BG103327A - Производни на антранилова киселина като модулатори на резистентност към много лекарствени средства - Google Patents

Info

Publication number

BG103327A

BG103327A BG103327A BG10332799A BG103327A BG 103327 A BG103327 A BG 103327A BG 103327 A BG103327 A BG 103327A BG 10332799 A BG10332799 A BG 10332799A BG 103327 A BG103327 A BG 103327A

Authority

BG

Bulgaria

Prior art keywords

dimethoxy

dihydro

ethyl

isoquinolin

phenyl

Prior art date

1996-10-18

Links

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• Global Dossier
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• RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 title claims abstract description 32
• 150000001875 compounds Chemical class 0.000 claims abstract description 194
• 238000002360 preparation method Methods 0.000 claims abstract description 38
• 150000003839 salts Chemical class 0.000 claims abstract description 24
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 14
• 230000001965 increasing effect Effects 0.000 claims abstract description 10
• 239000003112 inhibitor Substances 0.000 claims abstract description 8
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
• 125000001424 substituent group Chemical group 0.000 claims abstract description 6
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 4
• 231100000135 cytotoxicity Toxicity 0.000 claims abstract description 3
• 230000003013 cytotoxicity Effects 0.000 claims abstract description 3
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
• -1 methylenedioxy Chemical group 0.000 claims description 222
• 238000000034 method Methods 0.000 claims description 118
• 239000000203 mixture Substances 0.000 claims description 113
• 150000001412 amines Chemical class 0.000 claims description 75
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 45
• 229910052739 hydrogen Inorganic materials 0.000 claims description 39
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 36
• DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 claims description 34
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
• PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical compound NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 claims description 27
• 239000001257 hydrogen Substances 0.000 claims description 27
• VHVGFEDTMPYCSX-UHFFFAOYSA-N [1-[[2,2-dimethyl-3-[[4-(oxoazaniumylmethylidene)pyridin-1-yl]methoxy]propoxy]methyl]pyridin-4-ylidene]methyl-oxoazanium;dichloride Chemical compound [Cl-].[Cl-].C1=CC(=C[NH+]=O)C=CN1COCC(C)(C)COCN1C=CC(=C[NH+]=O)C=C1 VHVGFEDTMPYCSX-UHFFFAOYSA-N 0.000 claims description 24
• 239000003814 drug Substances 0.000 claims description 24
• 239000002253 acid Substances 0.000 claims description 22
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 21
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
• 125000004432 carbon atom Chemical group C* 0.000 claims description 19
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
• 229910052799 carbon Inorganic materials 0.000 claims description 18
• 150000001408 amides Chemical class 0.000 claims description 17
• 229940079593 drug Drugs 0.000 claims description 17
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 15
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 15
• 229910052736 halogen Inorganic materials 0.000 claims description 13
• 150000002367 halogens Chemical class 0.000 claims description 13
• 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 12
• UPUZGXILYFKSGE-UHFFFAOYSA-N quinoxaline-2-carboxylic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CN=C21 UPUZGXILYFKSGE-UHFFFAOYSA-N 0.000 claims description 12
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 11
• MVJZWRRXDKDIIG-UHFFFAOYSA-N 1,1-dimethoxy-3,4-dihydro-2h-isoquinoline Chemical compound C1=CC=C2C(OC)(OC)NCCC2=C1 MVJZWRRXDKDIIG-UHFFFAOYSA-N 0.000 claims description 9
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
• XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 9
• 229920006395 saturated elastomer Polymers 0.000 claims description 9
• 239000002246 antineoplastic agent Substances 0.000 claims description 8
• 125000006239 protecting group Chemical group 0.000 claims description 7
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
• CEIXWJHURKEBMQ-UHFFFAOYSA-N Heliamine Chemical compound C1CNCC2=C1C=C(OC)C(OC)=C2 CEIXWJHURKEBMQ-UHFFFAOYSA-N 0.000 claims description 6
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
• 238000010521 absorption reaction Methods 0.000 claims description 6
• 239000004480 active ingredient Substances 0.000 claims description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
• 229910052794 bromium Inorganic materials 0.000 claims description 6
• 229910052801 chlorine Inorganic materials 0.000 claims description 6
• 229940127089 cytotoxic agent Drugs 0.000 claims description 6
• 229910052731 fluorine Inorganic materials 0.000 claims description 6
• 150000002431 hydrogen Chemical class 0.000 claims description 6
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
• QPJWBLQMZLQKKV-UHFFFAOYSA-N n-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]-3-hydroxy-2-[(4-propan-2-ylbenzoyl)amino]benzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCNC(=O)C1=CC=CC(O)=C1NC(=O)C1=CC=C(C(C)C)C=C1 QPJWBLQMZLQKKV-UHFFFAOYSA-N 0.000 claims description 6
• IPBVNPXQWQGGJP-UHFFFAOYSA-N phenyl acetate Chemical compound CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 claims description 6
• KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 5
• 229940124597 therapeutic agent Drugs 0.000 claims description 5
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
• HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 claims description 4
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
• 230000008030 elimination Effects 0.000 claims description 4
• 238000003379 elimination reaction Methods 0.000 claims description 4
• 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 4
• SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims description 4
• 230000008569 process Effects 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 3
• 238000009826 distribution Methods 0.000 claims description 3
• 230000002708 enhancing effect Effects 0.000 claims description 3
• 230000004060 metabolic process Effects 0.000 claims description 3
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 3
• 230000036457 multidrug resistance Effects 0.000 claims description 3
• ULAAOSJIQBCTRS-UHFFFAOYSA-N n-[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]-2-[(2-hydroxybenzoyl)amino]benzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1NC(=O)C1=CC=CC=C1O ULAAOSJIQBCTRS-UHFFFAOYSA-N 0.000 claims description 3
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 claims description 3
• 230000001225 therapeutic effect Effects 0.000 claims description 3
• NDMFETHQFUOIQX-UHFFFAOYSA-N 1-(3-chloropropyl)imidazolidin-2-one Chemical compound ClCCCN1CCNC1=O NDMFETHQFUOIQX-UHFFFAOYSA-N 0.000 claims description 2
• CFLUZXBBAODGMU-UHFFFAOYSA-N 2-[(3-chlorobenzoyl)amino]-n-[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]benzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1NC(=O)C1=CC=CC(Cl)=C1 CFLUZXBBAODGMU-UHFFFAOYSA-N 0.000 claims description 2
• IZBRWILCDBHJNK-UHFFFAOYSA-N 2-[(4-bromobenzoyl)amino]-n-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]benzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCNC(=O)C1=CC=CC=C1NC(=O)C1=CC=C(Br)C=C1 IZBRWILCDBHJNK-UHFFFAOYSA-N 0.000 claims description 2
• CXGSVBMODMDXTE-UHFFFAOYSA-N 2-[(4-chlorobenzoyl)amino]-n-[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]benzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1NC(=O)C1=CC=C(Cl)C=C1 CXGSVBMODMDXTE-UHFFFAOYSA-N 0.000 claims description 2
• AFWNYCDOXGILNJ-UHFFFAOYSA-N 2-[(4-tert-butylbenzoyl)amino]-n-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]benzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCNC(=O)C1=CC=CC=C1NC(=O)C1=CC=C(C(C)(C)C)C=C1 AFWNYCDOXGILNJ-UHFFFAOYSA-N 0.000 claims description 2
• PNVUNEVYWIWKIR-UHFFFAOYSA-N 2-[[4-(diethylamino)benzoyl]amino]-n-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]benzamide Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)NC1=CC=CC=C1C(=O)NCCN1CC2=CC(OC)=C(OC)C=C2CC1 PNVUNEVYWIWKIR-UHFFFAOYSA-N 0.000 claims description 2
• SCQFRTPFUJVULZ-UHFFFAOYSA-N 2-benzamido-n-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]benzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCNC(=O)C1=CC=CC=C1NC(=O)C1=CC=CC=C1 SCQFRTPFUJVULZ-UHFFFAOYSA-N 0.000 claims description 2
• MAAPPGJUJOQIQQ-UHFFFAOYSA-N 2-benzamido-n-[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]-4-methylbenzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCC(C=C1)=CC=C1NC(=O)C1=CC=C(C)C=C1NC(=O)C1=CC=CC=C1 MAAPPGJUJOQIQQ-UHFFFAOYSA-N 0.000 claims description 2
• KYUQUCWNYQIEBR-UHFFFAOYSA-N 2-chloro-n-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]-6-[(4-propan-2-ylbenzoyl)amino]benzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCNC(=O)C1=C(Cl)C=CC=C1NC(=O)C1=CC=C(C(C)C)C=C1 KYUQUCWNYQIEBR-UHFFFAOYSA-N 0.000 claims description 2
• KJEFZSYHEXSHFS-UHFFFAOYSA-N 2-chloro-n-[2-[[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]carbamoyl]phenyl]quinoline-3-carboxamide Chemical compound C1=CC=C2N=C(Cl)C(C(=O)NC3=CC=CC=C3C(=O)NC3=CC=C(C=C3)CCN3CCC=4C=C(C(=CC=4C3)OC)OC)=CC2=C1 KJEFZSYHEXSHFS-UHFFFAOYSA-N 0.000 claims description 2
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
• MXUPRHVUKWLWKN-UHFFFAOYSA-N 4-chloro-n-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]-2-[(4-propan-2-ylbenzoyl)amino]benzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCNC(=O)C1=CC=C(Cl)C=C1NC(=O)C1=CC=C(C(C)C)C=C1 MXUPRHVUKWLWKN-UHFFFAOYSA-N 0.000 claims description 2
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 2
• NNJMFJSKMRYHSR-UHFFFAOYSA-N 4-phenylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1 NNJMFJSKMRYHSR-UHFFFAOYSA-N 0.000 claims description 2
• GHDUORLYUOIUNT-UHFFFAOYSA-N 5-chloro-n-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]-2-[(4-propan-2-ylbenzoyl)amino]benzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCNC(=O)C1=CC(Cl)=CC=C1NC(=O)C1=CC=C(C(C)C)C=C1 GHDUORLYUOIUNT-UHFFFAOYSA-N 0.000 claims description 2
• XXARIJKOAIKUFC-UHFFFAOYSA-N 6-benzamido-6-chloro-N-[4-[2-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)ethyl]phenyl]cyclohexa-2,4-diene-1-carboxamide Chemical compound ClC1(C(C(=O)NC2=CC=C(C=C2)CCN2CC3=CC(=C(C=C3CC2)OC)OC)C=CC=C1)NC(C1=CC=CC=C1)=O XXARIJKOAIKUFC-UHFFFAOYSA-N 0.000 claims description 2
• WQSMBJTXVXIMBT-UHFFFAOYSA-N COC1=C(C=C2CN(CCC2=C1)CCC3=CC=C(C=C3)NC(=O)C4=CC=CC=C4C5=C(SC=C5)C(=O)N)OC Chemical compound COC1=C(C=C2CN(CCC2=C1)CCC3=CC=C(C=C3)NC(=O)C4=CC=CC=C4C5=C(SC=C5)C(=O)N)OC WQSMBJTXVXIMBT-UHFFFAOYSA-N 0.000 claims description 2
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
• 150000001555 benzenes Chemical class 0.000 claims description 2
• 125000005805 dimethoxy phenyl group Chemical group 0.000 claims description 2
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
• 125000001041 indolyl group Chemical group 0.000 claims description 2
• XAAKCCMYRKZRAK-UHFFFAOYSA-N isoquinoline-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=NC=CC2=C1 XAAKCCMYRKZRAK-UHFFFAOYSA-N 0.000 claims description 2
• BEBNGNOBZMCMNT-UHFFFAOYSA-N n-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]-2-[(4-nitrobenzoyl)amino]benzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCNC(=O)C1=CC=CC=C1NC(=O)C1=CC=C([N+]([O-])=O)C=C1 BEBNGNOBZMCMNT-UHFFFAOYSA-N 0.000 claims description 2
• WHOCLXRJNYNVMS-UHFFFAOYSA-N n-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]-2-[(4-phenoxybenzoyl)amino]benzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCNC(=O)C1=CC=CC=C1NC(=O)C(C=C1)=CC=C1OC1=CC=CC=C1 WHOCLXRJNYNVMS-UHFFFAOYSA-N 0.000 claims description 2
• DYAVKLAUDQZKAQ-UHFFFAOYSA-N n-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]-2-[(4-propan-2-ylbenzoyl)amino]benzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCNC(=O)C1=CC=CC=C1NC(=O)C1=CC=C(C(C)C)C=C1 DYAVKLAUDQZKAQ-UHFFFAOYSA-N 0.000 claims description 2
• ATIGIJNPXYTTSA-UHFFFAOYSA-N n-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]-3-methoxy-2-[(4-propan-2-ylbenzoyl)amino]benzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCNC(=O)C1=CC=CC(OC)=C1NC(=O)C1=CC=C(C(C)C)C=C1 ATIGIJNPXYTTSA-UHFFFAOYSA-N 0.000 claims description 2
• YHLMVKOEXBOHDG-UHFFFAOYSA-N n-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]-3-methyl-2-[(4-propan-2-ylbenzoyl)amino]benzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCNC(=O)C1=CC=CC(C)=C1NC(=O)C1=CC=C(C(C)C)C=C1 YHLMVKOEXBOHDG-UHFFFAOYSA-N 0.000 claims description 2
• XSGXICYXNOYACJ-UHFFFAOYSA-N n-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]-4-fluoro-2-[(4-propan-2-ylbenzoyl)amino]benzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCNC(=O)C1=CC=C(F)C=C1NC(=O)C1=CC=C(C(C)C)C=C1 XSGXICYXNOYACJ-UHFFFAOYSA-N 0.000 claims description 2
• HWLACHUFHIZDNI-UHFFFAOYSA-N n-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]-4-nitro-2-[(4-propan-2-ylbenzoyl)amino]benzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCNC(=O)C1=CC=C([N+]([O-])=O)C=C1NC(=O)C1=CC=C(C(C)C)C=C1 HWLACHUFHIZDNI-UHFFFAOYSA-N 0.000 claims description 2
• NXDSYGAYPNMYGN-UHFFFAOYSA-N n-[2-[[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]carbamoyl]phenyl]-2,6-difluorobenzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1NC(=O)C1=C(F)C=CC=C1F NXDSYGAYPNMYGN-UHFFFAOYSA-N 0.000 claims description 2
• URTMDXKTCPYGBU-UHFFFAOYSA-N n-[2-[[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]carbamoyl]phenyl]-4-oxo-7-(trifluoromethyl)-1h-quinoline-3-carboxamide Chemical compound C1=C(C(F)(F)F)C=CC2=C(O)C(C(=O)NC3=CC=CC=C3C(=O)NC3=CC=C(C=C3)CCN3CCC=4C=C(C(=CC=4C3)OC)OC)=CN=C21 URTMDXKTCPYGBU-UHFFFAOYSA-N 0.000 claims description 2
• HKFOOHUJNPTUOS-UHFFFAOYSA-N n-[2-[[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]carbamoyl]phenyl]-6-methylpyridine-3-carboxamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1NC(=O)C1=CC=C(C)N=C1 HKFOOHUJNPTUOS-UHFFFAOYSA-N 0.000 claims description 2
• PPJLCZGIFHSLJC-UHFFFAOYSA-N n-[2-[[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]carbamoyl]phenyl]pyridine-3-carboxamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1NC(=O)C1=CC=CN=C1 PPJLCZGIFHSLJC-UHFFFAOYSA-N 0.000 claims description 2
• YKYCSDLADLZKGK-UHFFFAOYSA-N n-[2-[[4-[3-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)-2-hydroxypropoxy]phenyl]carbamoyl]phenyl]quinoline-3-carboxamide Chemical compound C1=CC=CC2=CC(C(=O)NC3=CC=CC=C3C(=O)NC3=CC=C(C=C3)OCC(O)CN3CCC=4C=C(C(=CC=4C3)OC)OC)=CN=C21 YKYCSDLADLZKGK-UHFFFAOYSA-N 0.000 claims description 2
• MOPNQMNIILJCSL-UHFFFAOYSA-N n-[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]-1,3-benzodioxole-2-carboxamide Chemical compound O1C2=CC=CC=C2OC1C(=O)NC(C=C1)=CC=C1CCN1CCC(C=C(C(=C2)OC)OC)=C2C1 MOPNQMNIILJCSL-UHFFFAOYSA-N 0.000 claims description 2
• DZQRYHQEBLFMMO-UHFFFAOYSA-N n-[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]-2-[(2-fluorobenzoyl)amino]benzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1NC(=O)C1=CC=CC=C1F DZQRYHQEBLFMMO-UHFFFAOYSA-N 0.000 claims description 2
• PXHXQLJGDGOYKQ-UHFFFAOYSA-N n-[4-[2-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]phenyl]-2-[(2-methoxybenzoyl)amino]benzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1NC(=O)C1=CC=CC=C1OC PXHXQLJGDGOYKQ-UHFFFAOYSA-N 0.000 claims description 2
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