JP2003527319A - トルセミド多形体 - Google Patents
トルセミド多形体Info
- Publication number
- JP2003527319A JP2003527319A JP2001514958A JP2001514958A JP2003527319A JP 2003527319 A JP2003527319 A JP 2003527319A JP 2001514958 A JP2001514958 A JP 2001514958A JP 2001514958 A JP2001514958 A JP 2001514958A JP 2003527319 A JP2003527319 A JP 2003527319A
- Authority
- JP
- Japan
- Prior art keywords
- torsemide
- modified
- solvent
- mixture
- dupont
- 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.)
- Withdrawn
Links
- 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 507
- 229960005461 torasemide Drugs 0.000 title claims abstract description 449
- 238000000034 method Methods 0.000 claims abstract description 134
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 102
- 239000000203 mixture Substances 0.000 claims abstract description 73
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 65
- 239000002904 solvent Substances 0.000 claims abstract description 63
- 238000004519 manufacturing process Methods 0.000 claims abstract description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 60
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 49
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 230000004048 modification Effects 0.000 claims description 24
- 238000012986 modification Methods 0.000 claims description 24
- 238000001035 drying 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 21
- 206010030113 Oedema Diseases 0.000 claims description 21
- 239000000725 suspension Substances 0.000 claims description 19
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 17
- 238000001914 filtration Methods 0.000 claims description 16
- 239000003937 drug carrier Substances 0.000 claims description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 14
- 239000011877 solvent mixture Substances 0.000 claims description 14
- 238000003756 stirring Methods 0.000 claims description 14
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical group [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 9
- 238000001556 precipitation Methods 0.000 claims description 9
- 239000000908 ammonium hydroxide Substances 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 238000004108 freeze drying Methods 0.000 claims description 5
- 238000002329 infrared spectrum Methods 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 3
- 239000011261 inert gas Substances 0.000 claims description 3
- 238000002441 X-ray diffraction Methods 0.000 claims description 2
- 125000003158 alcohol group Chemical group 0.000 claims 2
- 229910021529 ammonia Inorganic materials 0.000 claims 2
- 238000002955 isolation Methods 0.000 claims 2
- 238000002156 mixing Methods 0.000 claims 1
- 230000001376 precipitating effect Effects 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 24
- 239000002585 base Substances 0.000 description 15
- 235000011114 ammonium hydroxide Nutrition 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 238000002411 thermogravimetry Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 238000001757 thermogravimetry curve Methods 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000000843 powder 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
- 206010020772 Hypertension Diseases 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- 101100000208 Mus musculus Orm2 gene Proteins 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 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
- 239000011707 mineral Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- -1 torsemide modified ethanol Chemical class 0.000 description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 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
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 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
- 229940066468 demadex Drugs 0.000 description 1
- 238000004807 desolvation Methods 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- 238000002050 diffraction method Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 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
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 239000002171 loop diuretic Substances 0.000 description 1
- 239000000463 material 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
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 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 (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14830599P | 1999-08-11 | 1999-08-11 | |
| US60/148,305 | 1999-08-11 | ||
| US18312700P | 2000-02-17 | 2000-02-17 | |
| US60/183,127 | 2000-02-17 | ||
| US21527300P | 2000-06-30 | 2000-06-30 | |
| US60/215,273 | 2000-06-30 | ||
| PCT/US2000/022081 WO2001010441A1 (en) | 1999-08-11 | 2000-08-11 | Torsemide polymorphs |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003527319A true JP2003527319A (ja) | 2003-09-16 |
| JP2003527319A5 JP2003527319A5 (enExample) | 2006-01-12 |
Family
ID=27386674
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001514958A Withdrawn JP2003527319A (ja) | 1999-08-11 | 2000-08-11 | トルセミド多形体 |
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 |
| 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 |
| SI20816A (sl) | 2002-08-31 |
| BG106400A (en) | 2002-08-30 |
| KR20020025217A (ko) | 2002-04-03 |
| YU9502A (sh) | 2005-06-10 |
| AU6902600A (en) | 2001-03-05 |
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