TW200400197A - Pharmaceutical compositions of azithromycin - Google Patents
Pharmaceutical compositions of azithromycin Download PDFInfo
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- TW200400197A TW200400197A TW092116536A TW92116536A TW200400197A TW 200400197 A TW200400197 A TW 200400197A TW 092116536 A TW092116536 A TW 092116536A TW 92116536 A TW92116536 A TW 92116536A TW 200400197 A TW200400197 A TW 200400197A
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- azithromycin
- pharmaceutical composition
- grams
- monohydrate
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- 229960004099 azithromycin Drugs 0.000 title claims abstract description 24
- MQTOSJVFKKJCRP-BICOPXKESA-N azithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 MQTOSJVFKKJCRP-BICOPXKESA-N 0.000 title claims abstract description 23
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 13
- 150000004682 monohydrates Chemical class 0.000 claims abstract description 14
- 239000000945 filler Substances 0.000 claims abstract description 8
- 239000003765 sweetening agent Substances 0.000 claims abstract description 8
- 239000002562 thickening agent Substances 0.000 claims abstract description 8
- 239000000796 flavoring agent Substances 0.000 claims abstract description 7
- 235000003599 food sweetener Nutrition 0.000 claims abstract description 6
- 239000000725 suspension Substances 0.000 claims description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- 235000019634 flavors Nutrition 0.000 claims description 6
- 239000008187 granular material Substances 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 5
- 229920001285 xanthan gum Polymers 0.000 claims description 5
- 239000000839 emulsion Substances 0.000 claims description 4
- 235000013599 spices Nutrition 0.000 claims description 4
- 239000000230 xanthan gum Substances 0.000 claims description 4
- 235000010493 xanthan gum Nutrition 0.000 claims description 4
- 229940082509 xanthan gum Drugs 0.000 claims description 4
- 108010011485 Aspartame Proteins 0.000 claims description 3
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 3
- 229930006000 Sucrose Natural products 0.000 claims description 3
- 239000000605 aspartame Substances 0.000 claims description 3
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 claims description 3
- 229960003438 aspartame Drugs 0.000 claims description 3
- 235000010357 aspartame Nutrition 0.000 claims description 3
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 3
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 239000001488 sodium phosphate Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 239000005720 sucrose Substances 0.000 claims description 3
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 claims description 3
- 229910000406 trisodium phosphate Inorganic materials 0.000 claims description 3
- 235000019801 trisodium phosphate Nutrition 0.000 claims description 3
- 239000002552 dosage form Substances 0.000 claims description 2
- 239000006172 buffering agent Substances 0.000 claims 2
- HQUPLSLYZHKKQT-WVVFQGGUSA-N (2r,3s,4r,5r,8r,10r,11r,12s,13s,14r)-11-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-o Chemical compound O.O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 HQUPLSLYZHKKQT-WVVFQGGUSA-N 0.000 claims 1
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 claims 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 1
- 235000003704 aspartic acid Nutrition 0.000 claims 1
- 229960003256 azithromycin monohydrate Drugs 0.000 claims 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 239000001913 cellulose Substances 0.000 claims 1
- 229920002678 cellulose Polymers 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 239000008203 oral pharmaceutical composition Substances 0.000 claims 1
- 239000002304 perfume Substances 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 229960004793 sucrose Drugs 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 abstract description 2
- 235000000346 sugar Nutrition 0.000 description 7
- 239000008122 artificial sweetener Substances 0.000 description 6
- 235000021311 artificial sweeteners Nutrition 0.000 description 6
- 244000018633 Prunus armeniaca Species 0.000 description 5
- 235000009827 Prunus armeniaca Nutrition 0.000 description 5
- 244000290333 Vanilla fragrans Species 0.000 description 5
- 235000009499 Vanilla fragrans Nutrition 0.000 description 5
- 235000012036 Vanilla tahitensis Nutrition 0.000 description 5
- 150000004683 dihydrates Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- -1 Klucel LF® Polymers 0.000 description 3
- 238000002441 X-ray diffraction Methods 0.000 description 3
- 150000008163 sugars Chemical class 0.000 description 3
- 235000015149 toffees Nutrition 0.000 description 3
- 244000099147 Ananas comosus Species 0.000 description 2
- 235000007119 Ananas comosus Nutrition 0.000 description 2
- 229920003091 Methocel™ Polymers 0.000 description 2
- 235000011034 Rubus glaucus Nutrition 0.000 description 2
- 244000235659 Rubus idaeus Species 0.000 description 2
- 235000009122 Rubus idaeus Nutrition 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 229940100692 oral suspension Drugs 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- MIDXCONKKJTLDX-UHFFFAOYSA-N 3,5-dimethylcyclopentane-1,2-dione Chemical compound CC1CC(C)C(=O)C1=O MIDXCONKKJTLDX-UHFFFAOYSA-N 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- 244000144730 Amygdalus persica Species 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 244000307700 Fragaria vesca Species 0.000 description 1
- 235000016623 Fragaria vesca Nutrition 0.000 description 1
- 235000011363 Fragaria x ananassa Nutrition 0.000 description 1
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
- 240000001890 Ribes hudsonianum Species 0.000 description 1
- 235000016954 Ribes hudsonianum Nutrition 0.000 description 1
- 235000001466 Ribes nigrum Nutrition 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- SRMPHJKQVUDLQE-KUJJYQHYSA-N azithromycin dihydrate Chemical compound O.O.O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 SRMPHJKQVUDLQE-KUJJYQHYSA-N 0.000 description 1
- 239000012928 buffer substance Substances 0.000 description 1
- 235000013736 caramel Nutrition 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
Classifications
-
- 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
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Engineering & Computer Science (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Preparation (AREA)
Description
200400197 玖、發明說明： 【發明所屬之技術領域】 本發明係有關一種有機化合物，如阿爾奇徽素 (AZITHROMYCIN)。阿爾奇黴素為一種醫藥活性化合物，例 如作為抗細菌劑，參見例如：默克索引（Merck Index)，第12版 ，第946項。 【先前技術】 (安定）單水合物型阿爾奇黴素與其製劑揭示於例如：WO 0100640、EP 0984020(阿爾奇黴素呈單水合物異丙醇籠形水合 物）與 WO 0210181，且 WO 0100640、EP 0984020與 WO 0210181 中 所謂之（安定）單水合物型阿爾奇黴素。 【發明内容】 吾等已發現一種包含單水合物型阿爾奇黴素之醫藥組合 物，其可適當釋出阿爾奇黴素，且當於水性液體中再組處 時，其中之單水合物型阿爾奇黴素不會轉化成二水合物型·： 本發明一方面提供一種口服用醫藥組合物，其包含，例 如由以下所組成： -作為醫藥活性成分之（安定）單水合物型阿爾奇黴素， -甜味劑， -香料， -緩衝劑， ' -可視需要選用之填料，與 _ 可視需要選用之增稠劑。 每克單水合物型阿爾奇黴素最好包含： 85937 200400197 -12.50至22.50克甜味劑， -0.05至0.5克香料， -0.05至0.5克緩衝劑， -0.00至0.5克填料與 -0·00至1.0克增稠劑。 【實施方式】 甜味劑包括糖與人工甜味劑。糖包括一種或多種糖類， 如：蔑糖；且人工甜味劑包括一種或多種人工甜味劑， 0 如：阿斯巴甜。較佳甜味劑包括糖及糖與人工甜味劑之混 合物。甜味劑更佳為包括糖：人工甜味劑重量比為1:0至44:1 之糖與可視需要選用之人工甜味劑。 香料包括一種或多種香料，例如：如市售香料商品，例 如··選自下列各物組成之群中者：Antiamarum (IFlavopharm舍 司）、Toffee (Silesia公司）與來自Firmenich公司之香料，例如J 香草精（Vanilla Cream)、杏桃、金糖漿（Golden Syrup)、草莓、 鳳梨、黑醋栗、焦糖聚、覆盆子、杏桃Durarome、熱帶水 · 果、紅果實（Red Fruit)。香料組合包括例如：Antiamarum+紅 果實、Antiamarum+Toffee、香草精+鳳梨、香草精+杏桃、香 草精 + 覆盆子，較佳為 Antiamarum (Flavopharm 公司）+Toffee (Silesia公司）、香草精+杏桃（均來自Firmenich公司）。 緩衝劑包括單一緩衝劑物質或緩衝劑物質之組合，如：' 一般緩衝劑，較佳為磷酸三鈉。 填料包括一種或多種填料，例如：一般填料，較佳為 Si〇2，如：Aerosil(s)⑧。 85937 200400197 增稠劑包括一種或多種增稠劑，例如：一般增铜劑，較 佳為選自下列各物組成之群中者：甲基纖維素，例如：甲 基纖維素 A4C⑧、Methocel E3 Premium⑧、Methocel Κ 100 M Premium EP® ;羥丙基纖維素，例如：Klucel LF®、羧甲基纖維素，例 如：羧甲基纖維素鈉，如：Nycel ZSC®、聚乙烯吡咯啶酮， 例如：Kollidon 90®、天然與人造膠質例如··黃原膠；較佳為 黃原膠+經丙基纖維素。 根據本發明組合物可例如：依據一般方法適當製備， φ 如：混合成分形成均質組合物。 根據本發明組合物適合形成懸浮散劑/粒劑，亦即當於液 體中再組合時可形成口服用懸浮液或乳液之散劑/粒劑。該 液體包括水性液體，例如：水。 本發明另一方面提供一種由根據本發明醫藥組合物與水 性液體（例如：水）混合形成之懸浮液或乳液。 二= 本發明另一方面提供一種醫藥單位劑型，其包含含有稂 據本發明醫藥組合物之藥囊，其中各藥囊包含100 mg、200 ^ mg或300 mg (較佳為200 mg)單水合物型阿爾奇黴素。 儘管已知阿爾奇黴素在水性液體中形成二水合物型之傾 向遠高於形成單水合物型，但根據本發明懸浮液或乳液中 單水合物型阿爾奇黴素即使在高溫下，例如：40°C下，亦 驚人地沒有轉化成二水合物型阿爾奇黴素。可採用X-射線' 繞射圖形測定法測定阿爾奇黴素係呈單水合物型或呈二水 合物型，由懸浮液樣本取得之阿爾奇黴素之乾燥過程應溫 和。例如：由根據本發明醫藥組合物於水性液體中再組成 85937 200400197 之口服用懸浮液可經過離心，濾出所得之阿爾奇黴素，溫 和乾燥，例如：於室溫下或略高於室溫下乾燥，所得之乾 燥粉末即可進行X-射線繞射圖形測定法。 下列實例中之所有溫度均為攝氏溫度且未經校正。 實例 取1.2g單水合物型阿爾奇黴素與22.05 g蔗糖粉末、0.04 g黃 原膠、0.04 g羥丙基纖維素（Klucel®)、0.256 g磷酸三鈉、0.024 g 二氧化石夕（SiliciumdioxidXAerosil®) ; 0.18 g阿斯巴甜與 0.12 g香料 混合。 可使用之香料為 Antiamarum (Flavipharm) + Toffeee (Silesia)或香 草精（Firmenich) + 杏桃（Firmenich)。 所得均勻混合物分成6等分，將各等分填入各藥囊中。得 到6個各含200 mg單水合物型阿爾奇黴素之含口服用懸浮粒 劑之藥囊。 / 所得之懸浮粒劑於水中再組成得到懸浮液。取部份懸浮 液加溫至40°C。 自兩種懸浮液中單離出阿爾奇黴素，進行X-射線繞射圖 形測定。已發現自兩種懸浮液（加溫及不加溫）中單離之阿 爾奇黴素均呈單水合物型阿爾奇黴素（不呈二水合物型）。 85937 -9 -
Claims (1)
- 200400197 拾、申請專利範圍： 1. 一種口服用醫藥組合物，其包含： -作為醫藥活性成八士口口 r人t 取刀足早水合物 (AZITHROMYCIN)， 型阿爾奇黴素 -甜味劑， _香料， 2. -緩衝劑， -可視需要選用之填料，與 -可視需要選用之増稠劑。 根據申請專利範圍第1項之醫藥組合物 物型阿爾奇黴素包含： 其中每克單水合 -12.50至22.50克甜味劑， -0.05至0.5克香料， -〇·〇5至0.5克緩衝劑， -〇·〇〇皇0.5克填料與 -〇·〇〇至ι·ο克增稠劑。 3. 根據申請專利範圍第丨或2項中任一項之醫藥組合物，置 包含單水合物型阿爾奇黴素、蔗糖、阿斯巴甜、香料:、 鱗m切（SilidumdiQxide)、黃原膠㈣丙基纖 維素。 4·根據申請專利範圍第1或2項中任一項之醫藥組合物，其' 中母克單水合物型阿爾奇黴素包含丨5至2〇克蔗糖，〇 〇8至 0.2克阿斯巴甜，0·08至0.2克香料，0.1至0.3克磷酸三鈉， 〇·〇1至〇·1克二氧化石夕（Siliciumdioxide)，0.02至0.〇4克黃原膠與 85937 200400197 0.02至0.04克羥丙基纖維素。 5. 根據申請專利範圍第1至4項中任一項之醫藥組合物，其 係懸浮散劑/粒劑， 6. —種醫藥單位劑型，其包括含有根據申請專利範圍第1至 5項中任一項之醫藥組合物之藥囊，其中各藥囊包含200 mg單水合物型阿爾奇黴素。 7. 一種懸浮液或乳液，其係由根據申請專利範圍第5或6項 中任一項之醫藥組合物與水性液體混合製得。 85937 200400197 柒、指定代表圖： (一) 本案指定代表圖為：第（ ）圖。 (二) 本代表圖之元件代表符號簡單說明： 捌、本案若有化學式時，請揭示最能顯示發明特徵的化學 式： 85937
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0214277.6A GB0214277D0 (en) | 2002-06-20 | 2002-06-20 | Organic compounds |
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| TW092116536A TW200400197A (en) | 2002-06-20 | 2003-06-18 | Pharmaceutical compositions of azithromycin |
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| AU (1) | AU2003279392A1 (zh) |
| GB (1) | GB0214277D0 (zh) |
| TW (1) | TW200400197A (zh) |
| WO (1) | WO2004000865A1 (zh) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| GB0224197D0 (en) * | 2002-10-17 | 2002-11-27 | Biochemie Gmbh | Organic compounds |
| US20070185194A1 (en) * | 2003-07-01 | 2007-08-09 | Kamal Mehta | Stable oral compositions of azithromycin monohydrate |
| US20050013835A1 (en) * | 2003-07-15 | 2005-01-20 | Pfizer Inc. | Stable non-dihydrate azithromycin oral suspensions |
| BRPI0417348A (pt) | 2003-12-04 | 2007-03-13 | Pfizer Prod Inc | processo de gelatinização por spray com utilização de uma extrusora para preparação de composições de droga cristalina multiparticulada contendo preferencialmente um poloxámero e um glicerìdeo |
| US6984403B2 (en) | 2003-12-04 | 2006-01-10 | Pfizer Inc. | Azithromycin dosage forms with reduced side effects |
| US7468428B2 (en) | 2004-03-17 | 2008-12-23 | App Pharmaceuticals, Llc | Lyophilized azithromycin formulation |
| WO2006067577A2 (en) * | 2004-12-21 | 2006-06-29 | Pfizer Products Inc. | Stable non-dihydrate azithromycin oral suspensions |
| US8106111B2 (en) | 2009-05-15 | 2012-01-31 | Eastman Chemical Company | Antimicrobial effect of cycloaliphatic diol antimicrobial agents in coating compositions |
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| HRP20010956B1 (hr) * | 1999-06-29 | 2010-09-30 | Biochemie S.A. | Makrolidi |
| RU2188018C2 (ru) * | 2000-06-20 | 2002-08-27 | Нестерук Владимир Викторович | Композиционный состав антибактериального лекарственного средства |
| ES2172417B1 (es) * | 2000-07-31 | 2003-09-16 | Sint Quimica Sa | Nueva forma mejorada de azitromicina monohidrato de menor higroscopicidad, procedimiento de preparacion y composiciones farmaceuticas que la comprenden. |
| HRP20030430B1 (hr) * | 2000-11-27 | 2011-11-30 | Biochemie S.A. | Makrolidni solvati |
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2002
- 2002-06-20 GB GBGB0214277.6A patent/GB0214277D0/en not_active Ceased
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2003
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| GB0214277D0 (en) | 2002-07-31 |
| WO2004000865A1 (en) | 2003-12-31 |
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