JP2009539998A5

JP2009539998A5 -

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Publication number: JP2009539998A5
Authority: JP; Japan
Prior art keywords: indol; nicotinonitrile; methyl; amino; ylamino
Prior art date: 2007-06-13
Legal status : Withdrawn

Application number

JP2009515487A

Other languages

English (en)

Japanese (ja)

Other versions

JP2009539998A (ja

Filing date

2007-06-13

Publication date

2010-07-29

2007-06-13 Application filed filed Critical

2007-06-13 Priority claimed from PCT/US2007/013954 external-priority patent/WO2007146376A2/en

2009-11-19 Publication of JP2009539998A publication Critical patent/JP2009539998A/ja

2010-07-29 Publication of JP2009539998A5 publication Critical patent/JP2009539998A5/ja

Status Withdrawn legal-status Critical Current

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-1 benzodioxanyl group Chemical group 0.000 claims description 398
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 192
GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims description 160
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 68
125000000217 alkyl group Chemical group 0.000 claims description 54
150000001875 compounds Chemical class 0.000 claims description 53
150000002148 esters Chemical class 0.000 claims description 48
150000003839 salts Chemical class 0.000 claims description 48
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 36
125000001072 heteroaryl group Chemical group 0.000 claims description 34
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 32
125000000753 cycloalkyl group Chemical group 0.000 claims description 30
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
125000003118 aryl group Chemical group 0.000 claims description 29
125000001188 haloalkyl group Chemical group 0.000 claims description 28
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 24
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 24
125000000304 alkynyl group Chemical group 0.000 claims description 22
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 22
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 14
229910052736 halogen Inorganic materials 0.000 claims description 14
150000002367 halogens Chemical class 0.000 claims description 14
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 12
125000004093 cyano group Chemical group *C#N 0.000 claims description 12
125000003342 alkenyl group Chemical group 0.000 claims description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
LUQVCHRDAGWYMG-UHFFFAOYSA-N 4-phenylbenzamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=CC=CC=C1 LUQVCHRDAGWYMG-UHFFFAOYSA-N 0.000 claims description 6
241000124008 Mammalia Species 0.000 claims description 6
102000001253 Protein Kinase Human genes 0.000 claims description 6
206010003246 arthritis Diseases 0.000 claims description 6
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
208000035475 disorder Diseases 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
150000004677 hydrates Chemical class 0.000 claims description 6
125000001041 indolyl group Chemical group 0.000 claims description 6
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 6
108060006633 protein kinase Proteins 0.000 claims description 6
125000004076 pyridyl group Chemical group 0.000 claims description 6
125000000168 pyrrolyl group Chemical group 0.000 claims description 6
125000001544 thienyl group Chemical group 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 5
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
230000001575 pathological effect Effects 0.000 claims description 5
125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 4
125000006012 2-chloroethoxy group Chemical group 0.000 claims description 4
IMEYANPAYSSKRC-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[4-(piperazin-1-ylmethyl)phenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(C=C1)=CC=C1CN1CCNCC1 IMEYANPAYSSKRC-UHFFFAOYSA-N 0.000 claims description 4
125000000928 benzodioxinyl group Chemical group O1C(=COC2=C1C=CC=C2)* 0.000 claims description 4
125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 4
125000002541 furyl group Chemical group 0.000 claims description 4
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 4
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 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
230000001404 mediated effect Effects 0.000 claims description 4
125000002757 morpholinyl group Chemical group 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
125000001624 naphthyl group Chemical group 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
125000003367 polycyclic group Chemical group 0.000 claims description 4
125000003226 pyrazolyl group Chemical group 0.000 claims description 4
125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
125000004568 thiomorpholinyl group Chemical group 0.000 claims description 4
125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
125000006708 (C5-C14) heteroaryl group Chemical group 0.000 claims description 3
208000023275 Autoimmune disease Diseases 0.000 claims description 3
201000004681 Psoriasis Diseases 0.000 claims description 3
208000006673 asthma Diseases 0.000 claims description 3
206010009887 colitis Diseases 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
230000002401 inhibitory effect Effects 0.000 claims description 3
208000018937 joint inflammation Diseases 0.000 claims description 3
201000006417 multiple sclerosis Diseases 0.000 claims description 3
201000008482 osteoarthritis Diseases 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
GJKWRHRABCZMIU-UHFFFAOYSA-N 1-[4-[5-cyano-4-[(4-methyl-1h-indol-5-yl)amino]pyridin-3-yl]phenyl]-3-cyclopropylurea Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(C=C1)=CC=C1NC(=O)NC1CC1 GJKWRHRABCZMIU-UHFFFAOYSA-N 0.000 claims description 2
KTOSRFZTOAPGSV-UHFFFAOYSA-N 1-[4-[5-cyano-4-[(4-methyl-1h-indol-5-yl)amino]pyridin-3-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C KTOSRFZTOAPGSV-UHFFFAOYSA-N 0.000 claims description 2
CKNLVXULMPJWNO-UHFFFAOYSA-N 1-butyl-3-[4-[5-cyano-4-[(4-methyl-1h-indol-5-yl)amino]pyridin-3-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCCCC)=CC=C1C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C CKNLVXULMPJWNO-UHFFFAOYSA-N 0.000 claims description 2
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 claims description 2
HCRYHRHBOYXHAI-UHFFFAOYSA-N 2-[5-cyano-4-(1h-indol-4-ylamino)pyridin-3-yl]-n,n-dimethylbenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=CC=C1C1=CN=CC(C#N)=C1NC1=CC=CC2=C1C=CN2 HCRYHRHBOYXHAI-UHFFFAOYSA-N 0.000 claims description 2
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims description 2
KMWPZWCJOGJZFF-UHFFFAOYSA-N 3-[3-[5-cyano-4-(1h-indol-5-ylamino)pyridin-3-yl]phenyl]-n-cyclopentylbenzamide Chemical compound C=1C=CC(C=2C=C(C=CC=2)C=2C(=C(C#N)C=NC=2)NC=2C=C3C=CNC3=CC=2)=CC=1C(=O)NC1CCCC1 KMWPZWCJOGJZFF-UHFFFAOYSA-N 0.000 claims description 2
GUNHRJLTFBDYOS-UHFFFAOYSA-N 3-[4-[5-cyano-4-[(4-methyl-1h-indol-5-yl)amino]pyridin-3-yl]phenyl]-1,1-dimethylurea Chemical compound C1=CC(NC(=O)N(C)C)=CC=C1C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C GUNHRJLTFBDYOS-UHFFFAOYSA-N 0.000 claims description 2
QIXANBDZSYPCBY-UHFFFAOYSA-N 3-[5-cyano-4-(1h-indol-4-ylamino)pyridin-3-yl]-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC(C=2C(=C(C#N)C=NC=2)NC=2C=3C=CNC=3C=CC=2)=C1 QIXANBDZSYPCBY-UHFFFAOYSA-N 0.000 claims description 2
BKTWQXGKBHVHMZ-UHFFFAOYSA-N 3-[5-cyano-4-(1h-indol-4-ylamino)pyridin-3-yl]-n,n-dimethylbenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=CC(C=2C(=C(C#N)C=NC=2)NC=2C=3C=CNC=3C=CC=2)=C1 BKTWQXGKBHVHMZ-UHFFFAOYSA-N 0.000 claims description 2
RCBIKUQGUQRBRL-UHFFFAOYSA-N 3-[5-cyano-4-(1h-indol-4-ylamino)pyridin-3-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2C(=C(C#N)C=NC=2)NC=2C=3C=CNC=3C=CC=2)=C1 RCBIKUQGUQRBRL-UHFFFAOYSA-N 0.000 claims description 2
NEZMRASZNJZDQH-UHFFFAOYSA-N 3-[5-cyano-4-(1h-indol-4-ylamino)pyridin-3-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC(C=2C(=C(C#N)C=NC=2)NC=2C=3C=CNC=3C=CC=2)=C1 NEZMRASZNJZDQH-UHFFFAOYSA-N 0.000 claims description 2
PDUJSKGQCLEINP-UHFFFAOYSA-N 3-[5-cyano-4-[(4-methyl-1h-indol-5-yl)amino]pyridin-3-yl]benzoic acid Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C1=CC=CC(C(O)=O)=C1 PDUJSKGQCLEINP-UHFFFAOYSA-N 0.000 claims description 2
125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 2
125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 2
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
AYVCYBNEDAUCGX-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-ylamino)-5-(3,4-dimethoxyphenyl)pyridine-3-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1C1=CN=CC(C#N)=C1NC1=CC=C(OCO2)C2=C1 AYVCYBNEDAUCGX-UHFFFAOYSA-N 0.000 claims description 2
MYRDYXMQEOXLRT-UHFFFAOYSA-N 4-(1,3-benzothiazol-6-ylamino)-5-[3-methoxy-4-(2-methoxyethoxy)phenyl]pyridine-3-carbonitrile Chemical compound C1=C(OC)C(OCCOC)=CC=C1C1=CN=CC(C#N)=C1NC1=CC=C(N=CS2)C2=C1 MYRDYXMQEOXLRT-UHFFFAOYSA-N 0.000 claims description 2
BDTALRYKZNZRDD-UHFFFAOYSA-N 4-(1,3-benzothiazol-6-ylamino)-5-[4-methoxy-3-(2-methoxyethoxy)phenyl]pyridine-3-carbonitrile Chemical compound C1=C(OC)C(OCCOC)=CC(C=2C(=C(C#N)C=NC=2)NC=2C=C3SC=NC3=CC=2)=C1 BDTALRYKZNZRDD-UHFFFAOYSA-N 0.000 claims description 2
KAECSRGNEJKWJC-UHFFFAOYSA-N 4-(1h-indazol-5-ylamino)-5-(3-methoxyphenyl)pyridine-3-carbonitrile Chemical compound COC1=CC=CC(C=2C(=C(C#N)C=NC=2)NC=2C=C3C=NNC3=CC=2)=C1 KAECSRGNEJKWJC-UHFFFAOYSA-N 0.000 claims description 2
WEBWAJMEXBHJLH-UHFFFAOYSA-N 4-(1h-indazol-6-ylamino)-5-(3-methoxyphenyl)pyridine-3-carbonitrile Chemical compound COC1=CC=CC(C=2C(=C(C#N)C=NC=2)NC=2C=C3NN=CC3=CC=2)=C1 WEBWAJMEXBHJLH-UHFFFAOYSA-N 0.000 claims description 2
WHBKXCTYGHTRJY-UHFFFAOYSA-N 4-(1h-indol-4-ylamino)-5-(2-methoxyphenyl)pyridine-3-carbonitrile Chemical compound COC1=CC=CC=C1C1=CN=CC(C#N)=C1NC1=CC=CC2=C1C=CN2 WHBKXCTYGHTRJY-UHFFFAOYSA-N 0.000 claims description 2
ONBJHMOEYBCQIK-UHFFFAOYSA-N 4-(1h-indol-4-ylamino)-5-(3-methylsulfonylphenyl)pyridine-3-carbonitrile Chemical compound CS(=O)(=O)C1=CC=CC(C=2C(=C(C#N)C=NC=2)NC=2C=3C=CNC=3C=CC=2)=C1 ONBJHMOEYBCQIK-UHFFFAOYSA-N 0.000 claims description 2
UNYSCSDWXYXDRM-UHFFFAOYSA-N 4-(1h-indol-4-ylamino)-5-(4-methoxyphenyl)pyridine-3-carbonitrile Chemical compound C1=CC(OC)=CC=C1C1=CN=CC(C#N)=C1NC1=CC=CC2=C1C=CN2 UNYSCSDWXYXDRM-UHFFFAOYSA-N 0.000 claims description 2
VFNLQYOUKPRALX-UHFFFAOYSA-N 4-(1h-indol-4-ylamino)-5-[1-(4-methylphenyl)sulfonylindol-3-yl]pyridine-3-carbonitrile Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C(C=2C(=C(C#N)C=NC=2)NC=2C=3C=CNC=3C=CC=2)=C1 VFNLQYOUKPRALX-UHFFFAOYSA-N 0.000 claims description 2
OVMXFSZIFQUQRH-UHFFFAOYSA-N 4-(1h-indol-4-ylamino)-5-[3-(2-methoxyethoxy)phenyl]pyridine-3-carbonitrile Chemical compound COCCOC1=CC=CC(C=2C(=C(C#N)C=NC=2)NC=2C=3C=CNC=3C=CC=2)=C1 OVMXFSZIFQUQRH-UHFFFAOYSA-N 0.000 claims description 2
QEKLUEUSIGZNIT-UHFFFAOYSA-N 4-(1h-indol-4-ylamino)-5-[3-(2-morpholin-4-ylethoxy)phenyl]pyridine-3-carbonitrile Chemical compound C=1C=CC=2NC=CC=2C=1NC=1C(C#N)=CN=CC=1C(C=1)=CC=CC=1OCCN1CCOCC1 QEKLUEUSIGZNIT-UHFFFAOYSA-N 0.000 claims description 2
WMEKLMVCWRPPGA-UHFFFAOYSA-N 4-(1h-indol-4-ylamino)-5-[3-(2-piperidin-1-ylethoxy)phenyl]pyridine-3-carbonitrile Chemical compound C=1C=CC=2NC=CC=2C=1NC=1C(C#N)=CN=CC=1C(C=1)=CC=CC=1OCCN1CCCCC1 WMEKLMVCWRPPGA-UHFFFAOYSA-N 0.000 claims description 2
CDSMVYVAOJOBOE-UHFFFAOYSA-N 4-(1h-indol-4-ylamino)-5-[3-(2-pyrrolidin-1-ylethoxy)phenyl]pyridine-3-carbonitrile Chemical compound C=1C=CC=2NC=CC=2C=1NC=1C(C#N)=CN=CC=1C(C=1)=CC=CC=1OCCN1CCCC1 CDSMVYVAOJOBOE-UHFFFAOYSA-N 0.000 claims description 2
MMVHNEPFDQHBTM-UHFFFAOYSA-N 4-(1h-indol-4-ylamino)-5-[3-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CCOC1=CC=CC(C=2C(=C(C#N)C=NC=2)NC=2C=3C=CNC=3C=CC=2)=C1 MMVHNEPFDQHBTM-UHFFFAOYSA-N 0.000 claims description 2
NCPMIPMGHYJCNG-UHFFFAOYSA-N 4-(1h-indol-4-ylamino)-5-[3-[4-(pyrrolidine-1-carbonyl)phenyl]phenyl]pyridine-3-carbonitrile Chemical compound C=1C=C(C=2C=C(C=CC=2)C=2C(=C(C#N)C=NC=2)NC=2C=3C=CNC=3C=CC=2)C=CC=1C(=O)N1CCCC1 NCPMIPMGHYJCNG-UHFFFAOYSA-N 0.000 claims description 2
IWRCRIJOOGSJGK-UHFFFAOYSA-N 4-(1h-indol-4-ylamino)-5-[3-methoxy-4-(2-methoxyethoxy)phenyl]pyridine-3-carbonitrile Chemical compound C1=C(OC)C(OCCOC)=CC=C1C1=CN=CC(C#N)=C1NC1=CC=CC2=C1C=CN2 IWRCRIJOOGSJGK-UHFFFAOYSA-N 0.000 claims description 2
NYYMOTTUMJLICS-UHFFFAOYSA-N 4-(1h-indol-4-ylamino)-5-[4-(2-morpholin-4-ylethoxy)phenyl]pyridine-3-carbonitrile Chemical compound C=1C=CC=2NC=CC=2C=1NC=1C(C#N)=CN=CC=1C(C=C1)=CC=C1OCCN1CCOCC1 NYYMOTTUMJLICS-UHFFFAOYSA-N 0.000 claims description 2
ZPKBYERIJJCKAI-UHFFFAOYSA-N 4-(1h-indol-4-ylamino)-5-[4-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CCOC1=CC=C(C=2C(=C(C#N)C=NC=2)NC=2C=3C=CNC=3C=CC=2)C=C1 ZPKBYERIJJCKAI-UHFFFAOYSA-N 0.000 claims description 2
OQGXWJUPOQZCMP-UHFFFAOYSA-N 4-(1h-indol-4-ylamino)-5-[4-methoxy-3-(2-methoxyethoxy)phenyl]pyridine-3-carbonitrile Chemical compound C1=C(OC)C(OCCOC)=CC(C=2C(=C(C#N)C=NC=2)NC=2C=3C=CNC=3C=CC=2)=C1 OQGXWJUPOQZCMP-UHFFFAOYSA-N 0.000 claims description 2
SMSCTXBNQPWSJB-UHFFFAOYSA-N 4-(1h-indol-4-ylamino)-5-[4-methoxy-3-(2-morpholin-4-ylethoxy)phenyl]pyridine-3-carbonitrile Chemical compound COC1=CC=C(C=2C(=C(C#N)C=NC=2)NC=2C=3C=CNC=3C=CC=2)C=C1OCCN1CCOCC1 SMSCTXBNQPWSJB-UHFFFAOYSA-N 0.000 claims description 2
DLEATKJPWWNGHU-UHFFFAOYSA-N 4-(1h-indol-4-ylamino)-5-[4-methoxy-3-(2-piperidin-1-ylethoxy)phenyl]pyridine-3-carbonitrile Chemical compound COC1=CC=C(C=2C(=C(C#N)C=NC=2)NC=2C=3C=CNC=3C=CC=2)C=C1OCCN1CCCCC1 DLEATKJPWWNGHU-UHFFFAOYSA-N 0.000 claims description 2
UMYMVHQYASZFES-UHFFFAOYSA-N 4-(1h-indol-4-ylamino)-5-[4-methoxy-3-[2-(3-phenylpropylamino)ethoxy]phenyl]pyridine-3-carbonitrile Chemical compound COC1=CC=C(C=2C(=C(C#N)C=NC=2)NC=2C=3C=CNC=3C=CC=2)C=C1OCCNCCCC1=CC=CC=C1 UMYMVHQYASZFES-UHFFFAOYSA-N 0.000 claims description 2
DQUUANKBPSGREK-UHFFFAOYSA-N 4-(1h-indol-4-ylamino)-5-[4-methoxy-3-[2-(3-pyrrolidin-1-ylpropylamino)ethoxy]phenyl]pyridine-3-carbonitrile Chemical compound COC1=CC=C(C=2C(=C(C#N)C=NC=2)NC=2C=3C=CNC=3C=CC=2)C=C1OCCNCCCN1CCCC1 DQUUANKBPSGREK-UHFFFAOYSA-N 0.000 claims description 2
KRALBDOCPZMWIS-UHFFFAOYSA-N 4-(1h-indol-4-ylamino)-5-[4-methoxy-3-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl]pyridine-3-carbonitrile Chemical compound COC1=CC=C(C=2C(=C(C#N)C=NC=2)NC=2C=3C=CNC=3C=CC=2)C=C1OCCN1CCN(C)CC1 KRALBDOCPZMWIS-UHFFFAOYSA-N 0.000 claims description 2
FMHLBNDERLRCDO-UHFFFAOYSA-N 4-(1h-indol-4-ylamino)-5-[4-methoxy-3-[2-[2-(1-methylpyrrolidin-2-yl)ethylamino]ethoxy]phenyl]pyridine-3-carbonitrile Chemical compound COC1=CC=C(C=2C(=C(C#N)C=NC=2)NC=2C=3C=CNC=3C=CC=2)C=C1OCCNCCC1CCCN1C FMHLBNDERLRCDO-UHFFFAOYSA-N 0.000 claims description 2
VYKNGSAUNAORNC-UHFFFAOYSA-N 4-(1h-indol-4-ylamino)-5-[4-methoxy-3-[2-[3-(2-oxopyrrolidin-1-yl)propylamino]ethoxy]phenyl]pyridine-3-carbonitrile Chemical compound COC1=CC=C(C=2C(=C(C#N)C=NC=2)NC=2C=3C=CNC=3C=CC=2)C=C1OCCNCCCN1CCCC1=O VYKNGSAUNAORNC-UHFFFAOYSA-N 0.000 claims description 2
JBQXWZHNCFEWOV-UHFFFAOYSA-N 4-(1h-indol-4-ylamino)-5-[5-(morpholin-4-ylmethyl)-1-benzothiophen-2-yl]pyridine-3-carbonitrile Chemical compound C=1C=CC=2NC=CC=2C=1NC=1C(C#N)=CN=CC=1C(SC1=CC=2)=CC1=CC=2CN1CCOCC1 JBQXWZHNCFEWOV-UHFFFAOYSA-N 0.000 claims description 2
OMAALFXORIJCOD-UHFFFAOYSA-N 4-(1h-indol-4-ylamino)-5-[5-(piperidin-1-ylmethyl)-1-benzothiophen-2-yl]pyridine-3-carbonitrile Chemical compound C=1C=CC=2NC=CC=2C=1NC=1C(C#N)=CN=CC=1C(SC1=CC=2)=CC1=CC=2CN1CCCCC1 OMAALFXORIJCOD-UHFFFAOYSA-N 0.000 claims description 2
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LQKXDFOINGHQAV-UHFFFAOYSA-N 4-(1h-indol-4-ylamino)-5-[5-[(2-phenylethylamino)methyl]-1-benzothiophen-2-yl]pyridine-3-carbonitrile Chemical compound C=1C=CC=2NC=CC=2C=1NC=1C(C#N)=CN=CC=1C(SC1=CC=2)=CC1=CC=2CNCCC1=CC=CC=C1 LQKXDFOINGHQAV-UHFFFAOYSA-N 0.000 claims description 2
OEZNQDDIEIKNMM-UHFFFAOYSA-N 4-(1h-indol-4-ylamino)-5-[5-[(3-methoxypropylamino)methyl]-1-benzothiophen-2-yl]pyridine-3-carbonitrile Chemical compound C=1C2=CC(CNCCCOC)=CC=C2SC=1C1=CN=CC(C#N)=C1NC1=CC=CC2=C1C=CN2 OEZNQDDIEIKNMM-UHFFFAOYSA-N 0.000 claims description 2
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LUJMHNVJZUUOTA-UHFFFAOYSA-N 4-(1h-indol-4-ylamino)-5-[5-[(pyridin-2-ylmethylamino)methyl]-1-benzothiophen-2-yl]pyridine-3-carbonitrile Chemical compound C=1C=CC=2NC=CC=2C=1NC=1C(C#N)=CN=CC=1C(SC1=CC=2)=CC1=CC=2CNCC1=CC=CC=N1 LUJMHNVJZUUOTA-UHFFFAOYSA-N 0.000 claims description 2
DHOSIKFTTLKULC-UHFFFAOYSA-N 4-(1h-indol-4-ylamino)-5-[5-[(pyridin-3-ylmethylamino)methyl]-1-benzothiophen-2-yl]pyridine-3-carbonitrile Chemical compound C=1C=CC=2NC=CC=2C=1NC=1C(C#N)=CN=CC=1C(SC1=CC=2)=CC1=CC=2CNCC1=CC=CN=C1 DHOSIKFTTLKULC-UHFFFAOYSA-N 0.000 claims description 2
OGBYJZUJEJZKLG-UHFFFAOYSA-N 4-(1h-indol-4-ylamino)-5-[5-[(pyridin-4-ylmethylamino)methyl]-1-benzothiophen-2-yl]pyridine-3-carbonitrile Chemical compound C=1C=CC=2NC=CC=2C=1NC=1C(C#N)=CN=CC=1C(SC1=CC=2)=CC1=CC=2CNCC1=CC=NC=C1 OGBYJZUJEJZKLG-UHFFFAOYSA-N 0.000 claims description 2
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CFOJFWIJAOIFID-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-(2-thiophen-3-ylphenyl)pyridine-3-carbonitrile Chemical compound C=1C=C2NC=CC2=CC=1NC=1C(C#N)=CN=CC=1C1=CC=CC=C1C=1C=CSC=1 CFOJFWIJAOIFID-UHFFFAOYSA-N 0.000 claims description 2
RVJWVCDSWMKKRU-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-(3-nitrophenyl)pyridine-3-carbonitrile Chemical compound [O-][N+](=O)C1=CC=CC(C=2C(=C(C#N)C=NC=2)NC=2C=C3C=CNC3=CC=2)=C1 RVJWVCDSWMKKRU-UHFFFAOYSA-N 0.000 claims description 2
HMYMXCQGJNVKCG-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-(3-phenylmethoxyphenyl)pyridine-3-carbonitrile Chemical compound C=1C=C2NC=CC2=CC=1NC=1C(C#N)=CN=CC=1C(C=1)=CC=CC=1OCC1=CC=CC=C1 HMYMXCQGJNVKCG-UHFFFAOYSA-N 0.000 claims description 2
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KSKQFUGZPLPKMQ-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-(4-methoxy-3-thiophen-2-ylphenyl)pyridine-3-carbonitrile Chemical compound COC1=CC=C(C=2C(=C(C#N)C=NC=2)NC=2C=C3C=CNC3=CC=2)C=C1C1=CC=CS1 KSKQFUGZPLPKMQ-UHFFFAOYSA-N 0.000 claims description 2
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PJHNUSLVGYMBLI-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-[3-(2-pyrrolidin-1-ylethoxy)phenyl]pyridine-3-carbonitrile Chemical compound C=1C=C2NC=CC2=CC=1NC=1C(C#N)=CN=CC=1C(C=1)=CC=CC=1OCCN1CCCC1 PJHNUSLVGYMBLI-UHFFFAOYSA-N 0.000 claims description 2
ADGADKKJRSLCOU-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-[3-(3-methylphenyl)phenyl]pyridine-3-carbonitrile Chemical compound CC1=CC=CC(C=2C=C(C=CC=2)C=2C(=C(C#N)C=NC=2)NC=2C=C3C=CNC3=CC=2)=C1 ADGADKKJRSLCOU-UHFFFAOYSA-N 0.000 claims description 2
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ODXAULWFUALELN-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-[3-(4-methylthiophen-2-yl)phenyl]pyridine-3-carbonitrile Chemical compound CC1=CSC(C=2C=C(C=CC=2)C=2C(=C(C#N)C=NC=2)NC=2C=C3C=CNC3=CC=2)=C1 ODXAULWFUALELN-UHFFFAOYSA-N 0.000 claims description 2
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BGZMSBKNUPIITA-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-[3-[4-(4-methylpiperazine-1-carbonyl)phenyl]phenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(C=2C=C(C=CC=2)C=2C(=C(C#N)C=NC=2)NC=2C=C3C=CNC3=CC=2)C=C1 BGZMSBKNUPIITA-UHFFFAOYSA-N 0.000 claims description 2
JELLXGHLAJLQCK-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-[3-[4-(morpholine-4-carbonyl)phenyl]phenyl]pyridine-3-carbonitrile Chemical compound C=1C=C(C=2C=C(C=CC=2)C=2C(=C(C#N)C=NC=2)NC=2C=C3C=CNC3=CC=2)C=CC=1C(=O)N1CCOCC1 JELLXGHLAJLQCK-UHFFFAOYSA-N 0.000 claims description 2
RSNBFYSOOWDECP-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-[3-[4-(pyrrolidine-1-carbonyl)phenyl]phenyl]pyridine-3-carbonitrile Chemical compound C=1C=C(C=2C=C(C=CC=2)C=2C(=C(C#N)C=NC=2)NC=2C=C3C=CNC3=CC=2)C=CC=1C(=O)N1CCCC1 RSNBFYSOOWDECP-UHFFFAOYSA-N 0.000 claims description 2
YOAGSVCDXLNBFV-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-[3-[5-(morpholin-4-ylmethyl)thiophen-2-yl]phenyl]pyridine-3-carbonitrile Chemical compound C=1C=C2NC=CC2=CC=1NC=1C(C#N)=CN=CC=1C(C=1)=CC=CC=1C(S1)=CC=C1CN1CCOCC1 YOAGSVCDXLNBFV-UHFFFAOYSA-N 0.000 claims description 2
MEUHCFBRCAGXNY-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-[3-[5-[(4-methylpiperazin-1-yl)methyl]thiophen-2-yl]phenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CC1=CC=C(C=2C=C(C=CC=2)C=2C(=C(C#N)C=NC=2)NC=2C=C3C=CNC3=CC=2)S1 MEUHCFBRCAGXNY-UHFFFAOYSA-N 0.000 claims description 2
UKDISGSUKANYSO-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-[3-methoxy-4-(2-methoxyethoxy)phenyl]pyridine-3-carbonitrile Chemical compound C1=C(OC)C(OCCOC)=CC=C1C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1 UKDISGSUKANYSO-UHFFFAOYSA-N 0.000 claims description 2
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GCVMAALHEAODSM-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-[4-methoxy-3-(2-methoxyethoxy)phenyl]pyridine-3-carbonitrile Chemical compound C1=C(OC)C(OCCOC)=CC(C=2C(=C(C#N)C=NC=2)NC=2C=C3C=CNC3=CC=2)=C1 GCVMAALHEAODSM-UHFFFAOYSA-N 0.000 claims description 2
HBPQOGWJPPVRGU-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-[4-methoxy-3-(2-morpholin-4-ylethoxy)phenyl]pyridine-3-carbonitrile Chemical compound COC1=CC=C(C=2C(=C(C#N)C=NC=2)NC=2C=C3C=CNC3=CC=2)C=C1OCCN1CCOCC1 HBPQOGWJPPVRGU-UHFFFAOYSA-N 0.000 claims description 2
BMBGNJMERANPQW-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-[4-methoxy-3-(2-piperazin-1-ylethoxy)phenyl]pyridine-3-carbonitrile Chemical compound COC1=CC=C(C=2C(=C(C#N)C=NC=2)NC=2C=C3C=CNC3=CC=2)C=C1OCCN1CCNCC1 BMBGNJMERANPQW-UHFFFAOYSA-N 0.000 claims description 2
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CBQHRHWXTPJAJD-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-[4-methoxy-3-[2-(2-methoxyethylamino)ethoxy]phenyl]pyridine-3-carbonitrile Chemical compound C1=C(OC)C(OCCNCCOC)=CC(C=2C(=C(C#N)C=NC=2)NC=2C=C3C=CNC3=CC=2)=C1 CBQHRHWXTPJAJD-UHFFFAOYSA-N 0.000 claims description 2
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IMMRDRGADQVBCX-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-[4-methoxy-3-[2-(pyridin-2-ylmethylamino)ethoxy]phenyl]pyridine-3-carbonitrile Chemical compound COC1=CC=C(C=2C(=C(C#N)C=NC=2)NC=2C=C3C=CNC3=CC=2)C=C1OCCNCC1=CC=CC=N1 IMMRDRGADQVBCX-UHFFFAOYSA-N 0.000 claims description 2
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WPYYOSGZNDLLDS-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-pyrimidin-5-ylpyridine-3-carbonitrile Chemical compound C=1C=C2NC=CC2=CC=1NC=1C(C#N)=CN=CC=1C1=CN=CN=C1 WPYYOSGZNDLLDS-UHFFFAOYSA-N 0.000 claims description 2
SYTNKPCOORPMDR-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-thiophen-2-ylpyridine-3-carbonitrile Chemical compound C=1C=C2NC=CC2=CC=1NC=1C(C#N)=CN=CC=1C1=CC=CS1 SYTNKPCOORPMDR-UHFFFAOYSA-N 0.000 claims description 2
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SYYUJKCGTTVUDP-UHFFFAOYSA-N 4-(1h-indol-6-ylamino)-5-[3-(2-pyrrolidin-1-ylethoxy)phenyl]pyridine-3-carbonitrile Chemical compound C=1C=C2C=CNC2=CC=1NC=1C(C#N)=CN=CC=1C(C=1)=CC=CC=1OCCN1CCCC1 SYYUJKCGTTVUDP-UHFFFAOYSA-N 0.000 claims description 2
YAFRCXYTUBXBTD-UHFFFAOYSA-N 4-(1h-indol-6-ylamino)-5-[3-methoxy-4-(2-methoxyethoxy)phenyl]pyridine-3-carbonitrile Chemical compound C1=C(OC)C(OCCOC)=CC=C1C1=CN=CC(C#N)=C1NC1=CC=C(C=CN2)C2=C1 YAFRCXYTUBXBTD-UHFFFAOYSA-N 0.000 claims description 2
GPPFOSUKEIOMGW-UHFFFAOYSA-N 4-(1h-indol-6-ylamino)-5-[4-methoxy-3-(2-methoxyethoxy)phenyl]pyridine-3-carbonitrile Chemical compound C1=C(OC)C(OCCOC)=CC(C=2C(=C(C#N)C=NC=2)NC=2C=C3NC=CC3=CC=2)=C1 GPPFOSUKEIOMGW-UHFFFAOYSA-N 0.000 claims description 2
BZLQIUBUNGIWCF-UHFFFAOYSA-N 4-(2,1,3-benzothiadiazol-4-ylamino)-5-(3,4-dimethoxyphenyl)pyridine-3-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1C1=CN=CC(C#N)=C1NC1=CC=CC2=NSN=C12 BZLQIUBUNGIWCF-UHFFFAOYSA-N 0.000 claims description 2
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JFJXUGRUMFXVRP-UHFFFAOYSA-N 4-(2,3-dihydro-1h-inden-5-ylamino)-5-(3,4-dimethoxyphenyl)pyridine-3-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1C1=CN=CC(C#N)=C1NC1=CC=C(CCC2)C2=C1 JFJXUGRUMFXVRP-UHFFFAOYSA-N 0.000 claims description 2
SUEMXCWKNBMGDK-UHFFFAOYSA-N 4-(2h-benzotriazol-5-ylamino)-5-[4-methoxy-3-(2-methoxyethoxy)phenyl]pyridine-3-carbonitrile Chemical compound C1=C(OC)C(OCCOC)=CC(C=2C(=C(C#N)C=NC=2)NC=2C=C3N=NNC3=CC=2)=C1 SUEMXCWKNBMGDK-UHFFFAOYSA-N 0.000 claims description 2
HZPOVSDUDPDLQQ-UHFFFAOYSA-N 4-[(2,4-dimethyl-1h-indol-5-yl)amino]-5-[3-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CCOC1=CC=CC(C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=C(C)NC3=CC=2)C)=C1 HZPOVSDUDPDLQQ-UHFFFAOYSA-N 0.000 claims description 2
WSSFHMXXCVLHEY-UHFFFAOYSA-N 4-[(2,4-dimethyl-1h-indol-5-yl)amino]-5-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CC1=CC=C(C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=C(C)NC3=CC=2)C)C=C1 WSSFHMXXCVLHEY-UHFFFAOYSA-N 0.000 claims description 2
TXXIXYFCHWWATR-UHFFFAOYSA-N 4-[(2,4-dimethyl-1h-indol-5-yl)amino]-5-[4-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CCOC1=CC=C(C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=C(C)NC3=CC=2)C)C=C1 TXXIXYFCHWWATR-UHFFFAOYSA-N 0.000 claims description 2
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SEZHDSKHPIHIQM-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-(1,3-thiazol-2-yl)pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C1=NC=CS1 SEZHDSKHPIHIQM-UHFFFAOYSA-N 0.000 claims description 2
BAHPJGOILZHCLN-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-(1,3-thiazol-4-yl)pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C1=CSC=N1 BAHPJGOILZHCLN-UHFFFAOYSA-N 0.000 claims description 2
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ARMJUXPOHQQFRK-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-(2-piperidin-1-ylpyrimidin-5-yl)pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(C=N1)=CN=C1N1CCCCC1 ARMJUXPOHQQFRK-UHFFFAOYSA-N 0.000 claims description 2
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VSYBFJIYXCYUHS-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-(3-thiophen-2-ylphenyl)pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(C=1)=CC=CC=1C1=CC=CS1 VSYBFJIYXCYUHS-UHFFFAOYSA-N 0.000 claims description 2
GLHCOYIUVIWKGP-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-(6-morpholin-4-ylpyridin-3-yl)pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(C=N1)=CC=C1N1CCOCC1 GLHCOYIUVIWKGP-UHFFFAOYSA-N 0.000 claims description 2
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AGDJHMBOTVIESJ-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[2-(piperazin-1-ylmethyl)pyridin-4-yl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(C=1)=CC=NC=1CN1CCNCC1 AGDJHMBOTVIESJ-UHFFFAOYSA-N 0.000 claims description 2
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RCKJONRFOBKJOI-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[4-(2-piperazin-1-ylethoxy)phenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(C=C1)=CC=C1OCCN1CCNCC1 RCKJONRFOBKJOI-UHFFFAOYSA-N 0.000 claims description 2
KJYFFRNQSIBKHB-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[4-(2-pyrrolidin-1-ylethoxy)phenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(C=C1)=CC=C1OCCN1CCCC1 KJYFFRNQSIBKHB-UHFFFAOYSA-N 0.000 claims description 2
YYZFWJSCRFDEOP-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[4-(morpholin-4-ylmethyl)pyridin-2-yl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(N=CC=1)=CC=1CN1CCOCC1 YYZFWJSCRFDEOP-UHFFFAOYSA-N 0.000 claims description 2
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DPAHGIMSFFKBJW-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[4-[(4-methylpiperazin-1-yl)methyl]pyridin-2-yl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CC1=CC=NC(C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=C1 DPAHGIMSFFKBJW-UHFFFAOYSA-N 0.000 claims description 2
QKFGGOZXPGBIFV-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[4-[2-(4-morpholin-4-ylpiperidin-1-yl)ethoxy]phenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(C=C1)=CC=C1OCCN(CC1)CCC1N1CCOCC1 QKFGGOZXPGBIFV-UHFFFAOYSA-N 0.000 claims description 2
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LARLRFWKAHWFHS-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[4-[2-[(1-methylpiperidin-4-yl)methylamino]ethoxy]phenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCC1CNCCOC1=CC=C(C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)C=C1 LARLRFWKAHWFHS-UHFFFAOYSA-N 0.000 claims description 2
GTWLYEVXNCSGBU-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[5-(morpholin-4-ylmethyl)-1-benzofuran-2-yl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(OC1=CC=2)=CC1=CC=2CN1CCOCC1 GTWLYEVXNCSGBU-UHFFFAOYSA-N 0.000 claims description 2
VMRZSNDAPJYPND-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[5-(morpholin-4-ylmethyl)furan-2-yl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(O1)=CC=C1CN1CCOCC1 VMRZSNDAPJYPND-UHFFFAOYSA-N 0.000 claims description 2
RUPKAQMHKWJGIA-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[5-(morpholin-4-ylmethyl)pyridin-2-yl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(N=C1)=CC=C1CN1CCOCC1 RUPKAQMHKWJGIA-UHFFFAOYSA-N 0.000 claims description 2
GPXJATBMEGDDAU-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[5-(morpholin-4-ylmethyl)pyridin-3-yl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(C=1)=CN=CC=1CN1CCOCC1 GPXJATBMEGDDAU-UHFFFAOYSA-N 0.000 claims description 2
DHUPFOOXPODTRC-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[5-(piperazin-1-ylmethyl)-1-benzofuran-2-yl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(OC1=CC=2)=CC1=CC=2CN1CCNCC1 DHUPFOOXPODTRC-UHFFFAOYSA-N 0.000 claims description 2
PPSQGUQANTVARX-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[5-(piperazin-1-ylmethyl)pyridin-2-yl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(N=C1)=CC=C1CN1CCNCC1 PPSQGUQANTVARX-UHFFFAOYSA-N 0.000 claims description 2
JCDVJGWGMRZRMD-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[5-(piperazin-1-ylmethyl)pyridin-3-yl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(C=1)=CN=CC=1CN1CCNCC1 JCDVJGWGMRZRMD-UHFFFAOYSA-N 0.000 claims description 2
ZDISSWUDAVTQSK-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[5-(piperidin-1-ylmethyl)-1-benzothiophen-2-yl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(SC1=CC=2)=CC1=CC=2CN1CCCCC1 ZDISSWUDAVTQSK-UHFFFAOYSA-N 0.000 claims description 2
GHCPXYAHSHXFSC-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[5-(piperidin-1-ylmethyl)furan-2-yl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(O1)=CC=C1CN1CCCCC1 GHCPXYAHSHXFSC-UHFFFAOYSA-N 0.000 claims description 2
USYSUTGHQKSLCI-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[5-(pyrrolidin-1-ylmethyl)-1-benzofuran-2-yl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(OC1=CC=2)=CC1=CC=2CN1CCCC1 USYSUTGHQKSLCI-UHFFFAOYSA-N 0.000 claims description 2
FDIBZBJWWAQEFA-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[5-(pyrrolidin-1-ylmethyl)furan-2-yl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(O1)=CC=C1CN1CCCC1 FDIBZBJWWAQEFA-UHFFFAOYSA-N 0.000 claims description 2
INEBWSOWIIORFD-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[5-[(2-pyrrolidin-1-ylethylamino)methyl]-1-benzofuran-2-yl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(OC1=CC=2)=CC1=CC=2CNCCN1CCCC1 INEBWSOWIIORFD-UHFFFAOYSA-N 0.000 claims description 2
AGSDUOONWFEAKN-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[5-[(3-phenylpropylamino)methyl]furan-2-yl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(O1)=CC=C1CNCCCC1=CC=CC=C1 AGSDUOONWFEAKN-UHFFFAOYSA-N 0.000 claims description 2
DZIUPOCVDSYPSY-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[5-[(4-methylpiperazin-1-yl)methyl]-1-benzofuran-2-yl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CC1=CC=C(OC(=C2)C=3C(=C(C#N)C=NC=3)NC=3C(=C4C=CNC4=CC=3)C)C2=C1 DZIUPOCVDSYPSY-UHFFFAOYSA-N 0.000 claims description 2
MKCCHIFQLCHEBR-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[5-[(4-methylpiperazin-1-yl)methyl]-1-benzothiophen-2-yl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CC1=CC=C(SC(=C2)C=3C(=C(C#N)C=NC=3)NC=3C(=C4C=CNC4=CC=3)C)C2=C1 MKCCHIFQLCHEBR-UHFFFAOYSA-N 0.000 claims description 2
AWKZERSILQVXCP-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[5-[(4-methylpiperazin-1-yl)methyl]furan-3-yl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CC1=CC(C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=CO1 AWKZERSILQVXCP-UHFFFAOYSA-N 0.000 claims description 2
KYUNMPOAUPSUET-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[5-[(4-methylpiperazin-1-yl)methyl]pyridin-2-yl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CC1=CC=C(C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)N=C1 KYUNMPOAUPSUET-UHFFFAOYSA-N 0.000 claims description 2
HNEPHSYDSCBQIV-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[5-[(4-methylpiperazin-1-yl)methyl]pyridin-3-yl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CC1=CN=CC(C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=C1 HNEPHSYDSCBQIV-UHFFFAOYSA-N 0.000 claims description 2
XFBBVLBWLYXZTB-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[5-[(4-methylpiperazin-1-yl)methyl]thiophen-3-yl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CC1=CC(C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=CS1 XFBBVLBWLYXZTB-UHFFFAOYSA-N 0.000 claims description 2
SEIUNLLITIPADW-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[5-[(4-morpholin-4-ylpiperidin-1-yl)methyl]-1-benzofuran-2-yl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(OC1=CC=2)=CC1=CC=2CN(CC1)CCC1N1CCOCC1 SEIUNLLITIPADW-UHFFFAOYSA-N 0.000 claims description 2
ZNKTXYGGKTULIB-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[5-[(4-morpholin-4-ylpiperidin-1-yl)methyl]furan-2-yl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(O1)=CC=C1CN(CC1)CCC1N1CCOCC1 ZNKTXYGGKTULIB-UHFFFAOYSA-N 0.000 claims description 2
YVEIHMOVASHGDZ-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[5-[(4-piperidin-1-ylpiperidin-1-yl)methyl]-1-benzofuran-2-yl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(OC1=CC=2)=CC1=CC=2CN(CC1)CCC1N1CCCCC1 YVEIHMOVASHGDZ-UHFFFAOYSA-N 0.000 claims description 2
HIELPQSRAQDIQL-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[5-[(4-piperidin-1-ylpiperidin-1-yl)methyl]furan-2-yl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(O1)=CC=C1CN(CC1)CCC1N1CCCCC1 HIELPQSRAQDIQL-UHFFFAOYSA-N 0.000 claims description 2
FAQJIZKBJRQPIA-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[5-[(4-pyridin-2-ylpiperazin-1-yl)methyl]-1-benzofuran-2-yl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(OC1=CC=2)=CC1=CC=2CN(CC1)CCN1C1=CC=CC=N1 FAQJIZKBJRQPIA-UHFFFAOYSA-N 0.000 claims description 2
CYIIKCQBVSBYGQ-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[5-[(4-pyrrolidin-1-ylpiperidin-1-yl)methyl]-1-benzofuran-2-yl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(OC1=CC=2)=CC1=CC=2CN(CC1)CCC1N1CCCC1 CYIIKCQBVSBYGQ-UHFFFAOYSA-N 0.000 claims description 2
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LLOXHJCGECYXLA-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[5-[(pyridin-3-ylmethylamino)methyl]-1-benzofuran-2-yl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(OC1=CC=2)=CC1=CC=2CNCC1=CC=CN=C1 LLOXHJCGECYXLA-UHFFFAOYSA-N 0.000 claims description 2
IPTNCKGZXXRHSV-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[5-[(pyridin-4-ylmethylamino)methyl]-1-benzofuran-2-yl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(OC1=CC=2)=CC1=CC=2CNCC1=CC=NC=C1 IPTNCKGZXXRHSV-UHFFFAOYSA-N 0.000 claims description 2
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RVULSEQEDLMHMF-UHFFFAOYSA-N 4-[3-[5-cyano-4-(1h-indol-4-ylamino)pyridin-3-yl]phenyl]-n-cyclopentylbenzamide Chemical compound C=1C=C(C=2C=C(C=CC=2)C=2C(=C(C#N)C=NC=2)NC=2C=3C=CNC=3C=CC=2)C=CC=1C(=O)NC1CCCC1 RVULSEQEDLMHMF-UHFFFAOYSA-N 0.000 claims description 2
ASPUWPLRIIVILG-UHFFFAOYSA-N 4-[3-[5-cyano-4-(1h-indol-4-ylamino)pyridin-3-yl]phenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC(C=2C(=C(C#N)C=NC=2)NC=2C=3C=CNC=3C=CC=2)=C1 ASPUWPLRIIVILG-UHFFFAOYSA-N 0.000 claims description 2
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SYZMGTBRCDCPMC-UHFFFAOYSA-N 4-[3-[5-cyano-4-(1h-indol-5-ylamino)pyridin-3-yl]phenyl]-n-cyclopropylbenzamide Chemical compound C=1C=C(C=2C=C(C=CC=2)C=2C(=C(C#N)C=NC=2)NC=2C=C3C=CNC3=CC=2)C=CC=1C(=O)NC1CC1 SYZMGTBRCDCPMC-UHFFFAOYSA-N 0.000 claims description 2
BTFYBZIOOGCZKS-UHFFFAOYSA-N 4-[3-[5-cyano-4-(1h-indol-5-ylamino)pyridin-3-yl]phenyl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=CC=CC(C=2C(=C(C#N)C=NC=2)NC=2C=C3C=CNC3=CC=2)=C1 BTFYBZIOOGCZKS-UHFFFAOYSA-N 0.000 claims description 2
KYQBHNLZYKJKIS-UHFFFAOYSA-N 4-[5-[5-cyano-4-(1h-indol-5-ylamino)pyridin-3-yl]-2-methoxyphenyl]-n-cyclopentylbenzamide Chemical compound COC1=CC=C(C=2C(=C(C#N)C=NC=2)NC=2C=C3C=CNC3=CC=2)C=C1C(C=C1)=CC=C1C(=O)NC1CCCC1 KYQBHNLZYKJKIS-UHFFFAOYSA-N 0.000 claims description 2
KEJSNRKWHNIBJU-UHFFFAOYSA-N 4-[5-cyano-4-(1h-indol-4-ylamino)pyridin-3-yl]-n,n-dimethylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1C1=CN=CC(C#N)=C1NC1=CC=CC2=C1C=CN2 KEJSNRKWHNIBJU-UHFFFAOYSA-N 0.000 claims description 2
HURFUJIZLFTQMY-UHFFFAOYSA-N 4-[5-cyano-4-(1h-indol-4-ylamino)pyridin-3-yl]-n-(2-methoxyethyl)benzamide Chemical compound C1=CC(C(=O)NCCOC)=CC=C1C1=CN=CC(C#N)=C1NC1=CC=CC2=C1C=CN2 HURFUJIZLFTQMY-UHFFFAOYSA-N 0.000 claims description 2
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DKARVWYIBCKFNM-CVEARBPZSA-N 4-[[(1s,3r)-3-(aminomethyl)cyclohexyl]methylamino]-5-(3,4-dimethoxyphenyl)pyridine-3-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1C1=CN=CC(C#N)=C1NC[C@@H]1C[C@H](CN)CCC1 DKARVWYIBCKFNM-CVEARBPZSA-N 0.000 claims description 2
MEMBNXUNNXCINL-UHFFFAOYSA-N 5-(1,3-benzodioxol-5-yl)-4-(1h-indol-5-ylamino)pyridine-3-carbonitrile Chemical compound C1=C2NC=CC2=CC(NC2=C(C=3C=C4OCOC4=CC=3)C=NC=C2C#N)=C1 MEMBNXUNNXCINL-UHFFFAOYSA-N 0.000 claims description 2
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UHZDTZHRQUULMZ-UHFFFAOYSA-N 5-(1-benzothiophen-2-yl)-4-(1h-indol-4-ylamino)pyridine-3-carbonitrile Chemical compound N#CC1=CN=CC(C=2SC3=CC=CC=C3C=2)=C1NC1=CC=CC2=C1C=CN2 UHZDTZHRQUULMZ-UHFFFAOYSA-N 0.000 claims description 2
ASDRIDGWWRNUHE-UHFFFAOYSA-N 5-(1-benzothiophen-2-yl)-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC=C2SC(C3=CN=CC(=C3NC3=C(C=4C=CNC=4C=C3)C)C#N)=CC2=C1 ASDRIDGWWRNUHE-UHFFFAOYSA-N 0.000 claims description 2
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GPXAKRZLLXFCGT-UHFFFAOYSA-N 5-(2-bromo-4,5-dimethoxyphenyl)-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=C(OC)C(OC)=CC(Br)=C1C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C GPXAKRZLLXFCGT-UHFFFAOYSA-N 0.000 claims description 2
XROCFZZICKBYOE-UHFFFAOYSA-N 5-(2-bromophenyl)-4-(1h-indol-4-ylamino)pyridine-3-carbonitrile Chemical compound BrC1=CC=CC=C1C1=CN=CC(C#N)=C1NC1=CC=CC2=C1C=CN2 XROCFZZICKBYOE-UHFFFAOYSA-N 0.000 claims description 2
BDXPVTOQMJWFRX-UHFFFAOYSA-N 5-(2-bromophenyl)-4-(1h-indol-5-ylamino)pyridine-3-carbonitrile Chemical compound BrC1=CC=CC=C1C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1 BDXPVTOQMJWFRX-UHFFFAOYSA-N 0.000 claims description 2
CLBBTVAVQOWFGF-UHFFFAOYSA-N 5-(2-bromophenyl)-4-[(7-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C=1C=2C=CNC=2C(C)=CC=1NC1=C(C#N)C=NC=C1C1=CC=CC=C1Br CLBBTVAVQOWFGF-UHFFFAOYSA-N 0.000 claims description 2
ARDWBBJMZXFOTI-UHFFFAOYSA-N 5-(2-chloro-4-methoxyphenyl)-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound ClC1=CC(OC)=CC=C1C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C ARDWBBJMZXFOTI-UHFFFAOYSA-N 0.000 claims description 2
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DOJUIHNAEDAZRA-UHFFFAOYSA-N 5-[3-(4-aminophenyl)phenyl]-4-(1h-indol-5-ylamino)pyridine-3-carbonitrile Chemical compound C1=CC(N)=CC=C1C1=CC=CC(C=2C(=C(C#N)C=NC=2)NC=2C=C3C=CNC3=CC=2)=C1 DOJUIHNAEDAZRA-UHFFFAOYSA-N 0.000 claims description 2
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RKEGGBLOFQEOEI-UHFFFAOYSA-N 5-[3-(4-chlorophenyl)phenyl]-4-(1h-indol-5-ylamino)pyridine-3-carbonitrile Chemical compound C1=CC(Cl)=CC=C1C1=CC=CC(C=2C(=C(C#N)C=NC=2)NC=2C=C3C=CNC3=CC=2)=C1 RKEGGBLOFQEOEI-UHFFFAOYSA-N 0.000 claims description 2
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GRZZATGEGIKFBK-UHFFFAOYSA-N 5-[3-(5-formylthiophen-2-yl)phenyl]-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(C=1)=CC=CC=1C1=CC=C(C=O)S1 GRZZATGEGIKFBK-UHFFFAOYSA-N 0.000 claims description 2
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FUBRYDXRNUOWIT-UHFFFAOYSA-N 5-[3-(furan-3-yl)phenyl]-4-(1h-indol-5-ylamino)pyridine-3-carbonitrile Chemical compound C=1C=C2NC=CC2=CC=1NC=1C(C#N)=CN=CC=1C(C=1)=CC=CC=1C=1C=COC=1 FUBRYDXRNUOWIT-UHFFFAOYSA-N 0.000 claims description 2
PTQTWFYSQWOVIV-UHFFFAOYSA-N 5-[3-(hydroxymethyl)phenyl]-4-(1h-indol-4-ylamino)pyridine-3-carbonitrile Chemical compound OCC1=CC=CC(C=2C(=C(C#N)C=NC=2)NC=2C=3C=CNC=3C=CC=2)=C1 PTQTWFYSQWOVIV-UHFFFAOYSA-N 0.000 claims description 2
ZGDVXEMHDSITDS-UHFFFAOYSA-N 5-[3-[(dimethylamino)methyl]phenyl]-4-(1h-indol-4-ylamino)pyridine-3-carbonitrile Chemical compound CN(C)CC1=CC=CC(C=2C(=C(C#N)C=NC=2)NC=2C=3C=CNC=3C=CC=2)=C1 ZGDVXEMHDSITDS-UHFFFAOYSA-N 0.000 claims description 2
BQKKPNGQPGHFDJ-UHFFFAOYSA-N 5-[3-[2-(2-hydroxyethylamino)ethoxy]-4-methoxyphenyl]-4-(1h-indol-4-ylamino)pyridine-3-carbonitrile Chemical compound C1=C(OCCNCCO)C(OC)=CC=C1C1=CN=CC(C#N)=C1NC1=CC=CC2=C1C=CN2 BQKKPNGQPGHFDJ-UHFFFAOYSA-N 0.000 claims description 2
PHTOMLSOWZDDMM-UHFFFAOYSA-N 5-[3-[2-(2-hydroxyethylamino)ethoxy]phenyl]-4-(1h-indol-5-ylamino)pyridine-3-carbonitrile Chemical compound OCCNCCOC1=CC=CC(C=2C(=C(C#N)C=NC=2)NC=2C=C3C=CNC3=CC=2)=C1 PHTOMLSOWZDDMM-UHFFFAOYSA-N 0.000 claims description 2
ZTJLRRBAEXRIAC-UHFFFAOYSA-N 5-[3-[2-(4-ethylpiperazin-1-yl)ethoxy]-4-methoxyphenyl]-4-(1h-indol-5-ylamino)pyridine-3-carbonitrile Chemical compound C1CN(CC)CCN1CCOC1=CC(C=2C(=C(C#N)C=NC=2)NC=2C=C3C=CNC3=CC=2)=CC=C1OC ZTJLRRBAEXRIAC-UHFFFAOYSA-N 0.000 claims description 2
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WKGDVXHZYIYRMA-UHFFFAOYSA-N 5-[3-[2-(benzylamino)ethoxy]-4-methoxyphenyl]-4-(1h-indol-5-ylamino)pyridine-3-carbonitrile Chemical compound COC1=CC=C(C=2C(=C(C#N)C=NC=2)NC=2C=C3C=CNC3=CC=2)C=C1OCCNCC1=CC=CC=C1 WKGDVXHZYIYRMA-UHFFFAOYSA-N 0.000 claims description 2
APMUZKRELPHVTR-UHFFFAOYSA-N 5-[3-[2-(cyclohexylamino)ethoxy]-4-methoxyphenyl]-4-(1h-indol-5-ylamino)pyridine-3-carbonitrile Chemical compound COC1=CC=C(C=2C(=C(C#N)C=NC=2)NC=2C=C3C=CNC3=CC=2)C=C1OCCNC1CCCCC1 APMUZKRELPHVTR-UHFFFAOYSA-N 0.000 claims description 2
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LNRJZORBZIQYJF-UHFFFAOYSA-N 5-[3-[2-(dimethylamino)ethoxy]-4-methoxyphenyl]-4-(1h-indol-4-ylamino)pyridine-3-carbonitrile Chemical compound C1=C(OCCN(C)C)C(OC)=CC=C1C1=CN=CC(C#N)=C1NC1=CC=CC2=C1C=CN2 LNRJZORBZIQYJF-UHFFFAOYSA-N 0.000 claims description 2
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AKAGWPZGMALILS-UHFFFAOYSA-N 5-[3-[5-[(dimethylamino)methyl]thiophen-2-yl]phenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound S1C(CN(C)C)=CC=C1C1=CC=CC(C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=C1 AKAGWPZGMALILS-UHFFFAOYSA-N 0.000 claims description 2
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NRVANJHGIXJXLB-UHFFFAOYSA-N 5-[3-methoxy-4-(2-piperidin-1-ylethoxy)phenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound COC1=CC(C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=CC=C1OCCN1CCCCC1 NRVANJHGIXJXLB-UHFFFAOYSA-N 0.000 claims description 2
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GPBVMPXWBJHCCE-UHFFFAOYSA-N 5-[4-(2-chloroethoxy)-3-methoxyphenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=C(OCCCl)C(OC)=CC(C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=C1 GPBVMPXWBJHCCE-UHFFFAOYSA-N 0.000 claims description 2
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MFFLMUDUCGAIJB-UHFFFAOYSA-N 5-[4-(2-methoxyethoxy)phenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC(OCCOC)=CC=C1C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C MFFLMUDUCGAIJB-UHFFFAOYSA-N 0.000 claims description 2
WZSVJNXPSZHPGX-UHFFFAOYSA-N 5-[4-(dimethylamino)phenyl]-4-(1h-indazol-5-ylamino)pyridine-3-carbonitrile Chemical compound C1=CC(N(C)C)=CC=C1C1=CN=CC(C#N)=C1NC1=CC=C(NN=C2)C2=C1 WZSVJNXPSZHPGX-UHFFFAOYSA-N 0.000 claims description 2
XGPLLXUFNMGOCS-UHFFFAOYSA-N 5-[4-(dimethylamino)phenyl]-4-(1h-indazol-6-ylamino)pyridine-3-carbonitrile Chemical compound C1=CC(N(C)C)=CC=C1C1=CN=CC(C#N)=C1NC1=CC=C(C=NN2)C2=C1 XGPLLXUFNMGOCS-UHFFFAOYSA-N 0.000 claims description 2
PNNBDTCPVXEDMB-UHFFFAOYSA-N 5-[4-(dimethylamino)phenyl]-4-(pyridin-3-ylamino)pyridine-3-carbonitrile Chemical compound C1=CC(N(C)C)=CC=C1C1=CN=CC(C#N)=C1NC1=CC=CN=C1 PNNBDTCPVXEDMB-UHFFFAOYSA-N 0.000 claims description 2
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VDWXALODYRHOII-UHFFFAOYSA-N 5-[4-[2-(2-ethoxyethylamino)ethoxy]phenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC(OCCNCCOCC)=CC=C1C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C VDWXALODYRHOII-UHFFFAOYSA-N 0.000 claims description 2
QLXQPANNOMHFJD-UHFFFAOYSA-N 5-[4-[2-(2-hydroxyethylamino)ethoxy]phenyl]-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=CC=C(OCCNCCO)C=C1 QLXQPANNOMHFJD-UHFFFAOYSA-N 0.000 claims description 2
KSPJRYNFYLGDAA-UHFFFAOYSA-N 5-[4-[2-(3-hydroxypropylamino)ethoxy]phenyl]-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=CC=C(OCCNCCCO)C=C1 KSPJRYNFYLGDAA-UHFFFAOYSA-N 0.000 claims description 2
WYPWHJMAXGTFCT-UHFFFAOYSA-N 5-[4-[2-(4-butylpiperazin-1-yl)ethoxy]phenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1CN(CCCC)CCN1CCOC1=CC=C(C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)C=C1 WYPWHJMAXGTFCT-UHFFFAOYSA-N 0.000 claims description 2
STVBDFBEUALACU-UHFFFAOYSA-N 5-[4-[2-(4-ethylpiperazin-1-yl)ethoxy]phenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1CN(CC)CCN1CCOC1=CC=C(C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)C=C1 STVBDFBEUALACU-UHFFFAOYSA-N 0.000 claims description 2
KRDQYXZVHCXVNU-UHFFFAOYSA-N 5-[4-[2-(4-hydroxypiperidin-1-yl)ethoxy]phenyl]-4-[(6-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound CC1=CC=2NC=CC=2C=C1NC1=C(C#N)C=NC=C1C(C=C1)=CC=C1OCCN1CCC(O)CC1 KRDQYXZVHCXVNU-UHFFFAOYSA-N 0.000 claims description 2
UKEMHSCHHYSIDC-UHFFFAOYSA-N 5-[4-[2-(4-methyl-1,4-diazepan-1-yl)ethoxy]phenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1CN(C)CCCN1CCOC1=CC=C(C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)C=C1 UKEMHSCHHYSIDC-UHFFFAOYSA-N 0.000 claims description 2
CHXZCKDKEUSMQD-UHFFFAOYSA-N 5-[4-[2-(benzylamino)ethoxy]phenyl]-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(C=C1)=CC=C1OCCNCC1=CC=CC=C1 CHXZCKDKEUSMQD-UHFFFAOYSA-N 0.000 claims description 2
ZBUDCUMNDHVOKM-UHFFFAOYSA-N 5-[4-[2-(dimethylamino)ethoxy]-3-methoxyphenyl]-4-[(2,4-dimethyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=C(OCCN(C)C)C(OC)=CC(C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=C(C)NC3=CC=2)C)=C1 ZBUDCUMNDHVOKM-UHFFFAOYSA-N 0.000 claims description 2
ZRTHIYZKVPIBMW-UHFFFAOYSA-N 5-[4-[2-[2-(dimethylamino)ethylamino]ethoxy]phenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC(OCCNCCN(C)C)=CC=C1C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C ZRTHIYZKVPIBMW-UHFFFAOYSA-N 0.000 claims description 2
IFPLUMSPGLKAOT-UHFFFAOYSA-N 5-[4-[2-[4-(2-hydroxyethyl)piperazin-1-yl]ethoxy]phenyl]-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(C=C1)=CC=C1OCCN1CCN(CCO)CC1 IFPLUMSPGLKAOT-UHFFFAOYSA-N 0.000 claims description 2
XPKAGEVONQFELN-UHFFFAOYSA-N 5-[4-[2-[4-(hydroxymethyl)piperidin-1-yl]ethoxy]phenyl]-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(C=C1)=CC=C1OCCN1CCC(CO)CC1 XPKAGEVONQFELN-UHFFFAOYSA-N 0.000 claims description 2
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JBACXOGAOBGKOL-UHFFFAOYSA-N 5-[4-methoxy-3-(2-methoxyethoxy)phenyl]-4-[(2-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=C(OC)C(OCCOC)=CC(C=2C(=C(C#N)C=NC=2)NC=2C=C3C=C(C)NC3=CC=2)=C1 JBACXOGAOBGKOL-UHFFFAOYSA-N 0.000 claims description 2
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JP2009515487A 2006-06-13 2007-06-13 プロテインキナーゼ阻害剤としての置換３−シアノピリジン Withdrawn JP2009539998A (ja)