BRPI0207775B1 - lipossomos anfotéricos, método para carregamento dos mesmos com ingredientes ativos e sua utilização - Google Patents
lipossomos anfotéricos, método para carregamento dos mesmos com ingredientes ativos e sua utilização Download PDFInfo
- Publication number
- BRPI0207775B1 BRPI0207775B1 BRPI0207775A BR0207775A BRPI0207775B1 BR PI0207775 B1 BRPI0207775 B1 BR PI0207775B1 BR PI0207775 A BRPI0207775 A BR PI0207775A BR 0207775 A BR0207775 A BR 0207775A BR PI0207775 B1 BRPI0207775 B1 BR PI0207775B1
- Authority
- BR
- Brazil
- Prior art keywords
- liposomes
- amphoteric
- charge
- amphoteric liposomes
- liposome
- Prior art date
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Classifications
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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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7088—Compounds having three or more nucleosides or nucleotides
- A61K31/7105—Natural ribonucleic acids, i.e. containing only riboses attached to adenine, guanine, cytosine or uracil and having 3'-5' phosphodiester links
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7088—Compounds having three or more nucleosides or nucleotides
- A61K31/711—Natural deoxyribonucleic acids, i.e. containing only 2'-deoxyriboses attached to adenine, guanine, cytosine or thymine and having 3'-5' phosphodiester links
-
- 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
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
- Y10T428/2984—Microcapsule with fluid core [includes liposome]
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10109897A DE10109897A1 (de) | 2001-02-21 | 2001-02-21 | Fakultativ kationische Liposomen und Verwendung dieser |
| PCT/EP2002/001880 WO2002066012A2 (de) | 2001-02-21 | 2002-02-21 | Amphotere liposomen und verwendung dieser |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BR0207775A BR0207775A (pt) | 2004-03-30 |
| BRPI0207775B1 true BRPI0207775B1 (pt) | 2015-10-20 |
Family
ID=7675950
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0207775A BRPI0207775B1 (pt) | 2001-02-21 | 2002-02-21 | lipossomos anfotéricos, método para carregamento dos mesmos com ingredientes ativos e sua utilização |
Country Status (11)
| Country | Link |
|---|---|
| US (4) | US7371404B2 (https=) |
| EP (1) | EP1363601B1 (https=) |
| JP (5) | JP2004525898A (https=) |
| CN (1) | CN1241549C (https=) |
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Families Citing this family (136)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10109897A1 (de) * | 2001-02-21 | 2002-11-07 | Novosom Ag | Fakultativ kationische Liposomen und Verwendung dieser |
| DE10207177A1 (de) * | 2002-02-19 | 2003-09-04 | Novosom Ag | Fakultativ kationische Lipide |
| US7858117B2 (en) * | 2002-02-21 | 2010-12-28 | Novosom Ag | Amphoteric liposomes and their use |
| CA2487274A1 (en) * | 2002-05-06 | 2003-11-13 | Nucleonics Inc. | Spermine chemically linked to lipids and cell-specific targeting molecules as a transfection agent |
| US7718189B2 (en) | 2002-10-29 | 2010-05-18 | Transave, Inc. | Sustained release of antiinfectives |
| DE10255106A1 (de) * | 2002-11-24 | 2004-06-09 | Novosom Ag | Liposomale Glucocorticoide |
| EP1547580A1 (en) * | 2003-12-23 | 2005-06-29 | MediGene Oncology GmbH | Loading of a camptothecin drug into colloidal nanoparticles |
| DE102004054730A1 (de) * | 2004-03-28 | 2006-05-11 | Novosom Ag | Serumstabile amphotere Liposomen |
| US8815599B2 (en) * | 2004-06-01 | 2014-08-26 | Pronai Therapeutics, Inc. | Methods and compositions for the inhibition of gene expression |
| WO2006048329A1 (en) * | 2004-11-05 | 2006-05-11 | Novosom Ag | Improvements in or relating to pharmaceutical compositions comprising an oligonucleotide as an active agent |
| JP2008520600A (ja) * | 2004-11-19 | 2008-06-19 | ノヴォソム アクチェンゲゼルシャフト | 局所投与のための医薬組成物におけるまたはそれに関する改善 |
| EP1764090A1 (en) * | 2005-09-15 | 2007-03-21 | Novosom AG | Amphoteric liposomes for local drug applications |
| EP1676569A1 (en) * | 2004-12-30 | 2006-07-05 | Pevion Biotech Ltd. | Lyophilization of virosomes |
| EP1911443A1 (en) * | 2006-10-13 | 2008-04-16 | Novosom AG | Amphoteric liposomes, method of formulating an amphoteric liposome and a method of loading an amphoteric liposome |
| US20120021042A1 (en) * | 2005-09-15 | 2012-01-26 | Steffen Panzner | Efficient Method For Loading Amphoteric Liposomes With Nucleic Acid Active Substances |
| US20080088046A1 (en) * | 2006-10-13 | 2008-04-17 | Steffen Panzner | Amphoteric liposomes, a method of formulating an amphoteric liposome and a method of loading an amphoteric liposome |
| EP1764089A1 (en) * | 2005-09-15 | 2007-03-21 | Novosom AG | Serum stable liposomes comprising amphoter II lipid mixtures |
| AU2006291429B2 (en) * | 2005-09-15 | 2013-04-04 | Biontech Delivery Technologies Gmbh | Improvements in or relating to amphoteric liposomes |
| EP1934348B1 (en) * | 2005-10-11 | 2018-05-02 | Ben-Gurion University Of The Negev Research And Development Authority | Compositions for silencing the expression of vdac1 and uses thereof |
| PL1957044T3 (pl) * | 2005-12-01 | 2013-11-29 | Pronai Therapeutics Inc | Amfoteryczny preparat liposomowy |
| ES2548240T3 (es) | 2005-12-01 | 2015-10-15 | Pronai Therapeutics, Inc. | Terapias para el cáncer y composiciones farmacéuticas usadas en las mismas |
| EP3067047B1 (en) | 2005-12-08 | 2022-04-20 | Insmed Incorporated | Lipid-based compositions of antiinfectives for treating pulmonary infections |
| EP2012750B1 (en) * | 2006-04-06 | 2018-02-21 | Insmed Incorporated | Methods for coacervation induced liposomal encapsulation and formulations thereof |
| CA2665783C (en) | 2006-10-13 | 2015-12-15 | Novosom Ag | Improvements in or relating to amphoteric liposomes, a method of formulating an amphoteric liposome and a method of loading an amphoteric liposome |
| US20140178462A1 (en) * | 2006-10-13 | 2014-06-26 | Marina Biotech, Inc. | Amphoteric liposomes comprising neutral lipids |
| WO2008074487A2 (en) * | 2006-12-19 | 2008-06-26 | Novosom Ag | Lipids and lipid assemblies comprising transfection enhancer elements |
| PL2308514T3 (pl) | 2007-03-23 | 2013-11-29 | To Bbb Holding B V | Koniugaty do ukierunkowanego dostarczania leku poprzez barierę krew-mózg |
| US20080260895A1 (en) * | 2007-04-17 | 2008-10-23 | Vermeire Drew A | Milk replacer composition and product and method for producing the same |
| WO2008137717A1 (en) | 2007-05-04 | 2008-11-13 | Transave, Inc. | Compositions of multicationic drugs for reducing interactions with polyanionic biomolecules and methods and uses thereof |
| HUE040417T2 (hu) | 2007-05-04 | 2019-03-28 | Marina Biotech Inc | Aminosavlipidek és alkalmazásuk |
| US9119783B2 (en) | 2007-05-07 | 2015-09-01 | Insmed Incorporated | Method of treating pulmonary disorders with liposomal amikacin formulations |
| US9114081B2 (en) | 2007-05-07 | 2015-08-25 | Insmed Incorporated | Methods of treating pulmonary disorders with liposomal amikacin formulations |
| DE102007029471A1 (de) | 2007-06-20 | 2008-12-24 | Novosom Ag | Neue fakultativ kationische Sterole |
| US8822409B2 (en) | 2007-06-20 | 2014-09-02 | Phylogica Limited | Compositions and uses thereof for the treatment of acute respiratory distress syndrome (ARDS) and clinical disorders associated with therewith |
| AU2008295666B2 (en) * | 2007-09-07 | 2013-05-16 | Synvolux Ip B.V. | Improved liposomes and uses thereof |
| AU2008309880B2 (en) * | 2007-10-12 | 2014-07-10 | Biontech Delivery Technologies Gmbh | Amphoteric liposomes comprising neutral lipids |
| US8900627B2 (en) * | 2008-06-06 | 2014-12-02 | Mirna Therapeutics, Inc. | Compositions for the in vivo delivery of RNAi agents |
| JP2012505913A (ja) * | 2008-10-16 | 2012-03-08 | マリーナ バイオテック，インコーポレイテッド | 遺伝子発現を抑制する治療におけるリポソームによる効率的な送達のプロセスおよび組成物 |
| JP5392707B2 (ja) * | 2009-03-31 | 2014-01-22 | 株式会社Ｎｔｔドコモ | 膜小胞分裂システム |
| EP2414519A1 (en) * | 2009-03-31 | 2012-02-08 | Council of Scientific & Industrial Research | Amphoteric liposomal compositions for cellular delivery of small rna molecules for use in rna interference |
| WO2010135714A2 (en) | 2009-05-22 | 2010-11-25 | The Methodist Hospital Research Institute | Methods for modulating adipocyte expression using microrna compositions |
| ATE554749T1 (de) * | 2009-07-09 | 2012-05-15 | Marina Biotech Inc | Nachahmung von lipoproteinstrukturen |
| CN104744310A (zh) * | 2009-07-09 | 2015-07-01 | 玛瑞纳生物技术有限公司 | 包含亚氨基脂质的两性脂质体 |
| EP3318248B1 (en) * | 2009-12-01 | 2019-04-10 | Translate Bio, Inc. | Delivery of mrna for the augmentation of proteins and enzymes in human genetic diseases |
| WO2011120023A1 (en) | 2010-03-26 | 2011-09-29 | Marina Biotech, Inc. | Nucleic acid compounds for inhibiting survivin gene expression uses thereof |
| WO2011133584A2 (en) | 2010-04-19 | 2011-10-27 | Marina Biotech, Inc. | Nucleic acid compounds for inhibiting hras gene expression and uses thereof |
| WO2011139843A2 (en) | 2010-04-28 | 2011-11-10 | Marina Biotech, Inc. | Multi-sirna compositions for reducing gene expression |
| WO2012019168A2 (en) | 2010-08-06 | 2012-02-09 | Moderna Therapeutics, Inc. | Engineered nucleic acids and methods of use thereof |
| EP2625189B1 (en) | 2010-10-01 | 2018-06-27 | ModernaTX, Inc. | Engineered nucleic acids and methods of use thereof |
| US8853377B2 (en) | 2010-11-30 | 2014-10-07 | Shire Human Genetic Therapies, Inc. | mRNA for use in treatment of human genetic diseases |
| WO2012109495A1 (en) | 2011-02-09 | 2012-08-16 | Metabolic Solutions Development Company, Llc | Cellular targets of thiazolidinediones |
| AU2012236099A1 (en) | 2011-03-31 | 2013-10-03 | Moderna Therapeutics, Inc. | Delivery and formulation of engineered nucleic acids |
| WO2012159164A1 (en) | 2011-05-23 | 2012-11-29 | Phylogica Limited | Method of determining, identifying or isolating cell-penetrating peptides |
| RU2013154295A (ru) | 2011-06-08 | 2015-07-20 | Шир Хьюман Дженетик Терапис, Инк. | КОМПОЗИЦИИ ЛИПИДНЫХ НАНОЧАСТИЦ И СПОСОБЫ ДЛЯ ДОСТАВКИ мРНК |
| US9464124B2 (en) | 2011-09-12 | 2016-10-11 | Moderna Therapeutics, Inc. | Engineered nucleic acids and methods of use thereof |
| DE19216461T1 (de) | 2011-10-03 | 2021-10-07 | Modernatx, Inc. | Modifizierte nukleoside, nukleotide und nukleinsäuren und verwendungen davon |
| CA3018046A1 (en) | 2011-12-16 | 2013-06-20 | Moderna Therapeutics, Inc. | Modified nucleoside, nucleotide, and nucleic acid compositions |
| CN102532259A (zh) * | 2012-03-09 | 2012-07-04 | 中国药科大学 | 基于寡肽的阳离子脂质衍生物及在药剂制剂中的应用 |
| CN102603866B (zh) * | 2012-03-15 | 2014-01-15 | 中国药科大学 | 基于寡肽的pH敏感型两性离子及其在药剂中的应用 |
| US9283287B2 (en) | 2012-04-02 | 2016-03-15 | Moderna Therapeutics, Inc. | Modified polynucleotides for the production of nuclear proteins |
| US9254311B2 (en) | 2012-04-02 | 2016-02-09 | Moderna Therapeutics, Inc. | Modified polynucleotides for the production of proteins |
| US9572897B2 (en) | 2012-04-02 | 2017-02-21 | Modernatx, Inc. | Modified polynucleotides for the production of cytoplasmic and cytoskeletal proteins |
| WO2013151665A2 (en) | 2012-04-02 | 2013-10-10 | modeRNA Therapeutics | Modified polynucleotides for the production of proteins associated with human disease |
| PL2852391T3 (pl) | 2012-05-21 | 2022-04-11 | Insmed Incorporated | Układy do leczenia infekcji płuc |
| WO2013185067A1 (en) | 2012-06-08 | 2013-12-12 | Shire Human Genetic Therapies, Inc. | Nuclease resistant polynucleotides and uses thereof |
| IN2012DE01792A (https=) * | 2012-06-11 | 2015-10-16 | Council Scient Ind Res | |
| US10942184B2 (en) | 2012-10-23 | 2021-03-09 | Caris Science, Inc. | Aptamers and uses thereof |
| EP4170031A1 (en) | 2012-10-23 | 2023-04-26 | Caris Science, Inc. | Aptamers and uses thereof |
| CA2890725A1 (en) | 2012-11-05 | 2014-05-08 | Pronai Therapeutics, Inc. | Methods of using biomarkers for the treatment of cancer by modulation of bcl2|expression |
| PL2922554T3 (pl) | 2012-11-26 | 2022-06-20 | Modernatx, Inc. | Na zmodyfikowany na końcach |
| US10124066B2 (en) | 2012-11-29 | 2018-11-13 | Insmed Incorporated | Stabilized vancomycin formulations |
| AU2013361323B2 (en) | 2012-12-19 | 2018-09-06 | Caris Science, Inc. | Compositions and methods for aptamer screening |
| JP6586075B2 (ja) | 2013-03-14 | 2019-10-02 | トランスレイト バイオ， インコーポレイテッド | メッセンジャーｒｎａの精製方法 |
| RS57739B1 (sr) | 2013-03-14 | 2018-12-31 | Translate Bio Inc | Kompozicije cftr irnk i postupci i upotrebe u vezi sa njima |
| KR20150131312A (ko) | 2013-03-15 | 2015-11-24 | 미르나 테라퓨틱스 인코포레이티드 | 마이크로rna 및 egfr-tki 억제제를 이용한 조합 암 치료 |
| US8980864B2 (en) | 2013-03-15 | 2015-03-17 | Moderna Therapeutics, Inc. | Compositions and methods of altering cholesterol levels |
| CA2914685A1 (en) | 2013-06-24 | 2014-12-31 | Mirna Therapeutics, Inc. | Biomarkers of mir-34 activity |
| JP5914418B2 (ja) | 2013-06-26 | 2016-05-11 | 富士フイルム株式会社 | 脂質粒子、核酸送達キャリア、核酸送達キャリア製造用組成物、脂質粒子の製造方法及び遺伝子導入方法 |
| WO2015048744A2 (en) | 2013-09-30 | 2015-04-02 | Moderna Therapeutics, Inc. | Polynucleotides encoding immune modulating polypeptides |
| EP3052521A1 (en) | 2013-10-03 | 2016-08-10 | Moderna Therapeutics, Inc. | Polynucleotides encoding low density lipoprotein receptor |
| CN106413811A (zh) | 2013-10-22 | 2017-02-15 | 夏尔人类遗传性治疗公司 | 精氨基琥珀酸合成酶缺乏症的mrna疗法 |
| JP6506749B2 (ja) | 2013-10-22 | 2019-04-24 | 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 | フェニルケトン尿症のためのｍＲＮＡ療法 |
| EP3126496A1 (en) | 2014-04-01 | 2017-02-08 | Mirna Therapeutics, Inc. | Microrna dosing regimens |
| PL4023249T3 (pl) | 2014-04-23 | 2025-03-10 | Modernatx, Inc. | Szczepionki z kwasem nukleinowym |
| US9850269B2 (en) | 2014-04-25 | 2017-12-26 | Translate Bio, Inc. | Methods for purification of messenger RNA |
| LT3466432T (lt) | 2014-05-15 | 2020-12-28 | Insmed Incorporated | Būdai, skirti plaučių netuberkuliozinėms mikobakterinėms infekcijoms gydyti |
| JP6240570B2 (ja) | 2014-07-17 | 2017-11-29 | 富士フイルム株式会社 | 脂質粒子および核酸送達キャリア |
| WO2016125163A1 (en) | 2015-02-04 | 2016-08-11 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | LIPID ASSEMBLIES AND USES THEREOF AND SOME pH AND ELECTROSTATIC MODULATING LIPIDS TO BE USED IN SAID ASSEMBLIES |
| US11564893B2 (en) | 2015-08-17 | 2023-01-31 | Modernatx, Inc. | Methods for preparing particles and related compositions |
| JP6948313B6 (ja) | 2015-09-17 | 2022-01-14 | モデルナティエックス インコーポレイテッド | 治療剤の細胞内送達のための化合物および組成物 |
| PL3386484T3 (pl) | 2015-12-10 | 2022-07-25 | Modernatx, Inc. | Kompozycje i sposoby dostarczania środków terapeutycznych |
| LT3394030T (lt) | 2015-12-22 | 2022-04-11 | Modernatx, Inc. | Junginiai ir kompozicijos terapinei medžiagai teikti intraceliuliniu būdu |
| US11583504B2 (en) | 2016-11-08 | 2023-02-21 | Modernatx, Inc. | Stabilized formulations of lipid nanoparticles |
| EA201991747A1 (ru) | 2017-02-27 | 2020-06-04 | Транслейт Био, Инк. | НОВАЯ КОДОН-ОПТИМИЗИРОВАННАЯ мРНК CFTR |
| EP4186888B1 (en) | 2017-03-15 | 2025-11-26 | ModernaTX, Inc. | Compound and compositions for intracellular delivery of therapeutic agents |
| CA3055653A1 (en) | 2017-03-15 | 2018-09-20 | Modernatx, Inc. | Lipid nanoparticle formulation |
| WO2018170322A1 (en) | 2017-03-15 | 2018-09-20 | Modernatx, Inc. | Crystal forms of amino lipids |
| 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. |
| WO2018232120A1 (en) | 2017-06-14 | 2018-12-20 | Modernatx, Inc. | Compounds and compositions for intracellular delivery of agents |
| MA49421A (fr) | 2017-06-15 | 2020-04-22 | Modernatx Inc | Formulations d'arn |
| EP3675817A1 (en) | 2017-08-31 | 2020-07-08 | Modernatx, Inc. | Methods of making lipid nanoparticles |
| CN111132753B (zh) * | 2017-09-04 | 2022-05-27 | 一丸自然美健有限公司 | pH敏感性脂质体及其制造方法 |
| US20200208152A1 (en) | 2017-09-08 | 2020-07-02 | Mina Therapeutics Limited | Stabilized sarna compositions and methods of use |
| RS67724B1 (sr) | 2017-10-20 | 2026-03-31 | BioNTech SE | Priprema i skladištenje lipozomskih rnk formulacija koje su pogodne za terapiju |
| WO2019118806A1 (en) | 2017-12-14 | 2019-06-20 | Solid Biosciences Inc. | Non-viral production and delivery of genes |
| EP3773505B1 (en) | 2018-03-30 | 2026-04-29 | Insmed Incorporated | Methods for continuous manufacture of liposomal drug products |
| EP3775211B1 (en) | 2018-04-12 | 2023-04-05 | MiNA Therapeutics Limited | Sirt1-sarna compositions and methods of use |
| JP7449275B2 (ja) | 2018-05-02 | 2024-03-13 | インスメッド インコーポレイテッド | リポソーム薬物製剤の製造方法 |
| US20190381034A1 (en) * | 2018-06-14 | 2019-12-19 | Ming Fang | Pharmaceutical composition and method for acute on chronic liver failure and related liver diseases |
| KR102950141B1 (ko) | 2018-08-24 | 2026-04-07 | 트랜슬레이트 바이오 인코포레이티드 | 전령 rna의 정제 방법 |
| CA3110661A1 (en) | 2018-08-29 | 2020-03-05 | University Of Massachusetts | Inhibition of protein kinases to treat friedreich ataxia |
| WO2020061367A1 (en) | 2018-09-19 | 2020-03-26 | Modernatx, Inc. | Compounds and compositions for intracellular delivery of therapeutic agents |
| CA3113025A1 (en) | 2018-09-19 | 2020-03-26 | Modernatx, Inc. | Peg lipids and uses thereof |
| WO2020061295A1 (en) | 2018-09-19 | 2020-03-26 | Modernatx, Inc. | High-purity peg lipids and uses thereof |
| WO2020061457A1 (en) | 2018-09-20 | 2020-03-26 | Modernatx, Inc. | Preparation of lipid nanoparticles and methods of administration thereof |
| WO2020106946A1 (en) | 2018-11-21 | 2020-05-28 | Translate Bio, Inc. | TREATMENT OF CYSTIC FIBROSIS BY DELIVERY OF NEBULIZED mRNA ENCODING CFTR |
| EP3953473A1 (en) | 2019-04-12 | 2022-02-16 | MiNA Therapeutics Limited | Sirt1-sarna compositions and methods of use |
| CA3155015A1 (en) | 2019-09-19 | 2021-03-25 | Modernatx, Inc. | Carbonate containing lipid compounds and compositions for intracellular delivery of therapeutic agents |
| AU2020350759A1 (en) | 2019-09-19 | 2022-03-31 | Modernatx, Inc. | Branched tail lipid compounds and compositions for intracellular delivery of therapeutic agents |
| EP4031662A1 (en) | 2019-09-20 | 2022-07-27 | Translate Bio, Inc. | Mrna encoding engineered cftr |
| MX2022012683A (es) | 2020-04-09 | 2023-01-11 | Verve Therapeutics Inc | Edicion de bases de pcsk9 y metodos de uso de la misma para el tratamiento de enfermedades. |
| WO2021255262A1 (en) | 2020-06-19 | 2021-12-23 | Sylentis Sau | siRNA AND COMPOSITIONS FOR PROPHYLACTIC AND THERAPEUTIC TREATMENT OF VIRUS DISEASES |
| JP2023549011A (ja) | 2020-09-15 | 2023-11-22 | ヴァーヴ・セラピューティクス，インコーポレーテッド | 遺伝子編集のための脂質製剤 |
| GB2603454A (en) | 2020-12-09 | 2022-08-10 | Ucl Business Ltd | Novel therapeutics for the treatment of neurodegenerative disorders |
| EP4015634A1 (en) | 2020-12-15 | 2022-06-22 | Sylentis, S.A.U. | Sirna and compositions for prophylactic and therapeutic treatment of virus diseases |
| US11524023B2 (en) | 2021-02-19 | 2022-12-13 | Modernatx, Inc. | Lipid nanoparticle compositions and methods of formulating the same |
| TW202305133A (zh) | 2021-03-26 | 2023-02-01 | 英商米納治療有限公司 | Tmem173 sarna組合物及其使用方法 |
| WO2023099884A1 (en) | 2021-12-01 | 2023-06-08 | Mina Therapeutics Limited | Pax6 sarna compositions and methods of use |
| GB202117758D0 (en) | 2021-12-09 | 2022-01-26 | Ucl Business Ltd | Therapeutics for the treatment of neurodegenerative disorders |
| WO2023170435A1 (en) | 2022-03-07 | 2023-09-14 | Mina Therapeutics Limited | Il10 sarna compositions and methods of use |
| WO2024125597A1 (en) | 2022-12-14 | 2024-06-20 | Providence Therapeutics Holdings Inc. | Compositions and methods for infectious diseases |
| WO2024134199A1 (en) | 2022-12-22 | 2024-06-27 | Mina Therapeutics Limited | Chemically modified sarna compositions and methods of use |
| AU2023413766A1 (en) | 2022-12-23 | 2025-05-29 | Biontech Delivery Technologies Gmbh | Composition |
| IL326647A (en) | 2023-09-01 | 2026-04-01 | Novoarc Gmbh | Lipid nanoparticles with a nucleic acid charge and an ionizable lipid |
| WO2025136963A1 (en) * | 2023-12-22 | 2025-06-26 | Coty Inc. | Cationic micro-vesicles and functionalized exosome-like vectors for the delivery of functional agent to the skin |
| WO2026027887A2 (en) | 2024-08-02 | 2026-02-05 | Mina Therapeutics Limited | Hbg1/2-sarna compositions and methods of use |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4599227A (en) * | 1983-11-07 | 1986-07-08 | Wisconsin Alumni Research Foundation | Injectable pharmaceutical preparation for the induction of multiple follicular growth |
| US4891208A (en) * | 1985-04-10 | 1990-01-02 | The Liposome Company, Inc. | Steroidal liposomes |
| US5283122A (en) * | 1984-04-19 | 1994-02-01 | University Of Tennessee Research Corporation | Fused liposome and acid induced method for liposome fusion |
| ATE45744T1 (de) | 1984-07-25 | 1989-09-15 | Ciba Geigy Ag | Phosphatidylverbindungen, verfahren zu ihrer herstellung und ihre verwendung. |
| US5077211A (en) * | 1988-07-06 | 1991-12-31 | Applied Genetics, Inc. | Purification and administration of dna repair enzymes |
| US5290563A (en) * | 1989-07-27 | 1994-03-01 | Laboratoire Des Stallergenes | Method for combining a mixture of heterogeneous substances with liposomes |
| US5165994A (en) * | 1990-06-05 | 1992-11-24 | University Of Delaware | Spontaneous equilbrium surfactant vesicles |
| US5302389A (en) * | 1992-08-17 | 1994-04-12 | Board Of Regents, The University Of Texas System | Method for treating UV-induced suppression of contact hypersensitivity by administration of T4 endonuclease |
| DE69429337T3 (de) * | 1993-04-02 | 2012-08-30 | Anticancer Inc. | Verfahren zur verabreichung von förderlichen zusammensetzungen auf die haarfollikel |
| US5993850A (en) * | 1994-09-13 | 1999-11-30 | Skyepharma Inc. | Preparation of multivesicular liposomes for controlled release of encapsulated biologically active substances |
| US5981501A (en) * | 1995-06-07 | 1999-11-09 | Inex Pharmaceuticals Corp. | Methods for encapsulating plasmids in lipid bilayers |
| US6258792B1 (en) * | 1996-04-12 | 2001-07-10 | University Of Pittsburgh | Cationic cholesteryl derivatives containing cyclic polar groups |
| WO1997039019A1 (en) | 1996-04-12 | 1997-10-23 | University Of Pittsburgh | Novel cationic cholesteryl derivatives containing cyclic polar groups |
| US7384923B2 (en) | 1999-05-14 | 2008-06-10 | Lipoxen Technologies Limited | Liposomes |
| CN1138533C (zh) * | 1996-09-13 | 2004-02-18 | 利普森有限公司 | 脂质体 |
| US5962015A (en) * | 1997-05-02 | 1999-10-05 | Kobo Products S.A.R.L. | Stabilized liposomes |
| AU733310C (en) * | 1997-05-14 | 2001-11-29 | University Of British Columbia, The | High efficiency encapsulation of charged therapeutic agents in lipid vesicles |
| WO1999004819A1 (en) * | 1997-07-24 | 1999-02-04 | Inex Pharmaceuticals Corporation | Liposomal compositions for the delivery of nucleic acid catalysts |
| FR2766706B1 (fr) * | 1997-07-30 | 2001-05-25 | Biovector Therapeutics Sa | Complexes particulaires stables de charge globale neutre ou negative de structure multilamellaire composes par au moins une substance biologiquement active globalement anionique et un constituant cationique, leur preparation et utilisation |
| US6106858A (en) * | 1997-09-08 | 2000-08-22 | Skyepharma, Inc. | Modulation of drug loading in multivescular liposomes |
| JPH11302199A (ja) * | 1998-04-16 | 1999-11-02 | Sankyo Co Ltd | 薬物運搬体を構成するグラフト共重合体 |
| JP2000198731A (ja) * | 1998-10-29 | 2000-07-18 | Sankyo Co Ltd | 毒性の低減されたリポソ―ム |
| DE19852928C1 (de) * | 1998-11-17 | 2000-08-03 | Steffen Panzner | Strukturen in Form von Hohlkugeln |
| US6379698B1 (en) * | 1999-04-06 | 2002-04-30 | Isis Pharmaceuticals, Inc. | Fusogenic lipids and vesicles |
| DE10010264A1 (de) | 2000-03-02 | 2001-09-13 | Novosom Gmbh | Stabilisierte Liposomen und Hüllstrukturen |
| DE10109897A1 (de) | 2001-02-21 | 2002-11-07 | Novosom Ag | Fakultativ kationische Liposomen und Verwendung dieser |
| US7858117B2 (en) * | 2002-02-21 | 2010-12-28 | Novosom Ag | Amphoteric liposomes and their use |
| AU2006291429B2 (en) * | 2005-09-15 | 2013-04-04 | Biontech Delivery Technologies Gmbh | Improvements in or relating to amphoteric liposomes |
-
2001
- 2001-02-21 DE DE10109897A patent/DE10109897A1/de not_active Withdrawn
-
2002
- 2002-02-21 US US10/081,617 patent/US7371404B2/en not_active Expired - Lifetime
- 2002-02-21 DE DE50210271T patent/DE50210271D1/de not_active Expired - Lifetime
- 2002-02-21 AU AU2002234643A patent/AU2002234643B2/en not_active Ceased
- 2002-02-21 WO PCT/EP2002/001880 patent/WO2002066012A2/de not_active Ceased
- 2002-02-21 ES ES02701290T patent/ES2289079T3/es not_active Expired - Lifetime
- 2002-02-21 EP EP02701290A patent/EP1363601B1/de not_active Expired - Lifetime
- 2002-02-21 CN CNB028052137A patent/CN1241549C/zh not_active Expired - Fee Related
- 2002-02-21 CA CA2438116A patent/CA2438116C/en not_active Expired - Lifetime
- 2002-02-21 JP JP2002565572A patent/JP2004525898A/ja active Pending
- 2002-02-21 AT AT02701290T patent/ATE363893T1/de active
- 2002-02-21 BR BRPI0207775A patent/BRPI0207775B1/pt not_active IP Right Cessation
-
2006
- 2006-10-31 US US11/590,357 patent/US7780983B2/en not_active Expired - Lifetime
- 2006-10-31 US US11/590,143 patent/US20070269504A1/en not_active Abandoned
-
2010
- 2010-08-09 US US12/806,342 patent/US20110293695A1/en not_active Abandoned
- 2010-09-21 JP JP2010211089A patent/JP5480764B2/ja not_active Expired - Fee Related
-
2013
- 2013-11-18 JP JP2013237869A patent/JP2014031383A/ja active Pending
-
2014
- 2014-08-18 JP JP2014165961A patent/JP2014218520A/ja active Pending
-
2016
- 2016-01-07 JP JP2016001813A patent/JP2016104786A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| ES2289079T3 (es) | 2008-02-01 |
| US7371404B2 (en) | 2008-05-13 |
| BR0207775A (pt) | 2004-03-30 |
| US20070269504A1 (en) | 2007-11-22 |
| EP1363601B1 (de) | 2007-06-06 |
| JP2011021026A (ja) | 2011-02-03 |
| EP1363601A2 (de) | 2003-11-26 |
| ATE363893T1 (de) | 2007-06-15 |
| US7780983B2 (en) | 2010-08-24 |
| AU2002234643B2 (en) | 2007-06-21 |
| CA2438116C (en) | 2011-10-11 |
| US20070252295A1 (en) | 2007-11-01 |
| JP2004525898A (ja) | 2004-08-26 |
| JP2014218520A (ja) | 2014-11-20 |
| JP2014031383A (ja) | 2014-02-20 |
| US20110293695A1 (en) | 2011-12-01 |
| JP2016104786A (ja) | 2016-06-09 |
| DE10109897A1 (de) | 2002-11-07 |
| WO2002066012A2 (de) | 2002-08-29 |
| DE50210271D1 (de) | 2007-07-19 |
| WO2002066012A3 (de) | 2002-12-19 |
| CN1492756A (zh) | 2004-04-28 |
| CN1241549C (zh) | 2006-02-15 |
| US20030099697A1 (en) | 2003-05-29 |
| CA2438116A1 (en) | 2002-08-29 |
| JP5480764B2 (ja) | 2014-04-23 |
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