FI102276B - Menetelmä uusien terapeuttisesti käyttökelpoisten 5-N,N-dialkyylisulfa moyyli-1H-6,7,8,9-tetrahydro£g|indoli-2,3-dioni-3-oksiimien valmistami seksi - Google Patents
Menetelmä uusien terapeuttisesti käyttökelpoisten 5-N,N-dialkyylisulfa moyyli-1H-6,7,8,9-tetrahydro£g|indoli-2,3-dioni-3-oksiimien valmistami seksi Download PDFInfo
- Publication number
- FI102276B FI102276B FI923032A FI923032A FI102276B FI 102276 B FI102276 B FI 102276B FI 923032 A FI923032 A FI 923032A FI 923032 A FI923032 A FI 923032A FI 102276 B FI102276 B FI 102276B
- Authority
- FI
- Finland
- Prior art keywords
- indole
- dione
- oxime
- tetrahydro
- compounds
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- LNMAXZZQNSPQSR-UHFFFAOYSA-N 3-(hydroxyamino)indol-2-one Chemical class C1=CC=CC2=NC(=O)C(NO)=C21 LNMAXZZQNSPQSR-UHFFFAOYSA-N 0.000 claims description 11
- -1 1-pyrrolidinylsulfonyl Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- PGNRLPTYNKQQDY-UHFFFAOYSA-N 2,3-dihydroxyindole Chemical compound C1=CC=C2C(O)=C(O)NC2=C1 PGNRLPTYNKQQDY-UHFFFAOYSA-N 0.000 claims 1
- 241000124008 Mammalia Species 0.000 abstract description 4
- 108010011562 aspartic acid receptor Proteins 0.000 abstract description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000004122 cyclic group Chemical group 0.000 abstract 2
- OZDAOHVKBFBBMZ-UHFFFAOYSA-N 2-aminopentanedioic acid;hydrate Chemical compound O.OC(=O)C(N)CCC(O)=O OZDAOHVKBFBBMZ-UHFFFAOYSA-N 0.000 abstract 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 abstract 1
- 235000013922 glutamic acid Nutrition 0.000 abstract 1
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical class C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 13
- 230000002461 excitatory amino acid Effects 0.000 description 8
- 239000003257 excitatory amino acid Substances 0.000 description 8
- 206010010904 Convulsion Diseases 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 230000001419 dependent effect Effects 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 230000004071 biological effect Effects 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- WBRBPLKDONUGCM-UHFFFAOYSA-N 3-(hydroxyamino)benzo[g]indol-2-one Chemical compound C1=CC2=CC=CC=C2C2=C1C(=NO)C(=O)N2 WBRBPLKDONUGCM-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000003042 antagnostic effect Effects 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 208000026106 cerebrovascular disease Diseases 0.000 description 2
- 230000007850 degeneration Effects 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 230000002964 excitative effect Effects 0.000 description 2
- 125000005597 hydrazone group Chemical group 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 210000002569 neuron Anatomy 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FTUPWENJOYTVOJ-UHFFFAOYSA-N 1h-benzo[g]indole-2,3-dione Chemical compound C1=CC=C2C(NC(C3=O)=O)=C3C=CC2=C1 FTUPWENJOYTVOJ-UHFFFAOYSA-N 0.000 description 1
- NGXLTYPELAIUHE-UHFFFAOYSA-N 2-(hydroxyamino)indol-3-one Chemical class C1=CC=C2C(=O)C(NO)=NC2=C1 NGXLTYPELAIUHE-UHFFFAOYSA-N 0.000 description 1
- ADQOEXMBQYZXQN-UHFFFAOYSA-N 6,7,8,9-tetrahydro-1h-benzo[g]indole-2,3-dione Chemical compound C1CCCC2=C1C=CC1=C2NC(=O)C1=O ADQOEXMBQYZXQN-UHFFFAOYSA-N 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 206010008111 Cerebral haemorrhage Diseases 0.000 description 1
- 206010013647 Drowning Diseases 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 229940122459 Glutamate antagonist Drugs 0.000 description 1
- 208000032843 Hemorrhage Diseases 0.000 description 1
- 208000023105 Huntington disease Diseases 0.000 description 1
- 102000000079 Kainic Acid Receptors Human genes 0.000 description 1
- 108010069902 Kainic Acid Receptors Proteins 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
- 241000219729 Lathyrus Species 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 229940127523 NMDA Receptor Antagonists Drugs 0.000 description 1
- 238000011785 NMRI mouse Methods 0.000 description 1
- 208000027089 Parkinsonian disease Diseases 0.000 description 1
- 206010034010 Parkinsonism Diseases 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 239000003194 amino acid receptor blocking agent Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 208000029028 brain injury Diseases 0.000 description 1
- 230000006727 cell loss Effects 0.000 description 1
- 208000015114 central nervous system disease Diseases 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 206010008118 cerebral infarction Diseases 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 206010013663 drug dependence Diseases 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 108010025843 glutamine receptor Proteins 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 238000013421 nuclear magnetic resonance imaging Methods 0.000 description 1
- 125000003544 oxime group Chemical group 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- QUKUNZDPKPLYGS-UHFFFAOYSA-N propanoic acid;1h-pyrrole Chemical compound CCC(O)=O.C=1C=CNC=1 QUKUNZDPKPLYGS-UHFFFAOYSA-N 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 210000000689 upper leg Anatomy 0.000 description 1
- 230000002861 ventricular Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/60—Naphtho [b] pyrroles; Hydrogenated naphtho [b] pyrroles
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/06—Antimigraine agents
-
- 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
- A61P25/18—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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Anesthesiology (AREA)
- Hospice & Palliative Care (AREA)
- Addiction (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Diaphragms For Electromechanical Transducers (AREA)
- Supply Devices, Intensifiers, Converters, And Telemotors (AREA)
- Lubricants (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US72747991A | 1991-07-09 | 1991-07-09 | |
| US72747991 | 1991-07-09 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI923032A0 FI923032A0 (fi) | 1992-06-30 |
| FI923032L FI923032L (fi) | 1993-01-10 |
| FI102276B1 FI102276B1 (fi) | 1998-11-13 |
| FI102276B true FI102276B (fi) | 1998-11-13 |
Family
ID=24922831
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI923032A FI102276B (fi) | 1991-07-09 | 1992-06-30 | Menetelmä uusien terapeuttisesti käyttökelpoisten 5-N,N-dialkyylisulfa moyyli-1H-6,7,8,9-tetrahydro£g|indoli-2,3-dioni-3-oksiimien valmistami seksi |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP0522494B1 (cg-RX-API-DMAC10.html) |
| JP (1) | JP3270524B2 (cg-RX-API-DMAC10.html) |
| AT (1) | ATE143659T1 (cg-RX-API-DMAC10.html) |
| AU (1) | AU655643B2 (cg-RX-API-DMAC10.html) |
| CA (1) | CA2073281A1 (cg-RX-API-DMAC10.html) |
| DE (1) | DE69214205T2 (cg-RX-API-DMAC10.html) |
| DK (1) | DK0522494T3 (cg-RX-API-DMAC10.html) |
| ES (1) | ES2094850T3 (cg-RX-API-DMAC10.html) |
| FI (1) | FI102276B (cg-RX-API-DMAC10.html) |
| GR (1) | GR3021814T3 (cg-RX-API-DMAC10.html) |
| IE (1) | IE921730A1 (cg-RX-API-DMAC10.html) |
| NO (1) | NO178620C (cg-RX-API-DMAC10.html) |
| ZA (1) | ZA924118B (cg-RX-API-DMAC10.html) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK81593D0 (da) * | 1993-07-07 | 1993-07-07 | Neurosearch As | Nye isatinoximderivater, deres fremstilling og anvendelse |
| AR016384A1 (es) * | 1997-07-30 | 2001-07-04 | Smithkline Beecham Corp | Inhibidores de caspasas, composiciones farmaceuticas que comprenden dichos inhibidores de caspasas y uso de los inhibidores de caspasas para prepararun medicamento util para el tratamiento de apoptosis y desordenes asociados con excesiva actividad de la convertosa il-1 beta. |
| WO2000071102A2 (en) * | 1999-05-19 | 2000-11-30 | Neurosearch A/S | Inhibitors of proton-gated cation channels and their use in the treatment of ischaemic disorders |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE69677B1 (en) * | 1989-12-11 | 1996-10-02 | Neurosearch As | Isatine derivatives their preparation and use |
| US5164404A (en) * | 1991-03-15 | 1992-11-17 | Neurosearch A/S | Hydrazone derivatives and their use |
-
1992
- 1992-05-29 AU AU17268/92A patent/AU655643B2/en not_active Ceased
- 1992-06-05 ZA ZA924118A patent/ZA924118B/xx unknown
- 1992-06-30 FI FI923032A patent/FI102276B/fi active
- 1992-07-01 IE IE173092A patent/IE921730A1/en not_active Application Discontinuation
- 1992-07-07 AT AT92111478T patent/ATE143659T1/de not_active IP Right Cessation
- 1992-07-07 ES ES92111478T patent/ES2094850T3/es not_active Expired - Lifetime
- 1992-07-07 DE DE69214205T patent/DE69214205T2/de not_active Expired - Lifetime
- 1992-07-07 CA CA002073281A patent/CA2073281A1/en not_active Abandoned
- 1992-07-07 DK DK92111478.1T patent/DK0522494T3/da active
- 1992-07-07 JP JP17991692A patent/JP3270524B2/ja not_active Expired - Fee Related
- 1992-07-07 EP EP92111478A patent/EP0522494B1/en not_active Expired - Lifetime
- 1992-07-08 NO NO922686A patent/NO178620C/no unknown
-
1996
- 1996-11-28 GR GR960403205T patent/GR3021814T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO178620C (no) | 1996-05-02 |
| ATE143659T1 (de) | 1996-10-15 |
| DK0522494T3 (cg-RX-API-DMAC10.html) | 1997-03-03 |
| FI102276B1 (fi) | 1998-11-13 |
| FI923032L (fi) | 1993-01-10 |
| JP3270524B2 (ja) | 2002-04-02 |
| EP0522494A1 (en) | 1993-01-13 |
| NO922686D0 (no) | 1992-07-08 |
| DE69214205D1 (de) | 1996-11-07 |
| IE921730A1 (en) | 1993-01-13 |
| AU1726892A (en) | 1993-01-14 |
| NO922686L (no) | 1993-01-11 |
| EP0522494B1 (en) | 1996-10-02 |
| GR3021814T3 (en) | 1997-02-28 |
| FI923032A0 (fi) | 1992-06-30 |
| ES2094850T3 (es) | 1997-02-01 |
| DE69214205T2 (de) | 1997-02-06 |
| ZA924118B (en) | 1993-08-03 |
| JPH05201976A (ja) | 1993-08-10 |
| AU655643B2 (en) | 1995-01-05 |
| CA2073281A1 (en) | 1993-01-10 |
| NO178620B (no) | 1996-01-22 |
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