RU2114827C1 - Производные изатина или изатиноксима, способ получения производных изатиноксима и фармацевтическая композиция - Google Patents
Производные изатина или изатиноксима, способ получения производных изатиноксима и фармацевтическая композиция Download PDFInfo
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- RU2114827C1 RU2114827C1 RU94019425/04A RU94019425A RU2114827C1 RU 2114827 C1 RU2114827 C1 RU 2114827C1 RU 94019425/04 A RU94019425/04 A RU 94019425/04A RU 94019425 A RU94019425 A RU 94019425A RU 2114827 C1 RU2114827 C1 RU 2114827C1
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- Prior art keywords
- derivatives
- branched
- cyclic
- oxime
- isatinoksim
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- 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 description 1
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 description 1
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003194 amino acid receptor blocking agent Substances 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229940009098 aspartate Drugs 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 208000029028 brain injury Diseases 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- QOPVNWQGBQYBBP-UHFFFAOYSA-N chloroethyl chloroformate Chemical compound CC(Cl)OC(Cl)=O QOPVNWQGBQYBBP-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- CEJLBZWIKQJOAT-UHFFFAOYSA-N dichloroisocyanuric acid Chemical compound ClN1C(=O)NC(=O)N(Cl)C1=O CEJLBZWIKQJOAT-UHFFFAOYSA-N 0.000 description 1
- DBKKFIIYQGGHJO-UHFFFAOYSA-N diethyl 2-oxopropanedioate Chemical compound CCOC(=O)C(=O)C(=O)OCC DBKKFIIYQGGHJO-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 206010013663 drug dependence Diseases 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 208000028329 epileptic seizure Diseases 0.000 description 1
- XLYKCRIQSJLGDB-UHFFFAOYSA-N ethyl 2-(2,3-dioxo-1,6,8,9-tetrahydropyrrolo[2,3-f]isoquinolin-7-yl)acetate Chemical compound C1=C2CN(CC(=O)OCC)CCC2=C2NC(=O)C(=O)C2=C1 XLYKCRIQSJLGDB-UHFFFAOYSA-N 0.000 description 1
- BRPMKDLMTJBMTQ-UHFFFAOYSA-N ethyl 2-[3-(hydroxyamino)-2-oxo-8,9-dihydro-6h-pyrrolo[2,3-f]isoquinolin-7-yl]acetate Chemical compound C1=C2CN(CC(=O)OCC)CCC2=C2NC(=O)C(=NO)C2=C1 BRPMKDLMTJBMTQ-UHFFFAOYSA-N 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 230000002008 hemorrhagic effect Effects 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 230000007954 hypoxia Effects 0.000 description 1
- 125000001041 indolyl group Chemical group 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
- 208000001286 intracranial vasospasm Diseases 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 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
- 210000000664 rectum Anatomy 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000009424 thromboembolic effect Effects 0.000 description 1
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
- A61P25/06—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
- A61P25/18—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
- A61P25/28—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Medicinal Preparation (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75116591A | 1991-08-28 | 1991-08-28 | |
| US751165 | 1991-08-28 | ||
| US751,165 | 1991-08-28 | ||
| US83185192A | 1992-02-05 | 1992-02-05 | |
| US831851 | 1992-02-05 | ||
| US831,851 | 1992-02-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU94019425A RU94019425A (ru) | 1995-09-27 |
| RU2114827C1 true RU2114827C1 (ru) | 1998-07-10 |
Family
ID=27115380
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU94019425/04A RU2114827C1 (ru) | 1991-08-28 | 1992-08-27 | Производные изатина или изатиноксима, способ получения производных изатиноксима и фармацевтическая композиция |
Country Status (18)
| Country | Link |
|---|---|
| EP (1) | EP0529636B1 (enExample) |
| JP (1) | JP3170584B2 (enExample) |
| KR (1) | KR100277481B1 (enExample) |
| AT (1) | ATE181552T1 (enExample) |
| AU (1) | AU655672B2 (enExample) |
| CA (1) | CA2076948C (enExample) |
| CZ (1) | CZ282759B6 (enExample) |
| DE (1) | DE69229461T2 (enExample) |
| DK (1) | DK0529636T3 (enExample) |
| FI (1) | FI107156B (enExample) |
| GE (1) | GEP20002329B (enExample) |
| HU (2) | HUT70753A (enExample) |
| MX (1) | MX9204914A (enExample) |
| NO (1) | NO301117B1 (enExample) |
| PL (1) | PL170920B1 (enExample) |
| RU (1) | RU2114827C1 (enExample) |
| SK (1) | SK280578B6 (enExample) |
| WO (1) | WO1993005043A1 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08502483A (ja) | 1992-10-13 | 1996-03-19 | ワーナー−ランバート・コンパニー | 新規なキノキサリンジオン誘導体、それらの製造および使用 |
| US5843945A (en) * | 1993-05-13 | 1998-12-01 | Neurosearch A/S | AMPA antagonists and a method of treatment |
| FI954965L (fi) * | 1993-05-13 | 1995-11-10 | Neurosearch As | AMPA-antagonisteja ja hoitomenetelmä, jossa niitä käytetään |
| DK81593D0 (da) * | 1993-07-07 | 1993-07-07 | Neurosearch As | Nye isatinoximderivater, deres fremstilling og anvendelse |
| EP0781285B1 (en) * | 1994-09-14 | 2000-01-12 | Neurosearch A/S | Fused indole and quinoxaline derivatives, their preparation and use as glutamate antagonists |
| CA2199613C (en) * | 1994-09-14 | 2000-02-29 | Peter Moldt | Indole-2,3-dione-3-oxime derivatives, their preparation and use |
| UA54403C2 (uk) * | 1996-10-01 | 2003-03-17 | Н'Юросерч А/С | Похідні індол-2,3-діон-3-оксиму, фармацевтична композиція, спосіб лікування розладу чи захворювання ссавців, у тому числі людини та спосіб одержання похідних індол-2,3-діон-3-оксиму |
| FR2768624B1 (fr) * | 1997-09-25 | 1999-11-12 | Oreal | Utilisation d'un inhibiteur d'acides amines excitateurs dans une composition cosmetique ou dermatologique pour peaux sensibles et composition obtenue |
| DE60041399D1 (de) | 1999-05-19 | 2009-03-05 | Painceptor Pharma Corp | Hemmer der protonenabhängigen kationenkanäle und deren verwendung in der behandlung von ischemiebedingten erkrankungen |
| EP1736468A3 (en) | 2000-01-24 | 2007-01-03 | NeuroSearch A/S | Isatin derivatives with neurotrophic activity useful in the treatment of diseases mediated by the nerve growth factor (NGF) activation |
| WO2004039372A1 (en) | 2002-10-29 | 2004-05-13 | Sungkyunkwan University | Medicament component of berberine for the use of prevention and treatment of psycological dependence on and analgesic tolerance to morphine |
| EP1957486A4 (en) | 2005-11-23 | 2009-11-11 | Painceptor Pharma Corp | COMPOSITIONS AND METHODS FOR MODULATION OF IONIC CHANNELS |
| WO2014095675A1 (en) | 2012-12-19 | 2014-06-26 | Bayer Cropscience Ag | Difluoromethyl-nicotinic-indanyl carboxamides as fungicides |
| US9815768B2 (en) * | 2014-02-28 | 2017-11-14 | Sumitomo Chemical Company, Limited | Method for producing 2-(halogenomethyl)-3-methylnitrobenzene |
| HUE055651T2 (hu) | 2016-03-17 | 2021-12-28 | Fmc Corp | Eljárás S-enantiomer konvertálására racém formájává |
| CN112266368B (zh) * | 2017-11-15 | 2024-03-19 | 中山光禾医疗科技有限公司 | 光交联水凝胶材料的制备、原料、产品及应用 |
| CN108912127B (zh) * | 2018-08-27 | 2019-12-10 | 青岛农业大学 | 一种基于靛红骨架的苯并[b,e]氮杂卓化合物及其制备方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0432648B1 (en) * | 1989-12-11 | 1995-08-02 | Neurosearch A/S | Isatine derivatives, their preparation and use |
-
1992
- 1992-08-26 MX MX9204914A patent/MX9204914A/es not_active IP Right Cessation
- 1992-08-26 CA CA002076948A patent/CA2076948C/en not_active Expired - Fee Related
- 1992-08-27 KR KR1019940700676A patent/KR100277481B1/ko not_active Expired - Fee Related
- 1992-08-27 AU AU24820/92A patent/AU655672B2/en not_active Ceased
- 1992-08-27 JP JP50493393A patent/JP3170584B2/ja not_active Expired - Fee Related
- 1992-08-27 CZ CZ94395A patent/CZ282759B6/cs not_active IP Right Cessation
- 1992-08-27 SK SK238-94A patent/SK280578B6/sk unknown
- 1992-08-27 PL PL92302584A patent/PL170920B1/pl unknown
- 1992-08-27 GE GEAP19922683A patent/GEP20002329B/en unknown
- 1992-08-27 EP EP92114654A patent/EP0529636B1/en not_active Expired - Lifetime
- 1992-08-27 WO PCT/EP1992/001999 patent/WO1993005043A1/en not_active Ceased
- 1992-08-27 RU RU94019425/04A patent/RU2114827C1/ru not_active IP Right Cessation
- 1992-08-27 AT AT92114654T patent/ATE181552T1/de not_active IP Right Cessation
- 1992-08-27 DE DE69229461T patent/DE69229461T2/de not_active Expired - Lifetime
- 1992-08-27 HU HU9400595A patent/HUT70753A/hu unknown
- 1992-08-27 DK DK92114654T patent/DK0529636T3/da active
-
1994
- 1994-02-25 FI FI940889A patent/FI107156B/fi active
- 1994-02-25 NO NO940676A patent/NO301117B1/no unknown
-
1995
- 1995-06-21 HU HU95P/P00323P patent/HU211632A9/hu unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0432648B1 (en) * | 1989-12-11 | 1995-08-02 | Neurosearch A/S | Isatine derivatives, their preparation and use |
Also Published As
| Publication number | Publication date |
|---|---|
| WO1993005043A1 (en) | 1993-03-18 |
| AU655672B2 (en) | 1995-01-05 |
| FI107156B (fi) | 2001-06-15 |
| EP0529636A1 (en) | 1993-03-03 |
| FI940889A7 (fi) | 1994-02-25 |
| CZ39594A3 (en) | 1994-11-16 |
| NO940676D0 (no) | 1994-02-25 |
| SK23894A3 (en) | 1994-12-07 |
| NO301117B1 (no) | 1997-09-15 |
| MX9204914A (es) | 1993-07-01 |
| GEP20002329B (en) | 2000-12-25 |
| HU9400595D0 (en) | 1994-05-30 |
| DE69229461T2 (de) | 1999-10-21 |
| SK280578B6 (sk) | 2000-04-10 |
| JPH06510056A (ja) | 1994-11-10 |
| NO940676L (enExample) | 1994-04-27 |
| DK0529636T3 (da) | 1999-12-13 |
| CA2076948C (en) | 2002-04-16 |
| HUT70753A (en) | 1995-10-30 |
| FI940889A0 (fi) | 1994-02-25 |
| DE69229461D1 (de) | 1999-07-29 |
| HU211632A9 (en) | 1995-12-28 |
| AU2482092A (en) | 1993-04-05 |
| ATE181552T1 (de) | 1999-07-15 |
| JP3170584B2 (ja) | 2001-05-28 |
| PL170920B1 (pl) | 1997-02-28 |
| CA2076948A1 (en) | 1993-03-01 |
| EP0529636B1 (en) | 1999-06-23 |
| CZ282759B6 (cs) | 1997-09-17 |
| KR100277481B1 (ko) | 2001-02-01 |
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