ES2882255T3 - Sistemas de administración basados en polímeros de ácido múcico catiónicos - Google Patents
Sistemas de administración basados en polímeros de ácido múcico catiónicos Download PDFInfo
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- ES2882255T3 ES2882255T3 ES16818439T ES16818439T ES2882255T3 ES 2882255 T3 ES2882255 T3 ES 2882255T3 ES 16818439 T ES16818439 T ES 16818439T ES 16818439 T ES16818439 T ES 16818439T ES 2882255 T3 ES2882255 T3 ES 2882255T3
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G79/08—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing boron
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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Landscapes
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| US201562187366P | 2015-07-01 | 2015-07-01 | |
| PCT/US2016/037166 WO2017003668A1 (en) | 2015-07-01 | 2016-06-13 | Cationic mucic acid polymer-based delivery systems |
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| US9468681B2 (en) | 2013-03-01 | 2016-10-18 | California Institute Of Technology | Targeted nanoparticles |
| ES2882255T3 (es) | 2015-07-01 | 2021-12-01 | California Inst Of Techn | Sistemas de administración basados en polímeros de ácido múcico catiónicos |
| WO2019241327A1 (en) * | 2018-06-13 | 2019-12-19 | California Institute Of Technology | Nanoparticles for crossing the blood brain barrier and methods of treatment using the same |
| WO2020241819A1 (ja) * | 2019-05-29 | 2020-12-03 | 国立大学法人東京工業大学 | 複合体、医薬、癌治療剤、キット及び結合体 |
| CN119638713A (zh) | 2019-12-04 | 2025-03-18 | 艾达奈特公司 | 合成治疗性纳米颗粒的方法和组合物 |
| JP7343874B2 (ja) * | 2019-12-26 | 2023-09-13 | 株式会社島津製作所 | データ処理方法及びデータ処理装置 |
| AU2024246833A1 (en) | 2023-03-31 | 2025-09-25 | Toray Industries, Inc. | Pharmaceutical composition for treating and/or preventing cancer |
Family Cites Families (103)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4631190A (en) | 1981-06-26 | 1986-12-23 | Shen Wei C | Acidity-sensitive spacer molecule to control the release of pharmaceuticals from molecular carriers |
| US5217999A (en) | 1987-12-24 | 1993-06-08 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Styryl compounds which inhibit EGF receptor protein tyrosine kinase |
| WO1991015495A1 (en) | 1990-04-02 | 1991-10-17 | Pfizer Inc. | Benzylphosphonic acid tyrosine kinase inhibitors |
| US5302606A (en) | 1990-04-16 | 1994-04-12 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Styryl-substituted pyridyl compounds which inhibit EGF receptor tyrosine kinase |
| SG64322A1 (en) | 1991-05-10 | 1999-04-27 | Rhone Poulenc Rorer Int | Bis mono and bicyclic aryl and heteroaryl compounds which inhibit egf and/or pdgf receptor tyrosine kinase |
| FI935279L (fi) | 1991-05-29 | 1993-11-26 | Pfizer | Tricykliska polyhydroxyltyrosinkinasininhibitorer |
| GB9300059D0 (en) | 1992-01-20 | 1993-03-03 | Zeneca Ltd | Quinazoline derivatives |
| US5936079A (en) | 1992-04-06 | 1999-08-10 | Alton Ochsner Medical Foundation | Oligonucleotide which binds to a chromosomal binding site for p53 protein |
| WO1994003427A1 (en) | 1992-08-06 | 1994-02-17 | Warner-Lambert Company | 2-thioindoles (selenoindoles) and related disulfides (selenides) which inhibit protein tyrosine kinases and which have antitumor properties |
| US5330992A (en) | 1992-10-23 | 1994-07-19 | Sterling Winthrop Inc. | 1-cyclopropyl-4-pyridyl-quinolinones |
| GB9226855D0 (en) | 1992-12-23 | 1993-02-17 | Erba Carlo Spa | Vinylene-azaindole derivatives and process for their preparation |
| US5565215A (en) * | 1993-07-23 | 1996-10-15 | Massachusettes Institute Of Technology | Biodegradable injectable particles for imaging |
| WO1995024190A2 (en) | 1994-03-07 | 1995-09-14 | Sugen, Inc. | Receptor tyrosine kinase inhibitors for inhibiting cell proliferative disorders and compositions thereof |
| GB9412719D0 (en) | 1994-06-24 | 1994-08-17 | Erba Carlo Spa | Substituted azaindolylidene compounds and process for their preparation |
| US6007845A (en) | 1994-07-22 | 1999-12-28 | Massachusetts Institute Of Technology | Nanoparticles and microparticles of non-linear hydrophilic-hydrophobic multiblock copolymers |
| US6610832B1 (en) | 1995-03-23 | 2003-08-26 | Biopure Corporation | Preserving a hemoglobin blood substitute with a transparent overwrap |
| GB9508538D0 (en) | 1995-04-27 | 1995-06-14 | Zeneca Ltd | Quinazoline derivatives |
| US5693631A (en) | 1995-05-30 | 1997-12-02 | Buckman Laboratories International, Inc. | Potentiation of the microbicide 2-(thiocyanomethylthio) benzothiazole using an N-alkyl heterocyclic compound |
| US6034081A (en) | 1995-05-30 | 2000-03-07 | Buckman Laboratories International Inc | Potentiation of biocide activity using an N-alkyl heterocyclic compound |
| US5747498A (en) | 1996-05-28 | 1998-05-05 | Pfizer Inc. | Alkynyl and azido-substituted 4-anilinoquinazolines |
| US5710173A (en) | 1995-06-07 | 1998-01-20 | Sugen, Inc. | Thienyl compounds for inhibition of cell proliferative disorders |
| US5596878A (en) | 1995-06-26 | 1997-01-28 | Thermo King Corporation | Methods and apparatus for operating a refrigeration unit |
| AR004010A1 (es) | 1995-10-11 | 1998-09-30 | Glaxo Group Ltd | Compuestos heterociclicos |
| FR2749853B1 (fr) | 1996-06-12 | 1998-10-16 | Rhone Poulenc Chimie | Formulation amelioree a base d'un compose hydroxyle et d'un compose amphiphile complexant utilisable notamment pour modifier les proprietes rheologiques d'emulsions |
| JP2000514440A (ja) | 1996-07-09 | 2000-10-31 | ザ ジョーンズ ホプキンス ユニバーシティー | 遺伝子輸送システム |
| EA199900021A1 (ru) | 1996-07-13 | 1999-08-26 | Глаксо, Груп Лимитед | Бициклические гетероароматические соединения в качестве ингибиторов протеинтирозинкиназы |
| AR007857A1 (es) | 1996-07-13 | 1999-11-24 | Glaxo Group Ltd | Compuestos heterociclicos fusionados como inhibidores de proteina tirosina quinasa, sus metodos de preparacion, intermediarios uso en medicina ycomposiciones farmaceuticas que los contienen. |
| US5948878A (en) * | 1997-04-15 | 1999-09-07 | Burgess; Stephen W. | Cationic polymers for nucleic acid transfection and bioactive agent delivery |
| ES2210808T3 (es) | 1997-08-27 | 2004-07-01 | California Institute Of Technology | Composiciones y su uso para prevenir la formacion de adherencias en un tejido biologico. |
| US6225346B1 (en) | 1997-10-24 | 2001-05-01 | Sugen, Inc. | Tyrphostin like compounds |
| RS49779B (sr) | 1998-01-12 | 2008-06-05 | Glaxo Group Limited, | Biciklična heteroaromatična jedinjenja kao inhibitori protein tirozin kinaze |
| US6048736A (en) | 1998-04-29 | 2000-04-11 | Kosak; Kenneth M. | Cyclodextrin polymers for carrying and releasing drugs |
| US7091192B1 (en) | 1998-07-01 | 2006-08-15 | California Institute Of Technology | Linear cyclodextrin copolymers |
| WO2000010007A2 (en) | 1998-08-17 | 2000-02-24 | California Institute Of Technology | Devices and methods for analysis of non-ionic solutes |
| US6350527B1 (en) | 1998-08-27 | 2002-02-26 | Eidgenossische Technische Hochschule Zurich | Gels and multilayer surface structures from boronic acid containing polymers |
| UA71945C2 (en) | 1999-01-27 | 2005-01-17 | Pfizer Prod Inc | Substituted bicyclic derivatives being used as anticancer agents |
| UA74803C2 (uk) | 1999-11-11 | 2006-02-15 | Осі Фармасьютікалз, Інк. | Стійкий поліморф гідрохлориду n-(3-етинілфеніл)-6,7-біс(2-метоксіетокси)-4-хіназолінаміну, спосіб його одержання (варіанти) та фармацевтичне застосування |
| US7087613B2 (en) | 1999-11-11 | 2006-08-08 | Osi Pharmaceuticals, Inc. | Treating abnormal cell growth with a stable polymorph of N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)-4-quinazolinamine hydrochloride |
| PE20011178A1 (es) | 2000-04-07 | 2001-11-19 | Takeda Chemical Industries Ltd | Compuestos heterociclicos y su produccion |
| US6372250B1 (en) | 2000-04-25 | 2002-04-16 | The Regents Of The University Of California | Non-invasive gene targeting to the brain |
| US6335342B1 (en) | 2000-06-19 | 2002-01-01 | Pharmacia & Upjohn S.P.A. | Azaindole derivatives, process for their preparation, and their use as antitumor agents |
| EP1292591B1 (en) | 2000-06-22 | 2005-02-02 | Pfizer Products Inc. | Substituted bicyclic derivatives for the treatment of abnormal cell growth |
| AU2001273071B2 (en) | 2000-06-30 | 2005-09-08 | Glaxo Group Limited | Quinazoline ditosylate salt compounds |
| TWI321054B (en) | 2000-12-19 | 2010-03-01 | California Inst Of Techn | Compositions containing inclusion complexes |
| GB0115109D0 (en) | 2001-06-21 | 2001-08-15 | Aventis Pharma Ltd | Chemical compounds |
| US7041280B2 (en) | 2001-06-29 | 2006-05-09 | Genzyme Corporation | Aryl boronate functionalized polymers for treating obesity |
| JP2005511761A (ja) | 2001-07-10 | 2005-04-28 | ノース・キャロライナ・ステイト・ユニヴァーシティ | ナノ粒子送達ビヒクル |
| IL160010A0 (en) | 2001-07-23 | 2004-06-20 | Univ Ramot | Methods and compositions for treating fungal infections |
| US6737504B2 (en) | 2001-07-30 | 2004-05-18 | California Institute Of Technology | Synthesis of substituted poly(aniline)s |
| AU2002323501C1 (en) | 2001-08-30 | 2010-04-29 | Biorexis Technology, Inc | Modified transferrin fusion proteins |
| EP1439178A4 (en) | 2001-10-05 | 2005-11-16 | Takeda Pharmaceutical | Heterocyclic compounds, oxazole derivatives, process for their preparation and their use |
| US7157277B2 (en) | 2001-11-28 | 2007-01-02 | Neose Technologies, Inc. | Factor VIII remodeling and glycoconjugation of Factor VIII |
| AP2004003058A0 (en) | 2001-12-12 | 2004-06-30 | Pfizer Prod Inc | Quinazoline derivatives for the treatment of abnormal cell growth. |
| PL370858A1 (en) | 2001-12-12 | 2005-05-30 | Pfizer Products Inc. | Salt forms of e-2-methoxy-n-(3-{4-[3-methyl-4-(6-methyl-pyridin-3-yloxy)-phenylamino]-quinazolin-6-yl}-allyl)-acetamide and method of production |
| AU2002357193A1 (en) | 2001-12-19 | 2003-07-09 | Smithkline Beecham Corporation | Thienopyrimidine compounds as protein tyrosine kinase inhibitors |
| US7591994B2 (en) | 2002-12-13 | 2009-09-22 | Immunomedics, Inc. | Camptothecin-binding moiety conjugates |
| US7094427B2 (en) | 2002-05-29 | 2006-08-22 | Impax Laboratories, Inc. | Combination immediate release controlled release levodopa/carbidopa dosage forms |
| EP1510221A4 (en) | 2002-06-03 | 2009-04-29 | Mitsubishi Tanabe Pharma Corp | MEANS FOR THE PREVENTION AND / OR TREATMENT OF PERSONS EXPRESSING OR ACTIVATING HER2 AND / OR EGFR |
| ES2377318T3 (es) | 2002-09-06 | 2012-03-26 | Cerulean Pharma Inc. | Polímeros a base de ciclodextrina para el suministro de los agentes terapéuticos enlazados covalentemente a ellos |
| AU2003291567A1 (en) | 2002-11-19 | 2004-06-15 | Genzyme Corporation | Polymeric boronic acid derivatives as lipase inhibitors |
| EP1575562B1 (en) | 2002-11-26 | 2016-10-05 | Seacoast Neurosciene, Inc. | Buoyant polymer particles delivering therapeutic agents |
| EP1591446B1 (en) | 2003-01-29 | 2013-03-06 | Takeda Pharmaceutical Company Limited | Thienopyrimidine compounds and use thereof |
| JP2005119255A (ja) | 2003-10-17 | 2005-05-12 | San Quest:Kk | 携帯電話画像取り込み機能付き名刺印刷装置 |
| US20050090732A1 (en) | 2003-10-28 | 2005-04-28 | Triton Biosystems, Inc. | Therapy via targeted delivery of nanoscale particles |
| WO2005119255A2 (en) | 2004-05-12 | 2005-12-15 | Applera Corporation | Constrained cis-diol-borate bioconjugation system |
| EP1773900A4 (en) | 2004-07-30 | 2007-08-29 | Basf Ag | POLYMERIC BORONIC ACID DERIVATIVES AND USE IN THE MANUFACTURE OF PAPER |
| US7413173B2 (en) | 2004-09-10 | 2008-08-19 | Ric Investments, Llc | Molded water chamber base plate for use in a humidifier and ventilator assembly |
| JP4988578B2 (ja) | 2004-10-12 | 2012-08-01 | ルミネックス コーポレーション | ミクロスフェアの表面特性を変化させるための方法 |
| TW200618820A (en) | 2004-11-05 | 2006-06-16 | Alza Corp | Liposome formulations of boronic acid compounds |
| JP2008537551A (ja) | 2005-03-31 | 2008-09-18 | カランド ファーマシューティカルズ， インコーポレイテッド | リボヌクレオチドレダクターゼサブユニット２の阻害剤およびその使用 |
| CA2606018A1 (en) | 2005-04-28 | 2006-11-02 | Ventana Medical Systems, Inc. | Nanoparticle conjugates |
| EP1945240B1 (en) | 2005-09-16 | 2016-12-28 | Raptor Pharmaceutical Inc | Compositions comprising receptor-associated protein (rap) variants specific for cr-containing proteins and uses thereof |
| US20080267876A1 (en) | 2005-09-20 | 2008-10-30 | Yissum Research Development Company | Nanoparticles for Targeted Delivery of Active Agent |
| US7988988B2 (en) | 2005-11-21 | 2011-08-02 | Bausch & Lomb Incorporated | Contact lenses with mucin affinity |
| EP2046266A4 (en) | 2006-07-21 | 2009-11-04 | Massachusetts Inst Technology | ENDMODICIFIED POLY (BETA AMINO ESTER) AND ITS USE |
| CN101500546A (zh) | 2006-08-17 | 2009-08-05 | 诺瓦提斯公司 | 纳米粒组合物 |
| EP2066293A2 (en) | 2006-09-29 | 2009-06-10 | Genzyme Corporation | Amide dendrimer compositions |
| US7825127B2 (en) | 2006-12-28 | 2010-11-02 | Takeda Pharmaceutical Company, Limited | Method for treating cancer |
| WO2009036022A1 (en) | 2007-09-10 | 2009-03-19 | Board Of Regents, The University Of Texas System | Enhancement of polysaccharide-mediated nucleic acid delivery |
| CN101910113A (zh) | 2007-12-28 | 2010-12-08 | 怡百克制药公司 | 左旋多巴控释制剂及其用途 |
| US20100029545A1 (en) | 2008-08-04 | 2010-02-04 | Sumerlin Brent S | Boronic acid-containing block copolymers for controlled drug delivery |
| US8557292B2 (en) | 2008-08-13 | 2013-10-15 | California Institute Of Technology | Carrier nanoparticles and related compositions, methods and systems |
| US8367166B2 (en) | 2008-10-31 | 2013-02-05 | Chevron U.S.A. Inc. | Synthesis of higher diamondoids |
| US20120156138A1 (en) | 2009-04-14 | 2012-06-21 | Smith Larry J | Methods and Compositions for the Treatment of Medical Conditions Involving Cellular Reprogramming |
| BRPI1012036A2 (pt) | 2009-05-27 | 2017-10-10 | Selecta Biosciences Inc | nanocarreadores que possuem componentes com diferentes taxas de liberação |
| FR2946476B1 (fr) | 2009-06-05 | 2014-03-21 | Aeg Power Solutions Bv | Convertisseur continu-continu a regulation double alternance |
| US20100330686A1 (en) | 2009-06-29 | 2010-12-30 | Seung Bum Park | Nanosensor for sugar detection |
| CN102906127A (zh) | 2009-11-06 | 2013-01-30 | 华盛顿大学商业中心 | 来自两性离子聚合物的自组装颗粒以及相关的方法 |
| US9138418B2 (en) | 2009-12-09 | 2015-09-22 | William Marsh Rice University | Therapeutic compositions and methods for delivery of active agents cleavably linked to nanoparticles |
| US20120309691A1 (en) | 2010-02-04 | 2012-12-06 | Dapeng Zhou | Tumor targeted delivery of immunomodulators by nanopolymers |
| US20130157926A1 (en) | 2010-06-18 | 2013-06-20 | Johannes Franciscus Joseph Engbersen | Boronated polymers |
| WO2012024526A2 (en) | 2010-08-20 | 2012-02-23 | Cerulean Pharma Inc. | Conjugates, particles, compositions, and related methods |
| EP2648756A4 (en) | 2010-12-10 | 2016-06-08 | California Inst Of Techn | ATTAINING THE MESANGIUM WITH NANOPARTICLES OF DEFINED DIAMETER |
| US10106650B2 (en) | 2011-05-13 | 2018-10-23 | The Regents Of The University Of California | Reversibly crosslinked micelle systems |
| DE102012017025B4 (de) | 2012-08-28 | 2018-05-30 | Kennametal Inc. | Werkzeughalter für einen Schneideinsatz und Baugruppe mit einem solchen Werkzeughalter |
| GB201220474D0 (en) | 2012-11-14 | 2012-12-26 | Sagetis Biotech Sl | Polypeptides |
| US9468681B2 (en) | 2013-03-01 | 2016-10-18 | California Institute Of Technology | Targeted nanoparticles |
| EP2961395B1 (en) | 2013-03-01 | 2024-06-19 | California Institute Of Technology | Targeted nanoparticles |
| ES2737800T3 (es) * | 2013-03-01 | 2020-01-16 | California Inst Of Techn | Nanopartículas estabilizadas con composiciones de ácido nitrofenilborónico |
| US9132097B2 (en) | 2013-03-01 | 2015-09-15 | California Institute Of Technology | Nanoparticles stabilized with nitrophenylboronic acid compositions |
| WO2014185964A1 (en) | 2013-05-14 | 2014-11-20 | California Institute Of Technology | Method of delivering therapeutics and imaging agents by nanoparticles that cross the blood brain barrier |
| WO2016037166A1 (en) | 2014-09-07 | 2016-03-10 | Yu Zhang | Novel anti-oxidant compositions and methods of delivery |
| ES2882255T3 (es) | 2015-07-01 | 2021-12-01 | California Inst Of Techn | Sistemas de administración basados en polímeros de ácido múcico catiónicos |
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| EP3317323A1 (en) | 2018-05-09 |
| JP6914860B2 (ja) | 2021-08-04 |
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