NO312159B1 - Nye trisykliske forbindelser og medikamentsammensetninger inneholdende slike - Google Patents

Info

Publication number

NO312159B1

NO312159B1 NO19983197A NO983197A NO312159B1 NO 312159 B1 NO312159 B1 NO 312159B1 NO 19983197 A NO19983197 A NO 19983197A NO 983197 A NO983197 A NO 983197A NO 312159 B1 NO312159 B1 NO 312159B1

Authority

NO

Norway

Prior art keywords

yloxy

hydrogen atom

atom

ethylamino

carbazol

Prior art date

1996-01-10

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 453
• 229940079593 drug Drugs 0.000 title claims abstract description 20
• 239000003814 drug Substances 0.000 title claims abstract description 20
• 239000000203 mixture Substances 0.000 title claims description 186
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 262
• 238000000034 method Methods 0.000 claims abstract description 138
• -1 hydroxy, benzyloxy, amino Chemical group 0.000 claims abstract description 94
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 91
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 65
• 150000003839 salts Chemical class 0.000 claims abstract description 50
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 47
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 45
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 43
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 41
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 36
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract description 33
• 238000011282 treatment Methods 0.000 claims abstract description 32
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 28
• 208000008589 Obesity Diseases 0.000 claims abstract description 9
• 235000020824 obesity Nutrition 0.000 claims abstract description 9
• 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 7
• 201000005577 familial hyperlipidemia Diseases 0.000 claims abstract description 7
• 230000008569 process Effects 0.000 claims abstract description 4
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 240
• 125000006239 protecting group Chemical group 0.000 claims description 88
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 81
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 51
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 49
• 125000003277 amino group Chemical group 0.000 claims description 44
• 229910052799 carbon Inorganic materials 0.000 claims description 34
• 125000004432 carbon atom Chemical group C* 0.000 claims description 34
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 34
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 33
• 125000004434 sulfur atom Chemical group 0.000 claims description 33
• 125000005843 halogen group Chemical group 0.000 claims description 28
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 26
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 24
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 23
• 230000009467 reduction Effects 0.000 claims description 18
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 17
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 16
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 15
• 229910052731 fluorine Inorganic materials 0.000 claims description 13
• 238000004519 manufacturing process Methods 0.000 claims description 12
• HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 12
• 229910052801 chlorine Inorganic materials 0.000 claims description 11
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
• 125000001153 fluoro group Chemical group F* 0.000 claims description 11
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 9
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 8
• 229910052740 iodine Chemical group 0.000 claims description 8
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 7
• 230000003449 preventive effect Effects 0.000 claims description 6
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• 230000001225 therapeutic effect Effects 0.000 claims description 5
• 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 claims description 4
• NVKHCBMVFOJXJB-UHFFFAOYSA-N n-[5-[2-[2-[(7-amino-9h-fluoren-2-yl)oxy]ethylamino]-1-hydroxyethyl]-2-hydroxyphenyl]methanesulfonamide Chemical compound C1=C(O)C(NS(=O)(=O)C)=CC(C(O)CNCCOC=2C=C3C(C4=CC=C(N)C=C4C3)=CC=2)=C1 NVKHCBMVFOJXJB-UHFFFAOYSA-N 0.000 claims description 4
• OPYNTUQGVOERTC-UHFFFAOYSA-N 4-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]phenol Chemical compound C=1C=C(C2=CC=CC=C2N2)C2=CC=1OCCNCC(O)C1=CC=C(O)C=C1 OPYNTUQGVOERTC-UHFFFAOYSA-N 0.000 claims description 3
• PYAPJIBHIHRYAJ-UHFFFAOYSA-N n-[2-amino-5-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-methoxyethyl]phenyl]methanesulfonamide Chemical compound C=1C=C(C2=CC=CC=C2N2)C2=CC=1OCCNCC(OC)C1=CC=C(N)C(NS(C)(=O)=O)=C1 PYAPJIBHIHRYAJ-UHFFFAOYSA-N 0.000 claims description 3
• GOEGMKAAILGFAS-UHFFFAOYSA-N n-[5-[2-(2-dibenzothiophen-3-yloxyethylamino)-1-methoxyethyl]-2-hydroxyphenyl]methanesulfonamide Chemical compound C=1C=C(C2=CC=CC=C2S2)C2=CC=1OCCNCC(OC)C1=CC=C(O)C(NS(C)(=O)=O)=C1 GOEGMKAAILGFAS-UHFFFAOYSA-N 0.000 claims description 3
• MNQQHDGNJUBFGR-UHFFFAOYSA-N n-[5-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-methoxyethyl]-2-hydroxyphenyl]methanesulfonamide Chemical compound C=1C=C(C2=CC=CC=C2N2)C2=CC=1OCCNCC(OC)C1=CC=C(O)C(NS(C)(=O)=O)=C1 MNQQHDGNJUBFGR-UHFFFAOYSA-N 0.000 claims description 3
• 238000002360 preparation method Methods 0.000 claims description 3
• 230000001681 protective effect Effects 0.000 claims description 3
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
• IXJKCHZJMPZZKF-UHFFFAOYSA-N 1-(3-aminophenyl)-2-[2-(9h-carbazol-2-yloxy)ethylamino]ethanol Chemical compound NC1=CC=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 IXJKCHZJMPZZKF-UHFFFAOYSA-N 0.000 claims description 2
• IJHWHKZMLDZXPN-UHFFFAOYSA-N 2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-(2-fluorophenyl)ethanol Chemical compound C=1C=C(C2=CC=CC=C2N2)C2=CC=1OCCNCC(O)C1=CC=CC=C1F IJHWHKZMLDZXPN-UHFFFAOYSA-N 0.000 claims description 2
• MLUIHKSMGSSIAZ-UHFFFAOYSA-N 2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-(3-nitrophenyl)ethanol Chemical compound C=1C=C(C2=CC=CC=C2N2)C2=CC=1OCCNCC(O)C1=CC=CC([N+]([O-])=O)=C1 MLUIHKSMGSSIAZ-UHFFFAOYSA-N 0.000 claims description 2
• ZIKXIHALQFRIQE-UHFFFAOYSA-N 2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-[3-(methylamino)-4-phenylmethoxyphenyl]ethanol Chemical compound CNC1=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=CC=C1OCC1=CC=CC=C1 ZIKXIHALQFRIQE-UHFFFAOYSA-N 0.000 claims description 2
• NTYZRYQWVHOSFC-UHFFFAOYSA-N 2-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]phenol Chemical compound C=1C=C(C2=CC=CC=C2N2)C2=CC=1OCCNCC(O)C1=CC=CC=C1O NTYZRYQWVHOSFC-UHFFFAOYSA-N 0.000 claims description 2
• DUPOGPRETAXXJT-DEOSSOPVSA-N 2-[2-[[(2r)-2-[3-(dimethylsulfamoylamino)-4-hydroxyphenyl]-2-hydroxyethyl]amino]ethoxy]-9h-carbazole Chemical compound C1=C(O)C(NS(=O)(=O)N(C)C)=CC([C@@H](O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 DUPOGPRETAXXJT-DEOSSOPVSA-N 0.000 claims description 2
• DUPOGPRETAXXJT-XMMPIXPASA-N 2-[2-[[(2s)-2-[3-(dimethylsulfamoylamino)-4-hydroxyphenyl]-2-hydroxyethyl]amino]ethoxy]-9h-carbazole Chemical compound C1=C(O)C(NS(=O)(=O)N(C)C)=CC([C@H](O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 DUPOGPRETAXXJT-XMMPIXPASA-N 0.000 claims description 2
• OVUXYPOLJTVGNL-UHFFFAOYSA-N 2-[2-[[2-[3-(diethylsulfamoylamino)-4-hydroxyphenyl]-2-hydroxyethyl]amino]ethoxy]-9h-carbazole Chemical compound C1=C(O)C(NS(=O)(=O)N(CC)CC)=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 OVUXYPOLJTVGNL-UHFFFAOYSA-N 0.000 claims description 2
• OQSKLCAAJQXXNR-UHFFFAOYSA-N 2-[2-[[2-[3-(dimethylsulfamoylamino)-4-fluorophenyl]-2-hydroxyethyl]amino]ethoxy]-9h-carbazole Chemical compound C1=C(F)C(NS(=O)(=O)N(C)C)=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 OQSKLCAAJQXXNR-UHFFFAOYSA-N 0.000 claims description 2
• FIEWDKKCJXNSFS-UHFFFAOYSA-N 2-amino-4-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]phenol Chemical compound C1=C(O)C(N)=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 FIEWDKKCJXNSFS-UHFFFAOYSA-N 0.000 claims description 2
• NVMARZSMVAILSO-UHFFFAOYSA-N 3-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 NVMARZSMVAILSO-UHFFFAOYSA-N 0.000 claims description 2
• JPXPXAOXDULILV-QFIPXVFZSA-N 3-[2-[[(2r)-2-[3-(dimethylsulfamoylamino)-4-hydroxyphenyl]-2-hydroxyethyl]amino]ethoxy]dibenzofuran Chemical compound C1=C(O)C(NS(=O)(=O)N(C)C)=CC([C@@H](O)CNCCOC=2C=C3C(C4=CC=CC=C4O3)=CC=2)=C1 JPXPXAOXDULILV-QFIPXVFZSA-N 0.000 claims description 2
• NWRNHCJNFDISLJ-UHFFFAOYSA-N 4-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]-2-(hydroxymethyl)phenol Chemical compound C1=C(O)C(CO)=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 NWRNHCJNFDISLJ-UHFFFAOYSA-N 0.000 claims description 2
• IKCXSIRETPFEEO-UHFFFAOYSA-N 4-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]-2-(methylamino)phenol Chemical compound C1=C(O)C(NC)=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 IKCXSIRETPFEEO-UHFFFAOYSA-N 0.000 claims description 2
• KESXIKRVBNXWEA-UHFFFAOYSA-N 4-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]-2-nitrophenol Chemical compound C=1C=C(C2=CC=CC=C2N2)C2=CC=1OCCNCC(O)C1=CC=C(O)C([N+]([O-])=O)=C1 KESXIKRVBNXWEA-UHFFFAOYSA-N 0.000 claims description 2
• HBRDJLQNJOKSQG-UHFFFAOYSA-N [5-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]-2-hydroxyphenyl]urea Chemical compound C1=C(O)C(NC(=O)N)=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 HBRDJLQNJOKSQG-UHFFFAOYSA-N 0.000 claims description 2
• PMQYHUDCVLRMBX-UHFFFAOYSA-N [5-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]-2-phenylmethoxyphenyl]urea Chemical compound NC(=O)NC1=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=CC=C1OCC1=CC=CC=C1 PMQYHUDCVLRMBX-UHFFFAOYSA-N 0.000 claims description 2
• DWKVGEYYBUPTFU-UHFFFAOYSA-N n-[2-amino-5-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]phenyl]methanesulfonamide Chemical compound C1=C(N)C(NS(=O)(=O)C)=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 DWKVGEYYBUPTFU-UHFFFAOYSA-N 0.000 claims description 2
• HVSCONOCEJUEGP-UHFFFAOYSA-N n-[2-bromo-5-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]phenyl]methanesulfonamide Chemical compound C1=C(Br)C(NS(=O)(=O)C)=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 HVSCONOCEJUEGP-UHFFFAOYSA-N 0.000 claims description 2
• QQQJTXUWELTWSR-UHFFFAOYSA-N n-[2-chloro-5-[2-(2-dibenzofuran-3-yloxyethylamino)-1-hydroxyethyl]phenyl]methanesulfonamide Chemical compound C1=C(Cl)C(NS(=O)(=O)C)=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4O3)=CC=2)=C1 QQQJTXUWELTWSR-UHFFFAOYSA-N 0.000 claims description 2
• UWXISSDMCHBBEA-UHFFFAOYSA-N n-[2-chloro-5-[2-(2-dibenzothiophen-3-yloxyethylamino)-1-hydroxyethyl]phenyl]methanesulfonamide Chemical compound C1=C(Cl)C(NS(=O)(=O)C)=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4S3)=CC=2)=C1 UWXISSDMCHBBEA-UHFFFAOYSA-N 0.000 claims description 2
• VBXJNUVUFQZVBR-UHFFFAOYSA-N n-[2-hydroxy-5-[1-hydroxy-2-[2-[(3-hydroxy-9h-carbazol-2-yl)oxy]ethylamino]ethyl]phenyl]methanesulfonamide Chemical compound C1=C(O)C(NS(=O)(=O)C)=CC(C(O)CNCCOC=2C(=CC=3C4=CC=CC=C4NC=3C=2)O)=C1 VBXJNUVUFQZVBR-UHFFFAOYSA-N 0.000 claims description 2
• MEJURHFWXLRFTN-UHFFFAOYSA-N n-[2-hydroxy-5-[1-hydroxy-2-[2-[(6-hydroxy-9h-carbazol-2-yl)oxy]ethylamino]ethyl]phenyl]methanesulfonamide Chemical compound C1=C(O)C(NS(=O)(=O)C)=CC(C(O)CNCCOC=2C=C3C(C4=CC(O)=CC=C4N3)=CC=2)=C1 MEJURHFWXLRFTN-UHFFFAOYSA-N 0.000 claims description 2
• DTOHSKBTGDUVJL-QHCPKHFHSA-N n-[3-[(1r)-2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC([C@@H](O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 DTOHSKBTGDUVJL-QHCPKHFHSA-N 0.000 claims description 2
• DTOHSKBTGDUVJL-HSZRJFAPSA-N n-[3-[(1s)-2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC([C@H](O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 DTOHSKBTGDUVJL-HSZRJFAPSA-N 0.000 claims description 2
• JOZSWZXNFNAMQE-UHFFFAOYSA-N n-[3-[2-(2-dibenzofuran-3-yloxyethylamino)-1-hydroxyethyl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4O3)=CC=2)=C1 JOZSWZXNFNAMQE-UHFFFAOYSA-N 0.000 claims description 2
• GDAWGPRURXSDCE-UHFFFAOYSA-N n-[3-[2-(2-dibenzothiophen-3-yloxyethylamino)-1-hydroxyethyl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4S3)=CC=2)=C1 GDAWGPRURXSDCE-UHFFFAOYSA-N 0.000 claims description 2
• BRLFCGZMBLUHQH-UHFFFAOYSA-N n-[3-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]-2-hydroxyphenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1O BRLFCGZMBLUHQH-UHFFFAOYSA-N 0.000 claims description 2
• OEJMSTWQZJOZET-UHFFFAOYSA-N n-[3-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]-4-hydroxyphenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=C(O)C(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 OEJMSTWQZJOZET-UHFFFAOYSA-N 0.000 claims description 2
• QMHCLYPZXZLNIY-UHFFFAOYSA-N n-[3-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]-5-hydroxyphenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC(O)=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 QMHCLYPZXZLNIY-UHFFFAOYSA-N 0.000 claims description 2
• BZMKQOOKVCZRLZ-UHFFFAOYSA-N n-[3-[2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]phenyl]formamide Chemical compound C=1C=C(C2=CC=CC=C2N2)C2=CC=1OCCNCC(O)C1=CC=CC(NC=O)=C1 BZMKQOOKVCZRLZ-UHFFFAOYSA-N 0.000 claims description 2
• COCLADHXYWRUIH-UHFFFAOYSA-N n-[3-[2-[2-[(7-amino-9h-fluoren-2-yl)oxy]ethylamino]-1-hydroxyethyl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C(O)CNCCOC=2C=C3C(C4=CC=C(N)C=C4C3)=CC=2)=C1 COCLADHXYWRUIH-UHFFFAOYSA-N 0.000 claims description 2
• RHRGYGCGWSZVCU-NRFANRHFSA-N n-[5-[(1r)-2-(2-dibenzofuran-3-yloxyethylamino)-1-hydroxyethyl]-2-hydroxyphenyl]methanesulfonamide Chemical compound C1=C(O)C(NS(=O)(=O)C)=CC([C@@H](O)CNCCOC=2C=C3C(C4=CC=CC=C4O3)=CC=2)=C1 RHRGYGCGWSZVCU-NRFANRHFSA-N 0.000 claims description 2
• FXALXNZMNXWULQ-DEOSSOPVSA-N n-[5-[(1r)-2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]-2-(hydroxymethyl)phenyl]methanesulfonamide Chemical compound C1=C(CO)C(NS(=O)(=O)C)=CC([C@@H](O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 FXALXNZMNXWULQ-DEOSSOPVSA-N 0.000 claims description 2
• GJPWBSFNWKJIIC-QHCPKHFHSA-N n-[5-[(1r)-2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]-2-chlorophenyl]methanesulfonamide Chemical compound C1=C(Cl)C(NS(=O)(=O)C)=CC([C@@H](O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 GJPWBSFNWKJIIC-QHCPKHFHSA-N 0.000 claims description 2
• JANCFZMNYVRUDL-QHCPKHFHSA-N n-[5-[(1r)-2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]-2-fluorophenyl]methanesulfonamide Chemical compound C1=C(F)C(NS(=O)(=O)C)=CC([C@@H](O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 JANCFZMNYVRUDL-QHCPKHFHSA-N 0.000 claims description 2
• MWCDQOSTJHWLFI-QHCPKHFHSA-N n-[5-[(1r)-2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]-2-hydroxyphenyl]methanesulfonamide Chemical compound C1=C(O)C(NS(=O)(=O)C)=CC([C@@H](O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 MWCDQOSTJHWLFI-QHCPKHFHSA-N 0.000 claims description 2
• RHRGYGCGWSZVCU-OAQYLSRUSA-N n-[5-[(1s)-2-(2-dibenzofuran-3-yloxyethylamino)-1-hydroxyethyl]-2-hydroxyphenyl]methanesulfonamide Chemical compound C1=C(O)C(NS(=O)(=O)C)=CC([C@H](O)CNCCOC=2C=C3C(C4=CC=CC=C4O3)=CC=2)=C1 RHRGYGCGWSZVCU-OAQYLSRUSA-N 0.000 claims description 2
• GJPWBSFNWKJIIC-HSZRJFAPSA-N n-[5-[(1s)-2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]-2-chlorophenyl]methanesulfonamide Chemical compound C1=C(Cl)C(NS(=O)(=O)C)=CC([C@H](O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 GJPWBSFNWKJIIC-HSZRJFAPSA-N 0.000 claims description 2
• MWCDQOSTJHWLFI-HSZRJFAPSA-N n-[5-[(1s)-2-[2-(9h-carbazol-2-yloxy)ethylamino]-1-hydroxyethyl]-2-hydroxyphenyl]methanesulfonamide Chemical compound C1=C(O)C(NS(=O)(=O)C)=CC([C@H](O)CNCCOC=2C=C3C(C4=CC=CC=C4N3)=CC=2)=C1 MWCDQOSTJHWLFI-HSZRJFAPSA-N 0.000 claims description 2
• NJSOTNOENOAKJC-UHFFFAOYSA-N n-[5-[2-(2-dibenzofuran-3-yloxyethylamino)-1-hydroxyethyl]-2-fluorophenyl]methanesulfonamide Chemical compound C1=C(F)C(NS(=O)(=O)C)=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4O3)=CC=2)=C1 NJSOTNOENOAKJC-UHFFFAOYSA-N 0.000 claims description 2
• RHRGYGCGWSZVCU-UHFFFAOYSA-N n-[5-[2-(2-dibenzofuran-3-yloxyethylamino)-1-hydroxyethyl]-2-hydroxyphenyl]methanesulfonamide Chemical compound C1=C(O)C(NS(=O)(=O)C)=CC(C(O)CNCCOC=2C=C3C(C4=CC=CC=C4O3)=CC=2)=C1 RHRGYGCGWSZVCU-UHFFFAOYSA-N 0.000 claims description 2
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