NO323117B1 - Nye imidazolderivater - Google Patents
Nye imidazolderivater Download PDFInfo
- Publication number
- NO323117B1 NO323117B1 NO20023298A NO20023298A NO323117B1 NO 323117 B1 NO323117 B1 NO 323117B1 NO 20023298 A NO20023298 A NO 20023298A NO 20023298 A NO20023298 A NO 20023298A NO 323117 B1 NO323117 B1 NO 323117B1
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- compound according
- imidazole
- compound
- halogen
- Prior art date
Links
- 150000002460 imidazoles Chemical class 0.000 title claims description 7
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 87
- 150000003839 salts Chemical class 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 29
- -1 1,2,3,4-tetrahydronaphthyl Chemical group 0.000 claims description 21
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 208000035475 disorder Diseases 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 14
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 13
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000006239 protecting group Chemical group 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
- 208000001089 Multiple system atrophy Diseases 0.000 claims description 6
- 206010031127 Orthostatic hypotension Diseases 0.000 claims description 6
- 201000001880 Sexual dysfunction Diseases 0.000 claims description 6
- 208000010877 cognitive disease Diseases 0.000 claims description 6
- 206010012601 diabetes mellitus Diseases 0.000 claims description 6
- 230000002366 lipolytic effect Effects 0.000 claims description 6
- 230000000926 neurological effect Effects 0.000 claims description 6
- 208000020016 psychiatric disease Diseases 0.000 claims description 6
- 231100000872 sexual dysfunction Toxicity 0.000 claims description 6
- 208000012902 Nervous system disease Diseases 0.000 claims description 5
- 208000025966 Neurological disease Diseases 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 238000005984 hydrogenation reaction Methods 0.000 claims description 5
- 125000002950 monocyclic group Chemical group 0.000 claims description 5
- 125000006413 ring segment Chemical group 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- 239000000203 mixture Substances 0.000 description 53
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
- 239000000243 solution Substances 0.000 description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 238000005481 NMR spectroscopy Methods 0.000 description 28
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- 238000005160 1H NMR spectroscopy Methods 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 19
- 230000002829 reductive effect Effects 0.000 description 18
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 17
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- 238000003818 flash chromatography Methods 0.000 description 16
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 13
- 239000007858 starting material Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000012043 crude product Substances 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- 239000012074 organic phase Substances 0.000 description 11
- 238000010828 elution Methods 0.000 description 10
- 239000002585 base Substances 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- 125000002883 imidazolyl group Chemical group 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- RDAVSNJOLKWHAW-UHFFFAOYSA-N 5-[(6-methoxy-2-phenyl-2,3-dihydro-1h-inden-1-yl)methyl]-1h-imidazole Chemical compound C12=CC(OC)=CC=C2CC(C=2C=CC=CC=2)C1CC1=CNC=N1 RDAVSNJOLKWHAW-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 230000002093 peripheral effect Effects 0.000 description 6
- 239000005557 antagonist Substances 0.000 description 5
- 210000003169 central nervous system Anatomy 0.000 description 5
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 4
- MLXCJXRILGYHJL-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-(1h-imidazol-5-ylmethyl)-2,3-dihydro-1h-inden-5-ol Chemical compound C12=CC(O)=CC=C2C(C=2C=CC(F)=CC=2)CC1CC1=CNC=N1 MLXCJXRILGYHJL-UHFFFAOYSA-N 0.000 description 4
- TWCWRQKZLYENNZ-UHFFFAOYSA-N 3-(4-fluorophenyl)-1-(1-tritylimidazol-4-yl)-2,3-dihydroinden-1-ol Chemical compound C12=CC=CC=C2C(O)(C=2N=CN(C=2)C(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1C1=CC=C(F)C=C1 TWCWRQKZLYENNZ-UHFFFAOYSA-N 0.000 description 4
- SIUOTMYWHGODQX-UHFFFAOYSA-N 3-phenyl-2,3-dihydroinden-1-one Chemical compound C12=CC=CC=C2C(=O)CC1C1=CC=CC=C1 SIUOTMYWHGODQX-UHFFFAOYSA-N 0.000 description 4
- GOJFKMHLWLYNBH-UHFFFAOYSA-N 5-[[3-(3-fluorophenyl)-2,3-dihydro-1h-inden-1-yl]methyl]-1h-imidazole Chemical compound FC1=CC=CC(C2C3=CC=CC=C3C(CC=3N=CNC=3)C2)=C1 GOJFKMHLWLYNBH-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 208000008589 Obesity Diseases 0.000 description 4
- 239000000556 agonist Substances 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 235000020824 obesity Nutrition 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- WTXGWOZYWVGLDH-UHFFFAOYSA-N 1-(4-hydroxyphenyl)-3-(1h-imidazol-5-ylmethyl)-2,3-dihydro-1h-inden-5-ol Chemical compound C1=CC(O)=CC=C1C1C2=CC=C(O)C=C2C(CC=2N=CNC=2)C1 WTXGWOZYWVGLDH-UHFFFAOYSA-N 0.000 description 3
- BRFLLKLCDHLSCU-UHFFFAOYSA-N 1-benzyl-5-[(2-phenyl-2,3-dihydroinden-1-ylidene)methyl]imidazole Chemical compound C1=NC=C(C=C2C3=CC=CC=C3CC2C=2C=CC=CC=2)N1CC1=CC=CC=C1 BRFLLKLCDHLSCU-UHFFFAOYSA-N 0.000 description 3
- ITHXOKQJEXLMKO-UHFFFAOYSA-N 2-benzylidene-3h-inden-1-one Chemical compound C1C2=CC=CC=C2C(=O)C1=CC1=CC=CC=C1 ITHXOKQJEXLMKO-UHFFFAOYSA-N 0.000 description 3
- MVZZRCWDWNZKGX-UHFFFAOYSA-N 3-(4-fluorophenyl)-2,3-dihydroinden-1-one Chemical compound C1=CC(F)=CC=C1C1C2=CC=CC=C2C(=O)C1 MVZZRCWDWNZKGX-UHFFFAOYSA-N 0.000 description 3
- XOTQQHSMEGDQGO-UHFFFAOYSA-N 3-benzyl-2,3-dihydroinden-1-one Chemical compound C12=CC=CC=C2C(=O)CC1CC1=CC=CC=C1 XOTQQHSMEGDQGO-UHFFFAOYSA-N 0.000 description 3
- QONDAZCJAPQGRX-UHFFFAOYSA-N 3-benzylimidazole-4-carbaldehyde Chemical compound O=CC1=CN=CN1CC1=CC=CC=C1 QONDAZCJAPQGRX-UHFFFAOYSA-N 0.000 description 3
- QZYVNLNWFONUOG-UHFFFAOYSA-N 5-(3-benzyl-3h-inden-1-yl)-1h-imidazole Chemical compound C=1C=CC=CC=1CC(C1=CC=CC=C11)C=C1C1=CNC=N1 QZYVNLNWFONUOG-UHFFFAOYSA-N 0.000 description 3
- XQUZPPYDWLBMEA-UHFFFAOYSA-N 5-(3-phenyl-2,3-dihydro-1h-inden-1-yl)-1h-imidazole Chemical compound C12=CC=CC=C2C(C=2C=CC=CC=2)CC1C1=CNC=N1 XQUZPPYDWLBMEA-UHFFFAOYSA-N 0.000 description 3
- SQACLOFFUVKLKK-UHFFFAOYSA-N 5-[3-(4-fluorophenyl)-3h-inden-1-yl]-1h-imidazole Chemical compound C1=CC(F)=CC=C1C1C2=CC=CC=C2C(C=2N=CNC=2)=C1 SQACLOFFUVKLKK-UHFFFAOYSA-N 0.000 description 3
- VNFHZPUJRVFYNB-UHFFFAOYSA-N 5-[[3-(4-fluorophenyl)-2,3-dihydro-1h-inden-1-yl]methyl]-1h-imidazole Chemical compound C1=CC(F)=CC=C1C1C2=CC=CC=C2C(CC=2N=CNC=2)C1 VNFHZPUJRVFYNB-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- 239000007818 Grignard reagent Substances 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- DEQYTNZJHKPYEZ-UHFFFAOYSA-N ethyl acetate;heptane Chemical compound CCOC(C)=O.CCCCCCC DEQYTNZJHKPYEZ-UHFFFAOYSA-N 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 150000004795 grignard reagents Chemical class 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 2
- NHUQYXSTNXLJIW-PTNGSMBKSA-N (z)-3-(4-methoxyphenyl)-2-phenylprop-2-enoic acid Chemical compound C1=CC(OC)=CC=C1\C=C(/C(O)=O)C1=CC=CC=C1 NHUQYXSTNXLJIW-PTNGSMBKSA-N 0.000 description 2
- SWNMRBGOGHBQGB-UHFFFAOYSA-N 1-(3-benzylimidazol-4-yl)-4,4-diphenylbutan-1-ol Chemical compound C=1N=CN(CC=2C=CC=CC=2)C=1C(O)CCC(C=1C=CC=CC=1)C1=CC=CC=C1 SWNMRBGOGHBQGB-UHFFFAOYSA-N 0.000 description 2
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 2
- NPJJCEQBLQZWLT-UHFFFAOYSA-N 1-benzyl-5-[(3-phenyl-3,4-dihydro-2h-naphthalen-1-ylidene)methyl]imidazole Chemical compound C1=NC=C(C=C2C3=CC=CC=C3CC(C2)C=2C=CC=CC=2)N1CC1=CC=CC=C1 NPJJCEQBLQZWLT-UHFFFAOYSA-N 0.000 description 2
- PCRICPYPVZKEBZ-UHFFFAOYSA-N 2,3-diphenylpropanoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)CC1=CC=CC=C1 PCRICPYPVZKEBZ-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
- OCLCRYNZYRSURW-UHFFFAOYSA-N 2-phenyl-2,3-dihydroinden-1-one Chemical compound C1C2=CC=CC=C2C(=O)C1C1=CC=CC=C1 OCLCRYNZYRSURW-UHFFFAOYSA-N 0.000 description 2
- DXITZFQOLLONTP-UHFFFAOYSA-N 3-(1h-imidazol-5-ylmethyl)-2-phenyl-2,3-dihydro-1h-inden-5-ol Chemical compound C12=CC(O)=CC=C2CC(C=2C=CC=CC=2)C1CC1=CNC=N1 DXITZFQOLLONTP-UHFFFAOYSA-N 0.000 description 2
- GIROORGDVPRQFZ-UHFFFAOYSA-N 3-(4-methoxyphenyl)-2-phenylpropanoic acid Chemical compound C1=CC(OC)=CC=C1CC(C(O)=O)C1=CC=CC=C1 GIROORGDVPRQFZ-UHFFFAOYSA-N 0.000 description 2
- ZTGXKXXLYABOAU-UHFFFAOYSA-N 3-(4-methoxyphenyl)-2-phenylpropanoyl chloride Chemical compound C1=CC(OC)=CC=C1CC(C(Cl)=O)C1=CC=CC=C1 ZTGXKXXLYABOAU-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- HDEGFOUETXLYQV-UHFFFAOYSA-N 3-benzyl-1-(1-tritylimidazol-4-yl)-2,3-dihydroinden-1-ol Chemical compound C12=CC=CC=C2C(O)(C=2N=CN(C=2)C(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1CC1=CC=CC=C1 HDEGFOUETXLYQV-UHFFFAOYSA-N 0.000 description 2
- JPMMRLDUVLFPNX-UHFFFAOYSA-N 3-cyclohexyl-2,3-dihydroinden-1-one Chemical compound C12=CC=CC=C2C(=O)CC1C1CCCCC1 JPMMRLDUVLFPNX-UHFFFAOYSA-N 0.000 description 2
- DXJZJYPLPZEYBH-UHFFFAOYSA-N 4-iodo-1-tritylimidazole Chemical compound C1=NC(I)=CN1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 DXJZJYPLPZEYBH-UHFFFAOYSA-N 0.000 description 2
- DCPHEWUKTBAXET-UHFFFAOYSA-N 5-(1-hydroxy-3-phenyl-2,3-dihydroinden-1-yl)-n,n-dimethylimidazole-1-sulfonamide Chemical compound CN(C)S(=O)(=O)N1C=NC=C1C1(O)C2=CC=CC=C2C(C=2C=CC=CC=2)C1 DCPHEWUKTBAXET-UHFFFAOYSA-N 0.000 description 2
- GBSVRWVLYCSQDF-UHFFFAOYSA-N 5-(3-benzyl-2,3-dihydro-1h-inden-1-yl)-1h-imidazole Chemical compound C=1C=CC=CC=1CC(C1=CC=CC=C11)CC1C1=CNC=N1 GBSVRWVLYCSQDF-UHFFFAOYSA-N 0.000 description 2
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 229940126142 compound 16 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 229960003914 desipramine Drugs 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000011978 dissolution method Methods 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000000763 evoking effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- YRRWNBMOJMMXQY-UHFFFAOYSA-N n,n-dimethylimidazole-1-sulfonamide Chemical compound CN(C)S(=O)(=O)N1C=CN=C1 YRRWNBMOJMMXQY-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229960002748 norepinephrine Drugs 0.000 description 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 210000001428 peripheral nervous system Anatomy 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 210000001177 vas deferen Anatomy 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- BIDDLDNGQCUOJQ-SDNWHVSQSA-N α-phenylcinnamic acid Chemical compound C=1C=CC=CC=1/C(C(=O)O)=C\C1=CC=CC=C1 BIDDLDNGQCUOJQ-SDNWHVSQSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Reproductive Health (AREA)
- Emergency Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI20000073A FI20000073A0 (fi) | 2000-01-14 | 2000-01-14 | Uusia imidatsolijohdannaisia |
| PCT/FI2001/000030 WO2001051472A1 (en) | 2000-01-14 | 2001-01-12 | New imidazole derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20023298D0 NO20023298D0 (no) | 2002-07-08 |
| NO20023298L NO20023298L (no) | 2002-09-06 |
| NO323117B1 true NO323117B1 (no) | 2007-01-08 |
Family
ID=8557065
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20023298A NO323117B1 (no) | 2000-01-14 | 2002-07-08 | Nye imidazolderivater |
Country Status (30)
| Country | Link |
|---|---|
| EP (1) | EP1261588B1 (et) |
| JP (1) | JP2003519688A (et) |
| KR (1) | KR20020084091A (et) |
| CN (1) | CN1187336C (et) |
| AR (1) | AR029432A1 (et) |
| AT (1) | ATE280161T1 (et) |
| AU (1) | AU769896B2 (et) |
| BR (1) | BR0107644A (et) |
| CA (1) | CA2397283A1 (et) |
| CZ (1) | CZ20022358A3 (et) |
| DE (1) | DE60106572T2 (et) |
| DK (1) | DK1261588T3 (et) |
| EE (1) | EE200200389A (et) |
| ES (1) | ES2228884T3 (et) |
| FI (1) | FI20000073A0 (et) |
| GC (1) | GC0000218A (et) |
| HK (1) | HK1049999B (et) |
| HU (1) | HUP0301008A3 (et) |
| IL (1) | IL150506A0 (et) |
| MX (1) | MXPA02006872A (et) |
| NO (1) | NO323117B1 (et) |
| NZ (1) | NZ519919A (et) |
| PE (1) | PE20011230A1 (et) |
| PL (1) | PL207281B1 (et) |
| PT (1) | PT1261588E (et) |
| RU (1) | RU2265598C2 (et) |
| SI (1) | SI1261588T1 (et) |
| SK (1) | SK286320B6 (et) |
| WO (1) | WO2001051472A1 (et) |
| ZA (1) | ZA200205301B (et) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI20002756A0 (fi) * | 2000-12-15 | 2000-12-15 | Orion Yhtymae Oyj | Uusi hoitomenetelmä |
| TW200930291A (en) * | 2002-04-29 | 2009-07-16 | Bayer Cropscience Ag | Pesticidal heterocycles |
| FI20022159A0 (fi) * | 2002-12-05 | 2002-12-05 | Orion Corp | Uusia farmaseuttisia yhdisteitä |
| DE102004035322A1 (de) * | 2004-07-21 | 2006-02-16 | Universität des Saarlandes | Selektive Hemmstoffe humaner Corticoidsynthasen |
| ES2381589T3 (es) | 2006-10-19 | 2012-05-29 | F. Hoffmann-La Roche Ag | Aminometil-4-imidazoles |
| RU2456281C2 (ru) | 2006-11-16 | 2012-07-20 | Ф. Хоффманн-Ля Рош Аг | Замещенные 4-имидазолы, способ их получения и их применение |
| US20080146523A1 (en) | 2006-12-18 | 2008-06-19 | Guido Galley | Imidazole derivatives |
| AR090557A1 (es) * | 2012-04-02 | 2014-11-19 | Orion Corp | DERIVADOS IMIDAZOLICOS AGONISTAS ADRENERGICOS a2 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2225782A (en) * | 1988-12-09 | 1990-06-13 | Farmos Group Limited | Imidazole derivatives useful for treatment of diabetes |
| GB2244431A (en) * | 1990-05-31 | 1991-12-04 | Farmos Oy | Treatment of age related memory impairment and other cognitive disorders |
| US5541211A (en) * | 1991-06-18 | 1996-07-30 | Orion-Yhtyma Oy | Administration of atipamezole to elicit a yohimbine-like alpha-adrenoreceptor antagonistic noradrenergic transmission |
| GB9127050D0 (en) * | 1991-12-20 | 1992-02-19 | Orion Yhtymae Oy | Substituted imidazole derivatives and their preparation and use |
| GB9520150D0 (en) * | 1995-10-03 | 1995-12-06 | Orion Yhtymae Oy | New imidazole derivatives |
| NZ504667A (en) * | 1997-12-04 | 2003-03-28 | Allergan Sales Inc | Substituted imidazole derivatives having agonist-like activity at alpha 2B or 2B/2C adrenergic receptors |
| US6503935B1 (en) * | 1998-08-07 | 2003-01-07 | Abbott Laboratories | Imidazoles and related compounds as α1A agonists |
| TWI283669B (en) * | 1999-06-10 | 2007-07-11 | Allergan Inc | Compounds and method of treatment having agonist-like activity selective at alpha 2B or 2B/2C adrenergic receptors |
-
2000
- 2000-01-14 FI FI20000073A patent/FI20000073A0/fi unknown
-
2001
- 2001-01-10 GC GCP20011133 patent/GC0000218A/en active
- 2001-01-12 JP JP2001551854A patent/JP2003519688A/ja active Pending
- 2001-01-12 NZ NZ519919A patent/NZ519919A/en unknown
- 2001-01-12 SK SK998-2002A patent/SK286320B6/sk not_active IP Right Cessation
- 2001-01-12 CN CNB018037194A patent/CN1187336C/zh not_active Expired - Fee Related
- 2001-01-12 AU AU28532/01A patent/AU769896B2/en not_active Ceased
- 2001-01-12 SI SI200130256T patent/SI1261588T1/xx unknown
- 2001-01-12 PL PL356884A patent/PL207281B1/pl not_active IP Right Cessation
- 2001-01-12 PT PT01942360T patent/PT1261588E/pt unknown
- 2001-01-12 AR ARP010100140A patent/AR029432A1/es unknown
- 2001-01-12 RU RU2002121777/04A patent/RU2265598C2/ru not_active IP Right Cessation
- 2001-01-12 DK DK01942360T patent/DK1261588T3/da active
- 2001-01-12 AT AT01942360T patent/ATE280161T1/de not_active IP Right Cessation
- 2001-01-12 MX MXPA02006872A patent/MXPA02006872A/es active IP Right Grant
- 2001-01-12 KR KR1020027009037A patent/KR20020084091A/ko not_active Application Discontinuation
- 2001-01-12 ES ES01942360T patent/ES2228884T3/es not_active Expired - Lifetime
- 2001-01-12 CZ CZ20022358A patent/CZ20022358A3/cs unknown
- 2001-01-12 EE EEP200200389A patent/EE200200389A/et unknown
- 2001-01-12 EP EP01942360A patent/EP1261588B1/en not_active Expired - Lifetime
- 2001-01-12 PE PE2001000029A patent/PE20011230A1/es not_active Application Discontinuation
- 2001-01-12 BR BR0107644-2A patent/BR0107644A/pt not_active Application Discontinuation
- 2001-01-12 CA CA002397283A patent/CA2397283A1/en not_active Abandoned
- 2001-01-12 IL IL15050601A patent/IL150506A0/xx not_active IP Right Cessation
- 2001-01-12 DE DE60106572T patent/DE60106572T2/de not_active Expired - Lifetime
- 2001-01-12 WO PCT/FI2001/000030 patent/WO2001051472A1/en active IP Right Grant
- 2001-01-12 HU HU0301008A patent/HUP0301008A3/hu unknown
-
2002
- 2002-07-02 ZA ZA200205301A patent/ZA200205301B/xx unknown
- 2002-07-08 NO NO20023298A patent/NO323117B1/no not_active IP Right Cessation
-
2003
- 2003-03-19 HK HK03102023.4A patent/HK1049999B/zh not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |