AU729100B2 - Proliposome powders for inhalation stabilised by tocopherol - Google Patents
Proliposome powders for inhalation stabilised by tocopherol Download PDFInfo
- Publication number
- AU729100B2 AU729100B2 AU79456/98A AU7945698A AU729100B2 AU 729100 B2 AU729100 B2 AU 729100B2 AU 79456/98 A AU79456/98 A AU 79456/98A AU 7945698 A AU7945698 A AU 7945698A AU 729100 B2 AU729100 B2 AU 729100B2
- Authority
- AU
- Australia
- Prior art keywords
- powder according
- powder
- tocopherol
- dmpc
- dppc
- 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.)
- Ceased
Links
- 239000000843 powder Substances 0.000 title claims description 84
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 title claims description 21
- 229960001295 tocopherol Drugs 0.000 title claims description 19
- 239000011732 tocopherol Substances 0.000 title claims description 19
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 title claims description 17
- 229930003799 tocopherol Natural products 0.000 title claims description 17
- 235000010384 tocopherol Nutrition 0.000 title claims description 17
- 150000002632 lipids Chemical class 0.000 claims description 47
- 239000000203 mixture Substances 0.000 claims description 40
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol 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)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 26
- 239000002245 particle Substances 0.000 claims description 22
- KILNVBDSWZSGLL-KXQOOQHDSA-N 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC KILNVBDSWZSGLL-KXQOOQHDSA-N 0.000 claims description 20
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- OZSITQMWYBNPMW-GDLZYMKVSA-N 1,2-ditetradecanoyl-sn-glycerol-3-phosphate Chemical compound CCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCCCCCCCC OZSITQMWYBNPMW-GDLZYMKVSA-N 0.000 claims description 5
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 claims description 5
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- BPHQZTVXXXJVHI-AJQTZOPKSA-N ditetradecanoyl phosphatidylglycerol Chemical compound CCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@@H](O)CO)OC(=O)CCCCCCCCCCCCC BPHQZTVXXXJVHI-AJQTZOPKSA-N 0.000 claims description 5
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- NRJAVPSFFCBXDT-HUESYALOSA-N 1,2-distearoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC NRJAVPSFFCBXDT-HUESYALOSA-N 0.000 claims description 4
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- SNKAWJBJQDLSFF-NVKMUCNASA-N 1,2-dioleoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC SNKAWJBJQDLSFF-NVKMUCNASA-N 0.000 claims 3
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- CITHEXJVPOWHKC-UUWRZZSWSA-N 1,2-di-O-myristoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCC CITHEXJVPOWHKC-UUWRZZSWSA-N 0.000 description 13
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- IJFVSSZAOYLHEE-UHFFFAOYSA-N 2,3-di(dodecanoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CCCCCCCCCCCC(=O)OCC(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCC IJFVSSZAOYLHEE-UHFFFAOYSA-N 0.000 description 6
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- PORPENFLTBBHSG-MGBGTMOVSA-N 1,2-dihexadecanoyl-sn-glycerol-3-phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC PORPENFLTBBHSG-MGBGTMOVSA-N 0.000 description 2
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- QZXMUPATKGLZAP-DXLAUQRQSA-N [(2S)-1-hexadecanoyloxy-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxypropan-2-yl] (9Z,12Z)-octadeca-9,12-dienoate Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](OC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC)O[C@@H]1CO[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 QZXMUPATKGLZAP-DXLAUQRQSA-N 0.000 description 2
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- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
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- 229940105132 myristate Drugs 0.000 description 1
- VVGIYYKRAMHVLU-UHFFFAOYSA-N newbouldiamide Natural products CCCCCCCCCCCCCCCCCCCC(O)C(O)C(O)C(CO)NC(=O)CCCCCCCCCCCCCCCCC VVGIYYKRAMHVLU-UHFFFAOYSA-N 0.000 description 1
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- FKNXQNWAXFXVNW-BLLLJJGKSA-N procaterol Chemical compound N1C(=O)C=CC2=C1C(O)=CC=C2[C@@H](O)[C@@H](NC(C)C)CC FKNXQNWAXFXVNW-BLLLJJGKSA-N 0.000 description 1
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- 102000004169 proteins and genes Human genes 0.000 description 1
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- MIXMJCQRHVAJIO-TZHJZOAOSA-N qk4dys664x Chemical compound O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O MIXMJCQRHVAJIO-TZHJZOAOSA-N 0.000 description 1
- MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose 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[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 description 1
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- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
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- UQZIYBXSHAGNOE-XNSRJBNMSA-N stachyose 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[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO[C@@H]3[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O3)O)O2)O)O1 UQZIYBXSHAGNOE-XNSRJBNMSA-N 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
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- 235000019698 starch Nutrition 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 229930002534 steroid glycoside Natural products 0.000 description 1
- 150000008143 steroidal glycosides Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- 229950001669 tipredane Drugs 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 229960002117 triamcinolone acetonide Drugs 0.000 description 1
- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 description 1
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- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 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
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
-
- 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
- A61K9/007—Pulmonary tract; Aromatherapy
- A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
- A61K9/0075—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy for inhalation via a dry powder inhaler [DPI], e.g. comprising micronized drug mixed with lactose carrier particles
-
- 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
- A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
-
- 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
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
- A61K9/1277—Preparation processes; Proliposomes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- 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
- A61K9/19—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles lyophilised, i.e. freeze-dried, solutions or dispersions
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dispersion Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Pulmonology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Otolaryngology (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US88441997A | 1997-06-27 | 1997-06-27 | |
| US08/884419 | 1997-06-27 | ||
| PCT/SE1998/001090 WO1999000111A1 (en) | 1997-06-27 | 1998-06-08 | Proliposome powders for inhalation stabilised by tocopherol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU7945698A AU7945698A (en) | 1999-01-19 |
| AU729100B2 true AU729100B2 (en) | 2001-01-25 |
Family
ID=25384589
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU79456/98A Ceased AU729100B2 (en) | 1997-06-27 | 1998-06-08 | Proliposome powders for inhalation stabilised by tocopherol |
Country Status (18)
| Country | Link |
|---|---|
| EP (1) | EP1001749A1 (id) |
| JP (1) | JP2002510311A (id) |
| KR (1) | KR20010014163A (id) |
| CN (1) | CN1260713A (id) |
| AU (1) | AU729100B2 (id) |
| BR (1) | BR9810280A (id) |
| CA (1) | CA2295028A1 (id) |
| EE (1) | EE9900601A (id) |
| HU (1) | HUP0003207A3 (id) |
| ID (1) | ID23192A (id) |
| IL (1) | IL133478A0 (id) |
| IS (1) | IS5304A (id) |
| NO (1) | NO996439L (id) |
| NZ (1) | NZ501672A (id) |
| PL (1) | PL337723A1 (id) |
| SK (1) | SK184899A3 (id) |
| TR (1) | TR199903271T2 (id) |
| WO (1) | WO1999000111A1 (id) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030236236A1 (en) * | 1999-06-30 | 2003-12-25 | Feng-Jing Chen | Pharmaceutical compositions and dosage forms for administration of hydrophobic drugs |
| EP1138310A1 (de) * | 2000-03-28 | 2001-10-04 | Primacare S.A. | Pro-liposomen |
| EP1138311A1 (de) * | 2000-03-28 | 2001-10-04 | Primacare S.A. | Pro-liposomen |
| EP1138313A1 (de) * | 2000-03-28 | 2001-10-04 | Primacare S.A. | Pro-liposomen |
| ES2462541T3 (es) * | 2005-06-09 | 2014-05-23 | Meda Ab | Método y composición para el tratamiento de trastornos inflamatorios |
| US11304960B2 (en) | 2009-01-08 | 2022-04-19 | Chandrashekar Giliyar | Steroidal compositions |
| US9358241B2 (en) | 2010-11-30 | 2016-06-07 | Lipocine Inc. | High-strength testosterone undecanoate compositions |
| US20180153904A1 (en) | 2010-11-30 | 2018-06-07 | Lipocine Inc. | High-strength testosterone undecanoate compositions |
| US9034858B2 (en) | 2010-11-30 | 2015-05-19 | Lipocine Inc. | High-strength testosterone undecanoate compositions |
| US20120148675A1 (en) | 2010-12-10 | 2012-06-14 | Basawaraj Chickmath | Testosterone undecanoate compositions |
| WO2014180827A1 (en) * | 2013-05-06 | 2014-11-13 | Dsm Ip Assets B. V. | Powderous vitamin e formulation |
| WO2016033549A2 (en) | 2014-08-28 | 2016-03-03 | 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 |
| US20160361322A1 (en) | 2015-06-15 | 2016-12-15 | Lipocine Inc. | Composition and method for oral delivery of androgen prodrugs |
| CN105078963B (zh) * | 2015-09-29 | 2018-06-22 | 中山大学 | α-生育酚在制备治疗血吸虫病药物中的应用 |
| US11559530B2 (en) | 2016-11-28 | 2023-01-24 | Lipocine Inc. | Oral testosterone undecanoate therapy |
| AU2019308326B2 (en) | 2018-07-20 | 2025-07-31 | Lipocine Inc. | Liver disease |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996019199A1 (en) * | 1994-12-22 | 1996-06-27 | Astra Aktiebolag | Proliposome powders for inhalation |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05507090A (ja) * | 1990-05-08 | 1993-10-14 | リポサーム テクノロジー インコーポレイテッド | 直接噴霧乾燥された薬剤/脂質粉末組成物 |
-
1998
- 1998-06-08 EE EEP199900601A patent/EE9900601A/xx unknown
- 1998-06-08 KR KR1019997012234A patent/KR20010014163A/ko not_active Withdrawn
- 1998-06-08 HU HU0003207A patent/HUP0003207A3/hu unknown
- 1998-06-08 CN CN98806377A patent/CN1260713A/zh active Pending
- 1998-06-08 JP JP50548099A patent/JP2002510311A/ja active Pending
- 1998-06-08 SK SK1848-99A patent/SK184899A3/sk unknown
- 1998-06-08 TR TR1999/03271T patent/TR199903271T2/xx unknown
- 1998-06-08 WO PCT/SE1998/001090 patent/WO1999000111A1/en not_active Ceased
- 1998-06-08 CA CA002295028A patent/CA2295028A1/en not_active Abandoned
- 1998-06-08 PL PL98337723A patent/PL337723A1/xx unknown
- 1998-06-08 NZ NZ501672A patent/NZ501672A/en unknown
- 1998-06-08 AU AU79456/98A patent/AU729100B2/en not_active Ceased
- 1998-06-08 ID IDW991656A patent/ID23192A/id unknown
- 1998-06-08 EP EP98929963A patent/EP1001749A1/en not_active Withdrawn
- 1998-06-08 BR BR9810280-0A patent/BR9810280A/pt not_active IP Right Cessation
- 1998-06-08 IL IL13347898A patent/IL133478A0/xx unknown
-
1999
- 1999-12-15 IS IS5304A patent/IS5304A/is unknown
- 1999-12-23 NO NO996439A patent/NO996439L/no not_active Application Discontinuation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996019199A1 (en) * | 1994-12-22 | 1996-06-27 | Astra Aktiebolag | Proliposome powders for inhalation |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20010014163A (ko) | 2001-02-26 |
| IS5304A (is) | 1999-12-15 |
| HUP0003207A3 (en) | 2001-03-28 |
| SK184899A3 (en) | 2000-05-16 |
| CN1260713A (zh) | 2000-07-19 |
| BR9810280A (pt) | 2000-09-12 |
| NO996439L (no) | 2000-02-28 |
| TR199903271T2 (en) | 2000-08-21 |
| IL133478A0 (en) | 2001-04-30 |
| CA2295028A1 (en) | 1999-01-07 |
| AU7945698A (en) | 1999-01-19 |
| JP2002510311A (ja) | 2002-04-02 |
| NO996439D0 (no) | 1999-12-23 |
| NZ501672A (en) | 2001-06-29 |
| WO1999000111A1 (en) | 1999-01-07 |
| PL337723A1 (en) | 2000-08-28 |
| HUP0003207A2 (hu) | 2001-02-28 |
| EE9900601A (et) | 2000-08-15 |
| EP1001749A1 (en) | 2000-05-24 |
| ID23192A (id) | 2000-03-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |