HU187706B - Process for preparing n-/aryl-oxy.alkyl/-n'-/amino-alkyl/-carbamide derivatives - Google Patents
Process for preparing n-/aryl-oxy.alkyl/-n'-/amino-alkyl/-carbamide derivatives Download PDFInfo
- Publication number
- HU187706B HU187706B HU821580A HU158082A HU187706B HU 187706 B HU187706 B HU 187706B HU 821580 A HU821580 A HU 821580A HU 158082 A HU158082 A HU 158082A HU 187706 B HU187706 B HU 187706B
- Authority
- HU
- Hungary
- Prior art keywords
- ethyl
- starting materials
- urea
- dimethylamino
- reacted
- Prior art date
Links
- 125000000217 alkyl group Chemical group 0.000 title claims abstract description 10
- 125000004104 aryloxy group Chemical group 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
- 150000003585 thioureas Chemical class 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 206
- 238000000034 method Methods 0.000 claims description 164
- 239000000126 substance Substances 0.000 claims description 142
- 239000007858 starting material Substances 0.000 claims description 93
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 93
- -1 3,4-dichlorophenoxy Chemical group 0.000 claims description 86
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 86
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 82
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 66
- 229910052739 hydrogen Inorganic materials 0.000 claims description 53
- 238000002360 preparation method Methods 0.000 claims description 50
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 40
- 229910052757 nitrogen Inorganic materials 0.000 claims description 37
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 31
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 23
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 21
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 18
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
- 239000004202 carbamide Substances 0.000 claims description 12
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 6
- 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 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 150000004677 hydrates Chemical class 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 229940095064 tartrate Drugs 0.000 claims description 4
- 125000006564 (C4-C8) cycloalkyl group Chemical group 0.000 claims description 3
- GJFNRSDCSTVPCJ-UHFFFAOYSA-N 1,8-bis(dimethylamino)naphthalene Chemical compound C1=CC(N(C)C)=C2C(N(C)C)=CC=CC2=C1 GJFNRSDCSTVPCJ-UHFFFAOYSA-N 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 3
- ORPDIIJETKXXCU-UHFFFAOYSA-N C(C=C/C(=O)O)(=O)O.CC(C)NC(=O)N Chemical compound C(C=C/C(=O)O)(=O)O.CC(C)NC(=O)N ORPDIIJETKXXCU-UHFFFAOYSA-N 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- HLNZWQXAKLAOKH-WLHGVMLRSA-N (e)-but-2-enedioic acid;3-[2-(dimethylamino)ethyl]-1-(2-phenoxyethyl)-1-propan-2-ylurea Chemical compound OC(=O)\C=C\C(O)=O.CN(C)CCNC(=O)N(C(C)C)CCOC1=CC=CC=C1 HLNZWQXAKLAOKH-WLHGVMLRSA-N 0.000 claims description 2
- RPZLEHRDAQYZAJ-WLHGVMLRSA-N (e)-but-2-enedioic acid;3-[2-(dimethylamino)ethyl]-1-[2-(3,5-dimethylphenoxy)ethyl]-1-propan-2-ylurea Chemical compound OC(=O)\C=C\C(O)=O.CN(C)CCNC(=O)N(C(C)C)CCOC1=CC(C)=CC(C)=C1 RPZLEHRDAQYZAJ-WLHGVMLRSA-N 0.000 claims description 2
- YLFSVOKFKVDVSA-WLHGVMLRSA-N (e)-but-2-enedioic acid;3-[2-(dimethylamino)ethyl]-1-[2-(3-fluorophenoxy)ethyl]-1-propan-2-ylurea Chemical compound OC(=O)\C=C\C(O)=O.CN(C)CCNC(=O)N(C(C)C)CCOC1=CC=CC(F)=C1 YLFSVOKFKVDVSA-WLHGVMLRSA-N 0.000 claims description 2
- KHKHDEIXSOQXRV-BTJKTKAUSA-N (z)-but-2-enedioic acid;1-[2-(3,5-dichlorophenoxy)ethyl]-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)CCOC1=CC(Cl)=CC(Cl)=C1 KHKHDEIXSOQXRV-BTJKTKAUSA-N 0.000 claims description 2
- WESLVTHPINPNGQ-BTJKTKAUSA-N (z)-but-2-enedioic acid;1-[2-(4-chlorophenoxy)ethyl]-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)CCOC1=CC=C(Cl)C=C1 WESLVTHPINPNGQ-BTJKTKAUSA-N 0.000 claims description 2
- CMSDCZGTMRZMTR-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenoxy)ethyl]-3-[2-(dimethylamino)ethyl]-1-phenylurea;hydrochloride Chemical compound Cl.C=1C=CC=CC=1N(C(=O)NCCN(C)C)CCOC1=CC(Cl)=CC(Cl)=C1 CMSDCZGTMRZMTR-UHFFFAOYSA-N 0.000 claims description 2
- YRPHLFITRMZBAN-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenoxy)ethyl]-3-methyl-3-[2-(methylamino)ethyl]-1-propan-2-ylurea Chemical compound CNCCN(C)C(=O)N(C(C)C)CCOC1=CC(Cl)=CC(Cl)=C1 YRPHLFITRMZBAN-UHFFFAOYSA-N 0.000 claims description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
- VZJWDHISTHIBKY-UHFFFAOYSA-N 3-[2-(diethylamino)ethyl]-1-(2-phenoxyethyl)-1-propan-2-ylthiourea;oxalic acid Chemical compound OC(=O)C(O)=O.CCN(CC)CCNC(=S)N(C(C)C)CCOC1=CC=CC=C1 VZJWDHISTHIBKY-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 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
- VQGRLAXNKMDYKK-WLHGVMLRSA-N (e)-but-2-enedioic acid;3-[2-(dimethylamino)ethyl]-1-[2-(3,4-dimethylphenoxy)ethyl]-1-propan-2-ylurea Chemical compound OC(=O)\C=C\C(O)=O.CN(C)CCNC(=O)N(C(C)C)CCOC1=CC=C(C)C(C)=C1 VQGRLAXNKMDYKK-WLHGVMLRSA-N 0.000 claims 2
- GIGWPEHHEXJSTD-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenoxy)ethyl]-3-[2-(diethylamino)ethyl]-1-propan-2-ylurea Chemical compound CCN(CC)CCNC(=O)N(C(C)C)CCOC1=CC(Cl)=CC(Cl)=C1 GIGWPEHHEXJSTD-UHFFFAOYSA-N 0.000 claims 2
- LUARBZIBHJKZGZ-UHFFFAOYSA-N 1-[3-(3,5-dichlorophenoxy)propyl]-3-[2-(dimethylamino)ethyl]-1-propan-2-ylurea Chemical compound CN(C)CCNC(=O)N(C(C)C)CCCOC1=CC(Cl)=CC(Cl)=C1 LUARBZIBHJKZGZ-UHFFFAOYSA-N 0.000 claims 2
- WCAADOABRKEAGY-UHFFFAOYSA-N 3-[2-(dimethylamino)ethyl]-1-(2-naphthalen-2-yloxyethyl)-1-propan-2-ylurea Chemical compound C1=CC=CC2=CC(OCCN(C(C)C)C(=O)NCCN(C)C)=CC=C21 WCAADOABRKEAGY-UHFFFAOYSA-N 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- POXAIQSXNOEQGM-UHFFFAOYSA-N propan-2-ylthiourea Chemical compound CC(C)NC(N)=S POXAIQSXNOEQGM-UHFFFAOYSA-N 0.000 claims 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- TVMVFNLZYBGNEE-WLHGVMLRSA-N (e)-but-2-enedioic acid;1-[2-(3,5-dichlorophenoxy)ethyl]-3-[2-(dimethylamino)ethyl]urea Chemical compound OC(=O)\C=C\C(O)=O.CN(C)CCNC(=O)NCCOC1=CC(Cl)=CC(Cl)=C1 TVMVFNLZYBGNEE-WLHGVMLRSA-N 0.000 claims 1
- VWVIGIJVJWQHIL-WLHGVMLRSA-N (e)-but-2-enedioic acid;3-[2-(2,3-dihydro-1h-inden-4-yloxy)ethyl]-1-methyl-1-[2-(methylamino)ethyl]urea Chemical compound OC(=O)\C=C\C(O)=O.CNCCN(C)C(=O)NCCOC1=CC=CC2=C1CCC2 VWVIGIJVJWQHIL-WLHGVMLRSA-N 0.000 claims 1
- LCCCONVHFYNWLR-WLHGVMLRSA-N (e)-but-2-enedioic acid;3-[2-(dimethylamino)ethyl]-1-propan-2-yl-1-[2-[3-(trifluoromethyl)phenoxy]ethyl]urea Chemical compound OC(=O)\C=C\C(O)=O.CN(C)CCNC(=O)N(C(C)C)CCOC1=CC=CC(C(F)(F)F)=C1 LCCCONVHFYNWLR-WLHGVMLRSA-N 0.000 claims 1
- HAFWELDDNUXLCK-TYYBGVCCSA-N (e)-but-2-enedioic acid;hydrate Chemical compound O.OC(=O)\C=C\C(O)=O HAFWELDDNUXLCK-TYYBGVCCSA-N 0.000 claims 1
- LKWPVKCGEXUINL-BTJKTKAUSA-N (z)-but-2-enedioic acid;1-[2-(2-chlorophenoxy)ethyl]-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)CCOC1=CC=CC=C1Cl LKWPVKCGEXUINL-BTJKTKAUSA-N 0.000 claims 1
- BBOAUUXLTWITMC-BTJKTKAUSA-N (z)-but-2-enedioic acid;1-[2-(3,5-dichlorophenoxy)ethyl]-3-[2-(dimethylamino)ethyl]-1-methylurea Chemical compound OC(=O)\C=C/C(O)=O.CN(C)CCNC(=O)N(C)CCOC1=CC(Cl)=CC(Cl)=C1 BBOAUUXLTWITMC-BTJKTKAUSA-N 0.000 claims 1
- QEZPEVOLNNHLCF-BTJKTKAUSA-N (z)-but-2-enedioic acid;1-[2-(3,5-dichlorophenoxy)ethyl]-3-[2-(dimethylamino)ethyl]-1-propylurea Chemical compound OC(=O)\C=C/C(O)=O.CN(C)CCNC(=O)N(CCC)CCOC1=CC(Cl)=CC(Cl)=C1 QEZPEVOLNNHLCF-BTJKTKAUSA-N 0.000 claims 1
- TUDNAYZCGLAVJX-BTJKTKAUSA-N (z)-but-2-enedioic acid;1-[2-(3,5-dichlorophenoxy)ethyl]-3-methyl-3-[2-(methylamino)ethyl]-1-propan-2-ylurea Chemical compound OC(=O)\C=C/C(O)=O.CNCCN(C)C(=O)N(C(C)C)CCOC1=CC(Cl)=CC(Cl)=C1 TUDNAYZCGLAVJX-BTJKTKAUSA-N 0.000 claims 1
- WMVCORHYZGSHIN-BTJKTKAUSA-N (z)-but-2-enedioic acid;1-butyl-1-[2-(3,5-dichlorophenoxy)ethyl]-3-[2-(dimethylamino)ethyl]urea Chemical compound OC(=O)\C=C/C(O)=O.CN(C)CCNC(=O)N(CCCC)CCOC1=CC(Cl)=CC(Cl)=C1 WMVCORHYZGSHIN-BTJKTKAUSA-N 0.000 claims 1
- JSHMGPZVAYIWFP-BTJKTKAUSA-N (z)-but-2-enedioic acid;3-[2-(dimethylamino)ethyl]-1-(2-naphthalen-1-yloxyethyl)-1-propan-2-ylurea Chemical compound OC(=O)\C=C/C(O)=O.C1=CC=C2C(OCCN(C(C)C)C(=O)NCCN(C)C)=CC=CC2=C1 JSHMGPZVAYIWFP-BTJKTKAUSA-N 0.000 claims 1
- XZTMXMKXQJEICM-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)ethyl]-3-[3-(dimethylamino)propyl]-1-propan-2-ylurea Chemical compound CN(C)CCCNC(=O)N(C(C)C)CCOC1=CC=C(Cl)C(Cl)=C1 XZTMXMKXQJEICM-UHFFFAOYSA-N 0.000 claims 1
- LJHOHLMWLAPJSG-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)ethyl]-3-[3-(dimethylamino)propyl]-1-propan-2-ylurea;oxalic acid Chemical compound OC(=O)C(O)=O.CN(C)CCCNC(=O)N(C(C)C)CCOC1=CC=C(Cl)C(Cl)=C1 LJHOHLMWLAPJSG-UHFFFAOYSA-N 0.000 claims 1
- HVCVQHBPDDVNLW-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenoxy)ethyl]-3-(2-morpholin-4-ylethyl)-1-propan-2-ylurea Chemical compound C1COCCN1CCNC(=O)N(C(C)C)CCOC1=CC(Cl)=CC(Cl)=C1 HVCVQHBPDDVNLW-UHFFFAOYSA-N 0.000 claims 1
- IUXQCBQPUMECTQ-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenoxy)ethyl]-3-[2-(dimethylamino)ethyl]-1-methylurea Chemical compound CN(C)CCNC(=O)N(C)CCOC1=CC(Cl)=CC(Cl)=C1 IUXQCBQPUMECTQ-UHFFFAOYSA-N 0.000 claims 1
- YIPPFOLKDIACNA-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenoxy)ethyl]-3-[2-(dimethylamino)ethyl]-1-propylurea Chemical compound CN(C)CCNC(=O)N(CCC)CCOC1=CC(Cl)=CC(Cl)=C1 YIPPFOLKDIACNA-UHFFFAOYSA-N 0.000 claims 1
- QXIVVOYNMQUAHV-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenoxy)ethyl]-3-[2-(dimethylamino)ethyl]-3-methyl-1-propan-2-ylurea;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.CN(C)CCN(C)C(=O)N(C(C)C)CCOC1=CC(Cl)=CC(Cl)=C1 QXIVVOYNMQUAHV-UHFFFAOYSA-N 0.000 claims 1
- XMOPNRKLUAFQSB-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenoxy)ethyl]-3-[2-(dimethylamino)ethyl]urea Chemical compound CN(C)CCNC(=O)NCCOC1=CC(Cl)=CC(Cl)=C1 XMOPNRKLUAFQSB-UHFFFAOYSA-N 0.000 claims 1
- NWQNKBZWWDAEQO-UHFFFAOYSA-N 1-[2-(4-chlorophenoxy)ethyl]-3-[2-(dimethylamino)ethyl]-1-propan-2-ylurea Chemical compound CN(C)CCNC(=O)N(C(C)C)CCOC1=CC=C(Cl)C=C1 NWQNKBZWWDAEQO-UHFFFAOYSA-N 0.000 claims 1
- NHXAIZPKCJZNJE-UHFFFAOYSA-N 1-butyl-1-[2-(3,5-dichlorophenoxy)ethyl]-3-[2-(dimethylamino)ethyl]urea Chemical compound CN(C)CCNC(=O)N(CCCC)CCOC1=CC(Cl)=CC(Cl)=C1 NHXAIZPKCJZNJE-UHFFFAOYSA-N 0.000 claims 1
- ZQUBSJPCTJCEDK-UHFFFAOYSA-N 1-cyclohexyl-1-[2-(3,5-dichlorophenoxy)ethyl]-3-[2-(dimethylamino)ethyl]urea Chemical compound C1CCCCC1N(C(=O)NCCN(C)C)CCOC1=CC(Cl)=CC(Cl)=C1 ZQUBSJPCTJCEDK-UHFFFAOYSA-N 0.000 claims 1
- MBCBUMNEVIPUEC-UHFFFAOYSA-N 1-methyl-1-(2-phenoxyethyl)-3-(2-pyrrolidin-1-ylethyl)urea Chemical compound C1CCCN1CCNC(=O)N(C)CCOC1=CC=CC=C1 MBCBUMNEVIPUEC-UHFFFAOYSA-N 0.000 claims 1
- ZCBOCHUQPMQUSK-BTJKTKAUSA-N 3-(2-aminoethyl)-1-[2-(3,5-dichlorophenoxy)ethyl]-1-propan-2-ylurea;(z)-but-2-enedioic acid Chemical compound OC(=O)\C=C/C(O)=O.NCCNC(=O)N(C(C)C)CCOC1=CC(Cl)=CC(Cl)=C1 ZCBOCHUQPMQUSK-BTJKTKAUSA-N 0.000 claims 1
- OOTHUFABCRGNQT-UHFFFAOYSA-N 3-[2-(2,3-dihydro-1h-inden-4-yloxy)ethyl]-1-methyl-1-[2-(methylamino)ethyl]urea Chemical compound CNCCN(C)C(=O)NCCOC1=CC=CC2=C1CCC2 OOTHUFABCRGNQT-UHFFFAOYSA-N 0.000 claims 1
- GYSINKHJIMYDIR-UHFFFAOYSA-N 3-[2-(3,5-dichlorophenoxy)ethyl]-1-[2-(dimethylamino)ethyl]-1-methylurea Chemical compound CN(C)CCN(C)C(=O)NCCOC1=CC(Cl)=CC(Cl)=C1 GYSINKHJIMYDIR-UHFFFAOYSA-N 0.000 claims 1
- MYWSPBDVRYZYAI-UHFFFAOYSA-N 3-[2-(diethylamino)ethyl]-1-(2-phenoxyethyl)-1-propan-2-ylthiourea Chemical compound CCN(CC)CCNC(=S)N(C(C)C)CCOC1=CC=CC=C1 MYWSPBDVRYZYAI-UHFFFAOYSA-N 0.000 claims 1
- QPXNDIAYIZCYQC-UHFFFAOYSA-N 3-[2-(diethylamino)ethyl]-1-methyl-1-(2-phenoxyethyl)urea Chemical compound CCN(CC)CCNC(=O)N(C)CCOC1=CC=CC=C1 QPXNDIAYIZCYQC-UHFFFAOYSA-N 0.000 claims 1
- IMYQTUBRYKYGRX-UHFFFAOYSA-N 3-[2-(dimethylamino)ethyl]-1-(2-naphthalen-1-yloxyethyl)-1-propan-2-ylthiourea Chemical compound C1=CC=C2C(OCCN(C(C)C)C(=S)NCCN(C)C)=CC=CC2=C1 IMYQTUBRYKYGRX-UHFFFAOYSA-N 0.000 claims 1
- ZAWVTXXUHXXYQW-UHFFFAOYSA-N 3-[2-(dimethylamino)ethyl]-1-[2-(3,4-dimethylphenoxy)ethyl]-1-propan-2-ylurea Chemical compound CN(C)CCNC(=O)N(C(C)C)CCOC1=CC=C(C)C(C)=C1 ZAWVTXXUHXXYQW-UHFFFAOYSA-N 0.000 claims 1
- UKYDQWPGHHBUAE-UHFFFAOYSA-N 3-[2-(dimethylamino)ethyl]-1-[2-(3,5-dimethylphenoxy)ethyl]-1-propan-2-ylurea Chemical compound CN(C)CCNC(=O)N(C(C)C)CCOC1=CC(C)=CC(C)=C1 UKYDQWPGHHBUAE-UHFFFAOYSA-N 0.000 claims 1
- BBJQWYJYMQFHMK-UHFFFAOYSA-N 3-[2-(dimethylamino)ethyl]-1-propan-2-yl-1-[2-[3-(trifluoromethyl)phenoxy]ethyl]urea Chemical compound CN(C)CCNC(=O)N(C(C)C)CCOC1=CC=CC(C(F)(F)F)=C1 BBJQWYJYMQFHMK-UHFFFAOYSA-N 0.000 claims 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 claims 1
- AFCCDDWKHLHPDF-UHFFFAOYSA-M metam-sodium Chemical compound [Na+].CNC([S-])=S AFCCDDWKHLHPDF-UHFFFAOYSA-M 0.000 claims 1
- 206010003119 arrhythmia Diseases 0.000 abstract description 30
- 150000003672 ureas Chemical class 0.000 abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 2
- 235000013877 carbamide Nutrition 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 88
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 87
- 239000012458 free base Substances 0.000 description 81
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 78
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 73
- 239000000243 solution Substances 0.000 description 54
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 53
- 238000006243 chemical reaction Methods 0.000 description 43
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 38
- 239000011541 reaction mixture Substances 0.000 description 33
- 239000000203 mixture Substances 0.000 description 31
- 239000000460 chlorine Substances 0.000 description 29
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 28
- 239000011976 maleic acid Substances 0.000 description 28
- 230000006793 arrhythmia Effects 0.000 description 26
- 235000011167 hydrochloric acid Nutrition 0.000 description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 25
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 239000007787 solid Substances 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 239000012071 phase Substances 0.000 description 19
- 239000000047 product Substances 0.000 description 19
- 239000004480 active ingredient Substances 0.000 description 18
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
- 229910052801 chlorine Inorganic materials 0.000 description 13
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 13
- TYBARJRCFHUHSN-DMJRSANLSA-N 3-[(1r,3s,5s,8r,9s,10r,11r,13r,14s,17r)-1,5,11,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-3-[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2h-furan-5-one;octahydrate Chemical compound O.O.O.O.O.O.O.O.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 TYBARJRCFHUHSN-DMJRSANLSA-N 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- 235000019198 oils Nutrition 0.000 description 12
- 241000282472 Canis lupus familiaris Species 0.000 description 11
- 239000001530 fumaric acid Substances 0.000 description 11
- 235000011087 fumaric acid Nutrition 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- 238000010626 work up procedure Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 244000025254 Cannabis sativa Species 0.000 description 8
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
- 239000004615 ingredient 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
- HEZNWNFDRDZRBX-UHFFFAOYSA-N n-[2-(3,5-dichlorophenoxy)ethyl]propan-2-amine Chemical compound CC(C)NCCOC1=CC(Cl)=CC(Cl)=C1 HEZNWNFDRDZRBX-UHFFFAOYSA-N 0.000 description 8
- 235000006408 oxalic acid Nutrition 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 101100460584 Chaetomium thermophilum (strain DSM 1495 / CBS 144.50 / IMI 039719) NOC1 gene Proteins 0.000 description 7
- 101100022229 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) MAK21 gene Proteins 0.000 description 7
- 101100313929 Schizosaccharomyces pombe (strain 972 / ATCC 24843) tip1 gene Proteins 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 238000001802 infusion Methods 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 235000015165 citric acid Nutrition 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000008194 pharmaceutical composition Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 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 5
- 150000007513 acids Chemical class 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 description 5
- 235000019392 nitrosyl chloride Nutrition 0.000 description 5
- PUIRUKSEFBYKPI-UHFFFAOYSA-N 2-(2-bromoethyl)-1-[2-(2-bromoethyl)-3,5-dichlorophenoxy]-3,5-dichlorobenzene Chemical compound ClC1=CC(Cl)=C(CCBr)C(OC=2C(=C(Cl)C=C(Cl)C=2)CCBr)=C1 PUIRUKSEFBYKPI-UHFFFAOYSA-N 0.000 description 4
- 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 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 244000166550 Strophanthus gratus Species 0.000 description 4
- 239000007853 buffer solution Substances 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- BYXYCUABYHCYLY-UHFFFAOYSA-N isoindole-1,3-dione;potassium Chemical compound [K].C1=CC=C2C(=O)NC(=O)C2=C1 BYXYCUABYHCYLY-UHFFFAOYSA-N 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 4
- 229960003343 ouabain Drugs 0.000 description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 4
- 239000002244 precipitate Substances 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
- 230000033764 rhythmic process Effects 0.000 description 4
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 3
- FJMQDWMDXIGLLM-UHFFFAOYSA-N 2-(3,5-dichlorophenoxy)ethanamine Chemical compound NCCOC1=CC(Cl)=CC(Cl)=C1 FJMQDWMDXIGLLM-UHFFFAOYSA-N 0.000 description 3
- 206010003130 Arrhythmia supraventricular Diseases 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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 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 3
- 208000027418 Wounds and injury Diseases 0.000 description 3
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 3
- 229960004373 acetylcholine Drugs 0.000 description 3
- 230000003288 anthiarrhythmic effect Effects 0.000 description 3
- 230000004872 arterial blood pressure Effects 0.000 description 3
- 230000001746 atrial effect Effects 0.000 description 3
- 229940125717 barbiturate Drugs 0.000 description 3
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 3
- 210000004351 coronary vessel Anatomy 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 208000014674 injury Diseases 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 239000011975 tartaric acid Substances 0.000 description 3
- 235000002906 tartaric acid Nutrition 0.000 description 3
- 230000002861 ventricular Effects 0.000 description 3
- BUGZWLHKAJDSRW-UHFFFAOYSA-N 2-[2-(3,5-dichlorophenoxy)ethyl]isoindole-1,3-dione Chemical compound ClC1=CC(Cl)=CC(OCCN2C(C3=CC=CC=C3C2=O)=O)=C1 BUGZWLHKAJDSRW-UHFFFAOYSA-N 0.000 description 2
- JJFOBACUIRKUPN-UHFFFAOYSA-N 2-bromoethoxybenzene Chemical compound BrCCOC1=CC=CC=C1 JJFOBACUIRKUPN-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- WRXNJTBODVGDRY-UHFFFAOYSA-N 2-pyrrolidin-1-ylethanamine Chemical compound NCCN1CCCC1 WRXNJTBODVGDRY-UHFFFAOYSA-N 0.000 description 2
- ZBUYGEOTGLANGW-UHFFFAOYSA-N 3-(3,5-dichlorophenoxy)-n-propan-2-ylpropan-1-amine Chemical compound CC(C)NCCCOC1=CC(Cl)=CC(Cl)=C1 ZBUYGEOTGLANGW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 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
- 101000958664 Homo sapiens Nucleus accumbens-associated protein 1 Proteins 0.000 description 2
- 101000631760 Homo sapiens Sodium channel protein type 1 subunit alpha Proteins 0.000 description 2
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 2
- 102100028910 Sodium channel protein type 1 subunit alpha Human genes 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000003416 antiarrhythmic agent Substances 0.000 description 2
- 230000037396 body weight Effects 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
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 235000019504 cigarettes Nutrition 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
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 210000003191 femoral vein Anatomy 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- PEHSSTUGJUBZBI-UHFFFAOYSA-N indan-5-ol Chemical compound OC1=CC=C2CCCC2=C1 PEHSSTUGJUBZBI-UHFFFAOYSA-N 0.000 description 2
- 230000003601 intercostal effect Effects 0.000 description 2
- 229960004194 lidocaine Drugs 0.000 description 2
- 150000002688 maleic acid derivatives Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 2
- IKOVVHZXLBYZJZ-UHFFFAOYSA-N n-(2-naphthalen-1-yloxyethyl)propan-2-amine Chemical compound C1=CC=C2C(OCCNC(C)C)=CC=CC2=C1 IKOVVHZXLBYZJZ-UHFFFAOYSA-N 0.000 description 2
- WVFGRNGNOVCUFS-UHFFFAOYSA-N n-(2-phenoxyethyl)propan-2-amine Chemical compound CC(C)NCCOC1=CC=CC=C1 WVFGRNGNOVCUFS-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- UCFAXAMWQIQDOJ-UHFFFAOYSA-N n-[2-(3,4-dichlorophenoxy)ethyl]propan-2-amine Chemical compound CC(C)NCCOC1=CC=C(Cl)C(Cl)=C1 UCFAXAMWQIQDOJ-UHFFFAOYSA-N 0.000 description 2
- GUMBNOITRNRLCS-UHFFFAOYSA-N n-methyl-2-phenoxyethanamine Chemical compound CNCCOC1=CC=CC=C1 GUMBNOITRNRLCS-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 229960001404 quinidine Drugs 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 210000005245 right atrium Anatomy 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000008174 sterile solution Substances 0.000 description 2
- 238000001356 surgical procedure Methods 0.000 description 2
- 230000001960 triggered effect Effects 0.000 description 2
- DYPOEEJDEYWPAI-UHFFFAOYSA-N (1-azaniumyl-3-methylbutan-2-yl)azanium;dichloride Chemical compound Cl.Cl.CC(C)C(N)CN DYPOEEJDEYWPAI-UHFFFAOYSA-N 0.000 description 1
- 125000006833 (C1-C5) alkylene group Chemical group 0.000 description 1
- SYAWTWUNHDZHDX-BTJKTKAUSA-N (Z)-but-2-enedioic acid 1-[2-(3-chlorophenoxy)ethyl]-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)CCOC1=CC=CC(Cl)=C1 SYAWTWUNHDZHDX-BTJKTKAUSA-N 0.000 description 1
- KKUGLUXXIGKECX-TYYBGVCCSA-N (e)-but-2-enedioic acid;urea Chemical compound NC(N)=O.OC(=O)\C=C\C(O)=O KKUGLUXXIGKECX-TYYBGVCCSA-N 0.000 description 1
- CQRYMMOAFUTWPQ-BTJKTKAUSA-N (z)-but-2-enedioic acid;1-[2-(2,3-dichlorophenoxy)ethyl]-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)CCOC1=CC=CC(Cl)=C1Cl CQRYMMOAFUTWPQ-BTJKTKAUSA-N 0.000 description 1
- WUNGOYZKVUDBTF-BTJKTKAUSA-N (z)-but-2-enedioic acid;1-[2-(2,4-dichlorophenoxy)ethyl]-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)CCOC1=CC=C(Cl)C=C1Cl WUNGOYZKVUDBTF-BTJKTKAUSA-N 0.000 description 1
- JKBZZIHNGDUBIT-BTJKTKAUSA-N (z)-but-2-enedioic acid;3-[2-(3,5-dichlorophenoxy)ethyl]-1-[2-(dimethylamino)ethyl]-1-methylurea Chemical compound OC(=O)\C=C/C(O)=O.CN(C)CCN(C)C(=O)NCCOC1=CC(Cl)=CC(Cl)=C1 JKBZZIHNGDUBIT-BTJKTKAUSA-N 0.000 description 1
- AHGILFVRIWBZEF-BTJKTKAUSA-N (z)-but-2-enedioic acid;n-[2-[3-(trifluoromethyl)phenoxy]ethyl]propan-2-amine Chemical compound OC(=O)\C=C/C(O)=O.CC(C)NCCOC1=CC=CC(C(F)(F)F)=C1 AHGILFVRIWBZEF-BTJKTKAUSA-N 0.000 description 1
- IUGKWDIDGJORDL-ODZAUARKSA-N (z)-but-2-enedioic acid;thiourea Chemical compound NC(N)=S.OC(=O)\C=C/C(O)=O IUGKWDIDGJORDL-ODZAUARKSA-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
- MNOYLQOYSSCEPI-UHFFFAOYSA-N 1,3-dichloro-5-(3-chloropropoxy)benzene Chemical compound ClCCCOC1=CC(Cl)=CC(Cl)=C1 MNOYLQOYSSCEPI-UHFFFAOYSA-N 0.000 description 1
- OEYZGSRLAGSENP-UHFFFAOYSA-N 1-(2-bromoethoxy)-2,4-dichlorobenzene Chemical compound ClC1=CC=C(OCCBr)C(Cl)=C1 OEYZGSRLAGSENP-UHFFFAOYSA-N 0.000 description 1
- MNLWQUNSQVRNHQ-UHFFFAOYSA-N 1-(2-bromoethoxy)-3,5-dimethoxybenzene Chemical compound COC1=CC(OC)=CC(OCCBr)=C1 MNLWQUNSQVRNHQ-UHFFFAOYSA-N 0.000 description 1
- DMZQWLHBAZGMKK-UHFFFAOYSA-N 1-(2-bromoethoxy)-3,5-dimethylbenzene Chemical compound CC1=CC(C)=CC(OCCBr)=C1 DMZQWLHBAZGMKK-UHFFFAOYSA-N 0.000 description 1
- NZOCBKYAZHDTDD-UHFFFAOYSA-N 1-(2-bromoethoxy)-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(OCCBr)=C1 NZOCBKYAZHDTDD-UHFFFAOYSA-N 0.000 description 1
- HXGAHSFYRQKXQW-UHFFFAOYSA-N 1-(2-bromoethyl)-3-[3-(2-bromoethyl)-2,6-dichlorophenoxy]-2,4-dichlorobenzene Chemical compound ClC1=CC=C(CCBr)C(Cl)=C1OC1=C(Cl)C=CC(CCBr)=C1Cl HXGAHSFYRQKXQW-UHFFFAOYSA-N 0.000 description 1
- KBNRHECPGOKQAV-UHFFFAOYSA-N 1-(3-bromopropoxy)-3,5-dichlorobenzene Chemical compound ClC1=CC(Cl)=CC(OCCCBr)=C1 KBNRHECPGOKQAV-UHFFFAOYSA-N 0.000 description 1
- XJHDZQQJSNTLCS-UHFFFAOYSA-N 1-[2-(2,5-dichlorophenoxy)ethyl]-3-[2-(dimethylamino)ethyl]-1-propan-2-ylurea Chemical compound CN(C)CCNC(=O)N(C(C)C)CCOC1=CC(Cl)=CC=C1Cl XJHDZQQJSNTLCS-UHFFFAOYSA-N 0.000 description 1
- KTWXBQZIAQDPKY-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)ethyl]-3-[2-(dimethylamino)ethyl]-1-propan-2-ylurea Chemical compound CN(C)CCNC(=O)N(C(C)C)CCOC1=CC=C(Cl)C(Cl)=C1 KTWXBQZIAQDPKY-UHFFFAOYSA-N 0.000 description 1
- YMSSMMNIJPJMIB-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenoxy)ethyl]-3-[2-(dimethylamino)ethyl]-1-propan-2-ylthiourea Chemical compound CN(C)CCNC(=S)N(C(C)C)CCOC1=CC(Cl)=CC(Cl)=C1 YMSSMMNIJPJMIB-UHFFFAOYSA-N 0.000 description 1
- YULUXSYCORWEIH-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenoxy)ethyl]-3-[3-(dimethylamino)propyl]-1-propan-2-ylurea;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.CN(C)CCCNC(=O)N(C(C)C)CCOC1=CC(Cl)=CC(Cl)=C1 YULUXSYCORWEIH-UHFFFAOYSA-N 0.000 description 1
- SZJHWHLEIQZUND-UHFFFAOYSA-N 1-[3-(3,5-dichlorophenoxy)propyl]-3-[2-(dimethylamino)ethyl]-1-propan-2-ylurea;oxalic acid Chemical compound OC(=O)C(O)=O.CN(C)CCNC(=O)N(C(C)C)CCCOC1=CC(Cl)=CC(Cl)=C1 SZJHWHLEIQZUND-UHFFFAOYSA-N 0.000 description 1
- OULZFZPPERLSLP-UHFFFAOYSA-N 1-[3-(3,5-dichlorophenoxy)propyl]-3-[3-(dimethylamino)propyl]-1-propan-2-ylurea;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.CN(C)CCCNC(=O)N(C(C)C)CCCOC1=CC(Cl)=CC(Cl)=C1 OULZFZPPERLSLP-UHFFFAOYSA-N 0.000 description 1
- FOZVXADQAHVUSV-UHFFFAOYSA-N 1-bromo-2-(2-bromoethoxy)ethane Chemical compound BrCCOCCBr FOZVXADQAHVUSV-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- 125000005978 1-naphthyloxy group Chemical group 0.000 description 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- NKALVESVNGTFHZ-UHFFFAOYSA-N 2-(2-bromoethoxy)naphthalene Chemical compound C1=CC=CC2=CC(OCCBr)=CC=C21 NKALVESVNGTFHZ-UHFFFAOYSA-N 0.000 description 1
- RBXUEDHJCUJYCV-UHFFFAOYSA-N 2-(3,5-dichlorophenoxy)-N-methylethanamine hydrochloride Chemical compound Cl.CNCCOC1=CC(Cl)=CC(Cl)=C1 RBXUEDHJCUJYCV-UHFFFAOYSA-N 0.000 description 1
- KCDOLPRCLWOPQR-UHFFFAOYSA-N 2-(3,5-dichlorophenoxy)-n-methylethanamine Chemical compound CNCCOC1=CC(Cl)=CC(Cl)=C1 KCDOLPRCLWOPQR-UHFFFAOYSA-N 0.000 description 1
- HMSLGXIQEKOVTB-UHFFFAOYSA-N 2-(3,5-dichlorophenoxy)ethanamine;hydrochloride Chemical compound Cl.NCCOC1=CC(Cl)=CC(Cl)=C1 HMSLGXIQEKOVTB-UHFFFAOYSA-N 0.000 description 1
- HJBKBFDBNBYNDI-UHFFFAOYSA-N 2-(dimethylamino)ethylurea Chemical compound CN(C)CCNC(N)=O HJBKBFDBNBYNDI-UHFFFAOYSA-N 0.000 description 1
- BTEORONHDGJYJK-UHFFFAOYSA-N 3-[2-(dimethylamino)ethyl]-1-(2-naphthalen-2-yloxyethyl)-1-propan-2-ylurea;hydrochloride Chemical compound Cl.C1=CC=CC2=CC(OCCN(C(C)C)C(=O)NCCN(C)C)=CC=C21 BTEORONHDGJYJK-UHFFFAOYSA-N 0.000 description 1
- SQMJIYQANBYVEL-UHFFFAOYSA-N 4-(2-bromoethoxy)-1,2-dichlorobenzene Chemical compound ClC1=CC=C(OCCBr)C=C1Cl SQMJIYQANBYVEL-UHFFFAOYSA-N 0.000 description 1
- ISCXPRVQNSOSNL-UHFFFAOYSA-N 4-(2-bromoethoxy)-1,2-dimethylbenzene Chemical compound CC1=CC=C(OCCBr)C=C1C ISCXPRVQNSOSNL-UHFFFAOYSA-N 0.000 description 1
- CNBGRSVAXYHGMS-UHFFFAOYSA-N 4-(2-bromoethoxy)-2,3-dihydro-1h-indene Chemical compound BrCCOC1=CC=CC2=C1CCC2 CNBGRSVAXYHGMS-UHFFFAOYSA-N 0.000 description 1
- 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 1
- WNWVKZTYMQWFHE-UHFFFAOYSA-N 4-ethylmorpholine Chemical group [CH2]CN1CCOCC1 WNWVKZTYMQWFHE-UHFFFAOYSA-N 0.000 description 1
- ISUNZYFGWCNJLT-UHFFFAOYSA-N 4-nitrophenol;hydrochloride Chemical compound Cl.OC1=CC=C([N+]([O-])=O)C=C1 ISUNZYFGWCNJLT-UHFFFAOYSA-N 0.000 description 1
- 101100323010 Acinetobacter baylyi (strain ATCC 33305 / BD413 / ADP1) alkR gene Proteins 0.000 description 1
- 206010003658 Atrial Fibrillation Diseases 0.000 description 1
- 206010003662 Atrial flutter Diseases 0.000 description 1
- VKNSGZRYINSQAM-UHFFFAOYSA-N BrCCC1=C(C=CC(=C1OC)OC)OC1=C(C(=C(C=C1)OC)OC)CCBr Chemical compound BrCCC1=C(C=CC(=C1OC)OC)OC1=C(C(=C(C=C1)OC)OC)CCBr VKNSGZRYINSQAM-UHFFFAOYSA-N 0.000 description 1
- MGSJRQYMYPTIKH-BTJKTKAUSA-N C(\C=C/C(=O)O)(=O)O.CC(C)NCCOC1=CC(=CC(=C1)C)C Chemical compound C(\C=C/C(=O)O)(=O)O.CC(C)NCCOC1=CC(=CC(=C1)C)C MGSJRQYMYPTIKH-BTJKTKAUSA-N 0.000 description 1
- JDYIXCBQBGCRHV-BTJKTKAUSA-N C(\C=C/C(=O)O)(=O)O.CC(C)NCCOC1=CC(=CC(=C1)OC)OC Chemical compound C(\C=C/C(=O)O)(=O)O.CC(C)NCCOC1=CC(=CC(=C1)OC)OC JDYIXCBQBGCRHV-BTJKTKAUSA-N 0.000 description 1
- SCOXRJKOROAQEI-BTJKTKAUSA-N C(\C=C/C(=O)O)(=O)O.ClC1=C(OCCN(C(=O)NCCN(C)C)C(C)C)C=C(C=C1)Cl Chemical compound C(\C=C/C(=O)O)(=O)O.ClC1=C(OCCN(C(=O)NCCN(C)C)C(C)C)C=C(C=C1)Cl SCOXRJKOROAQEI-BTJKTKAUSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- VEAIOWADLUWXFX-UHFFFAOYSA-N Cl.C1=CC=CC2=CC(OCCNC(C)C)=CC=C21 Chemical compound Cl.C1=CC=CC2=CC(OCCNC(C)C)=CC=C21 VEAIOWADLUWXFX-UHFFFAOYSA-N 0.000 description 1
- CMXZDGLPMKSOSJ-UHFFFAOYSA-N Cl.CC(C)NCCOC1=CC=C(C)C(C)=C1 Chemical compound Cl.CC(C)NCCOC1=CC=C(C)C(C)=C1 CMXZDGLPMKSOSJ-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 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
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 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
- 244000246386 Mentha pulegium Species 0.000 description 1
- 235000016257 Mentha pulegium Nutrition 0.000 description 1
- 235000004357 Mentha x piperita Nutrition 0.000 description 1
- IJISFHZIEAQRIE-UHFFFAOYSA-N N-[2-(2,3-dichlorophenoxy)ethyl]propan-2-amine hydrochloride Chemical compound Cl.CC(C)NCCOC1=CC=CC(Cl)=C1Cl IJISFHZIEAQRIE-UHFFFAOYSA-N 0.000 description 1
- HKLWOGSWMMTLPO-UHFFFAOYSA-N N-[2-(3,4-dichlorophenoxy)ethyl]propan-2-amine hydrochloride Chemical compound Cl.CC(C)NCCOC1=CC=C(Cl)C(Cl)=C1 HKLWOGSWMMTLPO-UHFFFAOYSA-N 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241000700159 Rattus Species 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
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000005263 alkylenediamine group Chemical group 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- KBPWECBBZZNAIE-UHFFFAOYSA-N aniline;hydron;bromide Chemical compound Br.NC1=CC=CC=C1 KBPWECBBZZNAIE-UHFFFAOYSA-N 0.000 description 1
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000002763 arrhythmic effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000017531 blood circulation 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 235000019506 cigar Nutrition 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 125000006165 cyclic alkyl 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
- 125000000113 cyclohexyl group Chemical group [H]C1([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
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- OPSDMEFGPZWALM-UHFFFAOYSA-N ethylurea;hydrochloride Chemical compound Cl.CCNC(N)=O OPSDMEFGPZWALM-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 238000009499 grossing Methods 0.000 description 1
- 210000002837 heart atrium Anatomy 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
- IGMNYECMUMZDDF-UHFFFAOYSA-N homogentisic acid Chemical compound OC(=O)CC1=CC(O)=CC=C1O IGMNYECMUMZDDF-UHFFFAOYSA-N 0.000 description 1
- 235000001050 hortel pimenta Nutrition 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection 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
- 229910052740 iodine Inorganic materials 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
- 239000004922 lacquer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-M maleate(1-) Chemical compound OC(=O)\C=C/C([O-])=O VZCYOOQTPOCHFL-UPHRSURJSA-M 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000006203 morpholinoethyl group Chemical group [H]C([H])(*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- QXPRMANJAMOFLQ-UHFFFAOYSA-N n',n'-dimethyl-n-propan-2-ylethane-1,2-diamine Chemical compound CC(C)NCCN(C)C QXPRMANJAMOFLQ-UHFFFAOYSA-N 0.000 description 1
- HVOYZOQVDYHUPF-UHFFFAOYSA-N n,n',n'-trimethylethane-1,2-diamine Chemical compound CNCCN(C)C HVOYZOQVDYHUPF-UHFFFAOYSA-N 0.000 description 1
- RUJIRPLHNAOTPH-UHFFFAOYSA-N n-[2-(2,3-dichlorophenoxy)ethyl]propan-2-amine Chemical compound CC(C)NCCOC1=CC=CC(Cl)=C1Cl RUJIRPLHNAOTPH-UHFFFAOYSA-N 0.000 description 1
- YUVQUYIXSAUGMH-UHFFFAOYSA-N n-[2-(2,3-dihydro-1h-inden-4-yloxy)ethyl]propan-2-amine Chemical compound CC(C)NCCOC1=CC=CC2=C1CCC2 YUVQUYIXSAUGMH-UHFFFAOYSA-N 0.000 description 1
- XBKSXRGRBIDULY-UHFFFAOYSA-N n-[2-(2,3-dihydro-1h-inden-5-yloxy)ethyl]propan-2-amine Chemical compound CC(C)NCCOC1=CC=C2CCCC2=C1 XBKSXRGRBIDULY-UHFFFAOYSA-N 0.000 description 1
- OGCZOVMNLOSLEI-UHFFFAOYSA-N n-[2-(2,4-dichlorophenoxy)ethyl]propan-2-amine Chemical compound CC(C)NCCOC1=CC=C(Cl)C=C1Cl OGCZOVMNLOSLEI-UHFFFAOYSA-N 0.000 description 1
- PYXBHRQZXIEGDL-UHFFFAOYSA-N n-[2-(2,5-dichlorophenoxy)ethyl]propan-2-amine Chemical compound CC(C)NCCOC1=CC(Cl)=CC=C1Cl PYXBHRQZXIEGDL-UHFFFAOYSA-N 0.000 description 1
- GXFOXIPAHOEPMU-UHFFFAOYSA-N n-[2-(2,5-dichlorophenoxy)ethyl]propan-2-amine;hydrochloride Chemical compound Cl.CC(C)NCCOC1=CC(Cl)=CC=C1Cl GXFOXIPAHOEPMU-UHFFFAOYSA-N 0.000 description 1
- DFUWGHZBDYLIAQ-UHFFFAOYSA-N n-[2-(2-chlorophenoxy)ethyl]propan-2-amine Chemical compound CC(C)NCCOC1=CC=CC=C1Cl DFUWGHZBDYLIAQ-UHFFFAOYSA-N 0.000 description 1
- BNUGMOZSBICVIX-UHFFFAOYSA-N n-[2-(2-chlorophenoxy)ethyl]propan-2-amine;hydrochloride Chemical compound Cl.CC(C)NCCOC1=CC=CC=C1Cl BNUGMOZSBICVIX-UHFFFAOYSA-N 0.000 description 1
- OXHZTHRJEPNXIU-UHFFFAOYSA-N n-[2-(3,4-dimethylphenoxy)ethyl]propan-2-amine Chemical compound CC(C)NCCOC1=CC=C(C)C(C)=C1 OXHZTHRJEPNXIU-UHFFFAOYSA-N 0.000 description 1
- NDTTZKRCMRFPKX-UHFFFAOYSA-N n-[2-(3,5-dichlorophenoxy)ethyl]-2-methylpropan-1-amine Chemical compound CC(C)CNCCOC1=CC(Cl)=CC(Cl)=C1 NDTTZKRCMRFPKX-UHFFFAOYSA-N 0.000 description 1
- DONPPGXTDFQVQU-UHFFFAOYSA-N n-[2-(3,5-dichlorophenoxy)ethyl]-n-propan-2-ylcarbamoyl chloride Chemical compound CC(C)N(C(Cl)=O)CCOC1=CC(Cl)=CC(Cl)=C1 DONPPGXTDFQVQU-UHFFFAOYSA-N 0.000 description 1
- NXAWVRAAJQBDFI-UHFFFAOYSA-N n-[2-(3,5-dichlorophenoxy)ethyl]aniline Chemical compound ClC1=CC(Cl)=CC(OCCNC=2C=CC=CC=2)=C1 NXAWVRAAJQBDFI-UHFFFAOYSA-N 0.000 description 1
- TZNATXXWKLNSKN-UHFFFAOYSA-N n-[2-(3,5-dichlorophenoxy)ethyl]cyclohexanamine Chemical compound ClC1=CC(Cl)=CC(OCCNC2CCCCC2)=C1 TZNATXXWKLNSKN-UHFFFAOYSA-N 0.000 description 1
- STPPYMLOLFOVRU-UHFFFAOYSA-N n-[2-(3,5-dichlorophenoxy)ethyl]propan-1-amine Chemical compound CCCNCCOC1=CC(Cl)=CC(Cl)=C1 STPPYMLOLFOVRU-UHFFFAOYSA-N 0.000 description 1
- WOGOIKJVMDAKAN-UHFFFAOYSA-N n-[2-(3,5-dimethoxyphenoxy)ethyl]propan-2-amine Chemical compound COC1=CC(OC)=CC(OCCNC(C)C)=C1 WOGOIKJVMDAKAN-UHFFFAOYSA-N 0.000 description 1
- AEOIMAOUAGCASN-UHFFFAOYSA-N n-[2-(3-fluorophenoxy)ethyl]propan-2-amine Chemical compound CC(C)NCCOC1=CC=CC(F)=C1 AEOIMAOUAGCASN-UHFFFAOYSA-N 0.000 description 1
- KYIXJRRNTRWNCR-UHFFFAOYSA-N n-[2-(4-chlorophenoxy)ethyl]propan-2-amine Chemical compound CC(C)NCCOC1=CC=C(Cl)C=C1 KYIXJRRNTRWNCR-UHFFFAOYSA-N 0.000 description 1
- FSFWIEYKZYDEAJ-UHFFFAOYSA-N n-[2-(4-nitrophenoxy)ethyl]propan-2-amine Chemical compound CC(C)NCCOC1=CC=C([N+]([O-])=O)C=C1 FSFWIEYKZYDEAJ-UHFFFAOYSA-N 0.000 description 1
- UGBWTFOSUPTOPU-UHFFFAOYSA-N n-[2-[3-(trifluoromethyl)phenoxy]ethyl]propan-2-amine Chemical compound CC(C)NCCOC1=CC=CC(C(F)(F)F)=C1 UGBWTFOSUPTOPU-UHFFFAOYSA-N 0.000 description 1
- RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 1
- CASKQKBFZJNUSV-UHFFFAOYSA-N n-methyl-2-phenoxyethanamine;hydrochloride Chemical compound Cl.CNCCOC1=CC=CC=C1 CASKQKBFZJNUSV-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
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 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
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229920001223 polyethylene glycol Polymers 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
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- ZVUVJTQITHFYHV-UHFFFAOYSA-M potassium;naphthalene-1-carboxylate Chemical class [K+].C1=CC=C2C(C(=O)[O-])=CC=CC2=C1 ZVUVJTQITHFYHV-UHFFFAOYSA-M 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- DQMZLTXERSFNPB-UHFFFAOYSA-N primidone Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NCNC1=O DQMZLTXERSFNPB-UHFFFAOYSA-N 0.000 description 1
- ABTXGJFUQRCPNH-UHFFFAOYSA-N procainamide hydrochloride Chemical compound [H+].[Cl-].CCN(CC)CCNC(=O)C1=CC=C(N)C=C1 ABTXGJFUQRCPNH-UHFFFAOYSA-N 0.000 description 1
- ISYORFGKSZLPNW-UHFFFAOYSA-N propan-2-ylazanium;chloride Chemical compound [Cl-].CC(C)[NH3+] ISYORFGKSZLPNW-UHFFFAOYSA-N 0.000 description 1
- PYNUOAIJIQGACY-UHFFFAOYSA-N propylazanium;chloride Chemical compound Cl.CCCN PYNUOAIJIQGACY-UHFFFAOYSA-N 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
- 230000001681 protective effect Effects 0.000 description 1
- 210000003752 saphenous vein Anatomy 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000011593 sulfur Substances 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 210000001541 thymus gland Anatomy 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1809—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety
- C07C273/1818—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety from -N=C=O and XNR'R"
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
- C07C275/06—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
- C07C275/14—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
- C07C275/20—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
- C07C275/24—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26551081A | 1981-05-20 | 1981-05-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU187706B true HU187706B (en) | 1986-02-28 |
Family
ID=23010745
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU821580A HU187706B (en) | 1981-05-20 | 1982-05-18 | Process for preparing n-/aryl-oxy.alkyl/-n'-/amino-alkyl/-carbamide derivatives |
Country Status (22)
| Country | Link |
|---|---|
| EP (1) | EP0066987B1 (en:Method) |
| JP (1) | JPS57197215A (en:Method) |
| KR (1) | KR890001999B1 (en:Method) |
| AU (1) | AU544977B2 (en:Method) |
| CA (1) | CA1190228A (en:Method) |
| DE (1) | DE3272856D1 (en:Method) |
| DK (1) | DK228582A (en:Method) |
| EG (1) | EG15911A (en:Method) |
| ES (3) | ES512337A0 (en:Method) |
| FI (1) | FI76552C (en:Method) |
| GR (1) | GR76408B (en:Method) |
| HK (1) | HK86187A (en:Method) |
| HU (1) | HU187706B (en:Method) |
| IE (1) | IE53319B1 (en:Method) |
| IL (1) | IL65556A (en:Method) |
| IN (1) | IN156479B (en:Method) |
| NO (1) | NO153295C (en:Method) |
| NZ (1) | NZ200668A (en:Method) |
| PH (1) | PH20208A (en:Method) |
| PT (1) | PT74931B (en:Method) |
| SG (1) | SG48887G (en:Method) |
| ZA (1) | ZA823213B (en:Method) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4486344A (en) * | 1983-03-28 | 1984-12-04 | Miles Laboratories, Inc. | Urea-linked immunogens, antibodies, and preparative method |
| JPS61126065A (ja) * | 1984-11-26 | 1986-06-13 | Mitsui Petrochem Ind Ltd | 置換フエノキシ尿素、その製造法およびそれを有効成分として含有する除草剤 |
| 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 |
| JP2826826B2 (ja) * | 1988-04-11 | 1998-11-18 | 日本ケミファ株式会社 | アルキレンジアミン誘導体 |
| AU2031692A (en) * | 1991-07-22 | 1993-01-28 | Zyma S.A. | Arylalkylamine derivatives |
| US8106221B2 (en) | 2007-06-20 | 2012-01-31 | Vitae Pharmaceuticals, Inc. | Renin inhibitors |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2344934A (en) * | 1943-02-12 | 1944-03-21 | American Cyanamid Co | Quaternary nitrogen condensation products of methylol urea ethers |
| GB1031165A (en) * | 1965-08-18 | 1966-05-25 | Wellcome Found | Guanidines, isoureas and isothioureas |
-
1982
- 1982-04-20 IL IL65556A patent/IL65556A/xx unknown
- 1982-05-10 ZA ZA823213A patent/ZA823213B/xx unknown
- 1982-05-12 PH PH27277A patent/PH20208A/en unknown
- 1982-05-16 EG EG272/82A patent/EG15911A/xx active
- 1982-05-17 GR GR68173A patent/GR76408B/el unknown
- 1982-05-18 HU HU821580A patent/HU187706B/hu not_active IP Right Cessation
- 1982-05-18 IN IN556/CAL/82A patent/IN156479B/en unknown
- 1982-05-18 IE IE1192/82A patent/IE53319B1/en unknown
- 1982-05-18 CA CA000403157A patent/CA1190228A/en not_active Expired
- 1982-05-19 PT PT74931A patent/PT74931B/pt unknown
- 1982-05-19 ES ES512337A patent/ES512337A0/es active Granted
- 1982-05-19 DE DE8282302556T patent/DE3272856D1/de not_active Expired
- 1982-05-19 ES ES512335A patent/ES8303306A1/es not_active Expired
- 1982-05-19 FI FI821775A patent/FI76552C/fi not_active IP Right Cessation
- 1982-05-19 DK DK228582A patent/DK228582A/da not_active Application Discontinuation
- 1982-05-19 EP EP82302556A patent/EP0066987B1/en not_active Expired
- 1982-05-19 ES ES512338A patent/ES512338A0/es active Granted
- 1982-05-19 NZ NZ200668A patent/NZ200668A/en unknown
- 1982-05-19 NO NO821669A patent/NO153295C/no unknown
- 1982-05-20 AU AU83882/82A patent/AU544977B2/en not_active Ceased
- 1982-05-20 JP JP57085626A patent/JPS57197215A/ja active Pending
- 1982-05-20 KR KR8202210A patent/KR890001999B1/ko not_active Expired
-
1987
- 1987-06-03 SG SG48887A patent/SG48887G/en unknown
- 1987-11-19 HK HK861/87A patent/HK86187A/xx unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69133299T2 (de) | Aminosulfonylcarbamate | |
| US5015644A (en) | Antihyperlipidemic and antiatherosclerotic urea and carbamate compounds | |
| US5981595A (en) | Sulfonyl urea and carbamate ACAT inhibitors | |
| DE3587359T2 (de) | Benzensulfonamid-derivate. | |
| JPS6197256A (ja) | アルキルスルホンアミドフエニルアルキルアミン類 | |
| RU2045522C1 (ru) | Диаминовые соединения или их кислотно-аддитивные соли | |
| EP0158775A1 (en) | Substituted sulfonamidobenzamides, antiarrythmic agents and compositions thereof | |
| EP0549796B1 (en) | Diphenylpiperazine derivative and drug for circulatory organ containing the same | |
| 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 | |
| US4558155A (en) | N-(Aryloxyalkyl)-N'-(aminoalkyl)thioureas | |
| JPH02500029A (ja) | アリール‐ｎ‐アミノアルキル‐４‐（スルホンアミド）ベンズアミド、抗不整脈剤及びその組成物 | |
| CS214699B2 (en) | Method of making the 9-aminoalcylfluorenes | |
| HU187706B (en) | Process for preparing n-/aryl-oxy.alkyl/-n'-/amino-alkyl/-carbamide derivatives | |
| US4724235A (en) | N-(arylthioalkyl)-N'-(aminoalkyl)ureas useful in the treatment of arrhythmia | |
| EP0007184A1 (en) | Urea derivatives, processes for preparing them and compositions containing them | |
| US4597902A (en) | N-(arylthioalkyl)-N'-(aminoalkyl)ureas | |
| CH635831A5 (de) | Phenyltetrazolyloxypropanolamine und verfahren zu ihrer herstellung. | |
| EP0083712A1 (en) | 1-(3,4,5-Trimethoxycinnamoyl)-4-aminocarbonylethyl-substituted piperazine derivatives and a process for the preparation thereof | |
| KR890001811B1 (ko) | N-(아릴티오알킬)-n'-(아미노알킬)우레아 및 이의 제조방법 | |
| US4016284A (en) | Derivatives of 1,3-benzodioxole, the preparation and use thereof | |
| SK22296A3 (en) | Substituted benzenesulfonylureas and benzenesulfonylthioureas, method of their manufacture, their use for production of pharmaceutical compositions, and medicaments containing them | |
| JPH0357892B2 (en:Method) | ||
| CA2491989C (fr) | Composes a activite anti-parasitaire et medicaments les renfermant | |
| HU199792B (en) | Process for producing new indolecarboxamide derivatives and pharmaceutical compositions comprising such compounds |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |