CA2396380C - Improved pharmaceutical compositions for poorly soluble drugs - Google Patents
Improved pharmaceutical compositions for poorly soluble drugs Download PDFInfo
- Publication number
- CA2396380C CA2396380C CA2396380A CA2396380A CA2396380C CA 2396380 C CA2396380 C CA 2396380C CA 2396380 A CA2396380 A CA 2396380A CA 2396380 A CA2396380 A CA 2396380A CA 2396380 C CA2396380 C CA 2396380C
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- Prior art keywords
- pharmaceutical composition
- suspension
- composition according
- drug
- dispersion
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 239000004571 lime Substances 0.000 description 1
- 229940037627 magnesium lauryl sulfate Drugs 0.000 description 1
- HBNDBUATLJAUQM-UHFFFAOYSA-L magnesium;dodecyl sulfate Chemical compound [Mg+2].CCCCCCCCCCCCOS([O-])(=O)=O.CCCCCCCCCCCCOS([O-])(=O)=O HBNDBUATLJAUQM-UHFFFAOYSA-L 0.000 description 1
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- 238000002844 melting Methods 0.000 description 1
- 239000001525 mentha piperita l. herb oil Substances 0.000 description 1
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 1
- 229940117841 methacrylic acid copolymer Drugs 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
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- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
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- 239000000133 nasal decongestant Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
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- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
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- 229940126409 proton pump inhibitor Drugs 0.000 description 1
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- 239000004208 shellac Substances 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229940080313 sodium starch Drugs 0.000 description 1
- 239000007909 solid dosage form Substances 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- 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
- A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
- A61K9/146—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic macromolecular compounds
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
-
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4866—Organic macromolecular compounds
Landscapes
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AUPQ4854 | 1999-12-23 | ||
| AUPQ4854A AUPQ485499A0 (en) | 1999-12-23 | 1999-12-23 | Improved pharmaceutical compositions for poorly soluble drugs |
| AUPQ7450A AUPQ745000A0 (en) | 2000-05-12 | 2000-05-12 | Improved pharmaceutical compositions for poorly soluble drugs |
| AUPQ7450 | 2000-05-12 | ||
| PCT/AU2000/001592 WO2001047492A1 (en) | 1999-12-23 | 2000-12-22 | Improved pharmaceutical compositions for poorly soluble drugs |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2396380A1 CA2396380A1 (en) | 2001-07-05 |
| CA2396380C true CA2396380C (en) | 2015-04-21 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2396380A Expired - Lifetime CA2396380C (en) | 1999-12-23 | 2000-12-22 | Improved pharmaceutical compositions for poorly soluble drugs |
Country Status (8)
| Country | Link |
|---|---|
| US (3) | US20030086976A1 (cg-RX-API-DMAC7.html) |
| EP (2) | EP2415462A1 (cg-RX-API-DMAC7.html) |
| JP (2) | JP5159012B2 (cg-RX-API-DMAC7.html) |
| AU (2) | AU782469B2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2396380C (cg-RX-API-DMAC7.html) |
| ES (1) | ES2398643T3 (cg-RX-API-DMAC7.html) |
| PT (1) | PT1239831E (cg-RX-API-DMAC7.html) |
| WO (1) | WO2001047492A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (58)
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| US6248363B1 (en) * | 1999-11-23 | 2001-06-19 | Lipocine, Inc. | Solid carriers for improved delivery of active ingredients in pharmaceutical compositions |
| US20030236236A1 (en) * | 1999-06-30 | 2003-12-25 | Feng-Jing Chen | Pharmaceutical compositions and dosage forms for administration of hydrophobic drugs |
| JP5159012B2 (ja) * | 1999-12-23 | 2013-03-06 | メイン・ファ−マ・インタ−ナショナル・プロプライエタリ−・リミテッド | 不良溶解性の薬物に対する改良された医薬組成物 |
| GB0012448D0 (en) | 2000-05-24 | 2000-07-12 | Astrazeneca Ab | New process |
| DE10026698A1 (de) | 2000-05-30 | 2001-12-06 | Basf Ag | Selbstemulgierende Wirkstoffformulierung und Verwendung dieser Formulierung |
| GB0015239D0 (en) * | 2000-06-21 | 2000-08-16 | Biochemie Gmbh | Organic compounds |
| GB0104752D0 (en) * | 2001-02-27 | 2001-04-18 | Astrazeneca Ab | Pharmaceutical compositions |
| MXPA03011935A (es) * | 2001-06-22 | 2004-03-26 | Pfizer Prod Inc | Composiciones farmaceuticas que contienen conjuntos de polimero y farmaco. |
| KR100664822B1 (ko) | 2002-02-01 | 2007-01-04 | 화이자 프로덕츠 인코포레이티드 | 변형된 분무-건조 장치를 이용한 균질한 분무-건조된 고체비결정성 약물 분산액의 제조 방법 |
| AU2003290060A1 (en) * | 2002-12-17 | 2004-07-09 | Abbott Gmbh & Co. Kg | Formulation comprising fenofibric acid, a physiologically acceptable salt or derivative thereof |
| US20080051411A1 (en) * | 2002-12-17 | 2008-02-28 | Cink Russell D | Salts of Fenofibric Acid and Pharmaceutical Formulations Thereof |
| US20040115287A1 (en) * | 2002-12-17 | 2004-06-17 | Lipocine, Inc. | Hydrophobic active agent compositions and methods |
| US7259186B2 (en) * | 2002-12-17 | 2007-08-21 | Abbott Laboratories | Salts of fenofibric acid and pharmaceutical formulations thereof |
| CL2004001884A1 (es) * | 2003-08-04 | 2005-06-03 | Pfizer Prod Inc | Procedimiento de secado por pulverizacion para la formacion de dispersiones solidas amorfas de un farmaco y polimeros. |
| US8377952B2 (en) | 2003-08-28 | 2013-02-19 | Abbott Laboratories | Solid pharmaceutical dosage formulation |
| US8025899B2 (en) | 2003-08-28 | 2011-09-27 | Abbott Laboratories | Solid pharmaceutical dosage form |
| US20060003002A1 (en) * | 2003-11-03 | 2006-01-05 | Lipocine, Inc. | Pharmaceutical compositions with synchronized solubilizer release |
| US7507823B2 (en) | 2004-05-06 | 2009-03-24 | Bristol-Myers Squibb Company | Process of making aripiprazole particles |
| US20080152714A1 (en) * | 2005-04-08 | 2008-06-26 | Yi Gao | Pharmaceutical Formulations |
| JP2007308480A (ja) * | 2006-04-20 | 2007-11-29 | Shin Etsu Chem Co Ltd | 腸溶性固体分散体を含んでなる固形製剤 |
| US20070275052A1 (en) * | 2006-05-24 | 2007-11-29 | Glenmark Pharmaceuticals Limited | Pharmaceutical compositions containing sterol inhibitors |
| MX2009000035A (es) * | 2006-06-26 | 2009-05-28 | Mutual Pharmaceutical Co | Formulaciones de agente activo, procedimientos de preparacion y procedimientos de uso. |
| US8946200B2 (en) * | 2006-11-02 | 2015-02-03 | Southwest Research Institute | Pharmaceutically active nanosuspensions |
| KR100954828B1 (ko) * | 2006-12-22 | 2010-04-27 | 주식회사유한양행 | 레바프라잔 함유 고체분산체 및 그의 제조방법 |
| EP2134327A1 (en) * | 2007-03-13 | 2009-12-23 | Sandoz AG | Pharmaceutical compositions of poorly soluble drugs |
| US8404850B2 (en) * | 2008-03-13 | 2013-03-26 | Southwest Research Institute | Bis-quaternary pyridinium-aldoxime salts and treatment of exposure to cholinesterase inhibitors |
| CA2718416C (en) * | 2008-03-13 | 2018-01-02 | Mallinckrodt Inc. | Multi-function, foot-activated controller for imaging system |
| JP2011516612A (ja) * | 2008-04-15 | 2011-05-26 | シェーリング コーポレイション | 好ましくはポサコナゾールおよびｈｐｍｃａｓを含む固体分散物中の経口用薬学的組成物 |
| CA2720851A1 (en) * | 2008-04-15 | 2009-10-22 | Schering Corporation | Oral pharmaceutical compositions in a molecular solid dispersion |
| US8722706B2 (en) * | 2008-08-15 | 2014-05-13 | Southwest Research Institute | Two phase bioactive formulations of bis-quaternary pyridinium oxime sulfonate salts |
| US8309134B2 (en) * | 2008-10-03 | 2012-11-13 | Southwest Research Institute | Modified calcium phosphate nanoparticle formation |
| US20100159010A1 (en) * | 2008-12-24 | 2010-06-24 | Mutual Pharmaceutical Company, Inc. | Active Agent Formulations, Methods of Making, and Methods of Use |
| US11304960B2 (en) | 2009-01-08 | 2022-04-19 | Chandrashekar Giliyar | Steroidal compositions |
| AR077975A1 (es) | 2009-08-28 | 2011-10-05 | Irm Llc | Derivados de pirazol pirimidina y composiciones como inhibidores de cinasa de proteina |
| US9028873B2 (en) * | 2010-02-08 | 2015-05-12 | Southwest Research Institute | Nanoparticles for drug delivery to the central nervous system |
| US9034858B2 (en) | 2010-11-30 | 2015-05-19 | Lipocine Inc. | High-strength testosterone undecanoate compositions |
| US20180153904A1 (en) | 2010-11-30 | 2018-06-07 | Lipocine Inc. | High-strength testosterone undecanoate compositions |
| US9358241B2 (en) | 2010-11-30 | 2016-06-07 | Lipocine Inc. | High-strength testosterone undecanoate compositions |
| US20120148675A1 (en) | 2010-12-10 | 2012-06-14 | Basawaraj Chickmath | Testosterone undecanoate compositions |
| PE20141994A1 (es) * | 2011-11-23 | 2014-12-24 | Novartis Ag | Formulaciones farmaceuticas |
| US9650851B2 (en) | 2012-06-18 | 2017-05-16 | Schlumberger Technology Corporation | Autonomous untethered well object |
| MX366829B (es) * | 2012-06-21 | 2019-07-25 | Mayne Pharma Int Pty Ltd | Composiciones y formas de dosificacion de itraconazol y metodos de uso de las mismas. |
| US9192609B2 (en) * | 2013-04-17 | 2015-11-24 | Hedgepath Pharmaceuticals, Inc. | Treatment and prognostic monitoring of proliferation disorders using hedgehog pathway inhibitors |
| EP2837391B1 (en) | 2013-08-12 | 2017-05-10 | Shin-Etsu Chemical Co., Ltd. | Hypromellose acetate succinate for use as hot-melt extrusion carrier, hot-melt extrusion composition, and method for producing hot-melt extrudate |
| CN104644557B (zh) * | 2013-11-22 | 2017-10-31 | 上海宣泰医药科技有限公司 | 卟啉铁固体分散体及其制备方法 |
| US20170246187A1 (en) | 2014-08-28 | 2017-08-31 | Lipocine Inc. | (17-ß)-3-OXOANDROST-4-EN-17-YL TRIDECANOATE COMPOSITIONS AND METHODS OF THEIR PREPARATION AND USE |
| US9498485B2 (en) | 2014-08-28 | 2016-11-22 | Lipocine Inc. | Bioavailable solid state (17-β)-hydroxy-4-androsten-3-one esters |
| US12133911B2 (en) | 2015-06-09 | 2024-11-05 | Capsugel Belgium Nv | Formulations to achieve rapid dissolution of drug from spray-dried dispersions in capsules |
| WO2016205423A2 (en) | 2015-06-15 | 2016-12-22 | Lipocine Inc. | Composition and method for oral delivery of androgen prodrugs |
| US11559530B2 (en) | 2016-11-28 | 2023-01-24 | Lipocine Inc. | Oral testosterone undecanoate therapy |
| AU2018210141A1 (en) * | 2017-01-20 | 2019-08-29 | Constellation Pharmaceuticals, Inc. | Solid dispersions of (R)-N-((4-methoxy-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-2-methyl-1-(1-(1-(2,2,2-trifluoroethyl)piperidin-4-yl)ethyl)-1H-indole-3-carboxamide |
| AU2018321287A1 (en) | 2017-08-20 | 2020-04-02 | University Of Connecticut | Azole analogues and methods of use thereof |
| JP2021531348A (ja) | 2018-07-20 | 2021-11-18 | リポシン，インク． | 肝臓病 |
| WO2020159562A1 (en) | 2019-01-29 | 2020-08-06 | Slayback Pharma Llc | Pharmaceutical compositions of posaconazole |
| US11318107B2 (en) | 2019-02-22 | 2022-05-03 | Avior, Inc. | Pharmaceutical active-containing film delivery device for oral transmucosal administration |
| US12435067B2 (en) | 2019-08-09 | 2025-10-07 | University Of Connecticut | Truncated itraconazole analogues and methods of use thereof |
| AU2020336765A1 (en) * | 2019-08-28 | 2022-03-24 | Shenzhen Chipscreen Biosciences Co., Ltd. | Chidamide pharmaceutical composition, preparation method therefor and application thereof |
| WO2021226166A1 (en) | 2020-05-07 | 2021-11-11 | Liang Guibai | Prodrug of itraconazole and use thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02167219A (ja) * | 1988-12-20 | 1990-06-27 | Fujisawa Pharmaceut Co Ltd | 固体分散体の製造方法 |
| JP3110794B2 (ja) | 1991-06-05 | 2000-11-20 | ユーシービージャパン株式会社 | １，４−ジヒドロピリジン誘導体を含有する製剤 |
| US5340591A (en) * | 1992-01-24 | 1994-08-23 | Fujisawa Pharmaceutical Co., Ltd. | Method of producing a solid dispersion of the sparingly water-soluble drug, nilvadipine |
| PH30929A (en) * | 1992-09-03 | 1997-12-23 | Janssen Pharmaceutica Nv | Beads having a core coated with an antifungal and a polymer. |
| DE69628276T2 (de) * | 1995-07-26 | 2004-04-08 | Kyowa Hakko Kogyo Co., Ltd. | Zubereitung von xanthinderivaten als feste dispersion |
| ATE255883T1 (de) * | 1996-05-20 | 2003-12-15 | Janssen Pharmaceutica Nv | Fungizide mittel mit verbesserter bioverfügbarkeit |
| WO1998000113A1 (en) * | 1996-06-28 | 1998-01-08 | Schering Corporation | Solid solution of an antifungal agent with enhanced bioavailability |
| EP0901786B1 (en) * | 1997-08-11 | 2007-06-13 | Pfizer Products Inc. | Solid pharmaceutical dispersions with enhanced bioavailability |
| BR9814729A (pt) * | 1997-12-31 | 2002-01-08 | Choongwae Pharma Corp | Método e composição de uma preparação oral de itraconazol |
| KR100336090B1 (ko) * | 1998-06-27 | 2002-05-27 | 윤승원 | 오일, 지방산 또는 이들의 혼합물을 함유한 난용성 약물의 고형분산제제 |
| DE19843904A1 (de) * | 1998-09-24 | 2000-03-30 | Basf Ag | Feste Dosierungsform mit polymerem Bindemittel |
| EP1058539A1 (en) * | 1999-01-06 | 2000-12-13 | Korea Research Institute Of Chemical Technology | Method of preparing pharmaceutical active ingredient comprising water-insoluble drug and pharmaceutical composition for oral administration comprising the same |
| DE60039379D1 (de) * | 1999-02-10 | 2008-08-21 | Pfizer Prod Inc | Pharmazeutische feste Dispersionen |
| JP5159012B2 (ja) * | 1999-12-23 | 2013-03-06 | メイン・ファ−マ・インタ−ナショナル・プロプライエタリ−・リミテッド | 不良溶解性の薬物に対する改良された医薬組成物 |
-
2000
- 2000-12-22 JP JP2001548087A patent/JP5159012B2/ja not_active Expired - Fee Related
- 2000-12-22 CA CA2396380A patent/CA2396380C/en not_active Expired - Lifetime
- 2000-12-22 PT PT986890T patent/PT1239831E/pt unknown
- 2000-12-22 EP EP20110187961 patent/EP2415462A1/en not_active Withdrawn
- 2000-12-22 WO PCT/AU2000/001592 patent/WO2001047492A1/en not_active Ceased
- 2000-12-22 AU AU72529/00A patent/AU782469B2/en not_active Expired
- 2000-12-22 ES ES00986890T patent/ES2398643T3/es not_active Expired - Lifetime
- 2000-12-22 AU AU23318/01A patent/AU2331801A/en not_active Abandoned
- 2000-12-22 EP EP00986890A patent/EP1239831B1/en not_active Expired - Lifetime
-
2002
- 2002-06-21 US US10/175,883 patent/US20030086976A1/en not_active Abandoned
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2003
- 2003-06-16 US US10/461,503 patent/US6881745B2/en not_active Expired - Lifetime
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2007
- 2007-06-15 US US11/763,578 patent/US8771739B2/en not_active Expired - Lifetime
-
2012
- 2012-07-17 JP JP2012158751A patent/JP2012236837A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP5159012B2 (ja) | 2013-03-06 |
| US8771739B2 (en) | 2014-07-08 |
| WO2001047492A1 (en) | 2001-07-05 |
| JP2012236837A (ja) | 2012-12-06 |
| US20080260835A1 (en) | 2008-10-23 |
| EP1239831B1 (en) | 2012-10-31 |
| AU2331801A (en) | 2001-07-09 |
| ES2398643T3 (es) | 2013-03-20 |
| AU7252900A (en) | 2001-06-28 |
| CA2396380A1 (en) | 2001-07-05 |
| EP2415462A1 (en) | 2012-02-08 |
| PT1239831E (pt) | 2013-01-23 |
| US6881745B2 (en) | 2005-04-19 |
| EP1239831A1 (en) | 2002-09-18 |
| JP2003518483A (ja) | 2003-06-10 |
| EP1239831A4 (en) | 2009-07-22 |
| US20030086976A1 (en) | 2003-05-08 |
| US20030225104A1 (en) | 2003-12-04 |
| AU782469B2 (en) | 2005-08-04 |
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