UA74593C2 - Substituted imidazopyridines - Google Patents
Substituted imidazopyridines Download PDFInfo
- Publication number
- UA74593C2 UA74593C2 UA2003042937A UA2003042937A UA74593C2 UA 74593 C2 UA74593 C2 UA 74593C2 UA 2003042937 A UA2003042937 A UA 2003042937A UA 2003042937 A UA2003042937 A UA 2003042937A UA 74593 C2 UA74593 C2 UA 74593C2
- Authority
- UA
- Ukraine
- Prior art keywords
- alkyl
- compound
- aryl
- butyl
- animal
- Prior art date
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- 150000005232 imidazopyridines Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 128
- 102000004127 Cytokines Human genes 0.000 claims abstract description 28
- 108090000695 Cytokines Proteins 0.000 claims abstract description 28
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 21
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 20
- 201000010099 disease Diseases 0.000 claims abstract description 20
- 230000003612 virological effect Effects 0.000 claims abstract description 12
- 230000001613 neoplastic effect Effects 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 69
- 150000003839 salts Chemical class 0.000 claims description 33
- 241001465754 Metazoa Species 0.000 claims description 31
- 125000003342 alkenyl group Chemical group 0.000 claims description 25
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- -1 fluorobenzenesulfonamide monohydrate Chemical class 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 125000004450 alkenylene group Chemical group 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 8
- 230000001939 inductive effect Effects 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004043 oxo group Chemical group O=* 0.000 claims description 3
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 28
- 230000028993 immune response Effects 0.000 abstract description 14
- 238000011282 treatment Methods 0.000 abstract description 13
- 150000001412 amines Chemical group 0.000 abstract description 7
- 239000003607 modifier Substances 0.000 abstract description 6
- 125000004857 imidazopyridinyl group Chemical class N1C(=NC2=C1C=CC=N2)* 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 141
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 60
- 238000006243 chemical reaction Methods 0.000 description 60
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 239000011541 reaction mixture Substances 0.000 description 42
- 239000000243 solution Substances 0.000 description 42
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 31
- 239000003921 oil Substances 0.000 description 27
- 235000019198 oils Nutrition 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 21
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
- 239000000126 substance Substances 0.000 description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
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- 238000004458 analytical method Methods 0.000 description 11
- 239000000741 silica gel Substances 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- 230000003993 interaction Effects 0.000 description 10
- 239000010410 layer Substances 0.000 description 10
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 235000019341 magnesium sulphate Nutrition 0.000 description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
- 206010028980 Neoplasm Diseases 0.000 description 9
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- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 8
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- 239000012044 organic layer Substances 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
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- SKKTUOZKZKCGTB-UHFFFAOYSA-N butyl carbamate Chemical compound CCCCOC(N)=O SKKTUOZKZKCGTB-UHFFFAOYSA-N 0.000 description 7
- 230000006698 induction Effects 0.000 description 7
- 210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 238000007796 conventional method Methods 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000012442 inert solvent Substances 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 102000003390 tumor necrosis factor Human genes 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 102000014150 Interferons Human genes 0.000 description 4
- 108010050904 Interferons Proteins 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 208000036142 Viral infection Diseases 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 4
- 229940079322 interferon Drugs 0.000 description 4
- HNQIVZYLYMDVSB-NJFSPNSNSA-N methanesulfonamide Chemical compound [14CH3]S(N)(=O)=O HNQIVZYLYMDVSB-NJFSPNSNSA-N 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 239000012266 salt solution Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- QAHVHSLSRLSVGS-UHFFFAOYSA-N sulfamoyl chloride Chemical compound NS(Cl)(=O)=O QAHVHSLSRLSVGS-UHFFFAOYSA-N 0.000 description 4
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 230000009385 viral infection Effects 0.000 description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 3
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 3
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
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- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
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- 238000012360 testing method Methods 0.000 description 3
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 2
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- CEGLXJGCOGYSFS-UHFFFAOYSA-N 2,4-dichloro-5,6-dimethyl-3-nitropyridine Chemical compound CC1=NC(Cl)=C([N+]([O-])=O)C(Cl)=C1C CEGLXJGCOGYSFS-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
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- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 2
- XUXVVQKJULMMKX-UHFFFAOYSA-N 1,1,1-trimethoxypentane Chemical compound CCCCC(OC)(OC)OC XUXVVQKJULMMKX-UHFFFAOYSA-N 0.000 description 1
- HZPOJEMKSPPRCT-UHFFFAOYSA-N 1,2-dihydroimidazo[4,5-b]pyridin-4-amine Chemical class NN1C=CC=C2NCN=C12 HZPOJEMKSPPRCT-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25422800P | 2000-12-08 | 2000-12-08 | |
| PCT/US2001/046915 WO2002046194A2 (en) | 2000-12-08 | 2001-12-06 | Substituted imidazopyridines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA74593C2 true UA74593C2 (en) | 2006-01-16 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2003042937A UA74593C2 (en) | 2000-12-08 | 2001-06-12 | Substituted imidazopyridines |
Country Status (23)
| Country | Link |
|---|---|
| EP (1) | EP1343783A2 (cs) |
| JP (1) | JP2004525868A (cs) |
| KR (1) | KR20030070048A (cs) |
| CN (1) | CN1249062C (cs) |
| AR (1) | AR035670A1 (cs) |
| AU (2) | AU3954702A (cs) |
| BR (1) | BR0116034A (cs) |
| CA (1) | CA2431040A1 (cs) |
| CZ (1) | CZ20031593A3 (cs) |
| EE (1) | EE200300273A (cs) |
| HR (1) | HRP20030465A2 (cs) |
| HU (1) | HUP0600592A2 (cs) |
| IL (1) | IL155885A0 (cs) |
| MX (1) | MXPA03005013A (cs) |
| NO (1) | NO20032453L (cs) |
| NZ (1) | NZ526085A (cs) |
| PL (1) | PL365739A1 (cs) |
| RU (1) | RU2294934C2 (cs) |
| SK (1) | SK7142003A3 (cs) |
| TW (1) | TWI243819B (cs) |
| UA (1) | UA74593C2 (cs) |
| WO (1) | WO2002046194A2 (cs) |
| ZA (1) | ZA200305238B (cs) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2498984C2 (ru) * | 2007-09-12 | 2013-11-20 | Сентр Насьональ Де Ла Решерш Сьентифик | Перхаридины в качестве ингибиторов cdk |
Families Citing this family (71)
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|---|---|---|---|---|
| US5741908A (en) | 1996-06-21 | 1998-04-21 | Minnesota Mining And Manufacturing Company | Process for reparing imidazoquinolinamines |
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2001
- 2001-06-12 UA UA2003042937A patent/UA74593C2/uk unknown
- 2001-12-06 RU RU2003116648/04A patent/RU2294934C2/ru active
- 2001-12-06 KR KR10-2003-7007533A patent/KR20030070048A/ko not_active Withdrawn
- 2001-12-06 SK SK714-2003A patent/SK7142003A3/sk unknown
- 2001-12-06 JP JP2002547931A patent/JP2004525868A/ja active Pending
- 2001-12-06 AU AU3954702A patent/AU3954702A/xx active Pending
- 2001-12-06 WO PCT/US2001/046915 patent/WO2002046194A2/en not_active Ceased
- 2001-12-06 EP EP01987315A patent/EP1343783A2/en not_active Withdrawn
- 2001-12-06 HR HR20030465A patent/HRP20030465A2/hr not_active Application Discontinuation
- 2001-12-06 PL PL01365739A patent/PL365739A1/xx not_active Application Discontinuation
- 2001-12-06 HU HU0600592A patent/HUP0600592A2/hu unknown
- 2001-12-06 CN CNB018198570A patent/CN1249062C/zh not_active Expired - Fee Related
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- 2001-12-06 CA CA002431040A patent/CA2431040A1/en not_active Abandoned
- 2001-12-06 CZ CZ20031593A patent/CZ20031593A3/cs unknown
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2498984C2 (ru) * | 2007-09-12 | 2013-11-20 | Сентр Насьональ Де Ла Решерш Сьентифик | Перхаридины в качестве ингибиторов cdk |
Also Published As
| Publication number | Publication date |
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| EE200300273A (et) | 2004-02-16 |
| KR20030070048A (ko) | 2003-08-27 |
| HUP0600592A2 (en) | 2006-11-28 |
| AU2002239547B2 (en) | 2006-11-30 |
| CA2431040A1 (en) | 2002-06-13 |
| CN1478090A (zh) | 2004-02-25 |
| AR035670A1 (es) | 2004-06-23 |
| EP1343783A2 (en) | 2003-09-17 |
| NZ526085A (en) | 2004-12-24 |
| NO20032453D0 (no) | 2003-05-28 |
| AU3954702A (en) | 2002-06-18 |
| CN1249062C (zh) | 2006-04-05 |
| RU2294934C2 (ru) | 2007-03-10 |
| TWI243819B (en) | 2005-11-21 |
| CZ20031593A3 (cs) | 2004-01-14 |
| NO20032453L (no) | 2003-07-16 |
| JP2004525868A (ja) | 2004-08-26 |
| BR0116034A (pt) | 2004-08-03 |
| WO2002046194A3 (en) | 2003-02-06 |
| IL155885A0 (en) | 2003-12-23 |
| ZA200305238B (en) | 2004-08-27 |
| HK1063466A1 (en) | 2004-12-31 |
| PL365739A1 (en) | 2005-01-10 |
| SK7142003A3 (en) | 2003-10-07 |
| HRP20030465A2 (en) | 2004-06-30 |
| WO2002046194A2 (en) | 2002-06-13 |
| RU2003116648A (ru) | 2005-02-10 |
| MXPA03005013A (es) | 2003-09-05 |
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