TW558442B - Antimycotic agents having high active compound release - Google Patents
Antimycotic agents having high active compound release Download PDFInfo
- Publication number
- TW558442B TW558442B TW086113946A TW86113946A TW558442B TW 558442 B TW558442 B TW 558442B TW 086113946 A TW086113946 A TW 086113946A TW 86113946 A TW86113946 A TW 86113946A TW 558442 B TW558442 B TW 558442B
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- YPHMISFOHDHNIV-FSZOTQKASA-N cycloheximide Chemical compound C1[C@@H](C)C[C@H](C)C(=O)[C@@H]1[C@H](O)CC1CC(=O)NC(=O)C1 YPHMISFOHDHNIV-FSZOTQKASA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
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- AJAZMOFONMJGNP-WMZOPIPTSA-N n-[(2s)-4-methyl-1-oxo-1-[[(2s)-3-oxo-4-(pyridin-2-ylsulfonylamino)butan-2-yl]amino]pentan-2-yl]-1-benzofuran-2-carboxamide Chemical compound O=C([C@H](C)NC(=O)[C@@H](NC(=O)C=1OC2=CC=CC=C2C=1)CC(C)C)CNS(=O)(=O)C1=CC=CC=N1 AJAZMOFONMJGNP-WMZOPIPTSA-N 0.000 description 1
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- 125000002347 octyl group Chemical group [H]C([*])([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 description 1
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Classifications
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- 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
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4412—Non condensed pyridines; Hydrogenated derivatives thereof having oxo groups directly attached to the heterocyclic ring
-
- 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
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- 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
- A61K47/30—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
- A61K47/38—Cellulose; Derivatives thereof
-
- 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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Dermatology (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
- Pyridine Compounds (AREA)
- Steroid Compounds (AREA)
Description
558442 A7 _____B7 五、發明説明（！） 本發明相關於具有高活性化合物释出之局部應用之凝膠製 劑形式之抗真菌製劑，其包含至少一種來自羥4b咬酮類之 抗真菌物質以及至少一種形成親水性凝膠之試劑。 對於局部治療真菌病，尤其是皮膚之真菌病，各式羥呲 啶明衍生物之製劑形式，例如溶液劑、軟膏谢及散劑铪$ 為眾所熟知。皮膚真菌癖之最佳治療，然而，由於眾多樣 之理由，至今所使用之熟知羥吡啶_製劑形式，係未有無 限制之可能。 經濟部中央標準局員工消費合作社印製 (請先聞讀背面之注意事項再填寫本頁) 一般局部應用之液體製劑，係包括澄清水性或水性一酒精 性溶液。彼等一者係喷灑箪皮膚表面，一者則是用於洗滌 或沐浴〇特別地，可將該等使用於任何覆蓋有生長濃密毛 髮的皮廣區域，因為軟膏劑或散劑並不適合用於此等區 域。此外，可將其俵用在該等由於化粧之理由，而不願使 用其他醫藥形式之皮膚區域，例如臉土或高活動之身體部 位（如手肘、膝蓋等）。 活性化合物自溶液劑中釋出之速率通常為高的，因為待經 用藥後，藉由賦形劑組咸物之蒸發，在製劑與皮廣間可得 3 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 558442 A7 B7 五、發明説明（2 ) 經濟部中央標隼局員工消費合作社印製 高濃度梯度，於最終時，此將導致活性化合物可經由皮虜 之吸收，因而達到高的效力。 雖然如此，關於彼等用藥之性質，溶液劑在經評價時，係 稍嫌不受喜愛，因為其液體聚集狀態之理由，操作P難，、 尤其是在臉上。同時，對於限制性皮膚區域之特定用藥係 非可能。 軟膏劑或半固體醫藥形式係投藥形式，其一般在溫度範团 介於室溫及皮廣温度間時為可塗布的，因此可與液艟投藥 形式及該等具有固體特徵者區分開來。根據皮膚性賦形劑 物質之特徵，軟膏谢一般所知者，係指無水性之脂質基質， 或由油性與水相所組成，並藉由乳化劑而安定之乳化液。 由於彼等半固體之稠度，軟膏製劑不同於溶液劑，可經非 常特定地用藥於限制性皮廣區域。然而，因為脂質組成物 之含董，軟膏組成物中之親脂性經此啶酮衍生物之釋出係 受到高度限定。待經軟膏劑用藥而治、療成功後，進一步地 有著受到軟膏劑通常不會離開，而遠留下抗擦拭之薄膜於 皮膚上之事實的反向影響。一旦與衣服或床單接觸時，該 用藥產品可很容易地再度移除，因此不再能合適於成功的 治療。 粉末製舞I生要則係用於分泌增加時之吸附，以及保持皮膚 本紙張尺度適用中國國家榡準（CNS〉A4規格（210X297公嫠） (請先閲讀背面之注意事項再填寫本頁) 訂 558442
、發明説明（ 之乾燥；該黠，特別是在於治療皮膚真菌病，係扮演著重 要的一部份。由於實際應用之緣故，粉末製劑之投藥，幾 乎是唯一地限制在於足部真菌病之治療。 現已發現，經此咬_衍生物之凝膠形式試劑，其包含溶劑 和形成親水性凝膠試劑及常用配劑之輔助劑時，將使得高 度釋出活性化合物成為可能，並歸因於在皮廣中有著高滚 度之活性化合物，因而具有改良作用。根據本發明之製劑， 由於其半固體稠度，故可進一步輕易並特定地應用在受侵 犯之皮膚區域，並同時產生所需之乾透作用，特別是在於 足部真菌病之治療。 因此，本發明相關於一種醫藥製劑，其包含形成親水性凝 膠試劑、水及式I化合物 (請先閲讀背面之注意事項再填寫本頁)
I -5 經濟部中央標準局員工消費合作社印製
(I) 或式I化合物之生理上可耐受之鹽類， 其中R1、R2及R3，可相同或不同，係氫原子或具有1 至4個碳原子之烷基，而R4則為具有6至9個碳原子之 德和碟氣基β ( CNS ) Α4規格 558442
較佳之醫藥製劑，其中 R4為具有6至9個碳原子之餘和錢基，r1&r3、 為氩原子“-者為氩原子、_基或乙基，而r2為具有ι 之一 或2個碳原子之烷基 特別較佳之龍製船其中式ί化合物在r4位置上具有環 狀基Λ ^ 另外較佳者係一種醫藥製劑，其中R4為環己基或-CH2_CH(CH3)-CH2-C(CH3)3 〇 在本案中術語“飽和”，係指該等不包含艏族多重鍵，例 如無乙烯或炔鍵之基團。 ---------! (請先閲讀背面之注意事項再填寫本頁) 訂 經濟部中央標準局員工消費合作社印製 可經提及之適合的式I化合物，例如1-經4-甲各正-己基_、 -6-異-己棊-、-6-王-庚基•或-6-異庚基-2-4啶_、1“羥·4-甲-6“jL_辛基，或-6-異辛基·2-〇Λ咬網，特別是作為1-經·4· 甲-6-(2,4,4-三甲戊基)-2-此咬8¾、1-經-4-甲-6-環己基 咬酮、1-羥_4_甲-6-環己甲基-或6·環己-乙_2-此啶_ (其中 各例之環己基亦可攜帶甲基）、1，羥-4_甲-6-(2-雙環-[2、24】 庚基咬網、1，經-3,4-二甲-6-爷基-或6-二甲午基-2· 此啶酮以及1-羥4-甲-6·(β-苯乙基)-2-4啶酮。 本發明進一步係相關於使用醫藥褽劑以生摩一種用於治療 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X297公釐） 558442 A7 B7 五、發明説明（5 ) 經濟部中央標準局員工消費合作社印製 及預防真菌病之醫藥品。 使用稂據本發明之醫藥品在於真鏑病之治療時，可達徹底 的痊癒。根據本發明之醫藥品，亦可適合於對抗真菌病之 預防性應用。 根據本發明之醫藥製劑中，式I化合物之+量係視各個式I 化合物之結構而定，因此視其自糗膠之釋出、其於皮廣中 之穿透行為’以及其抗微生物性質而定。 於根據本發明之醫藥製劑中，式I化合物通常，按重量計， 係包含自0.05至2百分率之含量，較佳為，按鞏量計，01 至1 % 〇 可能之形成凝膠試劑為天然物質，例如動物醪、果膠、角 又菜膠、瓊脂、西黃耆縢及藻酸鹽，形成半合成凝膠試劑， 例如纖維素醚類（甲基織維素、乙基織維素、羥乙基纖維 素、羧甲基織維素鈉）、澱粉衍生物及果膠衍生物，以及 形成全人工合成凝膠試劑，例如聚丙烯睃酯、聚甲基丙烯 酸酯、聚乙烯醇及聚乙烯吡咯啶酮。聚丙烯酸酯尤其適合。 該等經應用之含量，對按100份終產物重量計時，係自0.3 至2 〇份（按重量計）。 適宜之溶劑為水，以及所有與水互溶之溶劑。適合之該等 __ 7 本紙張尺度適用巾關家樣準（CNS ) A4· ( 21GX297公釐） (請先閲讀背面之注意事項再填寫本頁) 訂 558442 A7 ______B7 五、發明説明（6 ) 有，例如烷醇，譬如乙醇或異丙醇，以及丙二醇和二甲亞 礙。可將一或更多種溶劑，使用在根據本發明配劑之製備 中。 用於率據本發明醫藥髯劑之適宜的添加溶解化劑為： 苯甲醇、2-辛十二醇、己二酸鹽、丙二酵及丙三醇。 此等溶解化劑係經包含在根據本發明之製劑中，按重量 計，自1至15百分率（按重量。/。）。 適宜之另外輔助劑為乳化劑、潤溼劑及拿布劑。 本製劑之製備係以本質上為熟知之方式，藉由將個別成分 组合及，若需要，更進一步處理以適合於特定之製法c 藉由底下之實施例詳細說明本發明，但非限定該等。除非 另經陳述，定量數據均係相關於重量而言。 ·、 經濟部中央標準局員工消費合作社印製 適 準 標 家 釐 7/> 29 558442 A7 B7 五、發明説明（7 ) 實施例1 一種根據本發明具有底下組合4之製劑： 、 1-經4-甲-6-(2,4,4-三甲戊基>2(1Η>Λ啶酮 0.50 % 羥乙基纖維素 1.50% 聚乙二醇-7椰子駿甘油酯 5.00 % 1，2-丙二醇 10.00% 異丙醇 20.00% 去礦質水 63.00% 實施例2 一種根據本發明具有底下組合物之製劑： 1-羥-4-甲·6-環己基-2(1H)吡啶酮 1.00 % 聚丙烯酸聚合物 (例如聚羧己烯製劑(Catbotner) 934P ) 0.70 % 氫氧化鈉 0.20 % 二辛基磺丁二酸鈉 0.05 % 經濟部中央標準局員工消費合作社印製 (請先閲讀背面之注意事項再填寫本頁) 2·辛十二醇 7.50% 異丙醇 25.00% 去礦質水 65.55 % 實施例3 一種根據本發明具有底下組合物之製劑： 9 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 558442 Α7 Β7 經濟部中央標準局員工消費合作社印製 五、發明説明u 1，羥-4-甲-6-環 $ 基-2(111)吡啶_ 0.50 % 聚丙烯酸聚合物 (例如聚羧己烯製劑(Carbomer) 940 ) 0,50 % 氫氧牝鈉 0.20 % 聚氧6烯(20)山梨聚糖單硬脂酸酯 3.50% 肉豆蔻酸異丙酯 1G.00% 乙醇 20,00% 去礦質水 65.30% 實施例4 一種根據本發明具有底下組合物之製劑： 1-羥·4-甲-6-(2Λ，4-三甲戊基)-2(1Η)-4啶酮 1.00 °/〇 羥丙基織維素 1.00% 1，2-丙二醇 2.50% 乙醇 20.00% 去礦質水 75.50% 實施例5 一種得自先前技藝而具有底下組合物之軟膏製劑： 1-經-4·甲-6-環己基-2(1Η)°Λ咬闕 石油膏 硬脂醇 1.00% 20.00 % 15.00% (請先閲讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS ) Α4規格（210Χ297公釐）
2-辛十二醇 10.00% 聚氧6烯(20)山梨聚糖單硬脂酸酯 3·50 % 山槊聚糖單硬脂酸酯 1.50% 去礦質水 49.00% 實施例6 活性測試 於穿透模式中，使用經切除之豬隻皮膚，測試根據本發明 醫藥製费丨中活性化合物之釋出。 於使用經切除之豬隻戋虜之穿透模式中，進行根據本發明 醫藥製劑中活性化合物釋出之測試。在此，對於根據本發 明組合物中，洁性化合物之釋出係藉由微生物測定方法， 經由穿透深度之測定，以獲得間接之結論·· 在以蒸汽消毒已死動物之前，自經屠宰之豬隻切除得到相 當大的一塊背部皮膚，經以溼潤紙及塑膠膜纏繞，並於-2〇 °C下快速冷凍，直至進行測試。 經濟部中央梂準局員工消費合作社印製 測試前，將皮膚表面脂肪组織去除，刮毛髮並為浦毒目的， 以異丙醇處理60分鐘。對於各測試批，係使用一塊單獨的 皮唐（大約2x3公分）。將皮詹表面以含有各種式j化合 物之製劑處理。待於各作用時間（05，丨及4小時）终 了後，藉由洗滌，將產品自皮廣表面移除。為探究活性化
558442 A7 B7五、發明説明（10 ) 合物不同之穿透能力，或製劑不同之釋出能力，於各例中， U蘇格蘭薄膜(Scotchfilm)置其上，而將各片皮膚剝出2 X，6 X及10 X三道執跡。然後將各軌跡以點狀之方式， 接種著 10 X 鬚髮癬菌(Trichophyton mentagrophytes) 100/25 (每個接種點大約200小分生孢手）。然後，將各片皮膚 在含添加青擻素、鍵徽素及環己醯亞胺之水瓊脂上，於28 ώ€下培養> B。自培養起第四S调始，每日將結果以巨觀 方式讀出。 結果： 待經含有活性化合物之凝膠製劑（根據實施例1至4)作 用4小時之後，各片皮唐，不同於相對應之安慰製劑，其 各個切片在巨觀上均無真菌〇 對於非根據本發明而含有活性化合物之軟奮製劑（根據實 施例5)，其係根據先前技藝而製備得者，4個小時之作 用時間，尚不足以殺死經接種之片段上之大分生孢子。 經濟部中央標準局員工消費合作社印製 ___ 12 本紙張尺度適用中國國家榡準（CNS ) Α4規格（21〇X297公釐） (請先聞讀背面之注意事項再填寫本頁)
Claims (1)
- 558442 A8 B8 C8 D8 六、申請專利範圍 第86113946號專利申請案 ROC Patent Appln. No. 86113946 修正之申請專利範圍中文本-附件(二） Amended Claims in Chinese - (Enel. II) (92年1月曰送呈） (Submitted on January ^ ? 2003) 10 1. 一種供治療及預防皮真菌之醫藥組合物，其係包括親 水性凝膠形成劑、潤濕劑或散佈劑或潤濕劑與散佈劑 之混合物、水以及式（I)化合物或該式(I)化合物生理上 可忍受之鹽類 2 15 RR Ο (I) 20 經濟部智慧財產局員工消费合作社印製 25 其中R1、R2與R3為相同或不同，且表氫原子或具有1 至4個碳原子之烷基，以及R4為飽和且具有6至9個 碳原子之烴基團， 其中所使用之親水性凝膠形成劑係為天然物質，如動 物膠、果膠、角叉菜膠、瓊脂、西黃耆膠或藻酸鹽， 為半合成化合物，如纖維素醚類（如曱基纖維素、乙 基纖維素、羥乙基纖維素、羥丙基纖維素或羧曱基纖 維素鈉），為澱粉衍生物或果膠衍生物，亦可為全合 成凝膠形成劑，如聚丙烯酸酯類、聚曱基丙烯酸酯 類、聚乙烯醇或聚乙烯吡咯啶酮類，或為上述親水性 凝膠形成劑之混合物； -13 - 本紙張尺度適用中國國家標準(CNS)A4規格（210 X 297公釐） 86476B-接 558442 A8 B8 C8 D8 六、申請專利範圍 該組合物可額外使用選自於苄基醇、2-辛基十二醇、丙 二醇、己二酸鹽及丙三醇中之增溶劑； 及/或該組合物可額外使用一可與水互溶之溶劑，如乙 醇及/或異丙醇，以及丙二醇或二甲亞砜。 5 2. 根據申請專利範圍第1項之組合物，其中R4為飽和且 具有6至9個碳原子之烴基團，基團R1與R3中之一者 為氫原子，而另一者為氫原子、甲基或乙基，以及R2 為具有1或2個碳原子之烷基。 10 3. 根據申請專利範圍第1項之組合物，其中式(I)化合物 係於R4之位置處具有環狀之基團。 4. 根據申請專利範圍第1或3項之組合物，其中R4為環 15 己基或-CH2-CH(CH3)_CH2-C(CH3)3。 5. 根據申請專利範圍第1項之組合物，其中係使用聚丙 烯酸酯做為親水性凝膠形成劑。 經濟部智慧財產局員工消費合作社印製 20 6.根據申請專利範圍第1項之組合物，其中式(I)化合物 之含量係0.05至2% (重量計），較佳為0.1至1% (重量計）；親水性凝膠形成劑之含量係〇·3至2°/〇 (重量計）。 25 7.根據申請專利範圍第1項之組合物，其中額外使用乳 化劑。 -14 - 本紙張尺度適用中國國家標準(CNS)A4規格（210 X 297公釐）
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| Application Number | Priority Date | Filing Date | Title |
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| DE19639816A DE19639816A1 (de) | 1996-09-27 | 1996-09-27 | Antimykotische Mittel mit hoher Wirkstofffreisetzung |
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| TW558442B true TW558442B (en) | 2003-10-21 |
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| TW086113946A TW558442B (en) | 1996-09-27 | 1997-09-25 | Antimycotic agents having high active compound release |
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| US (3) | US7018656B2 (zh) |
| EP (1) | EP0928192B1 (zh) |
| JP (1) | JP2001501609A (zh) |
| KR (1) | KR100457850B1 (zh) |
| CN (1) | CN1149992C (zh) |
| AR (1) | AR008858A1 (zh) |
| AT (1) | ATE216882T1 (zh) |
| AU (1) | AU718837B2 (zh) |
| BG (1) | BG63864B1 (zh) |
| BR (1) | BR9711559A (zh) |
| CA (1) | CA2267160C (zh) |
| CY (1) | CY2371B1 (zh) |
| CZ (1) | CZ291170B6 (zh) |
| DE (2) | DE19639816A1 (zh) |
| DK (1) | DK0928192T3 (zh) |
| ES (1) | ES2176702T3 (zh) |
| HU (1) | HU228297B1 (zh) |
| ID (1) | ID22149A (zh) |
| IL (1) | IL129140A (zh) |
| MA (1) | MA24331A1 (zh) |
| MY (1) | MY117863A (zh) |
| NO (1) | NO321899B1 (zh) |
| NZ (1) | NZ334849A (zh) |
| OA (1) | OA11026A (zh) |
| PL (1) | PL188840B1 (zh) |
| PT (1) | PT928192E (zh) |
| RS (1) | RS49596B (zh) |
| RU (1) | RU2181281C2 (zh) |
| SI (1) | SI0928192T1 (zh) |
| TR (1) | TR199900723T2 (zh) |
| TW (1) | TW558442B (zh) |
| UA (1) | UA52699C2 (zh) |
| WO (1) | WO1998013042A1 (zh) |
| ZA (1) | ZA978638B (zh) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19639816A1 (de) | 1996-09-27 | 1998-04-02 | Hoechst Ag | Antimykotische Mittel mit hoher Wirkstofffreisetzung |
| US20040039030A1 (en) * | 1996-09-27 | 2004-02-26 | Hoechst Akeengesellschaft | Use of 1-hydroxy-2-pyridones for the treatment of seborrheic dermatitis |
| AU2003242235A1 (en) * | 2002-06-18 | 2003-12-31 | Pola Chemical Industries Inc. | Antifungal medicinal composition |
| CN100425233C (zh) * | 2005-01-12 | 2008-10-15 | 复旦大学 | 一种鼻腔用尼莫地平凝胶剂 |
| US20080176908A1 (en) * | 2007-01-18 | 2008-07-24 | Mcanally Weylan R | Method of using squalene monooxygenase inhibitors to treat acne |
| MX2007009796A (es) * | 2007-08-14 | 2009-02-25 | Cell Therapy And Technology S | Gel conteniendo pirfenidona. |
| WO2010069519A1 (en) | 2008-12-18 | 2010-06-24 | Merz Pharma Gmbh & Co. Kgaa | Topical compositions comprising at least one active ingredient poorly soluble in water and biopolymers such as hyaluronic acid with a pka-value between 5-7 |
| WO2012009794A1 (en) * | 2010-07-19 | 2012-01-26 | Brusells Ventures Corp. | Antimicrobial medical gel composition comprising etherified hydroxyethylcellulose |
| CN105797696A (zh) * | 2016-03-23 | 2016-07-27 | 广东省工程技术研究所 | 一种分子印迹整体柱的制备方法 |
| WO2019198896A1 (ko) * | 2018-04-12 | 2019-10-17 | 숙명여자대학교산학협력단 | 식품 신선도 유지를 위한 항균성 하이드로겔 |
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-
1996
- 1996-09-27 DE DE19639816A patent/DE19639816A1/de not_active Withdrawn
-
1997
- 1997-09-16 SI SI9730324T patent/SI0928192T1/xx unknown
- 1997-09-16 US US09/068,894 patent/US7018656B2/en not_active Expired - Fee Related
- 1997-09-16 HU HU9903804A patent/HU228297B1/hu unknown
- 1997-09-16 ID IDW990127A patent/ID22149A/id unknown
- 1997-09-16 UA UA99042349A patent/UA52699C2/uk unknown
- 1997-09-16 RS YUP-135/99A patent/RS49596B/sr unknown
- 1997-09-16 PT PT97909278T patent/PT928192E/pt unknown
- 1997-09-16 TR TR1999/00723T patent/TR199900723T2/xx unknown
- 1997-09-16 AT AT97909278T patent/ATE216882T1/de active
- 1997-09-16 CA CA002267160A patent/CA2267160C/en not_active Expired - Lifetime
- 1997-09-16 IL IL12914097A patent/IL129140A/en not_active IP Right Cessation
- 1997-09-16 CZ CZ19991073A patent/CZ291170B6/cs not_active IP Right Cessation
- 1997-09-16 EP EP97909278A patent/EP0928192B1/de not_active Expired - Lifetime
- 1997-09-16 AU AU47037/97A patent/AU718837B2/en not_active Expired
- 1997-09-16 PL PL97332604A patent/PL188840B1/pl unknown
- 1997-09-16 BR BR9711559A patent/BR9711559A/pt not_active IP Right Cessation
- 1997-09-16 KR KR10-1999-7002561A patent/KR100457850B1/ko not_active Expired - Lifetime
- 1997-09-16 DE DE59707169T patent/DE59707169D1/de not_active Expired - Lifetime
- 1997-09-16 CN CNB971982643A patent/CN1149992C/zh not_active Expired - Lifetime
- 1997-09-16 ES ES97909278T patent/ES2176702T3/es not_active Expired - Lifetime
- 1997-09-16 WO PCT/EP1997/005068 patent/WO1998013042A1/de not_active Ceased
- 1997-09-16 NZ NZ334849A patent/NZ334849A/xx not_active IP Right Cessation
- 1997-09-16 JP JP10515221A patent/JP2001501609A/ja active Pending
- 1997-09-16 RU RU99108755/14A patent/RU2181281C2/ru active
- 1997-09-16 DK DK97909278T patent/DK0928192T3/da active
- 1997-09-25 TW TW086113946A patent/TW558442B/zh not_active IP Right Cessation
- 1997-09-25 AR ARP970104430A patent/AR008858A1/es not_active Application Discontinuation
- 1997-09-26 ZA ZA9708638A patent/ZA978638B/xx unknown
- 1997-09-26 MY MYPI97004500A patent/MY117863A/en unknown
- 1997-09-29 MA MA24812A patent/MA24331A1/fr unknown
-
1999
- 1999-03-17 BG BG103262A patent/BG63864B1/bg unknown
- 1999-03-25 NO NO19991458A patent/NO321899B1/no not_active IP Right Cessation
- 1999-03-26 OA OA9900069A patent/OA11026A/fr unknown
-
2003
- 2003-08-13 CY CY0300055A patent/CY2371B1/xx unknown
- 2003-10-23 US US10/690,597 patent/US7026337B2/en not_active Expired - Fee Related
-
2006
- 2006-01-31 US US11/342,546 patent/US20060121118A1/en not_active Abandoned
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