TW403740B - Novel crystal modifications of the compound 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide - Google Patents
Novel crystal modifications of the compound 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide Download PDFInfo
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- TW403740B TW403740B TW087108859A TW87108859A TW403740B TW 403740 B TW403740 B TW 403740B TW 087108859 A TW087108859 A TW 087108859A TW 87108859 A TW87108859 A TW 87108859A TW 403740 B TW403740 B TW 403740B
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- 238000012986 modification Methods 0.000 title claims abstract description 14
- 230000004048 modification Effects 0.000 title claims abstract description 14
- 239000013078 crystal Substances 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 title abstract description 6
- POGQSBRIGCQNEG-UHFFFAOYSA-N rufinamide Chemical compound N1=NC(C(=O)N)=CN1CC1=C(F)C=CC=C1F POGQSBRIGCQNEG-UHFFFAOYSA-N 0.000 title abstract 3
- 239000000843 powder Substances 0.000 claims abstract description 10
- 239000000126 substance Substances 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 18
- 238000002329 infrared spectrum Methods 0.000 claims description 11
- -1 2,6-difluorofluorenyl Chemical group 0.000 claims description 8
- 238000010521 absorption reaction Methods 0.000 claims description 8
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 5
- 230000002079 cooperative effect Effects 0.000 claims description 5
- 238000001028 reflection method Methods 0.000 claims description 5
- 206010015037 epilepsy Diseases 0.000 claims description 4
- 238000001228 spectrum Methods 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 238000004611 spectroscopical analysis Methods 0.000 claims description 2
- 230000009102 absorption Effects 0.000 claims 7
- 235000015170 shellfish Nutrition 0.000 claims 4
- 238000005079 FT-Raman Methods 0.000 claims 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 2
- 238000000634 powder X-ray diffraction Methods 0.000 claims 2
- 239000000654 additive Substances 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 238000004898 kneading Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract description 6
- 239000000047 product Substances 0.000 description 33
- 125000006508 2,6-difluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C(F)=C1[H])C([H])([H])* 0.000 description 11
- 239000003607 modifier Substances 0.000 description 8
- 238000001237 Raman spectrum Methods 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 3
- 238000001069 Raman spectroscopy Methods 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000875 corresponding effect Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
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- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
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- 239000004615 ingredient Substances 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
- MEHSHGNVSWRETD-UHFFFAOYSA-N 4-[(2,6-difluorophenyl)methyl]-2h-triazole Chemical compound FC1=CC=CC(F)=C1CC1=NNN=C1 MEHSHGNVSWRETD-UHFFFAOYSA-N 0.000 description 1
- 229920003084 Avicel® PH-102 Polymers 0.000 description 1
- 241000501308 Conus spectrum Species 0.000 description 1
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- 208000002193 Pain Diseases 0.000 description 1
- 239000004353 Polyethylene glycol 8000 Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000005147 X-ray Weissenberg Methods 0.000 description 1
- OMOVVBIIQSXZSZ-UHFFFAOYSA-N [6-(4-acetyloxy-5,9a-dimethyl-2,7-dioxo-4,5a,6,9-tetrahydro-3h-pyrano[3,4-b]oxepin-5-yl)-5-formyloxy-3-(furan-3-yl)-3a-methyl-7-methylidene-1a,2,3,4,5,6-hexahydroindeno[1,7a-b]oxiren-4-yl] 2-hydroxy-3-methylpentanoate Chemical class CC12C(OC(=O)C(O)C(C)CC)C(OC=O)C(C3(C)C(CC(=O)OC4(C)COC(=O)CC43)OC(C)=O)C(=C)C32OC3CC1C=1C=COC=1 OMOVVBIIQSXZSZ-UHFFFAOYSA-N 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 208000005298 acute pain Diseases 0.000 description 1
- 230000003556 anti-epileptic effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
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- 239000003795 chemical substances by application Substances 0.000 description 1
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- 239000012043 crude product Substances 0.000 description 1
- MAEBCGDGGATMSC-OSHGGGOQSA-N cyclamine Chemical compound O([C@H]1CO[C@H]([C@@H]([C@H]1O[C@@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O[C@@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O[C@H]1CC[C@]2(C)[C@H]3CCC45OCC6([C@@H](C[C@@]4(C)[C@]3(C)CCC2C1(C)C)O)CC[C@@](C[C@@H]65)(C)C=O)[C@@H]1OC[C@@H](O)[C@H](O)[C@H]1O MAEBCGDGGATMSC-OSHGGGOQSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 125000006287 difluorobenzyl group Chemical group 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
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- 238000002474 experimental method Methods 0.000 description 1
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 229960003943 hypromellose Drugs 0.000 description 1
- 239000003978 infusion fluid Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
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- 238000011160 research Methods 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical group [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH140497 | 1997-06-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW403740B true TW403740B (en) | 2000-09-01 |
Family
ID=4209650
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW087108859A TW403740B (en) | 1997-06-10 | 1998-06-04 | Novel crystal modifications of the compound 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide |
| TW087108858A TW526195B (en) | 1997-06-10 | 1998-06-04 | Crystal modifications of 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide and their use |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW087108858A TW526195B (en) | 1997-06-10 | 1998-06-04 | Crystal modifications of 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide and their use |
Country Status (36)
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW403740B (en) | 1997-06-10 | 2000-09-01 | Novartis Ag | Novel crystal modifications of the compound 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide |
| WO2003101991A1 (en) * | 2002-05-31 | 2003-12-11 | Schering Corporation | Xanthine phosphodiesterase v inhibitor polymorphs |
| GB0507298D0 (en) | 2005-04-11 | 2005-05-18 | Novartis Ag | Organic compounds |
| US7875284B2 (en) * | 2006-03-10 | 2011-01-25 | Cook Incorporated | Methods of manufacturing and modifying taxane coatings for implantable medical devices |
| US20090069390A1 (en) * | 2007-09-12 | 2009-03-12 | Protia, Llc | Deuterium-enriched rufinamide |
| US8183269B2 (en) | 2008-10-13 | 2012-05-22 | Cipla Limited | Process for the preparation of rufinamide |
| CN101768124B (zh) * | 2008-12-30 | 2012-01-04 | 北京本草天源药物研究院 | 一种药物晶体及其制备方法和用途 |
| IT1395736B1 (it) * | 2009-08-04 | 2012-10-19 | Dipharma Francis Srl | Forme cristalline di rufinamide |
| AU2010290049B2 (en) * | 2009-09-04 | 2013-09-19 | Tactical Therapeutics, Inc | Novel compositions and processes for preparing 5-amino or substituted amino 1,2,3-triazoles and triazole orotate formulations |
| EP2465853A1 (en) * | 2010-12-14 | 2012-06-20 | Laboratorios Lesvi, S.L. | Polymorph of rufinamide and process for obtaining it |
| JP2013525413A (ja) * | 2010-04-30 | 2013-06-20 | ラボラトリオス レスヴィ，エス．エル． | ルフィナマイド中間体の改良された製造方法 |
| ITMI20110718A1 (it) | 2011-04-29 | 2012-10-30 | Dipharma Francis Srl | Procedimento per la purificazione di rufinamide |
| US10206874B2 (en) | 2012-07-20 | 2019-02-19 | Hetero Research Foundation | Rufinamide solid dispersion |
| WO2021099481A1 (en) | 2019-11-20 | 2021-05-27 | Medichem, S.A. | Solid composition containing rufinamide |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3992378A (en) | 1973-12-26 | 1976-11-16 | Eli Lilly And Company | Fluoralkyl quinoxadinediones |
| US4156734A (en) | 1976-02-13 | 1979-05-29 | Merck & Co., Inc. | Antihypertensive compositions containing an aryl-substituted alanine azo and an arylhydrazino-propionic acid |
| GB1511195A (en) | 1976-10-18 | 1978-05-17 | Ici America Inc | Triazole derivatives |
| US4536518A (en) | 1979-11-01 | 1985-08-20 | Pfizer Inc. | Antidepressant derivatives of cis-4-phenyl-1,2,3,4-tetrahydro-1-naphthalenamine |
| US4346097A (en) * | 1980-09-30 | 1982-08-24 | Warner-Lambert Company | Method for treating convulsions with pyrazole-4-carboxamide derivatives |
| US4789680A (en) * | 1982-12-23 | 1988-12-06 | Ciba-Geigy Corporation | Aralkyltriazole compounds |
| FI834666A7 (fi) | 1982-12-23 | 1984-06-24 | Ciba Geigy Ag | Foerfarande foer framstaellning av nya aralkyltriazolfoereningar. |
| US4511572A (en) * | 1983-03-18 | 1985-04-16 | The University Of Kentucky Research Foundation | Triazoline anticonvulsant drugs |
| FI93544C (fi) * | 1985-04-18 | 1995-04-25 | Ciba Geigy Ag | Menetelmä fluorattujen, antikonvulsiivisesti vaikuttavien 1-bentsyyli-1H-1,2,3-triatsoliyhdisteiden valmistamiseksi |
| CA2002864C (en) | 1988-11-29 | 1999-11-16 | Eddy J. E. Freyne | (1h-azol-1-ylmethyl) substituted quinoline, quinazoline or quinoxaline derivatives |
| JPH02214504A (ja) | 1989-02-15 | 1990-08-27 | Nissan Chem Ind Ltd | 光学活性キノキサリン化合物の晶析法 |
| JPH04506967A (ja) | 1989-07-27 | 1992-12-03 | ジー．ディー．サール アンド カンパニー | 高血圧症治療用腎選択性生成物 |
| IL96507A0 (en) | 1989-12-08 | 1991-08-16 | Merck & Co Inc | Nitrogen-containing spirocycles and pharmaceutical compositions containing them |
| AU656154B2 (en) | 1990-11-06 | 1995-01-27 | Astellas Pharma Inc. | Fused pyrazine derivative |
| JP2753911B2 (ja) | 1991-12-06 | 1998-05-20 | キッセイ薬品工業株式会社 | Ｎ−ｔｅｒｔ−ブチル−１−メチル−３，３−ジフェニルプロピルアミン塩酸塩の結晶多形およびその製造方法 |
| DE4217952A1 (de) | 1992-05-30 | 1993-12-02 | Basf Ag | Chinoxalin-2,3(1H,4H)-dione |
| US5248699A (en) | 1992-08-13 | 1993-09-28 | Pfizer Inc. | Sertraline polymorph |
| US5631373A (en) | 1993-11-05 | 1997-05-20 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon, Eugene Oregon | Alkyl, azido, alkoxy, and fluoro-substituted and fused quinoxalinediones |
| GB9418443D0 (en) | 1994-09-13 | 1994-11-02 | Pfizer Ltd | Therapeutic agents |
| GB9419318D0 (en) | 1994-09-24 | 1994-11-09 | Pfizer Ltd | Therapeutic agents |
| DE69609314T2 (de) | 1995-02-22 | 2001-06-13 | Aventis Pharma Ltd., Tokio/Tokyo | Amorph piretanide, polymorphe davon, verfahren zur dessen herstellung und ihre verwendung |
| SI0918758T1 (en) * | 1996-07-11 | 2002-10-31 | Novartis Ag | Process for preparing 1-substituted 4-cyano-1,2,3-triazoles |
| TW403740B (en) * | 1997-06-10 | 2000-09-01 | Novartis Ag | Novel crystal modifications of the compound 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide |
-
1998
- 1998-06-04 TW TW087108859A patent/TW403740B/zh not_active IP Right Cessation
- 1998-06-04 TW TW087108858A patent/TW526195B/zh not_active IP Right Cessation
- 1998-06-08 IL IL12573298A patent/IL125732A/en not_active IP Right Cessation
- 1998-06-08 SK SK1093-98A patent/SK283685B6/sk not_active IP Right Cessation
- 1998-06-08 DE DE69813560T patent/DE69813560T2/de not_active Expired - Lifetime
- 1998-06-08 JP JP53628998A patent/JP3672575B2/ja not_active Expired - Lifetime
- 1998-06-08 SK SK1094-98A patent/SK283734B6/sk not_active IP Right Cessation
- 1998-06-08 JP JP53628898A patent/JP3672574B2/ja not_active Expired - Lifetime
- 1998-06-08 BR BR9804946A patent/BR9804946A/pt not_active Application Discontinuation
- 1998-06-08 US US09/125,329 patent/US6740669B1/en not_active Expired - Lifetime
- 1998-06-08 PT PT98934930T patent/PT994864E/pt unknown
- 1998-06-08 RU RU99104299/04A patent/RU2194041C2/ru active
- 1998-06-08 NZ NZ331370A patent/NZ331370A/xx not_active IP Right Cessation
- 1998-06-08 ES ES98934929T patent/ES2192779T3/es not_active Expired - Lifetime
- 1998-06-08 EP EP98934930A patent/EP0994864B1/en not_active Expired - Lifetime
- 1998-06-08 TR TR1998/01630T patent/TR199801630T1/xx unknown
- 1998-06-08 AU AU84371/98A patent/AU725528B2/en not_active Expired
- 1998-06-08 KR KR10-1998-0708149A patent/KR100409168B1/ko not_active Expired - Lifetime
- 1998-06-08 AU AU84372/98A patent/AU725517B2/en not_active Expired
- 1998-06-08 DK DK98934930T patent/DK0994864T3/da active
- 1998-06-08 DK DK98934929T patent/DK0994863T3/da active
- 1998-06-08 WO PCT/EP1998/003427 patent/WO1998056772A1/en active IP Right Grant
- 1998-06-08 ID IDW980065D patent/ID27660A/id unknown
- 1998-06-08 CA CA002256015A patent/CA2256015C/en not_active Expired - Lifetime
- 1998-06-08 HU HU0000798A patent/HU226107B1/hu unknown
- 1998-06-08 PE PE1998000478A patent/PE79799A1/es not_active IP Right Cessation
- 1998-06-08 AT AT98934929T patent/ATE232852T1/de active
- 1998-06-08 BR BR9804947A patent/BR9804947A/pt not_active Application Discontinuation
- 1998-06-08 CN CN988000113A patent/CN1132820C/zh not_active Expired - Lifetime
- 1998-06-08 PE PE1998000479A patent/PE80999A1/es not_active IP Right Cessation
- 1998-06-08 CZ CZ19982533A patent/CZ292481B6/cs not_active IP Right Cessation
- 1998-06-08 ES ES98934930T patent/ES2197485T3/es not_active Expired - Lifetime
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