JP6449873B2 - 抗生物質のドライシロップ製剤用の粉末混合物 - Google Patents
抗生物質のドライシロップ製剤用の粉末混合物 Download PDFInfo
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- JP6449873B2 JP6449873B2 JP2016526528A JP2016526528A JP6449873B2 JP 6449873 B2 JP6449873 B2 JP 6449873B2 JP 2016526528 A JP2016526528 A JP 2016526528A JP 2016526528 A JP2016526528 A JP 2016526528A JP 6449873 B2 JP6449873 B2 JP 6449873B2
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- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002433 hydrophilic molecules Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229960004903 invert sugar Drugs 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000010420 locust bean gum Nutrition 0.000 description 1
- 239000000711 locust bean gum Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- HHXMXAQDOUCLDN-RXMQYKEDSA-N penem Chemical compound S1C=CN2C(=O)C[C@H]21 HHXMXAQDOUCLDN-RXMQYKEDSA-N 0.000 description 1
- 229940056367 penicillin v Drugs 0.000 description 1
- BPLBGHOLXOTWMN-MBNYWOFBSA-N phenoxymethylpenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)COC1=CC=CC=C1 BPLBGHOLXOTWMN-MBNYWOFBSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 229940007042 proteus vulgaris Drugs 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005204 segregation Methods 0.000 description 1
- 238000001612 separation test Methods 0.000 description 1
- 229960003885 sodium benzoate Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- FKENQMMABCRJMK-RITPCOANSA-N sulbactam Chemical compound O=S1(=O)C(C)(C)[C@H](C(O)=O)N2C(=O)C[C@H]21 FKENQMMABCRJMK-RITPCOANSA-N 0.000 description 1
- 229960005256 sulbactam Drugs 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- OPYGFNJSCUDTBT-PMLPCWDUSA-N sultamicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(=O)OCOC(=O)[C@H]2C(S(=O)(=O)[C@H]3N2C(C3)=O)(C)C)(C)C)=CC=CC=C1 OPYGFNJSCUDTBT-PMLPCWDUSA-N 0.000 description 1
- 229960001326 sultamicillin Drugs 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 235000010491 tara gum Nutrition 0.000 description 1
- 239000000213 tara gum Substances 0.000 description 1
- LPQZKKCYTLCDGQ-WEDXCCLWSA-N tazobactam Chemical compound C([C@]1(C)S([C@H]2N(C(C2)=O)[C@H]1C(O)=O)(=O)=O)N1C=CN=N1 LPQZKKCYTLCDGQ-WEDXCCLWSA-N 0.000 description 1
- 229960003865 tazobactam Drugs 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
- 150000003952 β-lactams Chemical class 0.000 description 1
Classifications
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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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
-
- A—HUMAN NECESSITIES
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- 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
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
-
- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/397—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having four-membered rings, e.g. azetidine
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/429—Thiazoles condensed with heterocyclic ring systems
- A61K31/43—Compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula, e.g. penicillins, penems
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine
- A61K31/546—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine containing further heterocyclic rings, e.g. cephalothin
-
- 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
- A61K47/02—Inorganic compounds
-
- 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
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof
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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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
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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
- A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
- A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
-
- 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
- A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
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- 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
- A61P31/04—Antibacterial agents
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- Medicinal Chemistry (AREA)
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- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
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- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Description
ベータラクタム抗生物質、
80.0から95.0重量%の粉糖、
最大1.0重量%の保存剤、
0.1から2.0重量%の二酸化ケイ素
を含有する、製剤を提供する。
以下の組成物は、良好な流動性と優れた分離安定性を兼ね備えた、粉末混合物として調製されたベータラクタム抗生物質のドライシロップの製剤の成功例である。
粉ショ糖の平衡含水率を2日の異なる日に測定して(12.0%(w/w)、8.3%(w/w))、その結果平均平衡含水率10.2%(w/w)を決定した。比較として、非粉砕結晶性ショ糖RF(精製済み)をベースとする製剤については、平均平衡含水率10.1%(w/w)を決定した(3日の異なる日に測定、8.9%(w/w)、9.7%(w/w)、11.6%(w/w))。
調製された製剤の分離を決定するために、ホイバッハダストメーター(Heubach GmbH、独国)を使用する標準化法を実行した。その方法論は、ドイツ工業規格DIN55992に従って実施された。
流動性調整剤としてのコロイド状ケイ素(例えばエアロジル)の影響を、様々な撹拌速度で粉末混合物を撹拌している時のエネルギー入力を記録するフリーマンパウダーレオメーターを使用して決定した。そこで、等しい濃度のセフィキシム100mg/5mlおよび異なる濃度のエアロジル(1.0%、0.5%、1.5%)を有する異なる3つの製剤が比較された。基礎流動性エネルギー(BFE)は、1.5%、0.5%および1.0%エアロジルに対して、それぞれ345mJ、440mJおよび620mJであると決定された。これから、流動性は、エアロジルの量を1.5から1.0%に減少させると減少するが、エアロジルの量を0.5%に低下させると再び上昇することが実証される。
Claims (14)
- 流動性と分離安定性を兼ね備えた粉末として調製された、セフィキシムのドライシロップ剤の製剤であって、以下の成分:
セフィキシム、
80.0から95.0重量%の粉ショ糖、
最大1.0重量%の保存剤、
最大2.0重量%のコロイド状二酸化ケイ素
を含有し、
前記粉ショ糖の少なくとも95重量%が、250μm未満の粒子径を有する、製剤。 - 最大含水量が3重量%である乾燥粉末としての、請求項1に記載の製剤。
- 粉末の粒子が、50〜150μmのd50値および200μm未満のd90値を有することを特徴とする、請求項1または2に記載の製剤。
- セフィキシムが0.1から15.0重量%の濃度で存在する、請求項1から3のいずれか一項に記載の製剤。
- 追加の医薬活性物質を含有する、請求項1から4のいずれか一項に記載の製剤。
- 粉ショ糖の少なくとも97重量%が、210μm未満の粒子径を有する、請求項1から5のいずれか一項に記載の製剤。
- 粉ショ糖が、乾燥空気1kg当たり少なくとも17gの水分の絶対空気湿度条件で磨砕または粉砕された調整粉ショ糖である、請求項1から6のいずれか一項に記載の製剤。
- 保存剤が、安息香酸ナトリウム、ソルビン酸およびパラベンから選択される、請求項1から7のいずれか一項に記載の製剤。
- 最大1.0重量%のレオロジー改質剤をさらに含み、レオロジー改質剤は、改変多糖類の群から選択される、請求項1から8のいずれか一項に記載の製剤。
- 0.01から2.0重量%の香味成分をさらに含む、請求項1から9のいずれか一項に記載の製剤。
- 請求項1から10のいずれか一項に記載の製剤の製造方法であって、コロイド状二酸化ケイ素、保存剤、任意にレオロジー改質剤および任意の添加剤の予混物に、粉ショ糖を段階的に添加して、次いでセフィキシムを添加する、製造方法。
- 製剤が乾燥されて、4.0重量%未満の水分を含む、請求項11に記載の方法。
- 製剤が噴霧乾燥または蒸発乾燥される、請求項12に記載の方法。
- 医薬製剤の製造のための、請求項1から10のいずれか一項に記載の製剤の使用であって、前記製剤が適用される前に、水中で再構成される、使用。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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EP13177076.0 | 2013-07-18 | ||
EP13177076 | 2013-07-18 | ||
PCT/EP2014/064594 WO2015007571A1 (en) | 2013-07-18 | 2014-07-08 | Powder mixtures for antibiotic dry syrup formulations |
Publications (2)
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JP2016527222A JP2016527222A (ja) | 2016-09-08 |
JP6449873B2 true JP6449873B2 (ja) | 2019-01-09 |
Family
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JP2016526528A Active JP6449873B2 (ja) | 2013-07-18 | 2014-07-08 | 抗生物質のドライシロップ製剤用の粉末混合物 |
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US (1) | US9566337B2 (ja) |
EP (1) | EP3021831B1 (ja) |
JP (1) | JP6449873B2 (ja) |
CN (1) | CN105377236B (ja) |
AU (1) | AU2014292314B2 (ja) |
CA (1) | CA2914468A1 (ja) |
RU (1) | RU2676327C2 (ja) |
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CN112089693B (zh) * | 2020-09-28 | 2023-07-28 | 成都倍特药业股份有限公司 | 一种注射用青霉素类组合物及其制备方法 |
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DE2211019C3 (de) | 1972-03-08 | 1980-08-28 | Bayer Ag, 5090 Leverkusen | Geschmacksverbessernde Formulierungen oraler Penicilline |
US4371117A (en) * | 1979-06-29 | 1983-02-01 | Bennigsen Mackiewicz A Von | Production of powdered sugar |
DE4418957A1 (de) * | 1994-05-31 | 1995-12-07 | Merck Patent Gmbh | Cefixim-Zubereitung |
DE19643472C2 (de) * | 1996-10-22 | 2001-05-23 | Suedzucker Ag | Verfahren zur Konditionierung von feinvermahlenem Zucker durch Mahlraumbefeuchtung |
WO2000061109A1 (fr) | 1999-04-12 | 2000-10-19 | Shionogi & Co., Ltd. | Procede de production de composition medicamenteuse renfermant un compose medicamenteux hydrophobe basique |
GB2375049A (en) * | 2001-05-02 | 2002-11-06 | Athlone Lab Ltd | A process for preparing dry powder formulations comprising a beta-lactam antibiotic and sugar |
RU2332865C2 (ru) * | 2003-10-28 | 2008-09-10 | Дж. М. Хьюбер Корпорейшн | Средства для кондиционирования с покрывающим слоем для пищевых продуктов и фармацевтических препаратов |
JP2008540403A (ja) * | 2005-05-05 | 2008-11-20 | ルピン・リミテッド | セファロスポリンの安定化経口用医薬組成物 |
CN104383546B (zh) * | 2006-02-22 | 2021-03-02 | 曼金德公司 | 用于改善包含二酮哌嗪和活性剂的微粒的药物性质的方法 |
US9233112B2 (en) * | 2006-04-13 | 2016-01-12 | Lupin Limited | Pharmaceutical compositions of cefixime |
DE112007000920T5 (de) * | 2006-04-13 | 2009-02-12 | Lupin Ltd., Mumbai | Pharmazeutische Zusammensetzungen von Cefixim |
WO2008089775A1 (fr) * | 2007-01-22 | 2008-07-31 | Crd Saidal | Procede de fabrication d ' une poudre pour suspension d ' amoxicilline trihydrate contenant du saccharose |
-
2014
- 2014-07-08 AU AU2014292314A patent/AU2014292314B2/en active Active
- 2014-07-08 CA CA2914468A patent/CA2914468A1/en not_active Abandoned
- 2014-07-08 CN CN201480039918.5A patent/CN105377236B/zh active Active
- 2014-07-08 WO PCT/EP2014/064594 patent/WO2015007571A1/en active Application Filing
- 2014-07-08 US US14/901,950 patent/US9566337B2/en active Active
- 2014-07-08 EP EP14739379.7A patent/EP3021831B1/en active Active
- 2014-07-08 JP JP2016526528A patent/JP6449873B2/ja active Active
- 2014-07-08 RU RU2016103937A patent/RU2676327C2/ru active
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CA2914468A1 (en) | 2015-01-22 |
JP2016527222A (ja) | 2016-09-08 |
EP3021831A1 (en) | 2016-05-25 |
AU2014292314B2 (en) | 2019-03-07 |
WO2015007571A1 (en) | 2015-01-22 |
US9566337B2 (en) | 2017-02-14 |
CN105377236A (zh) | 2016-03-02 |
RU2016103937A (ru) | 2017-08-21 |
RU2016103937A3 (ja) | 2018-05-31 |
RU2676327C2 (ru) | 2018-12-28 |
US20160151501A1 (en) | 2016-06-02 |
CN105377236B (zh) | 2019-04-23 |
AU2014292314A1 (en) | 2015-12-10 |
EP3021831B1 (en) | 2022-08-17 |
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