TW406023B - Pharmaceutical formulations containing voriconazole - Google Patents
Pharmaceutical formulations containing voriconazole Download PDFInfo
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- TW406023B TW406023B TW087106918A TW87106918A TW406023B TW 406023 B TW406023 B TW 406023B TW 087106918 A TW087106918 A TW 087106918A TW 87106918 A TW87106918 A TW 87106918A TW 406023 B TW406023 B TW 406023B
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- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 5
- BCEHBSKCWLPMDN-MGPLVRAMSA-N voriconazole Chemical compound C1([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)=NC=NC=C1F BCEHBSKCWLPMDN-MGPLVRAMSA-N 0.000 title abstract 2
- 229960004740 voriconazole Drugs 0.000 title abstract 2
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical class O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000000203 mixture Substances 0.000 claims description 14
- 229920000858 Cyclodextrin Polymers 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- -1 alkali metal salt Chemical class 0.000 claims description 6
- 230000002079 cooperative effect Effects 0.000 claims description 5
- 238000001990 intravenous administration Methods 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 208000015181 infectious disease Diseases 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 238000007920 subcutaneous administration Methods 0.000 claims 2
- 208000035143 Bacterial infection Diseases 0.000 claims 1
- 241000233866 Fungi Species 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 claims 1
- 208000022362 bacterial infectious disease Diseases 0.000 claims 1
- 150000003839 salts Chemical class 0.000 abstract description 5
- NZAQRZWBQUIBSF-UHFFFAOYSA-N 4-(4-sulfobutoxy)butane-1-sulfonic acid Chemical compound OS(=O)(=O)CCCCOCCCCS(O)(=O)=O NZAQRZWBQUIBSF-UHFFFAOYSA-N 0.000 description 4
- 238000004108 freeze drying Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000008215 water for injection Substances 0.000 description 3
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000010253 intravenous injection Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical group CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical class OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- VNDHXHMRJVTMTK-WZVRVNPQSA-H hexasodium 4-[[(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecahydroxy-10-(hydroxymethyl)-15,20,25,30,35-pentakis(4-sulfonatobutoxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontan-5-yl]methoxy]butane-1-sulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].OC[C@H]1O[C@@H]2O[C@H]3[C@H](O)[C@@H](O)[C@H](O[C@@H]3COCCCCS([O-])(=O)=O)O[C@H]3[C@H](O)[C@@H](O)[C@H](O[C@@H]3COCCCCS([O-])(=O)=O)O[C@H]3[C@H](O)[C@@H](O)[C@H](O[C@@H]3COCCCCS([O-])(=O)=O)O[C@H]3[C@H](O)[C@@H](O)[C@H](O[C@@H]3COCCCCS([O-])(=O)=O)O[C@H]3[C@H](O)[C@@H](O)[C@H](O[C@@H]3COCCCCS([O-])(=O)=O)O[C@H]3[C@H](O)[C@@H](O)[C@H](O[C@@H]3COCCCCS([O-])(=O)=O)O[C@H]1[C@H](O)[C@H]2O VNDHXHMRJVTMTK-WZVRVNPQSA-H 0.000 description 1
- 239000000413 hydrolysate Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 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
- 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
- A61K47/40—Cyclodextrins; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- A61K47/50—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6949—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
- A61K47/6951—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes using cyclodextrin
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nanotechnology (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medical Informatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Biophysics (AREA)
- Biotechnology (AREA)
- General Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Communicable Diseases (AREA)
- Inorganic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
經濟部中央標準局員工消費合作社印繁 406023_B7__ 五、發明説明1() 本發明保屦I佛利-¾那潘具藤基T*-基崔沒谓屬..精之^ 新穎藥學組成物。 佛利可那唑係揭示於歐洲專利申請案0 4 4 0 3 7 2 中（見實例7 )。它具有下列結構：
且可用以治療黴菌感染。佛利可那唑具有低水溶性（ 0 . 2 m g /m 1 @ ρ Η 3 )，且於水中不安定（一 種無活性對掌異構體係由反- 丁間醛醇水解產物的重組作 用形成）。因此，具有足夠有效成份之水性靜脈內組成物 的發展是困難的。這些問題因化合物之半極性性質（ log D=l._ 8)而更形嚴重，其意指它在傳統方法 (諸如，油類，界面活性劑或水可相容之輔溶劑）下通常 不可溶解。 歐洲專利申請案0 4 4 0 3 7 2提及其中所揭示之化 合物可用環糊精調製：但是，現在吾人懷疑未衍化或未代 謝之環糊精對人體具有毒性作用，因此’並不適供作爲藥 學賦形劑，尤其是當非經腸投服時。 國際專利申請案WO 9 1/1 1 1 7 2號揭示通式 A所示磺基烷基醚環糊精衍生物’ 本纸張尺度適用中國國家標準（CNS ) Α4規格（210Χ297公釐） -4- (請先閲讀背面之注意事項再填寫本頁)
、1T *1 406GS3 A7 B7 五、發明説明4 )
經濟部中央標皁局員工消費合作社印12 式中： η示4，5或6 ; Ri-6各別示0_或0_ (C2-6伸烷基）一SO—，唯其 先條件至少R 1和R 2之一示0 — ( C 2 - 6伸烷基）— SO—;以及Si-9各別示藥學上可接受之陽離子（諸如， Η + 或 N a + )。 現在，吾人已發現佛利可那唑之水中溶解度可藉由使 用國際專利申請案W 0 9 1 / 1 1 1 7 2中所揭示之磺 基烷基醚環糊精衍生物類之分子膠囊化作用而提高，特別 是當η示5 (A -環糊精衍生物）且環糊精環經磺基丁基 取代時尤然。 因此，依本發明係提供包含佛利可那唑，或其藥學上 可接受衍生物以及通式I所示環糊精之藥學組成物： ----：— ^------^------11—-------t . (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 ) A4規格（210X297公釐） -5- 經濟部中央標率局員工消費合作社印製 406023 ^---- 五'發明説明i )
式中： ，尺23-8及113!1-8各別示〇H或 0(CH2)4S03H; 唯其先決條件爲至少有一 R 1 a — 8示 〇(CH2)4S〇3H; 或其藥學上可接受之鹽類。 最令人感興趣之藥學上可接受鹽類是： 〇 (CH2) 4S〇3H基團之鹽類，例如’驗金屬鹽類’ 諸如，鈉鹽。 較理想的是，通式I中，每分子內之 〇 (CH2) 4S〇3H基團的平均數目是在6 · 1 — 6 . 9範圍內，例如，6 . 5。此乃增強分子膠囊化作用 而增強佛利可那唑溶解度。此一作用並不能預期得到，因 爲取代程度提高會增加環糊精洞穴周圍之立體阻礙而可能 減低複合物效率。 較理想的是每一存在之0 (CH2) 4S〇3h基團係 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐_Γ I ' ' II 1! —l· - - - - - I !! i ---- - - ϋ ! m T (請先閱讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製 406023 A7 B7 五、發明説明4 ) 爲鹼金屬鹽X諸表暴I)形簾1-此河-增L加分子屏佛利可胳― 唑之親和力（其因佛利可那唑是不帶電荷的而不可預期） 〇 理想的是，此組成物係供非經腸投服的，例如，靜脈 內注射。 佛利可那唑-環糊精衍生物複合體之水溶性進一步藉 由低壓凍乾（冷凍乾燥）而加強。在本發明組成物中使用 之環糊精衍生物使最後加工完成之低壓凍乾產物可容納高 濕度（多達3%)而無損於安定性。再者，前述環糊精衍 生物之使用控制且使佛利可那唑之無活性對掌異構物之形 成減至最小。 通常，在本發明之水性靜脈內及肌內組成物中，佛利 可那唑將以5mg/ml至5〇mg/ml (例如，1〇 mg/m 1至3 Omg/m 1 )之濃度存在。通式I之環 糊精衍生物將以佛利可那唑：環糊精衍生物之莫耳比値爲 1 : 1至1 : 10 (例如，1 : 2至1 : 7，尤其是1 : 2至1:3)存在組成物在使用前可先予低壓凍乾（冷凍 乾燥）以供貯存，而在必要時再用水調製。 在以下實例中’磺基丁基醚/3 _環糊精具有每一環糊 精分子平均6 . 5之擴基丁基醚取代度，且每一磺基丁基 醚單元係以其鈉鹽形態存在。 實例1 : 佛利可那唑之靜脈內注射組成物 本紙張尺度適用中國國家標準（CNS ) A4规格（21〇X：297公釐） Γ" (請先閱讀背面之注意事項再填寫本頁)
^06023 、發明説明$ ) 成份 詳細說明書 mg/ml 佛利可那唑 輝瑞藥廠（Pfizer) 10.000 磺基丁基醚yS—環糊精 輝瑞藥廠（Pfizer) 160.000 注射用水 Ph.Eur. 至1.000ml 總共 1.000ml 方法： 1 .在固定攪拌同時，將磺基丁基醚/S —環糊精（ s B E CD)加至注射用水最後體積之8 0%，再持續攪 拌至SBECD溶解爲止。 2 ·加入佛利可那唑並攪拌溶解。 3 .加注射用水至溶液體積。 4 .經由無菌0 . 2 m m尼龍濾網過濾所得溶液至無 菌容器內。 5 .將2 0 m 1體積塡入無菌冷凍乾燥小玻瓶中並加 上栓塞密封。低壓凍乾。 · (請先閱讀背面之注意事項再填寫本頁)
、1T 經濟部中央標準局員工消費合作社印製 本紙張尺度適用中國國家標準（CNS ) Α4規格（210 Χ 297公釐）-8 -
Claims (1)
- A8 sr.i? 敝 六、申請專利範圍 附件一 ： __________________________________________________________________________________________________________________________________ _______ 第87 1 069 1 8號專利申請案 中文申請專利範圍修正本 民國88年9月修正 1 ·—種用於治療撤菌感染之藥學組成物，其包含佛 利可那唑爲活性成份，以及通式I所示環糊精：式中R 1 3 8 , R 2 a 8及R 3 a 1各別示Ο Η或 0 ( C Η 2 ) , S 0 3 Η ； 唯其先決條件爲R 1 1中至少有一個示 〇(C Η 2 ) , S 0 3 Η ； 或其藥學上可接受之鹼金屬鹽。 2 .如申請專利範圍第1項之組成物，其中，通式I 之每分子中0 ( C Η 2 ) 4 S Ο 3 Η的平均數目是在6 . 1 —6 . 9範圍內。 3 .如申請專利範圍第1或2項之組成物，其係供靜 脈內及皮下投服。 本紙張尺度適用中國國家標準（CNS ) Α4現格（210X297公釐） ---------#-- (請先聞讀背面之注意事項再填寫本頁) 、1Τ. 線 經濟部智慧財產局員工消費合作社印製 ，、 A8 B8 C8 D8 六、申請專利1¾023 · 4 .如申請-專利範菌第1或t項之—組成物，，中，通 式I所示環糊精衍生物係以佛利可那唑：環糊精衍生物之 莫耳比値爲1 : 2至1 : 7存在。 5 .如申請專利範圍第1或2項之組成物，其係爲水 中之溶液。 6 .如申請專利範圍第1或2項之組成物，其已經被 低壓凍乾。 ---------f------訂-------ii (請先閲讀背面之注意事項再填寫本頁) 經濟部智慧財產局員工消費合作社印製 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） -2- A8 sr.i? 敝 六、申請專利範圍 附件一 ： __________________________________________________________________________________________________________________________________ _______ 第87 1 069 1 8號專利申請案 中文申請專利範圍修正本 民國88年9月修正 1 ·—種用於治療撤菌感染之藥學組成物，其包含佛 利可那唑爲活性成份，以及通式I所示環糊精：式中R 1 3 8 , R 2 a 8及R 3 a 1各別示Ο Η或 0 ( C Η 2 ) , S 0 3 Η ； 唯其先決條件爲R 1 1中至少有一個示 〇(C Η 2 ) , S 0 3 Η ； 或其藥學上可接受之鹼金屬鹽。 2 .如申請專利範圍第1項之組成物，其中，通式I 之每分子中0 ( C Η 2 ) 4 S Ο 3 Η的平均數目是在6 . 1 —6 . 9範圍內。 3 .如申請專利範圍第1或2項之組成物，其係供靜 脈內及皮下投服。 本紙張尺度適用中國國家標準（CNS ) Α4現格（210X297公釐） ---------#-- (請先聞讀背面之注意事項再填寫本頁) 、1Τ. 線 經濟部智慧財產局員工消費合作社印製
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9713149.4A GB9713149D0 (en) | 1997-06-21 | 1997-06-21 | Pharmaceutical formulations |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW406023B true TW406023B (en) | 2000-09-21 |
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| TW087106918A TW406023B (en) | 1997-06-21 | 1998-05-05 | Pharmaceutical formulations containing voriconazole |
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| US20050176696A1 (en) * | 2003-12-08 | 2005-08-11 | Regents Of The University Of Arizona | Synergistic anit-cancer compounds |
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| WO2013103924A2 (en) * | 2012-01-05 | 2013-07-11 | Guilford Frederick Timothy | Liposomally encapsulated reduced glutathione for management of cancer, including with other pharmaceutical compositions |
| US8853248B2 (en) | 2012-04-05 | 2014-10-07 | Hubert Maehr | (1,2,3-triazolyl)sulfonyl derivatives |
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| ES2780363T3 (es) | 2013-01-11 | 2020-08-25 | Xellia Pharmaceuticals Aps | Complejos de inclusión de voriconazol |
| WO2014182368A2 (en) | 2013-03-14 | 2014-11-13 | Fresenius Kabi Usa, Llc | Voriconazole formulations |
| GB201312737D0 (en) | 2013-07-17 | 2013-08-28 | Univ Greenwich | Cyclodextrin |
| CN103690968A (zh) * | 2013-11-21 | 2014-04-02 | 石药集团中奇制药技术（石家庄）有限公司 | 一种伏立康唑组合物及其制备方法 |
| PT109117B (pt) * | 2016-01-28 | 2019-02-01 | Hovione Farm Sa | Complexação de ingredientes ativos farmacêuticos |
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| US11040958B2 (en) | 2017-02-17 | 2021-06-22 | Wuhan Ll Science And Technology Development Co., Ltd. | Triazole antimicrobial derivative, pharmaceutical composition and use thereof |
| CN113750034A (zh) * | 2020-06-05 | 2021-12-07 | 中南大学湘雅三医院 | 耳用温敏凝胶及其制备方法 |
| CN116570558B (zh) * | 2023-06-21 | 2023-12-26 | 广州仁恒医药科技股份有限公司 | 一种伏立康唑眼用纳米缓释组合物及其制备方法和应用 |
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-
1997
- 1997-06-21 GB GBGB9713149.4A patent/GB9713149D0/en active Pending
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1998
- 1998-02-06 UA UA99126910A patent/UA57083C2/uk unknown
- 1998-05-05 TW TW087106918A patent/TW406023B/zh not_active IP Right Cessation
- 1998-06-02 WO PCT/EP1998/003477 patent/WO1998058677A1/en not_active Ceased
- 1998-06-02 SI SI9830469T patent/SI1001813T1/xx unknown
- 1998-06-02 EA EA199900937A patent/EA001924B1/ru not_active IP Right Cessation
- 1998-06-02 DK DK98930793T patent/DK1001813T3/da active
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- 1998-06-02 NZ NZ501066A patent/NZ501066A/xx not_active IP Right Cessation
- 1998-06-02 PL PL337692A patent/PL191295B1/pl unknown
- 1998-06-02 HU HU0003323A patent/HU228338B1/hu unknown
- 1998-06-02 EP EP98930793.9A patent/EP1001813B8/en not_active Expired - Lifetime
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- 1998-06-02 AT AT98930793T patent/ATE238812T1/de active
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- 1998-06-02 KR KR10-1999-7012034A patent/KR100372988B1/ko not_active Expired - Lifetime
- 1998-06-02 US US09/402,289 patent/US6632803B1/en not_active Expired - Lifetime
- 1998-06-02 CA CA002295035A patent/CA2295035C/en not_active Expired - Lifetime
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- 1998-06-02 CN CN98806446A patent/CN1125653C/zh not_active Expired - Lifetime
- 1998-06-02 JP JP11503686A patent/JP2000513029A/ja not_active Withdrawn
- 1998-06-02 AU AU81104/98A patent/AU724799B2/en not_active Expired
- 1998-06-10 PA PA19988453201A patent/PA8453201A1/es unknown
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- 1998-06-17 DZ DZ980133A patent/DZ2523A1/xx active
- 1998-06-17 MA MA25117A patent/MA26508A1/fr unknown
- 1998-06-17 TN TNTNSN98090A patent/TNSN98090A1/fr unknown
- 1998-06-18 AP APAP/P/1998/001268A patent/AP912A/en active
- 1998-06-18 AR ARP980102924A patent/AR015900A1/es active IP Right Grant
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1999
- 1999-11-12 NO NO19995565A patent/NO313125B1/no not_active IP Right Cessation
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2002
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