CA2419429C - Elastomeric functional biodegradable copolyester amides and copolyester urethanes - Google Patents
Elastomeric functional biodegradable copolyester amides and copolyester urethanes Download PDFInfo
- Publication number
- CA2419429C CA2419429C CA2419429A CA2419429A CA2419429C CA 2419429 C CA2419429 C CA 2419429C CA 2419429 A CA2419429 A CA 2419429A CA 2419429 A CA2419429 A CA 2419429A CA 2419429 C CA2419429 C CA 2419429C
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- Prior art keywords
- polymer
- independently
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- alkyl
- residue
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- Expired - Lifetime
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- 150000003673 urethanes Chemical class 0.000 title abstract description 6
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- XXAYGJGDVLSEML-LBPRGKRZSA-N benzyl (2s)-2,6-diaminohexanoate Chemical compound NCCCC[C@H](N)C(=O)OCC1=CC=CC=C1 XXAYGJGDVLSEML-LBPRGKRZSA-N 0.000 claims description 71
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical group CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 68
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- ALBODLTZUXKBGZ-JUUVMNCLSA-N (2s)-2-amino-3-phenylpropanoic acid;(2s)-2,6-diaminohexanoic acid Chemical compound NCCCC[C@H](N)C(O)=O.OC(=O)[C@@H](N)CC1=CC=CC=C1 ALBODLTZUXKBGZ-JUUVMNCLSA-N 0.000 claims description 4
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- 238000006065 biodegradation reaction Methods 0.000 abstract description 30
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- 239000000243 solution Substances 0.000 description 44
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 44
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Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/44—Polyester-amides
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- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/59—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes
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- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/59—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes
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- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
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- A61K47/595—Polyamides, e.g. nylon
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G71/00—Macromolecular compounds obtained by reactions forming a ureide or urethane link, otherwise, than from isocyanate radicals in the main chain of the macromolecule
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Medicinal Preparation (AREA)
- Polyamides (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Biological Depolymerization Polymers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polyesters Or Polycarbonates (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/651,338 | 2000-08-30 | ||
| US09/651,338 US6503538B1 (en) | 2000-08-30 | 2000-08-30 | Elastomeric functional biodegradable copolyester amides and copolyester urethanes |
| PCT/US2001/027288 WO2002018477A2 (en) | 2000-08-30 | 2001-08-30 | Elastomeric functional biodegradable copolyester amides and copolyester urethanes |
Publications (2)
| Publication Number | Publication Date |
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| CA2419429A1 CA2419429A1 (en) | 2002-03-07 |
| CA2419429C true CA2419429C (en) | 2010-07-27 |
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| CA2419429A Expired - Lifetime CA2419429C (en) | 2000-08-30 | 2001-08-30 | Elastomeric functional biodegradable copolyester amides and copolyester urethanes |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6503538B1 (enExample) |
| EP (1) | EP1313794B1 (enExample) |
| JP (1) | JP5047446B2 (enExample) |
| AT (1) | ATE346878T1 (enExample) |
| AU (2) | AU8701501A (enExample) |
| CA (1) | CA2419429C (enExample) |
| DE (1) | DE60124929T2 (enExample) |
| ES (1) | ES2275724T3 (enExample) |
| WO (1) | WO2002018477A2 (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8652504B2 (en) | 2005-09-22 | 2014-02-18 | Medivas, Llc | Solid polymer delivery compositions and methods for use thereof |
| US9102830B2 (en) | 2005-09-22 | 2015-08-11 | Medivas, Llc | Bis-(α-amino)-diol-diester-containing poly (ester amide) and poly (ester urethane) compositions and methods of use |
| US9517203B2 (en) | 2000-08-30 | 2016-12-13 | Mediv As, Llc | Polymer particle delivery compositions and methods of use |
| CN104717962B (zh) * | 2012-10-02 | 2017-07-21 | 帝斯曼知识产权资产管理有限公司 | 包含蛋白质和可生物降解聚酯酰胺的药物递送组合物 |
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| US6776792B1 (en) * | 1997-04-24 | 2004-08-17 | Advanced Cardiovascular Systems Inc. | Coated endovascular stent |
| DE60038010T2 (de) | 1999-04-12 | 2009-03-05 | Cornell Research Foundation, Inc. | Hydrogel-formendes system mit hydrophoben und hydrophilen komponenten |
| US6716445B2 (en) | 1999-04-12 | 2004-04-06 | Cornell Research Foundation, Inc. | Hydrogel entrapping therapeutic agent and stent with coating comprising this |
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| US20070032853A1 (en) * | 2002-03-27 | 2007-02-08 | Hossainy Syed F | 40-O-(2-hydroxy)ethyl-rapamycin coated stent |
| US20050238686A1 (en) * | 1999-12-23 | 2005-10-27 | Advanced Cardiovascular Systems, Inc. | Coating for implantable devices and a method of forming the same |
| US6703040B2 (en) | 2000-01-11 | 2004-03-09 | Intralytix, Inc. | Polymer blends as biodegradable matrices for preparing biocomposites |
| US8088060B2 (en) * | 2000-03-15 | 2012-01-03 | Orbusneich Medical, Inc. | Progenitor endothelial cell capturing with a drug eluting implantable medical device |
| US9522217B2 (en) * | 2000-03-15 | 2016-12-20 | Orbusneich Medical, Inc. | Medical device with coating for capturing genetically-altered cells and methods for using same |
| US20160287708A9 (en) * | 2000-03-15 | 2016-10-06 | Orbusneich Medical, Inc. | Progenitor Endothelial Cell Capturing with a Drug Eluting Implantable Medical Device |
| US20050271701A1 (en) * | 2000-03-15 | 2005-12-08 | Orbus Medical Technologies, Inc. | Progenitor endothelial cell capturing with a drug eluting implantable medical device |
| US7304122B2 (en) | 2001-08-30 | 2007-12-04 | Cornell Research Foundation, Inc. | Elastomeric functional biodegradable copolyester amides and copolyester urethanes |
| US20060286064A1 (en) * | 2000-08-30 | 2006-12-21 | Medivas, Llc | Therapeutic polymers and methods |
| US6953560B1 (en) * | 2000-09-28 | 2005-10-11 | Advanced Cardiovascular Systems, Inc. | Barriers for polymer-coated implantable medical devices and methods for making the same |
| US6783793B1 (en) | 2000-10-26 | 2004-08-31 | Advanced Cardiovascular Systems, Inc. | Selective coating of medical devices |
| US7807210B1 (en) * | 2000-10-31 | 2010-10-05 | Advanced Cardiovascular Systems, Inc. | Hemocompatible polymers on hydrophobic porous polymers |
| US6780424B2 (en) * | 2001-03-30 | 2004-08-24 | Charles David Claude | Controlled morphologies in polymer drug for release of drugs from polymer films |
| SK287686B6 (sk) * | 2001-04-10 | 2011-06-06 | Ciba Specialty Chemicals Holding Inc. | Izolačná kompozícia na strednonapäťové a vysokonapäťové káble a spôsob jej výroby |
| DE60221009T2 (de) | 2001-05-07 | 2008-03-13 | Cornell Research Foundation, Inc. | Biologisch abbaubare copolymere, die an ein segment mit mehreren funktionellen gruppen gebunden sind |
| US6743462B1 (en) * | 2001-05-31 | 2004-06-01 | Advanced Cardiovascular Systems, Inc. | Apparatus and method for coating implantable devices |
| CA2349989A1 (en) * | 2001-06-07 | 2002-12-07 | Paul J. Santerre | Bioactive surface modifiers for polymers and articles made therefrom |
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| US7217426B1 (en) | 2002-06-21 | 2007-05-15 | Advanced Cardiovascular Systems, Inc. | Coatings containing polycationic peptides for cardiovascular therapy |
| US6994867B1 (en) | 2002-06-21 | 2006-02-07 | Advanced Cardiovascular Systems, Inc. | Biocompatible carrier containing L-arginine |
| US8506617B1 (en) | 2002-06-21 | 2013-08-13 | Advanced Cardiovascular Systems, Inc. | Micronized peptide coated stent |
| US7070798B1 (en) | 2002-06-21 | 2006-07-04 | Advanced Cardiovascular Systems, Inc. | Coatings for implantable medical devices incorporating chemically-bound polymers and oligomers of L-arginine |
| US7056523B1 (en) | 2002-06-21 | 2006-06-06 | Advanced Cardiovascular Systems, Inc. | Implantable medical devices incorporating chemically conjugated polymers and oligomers of L-arginine |
| US6896965B1 (en) * | 2002-11-12 | 2005-05-24 | Advanced Cardiovascular Systems, Inc. | Rate limiting barriers for implantable devices |
| 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 |
| US7074276B1 (en) * | 2002-12-12 | 2006-07-11 | Advanced Cardiovascular Systems, Inc. | Clamp mandrel fixture and a method of using the same to minimize coating defects |
| US7758881B2 (en) * | 2004-06-30 | 2010-07-20 | Advanced Cardiovascular Systems, Inc. | Anti-proliferative and anti-inflammatory agent combination for treatment of vascular disorders with an implantable medical device |
| US20060002968A1 (en) * | 2004-06-30 | 2006-01-05 | Gordon Stewart | Anti-proliferative and anti-inflammatory agent combination for treatment of vascular disorders |
| US7094256B1 (en) | 2002-12-16 | 2006-08-22 | Advanced Cardiovascular Systems, Inc. | Coatings for implantable medical device containing polycationic peptides |
| US8435550B2 (en) | 2002-12-16 | 2013-05-07 | Abbot Cardiovascular Systems Inc. | Anti-proliferative and anti-inflammatory agent combination for treatment of vascular disorders with an implantable medical device |
| US7063884B2 (en) * | 2003-02-26 | 2006-06-20 | Advanced Cardiovascular Systems, Inc. | Stent coating |
| CA2513443A1 (en) * | 2003-02-26 | 2004-09-10 | Medivas, Llc | Bioactive stents and methods for use thereof |
| US7279174B2 (en) * | 2003-05-08 | 2007-10-09 | Advanced Cardiovascular Systems, Inc. | Stent coatings comprising hydrophilic additives |
| US20050118344A1 (en) | 2003-12-01 | 2005-06-02 | Pacetti Stephen D. | Temperature controlled crimping |
| US20050021127A1 (en) * | 2003-07-21 | 2005-01-27 | Kawula Paul John | Porous glass fused onto stent for drug retention |
| US7056591B1 (en) | 2003-07-30 | 2006-06-06 | Advanced Cardiovascular Systems, Inc. | Hydrophobic biologically absorbable coatings for drug delivery devices and methods for fabricating the same |
| US7785512B1 (en) | 2003-07-31 | 2010-08-31 | Advanced Cardiovascular Systems, Inc. | Method and system of controlled temperature mixing and molding of polymers with active agents for implantable medical devices |
| ES2239516B2 (es) * | 2003-09-15 | 2007-06-16 | Universitat Politecnica De Catalunya | Proceso para la obtencion y aplicaciones biomedicas de poliesteramidasderivadas de acido glicolico y omega-aminoacidos. metodo para la incorporacion de unidades de acidoo glicolico en poliamidas derivadas de diaminas y acidos dicarboxilicos. |
| US7198675B2 (en) * | 2003-09-30 | 2007-04-03 | Advanced Cardiovascular Systems | Stent mandrel fixture and method for selectively coating surfaces of a stent |
| US20060188469A1 (en) * | 2003-10-14 | 2006-08-24 | Medivas, Llc | Vaccine delivery compositions and methods of use |
| WO2006083874A2 (en) * | 2005-02-01 | 2006-08-10 | Medivas, Llc. | Vaccine delivery compositions and methods of use |
| US20080160089A1 (en) * | 2003-10-14 | 2008-07-03 | Medivas, Llc | Vaccine delivery compositions and methods of use |
| US7794706B2 (en) | 2003-10-14 | 2010-09-14 | Medivas, Llc | Bioactive wound dressings and implantable devices and methods of use |
| US20060188486A1 (en) * | 2003-10-14 | 2006-08-24 | Medivas, Llc | Wound care polymer compositions and methods for use thereof |
| US9114198B2 (en) * | 2003-11-19 | 2015-08-25 | Advanced Cardiovascular Systems, Inc. | Biologically beneficial coatings for implantable devices containing fluorinated polymers and methods for fabricating the same |
| US8192752B2 (en) * | 2003-11-21 | 2012-06-05 | Advanced Cardiovascular Systems, Inc. | Coatings for implantable devices including biologically erodable polyesters and methods for fabricating the same |
| US7220816B2 (en) * | 2003-12-16 | 2007-05-22 | Advanced Cardiovascular Systems, Inc. | Biologically absorbable coatings for implantable devices based on poly(ester amides) and methods for fabricating the same |
| US7435788B2 (en) * | 2003-12-19 | 2008-10-14 | Advanced Cardiovascular Systems, Inc. | Biobeneficial polyamide/polyethylene glycol polymers for use with drug eluting stents |
| US7563324B1 (en) | 2003-12-29 | 2009-07-21 | Advanced Cardiovascular Systems Inc. | System and method for coating an implantable medical device |
| US8685431B2 (en) * | 2004-03-16 | 2014-04-01 | Advanced Cardiovascular Systems, Inc. | Biologically absorbable coatings for implantable devices based on copolymers having ester bonds and methods for fabricating the same |
| US20050208093A1 (en) * | 2004-03-22 | 2005-09-22 | Thierry Glauser | Phosphoryl choline coating compositions |
| WO2005097222A1 (en) * | 2004-03-26 | 2005-10-20 | Surmodics, Inc. | Process and systems for biocompatible surfaces |
| JP2007530169A (ja) | 2004-03-26 | 2007-11-01 | サーモディクス,インコーポレイティド | 生物適合性表面を調製するための組成物及び方法 |
| US8778014B1 (en) | 2004-03-31 | 2014-07-15 | Advanced Cardiovascular Systems, Inc. | Coatings for preventing balloon damage to polymer coated stents |
| US20060013855A1 (en) * | 2004-04-05 | 2006-01-19 | Medivas, Llc | Bioactive stents for type II diabetics and methods for use thereof |
| US8163269B2 (en) * | 2004-04-05 | 2012-04-24 | Carpenter Kenneth W | Bioactive stents for type II diabetics and methods for use thereof |
| US7553377B1 (en) | 2004-04-27 | 2009-06-30 | Advanced Cardiovascular Systems, Inc. | Apparatus and method for electrostatic coating of an abluminal stent surface |
| US20050265960A1 (en) * | 2004-05-26 | 2005-12-01 | Pacetti Stephen D | Polymers containing poly(ester amides) and agents for use with medical articles and methods of fabricating the same |
| US20050288481A1 (en) | 2004-04-30 | 2005-12-29 | Desnoyer Jessica R | Design of poly(ester amides) for the control of agent-release from polymeric compositions |
| US8293890B2 (en) * | 2004-04-30 | 2012-10-23 | Advanced Cardiovascular Systems, Inc. | Hyaluronic acid based copolymers |
| US7820732B2 (en) * | 2004-04-30 | 2010-10-26 | Advanced Cardiovascular Systems, Inc. | Methods for modulating thermal and mechanical properties of coatings on implantable devices |
| AU2005244848A1 (en) * | 2004-05-12 | 2005-12-01 | Medivas, Llc | Wound healing polymer compositions and methods for use thereof |
| US9561309B2 (en) * | 2004-05-27 | 2017-02-07 | Advanced Cardiovascular Systems, Inc. | Antifouling heparin coatings |
| US20050271700A1 (en) * | 2004-06-03 | 2005-12-08 | Desnoyer Jessica R | Poly(ester amide) coating composition for implantable devices |
| WO2005121250A2 (en) * | 2004-06-03 | 2005-12-22 | Cornell Research Foundation, Inc. | Unsaturated poly(ester-amide) biomaterials |
| US20110015367A1 (en) * | 2004-06-03 | 2011-01-20 | Cornell University | Unsaturated poly(ester-amide) and poly(ether ester amide) biomaterials |
| US7563780B1 (en) * | 2004-06-18 | 2009-07-21 | Advanced Cardiovascular Systems, Inc. | Heparin prodrugs and drug delivery stents formed therefrom |
| US20050287184A1 (en) * | 2004-06-29 | 2005-12-29 | Hossainy Syed F A | Drug-delivery stent formulations for restenosis and vulnerable plaque |
| US8709469B2 (en) | 2004-06-30 | 2014-04-29 | Abbott Cardiovascular Systems Inc. | Anti-proliferative and anti-inflammatory agent combination for treatment of vascular disorders with an implantable medical device |
| US8357391B2 (en) | 2004-07-30 | 2013-01-22 | Advanced Cardiovascular Systems, Inc. | Coatings for implantable devices comprising poly (hydroxy-alkanoates) and diacid linkages |
| US7494665B1 (en) * | 2004-07-30 | 2009-02-24 | Advanced Cardiovascular Systems, Inc. | Polymers containing siloxane monomers |
| US7311980B1 (en) | 2004-08-02 | 2007-12-25 | Advanced Cardiovascular Systems, Inc. | Polyactive/polylactic acid coatings for an implantable device |
| US8980300B2 (en) | 2004-08-05 | 2015-03-17 | Advanced Cardiovascular Systems, Inc. | Plasticizers for coating compositions |
| US7648727B2 (en) * | 2004-08-26 | 2010-01-19 | Advanced Cardiovascular Systems, Inc. | Methods for manufacturing a coated stent-balloon assembly |
| US7244443B2 (en) * | 2004-08-31 | 2007-07-17 | Advanced Cardiovascular Systems, Inc. | Polymers of fluorinated monomers and hydrophilic monomers |
| US8110211B2 (en) * | 2004-09-22 | 2012-02-07 | Advanced Cardiovascular Systems, Inc. | Medicated coatings for implantable medical devices including polyacrylates |
| US7166680B2 (en) * | 2004-10-06 | 2007-01-23 | Advanced Cardiovascular Systems, Inc. | Blends of poly(ester amide) polymers |
| US20060089485A1 (en) * | 2004-10-27 | 2006-04-27 | Desnoyer Jessica R | End-capped poly(ester amide) copolymers |
| US8603634B2 (en) | 2004-10-27 | 2013-12-10 | Abbott Cardiovascular Systems Inc. | End-capped poly(ester amide) copolymers |
| CA2585740A1 (en) * | 2004-10-28 | 2006-05-11 | Medivas, Llc | Bioactive wound dressings and implantable devices and methods of use |
| US7481835B1 (en) | 2004-10-29 | 2009-01-27 | Advanced Cardiovascular Systems, Inc. | Encapsulated covered stent |
| US20060095122A1 (en) * | 2004-10-29 | 2006-05-04 | Advanced Cardiovascular Systems, Inc. | Implantable devices comprising biologically absorbable star polymers and methods for fabricating the same |
| US7390497B2 (en) * | 2004-10-29 | 2008-06-24 | Advanced Cardiovascular Systems, Inc. | Poly(ester amide) filler blends for modulation of coating properties |
| WO2007001448A2 (en) | 2004-11-04 | 2007-01-04 | Massachusetts Institute Of Technology | Coated controlled release polymer particles as efficient oral delivery vehicles for biopharmaceuticals |
| US7214759B2 (en) * | 2004-11-24 | 2007-05-08 | Advanced Cardiovascular Systems, Inc. | Biologically absorbable coatings for implantable devices based on polyesters and methods for fabricating the same |
| US8609123B2 (en) * | 2004-11-29 | 2013-12-17 | Advanced Cardiovascular Systems, Inc. | Derivatized poly(ester amide) as a biobeneficial coating |
| US20060115449A1 (en) * | 2004-11-30 | 2006-06-01 | Advanced Cardiovascular Systems, Inc. | Bioabsorbable, biobeneficial, tyrosine-based polymers for use in drug eluting stent coatings |
| US7892592B1 (en) | 2004-11-30 | 2011-02-22 | Advanced Cardiovascular Systems, Inc. | Coating abluminal surfaces of stents and other implantable medical devices |
| US7632307B2 (en) | 2004-12-16 | 2009-12-15 | Advanced Cardiovascular Systems, Inc. | Abluminal, multilayer coating constructs for drug-delivery stents |
| US7604818B2 (en) * | 2004-12-22 | 2009-10-20 | Advanced Cardiovascular Systems, Inc. | Polymers of fluorinated monomers and hydrocarbon monomers |
| US7419504B2 (en) * | 2004-12-27 | 2008-09-02 | Advanced Cardiovascular Systems, Inc. | Poly(ester amide) block copolymers |
| US8007775B2 (en) * | 2004-12-30 | 2011-08-30 | Advanced Cardiovascular Systems, Inc. | Polymers containing poly(hydroxyalkanoates) and agents for use with medical articles and methods of fabricating the same |
| US7202325B2 (en) | 2005-01-14 | 2007-04-10 | Advanced Cardiovascular Systems, Inc. | Poly(hydroxyalkanoate-co-ester amides) and agents for use with medical articles |
| WO2006086621A2 (en) * | 2005-02-11 | 2006-08-17 | R.T. Vanderbilt Company, Inc. | Lubricating greases containing antimony dithiocarbamates |
| CN101115471B (zh) * | 2005-02-17 | 2011-02-09 | 梅迪沃什有限公司 | 聚合物颗粒输送组合物及使用方法 |
| US20060193891A1 (en) * | 2005-02-25 | 2006-08-31 | Robert Richard | Medical devices and therapeutic delivery devices composed of bioabsorbable polymers produced at room temperature, method of making the devices, and a system for making the devices |
| US7795467B1 (en) | 2005-04-26 | 2010-09-14 | Advanced Cardiovascular Systems, Inc. | Bioabsorbable, biobeneficial polyurethanes for use in medical devices |
| US8778375B2 (en) | 2005-04-29 | 2014-07-15 | Advanced Cardiovascular Systems, Inc. | Amorphous poly(D,L-lactide) coating |
| US7637941B1 (en) | 2005-05-11 | 2009-12-29 | Advanced Cardiovascular Systems, Inc. | Endothelial cell binding coatings for rapid encapsulation of bioerodable stents |
| WO2006132950A2 (en) * | 2005-06-03 | 2006-12-14 | Medivas, Llc | Therapeutic polymers and methods of use |
| US7622070B2 (en) * | 2005-06-20 | 2009-11-24 | Advanced Cardiovascular Systems, Inc. | Method of manufacturing an implantable polymeric medical device |
| US7823533B2 (en) * | 2005-06-30 | 2010-11-02 | Advanced Cardiovascular Systems, Inc. | Stent fixture and method for reducing coating defects |
| US8021676B2 (en) | 2005-07-08 | 2011-09-20 | Advanced Cardiovascular Systems, Inc. | Functionalized chemically inert polymers for coatings |
| US20070020312A1 (en) * | 2005-07-20 | 2007-01-25 | Desnoyer Jessica R | Method of fabricating a bioactive agent-releasing implantable medical device |
| US7785647B2 (en) * | 2005-07-25 | 2010-08-31 | Advanced Cardiovascular Systems, Inc. | Methods of providing antioxidants to a drug containing product |
| US7735449B1 (en) | 2005-07-28 | 2010-06-15 | Advanced Cardiovascular Systems, Inc. | Stent fixture having rounded support structures and method for use thereof |
| US8377462B2 (en) * | 2005-07-29 | 2013-02-19 | Advanced Cardiovascular Systems, Inc. | PEA-TEMPO/PEA-BZ coatings for controlled delivery of drug from implantable medical devices |
| CA2670355A1 (en) * | 2005-11-21 | 2008-04-24 | Medivas, Llc | Polymer particles for delivery of macromolecules and methods of use |
| US20070128246A1 (en) * | 2005-12-06 | 2007-06-07 | Hossainy Syed F A | Solventless method for forming a coating |
| WO2007067744A2 (en) * | 2005-12-07 | 2007-06-14 | Medivas, Llc | Method for assembling a polymer-biologic delivery composition |
| US20070135909A1 (en) * | 2005-12-08 | 2007-06-14 | Desnoyer Jessica R | Adhesion polymers to improve stent retention |
| US9267937B2 (en) | 2005-12-15 | 2016-02-23 | Massachusetts Institute Of Technology | System for screening particles |
| US7976891B1 (en) | 2005-12-16 | 2011-07-12 | Advanced Cardiovascular Systems, Inc. | Abluminal stent coating apparatus and method of using focused acoustic energy |
| US7591841B2 (en) | 2005-12-16 | 2009-09-22 | Advanced Cardiovascular Systems, Inc. | Implantable devices for accelerated healing |
| US8974815B2 (en) * | 2005-12-16 | 2015-03-10 | Cornell University | Fibrous membrane for biomedical application based on poly(ester-amide)s |
| US20070155273A1 (en) * | 2005-12-16 | 2007-07-05 | Cornell Research Foundation, Inc. | Non-woven fabric for biomedical application based on poly(ester-amide)s |
| US7638156B1 (en) | 2005-12-19 | 2009-12-29 | Advanced Cardiovascular Systems, Inc. | Apparatus and method for selectively coating a medical article |
| US7867547B2 (en) | 2005-12-19 | 2011-01-11 | Advanced Cardiovascular Systems, Inc. | Selectively coating luminal surfaces of stents |
| US20070160642A1 (en) * | 2006-01-12 | 2007-07-12 | Pacetti Stephen D | Implantable medical devices coated with a polymer-bound superoxide dismutase mimic |
| WO2007089870A2 (en) * | 2006-01-31 | 2007-08-09 | Medivas, Llc | Vaccine delivery compositions and methods of use |
| US20070196428A1 (en) * | 2006-02-17 | 2007-08-23 | Thierry Glauser | Nitric oxide generating medical devices |
| US7910152B2 (en) * | 2006-02-28 | 2011-03-22 | Advanced Cardiovascular Systems, Inc. | Poly(ester amide)-based drug delivery systems with controlled release rate and morphology |
| US7601383B2 (en) * | 2006-02-28 | 2009-10-13 | Advanced Cardiovascular Systems, Inc. | Coating construct containing poly (vinyl alcohol) |
| US7713637B2 (en) * | 2006-03-03 | 2010-05-11 | Advanced Cardiovascular Systems, Inc. | Coating containing PEGylated hyaluronic acid and a PEGylated non-hyaluronic acid polymer |
| US20070225799A1 (en) * | 2006-03-24 | 2007-09-27 | Medtronic Vascular, Inc. | Stent, intraluminal stent delivery system, and method of treating a vascular condition |
| EP2004145A4 (en) * | 2006-03-24 | 2013-07-03 | Medivas Llc | ALKYLENE DICARBOXYLATE-CONTAINING BIODEGRADABLE POLY (ESTER AMIDE) AND METHOD OF USE |
| US20070231363A1 (en) * | 2006-03-29 | 2007-10-04 | Yung-Ming Chen | Coatings formed from stimulus-sensitive material |
| US8658210B2 (en) | 2006-04-17 | 2014-02-25 | Advanced Cardiovascular Systems, Inc. | Polyesteramide platform for site specific drug delivery |
| US20070259101A1 (en) * | 2006-05-02 | 2007-11-08 | Kleiner Lothar W | Microporous coating on medical devices |
| EP2019645A4 (en) * | 2006-05-02 | 2013-03-06 | Medivas Llc | RELEASE OF OPHTHALMOLOGICAL ACTIVITIES OUTSIDE OR WITHIN THE EYE |
| US7985441B1 (en) | 2006-05-04 | 2011-07-26 | Yiwen Tang | Purification of polymers for coating applications |
| US8003156B2 (en) * | 2006-05-04 | 2011-08-23 | Advanced Cardiovascular Systems, Inc. | Rotatable support elements for stents |
| US8304012B2 (en) * | 2006-05-04 | 2012-11-06 | Advanced Cardiovascular Systems, Inc. | Method for drying a stent |
| EP2021141A4 (en) * | 2006-05-09 | 2013-07-03 | Medivas Llc | BIODEGRADABLE WATER SOLUBLE POLYMERS |
| EP2019691B1 (en) * | 2006-05-15 | 2020-08-12 | Massachusetts Institute of Technology | Polymers for functional particles |
| US7775178B2 (en) * | 2006-05-26 | 2010-08-17 | Advanced Cardiovascular Systems, Inc. | Stent coating apparatus and method |
| US8568764B2 (en) * | 2006-05-31 | 2013-10-29 | Advanced Cardiovascular Systems, Inc. | Methods of forming coating layers for medical devices utilizing flash vaporization |
| US9561351B2 (en) * | 2006-05-31 | 2017-02-07 | Advanced Cardiovascular Systems, Inc. | Drug delivery spiral coil construct |
| US8703167B2 (en) * | 2006-06-05 | 2014-04-22 | Advanced Cardiovascular Systems, Inc. | Coatings for implantable medical devices for controlled release of a hydrophilic drug and a hydrophobic drug |
| US20090258028A1 (en) * | 2006-06-05 | 2009-10-15 | Abbott Cardiovascular Systems Inc. | Methods Of Forming Coatings For Implantable Medical Devices For Controlled Release Of A Peptide And A Hydrophobic Drug |
| US8323676B2 (en) * | 2008-06-30 | 2012-12-04 | Abbott Cardiovascular Systems Inc. | Poly(ester-amide) and poly(amide) coatings for implantable medical devices for controlled release of a protein or peptide and a hydrophobic drug |
| US20080124372A1 (en) * | 2006-06-06 | 2008-05-29 | Hossainy Syed F A | Morphology profiles for control of agent release rates from polymer matrices |
| US8778376B2 (en) | 2006-06-09 | 2014-07-15 | Advanced Cardiovascular Systems, Inc. | Copolymer comprising elastin pentapeptide block and hydrophilic block, and medical device and method of treating |
| US20070286882A1 (en) * | 2006-06-09 | 2007-12-13 | Yiwen Tang | Solvent systems for coating medical devices |
| WO2007146119A2 (en) * | 2006-06-09 | 2007-12-21 | Medivas, Llc | Biodegradable polymer adhesion barriers |
| US20080095918A1 (en) * | 2006-06-14 | 2008-04-24 | Kleiner Lothar W | Coating construct with enhanced interfacial compatibility |
| US8603530B2 (en) | 2006-06-14 | 2013-12-10 | Abbott Cardiovascular Systems Inc. | Nanoshell therapy |
| US8114150B2 (en) | 2006-06-14 | 2012-02-14 | Advanced Cardiovascular Systems, Inc. | RGD peptide attached to bioabsorbable stents |
| US8048448B2 (en) * | 2006-06-15 | 2011-11-01 | Abbott Cardiovascular Systems Inc. | Nanoshells for drug delivery |
| US9381477B2 (en) | 2006-06-23 | 2016-07-05 | Massachusetts Institute Of Technology | Microfluidic synthesis of organic nanoparticles |
| US8017237B2 (en) * | 2006-06-23 | 2011-09-13 | Abbott Cardiovascular Systems, Inc. | Nanoshells on polymers |
| US8962697B2 (en) | 2006-06-30 | 2015-02-24 | Interface Biologics Inc. | Bioreponsive polymers |
| US7771739B2 (en) * | 2006-06-30 | 2010-08-10 | Abbott Cardiovascular Systems Inc. | Implantable medical devices comprising semi-crystalline poly(ester-amide) |
| US9028859B2 (en) * | 2006-07-07 | 2015-05-12 | Advanced Cardiovascular Systems, Inc. | Phase-separated block copolymer coatings for implantable medical devices |
| WO2008008437A1 (en) * | 2006-07-13 | 2008-01-17 | Abbott Cardiovascular Systems Inc. | Poly(ester-amide)s, derivatives thereof, and their use with implantable medical devices |
| US8030436B2 (en) * | 2006-07-13 | 2011-10-04 | Advanced Cardiovascular Systems, Inc. | Poly(ester-amide) elastomers and their use with implantable medical devices |
| US20090181063A1 (en) * | 2006-07-13 | 2009-07-16 | Michael Huy Ngo | Implantable medical device comprising a pro-healing poly(ester-amide) |
| US7731987B2 (en) * | 2006-07-13 | 2010-06-08 | Advanced Cardiovascular Systems, Inc. | Implantable medical device comprising a pro-healing poly(ester-amide) |
| US20080014245A1 (en) * | 2006-07-14 | 2008-01-17 | Stephen Pacetti | Drug-eluting implantable medical device with free radical scavenger for protecting drugs during sterilization and related method |
| US8685430B1 (en) | 2006-07-14 | 2014-04-01 | Abbott Cardiovascular Systems Inc. | Tailored aliphatic polyesters for stent coatings |
| US8952123B1 (en) | 2006-08-02 | 2015-02-10 | Abbott Cardiovascular Systems Inc. | Dioxanone-based copolymers for implantable devices |
| US8703169B1 (en) | 2006-08-15 | 2014-04-22 | Abbott Cardiovascular Systems Inc. | Implantable device having a coating comprising carrageenan and a biostable polymer |
| US8597673B2 (en) * | 2006-12-13 | 2013-12-03 | Advanced Cardiovascular Systems, Inc. | Coating of fast absorption or dissolution |
| US20080175882A1 (en) * | 2007-01-23 | 2008-07-24 | Trollsas Mikael O | Polymers of aliphatic thioester |
| EP2134830A2 (en) | 2007-02-09 | 2009-12-23 | Massachusetts Institute of Technology | Oscillating cell culture bioreactor |
| EP2144600A4 (en) | 2007-04-04 | 2011-03-16 | Massachusetts Inst Technology | POLY (AMINIC ACID) TARGET MOLECULES |
| US8147769B1 (en) | 2007-05-16 | 2012-04-03 | Abbott Cardiovascular Systems Inc. | Stent and delivery system with reduced chemical degradation |
| US9056155B1 (en) * | 2007-05-29 | 2015-06-16 | Abbott Cardiovascular Systems Inc. | Coatings having an elastic primer layer |
| US10155881B2 (en) * | 2007-05-30 | 2018-12-18 | Abbott Cardiovascular Systems Inc. | Substituted polycaprolactone for coating |
| US20080306584A1 (en) * | 2007-06-05 | 2008-12-11 | Pamela Kramer-Brown | Implantable medical devices for local and regional treatment |
| US8252361B2 (en) * | 2007-06-05 | 2012-08-28 | Abbott Cardiovascular Systems Inc. | Implantable medical devices for local and regional treatment |
| US9737638B2 (en) * | 2007-06-20 | 2017-08-22 | Abbott Cardiovascular Systems, Inc. | Polyester amide copolymers having free carboxylic acid pendant groups |
| US7927621B2 (en) * | 2007-06-25 | 2011-04-19 | Abbott Cardiovascular Systems Inc. | Thioester-ester-amide copolymers |
| US8109904B1 (en) | 2007-06-25 | 2012-02-07 | Abbott Cardiovascular Systems Inc. | Drug delivery medical devices |
| US8048441B2 (en) | 2007-06-25 | 2011-11-01 | Abbott Cardiovascular Systems, Inc. | Nanobead releasing medical devices |
| US20090004243A1 (en) | 2007-06-29 | 2009-01-01 | Pacetti Stephen D | Biodegradable triblock copolymers for implantable devices |
| EP2178541A4 (en) * | 2007-07-17 | 2012-11-14 | Medivas Llc | BIOABSORBABLE ELASTOMERIC ARTERIAL SUPPORT DEVICE AND METHODS OF USE |
| CA2709412A1 (en) * | 2007-07-24 | 2009-01-29 | Medivas, Llc | Biodegradable cationic polymer gene transfer compositions and methods of use |
| US20090041845A1 (en) * | 2007-08-08 | 2009-02-12 | Lothar Walter Kleiner | Implantable medical devices having thin absorbable coatings |
| CA2713185A1 (en) * | 2007-08-23 | 2009-02-26 | Medivas, Llc | Cationic alpha-amino acid-containing biodegradable polymer gene transfer compositions |
| US9814553B1 (en) | 2007-10-10 | 2017-11-14 | Abbott Cardiovascular Systems Inc. | Bioabsorbable semi-crystalline polymer for controlling release of drug from a coating |
| EP2620157A3 (en) | 2007-10-12 | 2013-10-16 | Massachusetts Institute of Technology | Vaccine nanotechnology |
| US20090104241A1 (en) * | 2007-10-23 | 2009-04-23 | Pacetti Stephen D | Random amorphous terpolymer containing lactide and glycolide |
| US8661630B2 (en) | 2008-05-21 | 2014-03-04 | Abbott Cardiovascular Systems Inc. | Coating comprising an amorphous primer layer and a semi-crystalline reservoir layer |
| US20090306120A1 (en) * | 2007-10-23 | 2009-12-10 | Florencia Lim | Terpolymers containing lactide and glycolide |
| US8642062B2 (en) * | 2007-10-31 | 2014-02-04 | Abbott Cardiovascular Systems Inc. | Implantable device having a slow dissolving polymer |
| US20090110713A1 (en) * | 2007-10-31 | 2009-04-30 | Florencia Lim | Biodegradable polymeric materials providing controlled release of hydrophobic drugs from implantable devices |
| WO2009073814A2 (en) * | 2007-12-06 | 2009-06-11 | Medivas, Llc | Oligo-ethylene glycol-based polymer compositions and methods of use |
| WO2009134303A2 (en) * | 2008-03-24 | 2009-11-05 | Clemson University | Method and compositions for biofouling deterrence |
| EP2271379B1 (en) | 2008-03-28 | 2015-11-25 | SurModics, Inc. | Insertable medical devices having microparticulate-associated elastic substrates and methods for drug delivery |
| US8128983B2 (en) * | 2008-04-11 | 2012-03-06 | Abbott Cardiovascular Systems Inc. | Coating comprising poly(ethylene glycol)-poly(lactide-glycolide-caprolactone) interpenetrating network |
| US8916188B2 (en) * | 2008-04-18 | 2014-12-23 | Abbott Cardiovascular Systems Inc. | Block copolymer comprising at least one polyester block and a poly (ethylene glycol) block |
| US20090285873A1 (en) * | 2008-04-18 | 2009-11-19 | Abbott Cardiovascular Systems Inc. | Implantable medical devices and coatings therefor comprising block copolymers of poly(ethylene glycol) and a poly(lactide-glycolide) |
| US20090297584A1 (en) * | 2008-04-18 | 2009-12-03 | Florencia Lim | Biosoluble coating with linear over time mass loss |
| US8889172B1 (en) | 2008-04-30 | 2014-11-18 | Abbott Cardiovascular Systems Inc. | Amorphous or semi-crystalline poly(ester amide) polymer with a high glass transition temperature |
| CA2723721A1 (en) * | 2008-05-07 | 2009-11-12 | Medivas, Llc | Biodegradable metal-chelating polymers and vaccines |
| US8697113B2 (en) * | 2008-05-21 | 2014-04-15 | Abbott Cardiovascular Systems Inc. | Coating comprising a terpolymer comprising caprolactone and glycolide |
| US8765162B2 (en) * | 2008-06-30 | 2014-07-01 | Abbott Cardiovascular Systems Inc. | Poly(amide) and poly(ester-amide) polymers and drug delivery particles and coatings containing same |
| EP2323671A4 (en) * | 2008-08-13 | 2012-09-26 | Medivas Llc | BIODEGRADABLE AABB POLY (DEPSIPEPTIDE) POLYMERS AND METHOD FOR THEIR USE |
| US20100047319A1 (en) * | 2008-08-21 | 2010-02-25 | Michael Huy Ngo | Biodegradable Poly(Ester-Amide) And Poly(Amide) Coatings For Implantable Medical Devices With Enhanced Bioabsorption Times |
| US8445603B2 (en) * | 2008-09-22 | 2013-05-21 | Tyrx, Inc. | Linear polyesteramides from aminophenolic esters |
| US8277812B2 (en) | 2008-10-12 | 2012-10-02 | Massachusetts Institute Of Technology | Immunonanotherapeutics that provide IgG humoral response without T-cell antigen |
| US8591905B2 (en) | 2008-10-12 | 2013-11-26 | The Brigham And Women's Hospital, Inc. | Nicotine immunonanotherapeutics |
| US8343498B2 (en) | 2008-10-12 | 2013-01-01 | Massachusetts Institute Of Technology | Adjuvant incorporation in immunonanotherapeutics |
| US8343497B2 (en) | 2008-10-12 | 2013-01-01 | The Brigham And Women's Hospital, Inc. | Targeting of antigen presenting cells with immunonanotherapeutics |
| EP2413909B1 (en) * | 2009-04-02 | 2016-11-30 | Cornell University | Multiamino acid-based poly (ester amide)s |
| US8697110B2 (en) * | 2009-05-14 | 2014-04-15 | Abbott Cardiovascular Systems Inc. | Polymers comprising amorphous terpolymers and semicrystalline blocks |
| US9839628B2 (en) | 2009-06-01 | 2017-12-12 | Tyrx, Inc. | Compositions and methods for preventing sternal wound infections |
| US20120135054A1 (en) * | 2009-06-29 | 2012-05-31 | Cornell University | Poly (Ester Ether Amide)s and Uses Thereof |
| CA2774036C (en) * | 2009-10-16 | 2018-04-03 | Dsm Ip Assets B.V. | Coatings comprising bis-(alpha-amino-diol-diester) containing polyesteramide |
| US8685433B2 (en) | 2010-03-31 | 2014-04-01 | Abbott Cardiovascular Systems Inc. | Absorbable coating for implantable device |
| EP3159368B1 (en) | 2011-06-23 | 2024-07-24 | DSM IP Assets B.V. | New biodegradable polyesteramide copolymers for drug delivery |
| US9873765B2 (en) | 2011-06-23 | 2018-01-23 | Dsm Ip Assets, B.V. | Biodegradable polyesteramide copolymers for drug delivery |
| EP3081937B1 (en) | 2011-07-18 | 2019-11-13 | President and Fellows of Harvard College | Engineered microbe-targeting molecules and uses thereof |
| EP2854890B1 (en) * | 2012-05-30 | 2019-02-06 | Boston Scientific Scimed, Inc. | Injectable biodegradable particles for controlled therapeutic agent release |
| WO2014004512A1 (en) | 2012-06-25 | 2014-01-03 | Surmodics, Inc. | Bioerodable poly(etheresteramides) and medical article uses |
| US10538864B2 (en) * | 2012-10-24 | 2020-01-21 | Dsm Ip Assets, B.V. | Fibers comprising polyesteramide copolymers for drug delivery |
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| WO2014096339A1 (en) * | 2012-12-20 | 2014-06-26 | Dsm Ip Assets B.V. | Coating comprising polyesteramide copolymers for drug delivery |
| EP3848045A1 (en) | 2013-05-21 | 2021-07-14 | President and Fellows of Harvard College | Engineered heme-binding compositions and uses thereof |
| WO2015095604A2 (en) | 2013-12-18 | 2015-06-25 | President And Fellows Of Harvard College | Methods and assays relating to circulating tumor cells |
| WO2016020545A1 (en) * | 2014-08-08 | 2016-02-11 | Dsm Ip Assets B.V. | Reduction sensitive biodegradable polyesteramides |
| US10519443B2 (en) | 2014-09-08 | 2019-12-31 | University Of Iowa Research Foundation | Microrna inhibitor system and methods of use thereof |
| AU2015366355B2 (en) | 2014-12-18 | 2020-05-28 | Dsm Ip Assets B.V. | Drug delivery system for delivery of acid sensitive drugs |
| WO2016207725A1 (en) | 2015-06-23 | 2016-12-29 | Phagelux (Canada), Inc. | Composition comprising amino acid polymers and a bioactive agent and method of preparing thereof |
| CN108289928B (zh) | 2015-08-06 | 2024-09-17 | 哈佛大学校长及研究员协会 | 改进的微生物-结合分子和其用途 |
| US10273476B2 (en) | 2016-04-30 | 2019-04-30 | University Of Iowa Research Foundation | MicroRNA-200 based approaches for modulating bone formation inhibition and bone regeneration |
| US11564894B2 (en) | 2016-06-21 | 2023-01-31 | Phagelux (Canada) Inc. | Composition comprising amino acid polymers and a bioactive agent and method of preparing thereof |
| US11413319B2 (en) | 2016-06-23 | 2022-08-16 | Phagelux (Canada) Inc. | Microencapsulation of bacteriophages and related products |
| CA3028338C (en) | 2016-06-23 | 2019-04-02 | Phagelux (Canada) Inc. | Microencapsulation of bacteriophages and related products |
| JP7196850B2 (ja) * | 2017-09-05 | 2022-12-27 | 味の素株式会社 | ポリリジン誘導体 |
| EP4240413A4 (en) * | 2020-11-06 | 2024-10-16 | NDPD Pharma, Inc. | POLYSACCHARIDES FOR USE IN THE TREATMENT OF SARS-COV-2 INFECTIONS |
| US12331439B2 (en) | 2021-12-21 | 2025-06-17 | Uncaged Innovations Inc | Plant protein based imitation leather material and methods of making same |
| JP2023163455A (ja) * | 2022-04-28 | 2023-11-10 | 東ソー株式会社 | 反応性官能基を有するポリマー |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU790725A1 (ru) | 1979-07-27 | 1983-01-23 | Ордена Ленина Институт Элементоорганических Соединений Ан Ссср | Способ получени алкилароматических полиимидов |
| SU872531A1 (ru) | 1979-08-07 | 1981-10-15 | Институт Физиологии Им.И.С.Бериташвили Ан Гсср | Способ получени полуретанов |
| SU811750A1 (ru) | 1979-08-07 | 1983-09-23 | Институт Физиологии Им.С.И.Бериташвили | Бис-карбонаты алифатических диолов-мономеры дл полиуретанов и поликарбонатов и способ их получени |
| SU876663A1 (ru) | 1979-11-11 | 1981-10-30 | Институт Физиологии Им. Академика И.С.Бериташвили Ан Гсср | Способ получени полиарилатов |
| SU1016314A1 (ru) | 1979-12-17 | 1983-05-07 | Институт Физиологии Им.И.С.Бериташвили | Способ получени полиэфируретанов |
| SU905228A1 (ru) | 1980-03-06 | 1982-02-15 | Институт Физиологии Им. Акад.И.С. Бериташвили Ан Гсср | Способ получени полимочевины |
| JPS6164728A (ja) * | 1984-09-05 | 1986-04-03 | Mitsubishi Chem Ind Ltd | ポリエステルアミドの製造法 |
| SU1293518A1 (ru) | 1985-04-11 | 1987-02-28 | Тбилисский зональный научно-исследовательский и проектный институт типового и экспериментального проектирования жилых и общественных зданий | Установка дл испытаний образца крестообразной строительной конструкции |
| US5721131A (en) | 1987-03-06 | 1998-02-24 | United States Of America As Represented By The Secretary Of The Navy | Surface modification of polymers with self-assembled monolayers that promote adhesion, outgrowth and differentiation of biological cells |
| IL90193A (en) | 1989-05-04 | 1993-02-21 | Biomedical Polymers Int | Polurethane-based polymeric materials and biomedical articles and pharmaceutical compositions utilizing the same |
| CA2038605C (en) | 1990-06-15 | 2000-06-27 | Leonard Pinchuk | Crack-resistant polycarbonate urethane polymer prostheses and the like |
| DE4224401A1 (de) | 1992-07-21 | 1994-01-27 | Pharmatech Gmbh | Neue biologisch abbaubare Polymere für die Arzneistoffgalenik |
| US5516881A (en) | 1994-08-10 | 1996-05-14 | Cornell Research Foundation, Inc. | Aminoxyl-containing radical spin labeling in polymers and copolymers |
| US5485496A (en) | 1994-09-22 | 1996-01-16 | Cornell Research Foundation, Inc. | Gamma irradiation sterilizing of biomaterial medical devices or products, with improved degradation and mechanical properties |
| US5610241A (en) | 1996-05-07 | 1997-03-11 | Cornell Research Foundation, Inc. | Reactive graft polymer with biodegradable polymer backbone and method for preparing reactive biodegradable polymers |
| DE69828387T2 (de) | 1997-01-28 | 2005-12-08 | United States Surgical Corp., Norwalk | Polyesteramid, seine darstellung und daraus fabrizierte chirurgische artikel |
| DE19902506A1 (de) * | 1999-01-22 | 2000-07-27 | Basf Ag | Hydrophobierungsmittel für harte Oberflächen |
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2000
- 2000-08-30 US US09/651,338 patent/US6503538B1/en not_active Expired - Lifetime
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- 2001-08-30 AU AU8701501A patent/AU8701501A/xx active Pending
- 2001-08-30 CA CA2419429A patent/CA2419429C/en not_active Expired - Lifetime
- 2001-08-30 AT AT01966509T patent/ATE346878T1/de not_active IP Right Cessation
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- 2001-08-30 EP EP01966509A patent/EP1313794B1/en not_active Expired - Lifetime
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- 2001-08-30 WO PCT/US2001/027288 patent/WO2002018477A2/en not_active Ceased
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9517203B2 (en) | 2000-08-30 | 2016-12-13 | Mediv As, Llc | Polymer particle delivery compositions and methods of use |
| US8652504B2 (en) | 2005-09-22 | 2014-02-18 | Medivas, Llc | Solid polymer delivery compositions and methods for use thereof |
| US9102830B2 (en) | 2005-09-22 | 2015-08-11 | Medivas, Llc | Bis-(α-amino)-diol-diester-containing poly (ester amide) and poly (ester urethane) compositions and methods of use |
| CN104717962B (zh) * | 2012-10-02 | 2017-07-21 | 帝斯曼知识产权资产管理有限公司 | 包含蛋白质和可生物降解聚酯酰胺的药物递送组合物 |
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| ES2275724T3 (es) | 2007-06-16 |
| US6503538B1 (en) | 2003-01-07 |
| AU2001287015B2 (en) | 2006-06-01 |
| ATE346878T1 (de) | 2006-12-15 |
| EP1313794A2 (en) | 2003-05-28 |
| JP5047446B2 (ja) | 2012-10-10 |
| JP2004507600A (ja) | 2004-03-11 |
| EP1313794B1 (en) | 2006-11-29 |
| CA2419429A1 (en) | 2002-03-07 |
| WO2002018477A3 (en) | 2002-05-30 |
| DE60124929D1 (de) | 2007-01-11 |
| AU8701501A (en) | 2002-03-13 |
| WO2002018477A2 (en) | 2002-03-07 |
| DE60124929T2 (de) | 2007-09-20 |
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