ZA200403711B - Substituted 4-phenyltetrahydroisoquinolines, method for the production thereof, the use thereof as medicaments, in addition to a medicament containing same. - Google Patents
Substituted 4-phenyltetrahydroisoquinolines, method for the production thereof, the use thereof as medicaments, in addition to a medicament containing same. Download PDFInfo
- Publication number
- ZA200403711B ZA200403711B ZA200403711A ZA200403711A ZA200403711B ZA 200403711 B ZA200403711 B ZA 200403711B ZA 200403711 A ZA200403711 A ZA 200403711A ZA 200403711 A ZA200403711 A ZA 200403711A ZA 200403711 B ZA200403711 B ZA 200403711B
- Authority
- ZA
- South Africa
- Prior art keywords
- methyl
- tetrahydro
- dichloro
- isoquinolin
- phenyl
- Prior art date
Links
- 239000003814 drug Substances 0.000 title claims description 21
- 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 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 212
- 125000001153 fluoro group Chemical group F* 0.000 claims description 211
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 77
- -1 N,N-dimethylaminoethyl Chemical group 0.000 claims description 73
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 38
- 229910052760 oxygen Inorganic materials 0.000 claims description 38
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 32
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 30
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 19
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-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
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 11
- 125000002883 imidazolyl group Chemical group 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
- 125000002971 oxazolyl group Chemical group 0.000 claims description 11
- 125000003386 piperidinyl group Chemical group 0.000 claims description 11
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 11
- 125000004076 pyridyl group Chemical group 0.000 claims description 11
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 11
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 11
- 125000000335 thiazolyl group Chemical group 0.000 claims description 11
- 125000001425 triazolyl group Chemical group 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 229940080818 propionamide Drugs 0.000 claims description 9
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 150000003254 radicals Chemical class 0.000 claims description 8
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 6
- 101150020251 NR13 gene Proteins 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- AJSBYWKHOANAIZ-UHFFFAOYSA-N 1-[3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]-3-methylurea Chemical compound CNC(=O)NC1=CC=CC(C2C3=CC(Cl)=CC(Cl)=C3CN(C)C2)=C1 AJSBYWKHOANAIZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 5
- 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 5
- WWMLHLXNNOJHCI-UHFFFAOYSA-N n-[3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]morpholine-4-carboxamide Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C(C=1)=CC=CC=1NC(=O)N1CCOCC1 WWMLHLXNNOJHCI-UHFFFAOYSA-N 0.000 claims description 5
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- FPRVCASHSFEVJD-UHFFFAOYSA-N 1-[3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]-3-ethylurea Chemical compound CCNC(=O)NC1=CC=CC(C2C3=CC(Cl)=CC(Cl)=C3CN(C)C2)=C1 FPRVCASHSFEVJD-UHFFFAOYSA-N 0.000 claims description 4
- JVZKSFQFKWZPOW-UHFFFAOYSA-N 1-[4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1C2=CC(Cl)=CC(Cl)=C2CN(C)C1 JVZKSFQFKWZPOW-UHFFFAOYSA-N 0.000 claims description 4
- JYHUZKWGHVORTI-UHFFFAOYSA-N 1-[4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]-3-methylthiourea Chemical compound C1=CC(NC(=S)NC)=CC=C1C1C2=CC(Cl)=CC(Cl)=C2CN(C)C1 JYHUZKWGHVORTI-UHFFFAOYSA-N 0.000 claims description 4
- APTIOEQOZBJPFQ-UHFFFAOYSA-N 1-acetyl-n-[4-(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)CC1C(C=C1)=CC=C1NC(=O)C1CCN(C(C)=O)CC1 APTIOEQOZBJPFQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 4
- 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
- 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
- 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 4
- 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 4
- JTXNWYHSDXNOAG-UHFFFAOYSA-N 4-[4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]morpholine Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C(C=C1)=CC=C1N1CCOCC1 JTXNWYHSDXNOAG-UHFFFAOYSA-N 0.000 claims description 4
- ZPXGMXNPRXENML-UHFFFAOYSA-N 5-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)-2-hydroxybenzoic acid Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=C(O)C(C(O)=O)=C1 ZPXGMXNPRXENML-UHFFFAOYSA-N 0.000 claims description 4
- WFKAJVHLWXSISD-UHFFFAOYSA-N anhydrous dimethyl-acetamide Natural products CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 claims description 4
- 229940047889 isobutyramide Drugs 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- XSTRCKXRNHVVTA-UHFFFAOYSA-N 1-[3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]-3-[2-(dimethylamino)ethyl]urea Chemical compound CN(C)CCNC(=O)NC1=CC=CC(C2C3=CC(Cl)=CC(Cl)=C3CN(C)C2)=C1 XSTRCKXRNHVVTA-UHFFFAOYSA-N 0.000 claims description 3
- ITHVMVOSCQULAU-UHFFFAOYSA-N 1-[3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]-3-ethylthiourea Chemical compound CCNC(=S)NC1=CC=CC(C2C3=CC(Cl)=CC(Cl)=C3CN(C)C2)=C1 ITHVMVOSCQULAU-UHFFFAOYSA-N 0.000 claims description 3
- NHJXZSFGEZQCQW-UHFFFAOYSA-N 1-[4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]-3-propylurea Chemical compound C1=CC(NC(=O)NCCC)=CC=C1C1C2=CC(Cl)=CC(Cl)=C2CN(C)C1 NHJXZSFGEZQCQW-UHFFFAOYSA-N 0.000 claims description 3
- LNBXSRHKTFMPBN-UHFFFAOYSA-N 2,6-diamino-n-[4-(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=C(NC(=O)C(N)CCCCN)C=C1 LNBXSRHKTFMPBN-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- FXDGSBKQIDBHPQ-UHFFFAOYSA-N 2-amino-n-[3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]butanamide Chemical compound CCC(N)C(=O)NC1=CC=CC(C2C3=CC(Cl)=CC(Cl)=C3CN(C)C2)=C1 FXDGSBKQIDBHPQ-UHFFFAOYSA-N 0.000 claims description 3
- ZNIDKPZEMMUEAU-UHFFFAOYSA-N 2-amino-n-[3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]propanamide Chemical compound CC(N)C(=O)NC1=CC=CC(C2C3=CC(Cl)=CC(Cl)=C3CN(C)C2)=C1 ZNIDKPZEMMUEAU-UHFFFAOYSA-N 0.000 claims description 3
- HWHOOFAFSRSPOT-UHFFFAOYSA-N 2-chloro-5-(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(Cl)C(S(N)(=O)=O)=C1 HWHOOFAFSRSPOT-UHFFFAOYSA-N 0.000 claims description 3
- KMZLUIVXQDYDEM-UHFFFAOYSA-N 2-methyl-4-phenyl-6,8-bis(trifluoromethyl)-3,4-dihydro-1h-isoquinoline Chemical compound C12=CC(C(F)(F)F)=CC(C(F)(F)F)=C2CN(C)CC1C1=CC=CC=C1 KMZLUIVXQDYDEM-UHFFFAOYSA-N 0.000 claims description 3
- VKMIFAXQPZVCKG-UHFFFAOYSA-N 3-[3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]-1,1-diethylurea Chemical compound CCN(CC)C(=O)NC1=CC=CC(C2C3=CC(Cl)=CC(Cl)=C3CN(C)C2)=C1 VKMIFAXQPZVCKG-UHFFFAOYSA-N 0.000 claims description 3
- OPKTYGMCIDQTHP-UHFFFAOYSA-N 4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)-n-propylbenzamide Chemical compound C1=CC(C(=O)NCCC)=CC=C1C1C2=CC(Cl)=CC(Cl)=C2CN(C)C1 OPKTYGMCIDQTHP-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- JWYJULAOMWNOJL-UHFFFAOYSA-N 4-[3-[bis(methylamino)sulfamoylamino]phenyl]-6,8-dichloro-2-methyl-3,4-dihydro-1H-isoquinoline Chemical compound CNN(NC)S(=O)(=O)NC1=CC=CC(C2C3=CC(Cl)=CC(Cl)=C3CN(C)C2)=C1 JWYJULAOMWNOJL-UHFFFAOYSA-N 0.000 claims description 3
- PSOOVXSNQHEDMM-UHFFFAOYSA-N 5-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)-2-hydroxy-n-methylbenzamide Chemical compound C1=C(O)C(C(=O)NC)=CC(C2C3=CC(Cl)=CC(Cl)=C3CN(C)C2)=C1 PSOOVXSNQHEDMM-UHFFFAOYSA-N 0.000 claims description 3
- CLZQZTZRISZXAP-UHFFFAOYSA-N 5-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)-n-[2-(dimethylamino)ethyl]-2-hydroxybenzamide Chemical compound C1=C(O)C(C(=O)NCCN(C)C)=CC(C2C3=CC(Cl)=CC(Cl)=C3CN(C)C2)=C1 CLZQZTZRISZXAP-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 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 3
- LEHSIQYEMSWARG-UHFFFAOYSA-N n-[2-(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=C1NS(C)(=O)=O LEHSIQYEMSWARG-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- VHPNMMFTCKVPQW-UHFFFAOYSA-N n-[3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]-1,4-dimethylpyrrole-2-carboxamide Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C(C=1)=CC=CC=1NC(=O)C1=CC(C)=CN1C VHPNMMFTCKVPQW-UHFFFAOYSA-N 0.000 claims description 3
- AWDVARDJXPUYRE-UHFFFAOYSA-N n-[3-(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=1)=CC=CC=1NC(=O)C1CCN(S(C)(=O)=O)CC1 AWDVARDJXPUYRE-UHFFFAOYSA-N 0.000 claims description 3
- UOWFCRXLHWYKTE-UHFFFAOYSA-N n-[3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]-2,2-dimethylpropanamide Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=CC(NC(=O)C(C)(C)C)=C1 UOWFCRXLHWYKTE-UHFFFAOYSA-N 0.000 claims description 3
- ZBTGHYLYYMVAEV-UHFFFAOYSA-N n-[3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]-4-nitro-1h-pyrrole-2-carboxamide Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C(C=1)=CC=CC=1NC(=O)C1=CC([N+]([O-])=O)=CN1 ZBTGHYLYYMVAEV-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- MTFHARGXDVSDNK-UHFFFAOYSA-N n-[4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]-1,2-dimethylimidazole-4-sulfonamide Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C(C=C1)=CC=C1NS(=O)(=O)C1=CN(C)C(C)=N1 MTFHARGXDVSDNK-UHFFFAOYSA-N 0.000 claims description 3
- MFOCFIBNNDJEAI-UHFFFAOYSA-N n-[4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]-1-methylpiperidine-4-carboxamide Chemical compound C1CN(C)CCC1C(=O)NC1=CC=C(C2C3=CC(Cl)=CC(Cl)=C3CN(C)C2)C=C1 MFOCFIBNNDJEAI-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- XOLKVTDSPGGFNP-UHFFFAOYSA-N n-[4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]-1h-pyrrole-2-carboxamide Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C(C=C1)=CC=C1NC(=O)C1=CC=CN1 XOLKVTDSPGGFNP-UHFFFAOYSA-N 0.000 claims description 3
- KVKHCCXAFAEQAA-UHFFFAOYSA-N n-[4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]-2,2-dimethylpropanamide Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C1=CC=C(NC(=O)C(C)(C)C)C=C1 KVKHCCXAFAEQAA-UHFFFAOYSA-N 0.000 claims description 3
- GIBGLOZYQRRBPY-UHFFFAOYSA-N n-[4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]-2-methylpropanamide Chemical compound C1=CC(NC(=O)C(C)C)=CC=C1C1C2=CC(Cl)=CC(Cl)=C2CN(C)C1 GIBGLOZYQRRBPY-UHFFFAOYSA-N 0.000 claims description 3
- CJKOAUWXSZLXLP-UHFFFAOYSA-N n-[4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]-4-nitro-1h-pyrrole-2-carboxamide Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C(C=C1)=CC=C1NC(=O)C1=CC([N+]([O-])=O)=CN1 CJKOAUWXSZLXLP-UHFFFAOYSA-N 0.000 claims description 3
- CUMPRBLVHDOHMH-UHFFFAOYSA-N n-[4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]ethanesulfonamide Chemical compound C1=CC(NS(=O)(=O)CC)=CC=C1C1C2=CC(Cl)=CC(Cl)=C2CN(C)C1 CUMPRBLVHDOHMH-UHFFFAOYSA-N 0.000 claims description 3
- MYHYDYGXHXLBPC-UHFFFAOYSA-N n-[4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]propanamide Chemical compound C1=CC(NC(=O)CC)=CC=C1C1C2=CC(Cl)=CC(Cl)=C2CN(C)C1 MYHYDYGXHXLBPC-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
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- 210000001428 peripheral nervous system Anatomy 0.000 claims 1
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- YOAVGGWPQOACQB-UHFFFAOYSA-N propan-2-yl n-[3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]carbamate Chemical compound CC(C)OC(=O)NC1=CC=CC(C2C3=CC(Cl)=CC(Cl)=C3CN(C)C2)=C1 YOAVGGWPQOACQB-UHFFFAOYSA-N 0.000 claims 1
- LCDCPQHFCOBUEF-UHFFFAOYSA-N pyrrolidine-1-carboxamide Chemical compound NC(=O)N1CCCC1 LCDCPQHFCOBUEF-UHFFFAOYSA-N 0.000 claims 1
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- 229960000581 salicylamide Drugs 0.000 claims 1
- 230000035939 shock Effects 0.000 claims 1
- 201000002859 sleep apnea Diseases 0.000 claims 1
- 229940124530 sulfonamide Drugs 0.000 claims 1
- 150000003456 sulfonamides Chemical class 0.000 claims 1
- 238000001356 surgical procedure Methods 0.000 claims 1
- 238000002054 transplantation Methods 0.000 claims 1
- 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 description 1
- 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 description 1
- IYPIAJKDKNPXNO-UHFFFAOYSA-N 1-[4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]-3-ethylthiourea Chemical compound C1=CC(NC(=S)NCC)=CC=C1C1C2=CC(Cl)=CC(Cl)=C2CN(C)C1 IYPIAJKDKNPXNO-UHFFFAOYSA-N 0.000 description 1
- RYPNUXKTTFMKFH-UHFFFAOYSA-N 5-bromo-n-[3-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]thiophene-2-sulfonamide Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C(C=1)=CC=CC=1NS(=O)(=O)C1=CC=C(Br)S1 RYPNUXKTTFMKFH-UHFFFAOYSA-N 0.000 description 1
- WJLVVYJYMZFJET-UHFFFAOYSA-N n-[2-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]butanamide Chemical compound CCCC(=O)NC1=CC=CC=C1C1C2=CC(Cl)=CC(Cl)=C2CN(C)C1 WJLVVYJYMZFJET-UHFFFAOYSA-N 0.000 description 1
- IUECDQZCOVVBQU-UHFFFAOYSA-N n-[4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]-5-(trifluoromethyl)-1h-pyrazole-4-carboxamide Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C(C=C1)=CC=C1NC(=O)C1=CNN=C1C(F)(F)F IUECDQZCOVVBQU-UHFFFAOYSA-N 0.000 description 1
- WSLYLXWYZBZFCE-UHFFFAOYSA-N n-[4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]butanamide Chemical compound C1=CC(NC(=O)CCC)=CC=C1C1C2=CC(Cl)=CC(Cl)=C2CN(C)C1 WSLYLXWYZBZFCE-UHFFFAOYSA-N 0.000 description 1
- VLXQFBRCVJQJIT-UHFFFAOYSA-N n-[4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]cyclobutanecarboxamide Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C(C=C1)=CC=C1NC(=O)C1CCC1 VLXQFBRCVJQJIT-UHFFFAOYSA-N 0.000 description 1
- ISLGZVHVMGDHPE-UHFFFAOYSA-N n-[4-(6,8-dichloro-2-methyl-3,4-dihydro-1h-isoquinolin-4-yl)phenyl]pyridine-4-carboxamide Chemical compound C12=CC(Cl)=CC(Cl)=C2CN(C)CC1C(C=C1)=CC=C1NC(=O)C1=CC=NC=C1 ISLGZVHVMGDHPE-UHFFFAOYSA-N 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
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- C—CHEMISTRY; METALLURGY
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Organic Chemistry (AREA)
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- Nutrition Science (AREA)
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- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Indole Compounds (AREA)
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Publications (1)
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| Publication number | Priority date | Publication date | Assignee | Title |
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| DE10312963A1 (de) * | 2003-03-24 | 2004-10-07 | Aventis Pharma Deutschland Gmbh | Substituierte 4-Phenyltetrahydroisochinoline, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament, sowie sie enthaltendes Medikament |
| TW200526626A (en) | 2003-09-13 | 2005-08-16 | Astrazeneca Ab | Chemical compounds |
| DE102004046492A1 (de) * | 2004-09-23 | 2006-03-30 | Sanofi-Aventis Deutschland Gmbh | Substituierte 4-Phenyltetrahydroisochinoline, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament, sowie sie enthaltendes Medikament |
| US20060111393A1 (en) * | 2004-11-22 | 2006-05-25 | Molino Bruce F | 4-Phenyl substituted tetrahydroisoquinolines and use thereof to block reuptake of norepinephrine, dopamine and serotonin |
| DE102005001411A1 (de) | 2005-01-12 | 2006-07-27 | Sanofi-Aventis Deutschland Gmbh | Substituierte 4-Phenyltetrahydroisochinoline, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament, sowie sie enthaltendes Medikament |
| UA94901C2 (ru) | 2005-02-18 | 2011-06-25 | Астразенека Аб | Антибактериальные производные пиперидина |
| CN101171247A (zh) * | 2005-03-04 | 2008-04-30 | 阿斯利康(瑞典)有限公司 | 作为dna促旋酶和拓扑异构酶抑制剂的吡咯衍生物 |
| DE102005044817A1 (de) * | 2005-09-20 | 2007-03-22 | Sanofi-Aventis Deutschland Gmbh | Substituierte 4-Phenyltetrahydroisochinoline, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament, sowie sie enthaltendes Medikament |
| DE102006012545A1 (de) * | 2006-03-18 | 2007-09-27 | Sanofi-Aventis | Substituierte 2-Amino-4-phenyl-dihydrochinoline, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament, sowie sie enthaltendes Medikament |
| US10543207B2 (en) | 2008-12-31 | 2020-01-28 | Ardelyx, Inc. | Compounds and methods for inhibiting NHE-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders |
| WO2018129556A1 (en) * | 2017-01-09 | 2018-07-12 | Ardelyx, Inc. | Compounds and methods for inhibiting nhe-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders |
| WO2010078449A2 (en) * | 2008-12-31 | 2010-07-08 | Ardelyx, Inc. | Compounds and methods for inhibiting nhe-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders |
| WO2010132437A1 (en) | 2009-05-12 | 2010-11-18 | Albany Molecular Research, Inc. | Aryl, heteroaryl, and heterocycle substituted tetrahydroisoquinolines and use thereof |
| RU2684097C2 (ru) * | 2012-08-21 | 2019-04-04 | Эрделикс, Инк. | Соединения и способы для ингибирования NHE-опосредованного антипорта в лечении расстройств, ассоциированных с задержкой жидкости или солевой перегрузкой, и заболеваний желудочно-кишечного тракта |
| BR112015025805A2 (pt) | 2013-04-12 | 2017-07-25 | Ardelyx Inc | compostos de ligação de nh3 e métodos para inibir o transporte de fosfato |
| CN103788084A (zh) * | 2014-03-02 | 2014-05-14 | 湖南华腾制药有限公司 | 四氢异喹啉衍生物及其合成方法 |
| SI3173408T1 (sl) * | 2014-07-25 | 2019-01-31 | Taisho Pharmaceutical Co., Ltd., | Spojina fenil tetrahidroizokinolin substituirana s heteroarilom |
| JP6903923B2 (ja) * | 2016-01-22 | 2021-07-14 | 大正製薬株式会社 | ヘテロアリールで置換されたフェニルテトラヒドロイソキノリン化合物を有効成分として含有する医薬 |
| EA201991676A1 (ru) | 2017-01-09 | 2020-01-30 | Арделикс, Инк. | Ингибиторы nhe-опосредованного антипорта |
| CN110267944B (zh) * | 2017-01-09 | 2024-03-08 | 阿德利克斯股份有限公司 | 可用于治疗胃肠道病症的化合物 |
| WO2022127917A1 (zh) * | 2020-12-18 | 2022-06-23 | 上海济煜医药科技有限公司 | 苯并杂环取代四氢异喹啉类化合物 |
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| DE19951702A1 (de) * | 1999-10-27 | 2001-05-03 | Aventis Pharma Gmbh | Verwendung von 2-Amino-3,4-dihydro-chinazolinen zur Herstellung eines Medikaments zur Behandlung oder Prophylaxe von durch ischämischen Zuständen bewirkten Krankheiten |
| KR100885986B1 (ko) * | 1999-11-03 | 2009-03-03 | 에이엠알 테크놀로지, 인크. | 노르에피네프린, 도파민 및 세로토닌의 재흡수를 방지하기위한 아릴 및 헤테로아릴 치환된테트라하이드로이소퀴놀린 및 이들의 용도 |
| BR0015307A (pt) * | 1999-11-03 | 2002-07-09 | Albany Molecular Res Inc | Composto, composição, composição farmacêutica, métodos para tratar um distúrbio que é criado pela ou é dependente da disponibilidade diminuìda de serotonina, norepinefrina ou dopamina, e para inibir a absorção de norepinefrina sináptica, de serotonina sináptica e de dopamina sináptica em um paciente em necessidade destas, e, conjunto |
| EP1113007A1 (en) * | 1999-12-24 | 2001-07-04 | Pfizer Inc. | Tetrahydroisoquinoline compounds as estrogen agonists/antagonists |
| DE10019062A1 (de) * | 2000-04-18 | 2001-10-25 | Merck Patent Gmbh | 2-Guanidino-4-aryl-chinazoline als NHE-3 Inhibitoren |
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