NO970689L - Anti-arrytmiske midler - Google Patents
Anti-arrytmiske midlerInfo
- Publication number
- NO970689L NO970689L NO970689A NO970689A NO970689L NO 970689 L NO970689 L NO 970689L NO 970689 A NO970689 A NO 970689A NO 970689 A NO970689 A NO 970689A NO 970689 L NO970689 L NO 970689L
- Authority
- NO
- Norway
- Prior art keywords
- butyl
- phenoxy
- imidazol
- benzenesulfonamide
- methyl
- Prior art date
Links
- 239000003416 antiarrhythmic agent Substances 0.000 title description 11
- 150000001875 compounds Chemical class 0.000 claims description 137
- 239000000203 mixture Substances 0.000 claims description 60
- 238000000034 method Methods 0.000 claims description 49
- -1 1-imidazolyl Chemical group 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 16
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 10
- 230000015572 biosynthetic process Effects 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 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
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 3
- 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 3
- YICWCAXQBGBRDJ-UHFFFAOYSA-N n-[4-(4-cyanophenoxy)butyl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NCCCCOC1=CC=C(C#N)C=C1 YICWCAXQBGBRDJ-UHFFFAOYSA-N 0.000 claims description 3
- 206010003119 arrhythmia Diseases 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 2
- JYTTXLSFYCTIQB-UHFFFAOYSA-N n-[4-(4-imidazol-1-ylphenoxy)butyl]benzenesulfonamide Chemical group C=1C=CC=CC=1S(=O)(=O)NCCCCOC(C=C1)=CC=C1N1C=CN=C1 JYTTXLSFYCTIQB-UHFFFAOYSA-N 0.000 claims 2
- LDDXTXPTJGEKNA-UHFFFAOYSA-N 2,5-dichloro-n-[4-(4-imidazol-1-ylphenoxy)butyl]benzenesulfonamide Chemical compound ClC1=CC=C(Cl)C(S(=O)(=O)NCCCCOC=2C=CC(=CC=2)N2C=NC=C2)=C1 LDDXTXPTJGEKNA-UHFFFAOYSA-N 0.000 claims 1
- ZCRIMOOGRBXUPS-UHFFFAOYSA-N 2-[4-(4-imidazol-1-ylphenoxy)butyl]-4-methoxybenzenesulfonamide Chemical group COC1=CC=C(S(N)(=O)=O)C(CCCCOC=2C=CC(=CC=2)N2C=NC=C2)=C1 ZCRIMOOGRBXUPS-UHFFFAOYSA-N 0.000 claims 1
- DDJRFTHHGLSBAQ-UHFFFAOYSA-N 2-bromo-n-[4-(4-imidazol-1-ylphenoxy)butyl]benzamide Chemical compound BrC1=CC=CC=C1C(=O)NCCCCOC1=CC=C(N2C=NC=C2)C=C1 DDJRFTHHGLSBAQ-UHFFFAOYSA-N 0.000 claims 1
- UZERMWSWPIRNKX-UHFFFAOYSA-N 3-bromo-n-[4-(4-imidazol-1-ylphenoxy)butyl]benzamide Chemical compound BrC1=CC=CC(C(=O)NCCCCOC=2C=CC(=CC=2)N2C=NC=C2)=C1 UZERMWSWPIRNKX-UHFFFAOYSA-N 0.000 claims 1
- LTYMIWSOMZWOJI-UHFFFAOYSA-N 4-bromo-n-[3-[4-(methanesulfonamido)phenoxy]propyl]benzamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1OCCCNC(=O)C1=CC=C(Br)C=C1 LTYMIWSOMZWOJI-UHFFFAOYSA-N 0.000 claims 1
- PCKLHILXEISMRU-UHFFFAOYSA-N 4-bromo-n-[4-(4-imidazol-1-ylphenoxy)butyl]benzenesulfonamide Chemical compound C1=CC(Br)=CC=C1S(=O)(=O)NCCCCOC1=CC=C(N2C=NC=C2)C=C1 PCKLHILXEISMRU-UHFFFAOYSA-N 0.000 claims 1
- IFXTXRJOFLANPM-UHFFFAOYSA-N 4-bromo-n-[4-(4-pyrimidin-4-ylphenoxy)butyl]benzenesulfonamide Chemical compound C1=CC(Br)=CC=C1S(=O)(=O)NCCCCOC1=CC=C(C=2N=CN=CC=2)C=C1 IFXTXRJOFLANPM-UHFFFAOYSA-N 0.000 claims 1
- ATDYDSYGGBABGY-UHFFFAOYSA-N 4-bromo-n-[4-[4-(tetrazol-1-yl)phenoxy]butyl]benzenesulfonamide Chemical group C1=CC(Br)=CC=C1S(=O)(=O)NCCCCOC1=CC=C(N2N=NN=C2)C=C1 ATDYDSYGGBABGY-UHFFFAOYSA-N 0.000 claims 1
- ASMJPRUEKJPTHS-UHFFFAOYSA-N 4-bromo-n-[5-(4-imidazol-1-ylphenoxy)pentyl]benzenesulfonamide Chemical group C1=CC(Br)=CC=C1S(=O)(=O)NCCCCCOC1=CC=C(N2C=NC=C2)C=C1 ASMJPRUEKJPTHS-UHFFFAOYSA-N 0.000 claims 1
- DRSPQRABKITGGB-UHFFFAOYSA-N 4-butoxy-n-[4-(4-imidazol-1-ylphenoxy)butyl]benzenesulfonamide Chemical group C1=CC(OCCCC)=CC=C1S(=O)(=O)NCCCCOC1=CC=C(N2C=NC=C2)C=C1 DRSPQRABKITGGB-UHFFFAOYSA-N 0.000 claims 1
- CZHOPESURGXOST-UHFFFAOYSA-N 4-chloro-2-[4-(4-imidazol-1-ylphenoxy)butyl]benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(Cl)C=C1CCCCOC1=CC=C(N2C=NC=C2)C=C1 CZHOPESURGXOST-UHFFFAOYSA-N 0.000 claims 1
- ORQQCFSNVXXGPI-UHFFFAOYSA-N 4-cyano-n-[4-(4-imidazol-1-ylphenoxy)butyl]benzenesulfonamide Chemical compound C=1C=C(C#N)C=CC=1S(=O)(=O)NCCCCOC(C=C1)=CC=C1N1C=CN=C1 ORQQCFSNVXXGPI-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
- VEZCVJOXCLIKAZ-UHFFFAOYSA-N 4-methyl-n-[4-[4-(tetrazol-1-yl)phenoxy]butyl]benzenesulfonamide Chemical group C1=CC(C)=CC=C1S(=O)(=O)NCCCCOC1=CC=C(N2N=NN=C2)C=C1 VEZCVJOXCLIKAZ-UHFFFAOYSA-N 0.000 claims 1
- FCQKPXLWWUGXCV-UHFFFAOYSA-N 4-tert-butyl-n-[4-(4-imidazol-1-ylphenoxy)butyl]benzenesulfonamide Chemical group C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)NCCCCOC1=CC=C(N2C=NC=C2)C=C1 FCQKPXLWWUGXCV-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 241000124008 Mammalia Species 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- ZHCSMNFSVQYPTO-UHFFFAOYSA-N n-(dimethylaminomethylidene)-4-[4-[(4-methylphenyl)sulfonylamino]butoxy]benzenecarbothioamide Chemical compound C1=CC(C(=S)N=CN(C)C)=CC=C1OCCCCNS(=O)(=O)C1=CC=C(C)C=C1 ZHCSMNFSVQYPTO-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- HAMCLKBMSLWVPK-UHFFFAOYSA-N n-[4-(4-imidazol-1-ylphenoxy)butyl]-1-methyl-2-oxobenzo[cd]indole-6-sulfonamide Chemical group 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 1
- 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 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
- RSZGLHFMQILRTH-UHFFFAOYSA-N n-[4-(4-imidazol-1-ylphenoxy)butyl]-2,4,6-trimethylbenzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NCCCCOC1=CC=C(N2C=NC=C2)C=C1 RSZGLHFMQILRTH-UHFFFAOYSA-N 0.000 claims 1
- DGYBHONWKWDUJS-UHFFFAOYSA-N n-[4-(4-imidazol-1-ylphenoxy)butyl]-4-(trifluoromethyl)benzenesulfonamide Chemical compound C1=CC(C(F)(F)F)=CC=C1S(=O)(=O)NCCCCOC1=CC=C(N2C=NC=C2)C=C1 DGYBHONWKWDUJS-UHFFFAOYSA-N 0.000 claims 1
- DYKSWAMCYYVZLO-UHFFFAOYSA-N n-[4-(4-imidazol-1-ylphenoxy)butyl]-4-iodobenzamide Chemical compound C1=CC(I)=CC=C1C(=O)NCCCCOC1=CC=C(N2C=NC=C2)C=C1 DYKSWAMCYYVZLO-UHFFFAOYSA-N 0.000 claims 1
- ABPCRHFNUPWMGG-UHFFFAOYSA-N n-[4-(4-imidazol-1-ylphenoxy)butyl]-4-iodobenzenesulfonamide Chemical compound C1=CC(I)=CC=C1S(=O)(=O)NCCCCOC1=CC=C(N2C=NC=C2)C=C1 ABPCRHFNUPWMGG-UHFFFAOYSA-N 0.000 claims 1
- BIUHPUXUAMJCKO-UHFFFAOYSA-N n-[4-(4-imidazol-1-ylphenoxy)butyl]-4-methoxybenzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NCCCCOC1=CC=C(N2C=NC=C2)C=C1 BIUHPUXUAMJCKO-UHFFFAOYSA-N 0.000 claims 1
- DWGQEENVPJAKJS-UHFFFAOYSA-N n-[4-(4-imidazol-1-ylphenoxy)butyl]-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)NCCCCOC1=CC=C(N2C=NC=C2)C=C1 DWGQEENVPJAKJS-UHFFFAOYSA-N 0.000 claims 1
- OXCDREJBKUDFJL-UHFFFAOYSA-N n-[4-(4-imidazol-1-ylphenoxy)butyl]-4-methylbenzenesulfonamide Chemical group 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 group C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NCCCCOC1=CC=C(N2C=NC=C2)C=C1 ADHWWGAPNDCATA-UHFFFAOYSA-N 0.000 claims 1
- TVNAOXOZEFTJNI-UHFFFAOYSA-N n-[4-(4-imidazol-1-ylphenoxy)butyl]benzamide Chemical compound C=1C=CC=CC=1C(=O)NCCCCOC(C=C1)=CC=C1N1C=CN=C1 TVNAOXOZEFTJNI-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
- 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 1
- 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 1
- STDYXNYZVIPYPC-UHFFFAOYSA-N n-[4-(4-imidazol-1-ylphenoxy)butyl]quinoline-8-sulfonamide Chemical group C=1C=CC2=CC=CN=C2C=1S(=O)(=O)NCCCCOC(C=C1)=CC=C1N1C=CN=C1 STDYXNYZVIPYPC-UHFFFAOYSA-N 0.000 claims 1
- PGLGVEBYEMPNSL-UHFFFAOYSA-N n-[4-(4-imidazol-1-ylphenoxy)butyl]thiophene-2-sulfonamide Chemical group C=1C=CSC=1S(=O)(=O)NCCCCOC(C=C1)=CC=C1N1C=CN=C1 PGLGVEBYEMPNSL-UHFFFAOYSA-N 0.000 claims 1
- RYDBDHLPYVLUSN-UHFFFAOYSA-N n-[4-[4-(4-imidazol-1-ylphenoxy)butylsulfamoyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)NCCCCOC1=CC=C(N2C=NC=C2)C=C1 RYDBDHLPYVLUSN-UHFFFAOYSA-N 0.000 claims 1
- BNYMAMOGZPHSAR-UHFFFAOYSA-N n-[4-[4-(tetrazol-1-yl)phenoxy]butyl]-2,1,3-benzothiadiazole-4-sulfonamide Chemical compound C=1C=CC2=NSN=C2C=1S(=O)(=O)NCCCCOC(C=C1)=CC=C1N1C=NN=N1 BNYMAMOGZPHSAR-UHFFFAOYSA-N 0.000 claims 1
- MMBXLNCLIFZLNY-UHFFFAOYSA-N n-[4-[4-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]phenoxy]butyl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NCCCCOC1=CC=C(C=2SC=C(N=2)C=2C=CC(Cl)=CC=2)C=C1 MMBXLNCLIFZLNY-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- ABOYDMHGKWRPFD-UHFFFAOYSA-N phenylmethanesulfonamide Chemical compound NS(=O)(=O)CC1=CC=CC=C1 ABOYDMHGKWRPFD-UHFFFAOYSA-N 0.000 claims 1
- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical compound NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 223
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 111
- 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 82
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 77
- 235000019441 ethanol Nutrition 0.000 description 75
- 239000007787 solid Substances 0.000 description 67
- 239000000243 solution Substances 0.000 description 60
- 239000002244 precipitate Substances 0.000 description 54
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 42
- 238000010992 reflux Methods 0.000 description 39
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 36
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 30
- 238000001953 recrystallisation Methods 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 28
- 239000000047 product Substances 0.000 description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- 239000000706 filtrate Substances 0.000 description 21
- 239000002904 solvent Substances 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 17
- 239000000725 suspension Substances 0.000 description 17
- 238000003756 stirring Methods 0.000 description 16
- 238000001816 cooling Methods 0.000 description 15
- 230000036982 action potential Effects 0.000 description 14
- 239000003921 oil Substances 0.000 description 14
- 235000019198 oils Nutrition 0.000 description 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 14
- 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 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- 238000009835 boiling Methods 0.000 description 10
- SFONMQPCERJOJE-UHFFFAOYSA-N 4-(4-imidazol-1-ylphenoxy)butan-1-amine;dihydrochloride Chemical compound Cl.Cl.C1=CC(OCCCCN)=CC=C1N1C=NC=C1 SFONMQPCERJOJE-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 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
- 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
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 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 6
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 6
- 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
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- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- AYEQJLOHMLYKAV-UHFFFAOYSA-N n-(4-sulfanylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(S)C=C1 AYEQJLOHMLYKAV-UHFFFAOYSA-N 0.000 description 1
- VHDKOFXDZZXIFH-UHFFFAOYSA-N n-[4-(4-aminobutylsulfanyl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(SCCCCN)C=C1 VHDKOFXDZZXIFH-UHFFFAOYSA-N 0.000 description 1
- MTTULIXDAYNDNY-UHFFFAOYSA-N n-[4-[3-(1,3-dioxoisoindol-2-yl)propoxy]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1OCCCN1C(=O)C2=CC=CC=C2C1=O MTTULIXDAYNDNY-UHFFFAOYSA-N 0.000 description 1
- HQUMWRHORLXTOV-UHFFFAOYSA-N n-[4-[3-(1,3-dioxoisoindol-2-yl)propoxy]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1OCCCN1C(=O)C2=CC=CC=C2C1=O HQUMWRHORLXTOV-UHFFFAOYSA-N 0.000 description 1
- PXEQJDPNFZGGIA-UHFFFAOYSA-N n-[4-[4-(1,3-dioxoisoindol-2-yl)butylsulfanyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1SCCCCN1C(=O)C2=CC=CC=C2C1=O PXEQJDPNFZGGIA-UHFFFAOYSA-N 0.000 description 1
- LBTPIFQNEKOAIM-UHFFFAOYSA-N n-phenylmethanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC=C1 LBTPIFQNEKOAIM-UHFFFAOYSA-N 0.000 description 1
- NSNPSJGHTQIXDO-UHFFFAOYSA-N naphthalene-1-carbonyl chloride Chemical compound C1=CC=C2C(C(=O)Cl)=CC=CC2=C1 NSNPSJGHTQIXDO-UHFFFAOYSA-N 0.000 description 1
- 230000003957 neurotransmitter release Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- WIVNTNLDTMNDNO-UHFFFAOYSA-N octane-1-sulfonyl chloride Chemical compound CCCCCCCCS(Cl)(=O)=O WIVNTNLDTMNDNO-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 229940043200 pentothal Drugs 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
- ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical class NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 description 1
- OAHKWDDSKCRNFE-UHFFFAOYSA-N phenylmethanesulfonyl chloride Chemical compound ClS(=O)(=O)CC1=CC=CC=C1 OAHKWDDSKCRNFE-UHFFFAOYSA-N 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 150000003109 potassium Chemical class 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 210000003742 purkinje fiber Anatomy 0.000 description 1
- 229960001404 quinidine Drugs 0.000 description 1
- JUYUYCIJACTHMK-UHFFFAOYSA-N quinoline-8-sulfonyl chloride Chemical compound C1=CN=C2C(S(=O)(=O)Cl)=CC=CC2=C1 JUYUYCIJACTHMK-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 210000005241 right ventricle Anatomy 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000003195 sodium channel blocking agent Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
- VNNLHYZDXIBHKZ-UHFFFAOYSA-N thiophene-2-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CS1 VNNLHYZDXIBHKZ-UHFFFAOYSA-N 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 208000003663 ventricular fibrillation Diseases 0.000 description 1
- 206010047302 ventricular tachycardia Diseases 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- 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
- 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
- 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)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US1241696P | 1996-02-28 | 1996-02-28 |
Publications (2)
Publication Number | Publication Date |
---|---|
NO970689D0 NO970689D0 (no) | 1997-02-14 |
NO970689L true NO970689L (no) | 1997-08-29 |
Family
ID=21754868
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO970689A NO970689L (no) | 1996-02-28 | 1997-02-14 | Anti-arrytmiske midler |
Country Status (14)
Country | Link |
---|---|
US (1) | US5877196A (de) |
EP (1) | EP0792873A1 (de) |
JP (1) | JPH09227482A (de) |
KR (1) | KR970061273A (de) |
AR (1) | AR005875A1 (de) |
AU (1) | AU1497497A (de) |
CA (1) | CA2197617A1 (de) |
CO (1) | CO4761059A1 (de) |
CZ (1) | CZ44697A3 (de) |
HU (1) | HUP9700457A3 (de) |
IL (1) | IL120177A0 (de) |
NO (1) | NO970689L (de) |
SK (1) | SK18097A3 (de) |
ZA (1) | ZA971741B (de) |
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 |
WO2008019302A1 (en) * | 2006-08-04 | 2008-02-14 | 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 |
JP2779240B2 (ja) * | 1987-12-11 | 1998-07-23 | 三井化学株式会社 | 新規アミン類およびその用途 |
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 |
EP0757988A4 (de) * | 1994-04-27 | 2000-07-26 | Nippon Soda Co | Imidazolderivat und ein verfahren zu seiner herstellung |
-
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 NO NO970689A patent/NO970689L/no 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
- 1997-02-15 KR KR1019970004568A patent/KR970061273A/ko not_active Application Discontinuation
- 1997-02-17 JP JP9031871A patent/JPH09227482A/ja active Pending
- 1997-02-17 AR ARP970100617A patent/AR005875A1/es unknown
- 1997-02-17 HU HU9700457A patent/HUP9700457A3/hu unknown
- 1997-02-21 EP EP97301151A patent/EP0792873A1/de not_active Withdrawn
- 1997-02-27 AU AU14974/97A patent/AU1497497A/en not_active Abandoned
- 1997-02-27 ZA ZA971741A patent/ZA971741B/xx unknown
Also Published As
Publication number | Publication date |
---|---|
KR970061273A (ko) | 1997-09-12 |
SK18097A3 (en) | 1997-10-08 |
EP0792873A1 (de) | 1997-09-03 |
US5877196A (en) | 1999-03-02 |
CA2197617A1 (en) | 1997-08-28 |
HU9700457D0 (en) | 1997-04-28 |
HUP9700457A2 (en) | 1997-10-28 |
HUP9700457A3 (en) | 1998-04-28 |
AU1497497A (en) | 1997-09-04 |
JPH09227482A (ja) | 1997-09-02 |
NO970689D0 (no) | 1997-02-14 |
IL120177A0 (en) | 1997-06-10 |
AR005875A1 (es) | 1999-07-21 |
CO4761059A1 (es) | 1999-04-27 |
CZ44697A3 (en) | 1997-10-15 |
ZA971741B (en) | 1998-08-27 |
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