NO309088B1 - Alkylaminderivater av substituerte kinoksalin-2,3-dioner, farmasøytiske preparater omfattende forbindelsene, samt anvendelse av forbindelsene - Google Patents
Alkylaminderivater av substituerte kinoksalin-2,3-dioner, farmasøytiske preparater omfattende forbindelsene, samt anvendelse av forbindelsene Download PDFInfo
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- NO309088B1 NO309088B1 NO975703A NO975703A NO309088B1 NO 309088 B1 NO309088 B1 NO 309088B1 NO 975703 A NO975703 A NO 975703A NO 975703 A NO975703 A NO 975703A NO 309088 B1 NO309088 B1 NO 309088B1
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- Prior art keywords
- methyl
- preparation
- hydrogen
- alkyl
- compounds
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- 150000001875 compounds Chemical class 0.000 title claims description 50
- 239000000825 pharmaceutical preparation Chemical class 0.000 title claims description 9
- SEPKUNXLGWMPHL-UHFFFAOYSA-N quinoxaline-2,3-dione Chemical class C1=CC=CC2=NC(=O)C(=O)N=C21 SEPKUNXLGWMPHL-UHFFFAOYSA-N 0.000 title description 11
- 150000003973 alkyl amines Chemical class 0.000 title description 3
- 238000002360 preparation method Methods 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 29
- 150000002431 hydrogen Chemical class 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 206010008118 cerebral infarction Diseases 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 201000006474 Brain Ischemia Diseases 0.000 claims description 8
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 208000035475 disorder Diseases 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 208000024827 Alzheimer disease Diseases 0.000 claims description 6
- 208000023105 Huntington disease Diseases 0.000 claims description 6
- 208000027089 Parkinsonian disease Diseases 0.000 claims description 6
- 206010034010 Parkinsonism Diseases 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
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- 229940125681 anticonvulsant agent Drugs 0.000 claims description 3
- SNBBOWVAVZWDBR-UHFFFAOYSA-N 5-(diethylaminomethyl)-6-methyl-7-nitro-1,4-dihydroquinoxaline-2,3-dione Chemical compound N1C(=O)C(=O)NC2=C1C=C([N+]([O-])=O)C(C)=C2CN(CC)CC SNBBOWVAVZWDBR-UHFFFAOYSA-N 0.000 claims description 2
- XCQWBELWEXDOLU-UHFFFAOYSA-N 5-[(cyclohexylmethylamino)methyl]-6-methyl-7-nitro-1,4-dihydroquinoxaline-2,3-dione Chemical compound C1=2NC(=O)C(=O)NC=2C=C([N+]([O-])=O)C(C)=C1CNCC1CCCCC1 XCQWBELWEXDOLU-UHFFFAOYSA-N 0.000 claims description 2
- VWTFQEVPLOCNNL-UHFFFAOYSA-N 5-[(dibutylamino)methyl]-6-methyl-7-nitro-1,4-dihydroquinoxaline-2,3-dione Chemical compound N1C(=O)C(=O)NC2=C1C=C([N+]([O-])=O)C(C)=C2CN(CCCC)CCCC VWTFQEVPLOCNNL-UHFFFAOYSA-N 0.000 claims description 2
- GBJGHHDLBLIZIG-UHFFFAOYSA-N 5-[(dimethylamino)methyl]-6-methyl-7-nitro-1,4-dihydroquinoxaline-2,3-dione Chemical compound N1C(=O)C(=O)NC2=C1C=C([N+]([O-])=O)C(C)=C2CN(C)C GBJGHHDLBLIZIG-UHFFFAOYSA-N 0.000 claims description 2
- WLZMNNRMJRBZPN-UHFFFAOYSA-N 5-[(dipropylamino)methyl]-6-methyl-7-nitro-1,4-dihydroquinoxaline-2,3-dione Chemical compound N1C(=O)C(=O)NC2=C1C=C([N+]([O-])=O)C(C)=C2CN(CCC)CCC WLZMNNRMJRBZPN-UHFFFAOYSA-N 0.000 claims description 2
- 208000002381 Brain Hypoxia Diseases 0.000 claims description 2
- 230000000903 blocking effect Effects 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 230000000848 glutamatergic effect Effects 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- 125000000217 alkyl group Chemical group 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
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- 239000000243 solution Substances 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
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- 239000002253 acid Substances 0.000 description 9
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- 238000000034 method Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 229940024606 amino acid Drugs 0.000 description 7
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- 102000005962 receptors Human genes 0.000 description 7
- 108020003175 receptors Proteins 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
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- 230000001419 dependent effect Effects 0.000 description 6
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- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 5
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
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- 230000008733 trauma Effects 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
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- 108090000078 AMPA Receptors Proteins 0.000 description 3
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- 241000976983 Anoxia Species 0.000 description 3
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical class [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 3
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- VIKJATPBGVVJNO-UHFFFAOYSA-N (2-acetamido-6-methyl-3-nitrophenyl)methyl acetate Chemical compound CC(=O)NC1=C(COC(C)=O)C(C)=CC=C1[N+]([O-])=O VIKJATPBGVVJNO-UHFFFAOYSA-N 0.000 description 2
- IRIQGMOSAUZEKK-UHFFFAOYSA-N (2-amino-6-methyl-3-nitrophenyl)methanol Chemical compound CC1=CC=C([N+]([O-])=O)C(N)=C1CO IRIQGMOSAUZEKK-UHFFFAOYSA-N 0.000 description 2
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- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
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- 125000005309 thioalkoxy group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
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Classifications
-
- 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
- C07D405/12—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 linked by a chain containing hetero atoms as chain links
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines 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 carbon atoms of the hetero ring
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Emergency Medicine (AREA)
- Psychiatry (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Hospice & Palliative Care (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Vascular Medicine (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/474,876 US5654303A (en) | 1995-06-07 | 1995-06-07 | Alkyl amine derivatives of substituted quinoxaline 2,3-diones as glutamate receptor antagonists |
| PCT/US1996/006818 WO1996040651A1 (en) | 1995-06-07 | 1996-05-13 | Alkyl amine derivatives of substituted quinoxaline 2,3-diones as glutamate receptor antagonists |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO975703D0 NO975703D0 (no) | 1997-12-05 |
| NO975703L NO975703L (no) | 1997-12-05 |
| NO309088B1 true NO309088B1 (no) | 2000-12-11 |
Family
ID=23885301
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO975703A NO309088B1 (no) | 1995-06-07 | 1997-12-05 | Alkylaminderivater av substituerte kinoksalin-2,3-dioner, farmasøytiske preparater omfattende forbindelsene, samt anvendelse av forbindelsene |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US5654303A (xx) |
| EP (1) | EP0837854B1 (xx) |
| JP (1) | JPH11506725A (xx) |
| KR (1) | KR19990022481A (xx) |
| AT (1) | ATE229512T1 (xx) |
| AU (1) | AU716156B2 (xx) |
| BG (1) | BG63462B1 (xx) |
| CA (1) | CA2219755A1 (xx) |
| CZ (1) | CZ290899B6 (xx) |
| DE (1) | DE69625361T2 (xx) |
| DK (1) | DK0837854T3 (xx) |
| EA (1) | EA000762B1 (xx) |
| EE (1) | EE03683B1 (xx) |
| ES (1) | ES2187650T3 (xx) |
| HU (2) | HUP9802568A3 (xx) |
| MX (1) | MX9708431A (xx) |
| NO (1) | NO309088B1 (xx) |
| NZ (1) | NZ308318A (xx) |
| PL (1) | PL186764B1 (xx) |
| PT (1) | PT837854E (xx) |
| SK (1) | SK283181B6 (xx) |
| UA (1) | UA48183C2 (xx) |
| WO (1) | WO1996040651A1 (xx) |
| ZA (1) | ZA964760B (xx) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2149873C1 (ru) * | 1994-09-27 | 2000-05-27 | Яманоути Фармасьютикал Ко., Лтд. | 1,2,3,4-тетрагидрохиноксалиндионовые производные и фармацевтическая композиция |
| AU3133697A (en) * | 1996-06-05 | 1998-01-05 | Warner-Lambert Company | Amide derivatives of substituted quinoxaline 2,3-diones as glutamate receptor antagonists |
| US6015800A (en) * | 1997-09-03 | 2000-01-18 | Warner-Lambert Company | Substituted quinoxaline-2-ones as glutamate receptor antagonists |
| IL125950A0 (en) * | 1997-09-05 | 1999-04-11 | Pfizer Prod Inc | Methods of administering ampa receptor antagonists to treat dyskinesias associated with dopamine agonist therapy |
| US6391922B1 (en) | 1998-01-13 | 2002-05-21 | Synchroneuron, Llc | Treatment of posttraumatic stress disorder, obsessive-compulsive disorder and related neuropsychiatric disorders |
| US20040152694A1 (en) * | 2003-02-04 | 2004-08-05 | Istvan Kurucz | Methods and compositions for treating inflammatory disorders of the airways |
| EP2338492A1 (en) | 2009-12-24 | 2011-06-29 | Universidad del Pais Vasco | Methods and compositions for the treatment of alzheimer |
| CN110642798B (zh) * | 2019-11-10 | 2020-07-24 | 湖南科技学院 | 一种n-取代-1,4-二氢-2,3-喹喔啉二酮化合物的绿色合成方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3992378A (en) * | 1973-12-26 | 1976-11-16 | Eli Lilly And Company | Fluoralkyl quinoxadinediones |
| JPH05117276A (ja) * | 1991-10-23 | 1993-05-14 | Sumitomo Pharmaceut Co Ltd | 新規な３環性キノキサリンジオン誘導体 |
| JPH06228112A (ja) * | 1993-02-05 | 1994-08-16 | Yamanouchi Pharmaceut Co Ltd | （１ｈ，４ｈ）キノキサリン誘導体 |
| TW260660B (xx) * | 1993-04-22 | 1995-10-21 | Sumitomo Pharma | |
| DE69407407T2 (de) * | 1993-05-13 | 1998-04-09 | Neurosearch As | Ampa antagonisten und behandlungsmethode |
| 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 |
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1995
- 1995-06-07 US US08/474,876 patent/US5654303A/en not_active Expired - Fee Related
-
1996
- 1996-05-13 CZ CZ19973872A patent/CZ290899B6/cs not_active IP Right Cessation
- 1996-05-13 HU HU9802568A patent/HUP9802568A3/hu unknown
- 1996-05-13 UA UA98010046A patent/UA48183C2/uk unknown
- 1996-05-13 WO PCT/US1996/006818 patent/WO1996040651A1/en not_active Application Discontinuation
- 1996-05-13 HU HU9900883A patent/HUP9900883A3/hu unknown
- 1996-05-13 JP JP9500558A patent/JPH11506725A/ja not_active Ceased
- 1996-05-13 NZ NZ308318A patent/NZ308318A/en unknown
- 1996-05-13 ES ES96914617T patent/ES2187650T3/es not_active Expired - Lifetime
- 1996-05-13 PT PT96914617T patent/PT837854E/pt unknown
- 1996-05-13 SK SK1690-97A patent/SK283181B6/sk unknown
- 1996-05-13 DE DE69625361T patent/DE69625361T2/de not_active Expired - Fee Related
- 1996-05-13 DK DK96914617T patent/DK0837854T3/da active
- 1996-05-13 AU AU57920/96A patent/AU716156B2/en not_active Ceased
- 1996-05-13 EA EA199800008A patent/EA000762B1/ru not_active IP Right Cessation
- 1996-05-13 KR KR1019970708962A patent/KR19990022481A/ko not_active Application Discontinuation
- 1996-05-13 MX MX9708431A patent/MX9708431A/es not_active IP Right Cessation
- 1996-05-13 EE EE9700338A patent/EE03683B1/xx not_active IP Right Cessation
- 1996-05-13 AT AT96914617T patent/ATE229512T1/de not_active IP Right Cessation
- 1996-05-13 EP EP96914617A patent/EP0837854B1/en not_active Expired - Lifetime
- 1996-05-13 CA CA002219755A patent/CA2219755A1/en not_active Abandoned
- 1996-05-13 PL PL96323824A patent/PL186764B1/pl unknown
- 1996-06-06 ZA ZA964760A patent/ZA964760B/xx unknown
-
1997
- 1997-11-27 BG BG102079A patent/BG63462B1/bg unknown
- 1997-12-05 NO NO975703A patent/NO309088B1/no not_active IP Right Cessation
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