KR102457145B1 - 항암제로서의 트리시클릭 화합물 - Google Patents

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Publication number

KR102457145B1

KR102457145B1 KR1020167019782A KR20167019782A KR102457145B1 KR 102457145 B1 KR102457145 B1 KR 102457145B1 KR 1020167019782 A KR1020167019782 A KR 1020167019782A KR 20167019782 A KR20167019782 A KR 20167019782A KR 102457145 B1 KR102457145 B1 KR 102457145B1

Authority

KR

South Korea

Prior art keywords

optionally substituted

methyl

alkyl

pyrido

indol

Prior art date

2013-12-24

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 223
• 239000002246 antineoplastic agent Substances 0.000 title 1
• 238000000034 method Methods 0.000 claims abstract description 101
• 238000011282 treatment Methods 0.000 claims abstract description 41
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 250
• 229910052739 hydrogen Inorganic materials 0.000 claims description 112
• -1 CD 3 Chemical class 0.000 claims description 107
• 239000001257 hydrogen Substances 0.000 claims description 106
• 125000001072 heteroaryl group Chemical group 0.000 claims description 79
• 125000000623 heterocyclic group Chemical group 0.000 claims description 79
• 125000003107 substituted aryl group Chemical group 0.000 claims description 70
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 63
• 229910052736 halogen Inorganic materials 0.000 claims description 54
• 150000002367 halogens Chemical class 0.000 claims description 53
• 150000003839 salts Chemical class 0.000 claims description 49
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 46
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 44
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 39
• 229910052757 nitrogen Inorganic materials 0.000 claims description 36
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 27
• 206010028980 Neoplasm Diseases 0.000 claims description 26
• 239000008194 pharmaceutical composition Substances 0.000 claims description 24
• 229920006395 saturated elastomer Polymers 0.000 claims description 24
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 23
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 22
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
• 201000011510 cancer Diseases 0.000 claims description 18
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
• 125000004432 carbon atom Chemical group C* 0.000 claims description 16
• 125000001188 haloalkyl group Chemical group 0.000 claims description 16
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
• 125000003118 aryl group Chemical group 0.000 claims description 15
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 14
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
• 229910052717 sulfur Inorganic materials 0.000 claims description 11
• 239000003937 drug carrier Substances 0.000 claims description 10
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 10
• 125000004122 cyclic group Chemical group 0.000 claims description 9
• 125000005842 heteroatom Chemical group 0.000 claims description 9
• 125000002950 monocyclic group Chemical group 0.000 claims description 8
• 229910052760 oxygen Inorganic materials 0.000 claims description 8
• 206010009944 Colon cancer Diseases 0.000 claims description 7
• 125000000304 alkynyl group Chemical group 0.000 claims description 7
• KGERZPVQIRYWRK-GDLZYMKVSA-N 2-[3-(3,5-dimethyltriazol-4-yl)-5-[(S)-oxan-4-yl(phenyl)methyl]pyrido[3,2-b]indol-7-yl]propan-2-ol Chemical compound CC=1N=NN(C=1C1=CC=2N(C=3C=C(C=CC=3C=2N=C1)C(C)(C)O)[C@H](C1=CC=CC=C1)C1CCOCC1)C KGERZPVQIRYWRK-GDLZYMKVSA-N 0.000 claims description 6
• FUDZXYQEMRWJGN-HHHXNRCGSA-N 2-[3-(5-methoxy-3-methyltriazol-4-yl)-5-[(S)-oxan-4-yl(phenyl)methyl]pyrido[3,2-b]indol-7-yl]propan-2-ol Chemical compound COC=1N=NN(C=1C1=CC=2N(C=3C=C(C=CC=3C=2N=C1)C(C)(C)O)[C@H](C1=CC=CC=C1)C1CCOCC1)C FUDZXYQEMRWJGN-HHHXNRCGSA-N 0.000 claims description 6
• 239000003085 diluting agent Substances 0.000 claims description 6
• 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 5
• 208000034578 Multiple myelomas Diseases 0.000 claims description 5
• 206010035226 Plasma cell myeloma Diseases 0.000 claims description 5
• 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 5
• 208000000587 small cell lung carcinoma Diseases 0.000 claims description 5
• 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 4
• 206010041067 Small cell lung cancer Diseases 0.000 claims description 4
• 125000002619 bicyclic group Chemical group 0.000 claims description 4
• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 4
• 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 4
• 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims description 3
• 206010029260 Neuroblastoma Diseases 0.000 claims description 3
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 3
• 201000005787 hematologic cancer Diseases 0.000 claims description 3
• 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 3
• 231100000844 hepatocellular carcinoma Toxicity 0.000 claims description 3
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 3
• 201000002528 pancreatic cancer Diseases 0.000 claims description 3
• 125000003367 polycyclic group Chemical group 0.000 claims description 3
• BPCOFZMFXLWUCE-XDFJSJKPSA-N (1R)-1-cyclopropyl-1-[3-(3,5-dimethyltriazol-4-yl)-6-fluoro-5-[(S)-(2-fluorophenyl)-(oxan-4-yl)methyl]pyrido[3,2-b]indol-7-yl]ethanol Chemical compound C1(CC1)[C@@](C)(O)C=1C=CC=2C3=C(N(C=2C=1F)[C@@H](C1CCOCC1)C1=C(C=CC=C1)F)C=C(C=N3)C1=C(N=NN1C)C BPCOFZMFXLWUCE-XDFJSJKPSA-N 0.000 claims description 2
• MSEKYFJKNKKJIR-XLJNKUFUSA-N (1R)-1-cyclopropyl-1-[3-(3,5-dimethyltriazol-4-yl)-6-fluoro-5-[(S)-oxan-4-yl(phenyl)methyl]pyrido[3,2-b]indol-7-yl]ethanol Chemical compound C1(CC1)[C@@](C)(O)C=1C=CC=2C3=C(N(C=2C=1F)[C@H](C1=CC=CC=C1)C1CCOCC1)C=C(C=N3)C1=C(N=NN1C)C MSEKYFJKNKKJIR-XLJNKUFUSA-N 0.000 claims description 2
• MSEKYFJKNKKJIR-QMGDAUJMSA-N (1R)-1-cyclopropyl-1-[6-fluoro-3-[3-methyl-5-(trideuteriomethyl)triazol-4-yl]-5-[(S)-oxan-4-yl(phenyl)methyl]pyrido[3,2-b]indol-7-yl]ethanol Chemical compound C1(CC1)[C@@](C)(O)C=1C=CC=2C3=C(N(C=2C=1F)[C@H](C1=CC=CC=C1)C1CCOCC1)C=C(C=N3)C1=C(N=NN1C)C([2H])([2H])[2H] MSEKYFJKNKKJIR-QMGDAUJMSA-N 0.000 claims description 2
• BPCOFZMFXLWUCE-MDSYIZKJSA-N (1R)-1-cyclopropyl-1-[6-fluoro-5-[(S)-(2-fluorophenyl)-(oxan-4-yl)methyl]-3-[3-methyl-5-(trideuteriomethyl)triazol-4-yl]pyrido[3,2-b]indol-7-yl]ethanol Chemical compound C1(CC1)[C@@](C)(O)C=1C=CC=2C3=C(N(C=2C=1F)[C@@H](C1CCOCC1)C1=C(C=CC=C1)F)C=C(C=N3)C1=C(N=NN1C)C([2H])([2H])[2H] BPCOFZMFXLWUCE-MDSYIZKJSA-N 0.000 claims description 2
• MSEKYFJKNKKJIR-CEKGIIEHSA-N (1S)-1-cyclopropyl-1-[6-fluoro-3-[3-methyl-5-(trideuteriomethyl)triazol-4-yl]-5-[(S)-oxan-4-yl(phenyl)methyl]pyrido[3,2-b]indol-7-yl]ethanol Chemical compound C1(CC1)[C@](C)(O)C=1C=CC=2C3=C(N(C=2C=1F)[C@H](C1=CC=CC=C1)C1CCOCC1)C=C(C=N3)C1=C(N=NN1C)C([2H])([2H])[2H] MSEKYFJKNKKJIR-CEKGIIEHSA-N 0.000 claims description 2
• BPCOFZMFXLWUCE-LFMMBFPVSA-N (1S)-1-cyclopropyl-1-[6-fluoro-5-[(S)-(2-fluorophenyl)-(oxan-4-yl)methyl]-3-[3-methyl-5-(trideuteriomethyl)triazol-4-yl]pyrido[3,2-b]indol-7-yl]ethanol Chemical compound C1(CC1)[C@](C)(O)C=1C=CC=2C3=C(N(C=2C=1F)[C@@H](C1CCOCC1)C1=C(C=CC=C1)F)C=C(C=N3)C1=C(N=NN1C)C([2H])([2H])[2H] BPCOFZMFXLWUCE-LFMMBFPVSA-N 0.000 claims description 2
• JZTHYZIZUIOGKF-SSEXGKCCSA-N 2-[3-(3,5-dimethyl-1,2-oxazol-4-yl)-5-[(S)-(4-fluorophenyl)-(oxan-4-yl)methyl]pyrido[3,2-b]indol-7-yl]propan-2-ol Chemical compound CC1=C(C(=NO1)C)C1=CC=2N(C=3C=C(C=CC=3C=2N=C1)C(C)(C)O)[C@@H](C1CCOCC1)C1=CC=C(C=C1)F JZTHYZIZUIOGKF-SSEXGKCCSA-N 0.000 claims description 2
• LZAPXWCSDTYFNB-SSEXGKCCSA-N 2-[3-(3,5-dimethyl-1,2-oxazol-4-yl)-5-[(S)-oxan-4-yl(phenyl)methyl]pyrido[3,2-b]indol-7-yl]propan-2-ol Chemical compound CC1=C(C(=NO1)C)C1=CC=2N(C=3C=C(C=CC=3C=2N=C1)C(C)(C)O)[C@H](C1=CC=CC=C1)C1CCOCC1 LZAPXWCSDTYFNB-SSEXGKCCSA-N 0.000 claims description 2
• BTZFFGCZYGLTFW-UHFFFAOYSA-N 2-[3-(3,5-dimethyltriazol-4-yl)-5-(1,1,1,7,7,7-hexafluoroheptan-4-yl)pyrido[3,2-b]indol-7-yl]propan-2-ol Chemical compound CC=1N=NN(C=1C1=CC=2N(C=3C=C(C=CC=3C=2N=C1)C(C)(C)O)C(CCC(F)(F)F)CCC(F)(F)F)C BTZFFGCZYGLTFW-UHFFFAOYSA-N 0.000 claims description 2
• DKJVGQHEKKNIQT-UHFFFAOYSA-N 2-[3-(3,5-dimethyltriazol-4-yl)-5-[(4-fluorophenyl)-(oxan-4-yl)methyl]pyrido[3,2-b]indol-7-yl]propan-2-ol Chemical compound CC=1N=NN(C=1C1=CC=2N(C=3C=C(C=CC=3C=2N=C1)C(C)(C)O)C(C1CCOCC1)C1=CC=C(C=C1)F)C DKJVGQHEKKNIQT-UHFFFAOYSA-N 0.000 claims description 2
• VAWJPFDOLDVDEV-NDEPHWFRSA-N 2-[3-(3,5-dimethyltriazol-4-yl)-6-fluoro-5-[(S)-(2-fluorophenyl)-(oxan-4-yl)methyl]pyrido[3,2-b]indol-7-yl]propan-2-ol Chemical compound CN1N=NC(C)=C1C1=CC2=C(N=C1)C1=CC=C(C(F)=C1N2[C@@H](C1CCOCC1)C1=C(F)C=CC=C1)C(C)(C)O VAWJPFDOLDVDEV-NDEPHWFRSA-N 0.000 claims description 2
• OYOOOLZFBKNGEJ-MUUNZHRXSA-N 2-[3-(3,5-dimethyltriazol-4-yl)-6-fluoro-5-[(S)-oxan-4-yl(phenyl)methyl]pyrido[3,2-b]indol-7-yl]propan-2-ol Chemical compound CC=1N=NN(C=1C1=CC=2N(C=3C(=C(C=CC=3C=2N=C1)C(C)(C)O)F)[C@H](C1=CC=CC=C1)C1CCOCC1)C OYOOOLZFBKNGEJ-MUUNZHRXSA-N 0.000 claims description 2
• OEFUOYSAXXZXCN-LJAQVGFWSA-N 2-[3-(3,5-dimethyltriazol-4-yl)-8-fluoro-5-[(S)-(2-fluorophenyl)-(oxan-4-yl)methyl]pyrido[3,2-b]indol-7-yl]propan-2-ol Chemical compound CN1N=NC(C)=C1C1=CC2=C(N=C1)C1=CC(F)=C(C=C1N2[C@@H](C1CCOCC1)C1=C(F)C=CC=C1)C(C)(C)O OEFUOYSAXXZXCN-LJAQVGFWSA-N 0.000 claims description 2
• UJARZGSRRXPOTK-GDLZYMKVSA-N 2-[3-(3,5-dimethyltriazol-4-yl)-8-fluoro-5-[(S)-oxan-4-yl(phenyl)methyl]pyrido[3,2-b]indol-7-yl]propan-2-ol Chemical compound CN1N=NC(C)=C1C1=CC2=C(N=C1)C1=CC(F)=C(C=C1N2[C@@H](C1CCOCC1)C1=CC=CC=C1)C(C)(C)O UJARZGSRRXPOTK-GDLZYMKVSA-N 0.000 claims description 2
• RMQALCZQOUJTEN-MUUNZHRXSA-N 2-[3-[5-(hydroxymethyl)-3-methyltriazol-4-yl]-5-[(S)-oxan-4-yl(phenyl)methyl]pyrido[3,2-b]indol-7-yl]propan-2-ol Chemical compound OCC=1N=NN(C=1C1=CC=2N(C=3C=C(C=CC=3C=2N=C1)C(C)(C)O)[C@H](C1=CC=CC=C1)C1CCOCC1)C RMQALCZQOUJTEN-MUUNZHRXSA-N 0.000 claims description 2
• FUDZXYQEMRWJGN-DVOXTMAASA-N 2-[3-[5-methoxy-3-(trideuteriomethyl)triazol-4-yl]-5-[(S)-oxan-4-yl(phenyl)methyl]pyrido[3,2-b]indol-7-yl]propan-2-ol Chemical compound COC=1N=NN(C=1C1=CC=2N(C=3C=C(C=CC=3C=2N=C1)C(C)(C)O)[C@H](C1=CC=CC=C1)C1CCOCC1)C([2H])([2H])[2H] FUDZXYQEMRWJGN-DVOXTMAASA-N 0.000 claims description 2
• MWFJOHMMTFRWQB-FIBGUPNXSA-N 2-[5-[(3-chloropyridin-2-yl)-(oxan-4-yl)methyl]-3-[3-methyl-5-(trideuteriomethyl)triazol-4-yl]pyrido[3,2-b]indol-7-yl]propan-2-ol Chemical compound ClC=1C(=NC=CC=1)C(N1C2=C(C=3C=CC(=CC1=3)C(C)(C)O)N=CC(=C2)C1=C(N=NN1C)C([2H])([2H])[2H])C1CCOCC1 MWFJOHMMTFRWQB-FIBGUPNXSA-N 0.000 claims description 2
• OAXDPZUDXBJTBA-FIBGUPNXSA-N 2-[5-[(3-fluoropyridin-2-yl)-(oxan-4-yl)methyl]-3-[3-methyl-5-(trideuteriomethyl)triazol-4-yl]pyrido[3,2-b]indol-7-yl]propan-2-ol Chemical compound FC=1C(=NC=CC=1)C(N1C2=C(C=3C=CC(=CC1=3)C(C)(C)O)N=CC(=C2)C1=C(N=NN1C)C([2H])([2H])[2H])C1CCOCC1 OAXDPZUDXBJTBA-FIBGUPNXSA-N 0.000 claims description 2
• ITCDSZBBRIDJGB-FIBGUPNXSA-N 2-[5-[(4,4-difluorocyclohexyl)-(3-fluoropyridin-2-yl)methyl]-6-fluoro-3-[3-methyl-5-(trideuteriomethyl)triazol-4-yl]pyrido[3,2-b]indol-7-yl]propan-2-ol Chemical compound FC1(CCC(CC1)C(N1C2=C(C=3C=CC(=C(C1=3)F)C(C)(C)O)N=CC(=C2)C1=C(N=NN1C)C([2H])([2H])[2H])C1=NC=CC=C1F)F ITCDSZBBRIDJGB-FIBGUPNXSA-N 0.000 claims description 2
• GRMFQZXBEVRHJS-FIBGUPNXSA-N 2-[5-[(4-chloropyridin-2-yl)-(oxan-4-yl)methyl]-3-[3-methyl-5-(trideuteriomethyl)triazol-4-yl]pyrido[3,2-b]indol-7-yl]propan-2-ol Chemical compound ClC1=CC(=NC=C1)C(N1C2=C(C=3C=CC(=CC1=3)C(C)(C)O)N=CC(=C2)C1=C(N=NN1C)C([2H])([2H])[2H])C1CCOCC1 GRMFQZXBEVRHJS-FIBGUPNXSA-N 0.000 claims description 2
• JKATWBOQPOZUSM-FIBGUPNXSA-N 2-[5-[(5-chloropyridin-2-yl)-(oxan-4-yl)methyl]-3-[3-methyl-5-(trideuteriomethyl)triazol-4-yl]pyrido[3,2-b]indol-7-yl]propan-2-ol Chemical compound ClC=1C=CC(=NC=1)C(N1C2=C(C=3C=CC(=CC1=3)C(C)(C)O)N=CC(=C2)C1=C(N=NN1C)C([2H])([2H])[2H])C1CCOCC1 JKATWBOQPOZUSM-FIBGUPNXSA-N 0.000 claims description 2
• DVGOMSURZGWXJT-GNUZTRDVSA-N 2-[5-[(S)-(4,4-difluorocyclohexyl)-phenylmethyl]-3-[3-methyl-5-(trideuteriomethyl)triazol-4-yl]pyrido[3,2-b]indol-7-yl]propan-2-ol Chemical compound FC1(CCC(CC1)[C@H](N1C2=C(C=3C=CC(=CC1=3)C(C)(C)O)N=CC(=C2)C1=C(N=NN1C)C([2H])([2H])[2H])C1=CC=CC=C1)F DVGOMSURZGWXJT-GNUZTRDVSA-N 0.000 claims description 2
• DKJVGQHEKKNIQT-GNUZTRDVSA-N 2-[5-[(S)-(4-fluorophenyl)-(oxan-4-yl)methyl]-3-[3-methyl-5-(trideuteriomethyl)triazol-4-yl]pyrido[3,2-b]indol-7-yl]propan-2-ol Chemical compound FC1=CC=C(C=C1)[C@@H](N1C2=C(C=3C=CC(=CC1=3)C(C)(C)O)N=CC(=C2)C1=C(N=NN1C)C([2H])([2H])[2H])C1CCOCC1 DKJVGQHEKKNIQT-GNUZTRDVSA-N 0.000 claims description 2
• IWRRLINMFXHEBN-MUUNZHRXSA-N 2-[6-chloro-3-(3,5-dimethyltriazol-4-yl)-5-[(S)-oxan-4-yl(phenyl)methyl]pyrido[3,2-b]indol-7-yl]propan-2-ol Chemical compound CN1N=NC(C)=C1C1=CC2=C(N=C1)C1=CC=C(C(Cl)=C1N2[C@@H](C1CCOCC1)C1=CC=CC=C1)C(C)(C)O IWRRLINMFXHEBN-MUUNZHRXSA-N 0.000 claims description 2
• GJGSUFHIMBFZFP-FIBGUPNXSA-N 2-[6-fluoro-5-[(3-fluoropyridin-2-yl)-(oxan-4-yl)methyl]-3-[3-methyl-5-(trideuteriomethyl)triazol-4-yl]pyrido[3,2-b]indol-7-yl]propan-2-ol Chemical compound FC1=C(C=CC=2C3=C(N(C1=2)C(C1CCOCC1)C1=NC=CC=C1F)C=C(C=N3)C1=C(N=NN1C)C([2H])([2H])[2H])C(C)(C)O GJGSUFHIMBFZFP-FIBGUPNXSA-N 0.000 claims description 2
• UUPBDBBRDHXXDR-BMSJAHLVSA-N 2-[6-fluoro-5-[(5-methyl-1,2-oxazol-3-yl)-(oxan-4-yl)methyl]-3-[3-methyl-5-(trideuteriomethyl)triazol-4-yl]pyrido[3,2-b]indol-7-yl]propan-2-ol Chemical compound FC1=C(C=CC=2C3=C(N(C1=2)C(C1CCOCC1)C1=NOC(=C1)C)C=C(C=N3)C1=C(N=NN1C)C([2H])([2H])[2H])C(C)(C)O UUPBDBBRDHXXDR-BMSJAHLVSA-N 0.000 claims description 2
• MUUQICROBARRSW-FIBGUPNXSA-N 2-[8-fluoro-5-[(3-fluoropyridin-2-yl)-(oxan-4-yl)methyl]-3-[3-methyl-5-(trideuteriomethyl)triazol-4-yl]pyrido[3,2-b]indol-7-yl]propan-2-ol Chemical compound FC1=CC=2C3=C(N(C=2C=C1C(C)(C)O)C(C1CCOCC1)C1=NC=CC=C1F)C=C(C=N3)C1=C(N=NN1C)C([2H])([2H])[2H] MUUQICROBARRSW-FIBGUPNXSA-N 0.000 claims description 2
• DIBNHWMOCZSWAS-BMSJAHLVSA-N 2-[8-fluoro-5-[(5-methyl-1,2-oxazol-3-yl)-(oxan-4-yl)methyl]-3-[3-methyl-5-(trideuteriomethyl)triazol-4-yl]pyrido[3,2-b]indol-7-yl]propan-2-ol Chemical compound FC1=CC=2C3=C(N(C=2C=C1C(C)(C)O)C(C1CCOCC1)C1=NOC(=C1)C)C=C(C=N3)C1=C(N=NN1C)C([2H])([2H])[2H] DIBNHWMOCZSWAS-BMSJAHLVSA-N 0.000 claims description 2
• PUHMOBALEOWSMA-HHHXNRCGSA-N 3-(3,5-dimethyltriazol-4-yl)-6-methylsulfonyl-5-[(S)-oxan-4-yl(phenyl)methyl]pyrido[3,2-b]indole Chemical compound CS(=O)(=O)C1=CC=CC=2C3=C(N(C1=2)[C@H](C1=CC=CC=C1)C1CCOCC1)C=C(C=N3)C1=C(N=NN1C)C PUHMOBALEOWSMA-HHHXNRCGSA-N 0.000 claims description 2
• WMGCUONRPGLRCM-GDLZYMKVSA-N 3-(3,5-dimethyltriazol-4-yl)-7-(methylsulfonylmethyl)-5-[(S)-oxan-4-yl(phenyl)methyl]pyrido[3,2-b]indole Chemical compound Cc1nnn(C)c1-c1cnc2c(c1)n([C@@H](C1CCOCC1)c1ccccc1)c1cc(CS(C)(=O)=O)ccc21 WMGCUONRPGLRCM-GDLZYMKVSA-N 0.000 claims description 2
• PEFBBFRPHUTZEM-HHHXNRCGSA-N 3-(3,5-dimethyltriazol-4-yl)-9-fluoro-6-methylsulfonyl-5-[(S)-oxan-4-yl(phenyl)methyl]pyrido[3,2-b]indole Chemical compound FC=1C=2C3=C(N(C=2C(=CC=1)S(=O)(=O)C)[C@H](C1=CC=CC=C1)C1CCOCC1)C=C(C=N3)C1=C(N=NN1C)C PEFBBFRPHUTZEM-HHHXNRCGSA-N 0.000 claims description 2
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