SI20816A - Polimorfi torsemid-a - Google Patents
Polimorfi torsemid-a Download PDFInfo
- Publication number
- SI20816A SI20816A SI200020037A SI200020037A SI20816A SI 20816 A SI20816 A SI 20816A SI 200020037 A SI200020037 A SI 200020037A SI 200020037 A SI200020037 A SI 200020037A SI 20816 A SI20816 A SI 20816A
- Authority
- SI
- Slovenia
- Prior art keywords
- torsemide
- modification
- solvent
- mixture
- preparation
- Prior art date
Links
- 229960005461 torasemide Drugs 0.000 title claims abstract description 416
- NGBFQHCMQULJNZ-UHFFFAOYSA-N Torsemide Chemical compound CC(C)NC(=O)NS(=O)(=O)C1=CN=CC=C1NC1=CC=CC(C)=C1 NGBFQHCMQULJNZ-UHFFFAOYSA-N 0.000 title claims abstract description 414
- 230000004048 modification Effects 0.000 claims abstract description 192
- 238000012986 modification Methods 0.000 claims abstract description 192
- 238000000034 method Methods 0.000 claims abstract description 88
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 80
- 239000002904 solvent Substances 0.000 claims abstract description 57
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 53
- 238000002360 preparation method Methods 0.000 claims abstract description 53
- 230000008569 process Effects 0.000 claims abstract description 46
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims description 74
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 49
- 239000000725 suspension Substances 0.000 claims description 45
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 42
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 26
- 238000002955 isolation Methods 0.000 claims description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- 238000001035 drying Methods 0.000 claims description 22
- 238000001914 filtration Methods 0.000 claims description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 16
- 238000003756 stirring Methods 0.000 claims description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 12
- 239000000908 ammonium hydroxide Substances 0.000 claims description 12
- 238000001556 precipitation Methods 0.000 claims description 12
- 230000009466 transformation Effects 0.000 claims description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 9
- 238000002329 infrared spectrum Methods 0.000 claims description 9
- 239000000843 powder Substances 0.000 claims description 9
- -1 torsemide compound Chemical class 0.000 claims description 9
- 238000004108 freeze drying Methods 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 239000011261 inert gas Substances 0.000 claims description 5
- 239000011877 solvent mixture Substances 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 3
- 206010030113 Oedema Diseases 0.000 claims 1
- 238000002441 X-ray diffraction Methods 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 17
- 238000000634 powder X-ray diffraction Methods 0.000 description 12
- 235000011114 ammonium hydroxide Nutrition 0.000 description 10
- 206010016807 Fluid retention Diseases 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000004566 IR spectroscopy Methods 0.000 description 8
- 206010042674 Swelling Diseases 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 230000008961 swelling Effects 0.000 description 8
- 239000003937 drug carrier Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000002411 thermogravimetry Methods 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000007707 calorimetry Methods 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000001757 thermogravimetry curve Methods 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 206010007559 Cardiac failure congestive Diseases 0.000 description 2
- 206010019280 Heart failures Diseases 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 210000003734 kidney Anatomy 0.000 description 2
- 208000017169 kidney disease Diseases 0.000 description 2
- 208000019423 liver disease Diseases 0.000 description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 2
- 239000000347 magnesium hydroxide Substances 0.000 description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 2
- 238000013507 mapping Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
- 239000013557 residual solvent Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 1
- WBDLSXCAFVEULB-UHFFFAOYSA-N acetonitrile;methylsulfinylmethane Chemical compound CC#N.CS(C)=O WBDLSXCAFVEULB-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 208000020832 chronic kidney disease Diseases 0.000 description 1
- 208000022831 chronic renal failure syndrome Diseases 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000002171 loop diuretic Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- QZIQJVCYUQZDIR-UHFFFAOYSA-N mechlorethamine hydrochloride Chemical compound Cl.ClCCN(C)CCCl QZIQJVCYUQZDIR-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 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
- A61K31/33—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- 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
- A61K31/64—Sulfonylureas, e.g. glibenclamide, tolbutamide, chlorpropamide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Details Of Garments (AREA)
- Measuring Pulse, Heart Rate, Blood Pressure Or Blood Flow (AREA)
- Pressure Welding/Diffusion-Bonding (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14830599P | 1999-08-11 | 1999-08-11 | |
| US18312700P | 2000-02-17 | 2000-02-17 | |
| US21527300P | 2000-06-30 | 2000-06-30 | |
| PCT/US2000/022081 WO2001010441A1 (en) | 1999-08-11 | 2000-08-11 | Torsemide polymorphs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SI20816A true SI20816A (sl) | 2002-08-31 |
Family
ID=27386674
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI200020037A SI20816A (sl) | 1999-08-11 | 2000-08-11 | Polimorfi torsemid-a |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US6465496B1 (enExample) |
| EP (1) | EP1207880A4 (enExample) |
| JP (1) | JP2003527319A (enExample) |
| KR (1) | KR20020025217A (enExample) |
| CN (1) | CN1378448A (enExample) |
| AU (1) | AU781461C (enExample) |
| BG (1) | BG106400A (enExample) |
| CA (1) | CA2379322A1 (enExample) |
| CZ (1) | CZ2002404A3 (enExample) |
| DE (1) | DE00957398T1 (enExample) |
| ES (1) | ES2204354T1 (enExample) |
| HK (1) | HK1046636A1 (enExample) |
| HR (1) | HRP20020120A2 (enExample) |
| HU (1) | HUP0204318A3 (enExample) |
| IL (1) | IL148031A0 (enExample) |
| LT (1) | LT5004B (enExample) |
| MX (1) | MXPA02001369A (enExample) |
| NO (1) | NO20020622L (enExample) |
| PL (1) | PL354262A1 (enExample) |
| SI (1) | SI20816A (enExample) |
| SK (1) | SK1912002A3 (enExample) |
| TR (1) | TR200200353T2 (enExample) |
| WO (1) | WO2001010441A1 (enExample) |
| YU (1) | YU9502A (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SK11632003A3 (sk) * | 2000-02-17 | 2004-04-06 | Teva Pharmaceutical Industries Ltd. | Stabilný farmaceutický prípravok obsahujúci modifikáciu II torsemidu |
| DE10013289A1 (de) * | 2000-03-17 | 2001-09-20 | Knoll Ag | Torasemid enthaltende pharmazeutische Zubereitungen |
| HRP20000162B1 (en) | 2000-03-20 | 2004-06-30 | Pliva D D | Amorphous torasemide modification |
| US20030022921A1 (en) * | 2001-02-21 | 2003-01-30 | Minutza Leibovici | Stable pharmaceutical formulation comprising torsemide modification II |
| EP1397343A1 (en) | 2001-05-31 | 2004-03-17 | Orion Corporation Fermion | Process for preparing sertraline hydrochloride polymorphic form ii |
| IN192178B (enExample) | 2001-08-03 | 2004-03-06 | Ranbaxy Lab | |
| US20030119882A1 (en) * | 2001-10-22 | 2003-06-26 | Markus Maegerlein | Solid pharmaceutical composition containing torasemide |
| ITMI20020639A1 (it) * | 2002-03-27 | 2003-09-29 | Cosma S P A | Composizioni farmaceutiche comprendenti come principio attivo 1-isopropil-3°(4-m-toluidino-3-pridil)sulfonil!-urea |
| HRP20020603B1 (en) * | 2002-07-19 | 2008-11-30 | Pliva D.D. | New process for the preparation of modification i n-(1-methylethylaminocarbonyl)-4-(3-methylphenylamino)-3-pyridinesulfonamide |
| CA2424644A1 (en) * | 2003-04-07 | 2004-10-07 | David John Mckenzie | Preparation of torasemide |
| ES2244324B1 (es) * | 2004-03-25 | 2006-11-16 | Ferrer Internacional, S.A. | Composiciones diureticas de liberacion prolongada. |
| AT500576B1 (de) * | 2004-07-28 | 2006-11-15 | Sanochemia Pharmazeutika Ag | Verfahren zur reindarstellung von kristallformen von torsemid |
| KR100845383B1 (ko) * | 2004-12-24 | 2008-07-09 | 일동제약주식회사 | 토르세미드 변형체(ⅰ)의 제조방법 |
| US20070122483A1 (en) * | 2005-11-29 | 2007-05-31 | Sharon Myers | Fluocinolone acetonide drug substance polymorphic interconversion |
| AU2014348523B2 (en) | 2013-11-15 | 2019-01-03 | Akebia Therapeutics, Inc. | Solid forms of {[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino}acetic acid, compositions, and uses thereof |
| CN105949115A (zh) * | 2016-05-26 | 2016-09-21 | 南京正科医药股份有限公司 | 一种新晶型托拉塞米 |
| CN115417810B (zh) * | 2022-09-22 | 2023-10-10 | 南京正科医药股份有限公司 | 一种托拉塞米晶型ⅰ的精制方法 |
| CN117486789A (zh) * | 2023-12-29 | 2024-02-02 | 江西中医药大学 | 一种托拉塞米共晶盐及其制备方法和应用 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US30633A (en) | 1860-11-13 | Improvement in fire-escapes | ||
| US34672A (en) | 1862-03-18 | Improved convertible boat, bridge, and tent | ||
| GB1477664A (en) | 1974-04-17 | 1977-06-22 | Christiaens Sa A | Pyridine derivatives |
| US4055650A (en) | 1974-04-17 | 1977-10-25 | A. Christiaens Societe Anonyme | Certain 4-phenoxy(or phenylthio)-3-n-acylated-sulfonamido-pyridines |
| DE3529529A1 (de) * | 1985-08-17 | 1987-02-19 | Boehringer Mannheim Gmbh | Verfahren zur herstellung einer stabilen modifikation von torasemid |
| DE3623620A1 (de) | 1986-07-12 | 1988-01-21 | Boehringer Mannheim Gmbh | Spritzfertige, waessrige, alkalische injektionsloesungen von torasemid und verfahren zu ihrer herstellung |
| HRP980532B1 (en) * | 1998-10-02 | 2005-06-30 | Pliva | Novel crystalline torasemide modification |
| US5914336A (en) * | 1998-06-02 | 1999-06-22 | Boehringer Mannheim Gmbh | Method of controlling the serum solubility of orally administered torasemide and composition relating thereto |
| US6166045A (en) * | 1998-06-02 | 2000-12-26 | Roche Diagnostics Gmbh | Torasemide of modification III |
| HRP20000162B1 (en) * | 2000-03-20 | 2004-06-30 | Pliva D D | Amorphous torasemide modification |
| CA2403382A1 (en) * | 2000-03-20 | 2001-09-27 | Teva Pharmaceutical Industries Ltd. | Novel processes for preparing torsemide intermediate |
| HRP20000328A2 (en) * | 2000-05-19 | 2002-02-28 | Pliva Farmaceutska Ind Dionik | Novel polymorph v of torasemide |
-
2000
- 2000-08-11 HR HR20020120A patent/HRP20020120A2/hr not_active Application Discontinuation
- 2000-08-11 WO PCT/US2000/022081 patent/WO2001010441A1/en not_active Ceased
- 2000-08-11 EP EP00957398A patent/EP1207880A4/en not_active Withdrawn
- 2000-08-11 DE DE0001207880T patent/DE00957398T1/de active Pending
- 2000-08-11 PL PL00354262A patent/PL354262A1/xx not_active Application Discontinuation
- 2000-08-11 HK HK02108111.5A patent/HK1046636A1/zh unknown
- 2000-08-11 AU AU69026/00A patent/AU781461C/en not_active Ceased
- 2000-08-11 TR TR2002/00353T patent/TR200200353T2/xx unknown
- 2000-08-11 KR KR1020027001867A patent/KR20020025217A/ko not_active Ceased
- 2000-08-11 MX MXPA02001369A patent/MXPA02001369A/es unknown
- 2000-08-11 US US09/638,106 patent/US6465496B1/en not_active Expired - Fee Related
- 2000-08-11 SK SK191-2002A patent/SK1912002A3/sk unknown
- 2000-08-11 CN CN00814045A patent/CN1378448A/zh active Pending
- 2000-08-11 CA CA002379322A patent/CA2379322A1/en not_active Abandoned
- 2000-08-11 SI SI200020037A patent/SI20816A/sl not_active IP Right Cessation
- 2000-08-11 CZ CZ2002404A patent/CZ2002404A3/cs unknown
- 2000-08-11 JP JP2001514958A patent/JP2003527319A/ja not_active Withdrawn
- 2000-08-11 ES ES00957398T patent/ES2204354T1/es active Pending
- 2000-08-11 IL IL14803100A patent/IL148031A0/xx unknown
- 2000-08-11 HU HU0204318A patent/HUP0204318A3/hu unknown
- 2000-08-11 YU YU9502A patent/YU9502A/sh unknown
-
2002
- 2002-02-08 NO NO20020622A patent/NO20020622L/no not_active Application Discontinuation
- 2002-02-08 BG BG106400A patent/BG106400A/xx unknown
- 2002-02-11 LT LT2002017A patent/LT5004B/lt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2204354T1 (es) | 2004-05-01 |
| US6465496B1 (en) | 2002-10-15 |
| HUP0204318A3 (en) | 2005-03-29 |
| CA2379322A1 (en) | 2001-02-15 |
| JP2003527319A (ja) | 2003-09-16 |
| NO20020622L (no) | 2002-03-14 |
| IL148031A0 (en) | 2002-09-12 |
| MXPA02001369A (es) | 2005-08-26 |
| HK1046636A1 (zh) | 2003-01-24 |
| PL354262A1 (en) | 2003-12-29 |
| NO20020622D0 (no) | 2002-02-08 |
| CZ2002404A3 (cs) | 2002-06-12 |
| EP1207880A1 (en) | 2002-05-29 |
| AU781461B2 (en) | 2005-05-26 |
| AU781461C (en) | 2006-02-23 |
| CN1378448A (zh) | 2002-11-06 |
| SK1912002A3 (en) | 2002-07-02 |
| EP1207880A4 (en) | 2004-09-01 |
| WO2001010441A1 (en) | 2001-02-15 |
| LT2002017A (en) | 2002-11-25 |
| HUP0204318A2 (en) | 2003-05-28 |
| DE00957398T1 (de) | 2004-04-15 |
| TR200200353T2 (tr) | 2002-06-21 |
| HRP20020120A2 (en) | 2003-10-31 |
| LT5004B (lt) | 2003-03-25 |
| BG106400A (en) | 2002-08-30 |
| KR20020025217A (ko) | 2002-04-03 |
| YU9502A (sh) | 2005-06-10 |
| AU6902600A (en) | 2001-03-05 |
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