JP2018522847A - ３−アミノ−１，５，６，７−テトラヒドロ−４ｈ−インドール−４−オン類 - Google Patents

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Publication number

JP2018522847A

JP2018522847A JP2017564846A JP2017564846A JP2018522847A JP 2018522847 A JP2018522847 A JP 2018522847A JP 2017564846 A JP2017564846 A JP 2017564846A JP 2017564846 A JP2017564846 A JP 2017564846A JP 2018522847 A JP2018522847 A JP 2018522847A

Authority

JP

Japan

Prior art keywords

tetrahydro

pyridin

oxo

phenylamino

methyl

Prior art date

2015-06-17

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.)

Withdrawn

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• KXDRGISZIXZIPR-UHFFFAOYSA-N 3-amino-1,5,6,7-tetrahydroindol-4-one Chemical class NC1=CNC=2CCCC(C1=2)=O KXDRGISZIXZIPR-UHFFFAOYSA-N 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 360
• 238000000034 method Methods 0.000 claims abstract description 83
• 238000002360 preparation method Methods 0.000 claims abstract description 33
• 239000002246 antineoplastic agent Substances 0.000 claims abstract description 6
• -1 C 1 -C 6 -alkoxy Chemical group 0.000 claims description 287
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 171
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 155
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 138
• UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 133
• 229910052736 halogen Inorganic materials 0.000 claims description 111
• 239000000203 mixture Substances 0.000 claims description 109
• 150000003839 salts Chemical class 0.000 claims description 104
• 150000002367 halogens Chemical class 0.000 claims description 103
• 239000001257 hydrogen Substances 0.000 claims description 98
• 229910052739 hydrogen Inorganic materials 0.000 claims description 98
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 92
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 89
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 81
• 239000003153 chemical reaction reagent Substances 0.000 claims description 67
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 63
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 61
• WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 61
• 125000001072 heteroaryl group Chemical group 0.000 claims description 60
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 57
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 55
• 206010028980 Neoplasm Diseases 0.000 claims description 53
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 52
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 49
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 43
• 239000002253 acid Substances 0.000 claims description 42
• 229910052757 nitrogen Inorganic materials 0.000 claims description 42
• 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 41
• 150000001204 N-oxides Chemical class 0.000 claims description 41
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 41
• 238000011282 treatment Methods 0.000 claims description 39
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 37
• 125000001424 substituent group Chemical group 0.000 claims description 36
• 201000010099 disease Diseases 0.000 claims description 33
• 125000001153 fluoro group Chemical group F* 0.000 claims description 33
• 125000005842 heteroatom Chemical group 0.000 claims description 28
• 239000004480 active ingredient Substances 0.000 claims description 26
• 208000035475 disorder Diseases 0.000 claims description 24
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 24
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 22
• 206010027476 Metastases Diseases 0.000 claims description 22
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 18
• 125000004432 carbon atom Chemical group C* 0.000 claims description 18
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
• NIIHRVHCOAQWRF-NGFYBIIMSA-N 3-anilino-2-[2-[[(1R,2R)-2-fluorocyclopropanecarbonyl]amino]pyridin-4-yl]-N-(2-hydroxyethyl)-N-methyl-4-oxo-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound F[C@H]1[C@H](C1)C(=O)NC1=NC=CC(=C1)C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)C(=O)N(C)CCO NIIHRVHCOAQWRF-NGFYBIIMSA-N 0.000 claims description 15
• 125000005843 halogen group Chemical group 0.000 claims description 14
• 125000003118 aryl group Chemical group 0.000 claims description 12
• 229910052799 carbon Inorganic materials 0.000 claims description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims description 12
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 11
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 11
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
• 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims description 9
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 9
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
• 230000030833 cell death Effects 0.000 claims description 9
• 201000005787 hematologic cancer Diseases 0.000 claims description 9
• 229910052760 oxygen Inorganic materials 0.000 claims description 9
• MRJFMHNSYCSPSB-UHFFFAOYSA-N 3-anilino-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxylic acid Chemical compound O=C1C=2C(=C(NC=2CC(C1)C(=O)O)C1=CC=NC=C1)NC1=CC=CC=C1 MRJFMHNSYCSPSB-UHFFFAOYSA-N 0.000 claims description 8
• 150000001412 amines Chemical class 0.000 claims description 8
• DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 8
• 230000003463 hyperproliferative effect Effects 0.000 claims description 8
• 230000002265 prevention Effects 0.000 claims description 8
• 239000002671 adjuvant Substances 0.000 claims description 7
• QROKOTBWFZITJZ-UHFFFAOYSA-N n-pyridin-2-ylacetamide Chemical compound CC(=O)NC1=CC=CC=N1 QROKOTBWFZITJZ-UHFFFAOYSA-N 0.000 claims description 7
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 7
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 6
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 6
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 6
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 201000001441 melanoma Diseases 0.000 claims description 6
• NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims description 6
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 5
• LPVZQVKRRGAUKD-UHFFFAOYSA-N 1-pyridin-4-yl-4,5,6,7-tetrahydroindole-6-carboxamide Chemical compound N1=CC=C(C=C1)N1C=CC=2CCC(CC1=2)C(=O)N LPVZQVKRRGAUKD-UHFFFAOYSA-N 0.000 claims description 5
• UXVCEKRAZBZVSL-UHFFFAOYSA-N 2-pyridin-2-ylacetamide Chemical compound NC(=O)CC1=CC=CC=N1 UXVCEKRAZBZVSL-UHFFFAOYSA-N 0.000 claims description 5
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 5
• OEHWDBVXVGYBEP-UHFFFAOYSA-N CC(C)(C)OC(=O)N(C)C1CC2=C(C(=O)C1)C(=C(N2)C3=CC=NC=C3)NC4=CC=CC=C4 Chemical compound CC(C)(C)OC(=O)N(C)C1CC2=C(C(=O)C1)C(=C(N2)C3=CC=NC=C3)NC4=CC=CC=C4 OEHWDBVXVGYBEP-UHFFFAOYSA-N 0.000 claims description 5
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 5
• 210000000481 breast Anatomy 0.000 claims description 5
• 230000006698 induction Effects 0.000 claims description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• XMSKDBWHCDMVES-UHFFFAOYSA-N methyl 3-anilino-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxylate Chemical compound N(C1=CC=CC=C1)C1=C(NC=2CC(CC(C1=2)=O)C(=O)OC)C1=CC=NC=C1 XMSKDBWHCDMVES-UHFFFAOYSA-N 0.000 claims description 5
• VHGRVXAFVFXZKR-UHFFFAOYSA-N tert-butyl N-(3-anilino-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-6-yl)carbamate Chemical compound O=C1C=2C(=C(NC=2CC(C1)NC(OC(C)(C)C)=O)C1=CC=NC=C1)NC1=CC=CC=C1 VHGRVXAFVFXZKR-UHFFFAOYSA-N 0.000 claims description 5
• SSJXIUAHEKJCMH-WDSKDSINSA-N (1s,2s)-cyclohexane-1,2-diamine Chemical compound N[C@H]1CCCC[C@@H]1N SSJXIUAHEKJCMH-WDSKDSINSA-N 0.000 claims description 4
• WSKTXRQWLLGTJP-UHFFFAOYSA-N 3-anilino-4-oxo-N-phenyl-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound O=C1C=2C(=C(NC=2CC(C1)C(=O)NC1=CC=CC=C1)C1=CC=NC=C1)NC1=CC=CC=C1 WSKTXRQWLLGTJP-UHFFFAOYSA-N 0.000 claims description 4
• WJEUWHLCNPRWCM-UHFFFAOYSA-N 3-anilino-6-(hydroxymethyl)-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-4-one Chemical compound N(C1=CC=CC=C1)C1=C(NC=2CC(CC(C1=2)=O)CO)C1=CC=NC=C1 WJEUWHLCNPRWCM-UHFFFAOYSA-N 0.000 claims description 4
• KHELHDGTKOZZPY-VOTSOKGWSA-N 3-anilino-6-[(E)-2-(4-fluorophenyl)ethenyl]-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-4-one Chemical compound FC1=CC=C(C=C1)/C=C/C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O KHELHDGTKOZZPY-VOTSOKGWSA-N 0.000 claims description 4
• WZRAYKVNVBNRIG-UHFFFAOYSA-N 3-anilino-N-(2-hydroxyethyl)-N-methyl-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound OCCN(C(=O)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O)C WZRAYKVNVBNRIG-UHFFFAOYSA-N 0.000 claims description 4
• YPBXCUXVWKRBQE-UHFFFAOYSA-N 3-anilino-N-methyl-4-oxo-N-propyl-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound CN(C(=O)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O)CCC YPBXCUXVWKRBQE-UHFFFAOYSA-N 0.000 claims description 4
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 4
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 4
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
• 125000006006 difluoroethoxy group Chemical group 0.000 claims description 4
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 4
• 125000003566 oxetanyl group Chemical group 0.000 claims description 4
• 239000007800 oxidant agent Substances 0.000 claims description 4
• NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 4
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
• LVMXOFRTJXFDPQ-UHFFFAOYSA-N 3-anilino-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound O=C1C=2C(=C(NC=2CC(C1)C(=O)N)C1=CC=NC=C1)NC1=CC=CC=C1 LVMXOFRTJXFDPQ-UHFFFAOYSA-N 0.000 claims description 3
• FJAZCWJNVFYVSB-UHFFFAOYSA-N 3-anilino-4-oxo-N-propyl-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound O=C1C=2C(=C(NC=2CC(C1)C(=O)NCCC)C1=CC=NC=C1)NC1=CC=CC=C1 FJAZCWJNVFYVSB-UHFFFAOYSA-N 0.000 claims description 3
• AOOSYONADGZHTI-UHFFFAOYSA-N 3-anilino-6-(phenylmethoxymethyl)-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-4-one Chemical compound C(C1=CC=CC=C1)OCC1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O AOOSYONADGZHTI-UHFFFAOYSA-N 0.000 claims description 3
• WQEADYSTLOZFBQ-UHFFFAOYSA-N 3-anilino-N,N-dimethyl-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound CN(C(=O)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O)C WQEADYSTLOZFBQ-UHFFFAOYSA-N 0.000 claims description 3
• QYRMGCMXLNAQEV-UHFFFAOYSA-N 3-anilino-N-methyl-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound CNC(=O)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O QYRMGCMXLNAQEV-UHFFFAOYSA-N 0.000 claims description 3
• 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 3
• PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims description 3
• ZHQLDVXCVPTWAM-UHFFFAOYSA-N N-(3-anilino-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-6-yl)cyclopropanecarboxamide Chemical compound C1(CC1)C(=O)NC1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O ZHQLDVXCVPTWAM-UHFFFAOYSA-N 0.000 claims description 3
• 210000001072 colon Anatomy 0.000 claims description 3
• 230000001590 oxidative effect Effects 0.000 claims description 3
• 210000002307 prostate Anatomy 0.000 claims description 3
• VDCIGGFJDILHCY-BFILVMDVSA-N (1S,2S)-N-[4-[3-anilino-6-[(3R)-3-(dimethylamino)pyrrolidine-1-carbonyl]-6-methyl-4-oxo-5,7-dihydro-1H-indol-2-yl]pyridin-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound N(C1=CC=CC=C1)C1=C(NC=2CC(CC(C1=2)=O)(C)C(=O)N1C[C@@H](CC1)N(C)C)C1=CC(=NC=C1)NC(=O)[C@H]1[C@H](C1)F VDCIGGFJDILHCY-BFILVMDVSA-N 0.000 claims description 2
• NMJIFNUYNSIJEF-SBCWPUQDSA-N (1S,2S)-N-[4-[3-anilino-6-methyl-4-oxo-6-(piperidine-1-carbonyl)-5,7-dihydro-1H-indol-2-yl]pyridin-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound N(C1=CC=CC=C1)C1=C(NC=2CC(CC(C1=2)=O)(C(=O)N1CCCCC1)C)C1=CC(=NC=C1)NC(=O)[C@H]1[C@H](C1)F NMJIFNUYNSIJEF-SBCWPUQDSA-N 0.000 claims description 2
• PHVVQELGHFWIAL-HZLHXKQSSA-N (1S,2S)-N-[4-[3-anilino-6-methyl-4-oxo-6-(pyrrolidine-1-carbonyl)-5,7-dihydro-1H-indol-2-yl]pyridin-2-yl]-2-fluorocyclopropane-1-carboxamide Chemical compound N(C1=CC=CC=C1)C1=C(NC=2CC(CC(C1=2)=O)(C(=O)N1CCCC1)C)C1=CC(=NC=C1)NC(=O)[C@H]1[C@H](C1)F PHVVQELGHFWIAL-HZLHXKQSSA-N 0.000 claims description 2
• KRZJRNZICWNMOA-GXSJLCMTSA-N (3s,4r)-4,8-dihydroxy-3-methoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=CC=C2[C@@H](O)[C@@H](OC)CC(=O)C2=C1O KRZJRNZICWNMOA-GXSJLCMTSA-N 0.000 claims description 2
• PBQCAWJBGNMOQM-OAQYLSRUSA-N (6R)-2-(2-aminopyridin-4-yl)-3-(3-fluoroanilino)-6-methyl-4-oxo-5,7-dihydro-1H-indole-6-carboxylic acid Chemical compound NC1=NC=CC(=C1)C=1NC=2C[C@](CC(C=2C=1NC1=CC(=CC=C1)F)=O)(C(=O)O)C PBQCAWJBGNMOQM-OAQYLSRUSA-N 0.000 claims description 2
• FKTVNYYVCSINFJ-ZMBIFBSDSA-N (6R)-2-(2-aminopyridin-4-yl)-3-(3-fluoroanilino)-6-methyl-4-oxo-5,7-dihydro-1H-indole-6-carboxylic acid hydrochloride Chemical compound Cl.C[C@]1(Cc2[nH]c(c(Nc3cccc(F)c3)c2C(=O)C1)-c1ccnc(N)c1)C(O)=O FKTVNYYVCSINFJ-ZMBIFBSDSA-N 0.000 claims description 2
• QWJVWOAGOYYIQL-LLVKDONJSA-N (6R)-3-anilino-2-(3-fluoropyridin-4-yl)-4-oxo-1,5,6,7-tetrahydroindole-6-carboxylic acid Chemical compound FC=1C=NC=CC=1C=1NC=2C[C@H](CC(C=2C=1NC1=CC=CC=C1)=O)C(=O)O QWJVWOAGOYYIQL-LLVKDONJSA-N 0.000 claims description 2
• SWAUXEWTUCKPAQ-CYBMUJFWSA-N (6R)-3-anilino-2-(3-fluoropyridin-4-yl)-N,N-dimethyl-4-oxo-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound FC=1C=NC=CC=1C=1NC=2C[C@H](CC(C=2C=1NC1=CC=CC=C1)=O)C(=O)N(C)C SWAUXEWTUCKPAQ-CYBMUJFWSA-N 0.000 claims description 2
• MRJFMHNSYCSPSB-CYBMUJFWSA-N (6R)-3-anilino-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxylic acid Chemical compound O=C1C=2C(=C(NC=2C[C@H](C1)C(=O)O)C1=CC=NC=C1)NC1=CC=CC=C1 MRJFMHNSYCSPSB-CYBMUJFWSA-N 0.000 claims description 2
• BXONSDKCJQOMEA-OAHLLOKOSA-N (6R)-3-anilino-6-(2-hydroxypropan-2-yl)-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-4-one Chemical compound OC(C)(C)[C@H]1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O BXONSDKCJQOMEA-OAHLLOKOSA-N 0.000 claims description 2
• WQEADYSTLOZFBQ-OAHLLOKOSA-N (6R)-3-anilino-N,N-dimethyl-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound CN(C(=O)[C@H]1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O)C WQEADYSTLOZFBQ-OAHLLOKOSA-N 0.000 claims description 2
• WZRAYKVNVBNRIG-MRXNPFEDSA-N (6R)-3-anilino-N-(2-hydroxyethyl)-N-methyl-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound OCCN(C(=O)[C@H]1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O)C WZRAYKVNVBNRIG-MRXNPFEDSA-N 0.000 claims description 2
• PVFXNXWMPDQWIK-GDBMZVCRSA-N (6R)-3-anilino-N-[(2R)-1-hydroxypropan-2-yl]-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound OC[C@@H](C)NC(=O)[C@H]1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O PVFXNXWMPDQWIK-GDBMZVCRSA-N 0.000 claims description 2
• PVFXNXWMPDQWIK-GOEBONIOSA-N (6R)-3-anilino-N-[(2S)-1-hydroxypropan-2-yl]-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound OC[C@H](C)NC(=O)[C@H]1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O PVFXNXWMPDQWIK-GOEBONIOSA-N 0.000 claims description 2
• PBQCAWJBGNMOQM-NRFANRHFSA-N (6S)-2-(2-aminopyridin-4-yl)-3-(3-fluoroanilino)-6-methyl-4-oxo-5,7-dihydro-1H-indole-6-carboxylic acid Chemical compound NC1=NC=CC(=C1)C=1NC=2C[C@@](CC(C=2C=1NC1=CC(=CC=C1)F)=O)(C(=O)O)C PBQCAWJBGNMOQM-NRFANRHFSA-N 0.000 claims description 2
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• BGTFBBLLAQQYQG-UHFFFAOYSA-N N-[4-[3-anilino-6-(3,3-difluoroazetidine-1-carbonyl)-6-methyl-4-oxo-5,7-dihydro-1H-indol-2-yl]pyridin-2-yl]acetamide Chemical compound C(C)(=O)NC1=NC=CC(=C1)C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)(C)C(=O)N1CC(C1)(F)F BGTFBBLLAQQYQG-UHFFFAOYSA-N 0.000 claims description 2
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• QKHHVINELRZHKX-UHFFFAOYSA-N N-[4-[3-anilino-6-(azidomethyl)-4-oxo-1,5,6,7-tetrahydroindol-2-yl]pyridin-2-yl]acetamide Chemical compound CC(=O)NC1=NC=CC(=C1)C1=C(NC2=CC=CC=C2)C2=C(CC(CN=[N+]=[N-])CC2=O)N1 QKHHVINELRZHKX-UHFFFAOYSA-N 0.000 claims description 2
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• WGHDMOMBCLHXSV-UHFFFAOYSA-N N-[4-[3-anilino-6-(tert-butylsulfanylmethyl)-4-oxo-1,5,6,7-tetrahydroindol-2-yl]pyridin-2-yl]acetamide Chemical compound CC(=O)NC1=NC=CC(=C1)C1=C(NC2=CC=CC=C2)C2=C(CC(CSC(C)(C)C)CC2=O)N1 WGHDMOMBCLHXSV-UHFFFAOYSA-N 0.000 claims description 2
• CRZKBMSBJUMOJN-UHFFFAOYSA-N N-[4-[3-anilino-6-(tert-butylsulfonylmethyl)-4-oxo-1,5,6,7-tetrahydroindol-2-yl]pyridin-2-yl]acetamide Chemical compound CC(=O)NC1=NC=CC(=C1)C1=C(NC2=CC=CC=C2)C2=C(CC(CS(=O)(=O)C(C)(C)C)CC2=O)N1 CRZKBMSBJUMOJN-UHFFFAOYSA-N 0.000 claims description 2
• LTJDNVJGJILYNC-QPCXQWPTSA-N N-[4-[3-anilino-6-[(2R,6S)-2,6-dimethylmorpholine-4-carbonyl]-6-methyl-4-oxo-5,7-dihydro-1H-indol-2-yl]pyridin-2-yl]acetamide Chemical compound N(C1=CC=CC=C1)C1=C(NC=2CC(CC(C1=2)=O)(C)C(=O)N1C[C@H](O[C@H](C1)C)C)C1=CC(=NC=C1)NC(C)=O LTJDNVJGJILYNC-QPCXQWPTSA-N 0.000 claims description 2
• YQVZXMILVPZMCH-QYWNIODHSA-N N-[4-[3-anilino-6-[(3R)-3-(dimethylamino)pyrrolidine-1-carbonyl]-6-methyl-4-oxo-5,7-dihydro-1H-indol-2-yl]pyridin-2-yl]acetamide Chemical compound CN(C)[C@@H]1CCN(C1)C(=O)C1(C)CC2=C(C(NC3=CC=CC=C3)=C(N2)C2=CC(NC(C)=O)=NC=C2)C(=O)C1 YQVZXMILVPZMCH-QYWNIODHSA-N 0.000 claims description 2
• XNWGBFQSCRYDOA-UHFFFAOYSA-N N-[4-[3-anilino-6-[(4-chlorophenyl)sulfanylmethyl]-4-oxo-1,5,6,7-tetrahydroindol-2-yl]pyridin-2-yl]acetamide Chemical compound N(C1=CC=CC=C1)C1=C(NC=2CC(CC(C1=2)=O)CSC1=CC=C(C=C1)Cl)C1=CC(=NC=C1)NC(C)=O XNWGBFQSCRYDOA-UHFFFAOYSA-N 0.000 claims description 2
• AXAHVCHJRCRDOS-UHFFFAOYSA-N N-[4-[3-anilino-6-[(4-fluorophenyl)methylsulfanylmethyl]-4-oxo-1,5,6,7-tetrahydroindol-2-yl]pyridin-2-yl]acetamide Chemical compound CC(=O)NC1=NC=CC(=C1)C1=C(NC2=CC=CC=C2)C2=C(CC(CSCC3=CC=C(F)C=C3)CC2=O)N1 AXAHVCHJRCRDOS-UHFFFAOYSA-N 0.000 claims description 2
• UKFLFJGHMIRUOW-UHFFFAOYSA-N N-[4-[3-anilino-6-[(4-fluorophenyl)methylsulfonylmethyl]-4-oxo-1,5,6,7-tetrahydroindol-2-yl]pyridin-2-yl]acetamide Chemical compound N(C1=CC=CC=C1)C1=C(NC=2CC(CC(C1=2)=O)CS(=O)(=O)CC1=CC=C(C=C1)F)C1=CC(=NC=C1)NC(C)=O UKFLFJGHMIRUOW-UHFFFAOYSA-N 0.000 claims description 2
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• VWDZCCTUSNPMOU-UHFFFAOYSA-N N-[4-[3-anilino-6-[2-(dimethylamino)ethylsulfanylmethyl]-4-oxo-1,5,6,7-tetrahydroindol-2-yl]pyridin-2-yl]acetamide Chemical compound C(C)(=O)NC1=NC=CC(=C1)C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)CSCCN(C)C VWDZCCTUSNPMOU-UHFFFAOYSA-N 0.000 claims description 2
• KROUUHJZKGBHRL-UHFFFAOYSA-N N-[4-[3-anilino-6-methyl-4-oxo-6-(pyrrolidine-1-carbonyl)-5,7-dihydro-1H-indol-2-yl]pyridin-2-yl]-2-fluoro-2-methylpropanamide Chemical compound CC(C)(F)C(=O)NC1=NC=CC(=C1)C1=C(NC2=CC=CC=C2)C2=C(CC(C)(CC2=O)C(=O)N2CCCC2)N1 KROUUHJZKGBHRL-UHFFFAOYSA-N 0.000 claims description 2
• UIJZWXWLZMBUES-UHFFFAOYSA-N N-[4-[3-anilino-6-methyl-6-(2-oxa-6-azaspiro[3.3]heptane-6-carbonyl)-4-oxo-5,7-dihydro-1H-indol-2-yl]pyridin-2-yl]acetamide Chemical compound CC(=O)NC1=NC=CC(=C1)C1=C(NC2=CC=CC=C2)C2=C(CC(C)(CC2=O)C(=O)N2CC3(COC3)C2)N1 UIJZWXWLZMBUES-UHFFFAOYSA-N 0.000 claims description 2
• QXGJWZCGYQDNHZ-UHFFFAOYSA-N N-[4-[3-anilino-6-methyl-6-(4-methylpiperazine-1-carbonyl)-4-oxo-5,7-dihydro-1H-indol-2-yl]pyridin-2-yl]acetamide Chemical compound N(C1=CC=CC=C1)C1=C(NC=2CC(CC(C1=2)=O)(C(=O)N1CCN(CC1)C)C)C1=CC(=NC=C1)NC(C)=O QXGJWZCGYQDNHZ-UHFFFAOYSA-N 0.000 claims description 2
• KMUMNUMTVVXNHW-UHFFFAOYSA-N N-[[2-(2-acetamidopyridin-4-yl)-3-anilino-4-oxo-1,5,6,7-tetrahydroindol-6-yl]methyl]-4-(4-methoxyphenyl)benzamide Chemical compound C(C)(=O)NC1=NC=CC(=C1)C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)CNC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)OC KMUMNUMTVVXNHW-UHFFFAOYSA-N 0.000 claims description 2
• DLAJCIXUJGNISC-UHFFFAOYSA-N N-[[2-(2-acetamidopyridin-4-yl)-3-anilino-4-oxo-1,5,6,7-tetrahydroindol-6-yl]methyl]acetamide Chemical compound C(C)(=O)NC1=NC=CC(=C1)C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)CNC(C)=O DLAJCIXUJGNISC-UHFFFAOYSA-N 0.000 claims description 2
• IQMYMKMUMCUVDK-UHFFFAOYSA-N N-[[3-(3-fluoroanilino)-2-[3-(2-methoxyethoxy)pyridin-4-yl]-4-oxo-1,5,6,7-tetrahydroindol-6-yl]methyl]acetamide Chemical compound FC=1C=C(C=CC=1)NC1=C(NC=2CC(CC(C1=2)=O)CNC(C)=O)C1=C(C=NC=C1)OCCOC IQMYMKMUMCUVDK-UHFFFAOYSA-N 0.000 claims description 2
• XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 claims description 2
• KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 2
• 230000000973 chemotherapeutic effect Effects 0.000 claims description 2
• AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims description 2
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 2
• 125000005350 hydroxycycloalkyl group Chemical group 0.000 claims description 2
• WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 claims description 2
• 210000004072 lung Anatomy 0.000 claims description 2
• DWCSALIFAUFXHZ-JOCHJYFZSA-N methyl (6R)-2-(2-aminopyridin-4-yl)-3-(3-fluoroanilino)-6-methyl-4-oxo-5,7-dihydro-1H-indole-6-carboxylate Chemical compound NC1=NC=CC(=C1)C=1NC=2C[C@](CC(C=2C=1NC1=CC(=CC=C1)F)=O)(C(=O)OC)C DWCSALIFAUFXHZ-JOCHJYFZSA-N 0.000 claims description 2
• OYUIYFFGOSAQAL-GFCCVEGCSA-N methyl (6R)-3-anilino-2-(3-fluoropyridin-4-yl)-4-oxo-1,5,6,7-tetrahydroindole-6-carboxylate Chemical compound FC=1C=NC=CC=1C=1NC=2C[C@H](CC(C=2C=1NC1=CC=CC=C1)=O)C(=O)OC OYUIYFFGOSAQAL-GFCCVEGCSA-N 0.000 claims description 2
• DWCSALIFAUFXHZ-QFIPXVFZSA-N methyl (6S)-2-(2-aminopyridin-4-yl)-3-(3-fluoroanilino)-6-methyl-4-oxo-5,7-dihydro-1H-indole-6-carboxylate Chemical compound NC1=NC=CC(=C1)C=1NC=2C[C@@](CC(C=2C=1NC1=CC(=CC=C1)F)=O)(C(=O)OC)C DWCSALIFAUFXHZ-QFIPXVFZSA-N 0.000 claims description 2
• OYUIYFFGOSAQAL-LBPRGKRZSA-N methyl (6S)-3-anilino-2-(3-fluoropyridin-4-yl)-4-oxo-1,5,6,7-tetrahydroindole-6-carboxylate Chemical compound FC=1C=NC=CC=1C=1NC=2C[C@@H](CC(C=2C=1NC1=CC=CC=C1)=O)C(=O)OC OYUIYFFGOSAQAL-LBPRGKRZSA-N 0.000 claims description 2
• XMSKDBWHCDMVES-AWEZNQCLSA-N methyl (6S)-3-anilino-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxylate Chemical compound O=C1C=2C(=C(NC=2C[C@@H](C1)C(=O)OC)C1=CC=NC=C1)NC1=CC=CC=C1 XMSKDBWHCDMVES-AWEZNQCLSA-N 0.000 claims description 2
• GJIGPGOJNZIBRT-UHFFFAOYSA-N methyl 2-(2-acetamidopyridin-4-yl)-3-anilino-4-oxo-1,5,6,7-tetrahydroindole-6-carboxylate Chemical compound C(C)(=O)NC1=NC=CC(=C1)C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)C(=O)OC GJIGPGOJNZIBRT-UHFFFAOYSA-N 0.000 claims description 2
• NSJKATUKZNWKCH-UHFFFAOYSA-N methyl 2-(2-aminopyridin-4-yl)-3-anilino-4-oxo-1,5,6,7-tetrahydroindole-6-carboxylate Chemical compound NC1=NC=CC(=C1)C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)C(=O)OC NSJKATUKZNWKCH-UHFFFAOYSA-N 0.000 claims description 2
• OYUIYFFGOSAQAL-UHFFFAOYSA-N methyl 3-anilino-2-(3-fluoropyridin-4-yl)-4-oxo-1,5,6,7-tetrahydroindole-6-carboxylate Chemical compound FC=1C=NC=CC=1C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)C(=O)OC OYUIYFFGOSAQAL-UHFFFAOYSA-N 0.000 claims description 2
• NVFPCZMBZFHOAP-UHFFFAOYSA-N methyl 3-anilino-2-(3-methoxypyridin-4-yl)-4-oxo-1,5,6,7-tetrahydroindole-6-carboxylate Chemical compound COC=1C=NC=CC=1C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)C(=O)OC NVFPCZMBZFHOAP-UHFFFAOYSA-N 0.000 claims description 2
• QCMUFMBINIZFCX-UHFFFAOYSA-N methyl 3-anilino-2-[2-[(2,2-difluorocyclopropanecarbonyl)amino]pyridin-4-yl]-4-oxo-1,5,6,7-tetrahydroindole-6-carboxylate Chemical compound N(C1=CC=CC=C1)C1=C(NC=2CC(CC(C1=2)=O)C(=O)OC)C1=CC(=NC=C1)NC(=O)C1C(C1)(F)F QCMUFMBINIZFCX-UHFFFAOYSA-N 0.000 claims description 2
• PAXPCSQCCCSKOJ-UHFFFAOYSA-N methyl 3-anilino-2-[3-(2,2-difluoroethoxy)pyridin-4-yl]-4-oxo-1,5,6,7-tetrahydroindole-6-carboxylate Chemical compound FC(COC=1C=NC=CC=1C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)C(=O)OC)F PAXPCSQCCCSKOJ-UHFFFAOYSA-N 0.000 claims description 2
• BDPBNWLTGQZHRV-UHFFFAOYSA-N methyl 3-anilino-2-[3-(2-methoxyethoxy)pyridin-4-yl]-4-oxo-1,5,6,7-tetrahydroindole-6-carboxylate Chemical compound COCCOC=1C=NC=CC=1C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)C(=O)OC BDPBNWLTGQZHRV-UHFFFAOYSA-N 0.000 claims description 2
• HEQGNXUKCPKYGR-UHFFFAOYSA-N methyl 4-oxo-2-pyridin-4-yl-3-(pyridin-2-ylamino)-1,5,6,7-tetrahydroindole-6-carboxylate Chemical compound O=C1C=2C(=C(NC=2CC(C1)C(=O)OC)C1=CC=NC=C1)NC1=NC=CC=C1 HEQGNXUKCPKYGR-UHFFFAOYSA-N 0.000 claims description 2
• YSSOWGMZFSGQQS-UHFFFAOYSA-N methyl N-[(3-anilino-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-6-yl)methyl]carbamate Chemical compound O=C1C=2C(=C(NC=2CC(C1)CNC(OC)=O)C1=CC=NC=C1)NC1=CC=CC=C1 YSSOWGMZFSGQQS-UHFFFAOYSA-N 0.000 claims description 2
• XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical compound [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 claims description 2
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
• ZKWFSTHEYLJLEL-UHFFFAOYSA-N morpholine-4-carboxamide Chemical compound NC(=O)N1CCOCC1 ZKWFSTHEYLJLEL-UHFFFAOYSA-N 0.000 claims description 2
• WYRKHYVWESLWKY-UHFFFAOYSA-N tert-butyl 3-anilino-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxylate Chemical compound O=C1C=2C(=C(NC=2CC(C1)C(=O)OC(C)(C)C)C1=CC=NC=C1)NC1=CC=CC=C1 WYRKHYVWESLWKY-UHFFFAOYSA-N 0.000 claims description 2
• 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 8
• 229940041181 antineoplastic drug Drugs 0.000 claims 2
• KBCJZUGWXZGGFG-UHFFFAOYSA-N 3-anilino-4-oxo-2-pyridin-4-yl-N-(2,2,2-trifluoroethyl)-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound O=C1C=2C(=C(NC=2CC(C1)C(=O)NCC(F)(F)F)C1=CC=NC=C1)NC1=CC=CC=C1 KBCJZUGWXZGGFG-UHFFFAOYSA-N 0.000 claims 1
• JQDDSKIDYJNVDV-UHFFFAOYSA-N 3-anilino-6-[(dimethylamino)methyl]-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-4-one Chemical compound CN(C)CC1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O JQDDSKIDYJNVDV-UHFFFAOYSA-N 0.000 claims 1
• LETOWYRZLIZEJO-UHFFFAOYSA-N 3-anilino-6-[[4-(dimethylamino)piperidin-1-yl]methyl]-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-4-one Chemical compound CN(C1CCN(CC1)CC1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O)C LETOWYRZLIZEJO-UHFFFAOYSA-N 0.000 claims 1
• RERIBTMJHAQDJQ-UHFFFAOYSA-N 6-methyl-1,5,6,7-tetrahydroindol-4-one Chemical compound O=C1CC(C)CC2=C1C=CN2 RERIBTMJHAQDJQ-UHFFFAOYSA-N 0.000 claims 1
• WJYBCSXRLKXKKO-UHFFFAOYSA-N N-[4-[3-anilino-4-oxo-6-(propan-2-ylsulfanylmethyl)-1,5,6,7-tetrahydroindol-2-yl]pyridin-2-yl]-3,4-dichlorobenzamide Chemical compound CC(C)SCC1CC2=C(C(NC3=CC=CC=C3)=C(N2)C2=CC(NC(=O)C3=CC(Cl)=C(Cl)C=C3)=NC=C2)C(=O)C1 WJYBCSXRLKXKKO-UHFFFAOYSA-N 0.000 claims 1
• DDABNGRNDNNHBK-UHFFFAOYSA-N N-[4-[3-anilino-6-(2-methoxyethylsulfonylmethyl)-4-oxo-1,5,6,7-tetrahydroindol-2-yl]pyridin-2-yl]acetamide Chemical compound C(C)(=O)NC1=NC=CC(=C1)C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)CS(=O)(=O)CCOC DDABNGRNDNNHBK-UHFFFAOYSA-N 0.000 claims 1
• KEKVBZWOXGTZTL-UHFFFAOYSA-N N-[4-[3-anilino-6-(ethylsulfonylmethyl)-4-oxo-1,5,6,7-tetrahydroindol-2-yl]pyridin-2-yl]acetamide Chemical compound CCS(=O)(=O)CC1CC2=C(C(NC3=CC=CC=C3)=C(N2)C2=CC(NC(C)=O)=NC=C2)C(=O)C1 KEKVBZWOXGTZTL-UHFFFAOYSA-N 0.000 claims 1
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