IE53342B1 - N-(arylthioalkyl)-n-(aminoalkyl)ureas - Google Patents
N-(arylthioalkyl)-n-(aminoalkyl)ureasInfo
- Publication number
- IE53342B1 IE53342B1 IE1191/82A IE119182A IE53342B1 IE 53342 B1 IE53342 B1 IE 53342B1 IE 1191/82 A IE1191/82 A IE 1191/82A IE 119182 A IE119182 A IE 119182A IE 53342 B1 IE53342 B1 IE 53342B1
- Authority
- IE
- Ireland
- Prior art keywords
- ethyl
- methylethyl
- urea
- dimethylamino
- sulphonyl
- Prior art date
Links
- 235000013877 carbamide Nutrition 0.000 title abstract description 37
- 150000003672 ureas Chemical class 0.000 title abstract description 7
- -1 sulphinyl Chemical group 0.000 claims abstract description 48
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims abstract description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 4
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 216
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 159
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 134
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 119
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 96
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 51
- 239000004202 carbamide Substances 0.000 claims description 47
- 239000000203 mixture Substances 0.000 claims description 45
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Natural products CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 29
- 206010003119 arrhythmia Diseases 0.000 claims description 28
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 23
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 22
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 17
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 14
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 11
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 10
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 8
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 229940095064 tartrate Drugs 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 230000001225 therapeutic effect Effects 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 150000004677 hydrates Chemical class 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- GPTFURBXHJWNHR-UHFFFAOYSA-N protopine Chemical compound C1=C2C(=O)CC3=CC=C4OCOC4=C3CN(C)CCC2=CC2=C1OCO2 GPTFURBXHJWNHR-UHFFFAOYSA-N 0.000 claims description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- LZMATGARSSLFMQ-UHFFFAOYSA-N propan-2-ylurea Chemical compound CC(C)NC(N)=O LZMATGARSSLFMQ-UHFFFAOYSA-N 0.000 claims 3
- POXAIQSXNOEQGM-UHFFFAOYSA-N propan-2-ylthiourea Chemical compound CC(C)NC(N)=S POXAIQSXNOEQGM-UHFFFAOYSA-N 0.000 claims 2
- WHDXATKYIKDLBG-WLHGVMLRSA-N (e)-but-2-enedioic acid;1-[2-(4-chlorophenyl)sulfanylethyl]-3-[2-(dimethylamino)ethyl]-1-propan-2-ylurea Chemical compound OC(=O)\C=C\C(O)=O.CN(C)CCNC(=O)N(C(C)C)CCSC1=CC=C(Cl)C=C1 WHDXATKYIKDLBG-WLHGVMLRSA-N 0.000 claims 1
- CRCCWPUORDJJEY-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)sulfonylethyl]-3-[2-(diethylamino)ethyl]-1-propan-2-ylurea Chemical compound CCN(CC)CCNC(=O)N(C(C)C)CCS(=O)(=O)C1=CC=C(Cl)C=C1 CRCCWPUORDJJEY-UHFFFAOYSA-N 0.000 claims 1
- WXVUWTMDBLIMIA-UHFFFAOYSA-N 1-[2-(dimethylamino)ethyl]-1-propan-2-ylurea Chemical compound CN(CCN(C(=O)N)C(C)C)C WXVUWTMDBLIMIA-UHFFFAOYSA-N 0.000 claims 1
- BDYZUNGZVADADC-UHFFFAOYSA-N 1-[3-(benzenesulfonyl)propyl]-3-[2-(diethylamino)ethyl]-1-propan-2-ylurea Chemical compound CCN(CC)CCNC(=O)N(C(C)C)CCCS(=O)(=O)C1=CC=CC=C1 BDYZUNGZVADADC-UHFFFAOYSA-N 0.000 claims 1
- 230000003647 oxidation Effects 0.000 abstract description 9
- 238000007254 oxidation reaction Methods 0.000 abstract description 9
- 150000003585 thioureas Chemical class 0.000 abstract description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 183
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 161
- 239000000243 solution Substances 0.000 description 116
- 238000002360 preparation method Methods 0.000 description 107
- 238000000034 method Methods 0.000 description 106
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 102
- 239000012458 free base Substances 0.000 description 82
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 64
- 239000010410 layer Substances 0.000 description 58
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 54
- 238000004458 analytical method Methods 0.000 description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 45
- 239000011976 maleic acid Substances 0.000 description 45
- 239000002904 solvent Substances 0.000 description 39
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- 239000007787 solid Substances 0.000 description 33
- 239000011541 reaction mixture Substances 0.000 description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- 239000000047 product Substances 0.000 description 26
- 235000011149 sulphuric acid Nutrition 0.000 description 26
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 25
- 239000001117 sulphuric acid Substances 0.000 description 24
- 239000002253 acid Substances 0.000 description 23
- 238000001704 evaporation Methods 0.000 description 23
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 22
- 230000008020 evaporation Effects 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 19
- 238000010992 reflux Methods 0.000 description 18
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 17
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 17
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 13
- 230000006793 arrhythmia Effects 0.000 description 13
- 241001465754 Metazoa Species 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 11
- 239000004615 ingredient Substances 0.000 description 11
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
- 235000019341 magnesium sulphate Nutrition 0.000 description 11
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 230000002378 acidificating effect Effects 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 241000282472 Canis lupus familiaris Species 0.000 description 8
- 238000007792 addition Methods 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- VPPLBSVKOFEITE-UHFFFAOYSA-N n-[2-(benzenesulfonyl)ethyl]propan-2-amine Chemical compound CC(C)NCCS(=O)(=O)C1=CC=CC=C1 VPPLBSVKOFEITE-UHFFFAOYSA-N 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 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 7
- 239000001257 hydrogen Substances 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 7
- LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 238000001802 infusion Methods 0.000 description 6
- 229960001922 sodium perborate Drugs 0.000 description 6
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 6
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
- 229960004132 diethyl ether Drugs 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000001530 fumaric acid Substances 0.000 description 5
- VEOXTCXOHHMWQD-UHFFFAOYSA-N n-[2-(4-chlorophenyl)sulfonylethyl]propan-2-amine Chemical compound CC(C)NCCS(=O)(=O)C1=CC=C(Cl)C=C1 VEOXTCXOHHMWQD-UHFFFAOYSA-N 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 239000000829 suppository Substances 0.000 description 5
- DPHNJPUOMLRELT-UHFFFAOYSA-N 2,3-dihydro-1h-inden-4-ol Chemical compound OC1=CC=CC2=C1CCC2 DPHNJPUOMLRELT-UHFFFAOYSA-N 0.000 description 4
- RFCQDOVPMUSZMN-UHFFFAOYSA-N 2-Naphthalenethiol Chemical compound C1=CC=CC2=CC(S)=CC=C21 RFCQDOVPMUSZMN-UHFFFAOYSA-N 0.000 description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
- RYECOJGRJDOGPP-UHFFFAOYSA-N Ethylurea Chemical compound CCNC(N)=O RYECOJGRJDOGPP-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000007853 buffer solution Substances 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 230000000747 cardiac effect Effects 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical compound Cl.CCN XWBDWHCCBGMXKG-UHFFFAOYSA-N 0.000 description 4
- FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 150000002688 maleic acid derivatives Chemical class 0.000 description 4
- 235000006408 oxalic acid Nutrition 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 4
- LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 4
- 125000001174 sulfone group Chemical group 0.000 description 4
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
- PZBLTCZCXLHCIW-UHFFFAOYSA-N 2-(benzenesulfonyl)-n-methylethanamine Chemical compound CNCCS(=O)(=O)C1=CC=CC=C1 PZBLTCZCXLHCIW-UHFFFAOYSA-N 0.000 description 3
- NUJGORANFDSMOL-UHFFFAOYSA-N 2-chloroethylsulfonylbenzene Chemical compound ClCCS(=O)(=O)C1=CC=CC=C1 NUJGORANFDSMOL-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 3
- 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 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- 210000004351 coronary vessel Anatomy 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002926 oxygen Chemical class 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 3
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229960001866 silicon dioxide Drugs 0.000 description 3
- 239000012418 sodium perborate tetrahydrate Substances 0.000 description 3
- IBDSNZLUHYKHQP-UHFFFAOYSA-N sodium;3-oxidodioxaborirane;tetrahydrate Chemical compound O.O.O.O.[Na+].[O-]B1OO1 IBDSNZLUHYKHQP-UHFFFAOYSA-N 0.000 description 3
- NYKRSGJRIJJRRK-UHFFFAOYSA-N 1-chloro-2-(2-chlorophenyl)sulfonylbenzene Chemical compound ClC1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1Cl NYKRSGJRIJJRRK-UHFFFAOYSA-N 0.000 description 2
- FWKSXVPFRPLQPN-UHFFFAOYSA-N 2-(4-fluorophenyl)sulfanylethanol Chemical compound OCCSC1=CC=C(F)C=C1 FWKSXVPFRPLQPN-UHFFFAOYSA-N 0.000 description 2
- VIJUOTGARMCBHS-UHFFFAOYSA-N 2-[methyl(2-phenylethyl)amino]acetonitrile Chemical compound N#CCN(C)CCC1=CC=CC=C1 VIJUOTGARMCBHS-UHFFFAOYSA-N 0.000 description 2
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 2
- WRXNJTBODVGDRY-UHFFFAOYSA-N 2-pyrrolidin-1-ylethanamine Chemical compound NCCN1CCCC1 WRXNJTBODVGDRY-UHFFFAOYSA-N 0.000 description 2
- LPMXVESGRSUGHW-UHFFFAOYSA-N Acolongiflorosid K Natural products OC1C(O)C(O)C(C)OC1OC1CC2(O)CCC3C4(O)CCC(C=5COC(=O)C=5)C4(C)CC(O)C3C2(CO)C(O)C1 LPMXVESGRSUGHW-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- 206010015856 Extrasystoles Diseases 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- LPMXVESGRSUGHW-GHYGWZAOSA-N Ouabain Natural products O([C@@H]1[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O1)[C@H]1C[C@@H](O)[C@@]2(CO)[C@@](O)(C1)CC[C@H]1[C@]3(O)[C@@](C)([C@H](C4=CC(=O)OC4)CC3)C[C@@H](O)[C@H]21 LPMXVESGRSUGHW-GHYGWZAOSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 244000166550 Strophanthus gratus Species 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000003288 anthiarrhythmic effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003637 basic solution Substances 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 2
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 125000001475 halogen functional group Chemical group 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- QNEUMPZMEXPLOM-UHFFFAOYSA-N n'-methyl-n'-(2-phenylethyl)ethane-1,2-diamine Chemical compound NCCN(C)CCC1=CC=CC=C1 QNEUMPZMEXPLOM-UHFFFAOYSA-N 0.000 description 2
- DKABNBXKCGDZGG-UHFFFAOYSA-N n-(2-benzylsulfanylethyl)propan-2-amine Chemical compound CC(C)NCCSCC1=CC=CC=C1 DKABNBXKCGDZGG-UHFFFAOYSA-N 0.000 description 2
- GRFABOAYPYVXJT-UHFFFAOYSA-N n-(2-benzylsulfonylethyl)propan-2-amine Chemical compound CC(C)NCCS(=O)(=O)CC1=CC=CC=C1 GRFABOAYPYVXJT-UHFFFAOYSA-N 0.000 description 2
- SCJZYLVKYNQSOK-UHFFFAOYSA-N n-(2-naphthalen-1-ylsulfinylethyl)propan-2-amine Chemical compound C1=CC=C2C(S(=O)CCNC(C)C)=CC=CC2=C1 SCJZYLVKYNQSOK-UHFFFAOYSA-N 0.000 description 2
- WQAIXBUCXJWZNX-UHFFFAOYSA-N n-[2-(4-bromophenyl)sulfonylethyl]propan-2-amine Chemical compound CC(C)NCCS(=O)(=O)C1=CC=C(Br)C=C1 WQAIXBUCXJWZNX-UHFFFAOYSA-N 0.000 description 2
- XEFZWTHZKFSASX-UHFFFAOYSA-N n-[2-(4-chlorophenyl)sulfanylethyl]propan-2-amine Chemical compound CC(C)NCCSC1=CC=C(Cl)C=C1 XEFZWTHZKFSASX-UHFFFAOYSA-N 0.000 description 2
- JCXSBCOZHOSPDT-UHFFFAOYSA-N n-[2-(benzenesulfonyl)ethyl]cyclohexanamine Chemical compound C=1C=CC=CC=1S(=O)(=O)CCNC1CCCCC1 JCXSBCOZHOSPDT-UHFFFAOYSA-N 0.000 description 2
- NNFWIFAFFBPMRJ-UHFFFAOYSA-N n-[2-(furan-2-ylmethylsulfinyl)ethyl]propan-2-amine Chemical compound CC(C)NCCS(=O)CC1=CC=CO1 NNFWIFAFFBPMRJ-UHFFFAOYSA-N 0.000 description 2
- SASNBVQSOZSTPD-UHFFFAOYSA-N n-methylphenethylamine Chemical compound CNCCC1=CC=CC=C1 SASNBVQSOZSTPD-UHFFFAOYSA-N 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229960003343 ouabain Drugs 0.000 description 2
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 229960001404 quinidine Drugs 0.000 description 2
- 238000005057 refrigeration Methods 0.000 description 2
- 230000033764 rhythmic process Effects 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000008174 sterile solution Substances 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 230000002861 ventricular Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- HWTGRABUGNLZHD-BTJKTKAUSA-N (z)-but-2-enedioic acid;3-[2-(diethylamino)ethyl]-1-[2-(furan-2-ylmethylsulfanyl)ethyl]-1-propan-2-ylurea Chemical compound OC(=O)\C=C/C(O)=O.CCN(CC)CCNC(=O)N(C(C)C)CCSCC1=CC=CO1 HWTGRABUGNLZHD-BTJKTKAUSA-N 0.000 description 1
- KKUGLUXXIGKECX-ODZAUARKSA-N (z)-but-2-enedioic acid;urea Chemical compound NC(N)=O.OC(=O)\C=C/C(O)=O KKUGLUXXIGKECX-ODZAUARKSA-N 0.000 description 1
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- AGILVNWURLRTPS-UHFFFAOYSA-N 1,3-dichloro-5-(2-chloroethylsulfonyl)benzene Chemical compound ClCCS(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 AGILVNWURLRTPS-UHFFFAOYSA-N 0.000 description 1
- YUZZZNBYRRMSPV-UHFFFAOYSA-N 1-(2-chloroethylsulfonyl)-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)CCCl)=C1 YUZZZNBYRRMSPV-UHFFFAOYSA-N 0.000 description 1
- GUJNICXLNHZNIH-UHFFFAOYSA-N 1-(2-chloroethylsulfonyl)-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(S(=O)(=O)CCCl)C=C1 GUJNICXLNHZNIH-UHFFFAOYSA-N 0.000 description 1
- XJTIHTHZQXELBZ-UHFFFAOYSA-N 1-(2-chloroethylsulfonyl)-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(S(=O)(=O)CCCl)C=C1 XJTIHTHZQXELBZ-UHFFFAOYSA-N 0.000 description 1
- OCPCBLSLNITXBN-UHFFFAOYSA-N 1-(2-naphthalen-1-ylsulfanylethylsulfanyl)naphthalene Chemical compound C1=CC=C2C(SCCSC=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 OCPCBLSLNITXBN-UHFFFAOYSA-N 0.000 description 1
- ZANGRJXMYUHWSM-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)sulfonylethyl]-3-[2-(diethylamino)ethyl]-1-propan-2-ylurea;2,3-dihydroxybutanedioic acid Chemical compound OC(=O)C(O)C(O)C(O)=O.CCN(CC)CCNC(=O)N(C(C)C)CCS(=O)(=O)C1=CC=C(Cl)C=C1 ZANGRJXMYUHWSM-UHFFFAOYSA-N 0.000 description 1
- OSTGVQSWUXGHKL-UHFFFAOYSA-N 1-[2-(benzenesulfonyl)ethyl]-3-[2-(diethylamino)ethyl]-1-propan-2-ylurea Chemical compound CCN(CC)CCNC(=O)N(C(C)C)CCS(=O)(=O)C1=CC=CC=C1 OSTGVQSWUXGHKL-UHFFFAOYSA-N 0.000 description 1
- CMKAKNPPMGLPRW-BTJKTKAUSA-N 1-[2-(benzenesulfonyl)ethyl]-3-[2-(diethylamino)ethyl]-1-propan-2-ylurea;(z)-but-2-enedioic acid Chemical compound OC(=O)\C=C/C(O)=O.CCN(CC)CCNC(=O)N(C(C)C)CCS(=O)(=O)C1=CC=CC=C1 CMKAKNPPMGLPRW-BTJKTKAUSA-N 0.000 description 1
- KUWGKJJQVYYXQK-UHFFFAOYSA-N 1-[2-(diethylamino)ethyl]-3-propan-2-ylurea Chemical compound CCN(CC)CCNC(=O)NC(C)C KUWGKJJQVYYXQK-UHFFFAOYSA-N 0.000 description 1
- BSSDAMWQINGNMC-UHFFFAOYSA-N 1-bromo-4-(2-chloroethylsulfonyl)benzene Chemical compound ClCCS(=O)(=O)C1=CC=C(Br)C=C1 BSSDAMWQINGNMC-UHFFFAOYSA-N 0.000 description 1
- JJMLCWKZDOCOPH-UHFFFAOYSA-N 1-chloro-2-(2-chlorophenyl)sulfanylbenzene Chemical compound ClC1=CC=CC=C1SC1=CC=CC=C1Cl JJMLCWKZDOCOPH-UHFFFAOYSA-N 0.000 description 1
- OEOIAJDPLKEFLD-UHFFFAOYSA-N 1-sulfonylethane Chemical compound CC=S(=O)=O OEOIAJDPLKEFLD-UHFFFAOYSA-N 0.000 description 1
- FNUJVDBGYDGKCO-UHFFFAOYSA-N 1-tert-butyl-4-(2-chloroethylsulfonyl)benzene Chemical compound CC(C)(C)C1=CC=C(S(=O)(=O)CCCl)C=C1 FNUJVDBGYDGKCO-UHFFFAOYSA-N 0.000 description 1
- QGRKONUHHGBHRB-UHFFFAOYSA-N 2,3-dichlorobenzenethiol Chemical compound SC1=CC=CC(Cl)=C1Cl QGRKONUHHGBHRB-UHFFFAOYSA-N 0.000 description 1
- VYAIVQVJGKOWOR-UHFFFAOYSA-N 2-(2-chloroethylsulfanylmethyl)furan Chemical compound ClCCSCC1=CC=CO1 VYAIVQVJGKOWOR-UHFFFAOYSA-N 0.000 description 1
- ATPDLCXUEWBQBM-UHFFFAOYSA-N 2-(2-chloroethylsulfonylmethyl)furan Chemical compound ClCCS(=O)(=O)CC1=CC=CO1 ATPDLCXUEWBQBM-UHFFFAOYSA-N 0.000 description 1
- HIQIUWWTDXZTLN-UHFFFAOYSA-N 2-(benzenesulfonyl)-n-benzylethanamine Chemical compound C=1C=CC=CC=1S(=O)(=O)CCNCC1=CC=CC=C1 HIQIUWWTDXZTLN-UHFFFAOYSA-N 0.000 description 1
- HEKKXNNVIAECAN-UHFFFAOYSA-N 2-(benzenesulfonyl)ethanamine Chemical compound NCCS(=O)(=O)C1=CC=CC=C1 HEKKXNNVIAECAN-UHFFFAOYSA-N 0.000 description 1
- HSFNBRHAUKLROY-UHFFFAOYSA-N 2-(benzenesulfonyl)ethanamine;hydrochloride Chemical compound Cl.NCCS(=O)(=O)C1=CC=CC=C1 HSFNBRHAUKLROY-UHFFFAOYSA-N 0.000 description 1
- JKCHZZGNGPFZII-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)sulfonylpropyl]isoindole-1,3-dione Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)CCCN1C(=O)C2=CC=CC=C2C1=O JKCHZZGNGPFZII-UHFFFAOYSA-N 0.000 description 1
- KUSXDIGALTYDLG-UHFFFAOYSA-N 2-[benzyl(methyl)amino]acetonitrile Chemical compound N#CCN(C)CC1=CC=CC=C1 KUSXDIGALTYDLG-UHFFFAOYSA-N 0.000 description 1
- ULQQGOGMQRGFFR-UHFFFAOYSA-N 2-chlorobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=CC=C1Cl ULQQGOGMQRGFFR-UHFFFAOYSA-N 0.000 description 1
- UQSMMTFBNJUPGW-UHFFFAOYSA-N 2-chloroethylsulfanylmethylbenzene Chemical compound ClCCSCC1=CC=CC=C1 UQSMMTFBNJUPGW-UHFFFAOYSA-N 0.000 description 1
- CKNUUVURUUCDGT-UHFFFAOYSA-N 2-chloroethylsulfonylmethylbenzene Chemical compound ClCCS(=O)(=O)CC1=CC=CC=C1 CKNUUVURUUCDGT-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical group CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- UHXSZWXBMDJJHR-UHFFFAOYSA-N 3-(benzenesulfonyl)-n-propan-2-ylpropan-1-amine Chemical compound CC(C)NCCCS(=O)(=O)C1=CC=CC=C1 UHXSZWXBMDJJHR-UHFFFAOYSA-N 0.000 description 1
- GHNFGRIDWGVTNH-UHFFFAOYSA-N 3-(benzenesulfonyl)propan-1-amine Chemical compound NCCCS(=O)(=O)C1=CC=CC=C1 GHNFGRIDWGVTNH-UHFFFAOYSA-N 0.000 description 1
- VKHRIAKIDXSHNO-UHFFFAOYSA-N 3-[2-(diethylamino)ethyl]-1-[2-(2-methoxyphenyl)sulfonylethyl]-1-propan-2-ylurea Chemical compound CCN(CC)CCNC(=O)N(C(C)C)CCS(=O)(=O)C1=CC=CC=C1OC VKHRIAKIDXSHNO-UHFFFAOYSA-N 0.000 description 1
- VCWLYEVMMSGHGM-UHFFFAOYSA-N 3-[3-(4-chlorophenyl)sulfonylpropyl]-1-[2-(diethylamino)ethyl]-1-propan-2-ylurea Chemical compound CCN(CC)CCN(C(C)C)C(=O)NCCCS(=O)(=O)C1=CC=C(Cl)C=C1 VCWLYEVMMSGHGM-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- SBRLITLVSMPPFI-UHFFFAOYSA-N 3-chloropropylsulfanylbenzene Chemical compound ClCCCSC1=CC=CC=C1 SBRLITLVSMPPFI-UHFFFAOYSA-N 0.000 description 1
- ZDLOJWNTNFPUJU-UHFFFAOYSA-N 4-(2-chloroethylsulfonyl)benzonitrile Chemical class ClCCS(=O)(=O)C1=CC=C(C#N)C=C1 ZDLOJWNTNFPUJU-UHFFFAOYSA-N 0.000 description 1
- OKIHXNKYYGUVTE-UHFFFAOYSA-N 4-Fluorothiophenol Chemical compound FC1=CC=C(S)C=C1 OKIHXNKYYGUVTE-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- RBSCTKPUPXBMHO-UHFFFAOYSA-N 4-chloro-1-[4-chloro-2-(2-chloroethyl)phenyl]sulfanyl-2-(2-chloroethyl)benzene Chemical compound ClCCC1=CC(Cl)=CC=C1SC1=CC=C(Cl)C=C1CCCl RBSCTKPUPXBMHO-UHFFFAOYSA-N 0.000 description 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 1
- DGPJRPKVUFBWLH-UHFFFAOYSA-N 5-(2-chloroethylsulfonyl)-1,2,3-trimethoxybenzene Chemical compound COC1=CC(S(=O)(=O)CCCl)=CC(OC)=C1OC DGPJRPKVUFBWLH-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 235000003911 Arachis Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- DZFREBJSNPYCOU-BTJKTKAUSA-N C(\C=C/C(=O)O)(=O)O.CN(CCN(C(=O)N)C(C)C)C Chemical compound C(\C=C/C(=O)O)(=O)O.CN(CCN(C(=O)N)C(C)C)C DZFREBJSNPYCOU-BTJKTKAUSA-N 0.000 description 1
- 101100005001 Caenorhabditis elegans cah-5 gene Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
- 244000147935 Condalia obovata Species 0.000 description 1
- 235000008317 Condalia obovata Nutrition 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 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 1
- 206010022998 Irritability Diseases 0.000 description 1
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 1
- 235000019759 Maize starch Nutrition 0.000 description 1
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 101100109871 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) aro-8 gene Proteins 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 240000006394 Sorghum bicolor Species 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 235000009430 Thespesia populnea Nutrition 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 229960004373 acetylcholine Drugs 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 239000003416 antiarrhythmic agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000002763 arrhythmic effect Effects 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 125000005164 aryl thioalkyl group Chemical group 0.000 description 1
- 229940125717 barbiturate Drugs 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 230000004087 circulation Effects 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 125000004802 cyanophenyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 210000003191 femoral vein Anatomy 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 208000021302 gastroesophageal reflux disease Diseases 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 229960004194 lidocaine Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- RHMQNXNXUZLEIY-UHFFFAOYSA-N methanol;2-propan-2-yloxypropane Chemical compound OC.CC(C)OC(C)C RHMQNXNXUZLEIY-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- CURJNMSGPBXOGK-UHFFFAOYSA-N n',n'-di(propan-2-yl)ethane-1,2-diamine Chemical compound CC(C)N(C(C)C)CCN CURJNMSGPBXOGK-UHFFFAOYSA-N 0.000 description 1
- MKDYQLJYEBWUIG-UHFFFAOYSA-N n',n'-diethyl-n-methylethane-1,2-diamine Chemical compound CCN(CC)CCNC MKDYQLJYEBWUIG-UHFFFAOYSA-N 0.000 description 1
- QUMIGAREEPSVLG-UHFFFAOYSA-N n',n'-diethyl-n-phenylethane-1,2-diamine Chemical compound CCN(CC)CCNC1=CC=CC=C1 QUMIGAREEPSVLG-UHFFFAOYSA-N 0.000 description 1
- YPLIFKZBNCNJJN-UHFFFAOYSA-N n,n-bis(ethylamino)ethanamine Chemical compound CCNN(CC)NCC YPLIFKZBNCNJJN-UHFFFAOYSA-N 0.000 description 1
- NYIODHFKZFKMSU-UHFFFAOYSA-N n,n-bis(methylamino)ethanamine Chemical compound CCN(NC)NC NYIODHFKZFKMSU-UHFFFAOYSA-N 0.000 description 1
- PHWISQNXPLXQRU-UHFFFAOYSA-N n,n-dimethylcarbamothioyl chloride Chemical compound CN(C)C(Cl)=S PHWISQNXPLXQRU-UHFFFAOYSA-N 0.000 description 1
- FOYMPUJQDJFILG-UHFFFAOYSA-N n-(2-benzylsulfanylethyl)propan-2-amine;hydrochloride Chemical compound Cl.CC(C)NCCSCC1=CC=CC=C1 FOYMPUJQDJFILG-UHFFFAOYSA-N 0.000 description 1
- BPRNKCYEIBFDIB-UHFFFAOYSA-N n-(2-benzylsulfinylethyl)propan-2-amine Chemical compound CC(C)NCCS(=O)CC1=CC=CC=C1 BPRNKCYEIBFDIB-UHFFFAOYSA-N 0.000 description 1
- SRFCIJNNCYQZCZ-UHFFFAOYSA-N n-(2-naphthalen-1-ylsulfanylethyl)propan-2-amine Chemical compound C1=CC=C2C(SCCNC(C)C)=CC=CC2=C1 SRFCIJNNCYQZCZ-UHFFFAOYSA-N 0.000 description 1
- URAKRIOXJINZMV-UHFFFAOYSA-N n-(2-naphthalen-2-ylsulfanylethyl)propan-2-amine Chemical compound C1=CC=CC2=CC(SCCNC(C)C)=CC=C21 URAKRIOXJINZMV-UHFFFAOYSA-N 0.000 description 1
- JJRLDBRKLPVIMT-UHFFFAOYSA-N n-[2-(2,3-dihydro-1h-inden-4-ylsulfanyl)ethyl]propan-2-amine Chemical compound CC(C)NCCSC1=CC=CC2=C1CCC2 JJRLDBRKLPVIMT-UHFFFAOYSA-N 0.000 description 1
- AIEUSKJORZMIQO-UHFFFAOYSA-N n-[2-(3,4,5-trimethoxyphenyl)sulfonylethyl]propan-2-amine Chemical compound COC1=CC(S(=O)(=O)CCNC(C)C)=CC(OC)=C1OC AIEUSKJORZMIQO-UHFFFAOYSA-N 0.000 description 1
- WCIDTRWIASQWMT-UHFFFAOYSA-N n-[2-(3,5-dichlorophenyl)sulfonylethyl]propan-2-amine Chemical compound CC(C)NCCS(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 WCIDTRWIASQWMT-UHFFFAOYSA-N 0.000 description 1
- ZODNMAISYLFSAN-UHFFFAOYSA-N n-[2-(4-fluorophenyl)sulfanylethyl]propan-2-amine;hydrochloride Chemical compound Cl.CC(C)NCCSC1=CC=C(F)C=C1 ZODNMAISYLFSAN-UHFFFAOYSA-N 0.000 description 1
- BPUCNLMISDDWMY-UHFFFAOYSA-N n-[2-(4-fluorophenyl)sulfonylethyl]propan-2-amine Chemical compound CC(C)NCCS(=O)(=O)C1=CC=C(F)C=C1 BPUCNLMISDDWMY-UHFFFAOYSA-N 0.000 description 1
- ABCMQEWNGOVMCX-UHFFFAOYSA-N n-[2-(4-methoxyphenyl)sulfonylethyl]propan-2-amine;hydrochloride Chemical compound Cl.COC1=CC=C(S(=O)(=O)CCNC(C)C)C=C1 ABCMQEWNGOVMCX-UHFFFAOYSA-N 0.000 description 1
- IKPAVDUNPTZDCN-UHFFFAOYSA-N n-[2-(4-methylphenyl)sulfonylethyl]propan-2-amine Chemical compound CC(C)NCCS(=O)(=O)C1=CC=C(C)C=C1 IKPAVDUNPTZDCN-UHFFFAOYSA-N 0.000 description 1
- SKHYEHVXXDIBAM-UHFFFAOYSA-N n-[2-(4-nitrophenyl)sulfonylethyl]propan-2-amine Chemical compound CC(C)NCCS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 SKHYEHVXXDIBAM-UHFFFAOYSA-N 0.000 description 1
- ZGHDQSWEJBOANY-UHFFFAOYSA-N n-[2-(4-tert-butylphenyl)sulfonylethyl]propan-2-amine Chemical compound CC(C)NCCS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 ZGHDQSWEJBOANY-UHFFFAOYSA-N 0.000 description 1
- MMRVDDICTIKIJC-UHFFFAOYSA-N n-[2-(benzenesulfonyl)ethyl]aniline Chemical compound C=1C=CC=CC=1S(=O)(=O)CCNC1=CC=CC=C1 MMRVDDICTIKIJC-UHFFFAOYSA-N 0.000 description 1
- NOEWBTOORVWZNV-UHFFFAOYSA-N n-[2-(furan-2-ylmethylsulfanyl)ethyl]propan-2-amine Chemical compound CC(C)NCCSCC1=CC=CO1 NOEWBTOORVWZNV-UHFFFAOYSA-N 0.000 description 1
- XCWAFUIMGXRLIK-UHFFFAOYSA-N n-[2-(furan-2-ylmethylsulfanyl)ethyl]propan-2-amine;hydrochloride Chemical compound Cl.CC(C)NCCSCC1=CC=CO1 XCWAFUIMGXRLIK-UHFFFAOYSA-N 0.000 description 1
- SPJICGMRZOQNLM-UHFFFAOYSA-N n-[2-(furan-2-ylmethylsulfonyl)ethyl]propan-2-amine Chemical compound CC(C)NCCS(=O)(=O)CC1=CC=CO1 SPJICGMRZOQNLM-UHFFFAOYSA-N 0.000 description 1
- VETFNHIGZPWDMO-UHFFFAOYSA-N n-[2-[3-(trifluoromethyl)phenyl]sulfonylethyl]propan-2-amine Chemical compound CC(C)NCCS(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 VETFNHIGZPWDMO-UHFFFAOYSA-N 0.000 description 1
- RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SEXOVMIIVBKGGM-UHFFFAOYSA-N naphthalene-1-thiol Chemical compound C1=CC=C2C(S)=CC=CC2=C1 SEXOVMIIVBKGGM-UHFFFAOYSA-N 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- YBSLUBPQYDULIZ-UHFFFAOYSA-N oxalic acid;urea Chemical compound NC(N)=O.OC(=O)C(O)=O YBSLUBPQYDULIZ-UHFFFAOYSA-N 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
- 238000007911 parenteral administration Methods 0.000 description 1
- KHFGNBZOAOLKTM-UHFFFAOYSA-N phenyl n-[2-(4-fluorophenyl)sulfanylethyl]-n-propan-2-ylcarbamate Chemical compound C=1C=CC=CC=1OC(=O)N(C(C)C)CCSC1=CC=C(F)C=C1 KHFGNBZOAOLKTM-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229940113116 polyethylene glycol 1000 Drugs 0.000 description 1
- 229940057838 polyethylene glycol 4000 Drugs 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000004685 tetrahydrates Chemical class 0.000 description 1
- 230000017105 transposition Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- 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
- C07C317/28—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 acyclic carbon atoms of the carbon skeleton
-
- 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
-
- 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
- C07C323/39—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 at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/43—Y being a hetero atom
- C07C323/44—X or Y being nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/06—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms
- C07C335/08—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms of a saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US26527881A | 1981-05-20 | 1981-05-20 | |
US34545282A | 1982-02-03 | 1982-02-03 |
Publications (2)
Publication Number | Publication Date |
---|---|
IE821191L IE821191L (en) | 1982-11-20 |
IE53342B1 true IE53342B1 (en) | 1988-10-26 |
Family
ID=26951096
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IE1191/82A IE53342B1 (en) | 1981-05-20 | 1982-05-18 | N-(arylthioalkyl)-n-(aminoalkyl)ureas |
Country Status (17)
Country | Link |
---|---|
EP (1) | EP0066415B1 (OSRAM) |
KR (1) | KR890001811B1 (OSRAM) |
AU (1) | AU544976B2 (OSRAM) |
CA (1) | CA1180013A (OSRAM) |
DE (1) | DE3266645D1 (OSRAM) |
DK (1) | DK228482A (OSRAM) |
ES (3) | ES512329A0 (OSRAM) |
FI (1) | FI76557C (OSRAM) |
GR (1) | GR76412B (OSRAM) |
HK (1) | HK96986A (OSRAM) |
IE (1) | IE53342B1 (OSRAM) |
IL (1) | IL65567A (OSRAM) |
IN (1) | IN155992B (OSRAM) |
NO (1) | NO153848C (OSRAM) |
NZ (1) | NZ200669A (OSRAM) |
PH (1) | PH23473A (OSRAM) |
PT (1) | PT74930B (OSRAM) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IL74140A (en) * | 1984-04-10 | 1988-05-31 | Robins Co Inc A H | Substituted n-((amino)alkyl)-1-pyrrolidine,-1-piperidine and-1-homopiperidine-carboxamides and pharmaceutical compositions containing them |
US4895840A (en) * | 1987-06-10 | 1990-01-23 | A. H. Robins Company, Incorporated | N-(aryl-,aryloxy-,arylthio-arylsulfinyl-and arylsulfonyl-)alkyl-N,N'-(or n'n')alkylaminoalkyl ureas and cyanoguanidines |
FR2664269B1 (fr) * | 1990-07-05 | 1992-10-02 | Roussel Uclaf | Nouveaux derives n-substitues d'alpha-mercapto alkylamines, leur procede de preparation, leur application a titre de medicaments et les compositions les renfermant. |
WO2001023350A1 (en) * | 1999-09-28 | 2001-04-05 | Nihon Nohyaku Co., Ltd. | Thioalkylamine derivatives and process for the preparation thereof |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2832756A (en) * | 1955-04-15 | 1958-04-29 | Rohm & Haas | Monomeric polymerizable ureido and thioureido compounds, methods for producing them and polymers thereof |
FR2296406A1 (fr) * | 1974-12-31 | 1976-07-30 | Oreal | Nouvelles compositions cosmetiques a base de derives sulfoxydes de la cysteamine |
GB1604674A (en) * | 1977-05-17 | 1981-12-16 | Allen & Hanburys Ltd | Aminoalkyl-benzene derivatives |
-
1982
- 1982-04-21 IL IL65567A patent/IL65567A/xx unknown
- 1982-05-12 PH PH27278A patent/PH23473A/en unknown
- 1982-05-13 GR GR68143A patent/GR76412B/el unknown
- 1982-05-18 IE IE1191/82A patent/IE53342B1/en unknown
- 1982-05-18 IN IN557/CAL/82A patent/IN155992B/en unknown
- 1982-05-19 ES ES512329A patent/ES512329A0/es active Granted
- 1982-05-19 CA CA000403325A patent/CA1180013A/en not_active Expired
- 1982-05-19 DK DK228482A patent/DK228482A/da not_active Application Discontinuation
- 1982-05-19 ES ES512328A patent/ES8303303A1/es not_active Expired
- 1982-05-19 NZ NZ200669A patent/NZ200669A/en unknown
- 1982-05-19 FI FI821776A patent/FI76557C/fi not_active IP Right Cessation
- 1982-05-19 PT PT74930A patent/PT74930B/pt unknown
- 1982-05-19 EP EP82302557A patent/EP0066415B1/en not_active Expired
- 1982-05-19 DE DE8282302557T patent/DE3266645D1/de not_active Expired
- 1982-05-19 ES ES512330A patent/ES512330A0/es active Granted
- 1982-05-19 NO NO821668A patent/NO153848C/no unknown
- 1982-05-20 KR KR8202205A patent/KR890001811B1/ko not_active Expired
- 1982-05-20 AU AU83881/82A patent/AU544976B2/en not_active Ceased
-
1986
- 1986-12-11 HK HK969/86A patent/HK96986A/xx unknown
Also Published As
Publication number | Publication date |
---|---|
EP0066415A2 (en) | 1982-12-08 |
KR890001811B1 (ko) | 1989-05-23 |
PH23473A (en) | 1989-08-07 |
ES512328A0 (es) | 1983-02-01 |
AU544976B2 (en) | 1985-06-27 |
NZ200669A (en) | 1985-12-13 |
NO153848B (no) | 1986-02-24 |
ES8303305A1 (es) | 1983-02-01 |
ES512330A0 (es) | 1983-02-01 |
IN155992B (OSRAM) | 1985-04-20 |
AU8388182A (en) | 1982-11-25 |
IL65567A (en) | 1985-11-29 |
NO821668L (no) | 1982-11-22 |
EP0066415A3 (en) | 1983-09-14 |
DE3266645D1 (de) | 1985-11-07 |
DK228482A (da) | 1982-11-21 |
KR830010057A (ko) | 1983-12-24 |
NO153848C (no) | 1986-06-04 |
EP0066415B1 (en) | 1985-10-02 |
IE821191L (en) | 1982-11-20 |
IL65567A0 (en) | 1982-07-30 |
PT74930A (en) | 1982-06-01 |
FI76557B (fi) | 1988-07-29 |
CA1180013A (en) | 1984-12-27 |
FI821776A0 (fi) | 1982-05-19 |
ES8303304A1 (es) | 1983-02-01 |
ES8303303A1 (es) | 1983-02-01 |
FI76557C (fi) | 1988-11-10 |
GR76412B (OSRAM) | 1984-08-10 |
ES512329A0 (es) | 1983-02-01 |
HK96986A (en) | 1986-12-19 |
PT74930B (en) | 1983-12-07 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CA1303616C (en) | N-1-azabicyclo¬2,2,2|-oct-3yl)-benzamide compounds | |
NO169485B (no) | Analogifremgangsmaate til fremstilling av farmakologisk aktive, substituerte benzamidderivater | |
US4500529A (en) | Method of treating cardiac disorders with N-(aryloxyalkyl)-N'-(aminoalkyl)ureas | |
US4895840A (en) | N-(aryl-,aryloxy-,arylthio-arylsulfinyl-and arylsulfonyl-)alkyl-N,N'-(or n'n')alkylaminoalkyl ureas and cyanoguanidines | |
IE911439A1 (en) | Therapeutic N-(2-Biphenylyl)guanidine derivatives | |
US4724235A (en) | N-(arylthioalkyl)-N'-(aminoalkyl)ureas useful in the treatment of arrhythmia | |
FR2459235A1 (fr) | Nouveaux derives de sulfonyl-aniline, leur procede de preparation et leur application therapeutique | |
US8183234B2 (en) | Tricyclic guanidine derivatives as sodium-proton exchange inhibitors | |
US4597902A (en) | N-(arylthioalkyl)-N'-(aminoalkyl)ureas | |
US4558155A (en) | N-(Aryloxyalkyl)-N'-(aminoalkyl)thioureas | |
IE49320B1 (en) | N-alkynyl-n'((optionally substituted thiazolyl)methylthio)alkyl-derivatives of n"-cyanoguanidine and of 1,1-diamino-2-substituted ethylene | |
IE53342B1 (en) | N-(arylthioalkyl)-n-(aminoalkyl)ureas | |
FI65243C (fi) | Foerfarande foer framstaellning av heterocykliska derivat av guanidin | |
FI76552B (fi) | Foerfarande foer framstaellning av farmakologiskt aktiva n-(aryloxialkyl)-n'-(aminoalkyl)-ureafoereningar. | |
CA1083171A (en) | Pharmacologically active isothioureas derivatives | |
JPH0357892B2 (OSRAM) | ||
CZ291094B6 (cs) | Substituované chromanylsulfonyl(thio)močoviny, způsob jejich přípravy, jejich pouľití ve farmaceutických preparátech jakoľ i léčiva, která je obsahují | |
JPH0433787B2 (OSRAM) | ||
EP0559569A1 (en) | Central nervous system antiischemic agents |