivery compositions and medical devices containing block copolymer |
| DE10114247A1 (de) * | 2001-03-22 | 2002-10-10 | Heraeus Kulzer Gmbh & Co Kg | Antibiotikum-/Antibiotika-Polymer-Kombination |
| US8101196B2 (en) * | 2001-06-26 | 2012-01-24 | Biointeractions, Ltd. | Polysaccharide biomaterials and methods of use thereof |
| GB0122393D0 (en) | 2001-09-17 | 2001-11-07 | Polybiomed Ltd | Treating metal surfaces to enhance bio-compatibility |
| US7491233B1 (en) * | 2002-07-19 | 2009-02-17 | Advanced Cardiovascular Systems Inc. | Purified polymers for coatings of implantable medical devices |
| US6806320B2 (en) * | 2002-11-15 | 2004-10-19 | 3M Innovative Properties Company | Block copolymer melt-processable compositions, methods of their preparation, and articles therefrom |
| US20040122161A1 (en) * | 2002-12-21 | 2004-06-24 | Paul Charles W. | Hot melt adhesive based on acrylic block copolymers |
| JP4791349B2 (ja) | 2003-02-28 | 2011-10-12 | バイオインターラクションズ リミテッド | 医療機器のためのポリマーネットワークシステム及び使用方法 |
| IES20030294A2 (en) | 2003-04-17 | 2004-10-20 | Medtronic Vascular Connaught | Coating for biomedical devices |
| US7186789B2 (en) * | 2003-06-11 | 2007-03-06 | Advanced Cardiovascular Systems, Inc. | Bioabsorbable, biobeneficial polyester polymers for use in drug eluting stent coatings |
| US7544381B2 (en) | 2003-09-09 | 2009-06-09 | Boston Scientific Scimed, Inc. | Lubricious coatings for medical device |
| US20050054774A1 (en) | 2003-09-09 | 2005-03-10 | Scimed Life Systems, Inc. | Lubricious coating |
| US20050070688A1 (en) | 2003-09-26 | 2005-03-31 | 3M Innovative Properties Company | Reactive hydrophilic oligomers |
| US7807722B2 (en) * | 2003-11-26 | 2010-10-05 | Advanced Cardiovascular Systems, Inc. | Biobeneficial coating compositions and methods of making and using thereof |
| US8309112B2 (en) | 2003-12-24 | 2012-11-13 | Advanced Cardiovascular Systems, Inc. | Coatings for implantable medical devices comprising hydrophilic substances and methods for fabricating the same |
| US7771740B2 (en) * | 2004-07-19 | 2010-08-10 | Boston Scientific Scimed, Inc. | Medical devices containing copolymers with graft copolymer endblocks for drug delivery |
| US7919110B2 (en) * | 2005-01-25 | 2011-04-05 | Boston Scientific Scimed, Inc. | Medical device drug release regions containing non-covalently bound polymers |
| CA2609198A1 (en) | 2005-06-02 | 2006-12-07 | Surmodics, Inc. | Hydrophilic polymeric coatings for medical articles |
| US20070155907A1 (en) | 2005-12-30 | 2007-07-05 | Zhao Jonathon Z | Biologically active block copolymers |
| US7622477B2 (en) | 2006-02-28 | 2009-11-24 | Cordis Corporation | Isomers and 42-epimers of rapamycin alkyl ether analogs, methods of making and using the same |
| US20090041923A1 (en) | 2007-08-06 | 2009-02-12 | Abbott Cardiovascular Systems Inc. | Medical device having a lubricious coating with a hydrophilic compound in an interlocking network |
| US8277826B2 (en) | 2008-06-25 | 2012-10-02 | Baxter International Inc. | Methods for making antimicrobial resins |
-
2004
- 2004-03-01 JP JP2006502480A patent/JP4791349B2/ja not_active Expired - Lifetime
- 2004-03-01 EP EP20040715966 patent/EP1603603B1/en not_active Expired - Lifetime
- 2004-03-01 CA CA2519503A patent/CA2519503C/en not_active Expired - Lifetime
- 2004-03-01 DK DK04715966.0T patent/DK1603603T3/en active
- 2004-03-01 US US10/790,338 patent/US7655038B2/en not_active Ceased
- 2004-03-01 PL PL04715966T patent/PL1603603T3/pl unknown
- 2004-03-01 EP EP14020085.8A patent/EP2918296A1/en not_active Withdrawn
- 2004-03-01 ES ES04715966T patent/ES2531326T3/es not_active Expired - Lifetime
- 2004-03-01 WO PCT/IB2004/000534 patent/WO2004075943A1/en not_active Ceased
- 2004-03-01 AU AU2004216404A patent/AU2004216404C1/en not_active Ceased
- 2004-03-01 PT PT04715966T patent/PT1603603E/pt unknown
-
2012
- 2012-02-02 US US13/365,092 patent/USRE45500E1/en not_active Expired - Lifetime
-
2016
- 2016-03-16 HK HK16103055.8A patent/HK1215199A1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2531326T3 (es) | 2015-03-13 |
| EP1603603A1 (en) | 2005-12-14 |
| USRE45500E1 (en) | 2015-04-28 |
| HK1215199A1 (en) | 2016-08-19 |
| JP2006519049A (ja) | 2006-08-24 |
| DK1603603T3 (en) | 2015-02-23 |
| AU2004216404A1 (en) | 2004-09-10 |
| WO2004075943A1 (en) | 2004-09-10 |
| JP4791349B2 (ja) | 2011-10-12 |
| US7655038B2 (en) | 2010-02-02 |
| EP1603603B1 (en) | 2014-11-19 |
| US20040170752A1 (en) | 2004-09-02 |
| PT1603603E (pt) | 2015-02-24 |
| AU2004216404C1 (en) | 2011-04-28 |
| CA2519503A1 (en) | 2004-09-10 |
| AU2004216404B2 (en) | 2010-11-25 |
| EP2918296A1 (en) | 2015-09-16 |
| PL1603603T3 (pl) | 2015-07-31 |
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