NO310655B1 - Forbindelse, preparat omfattende denne, fremgangsmåte for fremstilling av forbindelsen samt anvendelse - Google Patents
Forbindelse, preparat omfattende denne, fremgangsmåte for fremstilling av forbindelsen samt anvendelse Download PDFInfo
- Publication number
- NO310655B1 NO310655B1 NO19975663A NO975663A NO310655B1 NO 310655 B1 NO310655 B1 NO 310655B1 NO 19975663 A NO19975663 A NO 19975663A NO 975663 A NO975663 A NO 975663A NO 310655 B1 NO310655 B1 NO 310655B1
- Authority
- NO
- Norway
- Prior art keywords
- hydrogen
- semicarbazone
- benzaldehyde semicarbazone
- benzaldehyde
- oxygen
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 113
- 238000002360 preparation method Methods 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 12
- 239000000203 mixture Substances 0.000 title description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 65
- 239000001257 hydrogen Substances 0.000 claims abstract description 64
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 27
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 27
- 239000001301 oxygen Substances 0.000 claims abstract description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 25
- 206010010904 Convulsion Diseases 0.000 claims abstract description 20
- 241001465754 Metazoa Species 0.000 claims abstract description 20
- -1 C3-9cycloalkyl Chemical group 0.000 claims abstract description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 210000003169 central nervous system Anatomy 0.000 claims abstract description 11
- 230000036461 convulsion Effects 0.000 claims abstract description 8
- 229910052717 sulfur Chemical group 0.000 claims abstract description 8
- 239000011593 sulfur Chemical group 0.000 claims abstract description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 6
- 125000006545 (C1-C9) alkyl group Chemical group 0.000 claims abstract description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 37
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
- 150000001299 aldehydes Chemical class 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
- 239000002244 precipitate Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 229940079593 drug Drugs 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
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- 125000001475 halogen functional group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 150000002576 ketones Chemical class 0.000 claims description 5
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 claims description 5
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims description 5
- AKGUXECGGCUDCV-UXBLZVDNSA-N [(e)-benzylideneamino]urea Chemical compound NC(=O)N\N=C\C1=CC=CC=C1 AKGUXECGGCUDCV-UXBLZVDNSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
- KQSDBATZVOQQQY-UHFFFAOYSA-N (4-formylphenyl) 4-chlorobenzoate Chemical compound C1=CC(Cl)=CC=C1C(=O)OC1=CC=C(C=O)C=C1 KQSDBATZVOQQQY-UHFFFAOYSA-N 0.000 claims description 3
- KYZWJGYDXCOKRS-UHFFFAOYSA-N (4-formylphenyl) benzoate Chemical compound C1=CC(C=O)=CC=C1OC(=O)C1=CC=CC=C1 KYZWJGYDXCOKRS-UHFFFAOYSA-N 0.000 claims description 3
- ZWDVQMVZZYIAHO-UHFFFAOYSA-N 2-fluorobenzaldehyde Chemical compound FC1=CC=CC=C1C=O ZWDVQMVZZYIAHO-UHFFFAOYSA-N 0.000 claims description 3
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
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- 150000002367 halogens Chemical class 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- CPXYGYOMIMOSCX-YRNVUSSQSA-N [(e)-1-phenylethylideneamino]urea Chemical compound NC(=O)N\N=C(/C)C1=CC=CC=C1 CPXYGYOMIMOSCX-YRNVUSSQSA-N 0.000 claims 6
- CIRHAKPWVMBBTB-XFXZXTDPSA-N [(z)-1-phenylpropylideneamino]urea Chemical compound NC(=O)N/N=C(/CC)C1=CC=CC=C1 CIRHAKPWVMBBTB-XFXZXTDPSA-N 0.000 claims 4
- BHPATIXAOIQWHQ-QGMBQPNBSA-N [(e)-[4-(2,4-difluorophenoxy)phenyl]methylideneamino]urea Chemical compound C1=CC(/C=N/NC(=O)N)=CC=C1OC1=CC=C(F)C=C1F BHPATIXAOIQWHQ-QGMBQPNBSA-N 0.000 claims 2
- LMOPONJGKKKIHW-QGMBQPNBSA-N [(e)-[4-(2,5-difluorophenoxy)phenyl]methylideneamino]urea Chemical compound C1=CC(/C=N/NC(=O)N)=CC=C1OC1=CC(F)=CC=C1F LMOPONJGKKKIHW-QGMBQPNBSA-N 0.000 claims 2
- FXGVKAGWKGONDY-RQZCQDPDSA-N [(e)-[4-(2-fluorophenoxy)phenyl]methylideneamino]urea Chemical compound C1=CC(/C=N/NC(=O)N)=CC=C1OC1=CC=CC=C1F FXGVKAGWKGONDY-RQZCQDPDSA-N 0.000 claims 2
- ZUTQBSQKJGTKCW-LICLKQGHSA-N [(e)-[4-(2-methylphenoxy)phenyl]methylideneamino]urea Chemical compound CC1=CC=CC=C1OC1=CC=C(\C=N\NC(N)=O)C=C1 ZUTQBSQKJGTKCW-LICLKQGHSA-N 0.000 claims 2
- RMNIZJBVMFHIGN-QGMBQPNBSA-N [(e)-[4-(3,4-difluorophenoxy)phenyl]methylideneamino]urea Chemical compound C1=CC(/C=N/NC(=O)N)=CC=C1OC1=CC=C(F)C(F)=C1 RMNIZJBVMFHIGN-QGMBQPNBSA-N 0.000 claims 2
- SKSVDBVQOMQIQU-LICLKQGHSA-N [(e)-[4-(3-methylphenoxy)phenyl]methylideneamino]urea Chemical compound CC1=CC=CC(OC=2C=CC(\C=N\NC(N)=O)=CC=2)=C1 SKSVDBVQOMQIQU-LICLKQGHSA-N 0.000 claims 2
- WFKAOJIZWYQQOA-RQZCQDPDSA-N [(e)-[4-(4-bromophenoxy)phenyl]methylideneamino]urea Chemical compound C1=CC(/C=N/NC(=O)N)=CC=C1OC1=CC=C(Br)C=C1 WFKAOJIZWYQQOA-RQZCQDPDSA-N 0.000 claims 2
- BINXDPOTJMIGSI-RQZCQDPDSA-N [(e)-[4-(4-iodophenoxy)phenyl]methylideneamino]urea Chemical compound C1=CC(/C=N/NC(=O)N)=CC=C1OC1=CC=C(I)C=C1 BINXDPOTJMIGSI-RQZCQDPDSA-N 0.000 claims 2
- LPTHMNSRTDOFIV-LSCVHKIXSA-N [(z)-[4-(2,3-difluorophenoxy)phenyl]methylideneamino]urea Chemical compound C1=CC(\C=N/NC(=O)N)=CC=C1OC1=CC=CC(F)=C1F LPTHMNSRTDOFIV-LSCVHKIXSA-N 0.000 claims 2
- OUVRQJKXNVXDLL-MFOYZWKCSA-N [(z)-[4-(3-fluorophenoxy)phenyl]methylideneamino]urea Chemical compound C1=CC(\C=N/NC(=O)N)=CC=C1OC1=CC=CC(F)=C1 OUVRQJKXNVXDLL-MFOYZWKCSA-N 0.000 claims 2
- NDIGMDVZEBQULC-UHFFFAOYSA-N [[4-(2-bromo-4-fluorophenoxy)phenyl]methylideneamino]urea Chemical compound C1=CC(C=NNC(=O)N)=CC=C1OC1=CC=C(F)C=C1Br NDIGMDVZEBQULC-UHFFFAOYSA-N 0.000 claims 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/06—Compounds containing any of the groups, e.g. semicarbazides
- C07C281/08—Compounds containing any of the groups, e.g. semicarbazides the other nitrogen atom being further doubly-bound to a carbon atom, e.g. semicarbazones
- C07C281/14—Compounds containing any of the groups, e.g. semicarbazides the other nitrogen atom being further doubly-bound to a carbon atom, e.g. semicarbazones the carbon atom being further bound to a carbon atom of a six-membered aromatic ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/17—Amides, e.g. hydroxamic acids having the group >N—C(O)—N< or >N—C(S)—N<, e.g. urea, thiourea, carmustine
- A61K31/175—Amides, e.g. hydroxamic acids having the group >N—C(O)—N< or >N—C(S)—N<, e.g. urea, thiourea, carmustine having the group, >N—C(O)—N=N— or, e.g. carbonohydrazides, carbazones, semicarbazides, semicarbazones; Thioanalogues thereof
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurology (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
- Medicines Containing Plant Substances (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/475,313 US5741818A (en) | 1995-06-07 | 1995-06-07 | Semicarbazones having CNS activity and pharmaceutical preparations containing same |
| PCT/CA1996/000380 WO1996040628A1 (en) | 1995-06-07 | 1996-06-07 | Semicarbazones having cns activity and pharmaceutical preparations containing same |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO975663D0 NO975663D0 (no) | 1997-12-05 |
| NO975663L NO975663L (no) | 1998-02-09 |
| NO310655B1 true NO310655B1 (no) | 2001-08-06 |
Family
ID=23887035
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19975663A NO310655B1 (no) | 1995-06-07 | 1997-12-05 | Forbindelse, preparat omfattende denne, fremgangsmåte for fremstilling av forbindelsen samt anvendelse |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US5741818A (sv) |
| EP (1) | EP0836591B1 (sv) |
| JP (1) | JPH11506109A (sv) |
| KR (1) | KR19990022408A (sv) |
| CN (1) | CN1062263C (sv) |
| AT (1) | ATE206110T1 (sv) |
| AU (1) | AU715897B2 (sv) |
| BR (1) | BR9609408A (sv) |
| CA (1) | CA2223935A1 (sv) |
| CZ (1) | CZ387497A3 (sv) |
| DE (1) | DE69615558T2 (sv) |
| DK (1) | DK0836591T3 (sv) |
| ES (1) | ES2164889T3 (sv) |
| FI (1) | FI974447A (sv) |
| GE (1) | GEP20012414B (sv) |
| HU (1) | HUP9802637A3 (sv) |
| IL (1) | IL122350A0 (sv) |
| NO (1) | NO310655B1 (sv) |
| NZ (1) | NZ309707A (sv) |
| PL (1) | PL184048B1 (sv) |
| PT (1) | PT836591E (sv) |
| RU (1) | RU2174115C2 (sv) |
| UA (1) | UA62915C2 (sv) |
| WO (1) | WO1996040628A1 (sv) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5741818A (en) | 1995-06-07 | 1998-04-21 | University Of Saskatchewan | Semicarbazones having CNS activity and pharmaceutical preparations containing same |
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| AR029489A1 (es) | 2000-03-10 | 2003-07-02 | Euro Celtique Sa | Piridinas, pirimidinas, pirazinas, triazinas sustituidas por arilo, composiciones farmaceuticas y el uso de las mismas para la manufactura de un medicamento |
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| US3251064A (en) | 1962-11-13 | 1966-05-10 | Everett M Schultz | beta-aminoacylphenoxy-and beta-aminoacylphenylmercapto-derivatives of monocarboxylicacids |
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| US5266585A (en) | 1981-05-12 | 1993-11-30 | Ciba-Geigy Corporation | Arylphenyl ether derivatives, compositions containing these compounds and use thereof |
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| US4454337A (en) * | 1981-06-29 | 1984-06-12 | Smithkline Beckman Corporation | Semicarbazide intermediates for preparing 4-substituted indoles |
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| WO1994006758A1 (en) * | 1992-09-21 | 1994-03-31 | University Of Saskatchewan | Aryl semicarbazone anticonvulsants |
| AU2641295A (en) | 1994-05-17 | 1995-12-05 | Dowelanco | N-(5-isothiazolyl)amide pesticides |
| US5741818A (en) | 1995-06-07 | 1998-04-21 | University Of Saskatchewan | Semicarbazones having CNS activity and pharmaceutical preparations containing same |
| CZ132798A3 (cs) | 1995-10-30 | 1999-02-17 | Smithkline Beecham Corporation | Inhibitory proteázy |
-
1995
- 1995-06-07 US US08/475,313 patent/US5741818A/en not_active Ceased
-
1996
- 1996-06-07 PL PL96323666A patent/PL184048B1/pl unknown
- 1996-06-07 NZ NZ309707A patent/NZ309707A/en unknown
- 1996-06-07 CZ CZ973874A patent/CZ387497A3/cs unknown
- 1996-06-07 RU RU98100258/04A patent/RU2174115C2/ru not_active IP Right Cessation
- 1996-06-07 DK DK96917304T patent/DK0836591T3/da active
- 1996-06-07 JP JP9500044A patent/JPH11506109A/ja not_active Withdrawn
- 1996-06-07 AT AT96917304T patent/ATE206110T1/de not_active IP Right Cessation
- 1996-06-07 ES ES96917304T patent/ES2164889T3/es not_active Expired - Lifetime
- 1996-06-07 PT PT96917304T patent/PT836591E/pt unknown
- 1996-06-07 WO PCT/CA1996/000380 patent/WO1996040628A1/en not_active Application Discontinuation
- 1996-06-07 GE GEAP19964053A patent/GEP20012414B/en unknown
- 1996-06-07 KR KR1019970708888A patent/KR19990022408A/ko not_active Application Discontinuation
- 1996-06-07 HU HU9802637A patent/HUP9802637A3/hu unknown
- 1996-06-07 CN CN96195385A patent/CN1062263C/zh not_active Expired - Fee Related
- 1996-06-07 AU AU59938/96A patent/AU715897B2/en not_active Ceased
- 1996-06-07 DE DE69615558T patent/DE69615558T2/de not_active Expired - Fee Related
- 1996-06-07 BR BR9609408A patent/BR9609408A/pt not_active Application Discontinuation
- 1996-06-07 CA CA002223935A patent/CA2223935A1/en not_active Abandoned
- 1996-06-07 IL IL12235096A patent/IL122350A0/xx unknown
- 1996-06-07 EP EP96917304A patent/EP0836591B1/en not_active Expired - Lifetime
- 1996-07-06 UA UA98010024A patent/UA62915C2/uk unknown
-
1997
- 1997-12-05 NO NO19975663A patent/NO310655B1/no not_active IP Right Cessation
- 1997-12-05 FI FI974447A patent/FI974447A/sv unknown
-
2000
- 2000-04-20 US US09/556,910 patent/USRE38425E1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ES2164889T3 (es) | 2002-03-01 |
| EP0836591A1 (en) | 1998-04-22 |
| IL122350A0 (en) | 1998-04-05 |
| CN1190388A (zh) | 1998-08-12 |
| EP0836591B1 (en) | 2001-09-26 |
| US5741818A (en) | 1998-04-21 |
| PT836591E (pt) | 2002-03-28 |
| CZ387497A3 (cs) | 1998-07-15 |
| FI974447A0 (sv) | 1997-12-05 |
| ATE206110T1 (de) | 2001-10-15 |
| DE69615558T2 (de) | 2002-07-11 |
| BR9609408A (pt) | 1999-07-27 |
| FI974447A (sv) | 1997-12-05 |
| JPH11506109A (ja) | 1999-06-02 |
| AU715897B2 (en) | 2000-02-10 |
| CN1062263C (zh) | 2001-02-21 |
| NZ309707A (en) | 1998-11-25 |
| UA62915C2 (en) | 2004-01-15 |
| CA2223935A1 (en) | 1996-12-19 |
| RU2174115C2 (ru) | 2001-09-27 |
| PL184048B1 (pl) | 2002-08-30 |
| AU5993896A (en) | 1996-12-30 |
| HUP9802637A3 (en) | 2000-09-28 |
| NO975663L (no) | 1998-02-09 |
| KR19990022408A (ko) | 1999-03-25 |
| DE69615558D1 (de) | 2001-10-31 |
| HUP9802637A2 (hu) | 1999-02-01 |
| NO975663D0 (no) | 1997-12-05 |
| WO1996040628A1 (en) | 1996-12-19 |
| PL323666A1 (en) | 1998-04-14 |
| USRE38425E1 (en) | 2004-02-10 |
| DK0836591T3 (da) | 2001-11-26 |
| GEP20012414B (en) | 2001-04-25 |
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