SK18097A3 - Substituted omega £phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl| £alkyl, alkenyl or alkinyl|amino carboxamides, sulfonamides and phosphonyl amides, pharmaceutical preparation containing them, process for producing them and their use - Google Patents
Substituted omega £phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl| £alkyl, alkenyl or alkinyl|amino carboxamides, sulfonamides and phosphonyl amides, pharmaceutical preparation containing them, process for producing them and their use Download PDFInfo
- Publication number
- SK18097A3 SK18097A3 SK180-97A SK18097A SK18097A3 SK 18097 A3 SK18097 A3 SK 18097A3 SK 18097 A SK18097 A SK 18097A SK 18097 A3 SK18097 A3 SK 18097A3
- Authority
- SK
- Slovakia
- Prior art keywords
- butyl
- phenoxy
- imidazol
- benzenesulfonamide
- methyl
- Prior art date
Links
- -1 phenylthio, phenylsulfinyl Chemical group 0.000 title claims abstract description 33
- 229940124530 sulfonamide Drugs 0.000 title claims abstract description 6
- 238000000034 method Methods 0.000 title claims description 49
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 title claims description 23
- 125000000217 alkyl group Chemical group 0.000 title claims description 14
- 125000003342 alkenyl group Chemical group 0.000 title abstract description 3
- 150000003456 sulfonamides Chemical class 0.000 title abstract description 3
- 230000008569 process Effects 0.000 title description 3
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 title description 2
- 125000006193 alkinyl group Chemical group 0.000 title 1
- 239000000825 pharmaceutical preparation Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 108
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 26
- 229910052760 oxygen Inorganic materials 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 19
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- OOOGOCOFYSFFOK-UHFFFAOYSA-N 4-methyl-n-[4-(4-nitrophenoxy)butyl]benzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NCCCCOC1=CC=C([N+]([O-])=O)C=C1 OOOGOCOFYSFFOK-UHFFFAOYSA-N 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- XCOBRBQJQGKQHY-UHFFFAOYSA-N n-[4-(4-aminophenoxy)butyl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NCCCCOC1=CC=C(N)C=C1 XCOBRBQJQGKQHY-UHFFFAOYSA-N 0.000 claims description 4
- FIDDRSDUNJRIRR-UHFFFAOYSA-N n-[4-[4-[(4-methylphenyl)sulfonylamino]butylsulfanyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1SCCCCNS(=O)(=O)C1=CC=C(C)C=C1 FIDDRSDUNJRIRR-UHFFFAOYSA-N 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- 241000124008 Mammalia Species 0.000 claims description 3
- 206010003119 arrhythmia Diseases 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- KRCFUGNNUXRFGX-UHFFFAOYSA-N n-[4-(4-aminophenyl)sulfanylbutyl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NCCCCSC1=CC=C(N)C=C1 KRCFUGNNUXRFGX-UHFFFAOYSA-N 0.000 claims description 3
- NBJURKKEEIJFLX-UHFFFAOYSA-N 1-(4-bromophenyl)-3-[4-(4-imidazol-1-ylphenoxy)butyl]urea Chemical compound C1=CC(Br)=CC=C1NC(=O)NCCCCOC1=CC=C(N2C=NC=C2)C=C1 NBJURKKEEIJFLX-UHFFFAOYSA-N 0.000 claims description 2
- OUUYLYHUHZFEMN-UHFFFAOYSA-N 4-bromo-n-[3-(4-imidazol-1-ylphenoxy)propyl]benzamide Chemical compound C1=CC(Br)=CC=C1C(=O)NCCCOC1=CC=C(N2C=NC=C2)C=C1 OUUYLYHUHZFEMN-UHFFFAOYSA-N 0.000 claims description 2
- PMJXCXPDUMCWLB-UHFFFAOYSA-N 5-(aminomethyl)-n-[4-(4-imidazol-1-ylphenoxy)butyl]thiophene-2-sulfonamide Chemical compound S1C(CN)=CC=C1S(=O)(=O)NCCCCOC1=CC=C(N2C=NC=C2)C=C1 PMJXCXPDUMCWLB-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- DBFJCTHJACEXSG-UHFFFAOYSA-N n-[10-(4-imidazol-1-ylphenoxy)decyl]naphthalene-2-sulfonamide Chemical compound C=1C=C2C=CC=CC2=CC=1S(=O)(=O)NCCCCCCCCCCOC(C=C1)=CC=C1N1C=CN=C1 DBFJCTHJACEXSG-UHFFFAOYSA-N 0.000 claims description 2
- DWHOKBIEMWLGGE-UHFFFAOYSA-N n-[4-(4-acetylphenoxy)butyl]-4-bromobenzenesulfonamide Chemical compound C1=CC(C(=O)C)=CC=C1OCCCCNS(=O)(=O)C1=CC=C(Br)C=C1 DWHOKBIEMWLGGE-UHFFFAOYSA-N 0.000 claims description 2
- DLDVAWCWSRPZQR-UHFFFAOYSA-N n-[4-(4-benzoylphenoxy)butyl]-4-bromobenzenesulfonamide Chemical compound C1=CC(Br)=CC=C1S(=O)(=O)NCCCCOC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 DLDVAWCWSRPZQR-UHFFFAOYSA-N 0.000 claims description 2
- HAMCLKBMSLWVPK-UHFFFAOYSA-N n-[4-(4-imidazol-1-ylphenoxy)butyl]-1-methyl-2-oxobenzo[cd]indole-6-sulfonamide Chemical compound C1=CC(=C23)N(C)C(=O)C2=CC=CC3=C1S(=O)(=O)NCCCCOC(C=C1)=CC=C1N1C=CN=C1 HAMCLKBMSLWVPK-UHFFFAOYSA-N 0.000 claims description 2
- ZJSJOCXPWAFVMD-UHFFFAOYSA-N n-[4-(4-imidazol-1-ylphenoxy)butyl]-2,1,3-benzothiadiazole-4-sulfonamide Chemical compound C=1C=CC2=NSN=C2C=1S(=O)(=O)NCCCCOC(C=C1)=CC=C1N1C=CN=C1 ZJSJOCXPWAFVMD-UHFFFAOYSA-N 0.000 claims description 2
- JYTTXLSFYCTIQB-UHFFFAOYSA-N n-[4-(4-imidazol-1-ylphenoxy)butyl]benzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NCCCCOC(C=C1)=CC=C1N1C=CN=C1 JYTTXLSFYCTIQB-UHFFFAOYSA-N 0.000 claims description 2
- NPSCNELNMXQGKF-UHFFFAOYSA-N n-[4-(4-imidazol-1-ylphenoxy)butyl]naphthalene-2-sulfonamide Chemical compound C=1C=C2C=CC=CC2=CC=1S(=O)(=O)NCCCCOC(C=C1)=CC=C1N1C=CN=C1 NPSCNELNMXQGKF-UHFFFAOYSA-N 0.000 claims description 2
- FKMHTSVILZUKGI-UHFFFAOYSA-N n-[4-(4-imidazol-1-ylphenoxy)butyl]octane-1-sulfonamide Chemical compound C1=CC(OCCCCNS(=O)(=O)CCCCCCCC)=CC=C1N1C=NC=C1 FKMHTSVILZUKGI-UHFFFAOYSA-N 0.000 claims description 2
- STDYXNYZVIPYPC-UHFFFAOYSA-N n-[4-(4-imidazol-1-ylphenoxy)butyl]quinoline-8-sulfonamide Chemical compound C=1C=CC2=CC=CN=C2C=1S(=O)(=O)NCCCCOC(C=C1)=CC=C1N1C=CN=C1 STDYXNYZVIPYPC-UHFFFAOYSA-N 0.000 claims description 2
- PGLGVEBYEMPNSL-UHFFFAOYSA-N n-[4-(4-imidazol-1-ylphenoxy)butyl]thiophene-2-sulfonamide Chemical compound C=1C=CSC=1S(=O)(=O)NCCCCOC(C=C1)=CC=C1N1C=CN=C1 PGLGVEBYEMPNSL-UHFFFAOYSA-N 0.000 claims description 2
- KTDFNBDZADLIGL-UHFFFAOYSA-N n-[4-[4-(methanesulfonamido)phenyl]sulfanylbutyl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NCCCCSC1=CC=C(NS(C)(=O)=O)C=C1 KTDFNBDZADLIGL-UHFFFAOYSA-N 0.000 claims description 2
- SYOCHRVVTJBVMF-UHFFFAOYSA-N n-[5-(4-imidazol-1-ylphenoxy)pentyl]hexane-1-sulfonamide Chemical compound C1=CC(OCCCCCNS(=O)(=O)CCCCCC)=CC=C1N1C=NC=C1 SYOCHRVVTJBVMF-UHFFFAOYSA-N 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- QHKGOUZHYRYKDN-UHFFFAOYSA-N n-[4-(4-imidazol-1-ylphenoxy)butyl]-1-phenylmethanesulfonamide Chemical compound C=1C=C(N2C=NC=C2)C=CC=1OCCCCNS(=O)(=O)CC1=CC=CC=C1 QHKGOUZHYRYKDN-UHFFFAOYSA-N 0.000 claims 2
- ATDYDSYGGBABGY-UHFFFAOYSA-N 4-bromo-n-[4-[4-(tetrazol-1-yl)phenoxy]butyl]benzenesulfonamide Chemical compound C1=CC(Br)=CC=C1S(=O)(=O)NCCCCOC1=CC=C(N2N=NN=C2)C=C1 ATDYDSYGGBABGY-UHFFFAOYSA-N 0.000 claims 1
- QTLCZRXTNSWBAF-UHFFFAOYSA-N 4-bromo-n-[5-(4-imidazol-1-ylphenoxy)pentyl]benzamide Chemical compound C1=CC(Br)=CC=C1C(=O)NCCCCCOC1=CC=C(N2C=NC=C2)C=C1 QTLCZRXTNSWBAF-UHFFFAOYSA-N 0.000 claims 1
- ASMJPRUEKJPTHS-UHFFFAOYSA-N 4-bromo-n-[5-(4-imidazol-1-ylphenoxy)pentyl]benzenesulfonamide Chemical compound C1=CC(Br)=CC=C1S(=O)(=O)NCCCCCOC1=CC=C(N2C=NC=C2)C=C1 ASMJPRUEKJPTHS-UHFFFAOYSA-N 0.000 claims 1
- LMVFMSMZCMRSEY-UHFFFAOYSA-N 4-methyl-n-[4-[4-(2h-tetrazol-5-yl)phenoxy]butyl]benzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NCCCCOC1=CC=C(C=2NN=NN=2)C=C1 LMVFMSMZCMRSEY-UHFFFAOYSA-N 0.000 claims 1
- DLAIYOHLUSFTQS-UHFFFAOYSA-N n-[4-(4-imidazol-1-ylphenoxy)butyl]-2,1,3-benzoxadiazole-4-sulfonamide Chemical compound C=1C=CC2=NON=C2C=1S(=O)(=O)NCCCCOC(C=C1)=CC=C1N1C=CN=C1 DLAIYOHLUSFTQS-UHFFFAOYSA-N 0.000 claims 1
- OXCDREJBKUDFJL-UHFFFAOYSA-N n-[4-(4-imidazol-1-ylphenoxy)butyl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NCCCCOC1=CC=C(N2C=NC=C2)C=C1 OXCDREJBKUDFJL-UHFFFAOYSA-N 0.000 claims 1
- ADHWWGAPNDCATA-UHFFFAOYSA-N n-[4-(4-imidazol-1-ylphenoxy)butyl]-4-nitrobenzenesulfonamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NCCCCOC1=CC=C(N2C=NC=C2)C=C1 ADHWWGAPNDCATA-UHFFFAOYSA-N 0.000 claims 1
- UMLRJNJOZWRXSY-UHFFFAOYSA-N n-[4-(4-imidazol-1-ylphenoxy)butyl]naphthalene-1-carboxamide Chemical compound C=1C=CC2=CC=CC=C2C=1C(=O)NCCCCOC(C=C1)=CC=C1N1C=CN=C1 UMLRJNJOZWRXSY-UHFFFAOYSA-N 0.000 claims 1
- 239000003416 antiarrhythmic agent Substances 0.000 abstract description 11
- 150000003857 carboxamides Chemical class 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 221
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 105
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 99
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 79
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 78
- 235000019441 ethanol Nutrition 0.000 description 74
- 239000007787 solid Substances 0.000 description 66
- 239000000243 solution Substances 0.000 description 61
- 239000000203 mixture Substances 0.000 description 52
- 239000002244 precipitate Substances 0.000 description 52
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 41
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
- 239000011541 reaction mixture Substances 0.000 description 31
- 238000001953 recrystallisation Methods 0.000 description 29
- 238000010992 reflux Methods 0.000 description 29
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 28
- 239000000047 product Substances 0.000 description 28
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- 239000000706 filtrate Substances 0.000 description 21
- 239000002904 solvent Substances 0.000 description 18
- 239000000725 suspension Substances 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- 230000036982 action potential Effects 0.000 description 15
- 238000001816 cooling Methods 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- 239000007864 aqueous solution Substances 0.000 description 14
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 14
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 14
- 239000003921 oil Substances 0.000 description 13
- 235000019198 oils Nutrition 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 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 11
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
- 238000009835 boiling Methods 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- JQDUSOHGIHANJS-UHFFFAOYSA-N 2-[4-(4-acetylphenoxy)butyl]isoindole-1,3-dione Chemical compound C1=CC(C(=O)C)=CC=C1OCCCCN1C(=O)C2=CC=CC=C2C1=O JQDUSOHGIHANJS-UHFFFAOYSA-N 0.000 description 7
- QRIZORZKXLSBRO-UHFFFAOYSA-N 5-(4-imidazol-1-ylphenoxy)pentan-1-amine Chemical compound C1=CC(OCCCCCN)=CC=C1N1C=NC=C1 QRIZORZKXLSBRO-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 239000000523 sample Substances 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 238000004949 mass spectrometry Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- DENKGPBHLYFNGK-UHFFFAOYSA-N 4-bromobenzoyl chloride Chemical group ClC(=O)C1=CC=C(Br)C=C1 DENKGPBHLYFNGK-UHFFFAOYSA-N 0.000 description 5
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 5
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 5
- 230000003288 anthiarrhythmic effect Effects 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- DRLZMMIQNNWJQC-UHFFFAOYSA-N 2-[4-(4-nitrophenoxy)butyl]isoindole-1,3-dione Chemical compound C1=CC([N+](=O)[O-])=CC=C1OCCCCN1C(=O)C2=CC=CC=C2C1=O DRLZMMIQNNWJQC-UHFFFAOYSA-N 0.000 description 4
- ADGHNIFLKSLROX-UHFFFAOYSA-N 4-[4-(tetrazol-1-yl)phenoxy]butan-1-amine;hydrochloride Chemical compound Cl.C1=CC(OCCCCN)=CC=C1N1N=NN=C1 ADGHNIFLKSLROX-UHFFFAOYSA-N 0.000 description 4
- KMMHZIBWCXYAAH-UHFFFAOYSA-N 4-bromobenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C(Br)C=C1 KMMHZIBWCXYAAH-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 230000000747 cardiac effect Effects 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000002198 insoluble material Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 4
- 239000003039 volatile agent Substances 0.000 description 4
- JHMWPJKKCXHSPK-UHFFFAOYSA-N 2-[3-(4-imidazol-1-ylphenoxy)propyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCCOC(C=C1)=CC=C1N1C=CN=C1 JHMWPJKKCXHSPK-UHFFFAOYSA-N 0.000 description 3
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 239000007995 HEPES buffer Substances 0.000 description 3
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 3
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 3
- 102000004257 Potassium Channel Human genes 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 239000003570 air Substances 0.000 description 3
- MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 description 3
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- 229910052727 yttrium Inorganic materials 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
- C07D233/56—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/60—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/333—Radicals substituted by oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/17—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C317/34—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/46—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms
- C07C323/49—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms to sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/38—Amides of thiocarboxylic acids
- C07C327/48—Amides of thiocarboxylic acids having carbon atoms of thiocarboxamide groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/38—Amides of thiocarboxylic acids
- C07C327/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C327/52—Y being a hydrogen or a carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- C07D233/56—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/24—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/26—Radicals substituted by sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1241696P | 1996-02-28 | 1996-02-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK18097A3 true SK18097A3 (en) | 1997-10-08 |
Family
ID=21754868
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK180-97A SK18097A3 (en) | 1996-02-28 | 1997-02-06 | Substituted omega £phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl| £alkyl, alkenyl or alkinyl|amino carboxamides, sulfonamides and phosphonyl amides, pharmaceutical preparation containing them, process for producing them and their use |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US5877196A (cs) |
| EP (1) | EP0792873A1 (cs) |
| JP (1) | JPH09227482A (cs) |
| KR (1) | KR970061273A (cs) |
| AR (1) | AR005875A1 (cs) |
| AU (1) | AU1497497A (cs) |
| CA (1) | CA2197617A1 (cs) |
| CO (1) | CO4761059A1 (cs) |
| CZ (1) | CZ44697A3 (cs) |
| HU (1) | HUP9700457A3 (cs) |
| IL (1) | IL120177A0 (cs) |
| NO (1) | NO970689L (cs) |
| SK (1) | SK18097A3 (cs) |
| ZA (1) | ZA971741B (cs) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6500457B1 (en) | 2000-08-14 | 2002-12-31 | Peirce Management, Llc | Oral pharmaceutical dosage forms for pulsatile delivery of an antiarrhythmic agent |
| US8115005B2 (en) | 2006-08-04 | 2012-02-14 | Decode Genetics Ehf. | Pyrazolylphenyl and pyrrolylphenyl inhibitors of LTA4H for treating inflammation |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB769706A (en) * | 1954-04-30 | 1957-03-13 | May & Baker Ltd | Improvements in or relating to amines and to processes for their preparation |
| US2855401A (en) * | 1954-04-30 | 1958-10-07 | May & Baker Ltd | Certain n-(aminophenoxy pentyl) sulfonamide or saccharine compounds and higher homologues |
| US4804662A (en) * | 1987-05-05 | 1989-02-14 | Schering A.G. | Substituted 4-(1H-imidazol-1-yl)benzamides as antiarrhythmic agents |
| US4851526A (en) * | 1987-09-04 | 1989-07-25 | Schering A.G. | 1-(4-Substituted phenyl)-1H-imidazoles compounds |
| EP0424525B1 (en) * | 1987-12-11 | 1994-12-21 | Mitsui Petrochemical Industries, Ltd. | Novel amines and their use |
| US5149700A (en) * | 1990-05-30 | 1992-09-22 | American Home Products Corporation | Substituted arylsulfonamides and benzamides |
| US5395844A (en) * | 1993-06-10 | 1995-03-07 | The Du Pont Merck Pharmaceutical Company | Imidazole 5-position substituted angiotensin II antagonists |
| CA2189068A1 (en) * | 1994-04-27 | 1995-11-02 | Nobuo Mochizuki | Imidazole derivative and process for producing the same |
-
1997
- 1997-02-06 SK SK180-97A patent/SK18097A3/sk unknown
- 1997-02-07 IL IL12017797A patent/IL120177A0/xx unknown
- 1997-02-13 CZ CZ97446A patent/CZ44697A3/cs unknown
- 1997-02-14 CO CO97007674A patent/CO4761059A1/es unknown
- 1997-02-14 US US08/800,313 patent/US5877196A/en not_active Expired - Fee Related
- 1997-02-14 CA CA002197617A patent/CA2197617A1/en not_active Abandoned
- 1997-02-14 NO NO970689A patent/NO970689L/no unknown
- 1997-02-15 KR KR1019970004568A patent/KR970061273A/ko not_active Withdrawn
- 1997-02-17 AR ARP970100617A patent/AR005875A1/es unknown
- 1997-02-17 HU HU9700457A patent/HUP9700457A3/hu unknown
- 1997-02-17 JP JP9031871A patent/JPH09227482A/ja active Pending
- 1997-02-21 EP EP97301151A patent/EP0792873A1/en not_active Withdrawn
- 1997-02-27 ZA ZA971741A patent/ZA971741B/xx unknown
- 1997-02-27 AU AU14974/97A patent/AU1497497A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JPH09227482A (ja) | 1997-09-02 |
| AU1497497A (en) | 1997-09-04 |
| EP0792873A1 (en) | 1997-09-03 |
| CO4761059A1 (es) | 1999-04-27 |
| US5877196A (en) | 1999-03-02 |
| IL120177A0 (en) | 1997-06-10 |
| AR005875A1 (es) | 1999-07-21 |
| CZ44697A3 (en) | 1997-10-15 |
| HUP9700457A3 (en) | 1998-04-28 |
| NO970689D0 (no) | 1997-02-14 |
| CA2197617A1 (en) | 1997-08-28 |
| KR970061273A (ko) | 1997-09-12 |
| ZA971741B (en) | 1998-08-27 |
| NO970689L (no) | 1997-08-29 |
| HUP9700457A2 (en) | 1997-10-28 |
| HU9700457D0 (en) | 1997-04-28 |
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