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

5-alkyl/alcenyl-3-cyanopyridines en tant qu'inhibiteurs de kinase Download PDF

Info

Publication number: CA2709314A1
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

Application number

CA2709314A

Other languages

English (en)

Inventor

Lawrence Nathan Tumey

Diane Harris Boschelli

Niala Bhagirath

Joan Jowen Chen

Middleton Brawner Floyd, Jr.

Zhong Li

Chuansheng Niu

Jaechul Shim

Yan Wang

Yanong Daniel Wang

Biqi Wu

Clark N. Eid, Jr.

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Wyeth LLC

Original Assignee

Individual

Priority date (The priority date 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 date listed.)

2007-12-13

Filing date

2008-12-12

Publication date

2009-06-18

2008-12-12 Application filed by Individual filed Critical Individual

2009-06-18 Publication of CA2709314A1 publication Critical patent/CA2709314A1/fr

Status Abandoned legal-status Critical Current

Links

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
ZUCXCMPMMAYYRS-QPJJXVBHSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-(4-propoxyphenyl)ethenyl]pyridine-3-carbonitrile Chemical compound C1=CC(OCCC)=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C ZUCXCMPMMAYYRS-QPJJXVBHSA-N 0.000 claims description 3
DDVKURVSLBGSOS-CMDGGOBGSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[2-(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\C1=CC=CC=C1OCCN1CCCC1 DDVKURVSLBGSOS-CMDGGOBGSA-N 0.000 claims description 3
FJFFDARYCCTVRK-ONEGZZNKSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[2-[(4-methylpiperazin-1-yl)methyl]-1,3-thiazol-4-yl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CC1=NC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=CS1 FJFFDARYCCTVRK-ONEGZZNKSA-N 0.000 claims description 3
YAHQEFRFUBPDAT-BQYQJAHWSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[2-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CCOC1=CC=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C YAHQEFRFUBPDAT-BQYQJAHWSA-N 0.000 claims description 3
JAHZPHJVXCDNHO-VOTSOKGWSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[2-methyl-5-(4-methylpiperazine-1-carbonyl)phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(C)C(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=C1 JAHZPHJVXCDNHO-VOTSOKGWSA-N 0.000 claims description 3
IWZNOWDHBWUZLK-BQYQJAHWSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[3-(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=1)=CC=CC=1OCCN1CCCC1 IWZNOWDHBWUZLK-BQYQJAHWSA-N 0.000 claims description 3
BSXFBYYSEAPFKJ-VMPITWQZSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[4-(4-methylpiperazine-1-carbonyl)phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1C(=O)C(C=C1)=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C BSXFBYYSEAPFKJ-VMPITWQZSA-N 0.000 claims description 3
FHKKQNWDXIFLMF-VOTSOKGWSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[4-(piperazin-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=C1CN1CCNCC1 FHKKQNWDXIFLMF-VOTSOKGWSA-N 0.000 claims description 3
JVSULVHQOCWQHQ-ZZXKWVIFSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[4-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl]ethenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CCOC(C=C1)=CC=C1\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C JVSULVHQOCWQHQ-ZZXKWVIFSA-N 0.000 claims description 3
MDRIMBJNKSSQPG-HWKANZROSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[5-(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=C1)=CC=C1CN1CCNCC1 MDRIMBJNKSSQPG-HWKANZROSA-N 0.000 claims description 3
PBWBADGNVJJHFC-GQCTYLIASA-N 4-[(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=C(NC=C2)C2=C1C PBWBADGNVJJHFC-GQCTYLIASA-N 0.000 claims description 3
NDHZHSVRUCLNIU-AATRIKPKSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-pyridin-2-ylethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C1=CC=CC=N1 NDHZHSVRUCLNIU-AATRIKPKSA-N 0.000 claims description 3
RQVHOTCPICLKCR-NSCUHMNNSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-pyridin-4-ylethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C1=CC=NC=C1 RQVHOTCPICLKCR-NSCUHMNNSA-N 0.000 claims description 3
KADSBMDSVAYXRE-ONEGZZNKSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-3-(4-methylpiperazin-1-yl)prop-1-enyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1C\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C KADSBMDSVAYXRE-ONEGZZNKSA-N 0.000 claims description 3
DVVMJPTWLDQDTI-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[2-[5-[(4-methylpiperazin-1-yl)methyl]pyridin-2-yl]ethyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CC(C=N1)=CC=C1CCC1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C DVVMJPTWLDQDTI-UHFFFAOYSA-N 0.000 claims description 3
GOTCGCFQYSEZBA-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[3-(4-methylpiperazin-1-yl)propyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CCCC1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C GOTCGCFQYSEZBA-UHFFFAOYSA-N 0.000 claims description 3
QEQRMPXQCBZMSU-BQYQJAHWSA-N 4-[(7-chloro-4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-phenylethenyl]pyridine-3-carbonitrile Chemical compound C1=C(Cl)C=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C1=CC=CC=C1 QEQRMPXQCBZMSU-BQYQJAHWSA-N 0.000 claims description 3
CEZKOPFSESVPLR-UHFFFAOYSA-N 5-[(3,4-dimethoxyphenyl)methyl]-4-(1h-indol-4-ylamino)pyridine-3-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1CC1=CN=CC(C#N)=C1NC1=CC=CC2=C1C=CN2 CEZKOPFSESVPLR-UHFFFAOYSA-N 0.000 claims description 3
CRFCXGSXLCJBKY-UHFFFAOYSA-N 5-[(3,4-dimethoxyphenyl)methyl]-4-(1h-indol-5-ylamino)pyridine-3-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1CC1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1 CRFCXGSXLCJBKY-UHFFFAOYSA-N 0.000 claims description 3
KCIZMTAENFSKNK-SNAWJCMRSA-N 5-[(e)-2-(2-chloropyridin-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=CC=CN=C1Cl KCIZMTAENFSKNK-SNAWJCMRSA-N 0.000 claims description 3
OBXVDYPBMCLVEW-NSCUHMNNSA-N 5-[(e)-2-(2-chloropyridin-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=CC=NC(Cl)=C1 OBXVDYPBMCLVEW-NSCUHMNNSA-N 0.000 claims description 3
UBYKGUUITCIPSE-VOTSOKGWSA-N 5-[(e)-2-[2-methoxy-3-(piperazin-1-ylmethyl)phenyl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=C(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)C(OC)=C1CN1CCNCC1 UBYKGUUITCIPSE-VOTSOKGWSA-N 0.000 claims description 3
WDDVAVLWMWQQBQ-BQYQJAHWSA-N 5-[(e)-2-[2-methoxy-3-[(4-methylpiperazin-1-yl)methyl]phenyl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=C(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)C(OC)=C1CN1CCN(C)CC1 WDDVAVLWMWQQBQ-BQYQJAHWSA-N 0.000 claims description 3
KSMRTMFVFIYRHX-AATRIKPKSA-N 5-[(e)-2-[2-methoxy-4-(piperazin-1-ylmethyl)phenyl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C=1C=C(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)C(OC)=CC=1CN1CCNCC1 KSMRTMFVFIYRHX-AATRIKPKSA-N 0.000 claims description 3
HITLNOULVXHVOB-VOTSOKGWSA-N 5-[(e)-2-[2-methoxy-4-[(4-methylpiperazin-1-yl)methyl]phenyl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C=1C=C(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)C(OC)=CC=1CN1CCN(C)CC1 HITLNOULVXHVOB-VOTSOKGWSA-N 0.000 claims description 3
XZXCPMPENXYIQR-SNAWJCMRSA-N 5-[(e)-2-[2-methoxy-5-(piperazin-1-ylmethyl)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=C1CN1CCNCC1 XZXCPMPENXYIQR-SNAWJCMRSA-N 0.000 claims description 3
UXGKLLRQDMLRNB-MDZDMXLPSA-N 5-[(e)-2-[3-(diethylaminomethyl)phenyl]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)=C1 UXGKLLRQDMLRNB-MDZDMXLPSA-N 0.000 claims description 3
MIYSHTSTBSYTND-HWKANZROSA-N 5-[(e)-2-[3-methoxy-4-(piperazin-1-ylmethyl)phenyl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound COC1=CC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=CC=C1CN1CCNCC1 MIYSHTSTBSYTND-HWKANZROSA-N 0.000 claims description 3
DHAWAYZWVJESOH-GQCTYLIASA-N 5-[(e)-2-[3-methoxy-4-[(4-methylpiperazin-1-yl)methyl]phenyl]ethenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound COC1=CC(\C=C\C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=CC=C1CN1CCN(C)CC1 DHAWAYZWVJESOH-GQCTYLIASA-N 0.000 claims description 3
NZCYZBTXSFTTCS-HWKANZROSA-N 5-[(e)-2-[5-(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=C(CO)C=N1 NZCYZBTXSFTTCS-HWKANZROSA-N 0.000 claims description 3
ZPFHNHRLFFDIEE-HWKANZROSA-N 5-[(e)-4-(4-aminopiperidin-1-yl)but-1-enyl]-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\CCN1CCC(N)CC1 ZPFHNHRLFFDIEE-HWKANZROSA-N 0.000 claims description 3
ONVKMLLZJOUNDQ-UHFFFAOYSA-N 5-[2-[2-methoxy-4-[(4-methylpiperazin-1-yl)methyl]phenyl]ethyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C=1C=C(CCC=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)C(OC)=CC=1CN1CCN(C)CC1 ONVKMLLZJOUNDQ-UHFFFAOYSA-N 0.000 claims description 3
PAAFOMXCYCZMGU-UHFFFAOYSA-N 5-[4-(4-aminopiperidin-1-yl)butyl]-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)=C1CCCCN1CCC(N)CC1 PAAFOMXCYCZMGU-UHFFFAOYSA-N 0.000 claims description 3
YPYHSBQWPAUHCI-UHFFFAOYSA-N 5-benzyl-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)=C1CC1=CC=CC=C1 YPYHSBQWPAUHCI-UHFFFAOYSA-N 0.000 claims description 3
CVGFFBRUEVLMKY-MDZDMXLPSA-N 6-ethyl-4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-phenylethenyl]pyridine-3-carbonitrile Chemical compound CCC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1\C=C\C1=CC=CC=C1 CVGFFBRUEVLMKY-MDZDMXLPSA-N 0.000 claims description 3
PYQNWOJIGSDZLG-JXMROGBWSA-N 6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-[4-(2-pyrrolidin-1-ylethoxy)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=C1OCCN1CCCC1 PYQNWOJIGSDZLG-JXMROGBWSA-N 0.000 claims description 3
UBOJVUOKIQYEEW-VOTSOKGWSA-N 6-methyl-4-[(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=C(C)N=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C UBOJVUOKIQYEEW-VOTSOKGWSA-N 0.000 claims description 3
RDRWDCLWRAZUKF-BQYQJAHWSA-N 6-methyl-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=2C)NC=2C(=C3C=CNC3=CC=2)C)=N1 RDRWDCLWRAZUKF-BQYQJAHWSA-N 0.000 claims description 3
BSJGVZZZGOAZFN-CMDGGOBGSA-N 6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-phenylethenyl]pyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1\C=C\C1=CC=CC=C1 BSJGVZZZGOAZFN-CMDGGOBGSA-N 0.000 claims description 3
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 3
HOHBKMGNABWJKP-VOTSOKGWSA-N C1CN(C(=O)C)CCN1Cc1cccc(\C=C\c2cncc(C#N)c2Nc2ccc3[nH]ccc3c2C)n1 Chemical compound C1CN(C(=O)C)CCN1Cc1cccc(\C=C\c2cncc(C#N)c2Nc2ccc3[nH]ccc3c2C)n1 HOHBKMGNABWJKP-VOTSOKGWSA-N 0.000 claims description 3
DBAWMPDSUNOTMT-UHFFFAOYSA-N CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C#N)C=CC1=C(C=C(C=C1)CN1CCN(CC1)C)C Chemical compound CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C#N)C=CC1=C(C=C(C=C1)CN1CCN(CC1)C)C DBAWMPDSUNOTMT-UHFFFAOYSA-N 0.000 claims description 3
DRHTVOOUIIOMEO-UHFFFAOYSA-N ClC=1C=C(C(=C2C=CNC12)C)NC1=C(C=NC=C1C#N)C=CC1=CC(=CC=C1)OC Chemical compound ClC=1C=C(C(=C2C=CNC12)C)NC1=C(C=NC=C1C#N)C=CC1=CC(=CC=C1)OC DRHTVOOUIIOMEO-UHFFFAOYSA-N 0.000 claims description 3
101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims description 3
IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 3
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
125000002393 azetidinyl group Chemical group 0.000 claims description 3
125000001246 bromo group Chemical group Br* 0.000 claims description 3
MOAZBBLNNSXFNG-CSKARUKUSA-N c1cc2[nH]c(C)cc2cc1Nc1c(C#N)cnc(C)c1\C=C\c1ccccc1 Chemical compound c1cc2[nH]c(C)cc2cc1Nc1c(C#N)cnc(C)c1\C=C\c1ccccc1 MOAZBBLNNSXFNG-CSKARUKUSA-N 0.000 claims description 3
HHSLZBJAKOUCGR-CMDGGOBGSA-N c1cc2[nH]ccc2c(C)c1Nc(c(cnc1)C#N)c1\C=C\c(c1)cccc1CN(CC1)CCC1N1CCCCC1 Chemical compound c1cc2[nH]ccc2c(C)c1Nc(c(cnc1)C#N)c1\C=C\c(c1)cccc1CN(CC1)CCC1N1CCCCC1 HHSLZBJAKOUCGR-CMDGGOBGSA-N 0.000 claims description 3
UNYVCTHDVMFMSR-AATRIKPKSA-N c1cc2[nH]ccc2c(C)c1Nc(c(cnc1)C#N)c1\C=C\c1cccc(Cl)n1 Chemical compound c1cc2[nH]ccc2c(C)c1Nc(c(cnc1)C#N)c1\C=C\c1cccc(Cl)n1 UNYVCTHDVMFMSR-AATRIKPKSA-N 0.000 claims description 3
206010009887 colitis Diseases 0.000 claims description 3
RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 3
125000002757 morpholinyl group Chemical group 0.000 claims description 3
201000006417 multiple sclerosis Diseases 0.000 claims description 3
ORSMLITYQOYOSE-GQCTYLIASA-N n-[1-[(e)-4-[5-cyano-2-methyl-4-[(4-methyl-1h-indol-5-yl)amino]pyridin-3-yl]but-3-enyl]piperidin-4-yl]methanesulfonamide Chemical compound CC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1\C=C\CCN1CCC(NS(C)(=O)=O)CC1 ORSMLITYQOYOSE-GQCTYLIASA-N 0.000 claims description 3
XTCHBPCWJUSYFA-HWKANZROSA-N n-[1-[(e)-4-[5-cyano-4-[(4-methyl-1h-indol-5-yl)amino]pyridin-3-yl]but-3-enyl]piperidin-4-yl]methanesulfonamide Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CCN1CCC(NS(C)(=O)=O)CC1 XTCHBPCWJUSYFA-HWKANZROSA-N 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
JXCGYZJQEWQYLI-AATRIKPKSA-N tert-butyl 4-[(e)-2-[5-cyano-4-[(4-methyl-1h-indol-5-yl)amino]pyridin-3-yl]ethenyl]piperidine-1-carboxylate Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C1CCN(C(=O)OC(C)(C)C)CC1 JXCGYZJQEWQYLI-AATRIKPKSA-N 0.000 claims description 3
GRCVNVWSBMFCIA-UHFFFAOYSA-N tert-butyl 4-[5-cyano-4-[(4-methyl-1h-indol-5-yl)amino]pyridin-3-yl]-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C1=CCN(C(=O)OC(C)(C)C)CC1 GRCVNVWSBMFCIA-UHFFFAOYSA-N 0.000 claims description 3
125000004605 1,2,3,4-tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 2
125000005960 1,4-diazepanyl group Chemical group 0.000 claims description 2
QFARSZMCYNKGEE-MDZDMXLPSA-N 4-(1h-indol-4-yloxy)-5-[(e)-2-phenylethenyl]pyridine-3-carbonitrile Chemical compound C=1C=CC=2NC=CC=2C=1OC=1C(C#N)=CN=CC=1\C=C\C1=CC=CC=C1 QFARSZMCYNKGEE-MDZDMXLPSA-N 0.000 claims description 2
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
OTBKLEUJZBEEEQ-HWKANZROSA-N 5-[(e)-5-(4-aminopiperidin-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(N)CC1 OTBKLEUJZBEEEQ-HWKANZROSA-N 0.000 claims description 2
ILDHEIRDIFREKO-UHFFFAOYSA-N 6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]-5-(2-phenylethyl)pyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1CCC1=CC=CC=C1 ILDHEIRDIFREKO-UHFFFAOYSA-N 0.000 claims description 2
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
HQYRMPNNAVQTFC-GQCTYLIASA-N 6-methyl-4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-4-(4-methylsulfonylpiperazin-1-yl)but-1-enyl]pyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1\C=C\CCN1CCN(S(C)(=O)=O)CC1 HQYRMPNNAVQTFC-GQCTYLIASA-N 0.000 claims description 2
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
ZYOQJXCCNGOYBN-SOFGYWHQSA-N C(#N)C=1C(=C(C=NC1)/C=C/CCCN1CCC(CC1)NC(OC(C)(C)C)=O)NC=1C(=C2C=CNC2=CC1)C Chemical compound C(#N)C=1C(=C(C=NC1)/C=C/CCCN1CCC(CC1)NC(OC(C)(C)C)=O)NC=1C(=C2C=CNC2=CC1)C ZYOQJXCCNGOYBN-SOFGYWHQSA-N 0.000 claims description 2
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
ZEOPEMXLZOXMKJ-UHFFFAOYSA-N CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=NC=C(C=C1)CN1CCC(CC1)N1CCOCC1 Chemical compound CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=NC=C(C=C1)CN1CCC(CC1)N1CCOCC1 ZEOPEMXLZOXMKJ-UHFFFAOYSA-N 0.000 claims description 2
CKLBOZAZZULCNM-UHFFFAOYSA-N CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C#N)C=1CCN(CC1)C(=O)C1CCNCC1 Chemical compound CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C#N)C=1CCN(CC1)C(=O)C1CCNCC1 CKLBOZAZZULCNM-UHFFFAOYSA-N 0.000 claims description 2
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
HREUSCKYLBDOLC-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(4-methylpiperazin-1-yl)methyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CC1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C HREUSCKYLBDOLC-UHFFFAOYSA-N 0.000 claims 1
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
YUCSQCXOUZCBHF-CMDGGOBGSA-N 6-methyl-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=2C)NC=2C(=C3C=CNC3=CC=2)C)=C1 YUCSQCXOUZCBHF-CMDGGOBGSA-N 0.000 claims 1
BIIVSMXVOUFDKZ-SNAWJCMRSA-N C(#N)C=1C(=C(C=NC1)/C=C/C1CCN(CC1)C(=O)NCCC)NC=1C(=C2C=CNC2=CC1)C Chemical compound C(#N)C=1C(=C(C=NC1)/C=C/C1CCN(CC1)C(=O)NCCC)NC=1C(=C2C=CNC2=CC1)C BIIVSMXVOUFDKZ-SNAWJCMRSA-N 0.000 claims 1
HKVRESBPGLDQOS-UHFFFAOYSA-N C(#N)C=1C(=C(C=NC1)C=1CCN(CC1)C(=O)OCC)NC=1C(=C2C=CNC2=CC1)C Chemical compound C(#N)C=1C(=C(C=NC1)C=1CCN(CC1)C(=O)OCC)NC=1C(=C2C=CNC2=CC1)C HKVRESBPGLDQOS-UHFFFAOYSA-N 0.000 claims 1
NFOJNTOIDUWTDO-UHFFFAOYSA-N C(C)(C)(C)OC(NCCOC=1C=NC=C(C1)C=CC=1C=NC=C(C1NC=1C(=C2C=CNC2=CC1)C)C#N)=O Chemical compound C(C)(C)(C)OC(NCCOC=1C=NC=C(C1)C=CC=1C=NC=C(C1NC=1C(=C2C=CNC2=CC1)C)C#N)=O NFOJNTOIDUWTDO-UHFFFAOYSA-N 0.000 claims 1
MBOVJRSMWKMNMY-GQCTYLIASA-N C(C)(C)NCC/C=C/C=1C=NC=C(C#N)C1NC=1C(=C2C=CNC2=CC1)C Chemical compound C(C)(C)NCC/C=C/C=1C=NC=C(C#N)C1NC=1C(=C2C=CNC2=CC1)C MBOVJRSMWKMNMY-GQCTYLIASA-N 0.000 claims 1
VXYFMZFDPRTKKP-VAWYXSNFSA-N C(C)N(CC)CC1=CC=C(C=C1)/C=C/C=1C(=C(C=NC1C)C#N)NC=1C(=C2C=CNC2=CC1)C Chemical compound C(C)N(CC)CC1=CC=C(C=C1)/C=C/C=1C(=C(C=NC1C)C#N)NC=1C(=C2C=CNC2=CC1)C VXYFMZFDPRTKKP-VAWYXSNFSA-N 0.000 claims 1
SLTZOJAUIBSISH-ZHACJKMWSA-N C(C)N1C(CCC1)CNCC1=CC=C(C=C1)/C=C/C=1C(=C(C=NC1)C#N)NC=1C(=C2C=CNC2=CC1)C Chemical compound C(C)N1C(CCC1)CNCC1=CC=C(C=C1)/C=C/C=1C(=C(C=NC1)C#N)NC=1C(=C2C=CNC2=CC1)C SLTZOJAUIBSISH-ZHACJKMWSA-N 0.000 claims 1
UQBCIBLLAXJCFM-VAWYXSNFSA-N C(C)N1C(CCC1)CNCC1=CC=C(C=C1)/C=C/C=1C(=C(C=NC1C)C#N)NC=1C(=C2C=CNC2=CC1)C Chemical compound C(C)N1C(CCC1)CNCC1=CC=C(C=C1)/C=C/C=1C(=C(C=NC1C)C#N)NC=1C(=C2C=CNC2=CC1)C UQBCIBLLAXJCFM-VAWYXSNFSA-N 0.000 claims 1
LHVARIGYONZDLN-ZHACJKMWSA-N C(C)OCCCNCC1=CC=C(C=C1)/C=C/C=1C(=C(C=NC1C)C#N)NC=1C(=C2C=CNC2=CC1)C Chemical compound C(C)OCCCNCC1=CC=C(C=C1)/C=C/C=1C(=C(C=NC1C)C#N)NC=1C(=C2C=CNC2=CC1)C LHVARIGYONZDLN-ZHACJKMWSA-N 0.000 claims 1
NNDKOYJMZUUGHC-MDZDMXLPSA-N C(C)OCCCNCC1=CC=CC(=N1)/C=C/C=1C(=C(C=NC1C)C#N)NC=1C(=C2C=CNC2=CC1)C Chemical compound C(C)OCCCNCC1=CC=CC(=N1)/C=C/C=1C(=C(C=NC1C)C#N)NC=1C(=C2C=CNC2=CC1)C NNDKOYJMZUUGHC-MDZDMXLPSA-N 0.000 claims 1
NDQIAGZMYAFOGV-CMDGGOBGSA-N C(C)OCCCNCC=1C=CC(=NC1)/C=C/C=1C(=NC=C(C#N)C1NC=1C(=C2C=CNC2=CC1)C)C Chemical compound C(C)OCCCNCC=1C=CC(=NC1)/C=C/C=1C(=NC=C(C#N)C1NC=1C(=C2C=CNC2=CC1)C)C NDQIAGZMYAFOGV-CMDGGOBGSA-N 0.000 claims 1
TUAXWSXTWCMIKY-CMDGGOBGSA-N C(C)OCCNCC1=CC=C(C=C1)/C=C/C=1C(=C(C=NC1)C#N)NC=1C(=C2C=CNC2=CC1)C Chemical compound C(C)OCCNCC1=CC=C(C=C1)/C=C/C=1C(=C(C=NC1)C#N)NC=1C(=C2C=CNC2=CC1)C TUAXWSXTWCMIKY-CMDGGOBGSA-N 0.000 claims 1
UVJKTOZHPYBPQO-BQYQJAHWSA-N C(C)OCCNCC=1C=CC(=NC1)/C=C/C=1C(=NC=C(C#N)C1NC=1C(=C2C=CNC2=CC1)C)C Chemical compound C(C)OCCNCC=1C=CC(=NC1)/C=C/C=1C(=NC=C(C#N)C1NC=1C(=C2C=CNC2=CC1)C)C UVJKTOZHPYBPQO-BQYQJAHWSA-N 0.000 claims 1
PGOUUZDEEQZZHY-UHFFFAOYSA-N C(C1=CC=CC=C1)N1CCC(=CC1)C=1C(=NC=C(C1NC=1C(=C2C=CNC2=CC1)C)C#N)C Chemical compound C(C1=CC=CC=C1)N1CCC(=CC1)C=1C(=NC=C(C1NC=1C(=C2C=CNC2=CC1)C)C#N)C PGOUUZDEEQZZHY-UHFFFAOYSA-N 0.000 claims 1
UYFJIYCASWDDBK-ZHACJKMWSA-N C1(CCCC1)N1CCN(CC1)CC1=CC=C(C=C1)/C=C/C=1C(=C(C=NC1)C#N)NC=1C(=C2C=CNC2=CC1)C Chemical compound C1(CCCC1)N1CCN(CC1)CC1=CC=C(C=C1)/C=C/C=1C(=C(C=NC1)C#N)NC=1C(=C2C=CNC2=CC1)C UYFJIYCASWDDBK-ZHACJKMWSA-N 0.000 claims 1
MWGAWIWTMGKNMJ-MDZDMXLPSA-N C1(CCCC1)N1CCN(CC1)CC=1C=CC(=NC1)/C=C/C=1C(=C(C=NC1C)C#N)NC=1C(=C2C=CNC2=CC1)C Chemical compound C1(CCCC1)N1CCN(CC1)CC=1C=CC(=NC1)/C=C/C=1C(=C(C=NC1C)C#N)NC=1C(=C2C=CNC2=CC1)C MWGAWIWTMGKNMJ-MDZDMXLPSA-N 0.000 claims 1
FMYVNXGNYYSKOM-FNORWQNLSA-N C1(CCCCC1)NCC/C=C/C=1C=NC=C(C#N)C1NC=1C(=C2C=CNC2=CC1)C Chemical compound C1(CCCCC1)NCC/C=C/C=1C=NC=C(C#N)C1NC=1C(=C2C=CNC2=CC1)C FMYVNXGNYYSKOM-FNORWQNLSA-N 0.000 claims 1
JLAPFZLWYIDJDS-SNAWJCMRSA-N C1CN(C)CCN1Cc1nc(\C=C\c2c(ncc(C#N)c2Nc2ccc3[nH]ccc3c2C)C)cs1 Chemical compound C1CN(C)CCN1Cc1nc(\C=C\c2c(ncc(C#N)c2Nc2ccc3[nH]ccc3c2C)C)cs1 JLAPFZLWYIDJDS-SNAWJCMRSA-N 0.000 claims 1
DJMCULRJABJZGG-CMDGGOBGSA-N CC(CCN(CCOC=1C=C(C=NC1)/C=C/C=1C=NC=C(C#N)C1NC=1C(=C2C=CNC2=CC1)C)CCC(C)(C)C)(C)C Chemical compound CC(CCN(CCOC=1C=C(C=NC1)/C=C/C=1C=NC=C(C#N)C1NC=1C(=C2C=CNC2=CC1)C)CCC(C)(C)C)(C)C DJMCULRJABJZGG-CMDGGOBGSA-N 0.000 claims 1
CMZHRAUUXHDDHB-UHFFFAOYSA-N CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=CC(=CC=C1)CN1CCCC1 Chemical compound CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=CC(=CC=C1)CN1CCCC1 CMZHRAUUXHDDHB-UHFFFAOYSA-N 0.000 claims 1
UYFWQBVSHHNNMQ-UHFFFAOYSA-N CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=CC(=CC=C1)CN1CCN(CC1)C Chemical compound CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=CC(=CC=C1)CN1CCN(CC1)C UYFWQBVSHHNNMQ-UHFFFAOYSA-N 0.000 claims 1
LXQNOISDWHDBED-UHFFFAOYSA-N CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=CC(=CC=C1)CN1CCN(CC1)C(C)C Chemical compound CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=CC(=CC=C1)CN1CCN(CC1)C(C)C LXQNOISDWHDBED-UHFFFAOYSA-N 0.000 claims 1
XXNLBASSADACKL-UHFFFAOYSA-N CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=CC(=CC=C1)CN1CCOCC1 Chemical compound CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=CC(=CC=C1)CN1CCOCC1 XXNLBASSADACKL-UHFFFAOYSA-N 0.000 claims 1
SBDMFUVJNYWUAT-UHFFFAOYSA-N CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=CC(=CC=C1)CN1CCSCC1 Chemical compound CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=CC(=CC=C1)CN1CCSCC1 SBDMFUVJNYWUAT-UHFFFAOYSA-N 0.000 claims 1
ICCPAOFNPPETMX-UHFFFAOYSA-N CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=CC(=CC=C1)CNCCCN1CCN(CC1)C Chemical compound CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=CC(=CC=C1)CNCCCN1CCN(CC1)C ICCPAOFNPPETMX-UHFFFAOYSA-N 0.000 claims 1
DGCFLTVUZOPQRS-UHFFFAOYSA-N CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=CC(=CC=C1)CNCCN1CCCC1 Chemical compound CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=CC(=CC=C1)CNCCN1CCCC1 DGCFLTVUZOPQRS-UHFFFAOYSA-N 0.000 claims 1
ONQXVWSRSZFEKJ-UHFFFAOYSA-N CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=CC=C(C=C1)CN1CCC(CC1)N1CCOCC1 Chemical compound CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=CC=C(C=C1)CN1CCC(CC1)N1CCOCC1 ONQXVWSRSZFEKJ-UHFFFAOYSA-N 0.000 claims 1
GJXXMNWUVYJVAJ-UHFFFAOYSA-N CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=CC=C(C=C1)CN1CCCC1 Chemical compound CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=CC=C(C=C1)CN1CCCC1 GJXXMNWUVYJVAJ-UHFFFAOYSA-N 0.000 claims 1
HCPBJSAGBWEWAH-UHFFFAOYSA-N CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=CC=C(C=C1)CN1CCN(CC1)C(C)C Chemical compound CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=CC=C(C=C1)CN1CCN(CC1)C(C)C HCPBJSAGBWEWAH-UHFFFAOYSA-N 0.000 claims 1
AUNBJRCIGQNLMO-UHFFFAOYSA-N CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=CC=C(C=C1)CN1CCN(CCC1)C Chemical compound CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=CC=C(C=C1)CN1CCN(CCC1)C AUNBJRCIGQNLMO-UHFFFAOYSA-N 0.000 claims 1
VNLHTNFIGWKBQJ-UHFFFAOYSA-N CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=CC=C(C=C1)CN1CCOCC1 Chemical compound CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=CC=C(C=C1)CN1CCOCC1 VNLHTNFIGWKBQJ-UHFFFAOYSA-N 0.000 claims 1
GSZYYPHCDMMJCU-UHFFFAOYSA-N CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=CC=C(C=C1)CN1CCSCC1 Chemical compound CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=CC=C(C=C1)CN1CCSCC1 GSZYYPHCDMMJCU-UHFFFAOYSA-N 0.000 claims 1
SLZLAPYDZSPUOP-UHFFFAOYSA-N CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=CC=C(C=C1)CNCCC1=CC=NC=C1 Chemical compound CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=CC=C(C=C1)CNCCC1=CC=NC=C1 SLZLAPYDZSPUOP-UHFFFAOYSA-N 0.000 claims 1
LQAAWDJMDNIKLP-UHFFFAOYSA-N CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=CC=C(C=C1)CNCCC1=NC=CC=C1 Chemical compound CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=CC=C(C=C1)CNCCC1=NC=CC=C1 LQAAWDJMDNIKLP-UHFFFAOYSA-N 0.000 claims 1
QGMYPLNWULGBJV-UHFFFAOYSA-N CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=CC=C(C=C1)CNCCC=1C=NC=CC1 Chemical compound CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=CC=C(C=C1)CNCCC=1C=NC=CC1 QGMYPLNWULGBJV-UHFFFAOYSA-N 0.000 claims 1
MKPHYDUQHVLQRM-UHFFFAOYSA-N CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=CC=C(C=C1)CNCCN1C(CCC1)C Chemical compound CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=CC=C(C=C1)CNCCN1C(CCC1)C MKPHYDUQHVLQRM-UHFFFAOYSA-N 0.000 claims 1
LVQVUQRUIXRGRZ-UHFFFAOYSA-N CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=CC=C(C=C1)CNCCN1CCCCC1 Chemical compound CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=CC=C(C=C1)CNCCN1CCCCC1 LVQVUQRUIXRGRZ-UHFFFAOYSA-N 0.000 claims 1
VLASRIHFSDHVNE-UHFFFAOYSA-N CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=NC(=CC=C1)CN1CCC(CC1)N1CCCC1 Chemical compound CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=NC(=CC=C1)CN1CCC(CC1)N1CCCC1 VLASRIHFSDHVNE-UHFFFAOYSA-N 0.000 claims 1
QSSBEWSUZSMPOQ-UHFFFAOYSA-N CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=NC(=CC=C1)CN1CCC(CC1)N1CCOCC1 Chemical compound CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=NC(=CC=C1)CN1CCC(CC1)N1CCOCC1 QSSBEWSUZSMPOQ-UHFFFAOYSA-N 0.000 claims 1
ORCAOYDDDKBDAX-UHFFFAOYSA-N CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=NC(=CC=C1)CN1CCCC1 Chemical compound CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=NC(=CC=C1)CN1CCCC1 ORCAOYDDDKBDAX-UHFFFAOYSA-N 0.000 claims 1
OGUDUCRBOWNSPE-UHFFFAOYSA-N CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=NC(=CC=C1)CN1CCN(CC1)C(C)C Chemical compound CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=NC(=CC=C1)CN1CCN(CC1)C(C)C OGUDUCRBOWNSPE-UHFFFAOYSA-N 0.000 claims 1
QWABYFDFDJAZBI-UHFFFAOYSA-N CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=NC(=CC=C1)CN1CCN(CCC1)C Chemical compound CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=NC(=CC=C1)CN1CCN(CCC1)C QWABYFDFDJAZBI-UHFFFAOYSA-N 0.000 claims 1
PWLKGUPJQRLGTP-UHFFFAOYSA-N CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=NC(=CC=C1)CN1CCOCC1 Chemical compound CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=NC(=CC=C1)CN1CCOCC1 PWLKGUPJQRLGTP-UHFFFAOYSA-N 0.000 claims 1
IMJOKUJMJGYVAS-UHFFFAOYSA-N CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=NC(=CC=C1)CN1CCSCC1 Chemical compound CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=NC(=CC=C1)CN1CCSCC1 IMJOKUJMJGYVAS-UHFFFAOYSA-N 0.000 claims 1
WYGQTSGGBZJPLM-UHFFFAOYSA-N CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=NC(=CC=C1)CNCCC1=CC=NC=C1 Chemical compound CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=NC(=CC=C1)CNCCC1=CC=NC=C1 WYGQTSGGBZJPLM-UHFFFAOYSA-N 0.000 claims 1
ZMLVTVOPPWCTIS-UHFFFAOYSA-N CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=NC(=CC=C1)CNCCC=1C=NC=CC1 Chemical compound CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=NC(=CC=C1)CNCCC=1C=NC=CC1 ZMLVTVOPPWCTIS-UHFFFAOYSA-N 0.000 claims 1
OCZBHMXBPZZUSD-UHFFFAOYSA-N CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=NC(=CC=C1)CNCCCN1CCOCC1 Chemical compound CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=NC(=CC=C1)CNCCCN1CCOCC1 OCZBHMXBPZZUSD-UHFFFAOYSA-N 0.000 claims 1
RLXKJHPWWBRDFD-UHFFFAOYSA-N CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=NC(=CC=C1)CNCCN1CCOCC1 Chemical compound CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=NC(=CC=C1)CNCCN1CCOCC1 RLXKJHPWWBRDFD-UHFFFAOYSA-N 0.000 claims 1
XEGHFJCZZSQWFV-UHFFFAOYSA-N CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=NC=C(C=C1)CN1CCCCC1 Chemical compound CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=NC=C(C=C1)CN1CCCCC1 XEGHFJCZZSQWFV-UHFFFAOYSA-N 0.000 claims 1
LLYIRQMEWOODDF-UHFFFAOYSA-N CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=NC=C(C=C1)CN1CCOCC1 Chemical compound CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=NC=C(C=C1)CN1CCOCC1 LLYIRQMEWOODDF-UHFFFAOYSA-N 0.000 claims 1
VCEFKKBQDDQJTB-UHFFFAOYSA-N CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=NC=C(C=C1)CN1CCSCC1 Chemical compound CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=NC=C(C=C1)CN1CCSCC1 VCEFKKBQDDQJTB-UHFFFAOYSA-N 0.000 claims 1
PWOOQSVROJLBFK-UHFFFAOYSA-N CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=NC=C(C=C1)CNCCCN1CCOCC1 Chemical compound CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=NC=C(C=C1)CNCCCN1CCOCC1 PWOOQSVROJLBFK-UHFFFAOYSA-N 0.000 claims 1
XYSYHVZSOHJIMB-UHFFFAOYSA-N CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=NC=C(C=C1)CNCCN1CCOCC1 Chemical compound CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC1)C)C=CC1=NC=C(C=C1)CNCCN1CCOCC1 XYSYHVZSOHJIMB-UHFFFAOYSA-N 0.000 claims 1
PTTOAFFBLUGDAN-MDZDMXLPSA-N CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC=1)C)\C=C\C1=CC=C(C=C1)CNCCCN1CCN(CC1)C Chemical compound CC1=C(C(=C(C=N1)C#N)NC=1C(=C2C=CNC2=CC=1)C)\C=C\C1=CC=C(C=C1)CNCCCN1CCN(CC1)C PTTOAFFBLUGDAN-MDZDMXLPSA-N 0.000 claims 1
RBOYYLVNIZUWER-UHFFFAOYSA-N CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C#N)C=CC1=C(C=C(C=C1)C(=O)N1CCN(CC1)C)C Chemical compound CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C#N)C=CC1=C(C=C(C=C1)C(=O)N1CCN(CC1)C)C RBOYYLVNIZUWER-UHFFFAOYSA-N 0.000 claims 1
ITOMSBHWXQMNIZ-UHFFFAOYSA-N CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C#N)C=CC1=CC=C(C=C1)C=1N=NNN1 Chemical compound CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C#N)C=CC1=CC=C(C=C1)C=1N=NNN1 ITOMSBHWXQMNIZ-UHFFFAOYSA-N 0.000 claims 1
QIBKENGMLMALEZ-UHFFFAOYSA-N CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C#N)C=CC1=CC=C(C=C1)CN1CCSCC1 Chemical compound CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C#N)C=CC1=CC=C(C=C1)CN1CCSCC1 QIBKENGMLMALEZ-UHFFFAOYSA-N 0.000 claims 1
IGWWBKDNGSARBL-UHFFFAOYSA-N CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C#N)C=CCCN1CC(NCC1)=O Chemical compound CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C#N)C=CCCN1CC(NCC1)=O IGWWBKDNGSARBL-UHFFFAOYSA-N 0.000 claims 1
KJKZJUNRUKVEPY-UHFFFAOYSA-N CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C#N)C=CCCN1CCSCC1 Chemical compound CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C#N)C=CCCN1CCSCC1 KJKZJUNRUKVEPY-UHFFFAOYSA-N 0.000 claims 1
OOSKBCDKDIRGOL-UHFFFAOYSA-N CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C#N)C=CCCNC1CCNCC1 Chemical compound CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C#N)C=CCCNC1CCNCC1 OOSKBCDKDIRGOL-UHFFFAOYSA-N 0.000 claims 1
VDEPKBSLCMGINZ-UHFFFAOYSA-N CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C=CC1=CC(=CC=C1)CN1CCCC1)C#N Chemical compound CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C=CC1=CC(=CC=C1)CN1CCCC1)C#N VDEPKBSLCMGINZ-UHFFFAOYSA-N 0.000 claims 1
FZXVOJSAANWPFZ-UHFFFAOYSA-N CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C=CC1=CC(=CC=C1)CNCCCN1C(CCC1)=O)C#N Chemical compound CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C=CC1=CC(=CC=C1)CNCCCN1C(CCC1)=O)C#N FZXVOJSAANWPFZ-UHFFFAOYSA-N 0.000 claims 1
YSIMVZYCDBEJLL-UHFFFAOYSA-N CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C=CC1=CC=C(C=C1)CN1CCC(CC1)N1CCOCC1)C#N Chemical compound CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C=CC1=CC=C(C=C1)CN1CCC(CC1)N1CCOCC1)C#N YSIMVZYCDBEJLL-UHFFFAOYSA-N 0.000 claims 1
JMWUQBOFBLEKRJ-UHFFFAOYSA-N CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C=CC1=CC=C(C=C1)CNCCC1=NC=CC=C1)C#N Chemical compound CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C=CC1=CC=C(C=C1)CNCCC1=NC=CC=C1)C#N JMWUQBOFBLEKRJ-UHFFFAOYSA-N 0.000 claims 1
SLZLFZSBBUGUDY-UHFFFAOYSA-N CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C=CC1=CC=C(C=C1)CNCCC1N(CCC1)C)C#N Chemical compound CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C=CC1=CC=C(C=C1)CNCCC1N(CCC1)C)C#N SLZLFZSBBUGUDY-UHFFFAOYSA-N 0.000 claims 1
SXPGZSMAEGYHMX-UHFFFAOYSA-N CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C=CC1=CC=C(C=C1)CNCCC=1C=NC=CC1)C#N Chemical compound CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C=CC1=CC=C(C=C1)CNCCC=1C=NC=CC1)C#N SXPGZSMAEGYHMX-UHFFFAOYSA-N 0.000 claims 1
VZORSSNPWOTLLF-UHFFFAOYSA-N CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C=CC1=CC=C(C=C1)CNCCCN1CCN(CC1)C)C#N Chemical compound CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C=CC1=CC=C(C=C1)CNCCCN1CCN(CC1)C)C#N VZORSSNPWOTLLF-UHFFFAOYSA-N 0.000 claims 1
ACTLAWQOGTZVBY-UHFFFAOYSA-N CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C=CC1=CC=C(C=C1)CNCCCN1CCOCC1)C#N Chemical compound CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C=CC1=CC=C(C=C1)CNCCCN1CCOCC1)C#N ACTLAWQOGTZVBY-UHFFFAOYSA-N 0.000 claims 1
FYZLQPAZHLMRJB-UHFFFAOYSA-N CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C=CC1=CC=C(C=C1)CNCCN1CCCC1)C#N Chemical compound CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C=CC1=CC=C(C=C1)CNCCN1CCCC1)C#N FYZLQPAZHLMRJB-UHFFFAOYSA-N 0.000 claims 1
TVSBUOAETDDFSM-UHFFFAOYSA-N CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C=CC1=CC=C(C=C1)CNCCN1CCCCC1)C#N Chemical compound CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C=CC1=CC=C(C=C1)CNCCN1CCCCC1)C#N TVSBUOAETDDFSM-UHFFFAOYSA-N 0.000 claims 1
ZCSQYGUKAFGEQD-UHFFFAOYSA-N CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C=CC1=NC=C(C=C1)CNCCC1=CC=NC=C1)C#N Chemical compound CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C=CC1=NC=C(C=C1)CNCCC1=CC=NC=C1)C#N ZCSQYGUKAFGEQD-UHFFFAOYSA-N 0.000 claims 1
YTLPIECTHGNGSU-UHFFFAOYSA-N CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C=CC1=NC=C(C=C1)CNCCC1=NC=CC=C1)C#N Chemical compound CC1=C2C=CNC2=CC=C1NC1=C(C=NC=C1C=CC1=NC=C(C=C1)CNCCC1=NC=CC=C1)C#N YTLPIECTHGNGSU-UHFFFAOYSA-N 0.000 claims 1
XYYQSMCWDRYASB-UHFFFAOYSA-N CC1=NC=C(C#N)C(=C1C=CC1=CC=C(C=C1)CNCCN1CCCC1)NC=1C(=C2C=CNC2=CC1)C Chemical compound CC1=NC=C(C#N)C(=C1C=CC1=CC=C(C=C1)CNCCN1CCCC1)NC=1C(=C2C=CNC2=CC1)C XYYQSMCWDRYASB-UHFFFAOYSA-N 0.000 claims 1
VZKWXWPPVUOMSG-UHFFFAOYSA-N CC1=NC=C(C#N)C(=C1C=CC1=CC=C(C=C1)CNCCN1CCOCC1)NC=1C(=C2C=CNC2=CC1)C Chemical compound CC1=NC=C(C#N)C(=C1C=CC1=CC=C(C=C1)CNCCN1CCOCC1)NC=1C(=C2C=CNC2=CC1)C VZKWXWPPVUOMSG-UHFFFAOYSA-N 0.000 claims 1
GXZDZDJJPMBBDS-UHFFFAOYSA-N CC1=NC=C(C#N)C(=C1C=CC1=NC=C(C=C1)CN1CCN(CCC1)C)NC=1C(=C2C=CNC2=CC1)C Chemical compound CC1=NC=C(C#N)C(=C1C=CC1=NC=C(C=C1)CN1CCN(CCC1)C)NC=1C(=C2C=CNC2=CC1)C GXZDZDJJPMBBDS-UHFFFAOYSA-N 0.000 claims 1
ZVSXGVONPDALAC-UHFFFAOYSA-N CC1=NC=C(C#N)C(=C1C=CC1=NC=C(C=C1)CNCCC1=CC=NC=C1)NC=1C(=C2C=CNC2=CC1)C Chemical compound CC1=NC=C(C#N)C(=C1C=CC1=NC=C(C=C1)CNCCC1=CC=NC=C1)NC=1C(=C2C=CNC2=CC1)C ZVSXGVONPDALAC-UHFFFAOYSA-N 0.000 claims 1
IJFUMVZMDIZOCC-UHFFFAOYSA-N CC1=NC=C(C#N)C(=C1C=CC1=NC=C(C=C1)CNCCC=1C=NC=CC1)NC=1C(=C2C=CNC2=CC1)C Chemical compound CC1=NC=C(C#N)C(=C1C=CC1=NC=C(C=C1)CNCCC=1C=NC=CC1)NC=1C(=C2C=CNC2=CC1)C IJFUMVZMDIZOCC-UHFFFAOYSA-N 0.000 claims 1
VLCUXNAUCCCXDC-UHFFFAOYSA-N CC1=NC=C(C#N)C(=C1C=CC=1C=NC=CC1)NC=1C(=C2C=CNC2=CC1)C Chemical compound CC1=NC=C(C#N)C(=C1C=CC=1C=NC=CC1)NC=1C(=C2C=CNC2=CC1)C VLCUXNAUCCCXDC-UHFFFAOYSA-N 0.000 claims 1
OBHIDHDGRYOWII-UHFFFAOYSA-N CC1=NC=C(C(=C1C=1CCN(CC1)CC1CCN(CC1)C)NC=1C(=C2C=CNC2=CC1)C)C#N Chemical compound CC1=NC=C(C(=C1C=1CCN(CC1)CC1CCN(CC1)C)NC=1C(=C2C=CNC2=CC1)C)C#N OBHIDHDGRYOWII-UHFFFAOYSA-N 0.000 claims 1
UJHJNEAWRVSHJC-UHFFFAOYSA-N CC1=NC=C(C(=C1C=1CCN(CC1)S(=O)(=O)C)NC=1C(=C2C=CNC2=CC1)C)C#N Chemical compound CC1=NC=C(C(=C1C=1CCN(CC1)S(=O)(=O)C)NC=1C(=C2C=CNC2=CC1)C)C#N UJHJNEAWRVSHJC-UHFFFAOYSA-N 0.000 claims 1
UASBFIVQUHPNKX-UHFFFAOYSA-N CC1=NC=C(C(=C1C=1CCNCC1)NC=1C(=C2C=CNC2=CC1)C)C#N Chemical compound CC1=NC=C(C(=C1C=1CCNCC1)NC=1C(=C2C=CNC2=CC1)C)C#N UASBFIVQUHPNKX-UHFFFAOYSA-N 0.000 claims 1
JCGGBUKIBSSLAE-CMDGGOBGSA-N CCc1ncc(C#N)c(Nc2ccc3[nH]ccc3c2C)c1\C=C\c(c1)cccc1CN1CCN(C)CC1 Chemical compound CCc1ncc(C#N)c(Nc2ccc3[nH]ccc3c2C)c1\C=C\c(c1)cccc1CN1CCN(C)CC1 JCGGBUKIBSSLAE-CMDGGOBGSA-N 0.000 claims 1
HOKLCIRWLPNREW-CMDGGOBGSA-N CN(C)CC1=CC=CC(=N1)/C=C/C=1C(=C(C=NC1C)C#N)NC=1C(=C2C=CNC2=CC1)C Chemical compound CN(C)CC1=CC=CC(=N1)/C=C/C=1C(=C(C=NC1C)C#N)NC=1C(=C2C=CNC2=CC1)C HOKLCIRWLPNREW-CMDGGOBGSA-N 0.000 claims 1
FQMATLWMSPCPJK-UHFFFAOYSA-N CN(CC(=O)N1CCC(=CC1)C=1C=NC=C(C1NC=1C(=C2C=CNC2=CC1)C)C#N)C Chemical compound CN(CC(=O)N1CCC(=CC1)C=1C=NC=C(C1NC=1C(=C2C=CNC2=CC1)C)C#N)C FQMATLWMSPCPJK-UHFFFAOYSA-N 0.000 claims 1
HCPYFYZVJQHXMN-GQCTYLIASA-N CN(CC/C=C/C=1C=NC=C(C#N)C1NC=1C(=C2C=CNC2=CC1)C)C Chemical compound CN(CC/C=C/C=1C=NC=C(C#N)C1NC=1C(=C2C=CNC2=CC1)C)C HCPYFYZVJQHXMN-GQCTYLIASA-N 0.000 claims 1
JHHYDMRYZUPITG-ZHACJKMWSA-N CN(CCCNCC1=CC=C(C=C1)/C=C/C=1C(=C(C=NC1C)C#N)NC=1C(=C2C=CNC2=CC1)C)C Chemical compound CN(CCCNCC1=CC=C(C=C1)/C=C/C=1C(=C(C=NC1C)C#N)NC=1C(=C2C=CNC2=CC1)C)C JHHYDMRYZUPITG-ZHACJKMWSA-N 0.000 claims 1
PLYOLEQURRLLRH-MDZDMXLPSA-N CN(CCCNCC1=CC=C(C=C1)/C=C/C=1C=NC=C(C#N)C1NC=1C(=C2C=CNC2=CC1)C)C Chemical compound CN(CCCNCC1=CC=C(C=C1)/C=C/C=1C=NC=C(C#N)C1NC=1C(=C2C=CNC2=CC1)C)C PLYOLEQURRLLRH-MDZDMXLPSA-N 0.000 claims 1
ZYNASSIWTLOOJF-MDZDMXLPSA-N CN(CCCNCC1=CC=CC(=N1)/C=C/C=1C(=C(C=NC1C)C#N)NC=1C(=C2C=CNC2=CC1)C)C Chemical compound CN(CCCNCC1=CC=CC(=N1)/C=C/C=1C(=C(C=NC1C)C#N)NC=1C(=C2C=CNC2=CC1)C)C ZYNASSIWTLOOJF-MDZDMXLPSA-N 0.000 claims 1
WFERWQJALJYOQU-MDZDMXLPSA-N CN(CCNCC1=CC=C(C=C1)/C=C/C=1C(=C(C=NC1C)C#N)NC=1C(=C2C=CNC2=CC1)C)C Chemical compound CN(CCNCC1=CC=C(C=C1)/C=C/C=1C(=C(C=NC1C)C#N)NC=1C(=C2C=CNC2=CC1)C)C WFERWQJALJYOQU-MDZDMXLPSA-N 0.000 claims 1
JYIBHEKUXARTJS-CMDGGOBGSA-N CN1CCN(CCC1)CC1=CC=C(C=C1)/C=C/C=1C(=C(C=NC1)C#N)NC=1C(=C2C=CNC2=CC1)C Chemical compound CN1CCN(CCC1)CC1=CC=C(C=C1)/C=C/C=1C(=C(C=NC1)C#N)NC=1C(=C2C=CNC2=CC1)C JYIBHEKUXARTJS-CMDGGOBGSA-N 0.000 claims 1
QMBUJHVTAQQXCC-FNORWQNLSA-N COC=1C=C(C=CC1OC)/C=C/C=1C(=NC=C(C#N)C1NC=1C(=C2C=CNC2=CC1)C)C Chemical compound COC=1C=C(C=CC1OC)/C=C/C=1C(=NC=C(C#N)C1NC=1C(=C2C=CNC2=CC1)C)C QMBUJHVTAQQXCC-FNORWQNLSA-N 0.000 claims 1
VCOOFTWVWQJCLJ-CMDGGOBGSA-N COc1ccccc1\C=C\c1c(C)ncc(C#N)c1Nc1ccc2[nH]ccc2c1C Chemical compound COc1ccccc1\C=C\c1c(C)ncc(C#N)c1Nc1ccc2[nH]ccc2c1C VCOOFTWVWQJCLJ-CMDGGOBGSA-N 0.000 claims 1
USZCALARUJAWIF-ZHACJKMWSA-N Cc1ncc(C#N)c(Nc2ccc3[nH]ccc3c2C)c1\C=C\c(cc1)ccc1CN(CC1)CCC1N1CCCCC1 Chemical compound Cc1ncc(C#N)c(Nc2ccc3[nH]ccc3c2C)c1\C=C\c(cc1)ccc1CN(CC1)CCC1N1CCCCC1 USZCALARUJAWIF-ZHACJKMWSA-N 0.000 claims 1
FYQZJKMLGBRYOR-ZHACJKMWSA-N Cc1ncc(C#N)c(Nc2ccc3[nH]ccc3c2C)c1\C=C\c(cc1)ccc1CS(=O)(=O)N1CCCCC1 Chemical compound Cc1ncc(C#N)c(Nc2ccc3[nH]ccc3c2C)c1\C=C\c(cc1)ccc1CS(=O)(=O)N1CCCCC1 FYQZJKMLGBRYOR-ZHACJKMWSA-N 0.000 claims 1
YUMSVWHFFXAONU-CMDGGOBGSA-N Cc1ncc(C#N)c(Nc2ccc3[nH]ccc3c2C)c1\C=C\c(nc1)ccc1CN(CC1)CCC1N1CCCCC1 Chemical compound Cc1ncc(C#N)c(Nc2ccc3[nH]ccc3c2C)c1\C=C\c(nc1)ccc1CN(CC1)CCC1N1CCCCC1 YUMSVWHFFXAONU-CMDGGOBGSA-N 0.000 claims 1
YYRJFYABBFLWCU-BQYQJAHWSA-N Cc1ncc(C#N)c(Nc2ccc3[nH]ccc3c2C)c1\C=C\c(nc1)ccc1CN1CCCC1 Chemical compound Cc1ncc(C#N)c(Nc2ccc3[nH]ccc3c2C)c1\C=C\c(nc1)ccc1CN1CCCC1 YYRJFYABBFLWCU-BQYQJAHWSA-N 0.000 claims 1
SUDZKOYUTUYKCM-UHFFFAOYSA-N ClC=1C=C(C(=C2C=CNC12)C)NC1=C(C=NC=C1C#N)C=CC1=CC=NC=C1 Chemical compound ClC=1C=C(C(=C2C=CNC12)C)NC1=C(C=NC=C1C#N)C=CC1=CC=NC=C1 SUDZKOYUTUYKCM-UHFFFAOYSA-N 0.000 claims 1
CSWMTRLSJDVCOZ-UHFFFAOYSA-N ClC=1C=C(C(=C2C=CNC12)C)NC1=C(C=NC=C1C#N)C=CC1=NC=CC=C1 Chemical compound ClC=1C=C(C(=C2C=CNC12)C)NC1=C(C=NC=C1C#N)C=CC1=NC=CC=C1 CSWMTRLSJDVCOZ-UHFFFAOYSA-N 0.000 claims 1
WPNKSZXDQOTVRQ-UHFFFAOYSA-N FC1=C(CN2CCC(=CC2)C=2C=NC=C(C2NC=2C(=C3C=CNC3=CC2)C)C#N)C=CC=C1 Chemical compound FC1=C(CN2CCC(=CC2)C=2C=NC=C(C2NC=2C(=C3C=CNC3=CC2)C)C#N)C=CC=C1 WPNKSZXDQOTVRQ-UHFFFAOYSA-N 0.000 claims 1
HIVGIEFXEQSVAU-UHFFFAOYSA-N FC=1C=C(CN2CCC(=CC2)C=2C=NC=C(C2NC=2C(=C3C=CNC3=CC2)C)C#N)C=CC1 Chemical compound FC=1C=C(CN2CCC(=CC2)C=2C=NC=C(C2NC=2C(=C3C=CNC3=CC2)C)C#N)C=CC1 HIVGIEFXEQSVAU-UHFFFAOYSA-N 0.000 claims 1
OBFRSYPTAOLJCX-CMDGGOBGSA-N N1(CCCCC1)C1CCN(CC1)CC1=CC=CC(=N1)/C=C/C=1C(=C(C=NC1)C#N)NC=1C(=C2C=CNC2=CC1)C Chemical compound N1(CCCCC1)C1CCN(CC1)CC1=CC=CC(=N1)/C=C/C=1C(=C(C=NC1)C#N)NC=1C(=C2C=CNC2=CC1)C OBFRSYPTAOLJCX-CMDGGOBGSA-N 0.000 claims 1
GTPYFAVPRSUIOS-MDZDMXLPSA-N N1(CCCCC1)C1CCN(CC1)CC=1C=C(C=CC1)/C=C/C=1C(=C(C=NC1C)C#N)NC=1C(=C2C=CNC2=CC1)C Chemical compound N1(CCCCC1)C1CCN(CC1)CC=1C=C(C=CC1)/C=C/C=1C(=C(C=NC1C)C#N)NC=1C(=C2C=CNC2=CC1)C GTPYFAVPRSUIOS-MDZDMXLPSA-N 0.000 claims 1
JWBAOYWHYJJVPJ-ZHACJKMWSA-N N1(CCCCCC1)CCNCC1=CC=C(C=C1)/C=C/C=1C(=C(C=NC1)C#N)NC=1C(=C2C=CNC2=CC1)C Chemical compound N1(CCCCCC1)CCNCC1=CC=C(C=C1)/C=C/C=1C(=C(C=NC1)C#N)NC=1C(=C2C=CNC2=CC1)C JWBAOYWHYJJVPJ-ZHACJKMWSA-N 0.000 claims 1
QHTNHVXNVCRXMV-VAWYXSNFSA-N N1(CCCCCC1)CCNCC1=CC=C(C=C1)/C=C/C=1C(=C(C=NC1C)C#N)NC=1C(=C2C=CNC2=CC1)C Chemical compound N1(CCCCCC1)CCNCC1=CC=C(C=C1)/C=C/C=1C(=C(C=NC1C)C#N)NC=1C(=C2C=CNC2=CC1)C QHTNHVXNVCRXMV-VAWYXSNFSA-N 0.000 claims 1
CBRVBSHJAUMBHA-ZHACJKMWSA-N N1(CCCCCC1)CCNCC1=CC=CC(=N1)/C=C/C=1C(=C(C=NC1C)C#N)NC=1C(=C2C=CNC2=CC1)C Chemical compound N1(CCCCCC1)CCNCC1=CC=CC(=N1)/C=C/C=1C(=C(C=NC1C)C#N)NC=1C(=C2C=CNC2=CC1)C CBRVBSHJAUMBHA-ZHACJKMWSA-N 0.000 claims 1
TVQWPDFMIWQHSB-MDZDMXLPSA-N N1(CCCCCC1)CCNCC=1C=C(C=CC1)/C=C/C=1C(=C(C=NC1)C#N)NC=1C(=C2C=CNC2=CC1)C Chemical compound N1(CCCCCC1)CCNCC=1C=C(C=CC1)/C=C/C=1C(=C(C=NC1)C#N)NC=1C(=C2C=CNC2=CC1)C TVQWPDFMIWQHSB-MDZDMXLPSA-N 0.000 claims 1
QHRKHTPOYBUWTI-UHFFFAOYSA-N N1C=CC2=CC(=CC=C12)NC1=C(C=NC=C1C=CC1=NC=CC=C1)C#N Chemical compound N1C=CC2=CC(=CC=C12)NC1=C(C=NC=C1C=CC1=NC=CC=C1)C#N QHRKHTPOYBUWTI-UHFFFAOYSA-N 0.000 claims 1
DVCHDIIQCXDGBH-UHFFFAOYSA-N NCC(=O)N1CCC(=CC1)C=1C=NC=C(C1NC=1C(=C2C=CNC2=CC1)C)C#N Chemical compound NCC(=O)N1CCC(=CC1)C=1C=NC=C(C1NC=1C(=C2C=CNC2=CC1)C)C#N DVCHDIIQCXDGBH-UHFFFAOYSA-N 0.000 claims 1
PCMQRCTXYLUKAQ-FNORWQNLSA-N OC1(CCN(CC1)CC/C=C/C=1C=NC=C(C#N)C1NC=1C(=C2C=CNC2=CC1)C)C1=CC=CC=C1 Chemical compound OC1(CCN(CC1)CC/C=C/C=1C=NC=C(C#N)C1NC=1C(=C2C=CNC2=CC1)C)C1=CC=CC=C1 PCMQRCTXYLUKAQ-FNORWQNLSA-N 0.000 claims 1
UEJIYGJRIFFCIY-BQYQJAHWSA-N OC1CCN(CC1)CC1=CC=C(C=C1)/C=C/C=1C(=C(C=NC1C)C#N)NC=1C(=C2C=CNC2=CC1)C Chemical compound OC1CCN(CC1)CC1=CC=C(C=C1)/C=C/C=1C(=C(C=NC1C)C#N)NC=1C(=C2C=CNC2=CC1)C UEJIYGJRIFFCIY-BQYQJAHWSA-N 0.000 claims 1
QKEOVKBJCZVJHY-VOTSOKGWSA-N OC1CCN(CC1)CC1=CC=CC(=N1)/C=C/C=1C(=C(C=NC1C)C#N)NC=1C(=C2C=CNC2=CC1)C Chemical compound OC1CCN(CC1)CC1=CC=CC(=N1)/C=C/C=1C(=C(C=NC1C)C#N)NC=1C(=C2C=CNC2=CC1)C QKEOVKBJCZVJHY-VOTSOKGWSA-N 0.000 claims 1
NPEAUASUVOKSFB-AATRIKPKSA-N OC1CCN(CC1)CC=1C=CC(=NC1)/C=C/C=1C(=C(C=NC1C)C#N)NC=1C(=C2C=CNC2=CC1)C Chemical compound OC1CCN(CC1)CC=1C=CC(=NC1)/C=C/C=1C(=C(C=NC1C)C#N)NC=1C(=C2C=CNC2=CC1)C NPEAUASUVOKSFB-AATRIKPKSA-N 0.000 claims 1
UZRRFKCMCXGTFE-BQYQJAHWSA-N OC1CN(CC1)CC1=CC=C(C=C1)/C=C/C=1C(=C(C=NC1C)C#N)NC=1C(=C2C=CNC2=CC1)C Chemical compound OC1CN(CC1)CC1=CC=C(C=C1)/C=C/C=1C(=C(C=NC1C)C#N)NC=1C(=C2C=CNC2=CC1)C UZRRFKCMCXGTFE-BQYQJAHWSA-N 0.000 claims 1
CROQNYCRMAHLQK-VOTSOKGWSA-N OC1CN(CC1)CC1=CC=CC(=N1)/C=C/C=1C(=C(C=NC1C)C#N)NC=1C(=C2C=CNC2=CC1)C Chemical compound OC1CN(CC1)CC1=CC=CC(=N1)/C=C/C=1C(=C(C=NC1C)C#N)NC=1C(=C2C=CNC2=CC1)C CROQNYCRMAHLQK-VOTSOKGWSA-N 0.000 claims 1
CDBKEVDFPQMBAV-AATRIKPKSA-N OC1CN(CC1)CC=1C=CC(=NC1)/C=C/C=1C(=NC=C(C#N)C1NC=1C(=C2C=CNC2=CC1)C)C Chemical compound OC1CN(CC1)CC=1C=CC(=NC1)/C=C/C=1C(=NC=C(C#N)C1NC=1C(=C2C=CNC2=CC1)C)C CDBKEVDFPQMBAV-AATRIKPKSA-N 0.000 claims 1
AHRHXFYKXMUDFF-BQYQJAHWSA-N OCCN1CCN(CC1)CC1=CC=C(C=C1)/C=C/C=1C(=C(C=NC1C)C#N)NC=1C(=C2C=CNC2=CC1)C Chemical compound OCCN1CCN(CC1)CC1=CC=C(C=C1)/C=C/C=1C(=C(C=NC1C)C#N)NC=1C(=C2C=CNC2=CC1)C AHRHXFYKXMUDFF-BQYQJAHWSA-N 0.000 claims 1
OEVWCEONJYJAIQ-AATRIKPKSA-N OCCN1CCN(CC1)CC=1C=CC(=NC1)/C=C/C=1C(=NC=C(C#N)C1NC=1C(=C2C=CNC2=CC1)C)C Chemical compound OCCN1CCN(CC1)CC=1C=CC(=NC1)/C=C/C=1C(=NC=C(C#N)C1NC=1C(=C2C=CNC2=CC1)C)C OEVWCEONJYJAIQ-AATRIKPKSA-N 0.000 claims 1
PWSBRXJNZWIQIR-DUXPYHPUSA-N [(e)-4-[5-cyano-4-[(4-methyl-1h-indol-5-yl)amino]pyridin-3-yl]but-3-enyl] 1,1-dioxo-1,4-thiazinane-4-carboxylate Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CCOC(=O)N1CCS(=O)(=O)CC1 PWSBRXJNZWIQIR-DUXPYHPUSA-N 0.000 claims 1
XHUZCPHCLLUATP-QPJJXVBHSA-N [(e)-4-[5-cyano-4-[(4-methyl-1h-indol-5-yl)amino]pyridin-3-yl]but-3-enyl] 2,3-dihydroindole-1-carboxylate Chemical compound C1CC2=CC=CC=C2N1C(=O)OCC/C=C/C(C=NC=C1C#N)=C1NC1=C(C)C(C=CN2)=C2C=C1 XHUZCPHCLLUATP-QPJJXVBHSA-N 0.000 claims 1
BAKBLTFRFPIQBJ-DUXPYHPUSA-N c1cc2[nH]ccc2c(C)c1Nc(c(cnc1)C#N)c1\C=C\CCNCCN1CCOCC1 Chemical compound c1cc2[nH]ccc2c(C)c1Nc(c(cnc1)C#N)c1\C=C\CCNCCN1CCOCC1 BAKBLTFRFPIQBJ-DUXPYHPUSA-N 0.000 claims 1
MGRBBMYNYDAOPQ-AATRIKPKSA-N c1cc2[nH]ccc2c(C)c1Nc(c(cnc1)C#N)c1\C=C\CN1CCC(NC(=O)OC(C)(C)C)CC1 Chemical compound c1cc2[nH]ccc2c(C)c1Nc(c(cnc1)C#N)c1\C=C\CN1CCC(NC(=O)OC(C)(C)C)CC1 MGRBBMYNYDAOPQ-AATRIKPKSA-N 0.000 claims 1
UROFUBQPJZOJQY-VOTSOKGWSA-N c1cc2[nH]ccc2c(C)c1Nc(c(cnc1)C#N)c1\C=C\c(c1)cncc1OCCCN1CCCCC1 Chemical compound c1cc2[nH]ccc2c(C)c1Nc(c(cnc1)C#N)c1\C=C\c(c1)cncc1OCCCN1CCCCC1 UROFUBQPJZOJQY-VOTSOKGWSA-N 0.000 claims 1
ZDDQCOUAFZUHCV-MDZDMXLPSA-N c1cc2[nH]ccc2c(C)c1Nc(c(cnc1)C#N)c1\C=C\c(cc1)ccc1CN(CC1)CCC1N1CCCCC1 Chemical compound c1cc2[nH]ccc2c(C)c1Nc(c(cnc1)C#N)c1\C=C\c(cc1)ccc1CN(CC1)CCC1N1CCCCC1 ZDDQCOUAFZUHCV-MDZDMXLPSA-N 0.000 claims 1
XYYIWQGGUFFQBR-AATRIKPKSA-N c1cc2[nH]ccc2c(C)c1Nc(c(cnc1)C#N)c1\C=C\c(n1)csc1CCN(CC1)CCC1N1CCCCC1 Chemical compound c1cc2[nH]ccc2c(C)c1Nc(c(cnc1)C#N)c1\C=C\c(n1)csc1CCN(CC1)CCC1N1CCCCC1 XYYIWQGGUFFQBR-AATRIKPKSA-N 0.000 claims 1
SQSBBBZDDIKESI-SOFGYWHQSA-N c1cc2[nH]ccc2c(C)c1Nc(c(cnc1)C#N)c1\C=C\c(nc1)ccc1CN(CC1)CCC1N1CCCCC1 Chemical compound c1cc2[nH]ccc2c(C)c1Nc(c(cnc1)C#N)c1\C=C\c(nc1)ccc1CN(CC1)CCC1N1CCCCC1 SQSBBBZDDIKESI-SOFGYWHQSA-N 0.000 claims 1
CZPKEFWFVCFCTK-SNAWJCMRSA-N c1cc2[nH]ccc2c(C)c1Nc(c(cnc1)C#N)c1\C=C\c1cccnc1 Chemical compound c1cc2[nH]ccc2c(C)c1Nc(c(cnc1)C#N)c1\C=C\c1cccnc1 CZPKEFWFVCFCTK-SNAWJCMRSA-N 0.000 claims 1
108010011222 cyclo(Arg-Pro) Proteins 0.000 claims 1
CGZJWCJQOOVDSV-HWKANZROSA-N n-[1-[(e)-4-[5-cyano-4-[(4-methyl-1h-indol-5-yl)amino]pyridin-3-yl]but-3-enyl]piperidin-4-yl]acetamide Chemical compound C1CC(NC(=O)C)CCN1CC\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C CGZJWCJQOOVDSV-HWKANZROSA-N 0.000 claims 1
OSNSLFCSJAHEKW-FNORWQNLSA-N n-[1-[(e)-4-[5-cyano-4-[(4-methyl-1h-indol-5-yl)amino]pyridin-3-yl]but-3-enyl]piperidin-4-yl]benzenesulfonamide Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CCN(CC1)CCC1NS(=O)(=O)C1=CC=CC=C1 OSNSLFCSJAHEKW-FNORWQNLSA-N 0.000 claims 1
WGNCBVWINIDEOT-GQCTYLIASA-N n-[1-[(e)-4-[5-cyano-4-[(4-methyl-1h-indol-5-yl)amino]pyridin-3-yl]but-3-enyl]piperidin-4-yl]ethanesulfonamide Chemical compound C1CC(NS(=O)(=O)CC)CCN1CC\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C WGNCBVWINIDEOT-GQCTYLIASA-N 0.000 claims 1
NEBLJCMPKZILIG-GQCTYLIASA-N n-[1-[(e)-4-[5-cyano-4-[(4-methyl-1h-indol-5-yl)amino]pyridin-3-yl]but-3-enyl]piperidin-4-yl]propane-2-sulfonamide Chemical compound C1CC(NS(=O)(=O)C(C)C)CCN1CC\C=C\C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C NEBLJCMPKZILIG-GQCTYLIASA-N 0.000 claims 1
LARUDRJOKZLRQE-BQYQJAHWSA-N n1cc(CN(C)C)ccc1\C=C\c1c(C)ncc(C#N)c1Nc1ccc2[nH]ccc2c1C Chemical compound n1cc(CN(C)C)ccc1\C=C\c1c(C)ncc(C#N)c1Nc1ccc2[nH]ccc2c1C LARUDRJOKZLRQE-BQYQJAHWSA-N 0.000 claims 1
125000003107 substituted aryl group Chemical group 0.000 claims 1
QAOWAMXDNUSVQI-UHFFFAOYSA-N tert-butyl 4-[5-cyano-2-methyl-4-[(4-methyl-1h-indol-5-yl)amino]pyridin-3-yl]-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound CC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1C1=CCN(C(=O)OC(C)(C)C)CC1 QAOWAMXDNUSVQI-UHFFFAOYSA-N 0.000 claims 1
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
230000001575 pathological effect Effects 0.000 abstract description 8
230000001404 mediated effect Effects 0.000 abstract description 6
230000002401 inhibitory effect Effects 0.000 abstract description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 303
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 263
238000002360 preparation method Methods 0.000 description 240
238000004128 high performance liquid chromatography Methods 0.000 description 237
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 194
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 167
239000007787 solid Substances 0.000 description 147
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 134
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 133
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 120
238000006243 chemical reaction Methods 0.000 description 115
235000019439 ethyl acetate Nutrition 0.000 description 100
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 89
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 82
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 77
229920006395 saturated elastomer Polymers 0.000 description 77
229910001868 water Inorganic materials 0.000 description 76
239000011541 reaction mixture Substances 0.000 description 69
239000000243 solution Substances 0.000 description 68
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 63
235000017557 sodium bicarbonate Nutrition 0.000 description 62
229910000030 sodium bicarbonate Inorganic materials 0.000 description 62
229910052943 magnesium sulfate Inorganic materials 0.000 description 60
235000019341 magnesium sulphate Nutrition 0.000 description 60
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 53
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 51
235000002639 sodium chloride Nutrition 0.000 description 50
AIBQGNRVNUDNQT-UHFFFAOYSA-N 5-iodo-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(I)C=NC=C1C#N AIBQGNRVNUDNQT-UHFFFAOYSA-N 0.000 description 46
229940086542 triethylamine Drugs 0.000 description 45
239000000706 filtrate Substances 0.000 description 44
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 40
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 39
239000012044 organic layer Substances 0.000 description 37
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 35
238000010992 reflux Methods 0.000 description 35
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 34
ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical compound C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 description 33
239000002904 solvent Substances 0.000 description 32
NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 31
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 28
COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 28
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
238000004440 column chromatography Methods 0.000 description 25
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 24
238000001816 cooling Methods 0.000 description 23
239000006188 syrup Substances 0.000 description 23
235000020357 syrup Nutrition 0.000 description 23
239000000047 product Substances 0.000 description 22
YYXDQRRDNPRJFL-UHFFFAOYSA-N 2-aminopyridine-3-carbonitrile Chemical compound NC1=NC=CC=C1C#N YYXDQRRDNPRJFL-UHFFFAOYSA-N 0.000 description 21
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 20
238000001914 filtration Methods 0.000 description 20
229910000024 caesium carbonate Inorganic materials 0.000 description 19
UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 18
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
239000007788 liquid Substances 0.000 description 17
125000003118 aryl group Chemical group 0.000 description 16
238000003818 flash chromatography Methods 0.000 description 16
239000000543 intermediate Substances 0.000 description 16
238000010898 silica gel chromatography Methods 0.000 description 16
239000000725 suspension Substances 0.000 description 16
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 15
229960000583 acetic acid Drugs 0.000 description 15
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 15
238000003786 synthesis reaction Methods 0.000 description 15
URJMTRSLTCWFQP-UHFFFAOYSA-N 4-chloro-5-iodopyridine-3-carbonitrile Chemical compound ClC1=C(I)C=NC=C1C#N URJMTRSLTCWFQP-UHFFFAOYSA-N 0.000 description 13
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 13
235000011114 ammonium hydroxide Nutrition 0.000 description 13
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 13
150000002148 esters Chemical class 0.000 description 13
125000001072 heteroaryl group Chemical group 0.000 description 13
239000012321 sodium triacetoxyborohydride Substances 0.000 description 13
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 12
VKIJXFIYBAYHOE-VOTSOKGWSA-N [(e)-2-phenylethenyl]boronic acid Chemical compound OB(O)\C=C\C1=CC=CC=C1 VKIJXFIYBAYHOE-VOTSOKGWSA-N 0.000 description 12
230000015572 biosynthetic process Effects 0.000 description 12
239000012267 brine Substances 0.000 description 12
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
239000000284 extract Substances 0.000 description 11
239000010410 layer Substances 0.000 description 11
QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 11
238000005406 washing Methods 0.000 description 11
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 10
125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 10
108090000315 Protein Kinase C Proteins 0.000 description 10
102000003923 Protein Kinase C Human genes 0.000 description 10
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 10
239000013058 crude material Substances 0.000 description 10
125000001188 haloalkyl group Chemical group 0.000 description 10
239000003921 oil Substances 0.000 description 10
238000002953 preparative HPLC Methods 0.000 description 10
CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 10
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 9
KKJULHJTGFGPHO-WUXMJOGZSA-N [(e)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-enyl] 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC\C=C\B1OC(C)(C)C(C)(C)O1 KKJULHJTGFGPHO-WUXMJOGZSA-N 0.000 description 9
235000019198 oils Nutrition 0.000 description 9
229910000027 potassium carbonate Inorganic materials 0.000 description 9
239000000843 powder Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 9
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
229910004373 HOAc Inorganic materials 0.000 description 8
108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 8
102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 8
125000003545 alkoxy group Chemical group 0.000 description 8
208000035475 disorder Diseases 0.000 description 8
238000009472 formulation Methods 0.000 description 8
238000010438 heat treatment Methods 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
235000011121 sodium hydroxide Nutrition 0.000 description 8
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
RTMAXKVUWBOPCP-UHFFFAOYSA-N 1-[(6-ethenylpyridin-3-yl)methyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CC1=CC=C(C=C)N=C1 RTMAXKVUWBOPCP-UHFFFAOYSA-N 0.000 description 7
ZSGWFOMHWZIAEW-UHFFFAOYSA-N 4-oxo-1h-pyridine-3-carbonitrile Chemical compound O=C1C=CNC=C1C#N ZSGWFOMHWZIAEW-UHFFFAOYSA-N 0.000 description 7
HOUXWDSMADXKKQ-UHFFFAOYSA-N 5-bromo-4-chloro-6-methylpyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(Cl)=C1Br HOUXWDSMADXKKQ-UHFFFAOYSA-N 0.000 description 7
POVXMNTWCYPPGX-UHFFFAOYSA-N 5-bromo-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)=C1Br POVXMNTWCYPPGX-UHFFFAOYSA-N 0.000 description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
239000012359 Methanesulfonyl chloride Substances 0.000 description 7
ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 7
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
150000001336 alkenes Chemical class 0.000 description 7
239000012043 crude product Substances 0.000 description 7
125000000623 heterocyclic group Chemical group 0.000 description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 7
235000011181 potassium carbonates Nutrition 0.000 description 7
238000000746 purification Methods 0.000 description 7
229910052938 sodium sulfate Inorganic materials 0.000 description 7
235000011152 sodium sulphate Nutrition 0.000 description 7
KIWXRZCNWWBIOF-NSCUHMNNSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[(e)-2-pyrazin-2-ylethenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C1=CN=CC=N1 KIWXRZCNWWBIOF-NSCUHMNNSA-N 0.000 description 6
GMMIFTFUOIWOPM-VOTSOKGWSA-N 4-chloro-5-[(e)-2-phenylethenyl]pyridine-3-carbonitrile Chemical compound C1=NC=C(C#N)C(Cl)=C1\C=C\C1=CC=CC=C1 GMMIFTFUOIWOPM-VOTSOKGWSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000000908 ammonium hydroxide Substances 0.000 description 6
QCAWEPFNJXQPAN-UHFFFAOYSA-N methoxyfenozide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=C(C)C=C(C)C=2)C(C)(C)C)=C1C QCAWEPFNJXQPAN-UHFFFAOYSA-N 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
239000000829 suppository Substances 0.000 description 6
GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 5
NDHAYBONKWQJBC-UHFFFAOYSA-N 2-iodo-5-[(4-methylpiperazin-1-yl)methyl]phenol Chemical compound C1CN(C)CCN1CC1=CC=C(I)C(O)=C1 NDHAYBONKWQJBC-UHFFFAOYSA-N 0.000 description 5
HIMHZFMRAZKTLW-UHFFFAOYSA-N 4-[(2,4-dimethyl-1h-indol-5-yl)amino]-5-iodopyridine-3-carbonitrile Chemical compound C=1C=C2NC(C)=CC2=C(C)C=1NC1=C(I)C=NC=C1C#N HIMHZFMRAZKTLW-UHFFFAOYSA-N 0.000 description 5
OXIQAZMTJBCNLM-UHFFFAOYSA-N 4-[(7-chloro-4-methyl-1h-indol-5-yl)amino]-5-iodopyridine-3-carbonitrile Chemical compound C1=C(Cl)C=2NC=CC=2C(C)=C1NC1=C(I)C=NC=C1C#N OXIQAZMTJBCNLM-UHFFFAOYSA-N 0.000 description 5
LLUMZCODEQVYRF-UHFFFAOYSA-N 4-methyl-1h-indol-5-amine Chemical compound CC1=C(N)C=CC2=C1C=CN2 LLUMZCODEQVYRF-UHFFFAOYSA-N 0.000 description 5
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
108091000080 Phosphotransferase Proteins 0.000 description 5
239000002253 acid Substances 0.000 description 5
150000001335 aliphatic alkanes Chemical group 0.000 description 5
239000002775 capsule Substances 0.000 description 5
150000001721 carbon Chemical group 0.000 description 5
230000003197 catalytic effect Effects 0.000 description 5
229940125758 compound 15 Drugs 0.000 description 5
238000010511 deprotection reaction Methods 0.000 description 5
YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 5
201000010099 disease Diseases 0.000 description 5
125000001041 indolyl group Chemical group 0.000 description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
239000012038 nucleophile Substances 0.000 description 5
239000008194 pharmaceutical composition Substances 0.000 description 5
102000020233 phosphotransferase Human genes 0.000 description 5
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 5
125000006239 protecting group Chemical group 0.000 description 5
108020003175 receptors Proteins 0.000 description 5
102000005962 receptors Human genes 0.000 description 5
230000002829 reductive effect Effects 0.000 description 5
150000003335 secondary amines Chemical class 0.000 description 5
235000009518 sodium iodide Nutrition 0.000 description 5
239000003826 tablet Substances 0.000 description 5
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 5
CVNACBWETZPXOQ-UHFFFAOYSA-N 1-[(2-ethenylpyridin-4-yl)methyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CC1=CC=NC(C=C)=C1 CVNACBWETZPXOQ-UHFFFAOYSA-N 0.000 description 4
238000005160 1H NMR spectroscopy Methods 0.000 description 4
TYHYESDUJZRBKS-UHFFFAOYSA-N 2,3-dihydroindole-1-carboxylic acid Chemical compound C1=CC=C2N(C(=O)O)CCC2=C1 TYHYESDUJZRBKS-UHFFFAOYSA-N 0.000 description 4
FYHBHADHHWPOFL-SOFGYWHQSA-N 2-[(e)-5-chloropent-1-enyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound CC1(C)OB(\C=C\CCCCl)OC1(C)C FYHBHADHHWPOFL-SOFGYWHQSA-N 0.000 description 4
SZDPZQAPHXPVCN-UHFFFAOYSA-N 3-bromo-2-methoxybenzaldehyde Chemical compound COC1=C(Br)C=CC=C1C=O SZDPZQAPHXPVCN-UHFFFAOYSA-N 0.000 description 4
RVWOHBWQJGLXIJ-UHFFFAOYSA-N 3-iodo-4-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1I RVWOHBWQJGLXIJ-UHFFFAOYSA-N 0.000 description 4
CSNYGCVBIQMGFX-UHFFFAOYSA-N 4-(1h-indol-5-yloxy)-5-iodopyridine-3-carbonitrile Chemical compound IC1=CN=CC(C#N)=C1OC1=CC=C(NC=C2)C2=C1 CSNYGCVBIQMGFX-UHFFFAOYSA-N 0.000 description 4
MXEBPDNIQTVOCU-UHFFFAOYSA-N 4-chloro-5-[(3,4-dimethoxyphenyl)methyl]pyridine-3-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1CC1=CN=CC(C#N)=C1Cl MXEBPDNIQTVOCU-UHFFFAOYSA-N 0.000 description 4
PHSPBXTVMJOTQN-UHFFFAOYSA-N 4-iodo-3-methoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC=C1I PHSPBXTVMJOTQN-UHFFFAOYSA-N 0.000 description 4
QTBJCVGYQDMUCZ-UHFFFAOYSA-N 5-iodo-4-oxo-1h-pyridine-3-carbonitrile Chemical compound OC1=C(I)C=NC=C1C#N QTBJCVGYQDMUCZ-UHFFFAOYSA-N 0.000 description 4
YEBSZPPMTBMVAY-UHFFFAOYSA-N 5-iodo-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)=C1I YEBSZPPMTBMVAY-UHFFFAOYSA-N 0.000 description 4
UFNIEHDULKSNQU-UHFFFAOYSA-N 5-iodo-6-methyl-4-oxo-1h-pyridine-3-carboxamide Chemical compound CC=1NC=C(C(N)=O)C(=O)C=1I UFNIEHDULKSNQU-UHFFFAOYSA-N 0.000 description 4
JYAMNOJMPNSKGL-UHFFFAOYSA-N 5-tert-butyl-2-phenylpyrazole-3-carboxylic acid Chemical compound N1=C(C(C)(C)C)C=C(C(O)=O)N1C1=CC=CC=C1 JYAMNOJMPNSKGL-UHFFFAOYSA-N 0.000 description 4
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
101001051767 Homo sapiens Protein kinase C beta type Proteins 0.000 description 4
101001059454 Homo sapiens Serine/threonine-protein kinase MARK2 Proteins 0.000 description 4
108091054455 MAP kinase family Proteins 0.000 description 4
102000043136 MAP kinase family Human genes 0.000 description 4
241000699670 Mus sp. Species 0.000 description 4
238000005481 NMR spectroscopy Methods 0.000 description 4
102000001708 Protein Isoforms Human genes 0.000 description 4
108010029485 Protein Isoforms Proteins 0.000 description 4
102100024923 Protein kinase C beta type Human genes 0.000 description 4
102100028904 Serine/threonine-protein kinase MARK2 Human genes 0.000 description 4
238000006619 Stille reaction Methods 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
150000001345 alkine derivatives Chemical class 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
239000000969 carrier Substances 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
239000007819 coupling partner Substances 0.000 description 4
238000005859 coupling reaction Methods 0.000 description 4
239000006071 cream Substances 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
239000002552 dosage form Substances 0.000 description 4
239000003480 eluent Substances 0.000 description 4
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 4
210000003630 histaminocyte Anatomy 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
239000000463 material Substances 0.000 description 4
HXRAMSFGUAOAJR-UHFFFAOYSA-N n,n,n',n'-tetramethyl-1-[(2-methylpropan-2-yl)oxy]methanediamine Chemical compound CN(C)C(N(C)C)OC(C)(C)C HXRAMSFGUAOAJR-UHFFFAOYSA-N 0.000 description 4
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 4
239000003380 propellant Substances 0.000 description 4
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 4
230000019491 signal transduction Effects 0.000 description 4
239000011734 sodium Substances 0.000 description 4
239000008247 solid mixture Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
125000001544 thienyl group Chemical group 0.000 description 4
230000009466 transformation Effects 0.000 description 4
OXIDIXNJKFAHMG-UHFFFAOYSA-N (3-iodo-4-methylphenyl)-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(C)C(I)=C1 OXIDIXNJKFAHMG-UHFFFAOYSA-N 0.000 description 3
FQEOBYXEKYKLEO-UHFFFAOYSA-N (6-ethenylpyridin-2-yl)methanol Chemical compound OCC1=CC=CC(C=C)=N1 FQEOBYXEKYKLEO-UHFFFAOYSA-N 0.000 description 3
NPXRTHTXQJNMHF-UHFFFAOYSA-N (6-ethenylpyridin-3-yl)methanol Chemical compound OCC1=CC=C(C=C)N=C1 NPXRTHTXQJNMHF-UHFFFAOYSA-N 0.000 description 3
RUVMGYAFIIRKOB-UHFFFAOYSA-N 1-[(3-bromo-2-methoxyphenyl)methyl]-4-methylpiperazine Chemical compound COC1=C(Br)C=CC=C1CN1CCN(C)CC1 RUVMGYAFIIRKOB-UHFFFAOYSA-N 0.000 description 3
LVMPBTDKHPMXLK-UHFFFAOYSA-N 1-[(3-bromo-5-methoxyphenyl)methyl]-4-methylpiperazine Chemical compound COC1=CC(Br)=CC(CN2CCN(C)CC2)=C1 LVMPBTDKHPMXLK-UHFFFAOYSA-N 0.000 description 3
NDEXIUUGKHNOQH-UHFFFAOYSA-N 1-[(6-ethenylpyridin-2-yl)methyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CC1=CC=CC(C=C)=N1 NDEXIUUGKHNOQH-UHFFFAOYSA-N 0.000 description 3
IMQGYGVBPCFWOI-UHFFFAOYSA-N 1-[4-[(6-bromopyridin-2-yl)methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CC1=CC=CC(Br)=N1 IMQGYGVBPCFWOI-UHFFFAOYSA-N 0.000 description 3
JIHLGPMYZCDKNK-UHFFFAOYSA-N 1-[4-[(6-ethenylpyridin-2-yl)methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CC1=CC=CC(C=C)=N1 JIHLGPMYZCDKNK-UHFFFAOYSA-N 0.000 description 3
ZCBIFHNDZBSCEP-UHFFFAOYSA-N 1H-indol-5-amine Chemical compound NC1=CC=C2NC=CC2=C1 ZCBIFHNDZBSCEP-UHFFFAOYSA-N 0.000 description 3
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 3
OPXYNEYEDHAXOM-UHFFFAOYSA-N 3-oxobutanenitrile Chemical compound CC(=O)CC#N OPXYNEYEDHAXOM-UHFFFAOYSA-N 0.000 description 3
CKKWMSXZPICICA-UHFFFAOYSA-N 4,7-dimethyl-1h-indol-5-amine Chemical compound CC1=CC(N)=C(C)C2=C1NC=C2 CKKWMSXZPICICA-UHFFFAOYSA-N 0.000 description 3
UHRHJJYVWSYXSS-UHFFFAOYSA-N 4-(1h-indol-4-yloxy)-5-iodopyridine-3-carbonitrile Chemical compound IC1=CN=CC(C#N)=C1OC1=CC=CC2=C1C=CN2 UHRHJJYVWSYXSS-UHFFFAOYSA-N 0.000 description 3
FQWPEENCVQDWDK-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-iodopyridine-3-carbonitrile Chemical compound IC1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1 FQWPEENCVQDWDK-UHFFFAOYSA-N 0.000 description 3
LUNUNJFSHKSXGQ-UHFFFAOYSA-N 4-Aminoindole Chemical compound NC1=CC=CC2=C1C=CN2 LUNUNJFSHKSXGQ-UHFFFAOYSA-N 0.000 description 3
ACWRKBFMNZQQNE-UHFFFAOYSA-N 4-[(4,7-dimethyl-1h-indol-5-yl)amino]-5-iodopyridine-3-carbonitrile Chemical compound CC=1C=2C=CNC=2C(C)=CC=1NC1=C(I)C=NC=C1C#N ACWRKBFMNZQQNE-UHFFFAOYSA-N 0.000 description 3
IAOCPQXAWJXUKZ-UHFFFAOYSA-N 4-chloro-5-ethenylpyridine-3-carbonitrile Chemical compound ClC1=C(C=C)C=NC=C1C#N IAOCPQXAWJXUKZ-UHFFFAOYSA-N 0.000 description 3
GVOOAQOBOZJTJH-UHFFFAOYSA-N 4-chloro-5-iodo-6-methylpyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(Cl)=C1I GVOOAQOBOZJTJH-UHFFFAOYSA-N 0.000 description 3
NYTZJURBIUIUQY-UHFFFAOYSA-N 4-ethenyl-2-[(4-methylpiperazin-1-yl)methyl]-1,3-thiazole Chemical compound C1CN(C)CCN1CC1=NC(C=C)=CS1 NYTZJURBIUIUQY-UHFFFAOYSA-N 0.000 description 3
MSOMUMGPCHBUKG-UHFFFAOYSA-N 4-iodo-3-methylbenzaldehyde Chemical compound CC1=CC(C=O)=CC=C1I MSOMUMGPCHBUKG-UHFFFAOYSA-N 0.000 description 3
WGORLCHPUNEBLB-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-2-(dimethylaminomethylidene)-3-oxopentanenitrile Chemical compound COC1=CC=C(CCC(=O)C(=CN(C)C)C#N)C=C1OC WGORLCHPUNEBLB-UHFFFAOYSA-N 0.000 description 3
LKXCKZKQVYRFCF-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-3-oxopentanenitrile Chemical compound COC1=CC=C(CCC(=O)CC#N)C=C1OC LKXCKZKQVYRFCF-UHFFFAOYSA-N 0.000 description 3
MAQMWCBTQFYCPL-UHFFFAOYSA-N 5-(dimethylamino)-2-(dimethylaminomethylidene)-3-oxopent-4-enenitrile Chemical compound CN(C)C=CC(=O)C(C#N)=CN(C)C MAQMWCBTQFYCPL-UHFFFAOYSA-N 0.000 description 3
GHHDTICSEFKRHL-UHFFFAOYSA-N 5-[(3,4-dimethoxyphenyl)methyl]-4-oxo-1h-pyridine-3-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1CC1=CNC=C(C#N)C1=O GHHDTICSEFKRHL-UHFFFAOYSA-N 0.000 description 3
CFOPENUBRJEBGU-UHFFFAOYSA-N 5-bromo-4-(1h-indol-4-ylamino)-6-methylpyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C=3C=CNC=3C=CC=2)=C1Br CFOPENUBRJEBGU-UHFFFAOYSA-N 0.000 description 3
YDZSDTPNFSVQTE-UHFFFAOYSA-N 5-bromo-4-(1h-indol-5-ylamino)-6-methylpyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C=C3C=CNC3=CC=2)=C1Br YDZSDTPNFSVQTE-UHFFFAOYSA-N 0.000 description 3
LQTNXLPAIDOUOH-UHFFFAOYSA-N 5-bromo-4-(1h-indol-6-ylamino)-6-methylpyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C=C3NC=CC3=CC=2)=C1Br LQTNXLPAIDOUOH-UHFFFAOYSA-N 0.000 description 3
MCXRYOPARNHUKG-UHFFFAOYSA-N 5-bromo-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(Br)C=NC=C1C#N MCXRYOPARNHUKG-UHFFFAOYSA-N 0.000 description 3
UCTMXXZSXWOFPU-UHFFFAOYSA-N 5-bromo-4-chloro-6-ethylpyridine-3-carbonitrile Chemical compound CCC1=NC=C(C#N)C(Cl)=C1Br UCTMXXZSXWOFPU-UHFFFAOYSA-N 0.000 description 3
PRHCFBYVNSILBW-UHFFFAOYSA-N 5-bromo-4-chloropyridine-3-carbonitrile Chemical compound ClC1=C(Br)C=NC=C1C#N PRHCFBYVNSILBW-UHFFFAOYSA-N 0.000 description 3
JJNPXAFLCPYPCD-UHFFFAOYSA-N 5-bromo-4-oxo-1h-pyridine-3-carbonitrile Chemical compound BrC1=CNC=C(C#N)C1=O JJNPXAFLCPYPCD-UHFFFAOYSA-N 0.000 description 3
SUVWKOGPCNISMA-UHFFFAOYSA-N 5-bromo-6-methyl-4-oxo-1h-pyridine-3-carboxamide Chemical compound CC=1NC=C(C(N)=O)C(=O)C=1Br SUVWKOGPCNISMA-UHFFFAOYSA-N 0.000 description 3
AFOTZKWPHPDPAH-UHFFFAOYSA-N 5-bromo-6-methyl-4-oxo-1h-pyridine-3-carboxylic acid Chemical compound CC=1NC=C(C(O)=O)C(=O)C=1Br AFOTZKWPHPDPAH-UHFFFAOYSA-N 0.000 description 3
ARFUMKCIPQBDJF-UHFFFAOYSA-N 5-iodo-6-methyl-4-[(2-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C=1C=C2NC(C)=CC2=CC=1NC1=C(I)C(C)=NC=C1C#N ARFUMKCIPQBDJF-UHFFFAOYSA-N 0.000 description 3
AOJLDZLRTUWFFY-UHFFFAOYSA-N 6-methyl-4-oxo-1h-pyridine-3-carboxylic acid Chemical compound CC1=CC(=O)C(C(O)=O)=CN1 AOJLDZLRTUWFFY-UHFFFAOYSA-N 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 3
238000007341 Heck reaction Methods 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
208000002200 Respiratory Hypersensitivity Diseases 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 3
PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 3
230000009471 action Effects 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
239000000443 aerosol Substances 0.000 description 3
230000010085 airway hyperresponsiveness Effects 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
229940125810 compound 20 Drugs 0.000 description 3
229940126086 compound 21 Drugs 0.000 description 3
238000007906 compression Methods 0.000 description 3
230000006835 compression Effects 0.000 description 3
230000008878 coupling Effects 0.000 description 3
238000010168 coupling process Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
125000004122 cyclic group Chemical group 0.000 description 3
230000002950 deficient Effects 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
238000006073 displacement reaction Methods 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
125000001153 fluoro group Chemical group F* 0.000 description 3
235000011187 glycerol Nutrition 0.000 description 3
JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 3
125000001183 hydrocarbyl group Chemical group 0.000 description 3
239000011630 iodine Substances 0.000 description 3
239000008101 lactose Substances 0.000 description 3
239000003446 ligand Substances 0.000 description 3
125000002950 monocyclic group Chemical group 0.000 description 3
STUHQDIOZQUPGP-UHFFFAOYSA-N morpholin-4-ium-4-carboxylate Chemical compound OC(=O)N1CCOCC1 STUHQDIOZQUPGP-UHFFFAOYSA-N 0.000 description 3
IPRXWEPMOALPTO-UHFFFAOYSA-N n-(2,5-dimethyl-4-nitrophenyl)acetamide Chemical compound CC(=O)NC1=CC(C)=C([N+]([O-])=O)C=C1C IPRXWEPMOALPTO-UHFFFAOYSA-N 0.000 description 3
LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 3
238000007911 parenteral administration Methods 0.000 description 3
229920001223 polyethylene glycol Polymers 0.000 description 3
125000006238 prop-1-en-1-yl group Chemical group [H]\C(*)=C(/[H])C([H])([H])[H] 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
150000003254 radicals Chemical group 0.000 description 3
125000006413 ring segment Chemical group 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
230000006103 sulfonylation Effects 0.000 description 3
238000005694 sulfonylation reaction Methods 0.000 description 3
239000004094 surface-active agent Substances 0.000 description 3
239000000375 suspending agent Substances 0.000 description 3
208000024891 symptom Diseases 0.000 description 3
UGRXPDVLRCRMKP-UHFFFAOYSA-N tert-butyl 4-[(3-iodo-4-methoxyphenyl)methyl]piperazine-1-carboxylate Chemical compound C1=C(I)C(OC)=CC=C1CN1CCN(C(=O)OC(C)(C)C)CC1 UGRXPDVLRCRMKP-UHFFFAOYSA-N 0.000 description 3
BHOIHSGJJCTRMQ-UHFFFAOYSA-N tert-butyl 4-[(6-ethenylpyridin-3-yl)methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CC1=CC=C(C=C)N=C1 BHOIHSGJJCTRMQ-UHFFFAOYSA-N 0.000 description 3
150000003512 tertiary amines Chemical class 0.000 description 3
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 3
238000001665 trituration Methods 0.000 description 3
239000003039 volatile agent Substances 0.000 description 3
MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 description 2
KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 2
NJXYTXADXSRFTJ-UHFFFAOYSA-N 1,2-Dimethoxy-4-vinylbenzene Chemical compound COC1=CC=C(C=C)C=C1OC NJXYTXADXSRFTJ-UHFFFAOYSA-N 0.000 description 2
CFTYPNVBHHDBHO-UHFFFAOYSA-N 1-(5-amino-4,7-dimethylindol-1-yl)ethanone Chemical compound NC1=CC(C)=C2N(C(=O)C)C=CC2=C1C CFTYPNVBHHDBHO-UHFFFAOYSA-N 0.000 description 2
KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 2
RKGULGUMQWUUOY-UHFFFAOYSA-N 1-[(3-iodo-4-methylphenyl)methyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CC1=CC=C(C)C(I)=C1 RKGULGUMQWUUOY-UHFFFAOYSA-N 0.000 description 2
ZQPYMFANIVJVKT-UHFFFAOYSA-N 1-[(4-ethynylphenyl)methyl]pyrrolidine Chemical compound C1=CC(C#C)=CC=C1CN1CCCC1 ZQPYMFANIVJVKT-UHFFFAOYSA-N 0.000 description 2
PLUBPQCDHHDHBN-UHFFFAOYSA-N 1-[(4-iodo-3-methoxyphenyl)methyl]-4-methylpiperazine Chemical compound C1=C(I)C(OC)=CC(CN2CCN(C)CC2)=C1 PLUBPQCDHHDHBN-UHFFFAOYSA-N 0.000 description 2
UJLJUXIFSCIDCK-UHFFFAOYSA-N 1-[(4-iodo-3-methylphenyl)methyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CC1=CC=C(I)C(C)=C1 UJLJUXIFSCIDCK-UHFFFAOYSA-N 0.000 description 2
MUKOKIXKKLJMMH-UHFFFAOYSA-N 1-[(6-bromopyridin-3-yl)methyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CC1=CC=C(Br)N=C1 MUKOKIXKKLJMMH-UHFFFAOYSA-N 0.000 description 2
ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 2
BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 2
MIMYTSWNVBMNRH-UHFFFAOYSA-N 1h-indol-6-amine Chemical compound NC1=CC=C2C=CNC2=C1 MIMYTSWNVBMNRH-UHFFFAOYSA-N 0.000 description 2
VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 2
WGFNXGPBPIJYLI-UHFFFAOYSA-N 2,6-difluoro-3-[(3-fluorophenyl)sulfonylamino]-n-(3-methoxy-1h-pyrazolo[3,4-b]pyridin-5-yl)benzamide Chemical compound C1=C2C(OC)=NNC2=NC=C1NC(=O)C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC=CC(F)=C1 WGFNXGPBPIJYLI-UHFFFAOYSA-N 0.000 description 2
VMKLFIODENULHK-UHFFFAOYSA-N 2-(3-methoxyphenyl)ethenylboronic acid Chemical compound COC1=CC=CC(C=CB(O)O)=C1 VMKLFIODENULHK-UHFFFAOYSA-N 0.000 description 2
JWTZSVLLPKTZJP-UHFFFAOYSA-N 2-bromo-6-chloropyridine Chemical compound ClC1=CC=CC(Br)=N1 JWTZSVLLPKTZJP-UHFFFAOYSA-N 0.000 description 2
KANZWHBYRHQMKZ-UHFFFAOYSA-N 2-ethenylpyrazine Chemical compound C=CC1=CN=CC=N1 KANZWHBYRHQMKZ-UHFFFAOYSA-N 0.000 description 2
JQULCCZIXYRBSE-UHFFFAOYSA-N 2-methyl-1h-indol-5-amine Chemical compound NC1=CC=C2NC(C)=CC2=C1 JQULCCZIXYRBSE-UHFFFAOYSA-N 0.000 description 2
KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 2
QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 2
IHLOHISMHMTTAA-UHFFFAOYSA-N 3-hydroxy-4-iodobenzaldehyde Chemical compound OC1=CC(C=O)=CC=C1I IHLOHISMHMTTAA-UHFFFAOYSA-N 0.000 description 2
ARAINKADEARZLZ-ZHACJKMWSA-N 4,4,5,5-tetramethyl-2-[(e)-2-phenylethenyl]-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1\C=C\C1=CC=CC=C1 ARAINKADEARZLZ-ZHACJKMWSA-N 0.000 description 2
ZHUASKJVRUTKHP-UHFFFAOYSA-N 4-(1h-indol-4-ylamino)-5-iodo-6-methylpyridine-3-carbonitrile Chemical compound CC1=NC=C(C#N)C(NC=2C=3C=CNC=3C=CC=2)=C1I ZHUASKJVRUTKHP-UHFFFAOYSA-N 0.000 description 2
JNAVAEYSYAUXKN-UHFFFAOYSA-N 4-[(3,4-dimethoxyphenyl)methyl]-5-(dimethylamino)-2-(dimethylaminomethylidene)-3-oxopent-4-enenitrile Chemical compound COC1=CC=C(CC(=CN(C)C)C(=O)C(=CN(C)C)C#N)C=C1OC JNAVAEYSYAUXKN-UHFFFAOYSA-N 0.000 description 2
WPRALQOUSNATIP-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-propylpyridine-3-carbonitrile Chemical compound CCCC1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C WPRALQOUSNATIP-UHFFFAOYSA-N 0.000 description 2
HXTWKHXDFATMSP-UHFFFAOYSA-N 4-bromo-2-hydroxybenzaldehyde Chemical compound OC1=CC(Br)=CC=C1C=O HXTWKHXDFATMSP-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
KNUZTACRVSYPNI-UHFFFAOYSA-N 5-iodo-6-methyl-4-oxo-1h-pyridine-3-carboxylic acid Chemical compound CC=1NC=C(C(O)=O)C(=O)C=1I KNUZTACRVSYPNI-UHFFFAOYSA-N 0.000 description 2
QWFHFNGMCPMOCD-UHFFFAOYSA-N 6-bromopyridine-2-carbaldehyde Chemical compound BrC1=CC=CC(C=O)=N1 QWFHFNGMCPMOCD-UHFFFAOYSA-N 0.000 description 2
PVUKGNBRJFTFNJ-UHFFFAOYSA-N 6-bromopyridine-3-carbaldehyde Chemical compound BrC1=CC=C(C=O)C=N1 PVUKGNBRJFTFNJ-UHFFFAOYSA-N 0.000 description 2
ZKHQWZAMYRWXGA-KQYNXXCUSA-J ATP(4-) Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-J 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 2
239000005695 Ammonium acetate Substances 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
102000008130 Cyclic AMP-Dependent Protein Kinases Human genes 0.000 description 2
102000018233 Fibroblast Growth Factor Human genes 0.000 description 2
108050007372 Fibroblast Growth Factor Proteins 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
102000003816 Interleukin-13 Human genes 0.000 description 2
108090000176 Interleukin-13 Proteins 0.000 description 2
102000000588 Interleukin-2 Human genes 0.000 description 2
108010002350 Interleukin-2 Proteins 0.000 description 2
102000004388 Interleukin-4 Human genes 0.000 description 2
108090000978 Interleukin-4 Proteins 0.000 description 2
102000004889 Interleukin-6 Human genes 0.000 description 2
108090001005 Interleukin-6 Proteins 0.000 description 2
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
229920000168 Microcrystalline cellulose Polymers 0.000 description 2
108090000744 Mitogen-Activated Protein Kinase Kinases Proteins 0.000 description 2
102000004232 Mitogen-Activated Protein Kinase Kinases Human genes 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
108010038512 Platelet-Derived Growth Factor Proteins 0.000 description 2
102000010780 Platelet-Derived Growth Factor Human genes 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
238000006069 Suzuki reaction reaction Methods 0.000 description 2
230000006044 T cell activation Effects 0.000 description 2
108091008874 T cell receptors Proteins 0.000 description 2
102000016266 T-Cell Antigen Receptors Human genes 0.000 description 2
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 2
108060008682 Tumor Necrosis Factor Proteins 0.000 description 2
102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 2
108010073929 Vascular Endothelial Growth Factor A Proteins 0.000 description 2
102000005789 Vascular Endothelial Growth Factors Human genes 0.000 description 2
108010019530 Vascular Endothelial Growth Factors Proteins 0.000 description 2
LGSBCAPDUJYMOQ-VOTSOKGWSA-N [(e)-2-(4-methoxyphenyl)ethenyl]boronic acid Chemical compound COC1=CC=C(\C=C\B(O)O)C=C1 LGSBCAPDUJYMOQ-VOTSOKGWSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
239000000654 additive Substances 0.000 description 2
239000004479 aerosol dispenser Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
125000005907 alkyl ester group Chemical group 0.000 description 2
230000009435 amidation Effects 0.000 description 2
238000007112 amidation reaction Methods 0.000 description 2
229940043376 ammonium acetate Drugs 0.000 description 2
235000019257 ammonium acetate Nutrition 0.000 description 2
239000000538 analytical sample Substances 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
150000007860 aryl ester derivatives Chemical class 0.000 description 2
150000001502 aryl halides Chemical class 0.000 description 2
125000000732 arylene group Chemical group 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
125000002619 bicyclic group Chemical group 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
230000004071 biological effect Effects 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
239000008280 blood Substances 0.000 description 2
239000000872 buffer Substances 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
101150073031 cdk2 gene Proteins 0.000 description 2
210000004027 cell Anatomy 0.000 description 2
230000001413 cellular effect Effects 0.000 description 2
230000036755 cellular response Effects 0.000 description 2
235000010980 cellulose Nutrition 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
229940126142 compound 16 Drugs 0.000 description 2
229940125846 compound 25 Drugs 0.000 description 2
229940125877 compound 31 Drugs 0.000 description 2
GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 2
238000004132 cross linking Methods 0.000 description 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
230000001086 cytosolic effect Effects 0.000 description 2
125000004652 decahydroisoquinolinyl group Chemical group C1(NCCC2CCCCC12)* 0.000 description 2
230000007547 defect Effects 0.000 description 2
230000001419 dependent effect Effects 0.000 description 2
LHUZAYREVYDAGJ-UHFFFAOYSA-N dichloromethane;ethyl acetate;methanol Chemical compound OC.ClCCl.CCOC(C)=O LHUZAYREVYDAGJ-UHFFFAOYSA-N 0.000 description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
UCZLBERYFYDXOM-UHFFFAOYSA-N ethenyltin Chemical compound [Sn]C=C UCZLBERYFYDXOM-UHFFFAOYSA-N 0.000 description 2
DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 2
GFAGDEMAMZYNAI-UHFFFAOYSA-N ethyl 3-(3,4-dimethoxyphenyl)propanoate Chemical compound CCOC(=O)CCC1=CC=C(OC)C(OC)=C1 GFAGDEMAMZYNAI-UHFFFAOYSA-N 0.000 description 2
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
229940126864 fibroblast growth factor Drugs 0.000 description 2
239000000945 filler Substances 0.000 description 2
239000012065 filter cake Substances 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
239000006260 foam Substances 0.000 description 2
235000013355 food flavoring agent Nutrition 0.000 description 2
239000012458 free base Substances 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
150000004677 hydrates Chemical class 0.000 description 2
150000005828 hydrofluoroalkanes Chemical class 0.000 description 2
230000001771 impaired effect Effects 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
208000027866 inflammatory disease Diseases 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
229940028885 interleukin-4 Drugs 0.000 description 2
229940100601 interleukin-6 Drugs 0.000 description 2
238000007912 intraperitoneal administration Methods 0.000 description 2
239000007928 intraperitoneal injection Substances 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
150000002632 lipids Chemical class 0.000 description 2
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 2
239000006210 lotion Substances 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
239000012528 membrane Substances 0.000 description 2
210000004379 membrane Anatomy 0.000 description 2
TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
244000005700 microbiome Species 0.000 description 2
235000019813 microcrystalline cellulose Nutrition 0.000 description 2
239000002088 nanocapsule Substances 0.000 description 2
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
239000002674 ointment Substances 0.000 description 2
ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
235000015320 potassium carbonate Nutrition 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
102000004169 proteins and genes Human genes 0.000 description 2
108090000623 proteins and genes Proteins 0.000 description 2
108091008598 receptor tyrosine kinases Proteins 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000006722 reduction reaction Methods 0.000 description 2
238000006268 reductive amination reaction Methods 0.000 description 2
230000004044 response Effects 0.000 description 2
102220097509 rs876658798 Human genes 0.000 description 2
210000003491 skin Anatomy 0.000 description 2
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
235000019333 sodium laurylsulphate Nutrition 0.000 description 2
239000007921 spray Substances 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
239000008107 starch Substances 0.000 description 2
239000008174 sterile solution Substances 0.000 description 2
238000003860 storage Methods 0.000 description 2
239000007929 subcutaneous injection Substances 0.000 description 2
238000010254 subcutaneous injection Methods 0.000 description 2
235000000346 sugar Nutrition 0.000 description 2
150000008163 sugars Chemical class 0.000 description 2
OGZHMGNGPRNCAQ-UHFFFAOYSA-N tert-butyl 4-[(3-bromo-5-methoxyphenyl)methyl]piperazine-1-carboxylate Chemical compound COC1=CC(Br)=CC(CN2CCN(CC2)C(=O)OC(C)(C)C)=C1 OGZHMGNGPRNCAQ-UHFFFAOYSA-N 0.000 description 2
KGQLUGXBCYCKIX-UHFFFAOYSA-N tert-butyl 4-[(3-iodo-2-methoxyphenyl)methyl]piperazine-1-carboxylate Chemical compound COC1=C(I)C=CC=C1CN1CCN(C(=O)OC(C)(C)C)CC1 KGQLUGXBCYCKIX-UHFFFAOYSA-N 0.000 description 2
QRCIVOIEHSUADI-UHFFFAOYSA-N tert-butyl 4-[(6-bromopyridin-3-yl)methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CC1=CC=C(Br)N=C1 QRCIVOIEHSUADI-UHFFFAOYSA-N 0.000 description 2
IUIVSFUZFWYZHL-DHZHZOJOSA-N tert-butyl 4-[(e)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethenyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1\C=C\B1OC(C)(C)C(C)(C)O1 IUIVSFUZFWYZHL-DHZHZOJOSA-N 0.000 description 2
HHIFBKPLOWBBRN-MDZDMXLPSA-N tert-butyl 4-[2-[2-[(e)-2-[5-cyano-4-[(4-methyl-1h-indol-5-yl)amino]pyridin-3-yl]ethenyl]phenoxy]ethyl]piperazine-1-carboxylate Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C1=CC=CC=C1OCCN1CCN(C(=O)OC(C)(C)C)CC1 HHIFBKPLOWBBRN-MDZDMXLPSA-N 0.000 description 2
YZICPPFSUSDIBP-MDZDMXLPSA-N tert-butyl 4-[[4-[(e)-2-[5-cyano-4-[(4-methyl-1h-indol-5-yl)amino]pyridin-3-yl]ethenyl]phenyl]methyl]piperazine-1-carboxylate Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\C(C=C1)=CC=C1CN1CCN(C(=O)OC(C)(C)C)CC1 YZICPPFSUSDIBP-MDZDMXLPSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
238000012546 transfer Methods 0.000 description 2
238000000844 transformation Methods 0.000 description 2
NSYSSMYQPLSPOD-UHFFFAOYSA-N triacetate lactone Chemical compound CC1=CC(O)=CC(=O)O1 NSYSSMYQPLSPOD-UHFFFAOYSA-N 0.000 description 2
229960004418 trolamine Drugs 0.000 description 2
VBEQCZHXXJYVRD-GACYYNSASA-N uroanthelone Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CS)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C(C)C)[C@@H](C)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CS)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC(N)=O)C(C)C)[C@@H](C)CC)C1=CC=C(O)C=C1 VBEQCZHXXJYVRD-GACYYNSASA-N 0.000 description 2
239000001993 wax Substances 0.000 description 2
UGOMMVLRQDMAQQ-UHFFFAOYSA-N xphos Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 UGOMMVLRQDMAQQ-UHFFFAOYSA-N 0.000 description 2
MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 1
QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
FNHHVPPSBFQMEL-KQHDFZBMSA-N (3S)-5-N-[(1S,5R)-3-hydroxy-6-bicyclo[3.1.0]hexanyl]-7-N,3-dimethyl-3-phenyl-2H-1-benzofuran-5,7-dicarboxamide Chemical compound CNC(=O)c1cc(cc2c1OC[C@@]2(C)c1ccccc1)C(=O)NC1[C@H]2CC(O)C[C@@H]12 FNHHVPPSBFQMEL-KQHDFZBMSA-N 0.000 description 1
XDDGKNRSCDEWBR-UHFFFAOYSA-N (6-bromopyridin-2-yl)methanol Chemical compound OCC1=CC=CC(Br)=N1 XDDGKNRSCDEWBR-UHFFFAOYSA-N 0.000 description 1
QPPDKOIDAYZUHN-UHFFFAOYSA-N (6-bromopyridin-3-yl)methanol Chemical compound OCC1=CC=C(Br)N=C1 QPPDKOIDAYZUHN-UHFFFAOYSA-N 0.000 description 1
DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 description 1
DELJOESCKJGFML-RQOWECAXSA-N (z)-3-aminobut-2-enenitrile Chemical compound C\C(N)=C\C#N DELJOESCKJGFML-RQOWECAXSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
XMFAAIVNNSITSV-UHFFFAOYSA-N 1,3-dihydropyrrol-3-ide Chemical compound C1=CNC=[C-]1 XMFAAIVNNSITSV-UHFFFAOYSA-N 0.000 description 1
RFEDQTSVZVRTGH-UHFFFAOYSA-N 1-(4-bromophenyl)-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC=C(Br)C=C1 RFEDQTSVZVRTGH-UHFFFAOYSA-N 0.000 description 1
WOPRPBCAVLERJL-UHFFFAOYSA-N 1-[(2-bromopyridin-4-yl)methyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CC1=CC=NC(Br)=C1 WOPRPBCAVLERJL-UHFFFAOYSA-N 0.000 description 1
JWOHBPPVVDQMKB-UHFFFAOYSA-N 1-[(2-methylpropan-2-yl)oxycarbonyl]piperidine-4-carboxylic acid Chemical compound CC(C)(C)OC(=O)N1CCC(C(O)=O)CC1 JWOHBPPVVDQMKB-UHFFFAOYSA-N 0.000 description 1
OVXYTZQAXGEORT-UHFFFAOYSA-N 1-[(3-bromophenyl)methyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CC1=CC=CC(Br)=C1 OVXYTZQAXGEORT-UHFFFAOYSA-N 0.000 description 1
WPSNPDPTHSGVDE-UHFFFAOYSA-N 1-[(3-iodo-4-methoxyphenyl)methyl]-4-methylpiperazine Chemical compound C1=C(I)C(OC)=CC=C1CN1CCN(C)CC1 WPSNPDPTHSGVDE-UHFFFAOYSA-N 0.000 description 1
WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 1
YBLODWQYHLSYAD-UHFFFAOYSA-N 1-[(4-bromofuran-2-yl)methyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CC1=CC(Br)=CO1 YBLODWQYHLSYAD-UHFFFAOYSA-N 0.000 description 1
YEYMDHVVRPPLSH-UHFFFAOYSA-N 1-bromo-2-(2-chloroethoxy)benzene Chemical compound ClCCOC1=CC=CC=C1Br YEYMDHVVRPPLSH-UHFFFAOYSA-N 0.000 description 1
SKCZJIJRFHLPCY-UHFFFAOYSA-N 1-bromo-3-(2-chloroethoxy)benzene Chemical compound ClCCOC1=CC=CC(Br)=C1 SKCZJIJRFHLPCY-UHFFFAOYSA-N 0.000 description 1
VRODDNARFBDTNM-UHFFFAOYSA-N 1-bromo-4-(2-chloroethoxy)benzene Chemical compound ClCCOC1=CC=C(Br)C=C1 VRODDNARFBDTNM-UHFFFAOYSA-N 0.000 description 1
WGGLDBIZIQMEGH-UHFFFAOYSA-N 1-bromo-4-ethenylbenzene Chemical compound BrC1=CC=C(C=C)C=C1 WGGLDBIZIQMEGH-UHFFFAOYSA-N 0.000 description 1
VVPARGBRVKRZJC-UHFFFAOYSA-N 1-bromo-4-propoxybenzene Chemical compound CCCOC1=CC=C(Br)C=C1 VVPARGBRVKRZJC-UHFFFAOYSA-N 0.000 description 1
ITUNZCVRYICLQM-UHFFFAOYSA-N 1-ethenyl-1,2,4-triazole Chemical compound C=CN1C=NC=N1 ITUNZCVRYICLQM-UHFFFAOYSA-N 0.000 description 1
VSIIHWOJPSSIDI-UHFFFAOYSA-N 1-ethoxy-4-iodobenzene Chemical compound CCOC1=CC=C(I)C=C1 VSIIHWOJPSSIDI-UHFFFAOYSA-N 0.000 description 1
125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 description 1
HCKNAJXCHMACDN-UHFFFAOYSA-N 1-methylpiperidine-4-carboxylic acid Chemical compound CN1CCC(C(O)=O)CC1 HCKNAJXCHMACDN-UHFFFAOYSA-N 0.000 description 1
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
PKDPUENCROCRCH-UHFFFAOYSA-N 1-piperazin-1-ylethanone Chemical compound CC(=O)N1CCNCC1 PKDPUENCROCRCH-UHFFFAOYSA-N 0.000 description 1
XLXCHZCQTCBUOX-UHFFFAOYSA-N 1-prop-2-enylimidazole Chemical compound C=CCN1C=CN=C1 XLXCHZCQTCBUOX-UHFFFAOYSA-N 0.000 description 1
AAWSBPMMOLOACQ-UHFFFAOYSA-N 10-methyl-4,8,14-triazatetracyclo[7.7.0.02,7.011,15]hexadeca-1(16),2(7),3,5,9,11(15),12-heptaene-6-carbonitrile Chemical compound C12=CN=CC(C#N)=C2NC2=C1C=C1NC=CC1=C2C AAWSBPMMOLOACQ-UHFFFAOYSA-N 0.000 description 1
QNMQRFQSRKOKOK-UHFFFAOYSA-N 2,4-dimethyl-1h-indol-5-amine Chemical compound NC1=CC=C2NC(C)=CC2=C1C QNMQRFQSRKOKOK-UHFFFAOYSA-N 0.000 description 1
FEYDZHNIIMENOB-UHFFFAOYSA-N 2,6-dibromopyridine Chemical compound BrC1=CC=CC(Br)=N1 FEYDZHNIIMENOB-UHFFFAOYSA-N 0.000 description 1
YFTHTJAPODJVSL-UHFFFAOYSA-N 2-(1-benzothiophen-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(SC=C2)C2=C1 YFTHTJAPODJVSL-UHFFFAOYSA-N 0.000 description 1
HWSDRAPTZRYXHN-UHFFFAOYSA-N 2-(4-chlorophenyl)ethenylboronic acid Chemical compound OB(O)C=CC1=CC=C(Cl)C=C1 HWSDRAPTZRYXHN-UHFFFAOYSA-N 0.000 description 1
LYIUZNSEZMKOQV-UHFFFAOYSA-N 2-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=NC=CC=C1C#N LYIUZNSEZMKOQV-UHFFFAOYSA-N 0.000 description 1
UWVNHABAOFKMNW-YRNVUSSQSA-N 2-[(e)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-enyl]isoindole-1,3-dione Chemical compound O1C(C)(C)C(C)(C)OB1\C=C\CCN1C(=O)C2=CC=CC=C2C1=O UWVNHABAOFKMNW-YRNVUSSQSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
YNQSFJGDFNZZMI-UHFFFAOYSA-N 2-chloro-3-ethenylpyridine Chemical compound ClC1=NC=CC=C1C=C YNQSFJGDFNZZMI-UHFFFAOYSA-N 0.000 description 1
WWYFHDNQGVTJJJ-UHFFFAOYSA-N 2-cyclohexylpiperazine Chemical group C1CCCCC1C1NCCNC1 WWYFHDNQGVTJJJ-UHFFFAOYSA-N 0.000 description 1
LFOIDLOIBZFWDO-UHFFFAOYSA-N 2-methoxy-6-[6-methoxy-4-[(3-phenylmethoxyphenyl)methoxy]-1-benzofuran-2-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 LFOIDLOIBZFWDO-UHFFFAOYSA-N 0.000 description 1
BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical compound C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 1
MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 1
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
DIQOUXNTSMWQSA-UHFFFAOYSA-N 2-oxa-5-azabicyclo[2.2.1]heptane Chemical compound C1OC2CNC1C2 DIQOUXNTSMWQSA-UHFFFAOYSA-N 0.000 description 1
STBGLXMINLWCNL-UHFFFAOYSA-N 3-bromo-2-hydroxybenzaldehyde Chemical compound OC1=C(Br)C=CC=C1C=O STBGLXMINLWCNL-UHFFFAOYSA-N 0.000 description 1
LDDHMKANNXWUAK-UHFFFAOYSA-N 3-iodo-4-methylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C=C1I LDDHMKANNXWUAK-UHFFFAOYSA-N 0.000 description 1
SVSUYEJKNSMKKW-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-prop-1-en-2-yl-1,3,2-dioxaborolane Chemical compound CC(=C)B1OC(C)(C)C(C)(C)O1 SVSUYEJKNSMKKW-UHFFFAOYSA-N 0.000 description 1
DPGSPRJLAZGUBQ-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane Substances CC1(C)OB(C=C)OC1(C)C DPGSPRJLAZGUBQ-UHFFFAOYSA-N 0.000 description 1
YGLWFMUJSOYXOA-UHFFFAOYSA-N 4-(1h-indol-4-ylamino)-5-iodopyridine-3-carbonitrile Chemical compound IC1=CN=CC(C#N)=C1NC1=CC=CC2=C1C=CN2 YGLWFMUJSOYXOA-UHFFFAOYSA-N 0.000 description 1
IMMBFBPNPIRCBR-VOTSOKGWSA-N 4-(1h-indol-5-yloxy)-5-[(e)-2-phenylethenyl]pyridine-3-carbonitrile Chemical compound C=1C=C2NC=CC2=CC=1OC=1C(C#N)=CN=CC=1\C=C\C1=CC=CC=C1 IMMBFBPNPIRCBR-VOTSOKGWSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
NEFUYQPHPPCFIV-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[2-[4-(pyrrolidin-1-ylmethyl)phenyl]ethynyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C#CC(C=C1)=CC=C1CN1CCCC1 NEFUYQPHPPCFIV-UHFFFAOYSA-N 0.000 description 1
DTGFPQPPPFUQBC-MDZDMXLPSA-N 4-[(e)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethenyl]benzaldehyde Chemical compound O1C(C)(C)C(C)(C)OB1\C=C\C1=CC=C(C=O)C=C1 DTGFPQPPPFUQBC-MDZDMXLPSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
JHBGMSZDXLUBOZ-UHFFFAOYSA-N 4-bromo-1,2-bis(2-methoxyethoxy)benzene Chemical compound COCCOC1=CC=C(Br)C=C1OCCOC JHBGMSZDXLUBOZ-UHFFFAOYSA-N 0.000 description 1
FNOVBQBSXJHCTI-UHFFFAOYSA-N 4-bromo-2-[(4-methylpiperazin-1-yl)methyl]-1,3-thiazole Chemical compound C1CN(C)CCN1CC1=NC(Br)=CS1 FNOVBQBSXJHCTI-UHFFFAOYSA-N 0.000 description 1
ONHMWUXYIFULDO-UHFFFAOYSA-N 4-bromo-2-chloropyridine Chemical compound ClC1=CC(Br)=CC=N1 ONHMWUXYIFULDO-UHFFFAOYSA-N 0.000 description 1
MWMIGHFRASDROC-UHFFFAOYSA-N 4-bromo-5-iodopyridine-3-carbonitrile Chemical compound BrC1=C(I)C=NC=C1C#N MWMIGHFRASDROC-UHFFFAOYSA-N 0.000 description 1
GQWAOUOHRMHSHL-UHFFFAOYSA-N 4-ethenyl-n,n-dimethylaniline Chemical compound CN(C)C1=CC=C(C=C)C=C1 GQWAOUOHRMHSHL-UHFFFAOYSA-N 0.000 description 1
QBFNGLBSVFKILI-UHFFFAOYSA-N 4-ethenylbenzaldehyde Chemical compound C=CC1=CC=C(C=O)C=C1 QBFNGLBSVFKILI-UHFFFAOYSA-N 0.000 description 1
IRQWEODKXLDORP-UHFFFAOYSA-N 4-ethenylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=C)C=C1 IRQWEODKXLDORP-UHFFFAOYSA-N 0.000 description 1
KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 description 1
BGMHQBQFJYJLBP-UHFFFAOYSA-N 4-ethynylbenzaldehyde Chemical compound O=CC1=CC=C(C#C)C=C1 BGMHQBQFJYJLBP-UHFFFAOYSA-N 0.000 description 1
TTYVECQWCUJXCS-UHFFFAOYSA-N 4-fluoropyridine Chemical compound FC1=CC=NC=C1 TTYVECQWCUJXCS-UHFFFAOYSA-N 0.000 description 1
HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
NLMQHXUGJIAKTH-UHFFFAOYSA-N 4-hydroxyindole Chemical compound OC1=CC=CC2=C1C=CN2 NLMQHXUGJIAKTH-UHFFFAOYSA-N 0.000 description 1
GCNTZFIIOFTKIY-UHFFFAOYSA-N 4-hydroxypyridine Chemical compound OC1=CC=NC=C1 GCNTZFIIOFTKIY-UHFFFAOYSA-N 0.000 description 1
HLTCSOXVOUXEJH-UHFFFAOYSA-N 4-iodo-3-methylbenzonitrile Chemical compound CC1=CC(C#N)=CC=C1I HLTCSOXVOUXEJH-UHFFFAOYSA-N 0.000 description 1
KFELHBGMNBHIHF-UHFFFAOYSA-N 4-methyl-1h-indol-5-ol Chemical compound CC1=C(O)C=CC2=C1C=CN2 KFELHBGMNBHIHF-UHFFFAOYSA-N 0.000 description 1
ZMLBLPVLYMSOAU-DUXPYHPUSA-N 5-[(e)-2-(6-chloropyridin-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=CC=C(Cl)N=C1 ZMLBLPVLYMSOAU-DUXPYHPUSA-N 0.000 description 1
FTGLSLJARFJTHI-MDZDMXLPSA-N 5-[(e)-2-[3-[(4-cyclopentylpiperazin-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=1CN(CC1)CCN1C1CCCC1 FTGLSLJARFJTHI-MDZDMXLPSA-N 0.000 description 1
BELSGZUMEORXMW-CMDGGOBGSA-N 5-[(e)-2-[6-(6-bromopyridin-2-yl)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=1C1=CC=CC(Br)=N1 BELSGZUMEORXMW-CMDGGOBGSA-N 0.000 description 1
PEAOEIWYQVXZMB-UHFFFAOYSA-N 5-bromo-2-chloropyridine Chemical compound ClC1=CC=C(Br)C=N1 PEAOEIWYQVXZMB-UHFFFAOYSA-N 0.000 description 1
PSKBQZBUZCNPOI-UHFFFAOYSA-N 5-bromo-4-chloro-6-propan-2-ylpyridine-3-carbonitrile Chemical compound CC(C)C1=NC=C(C#N)C(Cl)=C1Br PSKBQZBUZCNPOI-UHFFFAOYSA-N 0.000 description 1
GZRZTOWRGYFEHP-UHFFFAOYSA-N 5-bromo-6-ethyl-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound CCC1=NC=C(C#N)C(NC=2C(=C3C=CNC3=CC=2)C)=C1Br GZRZTOWRGYFEHP-UHFFFAOYSA-N 0.000 description 1
UXFIKVWAAMKFQE-UHFFFAOYSA-N 5-chloropent-1-yne Chemical compound ClCCCC#C UXFIKVWAAMKFQE-UHFFFAOYSA-N 0.000 description 1
QUAMMXIRDIIGDJ-UHFFFAOYSA-N 5-ethenyl-4-methyl-1,3-thiazole Chemical compound CC=1N=CSC=1C=C QUAMMXIRDIIGDJ-UHFFFAOYSA-N 0.000 description 1
LMIQERWZRIFWNZ-UHFFFAOYSA-N 5-hydroxyindole Chemical compound OC1=CC=C2NC=CC2=C1 LMIQERWZRIFWNZ-UHFFFAOYSA-N 0.000 description 1
GLTAAVXVGLMEPV-UHFFFAOYSA-N 5-iodo-4-[(4-methyl-1h-indol-5-yl)oxy]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1OC1=C(I)C=NC=C1C#N GLTAAVXVGLMEPV-UHFFFAOYSA-N 0.000 description 1
GFHSQBPLTGCBOG-UHFFFAOYSA-N 5-iodo-6-methyl-4-oxo-1h-pyridine-3-carboxylic acid Chemical compound CC=1NC=C(C(O)=O)C(=O)C=1I.CC=1NC=C(C(O)=O)C(=O)C=1I GFHSQBPLTGCBOG-UHFFFAOYSA-N 0.000 description 1
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
YAQYIOUUDQZYID-UHFFFAOYSA-N 7-chloro-4-methyl-1h-indol-5-amine Chemical compound CC1=C(N)C=C(Cl)C2=C1C=CN2 YAQYIOUUDQZYID-UHFFFAOYSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
235000003911 Arachis Nutrition 0.000 description 1
244000105624 Arachis hypogaea Species 0.000 description 1
208000023275 Autoimmune disease Diseases 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
101150012716 CDK1 gene Proteins 0.000 description 1
108091007914 CDKs Proteins 0.000 description 1
VJVCQNMLNFJNTG-UHFFFAOYSA-N CN(C)Cc1ccc(C=C)nc1 Chemical compound CN(C)Cc1ccc(C=C)nc1 VJVCQNMLNFJNTG-UHFFFAOYSA-N 0.000 description 1
DCERHCFNWRGHLK-UHFFFAOYSA-N C[Si](C)C Chemical compound C[Si](C)C DCERHCFNWRGHLK-UHFFFAOYSA-N 0.000 description 1
101100005789 Caenorhabditis elegans cdk-4 gene Proteins 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
PTHCMJGKKRQCBF-UHFFFAOYSA-N Cellulose, microcrystalline Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC)C(CO)O1 PTHCMJGKKRQCBF-UHFFFAOYSA-N 0.000 description 1
108010003384 Colony-Stimulating Factor Receptors Proteins 0.000 description 1
102000004626 Colony-Stimulating Factor Receptors Human genes 0.000 description 1
108010049894 Cyclic AMP-Dependent Protein Kinases Proteins 0.000 description 1
102000002554 Cyclin A Human genes 0.000 description 1
108010068192 Cyclin A Proteins 0.000 description 1
102000002427 Cyclin B Human genes 0.000 description 1
108010068150 Cyclin B Proteins 0.000 description 1
102000003910 Cyclin D Human genes 0.000 description 1
108090000259 Cyclin D Proteins 0.000 description 1
102000003909 Cyclin E Human genes 0.000 description 1
108090000257 Cyclin E Proteins 0.000 description 1
102000003903 Cyclin-dependent kinases Human genes 0.000 description 1
108090000266 Cyclin-dependent kinases Proteins 0.000 description 1
238000010485 C−C bond formation reaction Methods 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
101100481404 Danio rerio tie1 gene Proteins 0.000 description 1
101100481408 Danio rerio tie2 gene Proteins 0.000 description 1
239000004375 Dextrin Substances 0.000 description 1
229920001353 Dextrin Polymers 0.000 description 1
235000019739 Dicalciumphosphate Nutrition 0.000 description 1
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
101100059559 Emericella nidulans (strain FGSC A4 / ATCC 38163 / CBS 112.46 / NRRL 194 / M139) nimX gene Proteins 0.000 description 1
102000009024 Epidermal Growth Factor Human genes 0.000 description 1
101800003838 Epidermal growth factor Proteins 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
CTKXFMQHOOWWEB-UHFFFAOYSA-N Ethylene oxide/propylene oxide copolymer Chemical compound CCCOC(C)COCCO CTKXFMQHOOWWEB-UHFFFAOYSA-N 0.000 description 1
108091008794 FGF receptors Proteins 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
241000233866 Fungi Species 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
108010009202 Growth Factor Receptors Proteins 0.000 description 1
102000009465 Growth Factor Receptors Human genes 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
101000692455 Homo sapiens Platelet-derived growth factor receptor beta Proteins 0.000 description 1
102000009438 IgE Receptors Human genes 0.000 description 1
108010073816 IgE Receptors Proteins 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
108060003951 Immunoglobulin Proteins 0.000 description 1
102220632799 Immunoglobulin heavy variable 1-69_R11A_mutation Human genes 0.000 description 1
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 1
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
240000003183 Manihot esculenta Species 0.000 description 1
235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
241001529936 Murinae Species 0.000 description 1
101100481410 Mus musculus Tek gene Proteins 0.000 description 1
101100481406 Mus musculus Tie1 gene Proteins 0.000 description 1
101100268066 Mus musculus Zap70 gene Proteins 0.000 description 1
108010032605 Nerve Growth Factor Receptors Proteins 0.000 description 1
102000007339 Nerve Growth Factor Receptors Human genes 0.000 description 1
101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
101150010978 PRKCE gene Proteins 0.000 description 1
102100026547 Platelet-derived growth factor receptor beta Human genes 0.000 description 1
206010035664 Pneumonia Diseases 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
102000001892 Protein Kinase C-theta Human genes 0.000 description 1
108010015499 Protein Kinase C-theta Proteins 0.000 description 1
YDWKSSWZGXRQET-UHFFFAOYSA-N Pyrrolidine, 1-[2-(4-bromophenoxy)ethyl]- Chemical compound C1=CC(Br)=CC=C1OCCN1CCCC1 YDWKSSWZGXRQET-UHFFFAOYSA-N 0.000 description 1
102100033810 RAC-alpha serine/threonine-protein kinase Human genes 0.000 description 1
101000852966 Rattus norvegicus Interleukin-1 receptor-like 1 Proteins 0.000 description 1
MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
244000061456 Solanum tuberosum Species 0.000 description 1
235000002595 Solanum tuberosum Nutrition 0.000 description 1
108010017622 Somatomedin Receptors Proteins 0.000 description 1
102000004584 Somatomedin Receptors Human genes 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
210000001744 T-lymphocyte Anatomy 0.000 description 1
210000004241 Th2 cell Anatomy 0.000 description 1
AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 1
239000004473 Threonine Substances 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
101100273808 Xenopus laevis cdk1-b gene Proteins 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
GBNJRIQSFJFDII-AATRIKPKSA-N [(e)-2-(4-fluorophenyl)ethenyl]boronic acid Chemical compound OB(O)\C=C\C1=CC=C(F)C=C1 GBNJRIQSFJFDII-AATRIKPKSA-N 0.000 description 1
JJOBVKVXRDHVRP-VOTSOKGWSA-N [(e)-2-(4-methylphenyl)ethenyl]boronic acid Chemical compound CC1=CC=C(\C=C\B(O)O)C=C1 JJOBVKVXRDHVRP-VOTSOKGWSA-N 0.000 description 1
NTRGFVQIGQYKIL-ZHACJKMWSA-N [(e)-2-(4-phenylphenyl)ethenyl]boronic acid Chemical compound C1=CC(/C=C/B(O)O)=CC=C1C1=CC=CC=C1 NTRGFVQIGQYKIL-ZHACJKMWSA-N 0.000 description 1
BBNQFBHQOPZKTI-AATRIKPKSA-N [(e)-2-[4-(trifluoromethyl)phenyl]ethenyl]boronic acid Chemical compound OB(O)\C=C\C1=CC=C(C(F)(F)F)C=C1 BBNQFBHQOPZKTI-AATRIKPKSA-N 0.000 description 1
JMTGSXGIIONQHI-OWOJBTEDSA-N [(e)-3-chloroprop-1-enyl]boronic acid Chemical compound OB(O)\C=C\CCl JMTGSXGIIONQHI-OWOJBTEDSA-N 0.000 description 1
GMGWFDHLFMBIDS-XBXARRHUSA-N [(e)-3-phenylprop-1-enyl]boronic acid Chemical compound OB(O)\C=C\CC1=CC=CC=C1 GMGWFDHLFMBIDS-XBXARRHUSA-N 0.000 description 1
230000002159 abnormal effect Effects 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000004913 activation Effects 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
230000002411 adverse Effects 0.000 description 1
125000003158 alcohol group Chemical group 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
125000000539 amino acid group Chemical group 0.000 description 1
239000001099 ammonium carbonate Substances 0.000 description 1
235000012501 ammonium carbonate Nutrition 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
229940121363 anti-inflammatory agent Drugs 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
239000008122 artificial sweetener Substances 0.000 description 1
XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 1
238000011914 asymmetric synthesis Methods 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
230000005784 autoimmunity Effects 0.000 description 1
125000003725 azepanyl group Chemical group 0.000 description 1
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
125000004069 aziridinyl group Chemical group 0.000 description 1
230000003385 bacteriostatic effect Effects 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
229960000686 benzalkonium chloride Drugs 0.000 description 1
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
230000033228 biological regulation Effects 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
210000001185 bone marrow Anatomy 0.000 description 1
UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
102220364121 c.35G>A Human genes 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
229940078456 calcium stearate Drugs 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
229940084030 carboxymethylcellulose calcium Drugs 0.000 description 1
230000032823 cell division Effects 0.000 description 1
230000003915 cell function Effects 0.000 description 1
238000004296 chiral HPLC Methods 0.000 description 1
238000005660 chlorination reaction Methods 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 1
125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
235000019864 coconut oil Nutrition 0.000 description 1
239000003240 coconut oil Substances 0.000 description 1
229940075614 colloidal silicon dioxide Drugs 0.000 description 1
239000003086 colorant Substances 0.000 description 1
229940125773 compound 10 Drugs 0.000 description 1
229940125961 compound 24 Drugs 0.000 description 1
229940125878 compound 36 Drugs 0.000 description 1
239000012059 conventional drug carrier Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
239000000287 crude extract Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
210000000805 cytoplasm Anatomy 0.000 description 1
210000001151 cytotoxic T lymphocyte Anatomy 0.000 description 1
125000005891 decahydronaphthyridinyl group Chemical group 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
230000005595 deprotonation Effects 0.000 description 1
238000010537 deprotonation reaction Methods 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
125000005959 diazepanyl group Chemical group 0.000 description 1
125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 description 1
JQKJEPJLCSCBGW-UHFFFAOYSA-N dibutoxy(ethenyl)borane Chemical compound CCCCOB(C=C)OCCCC JQKJEPJLCSCBGW-UHFFFAOYSA-N 0.000 description 1
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
229940038472 dicalcium phosphate Drugs 0.000 description 1
229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
MWPIIMNHWGOFBL-UHFFFAOYSA-N dichloromethane;toluene Chemical compound ClCCl.CC1=CC=CC=C1 MWPIIMNHWGOFBL-UHFFFAOYSA-N 0.000 description 1
PQZTVWVYCLIIJY-UHFFFAOYSA-N diethyl(propyl)amine Chemical group CCCN(CC)CC PQZTVWVYCLIIJY-UHFFFAOYSA-N 0.000 description 1
125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 1
125000004655 dihydropyridinyl group Chemical group N1(CC=CC=C1)* 0.000 description 1
125000005054 dihydropyrrolyl group Chemical group [H]C1=C([H])C([H])([H])C([H])([H])N1* 0.000 description 1
125000005057 dihydrothienyl group Chemical group S1C(CC=C1)* 0.000 description 1
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical group CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
125000000532 dioxanyl group Chemical group 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
229910000397 disodium phosphate Inorganic materials 0.000 description 1
235000019800 disodium phosphate Nutrition 0.000 description 1
239000002612 dispersion medium Substances 0.000 description 1
238000007908 dry granulation Methods 0.000 description 1
DDCSIHFTXGZHAT-UHFFFAOYSA-N e-3-carbonitrile Chemical compound C1C(C)CCC(S2)=C1C(C#N)C2N(C(C12)=O)C(=O)C1C1C2C2C=CC1C(C1=O)C2C(=O)N1C(C1C#N)SC2=C1CC(C)CC2 DDCSIHFTXGZHAT-UHFFFAOYSA-N 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000008387 emulsifying waxe Substances 0.000 description 1
210000002889 endothelial cell Anatomy 0.000 description 1
229940116977 epidermal growth factor Drugs 0.000 description 1
210000002615 epidermis Anatomy 0.000 description 1
210000000981 epithelium Anatomy 0.000 description 1
ZCRZCMUDOWDGOB-UHFFFAOYSA-N ethanesulfonimidic acid Chemical compound CCS(N)(=O)=O ZCRZCMUDOWDGOB-UHFFFAOYSA-N 0.000 description 1
FRYHCSODNHYDPU-UHFFFAOYSA-N ethanesulfonyl chloride Chemical compound CCS(Cl)(=O)=O FRYHCSODNHYDPU-UHFFFAOYSA-N 0.000 description 1
YFXCNIVBAVFOBX-UHFFFAOYSA-N ethenylboronic acid Chemical compound OB(O)C=C YFXCNIVBAVFOBX-UHFFFAOYSA-N 0.000 description 1
LDLDYFCCDKENPD-UHFFFAOYSA-N ethenylcyclohexane Chemical compound C=CC1CCCCC1 LDLDYFCCDKENPD-UHFFFAOYSA-N 0.000 description 1
WHQLQYRFIHPMNA-UHFFFAOYSA-N ethyl acetate;oxolane Chemical compound C1CCOC1.CCOC(C)=O WHQLQYRFIHPMNA-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
239000003925 fat Substances 0.000 description 1
235000019197 fats Nutrition 0.000 description 1
102000052178 fibroblast growth factor receptor activity proteins Human genes 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
235000015203 fruit juice Nutrition 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000008187 granular material Substances 0.000 description 1
239000003102 growth factor Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
125000006341 heptafluoro n-propyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
125000002632 imidazolidinyl group Chemical group 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
102000018358 immunoglobulin Human genes 0.000 description 1
239000007943 implant Substances 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
230000002757 inflammatory effect Effects 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
125000003965 isoxazolidinyl group Chemical group 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
238000011813 knockout mouse model Methods 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
RMGJCSHZTFKPNO-UHFFFAOYSA-M magnesium;ethene;bromide Chemical compound [Mg+2].[Br-].[CH-]=C RMGJCSHZTFKPNO-UHFFFAOYSA-M 0.000 description 1
210000004962 mammalian cell Anatomy 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
230000017522 mast cell cytokine production Effects 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
230000005012 migration Effects 0.000 description 1
238000013508 migration Methods 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000003607 modifier Substances 0.000 description 1
235000019799 monosodium phosphate Nutrition 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
210000004400 mucous membrane Anatomy 0.000 description 1
ZUHZZVMEUAUWHY-UHFFFAOYSA-N n,n-dimethylpropan-1-amine Chemical compound CCCN(C)C ZUHZZVMEUAUWHY-UHFFFAOYSA-N 0.000 description 1
SXEJQBLAVTUYPB-UHFFFAOYSA-N n-[(4-bromophenyl)methyl]-n-ethylethanamine Chemical compound CCN(CC)CC1=CC=C(Br)C=C1 SXEJQBLAVTUYPB-UHFFFAOYSA-N 0.000 description 1
125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
125000006574 non-aromatic ring group Chemical group 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
SFBTTWXNCQVIEC-UHFFFAOYSA-N o-Vinylanisole Chemical compound COC1=CC=CC=C1C=C SFBTTWXNCQVIEC-UHFFFAOYSA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
125000005889 octahydrochromenyl group Chemical group 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000005963 oxadiazolidinyl group Chemical group 0.000 description 1
125000001715 oxadiazolyl group Chemical group 0.000 description 1
125000005961 oxazepanyl group Chemical group 0.000 description 1
125000000160 oxazolidinyl group Chemical group 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
125000003551 oxepanyl group Chemical group 0.000 description 1
125000003566 oxetanyl group Chemical group 0.000 description 1
125000000466 oxiranyl group Chemical group 0.000 description 1
IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
239000006072 paste Substances 0.000 description 1
230000007310 pathophysiology Effects 0.000 description 1
230000037361 pathway Effects 0.000 description 1
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
RFIOZSIHFNEKFF-UHFFFAOYSA-N piperazine-1-carboxylic acid Chemical compound OC(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-N 0.000 description 1
HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 description 1
229920001993 poloxamer 188 Polymers 0.000 description 1
229940044519 poloxamer 188 Drugs 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
229920006316 polyvinylpyrrolidine Polymers 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
235000011118 potassium hydroxide Nutrition 0.000 description 1
235000019814 powdered cellulose Nutrition 0.000 description 1
229920003124 powdered cellulose Polymers 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
230000002265 prevention Effects 0.000 description 1
150000003140 primary amides Chemical class 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
238000012545 processing Methods 0.000 description 1
230000035755 proliferation Effects 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003072 pyrazolidinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
GZRKXKUVVPSREJ-UHFFFAOYSA-N pyridinylpiperazine Chemical compound C1CNCCN1C1=CC=CC=N1 GZRKXKUVVPSREJ-UHFFFAOYSA-N 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
JWEQRJSCTFBRSI-PCLIKHOPSA-N rboxylate Chemical compound COC(=O)C1C(N2C3=O)C4=CC=CC=C4OC1(C)N=C2S\C3=C\C(C=1)=CC=C(OC)C=1COC1=CC=CC=C1C JWEQRJSCTFBRSI-PCLIKHOPSA-N 0.000 description 1
238000004366 reverse phase liquid chromatography Methods 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000012363 selectfluor Substances 0.000 description 1
150000003354 serine derivatives Chemical class 0.000 description 1
230000011664 signaling Effects 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
210000002027 skeletal muscle Anatomy 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
235000011083 sodium citrates Nutrition 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
229940083575 sodium dodecyl sulfate Drugs 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
229910052717 sulfur Chemical group 0.000 description 1
239000011593 sulfur Chemical group 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000007916 tablet composition Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
BAKFOMLJJXOWFU-UHFFFAOYSA-N tert-butyl 2-aminoazetidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC1N BAKFOMLJJXOWFU-UHFFFAOYSA-N 0.000 description 1
AHFRRVAOFWGVGU-UHFFFAOYSA-N tert-butyl 4-[(4-iodo-3-methoxyphenyl)methyl]piperazine-1-carboxylate Chemical compound C1=C(I)C(OC)=CC(CN2CCN(CC2)C(=O)OC(C)(C)C)=C1 AHFRRVAOFWGVGU-UHFFFAOYSA-N 0.000 description 1
CXSFTBOFGWRFAU-FNORWQNLSA-N tert-butyl 4-[(e)-4-[5-cyano-4-[(4-methyl-1h-indol-5-yl)amino]pyridin-3-yl]but-3-enyl]piperazine-1-carboxylate Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CCN1CCN(C(=O)OC(C)(C)C)CC1 CXSFTBOFGWRFAU-FNORWQNLSA-N 0.000 description 1
NDQUICVVFNXJOZ-SOFGYWHQSA-N tert-butyl 4-[(e)-5-[5-cyano-4-[(4-methyl-1h-indol-5-yl)amino]pyridin-3-yl]pent-4-enyl]piperazine-1-carboxylate Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1\C=C\CCCN1CCN(C(=O)OC(C)(C)C)CC1 NDQUICVVFNXJOZ-SOFGYWHQSA-N 0.000 description 1
RBZYQVYATPQVIR-UHFFFAOYSA-N tert-butyl 4-[4-[5-cyano-4-[(4-methyl-1h-indol-5-yl)amino]pyridin-3-yl]butyl]piperazine-1-carboxylate Chemical compound C1=CC=2NC=CC=2C(C)=C1NC(C(=CN=C1)C#N)=C1CCCCN1CCN(C(=O)OC(C)(C)C)CC1 RBZYQVYATPQVIR-UHFFFAOYSA-N 0.000 description 1
CKXZPVPIDOJLLM-UHFFFAOYSA-N tert-butyl n-piperidin-4-ylcarbamate Chemical compound CC(C)(C)OC(=O)NC1CCNCC1 CKXZPVPIDOJLLM-UHFFFAOYSA-N 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 1
125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000001984 thiazolidinyl group Chemical group 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
239000012049 topical pharmaceutical composition Substances 0.000 description 1
230000002110 toxicologic effect Effects 0.000 description 1
231100000027 toxicology Toxicity 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
125000005310 triazolidinyl group Chemical group N1(NNCC1)* 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical group CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
PBIMIGNDTBRRPI-UHFFFAOYSA-N trifluoro borate Chemical compound FOB(OF)OF PBIMIGNDTBRRPI-UHFFFAOYSA-N 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
229910000406 trisodium phosphate Inorganic materials 0.000 description 1
235000019801 trisodium phosphate Nutrition 0.000 description 1
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
238000005303 weighing Methods 0.000 description 1
238000005550 wet granulation Methods 0.000 description 1
239000000230 xanthan gum Substances 0.000 description 1
235000010493 xanthan gum Nutrition 0.000 description 1
229920001285 xanthan gum Polymers 0.000 description 1
229940082509 xanthan gum Drugs 0.000 description 1
229910052727 yttrium Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Immunology (AREA)
Physical Education & Sports Medicine (AREA)
Pulmonology (AREA)
Rheumatology (AREA)
Transplantation (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Dermatology (AREA)
Orthopedic Medicine & Surgery (AREA)
Biomedical Technology (AREA)
Pain & Pain Management (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CA2709314A 2007-12-13 2008-12-12 5-alkyl/alcenyl-3-cyanopyridines en tant qu'inhibiteurs de kinase Abandoned CA2709314A1 (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US1345707P	2007-12-13	2007-12-13
US61/013,457		2007-12-13
PCT/US2008/086594 WO2009076602A1 (fr)	2007-12-13	2008-12-12	5-alkyl/alcényl-3-cyanopyridines en tant qu'inhibiteurs de kinase

Publications (1)

Publication Number	Publication Date
CA2709314A1 true CA2709314A1 (fr)	2009-06-18

Family

ID=40429261

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA2709314A Abandoned CA2709314A1 (fr)	2007-12-13	2008-12-12	5-alkyl/alcenyl-3-cyanopyridines en tant qu'inhibiteurs de kinase

Country Status (5)

Country	Link
EP (1)	EP2229377A1 (fr)
JP (1)	JP2011506475A (fr)
CA (1)	CA2709314A1 (fr)
CL (1)	CL2008003675A1 (fr)
WO (1)	WO2009076602A1 (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR101452579B1 (ko) *	2012-08-17	2014-10-21	주식회사 두산	신규 화합물 및 이를 포함하는 유기 전계 발광 소자
AR094812A1 (es) *	2013-02-20	2015-08-26	Eisai R&D Man Co Ltd	Derivado de piridina monocíclico como inhibidor del fgfr
KR102344105B1 (ko)	2014-08-18	2021-12-29	에자이 알앤드디 매니지먼트 가부시키가이샤	모노시클릭 피리딘 유도체의 염 및 이의 결정
EP3275442B1 (fr)	2015-03-25	2021-07-28	National Cancer Center	Agent thérapeutique contre le cancer du canal cholédoque
WO2017013593A1 (fr)	2015-07-22	2017-01-26	Lupin Limited	Dérivés d'isoquinolinone utilisés en tant qu'inhibiteurs de parp
CN108367000A (zh)	2015-12-17	2018-08-03	卫材R&D管理有限公司	用于乳腺癌的治疗剂
US11219619B2 (en)	2018-03-28	2022-01-11	Eisai R&D Management Co., Ltd.	Therapeutic agent for hepatocellular carcinoma
WO2024151919A1 (fr) *	2023-01-13	2024-07-18	Ifm Due, Inc.	Composés et compositions pour traiter des états pathologiques associés à une activité de sting

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7781591B2 (en) *	2006-06-13	2010-08-24	Wyeth Llc	Substituted 3-cyanopyridines as protein kinase inhibitors
EP1888529A2 (fr) *	2005-05-18	2008-02-20	Wyeth	Inhibiteurs 3-cyanoquinoline de la tpl2 kinase et procedes de production et d'utilisation associes

2008
- 2008-12-10 CL CL2008003675A patent/CL2008003675A1/es unknown
- 2008-12-12 EP EP08859530A patent/EP2229377A1/fr not_active Withdrawn
- 2008-12-12 WO PCT/US2008/086594 patent/WO2009076602A1/fr not_active Ceased
- 2008-12-12 JP JP2010538186A patent/JP2011506475A/ja not_active Withdrawn
- 2008-12-12 CA CA2709314A patent/CA2709314A1/fr not_active Abandoned

Also Published As

Publication number	Publication date
WO2009076602A8 (fr)	2010-02-18
EP2229377A1 (fr)	2010-09-22
CL2008003675A1 (es)	2009-03-20
JP2011506475A (ja)	2011-03-03
WO2009076602A1 (fr)	2009-06-18

Legal Events

Date	Code	Title	Description
2010-06-11	EEER	Examination request
2013-02-06	FZDE	Dead	Effective date: 20121212

Publication	Publication Date	Title
ES2543151T3 (es)	2015-08-17	Derivados de 2-piridina como moduladores del receptor Smoothened
JP5969054B2 (ja)	2016-08-10	Ｓｍａｃミメチックスとしての６−アルキニルピリジン
KR20170117479A (ko)	2017-10-23	치환된 모노- 및 폴리아자나프탈렌 유도체 및 이의 용도
CA2709314A1 (fr)	2009-06-18	5-alkyl/alcenyl-3-cyanopyridines en tant qu'inhibiteurs de kinase
AU2006297948A1 (en)	2007-04-12	Novel imidazo [4,5 -b] pyridine derivatives as inhibitors of glycogen synthase kinase 3 for use in the treatment of dementia and neurodegenerative disorders
TW200306180A (en)	2003-11-16	New compounds
WO2010080474A1 (fr)	2010-07-15	Carbazole et inhibiteurs de la carboline kinase
KR20130116287A (ko)	2013-10-23	3-(아미노아릴)-피리딘 화합물
JP2010514822A (ja)	2010-05-06	新規なフェニル（４−フェニルピリミジン−２−イル）アミン誘導体、薬物としてのこれらの調製、医薬組成物および基本的にｉｋｋ阻害剤としてのこれらの使用
JP2009501711A (ja)	2009-01-22	新規２，４−ジアニリノピリミジン誘導体、その調製、医薬、医薬組成物としての、特に、ｉｋｋ阻害剤としてのそれらの使用
KR20110118611A (ko)	2011-10-31	암의 치료를 위한 ｗｎｔ 신호전달 경로 억제제로서의 피리딘계 및 피리미딘계 화합물
CA2610446A1 (fr)	2006-10-26	Compose heterocyclique azote
CA2682340A1 (fr)	2008-10-16	[2,6]naphthyridines utiles en tant qu'inhibiteurs des proteines kinases
JP2008542433A (ja)	2008-11-27	ＣＤＫ−１インヒビターとしてのα−カルボリン
WO2013100672A1 (fr)	2013-07-04	Dérivé d'indazole 3,6-disubstitué ayant une activité d'inhibition de protéine kinase
CN115515589A (zh)	2022-12-23	Ulk1/2抑制剂及其使用方法
EP1657241A1 (fr)	2006-05-17	Nouveaux urées d' anthranylamide pyridine ayant une activité inhibitrice de kinase du récepteur de VEGF
WO2011019060A1 (fr)	2011-02-17	Inhibiteur de signal hedgehog
AU2021410926A1 (en)	2023-06-29	Tetrahydrothienopyrimidinesulfonamide compounds
CN113461670B (zh)	2024-08-09	作为转染期间重排激酶抑制剂的新的化合物
WO2014160177A2 (fr)	2014-10-02	Inhibiteurs quinazolines de pi3k
US12258328B2 (en)	2025-03-25	6-membered heteroaryl-containing aminopyridine compounds as EGFR inhibitors
WO2025163050A1 (fr)	2025-08-07	Nouveaux derives amides, compositions pharmaceutiques les contenant et leurs utilisations comme inhibiteurs de sos1
EP2229376A1 (fr)	2010-09-22	3-cyanopyridines indole-substituées en tant qu'inhibiteurs de kinase
HK40066516A (zh)	2022-08-19	作为治疗剂的4- (咪唑并[1，2-a]吡啶-3-基)-n-(吡啶基)嘧啶-2-胺的衍生物