NO311216B1 - Fremgangsmåte for fremstilling av 3-amino-1,2,4- benzotriazindioksyd - Google Patents
Fremgangsmåte for fremstilling av 3-amino-1,2,4- benzotriazindioksyd Download PDFInfo
- Publication number
- NO311216B1 NO311216B1 NO19982315A NO982315A NO311216B1 NO 311216 B1 NO311216 B1 NO 311216B1 NO 19982315 A NO19982315 A NO 19982315A NO 982315 A NO982315 A NO 982315A NO 311216 B1 NO311216 B1 NO 311216B1
- Authority
- NO
- Norway
- Prior art keywords
- solution
- amino
- benzotriazine
- dioxide
- water
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title description 7
- BHHRGAKNBXQGIO-UHFFFAOYSA-N 1,2,4-benzotriazin-3-amine Chemical compound C1=CC=CC2=NC(N)=NN=C21 BHHRGAKNBXQGIO-UHFFFAOYSA-N 0.000 title description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 71
- ORYDPOVDJJZGHQ-UHFFFAOYSA-N tirapazamine Chemical compound C1=CC=CC2=[N+]([O-])C(N)=N[N+]([O-])=C21 ORYDPOVDJJZGHQ-UHFFFAOYSA-N 0.000 claims abstract description 36
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 32
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 30
- 239000000203 mixture Substances 0.000 claims abstract description 28
- OKEAMBAZBICIFP-UHFFFAOYSA-N 3-oxido-2,1,3-benzoxadiazol-3-ium Chemical compound C1=CC=CC2=[N+]([O-])ON=C21 OKEAMBAZBICIFP-UHFFFAOYSA-N 0.000 claims abstract description 21
- FFNKZSVHHUBFHT-UHFFFAOYSA-N cyanamide;sodium Chemical compound [Na].[Na].NC#N FFNKZSVHHUBFHT-UHFFFAOYSA-N 0.000 claims abstract description 21
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000002425 crystallisation Methods 0.000 claims abstract description 6
- 230000008025 crystallization Effects 0.000 claims abstract description 6
- 239000008366 buffered solution Substances 0.000 claims abstract 2
- 239000000243 solution Substances 0.000 claims description 56
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 44
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 34
- 238000001914 filtration Methods 0.000 claims description 31
- 239000002245 particle Substances 0.000 claims description 30
- 239000007787 solid Substances 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 229960000583 acetic acid Drugs 0.000 claims description 24
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 17
- 239000000725 suspension Substances 0.000 claims description 15
- 239000012535 impurity Substances 0.000 claims description 14
- 239000000706 filtrate Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 9
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 8
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 8
- 239000002244 precipitate Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000001632 sodium acetate Substances 0.000 claims description 7
- 235000017281 sodium acetate Nutrition 0.000 claims description 7
- 159000000000 sodium salts Chemical class 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 6
- 230000036961 partial effect Effects 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 239000012362 glacial acetic acid Substances 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- 238000007865 diluting Methods 0.000 claims description 2
- 230000003472 neutralizing effect Effects 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims 2
- 238000000265 homogenisation Methods 0.000 claims 2
- 238000000746 purification Methods 0.000 abstract description 2
- 229950002376 tirapazamine Drugs 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- 239000008367 deionised water Substances 0.000 description 12
- 229910021641 deionized water Inorganic materials 0.000 description 12
- AMSQCSIKKROLCK-UHFFFAOYSA-N 1-oxido-1-benzofuran-1-ium Chemical compound C1=CC=C2[O+]([O-])C=CC2=C1 AMSQCSIKKROLCK-UHFFFAOYSA-N 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 8
- 206010028980 Neoplasm Diseases 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- JWEKFMCYIRVOQZ-UHFFFAOYSA-N cyanamide;sodium Chemical compound [Na].NC#N JWEKFMCYIRVOQZ-UHFFFAOYSA-N 0.000 description 2
- 229940127089 cytotoxic agent Drugs 0.000 description 2
- 239000002254 cytotoxic agent Substances 0.000 description 2
- 231100000599 cytotoxic agent Toxicity 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000008203 oral pharmaceutical composition Substances 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- FFISWZPYNKWIRR-UHFFFAOYSA-N 5-oxidophenazin-5-ium Chemical compound C1=CC=C2[N+]([O-])=C(C=CC=C3)C3=NC2=C1 FFISWZPYNKWIRR-UHFFFAOYSA-N 0.000 description 1
- 206010021143 Hypoxia Diseases 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000007952 growth promoter Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000001146 hypoxic effect Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910001112 rose gold Inorganic materials 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000007974 sodium acetate buffer Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/08—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 condensed with carbocyclic rings or ring systems
- C07D253/10—Condensed 1,2,4-triazines; Hydrogenated condensed 1,2,4-triazines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/566,979 US5672702A (en) | 1995-12-04 | 1995-12-04 | Process for preparing 3 amino 1, 2, 4-benzotriazine dioxide |
| PCT/US1996/018761 WO1997020828A1 (en) | 1995-12-04 | 1996-11-21 | Process for preparing 3-amino-1,2,4-benzotriazine dioxide |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO982315D0 NO982315D0 (no) | 1998-05-20 |
| NO982315L NO982315L (no) | 1998-05-20 |
| NO311216B1 true NO311216B1 (no) | 2001-10-29 |
Family
ID=24265255
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19982315A NO311216B1 (no) | 1995-12-04 | 1998-05-20 | Fremgangsmåte for fremstilling av 3-amino-1,2,4- benzotriazindioksyd |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US5672702A (de) |
| EP (1) | EP0865435B1 (de) |
| JP (1) | JP2000501705A (de) |
| KR (1) | KR100502041B1 (de) |
| CN (1) | CN1068595C (de) |
| AT (1) | ATE213234T1 (de) |
| AU (1) | AU721627B2 (de) |
| BR (1) | BR9611864A (de) |
| CZ (1) | CZ292732B6 (de) |
| DE (1) | DE69619267T2 (de) |
| DK (1) | DK0865435T3 (de) |
| ES (1) | ES2172696T3 (de) |
| HK (1) | HK1017358A1 (de) |
| MX (1) | MX9804421A (de) |
| NO (1) | NO311216B1 (de) |
| NZ (1) | NZ323602A (de) |
| PT (1) | PT865435E (de) |
| RU (1) | RU2178413C2 (de) |
| WO (1) | WO1997020828A1 (de) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003042192A1 (en) * | 2001-11-13 | 2003-05-22 | Sanofi-Synthelabo | Preparation of 3-amino-1,2,4-benzotriazine dioxide |
| US20090136521A1 (en) * | 2005-10-03 | 2009-05-28 | Genetix Pharmaceuticals , Inc. | Method for Selectively Depleting Hypoxic Cells |
| CN101683319B (zh) * | 2008-09-24 | 2012-09-05 | 杭州民生药业有限公司 | 一种替拉扎明非肠道给药含水制剂及其制备方法 |
| JP2015500295A (ja) * | 2011-12-07 | 2015-01-05 | エスアールアイ インターナショナルＳＲＩ Ｉｎｔｅｒｎａｔｉｏｎａｌ | ヒト結核菌を標的とする医薬としてのベンゾトリアジンオキサイド類 |
| WO2014062856A1 (en) | 2012-10-16 | 2014-04-24 | Halozyme, Inc. | Hypoxia and hyaluronan and markers thereof for diagnosis and monitoring of diseases and conditions and related methods |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3980779A (en) * | 1972-02-01 | 1976-09-14 | Bayer Aktiengesellschaft | 3-Amino-1,2,4-benzotriazine-1,4-di-N-oxide compositions and method of using same |
| BE794742A (fr) * | 1972-02-01 | 1973-07-30 | Bayer Ag | Nouveaux di-n-oxydes (1,4) de benzo-1,2,4-triazine, leur procede de preparation et leur application comme medicaments et additifs de nutrition |
| US3991189A (en) * | 1972-11-15 | 1976-11-09 | Bayer Aktiengesellschaft | Microbiocidal methods and compositions using substituted 1,2,4-triazine-1,4-di-N-oxide derivatives |
| US3957779A (en) * | 1972-11-15 | 1976-05-18 | Bayer Aktiengesellschaft | Benzo-1,2,4-triazines |
| DE2255947A1 (de) * | 1972-11-15 | 1974-05-22 | Bayer Ag | Substituierte 3-amino-benzo-1,2,4triazin-di-n-oxide (1,4), verfahren zu ihrer herstellung sowie ihre verwendung als antimikrobielle mittel |
| DE2255946A1 (de) * | 1972-11-15 | 1974-05-22 | Bayer Ag | Verfahren zur herstellung von neuen eckige klammer auf 3-benzo-1,2,4-triazinyldioxid (1,4) eckige klammer zu -harnstoffen, sowie ihre verwendung als arzneimittel und futterzusatzmittel |
| US5175287A (en) * | 1986-09-25 | 1992-12-29 | S R I International | Process for preparing 1,2,4-benzotriazine oxides |
| DE3790581T1 (de) * | 1986-09-25 | 1988-08-25 | ||
| EP0478545B1 (de) * | 1989-09-18 | 1999-08-11 | Sri International | 1,2,4-benzotriazinoxide als funkempfindliche und selektive zytotoxische mittel |
| US5484612A (en) * | 1993-09-22 | 1996-01-16 | The Board Of Trustees Of The Leland Stanford Junior University | Method of treating a mammal having a solid tumor susceptible to treatment with cisplatin |
-
1995
- 1995-12-04 US US08/566,979 patent/US5672702A/en not_active Expired - Lifetime
-
1996
- 1996-11-21 BR BR9611864A patent/BR9611864A/pt not_active Application Discontinuation
- 1996-11-21 DK DK96941445T patent/DK0865435T3/da active
- 1996-11-21 JP JP09521313A patent/JP2000501705A/ja not_active Ceased
- 1996-11-21 WO PCT/US1996/018761 patent/WO1997020828A1/en active IP Right Grant
- 1996-11-21 DE DE69619267T patent/DE69619267T2/de not_active Expired - Fee Related
- 1996-11-21 CN CN96199754A patent/CN1068595C/zh not_active Expired - Fee Related
- 1996-11-21 PT PT96941445T patent/PT865435E/pt unknown
- 1996-11-21 ES ES96941445T patent/ES2172696T3/es not_active Expired - Lifetime
- 1996-11-21 EP EP96941445A patent/EP0865435B1/de not_active Expired - Lifetime
- 1996-11-21 AT AT96941445T patent/ATE213234T1/de not_active IP Right Cessation
- 1996-11-21 KR KR10-1998-0704200A patent/KR100502041B1/ko not_active IP Right Cessation
- 1996-11-21 CZ CZ19981723A patent/CZ292732B6/cs not_active IP Right Cessation
- 1996-11-21 AU AU10588/97A patent/AU721627B2/en not_active Ceased
- 1996-11-21 NZ NZ323602A patent/NZ323602A/en unknown
- 1996-11-21 RU RU98112135/04A patent/RU2178413C2/ru not_active IP Right Cessation
-
1998
- 1998-05-20 NO NO19982315A patent/NO311216B1/no unknown
- 1998-06-03 MX MX9804421A patent/MX9804421A/es unknown
-
1999
- 1999-06-16 HK HK99102591A patent/HK1017358A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| KR100502041B1 (ko) | 2005-09-26 |
| CN1068595C (zh) | 2001-07-18 |
| WO1997020828A1 (en) | 1997-06-12 |
| JP2000501705A (ja) | 2000-02-15 |
| ES2172696T3 (es) | 2002-10-01 |
| EP0865435A1 (de) | 1998-09-23 |
| DK0865435T3 (da) | 2002-05-27 |
| HK1017358A1 (en) | 1999-11-19 |
| RU2178413C2 (ru) | 2002-01-20 |
| NZ323602A (en) | 1999-10-28 |
| ATE213234T1 (de) | 2002-02-15 |
| DE69619267D1 (de) | 2002-03-21 |
| BR9611864A (pt) | 1999-05-18 |
| AU721627B2 (en) | 2000-07-13 |
| CN1207736A (zh) | 1999-02-10 |
| CZ292732B6 (cs) | 2003-12-17 |
| DE69619267T2 (de) | 2003-12-24 |
| US5672702A (en) | 1997-09-30 |
| EP0865435A4 (de) | 1998-12-23 |
| EP0865435B1 (de) | 2002-02-13 |
| PT865435E (pt) | 2002-07-31 |
| CZ172398A3 (cs) | 1998-09-16 |
| MX9804421A (es) | 1998-09-30 |
| KR19990071913A (ko) | 1999-09-27 |
| NO982315D0 (no) | 1998-05-20 |
| AU1058897A (en) | 1997-06-27 |
| NO982315L (no) | 1998-05-20 |
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