EA027666B1 - Неводные лекарственные средства в форме проэмульсии на основе таксанов и способы их приготовления и использования - Google Patents
Неводные лекарственные средства в форме проэмульсии на основе таксанов и способы их приготовления и использования Download PDFInfo
- Publication number
- EA027666B1 EA027666B1 EA201201453A EA201201453A EA027666B1 EA 027666 B1 EA027666 B1 EA 027666B1 EA 201201453 A EA201201453 A EA 201201453A EA 201201453 A EA201201453 A EA 201201453A EA 027666 B1 EA027666 B1 EA 027666B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- drug
- docetaxel
- emulsion
- pro
- component
- Prior art date
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Classifications
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/337—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having four-membered rings, e.g. taxol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
-
- 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
- A61K9/107—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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Molecular Biology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biophysics (AREA)
- Dispersion Chemistry (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Oncology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
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| US33070510P | 2010-05-03 | 2010-05-03 | |
| PCT/US2011/034586 WO2011139899A2 (en) | 2010-05-03 | 2011-04-29 | Non-aqueous taxane pro-emulsion formulations and methods of making and using the same |
Publications (2)
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| EA201201453A1 EA201201453A1 (ru) | 2013-04-30 |
| EA027666B1 true EA027666B1 (ru) | 2017-08-31 |
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| NZ (1) | NZ603828A (enExample) |
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| SG (2) | SG10201503234SA (enExample) |
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| UA (1) | UA109275C2 (enExample) |
| WO (1) | WO2011139899A2 (enExample) |
| ZA (1) | ZA201208229B (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP5824511B2 (ja) | 2010-05-03 | 2015-11-25 | テイコク ファーマ ユーエスエー インコーポレーテッド | 非水タキサンプロエマルジョン配合物ならびにそれを調製および使用する方法 |
| JP5847942B2 (ja) * | 2012-07-19 | 2016-01-27 | 富士フイルム株式会社 | タキサン系活性成分含有液体組成物、その製造方法及び液体製剤 |
| JO3685B1 (ar) | 2012-10-01 | 2020-08-27 | Teikoku Pharma Usa Inc | صيغ التشتيت الجسيمي للتاكسين غير المائي وطرق استخدامها |
| CN104720070A (zh) * | 2013-12-20 | 2015-06-24 | 财团法人食品工业发展研究所 | 微乳液预浓缩物和微乳液及其制备方法 |
| TWI531318B (zh) | 2013-12-20 | 2016-05-01 | 財團法人食品工業發展研究所 | 微乳液預濃縮物和微乳液暨其製備方法 |
| CN106176599A (zh) * | 2015-05-06 | 2016-12-07 | 江苏天士力帝益药业有限公司 | 一种卡巴他赛脂肪乳注射剂及其制备方法 |
| JP6292267B2 (ja) * | 2016-09-13 | 2018-03-14 | ニプロ株式会社 | ドセタキセル製剤 |
| CN110709105A (zh) * | 2017-03-31 | 2020-01-17 | 技术防卫株式会社 | 载有药物的非水系组合物及其制备方法 |
| JP2018115178A (ja) * | 2018-03-15 | 2018-07-26 | ニプロ株式会社 | ドセタキセル製剤 |
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