CA3082130A1 - Nitric oxide-releasing hyperbranched compounds as antibacterial scaffolds and methods pertaining thereto - Google Patents
Nitric oxide-releasing hyperbranched compounds as antibacterial scaffolds and methods pertaining thereto Download PDFInfo
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- CA3082130A1 CA3082130A1 CA3082130A CA3082130A CA3082130A1 CA 3082130 A1 CA3082130 A1 CA 3082130A1 CA 3082130 A CA3082130 A CA 3082130A CA 3082130 A CA3082130 A CA 3082130A CA 3082130 A1 CA3082130 A1 CA 3082130A1
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- Prior art keywords
- hyperbranched
- amine
- compound
- group
- acrylate
- Prior art date
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- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 title claims abstract description 1289
- 238000000034 method Methods 0.000 title claims abstract description 150
- 150000001875 compounds Chemical class 0.000 title claims description 235
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- 150000001412 amines Chemical class 0.000 claims description 123
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 99
- QJSFZHSTNBFQKU-UHFFFAOYSA-N imino(dioxido)azanium Chemical compound [O-][N+]([O-])=N QJSFZHSTNBFQKU-UHFFFAOYSA-N 0.000 claims description 79
- 229920001577 copolymer Polymers 0.000 claims description 71
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- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 claims description 8
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
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- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 7
- DEGZUQBZHACZKW-UHFFFAOYSA-N 2-(methylamino)ethyl 2-methylprop-2-enoate Chemical compound CNCCOC(=O)C(C)=C DEGZUQBZHACZKW-UHFFFAOYSA-N 0.000 claims description 7
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- BEWCNXNIQCLWHP-UHFFFAOYSA-N 2-(tert-butylamino)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCNC(C)(C)C BEWCNXNIQCLWHP-UHFFFAOYSA-N 0.000 claims description 7
- XSHISXQEKIKSGC-UHFFFAOYSA-N 2-aminoethyl 2-methylprop-2-enoate;hydron;chloride Chemical compound Cl.CC(=C)C(=O)OCCN XSHISXQEKIKSGC-UHFFFAOYSA-N 0.000 claims description 7
- HFCUBKYHMMPGBY-UHFFFAOYSA-N 2-methoxyethyl prop-2-enoate Chemical compound COCCOC(=O)C=C HFCUBKYHMMPGBY-UHFFFAOYSA-N 0.000 claims description 7
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- JANUDBLANRHSLI-UHFFFAOYSA-N 5-butyl-1,3,4-oxadiazol-2-amine Chemical compound CCCCC1=NN=C(N)O1 JANUDBLANRHSLI-UHFFFAOYSA-N 0.000 claims description 7
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 7
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- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/028—Polyamidoamines
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/74—Synthetic polymeric materials
- A61K31/785—Polymers containing nitrogen
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
- A61L2/16—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using chemical substances
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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
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/002—Dendritic macromolecules
- C08G83/005—Hyperbranched macromolecules
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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
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/002—Dendritic macromolecules
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- C08G83/006—After treatment of hyperbranched macromolecules
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- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2202/00—Aspects relating to methods or apparatus for disinfecting or sterilising materials or objects
- A61L2202/20—Targets to be treated
- A61L2202/24—Medical instruments, e.g. endoscopes, catheters, sharps
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
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- Veterinary Medicine (AREA)
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- Pharmacology & Pharmacy (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Dental Tools And Instruments Or Auxiliary Dental Instruments (AREA)
- Materials For Medical Uses (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Polyamides (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Dental Prosthetics (AREA)
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| US201862737603P | 2018-09-27 | 2018-09-27 | |
| US62/737,603 | 2018-09-27 | ||
| PCT/US2018/061061 WO2019099525A1 (en) | 2017-11-15 | 2018-11-14 | Nitric oxide-releasing hyperbranched compounds as antibacterial scaffolds and methods pertaining thereto |
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| US11186681B2 (en) | 2016-10-07 | 2021-11-30 | The University Of North Carolina At Chapel Hill | S-Nitrosothiol-mediated hyperbranched polyesters |
| US11072668B2 (en) | 2017-01-03 | 2021-07-27 | The University Of North Carolina At Chapel Hill | Nitric oxide-releasing alginates as biodegradable antibacterial scaffolds and methods pertaining thereto |
| CN110461338A (zh) | 2017-03-28 | 2019-11-15 | 北卡罗来纳大学查佩尔希尔分校 | 作为可生物降解抗菌支架的释放一氧化氮的聚氨基糖苷类和其制备方法 |
| EP3710514B1 (en) | 2017-11-15 | 2023-06-07 | The University of North Carolina at Chapel Hill | Nitric oxide-releasing hyperbranched compounds as antibacterial scaffolds and methods pertaining thereto |
| EP3762039A4 (en) | 2018-03-06 | 2021-12-22 | The University of North Carolina at Chapel Hill | NITROGEN OXIDE RELEASING CYCLODEXTRIN AS BIODEGRADABLE ANTIBACTERIAL SCAFFOLDINGS AND RELATED PROCEDURES |
| EP3902841B1 (en) | 2018-12-28 | 2025-01-29 | The University of North Carolina at Chapel Hill | Nitric oxide-releasing antibacterial polymers and scaffolds fabricated therefrom and methods pertaining thereto |
| JP7338113B2 (ja) * | 2020-04-13 | 2023-09-05 | 大成建設株式会社 | 気体貯蔵放出化合物 |
| EP4167954A4 (en) * | 2020-06-18 | 2024-07-24 | Nanometics LLC (D.B.A. Phd Biosciences) | CHEMICALLY CROSS-LINKED ELASTOMERS FORMED BY MICHAEL ADDITION AND COMPOSITIONS COMPRISING SUCH ELASTOMERS |
| CN112023727B (zh) * | 2020-08-14 | 2022-07-12 | 万华化学集团股份有限公司 | 一种抗污染抑菌反渗透膜、制备方法及其应用 |
| CN114989265A (zh) * | 2022-05-30 | 2022-09-02 | 浙江大学 | 一种具有高效广谱抗细菌、真菌功能的营养型支化结构聚多肽 |
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| US4169079A (en) | 1977-10-24 | 1979-09-25 | Iwao Tabushi | Polystyrene based polymers containing cyclodextrin derivatives, metal complexes of the same, and process for the production of the same |
| US5574027A (en) | 1989-11-22 | 1996-11-12 | Bernstein; Lawrence R. | Pharmaceutical compositions of gallium complexes of 3-hydroxy-4-pyrones |
| US5234933A (en) | 1991-10-31 | 1993-08-10 | Board Of Governors Of Wayne State University And Vanderbilt University | Cyclic hydroxamic acids |
| DE4210332C1 (enExample) | 1992-03-30 | 1993-07-15 | Gruenenthal Gmbh, 5100 Aachen, De | |
| 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 |
| US5238832A (en) | 1992-06-08 | 1993-08-24 | Board Of Governors Of Wayne State University | Aryl aliphatic acids |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| AU685178B2 (en) | 1993-10-08 | 1998-01-15 | United States Of America, Represented By The Secretary, Department Of Health And Human Services, The | Use of nitric oxide-releasing compounds as hypoxic cell radiation sensitizers |
| US5840759A (en) | 1993-10-08 | 1998-11-24 | The United States Of America As Represented By The Department Of Health And Human Services | Use of nitric oxide releasing compounds to protect noncancerous cells from chemotherapeutic agents |
| AU704173B2 (en) | 1993-11-02 | 1999-04-15 | Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College, The | Use of nitric oxide releasing compounds as protective agents in ischemia reperfusion injury |
| CA2205564C (en) | 1994-11-22 | 2006-07-11 | The United States Of America, Represented By The Secretary, Department Of Health And Human Services | Pharmaceutical compositions comprising nitric oxide-releasing biopolymers |
| 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 |
| US6232434B1 (en) | 1996-08-02 | 2001-05-15 | Duke University Medical Center | Polymers for delivering nitric oxide in vivo |
| US5770645A (en) | 1996-08-02 | 1998-06-23 | Duke University Medical Center | Polymers for delivering nitric oxide in vivo |
| US20030093143A1 (en) | 1999-03-01 | 2003-05-15 | Yiju Zhao | Medical device having surface depressions containing nitric oxide releasing compound |
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|---|---|
| CN111491982A (zh) | 2020-08-04 |
| EP3710514A1 (en) | 2020-09-23 |
| JP2021503029A (ja) | 2021-02-04 |
| WO2019099525A1 (en) | 2019-05-23 |
| AU2018369760A1 (en) | 2020-06-25 |
| AU2018369760B2 (en) | 2025-01-02 |
| EP3710514B1 (en) | 2023-06-07 |
| JP2025084800A (ja) | 2025-06-03 |
| US20200332061A1 (en) | 2020-10-22 |
| CN111491982B (zh) | 2023-04-18 |
| US12460050B2 (en) | 2025-11-04 |
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