DD268937A5 - Verfahren zur herstellung bestimmter sulfonamide und ihre verwendung als antiarrhythmische mittel - Google Patents
Verfahren zur herstellung bestimmter sulfonamide und ihre verwendung als antiarrhythmische mittel Download PDFInfo
- Publication number
- DD268937A5 DD268937A5 DD87302295A DD30229587A DD268937A5 DD 268937 A5 DD268937 A5 DD 268937A5 DD 87302295 A DD87302295 A DD 87302295A DD 30229587 A DD30229587 A DD 30229587A DD 268937 A5 DD268937 A5 DD 268937A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- formula
- group
- alk
- alkyl
- item
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 26
- 229940124530 sulfonamide Drugs 0.000 title claims abstract description 8
- 150000003456 sulfonamides Chemical class 0.000 title claims abstract description 8
- 239000003416 antiarrhythmic agent Substances 0.000 title abstract description 11
- 238000004519 manufacturing process Methods 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 92
- -1 piperidino, morpholino Chemical group 0.000 claims abstract description 40
- 238000002360 preparation method Methods 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 230000008569 process Effects 0.000 claims abstract description 7
- 125000001424 substituent group Chemical group 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 4
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims abstract description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 32
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 32
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 16
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 16
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 13
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 claims description 10
- 239000012359 Methanesulfonyl chloride Substances 0.000 claims description 8
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 8
- LBTPIFQNEKOAIM-UHFFFAOYSA-N n-phenylmethanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC=C1 LBTPIFQNEKOAIM-UHFFFAOYSA-N 0.000 claims description 6
- 230000010933 acylation Effects 0.000 claims description 4
- 238000005917 acylation reaction Methods 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- ITYJDNHFRZSTJY-UHFFFAOYSA-N methanesulfonyl bromide Chemical compound CS(Br)(=O)=O ITYJDNHFRZSTJY-UHFFFAOYSA-N 0.000 claims 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- NBNBICNWNFQDDD-UHFFFAOYSA-N sulfuryl dibromide Chemical compound BrS(Br)(=O)=O NBNBICNWNFQDDD-UHFFFAOYSA-N 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 5
- 230000003288 anthiarrhythmic effect Effects 0.000 abstract description 3
- 125000005843 halogen group Chemical group 0.000 abstract description 2
- 239000002371 cardiac agent Substances 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 126
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 113
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 59
- 239000000243 solution Substances 0.000 description 51
- 235000019439 ethyl acetate Nutrition 0.000 description 39
- 239000007787 solid Substances 0.000 description 37
- 238000004458 analytical method Methods 0.000 description 36
- 239000003921 oil Substances 0.000 description 30
- 235000019198 oils Nutrition 0.000 description 30
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 27
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
- 239000000203 mixture Substances 0.000 description 19
- 238000010992 reflux Methods 0.000 description 18
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 18
- 238000005481 NMR spectroscopy Methods 0.000 description 17
- 239000000741 silica gel Substances 0.000 description 17
- 229910002027 silica gel Inorganic materials 0.000 description 17
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 239000007858 starting material Substances 0.000 description 14
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000012267 brine Substances 0.000 description 12
- 238000000605 extraction Methods 0.000 description 12
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 10
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 235000019341 magnesium sulphate Nutrition 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000002425 crystallisation Methods 0.000 description 9
- 230000008025 crystallization Effects 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 9
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 230000037024 effective refractory period Effects 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 239000007868 Raney catalyst Substances 0.000 description 6
- 229910000564 Raney nickel Inorganic materials 0.000 description 6
- 206010003119 arrhythmia Diseases 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 235000009518 sodium iodide Nutrition 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 239000012458 free base Substances 0.000 description 5
- NTURQZFFJDCTMZ-UHFFFAOYSA-N 1-(2-bromoethyl)-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(CCBr)C=C1 NTURQZFFJDCTMZ-UHFFFAOYSA-N 0.000 description 4
- 235000019502 Orange oil Nutrition 0.000 description 4
- 230000001746 atrial effect Effects 0.000 description 4
- PTPPVTUXJDJAGY-UHFFFAOYSA-N n-methyl-2-(4-nitrophenyl)ethanamine Chemical compound CNCCC1=CC=C([N+]([O-])=O)C=C1 PTPPVTUXJDJAGY-UHFFFAOYSA-N 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 239000010502 orange oil Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- CIIGWOXXOUVEAD-UHFFFAOYSA-N 2-chloroethyl benzenesulfonate Chemical compound ClCCOS(=O)(=O)C1=CC=CC=C1 CIIGWOXXOUVEAD-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- 230000006793 arrhythmia Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 230000002861 ventricular Effects 0.000 description 3
- 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 2
- QXSAKPUBHTZHKW-UHFFFAOYSA-N 4-hydroxybenzamide Chemical compound NC(=O)C1=CC=C(O)C=C1 QXSAKPUBHTZHKW-UHFFFAOYSA-N 0.000 description 2
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 206010003658 Atrial Fibrillation Diseases 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 206010042600 Supraventricular arrhythmias Diseases 0.000 description 2
- 206010047281 Ventricular arrhythmia Diseases 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 230000000747 cardiac effect Effects 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 210000002837 heart atrium Anatomy 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000003328 mesylation reaction Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- 230000002028 premature Effects 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 230000000644 propagated effect Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000036279 refractory period Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 238000001665 trituration Methods 0.000 description 2
- 208000003663 ventricular fibrillation Diseases 0.000 description 2
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- AHOFWSHLRKOJBS-UHFFFAOYSA-N 1-(2-bromoethoxy)-2-nitrobenzene Chemical class [O-][N+](=O)C1=CC=CC=C1OCCBr AHOFWSHLRKOJBS-UHFFFAOYSA-N 0.000 description 1
- YQWCBDNNEZHPMA-UHFFFAOYSA-N 1-(2-bromoethoxy)-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(OCCBr)C=C1 YQWCBDNNEZHPMA-UHFFFAOYSA-N 0.000 description 1
- LIBYGKUWXRBMPA-UHFFFAOYSA-N 1-(3-bromopropoxy)-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(OCCCBr)C=C1 LIBYGKUWXRBMPA-UHFFFAOYSA-N 0.000 description 1
- DBRBCFJUEVSKGZ-UHFFFAOYSA-N 1-(4-bromobutoxy)-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(OCCCCBr)C=C1 DBRBCFJUEVSKGZ-UHFFFAOYSA-N 0.000 description 1
- YFZHODLXYNDBSM-UHFFFAOYSA-N 1-ethenyl-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(C=C)C=C1 YFZHODLXYNDBSM-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- QXHDYMUPPXAMPQ-UHFFFAOYSA-N 2-(4-aminophenyl)ethanol Chemical compound NC1=CC=C(CCO)C=C1 QXHDYMUPPXAMPQ-UHFFFAOYSA-N 0.000 description 1
- IOXOZOPLBFXYLM-UHFFFAOYSA-N 2-(4-nitrophenyl)ethanamine Chemical compound NCCC1=CC=C([N+]([O-])=O)C=C1 IOXOZOPLBFXYLM-UHFFFAOYSA-N 0.000 description 1
- ZXNMIUJDTOMBPV-UHFFFAOYSA-N 2-chloroethyl 4-methylbenzenesulfonate Chemical compound CC1=CC=C(S(=O)(=O)OCCCl)C=C1 ZXNMIUJDTOMBPV-UHFFFAOYSA-N 0.000 description 1
- NGMMGKYJUWYIIG-UHFFFAOYSA-N 3-hydroxybenzamide Chemical compound NC(=O)C1=CC=CC(O)=C1 NGMMGKYJUWYIIG-UHFFFAOYSA-N 0.000 description 1
- WQYDIXCUOGOFRF-UHFFFAOYSA-N 4-(2-chloroethoxy)aniline;hydrochloride Chemical compound Cl.NC1=CC=C(OCCCl)C=C1 WQYDIXCUOGOFRF-UHFFFAOYSA-N 0.000 description 1
- CVQWYCCXJPYZQI-UHFFFAOYSA-N 4-(2-chloroethoxy)benzamide Chemical compound NC(=O)C1=CC=C(OCCCl)C=C1 CVQWYCCXJPYZQI-UHFFFAOYSA-N 0.000 description 1
- XPMZFKWAFWMRGF-UHFFFAOYSA-N 4-(2-chloroethoxy)benzoyl chloride Chemical compound ClCCOC1=CC=C(C(Cl)=O)C=C1 XPMZFKWAFWMRGF-UHFFFAOYSA-N 0.000 description 1
- AWMZEKGTWKVJHE-UHFFFAOYSA-N 4-[2-(ethylamino)ethyl]aniline Chemical compound CCNCCC1=CC=C(N)C=C1 AWMZEKGTWKVJHE-UHFFFAOYSA-N 0.000 description 1
- NNIPOYNUFNLQMO-UHFFFAOYSA-N 4-[2-(methylamino)ethyl]aniline Chemical compound CNCCC1=CC=C(N)C=C1 NNIPOYNUFNLQMO-UHFFFAOYSA-N 0.000 description 1
- MLSDRJAYBKIOPY-UHFFFAOYSA-N 4-[2-[2-(4-aminophenyl)ethyl-methylamino]ethyl]aniline Chemical compound C=1C=C(N)C=CC=1CCN(C)CCC1=CC=C(N)C=C1 MLSDRJAYBKIOPY-UHFFFAOYSA-N 0.000 description 1
- ZQVLMCKLNOXWQI-UHFFFAOYSA-N 4-[2-[ethyl(methyl)amino]ethyl]aniline Chemical compound CCN(C)CCC1=CC=C(N)C=C1 ZQVLMCKLNOXWQI-UHFFFAOYSA-N 0.000 description 1
- AZEIRPAUJXANCS-UHFFFAOYSA-N 4-ethoxybenzamide Chemical compound CCOC1=CC=C(C(N)=O)C=C1 AZEIRPAUJXANCS-UHFFFAOYSA-N 0.000 description 1
- AXBVSRMHOPMXBA-UHFFFAOYSA-N 4-nitrothiophenol Chemical compound [O-][N+](=O)C1=CC=C(S)C=C1 AXBVSRMHOPMXBA-UHFFFAOYSA-N 0.000 description 1
- KQTGCJMBUBYSLL-UHFFFAOYSA-N 4-piperidin-1-ylmorpholine Chemical compound C1CCCCN1N1CCOCC1 KQTGCJMBUBYSLL-UHFFFAOYSA-N 0.000 description 1
- NQXUSSVLFOBRSE-UHFFFAOYSA-N 5-methyl-2-nitrophenol Chemical compound CC1=CC=C([N+]([O-])=O)C(O)=C1 NQXUSSVLFOBRSE-UHFFFAOYSA-N 0.000 description 1
- BOFRXDMCQRTGII-UHFFFAOYSA-N 619-08-9 Chemical compound OC1=CC=C([N+]([O-])=O)C=C1Cl BOFRXDMCQRTGII-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241001233242 Lontra Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 101000650578 Salmonella phage P22 Regulatory protein C3 Proteins 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 101001040920 Triticum aestivum Alpha-amylase inhibitor 0.28 Proteins 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000036982 action potential Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000005422 alkyl sulfonamido group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- JECOSSASMXAXFV-UHFFFAOYSA-N chloroethane;hydrochloride Chemical compound Cl.CCCl JECOSSASMXAXFV-UHFFFAOYSA-N 0.000 description 1
- 125000006011 chloroethoxy group Chemical group 0.000 description 1
- 229940001468 citrate Drugs 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 239000012141 concentrate Substances 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
- 238000009109 curative therapy Methods 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- MXWRJMIKMODSCY-UHFFFAOYSA-N ethane;dihydrochloride Chemical compound Cl.Cl.CC MXWRJMIKMODSCY-UHFFFAOYSA-N 0.000 description 1
- FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 1
- XNWXLCYCBXGUHQ-UHFFFAOYSA-N ethyl acetate;hydrate;hydrochloride Chemical compound O.Cl.CCOC(C)=O XNWXLCYCBXGUHQ-UHFFFAOYSA-N 0.000 description 1
- MVEAAGBEUOMFRX-UHFFFAOYSA-N ethyl acetate;hydrochloride Chemical compound Cl.CCOC(C)=O MVEAAGBEUOMFRX-UHFFFAOYSA-N 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 229940050411 fumarate Drugs 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 210000003021 heart conduction system Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
- 229940001447 lactate Drugs 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- SRSRGGYRIOZFAT-UHFFFAOYSA-N methyl 4-(2-chloroethoxy)benzoate Chemical compound COC(=O)C1=CC=C(OCCCl)C=C1 SRSRGGYRIOZFAT-UHFFFAOYSA-N 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- OPWXJASBLYLBIH-UHFFFAOYSA-N n-[4-(2-chloroethoxy)phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=C(OCCCl)C=C1 OPWXJASBLYLBIH-UHFFFAOYSA-N 0.000 description 1
- MSZBIHITHNHHTL-UHFFFAOYSA-N n-[4-[2-(methylamino)ethyl]phenyl]methanesulfonamide Chemical compound CNCCC1=CC=C(NS(C)(=O)=O)C=C1 MSZBIHITHNHHTL-UHFFFAOYSA-N 0.000 description 1
- AJBFPKIKJQWYCI-UHFFFAOYSA-N n-ethyl-2-(4-nitrophenyl)ethanamine Chemical compound CCNCCC1=CC=C([N+]([O-])=O)C=C1 AJBFPKIKJQWYCI-UHFFFAOYSA-N 0.000 description 1
- FMYSLOHXMJLTRT-UHFFFAOYSA-N n-methyl-1-(4-nitrophenyl)propan-2-amine Chemical compound CNC(C)CC1=CC=C([N+]([O-])=O)C=C1 FMYSLOHXMJLTRT-UHFFFAOYSA-N 0.000 description 1
- XJJXMLGYSDKGEZ-UHFFFAOYSA-N n-methyl-2-(4-nitrophenyl)-n-[2-(4-nitrophenyl)ethyl]ethanamine Chemical compound C=1C=C([N+]([O-])=O)C=CC=1CCN(C)CCC1=CC=C([N+]([O-])=O)C=C1 XJJXMLGYSDKGEZ-UHFFFAOYSA-N 0.000 description 1
- XIFJZJPMHNUGRA-UHFFFAOYSA-N n-methyl-4-nitroaniline Chemical compound CNC1=CC=C([N+]([O-])=O)C=C1 XIFJZJPMHNUGRA-UHFFFAOYSA-N 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 210000003540 papillary muscle Anatomy 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000009090 positive inotropic effect Effects 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 210000005241 right ventricle Anatomy 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB868610668A GB8610668D0 (en) | 1986-05-01 | 1986-05-01 | Anti-arrhythmia agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD268937A5 true DD268937A5 (de) | 1989-06-14 |
Family
ID=10597176
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD87302295A DD268937A5 (de) | 1986-05-01 | 1987-04-30 | Verfahren zur herstellung bestimmter sulfonamide und ihre verwendung als antiarrhythmische mittel |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS62267250A (enrdf_load_stackoverflow) |
| DD (1) | DD268937A5 (enrdf_load_stackoverflow) |
| GB (1) | GB8610668D0 (enrdf_load_stackoverflow) |
| LV (1) | LV5466A3 (enrdf_load_stackoverflow) |
| MX (1) | MX6311A (enrdf_load_stackoverflow) |
| SU (1) | SU1591805A3 (enrdf_load_stackoverflow) |
| UA (1) | UA6154A1 (enrdf_load_stackoverflow) |
| ZA (1) | ZA873078B (enrdf_load_stackoverflow) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69531691T2 (de) * | 1994-08-04 | 2004-07-08 | C & C Research Labs | Neues amin-derivat, verfahren zur herstellung und dessen verwendung als anti-arrhythmisches mittel |
| EP1636191A2 (en) | 2003-06-17 | 2006-03-22 | Arena Pharmaceuticals, Inc. | Benzazepine derivatives useful for the treatment of 5ht2c receptor associated diseases |
| ES2331656T3 (es) | 2004-12-23 | 2010-01-12 | Arena Pharmaceuticals, Inc. | Composiciones de modulador del receptor 5ht2c y procedimientos de uso. |
| EP2518053A1 (en) | 2006-04-03 | 2012-10-31 | Arena Pharmaceuticals, Inc. | Process for the preparation of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine |
| KR20100045983A (ko) * | 2007-06-29 | 2010-05-04 | 에모리 유니버시티 | 신경보호를 위한 ｎｍｄａ 수용체 길항물질 |
| US8952197B2 (en) | 2009-06-18 | 2015-02-10 | Arena Pharmaceuticals, Inc. | Processes for the preparation of 5-HT2C receptor agonists |
| WO2011153206A1 (en) | 2010-06-02 | 2011-12-08 | Arena Pharmaceuticals, Inc. | Processes for the preparation of 5-ht2c receptor agonists |
| AU2011296033A1 (en) | 2010-09-01 | 2013-04-04 | Arena Pharmaceuticals, Inc. | Non-hygroscopic salts of 5-HT2C agonists |
| KR20130138770A (ko) | 2010-09-01 | 2013-12-19 | 아레나 파마슈티칼스, 인크. | 광학적으로 활성 산을 갖는 로르카세린의 염 |
| KR20180118801A (ko) | 2010-09-01 | 2018-10-31 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 체중 관리에 유용한 5-ｈｔ2ｃ 작동제의 변형-방출 투여 형태 |
| SG188365A1 (en) | 2010-09-01 | 2013-04-30 | Arena Pharm Inc | Administration of lorcaserin to individuals with renal impairment |
| MX2015004532A (es) | 2012-10-09 | 2016-01-20 | Arena Pharm Inc | Metodo de control del peso. |
-
1986
- 1986-05-01 GB GB868610668A patent/GB8610668D0/en active Pending
-
1987
- 1987-04-29 ZA ZA873078A patent/ZA873078B/xx unknown
- 1987-04-30 SU SU874202474A patent/SU1591805A3/ru active
- 1987-04-30 MX MX631187A patent/MX6311A/es unknown
- 1987-04-30 DD DD87302295A patent/DD268937A5/de not_active IP Right Cessation
- 1987-04-30 UA UA4202474A patent/UA6154A1/uk unknown
- 1987-05-01 JP JP62108720A patent/JPS62267250A/ja active Granted
-
1993
- 1993-12-03 LV LV931305A patent/LV5466A3/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| LV5466A3 (lv) | 1994-03-10 |
| JPS62267250A (ja) | 1987-11-19 |
| ZA873078B (en) | 1988-12-28 |
| JPH0360814B2 (enrdf_load_stackoverflow) | 1991-09-17 |
| MX6311A (es) | 1993-08-01 |
| GB8610668D0 (en) | 1986-06-04 |
| SU1591805A3 (ru) | 1990-09-07 |
| UA6154A1 (uk) | 1994-12-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR930001339B1 (ko) | 부정맥 치료제의 제조방법 | |
| AT363096B (de) | Verfahren zur herstellung von neuen phthalazinderivaten und deren salzen | |
| FI95245C (fi) | Menetelmä rytmihäiriöiden vastaisten pyrimidiinidionijohdannaisten valmistamiseksi | |
| DE69908156T2 (de) | Arylsulfonanilid-harnstoffe | |
| DE2922523C2 (de) | Aminothiazole und diese enthaltende Arzneimitte l | |
| DE68928262T2 (de) | Derivate von Alkanolaminen als kardiovaskuläre Mittel | |
| DE69023928T2 (de) | DIAMINVERBINDUNGEN UND ARZNEIMITTEL GEGEN CEREBRALE STöRUNGEN DIE DIESE ENTHALTEN. | |
| DD268937A5 (de) | Verfahren zur herstellung bestimmter sulfonamide und ihre verwendung als antiarrhythmische mittel | |
| DE10128331A1 (de) | Anthranilsäureamide mit Heteroarylsulfonyl-Seitenkette, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltende pharmazeutische Zubereitungen | |
| DE3248138C2 (enrdf_load_stackoverflow) | ||
| DE3875600T2 (de) | Antiarrythmische derivate 2. | |
| DD274210A5 (de) | Verfahren zur herstellung substituierter benzamide | |
| EP0212481B1 (de) | Indolinonderivate, Verfahren zu ihrer Herstellung, sie enthaltende Arzneimittel und deren Verwendung | |
| DE2505297A1 (de) | Neue 2-arylamino-2-imidazolinderivate und ein verfahren zu deren herstellung | |
| DE2434951C3 (de) | In 3-stellung basisch substituierte diphenylhydantoine | |
| DE2112249A1 (de) | Pharmakologisch wirksame Derivate von Phenylalkylaminen | |
| DD280965A5 (de) | Verfahren zur herstellung von antiarrhythmisch wirkenden mitteln | |
| DD281596A5 (de) | Verfahren zur hersteung antiarrhytmischer mittel | |
| DE2720545B2 (de) | Derivate des 2,4-Diamino-6,7-dimethoxychinazolins, ihre Herstellung und pharmazeutische Mittel | |
| DE69221106T2 (de) | Antitumorzusammensetzung und Verfahren zur Behandlung | |
| EP0018360B1 (de) | N-(5-Methoxybentofuran-2-ylcarbonyl)-N'-benzylpiperazin und Verfahren zu dessen Herstellung | |
| DE60025270T2 (de) | N-substituierte benzyl oder phenyl arylsulfamide und ihre verwendung | |
| DE69512104T2 (de) | Substituierte Sulfonamide, Verfahren zu deren Herstellung und sie enthaltende pharmazeutische Zusammensetzungen | |
| DE69713128T2 (de) | 4-(1-piperazinyl)benzosäurederivate, verfahren zu ihrer herstellung und ihre therapeutischen verwendungen | |
| DD296913A5 (de) | Substituierte (chinolin-2-yl-methoxy)phenyl-n,n'-sulfonylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NPV | Change in the person, the name or the address of the representative (addendum to changes before extension act) | ||
| ENJ | Ceased due to non-payment of renewal fee |