JP2001504093A - 融合性リポソーム組成物および方法 - Google Patents
融合性リポソーム組成物および方法Info
- Publication number
- JP2001504093A JP2001504093A JP51862998A JP51862998A JP2001504093A JP 2001504093 A JP2001504093 A JP 2001504093A JP 51862998 A JP51862998 A JP 51862998A JP 51862998 A JP51862998 A JP 51862998A JP 2001504093 A JP2001504093 A JP 2001504093A
- Authority
- JP
- Japan
- Prior art keywords
- liposome
- hydrophilic polymer
- lipid
- composition
- conjugate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
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- 102000035160 transmembrane proteins Human genes 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 239000002753 trypsin inhibitor Substances 0.000 description 1
- 102000003390 tumor necrosis factor Human genes 0.000 description 1
- 210000005166 vasculature Anatomy 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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Classifications
-
- 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
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Dispersion Chemistry (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- 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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2826996P | 1996-10-11 | 1996-10-11 | |
| US60/028,269 | 1996-10-11 | ||
| PCT/US1997/018838 WO1998016202A2 (en) | 1996-10-11 | 1997-10-10 | Fusogenic liposome composition and method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2001504093A true JP2001504093A (ja) | 2001-03-27 |
| JP2001504093A5 JP2001504093A5 (https=) | 2005-06-16 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51862998A Ceased JP2001504093A (ja) | 1996-10-11 | 1997-10-10 | 融合性リポソーム組成物および方法 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US5891468A (https=) |
| EP (1) | EP0932391B1 (https=) |
| JP (1) | JP2001504093A (https=) |
| AT (1) | ATE232086T1 (https=) |
| AU (1) | AU715063B2 (https=) |
| BR (1) | BR9712230A (https=) |
| CA (1) | CA2267904C (https=) |
| DE (1) | DE69718924T2 (https=) |
| DK (1) | DK0932391T3 (https=) |
| ES (1) | ES2191833T3 (https=) |
| HK (1) | HK1047550A1 (https=) |
| IL (1) | IL129292A0 (https=) |
| PT (1) | PT932391E (https=) |
| TW (1) | TW520297B (https=) |
| WO (1) | WO1998016202A2 (https=) |
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Families Citing this family (162)
| 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 |
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| 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 |
| US7087770B2 (en) | 1998-05-16 | 2006-08-08 | Mirus Bio Corporation | Compound containing a labile disulfide bond |
| US6936729B2 (en) * | 1998-05-16 | 2005-08-30 | Mirus Bio Corporation | Compound containing a labile disulfide bond |
| BR9914601A (pt) | 1998-09-16 | 2001-10-23 | Alza Corp | Inibidor de topoisomerase capturado por lipossoma |
| 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 |
| US6852334B1 (en) | 1999-04-20 | 2005-02-08 | The University Of British Columbia | Cationic peg-lipids and methods of use |
| CA2368793A1 (en) * | 1999-04-23 | 2000-11-02 | Alza Corporation | Releasable linkage and compositions containing same |
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| US7238368B2 (en) * | 1999-04-23 | 2007-07-03 | Alza Corporation | Releasable linkage and compositions containing same |
| AUPQ014799A0 (en) * | 1999-05-04 | 1999-05-27 | Access Pharmaceuticals Australia Pty Limited | Amplification of folate-mediated targeting to tumor cells using polymers |
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| EP1180242A1 (de) * | 1999-05-27 | 2002-02-20 | Zeptosens AG | Polymer-enthaltendes vesikel und darauf basierte sensor-nachweisverfahren |
| KR100758158B1 (ko) | 1999-07-14 | 2007-09-12 | 알자 코포레이션 | 중성 지질중합체 및 그를 함유하는 리포솜 조성물 |
| US20040197390A1 (en) * | 2001-05-29 | 2004-10-07 | Shi-Kun Huang | Neutral-cationic lipid for systemic delivery of factor VIII gene |
| WO2001026625A2 (en) | 1999-10-08 | 2001-04-19 | Alza Corp | 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 |
| ES2320193T3 (es) * | 1999-11-24 | 2009-05-20 | Transave, Inc. | Sistema de suministro liposomico dirigido modular. |
| US20030147944A1 (en) * | 1999-12-10 | 2003-08-07 | Mayer Lawrence D | Lipid carrier compositions with protected surface reactive functions |
| PT1274399E (pt) * | 2000-01-28 | 2005-07-29 | Alza Corp | Liposomas que contem um componente envolvente numa solucao supersaturada |
| US7189705B2 (en) | 2000-04-20 | 2007-03-13 | The University Of British Columbia | Methods of enhancing SPLP-mediated transfection using endosomal membrane destabilizers |
| 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 |
| 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 |
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| JP2004512345A (ja) * | 2000-11-02 | 2004-04-22 | スミスクライン・ビーチャム・コーポレイション | 受容体アンタゴニスト−脂質コンジュゲートおよびそれを含有するデリバリービヒクル |
| US6613280B2 (en) | 2001-03-20 | 2003-09-02 | Therox, Inc. | Disposable cartridge for producing gas-enriched fluids |
| US20030003114A1 (en) * | 2001-03-22 | 2003-01-02 | Pan Xing Qing | Enzyme-based anti-cancer compositions and methods |
| US7108863B2 (en) * | 2001-03-26 | 2006-09-19 | Alza Corporation | Liposome composition for improved intracellular delivery of a therapeutic agent |
| JP2004535388A (ja) * | 2001-04-30 | 2004-11-25 | ターゲティッド ジェネティクス コーポレイション | 脂質含有薬物送達複合体およびそれらの生成方法 |
| 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) |
| 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) |
| 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) |
| 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) |
| EP1572067A4 (en) * | 2001-05-18 | 2009-05-13 | Sirna Therapeutics Inc | CONJUGATES AND COMPOSITIONS FOR CELLULAR RELEASE |
| 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) |
| 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) |
| 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) |
| 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) |
| 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) |
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| US6939564B2 (en) * | 2001-06-08 | 2005-09-06 | Labopharm, Inc. | Water-soluble stabilized self-assembled polyelectrolytes |
| EP1575976A4 (en) | 2001-11-02 | 2006-08-23 | Insert Therapeutics Inc | METHODS AND COMPOSITIONS FOR THE THERAPEUTIC USE OF RNA INTERFERENCE |
| GB0129121D0 (en) * | 2001-12-05 | 2002-01-23 | Ic Vec Ltd | Compound |
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| 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) |
| CA2503094A1 (en) * | 2002-02-27 | 2003-09-04 | 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 |
| WO2003083443A2 (en) * | 2002-03-29 | 2003-10-09 | University Of Florida | Lipid mediated screening of drug candidates for identification of active compounds |
| AU2003278691A1 (en) * | 2002-04-23 | 2004-02-02 | The Research Foundation Of State University Of New York | 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 |
| EP1581582B2 (en) | 2003-01-06 | 2017-06-07 | Nektar Therapeutics | Thiol-selective water-soluble polmer derivatives |
| EP1591450A4 (en) * | 2003-01-10 | 2006-05-17 | Yamanouchi Pharma Co Ltd | CONJUGATE FOR RETENTION IN THE BLOOD AND CANCER-SPECIFIC ACTIVE EXTRACTION |
| EP1596829A2 (en) * | 2003-02-28 | 2005-11-23 | 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 |
| KR20060015265A (ko) * | 2003-05-30 | 2006-02-16 | 알자 코포레이션 | 제제의 폐 투여 방법 |
| 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 |
| 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 |
| CA2560901C (en) * | 2003-08-29 | 2012-08-21 | The University Of Newcastle Research Associates Limited | Stimulant sensitive flocculation and consolidation |
| US7943179B2 (en) | 2003-09-23 | 2011-05-17 | Massachusetts Institute Of Technology | pH triggerable polymeric particles |
| JP2007533647A (ja) * | 2003-10-24 | 2007-11-22 | アルザ・コーポレーシヨン | 脂質粒子の調製 |
| US9050378B2 (en) * | 2003-12-10 | 2015-06-09 | Board Of Regents, The University Of Texas System | N2S2 chelate-targeting ligand conjugates |
| EP1706149A2 (en) * | 2004-01-15 | 2006-10-04 | Alza Corporation | Liposome composition for delivery of therapeutic agents |
| 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 |
| 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 |
| ATE401057T1 (de) * | 2004-10-08 | 2008-08-15 | Alza Corp | Verfahren zur einführung eines lipid-verknüpften teils in eine vorgeformte lipidanordnung mit mikrowellen |
| CN101238142B (zh) * | 2005-02-18 | 2012-11-14 | 国立大学法人德岛大学 | 含聚氧化烯链的脂质衍生物及含有该衍生物的脂质膜结构体 |
| JP2006248978A (ja) * | 2005-03-10 | 2006-09-21 | Mebiopharm Co Ltd | 新規なリポソーム製剤 |
| KR20080042045A (ko) * | 2005-05-23 | 2008-05-14 | 에스디지,인코포레이티드 | 포유동물로의 인터페론 전달용 지질 구조물 |
| HUE029994T2 (en) | 2005-12-08 | 2017-04-28 | Insmed Inc | 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 |
| WO2007143659A2 (en) | 2006-06-05 | 2007-12-13 | 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 |
| US8343539B2 (en) * | 2006-07-14 | 2013-01-01 | Regents Of The University Of Minnesota | Compounds that bind α5β1 integrin and methods of use |
| CA2658768C (en) | 2006-07-21 | 2016-05-17 | 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 |
| MX2009003092A (es) * | 2006-09-22 | 2009-05-08 | Labopharm Inc | Composiciones y metodos para suministro de farmaco dirigido a ph. |
| 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 |
| JP5642673B2 (ja) | 2008-07-10 | 2014-12-17 | セリナ・セラピユーテイツクス・インコーポレーテツド | 不活性末端基を有するポリオキサゾリン類、保護された開始基から調製されるポリオキサゾリン類及び関連化合物 |
| ES2646630T3 (es) | 2008-11-07 | 2017-12-14 | Massachusetts Institute Of Technology | Lipidoides aminoalcohólicos y usos de los mismos |
| KR20110098849A (ko) | 2008-12-23 | 2011-09-01 | 파마셋 인코포레이티드 | 뉴클레오시드 유사체 |
| PT2376088T (pt) | 2008-12-23 | 2017-05-02 | Gilead Pharmasset Llc | Fosforamidatos de nucleósidos de 2-amino-purina 6-osubstituída |
| SG194404A1 (en) | 2008-12-23 | 2013-11-29 | Gilead Pharmasset Llc | Synthesis of purine nucleosides |
| EP2230515B1 (en) * | 2009-03-16 | 2014-12-17 | Agilent Technologies, Inc. | Passivation of surfaces after ligand coupling |
| KR20180094137A (ko) * | 2009-05-05 | 2018-08-22 | 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 |
| HUE042177T2 (hu) | 2009-12-01 | 2019-06-28 | Translate Bio Inc | Szteroidszármazék mRNS szállítására humán genetikai betegségekben |
| PT2609923T (pt) | 2010-03-31 | 2017-08-30 | Gilead Pharmasset Llc | Processo para a cristalização de 2-(((s)- (perfluorofenoxi)(fenoxi)fosforil)amino)propanoato de (s)-isopropilo |
| 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 |
| UY33312A (es) | 2010-03-31 | 2011-10-31 | Pharmasset Inc | Fosforamidato de nucleosido de purina |
| 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 |
| EP2609135A4 (en) | 2010-08-26 | 2015-05-20 | Massachusetts Inst Technology | POLY (BETA AMINO ALCOHOLS), THEIR PREPARATION AND USES THEREOF |
| WO2012058210A1 (en) | 2010-10-29 | 2012-05-03 | Merck Sharp & Dohme Corp. | RNA INTERFERENCE MEDIATED INHIBITION OF GENE EXPRESSION USING SHORT INTERFERING NUCLEIC ACIDS (siNA) |
| AU2011336632B2 (en) | 2010-11-30 | 2015-09-03 | Gilead Pharmasset Llc | Compounds |
| US9238716B2 (en) | 2011-03-28 | 2016-01-19 | Massachusetts Institute Of Technology | Conjugated lipomers and uses thereof |
| 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 |
| PL3586861T3 (pl) | 2011-06-08 | 2022-05-23 | Translate Bio, Inc. | Kompozycje nanocząstek lipidowych i sposoby dostarczania mrna |
| US8883989B2 (en) | 2011-10-18 | 2014-11-11 | Regents Of The University Of Minnesota | Fractalkine binding polynucleotides and methods of use |
| KR102451116B1 (ko) | 2011-10-27 | 2022-10-06 | 메사추세츠 인스티튜트 오브 테크놀로지 | 약물 캡슐화 마이크로스피어를 형성할 수 있는, n-말단 상에 관능화된 아미노산 유도체 |
| EP3536787A1 (en) | 2012-06-08 | 2019-09-11 | Translate Bio, Inc. | Nuclease resistant polynucleotides and uses thereof |
| WO2014015027A1 (en) | 2012-07-18 | 2014-01-23 | 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 |
| RU2018135921A (ru) | 2012-11-29 | 2019-02-05 | Инсмед Инкорпорейтед | Стабилизированные составы ванкомицина |
| CN105188675A (zh) * | 2013-03-13 | 2015-12-23 | 马林克罗特有限公司 | 经修饰多西他赛脂质体制剂 |
| PL3467108T3 (pl) | 2013-03-14 | 2024-09-30 | Translate Bio, Inc. | Sposoby oczyszczania informacyjnego rna |
| KR20210122917A (ko) | 2013-03-14 | 2021-10-12 | 샤이어 휴먼 지네틱 테라피즈 인크. | Cftr mrna 조성물 및 관련 방법 및 사용 |
| US10711106B2 (en) | 2013-07-25 | 2020-07-14 | The University Of Chicago | High aspect ratio nanofibril materials |
| ES2707966T3 (es) | 2013-10-22 | 2019-04-08 | Translate Bio Inc | Terapia de ARNm para la deficiencia en síntesis de argininosuccinato |
| EA034103B1 (ru) | 2013-10-22 | 2019-12-27 | Транслейт Био, Инк. | СПОСОБ ЛЕЧЕНИЯ ФЕНИЛКЕТОНУРИИ С ПРИМЕНЕНИЕМ мРНК |
| MX2016005238A (es) | 2013-10-22 | 2016-08-12 | Shire Human Genetic Therapies | Formulaciones de lipidos para la administracion de acido ribonucleico mensajero. |
| AU2014348683B2 (en) | 2013-11-18 | 2020-11-05 | Rubius Therapeutics, Inc. | Synthetic membrane-receiver complexes |
| ES2939542T3 (es) | 2014-01-31 | 2023-04-24 | Factor Bioscience Inc | Métodos y productos para la producción y la administración de ácido nucleico |
| WO2015148971A2 (en) | 2014-03-27 | 2015-10-01 | Research Foundation Of The City University Of New York | Method for detecting or treating triple negative breast cancer |
| ES2865825T3 (es) | 2014-04-01 | 2021-10-18 | Rubius Therapeutics Inc | Procedimientos y composiciones para inmunomodulación |
| PT3134506T (pt) | 2014-04-25 | 2019-10-31 | Translate Bio Inc | Métodos de purificação de rna mensageiro |
| SMT202000516T1 (it) | 2014-05-15 | 2020-11-10 | Insmed Inc | Metodi per trattamento di infezioni micobatteriche polmonati non tubercolari |
| JP6557722B2 (ja) | 2014-05-30 | 2019-08-07 | シャイアー ヒューマン ジェネティック セラピーズ インコーポレイテッド | 核酸の送達のための生分解性脂質 |
| EP3160959B1 (en) | 2014-06-24 | 2023-08-30 | Translate Bio, Inc. | Stereochemically enriched compositions for delivery of nucleic acids |
| 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 |
| JP7199809B2 (ja) | 2015-02-13 | 2023-01-06 | ファクター バイオサイエンス インコーポレイテッド | 核酸製品及びその投与方法 |
| ES2949540T3 (es) | 2015-06-19 | 2023-09-29 | Massachusetts Inst Technology | 2,5-piperazinadionas sustituidas con alquenilo y su uso en composiciones para suministrar un agente a un sujeto o una célula |
| EP3349729A4 (en) | 2015-09-14 | 2019-06-26 | VGSK Technologies, Inc. | STERILE-STABILIZED CARRIER FOR SUBCUTANEOUS, SUB-LINGUAL AND ORAL THERAPEUTICS, COMPOSITIONS AND METHOD FOR TREATING ANIMALS |
| 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 |
| US10576167B2 (en) | 2016-08-17 | 2020-03-03 | Factor Bioscience Inc. | Nucleic acid products and methods of administration thereof |
| EP3538546B1 (en) | 2016-11-14 | 2025-01-08 | Novartis AG | Compositions, methods, and therapeutic uses related to fusogenic protein minion |
| EA201991747A1 (ru) | 2017-02-27 | 2020-06-04 | Транслейт Био, Инк. | НОВАЯ КОДОН-ОПТИМИЗИРОВАННАЯ мРНК CFTR |
| US11260132B2 (en) | 2017-03-16 | 2022-03-01 | Children's Medical Center Corporation | Engineered liposomes as cancer-targeted therapeutics |
| JP2020517750A (ja) * | 2017-04-19 | 2020-06-18 | エイピーエイ− アドバンスト・テクノロジーズ・リミテッドApa− Advanced Technologies Ltd. | 癌処置のための融合性リポソーム、組成物、キットおよびその使用 |
| MX2019013752A (es) | 2017-05-16 | 2020-07-20 | Translate Bio Inc | Tratamiento de la fibrosis quística mediante el suministro de arnm que codifica cftr optimizado en codones. |
| US11464860B2 (en) | 2017-10-27 | 2022-10-11 | Massachusetts Institute Of Technology | Poly (beta-amino esters) and uses thereof |
| EP3773505B1 (en) | 2018-03-30 | 2026-04-29 | Insmed Incorporated | Methods for continuous manufacture of liposomal drug products |
| WO2019213398A1 (en) | 2018-05-02 | 2019-11-07 | Insmed Incorporated | Methods for the manufacture of liposomal drug formulations |
| CA3108544A1 (en) | 2018-08-24 | 2020-02-27 | Translate Bio, Inc. | Methods for purification of messenger rna |
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Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
-
1997
- 1997-10-09 TW TW086114833A patent/TW520297B/zh not_active IP Right Cessation
- 1997-10-10 PT PT97912775T patent/PT932391E/pt unknown
- 1997-10-10 ES ES97912775T patent/ES2191833T3/es not_active Expired - Lifetime
- 1997-10-10 IL IL12929297A patent/IL129292A0/xx not_active IP Right Cessation
- 1997-10-10 US US08/949,046 patent/US5891468A/en not_active Expired - Lifetime
- 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 DK DK97912775T patent/DK0932391T3/da active
- 1997-10-10 AU AU49878/97A patent/AU715063B2/en not_active Ceased
- 1997-10-10 DE DE69718924T patent/DE69718924T2/de not_active Expired - Fee Related
- 1997-10-10 EP EP97912775A patent/EP0932391B1/en not_active Expired - Lifetime
- 1997-10-10 CA CA002267904A patent/CA2267904C/en not_active Expired - Fee Related
- 1997-10-10 AT AT97912775T patent/ATE232086T1/de not_active IP Right Cessation
- 1997-10-10 BR BR9712230-0A patent/BR9712230A/pt not_active IP Right Cessation
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- 2002-12-19 HK HK02109224.7A patent/HK1047550A1/en unknown
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| JP2014519493A (ja) * | 2011-05-12 | 2014-08-14 | イッサム・リサーチ・ディベロップメント・カンパニー・オブ・ザ・ヘブルー・ユニバーシティ・オブ・エルサレム・リミテッド | ポリマー共役脂質を含むリポソームおよび関連用途 |
| JP2018519347A (ja) * | 2015-07-09 | 2018-07-19 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | 融合性リポソーム被覆多孔質ケイ素ナノ粒子 |
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE69718924T2 (de) | 2003-12-04 |
| PT932391E (pt) | 2003-06-30 |
| IL129292A0 (en) | 2000-02-17 |
| AU4987897A (en) | 1998-05-11 |
| EP0932391B1 (en) | 2003-02-05 |
| WO1998016202A3 (en) | 1998-07-16 |
| AU715063B2 (en) | 2000-01-13 |
| CA2267904C (en) | 2005-08-02 |
| DE69718924D1 (de) | 2003-03-13 |
| WO1998016202A2 (en) | 1998-04-23 |
| ATE232086T1 (de) | 2003-02-15 |
| EP0932391A2 (en) | 1999-08-04 |
| BR9712230A (pt) | 2000-01-25 |
| US5891468A (en) | 1999-04-06 |
| CA2267904A1 (en) | 1998-04-23 |
| HK1047550A1 (en) | 2003-02-28 |
| TW520297B (en) | 2003-02-11 |
| DK0932391T3 (da) | 2003-05-26 |
| ES2191833T3 (es) | 2003-09-16 |
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