OA12740A - Substituted 4-phenyltetrahydroisoquinolines, method for the production thereof, the use thereof as medicaments, in addition to a medicament containingsame. - Google Patents

Info

Publication number

OA12740A

OA12740A OA1200400166A OA1200400166A OA12740A OA 12740 A OA12740 A OA 12740A OA 1200400166 A OA1200400166 A OA 1200400166A OA 1200400166 A OA1200400166 A OA 1200400166A OA 12740 A OA12740 A OA 12740A

Authority

OA

OAPI

Prior art keywords

methyl

dichloro

tetrahydro

isoquinolin

phenyl

Prior art date

2001-12-05

Links

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• OSZMNJRKIPAVOS-UHFFFAOYSA-N 4-phenyl-1,2,3,4-tetrahydroisoquinoline Chemical class C1NCC2=CC=CC=C2C1C1=CC=CC=C1 OSZMNJRKIPAVOS-UHFFFAOYSA-N 0.000 title claims 2
• 239000003814 drug Substances 0.000 title abstract description 7
• 238000000034 method Methods 0.000 title description 72
• 150000001875 compounds Chemical class 0.000 claims abstract description 114
• 125000001153 fluoro group Chemical group F* 0.000 claims description 192
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 191
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 113
• -1 pyrrolidinoethyl Chemical group 0.000 claims description 74
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 70
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 51
• 239000004202 carbamide Substances 0.000 claims description 42
• 229910052801 chlorine Inorganic materials 0.000 claims description 40
• 229910052731 fluorine Inorganic materials 0.000 claims description 40
• 229910052739 hydrogen Inorganic materials 0.000 claims description 38
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 36
• 229910052794 bromium Inorganic materials 0.000 claims description 33
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 32
• 229910052760 oxygen Inorganic materials 0.000 claims description 30
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 28
• ATZPMMXKZFAFOP-UHFFFAOYSA-N 4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)aniline Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=C(N)C=C1 ATZPMMXKZFAFOP-UHFFFAOYSA-N 0.000 claims description 26
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 26
• 229910052740 iodine Inorganic materials 0.000 claims description 22
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 20
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
• 150000003839 salts Chemical class 0.000 claims description 18
• 125000001424 substituent group Chemical group 0.000 claims description 18
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 17
• 229910002091 carbon monoxide Inorganic materials 0.000 claims description 17
• ITSVCLWKVUKMHH-UHFFFAOYSA-N 3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)aniline Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=CC(N)=C1 ITSVCLWKVUKMHH-UHFFFAOYSA-N 0.000 claims description 16
• 229910004727 OSO3H Inorganic materials 0.000 claims description 16
• 229910006069 SO3H Inorganic materials 0.000 claims description 16
• DOYOPBSXEIZLRE-UHFFFAOYSA-N pyrrole-3-carboxylic acid Chemical compound OC(=O)C=1C=CNC=1 DOYOPBSXEIZLRE-UHFFFAOYSA-N 0.000 claims description 16
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 16
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
• 125000002883 imidazolyl group Chemical group 0.000 claims description 12
• 125000004552 isoquinolin-4-yl group Chemical group C1=NC=C(C2=CC=CC=C12)* 0.000 claims description 12
• STUHQDIOZQUPGP-UHFFFAOYSA-N morpholin-4-ium-4-carboxylate Chemical compound OC(=O)N1CCOCC1 STUHQDIOZQUPGP-UHFFFAOYSA-N 0.000 claims description 12
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 12
• WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 claims description 12
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 12
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 12
• 125000000335 thiazolyl group Chemical group 0.000 claims description 12
• 125000001425 triazolyl group Chemical group 0.000 claims description 12
• OGVXGNOUQNLCAU-UHFFFAOYSA-N 4-(4-bromophenyl)-6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=C(Br)C=C1 OGVXGNOUQNLCAU-UHFFFAOYSA-N 0.000 claims description 11
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 11
• 125000006203 morpholinoethyl group Chemical group [H]C([H])(*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 11
• 229910052757 nitrogen Inorganic materials 0.000 claims description 11
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 11
• 125000004076 pyridyl group Chemical group 0.000 claims description 11
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 11
• RTEVZCUIXXCDNH-UHFFFAOYSA-N 1-[2-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]-3-ethylurea Chemical compound CCNC(=O)NC1=CC=CC=C1C1C2=CC(Cl)=CC(Cl)=C2CN(C)C1 RTEVZCUIXXCDNH-UHFFFAOYSA-N 0.000 claims description 10
• KDXKERNSBIXSRK-UHFFFAOYSA-N lysine Chemical compound NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 10
• 125000003386 piperidinyl group Chemical group 0.000 claims description 10
• 229940080818 propionamide Drugs 0.000 claims description 10
• 229940057054 1,3-dimethylurea Drugs 0.000 claims description 9
• QETVYTNAHZLDNS-UHFFFAOYSA-N 4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)benzenesulfonamide Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=C(S(N)(=O)=O)C=C1 QETVYTNAHZLDNS-UHFFFAOYSA-N 0.000 claims description 9
• IMBBXSASDSZJSX-UHFFFAOYSA-N 4-Carboxypyrazole Chemical compound OC(=O)C=1C=NNC=1 IMBBXSASDSZJSX-UHFFFAOYSA-N 0.000 claims description 9
• KNWWGBNAUNTSRV-UHFFFAOYSA-N 4-methylpiperazine-1-carboxylic acid Chemical compound CN1CCN(C(O)=O)CC1 KNWWGBNAUNTSRV-UHFFFAOYSA-N 0.000 claims description 9
• 229910052799 carbon Inorganic materials 0.000 claims description 9
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
• VRKKCPDOYHNJPJ-UHFFFAOYSA-N n-[4-(6-bromo-8-chloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]acetamide Chemical compound C12=CC(Br)=CC(Cl)=C2CN(C)CC1C1=CC=C(NC(C)=O)C=C1 VRKKCPDOYHNJPJ-UHFFFAOYSA-N 0.000 claims description 9
• OOPDWMLXBWNOLH-UHFFFAOYSA-N 4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)benzoic acid Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=C(C(O)=O)C=C1 OOPDWMLXBWNOLH-UHFFFAOYSA-N 0.000 claims description 8
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
• YPEQXVPZMTVGCT-UHFFFAOYSA-N n-[3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]acetamide Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=CC(NC(C)=O)=C1 YPEQXVPZMTVGCT-UHFFFAOYSA-N 0.000 claims description 8
• DPQHWDSAFGLDQW-UHFFFAOYSA-N n-[3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]methanesulfonamide Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=CC(NS(C)(=O)=O)=C1 DPQHWDSAFGLDQW-UHFFFAOYSA-N 0.000 claims description 8
• 125000002971 oxazolyl group Chemical group 0.000 claims description 8
• DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical compound OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-N 0.000 claims description 7
• ROCHTQWNNZUYOK-UHFFFAOYSA-N 3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)benzoic acid Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=CC(C(O)=O)=C1 ROCHTQWNNZUYOK-UHFFFAOYSA-N 0.000 claims description 7
• 125000004432 carbon atom Chemical group C* 0.000 claims description 7
• SHYIEDSDUINFSE-UHFFFAOYSA-N ethyl 3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)benzoate Chemical compound CCOC(=O)C1=CC=CC(C2C3=CC(Cl)=CC(Cl)=C3CN(C)C2)=C1 SHYIEDSDUINFSE-UHFFFAOYSA-N 0.000 claims description 7
• 125000001072 heteroaryl group Chemical group 0.000 claims description 7
• KNIROMQEWJVMTR-UHFFFAOYSA-N n-[4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]acetamide Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=C(NC(C)=O)C=C1 KNIROMQEWJVMTR-UHFFFAOYSA-N 0.000 claims description 7
• NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims description 7
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 6
• XMYPFIYRTAOIFI-UHFFFAOYSA-N 2-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)aniline Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=CC=C1N XMYPFIYRTAOIFI-UHFFFAOYSA-N 0.000 claims description 6
• 125000004429 atom Chemical group 0.000 claims description 6
• CNFBIEVFBXQXMZ-UHFFFAOYSA-N n-[4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]formamide Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=C(NC=O)C=C1 CNFBIEVFBXQXMZ-UHFFFAOYSA-N 0.000 claims description 6
• AQZRISWBYMCHSD-UHFFFAOYSA-N 1-[3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]-3-(2-hydroxyethyl)urea Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=CC(NC(=O)NCCO)=C1 AQZRISWBYMCHSD-UHFFFAOYSA-N 0.000 claims description 5
• BQKRJALYXOHITF-UHFFFAOYSA-N 1-acetyl-n-[2-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]piperidine-4-carboxamide Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=CC=C1NC(=O)C1CCN(C(C)=O)CC1 BQKRJALYXOHITF-UHFFFAOYSA-N 0.000 claims description 5
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 5
• VJULFQSBRRZIFL-UHFFFAOYSA-N 3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)-n-methylaniline Chemical compound CNC1=CC=CC(C2C3=CC(Cl)=CC(Cl)=C3CN(C)C2)=C1 VJULFQSBRRZIFL-UHFFFAOYSA-N 0.000 claims description 5
• GTMHPRFXOPJRAN-UHFFFAOYSA-N methyl n-[3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]carbamate Chemical compound COC(=O)NC1=CC=CC(C2C3=CC(Cl)=CC(Cl)=C3CN(C)C2)=C1 GTMHPRFXOPJRAN-UHFFFAOYSA-N 0.000 claims description 5
• KSLUOYSGQYULGE-UHFFFAOYSA-N n-[2-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]cyclopropanecarboxamide Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=CC=C1NC(=O)C1CC1 KSLUOYSGQYULGE-UHFFFAOYSA-N 0.000 claims description 5
• QVLLBNWMNYZNPX-UHFFFAOYSA-N n-[3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]formamide Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=CC(NC=O)=C1 QVLLBNWMNYZNPX-UHFFFAOYSA-N 0.000 claims description 5
• TVYZDFMOBGEOGU-UHFFFAOYSA-N n-[4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]-2-(dimethylamino)acetamide Chemical compound C1=CC(NC(=O)CN(C)C)=CC=C1C1C2=CC(Cl)=CC(Cl)=C2CN(C)C1 TVYZDFMOBGEOGU-UHFFFAOYSA-N 0.000 claims description 5
• OSBUINWGQXMTBW-UHFFFAOYSA-N n-[4-[8-chloro-2-methyl-6-(4-methylpiperazin-1-yl)-3,4-dihydro-1h-isoquinolin-4-yl]phenyl]acetamide Chemical compound C1CN(C)CCN1C1=CC(Cl)=C(CN(C)CC2C=3C=CC(NC(C)=O)=CC=3)C2=C1 OSBUINWGQXMTBW-UHFFFAOYSA-N 0.000 claims description 5
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
• UNNPAFDYRLETBW-UHFFFAOYSA-N 3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)benzenesulfonamide Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=CC(S(N)(=O)=O)=C1 UNNPAFDYRLETBW-UHFFFAOYSA-N 0.000 claims description 4
• MUBZVQSJVOVBRY-UHFFFAOYSA-N 4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)-n,n-dimethylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1C1C2=CC(Cl)=CC(Cl)=C2CN(C)C1 MUBZVQSJVOVBRY-UHFFFAOYSA-N 0.000 claims description 4
• UAQVNFADDKMTMC-UHFFFAOYSA-N 4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)-n-[2-(dimethylamino)ethyl]benzamide Chemical compound C1=CC(C(=O)NCCN(C)C)=CC=C1C1C2=CC(Cl)=CC(Cl)=C2CN(C)C1 UAQVNFADDKMTMC-UHFFFAOYSA-N 0.000 claims description 4
• CTKAYSOAVWUWKF-UHFFFAOYSA-N 4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)-n-ethylbenzamide Chemical compound C1=CC(C(=O)NCC)=CC=C1C1C2=CC(Cl)=CC(Cl)=C2CN(C)C1 CTKAYSOAVWUWKF-UHFFFAOYSA-N 0.000 claims description 4
• AMVYEVIRFWDRSX-UHFFFAOYSA-N 5-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)-n-ethyl-2-hydroxybenzamide Chemical compound C1=C(O)C(C(=O)NCC)=CC(C2C3=CC(Cl)=CC(Cl)=C3CN(C)C2)=C1 AMVYEVIRFWDRSX-UHFFFAOYSA-N 0.000 claims description 4
• WOSRCHOJUSCXJV-UHFFFAOYSA-N 6,8-dichloro-2-cyclopropyl-4-phenyl-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C2CC2)CC1C1=CC=CC=C1 WOSRCHOJUSCXJV-UHFFFAOYSA-N 0.000 claims description 4
• LAXMGXGWGIBHHT-UHFFFAOYSA-N 6,8-dichloro-2-methyl-4-(4-piperidin-1-ylphenyl)-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C(C=C1)=CC=C1N1CCCCC1 LAXMGXGWGIBHHT-UHFFFAOYSA-N 0.000 claims description 4
• UCWLCWOJRHFLRB-UHFFFAOYSA-N 6,8-dichloro-2-methyl-4-[4-(4-methylpiperazin-1-yl)phenyl]-3,4-dihydro-1h-isoquinoline Chemical compound C1CN(C)CCN1C1=CC=C(C2C3=CC(Cl)=CC(Cl)=C3CN(C)C2)C=C1 UCWLCWOJRHFLRB-UHFFFAOYSA-N 0.000 claims description 4
• WZFGYXOOIXKUTM-UHFFFAOYSA-N ethyl n-[3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]carbamate Chemical compound CCOC(=O)NC1=CC=CC(C2C3=CC(Cl)=CC(Cl)=C3CN(C)C2)=C1 WZFGYXOOIXKUTM-UHFFFAOYSA-N 0.000 claims description 4
• LRYLUJZAQSAIMW-UHFFFAOYSA-N n-[3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]-1,1,1-trifluoromethanesulfonamide Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=CC(NS(=O)(=O)C(F)(F)F)=C1 LRYLUJZAQSAIMW-UHFFFAOYSA-N 0.000 claims description 4
• VTACXQBZRPNVPL-UHFFFAOYSA-N n-[3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]-2-(methylamino)acetamide Chemical compound CNCC(=O)NC1=CC=CC(C2C3=CC(Cl)=CC(Cl)=C3CN(C)C2)=C1 VTACXQBZRPNVPL-UHFFFAOYSA-N 0.000 claims description 4
• KFHHWUSTHZTJJO-UHFFFAOYSA-N n-[3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]-4-methylpiperazine-1-carboxamide Chemical compound C1CN(C)CCN1C(=O)NC1=CC=CC(C2C3=CC(Cl)=CC(Cl)=C3CN(C)C2)=C1 KFHHWUSTHZTJJO-UHFFFAOYSA-N 0.000 claims description 4
• WTTRVHXQTCGIJT-UHFFFAOYSA-N n-[3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]-n-methylpyrrolidine-1-carboxamide Chemical compound C=1C=CC(C2C3=CC(Cl)=CC(Cl)=C3CN(C)C2)=CC=1N(C)C(=O)N1CCCC1 WTTRVHXQTCGIJT-UHFFFAOYSA-N 0.000 claims description 4
• ZTVNCRHIUNTHFV-UHFFFAOYSA-N n-[3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]piperidine-1-carboxamide Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C(C=1)=CC=CC=1NC(=O)N1CCCCC1 ZTVNCRHIUNTHFV-UHFFFAOYSA-N 0.000 claims description 4
• HXYSUBQOVFAWTM-UHFFFAOYSA-N n-[3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]propanamide Chemical compound CCC(=O)NC1=CC=CC(C2C3=CC(Cl)=CC(Cl)=C3CN(C)C2)=C1 HXYSUBQOVFAWTM-UHFFFAOYSA-N 0.000 claims description 4
• FXKXMRNGDQZZGG-UHFFFAOYSA-N n-[3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]pyridine-3-carboxamide Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C(C=1)=CC=CC=1NC(=O)C1=CC=CN=C1 FXKXMRNGDQZZGG-UHFFFAOYSA-N 0.000 claims description 4
• WSBDGRSGRDDLAL-UHFFFAOYSA-N n-[4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]-1-methylsulfonylpiperidine-4-carboxamide Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C(C=C1)=CC=C1NC(=O)C1CCN(S(C)(=O)=O)CC1 WSBDGRSGRDDLAL-UHFFFAOYSA-N 0.000 claims description 4
• LIDLKEQMWPVUCP-UHFFFAOYSA-N n-[4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]-4-methylpiperazine-1-carboxamide Chemical compound C1CN(C)CCN1C(=O)NC1=CC=C(C2C3=CC(Cl)=CC(Cl)=C3CN(C)C2)C=C1 LIDLKEQMWPVUCP-UHFFFAOYSA-N 0.000 claims description 4
• RXJOGSUJFYNTKI-UHFFFAOYSA-N n-[4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]methanesulfonamide Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=C(NS(C)(=O)=O)C=C1 RXJOGSUJFYNTKI-UHFFFAOYSA-N 0.000 claims description 4
• 229960004889 salicylic acid Drugs 0.000 claims description 4
• 125000004434 sulfur atom Chemical group 0.000 claims description 4
• SDPZIVSAFCAYMC-UHFFFAOYSA-N 1-[2-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]-3-ethylthiourea Chemical compound CCNC(=S)NC1=CC=CC=C1C1C2=CC(Cl)=CC(Cl)=C2CN(C)C1 SDPZIVSAFCAYMC-UHFFFAOYSA-N 0.000 claims description 3
• BSVFEOVPMWUTHR-UHFFFAOYSA-N 2,2-dimethylpropyl n-[3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]carbamate Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=CC(NC(=O)OCC(C)(C)C)=C1 BSVFEOVPMWUTHR-UHFFFAOYSA-N 0.000 claims description 3
• GUCMMJZKXNYAJI-UHFFFAOYSA-N 2,2-dimethylpropyl n-[4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]carbamate Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=C(NC(=O)OCC(C)(C)C)C=C1 GUCMMJZKXNYAJI-UHFFFAOYSA-N 0.000 claims description 3
• DGHLDWUCDWSFFO-UHFFFAOYSA-N 2,6-diamino-n-[3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]hexanamide Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=CC(NC(=O)C(N)CCCCN)=C1 DGHLDWUCDWSFFO-UHFFFAOYSA-N 0.000 claims description 3
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