NO300374B1 - Pyrazolo£4,3-c|pyridiner, farmasöytiske sammensetninger inneholdende disse og deres anvendelse til fremstilling av hemmere av reopptak av serotonin - Google Patents
Pyrazolo£4,3-c|pyridiner, farmasöytiske sammensetninger inneholdende disse og deres anvendelse til fremstilling av hemmere av reopptak av serotonin Download PDFInfo
- Publication number
- NO300374B1 NO300374B1 NO933784A NO933784A NO300374B1 NO 300374 B1 NO300374 B1 NO 300374B1 NO 933784 A NO933784 A NO 933784A NO 933784 A NO933784 A NO 933784A NO 300374 B1 NO300374 B1 NO 300374B1
- Authority
- NO
- Norway
- Prior art keywords
- pyrazolo
- pyridine
- compound
- hydrogen
- give
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract 3
- 238000002360 preparation method Methods 0.000 title claims description 9
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 title description 8
- 229940076279 serotonin Drugs 0.000 title description 5
- 150000003222 pyridines Chemical class 0.000 title description 4
- 239000003112 inhibitor Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 62
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 4
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- PXPLVVXCLPDAOW-UHFFFAOYSA-N 3-phenyl-1H-pyrazolo[3,4-c]pyridine Chemical compound C1(=CC=CC=C1)C1=NNC2=CN=CC=C21 PXPLVVXCLPDAOW-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 230000000697 serotonin reuptake Effects 0.000 claims description 2
- FRQDLLHJSQLJFF-UHFFFAOYSA-N 1-[3-(2,3,4-trichlorophenyl)pyrazolo[4,3-c]pyridin-1-yl]propan-2-amine Chemical group C12=CN=CC=C2N(CC(N)C)N=C1C1=CC=C(Cl)C(Cl)=C1Cl FRQDLLHJSQLJFF-UHFFFAOYSA-N 0.000 claims 1
- LBUVGJROPPPWTK-UHFFFAOYSA-N 2-[3-(2,4-dichlorophenyl)pyrazolo[4,3-c]pyridin-1-yl]ethanamine Chemical group C12=CN=CC=C2N(CCN)N=C1C1=CC=C(Cl)C=C1Cl LBUVGJROPPPWTK-UHFFFAOYSA-N 0.000 claims 1
- YIBHPGQHXBAJDP-UHFFFAOYSA-N 4-[3-(2,4-dichlorophenyl)pyrazolo[4,3-c]pyridin-1-yl]butan-1-amine Chemical group C12=CN=CC=C2N(CCCCN)N=C1C1=CC=C(Cl)C=C1Cl YIBHPGQHXBAJDP-UHFFFAOYSA-N 0.000 claims 1
- 208000032544 Cicatrix Diseases 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 231100000241 scar Toxicity 0.000 claims 1
- 230000037387 scars Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 24
- 238000000034 method Methods 0.000 abstract description 10
- 230000003287 optical effect Effects 0.000 abstract 1
- 239000003772 serotonin uptake inhibitor Substances 0.000 abstract 1
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 35
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 31
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
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- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
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- 239000000725 suspension Substances 0.000 description 8
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- 238000003818 flash chromatography Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
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- 210000004556 brain Anatomy 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- -1 dialkylaminoalkyl chloride Chemical compound 0.000 description 6
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
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- 210000003568 synaptosome Anatomy 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 238000003556 assay Methods 0.000 description 5
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 5
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 4
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 4
- 238000001665 trituration Methods 0.000 description 4
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 3
- OFMKMVLDGZVWNW-UHFFFAOYSA-N 3-phenyl-1h-pyrazolo[4,3-c]pyridine Chemical compound C1=CC=CC=C1C1=NNC2=CC=NC=C12 OFMKMVLDGZVWNW-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
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- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/964,690 US5264576A (en) | 1992-10-22 | 1992-10-22 | Pyrazolo[4,3-c]pyridines which are intermediates |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO933784D0 NO933784D0 (no) | 1993-10-21 |
| NO933784L NO933784L (no) | 1994-04-25 |
| NO300374B1 true NO300374B1 (no) | 1997-05-20 |
Family
ID=25508857
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO933784A NO300374B1 (no) | 1992-10-22 | 1993-10-21 | Pyrazolo£4,3-c|pyridiner, farmasöytiske sammensetninger inneholdende disse og deres anvendelse til fremstilling av hemmere av reopptak av serotonin |
Country Status (18)
| Country | Link |
|---|---|
| US (4) | US5264576A (es) |
| EP (1) | EP0594001B1 (es) |
| JP (1) | JP2656211B2 (es) |
| KR (1) | KR100295026B1 (es) |
| CN (1) | CN1049658C (es) |
| AT (1) | ATE195522T1 (es) |
| AU (1) | AU671305B2 (es) |
| CA (1) | CA2108941A1 (es) |
| DE (1) | DE69329231T2 (es) |
| DK (1) | DK0594001T3 (es) |
| ES (1) | ES2152237T3 (es) |
| FI (1) | FI103890B1 (es) |
| GR (1) | GR3034819T3 (es) |
| MX (1) | MX9306552A (es) |
| NO (1) | NO300374B1 (es) |
| NZ (1) | NZ250003A (es) |
| PT (1) | PT594001E (es) |
| TW (1) | TW252114B (es) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5300498A (en) * | 1993-06-04 | 1994-04-05 | Hoechst-Roussel Pharmaceuticals Incorporated | 6-piperazinyl-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acids, esters, amides and related compounds |
| US5618824A (en) * | 1994-03-09 | 1997-04-08 | Merrell Pharmaceuticals Inc. | Treatment of obsessive-compulsive disorders with 5-HT2 antagonists |
| US5565413A (en) * | 1994-12-06 | 1996-10-15 | Zeneca Limited | Substituted pyridyl phenyl ketone herbicides |
| RU2317988C2 (ru) | 2000-08-14 | 2008-02-27 | Орто-Макнейл Фармасьютикал, Инк. | Замещенные пиразолы, фармацевтическая композиция на их основе, применение фармацевтической композиции и способ ингибирования активности катепсина s |
| EP1309592B9 (en) | 2000-08-14 | 2007-02-28 | Ortho-McNeil Pharmaceutical, Inc. | Substituted pyrazoles |
| US7332494B2 (en) | 2000-08-14 | 2008-02-19 | Janssen Pharmaceutica, N.V. | Method for treating allergies using substituted pyrazoles |
| WO2002014314A2 (en) | 2000-08-14 | 2002-02-21 | Ortho Mcneil Pharmaceutical, Inc. | Substituted pyrazoles |
| US20070117785A1 (en) * | 2000-08-14 | 2007-05-24 | Butler Christopher R | Substituted pyrazoles and methods of treatment with substituted pyrazoles |
| US20050101587A9 (en) * | 2000-08-14 | 2005-05-12 | Butler Christopher R. | Method for treating allergies using substituted pyrazoles |
| WO2002020002A2 (en) | 2000-09-06 | 2002-03-14 | Ortho Mcneil Pharmaceutical, Inc. | A method for treating allergies |
| KR20050004214A (ko) | 2002-05-31 | 2005-01-12 | 에자이 가부시키가이샤 | 피라졸 화합물 및 이것을 포함하여 이루어지는 의약 조성물 |
| WO2010031791A1 (en) * | 2008-09-16 | 2010-03-25 | Biovitrum Ab (Publ) | New compounds ii |
| CN102558174B (zh) * | 2011-08-23 | 2014-03-19 | 天津市斯芬克司药物研发有限公司 | 一种全新吡唑并[4,3-c]吡啶化合物的发明及其合成方法 |
| JP6242885B2 (ja) | 2012-06-27 | 2017-12-06 | エフ・ホフマン−ラ・ロシュ・アクチェンゲゼルシャフト | ５−アザインダゾール化合物及び使用方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3994890A (en) * | 1974-01-31 | 1976-11-30 | Chugai Seiyaku Kabushiki Kaisha | 1-Aminoalkyl, 3-phenyl indazoles |
| JPS5944314B2 (ja) * | 1975-01-15 | 1984-10-29 | 中外製薬株式会社 | インダゾ−ル誘導体の製法 |
| JPS5936627B2 (ja) * | 1975-07-25 | 1984-09-05 | 中外製薬株式会社 | インダゾ−ル誘導体の製法 |
| DK27383A (da) * | 1982-02-17 | 1983-08-18 | Lepetit Spa | Fremgangsmaade til fremstilling af pyrazol(4,3-c)pyridiner |
| JPH0615542B2 (ja) * | 1986-07-22 | 1994-03-02 | 吉富製薬株式会社 | ピラゾロピリジン化合物 |
| EP0338087A4 (en) * | 1987-10-13 | 1991-07-24 | Yoshitomi Pharmaceutical Industries, Ltd. | Fused pyrazole compounds, process for their preparation, and their medicinal use |
| DK181190D0 (da) * | 1990-07-30 | 1990-07-30 | Lundbeck & Co As H | 3-aryl-indol- eller 3-aryl-indazolderivater |
| EP0494774A1 (en) * | 1991-01-11 | 1992-07-15 | MERCK SHARP & DOHME LTD. | Indazole-substituted fivemembered heteroaromatic compounds |
| GB9216783D0 (en) * | 1992-08-07 | 1992-09-23 | Ici Plc | Heterocyclic derivatives |
| US5300478A (en) * | 1993-01-28 | 1994-04-05 | Zeneca Limited | Substituted fused pyrazolo compounds |
-
1992
- 1992-10-22 US US07/964,690 patent/US5264576A/en not_active Expired - Fee Related
-
1993
- 1993-08-17 US US08/106,953 patent/US5296491A/en not_active Expired - Fee Related
- 1993-10-08 AT AT93116317T patent/ATE195522T1/de not_active IP Right Cessation
- 1993-10-08 DE DE69329231T patent/DE69329231T2/de not_active Expired - Fee Related
- 1993-10-08 DK DK93116317T patent/DK0594001T3/da active
- 1993-10-08 ES ES93116317T patent/ES2152237T3/es not_active Expired - Lifetime
- 1993-10-08 PT PT93116317T patent/PT594001E/pt unknown
- 1993-10-08 EP EP93116317A patent/EP0594001B1/en not_active Expired - Lifetime
- 1993-10-20 FI FI934621A patent/FI103890B1/fi active
- 1993-10-20 NZ NZ250003A patent/NZ250003A/en unknown
- 1993-10-21 NO NO933784A patent/NO300374B1/no not_active IP Right Cessation
- 1993-10-21 MX MX9306552A patent/MX9306552A/es not_active IP Right Cessation
- 1993-10-21 AU AU49128/93A patent/AU671305B2/en not_active Ceased
- 1993-10-21 CA CA002108941A patent/CA2108941A1/en not_active Abandoned
- 1993-10-22 KR KR1019930022006A patent/KR100295026B1/ko not_active IP Right Cessation
- 1993-10-22 TW TW082108790A patent/TW252114B/zh active
- 1993-10-22 JP JP5265158A patent/JP2656211B2/ja not_active Expired - Fee Related
- 1993-10-22 CN CN93120396A patent/CN1049658C/zh not_active Expired - Fee Related
-
1994
- 1994-01-12 US US08/181,147 patent/US5380847A/en not_active Expired - Fee Related
- 1994-09-15 US US08/306,294 patent/US5428169A/en not_active Expired - Fee Related
-
2000
- 2000-11-10 GR GR20000402506T patent/GR3034819T3/el not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GR3034819T3 (en) | 2001-02-28 |
| EP0594001A1 (en) | 1994-04-27 |
| US5380847A (en) | 1995-01-10 |
| DE69329231T2 (de) | 2001-03-29 |
| TW252114B (es) | 1995-07-21 |
| JPH06192257A (ja) | 1994-07-12 |
| KR940009185A (ko) | 1994-05-20 |
| KR100295026B1 (ko) | 2001-09-17 |
| FI934621A (fi) | 1994-04-23 |
| CA2108941A1 (en) | 1994-04-23 |
| US5428169A (en) | 1995-06-27 |
| AU4912893A (en) | 1994-05-05 |
| PT594001E (pt) | 2001-01-31 |
| CN1099033A (zh) | 1995-02-22 |
| DK0594001T3 (da) | 2000-10-30 |
| FI934621A0 (fi) | 1993-10-20 |
| US5264576A (en) | 1993-11-23 |
| EP0594001B1 (en) | 2000-08-16 |
| ES2152237T3 (es) | 2001-02-01 |
| FI103890B (fi) | 1999-10-15 |
| MX9306552A (es) | 1994-06-30 |
| NO933784D0 (no) | 1993-10-21 |
| NO933784L (no) | 1994-04-25 |
| US5296491A (en) | 1994-03-22 |
| AU671305B2 (en) | 1996-08-22 |
| ATE195522T1 (de) | 2000-09-15 |
| FI103890B1 (fi) | 1999-10-15 |
| CN1049658C (zh) | 2000-02-23 |
| JP2656211B2 (ja) | 1997-09-24 |
| DE69329231D1 (de) | 2000-09-21 |
| NZ250003A (en) | 1996-03-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |
Free format text: LAPSED IN APRIL 2001 |