HRP20040392A2 - 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
- HRP20040392A2 HRP20040392A2 HR20040392A HRP20040392A HRP20040392A2 HR P20040392 A2 HRP20040392 A2 HR P20040392A2 HR 20040392 A HR20040392 A HR 20040392A HR P20040392 A HRP20040392 A HR P20040392A HR P20040392 A2 HRP20040392 A2 HR P20040392A2
- Authority
- HR
- Croatia
- Prior art keywords
- ylmethyl
- tetrahydroquinolin
- piperazine
- cyclohexanecarbonyl
- indolyl
- Prior art date
Links
- 238000011282 treatment Methods 0.000 title description 24
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title description 14
- 208000035475 disorder Diseases 0.000 title description 13
- 210000001635 urinary tract Anatomy 0.000 title description 6
- 150000002391 heterocyclic compounds Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 993
- -1 nitro, phenyl Chemical group 0.000 claims description 105
- 239000000203 mixture Substances 0.000 claims description 57
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 239000007787 solid Substances 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 125000002950 monocyclic group Chemical group 0.000 claims description 12
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 11
- 150000003839 salts Chemical class 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
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
- 150000001204 N-oxides Chemical class 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
- 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
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 239000012453 solvate Substances 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 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 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 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
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000002619 bicyclic 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
- 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 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- 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 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
- 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
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 3
- 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 3
- 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 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
- 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 description 3
- QPTNXKLYBYRNKB-UHFFFAOYSA-N cyclohexyl-[2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-2-methyl-3,4-dihydroquinolin-1-yl]methanone Chemical compound COC1=CC(F)=CC=C1N1CCN(CC2(C)N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 QPTNXKLYBYRNKB-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
- 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 description 3
- 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 3
- 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 3
- KFHJWOGSFBPDAZ-UHFFFAOYSA-N cyclohexyl-[5-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=CC(F)=C3CC2)C(=O)C2CCCCC2)CC1 KFHJWOGSFBPDAZ-UHFFFAOYSA-N 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
- 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 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
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 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
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- GYCUGTPELZXXHN-UHFFFAOYSA-N tert-butyl n-[1-(cyclohexanecarbonyl)-2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-6-yl]carbamate Chemical compound COC1=CC(F)=CC=C1N1CCN(CC2N(C3=CC=C(NC(=O)OC(C)(C)C)C=C3CC2)C(=O)C2CCCCC2)CC1 GYCUGTPELZXXHN-UHFFFAOYSA-N 0.000 claims description 3
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 3
- UWAVCANSRUIIEF-UHFFFAOYSA-N (2,6-difluorophenyl)-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound FC1=CC=CC(F)=C1C(=O)N1C2=CC=CC=C2CCC1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 UWAVCANSRUIIEF-UHFFFAOYSA-N 0.000 claims description 2
- PRKNDYOVWMMJJC-UHFFFAOYSA-N (3,5-dimethyl-1,2-oxazol-4-yl)-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound CC1=NOC(C)=C1C(=O)N1C2=CC=CC=C2CCC1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 PRKNDYOVWMMJJC-UHFFFAOYSA-N 0.000 claims description 2
- XTAUXGBMFAKINJ-UHFFFAOYSA-N (3-chlorophenyl)-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound ClC1=CC=CC(C(=O)N2C3=CC=CC=C3CCC2CN2CCN(CC2)C=2C=3C=CNC=3C=CC=2)=C1 XTAUXGBMFAKINJ-UHFFFAOYSA-N 0.000 claims description 2
- SYRMPIMATRZNDB-UHFFFAOYSA-N (4-chlorophenyl)-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)N1C2=CC=CC=C2CCC1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 SYRMPIMATRZNDB-UHFFFAOYSA-N 0.000 claims description 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 description 2
- 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 description 2
- IDIDGKSREBWEFX-UHFFFAOYSA-N 1,3-benzodioxol-5-yl-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=C2OCOC2=CC(C(N2C3=CC=CC=C3CCC2CN2CCN(CC2)C=2C=3C=CNC=3C=CC=2)=O)=C1 IDIDGKSREBWEFX-UHFFFAOYSA-N 0.000 claims description 2
- YQLROUAWIKGFHF-UHFFFAOYSA-N 1,3-benzodioxol-5-yl-[2-[[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=C2OCOC2=CC(C(N2C3=CC=CC=C3CCC2CN2CCN(CC2)C=2C=3OCCOC=3C=CC=2)=O)=C1 YQLROUAWIKGFHF-UHFFFAOYSA-N 0.000 claims description 2
- 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
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- UKGURBGWTBNFGT-UHFFFAOYSA-N 1-[2-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-2-oxoethyl]pyrrolidin-2-one Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)CN1CCCC1=O UKGURBGWTBNFGT-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
- HMGQDKMHRKUQLI-UHFFFAOYSA-N 1-[2-[[2-(2-methoxyphenoxy)ethyl-methylamino]methyl]-3,4-dihydro-2h-quinolin-1-yl]-4-phenoxybutan-1-one Chemical compound COC1=CC=CC=C1OCCN(C)CC1N(C(=O)CCCOC=2C=CC=CC=2)C2=CC=CC=C2CC1 HMGQDKMHRKUQLI-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- OMLRRPMKXIGYNN-UHFFFAOYSA-N 1-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-2-(2-methoxyphenyl)ethanone Chemical compound COC1=CC=CC=C1CC(=O)N1C2=CC=CC=C2CCC1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 OMLRRPMKXIGYNN-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
- KCHCOSIXRFUHGL-UHFFFAOYSA-N 1-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-2-methoxyethanone Chemical compound C1CC2=CC=CC=C2N(C(=O)COC)C1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 KCHCOSIXRFUHGL-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
- 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 description 2
- 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 description 2
- 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 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
- 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 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
- 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 description 2
- 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 description 2
- 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
- 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 description 2
- ZUMMTAFBVBJAFX-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-dimethylbutan-1-one Chemical compound C1CC2=CC=CC=C2N(C(=O)C(C)(C)CC)C1CN1CCN(C=2C=3OCCOC=3C=CC=2)CC1 ZUMMTAFBVBJAFX-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 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
- 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 description 2
- MASJVUZEAZHVHQ-UHFFFAOYSA-N 1-[2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-4-phenoxybutan-1-one Chemical compound COC1=CC(F)=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)CCCOC=2C=CC=CC=2)CC1 MASJVUZEAZHVHQ-UHFFFAOYSA-N 0.000 claims description 2
- HOVRKHMNYJHYFM-UHFFFAOYSA-N 1-[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]-4,4-dimethyl-1-(1,2,3,4-tetrahydroquinolin-2-yl)pentan-2-one Chemical compound COC1=CC(F)=CC=C1N1CCN(C(C2NC3=CC=CC=C3CC2)C(=O)CC(C)(C)C)CC1 HOVRKHMNYJHYFM-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- DHDXHLPNQUUWSW-UHFFFAOYSA-N 1-[4-[2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinoline-1-carbonyl]piperidin-1-yl]ethanone Chemical compound COC1=CC(F)=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCN(CC2)C(C)=O)CC1 DHDXHLPNQUUWSW-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
- 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 description 2
- KOABHJPVNFWDGF-UHFFFAOYSA-N 1-[5-[2-[[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinoline-1-carbonyl]-1h-pyrrol-3-yl]ethanone Chemical compound CC(=O)C1=CNC(C(=O)N2C3=CC=CC=C3CCC2CN2CCN(CC2)C=2C=3OCCOC=3C=CC=2)=C1 KOABHJPVNFWDGF-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- GIAROKICRMPTEE-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]ethanone Chemical compound C1=CC(Cl)=CC=C1CC(=O)N1C2=CC=CC=C2CCC1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 GIAROKICRMPTEE-UHFFFAOYSA-N 0.000 claims description 2
- ZAHDHZXAMGXFAA-UHFFFAOYSA-N 2-(4-fluorophenyl)-1-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]ethanone Chemical compound C1=CC(F)=CC=C1CC(=O)N1C2=CC=CC=C2CCC1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 ZAHDHZXAMGXFAA-UHFFFAOYSA-N 0.000 claims description 2
- 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 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
- 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 description 2
- KQPAJGZVMQGKPY-UHFFFAOYSA-N 2-[[2-(2-methoxyphenoxy)ethyl-methylamino]methyl]-n-(2-methylphenyl)-3,4-dihydro-2h-quinoline-1-carboxamide Chemical compound COC1=CC=CC=C1OCCN(C)CC1N(C(=O)NC=2C(=CC=CC=2)C)C2=CC=CC=C2CC1 KQPAJGZVMQGKPY-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- IZDHCZAZHOHZMH-UHFFFAOYSA-N 2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-n-propan-2-yl-3,4-dihydro-2h-quinoline-1-carboxamide Chemical compound C1CC2=CC=CC=C2N(C(=O)NC(C)C)C1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 IZDHCZAZHOHZMH-UHFFFAOYSA-N 0.000 claims description 2
- DTLXLALYDZQUEI-UHFFFAOYSA-N 2-[[4-(2,3-dihydro-1,4-benzodioxin-5-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=3OCCOC=3C=CC=2)CC1 DTLXLALYDZQUEI-UHFFFAOYSA-N 0.000 claims description 2
- 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 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
- 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 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
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 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
- 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 description 2
- WXTVWGCSHKBFDY-UHFFFAOYSA-N 3-bicyclo[2.2.2]octanyl-[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)C1C(CC2)CCC2C1 WXTVWGCSHKBFDY-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 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
- 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 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
- 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 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 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
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- JKMKIOWBBXYBNK-UHFFFAOYSA-N [2-[4-[[1-(cyclohexanecarbonyl)-3,4-dihydro-2H-quinolin-2-yl]methyl]piperazin-1-yl]phenyl] trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)OC1=C(C=CC=C1)N1CCN(CC2CCC3=CC=CC=C3N2C(=O)C2CCCCC2)CC1 JKMKIOWBBXYBNK-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 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
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 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
- LVSUQJYWMJQNBK-UHFFFAOYSA-N [2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-(2-methyl-5-piperidin-1-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)N1CCCCC1 LVSUQJYWMJQNBK-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- PUXUHFWVQDGQFQ-UHFFFAOYSA-N [2-[[4-(1h-indol-4-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=3C=CNC=3C=CC=2)CC1 PUXUHFWVQDGQFQ-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- NGGIVBYMKQZTJZ-UHFFFAOYSA-N [2-[[4-(1h-indol-4-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=3C=CNC=3C=CC=2)=C1C NGGIVBYMKQZTJZ-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 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
- POQWOGOCZUUPGX-UHFFFAOYSA-N [2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(F)(F)C1=CC=CC(C(=O)N2C3=CC=CC=C3CCC2CN2CCN(CC2)C=2C=3C=CNC=3C=CC=2)=C1 POQWOGOCZUUPGX-UHFFFAOYSA-N 0.000 claims description 2
- UYMLTWRKNHGXGF-UHFFFAOYSA-N [2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)N1C2=CC=CC=C2CCC1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 UYMLTWRKNHGXGF-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- OVLJFONYQAKLGU-UHFFFAOYSA-N [2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-pyridin-2-ylmethanone Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1=CC=CC=N1 OVLJFONYQAKLGU-UHFFFAOYSA-N 0.000 claims description 2
- 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 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
- 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 description 2
- 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 description 2
- FILQRFSCRGJKGS-UHFFFAOYSA-N [2-[[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1C2=CC=CC=C2CCC1CN1CCN(C=2C=3OCCOC=3C=CC=2)CC1 FILQRFSCRGJKGS-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- JKPHBJWKDLAINW-UHFFFAOYSA-N [2-[[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-[1-(trifluoromethyl)cyclopropyl]methanone Chemical compound C1CN(C=2C=3OCCOC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1(C(F)(F)F)CC1 JKPHBJWKDLAINW-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
- 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
- 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 description 2
- 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 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
- 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 description 2
- 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 description 2
- 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 description 2
- 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 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
- 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 description 2
- 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 description 2
- 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 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
- 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
- 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 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
- 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 description 2
- 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 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
- YREKISHFUKGZSF-UHFFFAOYSA-N [4-(dimethylamino)phenyl]-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)N1C2=CC=CC=C2CCC1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 YREKISHFUKGZSF-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 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 description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- NWLMWGVBBFUBGW-UHFFFAOYSA-N cyclobutyl-[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)C2CCC2)C2=CC=CC=C2CC1 NWLMWGVBBFUBGW-UHFFFAOYSA-N 0.000 claims description 2
- LHWFXECDLKBVQB-UHFFFAOYSA-N cyclobutyl-[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)C2CCC2)CC1 LHWFXECDLKBVQB-UHFFFAOYSA-N 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
- 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 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
- 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 description 2
- 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 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
- 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 description 2
- 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 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
- 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
- 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 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
- 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
- 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
- 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
- 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
- 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 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
- 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 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
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- URCRAZMQNZVMNG-UHFFFAOYSA-N cyclohexyl-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-6-methyl-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC(C)=CC=C2N1C(=O)C1CCCCC1 URCRAZMQNZVMNG-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
- 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
- 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
- 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
- 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 description 2
- 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 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
- 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
- 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 description 2
- 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 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
- 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 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
- 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 description 2
- 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 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
- 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
- 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
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 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
- 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
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 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
- 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 description 2
- 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 description 2
- 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 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
- 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 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
- 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 description 2
- 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 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
- 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
- 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
- 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 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
- 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
- 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
- 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
- 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 description 2
- 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 description 2
- JLTRBRRNHRJSKZ-UHFFFAOYSA-N cyclohexyl-[2-[[4-[2-nitro-4-(trifluoromethyl)phenyl]piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C2CCCCC2)CC1 JLTRBRRNHRJSKZ-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 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
- 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 description 2
- 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 description 2
- 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 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
- 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 description 2
- 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 description 2
- BAAYRXIREUFEQB-UHFFFAOYSA-N cyclohexyl-[6-(3,5-dimethyl-1,2-oxazol-4-yl)-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(C=C3CC2)C2=C(ON=C2C)C)C(=O)C2CCCCC2)CC1 BAAYRXIREUFEQB-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 description 2
- UJZNOSYNGRKJQY-UHFFFAOYSA-N cyclopentyl-[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)C1CCCC1 UJZNOSYNGRKJQY-UHFFFAOYSA-N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 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 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
- ZDZATLMSOZGVCN-UHFFFAOYSA-N n-[(1-benzylsulfonyl-3,4-dihydro-2h-quinolin-2-yl)methyl]-2-(2-methoxyphenoxy)-n-methylethanamine Chemical compound COC1=CC=CC=C1OCCN(C)CC1N(S(=O)(=O)CC=2C=CC=CC=2)C2=CC=CC=C2CC1 ZDZATLMSOZGVCN-UHFFFAOYSA-N 0.000 claims description 2
- 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 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
- 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 description 2
- 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 description 2
- STHKQUBDFBXFSM-UHFFFAOYSA-N n-tert-butyl-2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinoline-1-carboxamide Chemical compound COC1=CC(F)=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)NC(C)(C)C)CC1 STHKQUBDFBXFSM-UHFFFAOYSA-N 0.000 claims description 2
- 125000006413 ring segment Chemical group 0.000 claims description 2
- 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 description 2
- VDCLSGIQVFXWOZ-UHFFFAOYSA-N 1-(benzenesulfonyl)-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)C1=CC=CC=C1 VDCLSGIQVFXWOZ-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
- 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
- OTWPFXXSIBPIOM-UHFFFAOYSA-N 1-[4-[2-[[4-(2,3-dihydro-1,4-benzodioxin-5-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=3OCCOC=3C=CC=2)CC1 OTWPFXXSIBPIOM-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
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 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
- 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
- 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
- ZVGZCLSOJIMTPX-UHFFFAOYSA-N 2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-n-phenyl-3,4-dihydro-2h-quinoline-1-carboxamide Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)NC1=CC=CC=C1 ZVGZCLSOJIMTPX-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
- 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 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
- 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
- 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
- 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 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
- 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
- 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
- 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
- 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 1
- 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 1
- 125000001309 chloro group Chemical group Cl* 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
- 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 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
- 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 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
- 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 1
- HOIJYSMNPDDDRZ-UHFFFAOYSA-N cyclopropyl-[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)C1CC1 HOIJYSMNPDDDRZ-UHFFFAOYSA-N 0.000 claims 1
- WEYVCQFUGFRXOM-UHFFFAOYSA-N perazine Chemical compound C1CN(C)CCN1CCCN1C2=CC=CC=C2SC2=CC=CC=C21 WEYVCQFUGFRXOM-UHFFFAOYSA-N 0.000 claims 1
- 229960002195 perazine Drugs 0.000 claims 1
- ZJHNYROARADXIL-UHFFFAOYSA-N tert-butyl n-[3-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-3-oxopropyl]carbamate Chemical compound C1CC2=CC=CC=C2N(C(=O)CCNC(=O)OC(C)(C)C)C1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 ZJHNYROARADXIL-UHFFFAOYSA-N 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 282
- 238000003818 flash chromatography Methods 0.000 description 237
- 238000000034 method Methods 0.000 description 210
- 239000003208 petroleum Substances 0.000 description 177
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 162
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 157
- 239000012043 crude product Substances 0.000 description 117
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 99
- 239000000243 solution Substances 0.000 description 84
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 70
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 64
- 238000005917 acylation reaction Methods 0.000 description 61
- 230000010933 acylation Effects 0.000 description 60
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 52
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 description 48
- FUMGIQVAPCXQQN-UHFFFAOYSA-N 2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-1,2,3,4-tetrahydroquinoline Chemical compound C1CC2=CC=CC=C2NC1CN(CC1)CCN1C1=CC=CC2=C1C=CN2 FUMGIQVAPCXQQN-UHFFFAOYSA-N 0.000 description 47
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 210000003932 urinary bladder Anatomy 0.000 description 38
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 35
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- 239000012044 organic layer Substances 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 239000002904 solvent Substances 0.000 description 30
- 229910052938 sodium sulfate Inorganic materials 0.000 description 29
- 235000011152 sodium sulphate Nutrition 0.000 description 29
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 26
- 230000008602 contraction Effects 0.000 description 26
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 24
- 238000010992 reflux Methods 0.000 description 23
- 241000700159 Rattus Species 0.000 description 22
- 235000019439 ethyl acetate Nutrition 0.000 description 22
- 239000000543 intermediate Substances 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 21
- 238000003756 stirring Methods 0.000 description 21
- 239000007832 Na2SO4 Substances 0.000 description 20
- RVOJTCZRIKWHDX-UHFFFAOYSA-N cyclohexanecarbonyl chloride Chemical compound ClC(=O)C1CCCCC1 RVOJTCZRIKWHDX-UHFFFAOYSA-N 0.000 description 20
- 238000000746 purification Methods 0.000 description 20
- 229910021529 ammonia Inorganic materials 0.000 description 19
- 238000006722 reduction reaction Methods 0.000 description 18
- YZKSXUIOKWQABW-UHFFFAOYSA-N 4-piperazin-1-yl-1h-indole Chemical compound C1CNCCN1C1=CC=CC2=C1C=CN2 YZKSXUIOKWQABW-UHFFFAOYSA-N 0.000 description 17
- 230000009467 reduction Effects 0.000 description 17
- 230000002829 reductive effect Effects 0.000 description 17
- 238000003786 synthesis reaction Methods 0.000 description 17
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 16
- 239000000460 chlorine Substances 0.000 description 16
- 238000001914 filtration Methods 0.000 description 16
- 230000027939 micturition Effects 0.000 description 16
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 16
- SKAMJDANZANFOM-UHFFFAOYSA-N 2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]quinoline Chemical compound C1=CC=CC2=NC(CN3CCN(CC3)C=3C=4C=CNC=4C=CC=3)=CC=C21 SKAMJDANZANFOM-UHFFFAOYSA-N 0.000 description 15
- 150000001412 amines Chemical class 0.000 description 15
- 230000000694 effects Effects 0.000 description 15
- 239000003921 oil Substances 0.000 description 15
- 235000019198 oils Nutrition 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 14
- 239000003480 eluent Substances 0.000 description 14
- 239000007858 starting material Substances 0.000 description 14
- 239000000725 suspension Substances 0.000 description 14
- KMPOJKNMGCUFDT-UHFFFAOYSA-N [4-(1h-indol-4-yl)piperazin-1-yl]-(1,2,3,4-tetrahydroquinolin-2-yl)methanone Chemical compound C1CC2=CC=CC=C2NC1C(=O)N(CC1)CCN1C1=CC=CC2=C1C=CN2 KMPOJKNMGCUFDT-UHFFFAOYSA-N 0.000 description 13
- WBXQIAKHNGXXCJ-UHFFFAOYSA-N 1-(4-fluoro-2-methoxyphenyl)piperazine Chemical compound COC1=CC(F)=CC=C1N1CCNCC1 WBXQIAKHNGXXCJ-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 235000002639 sodium chloride Nutrition 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 239000003153 chemical reaction reagent Substances 0.000 description 11
- 239000002552 dosage form Substances 0.000 description 11
- 239000003814 drug Substances 0.000 description 11
- 239000012299 nitrogen atmosphere Substances 0.000 description 11
- DDEAEWMDOSXKBX-UHFFFAOYSA-N 2-(chloromethyl)quinoline Chemical compound C1=CC=CC2=NC(CCl)=CC=C21 DDEAEWMDOSXKBX-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 206010021639 Incontinence Diseases 0.000 description 10
- 229940079593 drug Drugs 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 description 9
- 102100022738 5-hydroxytryptamine receptor 1A Human genes 0.000 description 9
- XIQVNETUBQGFHX-UHFFFAOYSA-N Ditropan Chemical compound C=1C=CC=CC=1C(O)(C(=O)OCC#CCN(CC)CC)C1CCCCC1 XIQVNETUBQGFHX-UHFFFAOYSA-N 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- 230000004064 dysfunction Effects 0.000 description 9
- 229960005434 oxybutynin Drugs 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 9
- OSJVTYVKQNOXPP-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)CCC2=C1 OSJVTYVKQNOXPP-UHFFFAOYSA-N 0.000 description 8
- 101710138638 5-hydroxytryptamine receptor 1A Proteins 0.000 description 8
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
- 102000017911 HTR1A Human genes 0.000 description 8
- 101150015707 HTR1A gene Proteins 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 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 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- AMERLXMXGZUVRT-UHFFFAOYSA-N 1-(cyclohexanecarbonyl)-3,4-dihydro-2h-quinoline-2-carbaldehyde Chemical compound O=CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 AMERLXMXGZUVRT-UHFFFAOYSA-N 0.000 description 7
- ZZMRNWUKYUIBHS-UHFFFAOYSA-N 2-[[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]methyl]-1,2,3,4-tetrahydroquinoline Chemical compound O1CCOC2=C1C=CC=C2N(CC1)CCN1CC1NC2=CC=CC=C2CC1 ZZMRNWUKYUIBHS-UHFFFAOYSA-N 0.000 description 7
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 7
- GPIARMSVZOEZCV-UHFFFAOYSA-N 6-fluoro-2-methylquinoline Chemical compound C1=C(F)C=CC2=NC(C)=CC=C21 GPIARMSVZOEZCV-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
- 208000008967 Enuresis Diseases 0.000 description 7
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 7
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 7
- 230000027455 binding Effects 0.000 description 7
- 206010013990 dysuria Diseases 0.000 description 7
- 230000005764 inhibitory process Effects 0.000 description 7
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 7
- 210000003205 muscle Anatomy 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- UGPQPVWABPCSIP-UHFFFAOYSA-N 2-(bromomethyl)-6-fluoroquinoline Chemical compound N1=C(CBr)C=CC2=CC(F)=CC=C21 UGPQPVWABPCSIP-UHFFFAOYSA-N 0.000 description 6
- LUYISICIYVKBTA-UHFFFAOYSA-N 6-methylquinoline Chemical compound N1=CC=CC2=CC(C)=CC=C21 LUYISICIYVKBTA-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 241000124008 Mammalia Species 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 6
- 239000012346 acetyl chloride Substances 0.000 description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 6
- 239000012042 active reagent Substances 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 239000002207 metabolite Substances 0.000 description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 description 6
- 208000024891 symptom Diseases 0.000 description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
- GSWIBNDSQQMSAL-UHFFFAOYSA-N 2-(bromomethyl)-6-(trifluoromethoxy)quinoline Chemical compound N1=C(CBr)C=CC2=CC(OC(F)(F)F)=CC=C21 GSWIBNDSQQMSAL-UHFFFAOYSA-N 0.000 description 5
- CEBRECLDLNLXLK-UHFFFAOYSA-N 2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]quinolin-8-ol Chemical compound N1=C2C(O)=CC=CC2=CC=C1CN(CC1)CCN1C1=CC=CC2=C1C=CN2 CEBRECLDLNLXLK-UHFFFAOYSA-N 0.000 description 5
- PIXOJURPOFOAAL-UHFFFAOYSA-N 2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-1,2,3,4-tetrahydroquinoline Chemical compound COC1=CC(F)=CC=C1N1CCN(CC2NC3=CC=CC=C3CC2)CC1 PIXOJURPOFOAAL-UHFFFAOYSA-N 0.000 description 5
- NXUXYDJONMEQFV-UHFFFAOYSA-N 2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]quinoline Chemical compound COC1=CC(F)=CC=C1N1CCN(CC=2N=C3C=CC=CC3=CC=2)CC1 NXUXYDJONMEQFV-UHFFFAOYSA-N 0.000 description 5
- JHBNNVRMQVSXMX-UHFFFAOYSA-N 2-[[4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl]methyl]-1,2,3,4-tetrahydroquinoline Chemical compound FC(F)(F)COC1=CC=CC=C1N1CCN(CC2NC3=CC=CC=C3CC2)CC1 JHBNNVRMQVSXMX-UHFFFAOYSA-N 0.000 description 5
- OHPPATZVAKAYGQ-UHFFFAOYSA-N 2-methyl-6-(trifluoromethoxy)quinoline Chemical compound C1=C(OC(F)(F)F)C=CC2=NC(C)=CC=C21 OHPPATZVAKAYGQ-UHFFFAOYSA-N 0.000 description 5
- ODGIMMLDVSWADK-UHFFFAOYSA-N 4-trifluoromethylaniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1 ODGIMMLDVSWADK-UHFFFAOYSA-N 0.000 description 5
- NEJIMCKSORXBKF-UHFFFAOYSA-N 6-bromo-2-(iodomethyl)-1,2,3,4-tetrahydroquinoline Chemical compound N1C(CI)CCC2=CC(Br)=CC=C21 NEJIMCKSORXBKF-UHFFFAOYSA-N 0.000 description 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 5
- 239000004698 Polyethylene Substances 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 230000003042 antagnostic effect Effects 0.000 description 5
- 239000003937 drug carrier Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 125000001041 indolyl group Chemical group 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 5
- 230000001242 postsynaptic effect Effects 0.000 description 5
- XYKIUTSFQGXHOW-UHFFFAOYSA-N propan-2-one;toluene Chemical compound CC(C)=O.CC1=CC=CC=C1 XYKIUTSFQGXHOW-UHFFFAOYSA-N 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 230000001020 rhythmical effect Effects 0.000 description 5
- 230000000862 serotonergic effect Effects 0.000 description 5
- 239000012279 sodium borohydride Substances 0.000 description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 description 5
- 238000010561 standard procedure Methods 0.000 description 5
- 230000006103 sulfonylation Effects 0.000 description 5
- 238000005694 sulfonylation reaction Methods 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- SCNJYNSLUUZKIB-UHFFFAOYSA-N (6-chloro-1,2,3,4-tetrahydroquinolin-2-yl)methanol Chemical compound ClC1=CC=C2NC(CO)CCC2=C1 SCNJYNSLUUZKIB-UHFFFAOYSA-N 0.000 description 4
- NSCKMTKDMIHICL-UHFFFAOYSA-N 1-[4-(1,2,3,4-tetrahydroquinolin-2-ylmethyl)piperazin-1-yl]isoquinoline Chemical compound C1=CC=C2C(N3CCN(CC3)CC3NC4=CC=CC=C4CC3)=NC=CC2=C1 NSCKMTKDMIHICL-UHFFFAOYSA-N 0.000 description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- HWOSADLUKJVKES-UHFFFAOYSA-N 2-(2-methoxyphenoxy)-n-methyl-n-(1,2,3,4-tetrahydroquinolin-2-ylmethyl)ethanamine Chemical compound COC1=CC=CC=C1OCCN(C)CC1NC2=CC=CC=C2CC1 HWOSADLUKJVKES-UHFFFAOYSA-N 0.000 description 4
- JIFUUGHBYDMCDY-UHFFFAOYSA-N 2-(bromomethyl)-6-methoxyquinoline Chemical compound N1=C(CBr)C=CC2=CC(OC)=CC=C21 JIFUUGHBYDMCDY-UHFFFAOYSA-N 0.000 description 4
- XJIYZTAPBCUHEW-UHFFFAOYSA-N 2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-6-(trifluoromethoxy)-1,2,3,4-tetrahydroquinoline Chemical compound C1CC2=CC(OC(F)(F)F)=CC=C2NC1CN(CC1)CCN1C1=CC=CC2=C1C=CN2 XJIYZTAPBCUHEW-UHFFFAOYSA-N 0.000 description 4
- WMSIMCIGJDBNTP-UHFFFAOYSA-N 2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-6-(trifluoromethoxy)quinoline Chemical compound C1=CC2=CC(OC(F)(F)F)=CC=C2N=C1CN(CC1)CCN1C1=CC=CC2=C1C=CN2 WMSIMCIGJDBNTP-UHFFFAOYSA-N 0.000 description 4
- SDALTOQCKMYXOC-UHFFFAOYSA-N 2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-6-(trifluoromethyl)quinoline Chemical compound C1=CC2=CC(C(F)(F)F)=CC=C2N=C1CN(CC1)CCN1C1=CC=CC2=C1C=CN2 SDALTOQCKMYXOC-UHFFFAOYSA-N 0.000 description 4
- DGHLBVIXPRFTFN-UHFFFAOYSA-N 2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-6-methoxyquinoline Chemical compound C1=CC2=CC(OC)=CC=C2N=C1CN(CC1)CCN1C1=CC=CC2=C1C=CN2 DGHLBVIXPRFTFN-UHFFFAOYSA-N 0.000 description 4
- MOMAOYHGONKCJO-UHFFFAOYSA-N 2-[[4-(2-methoxyphenyl)piperazin-1-yl]methyl]-1,2,3,4-tetrahydroquinoline Chemical compound COC1=CC=CC=C1N1CCN(CC2NC3=CC=CC=C3CC2)CC1 MOMAOYHGONKCJO-UHFFFAOYSA-N 0.000 description 4
- GWVHGXBMFDQWGQ-UHFFFAOYSA-N 2-[[4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl]methyl]quinoline Chemical compound FC(F)(F)COC1=CC=CC=C1N1CCN(CC=2N=C3C=CC=CC3=CC=2)CC1 GWVHGXBMFDQWGQ-UHFFFAOYSA-N 0.000 description 4
- VHSCBEQRKQRFEK-UHFFFAOYSA-N 2-methyl-6-(trifluoromethyl)quinoline Chemical compound C1=C(C(F)(F)F)C=CC2=NC(C)=CC=C21 VHSCBEQRKQRFEK-UHFFFAOYSA-N 0.000 description 4
- MNIOKDAGSOZMIV-UHFFFAOYSA-N 5-chloro-2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-1,2,3,4-tetrahydroquinoline Chemical compound COC1=CC(F)=CC=C1N1CCN(CC2NC3=CC=CC(Cl)=C3CC2)CC1 MNIOKDAGSOZMIV-UHFFFAOYSA-N 0.000 description 4
- MQPSPUQAPOBPSB-UHFFFAOYSA-N 5-chloroquinoline-2-carboxylic acid Chemical compound ClC1=CC=CC2=NC(C(=O)O)=CC=C21 MQPSPUQAPOBPSB-UHFFFAOYSA-N 0.000 description 4
- BPHHPQVNDVZQQU-UHFFFAOYSA-N 5-fluoro-1,2,3,4-tetrahydroquinoline-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)CCC2=C1F BPHHPQVNDVZQQU-UHFFFAOYSA-N 0.000 description 4
- CWEULJFHHXIDPP-UHFFFAOYSA-N 6-chloro-2-(iodomethyl)-1,2,3,4-tetrahydroquinoline Chemical compound N1C(CI)CCC2=CC(Cl)=CC=C21 CWEULJFHHXIDPP-UHFFFAOYSA-N 0.000 description 4
- DSMAUCDQSXHDIX-UHFFFAOYSA-N 6-fluoro-2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]quinoline Chemical compound C1=CC2=CC(F)=CC=C2N=C1CN(CC1)CCN1C1=CC=CC2=C1C=CN2 DSMAUCDQSXHDIX-UHFFFAOYSA-N 0.000 description 4
- NTPKQYXIHNTIDJ-UHFFFAOYSA-N 6-methyl-1,2,3,4-tetrahydroquinoline-2-carboxylic acid Chemical compound N1C(C(O)=O)CCC2=CC(C)=CC=C21 NTPKQYXIHNTIDJ-UHFFFAOYSA-N 0.000 description 4
- YZICJAPFFGEMHO-UHFFFAOYSA-N 7-chloro-2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-1,2,3,4-tetrahydroquinoline Chemical compound COC1=CC(F)=CC=C1N1CCN(CC2NC3=CC(Cl)=CC=C3CC2)CC1 YZICJAPFFGEMHO-UHFFFAOYSA-N 0.000 description 4
- YZKVOXRTZSBXQS-UHFFFAOYSA-N 7-chloro-2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]quinoline Chemical compound COC1=CC(F)=CC=C1N1CCN(CC=2N=C3C=C(Cl)C=CC3=CC=2)CC1 YZKVOXRTZSBXQS-UHFFFAOYSA-N 0.000 description 4
- AYSKNDXTWPNRKG-UHFFFAOYSA-N 7-fluoro-2-methylquinoline Chemical compound C1=CC(F)=CC2=NC(C)=CC=C21 AYSKNDXTWPNRKG-UHFFFAOYSA-N 0.000 description 4
- ADRLENYQJOHPCN-UHFFFAOYSA-N 8-fluoro-2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]quinoline Chemical compound N1=C2C(F)=CC=CC2=CC=C1CN(CC1)CCN1C1=CC=CC2=C1C=CN2 ADRLENYQJOHPCN-UHFFFAOYSA-N 0.000 description 4
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 description 4
- 239000012448 Lithium borohydride Substances 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 208000004403 Prostatic Hyperplasia Diseases 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- 239000000674 adrenergic antagonist Substances 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 210000003169 central nervous system Anatomy 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 4
- 206010013663 drug dependence Diseases 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 238000001640 fractional crystallisation Methods 0.000 description 4
- 230000026030 halogenation Effects 0.000 description 4
- 238000005658 halogenation reaction Methods 0.000 description 4
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 4
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 4
- 238000001802 infusion Methods 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 230000037361 pathway Effects 0.000 description 4
- 239000006187 pill Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 description 4
- 102000005962 receptors Human genes 0.000 description 4
- 108020003175 receptors Proteins 0.000 description 4
- 230000011514 reflex Effects 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 208000011117 substance-related disease Diseases 0.000 description 4
- ZDXVDYPXUXWJBP-UHFFFAOYSA-N tert-butyl n-(2-methylquinolin-6-yl)carbamate Chemical compound C1=C(NC(=O)OC(C)(C)C)C=CC2=NC(C)=CC=C21 ZDXVDYPXUXWJBP-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 239000006211 transdermal dosage form Substances 0.000 description 4
- 210000002700 urine Anatomy 0.000 description 4
- IXYKFHYUYJPUCY-UHFFFAOYSA-N (6-bromo-1,2,3,4-tetrahydroquinolin-2-yl)methanol Chemical compound BrC1=CC=C2NC(CO)CCC2=C1 IXYKFHYUYJPUCY-UHFFFAOYSA-N 0.000 description 3
- WFZUKYTXWMODCF-UHFFFAOYSA-N (6-nitro-1,2,3,4-tetrahydroquinolin-2-yl)methanol Chemical compound [O-][N+](=O)C1=CC=C2NC(CO)CCC2=C1 WFZUKYTXWMODCF-UHFFFAOYSA-N 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- HQZYEBAHFPMNLX-UHFFFAOYSA-N 1-(methoxymethyl)-4-piperazin-1-ylindole Chemical compound C1=CC=C2N(COC)C=CC2=C1N1CCNCC1 HQZYEBAHFPMNLX-UHFFFAOYSA-N 0.000 description 3
- FRBWHZCMJAYPRZ-UHFFFAOYSA-N 1-benzoyl-5-chloro-2h-quinoline-2-carbonitrile Chemical compound N#CC1C=CC=2C(Cl)=CC=CC=2N1C(=O)C1=CC=CC=C1 FRBWHZCMJAYPRZ-UHFFFAOYSA-N 0.000 description 3
- KQKHKCPPVPHKRC-UHFFFAOYSA-N 1-benzoyl-5-fluoro-2h-quinoline-2-carbonitrile Chemical compound N#CC1C=CC=2C(F)=CC=CC=2N1C(=O)C1=CC=CC=C1 KQKHKCPPVPHKRC-UHFFFAOYSA-N 0.000 description 3
- IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical class C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 description 3
- RJNBEDAGIQODEK-UHFFFAOYSA-N 1-ethyl-4-piperazin-1-ylindole Chemical compound C1=CC=C2N(CC)C=CC2=C1N1CCNCC1 RJNBEDAGIQODEK-UHFFFAOYSA-N 0.000 description 3
- MXLHOIUHNDDDHF-UHFFFAOYSA-N 2,3-dihydro-1h-indol-2-yl-[4-(1h-indol-4-yl)piperazin-1-yl]methanone Chemical compound C1C2=CC=CC=C2NC1C(=O)N(CC1)CCN1C1=CC=CC2=C1C=CN2 MXLHOIUHNDDDHF-UHFFFAOYSA-N 0.000 description 3
- BELFSAVWJLQIBB-UHFFFAOYSA-N 2,8-dimethylquinoline Chemical compound C1=CC=C(C)C2=NC(C)=CC=C21 BELFSAVWJLQIBB-UHFFFAOYSA-N 0.000 description 3
- AMDXCOLHUAMJFV-UHFFFAOYSA-N 2-(bromomethyl)-2-methyl-3,4-dihydro-1h-quinoline Chemical compound C1=CC=C2NC(C)(CBr)CCC2=C1 AMDXCOLHUAMJFV-UHFFFAOYSA-N 0.000 description 3
- IRBKJWAECCCSMZ-UHFFFAOYSA-N 2-(bromomethyl)-6-(trifluoromethyl)quinoline Chemical compound N1=C(CBr)C=CC2=CC(C(F)(F)F)=CC=C21 IRBKJWAECCCSMZ-UHFFFAOYSA-N 0.000 description 3
- UGKKTRPHNPIVTN-UHFFFAOYSA-N 2-(bromomethyl)-6-nitro-1,2,3,4-tetrahydroquinoline Chemical compound N1C(CBr)CCC2=CC([N+](=O)[O-])=CC=C21 UGKKTRPHNPIVTN-UHFFFAOYSA-N 0.000 description 3
- KFEQBMRADNUXHN-UHFFFAOYSA-N 2-(bromomethyl)-7-chloro-1,2,3,4-tetrahydroquinoline Chemical compound C1CC(CBr)NC2=CC(Cl)=CC=C21 KFEQBMRADNUXHN-UHFFFAOYSA-N 0.000 description 3
- YHUBQGZOSVRSJN-UHFFFAOYSA-N 2-(bromomethyl)-7-fluoroquinoline Chemical compound C1=CC(CBr)=NC2=CC(F)=CC=C21 YHUBQGZOSVRSJN-UHFFFAOYSA-N 0.000 description 3
- VQONZJTWIQNLSW-UHFFFAOYSA-N 2-(bromomethyl)-8-fluoroquinoline Chemical compound C1=C(CBr)N=C2C(F)=CC=CC2=C1 VQONZJTWIQNLSW-UHFFFAOYSA-N 0.000 description 3
- UNDWLDXVEGAAOQ-UHFFFAOYSA-N 2-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-1,2,3,4-tetrahydroquinoline Chemical compound COC1=CC=CC=C1N1CCN(CCC2NC3=CC=CC=C3CC2)CC1 UNDWLDXVEGAAOQ-UHFFFAOYSA-N 0.000 description 3
- OPWPEWQJZHEBLE-UHFFFAOYSA-N 2-[[4-(1-benzofuran-7-yl)piperazin-1-yl]methyl]-1,2,3,4-tetrahydroquinoline Chemical compound C1CC2=CC=CC=C2NC1CN(CC1)CCN1C1=CC=CC2=C1OC=C2 OPWPEWQJZHEBLE-UHFFFAOYSA-N 0.000 description 3
- OYSGJBFPGRABFL-UHFFFAOYSA-N 2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-8-methoxy-1,2,3,4-tetrahydroquinoline Chemical compound N1C=2C(OC)=CC=CC=2CCC1CN(CC1)CCN1C1=CC=CC2=C1C=CN2 OYSGJBFPGRABFL-UHFFFAOYSA-N 0.000 description 3
- NHPHRZBEUVAIDM-UHFFFAOYSA-N 2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-8-methoxyquinoline Chemical compound N1=C2C(OC)=CC=CC2=CC=C1CN(CC1)CCN1C1=CC=CC2=C1C=CN2 NHPHRZBEUVAIDM-UHFFFAOYSA-N 0.000 description 3
- IOYPABIJNKSQFD-UHFFFAOYSA-N 2-[[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]methyl]quinoline Chemical compound C1=CC=CC2=NC(CN3CCN(CC3)C=3C=4OCCOC=4C=CC=3)=CC=C21 IOYPABIJNKSQFD-UHFFFAOYSA-N 0.000 description 3
- LDTRHHSRHUOJNI-UHFFFAOYSA-N 2-[[4-(2-methoxyphenyl)piperazin-1-yl]methyl]quinoline Chemical compound COC1=CC=CC=C1N1CCN(CC=2N=C3C=CC=CC3=CC=2)CC1 LDTRHHSRHUOJNI-UHFFFAOYSA-N 0.000 description 3
- KDQNPTKGGIYIPP-UHFFFAOYSA-N 2-[[4-(2-methoxyphenyl)piperidin-1-yl]methyl]quinoline Chemical compound COC1=CC=CC=C1C1CCN(CC=2N=C3C=CC=CC3=CC=2)CC1 KDQNPTKGGIYIPP-UHFFFAOYSA-N 0.000 description 3
- PAISDDDHJUGTEO-UHFFFAOYSA-N 2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-2-methyl-3,4-dihydro-1h-quinoline Chemical compound COC1=CC(F)=CC=C1N1CCN(CC2(C)NC3=CC=CC=C3CC2)CC1 PAISDDDHJUGTEO-UHFFFAOYSA-N 0.000 description 3
- KXHHTRWVBYQZHY-UHFFFAOYSA-N 2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-6-nitro-1,2,3,4-tetrahydroquinoline Chemical compound COC1=CC(F)=CC=C1N1CCN(CC2NC3=CC=C(C=C3CC2)[N+]([O-])=O)CC1 KXHHTRWVBYQZHY-UHFFFAOYSA-N 0.000 description 3
- VHUBEPFRNJVKJP-UHFFFAOYSA-N 2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-7-methyl-1,2,3,4-tetrahydroquinoline Chemical compound COC1=CC(F)=CC=C1N1CCN(CC2NC3=CC(C)=CC=C3CC2)CC1 VHUBEPFRNJVKJP-UHFFFAOYSA-N 0.000 description 3
- YWYCYCRBAAEPFA-UHFFFAOYSA-N 2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-8-methyl-1,2,3,4-tetrahydroquinoline Chemical compound COC1=CC(F)=CC=C1N1CCN(CC2NC3=C(C)C=CC=C3CC2)CC1 YWYCYCRBAAEPFA-UHFFFAOYSA-N 0.000 description 3
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 3
- SMUKODJVMQOSAB-UHFFFAOYSA-N 2-ethylbutanoyl chloride Chemical compound CCC(CC)C(Cl)=O SMUKODJVMQOSAB-UHFFFAOYSA-N 0.000 description 3
- USSQQASIZNTRAJ-UHFFFAOYSA-N 2-methylquinolin-6-ol Chemical compound C1=C(O)C=CC2=NC(C)=CC=C21 USSQQASIZNTRAJ-UHFFFAOYSA-N 0.000 description 3
- VMKYFYKSETWDMZ-UHFFFAOYSA-N 4-[4-(2,3-dihydro-1h-indol-2-ylmethyl)piperazin-1-yl]-1h-indole Chemical compound C1C2=CC=CC=C2NC1CN(CC1)CCN1C1=CC=CC2=C1C=CN2 VMKYFYKSETWDMZ-UHFFFAOYSA-N 0.000 description 3
- UIADWSXPNFQQCZ-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenyl)-5-phenyl-1,3-oxazol-2-yl]butanoic acid Chemical compound ClC=1C=C(C=CC=1Cl)C=1N=C(OC=1C1=CC=CC=C1)CCCC(=O)O UIADWSXPNFQQCZ-UHFFFAOYSA-N 0.000 description 3
- RXQSSBWYYXBJFX-UHFFFAOYSA-N 4-piperazin-1-yl-1-propan-2-ylindole Chemical compound C1=CC=C2N(C(C)C)C=CC2=C1N1CCNCC1 RXQSSBWYYXBJFX-UHFFFAOYSA-N 0.000 description 3
- IBTOZNWXKGZETJ-UHFFFAOYSA-N 5-chloro-1,2,3,4-tetrahydroquinoline-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)CCC2=C1Cl IBTOZNWXKGZETJ-UHFFFAOYSA-N 0.000 description 3
- DKVVECZQAACTNX-UHFFFAOYSA-N 5-fluoro-2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-1,2,3,4-tetrahydroquinoline Chemical compound COC1=CC(F)=CC=C1N1CCN(CC2NC3=CC=CC(F)=C3CC2)CC1 DKVVECZQAACTNX-UHFFFAOYSA-N 0.000 description 3
- RTVUNKIAMQMWTL-UHFFFAOYSA-N 5-fluoroquinoline-2-carboxylic acid Chemical compound FC1=CC=CC2=NC(C(=O)O)=CC=C21 RTVUNKIAMQMWTL-UHFFFAOYSA-N 0.000 description 3
- GABJAQNQVUYNKG-UHFFFAOYSA-N 6-bromo-2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-1,2,3,4-tetrahydroquinoline Chemical compound COC1=CC(F)=CC=C1N1CCN(CC2NC3=CC=C(Br)C=C3CC2)CC1 GABJAQNQVUYNKG-UHFFFAOYSA-N 0.000 description 3
- PLMSXXCVJBQMDQ-UHFFFAOYSA-N 6-fluoro-2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-1,2,3,4-tetrahydroquinoline Chemical compound C1CC2=CC(F)=CC=C2NC1CN(CC1)CCN1C1=CC=CC2=C1C=CN2 PLMSXXCVJBQMDQ-UHFFFAOYSA-N 0.000 description 3
- WPEQJEGNZGMHEZ-UHFFFAOYSA-N 6-methylquinoline-2-carboxylic acid Chemical compound N1=C(C(O)=O)C=CC2=CC(C)=CC=C21 WPEQJEGNZGMHEZ-UHFFFAOYSA-N 0.000 description 3
- WLNXIQXCYSXHGD-UHFFFAOYSA-N 7-fluoro-2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-1,2,3,4-tetrahydroquinoline Chemical compound N1C2=CC(F)=CC=C2CCC1CN(CC1)CCN1C1=CC=CC2=C1C=CN2 WLNXIQXCYSXHGD-UHFFFAOYSA-N 0.000 description 3
- AOSDHUYMTUVRPI-UHFFFAOYSA-N 7-fluoro-2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]quinoline Chemical compound N=1C2=CC(F)=CC=C2C=CC=1CN(CC1)CCN1C1=CC=CC2=C1C=CN2 AOSDHUYMTUVRPI-UHFFFAOYSA-N 0.000 description 3
- ASXGJMSKWNBENU-UHFFFAOYSA-N 8-OH-DPAT Chemical compound C1=CC(O)=C2CC(N(CCC)CCC)CCC2=C1 ASXGJMSKWNBENU-UHFFFAOYSA-N 0.000 description 3
- IQPXTSSTSUXGMX-UHFFFAOYSA-N 8-fluoro-2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-1,2,3,4-tetrahydroquinoline Chemical compound N1C=2C(F)=CC=CC=2CCC1CN(CC1)CCN1C1=CC=CC2=C1C=CN2 IQPXTSSTSUXGMX-UHFFFAOYSA-N 0.000 description 3
- HJHYMLQMBHHNRJ-UHFFFAOYSA-N 8-fluoro-2-methylquinoline Chemical compound C1=CC=C(F)C2=NC(C)=CC=C21 HJHYMLQMBHHNRJ-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- 208000019901 Anxiety disease Diseases 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- 206010020853 Hypertonic bladder Diseases 0.000 description 3
- 208000005615 Interstitial Cystitis Diseases 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
- 208000009722 Overactive Urinary Bladder Diseases 0.000 description 3
- 206010042008 Stereotypy Diseases 0.000 description 3
- 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 3
- JVSNSESFGQYRIB-UHFFFAOYSA-N [4-(1-benzofuran-7-yl)piperazin-1-yl]-(1,2,3,4-tetrahydroquinolin-2-yl)methanone Chemical compound C1CC2=CC=CC=C2NC1C(=O)N(CC1)CCN1C1=CC=CC2=C1OC=C2 JVSNSESFGQYRIB-UHFFFAOYSA-N 0.000 description 3
- IOADJVPXAIIWGM-UHFFFAOYSA-N [4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]-(5-fluoro-1,2,3,4-tetrahydroquinolin-2-yl)methanone Chemical compound COC1=CC(F)=CC=C1N1CCN(C(=O)C2NC3=CC=CC(F)=C3CC2)CC1 IOADJVPXAIIWGM-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 150000007513 acids Chemical class 0.000 description 3
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 3
- 238000000540 analysis of variance Methods 0.000 description 3
- 230000001022 anti-muscarinic effect Effects 0.000 description 3
- 230000036506 anxiety Effects 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 3
- 244000309464 bull Species 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000003729 cation exchange resin Substances 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 208000015114 central nervous system disease Diseases 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 229940125851 compound 27 Drugs 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- ZCIBRYGNPIXKDS-UHFFFAOYSA-N cyclohexyl-[2-(hydroxymethyl)-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound OCC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 ZCIBRYGNPIXKDS-UHFFFAOYSA-N 0.000 description 3
- 201000003146 cystitis Diseases 0.000 description 3
- 230000003111 delayed effect Effects 0.000 description 3
- 238000010511 deprotection reaction Methods 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 210000004744 fore-foot Anatomy 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- AUAAQBWEOAMYGG-UHFFFAOYSA-N methyl 6-bromo-1,2,3,4-tetrahydroquinoline-2-carboxylate Chemical compound BrC1=CC=C2NC(C(=O)OC)CCC2=C1 AUAAQBWEOAMYGG-UHFFFAOYSA-N 0.000 description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 3
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000002232 neuromuscular Effects 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 238000002414 normal-phase solid-phase extraction Methods 0.000 description 3
- 208000020629 overactive bladder Diseases 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 239000002504 physiological saline solution Substances 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 235000015320 potassium carbonate Nutrition 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 238000006268 reductive amination reaction Methods 0.000 description 3
- 238000010079 rubber tapping Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 3
- 230000001953 sensory effect Effects 0.000 description 3
- 230000007958 sleep Effects 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 210000005070 sphincter Anatomy 0.000 description 3
- 210000000278 spinal cord Anatomy 0.000 description 3
- 238000007920 subcutaneous administration Methods 0.000 description 3
- 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 3
- NFHYBJRTUIZVLD-UHFFFAOYSA-N tert-butyl 4-(1-ethylindol-4-yl)piperazine-1-carboxylate Chemical compound C1=CC=C2N(CC)C=CC2=C1N1CCN(C(=O)OC(C)(C)C)CC1 NFHYBJRTUIZVLD-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 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 3
- ODWSTMTWRDHMAL-UHFFFAOYSA-N tert-butyl n-[2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-1,2,3,4-tetrahydroquinolin-6-yl]carbamate Chemical compound COC1=CC(F)=CC=C1N1CCN(CC2NC3=CC=C(NC(=O)OC(C)(C)C)C=C3CC2)CC1 ODWSTMTWRDHMAL-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- OOGJQPCLVADCPB-HXUWFJFHSA-N tolterodine Chemical compound C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(C)C=2)O)=CC=CC=C1 OOGJQPCLVADCPB-HXUWFJFHSA-N 0.000 description 3
- 229960004045 tolterodine Drugs 0.000 description 3
- 230000002485 urinary effect Effects 0.000 description 3
- BDIAUFOIMFAIPU-UHFFFAOYSA-N valepotriate Natural products CC(C)CC(=O)OC1C=C(C(=COC2OC(=O)CC(C)C)COC(C)=O)C2C11CO1 BDIAUFOIMFAIPU-UHFFFAOYSA-N 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- KDODUHLJQAEGBK-UHFFFAOYSA-N (5-chloro-1,2,3,4-tetrahydroquinolin-2-yl)-[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methanone Chemical compound COC1=CC(F)=CC=C1N1CCN(C(=O)C2NC3=CC=CC(Cl)=C3CC2)CC1 KDODUHLJQAEGBK-UHFFFAOYSA-N 0.000 description 2
- VNICFCQJUVFULD-UHFFFAOYSA-N 1-(1-naphthalenyl)piperazine Chemical compound C1CNCCN1C1=CC=CC2=CC=CC=C12 VNICFCQJUVFULD-UHFFFAOYSA-N 0.000 description 2
- YSEWXFSLNGJJAO-UHFFFAOYSA-N 1-(4-chloro-2-methoxyphenyl)piperazine Chemical compound COC1=CC(Cl)=CC=C1N1CCNCC1 YSEWXFSLNGJJAO-UHFFFAOYSA-N 0.000 description 2
- PVVBTSALZGVEHI-UHFFFAOYSA-N 1-(4-piperazin-1-ylindol-1-yl)ethanone Chemical compound C1=CC=C2N(C(=O)C)C=CC2=C1N1CCNCC1 PVVBTSALZGVEHI-UHFFFAOYSA-N 0.000 description 2
- RTYUZFTYDVDLHW-UHFFFAOYSA-N 1-(5-fluoro-2-methylphenyl)piperazine Chemical compound CC1=CC=C(F)C=C1N1CCNCC1 RTYUZFTYDVDLHW-UHFFFAOYSA-N 0.000 description 2
- GGARUFCQRZCXHK-UHFFFAOYSA-N 1-[(2,4-difluorophenyl)methyl]piperazine Chemical compound FC1=CC(F)=CC=C1CN1CCNCC1 GGARUFCQRZCXHK-UHFFFAOYSA-N 0.000 description 2
- XVHSZKUVDNZYDF-UHFFFAOYSA-N 1-[(2-bromophenyl)methyl]piperazine Chemical compound BrC1=CC=CC=C1CN1CCNCC1 XVHSZKUVDNZYDF-UHFFFAOYSA-N 0.000 description 2
- NTIJTEBBAZRBAW-UHFFFAOYSA-N 1-benzoyl-6-methyl-2h-quinoline-2-carbonitrile Chemical compound N#CC1C=CC2=CC(C)=CC=C2N1C(=O)C1=CC=CC=C1 NTIJTEBBAZRBAW-UHFFFAOYSA-N 0.000 description 2
- XUIKTRIQTZTENL-UHFFFAOYSA-N 2,3-dimethyl-4-piperazin-1-yl-1h-indole Chemical compound C=12C(C)=C(C)NC2=CC=CC=1N1CCNCC1 XUIKTRIQTZTENL-UHFFFAOYSA-N 0.000 description 2
- VTVCBIREGNOIDG-UHFFFAOYSA-N 2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-1,2,3,4-tetrahydroquinolin-8-ol Chemical compound N1C=2C(O)=CC=CC=2CCC1CN(CC1)CCN1C1=CC=CC2=C1C=CN2 VTVCBIREGNOIDG-UHFFFAOYSA-N 0.000 description 2
- COTTUQJYHKWPPC-UHFFFAOYSA-N 2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-6-(trifluoromethyl)-1,2,3,4-tetrahydroquinoline Chemical compound C1CC2=CC(C(F)(F)F)=CC=C2NC1CN(CC1)CCN1C1=CC=CC2=C1C=CN2 COTTUQJYHKWPPC-UHFFFAOYSA-N 0.000 description 2
- ZMGBBUAJBKVYSM-UHFFFAOYSA-N 2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-6-methyl-1,2,3,4-tetrahydroquinoline Chemical compound C1CC2=CC(C)=CC=C2NC1CN(CC1)CCN1C1=CC=CC2=C1C=CN2 ZMGBBUAJBKVYSM-UHFFFAOYSA-N 0.000 description 2
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 2
- YUDQGXUXUKTOMZ-UHFFFAOYSA-N 2-methyl-7-nitro-1h-indole Chemical compound C1=CC([N+]([O-])=O)=C2NC(C)=CC2=C1 YUDQGXUXUKTOMZ-UHFFFAOYSA-N 0.000 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 description 2
- JSMDUOFOPDSKIQ-UHFFFAOYSA-N 3-methoxypropanoyl chloride Chemical compound COCCC(Cl)=O JSMDUOFOPDSKIQ-UHFFFAOYSA-N 0.000 description 2
- XJGNRXDOYOEFKR-UHFFFAOYSA-N 3-phenylmethoxypropanoyl chloride Chemical compound ClC(=O)CCOCC1=CC=CC=C1 XJGNRXDOYOEFKR-UHFFFAOYSA-N 0.000 description 2
- MCFBUIIRFZBRCU-UHFFFAOYSA-N 4-[1-[5-[6-(trifluoromethyl)-1h-benzimidazol-2-yl]pyridin-2-yl]piperidin-4-yl]oxycyclohexane-1-carboxylic acid Chemical compound C1CC(C(=O)O)CCC1OC1CCN(C=2N=CC(=CC=2)C=2NC3=CC(=CC=C3N=2)C(F)(F)F)CC1 MCFBUIIRFZBRCU-UHFFFAOYSA-N 0.000 description 2
- WMFXCDGQRHJFKL-UHFFFAOYSA-N 5-fluoroquinoline Chemical compound C1=CC=C2C(F)=CC=CC2=N1 WMFXCDGQRHJFKL-UHFFFAOYSA-N 0.000 description 2
- NAGJQQFMJKMXJQ-UHFFFAOYSA-N 6-methoxy-2-methylquinoline Chemical compound N1=C(C)C=CC2=CC(OC)=CC=C21 NAGJQQFMJKMXJQ-UHFFFAOYSA-N 0.000 description 2
- DPWOWJSIAITTFO-UHFFFAOYSA-N 7-bromo-4-piperazin-1-yl-1h-indole Chemical compound C1=2C=CNC=2C(Br)=CC=C1N1CCNCC1 DPWOWJSIAITTFO-UHFFFAOYSA-N 0.000 description 2
- SFCJDOGTXXAIDZ-UHFFFAOYSA-N 7-methoxy-4-piperazin-1-yl-1h-indole Chemical compound C1=2C=CNC=2C(OC)=CC=C1N1CCNCC1 SFCJDOGTXXAIDZ-UHFFFAOYSA-N 0.000 description 2
- DYKDPPROHYQWOP-UHFFFAOYSA-N 7-methyl-4-piperazin-1-yl-1h-indole Chemical compound C1=2C=CNC=2C(C)=CC=C1N1CCNCC1 DYKDPPROHYQWOP-UHFFFAOYSA-N 0.000 description 2
- MNRCIPOFTIYSAD-UHFFFAOYSA-N 8-methylquinoline-2-carbaldehyde Chemical compound C1=C(C=O)N=C2C(C)=CC=CC2=C1 MNRCIPOFTIYSAD-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 2
- 241000416162 Astragalus gummifer Species 0.000 description 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 206010012289 Dementia Diseases 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 description 2
- 206010022998 Irritability Diseases 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 2
- 240000007472 Leucaena leucocephala Species 0.000 description 2
- 206010071289 Lower urinary tract symptoms Diseases 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 206010027566 Micturition urgency Diseases 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
- 229910020667 PBr3 Inorganic materials 0.000 description 2
- 206010036018 Pollakiuria Diseases 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- 229910006124 SOCl2 Inorganic materials 0.000 description 2
- 229910018162 SeO2 Inorganic materials 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 206010066218 Stress Urinary Incontinence Diseases 0.000 description 2
- 208000006011 Stroke Diseases 0.000 description 2
- DRHKJLXJIQTDTD-OAHLLOKOSA-N Tamsulosine Chemical compound CCOC1=CC=CC=C1OCCN[C@H](C)CC1=CC=C(OC)C(S(N)(=O)=O)=C1 DRHKJLXJIQTDTD-OAHLLOKOSA-N 0.000 description 2
- 229920001615 Tragacanth Polymers 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 208000000921 Urge Urinary Incontinence Diseases 0.000 description 2
- 206010046542 Urinary hesitation Diseases 0.000 description 2
- 206010046555 Urinary retention Diseases 0.000 description 2
- 208000026723 Urinary tract disease Diseases 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 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 2
- DXGREQNZJTVPBB-UHFFFAOYSA-N [4-(1h-indol-4-yl)piperazin-1-yl]-(6-methyl-1,2,3,4-tetrahydroquinolin-2-yl)methanone Chemical compound C1CC2=CC(C)=CC=C2NC1C(=O)N(CC1)CCN1C1=CC=CC2=C1C=CN2 DXGREQNZJTVPBB-UHFFFAOYSA-N 0.000 description 2
- GNSGSDZQNIMGRG-UHFFFAOYSA-N [4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]-(7-methyl-1,2,3,4-tetrahydroquinolin-2-yl)methanone Chemical compound COC1=CC(F)=CC=C1N1CCN(C(=O)C2NC3=CC(C)=CC=C3CC2)CC1 GNSGSDZQNIMGRG-UHFFFAOYSA-N 0.000 description 2
- DMEPDNFRHUGNPT-UHFFFAOYSA-N [5-(diethylamino)-2-methylpent-3-yn-2-yl] 2-cyclohexyl-2-hydroxy-2-phenylacetate Chemical compound C=1C=CC=CC=1C(O)(C(=O)OC(C)(C)C#CCN(CC)CC)C1CCCCC1 DMEPDNFRHUGNPT-UHFFFAOYSA-N 0.000 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 description 2
- 230000004308 accommodation Effects 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 125000004442 acylamino group Chemical group 0.000 description 2
- WNMJYKCGWZFFKR-UHFFFAOYSA-N alfuzosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(C)CCCNC(=O)C1CCCO1 WNMJYKCGWZFFKR-UHFFFAOYSA-N 0.000 description 2
- 229960004607 alfuzosin Drugs 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- POJWUDADGALRAB-UHFFFAOYSA-N allantoin Chemical compound NC(=O)NC1NC(=O)NC1=O POJWUDADGALRAB-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 230000008485 antagonism Effects 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 229910000085 borane Inorganic materials 0.000 description 2
- MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 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 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 208000010877 cognitive disease Diseases 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 238000013270 controlled release Methods 0.000 description 2
- 230000001054 cortical effect Effects 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- 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 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 description 2
- 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 description 2
- WEPUZBYKXNKSDH-UHFFFAOYSA-N cyclopentanecarbonyl chloride Chemical compound ClC(=O)C1CCCC1 WEPUZBYKXNKSDH-UHFFFAOYSA-N 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- HXGBXQDTNZMWGS-RUZDIDTESA-N darifenacin Chemical compound C=1C=CC=CC=1C([C@H]1CN(CCC=2C=C3CCOC3=CC=2)CC1)(C(=O)N)C1=CC=CC=C1 HXGBXQDTNZMWGS-RUZDIDTESA-N 0.000 description 2
- 229960002677 darifenacin Drugs 0.000 description 2
- ZWWWLCMDTZFSOO-UHFFFAOYSA-N diethoxyphosphorylformonitrile Chemical compound CCOP(=O)(C#N)OCC ZWWWLCMDTZFSOO-UHFFFAOYSA-N 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000007884 disintegrant Substances 0.000 description 2
- 239000008157 edible vegetable oil Substances 0.000 description 2
- WVLHGCRWEHCIOT-UHFFFAOYSA-N eltoprazine Chemical compound C1CNCCN1C1=CC=CC2=C1OCCO2 WVLHGCRWEHCIOT-UHFFFAOYSA-N 0.000 description 2
- CMVAYPJYRXHDOB-UHFFFAOYSA-N ethyl 2-oxopiperidine-1-carboxylate Chemical class CCOC(=O)N1CCCCC1=O CMVAYPJYRXHDOB-UHFFFAOYSA-N 0.000 description 2
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 125000001475 halogen functional group Chemical group 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- 238000007918 intramuscular administration Methods 0.000 description 2
- 238000007913 intrathecal administration Methods 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 208000002551 irritable bowel syndrome Diseases 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 230000005923 long-lasting effect Effects 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 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 2
- GTWAQRQSOVSEEK-UHFFFAOYSA-N methyl 1-(cyclohexanecarbonyl)-6-nitro-3,4-dihydro-2h-quinoline-2-carboxylate Chemical compound COC(=O)C1CCC2=CC([N+]([O-])=O)=CC=C2N1C(=O)C1CCCCC1 GTWAQRQSOVSEEK-UHFFFAOYSA-N 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- 210000005036 nerve Anatomy 0.000 description 2
- 238000006396 nitration reaction Methods 0.000 description 2
- 206010029446 nocturia Diseases 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- 239000006186 oral dosage form Substances 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical class C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 2
- IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- IENZQIKPVFGBNW-UHFFFAOYSA-N prazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 IENZQIKPVFGBNW-UHFFFAOYSA-N 0.000 description 2
- 229960001289 prazosin Drugs 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 239000002287 radioligand Substances 0.000 description 2
- 229940044551 receptor antagonist Drugs 0.000 description 2
- 239000002464 receptor antagonist Substances 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 230000036299 sexual function Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 2
- 238000013222 sprague-dawley male rat Methods 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 208000022170 stress incontinence Diseases 0.000 description 2
- 238000010254 subcutaneous injection Methods 0.000 description 2
- 239000007929 subcutaneous injection Substances 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 239000003765 sweetening agent Substances 0.000 description 2
- 208000011580 syndromic disease Diseases 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- 229960002613 tamsulosin Drugs 0.000 description 2
- 229950000334 temiverine Drugs 0.000 description 2
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
- ALEZFKOBBFTXKQ-UHFFFAOYSA-N tert-butyl n-(2-formylquinolin-6-yl)carbamate Chemical compound N1=C(C=O)C=CC2=CC(NC(=O)OC(C)(C)C)=CC=C21 ALEZFKOBBFTXKQ-UHFFFAOYSA-N 0.000 description 2
- UHVYVOWWFVFBQW-UHFFFAOYSA-N tert-butyl n-[2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]quinolin-6-yl]carbamate Chemical compound COC1=CC(F)=CC=C1N1CCN(CC=2N=C3C=CC(NC(=O)OC(C)(C)C)=CC3=CC=2)CC1 UHVYVOWWFVFBQW-UHFFFAOYSA-N 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- 150000003530 tetrahydroquinolines Chemical class 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- 239000002691 unilamellar liposome Substances 0.000 description 2
- 210000003708 urethra Anatomy 0.000 description 2
- 206010046494 urge incontinence Diseases 0.000 description 2
- 208000022934 urinary frequency Diseases 0.000 description 2
- 208000014001 urinary system disease Diseases 0.000 description 2
- 230000036318 urination frequency Effects 0.000 description 2
- 230000003202 urodynamic effect Effects 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- QBQPILAIUXEVIO-UHFFFAOYSA-N (2-chlorophenyl)-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound ClC1=CC=CC=C1C(=O)N1C2=CC=CC=C2CCC1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 QBQPILAIUXEVIO-UHFFFAOYSA-N 0.000 description 1
- PDLZWHDVCTUYPW-UHFFFAOYSA-N (2-methyl-3,4-dihydro-1h-quinolin-2-yl)methanol Chemical compound C1=CC=C2NC(C)(CO)CCC2=C1 PDLZWHDVCTUYPW-UHFFFAOYSA-N 0.000 description 1
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- DIIFZCPZIRQDIJ-UHFFFAOYSA-N (3,5-dimethyl-1,2-oxazol-4-yl)boronic acid Chemical compound CC1=NOC(C)=C1B(O)O DIIFZCPZIRQDIJ-UHFFFAOYSA-N 0.000 description 1
- DCNMATSPQKWETQ-UHFFFAOYSA-N (5-acetylthiophen-2-yl)boronic acid Chemical compound CC(=O)C1=CC=C(B(O)O)S1 DCNMATSPQKWETQ-UHFFFAOYSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- QSDYZRIUFBMUGV-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinolin-2-ylmethanol Chemical compound C1=CC=C2NC(CO)CCC2=C1 QSDYZRIUFBMUGV-UHFFFAOYSA-N 0.000 description 1
- 238000011925 1,2-addition Methods 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
- DLLBLNFCUXJHHV-UHFFFAOYSA-N 1-(1,2,3,4-tetrahydronaphthalen-1-yl)piperazine Chemical compound C12=CC=CC=C2CCCC1N1CCNCC1 DLLBLNFCUXJHHV-UHFFFAOYSA-N 0.000 description 1
- KFVKNZPFYQDNAE-UHFFFAOYSA-N 1-(1-benzofuran-7-yl)piperazine Chemical compound C1CNCCN1C1=CC=CC2=C1OC=C2 KFVKNZPFYQDNAE-UHFFFAOYSA-N 0.000 description 1
- YSJHCQGGIPTMQM-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)piperazine Chemical compound ClC1=CC(Cl)=CC=C1N1CCNCC1 YSJHCQGGIPTMQM-UHFFFAOYSA-N 0.000 description 1
- JHICIIDUQBMMRM-UHFFFAOYSA-N 1-(2,5-dichlorophenyl)piperazine Chemical compound ClC1=CC=C(Cl)C(N2CCNCC2)=C1 JHICIIDUQBMMRM-UHFFFAOYSA-N 0.000 description 1
- IZFHRJZAZNTUOI-UHFFFAOYSA-N 1-(2,5-dimethoxyphenyl)piperazine Chemical compound COC1=CC=C(OC)C(N2CCNCC2)=C1 IZFHRJZAZNTUOI-UHFFFAOYSA-N 0.000 description 1
- MRBFGEHILMYPTF-UHFFFAOYSA-N 1-(2-Pyrimidyl)piperazine Chemical compound C1CNCCN1C1=NC=CC=N1 MRBFGEHILMYPTF-UHFFFAOYSA-N 0.000 description 1
- SFUOAFXJHFINLN-UHFFFAOYSA-N 1-(2-chloro-5-fluorophenyl)piperazine Chemical compound FC1=CC=C(Cl)C(N2CCNCC2)=C1 SFUOAFXJHFINLN-UHFFFAOYSA-N 0.000 description 1
- HGJFLOVNAPLBKM-UHFFFAOYSA-N 1-(2-ethoxy-4-fluorophenyl)piperazine Chemical compound CCOC1=CC(F)=CC=C1N1CCNCC1 HGJFLOVNAPLBKM-UHFFFAOYSA-N 0.000 description 1
- ZVFTVIGVSYNDEB-UHFFFAOYSA-N 1-(2-fluoro-5-methylphenyl)piperazine Chemical compound CC1=CC=C(F)C(N2CCNCC2)=C1 ZVFTVIGVSYNDEB-UHFFFAOYSA-N 0.000 description 1
- VNZLQLYBRIOLFZ-UHFFFAOYSA-N 1-(2-methoxyphenyl)piperazine Chemical compound COC1=CC=CC=C1N1CCNCC1 VNZLQLYBRIOLFZ-UHFFFAOYSA-N 0.000 description 1
- ZJDWMGREEOZXTH-UHFFFAOYSA-N 1-(2-methoxyphenyl)piperidine Chemical compound COC1=CC=CC=C1N1CCCCC1 ZJDWMGREEOZXTH-UHFFFAOYSA-N 0.000 description 1
- WICKLEOONJPMEQ-UHFFFAOYSA-N 1-(2-methylphenyl)piperazine Chemical compound CC1=CC=CC=C1N1CCNCC1 WICKLEOONJPMEQ-UHFFFAOYSA-N 0.000 description 1
- QJULELIONYLITF-UHFFFAOYSA-N 1-(2-propan-2-yloxyphenyl)piperazine Chemical compound CC(C)OC1=CC=CC=C1N1CCNCC1 QJULELIONYLITF-UHFFFAOYSA-N 0.000 description 1
- YJVWAFAWDZLZLX-UHFFFAOYSA-N 1-(4,5-dihydro-3h-1,2-benzodioxepin-6-yl)piperazine Chemical compound C1CNCCN1C1=CC=CC2=C1CCCOO2 YJVWAFAWDZLZLX-UHFFFAOYSA-N 0.000 description 1
- WRDWCKDQEXIPNC-UHFFFAOYSA-N 1-(4-chloro-2-ethoxyphenyl)piperazine Chemical compound CCOC1=CC(Cl)=CC=C1N1CCNCC1 WRDWCKDQEXIPNC-UHFFFAOYSA-N 0.000 description 1
- DDWNTNPKMAHGGQ-UHFFFAOYSA-N 1-(4-chloro-2-propoxyphenyl)piperazine Chemical compound CCCOC1=CC(Cl)=CC=C1N1CCNCC1 DDWNTNPKMAHGGQ-UHFFFAOYSA-N 0.000 description 1
- QBLQGSYVHVJZKI-UHFFFAOYSA-N 1-(4-fluoro-2-methylphenyl)piperazine Chemical compound CC1=CC(F)=CC=C1N1CCNCC1 QBLQGSYVHVJZKI-UHFFFAOYSA-N 0.000 description 1
- AWCWOLWZOQHONF-UHFFFAOYSA-N 1-(4-fluoro-2-propoxyphenyl)piperazine Chemical compound CCCOC1=CC(F)=CC=C1N1CCNCC1 AWCWOLWZOQHONF-UHFFFAOYSA-N 0.000 description 1
- FGFOOYFLDKFDAG-UHFFFAOYSA-N 1-(5-chloro-2-fluorophenyl)piperazine Chemical compound FC1=CC=C(Cl)C=C1N1CCNCC1 FGFOOYFLDKFDAG-UHFFFAOYSA-N 0.000 description 1
- LYPKLJIYXQVTPF-UHFFFAOYSA-N 1-(5-fluoro-2-methoxyphenyl)piperazine Chemical compound COC1=CC=C(F)C=C1N1CCNCC1 LYPKLJIYXQVTPF-UHFFFAOYSA-N 0.000 description 1
- OILYGSQXSLUZSY-UHFFFAOYSA-N 1-(6-methoxypyridin-2-yl)piperazine Chemical compound COC1=CC=CC(N2CCNCC2)=N1 OILYGSQXSLUZSY-UHFFFAOYSA-N 0.000 description 1
- CZXCOAOWGJWRHK-UHFFFAOYSA-N 1-(7-chloro-2,3-dihydro-1,4-benzodioxin-5-yl)piperazine Chemical compound C=1C(Cl)=CC=2OCCOC=2C=1N1CCNCC1 CZXCOAOWGJWRHK-UHFFFAOYSA-N 0.000 description 1
- OCDKHNIROLGDKR-UHFFFAOYSA-N 1-[(2,5-dichlorophenyl)methyl]piperazine Chemical compound ClC1=CC=C(Cl)C(CN2CCNCC2)=C1 OCDKHNIROLGDKR-UHFFFAOYSA-N 0.000 description 1
- VTKXPESKKMTHJP-UHFFFAOYSA-N 1-[(2,5-difluorophenyl)methyl]piperazine Chemical compound FC1=CC=C(F)C(CN2CCNCC2)=C1 VTKXPESKKMTHJP-UHFFFAOYSA-N 0.000 description 1
- HNUDCOJENMOJPE-UHFFFAOYSA-N 1-[(2-bromo-5-methoxyphenyl)methyl]piperazine Chemical compound COC1=CC=C(Br)C(CN2CCNCC2)=C1 HNUDCOJENMOJPE-UHFFFAOYSA-N 0.000 description 1
- JOWPEBYCPPLVNX-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]piperazine Chemical compound ClC1=CC=CC=C1CN1CCNCC1 JOWPEBYCPPLVNX-UHFFFAOYSA-N 0.000 description 1
- STALANBIHAODET-UHFFFAOYSA-N 1-[2-(2,2,2-trifluoroethoxy)phenyl]piperazine Chemical compound FC(F)(F)COC1=CC=CC=C1N1CCNCC1 STALANBIHAODET-UHFFFAOYSA-N 0.000 description 1
- NONHMRZXKRBXRX-UHFFFAOYSA-N 1-[2-(trifluoromethoxy)phenyl]piperazine Chemical compound FC(F)(F)OC1=CC=CC=C1N1CCNCC1 NONHMRZXKRBXRX-UHFFFAOYSA-N 0.000 description 1
- VZUBMIDXJRGARE-UHFFFAOYSA-N 1-[2-(trifluoromethyl)phenyl]piperazine Chemical compound FC(F)(F)C1=CC=CC=C1N1CCNCC1 VZUBMIDXJRGARE-UHFFFAOYSA-N 0.000 description 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 description 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 description 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 description 1
- VLYIMIRBUDAQGK-UHFFFAOYSA-N 1-[2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]prop-2-en-1-one Chemical compound C1CC2=CC=CC=C2N(C(=O)C=C)C1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 VLYIMIRBUDAQGK-UHFFFAOYSA-N 0.000 description 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 description 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 description 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 description 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 description 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 description 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 description 1
- SSWLUCQLJACPOR-UHFFFAOYSA-N 1-[2-methoxy-5-(trifluoromethyl)phenyl]piperazine Chemical compound COC1=CC=C(C(F)(F)F)C=C1N1CCNCC1 SSWLUCQLJACPOR-UHFFFAOYSA-N 0.000 description 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 description 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 description 1
- CALRMTBQHPJIOJ-UHFFFAOYSA-N 1-benzyl-4-naphthalen-1-ylpiperazine Chemical compound C1CN(C=2C3=CC=CC=C3C=CC=2)CCN1CC1=CC=CC=C1 CALRMTBQHPJIOJ-UHFFFAOYSA-N 0.000 description 1
- DLKQHBOKULLWDQ-UHFFFAOYSA-N 1-bromonaphthalene Chemical compound C1=CC=C2C(Br)=CC=CC2=C1 DLKQHBOKULLWDQ-UHFFFAOYSA-N 0.000 description 1
- VSTXCZGEEVFJES-UHFFFAOYSA-N 1-cycloundecyl-1,5-diazacycloundec-5-ene Chemical compound C1CCCCCC(CCCC1)N1CCCCCC=NCCC1 VSTXCZGEEVFJES-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- IDFYLSABDUMICK-UHFFFAOYSA-N 1-piperazin-1-ylisoquinoline Chemical compound C1CNCCN1C1=NC=CC2=CC=CC=C12 IDFYLSABDUMICK-UHFFFAOYSA-N 0.000 description 1
- OQZBAQXTXNIPRA-UHFFFAOYSA-N 1-pyridin-4-ylpiperazine Chemical compound C1CNCCN1C1=CC=NC=C1 OQZBAQXTXNIPRA-UHFFFAOYSA-N 0.000 description 1
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 1
- SHMNLEQWIMKCQA-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanoyl chloride Chemical compound FC(F)(F)C(F)(F)C(Cl)=O SHMNLEQWIMKCQA-UHFFFAOYSA-N 0.000 description 1
- FCDVTQPIRBFUEU-UHFFFAOYSA-N 2,2-bis(bromomethyl)-6-(trifluoromethoxy)-1h-quinoline Chemical compound N1C(CBr)(CBr)C=CC2=CC(OC(F)(F)F)=CC=C21 FCDVTQPIRBFUEU-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- SRBIHKSWFZJZFZ-UHFFFAOYSA-N 2,3-dimethyl-1h-indol-7-amine Chemical compound C1=CC=C2C(C)=C(C)NC2=C1N SRBIHKSWFZJZFZ-UHFFFAOYSA-N 0.000 description 1
- ONCCVOJTXZBTDY-UHFFFAOYSA-N 2,3-dimethyl-7-nitro-1h-indole Chemical compound C1=CC=C2C(C)=C(C)NC2=C1[N+]([O-])=O ONCCVOJTXZBTDY-UHFFFAOYSA-N 0.000 description 1
- VOIPEKOXTFLQNY-UHFFFAOYSA-N 2-(2-methoxyphenoxy)-n-methylethanamine Chemical compound CNCCOC1=CC=CC=C1OC VOIPEKOXTFLQNY-UHFFFAOYSA-N 0.000 description 1
- QPMPQCURMPKIID-UHFFFAOYSA-N 2-(chloromethyl)-1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2NC(CCl)CCC2=C1 QPMPQCURMPKIID-UHFFFAOYSA-N 0.000 description 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 description 1
- MFVCIOLUKKPQLX-UHFFFAOYSA-N 2-[(4-phenylpiperazin-1-yl)methyl]-1,2,3,4-tetrahydroquinoline Chemical compound C1CC2=CC=CC=C2NC1CN(CC1)CCN1C1=CC=CC=C1 MFVCIOLUKKPQLX-UHFFFAOYSA-N 0.000 description 1
- DLDKERYAZGDBHR-UHFFFAOYSA-N 2-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]quinoline Chemical compound COC1=CC=CC=C1N1CCN(CCC=2N=C3C=CC=CC3=CC=2)CC1 DLDKERYAZGDBHR-UHFFFAOYSA-N 0.000 description 1
- PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 description 1
- GXGWPYFYIZFGCH-UHFFFAOYSA-N 2-[[4-(1h-indol-4-yl)piperazin-1-yl]methyl]-n-[(4-methoxyphenyl)methyl]-3,4-dihydro-2h-quinoline-1-carboxamide Chemical compound C1=CC(OC)=CC=C1CNC(=O)N1C2=CC=CC=C2CCC1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 GXGWPYFYIZFGCH-UHFFFAOYSA-N 0.000 description 1
- AYSDVBUMTYYYTD-UHFFFAOYSA-N 2-[[4-(2-methoxyphenyl)piperidin-1-yl]methyl]-1,2,3,4-tetrahydroquinoline Chemical compound COC1=CC=CC=C1C1CCN(CC2NC3=CC=CC=C3CC2)CC1 AYSDVBUMTYYYTD-UHFFFAOYSA-N 0.000 description 1
- UWCVEKNQCTWPMM-UHFFFAOYSA-N 2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-8-methylquinoline Chemical compound COC1=CC(F)=CC=C1N1CCN(CC=2N=C3C(C)=CC=CC3=CC=2)CC1 UWCVEKNQCTWPMM-UHFFFAOYSA-N 0.000 description 1
- WPFVUPAQRXVCQV-UHFFFAOYSA-N 2-[[4-(4-fluorophenyl)piperazin-1-yl]methyl]-6-(trifluoromethyl)-1,2,3,4-tetrahydroquinoline Chemical compound C1=CC(F)=CC=C1N1CCN(CC2NC3=CC=C(C=C3CC2)C(F)(F)F)CC1 WPFVUPAQRXVCQV-UHFFFAOYSA-N 0.000 description 1
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
- YMDZDFSUDFLGMX-UHFFFAOYSA-N 2-chloro-n-(2-chloroethyl)ethanamine;hydron;chloride Chemical compound [Cl-].ClCC[NH2+]CCCl YMDZDFSUDFLGMX-UHFFFAOYSA-N 0.000 description 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 description 1
- XUGNJOCQALIQFG-UHFFFAOYSA-N 2-ethenylquinoline Chemical compound C1=CC=CC2=NC(C=C)=CC=C21 XUGNJOCQALIQFG-UHFFFAOYSA-N 0.000 description 1
- BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical class C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 1
- XQWCBTYHXJMGAU-UHFFFAOYSA-N 2-methyl-1h-indol-7-amine Chemical compound C1=CC(N)=C2NC(C)=CC2=C1 XQWCBTYHXJMGAU-UHFFFAOYSA-N 0.000 description 1
- CMQRMBNFYVGLRO-UHFFFAOYSA-N 2-methyl-4-piperazin-1-yl-1h-indole Chemical compound C1=CC=C2NC(C)=CC2=C1N1CCNCC1 CMQRMBNFYVGLRO-UHFFFAOYSA-N 0.000 description 1
- TYJFYUVDUUACKX-UHFFFAOYSA-N 2-methylquinolin-6-amine Chemical compound C1=C(N)C=CC2=NC(C)=CC=C21 TYJFYUVDUUACKX-UHFFFAOYSA-N 0.000 description 1
- UORNTHBBLYBAJJ-UHFFFAOYSA-N 2-piperazin-1-ylphenol Chemical compound OC1=CC=CC=C1N1CCNCC1 UORNTHBBLYBAJJ-UHFFFAOYSA-N 0.000 description 1
- HCGFLVDMFDHYJD-UHFFFAOYSA-N 2-piperazin-1-ylpyrazine Chemical compound C1CNCCN1C1=CN=CC=N1 HCGFLVDMFDHYJD-UHFFFAOYSA-N 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- VOSQLWCTKGQTAY-UHFFFAOYSA-N 3,3,3-trifluoropropanoyl chloride Chemical compound FC(F)(F)CC(Cl)=O VOSQLWCTKGQTAY-UHFFFAOYSA-N 0.000 description 1
- RJCICIFHSDEDBW-UHFFFAOYSA-N 3-(dimethylamino)-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)CCN(C)C)C1CN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 RJCICIFHSDEDBW-UHFFFAOYSA-N 0.000 description 1
- BKDMXVREWXKZLB-UHFFFAOYSA-N 3-benzylpiperidine Chemical compound C=1C=CC=CC=1CC1CCCNC1 BKDMXVREWXKZLB-UHFFFAOYSA-N 0.000 description 1
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
- QZVQQUVWFIZUBQ-UHFFFAOYSA-N 3-fluoroaniline Chemical compound NC1=CC=CC(F)=C1 QZVQQUVWFIZUBQ-UHFFFAOYSA-N 0.000 description 1
- KUCXRVACKIFDOV-UHFFFAOYSA-N 3-methoxy-4-piperazin-1-ylphenol Chemical compound COC1=CC(O)=CC=C1N1CCNCC1 KUCXRVACKIFDOV-UHFFFAOYSA-N 0.000 description 1
- QKOOBPCFTVGNFP-UHFFFAOYSA-N 3-propan-2-yloxypropanoyl chloride Chemical compound CC(C)OCCC(Cl)=O QKOOBPCFTVGNFP-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- VHXAVSKIFOOMGB-UHFFFAOYSA-N 4-(2-methoxyphenoxy)piperidine Chemical compound COC1=CC=CC=C1OC1CCNCC1 VHXAVSKIFOOMGB-UHFFFAOYSA-N 0.000 description 1
- XUJFOSLZQITUOI-UHFFFAOYSA-N 4-(trifluoromethoxy)aniline Chemical compound NC1=CC=C(OC(F)(F)F)C=C1 XUJFOSLZQITUOI-UHFFFAOYSA-N 0.000 description 1
- RHZUYYRZMJNUIL-UHFFFAOYSA-N 4-[2-[[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinoline-1-carbonyl]benzonitrile Chemical compound COC1=CC(F)=CC=C1N1CCN(CC2N(C3=CC=CC=C3CC2)C(=O)C=2C=CC(=CC=2)C#N)CC1 RHZUYYRZMJNUIL-UHFFFAOYSA-N 0.000 description 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 description 1
- LBCGFYCLVZBYPP-UHFFFAOYSA-N 4-chloro-2-piperazin-1-ylbenzonitrile Chemical compound ClC1=CC=C(C#N)C(N2CCNCC2)=C1 LBCGFYCLVZBYPP-UHFFFAOYSA-N 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- FGXAOQFRWBVXQC-UHFFFAOYSA-N 4-methoxy-3-piperazin-1-ylbenzonitrile Chemical compound COC1=CC=C(C#N)C=C1N1CCNCC1 FGXAOQFRWBVXQC-UHFFFAOYSA-N 0.000 description 1
- FXVZTWCWCWQGNW-UHFFFAOYSA-N 4-piperazin-1-yl-1h-indole-3-carbonitrile Chemical compound C=12C(C#N)=CNC2=CC=CC=1N1CCNCC1 FXVZTWCWCWQGNW-UHFFFAOYSA-N 0.000 description 1
- XFJBGINZIMNZBW-CRAIPNDOSA-N 5-chloro-2-[4-[(1r,2s)-2-[2-(5-methylsulfonylpyridin-2-yl)oxyethyl]cyclopropyl]piperidin-1-yl]pyrimidine Chemical compound N1=CC(S(=O)(=O)C)=CC=C1OCC[C@H]1[C@@H](C2CCN(CC2)C=2N=CC(Cl)=CN=2)C1 XFJBGINZIMNZBW-CRAIPNDOSA-N 0.000 description 1
- LAZSCXFXUBMGGC-UHFFFAOYSA-N 5-nitro-2-piperazin-1-ylbenzonitrile Chemical compound N#CC1=CC([N+](=O)[O-])=CC=C1N1CCNCC1 LAZSCXFXUBMGGC-UHFFFAOYSA-N 0.000 description 1
- RNGWPAAZTWTLEJ-UHFFFAOYSA-N 6-chloro-1,2,3,4-tetrahydroquinoline-2-carboxylic acid Chemical compound ClC1=CC=C2NC(C(=O)O)CCC2=C1 RNGWPAAZTWTLEJ-UHFFFAOYSA-N 0.000 description 1
- OCCIBGIEIBQGAJ-UHFFFAOYSA-N 6-chloro-2-methylquinoline Chemical compound C1=C(Cl)C=CC2=NC(C)=CC=C21 OCCIBGIEIBQGAJ-UHFFFAOYSA-N 0.000 description 1
- UEVBMCGIDNGKCL-UHFFFAOYSA-N 6-fluoro-2-[[4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl]methyl]quinoline Chemical compound C1=CC2=CC(F)=CC=C2N=C1CN(CC1)CCN1C1=CC=CC=C1OCC(F)(F)F UEVBMCGIDNGKCL-UHFFFAOYSA-N 0.000 description 1
- RMDCSDVIVXJELQ-UHFFFAOYSA-N 6-fluoroquinoline Chemical compound N1=CC=CC2=CC(F)=CC=C21 RMDCSDVIVXJELQ-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- WQZQFYRSYLXBGP-UHFFFAOYSA-N 7-chloro-2-methylquinoline Chemical compound C1=CC(Cl)=CC2=NC(C)=CC=C21 WQZQFYRSYLXBGP-UHFFFAOYSA-N 0.000 description 1
- ULPLMLOWDCHLGZ-UHFFFAOYSA-N 7-methoxy-1h-indol-4-amine Chemical compound COC1=CC=C(N)C2=C1NC=C2 ULPLMLOWDCHLGZ-UHFFFAOYSA-N 0.000 description 1
- LLEMQUFWHPCBIT-UHFFFAOYSA-N 7-methoxy-4-nitro-1h-indole Chemical compound COC1=CC=C([N+]([O-])=O)C2=C1NC=C2 LLEMQUFWHPCBIT-UHFFFAOYSA-N 0.000 description 1
- MFFDYVSTSNKVJX-UHFFFAOYSA-N 7-methyl-1,2,3,4-tetrahydroquinoline-2-carboxylic acid Chemical compound C1CC(C(O)=O)NC2=CC(C)=CC=C21 MFFDYVSTSNKVJX-UHFFFAOYSA-N 0.000 description 1
- JDQNDHBUAHUCOC-UHFFFAOYSA-N 7-methyl-1h-indol-4-amine Chemical compound CC1=CC=C(N)C2=C1NC=C2 JDQNDHBUAHUCOC-UHFFFAOYSA-N 0.000 description 1
- PGDQJLNWTYACPC-UHFFFAOYSA-N 7-methyl-4-nitro-1h-indole Chemical compound CC1=CC=C([N+]([O-])=O)C2=C1NC=C2 PGDQJLNWTYACPC-UHFFFAOYSA-N 0.000 description 1
- XKDAUEWDPSMDGG-UHFFFAOYSA-N 7-piperazin-1-yl-1h-indole Chemical compound C1CNCCN1C1=CC=CC2=C1NC=C2 XKDAUEWDPSMDGG-UHFFFAOYSA-N 0.000 description 1
- SLBPIHCMXPQAIQ-UHFFFAOYSA-N 8-hydroxyquinoline-2-carbaldehyde Chemical compound C1=C(C=O)N=C2C(O)=CC=CC2=C1 SLBPIHCMXPQAIQ-UHFFFAOYSA-N 0.000 description 1
- DCUZDOXGNVJQQL-UHFFFAOYSA-N 8-piperazin-1-ylquinoline Chemical compound C1CNCCN1C1=CC=CC2=CC=CN=C12 DCUZDOXGNVJQQL-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- POJWUDADGALRAB-PVQJCKRUSA-N Allantoin Natural products NC(=O)N[C@@H]1NC(=O)NC1=O POJWUDADGALRAB-PVQJCKRUSA-N 0.000 description 1
- 244000144927 Aloe barbadensis Species 0.000 description 1
- 235000002961 Aloe barbadensis Nutrition 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 206010056948 Automatic bladder Diseases 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 206010005033 Bladder dilatation Diseases 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OJRUSAPKCPIVBY-KQYNXXCUSA-N C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N Chemical compound C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N OJRUSAPKCPIVBY-KQYNXXCUSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 102000002004 Cytochrome P-450 Enzyme System Human genes 0.000 description 1
- 108010015742 Cytochrome P-450 Enzyme System Proteins 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 206010012335 Dependence Diseases 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 1
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
- 208000030814 Eating disease Diseases 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 208000019454 Feeding and Eating disease Diseases 0.000 description 1
- CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 description 1
- 229930182566 Gentamicin Natural products 0.000 description 1
- 102000016354 Glucuronosyltransferase Human genes 0.000 description 1
- 108010092364 Glucuronosyltransferase Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 238000006683 Mannich reaction Methods 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 229920003091 Methocel™ Polymers 0.000 description 1
- 238000006751 Mitsunobu reaction Methods 0.000 description 1
- 206010053236 Mixed incontinence Diseases 0.000 description 1
- ULMHMJAEGZPQRY-UHFFFAOYSA-N N-(tert-butoxycarbonyl)piperidin-2-one Chemical class CC(C)(C)OC(=O)N1CCCCC1=O ULMHMJAEGZPQRY-UHFFFAOYSA-N 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
- 230000006181 N-acylation Effects 0.000 description 1
- 229910018954 NaNH2 Inorganic materials 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000029726 Neurodevelopmental disease Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 206010033799 Paralysis Diseases 0.000 description 1
- DPWPWRLQFGFJFI-UHFFFAOYSA-N Pargyline Chemical compound C#CCN(C)CC1=CC=CC=C1 DPWPWRLQFGFJFI-UHFFFAOYSA-N 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920002873 Polyethylenimine Polymers 0.000 description 1
- 229920001710 Polyorthoester Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910019020 PtO2 Inorganic materials 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 201000001880 Sexual dysfunction Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 description 1
- 108050001286 Somatostatin Receptor Proteins 0.000 description 1
- 102000011096 Somatostatin receptor Human genes 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 238000006859 Swern oxidation reaction Methods 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
- XCCTYIAWTASOJW-XVFCMESISA-N Uridine-5'-Diphosphate Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(O)=O)O[C@H]1N1C(=O)NC(=O)C=C1 XCCTYIAWTASOJW-XVFCMESISA-N 0.000 description 1
- 206010046543 Urinary incontinence Diseases 0.000 description 1
- 229920001938 Vegetable gum Polymers 0.000 description 1
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- WWDJBJMMVDQYCH-UHFFFAOYSA-N [2-[(4-isoquinolin-1-ylpiperazin-1-yl)methyl]-3,4-dihydro-2h-quinolin-1-yl]-(1h-pyrrol-2-yl)methanone Chemical compound C1CN(C=2C3=CC=CC=C3C=CN=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1=CC=CN1 WWDJBJMMVDQYCH-UHFFFAOYSA-N 0.000 description 1
- FGLXYLYCGPTURI-UHFFFAOYSA-N [2-[[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]methyl]-3,4-dihydro-2h-quinolin-1-yl]-cyclohexylmethanone Chemical compound C1CN(CC=2C=C3OCOC3=CC=2)CCN1CC1CCC2=CC=CC=C2N1C(=O)C1CCCCC1 FGLXYLYCGPTURI-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 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 description 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 description 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 description 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 description 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 description 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 description 1
- 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 description 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 description 1
- 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 description 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 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 210000003815 abdominal wall Anatomy 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 230000001270 agonistic effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical class O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000004457 alkyl amino carbonyl group Chemical group 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
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 1
- 229960000458 allantoin Drugs 0.000 description 1
- 235000011399 aloe vera Nutrition 0.000 description 1
- 102000004305 alpha Adrenergic Receptors Human genes 0.000 description 1
- 108090000861 alpha Adrenergic Receptors Proteins 0.000 description 1
- 102000030619 alpha-1 Adrenergic Receptor Human genes 0.000 description 1
- 108020004102 alpha-1 Adrenergic Receptor Proteins 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000010775 animal oil Substances 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
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000001078 anti-cholinergic effect Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 1
- 230000002567 autonomic effect Effects 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000012216 bentonite Nutrition 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 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
- 230000000975 bioactive effect Effects 0.000 description 1
- 229920002988 biodegradable polymer Polymers 0.000 description 1
- 239000004621 biodegradable polymer Substances 0.000 description 1
- TXFLGZOGNOOEFZ-UHFFFAOYSA-N bis(2-chloroethyl)amine Chemical compound ClCCNCCCl TXFLGZOGNOOEFZ-UHFFFAOYSA-N 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- 208000029162 bladder disease Diseases 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 229910010277 boron hydride Inorganic materials 0.000 description 1
- UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 210000000133 brain stem Anatomy 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- UOPDWLKMAYCQLM-UHFFFAOYSA-N carbamoyl chloride;n-chloroformamide Chemical compound NC(Cl)=O.ClNC=O UOPDWLKMAYCQLM-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000007942 carboxylates Chemical group 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 210000003710 cerebral cortex Anatomy 0.000 description 1
- NCEXYHBECQHGNR-UHFFFAOYSA-N chembl421 Chemical compound C1=C(O)C(C(=O)O)=CC(N=NC=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-UHFFFAOYSA-N 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000010568 chiral column chromatography Methods 0.000 description 1
- RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 description 1
- 229960002327 chloral hydrate Drugs 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000011284 combination treatment Methods 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 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
- 239000013058 crude material Substances 0.000 description 1
- JWEKFMCYIRVOQZ-UHFFFAOYSA-N cyanamide;sodium Chemical compound [Na].NC#N JWEKFMCYIRVOQZ-UHFFFAOYSA-N 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 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 description 1
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 1
- CIYPNZYEUZQIHN-UHFFFAOYSA-N cycloheptanecarbonyl chloride Chemical compound ClC(=O)C1CCCCCC1 CIYPNZYEUZQIHN-UHFFFAOYSA-N 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- CXWMHIRIXVNVQN-UHFFFAOYSA-N cyclohex-3-ene-1-carbonyl chloride Chemical compound ClC(=O)C1CCC=CC1 CXWMHIRIXVNVQN-UHFFFAOYSA-N 0.000 description 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 description 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 description 1
- OATYGXSDGUMNFW-UHFFFAOYSA-N cyclohexyl-[2-[[2-(2-methoxyphenoxy)ethylamino]methyl]-3,4-dihydro-2h-quinolin-1-yl]methanone Chemical compound COC1=CC=CC=C1OCCNCC1N(C(=O)C2CCCCC2)C2=CC=CC=C2CC1 OATYGXSDGUMNFW-UHFFFAOYSA-N 0.000 description 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 description 1
- 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 description 1
- 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 description 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 description 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 description 1
- 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 description 1
- 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 description 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 description 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 description 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 description 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 description 1
- 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 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- UENYZHRJUHTRPY-UHFFFAOYSA-N cyclopentyl-[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)C2CCCC2)CC1 UENYZHRJUHTRPY-UHFFFAOYSA-N 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 239000007933 dermal patch Substances 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- VHILMKFSCRWWIJ-UHFFFAOYSA-N dimethyl acetylenedicarboxylate Chemical compound COC(=O)C#CC(=O)OC VHILMKFSCRWWIJ-UHFFFAOYSA-N 0.000 description 1
- 125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 150000002013 dioxins Chemical class 0.000 description 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 235000014632 disordered eating Nutrition 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- RUZYUOTYCVRMRZ-UHFFFAOYSA-N doxazosin Chemical compound C1OC2=CC=CC=C2OC1C(=O)N(CC1)CCN1C1=NC(N)=C(C=C(C(OC)=C2)OC)C2=N1 RUZYUOTYCVRMRZ-UHFFFAOYSA-N 0.000 description 1
- 229960001389 doxazosin Drugs 0.000 description 1
- 206010013781 dry mouth Diseases 0.000 description 1
- 210000001198 duodenum Anatomy 0.000 description 1
- 238000004836 empirical method Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 239000012055 enteric layer Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 1
- QQXQAEWRSVZPJM-UHFFFAOYSA-N ethyl 1h-indole-2-carboxylate Chemical compound C1=CC=C2NC(C(=O)OCC)=CC2=C1 QQXQAEWRSVZPJM-UHFFFAOYSA-N 0.000 description 1
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-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
- 238000000605 extraction Methods 0.000 description 1
- 230000035611 feeding Effects 0.000 description 1
- 230000004634 feeding behavior Effects 0.000 description 1
- 239000012091 fetal bovine serum Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 229960002518 gentamicin Drugs 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000000285 glutaminergic effect Effects 0.000 description 1
- 229960005150 glycerol Drugs 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 238000007163 homologation reaction Methods 0.000 description 1
- 210000005260 human cell Anatomy 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical class C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-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
- 150000002476 indolines Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 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
- FZWBNHMXJMCXLU-BLAUPYHCSA-N isomaltotriose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O)O1 FZWBNHMXJMCXLU-BLAUPYHCSA-N 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 210000004731 jugular vein Anatomy 0.000 description 1
- 230000003907 kidney function Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 239000008297 liquid dosage form Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 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
- 210000005229 liver cell Anatomy 0.000 description 1
- 230000003908 liver function Effects 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 229960001708 magnesium carbonate Drugs 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 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
- NQPIEWBAWBFGOB-UHFFFAOYSA-N methyl 1h-indole-2-carboxylate Chemical group C1=CC=C2NC(C(=O)OC)=CC2=C1 NQPIEWBAWBFGOB-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 230000036453 micturition reflex Effects 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 231100000324 minimal toxicity Toxicity 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229940078555 myristyl propionate Drugs 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
- WTFJTOMIZDBASO-UHFFFAOYSA-N n-[[1-(benzenesulfonyl)-3,4-dihydro-2h-quinolin-2-yl]methyl]-2-(2-methoxyphenoxy)-n-methylethanamine Chemical compound COC1=CC=CC=C1OCCN(C)CC1N(S(=O)(=O)C=2C=CC=CC=2)C2=CC=CC=C2CC1 WTFJTOMIZDBASO-UHFFFAOYSA-N 0.000 description 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 description 1
- MGNPLIACIXIYJE-UHFFFAOYSA-N n-fluoroaniline Chemical compound FNC1=CC=CC=C1 MGNPLIACIXIYJE-UHFFFAOYSA-N 0.000 description 1
- LKPFBGKZCCBZDK-UHFFFAOYSA-N n-hydroxypiperidine Chemical compound ON1CCCCC1 LKPFBGKZCCBZDK-UHFFFAOYSA-N 0.000 description 1
- DXDQLIOPEGWHHU-UHFFFAOYSA-N n-tert-butyl-2-[(4-isoquinolin-1-ylpiperazin-1-yl)methyl]-3,4-dihydro-2h-quinoline-1-carboxamide Chemical compound C1CC2=CC=CC=C2N(C(=O)NC(C)(C)C)C1CN1CCN(C=2C3=CC=CC=C3C=CN=2)CC1 DXDQLIOPEGWHHU-UHFFFAOYSA-N 0.000 description 1
- SGOFFVAYDIITAK-UHFFFAOYSA-N n-tert-butyl-2-[[2-(2-methoxyphenoxy)ethyl-methylamino]methyl]-3,4-dihydro-2h-quinoline-1-carboxamide Chemical compound COC1=CC=CC=C1OCCN(C)CC1N(C(=O)NC(C)(C)C)C2=CC=CC=C2CC1 SGOFFVAYDIITAK-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229920001206 natural gum Polymers 0.000 description 1
- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000007472 neurodevelopment Effects 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 208000024449 overflow incontinence Diseases 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 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
- 230000001734 parasympathetic effect Effects 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 229960001779 pargyline Drugs 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 210000003903 pelvic floor Anatomy 0.000 description 1
- 210000004197 pelvis Anatomy 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000004894 pentylamino group Chemical group C(CCCC)N* 0.000 description 1
- 230000002572 peristaltic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 125000003395 phenylethylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- 150000008105 phosphatidylcholines Chemical class 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 230000007084 physiological dysfunction Effects 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000004626 polylactic acid Substances 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 229940093916 potassium phosphate Drugs 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 201000007094 prostatitis Diseases 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- BHGCGZJIGFPIDE-UHFFFAOYSA-N pyrrolidine-3-carbonyl chloride Chemical compound ClC(=O)C1CCNC1 BHGCGZJIGFPIDE-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- WPYJKGWLDJECQD-UHFFFAOYSA-N quinoline-2-carbaldehyde Chemical compound C1=CC=CC2=NC(C=O)=CC=C21 WPYJKGWLDJECQD-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009153 reflex inhibition Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000003727 serotonin 1A antagonist Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 231100000872 sexual dysfunction Toxicity 0.000 description 1
- 210000000329 smooth muscle myocyte Anatomy 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- HBEXQFKVNOXMOD-UHFFFAOYSA-M sodium;2-hydroxy-2,2-diphenylacetate Chemical compound [Na+].C=1C=CC=CC=1C(C([O-])=O)(O)C1=CC=CC=C1 HBEXQFKVNOXMOD-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007892 solid unit dosage form Substances 0.000 description 1
- RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 238000013223 sprague-dawley female rat Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000004149 tartrazine Substances 0.000 description 1
- VCKUSRYTPJJLNI-UHFFFAOYSA-N terazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1CCCO1 VCKUSRYTPJJLNI-UHFFFAOYSA-N 0.000 description 1
- 229960001693 terazosin Drugs 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 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
- YRZGMTHQPGNLEK-UHFFFAOYSA-N tetradecyl propionate Chemical compound CCCCCCCCCCCCCCOC(=O)CC YRZGMTHQPGNLEK-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 238000011285 therapeutic regimen Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 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
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- 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
- 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
- C07D215/42—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- 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
- C07D401/12—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
-
- C—CHEMISTRY; METALLURGY
- 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
- C07D401/14—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- 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
-
- 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
- C07D413/08—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
-
- 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
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Urology & Nephrology (AREA)
- Addiction (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Anesthesiology (AREA)
- Vascular Medicine (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 Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT2001MI002060A ITMI20012060A1 (it) | 2001-10-05 | 2001-10-05 | Nuovi eterocilcli n-acilati |
PCT/EP2002/011282 WO2003031436A1 (fr) | 2001-10-05 | 2002-10-07 | Composes heterocycliques utilises pour traiter des troubles de la voie urinaire |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20040392A2 true HRP20040392A2 (en) | 2004-10-31 |
Family
ID=11448476
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HR20040392A HRP20040392A2 (en) | 2001-10-05 | 2004-05-04 | Heterocyclic compounds for use in the treatment of disorders of the urinary tract |
Country Status (33)
Country | Link |
---|---|
US (2) | US20030181446A1 (fr) |
EP (1) | EP1432701B1 (fr) |
JP (1) | JP2005508952A (fr) |
KR (1) | KR20040048930A (fr) |
CN (1) | CN1564820A (fr) |
AP (1) | AP1705A (fr) |
AR (1) | AR036743A1 (fr) |
AT (1) | ATE313540T1 (fr) |
AU (1) | AU2002346979B9 (fr) |
BR (1) | BR0213067A (fr) |
CA (1) | CA2458456A1 (fr) |
CO (1) | CO5570679A2 (fr) |
CY (1) | CY1104991T1 (fr) |
DE (1) | DE60208221T2 (fr) |
DK (1) | DK1432701T3 (fr) |
EA (1) | EA200400507A1 (fr) |
EC (1) | ECSP045095A (fr) |
ES (1) | ES2253568T3 (fr) |
HK (1) | HK1067362A1 (fr) |
HR (1) | HRP20040392A2 (fr) |
HU (1) | HUP0401598A2 (fr) |
IT (1) | ITMI20012060A1 (fr) |
MA (1) | MA27067A1 (fr) |
MX (1) | MXPA04002962A (fr) |
NO (1) | NO20041833L (fr) |
NZ (1) | NZ532511A (fr) |
OA (1) | OA12663A (fr) |
PL (1) | PL369763A1 (fr) |
SI (1) | SI1432701T1 (fr) |
TN (1) | TNSN04053A1 (fr) |
WO (1) | WO2003031436A1 (fr) |
YU (1) | YU27204A (fr) |
ZA (1) | ZA200403356B (fr) |
Families Citing this family (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AR035521A1 (es) * | 2000-12-22 | 2004-06-02 | Lundbeck & Co As H | Derivados de 3-indolina y composicion farmaceutica que los comprende |
ATE424825T1 (de) | 2001-07-20 | 2009-03-15 | Psychogenics Inc | Behandlung von hyperaktivitätsstörungen und aufmerksamkeitsdefiziten |
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 |
WO2005056552A1 (fr) * | 2003-12-09 | 2005-06-23 | Vertex Pharmaceuticals Incorporated | Derives de naphtyridine et leur utilisation en tant que modulateurs de recepteurs muscariniques |
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 |
DE102005027168A1 (de) * | 2005-06-13 | 2006-12-14 | Merck Patent Gmbh | Tetrahydrochinoline |
JP2009536954A (ja) | 2006-05-11 | 2009-10-22 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | Cetp阻害剤としての3,4−ジヒドロ−2h−ベンゾ[1,4]オキサジンおよびチアジン誘導体 |
US7928238B2 (en) | 2006-05-11 | 2011-04-19 | Janssen Pharmaceutica Nv | 1,2,3,4-tetrahydro-quinoline derivatives as CETP inhibitors |
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 |
TW200811158A (en) * | 2006-06-27 | 2008-03-01 | Sanofi Aventis | Piperidine or pyrrolidine urea derivatives, their preparation and their therapeutic application |
TW200811170A (en) | 2006-06-27 | 2008-03-01 | Sanofi Aventis | Urea derivatives of tropane, their preparation and their therapeutic application |
JP2009543871A (ja) | 2006-07-19 | 2009-12-10 | ジ・オハイオ・ステイト・ユニバーシティ・リサーチ・ファウンデイション | 選択的アンドロゲン受容体調節薬、その類似体及び誘導体とそれらの使用 |
KR20090018593A (ko) * | 2007-08-17 | 2009-02-20 | 주식회사 엘지생명과학 | 세포괴사 저해제로서의 인돌 및 인다졸 화합물 |
KR101640512B1 (ko) * | 2008-04-24 | 2016-07-18 | 더 리젠츠 오브 더 유니버시티 오브 캘리포니아 | 안드로겐 수용체의 소분자 억제제 |
FR2969151B1 (fr) * | 2010-12-17 | 2016-11-04 | Oreal | Derives du 4-amino et leur utilisation pour la coloration d'oxydation des fibres keratiniques. |
WO2015035278A1 (fr) * | 2013-09-09 | 2015-03-12 | Bristol-Myers Squibb Company | Modulateurs de rorγ |
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 |
Family Cites Families (40)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1027611A (en) * | 1962-01-04 | 1966-04-27 | May & Baker Ltd | Phenoxy- and phenylthio-alkylamines and acid addition salts thereof |
GB1166538A (en) * | 1967-06-10 | 1969-10-08 | Pfizer Ltd | Substituted Tetrahydroquinolines |
US3983121A (en) * | 1974-07-01 | 1976-09-28 | Council Of Scientific And Industrial Research | 1-Substituted 4-(β-2-quinolylethyl)piperazines and 1,2,3,4-tetrahydroquinolyl-ethyl analogues thereof |
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 |
US4461896A (en) * | 1979-02-07 | 1984-07-24 | Norwich Eaton Pharmaceuticals, Inc. | 1-[Acylthio) and (mercapto)-1-oxoalkyl]-1,2,3,4-tetrahydroquinoline-2-carboxylic acids |
CH653021A5 (fr) * | 1981-04-24 | 1985-12-13 | Delalande Sa | Derives piperidino, piperazino et homopiperazino, n-substitues par un groupe heterocyclique aromatique, leur procede de preparation et composition therapeutique les contenant. |
US4585773A (en) * | 1984-07-11 | 1986-04-29 | Bristol-Myers Company | Isoindolinyl-alkyl-piperazines |
ATE81975T1 (de) * | 1984-12-21 | 1992-11-15 | Duphar Int Res | Arzneimittel mit psychotroper wirkung. |
US4831031A (en) * | 1988-01-22 | 1989-05-16 | Pfizer Inc. | Aryl piperazinyl-(C2 or C4) alkylene heterocyclic compounds having neuroleptic activity |
US5641504A (en) * | 1988-06-09 | 1997-06-24 | Alza Corporation | Skin permeation enhancer compositions using glycerol monolinoleate |
WO1992011843A1 (fr) * | 1991-01-09 | 1992-07-23 | Alza Corporation | Dispositifs bioerodables et compositions pour liberer par diffusion des agents actifs |
US5443459A (en) * | 1991-01-30 | 1995-08-22 | Alza Corporation | Osmotic device for delayed delivery of agent |
JPH05117276A (ja) * | 1991-10-23 | 1993-05-14 | Sumitomo Pharmaceut Co Ltd | 新規な3環性キノキサリンジオン誘導体 |
US5629019A (en) * | 1992-02-27 | 1997-05-13 | Alza Corporation | Formulations with hydrophobic permeation enhancers |
ATE185694T1 (de) * | 1992-05-13 | 1999-11-15 | Alza Corp | Oxybutynin zur transdermalen verabreichung |
US5512293A (en) * | 1992-07-23 | 1996-04-30 | Alza Corporation | Oral sustained release drug delivery device |
US5573776A (en) * | 1992-12-02 | 1996-11-12 | Alza Corporation | Oral osmotic device with hydrogel driving member |
US5533971A (en) * | 1993-09-03 | 1996-07-09 | Alza Corporation | Reduction of skin irritation during electrotransport |
IT1270993B (it) * | 1994-03-18 | 1997-05-26 | Recordati Chem Pharm | Derivati chinzolilamminici attivi come alfa-antagonisti |
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 |
US5859014A (en) * | 1995-06-09 | 1999-01-12 | Syntex (U.S.A.) Inc. | Pyrimidinedione, pyrimidinetrione, triazinedione and tetrahydroquinazolinedione derivatives as α1 -adrenergic receptor antagonists |
US5780058A (en) * | 1995-07-21 | 1998-07-14 | Alza Corporation | Oral delivery of discrete units |
US6096339A (en) * | 1997-04-04 | 2000-08-01 | Alza Corporation | Dosage form, process of making and using same |
DK0882717T3 (da) * | 1996-10-01 | 2010-12-13 | Kyowa Hakko Kirin Co Ltd | Nitrogenholdige heterocykliske forbindelser |
CA2220649C (fr) * | 1996-12-03 | 2007-02-13 | F. Hoffmann-La Roche Ag | Derives de 4-hydroxy-piperidine |
EP0846683B1 (fr) * | 1996-12-03 | 2001-09-19 | F. Hoffmann-La Roche Ag | Dérivés de la 4-hydroxypipéridine |
US6281227B1 (en) * | 1996-12-13 | 2001-08-28 | Aventis Pharma Deutschland Gmbh | Sulfonic acid sulfonylamino n-(heteroaralkyl)-azaheterocyclylamide compounds |
US6331311B1 (en) * | 1996-12-20 | 2001-12-18 | Alza Corporation | Injectable depot gel composition and method of preparing the composition |
US6169086B1 (en) * | 1997-01-27 | 2001-01-02 | Daiichi Pharmaceutical Co., Ltd. | Pyrazole derivatives |
IT1293804B1 (it) * | 1997-08-01 | 1999-03-10 | Recordati Chem Pharm | Diarilalchilpiperazine attive sulle basse vie urinarie |
EP1000045A1 (fr) * | 1997-08-01 | 2000-05-17 | RECORDATI S.A. CHEMICAL and PHARMACEUTICAL COMPANY | Piperazines 1,4-disubstituees |
US6039977A (en) * | 1997-12-09 | 2000-03-21 | Alza Corporation | Pharmaceutical hydrogel formulations, and associated drug delivery devices and methods |
PL343249A1 (en) * | 1998-03-26 | 2001-07-30 | Shionogi & Co | Indole derivatives with antiviral activity |
US6174547B1 (en) * | 1999-07-14 | 2001-01-16 | Alza Corporation | Dosage form comprising liquid formulation |
US6306861B1 (en) * | 1999-07-30 | 2001-10-23 | Recordati S.A. Chemical And Pharmaceutical Company | Thienopyrancecarboxamide derivatives |
US6365591B1 (en) * | 1999-10-18 | 2002-04-02 | Recordati, S.A., Chemical And Pharmacueticals Company | Isoxazolecarboxamide derivatives |
US6403594B1 (en) * | 1999-10-18 | 2002-06-11 | Recordati, S.A. Chemical And Pharmaceutical Company | Benzopyran derivatives |
AR035521A1 (es) * | 2000-12-22 | 2004-06-02 | Lundbeck & Co As H | Derivados de 3-indolina y composicion farmaceutica que los comprende |
US20030060513A1 (en) * | 2001-09-27 | 2003-03-27 | Arneric Stephen P. | Pharmaceutical composition |
ITMI20012060A1 (it) * | 2001-10-05 | 2003-04-05 | Recordati Chem Pharm | Nuovi eterocilcli n-acilati |
-
2001
- 2001-10-05 IT IT2001MI002060A patent/ITMI20012060A1/it unknown
-
2002
- 2002-10-04 AR ARP020103760A patent/AR036743A1/es not_active Application Discontinuation
- 2002-10-07 KR KR10-2004-7004948A patent/KR20040048930A/ko not_active Application Discontinuation
- 2002-10-07 DE DE60208221T patent/DE60208221T2/de not_active Expired - Fee Related
- 2002-10-07 MX MXPA04002962A patent/MXPA04002962A/es unknown
- 2002-10-07 WO PCT/EP2002/011282 patent/WO2003031436A1/fr active IP Right Grant
- 2002-10-07 OA OA1200400088A patent/OA12663A/en unknown
- 2002-10-07 EA EA200400507A patent/EA200400507A1/ru unknown
- 2002-10-07 EP EP02782863A patent/EP1432701B1/fr not_active Expired - Lifetime
- 2002-10-07 AT AT02782863T patent/ATE313540T1/de not_active IP Right Cessation
- 2002-10-07 NZ NZ532511A patent/NZ532511A/en unknown
- 2002-10-07 AP APAP/P/2004/002997A patent/AP1705A/en active
- 2002-10-07 HU HU0401598A patent/HUP0401598A2/hu unknown
- 2002-10-07 AU AU2002346979A patent/AU2002346979B9/en not_active Ceased
- 2002-10-07 BR BR0213067-0A patent/BR0213067A/pt not_active IP Right Cessation
- 2002-10-07 PL PL02369763A patent/PL369763A1/xx not_active Application Discontinuation
- 2002-10-07 SI SI200230244T patent/SI1432701T1/sl unknown
- 2002-10-07 US US10/266,088 patent/US20030181446A1/en not_active Abandoned
- 2002-10-07 DK DK02782863T patent/DK1432701T3/da active
- 2002-10-07 US US10/266,104 patent/US20030162777A1/en not_active Abandoned
- 2002-10-07 CA CA002458456A patent/CA2458456A1/fr not_active Abandoned
- 2002-10-07 ES ES02782863T patent/ES2253568T3/es not_active Expired - Lifetime
- 2002-10-07 JP JP2003534419A patent/JP2005508952A/ja not_active Withdrawn
- 2002-10-07 CN CNA028197283A patent/CN1564820A/zh active Pending
- 2002-10-07 YU YU27204A patent/YU27204A/sh unknown
-
2004
- 2004-03-11 MA MA27571A patent/MA27067A1/fr unknown
- 2004-04-02 TN TNP2004000053A patent/TNSN04053A1/en unknown
- 2004-05-04 CO CO04040886A patent/CO5570679A2/es not_active Application Discontinuation
- 2004-05-04 NO NO20041833A patent/NO20041833L/no not_active Application Discontinuation
- 2004-05-04 HR HR20040392A patent/HRP20040392A2/hr not_active Application Discontinuation
- 2004-05-04 ZA ZA200403356A patent/ZA200403356B/en unknown
- 2004-05-05 EC EC2004005095A patent/ECSP045095A/es unknown
- 2004-10-11 HK HK04107812A patent/HK1067362A1/xx not_active IP Right Cessation
-
2006
- 2006-03-03 CY CY20061100304T patent/CY1104991T1/el unknown
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP1432701B1 (fr) | Composes heterocycliques utilises pour traiter des troubles de la voie urinaire | |
AU2002346979A1 (en) | Heterocyclic compounds for use in the treatment of disorders of the urinary tract | |
KR100813093B1 (ko) | 바닐로이드 수용체 리간드로서 사용하기 위한 피리미딘 유도체 및 이를 포함하는 약제학적 조성물 | |
CA2888210C (fr) | Modulateurs de ror-gamma-t de type quinolinyle a liaison methylene | |
JP5335426B2 (ja) | ジアリールアミン含有化合物および組成物、ならびにc−kit受容体のモジュレーターとしてのそれらの使用 | |
TWI386405B (zh) | 咪唑衍生物 | |
KR100722090B1 (ko) | 신규 화합물, 이의 용도 및 이의 제조 방법 | |
RU2257384C2 (ru) | Новые производные циклического амида | |
JP2011528341A (ja) | ベンズアゼピン誘導体及びそれらのヒスタミンh3拮抗薬としての使用 | |
JP2006504670A (ja) | バニロイド受容体リガンドおよびそれの治療での使用 | |
EP1497291B1 (fr) | Derives de quinoleine et d'aza-indole et leur utilisation comme ligands 5-ht6 | |
KR101386679B1 (ko) | 신규한 아릴피페라진-함유 이미다졸 4-카복사마이드 유도체 및 이를 포함하는 약학 조성물 | |
JP2005508952A5 (fr) | ||
KR100384906B1 (ko) | 무스카린성 수용체 길항제로서의2-아릴에틸-(피페리딘-4-일메틸)아민 유도체 | |
JPH01128968A (ja) | 置換n−(1−アルキル−3−ヒドロキシ−4−ピペリジニル)ベンズアミド類 | |
CA3085879A1 (fr) | Pyrrolidine amides ii substitues | |
CA2927153A1 (fr) | Modulateurs quinolinyle a liaison methylene de ror-gamma-t | |
JP2642955B2 (ja) | 置換n−(3−ヒドロキシ−4−ピペリジニル)ベンズアミド類 | |
JP4831903B2 (ja) | 新規化合物、その使用および製造 | |
US6562839B1 (en) | 6-substituted heteroquinolinecarboxylic acid derivatives and addition salts thereof and processes for the preparation of both | |
MXPA06009059A (en) | Pyrimidine derivatives for use as vanilloid receptor ligands and their use in the treatment of pain |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A1OB | Publication of a patent application | ||
AIPI | Request for the grant of a patent on the basis of a substantive examination of a patent application | ||
ODRP | Renewal fee for the maintenance of a patent |
Payment date: 20060926 Year of fee payment: 5 |
|
PPPP | Transfer of rights |
Owner name: RECORDATI IRELAND LIMITED, IE |
|
ODBC | Application rejected |