JP2005526727A - pH感受性カチオン脂質、それを含有するリポソーム及びナノカプセル - Google Patents
pH感受性カチオン脂質、それを含有するリポソーム及びナノカプセル Download PDFInfo
- Publication number
- JP2005526727A JP2005526727A JP2003569178A JP2003569178A JP2005526727A JP 2005526727 A JP2005526727 A JP 2005526727A JP 2003569178 A JP2003569178 A JP 2003569178A JP 2003569178 A JP2003569178 A JP 2003569178A JP 2005526727 A JP2005526727 A JP 2005526727A
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- JP
- Japan
- Prior art keywords
- liposome
- lipid
- active substance
- acid
- liposomes
- 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.)
- Abandoned
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- 239000002502 liposome Substances 0.000 title claims abstract description 127
- -1 cationic lipid Chemical class 0.000 title claims abstract description 28
- 239000002088 nanocapsule Substances 0.000 title claims description 31
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 16
- 150000001768 cations Chemical class 0.000 claims abstract description 13
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000005647 linker group Chemical group 0.000 claims abstract description 4
- 150000002632 lipids Chemical class 0.000 claims description 75
- 239000013543 active substance Substances 0.000 claims description 47
- 150000001875 compounds Chemical class 0.000 claims description 31
- 125000006850 spacer group Chemical group 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 22
- 108090000623 proteins and genes Proteins 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 claims description 18
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- 239000003814 drug Substances 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
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- 125000000217 alkyl group Chemical group 0.000 claims description 10
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- 238000009472 formulation Methods 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 9
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- OGQYPPBGSLZBEG-UHFFFAOYSA-N dimethyl(dioctadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC OGQYPPBGSLZBEG-UHFFFAOYSA-N 0.000 claims description 7
- 238000001727 in vivo Methods 0.000 claims description 7
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 claims description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 6
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- 238000001990 intravenous administration Methods 0.000 claims description 3
- 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000001419 myristoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 claims description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 2
- PORPENFLTBBHSG-MGBGTMOVSA-N 1,2-dihexadecanoyl-sn-glycerol-3-phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC PORPENFLTBBHSG-MGBGTMOVSA-N 0.000 claims description 2
- BLCJBICVQSYOIF-UHFFFAOYSA-N 2,2-diaminobutanoic acid Chemical compound CCC(N)(N)C(O)=O BLCJBICVQSYOIF-UHFFFAOYSA-N 0.000 claims description 2
- PECYZEOJVXMISF-UHFFFAOYSA-N 3-aminoalanine Chemical compound [NH3+]CC(N)C([O-])=O PECYZEOJVXMISF-UHFFFAOYSA-N 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 2
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims description 2
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004472 Lysine Substances 0.000 claims description 2
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- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
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- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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- Health & Medical Sciences (AREA)
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- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Dispersion Chemistry (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Molecular Biology (AREA)
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- Transplantation (AREA)
- Heart & Thoracic Surgery (AREA)
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- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medical Preparation Storing Or Oral Administration Devices (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10207177A DE10207177A1 (de) | 2002-02-19 | 2002-02-19 | Fakultativ kationische Lipide |
| PCT/EP2003/001661 WO2003070220A1 (de) | 2002-02-19 | 2003-02-19 | Ph sensitiv kationische lipide, lipsomen und nanokapseln, die diese umfassen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005526727A true JP2005526727A (ja) | 2005-09-08 |
| JP2005526727A5 JP2005526727A5 (enExample) | 2006-04-06 |
Family
ID=27674784
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003569178A Abandoned JP2005526727A (ja) | 2002-02-19 | 2003-02-19 | pH感受性カチオン脂質、それを含有するリポソーム及びナノカプセル |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8192753B2 (enExample) |
| EP (1) | EP1480621A1 (enExample) |
| JP (1) | JP2005526727A (enExample) |
| AU (1) | AU2003210303A1 (enExample) |
| DE (1) | DE10207177A1 (enExample) |
| WO (1) | WO2003070220A1 (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2009518297A (ja) * | 2005-12-01 | 2009-05-07 | プロネイ・セラピューティクス・インコーポレイテッド | 両性リポソーム製剤 |
| JP2009532056A (ja) * | 2006-04-06 | 2009-09-10 | ポリプラス トランスフェクション エスアー | 遺伝子サイレンシングに活性なオリゴヌクレオチドの形質導入用組成物およびその生物学適用と治療適用 |
| WO2010104128A1 (ja) * | 2009-03-11 | 2010-09-16 | 株式会社バイオナノシータ | pH応答性リポソーム |
| US9795566B2 (en) | 2014-07-17 | 2017-10-24 | Fujifilm Corporation | Imidazole compound and liposome containing same |
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| AU2003266014B2 (en) * | 2002-05-06 | 2009-05-14 | Alnylam Pharmaceuticals, Inc. | Methods for delivery of nucleic acids |
| 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 |
| 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 |
| WO2007031333A2 (en) | 2005-09-15 | 2007-03-22 | Novosom Ag | Improvements in or relating to amphoteric liposomes |
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| US9090648B2 (en) * | 2005-12-15 | 2015-07-28 | Centre National De La Recherche Scientifique (Cnrs) | Cationic oligonucleotides, automated methods for preparing same and their uses |
| EP2462924A3 (en) | 2006-10-13 | 2013-01-23 | Marina Biotech, Inc. | Improvements in or relating to amphoteric liposomes. |
| US8193246B2 (en) * | 2006-12-19 | 2012-06-05 | Marina Biotech, Inc. | Lipids and lipid assemblies comprising transfection enhancer elements |
| CA2710713C (en) | 2007-12-27 | 2017-09-19 | Protiva Biotherapeutics, Inc. | Silencing of polo-like kinase expression using interfering rna |
| FR2926818B1 (fr) * | 2008-01-30 | 2012-04-06 | Centre Nat Rech Scient | siRNA CATIONIQUES, SYNTHESE ET UTILISATION POUR L'ARN INTERFERENCE |
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| CA2784568A1 (en) | 2009-12-18 | 2011-06-23 | Martin A. Maier | Lipid particles for delivery of nucleic acids |
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| DE3572491D1 (en) * | 1984-07-25 | 1989-09-28 | Ciba Geigy Ag | Phosphatidyl compounds, process for their preparation and their use |
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| US5965434A (en) * | 1994-12-29 | 1999-10-12 | Wolff; Jon A. | Amphipathic PH sensitive compounds and delivery systems for delivering biologically active compounds |
| FR2756565B1 (fr) * | 1996-12-04 | 1998-12-31 | Oreal | Nouveaux derives d'histidine et leur utilisation en cosmetique ou en pharmacie |
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| JPH11217328A (ja) * | 1998-01-28 | 1999-08-10 | Nissin Food Prod Co Ltd | 抗hiv活性を発現する脂質集合体 |
| US6656498B1 (en) | 1998-11-25 | 2003-12-02 | Vanderbilt University | Cationic liposomes for gene transfer |
| US7112337B2 (en) | 1999-04-23 | 2006-09-26 | Alza Corporation | Liposome composition for delivery of nucleic acid |
| AU7868400A (en) * | 1999-10-08 | 2001-04-23 | Alza Corporation | Neutral-cationic lipid for nucleic acid and drug delivery |
| DE10109898A1 (de) * | 2001-02-21 | 2002-09-05 | Novosom Gmbh | Lipide mit veränderlicher Ladung |
| DE10109897A1 (de) * | 2001-02-21 | 2002-11-07 | Novosom Ag | Fakultativ kationische Liposomen und Verwendung dieser |
-
2002
- 2002-02-19 DE DE10207177A patent/DE10207177A1/de not_active Ceased
-
2003
- 2003-02-19 JP JP2003569178A patent/JP2005526727A/ja not_active Abandoned
- 2003-02-19 AU AU2003210303A patent/AU2003210303A1/en not_active Abandoned
- 2003-02-19 US US10/505,107 patent/US8192753B2/en active Active
- 2003-02-19 WO PCT/EP2003/001661 patent/WO2003070220A1/de not_active Ceased
- 2003-02-19 EP EP03742540A patent/EP1480621A1/de not_active Ceased
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009518297A (ja) * | 2005-12-01 | 2009-05-07 | プロネイ・セラピューティクス・インコーポレイテッド | 両性リポソーム製剤 |
| JP2009532056A (ja) * | 2006-04-06 | 2009-09-10 | ポリプラス トランスフェクション エスアー | 遺伝子サイレンシングに活性なオリゴヌクレオチドの形質導入用組成物およびその生物学適用と治療適用 |
| KR101414392B1 (ko) | 2006-04-06 | 2014-07-18 | 뽈리쁠뤼스-트랑스펙씨옹 | 유전자 침묵에 유효한 올리고뉴클레오티드의 형질감염용 조성물 및 이의 생물학적 및 치료적 용도 |
| WO2010104128A1 (ja) * | 2009-03-11 | 2010-09-16 | 株式会社バイオナノシータ | pH応答性リポソーム |
| JP2010209012A (ja) * | 2009-03-11 | 2010-09-24 | Ichimaru Pharcos Co Ltd | pH応答性リポソーム |
| US8871252B2 (en) | 2009-03-11 | 2014-10-28 | Nanotheta Co, Ltd. | pH-responsive liposome |
| US9795566B2 (en) | 2014-07-17 | 2017-10-24 | Fujifilm Corporation | Imidazole compound and liposome containing same |
Also Published As
| Publication number | Publication date |
|---|---|
| DE10207177A1 (de) | 2003-09-04 |
| WO2003070220A1 (de) | 2003-08-28 |
| EP1480621A1 (de) | 2004-12-01 |
| US8192753B2 (en) | 2012-06-05 |
| AU2003210303A1 (en) | 2003-09-09 |
| US20060002991A1 (en) | 2006-01-05 |
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