JP2004524368A - 低い水溶性を有する生物学的に活性な化合物を可溶化するための方法および組成物 - Google Patents
低い水溶性を有する生物学的に活性な化合物を可溶化するための方法および組成物 Download PDFInfo
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Classifications
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
- A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
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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
- A61K9/1277—Preparation processes; Proliposomes
- A61K9/1278—Post-loading, e.g. by ion or pH gradient
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
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- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
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- Biophysics (AREA)
- Molecular Biology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
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| WO2006098241A1 (ja) * | 2005-03-14 | 2006-09-21 | Otsuka Pharmaceutical Factory, Inc. | 難水溶性薬物を含有する医薬組成物 |
| JP2007507432A (ja) * | 2003-10-02 | 2007-03-29 | セムバイオシス ジェネティクス インコーポレイテッド | 活性成分を含む油体を調製するための方法 |
| JP2013536805A (ja) * | 2010-09-01 | 2013-09-26 | 北京大学 | 難溶性薬物の液体組成物及びその調製方法 |
| JP2016190881A (ja) * | 2008-05-23 | 2016-11-10 | ザ ユニヴァーシティ オブ ブリティッシュ コロンビア | リポソームナノ粒子中で使用するための修飾薬物 |
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Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7444383B2 (en) | 2000-06-17 | 2008-10-28 | Microsoft Corporation | Bounded-deferral policies for guiding the timing of alerting, interaction and communications using local sensory information |
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Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1202370B (it) * | 1976-07-12 | 1989-02-09 | Hoffmann La Roche | Soluzioni inietabili in cui l'atti vita' emolitica degli agenti di formazione di micelle naturali e' evitata mediante l'aggiunta di lipoidi e relativi prodotti |
| JPH0753661B2 (ja) * | 1984-03-08 | 1995-06-07 | フアレス フアーマスーチカル リサーチ エヌブイ | プロ―リポソーム組成物及びリポソームの水性分散物を作る方法 |
| US5616334A (en) * | 1987-03-05 | 1997-04-01 | The Liposome Company, Inc. | Low toxicity drug-lipid systems |
| CA1338702C (en) * | 1987-03-05 | 1996-11-12 | Lawrence D. Mayer | High drug:lipid formulations of liposomal- antineoplastic agents |
| MX9203808A (es) * | 1987-03-05 | 1992-07-01 | Liposome Co Inc | Formulaciones de alto contenido de medicamento: lipido, de agentes liposomicos-antineoplasticos. |
| US5811119A (en) * | 1987-05-19 | 1998-09-22 | Board Of Regents, The University Of Texas | Formulation and use of carotenoids in treatment of cancer |
| DE3883206T3 (de) * | 1987-09-07 | 2003-11-13 | Teijin Ltd., Osaka | Arzneistoff enthaltende fettemulsion des typs "kurz vor gebrauch hergestellt" sowie verfahren zur herstellung einer arzneihaltigen fettemulsion. |
| IL91664A (en) * | 1988-09-28 | 1993-05-13 | Yissum Res Dev Co | Ammonium transmembrane gradient system for efficient loading of liposomes with amphipathic drugs and their controlled release |
| US5741513A (en) * | 1990-02-08 | 1998-04-21 | A. Natterman & Cie. Gmbh | Alcoholic aqueous gel-like phospholipid composition, its use and topical preparations containing it |
| US5091188A (en) * | 1990-04-26 | 1992-02-25 | Haynes Duncan H | Phospholipid-coated microcrystals: injectable formulations of water-insoluble drugs |
| AU660288B2 (en) * | 1990-07-31 | 1995-06-22 | Transave, Inc. | Accumulation of amino acids and peptides into liposomes |
| CA2157489A1 (en) * | 1993-03-04 | 1994-09-15 | Masaaki Numata | Lewis-associated compound, process for producing the same, and anti-inflammatory |
| DE19609538A1 (de) * | 1996-03-11 | 1997-09-18 | Basf Ag | Feinverteilte Carotinoid- und Retinoidsuspensionen und Verfahren zu ihrer Herstellung |
| EP0699068B1 (en) * | 1993-05-21 | 2001-12-19 | The Liposome Company, Inc. | Reduction of liposome-induced adverse physiological reactions |
| EP0633024A1 (en) * | 1993-07-09 | 1995-01-11 | Ciba-Geigy Ag | Topically administrable zinc phthalocyanine compositions |
| US5415869A (en) * | 1993-11-12 | 1995-05-16 | The Research Foundation Of State University Of New York | Taxol formulation |
| DE69503629T2 (de) * | 1994-05-23 | 1998-11-26 | B. Braun Medical Inc., Bethlehem, Pa. 18018 | Vorrichtung zur herstellung einer formulierung |
| JP2740153B2 (ja) * | 1995-03-07 | 1998-04-15 | エフ・ホフマン−ラ ロシユ アーゲー | 混合ミセル |
| US6447800B2 (en) * | 1996-01-18 | 2002-09-10 | The University Of British Columbia | Method of loading preformed liposomes using ethanol |
| US6096336A (en) * | 1996-01-30 | 2000-08-01 | The Stehlin Foundation For Cancer Research | Liposomal prodrugs comprising derivatives of camptothecin and methods of treating cancer using these prodrugs |
| US6056973A (en) * | 1996-10-11 | 2000-05-02 | Sequus Pharmaceuticals, Inc. | Therapeutic liposome composition and method of preparation |
| EP0974364A4 (en) * | 1996-10-25 | 2000-12-20 | Yoshitomi Pharmaceutical | METHOD FOR PREVENTING THE PREPARATION OF MEDICINAL PRODUCTS |
| DE59710082D1 (de) * | 1996-12-13 | 2003-06-18 | Vesifact Ag Baar | Kosmetische Präparate in Form einer Nanodispersion |
| GB9726916D0 (en) * | 1997-12-19 | 1998-02-18 | Danbiosyst Uk | Nasal formulation |
| WO2000002534A1 (fr) * | 1998-07-10 | 2000-01-20 | Welfide Corporation | Kit a preparer avant usage avec preparation contenant un medicament et solvant destine a cette fin |
| DE19843968A1 (de) * | 1998-09-24 | 2000-04-13 | Hans Dietl | Taxane enthaltende pharmazeutische Zubereitung zur intravenösen Applikation und Verfahren zu ihrer Herstellung |
| US6682758B1 (en) * | 1998-12-22 | 2004-01-27 | The United States Of America As Represented By The Department Of Health And Human Services | Water-insoluble drug delivery system |
| EP1985285A3 (en) * | 1999-04-01 | 2009-08-12 | Hana Biosciences, Inc. | Compositions and methods for treating lymphoma |
| US20030144570A1 (en) * | 1999-11-12 | 2003-07-31 | Angiotech Pharmaceuticals, Inc. | Compositions and methods for treating disease utilizing a combination of radioactive therapy and cell-cycle inhibitors |
| US20020001613A1 (en) * | 2000-02-08 | 2002-01-03 | Susan Niemiec | Method of manufacturing liposomes |
-
2002
- 2002-03-26 PT PT02737899T patent/PT1389089E/pt unknown
- 2002-03-26 CA CA2442539A patent/CA2442539C/en not_active Expired - Fee Related
- 2002-03-26 ES ES02737899T patent/ES2332584T3/es not_active Expired - Lifetime
- 2002-03-26 AU AU2002312777A patent/AU2002312777B2/en not_active Ceased
- 2002-03-26 AT AT02737899T patent/ATE440593T1/de not_active IP Right Cessation
- 2002-03-26 DK DK02737899T patent/DK1389089T3/da active
- 2002-03-26 WO PCT/EP2002/003371 patent/WO2002080883A2/en not_active Ceased
- 2002-03-26 EP EP02737899A patent/EP1389089B1/en not_active Expired - Lifetime
- 2002-03-26 JP JP2002578922A patent/JP2004524368A/ja not_active Withdrawn
- 2002-03-26 DE DE60233484T patent/DE60233484D1/de not_active Expired - Lifetime
-
2003
- 2003-09-26 US US10/670,504 patent/US20040115255A1/en not_active Abandoned
-
2008
- 2008-01-02 US US12/003,849 patent/US20080131499A1/en not_active Abandoned
-
2009
- 2009-08-28 JP JP2009199056A patent/JP2010013461A/ja active Pending
-
2012
- 2012-07-24 JP JP2012163789A patent/JP2012207042A/ja active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007507432A (ja) * | 2003-10-02 | 2007-03-29 | セムバイオシス ジェネティクス インコーポレイテッド | 活性成分を含む油体を調製するための方法 |
| WO2006098241A1 (ja) * | 2005-03-14 | 2006-09-21 | Otsuka Pharmaceutical Factory, Inc. | 難水溶性薬物を含有する医薬組成物 |
| JP4929158B2 (ja) * | 2005-03-14 | 2012-05-09 | 株式会社大塚製薬工場 | 難水溶性薬物を含有する医薬組成物 |
| KR101391020B1 (ko) * | 2005-03-14 | 2014-04-30 | 가부시키가이샤 오츠까 세이야꾸 고죠 | 수난용성 약제를 함유한 약학 조성물 |
| JP2016190881A (ja) * | 2008-05-23 | 2016-11-10 | ザ ユニヴァーシティ オブ ブリティッシュ コロンビア | リポソームナノ粒子中で使用するための修飾薬物 |
| JP2017048188A (ja) * | 2008-09-27 | 2017-03-09 | ジャイナ ファーマシューティカルズ,インコーポレーテッド | 経口適用および局所適用のための脂質系薬学的調製物、ならびにそれらの組成物、方法、および使用 |
| JP2013536805A (ja) * | 2010-09-01 | 2013-09-26 | 北京大学 | 難溶性薬物の液体組成物及びその調製方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20040115255A1 (en) | 2004-06-17 |
| EP1389089A2 (en) | 2004-02-18 |
| DE60233484D1 (de) | 2009-10-08 |
| JP2010013461A (ja) | 2010-01-21 |
| US20080131499A1 (en) | 2008-06-05 |
| CA2442539A1 (en) | 2002-10-17 |
| AU2002312777B2 (en) | 2007-07-05 |
| ATE440593T1 (de) | 2009-09-15 |
| PT1389089E (pt) | 2009-11-30 |
| AU2002312777A2 (en) | 2002-10-21 |
| WO2002080883A2 (en) | 2002-10-17 |
| DK1389089T3 (da) | 2009-12-21 |
| WO2002080883A3 (en) | 2003-12-11 |
| ES2332584T3 (es) | 2010-02-09 |
| CA2442539C (en) | 2011-11-08 |
| EP1389089B1 (en) | 2009-08-26 |
| JP2012207042A (ja) | 2012-10-25 |
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