DE69916522T2 - Verfahren zur Herstellung wasserdispergierbare Sterol Formulierungen - Google Patents
Verfahren zur Herstellung wasserdispergierbare Sterol Formulierungen Download PDFInfo
- Publication number
- DE69916522T2 DE69916522T2 DE69916522T DE69916522T DE69916522T2 DE 69916522 T2 DE69916522 T2 DE 69916522T2 DE 69916522 T DE69916522 T DE 69916522T DE 69916522 T DE69916522 T DE 69916522T DE 69916522 T2 DE69916522 T2 DE 69916522T2
- Authority
- DE
- Germany
- Prior art keywords
- sitosterol
- water
- oryzanol
- dispersible
- surfactant
- 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
Links
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- 239000008172 hydrogenated vegetable oil Substances 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 229940071826 hydroxyethyl cellulose Drugs 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 229940071676 hydroxypropylcellulose Drugs 0.000 description 1
- 239000005414 inactive ingredient Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 229940037627 magnesium lauryl sulfate Drugs 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229940099273 magnesium trisilicate Drugs 0.000 description 1
- 229910000386 magnesium trisilicate Inorganic materials 0.000 description 1
- 235000019793 magnesium trisilicate Nutrition 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
- 229940035034 maltodextrin Drugs 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 229960002900 methylcellulose Drugs 0.000 description 1
- 235000010981 methylcellulose Nutrition 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
- 239000006072 paste Substances 0.000 description 1
- 235000014594 pastries Nutrition 0.000 description 1
- 229960000502 poloxamer Drugs 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 229940116317 potato starch Drugs 0.000 description 1
- 229920003124 powdered cellulose Polymers 0.000 description 1
- 235000019814 powdered cellulose Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical class O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000015500 sitosterol Nutrition 0.000 description 1
- NLQLSVXGSXCXFE-UHFFFAOYSA-N sitosterol Natural products CC=C(/CCC(C)C1CC2C3=CCC4C(C)C(O)CCC4(C)C3CCC2(C)C1)C(C)C NLQLSVXGSXCXFE-UHFFFAOYSA-N 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229940080313 sodium starch Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- LGJMUZUPVCAVPU-HRJGVYIJSA-N stigmastanol Chemical compound C([C@@H]1CC2)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]2(C)CC1 LGJMUZUPVCAVPU-HRJGVYIJSA-N 0.000 description 1
- HCXVJBMSMIARIN-PHZDYDNGSA-N stigmasterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)/C=C/[C@@H](CC)C(C)C)[C@@]1(C)CC2 HCXVJBMSMIARIN-PHZDYDNGSA-N 0.000 description 1
- 235000016831 stigmasterol Nutrition 0.000 description 1
- 229940032091 stigmasterol Drugs 0.000 description 1
- BFDNMXAIBMJLBB-UHFFFAOYSA-N stigmasterol Natural products CCC(C=CC(C)C1CCCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)C BFDNMXAIBMJLBB-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000005019 zein Substances 0.000 description 1
- 229940093612 zein Drugs 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/575—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
-
- 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
- A61K9/145—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 compounds
-
- 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
- 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
- A61K9/1617—Organic compounds, e.g. phospholipids, fats
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/38—Drugs for disorders of the endocrine system of the suprarenal hormones
- A61P5/42—Drugs for disorders of the endocrine system of the suprarenal hormones for decreasing, blocking or antagonising the activity of mineralocorticosteroids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/38—Drugs for disorders of the endocrine system of the suprarenal hormones
- A61P5/46—Drugs for disorders of the endocrine system of the suprarenal hormones for decreasing, blocking or antagonising the activity of glucocorticosteroids
Landscapes
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Steroid Compounds (AREA)
- Seeds, Soups, And Other Foods (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/025,952 US6110502A (en) | 1998-02-19 | 1998-02-19 | Method for producing water dispersible sterol formulations |
| US25952 | 1998-02-19 | ||
| US185788 | 1998-11-04 | ||
| US09/185,788 US6054144A (en) | 1998-02-19 | 1998-11-04 | Method for producing water dispersible sterol formulations |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69916522D1 DE69916522D1 (de) | 2004-05-27 |
| DE69916522T2 true DE69916522T2 (de) | 2005-07-21 |
Family
ID=26700515
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69916522T Expired - Lifetime DE69916522T2 (de) | 1998-02-19 | 1999-02-18 | Verfahren zur Herstellung wasserdispergierbare Sterol Formulierungen |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP0947197B1 (enExample) |
| JP (1) | JPH11313644A (enExample) |
| CN (1) | CN1161123C (enExample) |
| AT (1) | ATE264683T1 (enExample) |
| AU (1) | AU760314B2 (enExample) |
| BR (1) | BR9902325A (enExample) |
| CZ (1) | CZ298506B6 (enExample) |
| DE (1) | DE69916522T2 (enExample) |
| DK (1) | DK0947197T3 (enExample) |
| ES (1) | ES2216439T3 (enExample) |
| HU (1) | HUP9900434A2 (enExample) |
| IN (1) | IN185730B (enExample) |
| NO (1) | NO990747L (enExample) |
| NZ (1) | NZ334189A (enExample) |
| PL (1) | PL192906B1 (enExample) |
| PT (1) | PT947197E (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE512958C2 (sv) * | 1998-04-30 | 2000-06-12 | Triple Crown Ab | Kolesterolsänkande komposition innehållande beta-sitosterol och/eller beta-sitostanol samt förfarande för dess framställning |
| US6123978A (en) | 1998-08-31 | 2000-09-26 | Mcneil-Ppc, Inc. | Stable salad dressings |
| US6376481B2 (en) * | 1998-09-02 | 2002-04-23 | Mcneil-Ppc, Inc. | Sterol esters in tableted solid dosage forms |
| US6677327B1 (en) * | 1999-11-24 | 2004-01-13 | Archer-Daniels-Midland Company | Phytosterol and phytostanol compositions |
| GB0021498D0 (en) | 2000-09-01 | 2000-10-18 | Novartis Nutrition Ag | New formulation |
| AU2005234649B2 (en) * | 2000-09-01 | 2008-01-17 | Forbes Medi-Tech, Inc. | Water-dispersible encapsulated sterols |
| KR20020026053A (ko) | 2000-09-30 | 2002-04-06 | 노승권 | 음료용 식물성 스테롤의 분산방법 및 이를 함유하는 음료 |
| GB0104074D0 (en) * | 2001-02-19 | 2001-04-04 | Novartis Ag | New composition |
| US20030003131A1 (en) * | 2001-06-22 | 2003-01-02 | Matthew Dyer | Method for manufacture of free-flowing powder containing water-dispersible sterols |
| ATE541569T1 (de) | 2001-07-24 | 2012-02-15 | Cargill Inc | Verfahren zur isolation von phenolischen verbindungen |
| JP2005520508A (ja) * | 2002-03-20 | 2005-07-14 | ユージーン サイエンス インコーポレイテッド | 植物ステロールと乳化剤の混合粉末及びその製造方法 |
| US6623780B1 (en) | 2002-03-26 | 2003-09-23 | Cargill, Inc. | Aqueous dispersible sterol product |
| WO2003086108A1 (en) * | 2002-04-10 | 2003-10-23 | Archer-Daniels-Midland Company | Hydrothermically processed compositions containing phytosterols |
| DK1549159T3 (da) | 2002-06-12 | 2009-03-02 | Coca Cola Co | Drikkevarer indeholdende plantesteroler |
| US7306819B2 (en) | 2002-06-12 | 2007-12-11 | The Coca-Cola Company | Beverages containing plant sterols |
| US7732000B2 (en) | 2002-06-20 | 2010-06-08 | General Mills, Inc. | Food intermediate having sequestered phytosteryl esters in a polysaccharide matrix |
| US20060035009A1 (en) * | 2004-08-10 | 2006-02-16 | Kraft Foods Holdings, Inc. | Compositions and processes for water-dispersible phytosterols and phytostanols |
| US20080206407A1 (en) * | 2005-01-14 | 2008-08-28 | Veldhuizen Yvonne Susanna J | Sachets Comprising Plant Sterol |
| DE102005008445A1 (de) * | 2005-02-24 | 2006-08-31 | Cognis Ip Management Gmbh | Zuckerhaltige Sterolfeststoffdispersionen |
| DE102005039835A1 (de) * | 2005-08-23 | 2007-03-01 | Cognis Ip Management Gmbh | Pulverförmige Sterolformulierungen mit Kolloidbildnern |
| CN111529500B (zh) * | 2020-06-28 | 2021-09-24 | 江西谷物源食品有限公司 | 一种提高谷维素溶解度的药物组合物及其制备方法 |
| CN112618665B (zh) * | 2020-12-19 | 2022-06-14 | 杭州益品新五丰药业有限公司 | 一种提高免疫反应的糠甾醇-谷维素联合用药制剂 |
| CN118252251A (zh) * | 2022-12-28 | 2024-06-28 | 丰益(上海)生物技术研发中心有限公司 | 含植物甾醇酯的组合物及其制备方法及食品 |
| CN120754308A (zh) * | 2025-07-21 | 2025-10-10 | 暨南大学 | 一种多功能油凝胶伤口敷料及其制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3881005A (en) * | 1973-08-13 | 1975-04-29 | Lilly Co Eli | Pharmaceutical dispersible powder of sitosterols and a method for the preparation thereof |
| US4195084A (en) * | 1977-01-07 | 1980-03-25 | Eli Lilly And Company | Taste-stable aqueous pharmaceutical suspension of tall oil sitosterols and a method for the preparation thereof |
| DE3829643A1 (de) * | 1988-09-01 | 1990-03-15 | Roecar Holdings Nv | Phyto- und zoosterole und deren derivate mit verbesserter wasserloeslichkeit |
| DE59004337D1 (de) * | 1989-07-21 | 1994-03-03 | Marigen Sa | Sterole, deren fettsäureester und glucoside; verfahren zu ihrer herstellung; spontan dispergierbare mittel mit diesen verbindungen, sowie ihre verwendung zur behandlung von tumoren. |
| CH681153A5 (de) * | 1991-01-28 | 1993-01-29 | Marigen S.A. | Neue sterolester- und sterolphosphorverbindungen. |
| EP0594612B2 (en) * | 1991-05-03 | 2010-02-24 | Raisio Nutrition Ltd. | Process for the preparation of a substance comprising a beta-sitostanol fatty acid ester or a mixture thereof |
-
1999
- 1999-02-10 IN IN101CA1999 patent/IN185730B/en unknown
- 1999-02-15 NZ NZ334189A patent/NZ334189A/xx unknown
- 1999-02-16 JP JP11036991A patent/JPH11313644A/ja active Pending
- 1999-02-17 AU AU17358/99A patent/AU760314B2/en not_active Ceased
- 1999-02-18 ES ES99301209T patent/ES2216439T3/es not_active Expired - Lifetime
- 1999-02-18 AT AT99301209T patent/ATE264683T1/de active
- 1999-02-18 PL PL331546A patent/PL192906B1/pl not_active IP Right Cessation
- 1999-02-18 PT PT99301209T patent/PT947197E/pt unknown
- 1999-02-18 EP EP99301209A patent/EP0947197B1/en not_active Expired - Lifetime
- 1999-02-18 BR BR9902325-3A patent/BR9902325A/pt not_active Application Discontinuation
- 1999-02-18 DE DE69916522T patent/DE69916522T2/de not_active Expired - Lifetime
- 1999-02-18 DK DK99301209T patent/DK0947197T3/da active
- 1999-02-18 NO NO990747A patent/NO990747L/no not_active Application Discontinuation
- 1999-02-18 CZ CZ0054799A patent/CZ298506B6/cs not_active IP Right Cessation
- 1999-02-19 HU HU9900434A patent/HUP9900434A2/hu unknown
- 1999-02-19 CN CNB991030001A patent/CN1161123C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0947197A1 (en) | 1999-10-06 |
| HU9900434D0 (en) | 1999-04-28 |
| ATE264683T1 (de) | 2004-05-15 |
| CZ54799A3 (cs) | 1999-09-15 |
| AU760314B2 (en) | 2003-05-15 |
| ES2216439T3 (es) | 2004-10-16 |
| CZ298506B6 (cs) | 2007-10-24 |
| PL192906B1 (pl) | 2006-12-29 |
| PL331546A1 (en) | 1999-08-30 |
| NZ334189A (en) | 1999-07-29 |
| JPH11313644A (ja) | 1999-11-16 |
| IN185730B (enExample) | 2001-04-14 |
| PT947197E (pt) | 2004-08-31 |
| EP0947197B1 (en) | 2004-04-21 |
| DE69916522D1 (de) | 2004-05-27 |
| CN1232668A (zh) | 1999-10-27 |
| HUP9900434A2 (hu) | 2001-06-28 |
| CN1161123C (zh) | 2004-08-11 |
| DK0947197T3 (da) | 2004-07-26 |
| BR9902325A (pt) | 2000-04-11 |
| NO990747D0 (no) | 1999-02-18 |
| AU1735899A (en) | 2000-06-08 |
| NO990747L (no) | 1999-08-20 |
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