CA2267904C - Fusogenic liposome composition and method - Google Patents
Fusogenic liposome composition and method Download PDFInfo
- Publication number
- CA2267904C CA2267904C CA002267904A CA2267904A CA2267904C CA 2267904 C CA2267904 C CA 2267904C CA 002267904 A CA002267904 A CA 002267904A CA 2267904 A CA2267904 A CA 2267904A CA 2267904 C CA2267904 C CA 2267904C
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- Prior art keywords
- liposomes
- liposome
- hydrophilic polymer
- lipid
- composition
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- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
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- A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes or liposomes coated or grafted with polymers
- A61K9/1272—Non-conventional liposomes, e.g. PEGylated liposomes or liposomes coated or grafted with polymers comprising non-phosphatidyl surfactants as bilayer-forming substances, e.g. cationic lipids or non-phosphatidyl liposomes coated or grafted with polymers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
- A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes or liposomes coated or grafted with polymers
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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
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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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S436/00—Chemistry: analytical and immunological testing
- Y10S436/829—Liposomes, e.g. encapsulation
Landscapes
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- Biophysics (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Cosmetics (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002505445A CA2505445A1 (en) | 1996-10-11 | 1997-10-10 | Fusogenic liposome composition and method |
Applications Claiming Priority (3)
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Families Citing this family (171)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1223831A (en) | 1982-06-23 | 1987-07-07 | Dean Engelhardt | Modified nucleotides, methods of preparing and utilizing and compositions containing the same |
| US6008202A (en) * | 1995-01-23 | 1999-12-28 | University Of Pittsburgh | Stable lipid-comprising drug delivery complexes and methods for their production |
| US5795587A (en) * | 1995-01-23 | 1998-08-18 | University Of Pittsburgh | Stable lipid-comprising drug delivery complexes and methods for their production |
| US6056973A (en) * | 1996-10-11 | 2000-05-02 | Sequus Pharmaceuticals, Inc. | Therapeutic liposome composition and method of preparation |
| US20070036722A1 (en) * | 1996-10-28 | 2007-02-15 | Pal Rongved | Separation processes |
| US6331289B1 (en) | 1996-10-28 | 2001-12-18 | Nycomed Imaging As | Targeted diagnostic/therapeutic agents having more than one different vectors |
| PT956001E (pt) * | 1996-11-12 | 2012-12-06 | Univ California | Preparação de formulações estáveis de complexos do tipo lípido-ácido nucleico para uma entrega eficiente in vivo |
| US6210707B1 (en) * | 1996-11-12 | 2001-04-03 | The Regents Of The University Of California | Methods of forming protein-linked lipidic microparticles, and compositions thereof |
| DE19745950A1 (de) * | 1997-10-17 | 1999-04-22 | Dds Drug Delivery Service Ges | Arzneistoffträgerpartikel für die gewebespezifische Arzneistoffapplikation |
| US6426086B1 (en) * | 1998-02-03 | 2002-07-30 | The Regents Of The University Of California | pH-sensitive, serum-stable liposomes |
| US6372720B1 (en) | 1998-02-05 | 2002-04-16 | Kenneth J. Longmuir | Liposome fusion and delivery vehicle |
| US6936729B2 (en) * | 1998-05-16 | 2005-08-30 | Mirus Bio Corporation | Compound containing a labile disulfide bond |
| US7087770B2 (en) | 1998-05-16 | 2006-08-08 | Mirus Bio Corporation | Compound containing a labile disulfide bond |
| CA2346879A1 (en) * | 1998-09-16 | 2000-04-27 | Alza Corporation | Liposome-entrapped topoisomerase inhibitors |
| CA2353593A1 (en) * | 1998-12-18 | 2000-06-22 | Hadasit Medical Research Services & Development Ltd. | Method of administering a compound to multi-drug resistant cells |
| US6379698B1 (en) * | 1999-04-06 | 2002-04-30 | Isis Pharmaceuticals, Inc. | Fusogenic lipids and vesicles |
| US6613352B2 (en) | 1999-04-13 | 2003-09-02 | Universite De Montreal | Low-rigidity liposomal formulation |
| AU783647B2 (en) * | 1999-04-20 | 2005-11-17 | University Of British Columbia, The | Cationic peg-lipids and methods of use |
| US6852334B1 (en) | 1999-04-20 | 2005-02-08 | The University Of British Columbia | Cationic peg-lipids and methods of use |
| US7238368B2 (en) * | 1999-04-23 | 2007-07-03 | Alza Corporation | Releasable linkage and compositions containing same |
| US7303760B2 (en) * | 1999-04-23 | 2007-12-04 | Alza Corporation | Method for treating multi-drug resistant tumors |
| CA2368793A1 (en) * | 1999-04-23 | 2000-11-02 | Alza Corporation | Releasable linkage and compositions containing same |
| EP1880736A1 (en) * | 1999-04-23 | 2008-01-23 | Alza Corporation | Releasable linkage and composition containing same |
| AUPQ014699A0 (en) * | 1999-05-04 | 1999-05-27 | Access Pharmaceuticals Australia Pty Limited | Amplification of folate-mediated targeting to tumor cells using nanoparticles |
| AUPQ014799A0 (en) * | 1999-05-04 | 1999-05-27 | Access Pharmaceuticals Australia Pty Limited | Amplification of folate-mediated targeting to tumor cells using polymers |
| JP2003501631A (ja) * | 1999-05-27 | 2003-01-14 | ツェプトゼンス アクチエンゲゼルシャフト | 官能基化された小胞 |
| RU2250911C2 (ru) * | 1999-07-14 | 2005-04-27 | Элзэ Копэрейшн | Липосомальная композиция, нейтральный липополимер и способ увеличения времени циркуляции липосомы |
| US20040197390A1 (en) * | 2001-05-29 | 2004-10-07 | Shi-Kun Huang | Neutral-cationic lipid for systemic delivery of factor VIII gene |
| AU7868400A (en) * | 1999-10-08 | 2001-04-23 | Alza Corporation | Neutral-cationic lipid for nucleic acid and drug delivery |
| US7067111B1 (en) * | 1999-10-25 | 2006-06-27 | Board Of Regents, University Of Texas System | Ethylenedicysteine (EC)-drug conjugates, compositions and methods for tissue specific disease imaging |
| US6916488B1 (en) * | 1999-11-05 | 2005-07-12 | Biocure, Inc. | Amphiphilic polymeric vesicles |
| JP2003514843A (ja) * | 1999-11-24 | 2003-04-22 | ザ リポソーム カンパニー、インコーポレーテッド | モジュラー標的化リポソーム送達システム |
| WO2001041738A2 (en) * | 1999-12-10 | 2001-06-14 | Celator Technologies Inc. | Lipid carrier compositions with protected surface reactive functions |
| ES2236181T3 (es) * | 2000-01-28 | 2005-07-16 | Alza Corporation | Liposomas que contienen un compuesto atrapado en una solucion supersaturada. |
| JP2004508012A (ja) * | 2000-04-20 | 2004-03-18 | ザ ユニバーシティ オブ ブリティッシュ コロンビア | エンドソーム膜不安定剤を用いたｓｐｌｐ媒介性トランスフェクションの強化方法 |
| US7189705B2 (en) | 2000-04-20 | 2007-03-13 | The University Of British Columbia | Methods of enhancing SPLP-mediated transfection using endosomal membrane destabilizers |
| US10293056B1 (en) * | 2000-05-24 | 2019-05-21 | Board Of Regents, The University Of Texas System | Methods and compositions for non-viral gene therapy for treatment of hyperproliferative diseases |
| CA2410906C (en) * | 2000-06-02 | 2012-10-02 | Board Of Regents, The University Of Texas System | Ethylenedicysteine (ec)-drug conjugates |
| USRE43612E1 (en) | 2000-10-10 | 2012-08-28 | Massachusetts Institute Of Technology | Biodegradable poly(β-amino esters) and uses thereof |
| US6998115B2 (en) | 2000-10-10 | 2006-02-14 | Massachusetts Institute Of Technology | Biodegradable poly(β-amino esters) and uses thereof |
| WO2002036073A2 (en) * | 2000-11-02 | 2002-05-10 | Smithkline Beecham Corporation | Receptor antagonist-lipid conjugates and delivery vehicles containing same |
| US6613280B2 (en) | 2001-03-20 | 2003-09-02 | Therox, Inc. | Disposable cartridge for producing gas-enriched fluids |
| WO2002076394A2 (en) * | 2001-03-22 | 2002-10-03 | The Ohio State University Research Foundation | Enzyme-based anti-cancer compositions and methods |
| JP2004525138A (ja) * | 2001-03-26 | 2004-08-19 | アルザ・コーポレーシヨン | 治療剤の改良された細胞内送達のためのリポソーム組成物 |
| AU2002256398A2 (en) * | 2001-04-30 | 2002-11-11 | Targeted Genetics Corporation | Lipid-comprising drug delivery complexes and methods for their production |
| US20050196765A1 (en) * | 2001-05-18 | 2005-09-08 | Sirna Therapeutics, Inc. | RNA interference mediated inhibition of checkpoint Kinase-1 (CHK-1) gene expression using short interfering nucleic acid (siNA) |
| US20050176025A1 (en) * | 2001-05-18 | 2005-08-11 | Sirna Therapeutics, Inc. | RNA interference mediated inhibition of B-cell CLL/Lymphoma-2 (BCL-2) gene expression using short interfering nucleic acid (siNA) |
| US20050158735A1 (en) * | 2001-05-18 | 2005-07-21 | Sirna Therapeutics, Inc. | RNA interference mediated inhibition of proliferating cell nuclear antigen (PCNA) gene expression using short interfering nucleic acid (siNA) |
| US20050203040A1 (en) * | 2001-05-18 | 2005-09-15 | Sirna Therapeutics, Inc. | RNA interference mediated inhibition of vascular cell adhesion molecule (VCAM) gene expression using short interfering nucleic acid (siNA) |
| US20050233997A1 (en) * | 2001-05-18 | 2005-10-20 | Sirna Therapeutics, Inc. | RNA interference mediated inhibition of matrix metalloproteinase 13 (MMP13) gene expression using short interfering nucleic acid (siNA) |
| EP1572067A4 (en) * | 2001-05-18 | 2009-05-13 | Sirna Therapeutics Inc | CONJUGATES AND COMPOSITIONS FOR CELLULAR RELEASE |
| US20050124566A1 (en) * | 2001-05-18 | 2005-06-09 | Sirna Therapeutics, Inc. | RNA interference mediated inhibition of myostatin gene expression using short interfering nucleic acid (siNA) |
| US20050196767A1 (en) * | 2001-05-18 | 2005-09-08 | Sirna Therapeutics, Inc. | RNA interference mediated inhibition of GRB2 associated binding protein (GAB2) gene expression using short interfering nucleic acis (siNA) |
| US20050288242A1 (en) * | 2001-05-18 | 2005-12-29 | Sirna Therapeutics, Inc. | RNA interference mediated inhibition of RAS gene expression using short interfering nucleic acid (siNA) |
| US20050159382A1 (en) * | 2001-05-18 | 2005-07-21 | Sirna Therapeutics, Inc. | RNA interference mediated inhibition of polycomb group protein EZH2 gene expression using short interfering nucleic acid (siNA) |
| US8216585B2 (en) * | 2001-05-25 | 2012-07-10 | The Trustees Of The University Of Pennsylvania | Targeted particles and methods of using the same |
| US6939564B2 (en) * | 2001-06-08 | 2005-09-06 | Labopharm, Inc. | Water-soluble stabilized self-assembled polyelectrolytes |
| AU2002368202B2 (en) | 2001-11-02 | 2008-06-05 | Insert Therapeutics, Inc | Methods and compositions for therapeutic use of RNA interference |
| GB0129121D0 (en) * | 2001-12-05 | 2002-01-23 | Ic Vec Ltd | Compound |
| US9657294B2 (en) | 2002-02-20 | 2017-05-23 | Sirna Therapeutics, Inc. | RNA interference mediated inhibition of gene expression using chemically modified short interfering nucleic acid (siNA) |
| US9181551B2 (en) | 2002-02-20 | 2015-11-10 | Sirna Therapeutics, Inc. | RNA interference mediated inhibition of gene expression using chemically modified short interfering nucleic acid (siNA) |
| EP1485076A1 (en) * | 2002-02-27 | 2004-12-15 | The Ohio State University Research Foundation | Therapeutic methods for acute myeloid leukemia |
| US7018655B2 (en) * | 2002-03-18 | 2006-03-28 | Labopharm, Inc. | Amphiphilic diblock, triblock and star-block copolymers and their pharmaceutical compositions |
| AU2003233464A1 (en) * | 2002-03-29 | 2003-10-13 | Bristol-Myers Squibb Corporation | Lipid mediated screening of drug candidates for identification of active compounds |
| US20060094673A1 (en) * | 2002-04-23 | 2006-05-04 | Benjamin Chu | Polymer surfactants for gene therapy applications |
| US20040022842A1 (en) * | 2002-06-03 | 2004-02-05 | Mebiopharm Co., Ltd. | Liposome preparations containing oxaliplatin |
| JP3415131B1 (ja) * | 2002-06-03 | 2003-06-09 | メビオファーム株式会社 | リポソーム製剤 |
| US20040093198A1 (en) * | 2002-11-08 | 2004-05-13 | Carbon Design Systems | Hardware simulation with access restrictions |
| ATE485331T1 (de) | 2003-01-06 | 2010-11-15 | Nektar Therapeutics | Thiolselektive wasserlösliche polymerderivate |
| JPWO2004063216A1 (ja) * | 2003-01-10 | 2006-06-15 | アステラス製薬株式会社 | 血中滞留および癌組織特異的薬物送達のためのコンジュゲート |
| CA2517352A1 (en) * | 2003-02-28 | 2004-09-16 | Alza Corporation | Liposome composition for reduction of liposome-induced complement activation |
| CA2520864A1 (en) | 2003-03-31 | 2004-10-21 | Alza Corporation | Lipid particles having asymmetric lipid coating and method of preparing same |
| JP2007500239A (ja) * | 2003-05-30 | 2007-01-11 | アルザ・コーポレーシヨン | 薬剤の肺投与の方法 |
| US8846079B1 (en) * | 2004-12-01 | 2014-09-30 | Vgsk Technologies, Inc. | Sterically stabilized carrier for aerosol therapeutics, compositions and methods for treating the respiratory tract of a mammal |
| US11324698B2 (en) | 2003-08-28 | 2022-05-10 | Vgsk Technologies, Inc. | Sterically stabilized carrier for aerosol therapeutics, compositions and methods for treating the respiratory tract of a mammal |
| BRPI0418670B1 (pt) * | 2003-08-29 | 2015-10-20 | Univ Newcastle Res Ass | método de separação de partículas sólidas de uma suspensão comprendendo um líquido e método decontrole da consolidação de um leito de partículas sólidas dentro de um líquido. |
| US7943179B2 (en) | 2003-09-23 | 2011-05-17 | Massachusetts Institute Of Technology | pH triggerable polymeric particles |
| EP1677765A1 (en) * | 2003-10-24 | 2006-07-12 | Alza Corporation | Preparation of lipid particles |
| US9050378B2 (en) * | 2003-12-10 | 2015-06-09 | Board Of Regents, The University Of Texas System | N2S2 chelate-targeting ligand conjugates |
| JP2007520481A (ja) * | 2004-01-15 | 2007-07-26 | アルザ・コーポレーシヨン | 治療薬を送達するためのリポソーム組成物 |
| US8168222B2 (en) | 2004-09-07 | 2012-05-01 | Board Of Regents Of The University Of Nebraska | Amphiphilic polymer-protein conjugates and methods of use thereof |
| US8017151B2 (en) * | 2004-09-07 | 2011-09-13 | Board Of Regents Of The University Of Nebraska By And Behalf Of The University Of Nebraska Medical Center | Amphiphilic polymer-protein conjugates and methods of use thereof |
| EP1809246B1 (en) * | 2004-10-08 | 2008-07-16 | Alza Corporation | Method of insertion of a lipid-linked moiety into a pre-formed lipid assembly using microwaves |
| JPWO2006088245A1 (ja) * | 2005-02-18 | 2008-07-10 | 国立大学法人徳島大学 | ポリオキシアルキレン鎖含有脂質誘導体及び該誘導体を含有する脂質膜構造体 |
| JP2006248978A (ja) * | 2005-03-10 | 2006-09-21 | Mebiopharm Co Ltd | 新規なリポソーム製剤 |
| CA2609376A1 (en) * | 2005-05-23 | 2006-11-30 | Sdg, Inc. | Lipid construct for delivery of interferon to a mammal |
| US9505867B2 (en) | 2005-05-31 | 2016-11-29 | Ecole Polytechmique Fédérale De Lausanne | Triblock copolymers for cytoplasmic delivery of gene-based drugs |
| AU2006322076C1 (en) | 2005-12-08 | 2013-11-14 | Insmed Incorporated | Lipid-based compositions of antiinfectives for treating pulmonary infections |
| WO2007092944A2 (en) * | 2006-02-08 | 2007-08-16 | Introgen Therapeutics, Inc. | Compositions and methods involving gene therapy and proteasome modulation |
| US8758723B2 (en) | 2006-04-19 | 2014-06-24 | The Board Of Regents Of The University Of Texas System | Compositions and methods for cellular imaging and therapy |
| US8808681B2 (en) | 2006-06-05 | 2014-08-19 | Massachusetts Institute Of Technology | Crosslinked, degradable polymers and uses thereof |
| US20080031883A1 (en) * | 2006-07-13 | 2008-02-07 | Torchilin Vladimir P | Condition-dependent, multiple target delivery system |
| WO2008008523A1 (en) * | 2006-07-14 | 2008-01-17 | Regents Of The University Of Minnesota | COMPOUNDS THAT BIND α5β1 INTEGRIN AND METHODS OF USE |
| WO2008011561A2 (en) | 2006-07-21 | 2008-01-24 | Massachusetts Institute Of Technology | End-modified poly(beta-amino esters) and uses thereof |
| US20080213349A1 (en) * | 2006-09-11 | 2008-09-04 | Deepak Ramesh Thakker | Liposome Complexes Containing Pharmaceutical Agents and Methods |
| CA2699184A1 (en) * | 2006-09-22 | 2008-03-27 | Labopharm Inc. | Compositions and methods for ph targeted drug delivery |
| US10925977B2 (en) * | 2006-10-05 | 2021-02-23 | Ceil>Point, LLC | Efficient synthesis of chelators for nuclear imaging and radiotherapy: compositions and applications |
| US9119783B2 (en) | 2007-05-07 | 2015-09-01 | Insmed Incorporated | Method of treating pulmonary disorders with liposomal amikacin formulations |
| WO2009006311A2 (en) * | 2007-06-29 | 2009-01-08 | Wisconsin Alumni Research Foundation | Structuring effect of cholesterol in peg-phospholipid micelles, drug delivery of amphotericin b, and combination antifungals |
| US20110105995A1 (en) * | 2008-01-16 | 2011-05-05 | Zhu Ting F | Uniform-sized, multi-drug carrying, and photosensitive liposomes for advanced drug delivery |
| WO2009154688A1 (en) * | 2008-05-28 | 2009-12-23 | President And Fellows Of Harvard College | A pre-fabricated electron microscopy grid for monolayer purification and methods and kits therefor |
| US8173621B2 (en) | 2008-06-11 | 2012-05-08 | Gilead Pharmasset Llc | Nucleoside cyclicphosphates |
| WO2010006282A2 (en) * | 2008-07-10 | 2010-01-14 | Serina Therapeutics, Inc. | Polyoxazolines with inert terminating groups, polyoxazolines prepared from protected initiating groups and related compounds |
| MX353900B (es) | 2008-11-07 | 2018-02-01 | Massachusetts Inst Technology | Lipidoides de aminoalcohol y usos de los mismos. |
| JP5814793B2 (ja) | 2008-11-25 | 2015-11-17 | エコール ポリテクニク フェデラル ド ローザンヌ（エーペーエフエル） | ブロックコポリマーおよびその使用 |
| US8551973B2 (en) | 2008-12-23 | 2013-10-08 | Gilead Pharmasset Llc | Nucleoside analogs |
| SG172359A1 (en) | 2008-12-23 | 2011-07-28 | Pharmasset Inc | Nucleoside phosphoramidates |
| NZ593647A (en) | 2008-12-23 | 2013-08-30 | Gilead Pharmasset Llc | Synthesis of purine nucleosides |
| EP2230515B1 (en) * | 2009-03-16 | 2014-12-17 | Agilent Technologies, Inc. | Passivation of surfaces after ligand coupling |
| KR20210031549A (ko) * | 2009-05-05 | 2021-03-19 | 알닐람 파마슈티칼스 인코포레이티드 | 지질 조성물 |
| TWI598358B (zh) | 2009-05-20 | 2017-09-11 | 基利法瑪席特有限責任公司 | 核苷磷醯胺 |
| US9937128B2 (en) * | 2009-08-03 | 2018-04-10 | The University Of North Carolina At Chapel Hill | Liposomes comprising a calcium phosphate-containing precipitate |
| KR101689787B1 (ko) | 2009-08-31 | 2016-12-26 | 나노캐리어 가부시키가이샤 | 입자 조성물 및 이를 가진 의약 조성물 |
| EP3403647A1 (en) | 2009-12-01 | 2018-11-21 | Translate Bio, Inc. | Delivery of mrna for the augmentation of proteins and enzymes in human genetic diseases |
| JP4829351B2 (ja) | 2010-02-05 | 2011-12-07 | ナノキャリア株式会社 | 易崩壊型ポリマーミセル組成物 |
| TW201136945A (en) | 2010-03-31 | 2011-11-01 | Pharmasset Inc | Purine nucleoside phosphoramidate |
| PL3290428T3 (pl) | 2010-03-31 | 2022-02-07 | Gilead Pharmasset Llc | Tabletka zawierająca krystaliczny (S)-2-(((S)-(((2R,3R,4R,5R)-5-(2,4-diokso-3,4-dihydropirymidyn-1(2H)-ylo)-4-fluoro-3-hydroksy-4-metylotetrahydrofuran-2-ylo)metoksy)(fenoksy)fosforylo)amino)propanian izopropylu |
| JP2013527145A (ja) | 2010-03-31 | 2013-06-27 | ギリード・ファーマセット・エルエルシー | リン含有活性化剤の立体選択的合成 |
| CN105153307A (zh) | 2010-05-04 | 2015-12-16 | 梅里麦克制药股份有限公司 | 抗表皮生长因子受体(egfr)的抗体及其用途 |
| CN107261110A (zh) | 2010-06-19 | 2017-10-20 | 健康科学西部大学 | Peg化脂质体包封的糖肽抗生素的新制剂 |
| WO2012027675A2 (en) | 2010-08-26 | 2012-03-01 | Massachusetts Institute Of Technology | Poly(beta-amino alcohols), their preparation, and uses thereof |
| US9260471B2 (en) | 2010-10-29 | 2016-02-16 | Sirna Therapeutics, Inc. | RNA interference mediated inhibition of gene expression using short interfering nucleic acids (siNA) |
| PT3042910T (pt) | 2010-11-30 | 2019-04-16 | Gilead Pharmasset Llc | 2'-espiro-nucleósidos para utilização na terapia da hepatite c |
| US9238716B2 (en) | 2011-03-28 | 2016-01-19 | Massachusetts Institute Of Technology | Conjugated lipomers and uses thereof |
| AU2012254842A1 (en) * | 2011-05-12 | 2013-05-02 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Liposomes comprising polymer-conjugated lipids and related uses |
| US8691231B2 (en) | 2011-06-03 | 2014-04-08 | Merrimack Pharmaceuticals, Inc. | Methods of treatment of tumors expressing predominantly high affinity EGFR ligands or tumors expressing predominantly low affinity EGFR ligands with monoclonal and oligoclonal anti-EGFR antibodies |
| US20140206753A1 (en) | 2011-06-08 | 2014-07-24 | Shire Human Genetic Therapies, Inc. | Lipid nanoparticle compositions and methods for mrna delivery |
| US8883989B2 (en) | 2011-10-18 | 2014-11-11 | Regents Of The University Of Minnesota | Fractalkine binding polynucleotides and methods of use |
| PE20181541A1 (es) | 2011-10-27 | 2018-09-26 | Massachusetts Inst Technology | Derivados de aminoacidos funcionalizados en la terminal n capaces de formar microesferas encapsuladoras de farmaco |
| EP2859102A4 (en) | 2012-06-08 | 2016-05-11 | Shire Human Genetic Therapies | NUCLEASE RESISTANT POLYNUCLEOTIDES AND USES THEREOF |
| US10022326B2 (en) | 2012-07-18 | 2018-07-17 | Onyx Therapeutics, Inc. | Liposomal compositions of epoxyketone-based proteasome inhibitors |
| CN102920658B (zh) * | 2012-11-02 | 2015-01-21 | 艾韦特(溧阳)医药科技有限公司 | 与glp-1类似物和聚乙二醇结合的脂质体及其制备方法 |
| ES2743039T3 (es) | 2012-11-29 | 2020-02-18 | Insmed Inc | Formulaciones de vancomicina estabilizada |
| US20140271822A1 (en) * | 2013-03-13 | 2014-09-18 | Mallinckrodt Llc | Modified docetaxel liposome formulations |
| ES2981185T3 (es) | 2013-03-14 | 2024-10-07 | Translate Bio Inc | Métodos para la purificación de ARN mensajero |
| CA2904151C (en) | 2013-03-14 | 2023-09-12 | Shire Human Genetic Therapies, Inc. | Cftr mrna compositions and related methods and uses |
| US10711106B2 (en) | 2013-07-25 | 2020-07-14 | The University Of Chicago | High aspect ratio nanofibril materials |
| MX2016005238A (es) | 2013-10-22 | 2016-08-12 | Shire Human Genetic Therapies | Formulaciones de lipidos para la administracion de acido ribonucleico mensajero. |
| BR112016009014B1 (pt) | 2013-10-22 | 2024-02-06 | Translate Bio, Inc | USO DE COMPOSIÇÃO COMPREENDENDO mRNA PARA DEFICIÊNCIA DE ARGININOSSUCINATO SINTETASE |
| WO2015061491A1 (en) | 2013-10-22 | 2015-04-30 | Shire Human Genetic Therapies, Inc. | Mrna therapy for phenylketonuria |
| JP6702866B2 (ja) | 2013-11-18 | 2020-06-03 | ルビウス セラピューティクス， インコーポレイテッド | 合成膜−レシーバー複合体 |
| WO2015117021A1 (en) | 2014-01-31 | 2015-08-06 | Factor Bioscience Inc. | Methods and products for nucleic acid production and delivery |
| US20170173005A1 (en) | 2014-03-27 | 2017-06-22 | Research Foundation Of The City University Of New York | Method for detecting or treating triple negative breast cancer |
| WO2015153102A1 (en) | 2014-04-01 | 2015-10-08 | Rubius Therapeutics, Inc. | Methods and compositions for immunomodulation |
| MX373952B (es) | 2014-04-25 | 2020-07-13 | Shire Human Genetic Therapies | Métodos de purificación de arn mensajero. |
| EP3466432B1 (en) | 2014-05-15 | 2020-07-08 | Insmed Incorporated | Methods for treating pulmonary non-tuberculous mycobacterial infections |
| CN106659731A (zh) | 2014-05-30 | 2017-05-10 | 夏尔人类遗传性治疗公司 | 用于递送核酸的可生物降解脂质 |
| UA121863C2 (uk) | 2014-06-24 | 2020-08-10 | Транслейт Байо, Інк. | Стереохімічно збагачені композиції для доставки нуклеїнових кислот |
| US9840479B2 (en) | 2014-07-02 | 2017-12-12 | Massachusetts Institute Of Technology | Polyamine-fatty acid derived lipidoids and uses thereof |
| CN104546722B (zh) * | 2015-02-10 | 2017-05-24 | 中国医学科学院医药生物技术研究所 | 米铂脂质体和制法 |
| EP3543339A1 (en) | 2015-02-13 | 2019-09-25 | Factor Bioscience Inc. | Nucleic acid products and methods of administration thereof |
| RS64331B1 (sr) | 2015-06-19 | 2023-08-31 | Massachusetts Inst Technology | Alkenil supstituisani 2,5-piperazindioni i njihova primena u sastavima za isporuku agensa u organizam ili ćeliju subjekta |
| CN114533898B (zh) | 2015-07-09 | 2025-07-01 | 加利福尼亚大学董事会 | 融合脂质体包被的多孔硅纳米颗粒 |
| WO2017048860A1 (en) | 2015-09-14 | 2017-03-23 | Vgsk Technologies, Inc. | A sterically stabilized carrier for subcutaneous, sublingual and oral therapeutics, compositions and methods for treating a mammal |
| US10583083B1 (en) | 2016-08-10 | 2020-03-10 | Verily Life Sciences Llc | ROS-responsive multilamellar liposomal vesicles for targeting inflammatory macrophages |
| US10517823B1 (en) * | 2016-08-10 | 2019-12-31 | Verily Life Sciences Llc | ROS—responsive liposomes for specific targeting |
| CN109803977B (zh) | 2016-08-17 | 2023-03-17 | 菲克特生物科学股份有限公司 | 核酸产品及其施用方法 |
| US11339209B2 (en) | 2016-11-14 | 2022-05-24 | Novartis Ag | Compositions, methods, and therapeutic uses related to fusogenic protein minion |
| MX2019010155A (es) | 2017-02-27 | 2020-12-10 | Translate Bio Inc | Arnm de cftr optimizado por codón novedoso. |
| CA3056797A1 (en) | 2017-03-16 | 2018-09-20 | Children's Medical Center Corporation | Engineered liposomes as cancer-targeted therapeutics |
| CA3060442A1 (en) * | 2017-04-19 | 2018-10-25 | Apa- Advanced Technologies Ltd. | Fusogenic liposomes, compositions, kits and use thereof for treating cancer |
| MA49138A (fr) | 2017-05-16 | 2020-03-25 | Translate Bio Inc | Traitement de la fibrose kystique par administration d'arnm à codons optimisés codant pour la cftr |
| US11464860B2 (en) | 2017-10-27 | 2022-10-11 | Massachusetts Institute Of Technology | Poly (beta-amino esters) and uses thereof |
| WO2019191627A1 (en) | 2018-03-30 | 2019-10-03 | Insmed Incorporated | Methods for continuous manufacture of liposomal drug products |
| WO2020041793A1 (en) | 2018-08-24 | 2020-02-27 | Translate Bio, Inc. | Methods for purification of messenger rna |
| EP3870152A4 (en) * | 2018-10-24 | 2022-10-19 | APA- Advanced Technologies Ltd. | FUSOGENIC LIPOSOMES FOR SELECTIVE IMAGING OF TUMOR CELLS |
| CA3117781A1 (en) | 2018-10-26 | 2020-04-30 | Massachusetts Institute Of Technology | Polymer-lipids and compositions |
| AU2019384557B2 (en) | 2018-11-21 | 2025-07-17 | Translate Bio, Inc. | Treatment of cystic fibrosis by delivery of nebulized mRNA encoding CFTR |
| WO2022192176A1 (en) | 2021-03-09 | 2022-09-15 | Massachusetts Institute Of Technology | Branched poly(-amino esters) for the delivery of nucleic acids |
| CA3217928A1 (en) | 2021-05-05 | 2022-11-10 | Kameswari S. Konduri | Liposome-encapsulated corticosteriods inhibit sars-cov-2 replication and reduces lung inflammation |
| WO2023210671A1 (ja) * | 2022-04-26 | 2023-11-02 | 京セラ株式会社 | 共重合体、高分子膜、測定用装置および測定用担体 |
Family Cites Families (7)
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|---|---|---|---|---|
| US5136095A (en) * | 1987-05-19 | 1992-08-04 | Syntex (U.S.A.) Inc. | Reversible agglutination mediators |
| JPH0720857B2 (ja) * | 1988-08-11 | 1995-03-08 | テルモ株式会社 | リポソームおよびその製法 |
| US5620689A (en) * | 1989-10-20 | 1997-04-15 | Sequus Pharmaceuuticals, Inc. | Liposomes for treatment of B-cell and T-cell disorders |
| US5013556A (en) * | 1989-10-20 | 1991-05-07 | Liposome Technology, Inc. | Liposomes with enhanced circulation time |
| JP3220180B2 (ja) * | 1991-05-23 | 2001-10-22 | 三菱化学株式会社 | 薬剤含有タンパク質結合リポソーム |
| JPH07173079A (ja) * | 1992-12-22 | 1995-07-11 | Nippon Oil & Fats Co Ltd | 両親媒性ポリエチレングリコール誘導体および用途 |
| US5395619A (en) * | 1993-03-03 | 1995-03-07 | Liposome Technology, Inc. | Lipid-polymer conjugates and liposomes |
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1997
- 1997-10-09 TW TW086114833A patent/TW520297B/zh not_active IP Right Cessation
- 1997-10-10 BR BR9712230-0A patent/BR9712230A/pt not_active IP Right Cessation
- 1997-10-10 WO PCT/US1997/018838 patent/WO1998016202A2/en not_active Ceased
- 1997-10-10 JP JP51862998A patent/JP2001504093A/ja not_active Ceased
- 1997-10-10 IL IL12929297A patent/IL129292A0/xx not_active IP Right Cessation
- 1997-10-10 PT PT97912775T patent/PT932391E/pt unknown
- 1997-10-10 EP EP97912775A patent/EP0932391B1/en not_active Expired - Lifetime
- 1997-10-10 AT AT97912775T patent/ATE232086T1/de not_active IP Right Cessation
- 1997-10-10 US US08/949,046 patent/US5891468A/en not_active Expired - Lifetime
- 1997-10-10 ES ES97912775T patent/ES2191833T3/es not_active Expired - Lifetime
- 1997-10-10 DE DE69718924T patent/DE69718924T2/de not_active Expired - Fee Related
- 1997-10-10 DK DK97912775T patent/DK0932391T3/da active
- 1997-10-10 CA CA002267904A patent/CA2267904C/en not_active Expired - Fee Related
- 1997-10-10 AU AU49878/97A patent/AU715063B2/en not_active Ceased
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2002
- 2002-12-19 HK HK02109224.7A patent/HK1047550A1/en unknown
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| WO1998016202A3 (en) | 1998-07-16 |
| US5891468A (en) | 1999-04-06 |
| DE69718924D1 (de) | 2003-03-13 |
| WO1998016202A2 (en) | 1998-04-23 |
| BR9712230A (pt) | 2000-01-25 |
| ATE232086T1 (de) | 2003-02-15 |
| AU715063B2 (en) | 2000-01-13 |
| HK1047550A1 (en) | 2003-02-28 |
| ES2191833T3 (es) | 2003-09-16 |
| EP0932391A2 (en) | 1999-08-04 |
| AU4987897A (en) | 1998-05-11 |
| DK0932391T3 (da) | 2003-05-26 |
| JP2001504093A (ja) | 2001-03-27 |
| CA2267904A1 (en) | 1998-04-23 |
| TW520297B (en) | 2003-02-11 |
| PT932391E (pt) | 2003-06-30 |
| DE69718924T2 (de) | 2003-12-04 |
| IL129292A0 (en) | 2000-02-17 |
| EP0932391B1 (en) | 2003-02-05 |
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