JP2008531585A - 表面が両親媒性のポリマーおよびオリゴマー、それらの組成物そして癌治療方法におけるそれらの使用 - Google Patents
表面が両親媒性のポリマーおよびオリゴマー、それらの組成物そして癌治療方法におけるそれらの使用 Download PDFInfo
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
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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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/10—Peptides having 12 to 20 amino acids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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| CN102295744B (zh) * | 2001-03-08 | 2014-07-02 | 宾夕法尼亚州大学理事会 | 作为抗感染药的表面两亲聚合物 |
| CA2519023C (en) | 2003-03-17 | 2014-05-20 | The Trustees Of The University Of Pennsylvania | Facially amphiphilic polymers and oligomers and uses thereof |
| EP1711455A4 (en) | 2004-01-23 | 2007-11-07 | Univ Pennsylvania | FAZIAL AMPHIPHILE POLYARYL AND POLYARYL ALKINYL POLYMERS AND OLIGOMERS AND ITS APPLICATIONS |
| EP2380872B1 (en) | 2004-06-15 | 2014-04-23 | Cellceutix Corporation | Polycationic compounds and uses thereof |
| US20090092574A1 (en) * | 2006-12-29 | 2009-04-09 | Scott Richard W | Ophthalmic And Otic Compositions Of Facially Amphiphilic Polymers And Oligomers And Uses Thereof |
| KR100842351B1 (ko) * | 2007-01-04 | 2008-06-30 | 한국생명공학연구원 | 인돌 유도체를 유효성분으로 함유하는 암 예방 및 치료용약학적 조성물 |
| US8278309B2 (en) | 2008-10-27 | 2012-10-02 | Polymedix, Inc. | Synthetic mimetics of host defense and uses thereof |
| KR20110098800A (ko) * | 2008-12-10 | 2011-09-01 | 폴리메딕스, 인코포레이티드 | 마이코박테리움의 다중-약물 내성 및 광범위 약물 내성 균주를 치료하기 위한 항미생물 분자 |
| KR101094299B1 (ko) | 2009-12-17 | 2011-12-19 | 삼성모바일디스플레이주식회사 | 선형 증발원 및 이를 포함하는 증착 장치 |
| EP2709619B1 (en) | 2011-05-16 | 2017-10-11 | Cellceutix Corporation | Compounds for use in treatment of mucositis |
| WO2013090185A1 (en) | 2011-12-13 | 2013-06-20 | Polymedix, Inc. | Cyclic compounds and methods of making and using the same |
| CA2862170A1 (en) * | 2012-01-18 | 2013-07-25 | Cellceutix Corporation | Compounds and methods for treating candidiasis and aspergillus infections |
| CN109305926B (zh) * | 2018-10-18 | 2021-06-25 | 吉林大学 | 一种可形成分子内氢键的芳酰胺类金属配体及其制备方法与应用 |
| US11771694B2 (en) | 2020-06-05 | 2023-10-03 | Innovation Pharmaceuticals Inc. | Arylamide compounds for treatment and prevention of viral infections |
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| WO2004082634A2 (en) * | 2003-03-17 | 2004-09-30 | The Trustees Of The University Of Pennsylvania | Facially amphiphilic polymers and oligomers and uses thereof |
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| CH525898A (de) * | 1961-09-11 | 1972-07-31 | Wander Ag Dr A | Verfahren zur Herstellung mehrbasischer Verbindungen |
| CH479557A (de) * | 1961-09-11 | 1969-10-15 | Wander Ag Dr A | Verfahren zur Herstellung neuer mehrbasischer Verbindungen |
| GB1033776A (en) * | 1963-06-06 | 1966-06-22 | Sterling Drug Inc | Iodinated acid amides and esters and salts thereof |
| US3484407A (en) * | 1967-01-13 | 1969-12-16 | Monsanto Co | Linear condensation polymers containing carbonamide and heterocyclic linkages |
| US4118232A (en) * | 1971-04-07 | 1978-10-03 | Ciba-Geigy Ag | Photographic material containing sulphonic acid group containing disazo dyestuffs |
| US3878705A (en) | 1972-05-01 | 1975-04-22 | Roger L Iffland | Bearing cage and method for producing a bearing cage |
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| US4038416A (en) * | 1975-09-11 | 1977-07-26 | Chugai Seiyaku Kabushiki Kaisha | Pharmaceutical composition and method of the use thereof |
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| 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 |
| 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 |
| DE3533612A1 (de) * | 1985-09-20 | 1987-04-02 | Johannes Reinmueller | Neuartige verwendung von taurolin |
| 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 |
| US6083602A (en) * | 1988-03-14 | 2000-07-04 | Nextec Applications, Inc. | Incontinent garments |
| 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 |
| US6040251A (en) * | 1988-03-14 | 2000-03-21 | Nextec Applications Inc. | Garments of barrier webs |
| US5912116A (en) * | 1988-03-14 | 1999-06-15 | Nextec Applications, Inc. | Methods of measuring analytes with barrier webs |
| 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 |
| US5648070A (en) * | 1991-12-04 | 1997-07-15 | Cobe Laboratories, Inc. | Biocompatible anion exchange materials |
| 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 |
| WO1995000547A1 (en) * | 1993-06-22 | 1995-01-05 | E.I. Du Pont De Nemours And Company | Antimicrobial composition of a polymer and a peptide forming amphiphilic helices of the magainin-type |
| DE69413790T2 (de) * | 1993-07-14 | 1999-02-25 | Nippon Chemical Industrial Co., Ltd., Tokio/Tokyo | Antibakterielles polymer, kontaktlinse und kontaktlinsenpflegeprodukt |
| US6034129A (en) * | 1996-06-24 | 2000-03-07 | Geltex Pharmaceuticals, Inc. | Ionic polymers as anti-infective agents |
| 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 |
| US6107397A (en) * | 1997-03-24 | 2000-08-22 | Basf Aktiengesellschaft | Aqueous copolymer dispersions of water-soluble monomers with N-vinyl groups and hydrophobic monomers |
| 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 |
| 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 |
| HU226869B1 (en) * | 1999-02-01 | 2010-01-28 | Eisai R & D Man Co | Immunological adjuvant compound and composition containing thereof |
| 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 |
| 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 |
| CN102295744B (zh) | 2001-03-08 | 2014-07-02 | 宾夕法尼亚州大学理事会 | 作为抗感染药的表面两亲聚合物 |
| US20030130454A1 (en) * | 2001-11-07 | 2003-07-10 | Mitsubishi Rayon Co., Ltd. | Process for producing amphipathic polymers |
| JP2005529158A (ja) * | 2002-05-28 | 2005-09-29 | ザ・トラスティーズ・オブ・ザ・ユニバーシティ・オブ・ペンシルベニア | 両親媒性ポリマーのコンピュータ分析および設計のための方法、システムおよびコンピュータプログラム製品 |
| JP2005529604A (ja) * | 2002-06-13 | 2005-10-06 | ザ・トラスティーズ・オブ・ザ・ユニバーシティ・オブ・ペンシルベニア | 粗粒度モデルを用いる生体膜をシミュレートするための方法、システム、およびコンピュータプログラム製品 |
| 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 |
| 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. |
| JP2007516741A (ja) * | 2003-11-28 | 2007-06-28 | コロプラスト アクティーゼルスカブ | 一体化パッケージ |
| EP1711455A4 (en) * | 2004-01-23 | 2007-11-07 | Univ Pennsylvania | FAZIAL AMPHIPHILE POLYARYL AND POLYARYL ALKINYL POLYMERS AND OLIGOMERS AND ITS APPLICATIONS |
| EP2380872B1 (en) * | 2004-06-15 | 2014-04-23 | Cellceutix Corporation | Polycationic compounds and uses thereof |
| EP1771183B1 (en) * | 2004-07-23 | 2014-09-03 | The Trustees of The University of Pennsylvania | Antimicrobial copolymers and uses thereof |
-
2006
- 2006-02-24 KR KR1020077022131A patent/KR20080004475A/ko not_active Ceased
- 2006-02-24 EP EP10015189A patent/EP2301349A2/en not_active Withdrawn
- 2006-02-24 JP JP2007557169A patent/JP2008531585A/ja active Pending
- 2006-02-24 EP EP11010096A patent/EP2433628A1/en not_active Withdrawn
- 2006-02-24 EP EP06735949A patent/EP1855704A4/en not_active Withdrawn
- 2006-02-24 EP EP11010095A patent/EP2433627A1/en not_active Withdrawn
- 2006-02-24 US US11/361,050 patent/US20060241052A1/en not_active Abandoned
- 2006-02-24 EP EP10015892A patent/EP2298074A3/en not_active Withdrawn
- 2006-02-24 AU AU2006218805A patent/AU2006218805A1/en not_active Abandoned
- 2006-02-24 CA CA002599205A patent/CA2599205A1/en not_active Abandoned
- 2006-02-24 WO PCT/US2006/006487 patent/WO2006093813A2/en not_active Ceased
- 2006-02-27 TW TW101108505A patent/TW201231063A/zh unknown
- 2006-02-27 TW TW095106642A patent/TW200722098A/zh unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004082634A2 (en) * | 2003-03-17 | 2004-09-30 | The Trustees Of The University Of Pennsylvania | Facially amphiphilic polymers and oligomers and uses thereof |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011529502A (ja) * | 2008-07-28 | 2011-12-08 | ポリメディックス・インコーポレーテッド | 抗マラリア化合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2301349A2 (en) | 2011-03-30 |
| EP2433628A1 (en) | 2012-03-28 |
| EP1855704A4 (en) | 2009-12-02 |
| EP2433627A1 (en) | 2012-03-28 |
| EP2298074A3 (en) | 2011-10-26 |
| WO2006093813A2 (en) | 2006-09-08 |
| TW200722098A (en) | 2007-06-16 |
| EP1855704A2 (en) | 2007-11-21 |
| AU2006218805A1 (en) | 2006-09-08 |
| EP2298074A2 (en) | 2011-03-23 |
| KR20080004475A (ko) | 2008-01-09 |
| TW201231063A (en) | 2012-08-01 |
| CA2599205A1 (en) | 2006-09-08 |
| US20060241052A1 (en) | 2006-10-26 |
| WO2006093813A3 (en) | 2007-11-22 |
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