CA2709314A1 - 5-alkyl/alcenyl-3-cyanopyridines en tant qu'inhibiteurs de kinase - Google Patents

Info

Publication number

CA2709314A1

CA2709314A1 CA2709314A CA2709314A CA2709314A1 CA 2709314 A1 CA2709314 A1 CA 2709314A1 CA 2709314 A CA2709314 A CA 2709314A CA 2709314 A CA2709314 A CA 2709314A CA 2709314 A1 CA2709314 A1 CA 2709314A1

Authority

CA

Canada

Prior art keywords

methyl

amino

indol

nicotinonitrile

carbonitrile

Prior art date

2007-12-13

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
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• 229940043355 kinase inhibitor Drugs 0.000 title description 2
• 239000003757 phosphotransferase inhibitor Substances 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 281
• 238000000034 method Methods 0.000 claims abstract description 120
• 150000003839 salts Chemical class 0.000 claims abstract description 53
• 241000124008 Mammalia Species 0.000 claims abstract description 18
• 102000001253 Protein Kinase Human genes 0.000 claims abstract description 14
• 108060006633 protein kinase Proteins 0.000 claims abstract description 14
• -1 -O-R12" Chemical group 0.000 claims description 281
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 193
• 239000000203 mixture Substances 0.000 claims description 177
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 117
• GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims description 113
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 60
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 43
• 229920002554 vinyl polymer Polymers 0.000 claims description 43
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
• 125000000217 alkyl group Chemical group 0.000 claims description 31
• 229910052757 nitrogen Inorganic materials 0.000 claims description 30
• 125000004432 carbon atom Chemical group C* 0.000 claims description 29
• LBPFQPNAUVOEQD-UHFFFAOYSA-N 5-ethenyl-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C=C)C=NC=C1C#N LBPFQPNAUVOEQD-UHFFFAOYSA-N 0.000 claims description 27
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 25
• 239000002585 base Substances 0.000 claims description 24
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
• 125000005842 heteroatom Chemical group 0.000 claims description 23
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 23
• 230000008569 process Effects 0.000 claims description 22
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
• 229910052763 palladium Inorganic materials 0.000 claims description 18
• 125000005843 halogen group Chemical group 0.000 claims description 17
• 125000002947 alkylene group Chemical group 0.000 claims description 16
• 241001024304 Mino Species 0.000 claims description 14
• 150000001412 amines Chemical class 0.000 claims description 14
• 239000003054 catalyst Substances 0.000 claims description 14
• 125000001424 substituent group Chemical group 0.000 claims description 14
• IZWFJOYAEPNWTA-VOTSOKGWSA-N 5-[(e)-2-(4-formylphenyl)ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C1=CC=C(C=O)C=C1 IZWFJOYAEPNWTA-VOTSOKGWSA-N 0.000 claims description 13
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 12
• 229910052799 carbon Inorganic materials 0.000 claims description 12
• 239000003795 chemical substances by application Substances 0.000 claims description 12
• 239000012039 electrophile Substances 0.000 claims description 12
• PDRONDLFSQOAOR-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-(1,2,3,6-tetrahydropyridin-4-yl)pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C1=CCNCC1 PDRONDLFSQOAOR-UHFFFAOYSA-N 0.000 claims description 10
• 229910052794 bromium Inorganic materials 0.000 claims description 10
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
• IPPSROUBFNWADY-BQYQJAHWSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-(4-methylphenyl)ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC(C)=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C IPPSROUBFNWADY-BQYQJAHWSA-N 0.000 claims description 9
• JMBOYLIMLIXSDW-VOTSOKGWSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[3-[(4-methylpiperazin-1-yl)methyl]phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CC1=CC=CC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=C1 JMBOYLIMLIXSDW-VOTSOKGWSA-N 0.000 claims description 9
• DCLDPMOXNDZCQO-GORDUTHDSA-N 5-[(e)-2-(4-bromophenyl)ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C1=CC=C(Br)C=C1 DCLDPMOXNDZCQO-GORDUTHDSA-N 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 238000004519 manufacturing process Methods 0.000 claims description 9
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 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 8
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 8
• 239000003153 chemical reaction reagent Substances 0.000 claims description 8
• 125000004043 oxo group Chemical group O=* 0.000 claims description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
• RFIOZSIHFNEKFF-UHFFFAOYSA-M piperazine-1-carboxylate Chemical compound [O-]C(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-M 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
• TWDPQJRHLMLPRP-MDZDMXLPSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[4-(piperidin-1-ylmethyl)phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(C=C1)=CC=C1CN1CCCCC1 TWDPQJRHLMLPRP-MDZDMXLPSA-N 0.000 claims description 7
• 102000004190 Enzymes Human genes 0.000 claims description 7
• 108090000790 Enzymes Proteins 0.000 claims description 7
• 229910052740 iodine Inorganic materials 0.000 claims description 7
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 7
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 6
• YOSAIRCVRQVWFK-ONEGZZNKSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[4-[(4-methylpiperazin-1-yl)methyl]pyridin-2-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CC1=CC=NC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=C1 YOSAIRCVRQVWFK-ONEGZZNKSA-N 0.000 claims description 6
• MTLUUQAPDKXISA-NSCUHMNNSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-piperidin-4-ylethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C1CCNCC1 MTLUUQAPDKXISA-NSCUHMNNSA-N 0.000 claims description 6
• MBTPFASILYXEKX-VOTSOKGWSA-N 5-[(e)-2-[2-(2-chloroethoxy)phenyl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C1=CC=CC=C1OCCCl MBTPFASILYXEKX-VOTSOKGWSA-N 0.000 claims description 6
• KXLSRILGBPDSTI-AATRIKPKSA-N 5-[(e)-2-[6-(hydroxymethyl)pyridin-2-yl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C1=CC=CC(CO)=N1 KXLSRILGBPDSTI-AATRIKPKSA-N 0.000 claims description 6
• 206010052779 Transplant rejections Diseases 0.000 claims description 6
• 206010003246 arthritis Diseases 0.000 claims description 6
• 208000006673 asthma Diseases 0.000 claims description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
• 230000000694 effects Effects 0.000 claims description 6
• 125000002541 furyl group Chemical group 0.000 claims description 6
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
• DHGMIZFEATZVTF-JXMROGBWSA-N 4-(1h-indol-6-ylamino)-6-methyl-5-[(e)-2-phenylethenyl]pyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C=C3NC=CC3=CC=2)=C1\C=C\C1=CC=CC=C1 DHGMIZFEATZVTF-JXMROGBWSA-N 0.000 claims description 5
• UJYYVUFESIJSEY-BQYQJAHWSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CC(C=C1)=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C UJYYVUFESIJSEY-BQYQJAHWSA-N 0.000 claims description 5
• UPRQAYXZFHWKSB-AATRIKPKSA-N 5-[(e)-2-[3-(2-chloroethoxy)phenyl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C1=CC=CC(OCCCl)=C1 UPRQAYXZFHWKSB-AATRIKPKSA-N 0.000 claims description 5
• VFVLBIMRQSXFFH-FNORWQNLSA-N 5-[(e)-2-[5-[(dimethylamino)methyl]pyridin-2-yl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound N1=CC(CN(C)C)=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C VFVLBIMRQSXFFH-FNORWQNLSA-N 0.000 claims description 5
• RRHROYWZQZYXSU-UHFFFAOYSA-N 5-[2-(4-methoxyphenyl)ethyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC(OC)=CC=C1CCC1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C RRHROYWZQZYXSU-UHFFFAOYSA-N 0.000 claims description 5
• 206010061218 Inflammation Diseases 0.000 claims description 5
• 230000004054 inflammatory process Effects 0.000 claims description 5
• 230000009467 reduction Effects 0.000 claims description 5
• SNZVNMNNYCUJQI-SOFGYWHQSA-N tert-butyl 4-[(e)-4-[5-cyano-2-methyl-4-[(4-methyl-1h-indol-5-yl)amino]pyridin-3-yl]but-3-enyl]piperazine-1-carboxylate Chemical compound CC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1\C=C\CCN1CCN(C(=O)OC(C)(C)C)CC1 SNZVNMNNYCUJQI-SOFGYWHQSA-N 0.000 claims description 5
• 125000000335 thiazolyl group Chemical group 0.000 claims description 5
• 125000006585 (C6-C10) arylene group Chemical group 0.000 claims description 4
• PVYFCOHFBSTFLM-VOTSOKGWSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[2-(2-piperazin-1-ylethoxy)phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C1=CC=CC=C1OCCN1CCNCC1 PVYFCOHFBSTFLM-VOTSOKGWSA-N 0.000 claims description 4
• TUKOILYAIRACKC-VOTSOKGWSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[3-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CCOC1=CC=CC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=C1 TUKOILYAIRACKC-VOTSOKGWSA-N 0.000 claims description 4
• NFAJGQPKGVHQSQ-ONEGZZNKSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[5-[(4-methylpiperazin-1-yl)methyl]furan-3-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CC1=CC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=CO1 NFAJGQPKGVHQSQ-ONEGZZNKSA-N 0.000 claims description 4
• YOHRIASJHGRMLP-AATRIKPKSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[6-(piperazin-1-ylmethyl)pyridin-2-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(N=1)=CC=CC=1CN1CCNCC1 YOHRIASJHGRMLP-AATRIKPKSA-N 0.000 claims description 4
• NMRUWPRCOQSHGH-CMDGGOBGSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[6-(piperidin-1-ylmethyl)pyridin-2-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(N=1)=CC=CC=1CN1CCCCC1 NMRUWPRCOQSHGH-CMDGGOBGSA-N 0.000 claims description 4
• RDFXBYJUHGEYHA-VOTSOKGWSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[6-[(4-methylpiperazin-1-yl)methyl]pyridin-2-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CC1=CC=CC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=N1 RDFXBYJUHGEYHA-VOTSOKGWSA-N 0.000 claims description 4
• MPMGBIBECXBRBI-MDZDMXLPSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-phenylethenyl]-6-propan-2-ylpyridine-3-carbonitrile Chemical compound CC(C)C1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1\C=C\C1=CC=CC=C1 MPMGBIBECXBRBI-MDZDMXLPSA-N 0.000 claims description 4
• JSBPEIYUYLNLLN-BQYQJAHWSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-phenylethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C1=CC=CC=C1 JSBPEIYUYLNLLN-BQYQJAHWSA-N 0.000 claims description 4
• VPCNOHNBIYFVKC-BQYQJAHWSA-N 4-[(e)-2-[5-cyano-4-[(4-methyl-1h-indol-5-yl)amino]pyridin-3-yl]ethenyl]-n-phenylpiperidine-1-carboxamide Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(CC1)CCN1C(=O)NC1=CC=CC=C1 VPCNOHNBIYFVKC-BQYQJAHWSA-N 0.000 claims description 4
• PSBJYHVBFWJOOA-AATRIKPKSA-N 5-[(e)-2-[2-methoxy-5-[(4-methylpiperazin-1-yl)methyl]phenyl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=C(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)C(OC)=CC=C1CN1CCN(C)CC1 PSBJYHVBFWJOOA-AATRIKPKSA-N 0.000 claims description 4
• PFTJORZIXIECKA-UHFFFAOYSA-N 5-ethenyl-6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1C=C PFTJORZIXIECKA-UHFFFAOYSA-N 0.000 claims description 4
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 4
• LOIMCJURDAHHTR-SOFGYWHQSA-N Cc1ncc(C#N)c(Nc2ccc3[nH]ccc3c2C)c1\C=C\CCN1CCC(NC(=O)OC(C)(C)C)CC1 Chemical compound Cc1ncc(C#N)c(Nc2ccc3[nH]ccc3c2C)c1\C=C\CCN1CCC(NC(=O)OC(C)(C)C)CC1 LOIMCJURDAHHTR-SOFGYWHQSA-N 0.000 claims description 4
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
• 201000004681 Psoriasis Diseases 0.000 claims description 4
• 239000003638 chemical reducing agent Substances 0.000 claims description 4
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
• 125000005549 heteroarylene group Chemical group 0.000 claims description 4
• 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims description 4
• 208000018937 joint inflammation Diseases 0.000 claims description 4
• DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 4
• 210000000056 organ Anatomy 0.000 claims description 4
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• 125000004193 piperazinyl group Chemical group 0.000 claims description 4
• 125000003386 piperidinyl group Chemical group 0.000 claims description 4
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 3
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 3
• HETWGNHMXYNQPB-MDZDMXLPSA-N 4-(1h-indol-4-ylamino)-5-[(e)-2-phenylethenyl]pyridine-3-carbonitrile Chemical compound C=1C=CC=2NC=CC=2C=1NC=1C(C#N)=CN=CC=1\C=C\C1=CC=CC=C1 HETWGNHMXYNQPB-MDZDMXLPSA-N 0.000 claims description 3
• NCVZGIMYVRURRP-ZHACJKMWSA-N 4-(1h-indol-4-ylamino)-6-methyl-5-[(e)-2-phenylethenyl]pyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C=3C=CNC=3C=CC=2)=C1\C=C\C1=CC=CC=C1 NCVZGIMYVRURRP-ZHACJKMWSA-N 0.000 claims description 3
• SMJDWEZZDDDXJV-VQHVLOKHSA-N 4-(1h-indol-5-ylamino)-6-methyl-5-[(e)-2-phenylethenyl]pyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C=C3C=CNC3=CC=2)=C1\C=C\C1=CC=CC=C1 SMJDWEZZDDDXJV-VQHVLOKHSA-N 0.000 claims description 3
• DDIZHXIEUONSME-VOTSOKGWSA-N 4-(1h-indol-6-ylamino)-5-[(e)-2-phenylethenyl]pyridine-3-carbonitrile Chemical compound C=1C=C2C=CNC2=CC=1NC=1C(C#N)=CN=CC=1\C=C\C1=CC=CC=C1 DDIZHXIEUONSME-VOTSOKGWSA-N 0.000 claims description 3
• IPRVZHFGZBUQLP-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-(3-phenylpropyl)pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1CCCC1=CC=CC=C1 IPRVZHFGZBUQLP-UHFFFAOYSA-N 0.000 claims description 3
• VIFDLGHMGQUZHN-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-(4-piperazin-1-ylbutyl)pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1CCCCN1CCNCC1 VIFDLGHMGQUZHN-UHFFFAOYSA-N 0.000 claims description 3
• SRIXJFCFXOVOFD-FNORWQNLSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-(1,2,4-triazol-1-yl)ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\N1C=NC=N1 SRIXJFCFXOVOFD-FNORWQNLSA-N 0.000 claims description 3
• AJHIALAMYYAOQL-FMIVXFBMSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-(4-phenylphenyl)ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(C=C1)=CC=C1C1=CC=CC=C1 AJHIALAMYYAOQL-FMIVXFBMSA-N 0.000 claims description 3
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• HODJWAGLPIFAFX-HWKANZROSA-N 4-(1h-indol-5-ylamino)-5-[(e)-2-[5-[(4-methylpiperazin-1-yl)methyl]pyridin-2-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CC(C=N1)=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1 HODJWAGLPIFAFX-HWKANZROSA-N 0.000 claims description 2
• GLBDOEWDGNREFF-VOTSOKGWSA-N 4-(1h-indol-5-ylamino)-5-[(e)-2-phenylethenyl]pyridine-3-carbonitrile Chemical compound C=1C=C2NC=CC2=CC=1NC=1C(C#N)=CN=CC=1\C=C\C1=CC=CC=C1 GLBDOEWDGNREFF-VOTSOKGWSA-N 0.000 claims description 2
• CQRNLHYWYPDLME-FNORWQNLSA-N 4-[(2,4-dimethyl-1h-indol-5-yl)amino]-5-[(e)-2-[5-[(4-methylpiperazin-1-yl)methyl]pyridin-2-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CC(C=N1)=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC(C)=C2)C2=C1C CQRNLHYWYPDLME-FNORWQNLSA-N 0.000 claims description 2
• JBXKODTZBBUAQG-CMDGGOBGSA-N 4-[(2,4-dimethyl-1h-indol-5-yl)amino]-5-[(e)-2-phenylethenyl]pyridine-3-carbonitrile Chemical compound C=1C=C2NC(C)=CC2=C(C)C=1NC(C(=CN=C1)C#N)=C1\C=C\C1=CC=CC=C1 JBXKODTZBBUAQG-CMDGGOBGSA-N 0.000 claims description 2
• CLGKERUQODCNJI-BQYQJAHWSA-N 4-[(2-methyl-1h-indol-5-yl)amino]-5-[(e)-2-phenylethenyl]pyridine-3-carbonitrile Chemical compound C=1C=C2NC(C)=CC2=CC=1NC(C(=CN=C1)C#N)=C1\C=C\C1=CC=CC=C1 CLGKERUQODCNJI-BQYQJAHWSA-N 0.000 claims description 2
• POAUSQBRASMNQO-CMDGGOBGSA-N 4-[(4,7-dimethyl-1h-indol-5-yl)amino]-5-[(e)-2-phenylethenyl]pyridine-3-carbonitrile Chemical compound CC=1C=2C=CNC=2C(C)=CC=1NC(C(=CN=C1)C#N)=C1\C=C\C1=CC=CC=C1 POAUSQBRASMNQO-CMDGGOBGSA-N 0.000 claims description 2
• SBTUVVZTMJEJMZ-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-(2-phenylethyl)pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1CCC1=CC=CC=C1 SBTUVVZTMJEJMZ-UHFFFAOYSA-N 0.000 claims description 2
• GNRMJEZAFPCSFP-VOTSOKGWSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[2-methyl-5-[(4-methylpiperazin-1-yl)methyl]phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CC1=CC=C(C)C(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=C1 GNRMJEZAFPCSFP-VOTSOKGWSA-N 0.000 claims description 2
• GMQQMSKNSNVPOW-VOTSOKGWSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[3-(4-methylpiperazin-1-yl)sulfonylphenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1S(=O)(=O)C1=CC=CC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=C1 GMQQMSKNSNVPOW-VOTSOKGWSA-N 0.000 claims description 2
• KSLZXOKNNHDEQH-BQYQJAHWSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[3-[(4-pyrrolidin-1-ylpiperidin-1-yl)methyl]phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(C=1)=CC=CC=1CN(CC1)CCC1N1CCCC1 KSLZXOKNNHDEQH-BQYQJAHWSA-N 0.000 claims description 2
• MKEYDGKKBWRPJX-CMDGGOBGSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[3-[[2-(1-methylpyrrolidin-2-yl)ethylamino]methyl]phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound CN1CCCC1CCNCC1=CC=CC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=C1 MKEYDGKKBWRPJX-CMDGGOBGSA-N 0.000 claims description 2
• PEDXJGLVPJEZIK-QPJJXVBHSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[4-(2-pyrrolidin-1-ylethoxy)phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(C=C1)=CC=C1OCCN1CCCC1 PEDXJGLVPJEZIK-QPJJXVBHSA-N 0.000 claims description 2
• ZYGJWMUFFJZCFH-CMDGGOBGSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[4-(pyrrolidin-1-ylmethyl)phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(C=C1)=CC=C1CN1CCCC1 ZYGJWMUFFJZCFH-CMDGGOBGSA-N 0.000 claims description 2
• WHZFOBBBFYAYSL-BQYQJAHWSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[6-[(4-propan-2-ylpiperazin-1-yl)methyl]pyridin-2-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(C(C)C)CCN1CC1=CC=CC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=N1 WHZFOBBBFYAYSL-BQYQJAHWSA-N 0.000 claims description 2
• ZOCFPDBDIAIDCB-CMDGGOBGSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[6-[[2-(1-methylpyrrolidin-2-yl)ethylamino]methyl]pyridin-2-yl]ethenyl]pyridine-3-carbonitrile Chemical compound CN1CCCC1CCNCC1=CC=CC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=N1 ZOCFPDBDIAIDCB-CMDGGOBGSA-N 0.000 claims description 2
• OWGSYBDGJDKKHD-AATRIKPKSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-3-(4-phenylpiperazin-1-yl)prop-1-enyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CN(CC1)CCN1C1=CC=CC=C1 OWGSYBDGJDKKHD-AATRIKPKSA-N 0.000 claims description 2
• UQMWAUWHYVGIQS-WEVVVXLNSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-3-phenylprop-1-enyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CC1=CC=CC=C1 UQMWAUWHYVGIQS-WEVVVXLNSA-N 0.000 claims description 2
• QHFSWNIUUDZMSD-SNAWJCMRSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-3-pyrrolidin-1-ylprop-1-enyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CN1CCCC1 QHFSWNIUUDZMSD-SNAWJCMRSA-N 0.000 claims description 2
• UZHPHLWTNWZGRX-DUXPYHPUSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-4-morpholin-4-ylbut-1-enyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CCN1CCOCC1 UZHPHLWTNWZGRX-DUXPYHPUSA-N 0.000 claims description 2
• BUCGAQTZOOCIRW-DUXPYHPUSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-4-piperazin-1-ylbut-1-enyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CCN1CCNCC1 BUCGAQTZOOCIRW-DUXPYHPUSA-N 0.000 claims description 2
• QPOFNLCOWXWKRN-XVNBXDOJSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-4-piperidin-1-ylbut-1-enyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CCN1CCCCC1 QPOFNLCOWXWKRN-XVNBXDOJSA-N 0.000 claims description 2
• XHHYVFRQYUOODP-HWKANZROSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-5-morpholin-4-ylpent-1-enyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CCCN1CCOCC1 XHHYVFRQYUOODP-HWKANZROSA-N 0.000 claims description 2
• JSBPEIYUYLNLLN-FPLPWBNLSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(z)-2-phenylethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C/C1=CC=CC=C1 JSBPEIYUYLNLLN-FPLPWBNLSA-N 0.000 claims description 2
• AAFSXMVSVDLQQR-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[1-(1-methylpiperidine-4-carbonyl)-3,6-dihydro-2h-pyridin-4-yl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCC1C(=O)N1CC=C(C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)CC1 AAFSXMVSVDLQQR-UHFFFAOYSA-N 0.000 claims description 2
• ZFUWPVUVZGCICT-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[2-(4-phenylphenyl)ethyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1CCC(C=C1)=CC=C1C1=CC=CC=C1 ZFUWPVUVZGCICT-UHFFFAOYSA-N 0.000 claims description 2
• ZGVOFDPURVLPPJ-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[2-[4-(4-methylpiperazine-1-carbonyl)phenyl]ethyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1C(=O)C(C=C1)=CC=C1CCC1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C ZGVOFDPURVLPPJ-UHFFFAOYSA-N 0.000 claims description 2
• LNFKYEODTBKJLI-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[2-[4-(pyrrolidin-1-ylmethyl)phenyl]ethyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1CCC(C=C1)=CC=C1CN1CCCC1 LNFKYEODTBKJLI-UHFFFAOYSA-N 0.000 claims description 2
• HKBPNCLXXAODOZ-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[4-(4-methylpiperazin-1-yl)butyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CCCCC1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C HKBPNCLXXAODOZ-UHFFFAOYSA-N 0.000 claims description 2
• LABCSMNNXLSFPG-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-prop-1-en-2-ylpyridine-3-carbonitrile Chemical compound CC(=C)C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C LABCSMNNXLSFPG-UHFFFAOYSA-N 0.000 claims description 2
• FNZNXXYVWMRNAP-BQYQJAHWSA-N 4-[(4-methyl-1h-indol-5-yl)oxy]-5-[(e)-2-phenylethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1OC(C(=CN=C1)C#N)=C1\C=C\C1=CC=CC=C1 FNZNXXYVWMRNAP-BQYQJAHWSA-N 0.000 claims description 2
• RRWBGTISDGLEEB-QPJJXVBHSA-N 4-[(e)-2-[5-cyano-4-[(4-methyl-1h-indol-5-yl)amino]pyridin-3-yl]ethenyl]benzoic acid Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C1=CC=C(C(O)=O)C=C1 RRWBGTISDGLEEB-QPJJXVBHSA-N 0.000 claims description 2
• DQGXZJOMYLWAKM-BQYQJAHWSA-N 5-[(e)-2-(2-methoxyphenyl)ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound COC1=CC=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C DQGXZJOMYLWAKM-BQYQJAHWSA-N 0.000 claims description 2
• WYTOOCRBIYHQMA-GQCTYLIASA-N 5-[(e)-2-(3,4-dimethoxyphenyl)ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C WYTOOCRBIYHQMA-GQCTYLIASA-N 0.000 claims description 2
• JHSOAROIYKSHKX-VOTSOKGWSA-N 5-[(e)-2-(3-methoxyphenyl)ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound COC1=CC=CC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=C1 JHSOAROIYKSHKX-VOTSOKGWSA-N 0.000 claims description 2
• QPEFBDJDTOXTHX-BQYQJAHWSA-N 5-[(e)-2-(3-methoxyphenyl)ethenyl]-6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound COC1=CC=CC(\C=C\C=2C(=C(C#N)C=NC=2C)NC=2C(=C3C=CNC3=CC=2)C)=C1 QPEFBDJDTOXTHX-BQYQJAHWSA-N 0.000 claims description 2
• UICBGEORGNHIEI-ZHACJKMWSA-N 5-[(e)-2-(4-butylphenyl)ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC(CCCC)=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C UICBGEORGNHIEI-ZHACJKMWSA-N 0.000 claims description 2
• FCTOLTLXRRFHDZ-QPJJXVBHSA-N 5-[(e)-2-(4-ethoxyphenyl)ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC(OCC)=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C FCTOLTLXRRFHDZ-QPJJXVBHSA-N 0.000 claims description 2
• KHVIPMFUGNMWJU-GORDUTHDSA-N 5-[(e)-2-(4-fluorophenyl)ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C1=CC=C(F)C=C1 KHVIPMFUGNMWJU-GORDUTHDSA-N 0.000 claims description 2
• SWZXKBUPFISEFY-ZZXKWVIFSA-N 5-[(e)-2-(4-methoxyphenyl)ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC(OC)=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C SWZXKBUPFISEFY-ZZXKWVIFSA-N 0.000 claims description 2
• LFYRXLOZMPBXPI-RMKNXTFCSA-N 5-[(e)-2-(4-methoxyphenyl)ethenyl]-6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC(OC)=CC=C1\C=C\C1=C(C)N=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C LFYRXLOZMPBXPI-RMKNXTFCSA-N 0.000 claims description 2
• MIDJIYLXYVKKRS-NSCUHMNNSA-N 5-[(e)-2-(5-bromopyridin-3-yl)ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C1=CN=CC(Br)=C1 MIDJIYLXYVKKRS-NSCUHMNNSA-N 0.000 claims description 2
• LYECBHRKFSSVCP-AATRIKPKSA-N 5-[(e)-2-(6-bromopyridin-2-yl)ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C1=CC=CC(Br)=N1 LYECBHRKFSSVCP-AATRIKPKSA-N 0.000 claims description 2
• VCTCVGUHZCCXKP-GQCTYLIASA-N 5-[(e)-2-[3,4-bis(2-methoxyethoxy)phenyl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=C(OCCOC)C(OCCOC)=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C VCTCVGUHZCCXKP-GQCTYLIASA-N 0.000 claims description 2
• VUHCYARQLVMXDW-CMDGGOBGSA-N 5-[(e)-2-[3-[[2-(dimethylamino)ethylamino]methyl]phenyl]ethenyl]-6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound CN(C)CCNCC1=CC=CC(\C=C\C=2C(=C(C#N)C=NC=2C)NC=2C(=C3C=CNC3=CC=2)C)=C1 VUHCYARQLVMXDW-CMDGGOBGSA-N 0.000 claims description 2
• MMFFLYVAVCPQHO-BQYQJAHWSA-N 5-[(e)-2-[3-[[4-(dimethylamino)piperidin-1-yl]methyl]phenyl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1CC(N(C)C)CCN1CC1=CC=CC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=C1 MMFFLYVAVCPQHO-BQYQJAHWSA-N 0.000 claims description 2
• UUHGGGTUIOLZMO-CMDGGOBGSA-N 5-[(e)-2-[3-[[4-(dimethylamino)piperidin-1-yl]methyl]phenyl]ethenyl]-6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1CC(N(C)C)CCN1CC1=CC=CC(\C=C\C=2C(=C(C#N)C=NC=2C)NC=2C(=C3C=CNC3=CC=2)C)=C1 UUHGGGTUIOLZMO-CMDGGOBGSA-N 0.000 claims description 2
• SQDTUYNFUIDUQL-GORDUTHDSA-N 5-[(e)-2-[4-(2-chloroethoxy)phenyl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C1=CC=C(OCCCl)C=C1 SQDTUYNFUIDUQL-GORDUTHDSA-N 0.000 claims description 2
• MHYYWVGEAUERFB-BQYQJAHWSA-N 5-[(e)-2-[4-(azetidin-1-ylmethyl)phenyl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(C=C1)=CC=C1CN1CCC1 MHYYWVGEAUERFB-BQYQJAHWSA-N 0.000 claims description 2
• UBCHLQSKNIYBQP-QPJJXVBHSA-N 5-[(e)-2-[4-(dimethylamino)phenyl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC(N(C)C)=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C UBCHLQSKNIYBQP-QPJJXVBHSA-N 0.000 claims description 2
• WQDPSDBGWWMDHU-CMDGGOBGSA-N 5-[(e)-2-[4-[(dimethylamino)methyl]phenyl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC(CN(C)C)=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C WQDPSDBGWWMDHU-CMDGGOBGSA-N 0.000 claims description 2
• SPORZXBJCKJUIT-FNORWQNLSA-N 5-[(e)-2-[5-[(4-methyl-1,4-diazepan-1-yl)methyl]pyridin-2-yl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1CN(C)CCCN1CC(C=N1)=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C SPORZXBJCKJUIT-FNORWQNLSA-N 0.000 claims description 2
• VLEXKLPWUMHBQI-FNORWQNLSA-N 5-[(e)-2-[5-[[4-(dimethylamino)piperidin-1-yl]methyl]pyridin-2-yl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1CC(N(C)C)CCN1CC(C=N1)=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C VLEXKLPWUMHBQI-FNORWQNLSA-N 0.000 claims description 2
• JQSHVCXAYSCCOJ-BQYQJAHWSA-N 5-[(e)-2-[6-[(4-methyl-1,4-diazepan-1-yl)methyl]pyridin-2-yl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1CN(C)CCCN1CC1=CC=CC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=N1 JQSHVCXAYSCCOJ-BQYQJAHWSA-N 0.000 claims description 2
• AASWXJPXICMWTF-BQYQJAHWSA-N 5-[(e)-2-[6-[[2-(dimethylamino)ethylamino]methyl]pyridin-2-yl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound CN(C)CCNCC1=CC=CC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=N1 AASWXJPXICMWTF-BQYQJAHWSA-N 0.000 claims description 2
• WUJFWMRQXPIJIN-AATRIKPKSA-N 5-[(e)-2-[6-[[4-(2-hydroxyethyl)piperazin-1-yl]methyl]pyridin-2-yl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(N=1)=CC=CC=1CN1CCN(CCO)CC1 WUJFWMRQXPIJIN-AATRIKPKSA-N 0.000 claims description 2
• TZLVNGQSHBVJDQ-BQYQJAHWSA-N 5-[(e)-2-cyclohexylethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C1CCCCC1 TZLVNGQSHBVJDQ-BQYQJAHWSA-N 0.000 claims description 2
• BGLHPPIIHCSAHO-NSCUHMNNSA-N 5-[(e)-3-(4-hydroxypiperidin-1-yl)prop-1-enyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CN1CCC(O)CC1 BGLHPPIIHCSAHO-NSCUHMNNSA-N 0.000 claims description 2
• SZJIXBKHTOPEKG-DUXPYHPUSA-N 5-[(e)-4-(4-aminopiperidin-1-yl)but-1-enyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CCN1CCC(N)CC1 SZJIXBKHTOPEKG-DUXPYHPUSA-N 0.000 claims description 2
• ZQTCWRKVJWJCMV-GQCTYLIASA-N 5-[(e)-4-(4-ethylsulfonylpiperazin-1-yl)but-1-enyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1CN(S(=O)(=O)CC)CCN1CC\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C ZQTCWRKVJWJCMV-GQCTYLIASA-N 0.000 claims description 2
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• KRMLZRDHQHQPJW-BQYQJAHWSA-N 6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[3-(4-methylpiperazin-1-yl)sulfonylphenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1S(=O)(=O)C1=CC=CC(\C=C\C=2C(=C(C#N)C=NC=2C)NC=2C(=C3C=CNC3=CC=2)C)=C1 KRMLZRDHQHQPJW-BQYQJAHWSA-N 0.000 claims description 2
• ULAKUCVAGLXVSC-CMDGGOBGSA-N 6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CC(C=C1)=CC=C1\C=C\C1=C(C)N=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C ULAKUCVAGLXVSC-CMDGGOBGSA-N 0.000 claims description 2
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• VBWJOMJNVZBWBF-HWKANZROSA-N 6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-4-piperazin-1-ylbut-1-enyl]pyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1\C=C\CCN1CCNCC1 VBWJOMJNVZBWBF-HWKANZROSA-N 0.000 claims description 2
• ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 2
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• HBQYPLPEQCUHDF-ZHACJKMWSA-N C(C)N(CC)CC1=CC=C(C=C1)/C=C/C=1C=NC=C(C#N)C1NC=1C(=C2C=CNC2=CC1)C Chemical compound C(C)N(CC)CC1=CC=C(C=C1)/C=C/C=1C=NC=C(C#N)C1NC=1C(=C2C=CNC2=CC1)C HBQYPLPEQCUHDF-ZHACJKMWSA-N 0.000 claims description 2
• MCHPPDWLOGNDSQ-UHFFFAOYSA-N C(C1=CC=CC=C1)N1CCC(=CC1)C=1C=NC=C(C1NC=1C(=C2C=CNC2=CC1)C)C#N Chemical compound C(C1=CC=CC=C1)N1CCC(=CC1)C=1C=NC=C(C1NC=1C(=C2C=CNC2=CC1)C)C#N MCHPPDWLOGNDSQ-UHFFFAOYSA-N 0.000 claims description 2
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• ISTKJAPYBNWIQV-UHFFFAOYSA-N CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C#N)C=CC1=C(N=CS1)C Chemical compound CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C#N)C=CC1=C(N=CS1)C ISTKJAPYBNWIQV-UHFFFAOYSA-N 0.000 claims description 2
• YUMBAWKWNFXIIW-UHFFFAOYSA-N CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C#N)C=CC1=CC=C(C=C1)CN1CCC(CC1)N1CCCC1 Chemical compound CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C#N)C=CC1=CC=C(C=C1)CN1CCC(CC1)N1CCCC1 YUMBAWKWNFXIIW-UHFFFAOYSA-N 0.000 claims description 2
• PYWBQRZCFGAKJH-CMDGGOBGSA-N CN(CCNCC1=CC=C(C=C1)/C=C/C=1C(=C(C=NC1)C#N)NC=1C(=C2C=CNC2=CC1)C)C Chemical compound CN(CCNCC1=CC=C(C=C1)/C=C/C=1C(=C(C=NC1)C#N)NC=1C(=C2C=CNC2=CC1)C)C PYWBQRZCFGAKJH-CMDGGOBGSA-N 0.000 claims description 2
• GNXRZANHKUNYTK-DUXPYHPUSA-N [(e)-4-[5-cyano-4-[(4-methyl-1h-indol-5-yl)amino]pyridin-3-yl]but-3-enyl] morpholine-4-carboxylate Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CCOC(=O)N1CCOCC1 GNXRZANHKUNYTK-DUXPYHPUSA-N 0.000 claims description 2
• 230000003213 activating effect Effects 0.000 claims description 2
• 125000004429 atom Chemical group 0.000 claims description 2
• 229910052796 boron Inorganic materials 0.000 claims description 2
• VNMDUFRQSQDPPI-GORDUTHDSA-N c1cc2[nH]ccc2c(C)c1Nc(c(cnc1)C#N)c1\C=C\c1ccc(Cl)cc1 Chemical compound c1cc2[nH]ccc2c(C)c1Nc(c(cnc1)C#N)c1\C=C\c1ccc(Cl)cc1 VNMDUFRQSQDPPI-GORDUTHDSA-N 0.000 claims description 2
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 2
• ZWBZQNYPJKYVSP-SOFGYWHQSA-N tert-butyl 4-[[6-[(e)-2-[5-cyano-4-[(4-methyl-1h-indol-5-yl)amino]pyridin-3-yl]ethenyl]pyridin-3-yl]methyl]piperazine-1-carboxylate Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(N=C1)=CC=C1CN1CCN(C(=O)OC(C)(C)C)CC1 ZWBZQNYPJKYVSP-SOFGYWHQSA-N 0.000 claims description 2
• QRWFJIXLAFQZFS-FNORWQNLSA-N tert-butyl n-[1-[(e)-4-[5-cyano-4-[(4-methyl-1h-indol-5-yl)amino]pyridin-3-yl]but-3-enyl]piperidin-4-yl]carbamate Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CCN1CCC(NC(=O)OC(C)(C)C)CC1 QRWFJIXLAFQZFS-FNORWQNLSA-N 0.000 claims description 2
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 2
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
• 239000003814 drug Substances 0.000 claims 2
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
• CYLPGUOQLPQWEF-AATRIKPKSA-N 2-[[6-[(E)-2-[5-cyano-4-[(4-methyl-1H-indol-5-yl)amino]pyridin-3-yl]ethenyl]pyridin-2-yl]methoxy]ethyl hydrogen sulfate Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C1=CC=CC(COCCOS(O)(=O)=O)=N1 CYLPGUOQLPQWEF-AATRIKPKSA-N 0.000 claims 1
• QWVDEJAEFAVUFV-AATRIKPKSA-N 3-[(e)-2-[5-cyano-4-[(4-methyl-1h-indol-5-yl)amino]pyridin-3-yl]ethenyl]benzenesulfonamide Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C1=CC=CC(S(N)(=O)=O)=C1 QWVDEJAEFAVUFV-AATRIKPKSA-N 0.000 claims 1
• OLHUPCIDRDIHRN-CMDGGOBGSA-N 4-[(1,4-dimethylindol-5-yl)amino]-5-[(e)-2-phenylethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2N(C)C=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C1=CC=CC=C1 OLHUPCIDRDIHRN-CMDGGOBGSA-N 0.000 claims 1
• TWSGSMGLEVFTEX-BQYQJAHWSA-N 4-[(1-methylindol-5-yl)amino]-5-[(e)-2-phenylethenyl]pyridine-3-carbonitrile Chemical compound C=1C=C2N(C)C=CC2=CC=1NC(C(=CN=C1)C#N)=C1\C=C\C1=CC=CC=C1 TWSGSMGLEVFTEX-BQYQJAHWSA-N 0.000 claims 1
• NTUWLGXBCQXNEM-CMDGGOBGSA-N 4-[(4-methyl-1H-indol-5-yl)amino]-5-[(E)-2-[6-[(2-pyridin-2-ylethylamino)methyl]pyridin-2-yl]ethenyl]pyridine-3-carbonitrile Chemical compound c1cc2[nH]ccc2c(C)c1Nc(c(cnc1)C#N)c1\C=C\c(n1)cccc1CNCCc1ccccn1 NTUWLGXBCQXNEM-CMDGGOBGSA-N 0.000 claims 1
• GTDRXVHZELZVIQ-UHFFFAOYSA-N 4-[(4-methyl-1H-indol-5-yl)amino]-5-[(E)-2-[6-[(2-pyridin-3-ylethylamino)methyl]pyridin-2-yl]ethenyl]pyridine-3-carbonitrile Chemical compound CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C=CC1=NC(=CC=C1)CNCCC=1C=NC=CC1)C#N GTDRXVHZELZVIQ-UHFFFAOYSA-N 0.000 claims 1
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• WLDYAJMABHWMAG-SNAWJCMRSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-(1-propan-2-ylsulfonylpiperidin-4-yl)ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(S(=O)(=O)C(C)C)CCC1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C WLDYAJMABHWMAG-SNAWJCMRSA-N 0.000 claims 1
• JENPOADHHDMPGA-BQYQJAHWSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-(2-methylphenyl)ethenyl]pyridine-3-carbonitrile Chemical compound CC1=CC=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C JENPOADHHDMPGA-BQYQJAHWSA-N 0.000 claims 1
• UDPITYZQIVOTOD-CMDGGOBGSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-(3-piperidin-1-ylsulfonylphenyl)ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(C=1)=CC=CC=1S(=O)(=O)N1CCCCC1 UDPITYZQIVOTOD-CMDGGOBGSA-N 0.000 claims 1
• YXVARNRQCDABTC-VMPITWQZSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-(4-piperidin-1-ylsulfonylphenyl)ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(C=C1)=CC=C1S(=O)(=O)N1CCCCC1 YXVARNRQCDABTC-VMPITWQZSA-N 0.000 claims 1
• SONJXLIPDOXRGA-QPJJXVBHSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-(4-pyrrolidin-1-ylsulfonylphenyl)ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(C=C1)=CC=C1S(=O)(=O)N1CCCC1 SONJXLIPDOXRGA-QPJJXVBHSA-N 0.000 claims 1
• GJIHZDZOVHMYJS-BQYQJAHWSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[2-[(4-methylpiperazin-1-yl)methyl]phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CC1=CC=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C GJIHZDZOVHMYJS-BQYQJAHWSA-N 0.000 claims 1
• WWCLYPRMFVGSKN-SNAWJCMRSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[2-[(4-pyrrolidin-1-ylpiperidin-1-yl)methyl]-1,3-thiazol-4-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(N=1)=CSC=1CN(CC1)CCC1N1CCCC1 WWCLYPRMFVGSKN-SNAWJCMRSA-N 0.000 claims 1
• FLZQAEWJXRMKKK-CMDGGOBGSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[3-(4-piperidin-1-ylpiperidin-1-yl)sulfonylphenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(C=1)=CC=CC=1S(=O)(=O)N(CC1)CCC1N1CCCCC1 FLZQAEWJXRMKKK-CMDGGOBGSA-N 0.000 claims 1
• FPSGCBWWRUZTIV-AATRIKPKSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[3-(morpholin-4-ylmethyl)phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(C=1)=CC=CC=1CN1CCOCC1 FPSGCBWWRUZTIV-AATRIKPKSA-N 0.000 claims 1
• VKWRGMLRFOFLFQ-CMDGGOBGSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[3-(piperidin-1-ylmethyl)phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(C=1)=CC=CC=1CN1CCCCC1 VKWRGMLRFOFLFQ-CMDGGOBGSA-N 0.000 claims 1
• LFZROBFCNBQQTL-CMDGGOBGSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[3-(piperidin-1-ylsulfonylmethyl)phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(C=1)=CC=CC=1CS(=O)(=O)N1CCCCC1 LFZROBFCNBQQTL-CMDGGOBGSA-N 0.000 claims 1
• MGEVRDHVEDBHCP-BQYQJAHWSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[3-(pyrrolidin-1-ylsulfonylmethyl)phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(C=1)=CC=CC=1CS(=O)(=O)N1CCCC1 MGEVRDHVEDBHCP-BQYQJAHWSA-N 0.000 claims 1
• SMFZYCIKFUDNDM-AATRIKPKSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[3-[(2-morpholin-4-ylethylamino)methyl]phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(C=1)=CC=CC=1CNCCN1CCOCC1 SMFZYCIKFUDNDM-AATRIKPKSA-N 0.000 claims 1
• XOTNYFMXYDWFEU-VOTSOKGWSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[3-[(4-methylpiperazin-1-yl)sulfonylmethyl]phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1S(=O)(=O)CC1=CC=CC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=C1 XOTNYFMXYDWFEU-VOTSOKGWSA-N 0.000 claims 1
• QCURSJVBNWYAHF-BQYQJAHWSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[3-[(4-propan-2-ylpiperazin-1-yl)methyl]phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(C(C)C)CCN1CC1=CC=CC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=C1 QCURSJVBNWYAHF-BQYQJAHWSA-N 0.000 claims 1
• WXEYWIXOJDRUIB-ZZXKWVIFSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[4-(4-methylpiperazin-1-yl)sulfonylphenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1S(=O)(=O)C(C=C1)=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C WXEYWIXOJDRUIB-ZZXKWVIFSA-N 0.000 claims 1
• XJYBZBREOWBYIA-VOTSOKGWSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[4-(morpholin-4-ylmethyl)phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(C=C1)=CC=C1CN1CCOCC1 XJYBZBREOWBYIA-VOTSOKGWSA-N 0.000 claims 1
• QPOLHFLMHUMBTE-MDZDMXLPSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[4-(piperidin-1-ylsulfonylmethyl)phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(C=C1)=CC=C1CS(=O)(=O)N1CCCCC1 QPOLHFLMHUMBTE-MDZDMXLPSA-N 0.000 claims 1
• FLMIJNLDLOBMDE-CMDGGOBGSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[4-(pyrrolidin-1-ylsulfonylmethyl)phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(C=C1)=CC=C1CS(=O)(=O)N1CCCC1 FLMIJNLDLOBMDE-CMDGGOBGSA-N 0.000 claims 1
• XITXIIZNOASLSJ-GORDUTHDSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[4-(trifluoromethyl)phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C1=CC=C(C(F)(F)F)C=C1 XITXIIZNOASLSJ-GORDUTHDSA-N 0.000 claims 1
• JXOZXQUEQQLZTN-VOTSOKGWSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[4-[(2-morpholin-4-ylethylamino)methyl]phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(C=C1)=CC=C1CNCCN1CCOCC1 JXOZXQUEQQLZTN-VOTSOKGWSA-N 0.000 claims 1
• BULRBXVUYAWIPG-VOTSOKGWSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[4-[(2-pyridin-4-ylethylamino)methyl]phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(C=C1)=CC=C1CNCCC1=CC=NC=C1 BULRBXVUYAWIPG-VOTSOKGWSA-N 0.000 claims 1
• AIDAWWYINVACMN-ZZXKWVIFSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[4-[(4-methylpiperazin-1-yl)methyl]-1,3-thiazol-2-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CC1=CSC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=N1 AIDAWWYINVACMN-ZZXKWVIFSA-N 0.000 claims 1
• PHDOQFYDQFLEMJ-BQYQJAHWSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[4-[(4-methylpiperazin-1-yl)sulfonylmethyl]phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1S(=O)(=O)CC(C=C1)=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C PHDOQFYDQFLEMJ-BQYQJAHWSA-N 0.000 claims 1
• UNBIVXWVYOCJAH-BQYQJAHWSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[4-[(4-methylsulfonylpiperazin-1-yl)methyl]phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(C=C1)=CC=C1CN1CCN(S(C)(=O)=O)CC1 UNBIVXWVYOCJAH-BQYQJAHWSA-N 0.000 claims 1
• FFUHTRYFYONUSL-CMDGGOBGSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[4-[(4-propan-2-ylpiperazin-1-yl)methyl]phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(C(C)C)CCN1CC(C=C1)=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C FFUHTRYFYONUSL-CMDGGOBGSA-N 0.000 claims 1
• QHYWKHISVYLMIN-MDZDMXLPSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[4-[(4-pyridin-2-ylpiperazin-1-yl)methyl]phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(C=C1)=CC=C1CN(CC1)CCN1C1=CC=CC=N1 QHYWKHISVYLMIN-MDZDMXLPSA-N 0.000 claims 1
• KVPCAWMJGFMDHN-HWKANZROSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[5-(morpholin-4-ylmethyl)pyridin-2-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(N=C1)=CC=C1CN1CCOCC1 KVPCAWMJGFMDHN-HWKANZROSA-N 0.000 claims 1
• FQUIZYRWNTVYLN-SOFGYWHQSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[5-(piperidin-1-ylmethyl)pyridin-2-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(N=C1)=CC=C1CN1CCCCC1 FQUIZYRWNTVYLN-SOFGYWHQSA-N 0.000 claims 1
• DEMACVJHJMZHTI-FNORWQNLSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[5-(pyrrolidin-1-ylmethyl)pyridin-2-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(N=C1)=CC=C1CN1CCCC1 DEMACVJHJMZHTI-FNORWQNLSA-N 0.000 claims 1
• JGFHZDVQLSDEFS-HWKANZROSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[5-(thiomorpholin-4-ylmethyl)pyridin-2-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(N=C1)=CC=C1CN1CCSCC1 JGFHZDVQLSDEFS-HWKANZROSA-N 0.000 claims 1
• UOGAHAPIUYKFMV-HWKANZROSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[5-[(2-morpholin-4-ylethylamino)methyl]pyridin-2-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(N=C1)=CC=C1CNCCN1CCOCC1 UOGAHAPIUYKFMV-HWKANZROSA-N 0.000 claims 1
• FBTANDSHASAMPT-FNORWQNLSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[5-[(2-pyridin-3-ylethylamino)methyl]pyridin-2-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(N=C1)=CC=C1CNCCC1=CC=CN=C1 FBTANDSHASAMPT-FNORWQNLSA-N 0.000 claims 1
• VVIIQMPWRMLPQN-GQCTYLIASA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[5-[(3-morpholin-4-ylpropylamino)methyl]pyridin-2-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(N=C1)=CC=C1CNCCCN1CCOCC1 VVIIQMPWRMLPQN-GQCTYLIASA-N 0.000 claims 1
• HWWWZUWNASXKFZ-ONEGZZNKSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[5-[(4-methylpiperazin-1-yl)methyl]pyridin-3-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CC1=CN=CC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=C1 HWWWZUWNASXKFZ-ONEGZZNKSA-N 0.000 claims 1
• SWZGRWKHOORLKH-ONEGZZNKSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[5-[(4-methylpiperazin-1-yl)methyl]thiophen-3-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CC1=CC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=CS1 SWZGRWKHOORLKH-ONEGZZNKSA-N 0.000 claims 1
• MDQFYUBKWMFJKL-FNORWQNLSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[5-[(4-propan-2-ylpiperazin-1-yl)methyl]pyridin-2-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(C(C)C)CCN1CC(C=N1)=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C MDQFYUBKWMFJKL-FNORWQNLSA-N 0.000 claims 1
• XHCRQLXAKDZJHC-FNORWQNLSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[5-[(4-pyrrolidin-1-ylpiperidin-1-yl)methyl]pyridin-2-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(N=C1)=CC=C1CN(CC1)CCC1N1CCCC1 XHCRQLXAKDZJHC-FNORWQNLSA-N 0.000 claims 1
• OTAYLIJEELQHMS-ONEGZZNKSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[5-[2-(4-methylpiperazin-1-yl)ethoxy]pyridin-3-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CCOC1=CN=CC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=C1 OTAYLIJEELQHMS-ONEGZZNKSA-N 0.000 claims 1
• MOUHBEYNCKDLCR-ONEGZZNKSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[5-[2-[(1-methylpiperidin-4-yl)amino]ethoxy]pyridin-3-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCC1NCCOC1=CN=CC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=C1 MOUHBEYNCKDLCR-ONEGZZNKSA-N 0.000 claims 1
• RTASKUYJDHESDG-SNAWJCMRSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[5-[2-[(1-propan-2-ylpiperidin-4-yl)amino]ethoxy]pyridin-3-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(C(C)C)CCC1NCCOC1=CN=CC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=C1 RTASKUYJDHESDG-SNAWJCMRSA-N 0.000 claims 1
• MRWPMELQBWWJBU-SNAWJCMRSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[5-[2-[(1-propylpiperidin-4-yl)amino]ethoxy]pyridin-3-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(CCC)CCC1NCCOC1=CN=CC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=C1 MRWPMELQBWWJBU-SNAWJCMRSA-N 0.000 claims 1
• IJFOYKRTLGSDIY-SNAWJCMRSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[5-[2-[[1-(2-methylpropyl)piperidin-4-yl]amino]ethoxy]pyridin-3-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(CC(C)C)CCC1NCCOC1=CN=CC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=C1 IJFOYKRTLGSDIY-SNAWJCMRSA-N 0.000 claims 1
• JSEFRYMUQPHVER-SOFGYWHQSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[5-[[2-(1-methylpyrrolidin-2-yl)ethylamino]methyl]pyridin-2-yl]ethenyl]pyridine-3-carbonitrile Chemical compound CN1CCCC1CCNCC(C=N1)=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C JSEFRYMUQPHVER-SOFGYWHQSA-N 0.000 claims 1
• JIEYEAZFFZTWMS-SOFGYWHQSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[5-[[3-(2-oxopyrrolidin-1-yl)propylamino]methyl]pyridin-2-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(N=C1)=CC=C1CNCCCN1CCCC1=O JIEYEAZFFZTWMS-SOFGYWHQSA-N 0.000 claims 1
• LGGPJQQJTOCGDY-FNORWQNLSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[6-(2-piperidin-1-ylethylamino)pyridin-3-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(C=N1)=CC=C1NCCN1CCCCC1 LGGPJQQJTOCGDY-FNORWQNLSA-N 0.000 claims 1
• WALDOGJQTYJBFG-AATRIKPKSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[6-(morpholin-4-ylmethyl)pyridin-2-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(N=1)=CC=CC=1CN1CCOCC1 WALDOGJQTYJBFG-AATRIKPKSA-N 0.000 claims 1
• AMZGHEDJISAUOX-AATRIKPKSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[6-(thiomorpholin-4-ylmethyl)pyridin-2-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(N=1)=CC=CC=1CN1CCSCC1 AMZGHEDJISAUOX-AATRIKPKSA-N 0.000 claims 1
• YDOHJFWQVJKNBS-AATRIKPKSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[6-[(2-morpholin-4-ylethylamino)methyl]pyridin-2-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(N=1)=CC=CC=1CNCCN1CCOCC1 YDOHJFWQVJKNBS-AATRIKPKSA-N 0.000 claims 1
• ZZINMPJFEOGPEP-AATRIKPKSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[6-[(2-pyridin-4-ylethylamino)methyl]pyridin-2-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(N=1)=CC=CC=1CNCCC1=CC=NC=C1 ZZINMPJFEOGPEP-AATRIKPKSA-N 0.000 claims 1
• UTCVIQCKEYBYBV-VOTSOKGWSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[6-[(3-morpholin-4-ylpropylamino)methyl]pyridin-2-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(N=1)=CC=CC=1CNCCCN1CCOCC1 UTCVIQCKEYBYBV-VOTSOKGWSA-N 0.000 claims 1
• YBIYFYAUFOCSEH-HWKANZROSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[6-[(4-methylpiperazin-1-yl)methyl]pyridin-3-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CC(N=C1)=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C YBIYFYAUFOCSEH-HWKANZROSA-N 0.000 claims 1
• OZBWHIIGUJDFSV-AATRIKPKSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[6-[(4-morpholin-4-ylpiperidin-1-yl)methyl]pyridin-2-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(N=1)=CC=CC=1CN(CC1)CCC1N1CCOCC1 OZBWHIIGUJDFSV-AATRIKPKSA-N 0.000 claims 1
• BSVNIAMOWYYSDW-BQYQJAHWSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[6-[(4-pyrrolidin-1-ylpiperidin-1-yl)methyl]pyridin-2-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(N=1)=CC=CC=1CN(CC1)CCC1N1CCCC1 BSVNIAMOWYYSDW-BQYQJAHWSA-N 0.000 claims 1
• JCYANVAXWJXLBJ-CMDGGOBGSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[6-[[3-(2-oxopyrrolidin-1-yl)propylamino]methyl]pyridin-2-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(N=1)=CC=CC=1CNCCCN1CCCC1=O JCYANVAXWJXLBJ-CMDGGOBGSA-N 0.000 claims 1
• KCUVHAOVOXILQA-NSCUHMNNSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-3-(2-morpholin-4-ylethylamino)prop-1-enyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CNCCN1CCOCC1 KCUVHAOVOXILQA-NSCUHMNNSA-N 0.000 claims 1
• MWKQDYOZWRAWMS-NSCUHMNNSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-3-morpholin-4-ylprop-1-enyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CN1CCOCC1 MWKQDYOZWRAWMS-NSCUHMNNSA-N 0.000 claims 1
• MODWLWDUUDGOEB-NSCUHMNNSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-3-piperazin-1-ylprop-1-enyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CN1CCNCC1 MODWLWDUUDGOEB-NSCUHMNNSA-N 0.000 claims 1
• LOLIGEKXJXAKFQ-AATRIKPKSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-3-piperidin-1-ylprop-1-enyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CN1CCCCC1 LOLIGEKXJXAKFQ-AATRIKPKSA-N 0.000 claims 1
• COOZRRUJSWPFHC-HWKANZROSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-4-(4-methylpiperazin-1-yl)but-1-enyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CC\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C COOZRRUJSWPFHC-HWKANZROSA-N 0.000 claims 1
• SUMGTNPLBQXBDN-HWKANZROSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-4-(4-methylsulfonylpiperazin-1-yl)but-1-enyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CCN1CCN(S(C)(=O)=O)CC1 SUMGTNPLBQXBDN-HWKANZROSA-N 0.000 claims 1
• CPGBKOVXKSMSKV-DUXPYHPUSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-4-(4-morpholin-4-ylpiperidin-1-yl)but-1-enyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CCN(CC1)CCC1N1CCOCC1 CPGBKOVXKSMSKV-DUXPYHPUSA-N 0.000 claims 1
• BDJSJCPWFZBQRA-FNORWQNLSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-4-(4-phenylpiperazin-1-yl)but-1-enyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CCN(CC1)CCN1C1=CC=CC=C1 BDJSJCPWFZBQRA-FNORWQNLSA-N 0.000 claims 1
• MOJGUBLPDOMBJL-WEVVVXLNSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-4-(4-phenylpiperidin-1-yl)but-1-enyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CCN(CC1)CCC1C1=CC=CC=C1 MOJGUBLPDOMBJL-WEVVVXLNSA-N 0.000 claims 1
• HAYBNIARWRGYIC-GQCTYLIASA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-4-(4-propan-2-ylsulfonylpiperazin-1-yl)but-1-enyl]pyridine-3-carbonitrile Chemical compound C1CN(S(=O)(=O)C(C)C)CCN1CC\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C HAYBNIARWRGYIC-GQCTYLIASA-N 0.000 claims 1
• YXMRHIYWYCHKLM-QHHAFSJGSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-4-[4-(pyrrolidine-1-carbonyl)piperidin-1-yl]but-1-enyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CCN(CC1)CCC1C(=O)N1CCCC1 YXMRHIYWYCHKLM-QHHAFSJGSA-N 0.000 claims 1
• SVXRJJMIHITVJJ-QHHAFSJGSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-4-pyrrolidin-1-ylbut-1-enyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CCN1CCCC1 SVXRJJMIHITVJJ-QHHAFSJGSA-N 0.000 claims 1
• LBDMJMNVJZNONC-GQCTYLIASA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-5-(4-methylpiperazin-1-yl)pent-1-enyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CCC\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C LBDMJMNVJZNONC-GQCTYLIASA-N 0.000 claims 1
• IFLKFPIAJMOXTG-HWKANZROSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-5-piperazin-1-ylpent-1-enyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CCCN1CCNCC1 IFLKFPIAJMOXTG-HWKANZROSA-N 0.000 claims 1
• KIAJUGUFTMKTNB-XBXARRHUSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-5-piperidin-1-ylpent-1-enyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CCCN1CCCCC1 KIAJUGUFTMKTNB-XBXARRHUSA-N 0.000 claims 1
• XBLOMGDUUHWILK-XVNBXDOJSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-5-pyrrolidin-1-ylpent-1-enyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CCCN1CCCC1 XBLOMGDUUHWILK-XVNBXDOJSA-N 0.000 claims 1
• SUPGHANJFXUBTJ-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[1-(2-phenylethyl)-3,6-dihydro-2h-pyridin-4-yl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(CC1)=CCN1CCC1=CC=CC=C1 SUPGHANJFXUBTJ-UHFFFAOYSA-N 0.000 claims 1
• OCPRMRJZPAHBIV-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[1-(pyrrolidine-3-carbonyl)-3,6-dihydro-2h-pyridin-4-yl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(CC1)=CCN1C(=O)C1CCNC1 OCPRMRJZPAHBIV-UHFFFAOYSA-N 0.000 claims 1
• ZUAPCNMKVRHHGV-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[1-[(1-methylpiperidin-4-yl)methyl]-3,6-dihydro-2h-pyridin-4-yl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCC1CN1CC=C(C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)CC1 ZUAPCNMKVRHHGV-UHFFFAOYSA-N 0.000 claims 1
• HNHSIUNGWAYYDV-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[2-[6-[(4-piperidin-1-ylpiperidin-1-yl)methyl]pyridin-2-yl]ethyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1CCC(N=1)=CC=CC=1CN(CC1)CCC1N1CCCCC1 HNHSIUNGWAYYDV-UHFFFAOYSA-N 0.000 claims 1
• FWIQFMHFJMEYPO-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[2-[6-[(4-pyrrolidin-1-ylpiperidin-1-yl)methyl]pyridin-2-yl]ethyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1CCC(N=1)=CC=CC=1CN(CC1)CCC1N1CCCC1 FWIQFMHFJMEYPO-UHFFFAOYSA-N 0.000 claims 1
• KAWMNMBJDDWUNT-VOTSOKGWSA-N 4-[(6-chloro-1h-indol-5-yl)amino]-5-[(e)-2-phenylethenyl]pyridine-3-carbonitrile Chemical compound ClC1=CC=2NC=CC=2C=C1NC(C(=CN=C1)C#N)=C1\C=C\C1=CC=CC=C1 KAWMNMBJDDWUNT-VOTSOKGWSA-N 0.000 claims 1
• SVMGWLYENDWTOO-GQCTYLIASA-N 4-[(7-chloro-4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[5-[(4-methylpiperazin-1-yl)methyl]pyridin-2-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CC(C=N1)=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC(Cl)=C(NC=C2)C2=C1C SVMGWLYENDWTOO-GQCTYLIASA-N 0.000 claims 1
• PZQVFXKYWQOYJX-VOTSOKGWSA-N 4-[(7-chloro-4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[6-[(4-methylpiperazin-1-yl)methyl]pyridin-2-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CC1=CC=CC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=C(Cl)C=2)C)=N1 PZQVFXKYWQOYJX-VOTSOKGWSA-N 0.000 claims 1
• JNHIVFKZCQPBAR-CMDGGOBGSA-N 4-[(7-chloro-4-methyl-1h-indol-5-yl)amino]-6-methyl-5-[(e)-2-phenylethenyl]pyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=C(Cl)C=2)C)=C1\C=C\C1=CC=CC=C1 JNHIVFKZCQPBAR-CMDGGOBGSA-N 0.000 claims 1
• WIMTWVOAYCSJHC-RMKNXTFCSA-N 4-[(e)-2-[5-cyano-4-[(4-methyl-1h-indol-5-yl)amino]pyridin-3-yl]ethenyl]-n,n-diethylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N(CC)CC)=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C WIMTWVOAYCSJHC-RMKNXTFCSA-N 0.000 claims 1
• OOLJOHRMOKSYKO-QPJJXVBHSA-N 4-[(e)-2-[5-cyano-4-[(4-methyl-1h-indol-5-yl)amino]pyridin-3-yl]ethenyl]-n,n-dimethylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C OOLJOHRMOKSYKO-QPJJXVBHSA-N 0.000 claims 1
• MCHMAFDKRZTSDC-RMKNXTFCSA-N 4-[(e)-2-[5-cyano-4-[(4-methyl-1h-indol-5-yl)amino]pyridin-3-yl]ethenyl]-n,n-dipropylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N(CCC)CCC)=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C MCHMAFDKRZTSDC-RMKNXTFCSA-N 0.000 claims 1
• BTFQHCKJTLZZRE-GORDUTHDSA-N 4-[(e)-2-[5-cyano-4-[(4-methyl-1h-indol-5-yl)amino]pyridin-3-yl]ethenyl]benzenesulfonamide Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C1=CC=C(S(N)(=O)=O)C=C1 BTFQHCKJTLZZRE-GORDUTHDSA-N 0.000 claims 1
• IXCRWOJIHRXWSN-BQYQJAHWSA-N 4-[1h-indol-5-yl(methyl)amino]-5-[(e)-2-phenylethenyl]pyridine-3-carbonitrile Chemical compound C=1C=C2NC=CC2=CC=1N(C)C(C(=CN=C1)C#N)=C1\C=C\C1=CC=CC=C1 IXCRWOJIHRXWSN-BQYQJAHWSA-N 0.000 claims 1
• XOOCGCLVROAEKB-UHFFFAOYSA-N 4-[5-cyano-4-[(4-methyl-1h-indol-5-yl)amino]pyridin-3-yl]-n-ethyl-3,6-dihydro-2h-pyridine-1-carboxamide Chemical compound C1N(C(=O)NCC)CCC(C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=C1 XOOCGCLVROAEKB-UHFFFAOYSA-N 0.000 claims 1
• LGHZBAZNASMMFL-UHFFFAOYSA-N 5-(1-acetyl-3,6-dihydro-2h-pyridin-4-yl)-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1N(C(=O)C)CCC(C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=C1 LGHZBAZNASMMFL-UHFFFAOYSA-N 0.000 claims 1
• PZLSUIJNWJPJTM-SNAWJCMRSA-N 5-[(1e)-buta-1,3-dienyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(\C=C\C=C)C=NC=C1C#N PZLSUIJNWJPJTM-SNAWJCMRSA-N 0.000 claims 1
• BZLBLERQDQMBBK-BQYQJAHWSA-N 5-[(e)-2-(1-benzoylpiperidin-4-yl)ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(CC1)CCN1C(=O)C1=CC=CC=C1 BZLBLERQDQMBBK-BQYQJAHWSA-N 0.000 claims 1
• LQZYFHRRMLABSU-CMDGGOBGSA-N 5-[(e)-2-(2-ethylphenyl)ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound CCC1=CC=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C LQZYFHRRMLABSU-CMDGGOBGSA-N 0.000 claims 1
• FVORXZIFPSHSRU-AATRIKPKSA-N 5-[(e)-2-(3-formylphenyl)ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C1=CC=CC(C=O)=C1 FVORXZIFPSHSRU-AATRIKPKSA-N 0.000 claims 1
• NWYIZEWBIOMESV-VOTSOKGWSA-N 5-[(e)-2-(3-formylphenyl)ethenyl]-6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1\C=C\C1=CC=CC(C=O)=C1 NWYIZEWBIOMESV-VOTSOKGWSA-N 0.000 claims 1
• HTVSNNDJDMAESV-BQYQJAHWSA-N 5-[(e)-2-(4-benzylmorpholin-2-yl)ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(OCC1)CN1CC1=CC=CC=C1 HTVSNNDJDMAESV-BQYQJAHWSA-N 0.000 claims 1
• ZALUBVAZDXRDHI-BQYQJAHWSA-N 5-[(e)-2-(4-formylphenyl)ethenyl]-6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1\C=C\C1=CC=C(C=O)C=C1 ZALUBVAZDXRDHI-BQYQJAHWSA-N 0.000 claims 1
• KAFUVGSKZJYGOV-ONEGZZNKSA-N 5-[(e)-2-(5-methoxypyridin-3-yl)ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound COC1=CN=CC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=C1 KAFUVGSKZJYGOV-ONEGZZNKSA-N 0.000 claims 1
• IOIGKOCDHPMRDW-BQYQJAHWSA-N 5-[(e)-2-[1-(benzenesulfonyl)piperidin-4-yl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(CC1)CCN1S(=O)(=O)C1=CC=CC=C1 IOIGKOCDHPMRDW-BQYQJAHWSA-N 0.000 claims 1
• CVDNFKGKPRUMQB-NSCUHMNNSA-N 5-[(e)-2-[2-(hydroxymethyl)-1,3-thiazol-4-yl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C1=CSC(CO)=N1 CVDNFKGKPRUMQB-NSCUHMNNSA-N 0.000 claims 1
• RRDRIOLXAWYPMH-SNAWJCMRSA-N 5-[(e)-2-[2-[[4-(dimethylamino)piperidin-1-yl]methyl]-1,3-thiazol-4-yl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1CC(N(C)C)CCN1CC1=NC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=CS1 RRDRIOLXAWYPMH-SNAWJCMRSA-N 0.000 claims 1
• GFFNYOSNGTXLSJ-BQYQJAHWSA-N 5-[(e)-2-[2-ethyl-5-[(4-methylpiperazin-1-yl)methyl]phenyl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=C(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)C(CC)=CC=C1CN1CCN(C)CC1 GFFNYOSNGTXLSJ-BQYQJAHWSA-N 0.000 claims 1
• BFDGENJWDOTZQZ-CMDGGOBGSA-N 5-[(e)-2-[2-ethyl-5-[(4-methylpiperazin-1-yl)methyl]phenyl]ethenyl]-6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=C(\C=C\C=2C(=C(C#N)C=NC=2C)NC=2C(=C3C=CNC3=CC=2)C)C(CC)=CC=C1CN1CCN(C)CC1 BFDGENJWDOTZQZ-CMDGGOBGSA-N 0.000 claims 1
• CBYLEUOLHUNXBU-ZHACJKMWSA-N 5-[(e)-2-[3-(diethylaminomethyl)phenyl]ethenyl]-6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound CCN(CC)CC1=CC=CC(\C=C\C=2C(=C(C#N)C=NC=2C)NC=2C(=C3C=CNC3=CC=2)C)=C1 CBYLEUOLHUNXBU-ZHACJKMWSA-N 0.000 claims 1
• VEDNOXRGJVASTQ-BQYQJAHWSA-N 5-[(e)-2-[3-[(2-ethoxyethylamino)methyl]phenyl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound CCOCCNCC1=CC=CC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=C1 VEDNOXRGJVASTQ-BQYQJAHWSA-N 0.000 claims 1
• PUHVFMHICYZPFY-MDZDMXLPSA-N 5-[(e)-2-[3-[(3-ethoxypropylamino)methyl]phenyl]ethenyl]-6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound CCOCCCNCC1=CC=CC(\C=C\C=2C(=C(C#N)C=NC=2C)NC=2C(=C3C=CNC3=CC=2)C)=C1 PUHVFMHICYZPFY-MDZDMXLPSA-N 0.000 claims 1
• DWGPEJYRXFXARC-VOTSOKGWSA-N 5-[(e)-2-[3-[(3-hydroxypyrrolidin-1-yl)methyl]phenyl]ethenyl]-6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1\C=C\C(C=1)=CC=CC=1CN1CCC(O)C1 DWGPEJYRXFXARC-VOTSOKGWSA-N 0.000 claims 1
• UJBAYCIQPBHHBB-AATRIKPKSA-N 5-[(e)-2-[3-[(4-hydroxypiperidin-1-yl)methyl]phenyl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(C=1)=CC=CC=1CN1CCC(O)CC1 UJBAYCIQPBHHBB-AATRIKPKSA-N 0.000 claims 1
• ZPXFHRBJZSZASA-BQYQJAHWSA-N 5-[(e)-2-[3-[(4-methyl-1,4-diazepan-1-yl)methyl]phenyl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1CN(C)CCCN1CC1=CC=CC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=C1 ZPXFHRBJZSZASA-BQYQJAHWSA-N 0.000 claims 1
• PFXRVSMQCWTZCU-BQYQJAHWSA-N 5-[(e)-2-[3-[[2-(dimethylamino)ethylamino]methyl]phenyl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound CN(C)CCNCC1=CC=CC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=C1 PFXRVSMQCWTZCU-BQYQJAHWSA-N 0.000 claims 1
• CPZLSJBXNHMFET-MDZDMXLPSA-N 5-[(e)-2-[3-[[3-(dimethylamino)propylamino]methyl]phenyl]ethenyl]-6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound CN(C)CCCNCC1=CC=CC(\C=C\C=2C(=C(C#N)C=NC=2C)NC=2C(=C3C=CNC3=CC=2)C)=C1 CPZLSJBXNHMFET-MDZDMXLPSA-N 0.000 claims 1
• JPINQKLMVKTGTL-AATRIKPKSA-N 5-[(e)-2-[3-[[4-(2-hydroxyethyl)piperazin-1-yl]methyl]phenyl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(C=1)=CC=CC=1CN1CCN(CCO)CC1 JPINQKLMVKTGTL-AATRIKPKSA-N 0.000 claims 1
• NEPKDQKAVIMOTJ-VOTSOKGWSA-N 5-[(e)-2-[3-[[4-(2-hydroxyethyl)piperazin-1-yl]methyl]phenyl]ethenyl]-6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1\C=C\C(C=1)=CC=CC=1CN1CCN(CCO)CC1 NEPKDQKAVIMOTJ-VOTSOKGWSA-N 0.000 claims 1
• GFLGIZVUCFIBRB-BQYQJAHWSA-N 5-[(e)-2-[4-[(2-methoxyethylamino)methyl]phenyl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC(CNCCOC)=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C GFLGIZVUCFIBRB-BQYQJAHWSA-N 0.000 claims 1
• IZQJJKRJOBKIJN-VOTSOKGWSA-N 5-[(e)-2-[4-[(3-hydroxypyrrolidin-1-yl)methyl]phenyl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(C=C1)=CC=C1CN1CCC(O)C1 IZQJJKRJOBKIJN-VOTSOKGWSA-N 0.000 claims 1
• AYWUQHYZZPXJNR-VAWYXSNFSA-N 5-[(e)-2-[4-[(4-cyclopentylpiperazin-1-yl)methyl]phenyl]ethenyl]-6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1\C=C\C(C=C1)=CC=C1CN(CC1)CCN1C1CCCC1 AYWUQHYZZPXJNR-VAWYXSNFSA-N 0.000 claims 1
• CLENZPTUQALSKC-VOTSOKGWSA-N 5-[(e)-2-[4-[(4-hydroxypiperidin-1-yl)methyl]phenyl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(C=C1)=CC=C1CN1CCC(O)CC1 CLENZPTUQALSKC-VOTSOKGWSA-N 0.000 claims 1
• AGNLBCUGBVFJNH-VOTSOKGWSA-N 5-[(e)-2-[4-[(azetidin-3-ylamino)methyl]phenyl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(C=C1)=CC=C1CNC1CNC1 AGNLBCUGBVFJNH-VOTSOKGWSA-N 0.000 claims 1
• QQTCQPRRLZECIK-VAWYXSNFSA-N 5-[(e)-2-[4-[[1h-indol-3-ylmethyl(methyl)amino]methyl]phenyl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=C2NC=CC2=C(C)C(NC2=C(C#N)C=NC=C2/C=C/C2=CC=C(C=C2)CN(CC=2C3=CC=CC=C3NC=2)C)=C1 QQTCQPRRLZECIK-VAWYXSNFSA-N 0.000 claims 1
• OFAWVNTWBAYIQM-VOTSOKGWSA-N 5-[(e)-2-[4-[[4-(2-hydroxyethyl)piperazin-1-yl]methyl]phenyl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(C=C1)=CC=C1CN1CCN(CCO)CC1 OFAWVNTWBAYIQM-VOTSOKGWSA-N 0.000 claims 1
• XEHZTUCPROUDNJ-CMDGGOBGSA-N 5-[(e)-2-[4-[[4-(dimethylamino)piperidin-1-yl]methyl]phenyl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1CC(N(C)C)CCN1CC(C=C1)=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C XEHZTUCPROUDNJ-CMDGGOBGSA-N 0.000 claims 1
• CDGWFYAVASCGKN-MDZDMXLPSA-N 5-[(e)-2-[4-[[4-(dimethylamino)piperidin-1-yl]methyl]phenyl]ethenyl]-6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1CC(N(C)C)CCN1CC(C=C1)=CC=C1\C=C\C1=C(C)N=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C CDGWFYAVASCGKN-MDZDMXLPSA-N 0.000 claims 1
• OSHUNISXMHIJKT-NSCUHMNNSA-N 5-[(e)-2-[5-(2-aminoethoxy)pyridin-3-yl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C1=CN=CC(OCCN)=C1 OSHUNISXMHIJKT-NSCUHMNNSA-N 0.000 claims 1
• XOAVSTPPHHBYOZ-VQHVLOKHSA-N 5-[(e)-2-[5-(diethylaminomethyl)pyridin-2-yl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound N1=CC(CN(CC)CC)=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C XOAVSTPPHHBYOZ-VQHVLOKHSA-N 0.000 claims 1
• IVMIVGCWAIGMEC-AATRIKPKSA-N 5-[(e)-2-[5-(hydroxymethyl)pyridin-2-yl]ethenyl]-6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1\C=C\C1=CC=C(CO)C=N1 IVMIVGCWAIGMEC-AATRIKPKSA-N 0.000 claims 1
• RJDSZGHRIWRIMZ-FNORWQNLSA-N 5-[(e)-2-[5-[(2-ethoxyethylamino)methyl]pyridin-2-yl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound N1=CC(CNCCOCC)=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C RJDSZGHRIWRIMZ-FNORWQNLSA-N 0.000 claims 1
• DAQIKFLEHCFYPH-GQCTYLIASA-N 5-[(e)-2-[5-[(2-methoxyethylamino)methyl]pyridin-2-yl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound N1=CC(CNCCOC)=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C DAQIKFLEHCFYPH-GQCTYLIASA-N 0.000 claims 1
• KSCRYLZNEMMUOP-SOFGYWHQSA-N 5-[(e)-2-[5-[(3-ethoxypropylamino)methyl]pyridin-2-yl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound N1=CC(CNCCCOCC)=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C KSCRYLZNEMMUOP-SOFGYWHQSA-N 0.000 claims 1
• MCACOGVUYBGWIJ-HWKANZROSA-N 5-[(e)-2-[5-[(3-hydroxypyrrolidin-1-yl)methyl]pyridin-2-yl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(N=C1)=CC=C1CN1CCC(O)C1 MCACOGVUYBGWIJ-HWKANZROSA-N 0.000 claims 1
• SKGBENJJSTVJLC-VQHVLOKHSA-N 5-[(e)-2-[5-[(4-cyclopentylpiperazin-1-yl)methyl]pyridin-2-yl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(N=C1)=CC=C1CN(CC1)CCN1C1CCCC1 SKGBENJJSTVJLC-VQHVLOKHSA-N 0.000 claims 1
• UYICUHDKBPIZCB-HWKANZROSA-N 5-[(e)-2-[5-[(4-hydroxypiperidin-1-yl)methyl]pyridin-2-yl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(N=C1)=CC=C1CN1CCC(O)CC1 UYICUHDKBPIZCB-HWKANZROSA-N 0.000 claims 1
• YUEZLQGZBNONLF-AATRIKPKSA-N 5-[(e)-2-[5-[2-(2,2-dimethylpropylamino)ethoxy]pyridin-3-yl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C1=CN=CC(OCCNCC(C)(C)C)=C1 YUEZLQGZBNONLF-AATRIKPKSA-N 0.000 claims 1
• CRBGKGQMDAREJW-VOTSOKGWSA-N 5-[(e)-2-[5-[2-(azepan-1-yl)ethoxy]pyridin-3-yl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(C=1)=CN=CC=1OCCN1CCCCCC1 CRBGKGQMDAREJW-VOTSOKGWSA-N 0.000 claims 1
• RNTMPDULFIBYGT-AATRIKPKSA-N 5-[(e)-2-[5-[3-(dimethylamino)propoxy]pyridin-3-yl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound CN(C)CCCOC1=CN=CC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=C1 RNTMPDULFIBYGT-AATRIKPKSA-N 0.000 claims 1
• SHYQCIHVQAPFRP-VQHVLOKHSA-N 5-[(e)-2-[5-[[2-(azepan-1-yl)ethylamino]methyl]pyridin-2-yl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(N=C1)=CC=C1CNCCN1CCCCCC1 SHYQCIHVQAPFRP-VQHVLOKHSA-N 0.000 claims 1
• FFAAOBUUZRSQLI-MDZDMXLPSA-N 5-[(e)-2-[5-[[2-(azepan-1-yl)ethylamino]methyl]pyridin-2-yl]ethenyl]-6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1\C=C\C(N=C1)=CC=C1CNCCN1CCCCCC1 FFAAOBUUZRSQLI-MDZDMXLPSA-N 0.000 claims 1
• PVQGGYQUBYQUQM-FNORWQNLSA-N 5-[(e)-2-[5-[[2-(dimethylamino)ethylamino]methyl]pyridin-2-yl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound N1=CC(CNCCN(C)C)=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C PVQGGYQUBYQUQM-FNORWQNLSA-N 0.000 claims 1
• MURYVRVTQLJRBG-SOFGYWHQSA-N 5-[(e)-2-[5-[[3-(dimethylamino)propylamino]methyl]pyridin-2-yl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound N1=CC(CNCCCN(C)C)=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C MURYVRVTQLJRBG-SOFGYWHQSA-N 0.000 claims 1
• CMKJRKRMLVBWMM-CMDGGOBGSA-N 5-[(e)-2-[5-[[3-(dimethylamino)propylamino]methyl]pyridin-2-yl]ethenyl]-6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound N1=CC(CNCCCN(C)C)=CC=C1\C=C\C1=C(C)N=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C CMKJRKRMLVBWMM-CMDGGOBGSA-N 0.000 claims 1
• LPIJVXOQOOJCRR-HWKANZROSA-N 5-[(e)-2-[5-[[4-(2-hydroxyethyl)piperazin-1-yl]methyl]pyridin-2-yl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(N=C1)=CC=C1CN1CCN(CCO)CC1 LPIJVXOQOOJCRR-HWKANZROSA-N 0.000 claims 1
• XHPBRPFACZNPRQ-MDZDMXLPSA-N 5-[(e)-2-[6-(diethylaminomethyl)pyridin-2-yl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound CCN(CC)CC1=CC=CC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=N1 XHPBRPFACZNPRQ-MDZDMXLPSA-N 0.000 claims 1
• OMPFNQKROIXYOK-ZHACJKMWSA-N 5-[(e)-2-[6-(diethylaminomethyl)pyridin-2-yl]ethenyl]-6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound CCN(CC)CC1=CC=CC(\C=C\C=2C(=C(C#N)C=NC=2C)NC=2C(=C3C=CNC3=CC=2)C)=N1 OMPFNQKROIXYOK-ZHACJKMWSA-N 0.000 claims 1
• KLYSFBLXQCEGLE-VOTSOKGWSA-N 5-[(e)-2-[6-(hydroxymethyl)pyridin-2-yl]ethenyl]-6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1\C=C\C1=CC=CC(CO)=N1 KLYSFBLXQCEGLE-VOTSOKGWSA-N 0.000 claims 1
• OFPJHNAYGOZJLI-BQYQJAHWSA-N 5-[(e)-2-[6-[(2-ethoxyethylamino)methyl]pyridin-2-yl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound CCOCCNCC1=CC=CC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=N1 OFPJHNAYGOZJLI-BQYQJAHWSA-N 0.000 claims 1
• HQABGZSOARFEQR-CMDGGOBGSA-N 5-[(e)-2-[6-[(2-ethoxyethylamino)methyl]pyridin-2-yl]ethenyl]-6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound CCOCCNCC1=CC=CC(\C=C\C=2C(=C(C#N)C=NC=2C)NC=2C(=C3C=CNC3=CC=2)C)=N1 HQABGZSOARFEQR-CMDGGOBGSA-N 0.000 claims 1
• AZHZQWZIQCSEHF-VOTSOKGWSA-N 5-[(e)-2-[6-[(2-methoxyethylamino)methyl]pyridin-2-yl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound COCCNCC1=CC=CC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=N1 AZHZQWZIQCSEHF-VOTSOKGWSA-N 0.000 claims 1
• DOTITHQJPLBCGK-CMDGGOBGSA-N 5-[(e)-2-[6-[(3-ethoxypropylamino)methyl]pyridin-2-yl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound CCOCCCNCC1=CC=CC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=N1 DOTITHQJPLBCGK-CMDGGOBGSA-N 0.000 claims 1
• ZKQHWLOETKAUMM-AATRIKPKSA-N 5-[(e)-2-[6-[(3-hydroxypyrrolidin-1-yl)methyl]pyridin-2-yl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(N=1)=CC=CC=1CN1CCC(O)C1 ZKQHWLOETKAUMM-AATRIKPKSA-N 0.000 claims 1
• LDXSKTZBRWLBHB-MDZDMXLPSA-N 5-[(e)-2-[6-[(4-cyclopentylpiperazin-1-yl)methyl]pyridin-2-yl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(N=1)=CC=CC=1CN(CC1)CCN1C1CCCC1 LDXSKTZBRWLBHB-MDZDMXLPSA-N 0.000 claims 1
• JFURDLFHSFQXAW-ZHACJKMWSA-N 5-[(e)-2-[6-[(4-cyclopentylpiperazin-1-yl)methyl]pyridin-2-yl]ethenyl]-6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1\C=C\C(N=1)=CC=CC=1CN(CC1)CCN1C1CCCC1 JFURDLFHSFQXAW-ZHACJKMWSA-N 0.000 claims 1
• OXPLGRNOXPCLEB-AATRIKPKSA-N 5-[(e)-2-[6-[(4-hydroxypiperidin-1-yl)methyl]pyridin-2-yl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(N=1)=CC=CC=1CN1CCC(O)CC1 OXPLGRNOXPCLEB-AATRIKPKSA-N 0.000 claims 1
• LWRLDPXHLWJWQD-BQYQJAHWSA-N 5-[(e)-2-[6-[(dimethylamino)methyl]pyridin-2-yl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound CN(C)CC1=CC=CC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=N1 LWRLDPXHLWJWQD-BQYQJAHWSA-N 0.000 claims 1
• OMQHPZYHDAQKAQ-MDZDMXLPSA-N 5-[(e)-2-[6-[[2-(azepan-1-yl)ethylamino]methyl]pyridin-2-yl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(N=1)=CC=CC=1CNCCN1CCCCCC1 OMQHPZYHDAQKAQ-MDZDMXLPSA-N 0.000 claims 1
• CFVFCSXLFYFMFT-CMDGGOBGSA-N 5-[(e)-2-[6-[[3-(dimethylamino)propylamino]methyl]pyridin-2-yl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound CN(C)CCCNCC1=CC=CC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=N1 CFVFCSXLFYFMFT-CMDGGOBGSA-N 0.000 claims 1
• NINRYXWFHXFNOX-VOTSOKGWSA-N 5-[(e)-2-[6-[[4-(2-hydroxyethyl)piperazin-1-yl]methyl]pyridin-2-yl]ethenyl]-6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1\C=C\C(N=1)=CC=CC=1CN1CCN(CCO)CC1 NINRYXWFHXFNOX-VOTSOKGWSA-N 0.000 claims 1
• ICQQDVZUHPTFPS-BQYQJAHWSA-N 5-[(e)-2-[6-[[4-(dimethylamino)piperidin-1-yl]methyl]pyridin-2-yl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1CC(N(C)C)CCN1CC1=CC=CC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=N1 ICQQDVZUHPTFPS-BQYQJAHWSA-N 0.000 claims 1
• JWISNBUEXWWZBH-CMDGGOBGSA-N 5-[(e)-2-[6-[[4-(dimethylamino)piperidin-1-yl]methyl]pyridin-2-yl]ethenyl]-6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1CC(N(C)C)CCN1CC1=CC=CC(\C=C\C=2C(=C(C#N)C=NC=2C)NC=2C(=C3C=CNC3=CC=2)C)=N1 JWISNBUEXWWZBH-CMDGGOBGSA-N 0.000 claims 1
• WLHQSLXAYMTDTJ-QPJJXVBHSA-N 5-[(e)-3-(3,4-dihydro-1h-isoquinolin-2-yl)prop-1-enyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1CC2=CC=CC=C2CN1C/C=C/C(C=NC=C1C#N)=C1NC1=C(C)C(C=CN2)=C2C=C1 WLHQSLXAYMTDTJ-QPJJXVBHSA-N 0.000 claims 1
• XUDDPIKSCLCQKJ-NSCUHMNNSA-N 5-[(e)-3-(4-aminopiperidin-1-yl)prop-1-enyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CN1CCC(N)CC1 XUDDPIKSCLCQKJ-NSCUHMNNSA-N 0.000 claims 1
• WCFHRFMQBILNAF-NSCUHMNNSA-N 5-[(e)-3-aminoprop-1-enyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(\C=C\CN)C=NC=C1C#N WCFHRFMQBILNAF-NSCUHMNNSA-N 0.000 claims 1
• LWCCPIYUKXEVFE-NSCUHMNNSA-N 5-[(e)-3-imidazol-1-ylprop-1-enyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CN1C=CN=C1 LWCCPIYUKXEVFE-NSCUHMNNSA-N 0.000 claims 1
• IVNAWZAGFRROFH-GQCTYLIASA-N 5-[(e)-4-(1,3-dioxoisoindol-2-yl)but-1-enyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound O=C1C2=CC=CC=C2C(=O)N1CC/C=C/C(C=NC=C1C#N)=C1NC1=C(C)C(C=CN2)=C2C=C1 IVNAWZAGFRROFH-GQCTYLIASA-N 0.000 claims 1
• HFSXGAKDODZJBV-GORDUTHDSA-N 5-[(e)-4-(1,4-diazepan-1-yl)but-1-enyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CCN1CCCNCC1 HFSXGAKDODZJBV-GORDUTHDSA-N 0.000 claims 1
• HNRNONZUODAMHR-DUXPYHPUSA-N 5-[(e)-4-(2,5-diazabicyclo[2.2.1]heptan-2-yl)but-1-enyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CCN1C(CN2)CC2C1 HNRNONZUODAMHR-DUXPYHPUSA-N 0.000 claims 1
• NDPCMXFATSKLHE-DUXPYHPUSA-N 5-[(e)-4-(3-aminoazetidin-1-yl)but-1-enyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CCN1CC(N)C1 NDPCMXFATSKLHE-DUXPYHPUSA-N 0.000 claims 1
• KEBDGBLZUWTDQL-HWKANZROSA-N 5-[(e)-4-(4-acetylpiperazin-1-yl)but-1-enyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1CN(C(=O)C)CCN1CC\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C KEBDGBLZUWTDQL-HWKANZROSA-N 0.000 claims 1
• KRSQMQFKFCQXKG-DUXPYHPUSA-N 5-[(e)-4-(4-hydroxypiperidin-1-yl)but-1-enyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CCN1CCC(O)CC1 KRSQMQFKFCQXKG-DUXPYHPUSA-N 0.000 claims 1
• JMRDOCPDIXFWLY-HWKANZROSA-N 5-[(e)-4-(4-methoxypiperidin-1-yl)but-1-enyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1CC(OC)CCN1CC\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C JMRDOCPDIXFWLY-HWKANZROSA-N 0.000 claims 1
• KAJIDAUQCMSGGN-XQASTXFUSA-N 5-[(e)-4-[(3r)-3-aminopiperidin-1-yl]but-1-enyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CCN1CCC[C@@H](N)C1 KAJIDAUQCMSGGN-XQASTXFUSA-N 0.000 claims 1
• DNZGKSANTHABGF-NLJSWGTCSA-N 5-[(e)-4-[(3r)-3-aminopyrrolidin-1-yl]but-1-enyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CCN1CC[C@@H](N)C1 DNZGKSANTHABGF-NLJSWGTCSA-N 0.000 claims 1
• PQUHKNDRTYATRD-XQASTXFUSA-N 5-[(e)-4-[(3r)-3-hydroxypiperidin-1-yl]but-1-enyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CCN1CCC[C@@H](O)C1 PQUHKNDRTYATRD-XQASTXFUSA-N 0.000 claims 1
• KEUYDWVTHJQHIH-NLJSWGTCSA-N 5-[(e)-4-[(3r)-3-hydroxypyrrolidin-1-yl]but-1-enyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CCN1CC[C@@H](O)C1 KEUYDWVTHJQHIH-NLJSWGTCSA-N 0.000 claims 1
• KAJIDAUQCMSGGN-BFJGLSHQSA-N 5-[(e)-4-[(3s)-3-aminopiperidin-1-yl]but-1-enyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CCN1CCC[C@H](N)C1 KAJIDAUQCMSGGN-BFJGLSHQSA-N 0.000 claims 1
• DNZGKSANTHABGF-GVTIMSHASA-N 5-[(e)-4-[(3s)-3-aminopyrrolidin-1-yl]but-1-enyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CCN1CC[C@H](N)C1 DNZGKSANTHABGF-GVTIMSHASA-N 0.000 claims 1
• PQUHKNDRTYATRD-BFJGLSHQSA-N 5-[(e)-4-[(3s)-3-hydroxypiperidin-1-yl]but-1-enyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CCN1CCC[C@H](O)C1 PQUHKNDRTYATRD-BFJGLSHQSA-N 0.000 claims 1
• KEUYDWVTHJQHIH-GVTIMSHASA-N 5-[(e)-4-[(3s)-3-hydroxypyrrolidin-1-yl]but-1-enyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CCN1CC[C@H](O)C1 KEUYDWVTHJQHIH-GVTIMSHASA-N 0.000 claims 1
• GNTJQYWONXEJPV-FNORWQNLSA-N 5-[(e)-4-[4-(2,2-dimethylpropanoyl)piperazin-1-yl]but-1-enyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CCN1CCN(C(=O)C(C)(C)C)CC1 GNTJQYWONXEJPV-FNORWQNLSA-N 0.000 claims 1
• BSPJFZBMQCBCCJ-DUXPYHPUSA-N 5-[(e)-4-[4-(aminomethyl)piperidin-1-yl]but-1-enyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CCN1CCC(CN)CC1 BSPJFZBMQCBCCJ-DUXPYHPUSA-N 0.000 claims 1
• DOCCMHSNEKDEOV-FNORWQNLSA-N 5-[(e)-4-[4-(benzenesulfonyl)piperazin-1-yl]but-1-enyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CCN(CC1)CCN1S(=O)(=O)C1=CC=CC=C1 DOCCMHSNEKDEOV-FNORWQNLSA-N 0.000 claims 1
• CLAXUCQFRATVEQ-GQCTYLIASA-N 5-[(e)-4-[4-(dimethylamino)piperidin-1-yl]but-1-enyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1CC(N(C)C)CCN1CC\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C CLAXUCQFRATVEQ-GQCTYLIASA-N 0.000 claims 1
• IJYPXTWDRNLKMU-DUXPYHPUSA-N 5-[(e)-4-[4-(hydroxymethyl)piperidin-1-yl]but-1-enyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CCN1CCC(CO)CC1 IJYPXTWDRNLKMU-DUXPYHPUSA-N 0.000 claims 1
• GDEWTWLRSSWVEX-HWKANZROSA-N 5-[(e)-4-[4-(methylamino)piperidin-1-yl]but-1-enyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1CC(NC)CCN1CC\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C GDEWTWLRSSWVEX-HWKANZROSA-N 0.000 claims 1
• XUTVDDSSDRVGAE-DUXPYHPUSA-N 5-[(e)-4-aminobut-1-enyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(\C=C\CCN)C=NC=C1C#N XUTVDDSSDRVGAE-DUXPYHPUSA-N 0.000 claims 1
• LCLDOTQNYVMPRQ-HWKANZROSA-N 5-[(e)-5-(4-hydroxypiperidin-1-yl)pent-1-enyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CCCN1CCC(O)CC1 LCLDOTQNYVMPRQ-HWKANZROSA-N 0.000 claims 1
• DJYABBJHTDRUBN-UHFFFAOYSA-N 5-[1-(2-amino-2-methylpropanoyl)-3,6-dihydro-2h-pyridin-4-yl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C1=CCN(C(=O)C(C)(C)N)CC1 DJYABBJHTDRUBN-UHFFFAOYSA-N 0.000 claims 1
• XRBYFRXKMOPFKK-UHFFFAOYSA-N 5-[1-(benzenesulfonyl)-3,6-dihydro-2h-pyridin-4-yl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(CC1)=CCN1S(=O)(=O)C1=CC=CC=C1 XRBYFRXKMOPFKK-UHFFFAOYSA-N 0.000 claims 1
• UKTOKIOAKFNZKO-HSZRJFAPSA-N 5-[1-[(2r)-2-amino-3-methylbutanoyl]-3,6-dihydro-2h-pyridin-4-yl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1N(C(=O)[C@H](N)C(C)C)CCC(C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=C1 UKTOKIOAKFNZKO-HSZRJFAPSA-N 0.000 claims 1
• RDUGMJKOLIUGRY-UHFFFAOYSA-N 5-[2-[6-(hydroxymethyl)pyridin-2-yl]ethyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1CCC1=CC=CC(CO)=N1 RDUGMJKOLIUGRY-UHFFFAOYSA-N 0.000 claims 1
• DZFDSLOBMXYLRX-UHFFFAOYSA-N 5-[2-[6-[[4-(2-hydroxyethyl)piperazin-1-yl]methyl]pyridin-2-yl]ethyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1CCC(N=1)=CC=CC=1CN1CCN(CCO)CC1 DZFDSLOBMXYLRX-UHFFFAOYSA-N 0.000 claims 1
• OGWUWPJRLWZLAS-UHFFFAOYSA-N 5-[2-[6-[[4-(dimethylamino)piperidin-1-yl]methyl]pyridin-2-yl]ethyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1CC(N(C)C)CCN1CC1=CC=CC(CCC=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=N1 OGWUWPJRLWZLAS-UHFFFAOYSA-N 0.000 claims 1
• VGXGNTUDKHFRIH-UHFFFAOYSA-N 6-ethyl-4-[(4-methyl-1h-indol-5-yl)amino]-5-(2-phenylethyl)pyridine-3-carbonitrile Chemical compound CCC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1CCC1=CC=CC=C1 VGXGNTUDKHFRIH-UHFFFAOYSA-N 0.000 claims 1
• FESYGZLLMAMOSD-MDZDMXLPSA-N 6-ethyl-4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound CCC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1\C=C\C(C=C1)=CC=C1CN1CCN(C)CC1 FESYGZLLMAMOSD-MDZDMXLPSA-N 0.000 claims 1
• CVCDHPFTSJNSAW-UHFFFAOYSA-N 6-methyl-4-[(4-methyl-1H-indol-5-yl)amino]-5-[(E)-2-[2-methyl-4-(4-methylpiperazine-1-carbonyl)phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=C(C=C(C=C1)C(=O)N1CCN(CC1)C)C CVCDHPFTSJNSAW-UHFFFAOYSA-N 0.000 claims 1
• XRXANZJSYXEDNS-UHFFFAOYSA-N 6-methyl-4-[(4-methyl-1H-indol-5-yl)amino]-5-[(E)-2-pyridin-4-ylethenyl]pyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(=C1C=CC1=CC=NC=C1)NC=1C(=C2C=CNC2=CC1)C XRXANZJSYXEDNS-UHFFFAOYSA-N 0.000 claims 1
• XSORNMJEIAQEKP-UHFFFAOYSA-N 6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]-5-(2-pyridin-2-ylethyl)pyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1CCC1=CC=CC=N1 XSORNMJEIAQEKP-UHFFFAOYSA-N 0.000 claims 1
• LIBYFWGPQJFMMW-MDZDMXLPSA-N 6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-(3-piperidin-1-ylsulfonylphenyl)ethenyl]pyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1\C=C\C(C=1)=CC=CC=1S(=O)(=O)N1CCCCC1 LIBYFWGPQJFMMW-MDZDMXLPSA-N 0.000 claims 1
• UVUMDKAWNBACHR-CMDGGOBGSA-N 6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-(3-pyrrolidin-1-ylsulfonylphenyl)ethenyl]pyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1\C=C\C(C=1)=CC=CC=1S(=O)(=O)N1CCCC1 UVUMDKAWNBACHR-CMDGGOBGSA-N 0.000 claims 1
• SMLLPOGPGMEJFX-QPJJXVBHSA-N 6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl]pyridine-3-carbonitrile Chemical compound N1=CSC(\C=C\C=2C(=C(C#N)C=NC=2C)NC=2C(=C3C=CNC3=CC=2)C)=C1C SMLLPOGPGMEJFX-QPJJXVBHSA-N 0.000 claims 1
• JBSXQSFCUDTPCT-JXMROGBWSA-N 6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-(4-pyrrolidin-1-ylsulfonylphenyl)ethenyl]pyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1\C=C\C(C=C1)=CC=C1S(=O)(=O)N1CCCC1 JBSXQSFCUDTPCT-JXMROGBWSA-N 0.000 claims 1
• BCPPYUCSCCHXEP-BQYQJAHWSA-N 6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[2-methyl-4-[(4-methylpiperazin-1-yl)methyl]phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CC(C=C1C)=CC=C1\C=C\C1=C(C)N=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C BCPPYUCSCCHXEP-BQYQJAHWSA-N 0.000 claims 1
• OLVHVRWZUJMRCE-MDZDMXLPSA-N 6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[3-(piperidin-1-ylmethyl)phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1\C=C\C(C=1)=CC=CC=1CN1CCCCC1 OLVHVRWZUJMRCE-MDZDMXLPSA-N 0.000 claims 1
• UCMQFYFEELLVFT-MDZDMXLPSA-N 6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[3-(piperidin-1-ylsulfonylmethyl)phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1\C=C\C(C=1)=CC=CC=1CS(=O)(=O)N1CCCCC1 UCMQFYFEELLVFT-MDZDMXLPSA-N 0.000 claims 1
• PTZCRBJXVHTMHN-CMDGGOBGSA-N 6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[3-(pyrrolidin-1-ylsulfonylmethyl)phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1\C=C\C(C=1)=CC=CC=1CS(=O)(=O)N1CCCC1 PTZCRBJXVHTMHN-CMDGGOBGSA-N 0.000 claims 1
• HWXYGJJLWKICNX-BQYQJAHWSA-N 6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[3-[(3-morpholin-4-ylpropylamino)methyl]phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1\C=C\C(C=1)=CC=CC=1CNCCCN1CCOCC1 HWXYGJJLWKICNX-BQYQJAHWSA-N 0.000 claims 1
• ZQKCTEOSJBBWBB-BQYQJAHWSA-N 6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[3-[(4-methylpiperazin-1-yl)sulfonylmethyl]phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1S(=O)(=O)CC1=CC=CC(\C=C\C=2C(=C(C#N)C=NC=2C)NC=2C(=C3C=CNC3=CC=2)C)=C1 ZQKCTEOSJBBWBB-BQYQJAHWSA-N 0.000 claims 1
• XUAWHQOGUHAHKQ-VOTSOKGWSA-N 6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[3-[(4-morpholin-4-ylpiperidin-1-yl)methyl]phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1\C=C\C(C=1)=CC=CC=1CN(CC1)CCC1N1CCOCC1 XUAWHQOGUHAHKQ-VOTSOKGWSA-N 0.000 claims 1
• ZVHIPNQRQACBGL-CMDGGOBGSA-N 6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[3-[(4-pyrrolidin-1-ylpiperidin-1-yl)methyl]phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1\C=C\C(C=1)=CC=CC=1CN(CC1)CCC1N1CCCC1 ZVHIPNQRQACBGL-CMDGGOBGSA-N 0.000 claims 1
• BOBBYUSYHORXQS-RMKNXTFCSA-N 6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[4-(4-methylpiperazin-1-yl)sulfonylphenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1S(=O)(=O)C(C=C1)=CC=C1\C=C\C1=C(C)N=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C BOBBYUSYHORXQS-RMKNXTFCSA-N 0.000 claims 1
• PRBLDJTXXPWZML-ZHACJKMWSA-N 6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[4-(piperidin-1-ylmethyl)phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1\C=C\C(C=C1)=CC=C1CN1CCCCC1 PRBLDJTXXPWZML-ZHACJKMWSA-N 0.000 claims 1
• MDMLZBQTUJQVPH-MDZDMXLPSA-N 6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[4-(pyrrolidin-1-ylsulfonylmethyl)phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1\C=C\C(C=C1)=CC=C1CS(=O)(=O)N1CCCC1 MDMLZBQTUJQVPH-MDZDMXLPSA-N 0.000 claims 1
• NIAJEEMQNUPFJB-CMDGGOBGSA-N 6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[4-[(4-methylpiperazin-1-yl)sulfonylmethyl]phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1S(=O)(=O)CC(C=C1)=CC=C1\C=C\C1=C(C)N=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C NIAJEEMQNUPFJB-CMDGGOBGSA-N 0.000 claims 1
• NQMBFDOHLMJFMB-MDZDMXLPSA-N 6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[4-[(4-pyrrolidin-1-ylpiperidin-1-yl)methyl]phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1\C=C\C(C=C1)=CC=C1CN(CC1)CCC1N1CCCC1 NQMBFDOHLMJFMB-MDZDMXLPSA-N 0.000 claims 1
• YWIONXHDZMLFRW-AATRIKPKSA-N 6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[5-(2-pyrrolidin-1-ylethoxy)pyridin-3-yl]ethenyl]pyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1\C=C\C(C=1)=CN=CC=1OCCN1CCCC1 YWIONXHDZMLFRW-AATRIKPKSA-N 0.000 claims 1
• LYINFTDFQMKAEX-CMDGGOBGSA-N 6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[5-[(2-pyridin-2-ylethylamino)methyl]pyridin-2-yl]ethenyl]pyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1\C=C\C(N=C1)=CC=C1CNCCC1=CC=CC=N1 LYINFTDFQMKAEX-CMDGGOBGSA-N 0.000 claims 1
• JGWDGUAZEIXWLG-BQYQJAHWSA-N 6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[5-[(4-pyrrolidin-1-ylpiperidin-1-yl)methyl]pyridin-2-yl]ethenyl]pyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1\C=C\C(N=C1)=CC=C1CN(CC1)CCC1N1CCCC1 JGWDGUAZEIXWLG-BQYQJAHWSA-N 0.000 claims 1
• XWNMABCRFUZTGL-CMDGGOBGSA-N 6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[5-[[2-(1-methylpyrrolidin-2-yl)ethylamino]methyl]pyridin-2-yl]ethenyl]pyridine-3-carbonitrile Chemical compound CN1CCCC1CCNCC(C=N1)=CC=C1\C=C\C1=C(C)N=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C XWNMABCRFUZTGL-CMDGGOBGSA-N 0.000 claims 1
• GXTFNLBRGNPFQO-MDZDMXLPSA-N 6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[6-[(2-pyridin-2-ylethylamino)methyl]pyridin-2-yl]ethenyl]pyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1\C=C\C(N=1)=CC=CC=1CNCCC1=CC=CC=N1 GXTFNLBRGNPFQO-MDZDMXLPSA-N 0.000 claims 1
• XBAOCTVIKCKESJ-ONEGZZNKSA-N 6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-pyrazin-2-ylethenyl]pyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1\C=C\C1=CN=CC=N1 XBAOCTVIKCKESJ-ONEGZZNKSA-N 0.000 claims 1
• MWAHGRUIQHNHLB-VOTSOKGWSA-N 6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-pyridin-2-ylethenyl]pyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1\C=C\C1=CC=CC=N1 MWAHGRUIQHNHLB-VOTSOKGWSA-N 0.000 claims 1
• GZYIIRHCFMIKRC-UHFFFAOYSA-N 6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]-5-[2-(4-methylphenyl)ethyl]pyridine-3-carbonitrile Chemical compound C1=CC(C)=CC=C1CCC1=C(C)N=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C GZYIIRHCFMIKRC-UHFFFAOYSA-N 0.000 claims 1
• FBXWZLJPOYWXBS-UHFFFAOYSA-N 6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]-5-[2-[2-methyl-4-[(4-methylpiperazin-1-yl)methyl]phenyl]ethyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CC(C=C1C)=CC=C1CCC1=C(C)N=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C FBXWZLJPOYWXBS-UHFFFAOYSA-N 0.000 claims 1
• QQFQZWJORAQIPY-UHFFFAOYSA-N 6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]-5-[2-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]ethyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CC(C=C1)=CC=C1CCC1=C(C)N=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C QQFQZWJORAQIPY-UHFFFAOYSA-N 0.000 claims 1
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