JP2005508952A5

JP2005508952A5 -

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Publication number: JP2005508952A5
Authority: JP; Japan
Prior art keywords: ylmethyl; tetrahydroquinolin; piperazine; cyclohexanecarbonyl; indolyl
Prior art date: 2002-10-07
Legal status : Withdrawn

Application number

JP2003534419A

Other languages

English (en)

Japanese (ja)

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JP2005508952A (ja

Filing date

2002-10-07

Publication date

2006-01-05

2001-10-05 Priority claimed from IT2001MI002060A external-priority patent/ITMI20012060A1/it

2002-10-07 Application filed filed Critical

2005-04-07 Publication of JP2005508952A publication Critical patent/JP2005508952A/ja

2006-01-05 Publication of JP2005508952A5 publication Critical patent/JP2005508952A5/ja

Status Withdrawn legal-status Critical Current

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150000001875 compounds Chemical class 0.000 claims description 427
-1 nitro, phenyl Chemical group 0.000 claims description 179
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 30
239000000203 mixture Substances 0.000 claims description 24
229910052757 nitrogen Inorganic materials 0.000 claims description 5
JQAJCCMIECJCNZ-UHFFFAOYSA-N [2-[(3-benzylpiperidin-1-yl)methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound C1CCC(CC=2C=CC=CC=2)CN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 JQAJCCMIECJCNZ-UHFFFAOYSA-N 0.000 claims description 4
DLPBHGLDLOXGOD-UHFFFAOYSA-N [5-chloro-2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound COC1=CC(F)=CC=C1N1CCN(CC2N(C3=CC=CC(Cl)=C3CC2)C(=O)C2CCCCC2)CC1 DLPBHGLDLOXGOD-UHFFFAOYSA-N 0.000 claims description 3
KGYXHCAPLRHRJA-UHFFFAOYSA-N [6-bromo-2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC(Br)=CC=C2N1C(=O)C1CCCCC1 KGYXHCAPLRHRJA-UHFFFAOYSA-N 0.000 claims description 3
SVUKNYUTGFVFPP-UHFFFAOYSA-N [6-bromo-2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound COC1=CC(F)=CC=C1N1CCN(CC2N(C3=CC=C(Br)C=C3CC2)C(=O)C2CCCCC2)CC1 SVUKNYUTGFVFPP-UHFFFAOYSA-N 0.000 claims description 3
MNWUTTMODAEUBX-UHFFFAOYSA-N [6-chloro-2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC(Cl)=CC=C2N1C(=O)C1CCCCC1 MNWUTTMODAEUBX-UHFFFAOYSA-N 0.000 claims description 3
MNTMIQGOSDSQRB-UHFFFAOYSA-N [7-chloro-2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound COC1=CC(F)=CC=C1N1CCN(CC2N(C3=CC(Cl)=CC=C3CC2)C(=O)C2CCCCC2)CC1 MNTMIQGOSDSQRB-UHFFFAOYSA-N 0.000 claims description 3
LPZSUJFMTQJYQJ-UHFFFAOYSA-N cyclohexyl-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-2,3-dihydroindol-1-yl]methanone Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CC2=CC=CC=C2N1C(=O)C1CCCCC1 LPZSUJFMTQJYQJ-UHFFFAOYSA-N 0.000 claims description 3
AVCZGPDNPQHYBX-UHFFFAOYSA-N cyclohexyl-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-6-(trifluoromethoxy)-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC(OC(F)(F)F)=CC=C2N1C(=O)C1CCCCC1 AVCZGPDNPQHYBX-UHFFFAOYSA-N 0.000 claims description 3
XMYJLJOWUZAGOS-UHFFFAOYSA-N cyclohexyl-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-6-(trifluoromethyl)-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC(C(F)(F)F)=CC=C2N1C(=O)C1CCCCC1 XMYJLJOWUZAGOS-UHFFFAOYSA-N 0.000 claims description 3
VOAPKRKXJSXJQP-UHFFFAOYSA-N cyclohexyl-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-8-methoxy-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=2C(OC)=CC=CC=2CCC(CN2CCN(CC2)C=2C=3C=CNC=3C=CC=2)N1C(=O)C1CCCCC1 VOAPKRKXJSXJQP-UHFFFAOYSA-N 0.000 claims description 3
LWIYPSCIDGDLRY-UHFFFAOYSA-N cyclohexyl-[2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound COC1=CC(F)=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 LWIYPSCIDGDLRY-UHFFFAOYSA-N 0.000 claims description 3
CPUGOFFBAVPXFR-UHFFFAOYSA-N cyclohexyl-[2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-6-methyl-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound COC1=CC(F)=CC=C1N1CCN(CC2N(C3=CC=C(C)C=C3CC2)C(=O)C2CCCCC2)CC1 CPUGOFFBAVPXFR-UHFFFAOYSA-N 0.000 claims description 3
YQEUJYBKYYTPTG-UHFFFAOYSA-N cyclohexyl-[6-hydroxy-2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC(O)=CC=C2N1C(=O)C1CCCCC1 YQEUJYBKYYTPTG-UHFFFAOYSA-N 0.000 claims description 3
HBOPEKPLQMYFQC-UHFFFAOYSA-N cyclohexyl-[7-fluoro-2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C12=CC(F)=CC=C2CCC(CN2CCN(CC2)C=2C=3C=CNC=3C=CC=2)N1C(=O)C1CCCCC1 HBOPEKPLQMYFQC-UHFFFAOYSA-N 0.000 claims description 3
STUPXLTYVIIPEU-UHFFFAOYSA-N cyclohexyl-[8-fluoro-2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=2C(F)=CC=CC=2CCC(CN2CCN(CC2)C=2C=3C=CNC=3C=CC=2)N1C(=O)C1CCCCC1 STUPXLTYVIIPEU-UHFFFAOYSA-N 0.000 claims description 3
MOWSFFJPJLNJLV-UHFFFAOYSA-N cyclohexyl-[8-hydroxy-2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=2C(O)=CC=CC=2CCC(CN2CCN(CC2)C=2C=3C=CNC=3C=CC=2)N1C(=O)C1CCCCC1 MOWSFFJPJLNJLV-UHFFFAOYSA-N 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
HGISEXWJSBBYFW-UHFFFAOYSA-N 1-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]pentan-1-one Chemical compound C1CC2=CC=CC=C2N(C(=O)CCCC)C1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 HGISEXWJSBBYFW-UHFFFAOYSA-N 0.000 claims description 2
NWNNMHFUXRIMJR-UHFFFAOYSA-N 1-[4-[4-[[1-(cyclohexanecarbonyl)-3,4-dihydro-2h-quinolin-2-yl]methyl]piperazin-1-yl]indol-1-yl]ethanone Chemical compound C1=CC=C2N(C(=O)C)C=CC2=C1N(CC1)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 NWNNMHFUXRIMJR-UHFFFAOYSA-N 0.000 claims description 2
WIHCMMAJXDEQDL-UHFFFAOYSA-N 2-[4-[[1-(cyclohexanecarbonyl)-3,4-dihydro-2h-quinolin-2-yl]methyl]piperazin-1-yl]-5-nitrobenzonitrile Chemical compound N#CC1=CC([N+](=O)[O-])=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 WIHCMMAJXDEQDL-UHFFFAOYSA-N 0.000 claims description 2
YSESSUUFMLKDBH-UHFFFAOYSA-N 3-(benzylamino)-1-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]propan-1-one Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)CCNCC1=CC=CC=C1 YSESSUUFMLKDBH-UHFFFAOYSA-N 0.000 claims description 2
FBKAOUCNXKVSIX-UHFFFAOYSA-N 3-[4-[[1-(cyclohexanecarbonyl)-3,4-dihydro-2h-quinolin-2-yl]methyl]piperazin-1-yl]-4-methoxybenzonitrile Chemical compound COC1=CC=C(C#N)C=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 FBKAOUCNXKVSIX-UHFFFAOYSA-N 0.000 claims description 2
GOYLMLJDDRUSIW-UHFFFAOYSA-N 4-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-4-oxobutanenitrile Chemical compound C1CC2=CC=CC=C2N(C(CCC#N)=O)C1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 GOYLMLJDDRUSIW-UHFFFAOYSA-N 0.000 claims description 2
ZJKQPVKXAVTXBP-UHFFFAOYSA-N 4-[4-[[1-(cyclohexanecarbonyl)-3,4-dihydro-2h-quinolin-2-yl]methyl]piperazin-1-yl]-1h-indole-3-carbonitrile Chemical compound C1CN(C=2C=3C(C#N)=CNC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 ZJKQPVKXAVTXBP-UHFFFAOYSA-N 0.000 claims description 2
QBFLHYVTWFKESF-UHFFFAOYSA-N 4-chloro-2-[4-[[1-(cyclohexanecarbonyl)-3,4-dihydro-2h-quinolin-2-yl]methyl]piperazin-1-yl]benzonitrile Chemical compound ClC1=CC=C(C#N)C(N2CCN(CC3N(C4=CC=CC=C4CC3)C(=O)C3CCCCC3)CC2)=C1 QBFLHYVTWFKESF-UHFFFAOYSA-N 0.000 claims description 2
FKVPOPQDQMLFQP-UHFFFAOYSA-N [2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-piperidin-1-ylmethanone Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)N1CCCCC1 FKVPOPQDQMLFQP-UHFFFAOYSA-N 0.000 claims description 2
FLEPAGXADTZKRB-UHFFFAOYSA-N [2-[[4-(2-chloro-5-fluorophenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound FC1=CC=C(Cl)C(N2CCN(CC3N(C4=CC=CC=C4CC3)C(=O)C3CCCCC3)CC2)=C1 FLEPAGXADTZKRB-UHFFFAOYSA-N 0.000 claims description 2
IQHYIGSKUMHCMC-UHFFFAOYSA-N [2-[[4-(5-chloro-2-fluorophenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound FC1=CC=C(Cl)C=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 IQHYIGSKUMHCMC-UHFFFAOYSA-N 0.000 claims description 2
RHZLPIXKYNZRJC-UHFFFAOYSA-N [2-[[4-(7-bromo-1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound C1=2C=CNC=2C(Br)=CC=C1N(CC1)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 RHZLPIXKYNZRJC-UHFFFAOYSA-N 0.000 claims description 2
XWXBYEPNDJAMPV-UHFFFAOYSA-N [2-[[4-(7-chloro-2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound C=1C(Cl)=CC=2OCCOC=2C=1N(CC1)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 XWXBYEPNDJAMPV-UHFFFAOYSA-N 0.000 claims description 2
KCBKZCRICOPUOZ-UHFFFAOYSA-N [2-[[4-[(2-bromophenyl)methyl]piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound BrC1=CC=CC=C1CN1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 KCBKZCRICOPUOZ-UHFFFAOYSA-N 0.000 claims description 2
QDYHIMIMFNNKFP-UHFFFAOYSA-N [2-[[4-[(2-chlorophenyl)methyl]piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound ClC1=CC=CC=C1CN1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 QDYHIMIMFNNKFP-UHFFFAOYSA-N 0.000 claims description 2
NCZLGFUZABLCIY-UHFFFAOYSA-N [3-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-3-oxopropyl]urea Chemical compound C1CC2=CC=CC=C2N(C(=O)CCNC(=O)N)C1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 NCZLGFUZABLCIY-UHFFFAOYSA-N 0.000 claims description 2
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
125000002252 acyl group Chemical group 0.000 claims description 2
LVJZKZJKNXQWPA-UHFFFAOYSA-N cycloheptyl-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCCC1 LVJZKZJKNXQWPA-UHFFFAOYSA-N 0.000 claims description 2
UJNPUSTUAVEPHL-RUZDIDTESA-N cyclohexyl-[(2r)-2-[[4-(1-methylindol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C([C@@H]1CN2CCN(CC2)C2=C3C=CN(C3=CC=C2)C)CC2=CC=CC=C2N1C(=O)C1CCCCC1 UJNPUSTUAVEPHL-RUZDIDTESA-N 0.000 claims description 2
WDRJUTQZKUESAR-UHFFFAOYSA-N cyclohexyl-[2-[(4-naphthalen-1-ylpiperazin-1-yl)methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CN(C=2C3=CC=CC=C3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 WDRJUTQZKUESAR-UHFFFAOYSA-N 0.000 claims description 2
COLQKQKVOYMVRR-UHFFFAOYSA-N cyclohexyl-[2-[(4-phenylpiperazin-1-yl)methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CN(C=2C=CC=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 COLQKQKVOYMVRR-UHFFFAOYSA-N 0.000 claims description 2
PGEPKYZCTUPEBL-UHFFFAOYSA-N cyclohexyl-[2-[(4-pyrazin-2-ylpiperazin-1-yl)methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CN(C=2N=CC=NC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 PGEPKYZCTUPEBL-UHFFFAOYSA-N 0.000 claims description 2
ADGKJQPNASNSJS-UHFFFAOYSA-N cyclohexyl-[2-[(4-pyridin-4-ylpiperazin-1-yl)methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CN(C=2C=CN=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 ADGKJQPNASNSJS-UHFFFAOYSA-N 0.000 claims description 2
FNDNXNDRXGNKCW-UHFFFAOYSA-N cyclohexyl-[2-[(4-pyrimidin-2-ylpiperazin-1-yl)methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CN(C=2N=CC=CN=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 FNDNXNDRXGNKCW-UHFFFAOYSA-N 0.000 claims description 2
CMSFPWSFDFEBSE-UHFFFAOYSA-N cyclohexyl-[2-[(4-quinolin-8-ylpiperazin-1-yl)methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CN(C=2C3=NC=CC=C3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 CMSFPWSFDFEBSE-UHFFFAOYSA-N 0.000 claims description 2
JMHKUAMZUCUOQP-UHFFFAOYSA-N cyclohexyl-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-6-phenyl-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC(C=3C=CC=CC=3)=CC=C2N1C(=O)C1CCCCC1 JMHKUAMZUCUOQP-UHFFFAOYSA-N 0.000 claims description 2
MHAXERMFJFACGE-UHFFFAOYSA-N cyclohexyl-[2-[[4-(1h-indol-7-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CN(C=2C=3NC=CC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 MHAXERMFJFACGE-UHFFFAOYSA-N 0.000 claims description 2
SEWLKSYTQVXVSL-UHFFFAOYSA-N cyclohexyl-[2-[[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CN(C=2C=3OCCOC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 SEWLKSYTQVXVSL-UHFFFAOYSA-N 0.000 claims description 2
UVDPAGVITBFKGW-UHFFFAOYSA-N cyclohexyl-[2-[[4-(2,3-dihydro-1-benzofuran-7-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CN(C=2C=3OCCC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 UVDPAGVITBFKGW-UHFFFAOYSA-N 0.000 claims description 2
WZPOOLKFXIYCIA-UHFFFAOYSA-N cyclohexyl-[2-[[4-(2,3-dimethyl-1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C=12C(C)=C(C)NC2=CC=CC=1N(CC1)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 WZPOOLKFXIYCIA-UHFFFAOYSA-N 0.000 claims description 2
AKIOPBNQYIESAE-UHFFFAOYSA-N cyclohexyl-[2-[[4-(2,4-dichlorophenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound ClC1=CC(Cl)=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 AKIOPBNQYIESAE-UHFFFAOYSA-N 0.000 claims description 2
UVSIHBBYABDFSX-UHFFFAOYSA-N cyclohexyl-[2-[[4-(2,5-dimethoxyphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound COC1=CC=C(OC)C(N2CCN(CC3N(C4=CC=CC=C4CC3)C(=O)C3CCCCC3)CC2)=C1 UVSIHBBYABDFSX-UHFFFAOYSA-N 0.000 claims description 2
VYASCFBZIKVFLP-UHFFFAOYSA-N cyclohexyl-[2-[[4-(2-ethoxy-4-fluorophenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound CCOC1=CC(F)=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 VYASCFBZIKVFLP-UHFFFAOYSA-N 0.000 claims description 2
JPWMWBUNIMTZFH-UHFFFAOYSA-N cyclohexyl-[2-[[4-(2-ethoxyphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound CCOC1=CC=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 JPWMWBUNIMTZFH-UHFFFAOYSA-N 0.000 claims description 2
WBNQTNVIPYIINP-UHFFFAOYSA-N cyclohexyl-[2-[[4-(2-fluoro-5-methylphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound CC1=CC=C(F)C(N2CCN(CC3N(C4=CC=CC=C4CC3)C(=O)C3CCCCC3)CC2)=C1 WBNQTNVIPYIINP-UHFFFAOYSA-N 0.000 claims description 2
OQEWRUCJJNUMMR-UHFFFAOYSA-N cyclohexyl-[2-[[4-(2-hydroxyphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound OC1=CC=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 OQEWRUCJJNUMMR-UHFFFAOYSA-N 0.000 claims description 2
NMCQPNAONDBHTA-UHFFFAOYSA-N cyclohexyl-[2-[[4-(2-methyl-1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=CC=C2NC(C)=CC2=C1N(CC1)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 NMCQPNAONDBHTA-UHFFFAOYSA-N 0.000 claims description 2
DNEWRQFMXUOEDV-UHFFFAOYSA-N cyclohexyl-[2-[[4-(2-methylphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound CC1=CC=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 DNEWRQFMXUOEDV-UHFFFAOYSA-N 0.000 claims description 2
YVGZTMIEFMBERQ-UHFFFAOYSA-N cyclohexyl-[2-[[4-(2-propan-2-yloxyphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound CC(C)OC1=CC=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 YVGZTMIEFMBERQ-UHFFFAOYSA-N 0.000 claims description 2
YNBALIXLLXCGCT-UHFFFAOYSA-N cyclohexyl-[2-[[4-(3,4-dihydro-2h-1,5-benzodioxepin-6-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CN(C=2C=3OCCCOC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 YNBALIXLLXCGCT-UHFFFAOYSA-N 0.000 claims description 2
ILPJGJALEJHLOU-UHFFFAOYSA-N cyclohexyl-[2-[[4-(4-fluoro-2-methylphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound CC1=CC(F)=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 ILPJGJALEJHLOU-UHFFFAOYSA-N 0.000 claims description 2
BYPZVDNTPRNSST-UHFFFAOYSA-N cyclohexyl-[2-[[4-(4-hydroxy-2-methoxyphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound COC1=CC(O)=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 BYPZVDNTPRNSST-UHFFFAOYSA-N 0.000 claims description 2
VBYJAFFZOAYAAQ-UHFFFAOYSA-N cyclohexyl-[2-[[4-(5-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound COC1=CC=C(F)C=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 VBYJAFFZOAYAAQ-UHFFFAOYSA-N 0.000 claims description 2
CIXYHVPQNQKMBH-UHFFFAOYSA-N cyclohexyl-[2-[[4-(7-methoxy-1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=2C=CNC=2C(OC)=CC=C1N(CC1)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 CIXYHVPQNQKMBH-UHFFFAOYSA-N 0.000 claims description 2
HUYBUPGTAVMMQN-UHFFFAOYSA-N cyclohexyl-[2-[[4-[(2,4-difluorophenyl)methyl]piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound FC1=CC(F)=CC=C1CN1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 HUYBUPGTAVMMQN-UHFFFAOYSA-N 0.000 claims description 2
XWUWAHYAOMTSQP-UHFFFAOYSA-N cyclohexyl-[2-[[4-[(2,5-dichlorophenyl)methyl]piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound ClC1=CC=C(Cl)C(CN2CCN(CC3N(C4=CC=CC=C4CC3)C(=O)C3CCCCC3)CC2)=C1 XWUWAHYAOMTSQP-UHFFFAOYSA-N 0.000 claims description 2
AUMHECZQJQZUKM-UHFFFAOYSA-N cyclohexyl-[2-[[4-[(2,5-difluorophenyl)methyl]piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound FC1=CC=C(F)C(CN2CCN(CC3N(C4=CC=CC=C4CC3)C(=O)C3CCCCC3)CC2)=C1 AUMHECZQJQZUKM-UHFFFAOYSA-N 0.000 claims description 2
PPEOHUAXWKUPLM-UHFFFAOYSA-N cyclohexyl-[2-[[4-[2-(trifluoromethoxy)phenyl]piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound FC(F)(F)OC1=CC=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 PPEOHUAXWKUPLM-UHFFFAOYSA-N 0.000 claims description 2
WIDZAWCYYDYHBV-UHFFFAOYSA-N cyclohexyl-[2-[[4-[2-(trifluoromethyl)phenyl]piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound FC(F)(F)C1=CC=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 WIDZAWCYYDYHBV-UHFFFAOYSA-N 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
VIAZDSBSIDCDLM-UHFFFAOYSA-N n-[3-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-3-oxopropyl]acetamide Chemical compound C1CC2=CC=CC=C2N(C(=O)CCNC(=O)C)C1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 VIAZDSBSIDCDLM-UHFFFAOYSA-N 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
125000000217 alkyl group Chemical group 0.000 claims 4
125000000623 heterocyclic group Chemical group 0.000 claims 4
125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 claims 3
125000003118 aryl group Chemical group 0.000 claims 3
RVOSVNZKHRFKBX-UHFFFAOYSA-N cyclohexyl-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 RVOSVNZKHRFKBX-UHFFFAOYSA-N 0.000 claims 3
125000002950 monocyclic group Chemical group 0.000 claims 3
125000001424 substituent group Chemical group 0.000 claims 3
WPHSZXCGRXTJTJ-GEPVFLLWSA-N 2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-n-[(1r)-1-phenylethyl]-3,4-dihydro-2h-quinoline-1-carboxamide Chemical compound C1([C@H](NC(=O)N2C3=CC=CC=C3CCC2CN2CCN(CC2)C=2C=3C=CNC=3C=CC=2)C)=CC=CC=C1 WPHSZXCGRXTJTJ-GEPVFLLWSA-N 0.000 claims 2
125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims 2
150000001204 N-oxides Chemical class 0.000 claims 2
125000002619 bicyclic group Chemical group 0.000 claims 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
QEDSJCPDLIXAJJ-UHFFFAOYSA-N cyclohexyl-[2-[[2-(2-methoxyphenoxy)ethyl-methylamino]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound COC1=CC=CC=C1OCCN(C)CC1N(C(=O)C2CCCCC2)C2=CC=CC=C2CC1 QEDSJCPDLIXAJJ-UHFFFAOYSA-N 0.000 claims 2
125000004433 nitrogen atom Chemical group N* 0.000 claims 2
150000003839 salts Chemical class 0.000 claims 2
239000012453 solvate Substances 0.000 claims 2
WIWLDIDKEQRUHY-UHFFFAOYSA-N (4-ethoxyphenyl)-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=CC(OCC)=CC=C1C(=O)N1C2=CC=CC=C2CCC1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 WIWLDIDKEQRUHY-UHFFFAOYSA-N 0.000 claims 1
PQKOOVBWHPJCKN-UHFFFAOYSA-N (4-hydroxyphenyl)-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=CC(O)=CC=C1C(=O)N1C2=CC=CC=C2CCC1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 PQKOOVBWHPJCKN-UHFFFAOYSA-N 0.000 claims 1
VARVBTSRTCOTIV-UHFFFAOYSA-N 1-(1-adamantyl)-2-[4-(1h-indol-4-yl)piperazin-1-yl]-2-(1,2,3,4-tetrahydroquinolin-2-yl)ethanone Chemical compound C1C(C2)CC(C3)CC2CC13C(=O)C(N1CCN(CC1)C=1C=2C=CNC=2C=CC=1)C1NC2=CC=CC=C2CC1 VARVBTSRTCOTIV-UHFFFAOYSA-N 0.000 claims 1
ODDRIMXYIULQHB-UHFFFAOYSA-N 1-(4-fluorophenyl)sulfonyl-2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinoline Chemical compound C1=CC(F)=CC=C1S(=O)(=O)N1C2=CC=CC=C2CCC1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 ODDRIMXYIULQHB-UHFFFAOYSA-N 0.000 claims 1
GYAUTLQCVSYKOH-UHFFFAOYSA-N 1-(benzenesulfonyl)-2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinoline Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1S(=O)(=O)C1=CC=CC=C1 GYAUTLQCVSYKOH-UHFFFAOYSA-N 0.000 claims 1
FSGCMGDWVATVJB-UHFFFAOYSA-N 1-(benzenesulfonyl)-2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinoline Chemical compound COC1=CC(F)=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)S(=O)(=O)C=2C=CC=CC=2)CC1 FSGCMGDWVATVJB-UHFFFAOYSA-N 0.000 claims 1
HAYWVRNBPUNASO-UHFFFAOYSA-N 1-(furan-2-yl)-2-[4-(1h-indol-4-yl)piperazin-1-yl]-2-(1,2,3,4-tetrahydroquinolin-2-yl)ethanone Chemical compound C1CC2=CC=CC=C2NC1C(N1CCN(CC1)C=1C=2C=CNC=2C=CC=1)C(=O)C1=CC=CO1 HAYWVRNBPUNASO-UHFFFAOYSA-N 0.000 claims 1
SCNXRWRORJVEPH-UHFFFAOYSA-N 1-[1-[[1-(cyclohexanecarbonyl)-3,4-dihydro-2h-quinolin-2-yl]methyl]-4-phenylpiperidin-4-yl]ethanone Chemical compound C1CC(C(=O)C)(C=2C=CC=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 SCNXRWRORJVEPH-UHFFFAOYSA-N 0.000 claims 1
LLEKUGQQYLRHDX-UHFFFAOYSA-N 1-[2-[(4-isoquinolin-1-ylpiperazin-1-yl)methyl]-3,4-dihydro-2h-quinolin-1-yl]-2-thiophen-2-ylethanone Chemical compound C1CN(C=2C3=CC=CC=C3C=CN=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)CC1=CC=CS1 LLEKUGQQYLRHDX-UHFFFAOYSA-N 0.000 claims 1
UGWZXIKTGNZWAD-UHFFFAOYSA-N 1-[2-[(4-isoquinolin-1-ylpiperazin-1-yl)methyl]-3,4-dihydro-2h-quinolin-1-yl]-2-thiophen-3-ylethanone Chemical compound C1CN(C=2C3=CC=CC=C3C=CN=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)CC=1C=CSC=1 UGWZXIKTGNZWAD-UHFFFAOYSA-N 0.000 claims 1
GOAHRRBVPGQWLX-UHFFFAOYSA-N 1-[2-[(4-isoquinolin-1-ylpiperazin-1-yl)methyl]-3,4-dihydro-2h-quinolin-1-yl]-3,3-dimethylbutan-1-one Chemical compound C1CC2=CC=CC=C2N(C(=O)CC(C)(C)C)C1CN1CCN(C=2C3=CC=CC=C3C=CN=2)CC1 GOAHRRBVPGQWLX-UHFFFAOYSA-N 0.000 claims 1
XOSQAUIVDLZHCK-UHFFFAOYSA-N 1-[2-[(4-isoquinolin-1-ylpiperazin-1-yl)methyl]-3,4-dihydro-2h-quinolin-1-yl]-3-methylbutan-1-one Chemical compound C1CC2=CC=CC=C2N(C(=O)CC(C)C)C1CN1CCN(C=2C3=CC=CC=C3C=CN=2)CC1 XOSQAUIVDLZHCK-UHFFFAOYSA-N 0.000 claims 1
ZVHCHDQVEVNOJQ-UHFFFAOYSA-N 1-[2-[(4-isoquinolin-1-ylpiperazin-1-yl)methyl]-3,4-dihydro-2h-quinolin-1-yl]-4-phenoxybutan-1-one Chemical compound C1CN(C=2C3=CC=CC=C3C=CN=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)CCCOC1=CC=CC=C1 ZVHCHDQVEVNOJQ-UHFFFAOYSA-N 0.000 claims 1
ZFSOFDMKFQZWRF-UHFFFAOYSA-N 1-[2-[[2-(2-methoxyphenoxy)ethyl-methylamino]methyl]-3,4-dihydro-2h-quinolin-1-yl]-2-thiophen-2-ylethanone Chemical compound COC1=CC=CC=C1OCCN(C)CC1N(C(=O)CC=2SC=CC=2)C2=CC=CC=C2CC1 ZFSOFDMKFQZWRF-UHFFFAOYSA-N 0.000 claims 1
OONGZXYTPJLYBD-UHFFFAOYSA-N 1-[2-[[2-(2-methoxyphenoxy)ethyl-methylamino]methyl]-3,4-dihydro-2h-quinolin-1-yl]-3,3-dimethylbutan-1-one Chemical compound COC1=CC=CC=C1OCCN(C)CC1N(C(=O)CC(C)(C)C)C2=CC=CC=C2CC1 OONGZXYTPJLYBD-UHFFFAOYSA-N 0.000 claims 1
PGZXJUWNNAZMBQ-UHFFFAOYSA-N 1-[2-[[2-(2-methoxyphenoxy)ethyl-methylamino]methyl]-3,4-dihydro-2h-quinolin-1-yl]-3-methylbutan-1-one Chemical compound COC1=CC=CC=C1OCCN(C)CC1N(C(=O)CC(C)C)C2=CC=CC=C2CC1 PGZXJUWNNAZMBQ-UHFFFAOYSA-N 0.000 claims 1
ZGFHOQWPCMYUBO-UHFFFAOYSA-N 1-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-2,2-dimethylpropan-1-one Chemical compound C1CC2=CC=CC=C2N(C(=O)C(C)(C)C)C1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 ZGFHOQWPCMYUBO-UHFFFAOYSA-N 0.000 claims 1
LPONQVDTLZOTSG-UHFFFAOYSA-N 1-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-2-[2-(trifluoromethyl)phenyl]ethanone Chemical compound FC(F)(F)C1=CC=CC=C1CC(=O)N1C2=CC=CC=C2CCC1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 LPONQVDTLZOTSG-UHFFFAOYSA-N 0.000 claims 1
PERUJZKNWQBKCG-UHFFFAOYSA-N 1-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-2-phenoxyethanone Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)COC1=CC=CC=C1 PERUJZKNWQBKCG-UHFFFAOYSA-N 0.000 claims 1
GLXXPWDLHHKXGU-UHFFFAOYSA-N 1-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-2-phenylmethoxyethanone Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)COCC1=CC=CC=C1 GLXXPWDLHHKXGU-UHFFFAOYSA-N 0.000 claims 1
VRGFRRUQSIAOOJ-UHFFFAOYSA-N 1-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-2-pyridin-3-ylethanone Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)CC1=CC=CN=C1 VRGFRRUQSIAOOJ-UHFFFAOYSA-N 0.000 claims 1
GDSXHTKWFJZKHC-UHFFFAOYSA-N 1-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-3,3-dimethylbutan-1-one Chemical compound C1CC2=CC=CC=C2N(C(=O)CC(C)(C)C)C1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 GDSXHTKWFJZKHC-UHFFFAOYSA-N 0.000 claims 1
YHFJKIRCAPZPFE-UHFFFAOYSA-N 1-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-3-methoxypropan-1-one Chemical compound C1CC2=CC=CC=C2N(C(=O)CCOC)C1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 YHFJKIRCAPZPFE-UHFFFAOYSA-N 0.000 claims 1
XLSLSHIFFVEBBA-UHFFFAOYSA-N 1-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-3-methylbutan-1-one Chemical compound C1CC2=CC=CC=C2N(C(=O)CC(C)C)C1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 XLSLSHIFFVEBBA-UHFFFAOYSA-N 0.000 claims 1
AGEAWHGEENMAST-UHFFFAOYSA-N 1-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-3-phenoxypropan-1-one Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)CCOC1=CC=CC=C1 AGEAWHGEENMAST-UHFFFAOYSA-N 0.000 claims 1
VHISNWBBRILMQT-UHFFFAOYSA-N 1-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-3-phenylmethoxypropan-1-one Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)CCOCC1=CC=CC=C1 VHISNWBBRILMQT-UHFFFAOYSA-N 0.000 claims 1
WGNOWQFNGOIFFJ-UHFFFAOYSA-N 1-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-3-propan-2-yloxypropan-1-one Chemical compound C1CC2=CC=CC=C2N(C(=O)CCOC(C)C)C1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 WGNOWQFNGOIFFJ-UHFFFAOYSA-N 0.000 claims 1
AANGUYNMIFVTGM-UHFFFAOYSA-N 1-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]ethanone Chemical compound C1CC2=CC=CC=C2N(C(=O)C)C1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 AANGUYNMIFVTGM-UHFFFAOYSA-N 0.000 claims 1
YMNBWBNSULJLSB-UHFFFAOYSA-N 1-[2-[[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-2,2,3,3,3-pentafluoropropan-1-one Chemical compound C1CC2=CC=CC=C2N(C(=O)C(F)(F)C(F)(F)F)C1CN1CCN(C=2C=3OCCOC=3C=CC=2)CC1 YMNBWBNSULJLSB-UHFFFAOYSA-N 0.000 claims 1
CGQWVHJUYHXJJE-UHFFFAOYSA-N 1-[2-[[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-2-thiophen-2-ylethanone Chemical compound C1CN(C=2C=3OCCOC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)CC1=CC=CS1 CGQWVHJUYHXJJE-UHFFFAOYSA-N 0.000 claims 1
QHABIQFEBBDDLZ-UHFFFAOYSA-N 1-[2-[[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-2-thiophen-3-ylethanone Chemical compound C1CN(C=2C=3OCCOC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)CC=1C=CSC=1 QHABIQFEBBDDLZ-UHFFFAOYSA-N 0.000 claims 1
YAUYYVQBVGXARX-UHFFFAOYSA-N 1-[2-[[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-3,3,3-trifluoropropan-1-one Chemical compound C1CC2=CC=CC=C2N(C(=O)CC(F)(F)F)C1CN1CCN(C=2C=3OCCOC=3C=CC=2)CC1 YAUYYVQBVGXARX-UHFFFAOYSA-N 0.000 claims 1
WUUSQWQKWAKLLQ-UHFFFAOYSA-N 1-[2-[[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-3,3-dimethylbutan-1-one Chemical compound C1CC2=CC=CC=C2N(C(=O)CC(C)(C)C)C1CN1CCN(C=2C=3OCCOC=3C=CC=2)CC1 WUUSQWQKWAKLLQ-UHFFFAOYSA-N 0.000 claims 1
ANXSUZAHWRYRLQ-UHFFFAOYSA-N 1-[2-[[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-3-(4-fluorophenyl)prop-2-en-1-one Chemical compound C1=CC(F)=CC=C1C=CC(=O)N1C2=CC=CC=C2CCC1CN1CCN(C=2C=3OCCOC=3C=CC=2)CC1 ANXSUZAHWRYRLQ-UHFFFAOYSA-N 0.000 claims 1
BDQUSPYLJRAYTG-UHFFFAOYSA-N 1-[2-[[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-3-methylbutan-1-one Chemical compound C1CC2=CC=CC=C2N(C(=O)CC(C)C)C1CN1CCN(C=2C=3OCCOC=3C=CC=2)CC1 BDQUSPYLJRAYTG-UHFFFAOYSA-N 0.000 claims 1
ODVAFJUAGSJZHA-UHFFFAOYSA-N 1-[2-[[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-3-phenylprop-2-en-1-one Chemical compound C1CN(C=2C=3OCCOC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C=CC1=CC=CC=C1 ODVAFJUAGSJZHA-UHFFFAOYSA-N 0.000 claims 1
PSSIYWUGESITIY-UHFFFAOYSA-N 1-[2-[[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-4-phenoxybutan-1-one Chemical compound C1CN(C=2C=3OCCOC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)CCCOC1=CC=CC=C1 PSSIYWUGESITIY-UHFFFAOYSA-N 0.000 claims 1
MHCYXYPOQINSSV-UHFFFAOYSA-N 1-[2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-2-thiophen-2-ylethanone Chemical compound COC1=CC(F)=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)CC=2SC=CC=2)CC1 MHCYXYPOQINSSV-UHFFFAOYSA-N 0.000 claims 1
FXICKKNNEAFATC-UHFFFAOYSA-N 1-[2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-2-thiophen-3-ylethanone Chemical compound COC1=CC(F)=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)CC2=CSC=C2)CC1 FXICKKNNEAFATC-UHFFFAOYSA-N 0.000 claims 1
NQMIBKDUPDKQGS-UHFFFAOYSA-N 1-[2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-3-methylbutan-1-one Chemical compound COC1=CC(F)=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)CC(C)C)CC1 NQMIBKDUPDKQGS-UHFFFAOYSA-N 0.000 claims 1
QWAOOMNFJUUXKV-UHFFFAOYSA-N 1-[2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]hexan-1-one Chemical compound C1CC2=CC=CC=C2N(C(=O)CCCCC)C1CN(CC1)CCN1C1=CC=C(F)C=C1OC QWAOOMNFJUUXKV-UHFFFAOYSA-N 0.000 claims 1
YOBUPGXTLFRIJD-UHFFFAOYSA-N 1-[2-nitro-4-(trifluoromethyl)phenyl]piperazine Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC=C1N1CCNCC1 YOBUPGXTLFRIJD-UHFFFAOYSA-N 0.000 claims 1
IHLRJLNBVJKMTQ-UHFFFAOYSA-N 1-[4-[(1-benzylsulfonyl-3,4-dihydro-2h-quinolin-2-yl)methyl]piperazin-1-yl]isoquinoline Chemical compound C1CN(C=2C3=CC=CC=C3C=CN=2)CCN1CC1CCC2=CC=CC=C2N1S(=O)(=O)CC1=CC=CC=C1 IHLRJLNBVJKMTQ-UHFFFAOYSA-N 0.000 claims 1
ZNYWFABKMTYNHI-UHFFFAOYSA-N 1-[4-[2-[(4-isoquinolin-1-ylpiperazin-1-yl)methyl]-3,4-dihydro-2h-quinoline-1-carbonyl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C(=O)N1C2=CC=CC=C2CCC1CN1CCN(C=2C3=CC=CC=C3C=CN=2)CC1 ZNYWFABKMTYNHI-UHFFFAOYSA-N 0.000 claims 1
UYTRXBXQHRGMRU-UHFFFAOYSA-N 1-[4-[2-[[2-(2-methoxyphenoxy)ethyl-methylamino]methyl]-3,4-dihydro-2h-quinoline-1-carbonyl]piperidin-1-yl]ethanone Chemical compound COC1=CC=CC=C1OCCN(C)CC1N(C(=O)C2CCN(CC2)C(C)=O)C2=CC=CC=C2CC1 UYTRXBXQHRGMRU-UHFFFAOYSA-N 0.000 claims 1
HUXMIBXWTRBTCN-UHFFFAOYSA-N 1-[4-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinoline-1-carbonyl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C(=O)N1C2=CC=CC=C2CCC1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 HUXMIBXWTRBTCN-UHFFFAOYSA-N 0.000 claims 1
GPDCBRMFVQYYIO-UHFFFAOYSA-N 1-[4-[4-[[1-(cyclohexanecarbonyl)-3,4-dihydro-2h-quinolin-2-yl]methyl]piperazin-1-yl]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 GPDCBRMFVQYYIO-UHFFFAOYSA-N 0.000 claims 1
MNJRMRVKBLVKNC-UHFFFAOYSA-N 1-[4-[[1-(benzenesulfonyl)-3,4-dihydro-2h-quinolin-2-yl]methyl]piperazin-1-yl]isoquinoline Chemical compound C1CN(C=2C3=CC=CC=C3C=CN=2)CCN1CC1CCC2=CC=CC=C2N1S(=O)(=O)C1=CC=CC=C1 MNJRMRVKBLVKNC-UHFFFAOYSA-N 0.000 claims 1
FGQBSIUYHAKTTK-UHFFFAOYSA-N 1-[[1-(cyclohexanecarbonyl)-3,4-dihydro-2h-quinolin-2-yl]methyl]-4-phenylpiperidine-4-carbonitrile Chemical compound C1CC(C=2C=CC=CC=2)(C#N)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 FGQBSIUYHAKTTK-UHFFFAOYSA-N 0.000 claims 1
GJXGLSXSJBDDHF-UHFFFAOYSA-N 1-benzyl-3-[1-[[1-(cyclohexanecarbonyl)-3,4-dihydro-2h-quinolin-2-yl]methyl]piperidin-4-yl]urea Chemical compound C1CN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CCC1NC(=O)NCC1=CC=CC=C1 GJXGLSXSJBDDHF-UHFFFAOYSA-N 0.000 claims 1
DVFLRDPDNSUYPQ-UHFFFAOYSA-N 1-benzylsulfonyl-2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinoline Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1S(=O)(=O)CC1=CC=CC=C1 DVFLRDPDNSUYPQ-UHFFFAOYSA-N 0.000 claims 1
JWSRLTUYKQMBGU-UHFFFAOYSA-N 1-benzylsulfonyl-2-[[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinoline Chemical compound C1CN(C=2C=3OCCOC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1S(=O)(=O)CC1=CC=CC=C1 JWSRLTUYKQMBGU-UHFFFAOYSA-N 0.000 claims 1
SBBQNUHHVRBBEW-UHFFFAOYSA-N 1-benzylsulfonyl-2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinoline Chemical compound COC1=CC(F)=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)S(=O)(=O)CC=2C=CC=CC=2)CC1 SBBQNUHHVRBBEW-UHFFFAOYSA-N 0.000 claims 1
125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims 1
JGPDNGPUNVCBBG-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-1-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]ethanone Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)CC1=CC=C(OCO2)C2=C1 JGPDNGPUNVCBBG-UHFFFAOYSA-N 0.000 claims 1
WZECHBHWSKWKSE-UHFFFAOYSA-N 2-(2-fluorophenyl)-1-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]ethanone Chemical compound FC1=CC=CC=C1CC(=O)N1C2=CC=CC=C2CCC1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 WZECHBHWSKWKSE-UHFFFAOYSA-N 0.000 claims 1
YEULCKXXJNMFML-UHFFFAOYSA-N 2-[(4-isoquinolin-1-ylpiperazin-1-yl)methyl]-n-(2-methylphenyl)-3,4-dihydro-2h-quinoline-1-carboxamide Chemical compound CC1=CC=CC=C1NC(=O)N1C2=CC=CC=C2CCC1CN1CCN(C=2C3=CC=CC=C3C=CN=2)CC1 YEULCKXXJNMFML-UHFFFAOYSA-N 0.000 claims 1
KCIGWTSIDCZJFT-UHFFFAOYSA-N 2-[4-(1h-indol-4-yl)piperazin-1-yl]-n-(4-methoxyphenyl)-2-(1,2,3,4-tetrahydroquinolin-2-yl)acetamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C(N1CCN(CC1)C=1C=2C=CNC=2C=CC=1)C1NC2=CC=CC=C2CC1 KCIGWTSIDCZJFT-UHFFFAOYSA-N 0.000 claims 1
BFGMTOWVUWAVOZ-UHFFFAOYSA-N 2-[4-(1h-indol-4-yl)piperazin-1-yl]-n-[(4-methoxyphenyl)methyl]-2-(1,2,3,4-tetrahydroquinolin-2-yl)acetamide Chemical compound C1=CC(OC)=CC=C1CNC(=O)C(N1CCN(CC1)C=1C=2C=CNC=2C=CC=1)C1NC2=CC=CC=C2CC1 BFGMTOWVUWAVOZ-UHFFFAOYSA-N 0.000 claims 1
IHZZTMGTWQEKLV-UHFFFAOYSA-N 2-[4-[[1-(cyclohexanecarbonyl)-3,4-dihydro-2h-quinolin-2-yl]methyl]piperazin-1-yl]benzonitrile Chemical compound C1CN(C=2C(=CC=CC=2)C#N)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 IHZZTMGTWQEKLV-UHFFFAOYSA-N 0.000 claims 1
IIVUNQBYEVPNPK-UHFFFAOYSA-N 2-[4-[[1-(cyclohexanecarbonyl)-3,4-dihydro-2h-quinolin-2-yl]methyl]piperazin-1-yl]pyridine-3-carbonitrile Chemical compound C1CN(C=2C(=CC=CN=2)C#N)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 IIVUNQBYEVPNPK-UHFFFAOYSA-N 0.000 claims 1
MMAKORLBQYOUEZ-UHFFFAOYSA-N 2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-1-(4-methoxyphenyl)sulfonyl-3,4-dihydro-2h-quinoline Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=CC=C2CCC1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 MMAKORLBQYOUEZ-UHFFFAOYSA-N 0.000 claims 1
GKYOBTKDWXBERF-UHFFFAOYSA-N 2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-1-(4-methylphenyl)sulfonyl-3,4-dihydro-2h-quinoline Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C2=CC=CC=C2CCC1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 GKYOBTKDWXBERF-UHFFFAOYSA-N 0.000 claims 1
NRDGFKDYXCRGLI-UHFFFAOYSA-N 2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-1-thiophen-2-ylsulfonyl-3,4-dihydro-2h-quinoline Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1S(=O)(=O)C1=CC=CS1 NRDGFKDYXCRGLI-UHFFFAOYSA-N 0.000 claims 1
MSTIGGVRXDIXPV-UHFFFAOYSA-N 2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-n,n-dimethyl-3,4-dihydro-2h-quinoline-1-carboxamide Chemical compound C1CC2=CC=CC=C2N(C(=O)N(C)C)C1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 MSTIGGVRXDIXPV-UHFFFAOYSA-N 0.000 claims 1
JLJDHCOHQRKDLJ-UHFFFAOYSA-N 2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-n-(2-methylphenyl)-3,4-dihydro-2h-quinoline-1-carboxamide Chemical compound CC1=CC=CC=C1NC(=O)N1C2=CC=CC=C2CCC1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 JLJDHCOHQRKDLJ-UHFFFAOYSA-N 0.000 claims 1
ROYGCCMTOMOLHS-UHFFFAOYSA-N 2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-n-(2-phenylethyl)-3,4-dihydro-2h-quinoline-1-carboxamide Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)NCCC1=CC=CC=C1 ROYGCCMTOMOLHS-UHFFFAOYSA-N 0.000 claims 1
CVCGFNGYZRFIHI-UHFFFAOYSA-N 2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-n-(3-methylphenyl)-3,4-dihydro-2h-quinoline-1-carboxamide Chemical compound CC1=CC=CC(NC(=O)N2C3=CC=CC=C3CCC2CN2CCN(CC2)C=2C=3C=CNC=3C=CC=2)=C1 CVCGFNGYZRFIHI-UHFFFAOYSA-N 0.000 claims 1
UFLGXHHFVGLTPP-UHFFFAOYSA-N 2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-n-(4-methylphenyl)-3,4-dihydro-2h-quinoline-1-carboxamide Chemical compound C1=CC(C)=CC=C1NC(=O)N1C2=CC=CC=C2CCC1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 UFLGXHHFVGLTPP-UHFFFAOYSA-N 0.000 claims 1
WPHSZXCGRXTJTJ-ZZHFZYNASA-N 2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-n-[(1s)-1-phenylethyl]-3,4-dihydro-2h-quinoline-1-carboxamide Chemical compound C1([C@@H](NC(=O)N2C3=CC=CC=C3CCC2CN2CCN(CC2)C=2C=3C=CNC=3C=CC=2)C)=CC=CC=C1 WPHSZXCGRXTJTJ-ZZHFZYNASA-N 0.000 claims 1
COGZIBOFPFFSJQ-UHFFFAOYSA-N 2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-n-(2-methylphenyl)-3,4-dihydro-2h-quinoline-1-carboxamide Chemical compound COC1=CC(F)=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)NC=2C(=CC=CC=2)C)CC1 COGZIBOFPFFSJQ-UHFFFAOYSA-N 0.000 claims 1
125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 claims 1
HVNOSWGZPSXACV-UHFFFAOYSA-N 2-cyclopropyl-1-[2-[(4-isoquinolin-1-ylpiperazin-1-yl)methyl]-3,4-dihydro-2h-quinolin-1-yl]ethanone Chemical compound C1CN(C=2C3=CC=CC=C3C=CN=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)CC1CC1 HVNOSWGZPSXACV-UHFFFAOYSA-N 0.000 claims 1
WIZSHQCBYKIGNZ-UHFFFAOYSA-N 2-cyclopropyl-1-[2-[[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]ethanone Chemical compound C1CN(C=2C=3OCCOC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)CC1CC1 WIZSHQCBYKIGNZ-UHFFFAOYSA-N 0.000 claims 1
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
DNECISGLXIXRMG-UHFFFAOYSA-N 3-bicyclo[2.2.2]octanyl-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1C(CC2)CCC2C1 DNECISGLXIXRMG-UHFFFAOYSA-N 0.000 claims 1
ZPYCJPZQAGWBDD-UHFFFAOYSA-N 3-cyclopropyl-1-[4-(1h-indol-4-yl)piperazin-1-yl]-1-(1,2,3,4-tetrahydroquinolin-2-yl)propan-2-one Chemical compound C1CC2=CC=CC=C2NC1C(N1CCN(CC1)C=1C=2C=CNC=2C=CC=1)C(=O)CC1CC1 ZPYCJPZQAGWBDD-UHFFFAOYSA-N 0.000 claims 1
PZKWTDIZEWHKFC-UHFFFAOYSA-N 3-ethyl-1-[4-(1h-indol-4-yl)piperazin-1-yl]-1-(1,2,3,4-tetrahydroquinolin-2-yl)pentan-2-one Chemical compound C1CC2=CC=CC=C2NC1C(C(=O)C(CC)CC)N(CC1)CCN1C1=CC=CC2=C1C=CN2 PZKWTDIZEWHKFC-UHFFFAOYSA-N 0.000 claims 1
GGUOHCXLTHVAJH-UHFFFAOYSA-N 3-hydroxy-1-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]propan-1-one Chemical compound C1CC2=CC=CC=C2N(C(=O)CCO)C1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 GGUOHCXLTHVAJH-UHFFFAOYSA-N 0.000 claims 1
GYOFMNRYFSKDDN-UHFFFAOYSA-N 3-hydroxy-1-[2-[[4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]propan-1-one Chemical compound C1CC2=CC=CC=C2N(C(=O)CCO)C1CN(CC1)CCN1C1=CC=CC=C1OCC(F)(F)F GYOFMNRYFSKDDN-UHFFFAOYSA-N 0.000 claims 1
QNGZOZXXCUUBNN-UHFFFAOYSA-N 3-methoxy-1-[2-[[4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]propan-1-one Chemical compound C1CC2=CC=CC=C2N(C(=O)CCOC)C1CN(CC1)CCN1C1=CC=CC=C1OCC(F)(F)F QNGZOZXXCUUBNN-UHFFFAOYSA-N 0.000 claims 1
PMJFGUCPHMKVIJ-UHFFFAOYSA-N 3-phenylmethoxy-1-[2-[[4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]propan-1-one Chemical compound FC(F)(F)COC1=CC=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)CCOCC=2C=CC=CC=2)CC1 PMJFGUCPHMKVIJ-UHFFFAOYSA-N 0.000 claims 1
IIXTWWLSIBGZDC-UHFFFAOYSA-N 4-[2-[(4-isoquinolin-1-ylpiperazin-1-yl)methyl]-3,4-dihydro-2h-quinoline-1-carbonyl]benzonitrile Chemical compound C1CN(C=2C3=CC=CC=C3C=CN=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1=CC=C(C#N)C=C1 IIXTWWLSIBGZDC-UHFFFAOYSA-N 0.000 claims 1
VIRDXOVOKLQDCD-UHFFFAOYSA-N 4-[2-[[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinoline-1-carbonyl]benzonitrile Chemical compound C1CN(C=2C=3OCCOC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1=CC=C(C#N)C=C1 VIRDXOVOKLQDCD-UHFFFAOYSA-N 0.000 claims 1
IXJBXEPUQZTSST-UHFFFAOYSA-N 4-[4-[[1-(cyclohexanecarbonyl)-3,4-dihydro-2h-quinolin-2-yl]methyl]piperazin-1-yl]-3-(trifluoromethoxy)benzonitrile Chemical compound FC(F)(F)OC1=CC(C#N)=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 IXJBXEPUQZTSST-UHFFFAOYSA-N 0.000 claims 1
RBYLZOILVYUVMA-UHFFFAOYSA-N 4-[[1-(cyclohexanecarbonyl)-3,4-dihydro-2h-quinolin-2-yl]methyl]-1-phenylpiperazin-2-one Chemical compound C1CN(C=2C=CC=CC=2)C(=O)CN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 RBYLZOILVYUVMA-UHFFFAOYSA-N 0.000 claims 1
RLUMDYAJIJPZAY-UHFFFAOYSA-N 4-[[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]sulfonyl]benzonitrile Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1S(=O)(=O)C1=CC=C(C#N)C=C1 RLUMDYAJIJPZAY-UHFFFAOYSA-N 0.000 claims 1
VOXRWVDQHUNCDB-UHFFFAOYSA-N 4-amino-1-[4-(1h-indol-4-yl)piperazin-1-yl]-1-(1,2,3,4-tetrahydroquinolin-2-yl)butan-2-one Chemical compound C1CC2=CC=CC=C2NC1C(C(=O)CCN)N(CC1)CCN1C1=CC=CC2=C1C=CN2 VOXRWVDQHUNCDB-UHFFFAOYSA-N 0.000 claims 1
125000006418 4-methylphenylsulfonyl group Chemical group 0.000 claims 1
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 1
SXYAWGHBNSVMCW-UHFFFAOYSA-N 6-[4-[[1-(cyclohexanecarbonyl)-3,4-dihydro-2h-quinolin-2-yl]methyl]piperazin-1-yl]pyridine-3-carbonitrile Chemical compound C1CN(C=2N=CC(=CC=2)C#N)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 SXYAWGHBNSVMCW-UHFFFAOYSA-N 0.000 claims 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
OZVLPUHTALMTDM-UHFFFAOYSA-N N-(4-fluorophenyl)-2-[[4-(1H-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2H-quinoline-1-carboxamide Chemical compound C1=CC(F)=CC=C1NC(=O)N1C2=CC=CC=C2CCC1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 OZVLPUHTALMTDM-UHFFFAOYSA-N 0.000 claims 1
NIRQTIWDIMOTCP-UHFFFAOYSA-N [1-[[1-(cyclohexanecarbonyl)-3,4-dihydro-2h-quinolin-2-yl]methyl]piperidin-4-yl]-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)C1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 NIRQTIWDIMOTCP-UHFFFAOYSA-N 0.000 claims 1
KSFQFBDNAMXUSZ-UHFFFAOYSA-N [1-[[1-(cyclohexanecarbonyl)-3,4-dihydro-2h-quinolin-2-yl]methyl]piperidin-4-yl]-phenylmethanone Chemical compound C1CC(C(=O)C=2C=CC=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 KSFQFBDNAMXUSZ-UHFFFAOYSA-N 0.000 claims 1
TUXDTCUJDPGIPG-UHFFFAOYSA-N [2-[(2-benzylpyrrolidin-1-yl)methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound C1CCC(CC=2C=CC=CC=2)N1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 TUXDTCUJDPGIPG-UHFFFAOYSA-N 0.000 claims 1
VDXFEAPIZRPNOL-UHFFFAOYSA-N [2-[(4-benzoylpiperazin-1-yl)methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound C1CN(C(=O)C=2C=CC=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 VDXFEAPIZRPNOL-UHFFFAOYSA-N 0.000 claims 1
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UXBTVFRFWGLVAI-UHFFFAOYSA-N [2-[(4-benzylpiperidin-1-yl)methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound C1CC(CC=2C=CC=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 UXBTVFRFWGLVAI-UHFFFAOYSA-N 0.000 claims 1
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SHVKMKOTBBXEIE-UHFFFAOYSA-N [2-[(4-isoquinolin-1-ylpiperazin-1-yl)methyl]-3,4-dihydro-2h-quinolin-1-yl]-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)N1C2=CC=CC=C2CCC1CN1CCN(C=2C3=CC=CC=C3C=CN=2)CC1 SHVKMKOTBBXEIE-UHFFFAOYSA-N 0.000 claims 1
IPQYMTMLPONSAM-UHFFFAOYSA-N [2-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-2-oxoethyl] acetate Chemical compound C1CC2=CC=CC=C2N(C(=O)COC(=O)C)C1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 IPQYMTMLPONSAM-UHFFFAOYSA-N 0.000 claims 1
SRSGBFZHLVLOLX-UHFFFAOYSA-N [2-[[1-(1-benzofuran-3-yl)piperidin-4-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound C1CN(C=2C3=CC=CC=C3OC=2)CCC1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 SRSGBFZHLVLOLX-UHFFFAOYSA-N 0.000 claims 1
KPVJXTFJTMHFQM-UHFFFAOYSA-N [2-[[2-(2-chlorophenoxy)ethyl-methylamino]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound C1CC2=CC=CC=C2N(C(=O)C2CCCCC2)C1CN(C)CCOC1=CC=CC=C1Cl KPVJXTFJTMHFQM-UHFFFAOYSA-N 0.000 claims 1
ZPUAPRJGCLKGKH-UHFFFAOYSA-N [2-[[2-(2-methoxyphenoxy)ethyl-methylamino]methyl]-3,4-dihydro-2h-quinolin-1-yl]-(1h-pyrrol-2-yl)methanone Chemical compound COC1=CC=CC=C1OCCN(C)CC1N(C(=O)C=2NC=CC=2)C2=CC=CC=C2CC1 ZPUAPRJGCLKGKH-UHFFFAOYSA-N 0.000 claims 1
OSGADGPXLPFMOV-UHFFFAOYSA-N [2-[[2-(2-methoxyphenoxy)ethyl-methylamino]methyl]-3,4-dihydro-2h-quinolin-1-yl]-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)N1C2=CC=CC=C2CCC1CN(C)CCOC1=CC=CC=C1OC OSGADGPXLPFMOV-UHFFFAOYSA-N 0.000 claims 1
ITSQOCZSMBBYAD-UHFFFAOYSA-N [2-[[2-(3-chlorophenoxy)ethyl-methylamino]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound C1CC2=CC=CC=C2N(C(=O)C2CCCCC2)C1CN(C)CCOC1=CC=CC(Cl)=C1 ITSQOCZSMBBYAD-UHFFFAOYSA-N 0.000 claims 1
CWKPURANLOXVIO-UHFFFAOYSA-N [2-[[2-(4-chlorophenoxy)ethyl-methylamino]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound C1CC2=CC=CC=C2N(C(=O)C2CCCCC2)C1CN(C)CCOC1=CC=C(Cl)C=C1 CWKPURANLOXVIO-UHFFFAOYSA-N 0.000 claims 1
KIXYPTHAQMLKKL-UHFFFAOYSA-N [2-[[2-(4-chlorophenyl)piperidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound C1=CC(Cl)=CC=C1C1N(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CCCC1 KIXYPTHAQMLKKL-UHFFFAOYSA-N 0.000 claims 1
IVYXAMXAEWEKIM-UHFFFAOYSA-N [2-[[2-(4-chlorophenyl)pyrrolidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound C1=CC(Cl)=CC=C1C1N(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CCC1 IVYXAMXAEWEKIM-UHFFFAOYSA-N 0.000 claims 1
KRCCMQDSELXPOB-UHFFFAOYSA-N [2-[[4-(1,3-benzodioxol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound C1CN(C=2C=3OCOC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 KRCCMQDSELXPOB-UHFFFAOYSA-N 0.000 claims 1
YHZJMDYANXKTTO-UHFFFAOYSA-N [2-[[4-(1-benzofuran-7-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound C1CN(C=2C=3OC=CC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 YHZJMDYANXKTTO-UHFFFAOYSA-N 0.000 claims 1
ZGLFIHWLZVSHEG-UHFFFAOYSA-N [2-[[4-(1h-benzimidazol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound C1CN(C=2C=3N=CNC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 ZGLFIHWLZVSHEG-UHFFFAOYSA-N 0.000 claims 1
JCCJNKNNMIYJJF-UHFFFAOYSA-N [2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-(1,2-oxazol-5-yl)methanone Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1=CC=NO1 JCCJNKNNMIYJJF-UHFFFAOYSA-N 0.000 claims 1
TUOJVPQQLPCVLY-UHFFFAOYSA-N [2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-(1-methylindol-3-yl)methanone Chemical compound C12=CC=CC=C2N(C)C=C1C(=O)N1C2=CC=CC=C2CCC1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 TUOJVPQQLPCVLY-UHFFFAOYSA-N 0.000 claims 1
TWQYPKYIPIYLNI-UHFFFAOYSA-N [2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-(3-methoxyphenyl)methanone Chemical compound COC1=CC=CC(C(=O)N2C3=CC=CC=C3CCC2CN2CCN(CC2)C=2C=3C=CNC=3C=CC=2)=C1 TWQYPKYIPIYLNI-UHFFFAOYSA-N 0.000 claims 1
SEKDZDNBXXNPKD-UHFFFAOYSA-N [2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)N1C2=CC=CC=C2CCC1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 SEKDZDNBXXNPKD-UHFFFAOYSA-N 0.000 claims 1
XNVOYBFHQCJMOP-UHFFFAOYSA-N [2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-(oxolan-2-yl)methanone Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCO1 XNVOYBFHQCJMOP-UHFFFAOYSA-N 0.000 claims 1
ONYMGUDGRNPWOV-UHFFFAOYSA-N [2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-(oxolan-3-yl)methanone Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCOC1 ONYMGUDGRNPWOV-UHFFFAOYSA-N 0.000 claims 1
YYFCOVWHMZBGMO-UHFFFAOYSA-N [2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-phenylmethanone Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1=CC=CC=C1 YYFCOVWHMZBGMO-UHFFFAOYSA-N 0.000 claims 1
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QWTNCBDQPRLFQE-UHFFFAOYSA-N [2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-pyridin-3-ylmethanone Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1=CC=CN=C1 QWTNCBDQPRLFQE-UHFFFAOYSA-N 0.000 claims 1
AYHHYEUQDQZUQZ-UHFFFAOYSA-N [2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-pyridin-4-ylmethanone Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1=CC=NC=C1 AYHHYEUQDQZUQZ-UHFFFAOYSA-N 0.000 claims 1
OPHRAGOIHCAUHD-UHFFFAOYSA-N [2-[[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-(1h-pyrrol-2-yl)methanone Chemical compound C1CN(C=2C=3OCCOC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1=CC=CN1 OPHRAGOIHCAUHD-UHFFFAOYSA-N 0.000 claims 1
TYMMVGPVKMHQCQ-UHFFFAOYSA-N [2-[[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-(2-methylfuran-3-yl)methanone Chemical compound O1C=CC(C(=O)N2C3=CC=CC=C3CCC2CN2CCN(CC2)C=2C=3OCCOC=3C=CC=2)=C1C TYMMVGPVKMHQCQ-UHFFFAOYSA-N 0.000 claims 1
GAMVOIGHAZWUBO-UHFFFAOYSA-N [2-[[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-(3-methylthiophen-2-yl)methanone Chemical compound C1=CSC(C(=O)N2C3=CC=CC=C3CCC2CN2CCN(CC2)C=2C=3OCCOC=3C=CC=2)=C1C GAMVOIGHAZWUBO-UHFFFAOYSA-N 0.000 claims 1
BBRYOCHBEPEBRD-UHFFFAOYSA-N [2-[[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)N1C2=CC=CC=C2CCC1CN1CCN(C=2C=3OCCOC=3C=CC=2)CC1 BBRYOCHBEPEBRD-UHFFFAOYSA-N 0.000 claims 1
KKUAJVFAJZFMNL-UHFFFAOYSA-N [2-[[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-(5-methyl-1,2-oxazol-4-yl)methanone Chemical compound O1N=CC(C(=O)N2C3=CC=CC=C3CCC2CN2CCN(CC2)C=2C=3OCCOC=3C=CC=2)=C1C KKUAJVFAJZFMNL-UHFFFAOYSA-N 0.000 claims 1
YQRUUOOMAUPXMZ-UHFFFAOYSA-N [2-[[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-(furan-2-yl)methanone Chemical compound C1CN(C=2C=3OCCOC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1=CC=CO1 YQRUUOOMAUPXMZ-UHFFFAOYSA-N 0.000 claims 1
UDAUNCZCVCZUBR-UHFFFAOYSA-N [2-[[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-(furan-3-yl)methanone Chemical compound C1CN(C=2C=3OCCOC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C=1C=COC=1 UDAUNCZCVCZUBR-UHFFFAOYSA-N 0.000 claims 1
DMHXMLSQUSSIBU-UHFFFAOYSA-N [2-[[4-(2-bromophenyl)piperidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound BrC1=CC=CC=C1C1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 DMHXMLSQUSSIBU-UHFFFAOYSA-N 0.000 claims 1
SSJXZASEOJZBME-UHFFFAOYSA-N [2-[[4-(2-chloro-6-fluorophenyl)piperidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound FC1=CC=CC(Cl)=C1C1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 SSJXZASEOJZBME-UHFFFAOYSA-N 0.000 claims 1
KGXVAJKYXNPTQJ-UHFFFAOYSA-N [2-[[4-(2-chlorophenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound ClC1=CC=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 KGXVAJKYXNPTQJ-UHFFFAOYSA-N 0.000 claims 1
USSQCRVDMHLAOE-UHFFFAOYSA-N [2-[[4-(2-chlorophenyl)piperidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound ClC1=CC=CC=C1C1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 USSQCRVDMHLAOE-UHFFFAOYSA-N 0.000 claims 1
UVHXWXVFQVYHQW-UHFFFAOYSA-N [2-[[4-(2h-benzotriazol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound C1CN(C=2C=3NN=NC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 UVHXWXVFQVYHQW-UHFFFAOYSA-N 0.000 claims 1
BDCDYCXXZRDFFN-UHFFFAOYSA-N [2-[[4-(3-bromophenyl)piperidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound BrC1=CC=CC(C2CCN(CC3N(C4=CC=CC=C4CC3)C(=O)C3CCCCC3)CC2)=C1 BDCDYCXXZRDFFN-UHFFFAOYSA-N 0.000 claims 1
QYRLYLWOJQPRAW-UHFFFAOYSA-N [2-[[4-(3-chlorophenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound ClC1=CC=CC(N2CCN(CC3N(C4=CC=CC=C4CC3)C(=O)C3CCCCC3)CC2)=C1 QYRLYLWOJQPRAW-UHFFFAOYSA-N 0.000 claims 1
KUNALHQYCTZCSU-UHFFFAOYSA-N [2-[[4-(3-chlorophenyl)piperidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound ClC1=CC=CC(C2CCN(CC3N(C4=CC=CC=C4CC3)C(=O)C3CCCCC3)CC2)=C1 KUNALHQYCTZCSU-UHFFFAOYSA-N 0.000 claims 1
PVVNVAMYWPYYRM-UHFFFAOYSA-N [2-[[4-(4-aminophenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound C1=CC(N)=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 PVVNVAMYWPYYRM-UHFFFAOYSA-N 0.000 claims 1
CQZSCURZCZMBSY-UHFFFAOYSA-N [2-[[4-(4-butoxyphenyl)piperidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound C1=CC(OCCCC)=CC=C1C1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 CQZSCURZCZMBSY-UHFFFAOYSA-N 0.000 claims 1
YPSCWYZSZPTGOC-UHFFFAOYSA-N [2-[[4-(4-chloro-2-ethoxyphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound CCOC1=CC(Cl)=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 YPSCWYZSZPTGOC-UHFFFAOYSA-N 0.000 claims 1
AKMDPLGQQMFVMH-UHFFFAOYSA-N [2-[[4-(4-chloro-2-methoxyphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound COC1=CC(Cl)=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 AKMDPLGQQMFVMH-UHFFFAOYSA-N 0.000 claims 1
KQFPPSNRXUYUAU-UHFFFAOYSA-N [2-[[4-(4-chloro-2-nitrophenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 KQFPPSNRXUYUAU-UHFFFAOYSA-N 0.000 claims 1
YRLKIPBBJDHTCQ-UHFFFAOYSA-N [2-[[4-(4-chloro-2-propoxyphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound CCCOC1=CC(Cl)=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 YRLKIPBBJDHTCQ-UHFFFAOYSA-N 0.000 claims 1
OMGKNEGPVRCURH-UHFFFAOYSA-N [2-[[4-(4-chlorophenyl)piperidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound C1=CC(Cl)=CC=C1C1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 OMGKNEGPVRCURH-UHFFFAOYSA-N 0.000 claims 1
ZAVLIQVLWGERFH-UHFFFAOYSA-N [2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-(1h-pyrrol-2-yl)methanone Chemical compound COC1=CC(F)=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C=2NC=CC=2)CC1 ZAVLIQVLWGERFH-UHFFFAOYSA-N 0.000 claims 1
WHCRNPZCTMWYHA-UHFFFAOYSA-N [2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)N1C2=CC=CC=C2CCC1CN1CCN(C=2C(=CC(F)=CC=2)OC)CC1 WHCRNPZCTMWYHA-UHFFFAOYSA-N 0.000 claims 1
OMYYGOQWLGJQMB-UHFFFAOYSA-N [2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-(furan-2-yl)methanone Chemical compound COC1=CC(F)=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C=2OC=CC=2)CC1 OMYYGOQWLGJQMB-UHFFFAOYSA-N 0.000 claims 1
PZKFKFYTQHWIGK-UHFFFAOYSA-N [2-[[4-(5-chloro-2-methoxyphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound COC1=CC=C(Cl)C=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 PZKFKFYTQHWIGK-UHFFFAOYSA-N 0.000 claims 1
UTJNWHMTIQZVTN-UHFFFAOYSA-N [2-[[4-(5-chloro-2-methylphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound CC1=CC=C(Cl)C=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 UTJNWHMTIQZVTN-UHFFFAOYSA-N 0.000 claims 1
CGQFQKOAZYXUDL-UHFFFAOYSA-N [2-[[4-(6-chloropyridin-2-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound ClC1=CC=CC(N2CCN(CC3N(C4=CC=CC=C4CC3)C(=O)C3CCCCC3)CC2)=N1 CGQFQKOAZYXUDL-UHFFFAOYSA-N 0.000 claims 1
FWFVWQUTPSSXTA-UHFFFAOYSA-N [2-[[4-(benzimidazol-1-yl)piperidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound C1CC(N2C3=CC=CC=C3N=C2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 FWFVWQUTPSSXTA-UHFFFAOYSA-N 0.000 claims 1
BWWGZHRODQXUQQ-UHFFFAOYSA-N [2-[[4-[(2-bromo-5-methoxyphenyl)methyl]piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound COC1=CC=C(Br)C(CN2CCN(CC3N(C4=CC=CC=C4CC3)C(=O)C3CCCCC3)CC2)=C1 BWWGZHRODQXUQQ-UHFFFAOYSA-N 0.000 claims 1
LVIFPPXTSWQAIC-UHFFFAOYSA-N [2-[[4-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound ClC1=CC(C(F)(F)F)=CN=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 LVIFPPXTSWQAIC-UHFFFAOYSA-N 0.000 claims 1
NUVHJHOXAOBRCB-UHFFFAOYSA-N [2-[[4-[4-chloro-3-(trifluoromethyl)phenyl]piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(N2CCN(CC3N(C4=CC=CC=C4CC3)C(=O)C3CCCCC3)CC2)=C1 NUVHJHOXAOBRCB-UHFFFAOYSA-N 0.000 claims 1
DXVKSTZSGBWYSF-UHFFFAOYSA-N [2-[[benzyl-[2-(2-methoxyphenoxy)ethyl]amino]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound COC1=CC=CC=C1OCCN(CC=1C=CC=CC=1)CC1N(C(=O)C2CCCCC2)C2=CC=CC=C2CC1 DXVKSTZSGBWYSF-UHFFFAOYSA-N 0.000 claims 1
MLOFUVQLEZCCRR-UHFFFAOYSA-N [6-amino-2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound COC1=CC(F)=CC=C1N1CCN(CC2N(C3=CC=C(N)C=C3CC2)C(=O)C2CCCCC2)CC1 MLOFUVQLEZCCRR-UHFFFAOYSA-N 0.000 claims 1
125000003342 alkenyl group Chemical group 0.000 claims 1
125000003545 alkoxy group Chemical group 0.000 claims 1
125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
125000003282 alkyl amino group Chemical group 0.000 claims 1
125000001691 aryl alkyl amino group Chemical group 0.000 claims 1
125000001769 aryl amino group Chemical group 0.000 claims 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
125000002618 bicyclic heterocycle group Chemical group 0.000 claims 1
125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
125000000392 cycloalkenyl group Chemical group 0.000 claims 1
125000000753 cycloalkyl group Chemical group 0.000 claims 1
YMVMAEGGDXCSJN-UHFFFAOYSA-N cyclobutyl-[2-[(4-isoquinolin-1-ylpiperazin-1-yl)methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CN(C=2C3=CC=CC=C3C=CN=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCC1 YMVMAEGGDXCSJN-UHFFFAOYSA-N 0.000 claims 1
RNYFEWOEILCXMS-UHFFFAOYSA-N cyclobutyl-[2-[[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CN(C=2C=3OCCOC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCC1 RNYFEWOEILCXMS-UHFFFAOYSA-N 0.000 claims 1
HABVUAVVHZRFSG-UHFFFAOYSA-N cyclohex-3-en-1-yl-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCC=CC1 HABVUAVVHZRFSG-UHFFFAOYSA-N 0.000 claims 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 claims 1
MWTCHAXJOWXTPM-UHFFFAOYSA-N cyclohexyl-[2-[(2-phenylpyrrolidin-1-yl)methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CCC(C=2C=CC=CC=2)N1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 MWTCHAXJOWXTPM-UHFFFAOYSA-N 0.000 claims 1
BQRSIQQXNXEBAO-UHFFFAOYSA-N cyclohexyl-[2-[(2-pyridin-2-yloxyethylamino)methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C=1C=CC=NC=1OCCNCC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 BQRSIQQXNXEBAO-UHFFFAOYSA-N 0.000 claims 1
SXCLSGCCAPYAHB-UHFFFAOYSA-N cyclohexyl-[2-[(2-pyridin-2-ylpyrrolidin-1-yl)methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CCC(C=2N=CC=CC=2)N1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 SXCLSGCCAPYAHB-UHFFFAOYSA-N 0.000 claims 1
NHELCQJCDBWRDI-UHFFFAOYSA-N cyclohexyl-[2-[(2-pyridin-3-ylpyrrolidin-1-yl)methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CCC(C=2C=NC=CC=2)N1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 NHELCQJCDBWRDI-UHFFFAOYSA-N 0.000 claims 1
VSEBYRQTJIRMNG-UHFFFAOYSA-N cyclohexyl-[2-[(2-thiophen-2-ylpyrrolidin-1-yl)methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CCC(C=2SC=CC=2)N1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 VSEBYRQTJIRMNG-UHFFFAOYSA-N 0.000 claims 1
VPFGMVRQWFGXOZ-UHFFFAOYSA-N cyclohexyl-[2-[(4-isoquinolin-1-ylpiperazin-1-yl)methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CN(C=2C3=CC=CC=C3C=CN=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 VPFGMVRQWFGXOZ-UHFFFAOYSA-N 0.000 claims 1
RJSZPVTUIFMAIV-UHFFFAOYSA-N cyclohexyl-[2-[(4-phenylmethoxypiperidin-1-yl)methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CC(OCC=2C=CC=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 RJSZPVTUIFMAIV-UHFFFAOYSA-N 0.000 claims 1
HPUBXQOMWPHNMN-UHFFFAOYSA-N cyclohexyl-[2-[(4-phenylpiperidin-1-yl)methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CC(C=2C=CC=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 HPUBXQOMWPHNMN-UHFFFAOYSA-N 0.000 claims 1
WAVFFOAAMPSSLB-UHFFFAOYSA-N cyclohexyl-[2-[(4-pyridin-2-ylpiperazin-1-yl)methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CN(C=2N=CC=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 WAVFFOAAMPSSLB-UHFFFAOYSA-N 0.000 claims 1
MVONVEBLJNRVQI-UHFFFAOYSA-N cyclohexyl-[2-[(4-quinolin-4-ylpiperazin-1-yl)methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CN(C=2C3=CC=CC=C3N=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 MVONVEBLJNRVQI-UHFFFAOYSA-N 0.000 claims 1
ABODQEKJSXJOFT-UHFFFAOYSA-N cyclohexyl-[2-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound COC1=CC=CC=C1N1CCN(CCC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 ABODQEKJSXJOFT-UHFFFAOYSA-N 0.000 claims 1
VPHGODCMXYLHKW-UHFFFAOYSA-N cyclohexyl-[2-[[2,3-dihydro-1,4-benzodioxin-3-ylmethyl(methyl)amino]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1OC2=CC=CC=C2OC1CN(C)CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 VPHGODCMXYLHKW-UHFFFAOYSA-N 0.000 claims 1
ZEHFQTVKHYOZHB-UHFFFAOYSA-N cyclohexyl-[2-[[2-(1h-indol-4-yloxy)ethyl-methylamino]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C=1C=CC=2NC=CC=2C=1OCCN(C)CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 ZEHFQTVKHYOZHB-UHFFFAOYSA-N 0.000 claims 1
KNYDICIHFGUUEI-UHFFFAOYSA-N cyclohexyl-[2-[[2-(2,4-dimethoxyphenyl)pyrrolidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound COC1=CC(OC)=CC=C1C1N(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CCC1 KNYDICIHFGUUEI-UHFFFAOYSA-N 0.000 claims 1
KYRPPGBOOZTOHL-UHFFFAOYSA-N cyclohexyl-[2-[[2-(4-methoxyphenyl)piperidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=CC(OC)=CC=C1C1N(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CCCC1 KYRPPGBOOZTOHL-UHFFFAOYSA-N 0.000 claims 1
DKDXLEZVGHVTKX-UHFFFAOYSA-N cyclohexyl-[2-[[2-(furan-2-yl)pyrrolidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CCC(C=2OC=CC=2)N1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 DKDXLEZVGHVTKX-UHFFFAOYSA-N 0.000 claims 1
VSEUQEFGRZPKFQ-UHFFFAOYSA-N cyclohexyl-[2-[[2-[(4-fluorophenyl)methyl]piperidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1CC1N(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CCCC1 VSEUQEFGRZPKFQ-UHFFFAOYSA-N 0.000 claims 1
XKKPSRXUFARVBJ-UHFFFAOYSA-N cyclohexyl-[2-[[2-[(4-methoxyphenyl)methyl]piperidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=CC(OC)=CC=C1CC1N(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CCCC1 XKKPSRXUFARVBJ-UHFFFAOYSA-N 0.000 claims 1
KMSLJEHYHFFMCY-UHFFFAOYSA-N cyclohexyl-[2-[[2-[(4-methoxyphenyl)methyl]pyrrolidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=CC(OC)=CC=C1CC1N(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CCC1 KMSLJEHYHFFMCY-UHFFFAOYSA-N 0.000 claims 1
MAVYGECMQDOQBW-UHFFFAOYSA-N cyclohexyl-[2-[[2-[hydroxy(phenyl)methyl]piperidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C=1C=CC=CC=1C(O)C1CCCCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 MAVYGECMQDOQBW-UHFFFAOYSA-N 0.000 claims 1
DNHWTJHITPZSSF-UHFFFAOYSA-N cyclohexyl-[2-[[3-(2-methoxyphenoxy)propylamino]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound COC1=CC=CC=C1OCCCNCC1N(C(=O)C2CCCCC2)C2=CC=CC=C2CC1 DNHWTJHITPZSSF-UHFFFAOYSA-N 0.000 claims 1
LEJPAVYPZRCHLY-UHFFFAOYSA-N cyclohexyl-[2-[[3-(2-methoxyphenyl)propyl-methylamino]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound COC1=CC=CC=C1CCCN(C)CC1N(C(=O)C2CCCCC2)C2=CC=CC=C2CC1 LEJPAVYPZRCHLY-UHFFFAOYSA-N 0.000 claims 1
VUCDXWOELNSHTH-UHFFFAOYSA-N cyclohexyl-[2-[[4-(1-ethylindol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=CC=C2N(CC)C=CC2=C1N(CC1)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 VUCDXWOELNSHTH-UHFFFAOYSA-N 0.000 claims 1
UJNPUSTUAVEPHL-UHFFFAOYSA-N cyclohexyl-[2-[[4-(1-methylindol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=CC=C2N(C)C=CC2=C1N(CC1)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 UJNPUSTUAVEPHL-UHFFFAOYSA-N 0.000 claims 1
LBVBROJVVYVMIR-UHFFFAOYSA-N cyclohexyl-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-6-methoxy-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC(OC)=CC=C2N1C(=O)C1CCCCC1 LBVBROJVVYVMIR-UHFFFAOYSA-N 0.000 claims 1
KRNWUYDPYUFPEA-UHFFFAOYSA-N cyclohexyl-[2-[[4-(2,3-dichlorophenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound ClC1=CC=CC(N2CCN(CC3N(C4=CC=CC=C4CC3)C(=O)C3CCCCC3)CC2)=C1Cl KRNWUYDPYUFPEA-UHFFFAOYSA-N 0.000 claims 1
QZWLKCFVVLVEBM-UHFFFAOYSA-N cyclohexyl-[2-[[4-(2,3-dichlorophenyl)piperidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound ClC1=CC=CC(C2CCN(CC3N(C4=CC=CC=C4CC3)C(=O)C3CCCCC3)CC2)=C1Cl QZWLKCFVVLVEBM-UHFFFAOYSA-N 0.000 claims 1
AJXSVLSZIVRNAW-UHFFFAOYSA-N cyclohexyl-[2-[[4-(2,4-difluorophenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound FC1=CC(F)=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 AJXSVLSZIVRNAW-UHFFFAOYSA-N 0.000 claims 1
AEAGJJPVYBBCOY-UHFFFAOYSA-N cyclohexyl-[2-[[4-(2,4-dimethoxyphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound COC1=CC(OC)=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 AEAGJJPVYBBCOY-UHFFFAOYSA-N 0.000 claims 1
VSUYDGUSRYJGQE-UHFFFAOYSA-N cyclohexyl-[2-[[4-(2,5-difluorophenyl)piperidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound FC1=CC=C(F)C(C2CCN(CC3N(C4=CC=CC=C4CC3)C(=O)C3CCCCC3)CC2)=C1 VSUYDGUSRYJGQE-UHFFFAOYSA-N 0.000 claims 1
UAQJMVGBHDKDSD-UHFFFAOYSA-N cyclohexyl-[2-[[4-(2,5-dimethylphenyl)piperidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound CC1=CC=C(C)C(C2CCN(CC3N(C4=CC=CC=C4CC3)C(=O)C3CCCCC3)CC2)=C1 UAQJMVGBHDKDSD-UHFFFAOYSA-N 0.000 claims 1
IIEOUCMXYTVCJM-UHFFFAOYSA-N cyclohexyl-[2-[[4-(2,6-dichlorophenyl)piperidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound ClC1=CC=CC(Cl)=C1C1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 IIEOUCMXYTVCJM-UHFFFAOYSA-N 0.000 claims 1
TVQOJTUZVYOZCL-UHFFFAOYSA-N cyclohexyl-[2-[[4-(2,6-difluorophenyl)piperidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound FC1=CC=CC(F)=C1C1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 TVQOJTUZVYOZCL-UHFFFAOYSA-N 0.000 claims 1
QQHLRIZXTBCOAC-UHFFFAOYSA-N cyclohexyl-[2-[[4-(2,6-dimethylphenyl)piperidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound CC1=CC=CC(C)=C1C1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 QQHLRIZXTBCOAC-UHFFFAOYSA-N 0.000 claims 1
PPSICNBMTBFXGE-UHFFFAOYSA-N cyclohexyl-[2-[[4-(2-ethylphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound CCC1=CC=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 PPSICNBMTBFXGE-UHFFFAOYSA-N 0.000 claims 1
FMMSRMDPLURDEY-UHFFFAOYSA-N cyclohexyl-[2-[[4-(2-fluorophenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound FC1=CC=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 FMMSRMDPLURDEY-UHFFFAOYSA-N 0.000 claims 1
YDTPIZOUBHPWOI-UHFFFAOYSA-N cyclohexyl-[2-[[4-(2-fluorophenyl)piperidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound FC1=CC=CC=C1C1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 YDTPIZOUBHPWOI-UHFFFAOYSA-N 0.000 claims 1
OIABDHZYMOQJGT-UHFFFAOYSA-N cyclohexyl-[2-[[4-(2-methoxy-4-methylphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound COC1=CC(C)=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 OIABDHZYMOQJGT-UHFFFAOYSA-N 0.000 claims 1
QKZPLDMOROPWBA-UHFFFAOYSA-N cyclohexyl-[2-[[4-(2-methoxyphenoxy)piperidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound COC1=CC=CC=C1OC1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 QKZPLDMOROPWBA-UHFFFAOYSA-N 0.000 claims 1
HRMYFHMLOJOJQT-UHFFFAOYSA-N cyclohexyl-[2-[[4-(2-methoxyphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound COC1=CC=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 HRMYFHMLOJOJQT-UHFFFAOYSA-N 0.000 claims 1
TVUKEZAIPGOPIG-UHFFFAOYSA-N cyclohexyl-[2-[[4-(2-methoxyphenyl)piperidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound COC1=CC=CC=C1C1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 TVUKEZAIPGOPIG-UHFFFAOYSA-N 0.000 claims 1
QPPKHEVPBYMNDI-UHFFFAOYSA-N cyclohexyl-[2-[[4-(2-methylphenyl)piperidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound CC1=CC=CC=C1C1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 QPPKHEVPBYMNDI-UHFFFAOYSA-N 0.000 claims 1
OHZQSBZTXMQJJO-UHFFFAOYSA-N cyclohexyl-[2-[[4-(2-methylquinolin-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C=12C=CC=CC2=NC(C)=CC=1N(CC1)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 OHZQSBZTXMQJJO-UHFFFAOYSA-N 0.000 claims 1
ZXRFWFTWKCASJZ-UHFFFAOYSA-N cyclohexyl-[2-[[4-(2-methylsulfanylphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound CSC1=CC=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 ZXRFWFTWKCASJZ-UHFFFAOYSA-N 0.000 claims 1
BQSKSGHTWVKNQE-UHFFFAOYSA-N cyclohexyl-[2-[[4-(2-nitrophenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound [O-][N+](=O)C1=CC=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 BQSKSGHTWVKNQE-UHFFFAOYSA-N 0.000 claims 1
YZUZBQXQFYFTCW-UHFFFAOYSA-N cyclohexyl-[2-[[4-(3,4-dichlorophenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=C(Cl)C(Cl)=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 YZUZBQXQFYFTCW-UHFFFAOYSA-N 0.000 claims 1
KPRPIBAUWHXGLP-UHFFFAOYSA-N cyclohexyl-[2-[[4-(3,4-dimethoxyphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=C(OC)C(OC)=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 KPRPIBAUWHXGLP-UHFFFAOYSA-N 0.000 claims 1
OCXXSXSHGOLODF-UHFFFAOYSA-N cyclohexyl-[2-[[4-(3,5-dichloropyridin-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound ClC1=CN=CC(Cl)=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 OCXXSXSHGOLODF-UHFFFAOYSA-N 0.000 claims 1
UBZNGFQJFFDGIS-UHFFFAOYSA-N cyclohexyl-[2-[[4-(3,5-difluorophenyl)piperidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound FC1=CC(F)=CC(C2CCN(CC3N(C4=CC=CC=C4CC3)C(=O)C3CCCCC3)CC2)=C1 UBZNGFQJFFDGIS-UHFFFAOYSA-N 0.000 claims 1
MIJDKAJUFSYKEY-UHFFFAOYSA-N cyclohexyl-[2-[[4-(3,5-dimethoxyphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound COC1=CC(OC)=CC(N2CCN(CC3N(C4=CC=CC=C4CC3)C(=O)C3CCCCC3)CC2)=C1 MIJDKAJUFSYKEY-UHFFFAOYSA-N 0.000 claims 1
KUPPTDCYQXTEQM-UHFFFAOYSA-N cyclohexyl-[2-[[4-(3,5-dimethylphenyl)piperidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound CC1=CC(C)=CC(C2CCN(CC3N(C4=CC=CC=C4CC3)C(=O)C3CCCCC3)CC2)=C1 KUPPTDCYQXTEQM-UHFFFAOYSA-N 0.000 claims 1
UTTMYDMZOISCPU-UHFFFAOYSA-N cyclohexyl-[2-[[4-(3-fluoro-2-methylphenyl)piperidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound CC1=C(F)C=CC=C1C1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 UTTMYDMZOISCPU-UHFFFAOYSA-N 0.000 claims 1
DIGUPVXQONRJAK-UHFFFAOYSA-N cyclohexyl-[2-[[4-(3-fluorophenyl)piperidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound FC1=CC=CC(C2CCN(CC3N(C4=CC=CC=C4CC3)C(=O)C3CCCCC3)CC2)=C1 DIGUPVXQONRJAK-UHFFFAOYSA-N 0.000 claims 1
AYHXCBGCAVROIG-UHFFFAOYSA-N cyclohexyl-[2-[[4-(3-hydroxyphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound OC1=CC=CC(N2CCN(CC3N(C4=CC=CC=C4CC3)C(=O)C3CCCCC3)CC2)=C1 AYHXCBGCAVROIG-UHFFFAOYSA-N 0.000 claims 1
CMIRDIOHTJFKSQ-UHFFFAOYSA-N cyclohexyl-[2-[[4-(3-methoxyphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound COC1=CC=CC(N2CCN(CC3N(C4=CC=CC=C4CC3)C(=O)C3CCCCC3)CC2)=C1 CMIRDIOHTJFKSQ-UHFFFAOYSA-N 0.000 claims 1
SWZHTTAYHURKTE-UHFFFAOYSA-N cyclohexyl-[2-[[4-(3-methoxyphenyl)piperidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound COC1=CC=CC(C2CCN(CC3N(C4=CC=CC=C4CC3)C(=O)C3CCCCC3)CC2)=C1 SWZHTTAYHURKTE-UHFFFAOYSA-N 0.000 claims 1
JJUBFTWNVHYEPP-UHFFFAOYSA-N cyclohexyl-[2-[[4-(3-methylphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound CC1=CC=CC(N2CCN(CC3N(C4=CC=CC=C4CC3)C(=O)C3CCCCC3)CC2)=C1 JJUBFTWNVHYEPP-UHFFFAOYSA-N 0.000 claims 1
IUKFFKFYJVTSDL-UHFFFAOYSA-N cyclohexyl-[2-[[4-(3-methylphenyl)piperidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound CC1=CC=CC(C2CCN(CC3N(C4=CC=CC=C4CC3)C(=O)C3CCCCC3)CC2)=C1 IUKFFKFYJVTSDL-UHFFFAOYSA-N 0.000 claims 1
NWFROHITSDKTSQ-UHFFFAOYSA-N cyclohexyl-[2-[[4-(4-fluoro-2-methoxyanilino)piperidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound COC1=CC(F)=CC=C1NC1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 NWFROHITSDKTSQ-UHFFFAOYSA-N 0.000 claims 1
GJSDVWYQKVTJJT-UHFFFAOYSA-N cyclohexyl-[2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-4-methyl-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound COC1=CC(F)=CC=C1N1CCN(CC2N(C3=CC=CC=C3C(C)C2)C(=O)C2CCCCC2)CC1 GJSDVWYQKVTJJT-UHFFFAOYSA-N 0.000 claims 1
VOXIJURPYLSPLA-UHFFFAOYSA-N cyclohexyl-[2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-6-nitro-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound COC1=CC(F)=CC=C1N1CCN(CC2N(C3=CC=C(C=C3CC2)[N+]([O-])=O)C(=O)C2CCCCC2)CC1 VOXIJURPYLSPLA-UHFFFAOYSA-N 0.000 claims 1
ANNRFMBHCUEWGY-UHFFFAOYSA-N cyclohexyl-[2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-7-methyl-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound COC1=CC(F)=CC=C1N1CCN(CC2N(C3=CC(C)=CC=C3CC2)C(=O)C2CCCCC2)CC1 ANNRFMBHCUEWGY-UHFFFAOYSA-N 0.000 claims 1
KFDBVOVGFNSOHG-UHFFFAOYSA-N cyclohexyl-[2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-8-methyl-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound COC1=CC(F)=CC=C1N1CCN(CC2N(C3=C(C)C=CC=C3CC2)C(=O)C2CCCCC2)CC1 KFDBVOVGFNSOHG-UHFFFAOYSA-N 0.000 claims 1
DBURITQTUHEMPT-UHFFFAOYSA-N cyclohexyl-[2-[[4-(4-fluoro-2-nitrophenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound [O-][N+](=O)C1=CC(F)=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 DBURITQTUHEMPT-UHFFFAOYSA-N 0.000 claims 1
IUMNRUCXUIEICF-UHFFFAOYSA-N cyclohexyl-[2-[[4-(4-fluoro-2-propoxyphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound CCCOC1=CC(F)=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 IUMNRUCXUIEICF-UHFFFAOYSA-N 0.000 claims 1
REVHUESMTMONAM-UHFFFAOYSA-N cyclohexyl-[2-[[4-(4-fluorophenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 REVHUESMTMONAM-UHFFFAOYSA-N 0.000 claims 1
QZJPSVBJZXXAEI-UHFFFAOYSA-N cyclohexyl-[2-[[4-(4-fluorophenyl)piperidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 QZJPSVBJZXXAEI-UHFFFAOYSA-N 0.000 claims 1
POCGNGWIPIAVAR-UHFFFAOYSA-N cyclohexyl-[2-[[4-(4-hydroxyphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=CC(O)=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 POCGNGWIPIAVAR-UHFFFAOYSA-N 0.000 claims 1
ICZRXTPYPMSTAY-UHFFFAOYSA-N cyclohexyl-[2-[[4-(4-methoxyphenyl)piperidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=CC(OC)=CC=C1C1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 ICZRXTPYPMSTAY-UHFFFAOYSA-N 0.000 claims 1
MFHDUBYJIPBRHU-UHFFFAOYSA-N cyclohexyl-[2-[[4-(4-methylphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=CC(C)=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 MFHDUBYJIPBRHU-UHFFFAOYSA-N 0.000 claims 1
PGBWPHILMRBIMM-UHFFFAOYSA-N cyclohexyl-[2-[[4-(6-methoxypyridin-2-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound COC1=CC=CC(N2CCN(CC3N(C4=CC=CC=C4CC3)C(=O)C3CCCCC3)CC2)=N1 PGBWPHILMRBIMM-UHFFFAOYSA-N 0.000 claims 1
VDQPWMSPJLNAGX-UHFFFAOYSA-N cyclohexyl-[2-[[4-(6-methylpyridin-2-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound CC1=CC=CC(N2CCN(CC3N(C4=CC=CC=C4CC3)C(=O)C3CCCCC3)CC2)=N1 VDQPWMSPJLNAGX-UHFFFAOYSA-N 0.000 claims 1
KRSDMYZYSKCKQJ-UHFFFAOYSA-N cyclohexyl-[2-[[4-(7-methoxyquinolin-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1N(CC1)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 KRSDMYZYSKCKQJ-UHFFFAOYSA-N 0.000 claims 1
OHXCJTJAQXHJML-UHFFFAOYSA-N cyclohexyl-[2-[[4-(7-methyl-1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=2C=CNC=2C(C)=CC=C1N(CC1)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 OHXCJTJAQXHJML-UHFFFAOYSA-N 0.000 claims 1
JNEJRVMLEOEPQV-UHFFFAOYSA-N cyclohexyl-[2-[[4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound FC(F)(F)COC1=CC=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 JNEJRVMLEOEPQV-UHFFFAOYSA-N 0.000 claims 1
HMLWIFHIVYPRHD-UHFFFAOYSA-N cyclohexyl-[2-[[4-[2-(trifluoromethyl)phenyl]piperidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound FC(F)(F)C1=CC=CC=C1C1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 HMLWIFHIVYPRHD-UHFFFAOYSA-N 0.000 claims 1
LEIZHNCTVFLEAF-UHFFFAOYSA-N cyclohexyl-[2-[[4-[2-(trifluoromethyl)quinolin-4-yl]piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C=12C=CC=CC2=NC(C(F)(F)F)=CC=1N(CC1)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 LEIZHNCTVFLEAF-UHFFFAOYSA-N 0.000 claims 1
SQLDEBUKSDSXSF-UHFFFAOYSA-N cyclohexyl-[2-[[4-[2-methoxy-5-(trifluoromethyl)phenyl]piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound COC1=CC=C(C(F)(F)F)C=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 SQLDEBUKSDSXSF-UHFFFAOYSA-N 0.000 claims 1
CYQSRVFQIYTXKG-UHFFFAOYSA-N cyclohexyl-[2-[[4-[3-(furan-2-yl)-1h-pyrazol-5-yl]piperidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CC(C=2NN=C(C=2)C=2OC=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 CYQSRVFQIYTXKG-UHFFFAOYSA-N 0.000 claims 1
KQEKEHJQUOXFBO-UHFFFAOYSA-N cyclohexyl-[2-[[4-[3-(trifluoromethyl)phenyl]piperidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound FC(F)(F)C1=CC=CC(C2CCN(CC3N(C4=CC=CC=C4CC3)C(=O)C3CCCCC3)CC2)=C1 KQEKEHJQUOXFBO-UHFFFAOYSA-N 0.000 claims 1
VROYHYBKTAPFSS-UHFFFAOYSA-N cyclohexyl-[2-[[4-[3-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound FC(F)(F)C1=CC=CN=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 VROYHYBKTAPFSS-UHFFFAOYSA-N 0.000 claims 1
GFFGFWJXFWSNGF-UHFFFAOYSA-N cyclohexyl-[2-[[4-[4-(trifluoromethyl)phenyl]piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=CC(C(F)(F)F)=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 GFFGFWJXFWSNGF-UHFFFAOYSA-N 0.000 claims 1
VUYNSPDRGQUACK-UHFFFAOYSA-N cyclohexyl-[2-[[4-[4-(trifluoromethyl)phenyl]piperidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=CC(C(F)(F)F)=CC=C1C1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 VUYNSPDRGQUACK-UHFFFAOYSA-N 0.000 claims 1
OHMYOVGJRCOQMR-UHFFFAOYSA-N cyclohexyl-[2-[[4-[5-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound N1=CC(C(F)(F)F)=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 OHMYOVGJRCOQMR-UHFFFAOYSA-N 0.000 claims 1
KQBDFYOWCLWJCA-UHFFFAOYSA-N cyclohexyl-[2-[[methyl(2-pyridin-2-yloxyethyl)amino]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CC2=CC=CC=C2N(C(=O)C2CCCCC2)C1CN(C)CCOC1=CC=CC=N1 KQBDFYOWCLWJCA-UHFFFAOYSA-N 0.000 claims 1
CWVKUZAGSWQCAE-UHFFFAOYSA-N cyclohexyl-[2-[[methyl(3-phenylpropyl)amino]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CC2=CC=CC=C2N(C(=O)C2CCCCC2)C1CN(C)CCCC1=CC=CC=C1 CWVKUZAGSWQCAE-UHFFFAOYSA-N 0.000 claims 1
STRONQVXZYPXDJ-UHFFFAOYSA-N cyclohexyl-[2-[[methyl-[2-[2-(trifluoromethoxy)phenoxy]ethyl]amino]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CC2=CC=CC=C2N(C(=O)C2CCCCC2)C1CN(C)CCOC1=CC=CC=C1OC(F)(F)F STRONQVXZYPXDJ-UHFFFAOYSA-N 0.000 claims 1
IPSJIKLVDJWYTP-UHFFFAOYSA-N cyclohexyl-[6-fluoro-2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC(F)=CC=C2N1C(=O)C1CCCCC1 IPSJIKLVDJWYTP-UHFFFAOYSA-N 0.000 claims 1
MFUZQWWFOZGGEJ-UHFFFAOYSA-N cyclohexyl-[6-fluoro-2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound COC1=CC(F)=CC=C1N1CCN(CC2N(C3=CC=C(F)C=C3CC2)C(=O)C2CCCCC2)CC1 MFUZQWWFOZGGEJ-UHFFFAOYSA-N 0.000 claims 1
ZHMLQNDPEIXZIT-UHFFFAOYSA-N cyclohexyl-[6-fluoro-2-[[4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CC2=CC(F)=CC=C2N(C(=O)C2CCCCC2)C1CN(CC1)CCN1C1=CC=CC=C1OCC(F)(F)F ZHMLQNDPEIXZIT-UHFFFAOYSA-N 0.000 claims 1
KAPJURBWWLESHV-UHFFFAOYSA-N cyclopentyl-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCC1 KAPJURBWWLESHV-UHFFFAOYSA-N 0.000 claims 1
125000004663 dialkyl amino group Chemical group 0.000 claims 1
239000003085 diluting agent Substances 0.000 claims 1
125000004311 dioxin-2-yl group Chemical group [H]C1=C([H])OC(*)=C([H])O1 0.000 claims 1
239000011737 fluorine Substances 0.000 claims 1
229910052731 fluorine Inorganic materials 0.000 claims 1
125000001153 fluoro group Chemical group F* 0.000 claims 1
GOEZBLVEUDTOTA-UHFFFAOYSA-N furan-2-yl-[2-[(4-isoquinolin-1-ylpiperazin-1-yl)methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CN(C=2C3=CC=CC=C3C=CN=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1=CC=CO1 GOEZBLVEUDTOTA-UHFFFAOYSA-N 0.000 claims 1
FGUNBENNZSEBAD-UHFFFAOYSA-N furan-2-yl-[2-[[2-(2-methoxyphenoxy)ethyl-methylamino]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound COC1=CC=CC=C1OCCN(C)CC1N(C(=O)C=2OC=CC=2)C2=CC=CC=C2CC1 FGUNBENNZSEBAD-UHFFFAOYSA-N 0.000 claims 1
125000004438 haloalkoxy group Chemical group 0.000 claims 1
125000001188 haloalkyl group Chemical group 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
239000001257 hydrogen Substances 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
DUINDQXUQUAJLV-UHFFFAOYSA-N n-[1-[[1-(cyclohexanecarbonyl)-3,4-dihydro-2h-quinolin-2-yl]methyl]piperidin-4-yl]benzamide Chemical compound C1CC(NC(=O)C=2C=CC=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 DUINDQXUQUAJLV-UHFFFAOYSA-N 0.000 claims 1
RWNIYTUNTUUFJF-UHFFFAOYSA-N n-benzyl-2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinoline-1-carboxamide Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)NCC1=CC=CC=C1 RWNIYTUNTUUFJF-UHFFFAOYSA-N 0.000 claims 1
TYXLIYGUDAYYOJ-UHFFFAOYSA-N n-ethyl-2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinoline-1-carboxamide Chemical compound C1CC2=CC=CC=C2N(C(=O)NCC)C1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 TYXLIYGUDAYYOJ-UHFFFAOYSA-N 0.000 claims 1
XFGUPIVVBXZDKV-UHFFFAOYSA-N n-tert-butyl-2-[[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinoline-1-carboxamide Chemical compound C1CC2=CC=CC=C2N(C(=O)NC(C)(C)C)C1CN1CCN(C=2C=3OCCOC=3C=CC=2)CC1 XFGUPIVVBXZDKV-UHFFFAOYSA-N 0.000 claims 1
239000001301 oxygen Substances 0.000 claims 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
125000006413 ring segment Chemical group 0.000 claims 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
229910052717 sulfur Inorganic materials 0.000 claims 1
125000004434 sulfur atom Chemical group 0.000 claims 1
ZJCNTVUGLJQUEP-UHFFFAOYSA-N tert-butyl 4-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinoline-1-carbonyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C(=O)N1C2=CC=CC=C2CCC1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 ZJCNTVUGLJQUEP-UHFFFAOYSA-N 0.000 claims 1
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239000012448 Lithium borohydride Substances 0.000 description 1
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
239000007832 Na2SO4 Substances 0.000 description 1
235000019502 Orange oil Nutrition 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
LHKBYTLLCFZTME-UHFFFAOYSA-N [1-(cyclohexanecarbonyl)-2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-8-yl] cyclohexanecarboxylate Chemical compound C1CCCCC1C(=O)OC(C1=2)=CC=CC=2CCC(CN2CCN(CC2)C=2C=3C=CNC=3C=CC=2)N1C(=O)C1CCCCC1 LHKBYTLLCFZTME-UHFFFAOYSA-N 0.000 description 1
XQUGSSGNOSMAQH-UHFFFAOYSA-N [2-(bromomethyl)quinolin-6-yl] tert-butyl carbonate Chemical compound N1=C(CBr)C=CC2=CC(OC(=O)OC(C)(C)C)=CC=C21 XQUGSSGNOSMAQH-UHFFFAOYSA-N 0.000 description 1
PVRAKXNTLGMKEB-UHFFFAOYSA-N [2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-pyrrolidin-1-ylmethanone Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)N1CCCC1 PVRAKXNTLGMKEB-UHFFFAOYSA-N 0.000 description 1
AJFHLFPZBCUMMJ-UHFFFAOYSA-N [4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]-(6-methyl-1,2,3,4-tetrahydroquinolin-2-yl)methanone Chemical compound COC1=CC(F)=CC=C1N1CCN(C(=O)C2NC3=CC=C(C)C=C3CC2)CC1 AJFHLFPZBCUMMJ-UHFFFAOYSA-N 0.000 description 1
JFUZQTIGCHJVIS-UHFFFAOYSA-N [5-chloro-2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)N1C2=CC=CC(Cl)=C2CCC1CN1CCN(C=2C(=CC(F)=CC=2)OC)CC1 JFUZQTIGCHJVIS-UHFFFAOYSA-N 0.000 description 1
HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 1
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
229910000024 caesium carbonate Inorganic materials 0.000 description 1
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
229940125758 compound 15 Drugs 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
CIYPNZYEUZQIHN-UHFFFAOYSA-N cycloheptanecarbonyl chloride Chemical compound ClC(=O)C1CCCCCC1 CIYPNZYEUZQIHN-UHFFFAOYSA-N 0.000 description 1
FDODVZVWGKVMBO-UHFFFAOYSA-N cyclohex-2-ene-1,4-diol Chemical compound OC1CCC(O)C=C1 FDODVZVWGKVMBO-UHFFFAOYSA-N 0.000 description 1
XRFQHOMQNWIABP-UHFFFAOYSA-N cyclohexyl-[2-[[4-(5-fluoro-2-methylphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound CC1=CC=C(F)C=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 XRFQHOMQNWIABP-UHFFFAOYSA-N 0.000 description 1
WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
WVLHGCRWEHCIOT-UHFFFAOYSA-N eltoprazine Chemical compound C1CNCCN1C1=CC=CC2=C1OCCO2 WVLHGCRWEHCIOT-UHFFFAOYSA-N 0.000 description 1
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
QNRXNRGSOJZINA-UHFFFAOYSA-N indoline-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)CC2=C1 QNRXNRGSOJZINA-UHFFFAOYSA-N 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
NIZHERJWXFHGGU-UHFFFAOYSA-N isocyanato(trimethyl)silane Chemical compound C[Si](C)(C)N=C=O NIZHERJWXFHGGU-UHFFFAOYSA-N 0.000 description 1
GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 1
229940040692 lithium hydroxide monohydrate Drugs 0.000 description 1
ACEPYLDNGYGKDY-UHFFFAOYSA-N methyl 1,2,3,4-tetrahydroquinoline-2-carboxylate Chemical compound C1=CC=C2NC(C(=O)OC)CCC2=C1 ACEPYLDNGYGKDY-UHFFFAOYSA-N 0.000 description 1
BBVXYOJRQUMFHG-UHFFFAOYSA-N methyl 1-(cyclohexanecarbonyl)-3,4-dihydro-2h-quinoline-2-carboxylate Chemical compound COC(=O)C1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 BBVXYOJRQUMFHG-UHFFFAOYSA-N 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
239000004533 oil dispersion Substances 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
235000011837 pasties Nutrition 0.000 description 1
XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
XYKIUTSFQGXHOW-UHFFFAOYSA-N propan-2-one;toluene Chemical compound CC(C)=O.CC1=CC=CC=C1 XYKIUTSFQGXHOW-UHFFFAOYSA-N 0.000 description 1
BHGCGZJIGFPIDE-UHFFFAOYSA-N pyrrolidine-3-carbonyl chloride Chemical compound ClC(=O)C1CCNC1 BHGCGZJIGFPIDE-UHFFFAOYSA-N 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
XCBMLCCTGRTOJS-UHFFFAOYSA-N tert-butyl (2-methylquinolin-6-yl) carbonate Chemical compound C1=C(OC(=O)OC(C)(C)C)C=CC2=NC(C)=CC=C21 XCBMLCCTGRTOJS-UHFFFAOYSA-N 0.000 description 1
OEAMZRWFIQSVJQ-UHFFFAOYSA-N tert-butyl 4-(1h-indol-4-yl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=CC=CC2=C1C=CN2 OEAMZRWFIQSVJQ-UHFFFAOYSA-N 0.000 description 1
CTZQQLPXRKSALV-UHFFFAOYSA-N tert-butyl 4-(7-bromo-1h-indol-4-yl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=CC=C(Br)C2=C1C=CN2 CTZQQLPXRKSALV-UHFFFAOYSA-N 0.000 description 1
XKKDWSQNSJBRSR-UHFFFAOYSA-N tert-butyl [1-(cyclohexanecarbonyl)-2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-6-yl] carbonate Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC(OC(=O)OC(C)(C)C)=CC=C2N1C(=O)C1CCCCC1 XKKDWSQNSJBRSR-UHFFFAOYSA-N 0.000 description 1
AXWVSDWJZLQYJI-UHFFFAOYSA-N tert-butyl [2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-1,2,3,4-tetrahydroquinolin-6-yl] carbonate Chemical compound C1CC2=CC(OC(=O)OC(C)(C)C)=CC=C2NC1CN(CC1)CCN1C1=CC=CC2=C1C=CN2 AXWVSDWJZLQYJI-UHFFFAOYSA-N 0.000 description 1
UKXFNMRZVJTBBP-UHFFFAOYSA-N tert-butyl [2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]quinolin-6-yl] carbonate Chemical compound C1=CC2=CC(OC(=O)OC(C)(C)C)=CC=C2N=C1CN(CC1)CCN1C1=CC=CC2=C1C=CN2 UKXFNMRZVJTBBP-UHFFFAOYSA-N 0.000 description 1
UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1

JP2003534419A 2001-10-05 2002-10-07 尿路障害の処置における使用のためのヘテロ環式化合物 Withdrawn JP2005508952A (ja)