UA65572C2 - Substituted imidazoles, intermediate compounds for the preparation thereof, a method for the preparation of substituted imidazoles and a method for the treatment of inflammatory diseases - Google Patents
Substituted imidazoles, intermediate compounds for the preparation thereof, a method for the preparation of substituted imidazoles and a method for the treatment of inflammatory diseases Download PDFInfo
- Publication number
- UA65572C2 UA65572C2 UA99105811A UA99105811A UA65572C2 UA 65572 C2 UA65572 C2 UA 65572C2 UA 99105811 A UA99105811 A UA 99105811A UA 99105811 A UA99105811 A UA 99105811A UA 65572 C2 UA65572 C2 UA 65572C2
- Authority
- UA
- Ukraine
- Prior art keywords
- group
- alkyl
- substituted
- fluorophenyl
- imidazole
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 123
- 150000002460 imidazoles Chemical class 0.000 title claims abstract description 33
- 238000000034 method Methods 0.000 title claims description 22
- 208000027866 inflammatory disease Diseases 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 5
- 102000004127 Cytokines Human genes 0.000 claims abstract description 21
- 108090000695 Cytokines Proteins 0.000 claims abstract description 21
- 239000000543 intermediate Substances 0.000 claims abstract description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 17
- 201000010099 disease Diseases 0.000 claims abstract description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 56
- -1 vinylene, ethynylene Chemical group 0.000 claims description 44
- 125000001072 heteroaryl group Chemical group 0.000 claims description 35
- 229910052736 halogen Inorganic materials 0.000 claims description 34
- 150000002367 halogens Chemical class 0.000 claims description 34
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 29
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 16
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- 229910052740 iodine Inorganic materials 0.000 claims description 12
- 150000002825 nitriles Chemical class 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 11
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 229920002554 vinyl polymer Polymers 0.000 claims description 11
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 10
- 239000011630 iodine Substances 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 10
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 9
- 125000006413 ring segment Chemical group 0.000 claims description 9
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 8
- 229910052763 palladium Inorganic materials 0.000 claims description 8
- 125000005544 phthalimido group Chemical group 0.000 claims description 8
- 239000007822 coupling agent Substances 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000002560 nitrile group Chemical group 0.000 claims description 6
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 6
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
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- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 5
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 150000007530 organic bases Chemical class 0.000 claims description 4
- QSUSKMBNZQHHPA-UHFFFAOYSA-N 4-[4-(4-fluorophenyl)-1-(3-phenylpropyl)-5-pyridin-4-ylimidazol-2-yl]but-3-yn-1-ol Chemical compound C=1C=CC=CC=1CCCN1C(C#CCCO)=NC(C=2C=CC(F)=CC=2)=C1C1=CC=NC=C1 QSUSKMBNZQHHPA-UHFFFAOYSA-N 0.000 claims description 3
- IMWNIKIDZJRIGK-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)-2-iodo-3-(3-phenylpropyl)imidazol-4-yl]pyridine Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CN=CC=2)N(CCCC=2C=CC=CC=2)C(I)=N1 IMWNIKIDZJRIGK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- QOERMZSCFCZYCO-UHFFFAOYSA-N 4-[4-(4-fluorophenyl)-1-(3-phenylpropyl)-5-pyridin-4-ylimidazol-2-yl]-n,n-dimethylbut-3-yn-1-amine Chemical compound C=1C=CC=CC=1CCCN1C(C#CCCN(C)C)=NC(C=2C=CC(F)=CC=2)=C1C1=CC=NC=C1 QOERMZSCFCZYCO-UHFFFAOYSA-N 0.000 claims description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000003544 oxime group Chemical group 0.000 claims description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 8
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- YJYGOGWMDDTIIU-UHFFFAOYSA-N 3-[4-(4-fluorophenyl)-1-(3-phenylpropyl)-5-pyridin-4-ylimidazol-2-yl]prop-2-yn-1-ol Chemical compound C=1C=CC=CC=1CCCN1C(C#CCO)=NC(C=2C=CC(F)=CC=2)=C1C1=CC=NC=C1 YJYGOGWMDDTIIU-UHFFFAOYSA-N 0.000 claims 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- HCXJFMDOHDNDCC-UHFFFAOYSA-N 5-$l^{1}-oxidanyl-3,4-dihydropyrrol-2-one Chemical group O=C1CCC(=O)[N]1 HCXJFMDOHDNDCC-UHFFFAOYSA-N 0.000 claims 2
- IHHLHKLBHIEAOK-UHFFFAOYSA-N 5-[4-(4-fluorophenyl)-1-(3-phenylpropyl)-5-pyridin-4-ylimidazol-2-yl]pent-4-yn-1-ol Chemical compound C=1C=CC=CC=1CCCN1C(C#CCCCO)=NC(C=2C=CC(F)=CC=2)=C1C1=CC=NC=C1 IHHLHKLBHIEAOK-UHFFFAOYSA-N 0.000 claims 2
- 230000001419 dependent effect Effects 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000006596 (C1-C3) alkylcarbonyloxy group Chemical group 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
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- ADFYINPKHOEJJY-UHFFFAOYSA-N 4-[2-bromo-5-(4-fluorophenyl)-3-(3-phenylpropyl)imidazol-4-yl]pyridine Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CN=CC=2)N(CCCC=2C=CC=CC=2)C(Br)=N1 ADFYINPKHOEJJY-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4425297P | 1997-04-24 | 1997-04-24 | |
| PCT/US1998/007910 WO1998047892A1 (en) | 1997-04-24 | 1998-04-17 | Substituted imidazoles useful in the treatment of inflammatory diseases |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA65572C2 true UA65572C2 (en) | 2004-04-15 |
Family
ID=21931339
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA99105811A UA65572C2 (en) | 1997-04-24 | 1998-04-17 | Substituted imidazoles, intermediate compounds for the preparation thereof, a method for the preparation of substituted imidazoles and a method for the treatment of inflammatory diseases |
Country Status (24)
| Country | Link |
|---|---|
| US (3) | US5965583A (da) |
| EP (1) | EP1028954B1 (da) |
| JP (1) | JP2001522357A (da) |
| KR (1) | KR100568438B1 (da) |
| CN (1) | CN1211381C (da) |
| AR (1) | AR012594A1 (da) |
| AT (1) | ATE244234T1 (da) |
| AU (1) | AU7138298A (da) |
| BR (1) | BR9808998A (da) |
| CA (1) | CA2297176A1 (da) |
| DE (1) | DE69816109T2 (da) |
| DK (1) | DK1028954T3 (da) |
| ES (1) | ES2202840T3 (da) |
| HU (1) | HUP0002842A3 (da) |
| IL (1) | IL132318A0 (da) |
| NO (1) | NO318937B1 (da) |
| NZ (1) | NZ500447A (da) |
| PL (1) | PL191111B1 (da) |
| PT (1) | PT1028954E (da) |
| RU (1) | RU2222534C2 (da) |
| TR (1) | TR199902622T2 (da) |
| UA (1) | UA65572C2 (da) |
| WO (1) | WO1998047892A1 (da) |
| ZA (1) | ZA983451B (da) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2963572D1 (en) * | 1978-04-11 | 1982-10-21 | Ciba Geigy Ag | Mercapto-imidazole derivatives, their preparation, mercapto-imidazole derivatives for the treatment of inflammatory diseases and their pharmaceutical compositions |
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-
1998
- 1998-04-17 UA UA99105811A patent/UA65572C2/uk unknown
- 1998-04-17 RU RU99122164/04A patent/RU2222534C2/ru not_active IP Right Cessation
- 1998-04-17 CN CNB988045230A patent/CN1211381C/zh not_active Expired - Fee Related
- 1998-04-17 US US09/062,304 patent/US5965583A/en not_active Expired - Lifetime
- 1998-04-17 DK DK98918463T patent/DK1028954T3/da active
- 1998-04-17 CA CA002297176A patent/CA2297176A1/en not_active Abandoned
- 1998-04-17 EP EP98918463A patent/EP1028954B1/en not_active Expired - Lifetime
- 1998-04-17 PT PT98918463T patent/PT1028954E/pt unknown
- 1998-04-17 HU HU0002842A patent/HUP0002842A3/hu unknown
- 1998-04-17 WO PCT/US1998/007910 patent/WO1998047892A1/en not_active Application Discontinuation
- 1998-04-17 JP JP54623198A patent/JP2001522357A/ja not_active Withdrawn
- 1998-04-17 IL IL13231898A patent/IL132318A0/xx not_active IP Right Cessation
- 1998-04-17 ES ES98918463T patent/ES2202840T3/es not_active Expired - Lifetime
- 1998-04-17 AU AU71382/98A patent/AU7138298A/en not_active Abandoned
- 1998-04-17 TR TR1999/02622T patent/TR199902622T2/xx unknown
- 1998-04-17 KR KR1019997009785A patent/KR100568438B1/ko not_active IP Right Cessation
- 1998-04-17 NZ NZ500447A patent/NZ500447A/en unknown
- 1998-04-17 AT AT98918463T patent/ATE244234T1/de not_active IP Right Cessation
- 1998-04-17 BR BR9808998-6A patent/BR9808998A/pt not_active Application Discontinuation
- 1998-04-17 DE DE69816109T patent/DE69816109T2/de not_active Expired - Fee Related
- 1998-04-17 PL PL336758A patent/PL191111B1/pl not_active IP Right Cessation
- 1998-04-23 AR ARP980101886A patent/AR012594A1/es not_active Application Discontinuation
- 1998-04-23 ZA ZA9803451A patent/ZA983451B/xx unknown
-
1999
- 1999-04-20 US US09/295,156 patent/US6214830B1/en not_active Expired - Lifetime
- 1999-10-19 NO NO19995095A patent/NO318937B1/no unknown
-
2000
- 2000-11-03 US US09/705,508 patent/US6521655B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP2001522357A (ja) | 2001-11-13 |
| PL336758A1 (en) | 2000-07-17 |
| US5965583A (en) | 1999-10-12 |
| AU7138298A (en) | 1998-11-13 |
| CN1253558A (zh) | 2000-05-17 |
| IL132318A0 (en) | 2001-03-19 |
| DE69816109D1 (de) | 2003-08-07 |
| ES2202840T3 (es) | 2004-04-01 |
| US6521655B1 (en) | 2003-02-18 |
| EP1028954B1 (en) | 2003-07-02 |
| KR100568438B1 (ko) | 2006-04-07 |
| CA2297176A1 (en) | 1998-10-29 |
| TR199902622T2 (xx) | 2000-05-22 |
| NO318937B1 (no) | 2005-05-30 |
| PL191111B1 (pl) | 2006-03-31 |
| CN1211381C (zh) | 2005-07-20 |
| NO995095D0 (no) | 1999-10-19 |
| ZA983451B (en) | 1999-10-25 |
| BR9808998A (pt) | 2000-08-08 |
| RU2222534C2 (ru) | 2004-01-27 |
| DK1028954T3 (da) | 2003-10-27 |
| KR20010020204A (ko) | 2001-03-15 |
| AR012594A1 (es) | 2000-11-08 |
| PT1028954E (pt) | 2003-11-28 |
| US6214830B1 (en) | 2001-04-10 |
| DE69816109T2 (de) | 2004-04-22 |
| EP1028954A1 (en) | 2000-08-23 |
| HUP0002842A3 (en) | 2002-01-28 |
| HUP0002842A2 (hu) | 2001-06-28 |
| NO995095L (no) | 1999-12-09 |
| ATE244234T1 (de) | 2003-07-15 |
| NZ500447A (en) | 2001-09-28 |
| WO1998047892A1 (en) | 1998-10-29 |
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