CA2628055C - Polysaccharide-derived nitric oxide-releasing carbon-bound diazeniumdiolates - Google Patents
Polysaccharide-derived nitric oxide-releasing carbon-bound diazeniumdiolates Download PDFInfo
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- CA2628055C CA2628055C CA2628055A CA2628055A CA2628055C CA 2628055 C CA2628055 C CA 2628055C CA 2628055 A CA2628055 A CA 2628055A CA 2628055 A CA2628055 A CA 2628055A CA 2628055 C CA2628055 C CA 2628055C
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- Prior art keywords
- nitric oxide
- saccharide
- releasing
- polysaccharide
- diazeniumdiolated
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- A61K47/00—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
- 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
- A61K47/61—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 the organic macromolecular compound being a polysaccharide or a derivative thereof
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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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
- A61K47/54—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 compound
- A61K47/549—Sugars, nucleosides, nucleotides or nucleic acids
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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| US73194605P | 2005-10-31 | 2005-10-31 | |
| US60/731,946 | 2005-10-31 | ||
| PCT/US2006/040456 WO2007053292A2 (en) | 2005-10-31 | 2006-10-16 | Polysaccharide-derived nitric oxide-releasing carbon-bound diazeniumdiolates |
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| CA2628055C true CA2628055C (en) | 2013-10-01 |
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| DE10209821A1 (de) | 2002-03-06 | 2003-09-25 | Biotechnologie Ges Mittelhesse | Kopplung von Proteinen an ein modifiziertes Polysaccharid |
| WO2004024776A1 (en) | 2002-09-11 | 2004-03-25 | Fresenius Kabi Deutschland Gmbh | Method of producing hydroxyalkyl starch derivatives |
| WO2005014655A2 (en) | 2003-08-08 | 2005-02-17 | Fresenius Kabi Deutschland Gmbh | Conjugates of hydroxyalkyl starch and a protein |
| WO2005092928A1 (en) | 2004-03-11 | 2005-10-06 | Fresenius Kabi Deutschland Gmbh | Conjugates of hydroxyalkyl starch and a protein, prepared by reductive amination |
| EP3556401A1 (en) | 2005-05-27 | 2019-10-23 | The University of North Carolina at Chapel Hill | Nitric oxide-releasing particles for nitric oxide therapeutics and biomedical applications |
| US8021679B2 (en) | 2005-08-25 | 2011-09-20 | Medtronic Vascular, Inc | Nitric oxide-releasing biodegradable polymers useful as medical devices and coatings therefore |
| EP1968615A4 (en) * | 2005-12-06 | 2010-08-04 | Amulet Pharmaceuticals Inc | POLYMERS RELEASING NITRIC OXIDE |
| US8241619B2 (en) | 2006-05-15 | 2012-08-14 | Medtronic Vascular, Inc. | Hindered amine nitric oxide donating polymers for coating medical devices |
| US11229746B2 (en) | 2006-06-22 | 2022-01-25 | Excelsior Medical Corporation | Antiseptic cap |
| US9259535B2 (en) | 2006-06-22 | 2016-02-16 | Excelsior Medical Corporation | Antiseptic cap equipped syringe |
| US7811600B2 (en) | 2007-03-08 | 2010-10-12 | Medtronic Vascular, Inc. | Nitric oxide donating medical devices and methods of making same |
| US8273828B2 (en) | 2007-07-24 | 2012-09-25 | Medtronic Vascular, Inc. | Methods for introducing reactive secondary amines pendant to polymers backbones that are useful for diazeniumdiolation |
| US20090232863A1 (en) * | 2008-03-17 | 2009-09-17 | Medtronic Vascular, Inc. | Biodegradable Carbon Diazeniumdiolate Based Nitric Oxide Donating Polymers |
| US9078992B2 (en) | 2008-10-27 | 2015-07-14 | Pursuit Vascular, Inc. | Medical device for applying antimicrobial to proximal end of catheter |
| US8158187B2 (en) | 2008-12-19 | 2012-04-17 | Medtronic Vascular, Inc. | Dry diazeniumdiolation methods for producing nitric oxide releasing medical devices |
| US8816391B2 (en) * | 2009-04-01 | 2014-08-26 | Taiwan Semiconductor Manufacturing Company, Ltd. | Source/drain engineering of devices with high-mobility channels |
| US8709465B2 (en) | 2009-04-13 | 2014-04-29 | Medtronic Vascular, Inc. | Diazeniumdiolated phosphorylcholine polymers for nitric oxide release |
| WO2011022652A1 (en) | 2009-08-21 | 2011-02-24 | Novan, Inc. | Topical gels |
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| WO2012004004A1 (en) | 2010-07-09 | 2012-01-12 | Fresenius Kabi Deutschland Gmbh | Nitric oxide delivering hydroxyalkyl starch derivatives |
| US8591876B2 (en) | 2010-12-15 | 2013-11-26 | Novan, Inc. | Methods of decreasing sebum production in the skin |
| US9034355B2 (en) | 2011-02-24 | 2015-05-19 | Colorado State University Research Foundation | Materials for modulating biological responses and methods of making |
| WO2012118829A2 (en) | 2011-02-28 | 2012-09-07 | Novan, Inc. | Tertiary s-nitrosothiol-modified nitricoxide-releasing xerogels and methods of using the same |
| WO2013006613A1 (en) * | 2011-07-05 | 2013-01-10 | Novan, Inc. | Methods of manufacturing topical compositions and apparatus for same |
| ES2797649T3 (es) | 2011-07-12 | 2020-12-03 | Icu Medical Inc | Dispositivo para entrega de agente antimicrobiano en un catéter transdérmico |
| US20130251855A1 (en) * | 2012-03-21 | 2013-09-26 | Pepsico, Inc. | Aqueous product comprising oil-containing microcapsules and method for the manufacture thereof |
| US9024096B2 (en) | 2012-12-11 | 2015-05-05 | Lummus Technology Inc. | Conversion of triacylglycerides-containing oils |
| US9162938B2 (en) | 2012-12-11 | 2015-10-20 | Chevron Lummus Global, Llc | Conversion of triacylglycerides-containing oils to hydrocarbons |
| CA2982456A1 (en) | 2015-05-08 | 2016-11-17 | Icu Medical, Inc. | Medical connectors configured to receive emitters of therapeutic agents |
| WO2018067838A1 (en) | 2016-10-07 | 2018-04-12 | The University Of North Carolina At Chapel Hill | S-nitrosothiol-mediated hyperbranched polyesters |
| AU2017341782B2 (en) | 2016-10-14 | 2023-03-16 | Icu Medical, Inc. | Sanitizing caps for medical connectors |
| WO2018127819A1 (en) | 2017-01-03 | 2018-07-12 | The University Of North Carolina At Chapel Hill | Nitric oxide-releasing alginates as biodegradable antibacterial scaffolds and methods pertaining thereto |
| CA3055474A1 (en) | 2017-03-28 | 2018-10-04 | The University Of North Carolina At Chapel Hill | Nitric oxide-releasing polyaminoglycosides as biodegradable antibacterial scaffolds and methods pertaining thereto |
| US11883807B2 (en) | 2017-04-11 | 2024-01-30 | Colorado State University Research Foundation | Functionalization of metal-organic frameworks |
| WO2018204206A2 (en) | 2017-05-01 | 2018-11-08 | Icu Medical, Inc. | Medical fluid connectors and methods for providing additives in medical fluid lines |
| JP2021515083A (ja) | 2018-03-06 | 2021-06-17 | ザ ユニバーシティ オブ ノース カロライナ アット チャペル ヒルＴｈｅ Ｕｎｉｖｅｒｓｉｔｙ Ｏｆ Ｎｏｒｔｈ Ｃａｒｏｌｉｎａ Ａｔ Ｃｈａｐｅｌ Ｈｉｌｌ | 生分解性の抗菌性足場としての一酸化窒素放出性シクロデキストリンおよびそれに関する方法 |
| US11517732B2 (en) | 2018-11-07 | 2022-12-06 | Icu Medical, Inc. | Syringe with antimicrobial properties |
| US11541221B2 (en) | 2018-11-07 | 2023-01-03 | Icu Medical, Inc. | Tubing set with antimicrobial properties |
| US11534595B2 (en) | 2018-11-07 | 2022-12-27 | Icu Medical, Inc. | Device for delivering an antimicrobial composition into an infusion device |
| US11400195B2 (en) | 2018-11-07 | 2022-08-02 | Icu Medical, Inc. | Peritoneal dialysis transfer set with antimicrobial properties |
| US11541220B2 (en) | 2018-11-07 | 2023-01-03 | Icu Medical, Inc. | Needleless connector with antimicrobial properties |
| CA3118905A1 (en) | 2018-11-21 | 2020-05-28 | Icu Medical, Inc. | Antimicrobial device comprising a cap with ring and insert |
| US11421044B2 (en) | 2018-12-28 | 2022-08-23 | The University Of North Carolina At Chapel Hill | Nitric oxide-releasing antibacterial polymers and scaffolds fabricated therefrom and methods pertaining thereto |
| EP4093205A4 (en) * | 2020-02-07 | 2024-02-21 | Know Bio Llc | NITRIC OXIDE-RELEASING ANTIBACTERIAL COMPOUNDS, FORMULATIONS AND ASSOCIATED METHODS |
| EP4255552A1 (en) | 2020-12-07 | 2023-10-11 | ICU Medical, Inc. | Peritoneal dialysis caps, systems and methods |
Family Cites Families (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4954526A (en) * | 1989-02-28 | 1990-09-04 | The United States Of America As Represented By The Department Of Health And Human Services | Stabilized nitric oxide - primary amine complexes useful as cardiovascular agents |
| US5208233A (en) * | 1989-09-15 | 1993-05-04 | The United States Of America As Represented By The Department Of Health And Human Services | Anti-hypertensive compositions of secondary amine-nitric oxide adducts and use thereof |
| US5039705A (en) * | 1989-09-15 | 1991-08-13 | The United States Of America As Represented By The Department Of Health And Human Services | Anti-hypertensive compositions of secondary amine-nitric oxide adducts and use thereof |
| US5721365A (en) * | 1989-09-15 | 1998-02-24 | Us Health | N-substituted piperazine NONOates |
| US5212204A (en) * | 1989-10-18 | 1993-05-18 | The United States Of America As Represented By The Department Of Health And Human Services | Antihypertensive compositions and use thereof |
| US5155137A (en) * | 1990-09-20 | 1992-10-13 | The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | Complexes of nitric oxide with polyamines |
| US5683668A (en) * | 1990-09-20 | 1997-11-04 | The United States Of America As Represented By The Department Of Health And Human Services | Method of generating nitric oxide gas using nitric oxide complexes |
| US5268465A (en) * | 1991-01-18 | 1993-12-07 | The Johns Hopkins University | Purification and molecular cloning of nitric oxide synthase |
| US5185376A (en) | 1991-09-24 | 1993-02-09 | The United States Of America As Represented By The Department Of Health And Human Services | Therapeutic inhibition of platelet aggregation by nucleophile-nitric oxide complexes and derivatives thereof |
| WO1993007114A1 (en) * | 1991-09-24 | 1993-04-15 | The United States Of America, Represented By The Secretary, Department Of Health And Human Services | Oxygen substituted derivatives of nucleophile-nitric oxide adducts as nitric oxide donor prodrugs |
| US5389675A (en) * | 1992-03-27 | 1995-02-14 | The United States Of America As Represented By The Department Of Health And Human Services | Mixed ligand metal complexes of nitric oxide-nucleophile adducts useful as cardiovascular agents |
| US5814666A (en) * | 1992-04-13 | 1998-09-29 | The United States As Represented By The Department Of Health And Human Services | Encapsulated and non-encapsulated nitric oxide generators used as antimicrobial agents |
| US6200558B1 (en) * | 1993-09-14 | 2001-03-13 | The United States Of America As Represented By The Department Of Health And Human Services | Biopolymer-bound nitric oxide-releasing compositions, pharmaceutical compositions incorporating same and methods of treating biological disorders using same |
| US5632981A (en) * | 1992-08-24 | 1997-05-27 | The United States Of America As Represented By The Department Of Health And Human Services | Biopolymer-bound nitric oxide-releasing compositions, pharmaceutical compositions incorporating same and methods of treating biological disorders using same |
| US5650447A (en) * | 1992-08-24 | 1997-07-22 | The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | Nitric oxide-releasing polymers to treat restenosis and related disorders |
| US5691423A (en) * | 1992-08-24 | 1997-11-25 | The United States Of America As Represented By The Department Of Health And Human Services | Polysaccharide-bound nitric oxide-nucleophile adducts |
| US5525357A (en) * | 1992-08-24 | 1996-06-11 | The United States Of America As Represented By The Department Of Health And Human Services | Polymer-bound nitric oxide/nucleophile adduct compositions, pharmaceutical compositions incorporating same and methods of treating biological disorders using same |
| US5405919A (en) * | 1992-08-24 | 1995-04-11 | The United States Of America As Represented By The Secretary Of Health And Human Services | Polymer-bound nitric oxide/nucleophile adduct compositions, pharmaceutical compositions and methods of treating biological disorders |
| US5910316A (en) * | 1992-08-24 | 1999-06-08 | The United States Of America, As Represented By The Department Of Health And Human Services | Use of nitric oxide-releasing agents to treat impotency |
| US5658565A (en) * | 1994-06-24 | 1997-08-19 | University Of Pittsburgh Of The Commonwealth System Of Higher Education | Inducible nitric oxide synthase gene for treatment of disease |
| JPH08503852A (ja) * | 1992-11-25 | 1996-04-30 | ユニバーシティ オブ ピッツバーグ オブ ザ コモンウェルス システム オブハイヤー エデュケーション | ヒト誘導性一酸化窒素シンターゼのｃＤＮＡクローンおよびその作製方法 |
| US5891459A (en) * | 1993-06-11 | 1999-04-06 | The Board Of Trustees Of The Leland Stanford Junior University | Enhancement of vascular function by modulation of endogenous nitric oxide production or activity |
| US5428070A (en) * | 1993-06-11 | 1995-06-27 | The Board Of Trustees Of The Leland Stanford Junior University | Treatment of vascular degenerative diseases by modulation of endogenous nitric oxide production of activity |
| US5945452A (en) * | 1993-06-11 | 1999-08-31 | The Board Of Trustees Of The Leland Stanford Junior University | Treatment of vascular degenerative diseases by modulation of endogenous nitric oxide production or activity |
| US5482925A (en) * | 1994-03-17 | 1996-01-09 | Comedicus Incorporated | Complexes of nitric oxide with cardiovascular amines as dual acting cardiovascular agents |
| US5700830A (en) * | 1994-11-22 | 1997-12-23 | The United States Of America As Represented By The Department Of Health And Human Services | Use of nitric oxide-releasing agents for reducing metastasis risk |
| US5814565A (en) * | 1995-02-23 | 1998-09-29 | University Of Utah Research Foundation | Integrated optic waveguide immunosensor |
| US5698738A (en) | 1995-05-15 | 1997-12-16 | Board Of Regents, The University Of Texas System | N-nitroso-N-substituted hydroxylamines as nitric oxide donors |
| US5609629A (en) * | 1995-06-07 | 1997-03-11 | Med Institute, Inc. | Coated implantable medical device |
| US5714511A (en) * | 1995-07-31 | 1998-02-03 | The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | Selective prevention of organ injury in sepsis and shock using selection release of nitric oxide in vulnerable organs |
| US6610660B1 (en) * | 1996-09-27 | 2003-08-26 | The United States Of America As Represented By The Department Of Health And Human Services | O2-arylated or O2-glycosylated 1-substituted diazen-1-ium-1,2-diolates and O2-substituted 1-[(2-carboxylato) pyrrolidin-1-yl] diazen-1-ium-1,2-diolates |
| EP1439187B1 (en) | 1996-09-27 | 2013-12-18 | THE UNITED STATES GOVERNMENT as represented by THE DEPARTMENT OF HEALTH AND HUMAN SERVICES | O2-arylated or o2-glycosylated 1-substituted diazen-1-ium-1,2-diolates and o2-substituted 1- (2-carboxylato)pyrrolidin-1-yl diazen-1-ium-1,2-diolates |
| AU726861B2 (en) * | 1997-07-03 | 2000-11-23 | Government Of The United States Of America, As Represented By The Secretary Of The Department Of Health And Human Services, The | Novel nitric oxide-releasing amidine- and enamine-derived diazeniumdiolates, compositions and uses thereof and method of making same |
| US6261594B1 (en) * | 1998-11-25 | 2001-07-17 | The University Of Akron | Chitosan-based nitric oxide donor compositions |
| AU4556200A (en) | 1999-04-14 | 2000-11-02 | University Of Cincinnati, The | Silane coatings for adhesion promotion |
| US6270779B1 (en) * | 2000-05-10 | 2001-08-07 | United States Of America | Nitric oxide-releasing metallic medical devices |
| US6673338B1 (en) * | 2001-09-10 | 2004-01-06 | The United States Of America As Represented By The Department Of Health And Human Services | Nitric oxide-releasing imidate and thioimidate diazeniumdiolates, compositions, uses thereof and method of making same |
| US6703046B2 (en) * | 2001-10-04 | 2004-03-09 | Medtronic Ave Inc. | Highly cross-linked, extremely hydrophobic nitric oxide-releasing polymers and methods for their manufacture and use |
| US6951902B2 (en) * | 2002-08-16 | 2005-10-04 | Michigan Biotechnology Institute | Two dimensional polymer that generates nitric oxide |
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- 2006-10-16 AU AU2006309212A patent/AU2006309212B2/en not_active Ceased
- 2006-10-16 EP EP06826062A patent/EP1942942A2/en not_active Ceased
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| AU2006309212A1 (en) | 2007-05-10 |
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| WO2007053292A2 (en) | 2007-05-10 |
| US7928079B2 (en) | 2011-04-19 |
| CA2628055A1 (en) | 2007-05-10 |
| WO2007053292A3 (en) | 2008-03-27 |
| EP1942942A2 (en) | 2008-07-16 |
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