SK14832000A3 - Kryštalické formy 5,6-dichlór-2-(izopropylamino)-1-(beta-l- ribofuranozyl)-1h-benzimidazolu, spôsob ich prípravy, farmaceutický prostriedok s ich obsahom a ich použitie - Google Patents
Kryštalické formy 5,6-dichlór-2-(izopropylamino)-1-(beta-l- ribofuranozyl)-1h-benzimidazolu, spôsob ich prípravy, farmaceutický prostriedok s ich obsahom a ich použitie Download PDFInfo
- Publication number
- SK14832000A3 SK14832000A3 SK1483-2000A SK14832000A SK14832000A3 SK 14832000 A3 SK14832000 A3 SK 14832000A3 SK 14832000 A SK14832000 A SK 14832000A SK 14832000 A3 SK14832000 A3 SK 14832000A3
- Authority
- SK
- Slovakia
- Prior art keywords
- ribofuranosyl
- dichloro
- isopropylamino
- benzimidazole
- powder diffraction
- Prior art date
Links
- -1 benzimidazole compound Chemical class 0.000 title claims description 17
- 230000000840 anti-viral effect Effects 0.000 title description 4
- 238000000034 method Methods 0.000 claims abstract description 33
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims description 94
- KJFBVJALEQWJBS-XUXIUFHCSA-N maribavir Chemical compound CC(C)NC1=NC2=CC(Cl)=C(Cl)C=C2N1[C@H]1O[C@@H](CO)[C@H](O)[C@@H]1O KJFBVJALEQWJBS-XUXIUFHCSA-N 0.000 claims description 61
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 58
- 239000000203 mixture Substances 0.000 claims description 56
- 239000012453 solvate Substances 0.000 claims description 50
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 39
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 claims description 26
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
- 229910002804 graphite Inorganic materials 0.000 claims description 16
- 239000010439 graphite Substances 0.000 claims description 16
- 238000002441 X-ray diffraction Methods 0.000 claims description 14
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- 150000003839 salts Chemical class 0.000 claims description 2
- VQJDOEMQZNKEMJ-KBIHSYGRSA-N (3r,4s,5r)-2-(benzimidazol-1-yl)-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)OC1N1C2=CC=CC=C2N=C1 VQJDOEMQZNKEMJ-KBIHSYGRSA-N 0.000 claims 1
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose 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)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
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- 235000019634 flavors Nutrition 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 229940100692 oral suspension Drugs 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
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- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- BTAJWXYZNWITTK-UHFFFAOYSA-L C(CC(O)(C(=O)O)CC(=O)O)(=O)[O-].[Na+].C(CC(O)(C(=O)O)CC(=O)O)(=O)O.[Cl-].[Na+].C(C(C)O)O Chemical compound C(CC(O)(C(=O)O)CC(=O)O)(=O)[O-].[Na+].C(CC(O)(C(=O)O)CC(=O)O)(=O)O.[Cl-].[Na+].C(C(C)O)O BTAJWXYZNWITTK-UHFFFAOYSA-L 0.000 description 1
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- 206010019973 Herpes virus infection Diseases 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
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- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
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- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- OJJVNLOIGPRKSI-UHFFFAOYSA-M sodium methyl 4-hydroxybenzoate benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1.COC(=O)C1=CC=C(O)C=C1 OJJVNLOIGPRKSI-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
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- 238000002560 therapeutic procedure Methods 0.000 description 1
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- XPFJYKARVSSRHE-UHFFFAOYSA-K trisodium;2-hydroxypropane-1,2,3-tricarboxylate;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound [Na+].[Na+].[Na+].OC(=O)CC(O)(C(O)=O)CC(O)=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O XPFJYKARVSSRHE-UHFFFAOYSA-K 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/052—Imidazole 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/7056—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing five-membered rings with nitrogen as a ring hetero atom
-
- 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
- A61P31/12—Antivirals
-
- 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
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Biotechnology (AREA)
- Engineering & Computer Science (AREA)
- Virology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9807354.7A GB9807354D0 (en) | 1998-04-07 | 1998-04-07 | Antiviral compound |
| PCT/EP1999/002214 WO1999051618A1 (en) | 1998-04-07 | 1999-04-01 | Novel crystalline forms of an antiviral benzimidazole compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK14832000A3 true SK14832000A3 (sk) | 2001-07-10 |
Family
ID=10829932
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1483-2000A SK14832000A3 (sk) | 1998-04-07 | 1999-04-01 | Kryštalické formy 5,6-dichlór-2-(izopropylamino)-1-(beta-l- ribofuranozyl)-1h-benzimidazolu, spôsob ich prípravy, farmaceutický prostriedok s ich obsahom a ich použitie |
Country Status (28)
| Country | Link |
|---|---|
| US (9) | US6469160B1 (et) |
| EP (1) | EP1071693B1 (et) |
| JP (1) | JP2002510703A (et) |
| KR (1) | KR20010074472A (et) |
| CN (1) | CN1303390A (et) |
| AP (1) | AP2000001947A0 (et) |
| AT (1) | ATE261452T1 (et) |
| AU (1) | AU752877B2 (et) |
| BR (1) | BR9909474A (et) |
| CA (1) | CA2327494C (et) |
| DE (1) | DE69915461T2 (et) |
| EA (1) | EA002970B1 (et) |
| EE (1) | EE04120B1 (et) |
| ES (1) | ES2216503T3 (et) |
| GB (1) | GB9807354D0 (et) |
| HR (1) | HRP20000669A2 (et) |
| HU (1) | HUP0101669A3 (et) |
| ID (1) | ID27109A (et) |
| IL (1) | IL138697A0 (et) |
| IS (1) | IS5640A (et) |
| NO (1) | NO20005005L (et) |
| NZ (1) | NZ507173A (et) |
| PL (1) | PL343397A1 (et) |
| SK (1) | SK14832000A3 (et) |
| TR (1) | TR200002860T2 (et) |
| WO (1) | WO1999051618A1 (et) |
| YU (1) | YU60900A (et) |
| ZA (1) | ZA200005153B (et) |
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| GB0008939D0 (en) * | 2000-04-11 | 2000-05-31 | Glaxo Group Ltd | Process for preparing substituted benzimidazole compounds |
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| WO2005118586A1 (en) * | 2004-06-02 | 2005-12-15 | Sandoz Ag | Meropenem intermediate in crystalline form |
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| WO2007052289A2 (en) * | 2005-07-22 | 2007-05-10 | Rubicon Research Pvt Ltd. | Novel dispersible tablet composition |
| US8188138B2 (en) * | 2005-09-21 | 2012-05-29 | 4Sc Ag | Sulphonylpyrrole hydrochloride salts as histone deacetylases inhibitors |
| EA201001799A1 (ru) * | 2005-10-31 | 2011-06-30 | Янссен Фармацевтика Н.В. | Новые способы получения пиперазинильных и диазепанильных производных бензамида |
| CA2656057C (en) * | 2006-06-16 | 2012-10-02 | H. Lundbeck A/S | Crystalline forms of 4-[2-(4-methylphenylsulfanyl)-phenyl]piperidine with combined serotonin and norepinephrine reuptake inhibition for the treatment of neuropathic pain |
| US7919598B2 (en) * | 2006-06-28 | 2011-04-05 | Bristol-Myers Squibb Company | Crystal structures of SGLT2 inhibitors and processes for preparing same |
| NZ598071A (en) * | 2006-10-27 | 2013-08-30 | Signal Pharm Llc | Uses of and pharmaceutical compositions comprising 4-[9-(tetrahydro-furan-3-yl)-8-(2,4,6-trifluoro-phenylamino)-9h-purin-2-ylamino]-cyclohexan-1-ol compounds |
| EP2085397A1 (en) * | 2008-01-21 | 2009-08-05 | Esteve Quimica, S.A. | Crystalline form of abacavir |
| US7935817B2 (en) * | 2008-03-31 | 2011-05-03 | Apotex Pharmachem Inc. | Salt form and cocrystals of adefovir dipivoxil and processes for preparation thereof |
| AR071318A1 (es) * | 2008-04-15 | 2010-06-09 | Basilea Pharmaceutica Ag | Benzhidril ester del acido (6r,7r)-7-{2-(5-amino-[1,2,4]tiadiazol-3-il)-2-[(z)-tritiloxiimino]-acetilamino}-3-[(r)-1'-terc-butoxicarbonil-2-oxo-[1,3']bipirrolidinil-(3e)-ilidenometil]-8-oxo-5-tia-1-aza-biciclo[4.2.0]oct-2-eno-2-carboxilico cristalino; su elaboracion y uso |
| US8097719B2 (en) * | 2008-07-15 | 2012-01-17 | Genesen Labs | Meropenem intermediate in novel crystalline form and a method of manufacture of meropenem |
| KR101043794B1 (ko) * | 2009-04-13 | 2011-06-27 | 청우산업 주식회사 | 황토판재로 제공되는 기능성 황토방 |
| KR101512548B1 (ko) | 2010-03-12 | 2015-04-15 | 오메로스 코포레이션 | Pde10 억제제 및 관련 조성물 및 방법 |
| MX2013002421A (es) * | 2010-09-01 | 2013-05-17 | Arena Pharm Inc | Sales no hidroscopicas de agonistas de 5-ht2c. |
| US8940707B2 (en) | 2010-10-28 | 2015-01-27 | Viropharma Incorporated | Maribavir isomers, compositions, methods of making and methods of using |
| US8541391B2 (en) | 2010-10-28 | 2013-09-24 | Viropharma Incorporated | Crystalline phases of 5,6-dichloro-2-(isopropylamino)-1-β-L-ribofuranosyl-1H-benzimidazole |
| US8546344B2 (en) | 2010-10-28 | 2013-10-01 | Viropharma Incorporated | Crystalline phases of 5,6-dichloro-2-(isopropylamino)-1-β-L-ribofuranosyl)-1H-benzimidazole |
| WO2013044816A1 (en) * | 2011-09-30 | 2013-04-04 | Sunshine Lake Pharma Co., Ltd. | Crystalline forms of azilsartan and preparation and uses thereof |
| NZ630803A (en) * | 2014-04-28 | 2016-03-31 | Omeros Corp | Optically active pde10 inhibitor |
| NZ716494A (en) | 2014-04-28 | 2017-07-28 | Omeros Corp | Processes and intermediates for the preparation of a pde10 inhibitor |
| AU2016250843A1 (en) | 2015-04-24 | 2017-10-12 | Omeros Corporation | PDE10 inhibitors and related compositions and methods |
| WO2017079678A1 (en) | 2015-11-04 | 2017-05-11 | Omeros Corporation | Solid state forms of a pde10 inhibitor |
| EP3870292A4 (en) | 2018-10-26 | 2022-11-09 | The Research Foundation for The State University of New York | COMBINATION OF SEROTONIN-SPECIFIC RESUPPUT INHIBITOR AND SEROTONIN 1A RECEPTOR PARTIAL AGONIST TO REDUCE L-DOPA-INDUCED DYSKINESIA |
| CN111303230B (zh) * | 2020-03-09 | 2021-07-13 | 中国食品药品检定研究院 | 一种黄体酮共晶物及其制备方法和用途 |
| CN119751358A (zh) | 2022-10-12 | 2025-04-04 | 武田药品工业株式会社 | 制备马立巴韦的方法 |
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| US3399987A (en) * | 1965-08-02 | 1968-09-03 | United States Borax Chem | 2-alkylaminobenzimidazoles as herbicides |
| CH443777A (de) * | 1965-08-06 | 1968-02-15 | Agripat Sa | Verfahren zum Schützen textiler Keratinfasern vor Insektenfrass und Mittel zur Durchführung dieses Verfahrens |
| US3655901A (en) * | 1970-07-30 | 1972-04-11 | Merck & Co Inc | Method of inhibiting the formation of phenylethanalamine-n-methyl transferase with 2-aminobenzimidazoles |
| SE9003151D0 (sv) * | 1990-10-02 | 1990-10-02 | Medivir Ab | Nucleoside derivatives |
| US5248672A (en) * | 1990-11-01 | 1993-09-28 | The Regents Of The University Of Michigan | Polysubstituted benzimidazole nucleosides as antiviral agents |
| WO1994008456A1 (en) * | 1992-10-21 | 1994-04-28 | The Regents Of The University Of Michigan | Polysubstituted benzimidazoles as antiviral agents |
| GB9413724D0 (en) * | 1994-07-07 | 1994-08-24 | Wellcome Found | Therapeutic nucleosides |
| GB9600143D0 (en) | 1996-01-05 | 1996-03-06 | Wellcome Found | Therapeutic compounds |
| GB9807354D0 (en) * | 1998-04-07 | 1998-06-03 | Glaxo Group Ltd | Antiviral compound |
| GB9807355D0 (en) | 1998-04-07 | 1998-06-03 | Glaxo Group Ltd | Antiviral compound |
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1998
- 1998-04-07 GB GBGB9807354.7A patent/GB9807354D0/en not_active Ceased
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1999
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- 1999-04-01 WO PCT/EP1999/002214 patent/WO1999051618A1/en not_active Ceased
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- 1999-04-01 KR KR1020007011089A patent/KR20010074472A/ko not_active Withdrawn
- 1999-04-01 ES ES99917935T patent/ES2216503T3/es not_active Expired - Lifetime
- 1999-04-01 JP JP2000542339A patent/JP2002510703A/ja active Pending
- 1999-04-01 HR HR20000669A patent/HRP20000669A2/hr not_active Application Discontinuation
- 1999-04-01 EE EEP200000584A patent/EE04120B1/et not_active IP Right Cessation
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2001
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