ZA200403356B - Heterocyclic compounds for use in the treatment of disorders of the urinary tract. - Google Patents
Heterocyclic compounds for use in the treatment of disorders of the urinary tract. Download PDFInfo
- Publication number
- ZA200403356B ZA200403356B ZA200403356A ZA200403356A ZA200403356B ZA 200403356 B ZA200403356 B ZA 200403356B ZA 200403356 A ZA200403356 A ZA 200403356A ZA 200403356 A ZA200403356 A ZA 200403356A ZA 200403356 B ZA200403356 B ZA 200403356B
- Authority
- ZA
- South Africa
- Prior art keywords
- piperazine
- ylmethyl
- tetrahydroquinoline
- cyclohexanecarbonyl
- tetrahydroquinolin
- Prior art date
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- 238000011282 treatment Methods 0.000 title description 23
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title description 15
- 208000035475 disorder Diseases 0.000 title description 14
- 210000001635 urinary tract Anatomy 0.000 title description 7
- 150000002391 heterocyclic compounds Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 996
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 228
- -1 nitro, phenyl Chemical group 0.000 claims description 85
- 239000000203 mixture Substances 0.000 claims description 57
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 125000002950 monocyclic group Chemical group 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- LBUJPTNKIBCYBY-UHFFFAOYSA-N tetrahydroquinoline Natural products C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 125000001041 indolyl group Chemical group 0.000 claims description 7
- 150000001204 N-oxides Chemical class 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 5
- 125000001769 aryl amino group Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000002619 bicyclic group Chemical group 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000006413 ring segment Chemical group 0.000 claims description 5
- 239000012453 solvate Substances 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 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 description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 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
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 3
- 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 description 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 3
- 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 description 2
- 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 description 2
- ZXMJUIFVZZCTKB-UHFFFAOYSA-N 1-[2-[[2-(2-methoxyphenoxy)ethyl-methylamino]methyl]-3,4-dihydro-2h-quinolin-1-yl]-2-thiophen-3-ylethanone Chemical compound COC1=CC=CC=C1OCCN(C)CC1N(C(=O)CC2=CSC=C2)C2=CC=CC=C2CC1 ZXMJUIFVZZCTKB-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- PMZBLWQRCHWEID-UHFFFAOYSA-N 1-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-2-methylpropan-1-one Chemical compound C1CC2=CC=CC=C2N(C(=O)C(C)C)C1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 PMZBLWQRCHWEID-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 2
- 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 description 2
- VLGOCCUGRXACJL-UHFFFAOYSA-N 2-cyclohexyl-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)CC1CCCCC1 VLGOCCUGRXACJL-UHFFFAOYSA-N 0.000 claims description 2
- XWUJRYWKNAAWSD-UHFFFAOYSA-N 2-ethyl-1-[2-[[4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]butan-1-one Chemical compound C1CC2=CC=CC=C2N(C(=O)C(CC)CC)C1CN(CC1)CCN1C1=CC=CC=C1OCC(F)(F)F XWUJRYWKNAAWSD-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
- HJUULWUBMMDLCJ-UHFFFAOYSA-N 4-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinoline-1-carbonyl]-n,n,5-trimethylfuran-2-sulfonamide Chemical compound O1C(S(=O)(=O)N(C)C)=CC(C(=O)N2C3=CC=CC=C3CCC2CN2CCN(CC2)C=2C=3C=CNC=3C=CC=2)=C1C HJUULWUBMMDLCJ-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- ZFQCXKHKPJXQCC-UHFFFAOYSA-N [2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-(2-methoxyphenyl)methanone Chemical compound COC1=CC=CC=C1C(=O)N1C2=CC=CC=C2CCC1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 ZFQCXKHKPJXQCC-UHFFFAOYSA-N 0.000 claims description 2
- WWNCYTOECGVWJD-UHFFFAOYSA-N [2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-(2-methyl-5-morpholin-4-ylsulfonylfuran-3-yl)methanone Chemical compound C=1C(C(=O)N2C3=CC=CC=C3CCC2CN2CCN(CC2)C=2C=3C=CNC=3C=CC=2)=C(C)OC=1S(=O)(=O)N1CCOCC1 WWNCYTOECGVWJD-UHFFFAOYSA-N 0.000 claims description 2
- XJDGHHURXRNPDV-UHFFFAOYSA-N [2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-[1-(4-methylphenyl)sulfonylpyrrol-3-yl]methanone Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C=C(C(=O)N2C3=CC=CC=C3CCC2CN2CCN(CC2)C=2C=3C=CNC=3C=CC=2)C=C1 XJDGHHURXRNPDV-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- FZXRMONPASOMSI-UHFFFAOYSA-N [2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-thiophen-3-ylmethanone Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C=1C=CSC=1 FZXRMONPASOMSI-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 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 description 2
- 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 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
- 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 description 2
- 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 description 2
- 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 description 2
- HLCIEUWICBLQAK-UHFFFAOYSA-N cyclohexyl-[2-[[2-(1h-indol-2-yl)pyrrolidin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CCC(C=2NC3=CC=CC=C3C=2)N1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 HLCIEUWICBLQAK-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 claims description 2
- 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 description 2
- YMRUZFBSYZXYMR-UHFFFAOYSA-N cyclohexyl-[2-[[4-[1-(methoxymethyl)indol-4-yl]piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=CC=C2N(COC)C=CC2=C1N(CC1)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 YMRUZFBSYZXYMR-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- IHHGVNZMPNXAST-UHFFFAOYSA-N cyclohexyl-[2-[[methyl(2-quinolin-8-yloxyethyl)amino]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C=1C=CC2=CC=CN=C2C=1OCCN(C)CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 IHHGVNZMPNXAST-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 2
- 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 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 5
- 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
- DTAJNSDFOIIXBN-UHFFFAOYSA-N 1-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-2-phenylethanone Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)CC1=CC=CC=C1 DTAJNSDFOIIXBN-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
- 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
- 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
- JHNWOYXWWFWMPA-UHFFFAOYSA-N 1-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-3-phenylpropan-1-one Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)CCC1=CC=CC=C1 JHNWOYXWWFWMPA-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
- 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
- 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
- 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
- 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
- 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 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
- 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
- QKEZGNBWOGWPPY-UHFFFAOYSA-N 4-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinoline-1-carbonyl]benzonitrile Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1=CC=C(C#N)C=C1 QKEZGNBWOGWPPY-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-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
- UXJVQKGQTSSNFK-UHFFFAOYSA-N [2-[(4-benzyl-4-hydroxypiperidin-1-yl)methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound C1CN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CCC1(O)CC1=CC=CC=C1 UXJVQKGQTSSNFK-UHFFFAOYSA-N 0.000 claims 1
- 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
- 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
- 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
- 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
- GPFPQMPEUHXRRD-UHFFFAOYSA-N [2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-(1h-pyrrol-2-yl)methanone Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1=CC=CN1 GPFPQMPEUHXRRD-UHFFFAOYSA-N 0.000 claims 1
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- 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
- 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
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- YCMHBDXEBFFBOL-UHFFFAOYSA-N cyclohexyl-[2-[[4-(1-propan-2-ylindol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=CC=C2N(C(C)C)C=CC2=C1N(CC1)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 YCMHBDXEBFFBOL-UHFFFAOYSA-N 0.000 claims 1
- 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 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
- 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 1
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- 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
- 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
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- 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 1
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- WPYJKGWLDJECQD-UHFFFAOYSA-N quinoline-2-carbaldehyde Chemical compound C1=CC=CC2=NC(C=O)=CC=C21 WPYJKGWLDJECQD-UHFFFAOYSA-N 0.000 description 1
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
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- 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
- YRZGMTHQPGNLEK-UHFFFAOYSA-N tetradecyl propionate Chemical compound CCCCCCCCCCCCCCOC(=O)CC YRZGMTHQPGNLEK-UHFFFAOYSA-N 0.000 description 1
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- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/18—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/40—Nitrogen atoms attached in position 8
-
- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/08—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing alicyclic rings
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- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/08—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing alicyclic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Urology & Nephrology (AREA)
- Psychiatry (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Addiction (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Quinoline Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
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| IT2001MI002060A ITMI20012060A1 (it) | 2001-10-05 | 2001-10-05 | Nuovi eterocilcli n-acilati |
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| AR035521A1 (es) * | 2000-12-22 | 2004-06-02 | Lundbeck & Co As H | Derivados de 3-indolina y composicion farmaceutica que los comprende |
| AU2002322539B2 (en) | 2001-07-20 | 2007-09-27 | Psychogenics Inc. | Treatment for attention-deficit hyperactivity disorder |
| ITMI20012060A1 (it) * | 2001-10-05 | 2003-04-05 | Recordati Chem Pharm | Nuovi eterocilcli n-acilati |
| US20040058962A1 (en) * | 2002-06-14 | 2004-03-25 | Amedeo Leonardi | Phenylalkylamines and pyridylalkylamines |
| US20040215284A1 (en) * | 2003-01-30 | 2004-10-28 | Recordati S.A. | Treatment of neuromuscular dysfunction of the lower urinary tract with selective mGlu5 antagonists |
| UY28538A1 (es) * | 2003-09-26 | 2005-04-29 | Vertex Pharma | Derivados de fenil-piperazina como moduladores de receptores muscarínicos |
| RU2006124559A (ru) * | 2003-12-09 | 2008-01-20 | Вертекс Фармасьютикалз Инкорпорейтед (Us) | Производные нафтиридина и применение указанных производныхых в качестве модуляторов мускариновых рецепторов |
| US20050165025A1 (en) * | 2004-01-22 | 2005-07-28 | Recordati Ireland Ltd. | Combination therapy with 5HT 1A and 5HT 1B-receptor antagonists |
| US7553967B2 (en) * | 2004-03-12 | 2009-06-30 | Wyeth | 1,2-Dihydroquinoline derivatives and method for using the same to treat HIV infections |
| US7534796B2 (en) | 2005-02-18 | 2009-05-19 | Wyeth | Imidazo[4,5-b]pyridine antagonists of gonadotropin releasing hormone receptor |
| US7538113B2 (en) | 2005-02-18 | 2009-05-26 | Wyeth | 4-substituted imidazo[4,5-c]pyridine antagonists of gonadotropin releasing hormone receptor |
| US7582634B2 (en) | 2005-02-18 | 2009-09-01 | Wyeth | 7-substituted imidazo[4,5-c]pyridine antagonists of gonadotropin releasing hormone receptor |
| US7531542B2 (en) | 2005-05-18 | 2009-05-12 | Wyeth | Benzooxazole and benzothiazole antagonists of gonadotropin releasing hormone receptor |
| US7582636B2 (en) | 2005-05-26 | 2009-09-01 | Wyeth | Piperazinylimidazopyridine and piperazinyltriazolopyridine antagonists of Gonadotropin Releasing Hormone receptor |
| DE102005027168A1 (de) * | 2005-06-13 | 2006-12-14 | Merck Patent Gmbh | Tetrahydrochinoline |
| CA2651817A1 (en) | 2006-05-11 | 2007-11-22 | Janssen Pharmaceutica N.V. | 3,4-dihydro-2h-benzo[1,4]oxazine and thiazine derivatives as cetp inhibitors |
| WO2008079427A1 (en) | 2006-05-11 | 2008-07-03 | Janssen Pharmaceutica N.V. | 1,2,3,4-tetrahydro-quinoline derivatives as cetp inhibitors |
| TW200811170A (en) | 2006-06-27 | 2008-03-01 | Sanofi Aventis | Urea derivatives of tropane, their preparation and their therapeutic application |
| PE20080212A1 (es) * | 2006-06-27 | 2008-04-25 | Sanofi Aventis | Derivados de ureas de piperidina o pirrolidina como moduladores de la 11b-hidroxiesteroide deshidrogenasa tipo 1 (11bhsd1) |
| FR2902790A1 (fr) * | 2006-06-27 | 2007-12-28 | Sanofi Aventis Sa | Derives d'urees de piperidine ou pyrrolidine,leur preparation et leur application en therapeutique |
| WO2008011072A2 (en) | 2006-07-19 | 2008-01-24 | Osurf (Ohio State University Research Foundation) | Selective androgen receptor modulators, analogs and derivatives thereof and uses thereof |
| KR20090018593A (ko) * | 2007-08-17 | 2009-02-20 | 주식회사 엘지생명과학 | 세포괴사 저해제로서의 인돌 및 인다졸 화합물 |
| US8354538B2 (en) * | 2008-04-24 | 2013-01-15 | The Regents Of The University Of California | Small-molecule inhibitors of the androgen receptor |
| FR2969151B1 (fr) | 2010-12-17 | 2016-11-04 | Oreal | Derives du 4-amino et leur utilisation pour la coloration d'oxydation des fibres keratiniques. |
| CN105705501B (zh) * | 2013-09-09 | 2019-04-19 | 百时美施贵宝公司 | RORγ调节剂 |
| CN105555768B (zh) * | 2013-09-20 | 2018-10-16 | 百时美施贵宝公司 | RORγ调节剂 |
| AR107032A1 (es) * | 2015-12-09 | 2018-03-14 | Padlock Therapeutics Inc | Inhibidores bicíclicos de pad4 |
| CN108299397B (zh) * | 2018-03-21 | 2019-01-29 | 佳木斯大学附属第一医院 | 一种用于降血压的活性药物及其制备方法 |
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| US4011324A (en) * | 1976-01-20 | 1977-03-08 | Pfizer Inc. | Esters and amides of pyrimido[4,5-b]quinolin-4(3H)-one-2-carboxylic acids as antiulcer agents |
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| US4585773A (en) * | 1984-07-11 | 1986-04-29 | Bristol-Myers Company | Isoindolinyl-alkyl-piperazines |
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| FR2729144A1 (fr) * | 1995-01-06 | 1996-07-12 | Smithkline Beecham Lab | Nouvelles diamines, leur procede de preparation et leur utilisation en tant que medicaments et notamment en tant qu' agents anti-arythmiques |
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| ITMI20012060A1 (it) * | 2001-10-05 | 2003-04-05 | Recordati Chem Pharm | Nuovi eterocilcli n-acilati |
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- 2002-10-07 JP JP2003534419A patent/JP2005508952A/ja not_active Withdrawn
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- 2002-10-07 AT AT02782863T patent/ATE313540T1/de not_active IP Right Cessation
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