ES2698998T3 - Compuestos tricíclicos como agentes antineoplásicos - Google Patents

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Publication number

ES2698998T3

ES2698998T3 ES14824743T ES14824743T ES2698998T3 ES 2698998 T3 ES2698998 T3 ES 2698998T3 ES 14824743 T ES14824743 T ES 14824743T ES 14824743 T ES14824743 T ES 14824743T ES 2698998 T3 ES2698998 T3 ES 2698998T3

Authority

ES

Spain

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 239
• 229940034982 antineoplastic agent Drugs 0.000 title description 2
• 239000002246 antineoplastic agent Substances 0.000 title description 2
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 100
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 85
• 239000001257 hydrogen Substances 0.000 claims abstract description 83
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 65
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 60
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 57
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 52
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 45
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 42
• 150000002367 halogens Chemical class 0.000 claims abstract description 41
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 38
• 150000003839 salts Chemical class 0.000 claims abstract description 38
• 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 35
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims abstract description 34
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 33
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 23
• 125000003118 aryl group Chemical group 0.000 claims abstract description 21
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 21
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 17
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 17
• 229920006395 saturated elastomer Polymers 0.000 claims abstract description 17
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 16
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 16
• 125000002950 monocyclic group Chemical group 0.000 claims abstract description 14
• 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 13
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 12
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 11
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims abstract description 10
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 8
• 125000002619 bicyclic group Chemical group 0.000 claims abstract description 8
• 125000004122 cyclic group Chemical group 0.000 claims abstract description 8
• 125000003367 polycyclic group Chemical group 0.000 claims abstract description 8
• 125000004966 cyanoalkyl group Chemical group 0.000 claims abstract description 5
• 125000005017 substituted alkenyl group Chemical group 0.000 claims abstract 12
• 125000004426 substituted alkynyl group Chemical group 0.000 claims abstract 2
• -1 CD 3 Chemical class 0.000 claims description 266
• 238000000034 method Methods 0.000 claims description 105
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 96
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 52
• 238000011282 treatment Methods 0.000 claims description 42
• 206010028980 Neoplasm Diseases 0.000 claims description 25
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 24
• 239000008194 pharmaceutical composition Substances 0.000 claims description 21
• 125000005415 substituted alkoxy group Chemical group 0.000 claims description 19
• 201000010099 disease Diseases 0.000 claims description 18
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 17
• 201000011510 cancer Diseases 0.000 claims description 17
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 17
• 125000003545 alkoxy group Chemical group 0.000 claims description 16
• 229940125763 bromodomain inhibitor Drugs 0.000 claims description 14
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 13
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 9
• 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 9
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 9
• 239000003937 drug carrier Substances 0.000 claims description 8
• 206010009944 Colon cancer Diseases 0.000 claims description 6
• 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 6
• 238000002560 therapeutic procedure Methods 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 5
• 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
• 239000003085 diluting agent Substances 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
• 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims description 4
• 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 4
• 206010041067 Small cell lung cancer Diseases 0.000 claims description 4
• 125000000304 alkynyl group Chemical group 0.000 claims description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• 208000014018 liver neoplasm Diseases 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
• 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 3
• 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 3
• 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 3
• 206010029260 Neuroblastoma Diseases 0.000 claims description 3
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 3
• 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 3
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 3
• 201000002528 pancreatic cancer Diseases 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-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
• 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
• 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
• UWIXBDZWGJDKJL-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-amine Chemical compound CC=1N=NN(C=1C1=CC=2N(C=3C(=C(C=CC=3C=2N=C1)C(C)(C)N)F)[C@H](C1=CC=CC=C1)C1CCOCC1)C UWIXBDZWGJDKJL-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
• LZAPXWCSDTYFNB-QJDFRVHCSA-N 2-[3-[3-methyl-5-(trideuteriomethyl)-1,2-oxazol-4-yl]-5-[(S)-oxan-4-yl(phenyl)methyl]pyrido[3,2-b]indol-7-yl]propan-2-ol Chemical compound [2H]C([2H])([2H])C1=C(C(C)=NO1)C1=CC2=C(N=C1)C1=CC=C(C=C1N2[C@@H](C1CCOCC1)C1=CC=CC=C1)C(C)(C)O LZAPXWCSDTYFNB-QJDFRVHCSA-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
• 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
• 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
• NWGRIRJJSNFTFM-MUUNZHRXSA-N 3-(3,5-dimethyltriazol-4-yl)-9-methoxy-6-methylsulfonyl-5-[(S)-oxan-4-yl(phenyl)methyl]pyrido[3,2-b]indole Chemical compound CS(=O)(=O)C1=CC=C(C=2C3=C(N(C1=2)[C@H](C1=CC=CC=C1)C1CCOCC1)C=C(C=N3)C1=C(N=NN1C)C)OC NWGRIRJJSNFTFM-MUUNZHRXSA-N 0.000 claims description 2
• HQGZYVXIERSSDA-MUUNZHRXSA-N 3-(3,5-dimethyltriazol-4-yl)-9-methylsulfonyl-5-[(S)-oxan-4-yl(phenyl)methyl]pyrido[3,2-b]indole Chemical compound CS(=O)(=O)C=1C=2C3=C(N(C=2C=CC=1)[C@H](C1=CC=CC=C1)C1CCOCC1)C=C(C=N3)C1=C(N=NN1C)C HQGZYVXIERSSDA-MUUNZHRXSA-N 0.000 claims description 2
• RLXUBJLRVMWJTK-AREMUKBSSA-N 3-(5-methoxy-3-methyltriazol-4-yl)-7-methylsulfonyl-5-[(S)-oxan-4-yl(phenyl)methyl]pyrido[3,2-b]indole Chemical compound CS(=O)(=O)C=1C=CC=2C3=C(N(C=2C=1)[C@H](C1=CC=CC=C1)C1CCOCC1)C=C(C=N3)C1=C(N=NN1C)OC RLXUBJLRVMWJTK-AREMUKBSSA-N 0.000 claims description 2
• 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 2
• UIWQTEYTWQYNMF-GDLZYMKVSA-N 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-yl]methanesulfonamide Chemical compound CC=1N=NN(C=1C1=CC=2N(C=3C(=C(C=CC=3C=2N=C1)C(C)(C)NS(=O)(=O)C)F)[C@H](C1=CC=CC=C1)C1CCOCC1)C UIWQTEYTWQYNMF-GDLZYMKVSA-N 0.000 claims description 2
• 239000013543 active substance Substances 0.000 claims description 2
• WMSPXQIQBQAWLL-UHFFFAOYSA-N cyclopropanesulfonamide Chemical compound NS(=O)(=O)C1CC1 WMSPXQIQBQAWLL-UHFFFAOYSA-N 0.000 claims description 2
• 201000005787 hematologic cancer Diseases 0.000 claims description 2
• 201000007270 liver cancer Diseases 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 26
• OJAWOLWHEQUTDE-UHFFFAOYSA-N 1,4-dimethyltriazole Chemical compound CC1=CN(C)N=N1 OJAWOLWHEQUTDE-UHFFFAOYSA-N 0.000 claims 3
• 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 1
• GGUNMQZRJAUVAP-MLBVKCQFSA-N 9-fluoro-7-methylsulfonyl-3-[3-methyl-5-(trideuteriomethyl)triazol-4-yl]-5-[(S)-oxan-4-yl(phenyl)methyl]pyrido[3,2-b]indole Chemical compound [2H]C([2H])([2H])C1=C(N(C)N=N1)C1=CC2=C(N=C1)C1=C(F)C=C(C=C1N2[C@@H](C1CCOCC1)C1=CC=CC=C1)S(C)(=O)=O GGUNMQZRJAUVAP-MLBVKCQFSA-N 0.000 claims 1
• 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims 1
• 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
• 239000000825 pharmaceutical preparation Substances 0.000 claims 1
• 229940127557 pharmaceutical product Drugs 0.000 claims 1
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 1
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