CN102432511B - 表面两亲聚合物和低聚物及其应用 - Google Patents
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- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
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- Organic Chemistry (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
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| EP2471526A3 (en) | 2003-03-17 | 2012-12-12 | The Trustees Of The University Of Pennsylvania | Facially amphiphillic polymers and oligomers and uses thereof |
| CN1922133A (zh) | 2004-01-23 | 2007-02-28 | 宾夕法尼亚州大学理事会 | 表面两亲性聚芳基和聚芳基炔基聚合物和低聚物及其用途 |
| AU2005254574B2 (en) | 2004-06-15 | 2012-02-02 | Polymedix, Inc. | Polycationic compounds and uses thereof |
| US20060241052A1 (en) | 2005-02-25 | 2006-10-26 | Degrado William F | Facially amphiphilic polymers and oligomers, compositions thereof, and use thereof in methods of treating cancer |
| US20090092574A1 (en) | 2006-12-29 | 2009-04-09 | Scott Richard W | Ophthalmic And Otic Compositions Of Facially Amphiphilic Polymers And Oligomers And Uses Thereof |
| DE102008027133A1 (de) * | 2008-05-30 | 2009-12-03 | Ls Medcap Gmbh | Vollsynthetisches Albumin-Analogon |
| RU2530899C2 (ru) * | 2008-07-28 | 2014-10-20 | Селлсьютикс Корпорейшн | Противомалярийные соединения |
| TWI478915B (zh) * | 2008-10-27 | 2015-04-01 | Cellceutix Corp | 宿主防禦之合成模擬物及其用途 |
| CA2746421A1 (en) * | 2008-12-10 | 2010-06-17 | Polymedix, Inc. | Antimicrobial molecules for treating multi-drug resistant and extensively drug resistant strains of mycobacterium |
| US9481719B2 (en) | 2009-06-03 | 2016-11-01 | Basf Se | Recombinant production of peptides |
| MX2012007662A (es) * | 2010-01-07 | 2012-08-23 | Polymedix Inc | Compuestos anti-heparina. |
| SG188281A1 (en) * | 2010-08-23 | 2013-04-30 | Univ California | Compositions and uses of materials with high antimicrobial activity and low toxicity |
| EP2709619B1 (en) | 2011-05-16 | 2017-10-11 | Cellceutix Corporation | Compounds for use in treatment of mucositis |
| CA2937128A1 (en) * | 2011-05-19 | 2012-11-22 | Eugene J. Oliva | Heparin-based compostions and methods for the inhibition of metastasis |
| AU2012352621A1 (en) | 2011-12-13 | 2014-07-24 | Cellceutix Corporation | Cyclic compounds and methods of making and using the same |
| MX2014008763A (es) * | 2012-01-18 | 2015-04-13 | Cellceutix Corp | Compuestos y metodos para tratar infecciones por candidosis y aspergillus. |
| CN103373938B (zh) * | 2012-04-17 | 2016-03-30 | 天津理工大学 | 一种4-乙氧基-1,3-苯二甲酰胺类化合物及其制备和应用 |
| EP2986625B1 (en) * | 2014-03-14 | 2020-03-11 | Bio-rad Laboratories, Inc. | Mixed mode ligands |
| CN108289926A (zh) | 2015-10-14 | 2018-07-17 | 西北大学 | 用于生长因子递送和骨再生的纳米纤维糊剂 |
| CN107390307A (zh) * | 2016-05-16 | 2017-11-24 | 惠和株式会社 | 液晶显示装置用光学片、液晶显示装置用背光单元及液晶显示装置用光学片的制造方法 |
| WO2018075885A1 (en) | 2016-10-21 | 2018-04-26 | Northwestern University | Anti-microbial supramolecular structures |
| WO2019067676A1 (en) | 2017-09-28 | 2019-04-04 | The Regents Of The University Of California | HYDROGELS OF POLYIONIC POLYPEPTIDE COMPLEXES AND USES THEREOF |
| JP7560884B2 (ja) | 2019-01-24 | 2024-10-03 | ノースウエスタン ユニバーシティ | 超分子ikvavマトリックス内の動力学は、ヒトipsc由来のニューロンの機能的成熟と再生を増強する |
| US12214076B2 (en) | 2019-02-18 | 2025-02-04 | Northwestern University | Drug delivery vehicles for atherosclerosis nanomedicine |
| CN111407764B (zh) * | 2020-03-27 | 2021-09-10 | 广州中医药大学(广州中医药研究院) | 一种杂萜衍生物在制备抗非酒精性脂肪性肝炎及肝纤维化的药物中的应用 |
| US12090206B2 (en) | 2020-04-23 | 2024-09-17 | The Regents Of The University Of California | Compositions comprising tri- and penta-block synthetic copolypeptide hydrogels |
| WO2021248008A1 (en) | 2020-06-05 | 2021-12-09 | Innovation Pharmaceuticals Inc. | Arylamide compounds for treatment and prevention of viral infections |
| US12247063B2 (en) | 2020-07-13 | 2025-03-11 | Northwestern University | Cell surface modification by coating with peptide amphiphiles (PAs) |
| US11998589B2 (en) | 2020-07-13 | 2024-06-04 | Northwestern University | PEGylated peptide amphiphile nanofibers and methods of use |
| US12116461B2 (en) | 2020-08-21 | 2024-10-15 | Northwestern University | Host-guest interactions for pa superstructure formation |
| CA3225407A1 (en) | 2021-07-29 | 2023-02-02 | Shelby Chi YUAN | Self-assembling peptide amphiphiles displaying a transforming growth factor beta 1 (tgf-.beta.1) mimetic epitope |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997049413A1 (en) * | 1996-06-24 | 1997-12-31 | Geltex Pharmaceuticals, Inc. | Ionic polymers as anti-infective agents |
| WO2001051456A2 (en) * | 2000-01-13 | 2001-07-19 | Tularik Inc. | Antibacterial agents |
| WO2002100295A2 (en) * | 2001-03-08 | 2002-12-19 | The Trustees Of The University Of Pennsylvania | Facially amphiphilic polymers as anti-infective agents |
Family Cites Families (93)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH479557A (de) | 1961-09-11 | 1969-10-15 | Wander Ag Dr A | Verfahren zur Herstellung neuer mehrbasischer Verbindungen |
| CH525898A (de) | 1961-09-11 | 1972-07-31 | Wander Ag Dr A | Verfahren zur Herstellung mehrbasischer Verbindungen |
| GB1033777A (en) * | 1963-06-06 | 1966-06-22 | Sterling Drug Inc | Bis-anilide derivatives |
| CH475331A (de) * | 1965-07-05 | 1969-07-15 | Ciba Geigy | Verfahren zum Härten von Gelatine |
| US3484407A (en) * | 1967-01-13 | 1969-12-16 | Monsanto Co | Linear condensation polymers containing carbonamide and heterocyclic linkages |
| GB1324087A (en) | 1969-07-18 | 1973-07-18 | Commw Scient Ind Res Org | Copolymers and veterinary compositions treated therewith |
| US4118232A (en) * | 1971-04-07 | 1978-10-03 | Ciba-Geigy Ag | Photographic material containing sulphonic acid group containing disazo dyestuffs |
| US3829563A (en) * | 1972-11-30 | 1974-08-13 | Hoffmann La Roche | Emollient cleansing compositions |
| US4038416A (en) * | 1975-09-11 | 1977-07-26 | Chugai Seiyaku Kabushiki Kaisha | Pharmaceutical composition and method of the use thereof |
| JPS5285133A (en) * | 1976-01-05 | 1977-07-15 | Chugai Pharmaceut Co Ltd | Bis-(benzamide)-benzene derivatives |
| DE2616479C2 (de) | 1976-04-14 | 1986-12-04 | Brickl, Rolf, Dr., 7951 Warthausen | Substituierte Fluoracylresorcine, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel und Kosmetika |
| US4392848A (en) * | 1979-06-25 | 1983-07-12 | The Procter & Gamble Company | Catheterization |
| US4343788A (en) * | 1979-06-29 | 1982-08-10 | The Procter & Gamble Company | Antimicrobial polymer compositions |
| US4252951A (en) * | 1979-10-09 | 1981-02-24 | Eli Lilly And Company | Isolation of syn-7-(2-amino-4-thiazolyl)-(methoxyimino)acetamido-3-acetoxymethyl-3-cephem-4-carboxylic acid |
| JPS5928521B2 (ja) | 1980-03-04 | 1984-07-13 | 兼商株式会社 | 殺線虫組成物 |
| FR2527618A1 (fr) * | 1982-05-25 | 1983-12-02 | Thomson Csf | Polymeres contenant des heterocycles et des noyaux aromatiques et materiaux organiques conducteurs formes a partir de ces polymeres |
| US4515910A (en) * | 1983-01-26 | 1985-05-07 | Rawls Henry R | Interpolymeric resin for treatment of teeth |
| JPS59177558U (ja) | 1983-05-14 | 1984-11-27 | ヤンマーディーゼル株式会社 | 農用トラクタ−のパワ−ステアリング装置 |
| DE3533612A1 (de) | 1985-09-20 | 1987-04-02 | Johannes Reinmueller | Neuartige verwendung von taurolin |
| CA1290490C (en) | 1985-11-20 | 1991-10-08 | Masakazu Uekita | Amphiphilic high polymer and process for producing the same |
| JPS6322067A (ja) | 1986-03-10 | 1988-01-29 | Nippon Soda Co Ltd | ピロ−ル誘導体のlb膜およびその製造方法 |
| JPS62224090A (ja) | 1986-03-26 | 1987-10-02 | Polyplastics Co | 高分子圧電材料 |
| JPH0739457B2 (ja) * | 1986-05-14 | 1995-05-01 | タキロン株式会社 | 両親媒性セグメントポリウレタン |
| US4826829A (en) * | 1986-07-23 | 1989-05-02 | Fmc Corporation | 2-Substituted ethynyl thiophene pesticides |
| US4847353A (en) * | 1986-11-20 | 1989-07-11 | Nippon Steel Chemical Co., Ltd. | Resins of low thermal expansivity |
| US6040251A (en) * | 1988-03-14 | 2000-03-21 | Nextec Applications Inc. | Garments of barrier webs |
| US6083602A (en) * | 1988-03-14 | 2000-07-04 | Nextec Applications, Inc. | Incontinent garments |
| US5912116A (en) * | 1988-03-14 | 1999-06-15 | Nextec Applications, Inc. | Methods of measuring analytes with barrier webs |
| US5874164A (en) * | 1988-03-14 | 1999-02-23 | Nextec Applications, Inc. | Barrier webs having bioactive surfaces |
| US5856245A (en) * | 1988-03-14 | 1999-01-05 | Nextec Applications, Inc. | Articles of barrier webs |
| JPH0229436A (ja) | 1988-07-19 | 1990-01-31 | Ricoh Co Ltd | 導電性ピロール類重合膜の光化学的製造方法 |
| JP2597160B2 (ja) * | 1988-09-02 | 1997-04-02 | 富士写真フイルム株式会社 | 電子写真感光体 |
| US4943624A (en) * | 1988-10-28 | 1990-07-24 | Lehigh University | Supramolecular surfactants: amphiphilic polymers designed to disrupt lipid membranes |
| US5071648A (en) * | 1989-04-06 | 1991-12-10 | Merocel Corporation | Polymeric broad-spectrum antimicrobial materials |
| US5073564A (en) * | 1990-07-06 | 1991-12-17 | Fmc Corporation | Ethynylbenzothiophene pesticides |
| US5219965A (en) * | 1990-11-27 | 1993-06-15 | Bausch & Lomb Incorporated | Surface modification of polymer objects |
| EP0489660B1 (fr) | 1990-12-06 | 1994-11-02 | Roussel-Uclaf | Utilisation de thiazolylalkoxy acrylates pour la fabrication de compositions insecticides et/ou acaricides |
| US5648070A (en) * | 1991-12-04 | 1997-07-15 | Cobe Laboratories, Inc. | Biocompatible anion exchange materials |
| US5424063A (en) * | 1992-01-09 | 1995-06-13 | The Dow Chemical Company | Narrow poly- and mono-dispersed anionic oligomers, and their uses, formulations and process |
| US5262476A (en) * | 1992-03-10 | 1993-11-16 | The Dow Chemical Company | Polycarbonate/polyester blends modified with poly(phenylene ether) |
| DE19709075A1 (de) * | 1997-03-06 | 1998-09-10 | Huels Chemische Werke Ag | Verfahren zur Herstellung antimikrobieller Kunststoffe |
| US5847047A (en) * | 1993-06-22 | 1998-12-08 | E. I. Du Pont De Nemours And Company | Antimicrobial composition of a polymer and a peptide forming amphiphilic helices of the magainin-type |
| US5520910A (en) * | 1993-07-14 | 1996-05-28 | Nippon Chemical Industrial | Antimicrobial polymer, contact lens and contact lens-care articles |
| WO1995019974A2 (en) | 1994-01-24 | 1995-07-27 | Harris Stephen J | Calixarene-based compounds having antibacterial, antifungal, anticancer-hiv activity |
| ATE198119T1 (de) | 1994-09-01 | 2001-01-15 | Novo Nordisk As | Eine grundlegende proteinzusammensetzung zur abtötung oder inhibierung mikrobieller zellen |
| GB9419206D0 (en) | 1994-09-23 | 1994-11-09 | Nycomed Innovation Ab | Contrast media |
| WO1997029160A1 (en) | 1996-02-09 | 1997-08-14 | Surface Solutions Laboratories, Inc. | Water-based hydrophilic coating compositions and articles prepared therefrom |
| FR2753094B1 (fr) | 1996-09-06 | 1998-10-16 | Oreal | Composition de teinture d'oxydation pour fibres keratiniques comprenant un polymere amphiphile anionique |
| US5962521A (en) * | 1997-04-04 | 1999-10-05 | Guilford Pharmaceuticals Inc. | Hydroxamic acid derivatives |
| WO1998017625A1 (en) | 1996-10-22 | 1998-04-30 | Daiichi Pharmaceutical Co., Ltd. | Novel remedies for infectious diseases |
| US6107397A (en) * | 1997-03-24 | 2000-08-22 | Basf Aktiengesellschaft | Aqueous copolymer dispersions of water-soluble monomers with N-vinyl groups and hydrophobic monomers |
| US6217886B1 (en) | 1997-07-14 | 2001-04-17 | The Board Of Trustees Of The University Of Illinois | Materials and methods for making improved micelle compositions |
| DE19735715A1 (de) | 1997-08-18 | 1999-02-25 | Huels Chemische Werke Ag | Amphiphile Polymere auf Basis von Polyestern mit einkondensierten acetalischen Gruppen, die bei Raumtemperatur flüssig sind, sowie ihr Einsatz in Wasch- und Reinigungsmitteln |
| US5994340A (en) * | 1997-08-29 | 1999-11-30 | Synphar Laboratories, Inc. | Azetidinone derivatives as β-lactamase inhibitors |
| JPH11152329A (ja) | 1997-11-21 | 1999-06-08 | Hitachi Chem Co Ltd | ポリアミド又はその誘導体の製造法 |
| JP2002507557A (ja) | 1998-03-26 | 2002-03-12 | デパートメント オブ ジ アーミー, ユー.エス. ガバメント | 抗生物質抵抗性感染の処置のための置換芳香族化合物 |
| CA2234410C (en) * | 1998-05-01 | 2002-07-16 | Jih Ru Hwu | Novel phloroglucide derivatives and their pharmaceutical use |
| US6399629B1 (en) * | 1998-06-01 | 2002-06-04 | Microcide Pharmaceuticals, Inc. | Efflux pump inhibitors |
| US6686345B2 (en) * | 1998-07-16 | 2004-02-03 | Research Development Foundation | DNA-cleaving antitumor agents |
| DE19845358A1 (de) * | 1998-10-02 | 2000-04-06 | Roehm Gmbh | Überzogene Arzneiformen mit kontrollierter Wirkstoffabgabe |
| AR024237A1 (es) | 1998-12-21 | 2002-09-25 | Novartis Ag | Copolimeros en bloque anfifilicos, procedimiento y precursores para su preparacion, y articulo moldeado obtenible a partir de los mismos |
| ES2223464T3 (es) * | 1999-02-01 | 2005-03-01 | Eisai Co., Ltd. | Compuestos adyuvantes inmunologicos. |
| US6166172A (en) * | 1999-02-10 | 2000-12-26 | Carnegie Mellon University | Method of forming poly-(3-substituted) thiophenes |
| DE19908184A1 (de) * | 1999-02-25 | 2000-08-31 | Basf Ag | Verfahren zur Herstellung wässriger Dispersionen von Copolymerisaten aus hydrophilen und hydrophoben Monomeren sowie daraus erhältliche Copolymerisate und deren Anwendungen |
| DE19921902A1 (de) | 1999-05-12 | 2000-11-16 | Creavis Tech & Innovation Gmbh | Mikrobizide Copolymere |
| US6309633B1 (en) * | 1999-06-19 | 2001-10-30 | Nobex Corporation | Amphiphilic drug-oligomer conjugates with hydroyzable lipophile components and methods for making and using the same |
| JP2001133975A (ja) | 1999-08-23 | 2001-05-18 | Toray Ind Inc | ポジ型感光性樹脂前駆体組成物 |
| AU2831901A (en) | 2000-01-28 | 2001-08-07 | Novo Nordisk A/S | Propionic acid derivatives and their use in the treatment of diabetes and obesity |
| US6768009B1 (en) | 2000-03-24 | 2004-07-27 | The Regents Of The University Of California | N-halamine vinyl compounds and their polymeric biocides |
| WO2002095044A2 (en) | 2001-05-21 | 2002-11-28 | Molecular Electronics Corporation | Lipase catalyzed esterification, transesterification, and hydrolysis of arylthiols and aryl-thioesters |
| JP2002363261A (ja) | 2001-06-06 | 2002-12-18 | Sumitomo Bakelite Co Ltd | 難燃性エポキシ樹脂組成物、半導体封止材料及び半導体装置 |
| CN1170816C (zh) | 2001-07-19 | 2004-10-13 | 温州师范学院 | N、n'-二取代苯胺基芳香二甲酰胺及其衍生物、制备方法和用途 |
| US20030073712A1 (en) | 2001-07-23 | 2003-04-17 | Bing Wang | Cytoprotective compounds, pharmaceutical and cosmetic formulations, and methods |
| US20030130454A1 (en) * | 2001-11-07 | 2003-07-10 | Mitsubishi Rayon Co., Ltd. | Process for producing amphipathic polymers |
| JP2003165805A (ja) | 2001-11-28 | 2003-06-10 | Mitsubishi Rayon Co Ltd | 両親媒性重合体の製造方法 |
| CA2487454A1 (en) * | 2002-05-28 | 2003-12-04 | The Trustees Of The University Of Pennsylvania | Methods, systems, and computer program products for computational analysis and design of amphiphilic polymers |
| EP1513622A4 (en) * | 2002-06-13 | 2005-09-14 | Univ Pennsylvania | METHODS, SYSTEMS AND COMPUTER PROGRAM PRODUCTS FOR STIMULATING BIOMEMBRANES USING ROUGH GRAIN MODELS |
| CA2494695C (en) | 2002-08-02 | 2011-04-05 | Ab Science | 2-(3-aminoaryl)amino-4-aryl-thiazoles and their use as c-kit inhibitors |
| US7378479B2 (en) * | 2002-09-13 | 2008-05-27 | Lubrizol Advanced Materials, Inc. | Multi-purpose polymers, methods and compositions |
| US7141519B2 (en) | 2002-09-20 | 2006-11-28 | Kimberly-Clark Worldwide, Inc. | Ion triggerable, cationic polymers, a method of making same and items using same |
| JP3836420B2 (ja) | 2002-11-18 | 2006-10-25 | 孝志 澤口 | 両親媒性メタクリレート及びその重合体 |
| EP2471526A3 (en) | 2003-03-17 | 2012-12-12 | The Trustees Of The University Of Pennsylvania | Facially amphiphillic polymers and oligomers and uses thereof |
| JP2004323688A (ja) | 2003-04-25 | 2004-11-18 | Mitsubishi Rayon Co Ltd | 両親媒性重合体およびその製造方法 |
| US7332623B2 (en) * | 2003-06-30 | 2008-02-19 | Kaohsiung Medical University | Aryl-substituted acyclic enediyne compounds |
| US20050004211A1 (en) * | 2003-06-30 | 2005-01-06 | Kaohsiung Medical University | Pharmaceutical compositions comprising aryl-substituted acyclic enediyne compounds |
| US7781498B2 (en) * | 2003-07-03 | 2010-08-24 | Mallard Creek Polymers, Inc. | Cationic latex as a carrier for bioactive ingredients and methods for making and using the same |
| ITMI20031790A1 (it) * | 2003-09-19 | 2005-03-20 | Consiglio Nazionale Ricerche | Antagonistici abiotici dell'eparina. |
| US20070173752A1 (en) * | 2003-11-28 | 2007-07-26 | Troels Schonfeldt | Integrated package |
| CN1922133A (zh) * | 2004-01-23 | 2007-02-28 | 宾夕法尼亚州大学理事会 | 表面两亲性聚芳基和聚芳基炔基聚合物和低聚物及其用途 |
| AU2005254574B2 (en) | 2004-06-15 | 2012-02-02 | Polymedix, Inc. | Polycationic compounds and uses thereof |
| JP5027659B2 (ja) | 2004-07-23 | 2012-09-19 | ザ トラスティーズ オブ ザ ユニバーシティ オブ ペンシルバニア | 抗菌コポリマーおよびその使用 |
| EP2404895A1 (en) | 2004-10-04 | 2012-01-11 | Regents of the University of Minnesota | Calixarene-based peptide conformation mimetics, methods of use, and methods of making |
| US20060241052A1 (en) * | 2005-02-25 | 2006-10-26 | Degrado William F | Facially amphiphilic polymers and oligomers, compositions thereof, and use thereof in methods of treating cancer |
-
2004
- 2004-03-17 EP EP12000364A patent/EP2471526A3/en not_active Withdrawn
- 2004-03-17 EP EP12000362A patent/EP2471524A3/en not_active Withdrawn
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- 2004-03-17 KR KR1020057017578A patent/KR101241176B1/ko not_active Expired - Lifetime
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997049413A1 (en) * | 1996-06-24 | 1997-12-31 | Geltex Pharmaceuticals, Inc. | Ionic polymers as anti-infective agents |
| WO2001051456A2 (en) * | 2000-01-13 | 2001-07-19 | Tularik Inc. | Antibacterial agents |
| WO2002100295A2 (en) * | 2001-03-08 | 2002-12-19 | The Trustees Of The University Of Pennsylvania | Facially amphiphilic polymers as anti-infective agents |
Non-Patent Citations (1)
| Title |
|---|
| De novo design of biomimetic antimicrobial polymers;Gregory N. Tew, et al.;《Proceedings of the national academy of sciences of USA》;20020416;第99卷(第8期);5110-5114 * |
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