CA2989469A1

CA2989469A1 - 3-amino-1,5,6,7-tetrahydro-4h-indol-4-ones

3-amino-1,5,6,7-tetrahydro-4h-indol-4-ones Download PDF

Info

Publication number: CA2989469A1
Authority: CA; Canada
Prior art keywords: tetrahydro; pyridin; oxo; phenylamino; methyl
Prior art date: 2015-06-17
Legal status : Abandoned

Application number

CA2989469A

Other languages

English (en)

French (fr)

Inventor

Keith Graham

Ulrich Klar

Hans Briem

Gerhard Siemeister

Ursula Monning

Jozsef Balint

Current Assignee

Bayer Pharma AG

Original Assignee

Bayer Pharma AG

Priority date

2015-06-17

Filing date

2016-06-14

Publication date

2016-12-22

2015-06-17 Priority claimed from PCT/EP2015/063527 external-priority patent/WO2015193339A1/en

2016-06-14 Application filed by Bayer Pharma AG filed Critical Bayer Pharma AG

2016-12-22 Publication of CA2989469A1 publication Critical patent/CA2989469A1/en

Status Abandoned legal-status Critical Current

Links

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 1
150000001875 compounds Chemical class 0.000 claims abstract description 378
239000002246 antineoplastic agent Substances 0.000 claims abstract description 6
-1 C4-haloalkyl Chemical group 0.000 claims description 275
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 172
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 164
239000000203 mixture Substances 0.000 claims description 148
229910052736 halogen Inorganic materials 0.000 claims description 111
238000000034 method Methods 0.000 claims description 110
150000002367 halogens Chemical class 0.000 claims description 109
150000003839 salts Chemical class 0.000 claims description 103
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 101
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 96
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 88
239000003153 chemical reaction reagent Substances 0.000 claims description 86
206010028980 Neoplasm Diseases 0.000 claims description 72
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 60
125000001072 heteroaryl group Chemical group 0.000 claims description 58
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 57
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 54
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 53
125000004093 cyano group Chemical group *C#N 0.000 claims description 49
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 43
238000011282 treatment Methods 0.000 claims description 43
150000001204 N-oxides Chemical class 0.000 claims description 42
125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 41
150000002431 hydrogen Chemical class 0.000 claims description 39
125000001424 substituent group Chemical group 0.000 claims description 36
125000001153 fluoro group Chemical group F* 0.000 claims description 33
229910052757 nitrogen Inorganic materials 0.000 claims description 33
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 32
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 32
201000010099 disease Diseases 0.000 claims description 28
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 26
239000004480 active ingredient Substances 0.000 claims description 26
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 26
208000035475 disorder Diseases 0.000 claims description 25
125000004433 nitrogen atom Chemical group N* 0.000 claims description 25
125000000623 heterocyclic group Chemical group 0.000 claims description 23
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 22
206010027476 Metastases Diseases 0.000 claims description 22
125000005842 heteroatom Chemical group 0.000 claims description 20
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 19
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 18
125000004432 carbon atom Chemical group C* 0.000 claims description 17
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
239000008194 pharmaceutical composition Substances 0.000 claims description 12
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
125000001309 chloro group Chemical group Cl* 0.000 claims description 11
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 11
230000002489 hematologic effect Effects 0.000 claims description 11
125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims description 9
229910052799 carbon Inorganic materials 0.000 claims description 9
230000030833 cell death Effects 0.000 claims description 9
238000011321 prophylaxis Methods 0.000 claims description 9
210000002307 prostate Anatomy 0.000 claims description 9
150000001412 amines Chemical class 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 8
230000003463 hyperproliferative effect Effects 0.000 claims description 8
125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 7
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 7
210000000481 breast Anatomy 0.000 claims description 7
210000001072 colon Anatomy 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 6
210000004072 lung Anatomy 0.000 claims description 6
201000001441 melanoma Diseases 0.000 claims description 6
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
125000002915 carbonyl group Chemical group [*: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
230000006698 induction Effects 0.000 claims description 4
125000003566 oxetanyl group Chemical group 0.000 claims description 4
239000007800 oxidant agent Substances 0.000 claims description 4
125000004737 (C1-C6) haloalkoxy group Chemical group 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
OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 claims description 3
230000000973 chemotherapeutic effect Effects 0.000 claims description 3
125000006125 ethylsulfonyl group Chemical group 0.000 claims description 3
125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 3
230000001590 oxidative effect Effects 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
XXUNIGZDNWWYED-UHFFFAOYSA-N 2-methylbenzamide Chemical compound CC1=CC=CC=C1C(N)=O XXUNIGZDNWWYED-UHFFFAOYSA-N 0.000 claims description 2
MNLRMABKIMQDDX-UHFFFAOYSA-N N-[4-[3-anilino-4-oxo-6-(propan-2-ylsulfinylmethyl)-1,5,6,7-tetrahydroindol-2-yl]pyridin-2-yl]-3,4-dichlorobenzamide Chemical compound ClC=1C=C(C(=O)NC2=NC=CC(=C2)C=2NC=3CC(CC(C=3C=2NC2=CC=CC=C2)=O)CS(=O)C(C)C)C=CC=1Cl MNLRMABKIMQDDX-UHFFFAOYSA-N 0.000 claims description 2
IKCCZRINHIHITD-UHFFFAOYSA-N N-[4-[3-anilino-4-oxo-6-(propan-2-ylsulfinylmethyl)-1,5,6,7-tetrahydroindol-2-yl]pyridin-2-yl]-4-chlorobenzamide Chemical compound ClC1=CC=C(C(=O)NC2=NC=CC(=C2)C=2NC=3CC(CC(C=3C=2NC2=CC=CC=C2)=O)CS(=O)C(C)C)C=C1 IKCCZRINHIHITD-UHFFFAOYSA-N 0.000 claims description 2
PROVDZGNODBBRG-UHFFFAOYSA-N N-[4-[3-anilino-4-oxo-6-(propan-2-ylsulfonylmethyl)-1,5,6,7-tetrahydroindol-2-yl]pyridin-2-yl]morpholine-4-carboxamide Chemical compound N1(CCOCC1)C(=O)NC1=NC=CC(=C1)C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)CS(=O)(=O)C(C)C PROVDZGNODBBRG-UHFFFAOYSA-N 0.000 claims description 2
YBRLJAVXAQQPCG-UHFFFAOYSA-N N-[4-[3-anilino-6-(2-methoxyethylsulfanylmethyl)-4-oxo-1,5,6,7-tetrahydroindol-2-yl]pyridin-2-yl]acetamide Chemical compound COCCSCC1CC2=C(C(NC3=CC=CC=C3)=C(N2)C2=CC(NC(C)=O)=NC=C2)C(=O)C1 YBRLJAVXAQQPCG-UHFFFAOYSA-N 0.000 claims description 2
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
WTYKJVQIVMUGBO-UHFFFAOYSA-N N-[4-[3-anilino-6-[(3,4-difluorophenyl)sulfanylmethyl]-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(CSC3=CC(F)=C(F)C=C3)CC2=O)N1 WTYKJVQIVMUGBO-UHFFFAOYSA-N 0.000 claims description 2
RUWXSIMMQMHCIE-UHFFFAOYSA-N N-[4-[3-anilino-6-[(4-fluoro-3-methoxyphenyl)sulfanylmethyl]-4-oxo-1,5,6,7-tetrahydroindol-2-yl]pyridin-2-yl]acetamide Chemical compound COC1=C(F)C=CC(SCC2CC3=C(C(NC4=CC=CC=C4)=C(N3)C3=CC(NC(C)=O)=NC=C3)C(=O)C2)=C1 RUWXSIMMQMHCIE-UHFFFAOYSA-N 0.000 claims description 2
AYAILIOIUUFYPS-UHFFFAOYSA-N N-[4-[3-anilino-6-[(4-methoxyphenyl)sulfanylmethyl]-4-oxo-1,5,6,7-tetrahydroindol-2-yl]pyridin-2-yl]acetamide Chemical compound COC1=CC=C(SCC2CC3=C(C(NC4=CC=CC=C4)=C(N3)C3=CC(NC(C)=O)=NC=C3)C(=O)C2)C=C1 AYAILIOIUUFYPS-UHFFFAOYSA-N 0.000 claims description 2
MNGLCZCJMCCPKP-UHFFFAOYSA-N N-[4-[6-(aminomethyl)-3-anilino-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)CC2=O)N1 MNGLCZCJMCCPKP-UHFFFAOYSA-N 0.000 claims description 2
ZCRZCMUDOWDGOB-UHFFFAOYSA-N ethanesulfonimidic acid Chemical compound CCS(N)(=O)=O ZCRZCMUDOWDGOB-UHFFFAOYSA-N 0.000 claims description 2
125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 4
SSJXIUAHEKJCMH-WDSKDSINSA-N (1s,2s)-cyclohexane-1,2-diamine Chemical compound N[C@H]1CCCC[C@@H]1N SSJXIUAHEKJCMH-WDSKDSINSA-N 0.000 claims 2
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 2
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 2
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 2
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 2
QLQRLMFTMWBDKJ-FHOYKIJDSA-N (1S,2S)-N-[4-[3-anilino-4-oxo-6-(propan-2-ylsulfinylmethyl)-1,5,6,7-tetrahydroindol-2-yl]pyridin-2-yl]-2-fluorocyclopropane-1-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)CS(=O)C(C)C QLQRLMFTMWBDKJ-FHOYKIJDSA-N 0.000 claims 1
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 1
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 1
WNWPPAXJMBXUTF-MLCCFXAWSA-N (2S)-N-[(3-anilino-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-6-yl)methyl]-2-hydroxypropanamide Chemical compound O[C@H](C(=O)NCC1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O)C WNWPPAXJMBXUTF-MLCCFXAWSA-N 0.000 claims 1
PFPUTSWSTXKRMG-XPCCGILXSA-N (3R)-N-(3-anilino-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-6-yl)-3-hydroxybutanamide Chemical compound O[C@@H](CC(=O)NC1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O)C PFPUTSWSTXKRMG-XPCCGILXSA-N 0.000 claims 1
PFPUTSWSTXKRMG-MBIQTGHCSA-N (3S)-N-(3-anilino-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-6-yl)-3-hydroxybutanamide Chemical compound O[C@H](CC(=O)NC1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O)C PFPUTSWSTXKRMG-MBIQTGHCSA-N 0.000 claims 1
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 1
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 1
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 1
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 1
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 1
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 1
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 1
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 1
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 1
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 1
YPBXCUXVWKRBQE-QGZVFWFLSA-N (6R)-3-anilino-N-methyl-4-oxo-N-propyl-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)CCC YPBXCUXVWKRBQE-QGZVFWFLSA-N 0.000 claims 1
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 1
FKTVNYYVCSINFJ-BOXHHOBZSA-N (6S)-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-BOXHHOBZSA-N 0.000 claims 1
QWJVWOAGOYYIQL-NSHDSACASA-N (6S)-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-NSHDSACASA-N 0.000 claims 1
SWAUXEWTUCKPAQ-ZDUSSCGKSA-N (6S)-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-ZDUSSCGKSA-N 0.000 claims 1
MRJFMHNSYCSPSB-ZDUSSCGKSA-N (6S)-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-ZDUSSCGKSA-N 0.000 claims 1
BXONSDKCJQOMEA-HNNXBMFYSA-N (6S)-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-HNNXBMFYSA-N 0.000 claims 1
WQEADYSTLOZFBQ-HNNXBMFYSA-N (6S)-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-HNNXBMFYSA-N 0.000 claims 1
WZRAYKVNVBNRIG-INIZCTEOSA-N (6S)-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-INIZCTEOSA-N 0.000 claims 1
PVFXNXWMPDQWIK-ZBFHGGJFSA-N (6S)-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-ZBFHGGJFSA-N 0.000 claims 1
PVFXNXWMPDQWIK-HOCLYGCPSA-N (6S)-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-HOCLYGCPSA-N 0.000 claims 1
YPBXCUXVWKRBQE-KRWDZBQOSA-N (6S)-3-anilino-N-methyl-4-oxo-N-propyl-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)CCC YPBXCUXVWKRBQE-KRWDZBQOSA-N 0.000 claims 1
VWWJOGVHQUDPTP-GQCTYLIASA-N (E)-5-(3-anilino-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-6-yl)pent-4-enoic acid Chemical compound O=C1C=2C(=C(NC=2CC(C1)/C=C/CCC(=O)O)C1=CC=NC=C1)NC1=CC=CC=C1 VWWJOGVHQUDPTP-GQCTYLIASA-N 0.000 claims 1
KYPPBJCRXGUFKA-FNORWQNLSA-N (E)-5-[2-(2-acetamidopyridin-4-yl)-3-anilino-4-oxo-1,5,6,7-tetrahydroindol-6-yl]pent-4-enoic acid Chemical compound C(C)(=O)NC1=NC=CC(=C1)C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)/C=C/CCC(=O)O KYPPBJCRXGUFKA-FNORWQNLSA-N 0.000 claims 1
VWWJOGVHQUDPTP-XQRVVYSFSA-N (Z)-5-(3-anilino-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-6-yl)pent-4-enoic acid Chemical compound O=C1C=2C(=C(NC=2CC(C1)\C=C/CCC(=O)O)C1=CC=NC=C1)NC1=CC=CC=C1 VWWJOGVHQUDPTP-XQRVVYSFSA-N 0.000 claims 1
BPKRGUGOOOSKCS-UHFFFAOYSA-N 1-[(3-anilino-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-6-yl)methyl]-3-(3-chloro-4-fluorophenyl)urea Chemical compound ClC=1C=C(C=CC=1F)NC(=O)NCC1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O BPKRGUGOOOSKCS-UHFFFAOYSA-N 0.000 claims 1
GTZYHMCWCFBGFF-UHFFFAOYSA-N 1-[(3-anilino-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-6-yl)methyl]-3-(furan-2-ylmethyl)urea Chemical compound O1C(=CC=C1)CNC(=O)NCC1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O GTZYHMCWCFBGFF-UHFFFAOYSA-N 0.000 claims 1
BGSDVUVAVJETSS-UHFFFAOYSA-N 1-[(3-anilino-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-6-yl)methyl]-3-(oxolan-2-ylmethyl)urea Chemical compound O=C1C=2C(=C(NC=2CC(C1)CNC(=O)NCC1OCCC1)C1=CC=NC=C1)NC1=CC=CC=C1 BGSDVUVAVJETSS-UHFFFAOYSA-N 0.000 claims 1
JKYJNJRJXDKOEK-UHFFFAOYSA-N 1-[(3-anilino-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-6-yl)methyl]-3-cyclopropylurea Chemical compound C1(CC1)NC(=O)NCC1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O JKYJNJRJXDKOEK-UHFFFAOYSA-N 0.000 claims 1
LHCPCZVGKWGKEC-UHFFFAOYSA-N 1-[(3-anilino-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-6-yl)methyl]-3-ethylurea Chemical compound C(C)NC(=O)NCC1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O LHCPCZVGKWGKEC-UHFFFAOYSA-N 0.000 claims 1
BIYDHXMTAKJCIO-UHFFFAOYSA-N 1-[(3-anilino-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-6-yl)methyl]-3-propan-2-ylurea Chemical compound O=C1C=2C(=C(NC=2CC(C1)CNC(=O)NC(C)C)C1=CC=NC=C1)NC1=CC=CC=C1 BIYDHXMTAKJCIO-UHFFFAOYSA-N 0.000 claims 1
ZWOSGMNGWMFKOQ-UHFFFAOYSA-N 1-[4-[3-anilino-4-oxo-6-(propan-2-ylsulfanylmethyl)-1,5,6,7-tetrahydroindol-2-yl]pyridin-2-yl]-3-cyclopropylurea Chemical compound N(C1=CC=CC=C1)C1=C(NC=2CC(CC(C1=2)=O)CSC(C)C)C1=CC(=NC=C1)NC(=O)NC1CC1 ZWOSGMNGWMFKOQ-UHFFFAOYSA-N 0.000 claims 1
CPALOHRDTHKXRM-UHFFFAOYSA-N 1-[4-[3-anilino-4-oxo-6-(propan-2-ylsulfonylmethyl)-1,5,6,7-tetrahydroindol-2-yl]pyridin-2-yl]-3-cyclopropylurea Chemical compound N(C1=CC=CC=C1)C1=C(NC=2CC(CC(C1=2)=O)CS(=O)(=O)C(C)C)C1=CC(=NC=C1)NC(=O)NC1CC1 CPALOHRDTHKXRM-UHFFFAOYSA-N 0.000 claims 1
HUYXKUZFFKKZJN-UHFFFAOYSA-N 2-(2-acetamidopyridin-4-yl)-3-anilino-4-oxo-1,5,6,7-tetrahydroindole-6-carboxylic acid Chemical compound C(C)(=O)NC1=NC=CC(=C1)C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)C(=O)O HUYXKUZFFKKZJN-UHFFFAOYSA-N 0.000 claims 1
VUMYIMGCCABAPA-UHFFFAOYSA-N 2-(2-acetamidopyridin-4-yl)-3-anilino-6-methyl-4-oxo-5,7-dihydro-1H-indole-6-carboxylic acid Chemical compound C(C)(=O)NC1=NC=CC(=C1)C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)(C(=O)O)C VUMYIMGCCABAPA-UHFFFAOYSA-N 0.000 claims 1
ZHFLLACVUCWVBM-UHFFFAOYSA-N 2-(2-acetamidopyridin-4-yl)-3-anilino-N,6-dimethyl-4-oxo-N-propyl-5,7-dihydro-1H-indole-6-carboxamide Chemical compound C(C)(=O)NC1=NC=CC(=C1)C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)(C(=O)N(CCC)C)C ZHFLLACVUCWVBM-UHFFFAOYSA-N 0.000 claims 1
RAXPLLWVQNHDIN-UHFFFAOYSA-N 2-(2-acetamidopyridin-4-yl)-3-anilino-N,6-dimethyl-N-(2-methylpropyl)-4-oxo-5,7-dihydro-1H-indole-6-carboxamide Chemical compound C(C)(=O)NC1=NC=CC(=C1)C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)(C(=O)N(CC(C)C)C)C RAXPLLWVQNHDIN-UHFFFAOYSA-N 0.000 claims 1
ZKJSREDIFHCBLQ-UHFFFAOYSA-N 2-(2-acetamidopyridin-4-yl)-3-anilino-N,N,6-trimethyl-4-oxo-5,7-dihydro-1H-indole-6-carboxamide Chemical compound C(C)(=O)NC1=NC=CC(=C1)C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)(C(=O)N(C)C)C ZKJSREDIFHCBLQ-UHFFFAOYSA-N 0.000 claims 1
UBLXXTKPPSQIOR-UHFFFAOYSA-N 2-(2-acetamidopyridin-4-yl)-3-anilino-N,N-diethyl-6-methyl-4-oxo-5,7-dihydro-1H-indole-6-carboxamide Chemical compound C(C)(=O)NC1=NC=CC(=C1)C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)(C(=O)N(CC)CC)C UBLXXTKPPSQIOR-UHFFFAOYSA-N 0.000 claims 1
VMAROZXOBXSVDU-UHFFFAOYSA-N 2-(2-acetamidopyridin-4-yl)-3-anilino-N,N-dimethyl-4-oxo-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound C(C)(=O)NC1=NC=CC(=C1)C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)C(=O)N(C)C VMAROZXOBXSVDU-UHFFFAOYSA-N 0.000 claims 1
WIFBIVULBUFXIW-UHFFFAOYSA-N 2-(2-acetamidopyridin-4-yl)-3-anilino-N-(2,2-dimethylpropyl)-N,6-dimethyl-4-oxo-5,7-dihydro-1H-indole-6-carboxamide Chemical compound C(C)(=O)NC1=NC=CC(=C1)C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)(C(=O)N(C)CC(C)(C)C)C WIFBIVULBUFXIW-UHFFFAOYSA-N 0.000 claims 1
GEEDDQQEBNHBDU-UHFFFAOYSA-N 2-(2-acetamidopyridin-4-yl)-3-anilino-N-(2-hydroxyethyl)-N-methyl-4-oxo-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound C(C)(=O)NC1=NC=CC(=C1)C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)C(=O)N(C)CCO GEEDDQQEBNHBDU-UHFFFAOYSA-N 0.000 claims 1
CSOZXLBDKMGGLU-UHFFFAOYSA-N 2-(2-acetamidopyridin-4-yl)-3-anilino-N-(2-methoxy-2-methylpropyl)-N,6-dimethyl-4-oxo-5,7-dihydro-1H-indole-6-carboxamide Chemical compound C(C)(=O)NC1=NC=CC(=C1)C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)(C(=O)N(C)CC(C)(C)OC)C CSOZXLBDKMGGLU-UHFFFAOYSA-N 0.000 claims 1
ZQHAEOJTAVZBLI-UHFFFAOYSA-N 2-(2-acetamidopyridin-4-yl)-3-anilino-N-(2-methoxyethyl)-N,6-dimethyl-4-oxo-5,7-dihydro-1H-indole-6-carboxamide Chemical compound C(C)(=O)NC1=NC=CC(=C1)C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)(C(=O)N(C)CCOC)C ZQHAEOJTAVZBLI-UHFFFAOYSA-N 0.000 claims 1
KKLSHQFFVBGXDH-FQSKIORSSA-N 2-(2-acetamidopyridin-4-yl)-3-anilino-N-[(2S)-1-methoxypropan-2-yl]-N,6-dimethyl-4-oxo-5,7-dihydro-1H-indole-6-carboxamide Chemical compound C(C)(=O)NC1=NC=CC(=C1)C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)(C(=O)N(C)[C@H](COC)C)C KKLSHQFFVBGXDH-FQSKIORSSA-N 0.000 claims 1
QTOOBTOIZNFODD-FQSKIORSSA-N 2-(2-acetamidopyridin-4-yl)-3-anilino-N-[(2S)-2-methoxypropyl]-N,6-dimethyl-4-oxo-5,7-dihydro-1H-indole-6-carboxamide Chemical compound C(C)(=O)NC1=NC=CC(=C1)C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)(C(=O)N(C)C[C@H](C)OC)C QTOOBTOIZNFODD-FQSKIORSSA-N 0.000 claims 1
YIKGHHKNYGGXHA-UHFFFAOYSA-N 2-(2-aminopyridin-4-yl)-3-anilino-6-(hydroxymethyl)-1,5,6,7-tetrahydroindol-4-one Chemical compound NC1=NC=CC(=C1)C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)CO YIKGHHKNYGGXHA-UHFFFAOYSA-N 0.000 claims 1
FJWNGPKFMNNAQK-UHFFFAOYSA-N 2-(2-aminopyridin-4-yl)-3-anilino-6-(hydroxymethyl)-6-methyl-5,7-dihydro-1H-indol-4-one Chemical compound NC1=NC=CC(=C1)C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)(C)CO FJWNGPKFMNNAQK-UHFFFAOYSA-N 0.000 claims 1
RMMJZHOOLMRAPA-UHFFFAOYSA-N 2-(2-aminopyridin-4-yl)-3-anilino-6-(propan-2-ylsulfanylmethyl)-1,5,6,7-tetrahydroindol-4-one Chemical compound NC1=NC=CC(=C1)C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)CSC(C)C RMMJZHOOLMRAPA-UHFFFAOYSA-N 0.000 claims 1
HTXRVMDNCFZRCT-UHFFFAOYSA-N 2-(2-aminopyridin-4-yl)-3-anilino-6-(propan-2-ylsulfinylmethyl)-1,5,6,7-tetrahydroindol-4-one Chemical compound CC(C)S(=O)CC1Cc2[nH]c(c(Nc3ccccc3)c2C(=O)C1)-c1ccnc(N)c1 HTXRVMDNCFZRCT-UHFFFAOYSA-N 0.000 claims 1
SWMZVNMYTSTNKJ-UHFFFAOYSA-N 2-(2-aminopyridin-4-yl)-3-anilino-6-(propan-2-ylsulfonylmethyl)-1,5,6,7-tetrahydroindol-4-one Chemical compound NC1=NC=CC(=C1)C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)CS(=O)(=O)C(C)C SWMZVNMYTSTNKJ-UHFFFAOYSA-N 0.000 claims 1
KGCDSGADDFYVBB-UHFFFAOYSA-N 2-(2-aminopyridin-4-yl)-3-anilino-6-methyl-4-oxo-5,7-dihydro-1H-indole-6-carboxylic acid Chemical compound NC1=NC=CC(=C1)C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)(C(=O)O)C KGCDSGADDFYVBB-UHFFFAOYSA-N 0.000 claims 1
YORWLIDHYDBDTK-UHFFFAOYSA-N 2-(2-aminopyridin-4-yl)-3-anilino-6-methyl-6-(propan-2-ylsulfanylmethyl)-5,7-dihydro-1H-indol-4-one Chemical compound NC1=NC=CC(=C1)C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)(C)CSC(C)C YORWLIDHYDBDTK-UHFFFAOYSA-N 0.000 claims 1
SMFDITGRPKTNFZ-UHFFFAOYSA-N 2-fluoroethyl 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(OCCF)=O)C1=CC=NC=C1)NC1=CC=CC=C1 SMFDITGRPKTNFZ-UHFFFAOYSA-N 0.000 claims 1
LQJQZMXKBZXDDQ-UHFFFAOYSA-N 2-methoxyethyl 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(OCCOC)=O)C1=CC=NC=C1)NC1=CC=CC=C1 LQJQZMXKBZXDDQ-UHFFFAOYSA-N 0.000 claims 1
VSWRACLMPLHJEV-UHFFFAOYSA-N 3-(3-fluoroanilino)-6-(hydroxymethyl)-2-[3-(2-methoxyethoxy)pyridin-4-yl]-1,5,6,7-tetrahydroindol-4-one Chemical compound FC=1C=C(C=CC=1)NC1=C(NC=2CC(CC(C1=2)=O)CO)C1=C(C=NC=C1)OCCOC VSWRACLMPLHJEV-UHFFFAOYSA-N 0.000 claims 1
SNPQORGDWGLGKG-UHFFFAOYSA-N 3-(3-fluoroanilino)-6-(hydroxymethyl)-2-[3-(2-methoxyethoxy)pyridin-4-yl]-6-methyl-5,7-dihydro-1H-indol-4-one Chemical compound FC=1C=C(C=CC=1)NC1=C(NC=2CC(CC(C1=2)=O)(C)CO)C1=C(C=NC=C1)OCCOC SNPQORGDWGLGKG-UHFFFAOYSA-N 0.000 claims 1
NUWUPAJPQNBDMP-UHFFFAOYSA-N 3-anilino-1-ethyl-6-(hydroxymethyl)-2-pyridin-4-yl-6,7-dihydro-5H-indol-4-one Chemical compound C(C)N1C(=C(C=2C(CC(CC1=2)CO)=O)NC1=CC=CC=C1)C1=CC=NC=C1 NUWUPAJPQNBDMP-UHFFFAOYSA-N 0.000 claims 1
QWJVWOAGOYYIQL-UHFFFAOYSA-N 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=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)C(=O)O QWJVWOAGOYYIQL-UHFFFAOYSA-N 0.000 claims 1
XDHGZSFTHJKLHN-UHFFFAOYSA-N 3-anilino-2-(3-fluoropyridin-4-yl)-6-(2-hydroxypropan-2-yl)-1,5,6,7-tetrahydroindol-4-one Chemical compound FC=1C=NC=CC=1C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)C(C)(C)O XDHGZSFTHJKLHN-UHFFFAOYSA-N 0.000 claims 1
SWAUXEWTUCKPAQ-UHFFFAOYSA-N 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=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)C(=O)N(C)C SWAUXEWTUCKPAQ-UHFFFAOYSA-N 0.000 claims 1
WGOBFZICLXHJLE-UHFFFAOYSA-N 3-anilino-2-(3-fluoropyridin-4-yl)-N-(2-hydroxyethyl)-N-methyl-4-oxo-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound FC=1C=NC=CC=1C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)C(=O)N(C)CCO WGOBFZICLXHJLE-UHFFFAOYSA-N 0.000 claims 1
VXCUGDXPBLTIGI-UHFFFAOYSA-N 3-anilino-2-(3-methoxypyridin-4-yl)-N,N-dimethyl-4-oxo-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound COC=1C=NC=CC=1C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)C(=O)N(C)C VXCUGDXPBLTIGI-UHFFFAOYSA-N 0.000 claims 1
RASCKGWOHNSHBV-UHFFFAOYSA-N 3-anilino-2-[2-[(2,2-difluorocyclopropanecarbonyl)amino]pyridin-4-yl]-4-oxo-1,5,6,7-tetrahydroindole-6-carboxylic acid Chemical compound N(C1=CC=CC=C1)C1=C(NC=2CC(CC(C1=2)=O)C(=O)O)C1=CC(=NC=C1)NC(=O)C1C(C1)(F)F RASCKGWOHNSHBV-UHFFFAOYSA-N 0.000 claims 1
DPEPQQORFGIGFO-UHFFFAOYSA-N 3-anilino-2-[2-[(2,2-difluorocyclopropanecarbonyl)amino]pyridin-4-yl]-N,N-dimethyl-4-oxo-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound N(C1=CC=CC=C1)C1=C(NC=2CC(CC(C1=2)=O)C(=O)N(C)C)C1=CC(=NC=C1)NC(=O)C1C(C1)(F)F DPEPQQORFGIGFO-UHFFFAOYSA-N 0.000 claims 1
KCQPTHUBJQRMFC-PXWJKWRZSA-N 3-anilino-2-[2-[[(1R,2R)-2-fluorocyclopropanecarbonyl]amino]pyridin-4-yl]-4-oxo-1,5,6,7-tetrahydroindole-6-carboxylic acid 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)O KCQPTHUBJQRMFC-PXWJKWRZSA-N 0.000 claims 1
AMJFRZOXQGWHPH-XSRYCBBQSA-N 3-anilino-2-[2-[[(1R,2R)-2-fluorocyclopropanecarbonyl]amino]pyridin-4-yl]-N,N-dimethyl-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)C AMJFRZOXQGWHPH-XSRYCBBQSA-N 0.000 claims 1
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 1
LHWCVUMMFDOINI-ZUDGUFDASA-N 3-anilino-2-[2-[[(1S,2S)-2-fluorocyclopropanecarbonyl]amino]pyridin-4-yl]-N,6-dimethyl-4-oxo-N-(3,3,3-trifluoropropyl)-5,7-dihydro-1H-indole-6-carboxamide Chemical compound N(C1=CC=CC=C1)C1=C(NC=2CC(CC(C1=2)=O)(C(=O)N(CCC(F)(F)F)C)C)C1=CC(=NC=C1)NC(=O)[C@H]1[C@H](C1)F LHWCVUMMFDOINI-ZUDGUFDASA-N 0.000 claims 1
SPAOPPRPJPGJLT-HZLHXKQSSA-N 3-anilino-2-[2-[[(1S,2S)-2-fluorocyclopropanecarbonyl]amino]pyridin-4-yl]-N,6-dimethyl-4-oxo-N-propyl-5,7-dihydro-1H-indole-6-carboxamide Chemical compound N(C1=CC=CC=C1)C1=C(NC=2CC(CC(C1=2)=O)(C(=O)N(CCC)C)C)C1=CC(=NC=C1)NC(=O)[C@H]1[C@H](C1)F SPAOPPRPJPGJLT-HZLHXKQSSA-N 0.000 claims 1
JNTCGFSYBCUXJE-SBCWPUQDSA-N 3-anilino-2-[2-[[(1S,2S)-2-fluorocyclopropanecarbonyl]amino]pyridin-4-yl]-N,6-dimethyl-N-(2-methylpropyl)-4-oxo-5,7-dihydro-1H-indole-6-carboxamide Chemical compound N(C1=CC=CC=C1)C1=C(NC=2CC(CC(C1=2)=O)(C(=O)N(C)CC(C)C)C)C1=CC(=NC=C1)NC(=O)[C@H]1[C@H](C1)F JNTCGFSYBCUXJE-SBCWPUQDSA-N 0.000 claims 1
XSYLKMNBEPMYTO-QIXCQHHOSA-N 3-anilino-2-[2-[[(1S,2S)-2-fluorocyclopropanecarbonyl]amino]pyridin-4-yl]-N,N,6-trimethyl-4-oxo-5,7-dihydro-1H-indole-6-carboxamide Chemical compound N(C1=CC=CC=C1)C1=C(NC=2CC(CC(C1=2)=O)(C(=O)N(C)C)C)C1=CC(=NC=C1)NC(=O)[C@H]1[C@H](C1)F XSYLKMNBEPMYTO-QIXCQHHOSA-N 0.000 claims 1
DJDCYXWLGHUNEK-UHFFFAOYSA-N 3-anilino-2-[3-(2,2-difluoroethoxy)pyridin-4-yl]-4-oxo-1,5,6,7-tetrahydroindole-6-carboxylic acid Chemical compound FC(COC=1C=NC=CC=1C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)C(=O)O)F DJDCYXWLGHUNEK-UHFFFAOYSA-N 0.000 claims 1
GMODEEMIZHSOOO-UHFFFAOYSA-N 3-anilino-2-[3-(2,2-difluoroethoxy)pyridin-4-yl]-N-(2-hydroxyethyl)-N-methyl-4-oxo-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound N(C1=CC=CC=C1)C1=C(NC=2CC(CC(C1=2)=O)C(=O)N(C)CCO)C1=C(C=NC=C1)OCC(F)F GMODEEMIZHSOOO-UHFFFAOYSA-N 0.000 claims 1
RDUAHKZYAAPIGE-UHFFFAOYSA-N 3-anilino-2-[3-(2-hydroxyethoxy)pyridin-4-yl]-4-oxo-1,5,6,7-tetrahydroindole-6-carboxylic acid Chemical compound OCCOC=1C=NC=CC=1C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)C(=O)O RDUAHKZYAAPIGE-UHFFFAOYSA-N 0.000 claims 1
SICYLCBBKASRPL-UHFFFAOYSA-N 3-anilino-2-[3-(2-hydroxyethoxy)pyridin-4-yl]-N,N-dimethyl-4-oxo-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound N(C1=CC=CC=C1)C1=C(NC=2CC(CC(C1=2)=O)C(=O)N(C)C)C1=C(C=NC=C1)OCCO SICYLCBBKASRPL-UHFFFAOYSA-N 0.000 claims 1
YPFABYOBKVJBHR-UHFFFAOYSA-N 3-anilino-2-[3-(2-hydroxyethoxy)pyridin-4-yl]-N-(2-hydroxyethyl)-N-methyl-4-oxo-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound N(C1=CC=CC=C1)C1=C(NC=2CC(CC(C1=2)=O)C(=O)N(C)CCO)C1=C(C=NC=C1)OCCO YPFABYOBKVJBHR-UHFFFAOYSA-N 0.000 claims 1
VMECXKSJRTUHNC-UHFFFAOYSA-N 3-anilino-2-[3-(2-methoxyethoxy)pyridin-4-yl]-4-oxo-1,5,6,7-tetrahydroindole-6-carboxylic acid Chemical compound N(C1=CC=CC=C1)C1=C(NC=2CC(CC(C1=2)=O)C(=O)O)C1=C(C=NC=C1)OCCOC VMECXKSJRTUHNC-UHFFFAOYSA-N 0.000 claims 1
SWKTULOPJLFUIR-UHFFFAOYSA-N 3-anilino-2-[3-(2-methoxyethoxy)pyridin-4-yl]-6-prop-2-enyl-1,5,6,7-tetrahydroindol-4-one Chemical compound COCCOC=1C=NC=CC=1C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)CC=C SWKTULOPJLFUIR-UHFFFAOYSA-N 0.000 claims 1
JXPQDQQBQSTOJI-UHFFFAOYSA-N 3-anilino-2-[3-(2-methoxyethoxy)pyridin-4-yl]-N,N-dimethyl-4-oxo-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound COCCOC=1C=NC=CC=1C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)C(=O)N(C)C JXPQDQQBQSTOJI-UHFFFAOYSA-N 0.000 claims 1
SOAKDJLCGUGMBG-UHFFFAOYSA-N 3-anilino-2-[3-(cyclopropylmethoxy)pyridin-4-yl]-4-oxo-1,5,6,7-tetrahydroindole-6-carboxylic acid Chemical compound N(C1=CC=CC=C1)C1=C(NC=2CC(CC(C1=2)=O)C(=O)O)C1=C(C=NC=C1)OCC1CC1 SOAKDJLCGUGMBG-UHFFFAOYSA-N 0.000 claims 1
CVKSDZDGUUIAQT-UHFFFAOYSA-N 3-anilino-2-[3-(cyclopropylmethoxy)pyridin-4-yl]-6-prop-2-enyl-1,5,6,7-tetrahydroindol-4-one Chemical compound C1(CC1)COC=1C=NC=CC=1C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)CC=C CVKSDZDGUUIAQT-UHFFFAOYSA-N 0.000 claims 1
LKWZZKSNZRFLBJ-UHFFFAOYSA-N 3-anilino-2-[3-(cyclopropylmethoxy)pyridin-4-yl]-N,N-dimethyl-4-oxo-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound N(C1=CC=CC=C1)C1=C(NC=2CC(CC(C1=2)=O)C(=O)N(C)C)C1=C(C=NC=C1)OCC1CC1 LKWZZKSNZRFLBJ-UHFFFAOYSA-N 0.000 claims 1
PUXCJQYNOVCAHI-UHFFFAOYSA-N 3-anilino-2-pyridin-4-yl-6-(pyrrolidine-1-carbonyl)-1,5,6,7-tetrahydroindol-4-one Chemical compound C1(=CC=CC=C1)NC1=C(NC=2CC(CC(C1=2)=O)C(=O)N1CCCC1)C1=CC=NC=C1 PUXCJQYNOVCAHI-UHFFFAOYSA-N 0.000 claims 1
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 1
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
DBMYKEXKXSCIAM-UHFFFAOYSA-N 3-anilino-4-oxo-2-pyridin-4-yl-N-(3,3,3-trifluoropropyl)-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound O=C1C=2C(=C(NC=2CC(C1)C(=O)NCCC(F)(F)F)C1=CC=NC=C1)NC1=CC=CC=C1 DBMYKEXKXSCIAM-UHFFFAOYSA-N 0.000 claims 1
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 1
XPSJJCKNPPJPKO-UHFFFAOYSA-N 3-anilino-4-oxo-N-propan-2-yl-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound O=C1C=2C(=C(NC=2CC(C1)C(=O)NC(C)C)C1=CC=NC=C1)NC1=CC=CC=C1 XPSJJCKNPPJPKO-UHFFFAOYSA-N 0.000 claims 1
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 1
GEPMWJWWWXVSRA-UHFFFAOYSA-N 3-anilino-6-(1,3-benzothiazol-2-ylsulfanylmethyl)-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-4-one Chemical compound S1C(=NC2=C1C=CC=C2)SCC1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O GEPMWJWWWXVSRA-UHFFFAOYSA-N 0.000 claims 1
UZGZOQQQOXSXGR-UHFFFAOYSA-N 3-anilino-6-(1,3-benzothiazol-2-ylsulfonylmethyl)-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-4-one Chemical compound S1C(=NC2=C1C=CC=C2)S(=O)(=O)CC1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O UZGZOQQQOXSXGR-UHFFFAOYSA-N 0.000 claims 1
BXONSDKCJQOMEA-UHFFFAOYSA-N 3-anilino-6-(2-hydroxypropan-2-yl)-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-4-one Chemical compound OC(C)(C)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O BXONSDKCJQOMEA-UHFFFAOYSA-N 0.000 claims 1
GOOXUGSBCXDDNS-UHFFFAOYSA-N 3-anilino-6-(3-hydroxyazetidine-1-carbonyl)-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-4-one Chemical compound OC1CN(C1)C(=O)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O GOOXUGSBCXDDNS-UHFFFAOYSA-N 0.000 claims 1
VTBVNABAMHWDHA-UHFFFAOYSA-N 3-anilino-6-(4-methylpiperazine-1-carbonyl)-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-4-one Chemical compound CN1CCN(CC1)C(=O)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O VTBVNABAMHWDHA-UHFFFAOYSA-N 0.000 claims 1
PXZFTXAFGJTZKE-UHFFFAOYSA-N 3-anilino-6-(azetidine-1-carbonyl)-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-4-one Chemical compound N1(CCC1)C(=O)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O PXZFTXAFGJTZKE-UHFFFAOYSA-N 0.000 claims 1
AEAALKMCMDRQAF-UHFFFAOYSA-N 3-anilino-6-(azidomethyl)-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-4-one Chemical compound N(=[N+]=[N-])CC1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O AEAALKMCMDRQAF-UHFFFAOYSA-N 0.000 claims 1
QBANRMLJINHQHB-UHFFFAOYSA-N 3-anilino-6-(ethylsulfanylmethyl)-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-4-one Chemical compound C(C)SCC1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O QBANRMLJINHQHB-UHFFFAOYSA-N 0.000 claims 1
AJMDEPMOARPSKQ-UHFFFAOYSA-N 3-anilino-6-(ethylsulfonylmethyl)-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-4-one Chemical compound C(C)S(=O)(=O)CC1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O AJMDEPMOARPSKQ-UHFFFAOYSA-N 0.000 claims 1
OWLQGXQXOWHBKT-UHFFFAOYSA-N 3-anilino-6-(hydroxymethyl)-1-methyl-2-pyridin-4-yl-6,7-dihydro-5H-indol-4-one Chemical compound OCC1CC(C=2C(=C(N(C=2C1)C)C1=CC=NC=C1)NC1=CC=CC=C1)=O OWLQGXQXOWHBKT-UHFFFAOYSA-N 0.000 claims 1
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 1
APMYDDHAGZKAPX-UHFFFAOYSA-N 3-anilino-6-(hydroxymethyl)-6-methyl-2-pyridin-4-yl-5,7-dihydro-1H-indol-4-one Chemical compound OCC1(CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O)C APMYDDHAGZKAPX-UHFFFAOYSA-N 0.000 claims 1
SHQXZWHUIDNCOX-UHFFFAOYSA-N 3-anilino-6-(morpholin-4-ylmethyl)-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-4-one Chemical compound N1(CCOCC1)CC1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O SHQXZWHUIDNCOX-UHFFFAOYSA-N 0.000 claims 1
BQAWJIGVZVATFY-UHFFFAOYSA-N 3-anilino-6-(morpholine-4-carbonyl)-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-4-one Chemical compound N1(CCOCC1)C(=O)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O BQAWJIGVZVATFY-UHFFFAOYSA-N 0.000 claims 1
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 1
RDRHZQBZDDCILF-UHFFFAOYSA-N 3-anilino-6-(propan-2-ylsulfanylmethyl)-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-4-one Chemical compound C1(=CC=CC=C1)NC1=C(NC=2CC(CC(C1=2)=O)CSC(C)C)C1=CC=NC=C1 RDRHZQBZDDCILF-UHFFFAOYSA-N 0.000 claims 1
OACQINFLUGYQEU-UHFFFAOYSA-N 3-anilino-6-(propan-2-ylsulfonylmethyl)-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-4-one Chemical compound C1(=CC=CC=C1)NC1=C(NC=2CC(CC(C1=2)=O)CS(=O)(=O)C(C)C)C1=CC=NC=C1 OACQINFLUGYQEU-UHFFFAOYSA-N 0.000 claims 1
PNGVPNKHNKSAHV-UHUGOGIASA-N 3-anilino-6-[(3R)-3-hydroxypyrrolidine-1-carbonyl]-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-4-one Chemical compound O[C@H]1CN(CC1)C(=O)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O PNGVPNKHNKSAHV-UHUGOGIASA-N 0.000 claims 1
PNGVPNKHNKSAHV-DAFXYXGESA-N 3-anilino-6-[(3S)-3-hydroxypyrrolidine-1-carbonyl]-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-4-one Chemical compound O[C@@H]1CN(CC1)C(=O)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O PNGVPNKHNKSAHV-DAFXYXGESA-N 0.000 claims 1
WKOOUKZPLMCIMQ-UHFFFAOYSA-N 3-anilino-6-[(4-methylpiperazin-1-yl)methyl]-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-4-one Chemical compound CN1CCN(CC1)CC1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O WKOOUKZPLMCIMQ-UHFFFAOYSA-N 0.000 claims 1
UCOXTXDVLOWFQX-VOTSOKGWSA-N 3-anilino-6-[(E)-3-(dimethylamino)prop-1-enyl]-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-4-one Chemical compound CN(C/C=C/C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O)C UCOXTXDVLOWFQX-VOTSOKGWSA-N 0.000 claims 1
UCOXTXDVLOWFQX-SREVYHEPSA-N 3-anilino-6-[(Z)-3-(dimethylamino)prop-1-enyl]-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-4-one Chemical compound CN(C\C=C/C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O)C UCOXTXDVLOWFQX-SREVYHEPSA-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
KWJPIKQVMZYJMN-UHFFFAOYSA-N 3-anilino-6-[[2-(dimethylamino)ethyl-methylamino]methyl]-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-4-one Chemical compound CN(CCN(C)CC1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O)C KWJPIKQVMZYJMN-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
SDVLDVXVTGCMER-UHFFFAOYSA-N 3-anilino-6-[[methyl(propan-2-yl)amino]methyl]-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-4-one Chemical compound CN(C(C)C)CC1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O SDVLDVXVTGCMER-UHFFFAOYSA-N 0.000 claims 1
OGCJRSNKDSSHEO-UHFFFAOYSA-N 3-anilino-6-[tert-butyl(dimethyl)silyl]oxy-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-4-one Chemical compound [Si](C)(C)(C(C)(C)C)OC1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O OGCJRSNKDSSHEO-UHFFFAOYSA-N 0.000 claims 1
AKSBEPYPLGGRLM-UHFFFAOYSA-N 3-anilino-6-ethenyl-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-4-one Chemical compound C(=C)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O AKSBEPYPLGGRLM-UHFFFAOYSA-N 0.000 claims 1
ZLXFAUKQUKVYPF-UHFFFAOYSA-N 3-anilino-6-hydroxy-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-4-one Chemical compound OC1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O ZLXFAUKQUKVYPF-UHFFFAOYSA-N 0.000 claims 1
YMXIGQBXFMEYFJ-UHFFFAOYSA-N 3-anilino-6-prop-2-enyl-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-4-one Chemical compound C1(=CC=CC=C1)NC1=C(NC=2CC(CC(C1=2)=O)CC=C)C1=CC=NC=C1 YMXIGQBXFMEYFJ-UHFFFAOYSA-N 0.000 claims 1
GDMZMMXIHUDUAD-HZLHXKQSSA-N 3-anilino-N,N-diethyl-2-[2-[[(1S,2S)-2-fluorocyclopropanecarbonyl]amino]pyridin-4-yl]-6-methyl-4-oxo-5,7-dihydro-1H-indole-6-carboxamide Chemical compound N(C1=CC=CC=C1)C1=C(NC=2CC(CC(C1=2)=O)(C(=O)N(CC)CC)C)C1=CC(=NC=C1)NC(=O)[C@H]1[C@H](C1)F GDMZMMXIHUDUAD-HZLHXKQSSA-N 0.000 claims 1
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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 1
MEGOFTRVPKISMV-UHFFFAOYSA-N 3-anilino-N-(1-hydroxy-2-methylpropan-2-yl)-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound OCC(C)(C)NC(=O)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O MEGOFTRVPKISMV-UHFFFAOYSA-N 0.000 claims 1
VVPFPPWYMLXSBZ-UHFFFAOYSA-N 3-anilino-N-(1-methoxy-2-methylpropan-2-yl)-N-methyl-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound COCC(C)(C)N(C(=O)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O)C VVPFPPWYMLXSBZ-UHFFFAOYSA-N 0.000 claims 1
ZRIRRKZCLFBNAS-UHFFFAOYSA-N 3-anilino-N-(2,2-difluoroethyl)-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound FC(CNC(=O)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O)F ZRIRRKZCLFBNAS-UHFFFAOYSA-N 0.000 claims 1
SPFGGAGTLQBWCW-UHFFFAOYSA-N 3-anilino-N-(2,2-difluoroethyl)-N-methyl-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound FC(CN(C(=O)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O)C)F SPFGGAGTLQBWCW-UHFFFAOYSA-N 0.000 claims 1
CBJQTOLNBPPWMY-UHFFFAOYSA-N 3-anilino-N-(2,2-dimethylpropyl)-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound CC(CNC(=O)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O)(C)C CBJQTOLNBPPWMY-UHFFFAOYSA-N 0.000 claims 1
FQXKBFZWIWPNSS-UHFFFAOYSA-N 3-anilino-N-(2,2-dimethylpropyl)-N-methyl-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound CC(CN(C(=O)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O)C)(C)C FQXKBFZWIWPNSS-UHFFFAOYSA-N 0.000 claims 1
JAYWWERGQCTNBK-UHFFFAOYSA-N 3-anilino-N-(2-hydroxy-2-methylpropyl)-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound OC(CNC(=O)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O)(C)C JAYWWERGQCTNBK-UHFFFAOYSA-N 0.000 claims 1
NBCZKSKSTREDKR-UHFFFAOYSA-N 3-anilino-N-(2-hydroxy-2-methylpropyl)-N-methyl-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound OC(CN(C(=O)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O)C)(C)C NBCZKSKSTREDKR-UHFFFAOYSA-N 0.000 claims 1
VLSWMBARALVIRQ-UHFFFAOYSA-N 3-anilino-N-(2-hydroxyethyl)-2-(3-methoxypyridin-4-yl)-N-methyl-4-oxo-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound OCCN(C(=O)C1CC(C=2C(=C(NC=2C1)C1=C(C=NC=C1)OC)NC1=CC=CC=C1)=O)C VLSWMBARALVIRQ-UHFFFAOYSA-N 0.000 claims 1
NZHFBBNKVWIBMA-UHFFFAOYSA-N 3-anilino-N-(2-hydroxyethyl)-2-[3-(2-methoxyethoxy)pyridin-4-yl]-N-methyl-4-oxo-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound OCCN(C(=O)C1CC(C=2C(=C(NC=2C1)C1=C(C=NC=C1)OCCOC)NC1=CC=CC=C1)=O)C NZHFBBNKVWIBMA-UHFFFAOYSA-N 0.000 claims 1
QQFOHXSBDOEWRX-UHFFFAOYSA-N 3-anilino-N-(2-hydroxyethyl)-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound OCCNC(=O)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O QQFOHXSBDOEWRX-UHFFFAOYSA-N 0.000 claims 1
YYQRODQHKYKLBH-UHFFFAOYSA-N 3-anilino-N-(2-hydroxyethyl)-4-oxo-N-propan-2-yl-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(C)C YYQRODQHKYKLBH-UHFFFAOYSA-N 0.000 claims 1
LKCQEKWLRHRFSE-UHFFFAOYSA-N 3-anilino-N-(2-methoxyethyl)-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound COCCNC(=O)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O LKCQEKWLRHRFSE-UHFFFAOYSA-N 0.000 claims 1
VVEYDNHTAAPTIE-UHFFFAOYSA-N 3-anilino-N-(2-methoxyethyl)-N-methyl-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound COCCN(C(=O)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O)C VVEYDNHTAAPTIE-UHFFFAOYSA-N 0.000 claims 1
NLTFKTCFLWDQAM-UHFFFAOYSA-N 3-anilino-N-(2-methylpropyl)-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound CC(CNC(=O)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O)C NLTFKTCFLWDQAM-UHFFFAOYSA-N 0.000 claims 1
WGPMMHVBKWAJAT-SBCWPUQDSA-N 3-anilino-N-(cyclopropylmethyl)-2-[2-[[(1S,2S)-2-fluorocyclopropanecarbonyl]amino]pyridin-4-yl]-N,6-dimethyl-4-oxo-5,7-dihydro-1H-indole-6-carboxamide Chemical compound N(C1=CC=CC=C1)C1=C(NC=2CC(CC(C1=2)=O)(C(=O)N(C)CC1CC1)C)C1=CC(=NC=C1)NC(=O)[C@H]1[C@H](C1)F WGPMMHVBKWAJAT-SBCWPUQDSA-N 0.000 claims 1
WQDKWOSDJCLJMF-UHFFFAOYSA-N 3-anilino-N-(cyclopropylmethyl)-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound C1(CC1)CNC(=O)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O WQDKWOSDJCLJMF-UHFFFAOYSA-N 0.000 claims 1
CJYHPBCNUNAHBM-UHFFFAOYSA-N 3-anilino-N-(cyclopropylmethyl)-N-methyl-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound C1(CC1)CN(C(=O)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O)C CJYHPBCNUNAHBM-UHFFFAOYSA-N 0.000 claims 1
GLNDONBADFSQAS-UHFFFAOYSA-N 3-anilino-N-[(1-hydroxycyclobutyl)methyl]-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound OC1(CCC1)CNC(=O)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O GLNDONBADFSQAS-UHFFFAOYSA-N 0.000 claims 1
OWAITRHCOFWHGF-UHFFFAOYSA-N 3-anilino-N-[(1-hydroxycyclobutyl)methyl]-N-methyl-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound OC1(CCC1)CN(C(=O)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O)C OWAITRHCOFWHGF-UHFFFAOYSA-N 0.000 claims 1
KATYYDPSNBJXHX-UHFFFAOYSA-N 3-anilino-N-[(1-hydroxycyclopropyl)methyl]-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound OC1(CC1)CNC(=O)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O KATYYDPSNBJXHX-UHFFFAOYSA-N 0.000 claims 1
PVFXNXWMPDQWIK-IURRXHLWSA-N 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)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O PVFXNXWMPDQWIK-IURRXHLWSA-N 0.000 claims 1
KNRHAEYSQVLDNE-IURRXHLWSA-N 3-anilino-N-[(2R)-2-hydroxypropyl]-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound O[C@@H](CNC(=O)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O)C KNRHAEYSQVLDNE-IURRXHLWSA-N 0.000 claims 1
VIUKXFNFAKVMCS-LDCVWXEPSA-N 3-anilino-N-[(2R)-2-hydroxypropyl]-N-methyl-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound O[C@@H](CN(C(=O)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O)C)C VIUKXFNFAKVMCS-LDCVWXEPSA-N 0.000 claims 1
PVFXNXWMPDQWIK-LBAUFKAWSA-N 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)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O PVFXNXWMPDQWIK-LBAUFKAWSA-N 0.000 claims 1
KNRHAEYSQVLDNE-LBAUFKAWSA-N 3-anilino-N-[(2S)-2-hydroxypropyl]-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound O[C@H](CNC(=O)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O)C KNRHAEYSQVLDNE-LBAUFKAWSA-N 0.000 claims 1
VIUKXFNFAKVMCS-MYJWUSKBSA-N 3-anilino-N-[(2S)-2-hydroxypropyl]-N-methyl-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound O[C@H](CN(C(=O)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O)C)C VIUKXFNFAKVMCS-MYJWUSKBSA-N 0.000 claims 1
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QIWGGCXQEWKNJU-UHFFFAOYSA-N 3-anilino-N-[2-(dimethylamino)ethyl]-N-methyl-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound CN(CCN(C(=O)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O)C)C QIWGGCXQEWKNJU-UHFFFAOYSA-N 0.000 claims 1
DWXBSVKFBYDZKF-UHFFFAOYSA-N 3-anilino-N-[2-(methylamino)ethyl]-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound CNCCNC(=O)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O DWXBSVKFBYDZKF-UHFFFAOYSA-N 0.000 claims 1
HJOOBUWSVOTXQU-UHFFFAOYSA-N 3-anilino-N-cyclobutyl-N-methyl-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound C1(CCC1)N(C(=O)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O)C HJOOBUWSVOTXQU-UHFFFAOYSA-N 0.000 claims 1
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ORZLUYBECSUCFP-UHFFFAOYSA-N 3-anilino-N-ethyl-N-methyl-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound C(C)N(C(=O)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O)C ORZLUYBECSUCFP-UHFFFAOYSA-N 0.000 claims 1
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WPSDZAFIPKWWQD-UHFFFAOYSA-N 3-anilino-N-methyl-4-oxo-2-pyridin-4-yl-N-(2-pyrrolidin-1-ylethyl)-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)CCN1CCCC1 WPSDZAFIPKWWQD-UHFFFAOYSA-N 0.000 claims 1
JQXRDOHKHLHKST-UHFFFAOYSA-N 3-anilino-N-methyl-4-oxo-2-pyridin-4-yl-N-(3,3,3-trifluoropropyl)-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(F)(F)F JQXRDOHKHLHKST-UHFFFAOYSA-N 0.000 claims 1
UBDWVQPTJGDYTJ-UHFFFAOYSA-N 3-anilino-N-methyl-N-(2-methylpropyl)-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)CC(C)C UBDWVQPTJGDYTJ-UHFFFAOYSA-N 0.000 claims 1
JVLHYJWGSDBUNJ-UHFFFAOYSA-N 3-anilino-N-methyl-N-(2-morpholin-4-ylethyl)-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)CCN1CCOCC1 JVLHYJWGSDBUNJ-UHFFFAOYSA-N 0.000 claims 1
YLFOIFYTWZRMRF-UHFFFAOYSA-N 3-anilino-N-methyl-N-[2-(methylamino)ethyl]-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)CCNC YLFOIFYTWZRMRF-UHFFFAOYSA-N 0.000 claims 1
UHVHGKZKXDTLCZ-UHFFFAOYSA-N 3-anilino-N-tert-butyl-N-methyl-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound C(C)(C)(C)N(C(=O)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O)C UHVHGKZKXDTLCZ-UHFFFAOYSA-N 0.000 claims 1
ZVIQUYOKNAQHIO-UHFFFAOYSA-N 4-oxo-2-pyridin-4-yl-3-(pyridin-2-ylamino)-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=NC=CC=C1 ZVIQUYOKNAQHIO-UHFFFAOYSA-N 0.000 claims 1
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
FDPRABYDEGLAHE-UHFFFAOYSA-N 5-[2-(2-acetamidopyridin-4-yl)-3-anilino-4-oxo-1,5,6,7-tetrahydroindol-6-yl]pentanoic acid Chemical compound C(C)(=O)NC1=NC=CC(=C1)C=1NC=2CC(CC(C=2C=1NC1=CC=CC=C1)=O)CCCCC(=O)O FDPRABYDEGLAHE-UHFFFAOYSA-N 0.000 claims 1
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ZUTWKELXGKEUHS-UHFFFAOYSA-N CC(=O)NC1=NC=CC(=C1)C2=C(C3=C(N2)CC(CC3=O)(C)C(=O)N4CC5CC4CN5C)NC6=CC=CC=C6 Chemical compound CC(=O)NC1=NC=CC(=C1)C2=C(C3=C(N2)CC(CC3=O)(C)C(=O)N4CC5CC4CN5C)NC6=CC=CC=C6 ZUTWKELXGKEUHS-UHFFFAOYSA-N 0.000 claims 1
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FFYGYWCVPQUDHZ-UHFFFAOYSA-N N,N-dimethyl-4-oxo-2-pyridin-4-yl-3-(pyridin-2-ylamino)-1,5,6,7-tetrahydroindole-6-carboxamide Chemical compound CN(C(=O)C1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=NC=CC=C1)=O)C FFYGYWCVPQUDHZ-UHFFFAOYSA-N 0.000 claims 1
ZQIDMKWFMWGBNB-UHFFFAOYSA-N N-(3-anilino-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-6-yl)-2-cyclopropylacetamide Chemical compound C1(CC1)CC(=O)NC1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O ZQIDMKWFMWGBNB-UHFFFAOYSA-N 0.000 claims 1
GCXPHUJTBGSGGU-UHFFFAOYSA-N N-(3-anilino-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-6-yl)-2-methylpropanamide Chemical compound CC(C(=O)NC1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O)C GCXPHUJTBGSGGU-UHFFFAOYSA-N 0.000 claims 1
PFZQMLFBNDANOH-UHFFFAOYSA-N N-(3-anilino-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-6-yl)-3,3-dimethylbutanamide Chemical compound CC(CC(=O)NC1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O)(C)C PFZQMLFBNDANOH-UHFFFAOYSA-N 0.000 claims 1
AQXOTMAETJEANA-UHFFFAOYSA-N N-(3-anilino-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-6-yl)-3-(methylamino)propanamide 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CNCCC(=O)NC1Cc2[nH]c(c(Nc3ccccc3)c2C(=O)C1)-c1ccncc1 AQXOTMAETJEANA-UHFFFAOYSA-N 0.000 claims 1
MTJPSGSUJOWNJG-UHFFFAOYSA-N N-(3-anilino-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-6-yl)-3-hydroxy-2,2-dimethylpropanamide Chemical compound OCC(C(=O)NC1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O)(C)C MTJPSGSUJOWNJG-UHFFFAOYSA-N 0.000 claims 1
SYRJNVPXMKUJAO-UHFFFAOYSA-N N-(3-anilino-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-6-yl)-3-hydroxy-3-methylbutanamide Chemical compound OC(CC(=O)NC1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O)(C)C SYRJNVPXMKUJAO-UHFFFAOYSA-N 0.000 claims 1
PIZLSUIISMGOEO-UHFFFAOYSA-N N-(3-anilino-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-6-yl)-3-methylbutanamide Chemical compound CC(CC(=O)NC1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O)C PIZLSUIISMGOEO-UHFFFAOYSA-N 0.000 claims 1
MGDKLOHYBKWLHS-UHFFFAOYSA-N N-(3-anilino-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-6-yl)acetamide Chemical compound C(C)(=O)NC1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O MGDKLOHYBKWLHS-UHFFFAOYSA-N 0.000 claims 1
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 1
RQHDUCKXPQSBKE-UHFFFAOYSA-N N-[(3-anilino-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-6-yl)methyl]-1,3-thiazole-2-carboxamide Chemical compound O=C1C=2C(=C(NC=2CC(C1)CNC(=O)C=1SC=CN=1)C1=CC=NC=C1)NC1=CC=CC=C1 RQHDUCKXPQSBKE-UHFFFAOYSA-N 0.000 claims 1
OBTQTOPPRLZSNZ-UHFFFAOYSA-N N-[(3-anilino-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-6-yl)methyl]-1-methylpyrrole-2-carboxamide Chemical compound CN1C(=CC=C1)C(=O)NCC1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O OBTQTOPPRLZSNZ-UHFFFAOYSA-N 0.000 claims 1
IJZAWRPNVKJTME-UHFFFAOYSA-N N-[(3-anilino-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-6-yl)methyl]-2-methoxyacetamide Chemical compound COCC(=O)NCC1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O IJZAWRPNVKJTME-UHFFFAOYSA-N 0.000 claims 1
JMDFZAAMRKJCCS-UHFFFAOYSA-N N-[(3-anilino-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-6-yl)methyl]-2-methylpropanamide Chemical compound CC(C(=O)NCC1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O)C JMDFZAAMRKJCCS-UHFFFAOYSA-N 0.000 claims 1
XERHHOHEWXQGHG-UHFFFAOYSA-N N-[(3-anilino-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-6-yl)methyl]-3-methoxypropanamide Chemical compound COCCC(=O)NCC1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O XERHHOHEWXQGHG-UHFFFAOYSA-N 0.000 claims 1
IGWZDHTYEVMNKG-UHFFFAOYSA-N N-[(3-anilino-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-6-yl)methyl]-4-fluorobenzenesulfonamide Chemical compound FC1=CC=C(C=C1)S(=O)(=O)NCC1CC(C=2C(=C(NC=2C1)C1=CC=NC=C1)NC1=CC=CC=C1)=O IGWZDHTYEVMNKG-UHFFFAOYSA-N 0.000 claims 1
XWWZHZHKOXJPTE-UHFFFAOYSA-N N-[(3-anilino-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-6-yl)methyl]cyclobutanecarboxamide Chemical compound O=C1C=2C(=C(NC=2CC(C1)CNC(=O)C1CCC1)C1=CC=NC=C1)NC1=CC=CC=C1 XWWZHZHKOXJPTE-UHFFFAOYSA-N 0.000 claims 1
ZPANJMPBINGDRN-UHFFFAOYSA-N N-[(3-anilino-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-6-yl)methyl]cyclopropanecarboxamide Chemical compound O=C1C=2C(=C(NC=2CC(C1)CNC(=O)C1CC1)C1=CC=NC=C1)NC1=CC=CC=C1 ZPANJMPBINGDRN-UHFFFAOYSA-N 0.000 claims 1
QQSNLYIUWSJQMY-UHFFFAOYSA-N N-[(3-anilino-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-6-yl)methyl]furan-2-carboxamide Chemical compound O=C1C=2C(=C(NC=2CC(C1)CNC(=O)C=1OC=CC=1)C1=CC=NC=C1)NC1=CC=CC=C1 QQSNLYIUWSJQMY-UHFFFAOYSA-N 0.000 claims 1
IKFUPGOQBONXHZ-UHFFFAOYSA-N N-[(3-anilino-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-6-yl)methyl]oxane-4-carboxamide Chemical compound O=C1C=2C(=C(NC=2CC(C1)CNC(=O)C1CCOCC1)C1=CC=NC=C1)NC1=CC=CC=C1 IKFUPGOQBONXHZ-UHFFFAOYSA-N 0.000 claims 1
QUGNBJORJVFHPA-UHFFFAOYSA-N N-[(3-anilino-4-oxo-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-6-yl)methyl]propane-2-sulfonamide Chemical compound O=C1C=2C(=C(NC=2CC(C1)CNS(=O)(=O)C(C)C)C1=CC=NC=C1)NC1=CC=CC=C1 QUGNBJORJVFHPA-UHFFFAOYSA-N 0.000 claims 1
RTYLHMXSDOPNRC-UHFFFAOYSA-N N-[4-[3-anilino-4-oxo-6-(1,3-thiazol-2-ylsulfonylmethyl)-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)C=1SC=CN=1 RTYLHMXSDOPNRC-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
JVLRYRQHGNOMBF-UHFFFAOYSA-N N-[4-[3-anilino-4-oxo-6-(propan-2-ylsulfanylmethyl)-1,5,6,7-tetrahydroindol-2-yl]pyridin-2-yl]-4-chlorobenzamide Chemical compound CC(C)SCC1CC2=C(C(NC3=CC=CC=C3)=C(N2)C2=CC(NC(=O)C3=CC=C(Cl)C=C3)=NC=C2)C(=O)C1 JVLRYRQHGNOMBF-UHFFFAOYSA-N 0.000 claims 1
PWUYDXUKCDVNTC-UHFFFAOYSA-N N-[4-[3-anilino-4-oxo-6-(propan-2-ylsulfanylmethyl)-1,5,6,7-tetrahydroindol-2-yl]pyridin-2-yl]-4-fluoro-3-methoxybenzamide Chemical compound N(C1=CC=CC=C1)C1=C(NC=2CC(CC(C1=2)=O)CSC(C)C)C1=CC(=NC=C1)NC(C1=CC(=C(C=C1)F)OC)=O PWUYDXUKCDVNTC-UHFFFAOYSA-N 0.000 claims 1
VJMZRIZKZXETQU-UHFFFAOYSA-N N-[4-[3-anilino-4-oxo-6-(propan-2-ylsulfanylmethyl)-1,5,6,7-tetrahydroindol-2-yl]pyridin-2-yl]-4-fluorobenzamide Chemical compound CC(C)SCC1CC2=C(C(NC3=CC=CC=C3)=C(N2)C2=CC(NC(=O)C3=CC=C(F)C=C3)=NC=C2)C(=O)C1 VJMZRIZKZXETQU-UHFFFAOYSA-N 0.000 claims 1
QDYIZSOZMYJZGY-UHFFFAOYSA-N N-[4-[3-anilino-4-oxo-6-(propan-2-ylsulfinylmethyl)-1,5,6,7-tetrahydroindol-2-yl]pyridin-2-yl]-1,3-thiazole-5-carboxamide Chemical compound O=C1C=2C(=C(NC=2CC(C1)CS(=O)C(C)C)C1=CC(=NC=C1)NC(=O)C1=CN=CS1)NC1=CC=CC=C1 QDYIZSOZMYJZGY-UHFFFAOYSA-N 0.000 claims 1
HSCPQNZMRXUFJI-UHFFFAOYSA-N N-[4-[3-anilino-4-oxo-6-(propan-2-ylsulfinylmethyl)-1,5,6,7-tetrahydroindol-2-yl]pyridin-2-yl]-4-fluorobenzamide Chemical compound FC1=CC=C(C(=O)NC2=NC=CC(=C2)C=2NC=3CC(CC(C=3C=2NC2=CC=CC=C2)=O)CS(=O)C(C)C)C=C1 HSCPQNZMRXUFJI-UHFFFAOYSA-N 0.000 claims 1
HQWRDEHQKXGDMV-UHFFFAOYSA-N N-[4-[3-anilino-4-oxo-6-(propan-2-ylsulfonylmethyl)-1,5,6,7-tetrahydroindol-2-yl]pyridin-2-yl]-2-fluoro-2-methylpropanamide Chemical compound CC(C)S(=O)(=O)CC1CC2=C(C(NC3=CC=CC=C3)=C(N2)C2=CC(NC(=O)C(C)(C)F)=NC=C2)C(=O)C1 HQWRDEHQKXGDMV-UHFFFAOYSA-N 0.000 claims 1
PYKXBSPUDKVMOK-UHFFFAOYSA-N N-[4-[3-anilino-4-oxo-6-(propan-2-ylsulfonylmethyl)-1,5,6,7-tetrahydroindol-2-yl]pyridin-2-yl]-4-fluoro-3-methoxybenzamide Chemical compound COC1=C(F)C=CC(=C1)C(=O)NC1=NC=CC(=C1)C1=C(NC2=CC=CC=C2)C2=C(CC(CS(=O)(=O)C(C)C)CC2=O)N1 PYKXBSPUDKVMOK-UHFFFAOYSA-N 0.000 claims 1
GPRZOEHMGSSKBM-UHFFFAOYSA-N N-[4-[3-anilino-4-oxo-6-(propan-2-ylsulfonylmethyl)-1,5,6,7-tetrahydroindol-2-yl]pyridin-2-yl]-4-fluoro-N-methylbenzamide Chemical compound N(C1=CC=CC=C1)C1=C(NC=2CC(CC(C1=2)=O)CS(=O)(=O)C(C)C)C1=CC(=NC=C1)N(C(C1=CC=C(C=C1)F)=O)C GPRZOEHMGSSKBM-UHFFFAOYSA-N 0.000 claims 1
KRERNOJVFCFUQT-UHFFFAOYSA-N N-[4-[3-anilino-6-(1,3-oxazol-2-ylsulfanylmethyl)-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(CSC3=NC=CO3)CC2=O)N1 KRERNOJVFCFUQT-UHFFFAOYSA-N 0.000 claims 1
BULZSUFVFGFPLL-UHFFFAOYSA-N N-[4-[3-anilino-6-(2-hydroxypropan-2-yl)-4-oxo-1,5,6,7-tetrahydroindol-2-yl]pyridin-2-yl]acetamide Chemical compound OC(C)(C)C1CC(C=2C(=C(NC=2C1)C1=CC(=NC=C1)NC(C)=O)NC1=CC=CC=C1)=O BULZSUFVFGFPLL-UHFFFAOYSA-N 0.000 claims 1
UZWLQMHGWPONOP-UHFFFAOYSA-N N-[4-[3-anilino-6-(2-hydroxypropan-2-yl)-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(C)(C)O UZWLQMHGWPONOP-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
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 1
YJUJSVPEPQDBCB-UHFFFAOYSA-N N-[4-[3-anilino-6-(3-fluoroazetidine-1-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)N1CC(C1)F)C1=CC(=NC=C1)NC(C)=O YJUJSVPEPQDBCB-UHFFFAOYSA-N 0.000 claims 1
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 1
CISBXJYQUFAOES-UHFFFAOYSA-N N-[4-[3-anilino-6-(methanesulfonamidomethyl)-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)CNS(=O)(=O)C CISBXJYQUFAOES-UHFFFAOYSA-N 0.000 claims 1
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 1
LXDLQOTXYIVQEH-UHFFFAOYSA-N N-[4-[3-anilino-6-[(3,4-dichlorophenyl)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)Cl)C1=CC(=NC=C1)NC(C)=O LXDLQOTXYIVQEH-UHFFFAOYSA-N 0.000 claims 1
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 1
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 1
MARIURJLOZGSDR-UHFFFAOYSA-N N-[4-[3-anilino-6-[(4-fluoro-3-hydroxyphenyl)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)F)O)C1=CC(=NC=C1)NC(C)=O MARIURJLOZGSDR-UHFFFAOYSA-N 0.000 claims 1
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 1
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 1
USBNAOLXSKGHFO-UHFFFAOYSA-N N-[4-[3-anilino-6-[(4-fluorophenyl)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)F)C1=CC(=NC=C1)NC(C)=O USBNAOLXSKGHFO-UHFFFAOYSA-N 0.000 claims 1
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 1
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 1
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 1
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 1
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 1
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 1
AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims 1
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 1
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 1
XMSKDBWHCDMVES-CQSZACIVSA-N methyl (6R)-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-CQSZACIVSA-N 0.000 claims 1
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 1
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 1
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 1
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 1
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 1
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 1
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 1
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 1
VOBKZFNIDPYNER-MWSTZMHHSA-N methyl 3-anilino-2-[2-[[(1R,2R)-2-fluorocyclopropanecarbonyl]amino]pyridin-4-yl]-4-oxo-1,5,6,7-tetrahydroindole-6-carboxylate 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)OC VOBKZFNIDPYNER-MWSTZMHHSA-N 0.000 claims 1
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 1
ANGSGHGASKJJDC-UHFFFAOYSA-N methyl 3-anilino-2-[3-(2-hydroxyethoxy)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=C(C=NC=C1)OCCO ANGSGHGASKJJDC-UHFFFAOYSA-N 0.000 claims 1
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 1
AEXGDUUPZFXNND-UHFFFAOYSA-N methyl 3-anilino-2-[3-(cyclopropylmethoxy)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=C(C=NC=C1)OCC1CC1 AEXGDUUPZFXNND-UHFFFAOYSA-N 0.000 claims 1
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 1
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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 1
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