CA2654515C - Substituted 3-cyanopyridines as protein kinase inhibitors - Google Patents

Info

Publication number

CA2654515C

CA2654515C CA2654515A CA2654515A CA2654515C CA 2654515 C CA2654515 C CA 2654515C CA 2654515 A CA2654515 A CA 2654515A CA 2654515 A CA2654515 A CA 2654515A CA 2654515 C CA2654515 C CA 2654515C

Authority

CA

Canada

Prior art keywords

indol

nicotinonitrile

methyl

amino

ylamino

Prior art date

2006-06-13

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.)

Expired - Fee Related

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• GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical class N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 title claims description 689
• 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 title description 2
• 239000003909 protein kinase inhibitor Substances 0.000 title description 2
• -1 hydrate Chemical class 0.000 claims abstract description 333
• 150000001875 compounds Chemical class 0.000 claims abstract description 297
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 63
• 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 claims abstract description 56
• 125000003118 aryl group Chemical group 0.000 claims abstract description 55
• 150000002148 esters Chemical class 0.000 claims abstract description 43
• 150000003839 salts Chemical class 0.000 claims abstract description 43
• 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 33
• 125000005915 C6-C14 aryl group Chemical group 0.000 claims abstract description 31
• 125000000304 alkynyl group Chemical group 0.000 claims abstract description 31
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract description 26
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims abstract description 20
• 241000124008 Mammalia Species 0.000 claims abstract description 12
• 229910052727 yttrium Inorganic materials 0.000 claims abstract description 12
• 125000003367 polycyclic group Chemical group 0.000 claims abstract description 10
• 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 6
• 208000027866 inflammatory disease Diseases 0.000 claims abstract description 6
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 391
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 187
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 100
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 92
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 42
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 32
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
• 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 17
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
• 150000002367 halogens Chemical class 0.000 claims description 16
• 229910052736 halogen Inorganic materials 0.000 claims description 15
• 125000001544 thienyl group Chemical group 0.000 claims description 14
• 125000002837 carbocyclic group Chemical group 0.000 claims description 13
• DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 13
• 125000003342 alkenyl group Chemical group 0.000 claims description 12
• 208000035475 disorder Diseases 0.000 claims description 12
• 229910052739 hydrogen Inorganic materials 0.000 claims description 11
• 230000001575 pathological effect Effects 0.000 claims description 11
• 125000004076 pyridyl group Chemical group 0.000 claims description 11
• 102000001253 Protein Kinase Human genes 0.000 claims description 10
• 108090000315 Protein Kinase C Proteins 0.000 claims description 10
• 102000003923 Protein Kinase C Human genes 0.000 claims description 10
• 206010003246 arthritis Diseases 0.000 claims description 10
• 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 10
• 125000002541 furyl group Chemical group 0.000 claims description 10
• 239000008194 pharmaceutical composition Substances 0.000 claims description 10
• 108060006633 protein kinase Proteins 0.000 claims description 10
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
• LUQVCHRDAGWYMG-UHFFFAOYSA-N 4-phenylbenzamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=CC=CC=C1 LUQVCHRDAGWYMG-UHFFFAOYSA-N 0.000 claims description 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
• 230000001404 mediated effect Effects 0.000 claims description 9
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
• 125000001041 indolyl group Chemical group 0.000 claims description 8
• 125000002757 morpholinyl group Chemical group 0.000 claims description 8
• 125000004193 piperazinyl group Chemical group 0.000 claims description 8
• 125000003386 piperidinyl group Chemical group 0.000 claims description 8
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 8
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
• 239000003937 drug carrier Substances 0.000 claims description 7
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 7
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 7
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 6
• 208000006673 asthma Diseases 0.000 claims description 6
• 125000003725 azepanyl group Chemical group 0.000 claims description 6
• 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 6
• 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 6
• 125000002883 imidazolyl group Chemical group 0.000 claims description 6
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 5
• 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
• 125000002619 bicyclic group Chemical group 0.000 claims description 5
• 125000005959 diazepanyl group Chemical group 0.000 claims description 5
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 5
• 230000005764 inhibitory process Effects 0.000 claims description 5
• RFIOZSIHFNEKFF-UHFFFAOYSA-M piperazine-1-carboxylate Chemical compound [O-]C(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-M 0.000 claims description 5
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
• 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 4
• 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 201000004681 Psoriasis Diseases 0.000 claims description 4
• 125000000928 benzodioxinyl group Chemical group O1C(=COC2=C1C=CC=C2)* 0.000 claims description 4
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
• 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
• 206010009887 colitis Diseases 0.000 claims description 4
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 4
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
• 208000018937 joint inflammation Diseases 0.000 claims description 4
• 201000006417 multiple sclerosis Diseases 0.000 claims description 4
• 125000001624 naphthyl group Chemical group 0.000 claims description 4
• 201000008482 osteoarthritis Diseases 0.000 claims description 4
• 125000002971 oxazolyl group Chemical group 0.000 claims description 4
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
• 125000003373 pyrazinyl 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
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
• 125000000335 thiazolyl group Chemical group 0.000 claims description 4
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
• 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 3
• SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 claims description 3
• 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims description 3
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
• 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
• 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
• 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 3
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
• 125000006309 butyl amino group Chemical group 0.000 claims description 3
• 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 claims description 3
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 3
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 3
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 3
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 3
• 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 2
• 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 2
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 2
• 125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 2
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
• 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
• 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 2
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound 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 2
• 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims description 2
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 2
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• CDGQTSAIQQDFHB-UHFFFAOYSA-N 4-(1h-indol-4-ylamino)-5-(3-thiophen-2-ylphenyl)pyridine-3-carbonitrile Chemical compound C=1C=CC=2NC=CC=2C=1NC=1C(C#N)=CN=CC=1C(C=1)=CC=CC=1C1=CC=CS1 CDGQTSAIQQDFHB-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• VETFSBQHCHOXGN-UHFFFAOYSA-N 4-(1h-indol-4-ylamino)-5-[4-[2-(3-phenylpropylamino)ethoxy]phenyl]pyridine-3-carbonitrile Chemical compound C=1C=CC=2NC=CC=2C=1NC=1C(C#N)=CN=CC=1C(C=C1)=CC=C1OCCNCCCC1=CC=CC=C1 VETFSBQHCHOXGN-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 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 1
• CVGJDIBDNAAONY-UHFFFAOYSA-N 4-(1h-indol-4-ylamino)-5-[4-methoxy-3-[2-(2-phenylethylamino)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=C1OCCNCCC1=CC=CC=C1 CVGJDIBDNAAONY-UHFFFAOYSA-N 0.000 claims 1
• RKZCXFAMSSDIST-UHFFFAOYSA-N 4-(1h-indol-4-ylamino)-5-[4-methoxy-3-[2-(2-pyridin-3-ylethylamino)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=C1OCCNCCC1=CC=CN=C1 RKZCXFAMSSDIST-UHFFFAOYSA-N 0.000 claims 1
• RBXXMGRRGQXVMG-UHFFFAOYSA-N 4-(1h-indol-4-ylamino)-5-[4-methoxy-3-[2-(3-morpholin-4-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=C1OCCNCCCN1CCOCC1 RBXXMGRRGQXVMG-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• YHWQBDGAZNTBQG-UHFFFAOYSA-N 4-(1h-indol-4-ylamino)-5-[5-(piperazin-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=2CN1CCNCC1 YHWQBDGAZNTBQG-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• GMJJEAMQSAPUFF-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-(3-pyridin-3-ylphenyl)pyridine-3-carbonitrile Chemical compound C=1C=C2NC=CC2=CC=1NC=1C(C#N)=CN=CC=1C(C=1)=CC=CC=1C1=CC=CN=C1 GMJJEAMQSAPUFF-UHFFFAOYSA-N 0.000 claims 1
• XUPHMGMTPYXAAP-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-(3-pyrimidin-2-ylphenyl)pyridine-3-carbonitrile Chemical compound C=1C=C2NC=CC2=CC=1NC=1C(C#N)=CN=CC=1C(C=1)=CC=CC=1C1=NC=CC=N1 XUPHMGMTPYXAAP-UHFFFAOYSA-N 0.000 claims 1
• YPYXCJWXOFMVIY-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-(3-thiophen-2-ylphenyl)pyridine-3-carbonitrile Chemical compound C=1C=C2NC=CC2=CC=1NC=1C(C#N)=CN=CC=1C(C=1)=CC=CC=1C1=CC=CS1 YPYXCJWXOFMVIY-UHFFFAOYSA-N 0.000 claims 1
• QXAKPSXXUAOVED-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-(3-thiophen-3-ylphenyl)pyridine-3-carbonitrile Chemical compound C=1C=C2NC=CC2=CC=1NC=1C(C#N)=CN=CC=1C(C=1)=CC=CC=1C=1C=CSC=1 QXAKPSXXUAOVED-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• SDONPVNGLJQDAD-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-(4-phenylmethoxyphenyl)pyridine-3-carbonitrile Chemical compound C=1C=C2NC=CC2=CC=1NC=1C(C#N)=CN=CC=1C(C=C1)=CC=C1OCC1=CC=CC=C1 SDONPVNGLJQDAD-UHFFFAOYSA-N 0.000 claims 1
• PNCPCHTVYFDRTP-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-[3-(2-morpholin-4-ylethoxy)phenyl]pyridine-3-carbonitrile Chemical compound C=1C=C2NC=CC2=CC=1NC=1C(C#N)=CN=CC=1C(C=1)=CC=CC=1OCCN1CCOCC1 PNCPCHTVYFDRTP-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• JUJIKGIIGMCUHF-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-[3-[2-(2-pyrrolidin-1-ylethylamino)ethoxy]phenyl]pyridine-3-carbonitrile Chemical compound C=1C=C2NC=CC2=CC=1NC=1C(C#N)=CN=CC=1C(C=1)=CC=CC=1OCCNCCN1CCCC1 JUJIKGIIGMCUHF-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• KDBBLBJUXVJIKC-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-[3-[5-(piperidin-1-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=C1CN1CCCCC1 KDBBLBJUXVJIKC-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• VYIMDEHSEMUAKI-UHFFFAOYSA-N 4-(1h-indol-5-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=C3C=CNC3=CC=2)C=C1 VYIMDEHSEMUAKI-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• SEUUIZPJORKBNB-UHFFFAOYSA-N 4-(1h-indol-5-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=C3C=CNC3=CC=2)C=C1OCCN1CCCCC1 SEUUIZPJORKBNB-UHFFFAOYSA-N 0.000 claims 1
• GKJGXBMDUQEHKS-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-[4-methoxy-3-(2-thiomorpholin-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=C1OCCN1CCSCC1 GKJGXBMDUQEHKS-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• FYIOHKKNAIVYEX-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-[4-methoxy-3-[2-(2-phenylethylamino)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=C1OCCNCCC1=CC=CC=C1 FYIOHKKNAIVYEX-UHFFFAOYSA-N 0.000 claims 1
• LFIDWWNWFIAPDQ-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-[4-methoxy-3-[2-(2-pyridin-2-ylethylamino)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=C1OCCNCCC1=CC=CC=N1 LFIDWWNWFIAPDQ-UHFFFAOYSA-N 0.000 claims 1
• IJCIWXUNIIFZDR-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-[4-methoxy-3-[2-(2-pyridin-3-ylethylamino)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=C1OCCNCCC1=CC=CN=C1 IJCIWXUNIIFZDR-UHFFFAOYSA-N 0.000 claims 1
• MVDYKHCBROMROC-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-[4-methoxy-3-[2-(2-pyridin-4-ylethylamino)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=C1OCCNCCC1=CC=NC=C1 MVDYKHCBROMROC-UHFFFAOYSA-N 0.000 claims 1
• MWTQOWIVAXWLFQ-UHFFFAOYSA-N 4-(1h-indol-5-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=C3C=CNC3=CC=2)C=C1OCCNCCCC1=CC=CC=C1 MWTQOWIVAXWLFQ-UHFFFAOYSA-N 0.000 claims 1
• AIBFXDWCNJZNTF-UHFFFAOYSA-N 4-(1h-indol-5-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=C3C=CNC3=CC=2)C=C1OCCN1CCN(C)CC1 AIBFXDWCNJZNTF-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• RWPUYWOWGVVDFS-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-[4-methoxy-3-[2-(pyridin-3-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=CN=C1 RWPUYWOWGVVDFS-UHFFFAOYSA-N 0.000 claims 1
• WPOUYYQJJMAVBQ-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-[4-methoxy-3-[2-(pyridin-4-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=NC=C1 WPOUYYQJJMAVBQ-UHFFFAOYSA-N 0.000 claims 1
• VZQVHWBTISVUMY-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-[4-methoxy-3-[2-[(5-methyl-1,3,4-thiadiazol-2-yl)amino]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=C1OCCNC1=NN=C(C)S1 VZQVHWBTISVUMY-UHFFFAOYSA-N 0.000 claims 1
• PAPZJUXIXRHMOW-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-phenylpyridine-3-carbonitrile Chemical compound C=1C=C2NC=CC2=CC=1NC=1C(C#N)=CN=CC=1C1=CC=CC=C1 PAPZJUXIXRHMOW-UHFFFAOYSA-N 0.000 claims 1
• SXBZPGZEYQIMMX-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-pyridin-3-ylpyridine-3-carbonitrile Chemical compound C=1C=C2NC=CC2=CC=1NC=1C(C#N)=CN=CC=1C1=CC=CN=C1 SXBZPGZEYQIMMX-UHFFFAOYSA-N 0.000 claims 1
• XNWDQXJPWQGSMV-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-5-thiophen-3-ylpyridine-3-carbonitrile Chemical compound C=1C=C2NC=CC2=CC=1NC=1C(C#N)=CN=CC=1C=1C=CSC=1 XNWDQXJPWQGSMV-UHFFFAOYSA-N 0.000 claims 1
• QGMUCFXYMTZMAK-UHFFFAOYSA-N 4-(1h-indol-6-ylamino)-5-[3-(2-morpholin-4-ylethoxy)phenyl]pyridine-3-carbonitrile Chemical compound C=1C=C2C=CNC2=CC=1NC=1C(C#N)=CN=CC=1C(C=1)=CC=CC=1OCCN1CCOCC1 QGMUCFXYMTZMAK-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 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 1
• ZEVZHZYRMSLQDD-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-(4-nitrophenyl)pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C1=CC=C([N+]([O-])=O)C=C1 ZEVZHZYRMSLQDD-UHFFFAOYSA-N 0.000 claims 1
• QXSGQFAFCKIWMU-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-(6-piperidin-1-ylpyridin-3-yl)pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(C=N1)=CC=C1N1CCCCC1 QXSGQFAFCKIWMU-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• HVILCFAEPQUXBH-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[2-[(4-methylpiperazin-1-yl)methyl]pyridin-4-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)=CC=N1 HVILCFAEPQUXBH-UHFFFAOYSA-N 0.000 claims 1
• KKJPRKYEBAZSSW-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[3-(piperazin-1-ylmethyl)phenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(C=1)=CC=CC=1CN1CCNCC1 KKJPRKYEBAZSSW-UHFFFAOYSA-N 0.000 claims 1
• QDSASUQCGCJAGJ-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[3-methyl-2-[(4-methylpiperazin-1-yl)methyl]imidazol-4-yl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCN1CC(N1C)=NC=C1C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C QDSASUQCGCJAGJ-UHFFFAOYSA-N 0.000 claims 1
• YUZANCJQMKLODH-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[4-(2-morpholin-4-ylethoxy)phenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(C=C1)=CC=C1OCCN1CCOCC1 YUZANCJQMKLODH-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• BUXVHQQXZAMBOF-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[4-(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=CC=1)=CC=1CN1CCNCC1 BUXVHQQXZAMBOF-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• VPIKNWGXSGSWSG-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[4-[2-(3-phenylpropylamino)ethoxy]phenyl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(C=C1)=CC=C1OCCNCCCC1=CC=CC=C1 VPIKNWGXSGSWSG-UHFFFAOYSA-N 0.000 claims 1
• LTGPAFCQBMWTBC-UHFFFAOYSA-N 4-[(4-methyl-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=CNC3=CC=2)C)C=C1 LTGPAFCQBMWTBC-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• FLWBAZOREVFEAD-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[4-[2-(4-pyrrolidin-1-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)CCC1N1CCCC1 FLWBAZOREVFEAD-UHFFFAOYSA-N 0.000 claims 1
• ZCMFIKVSYHLDQJ-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[4-[2-[(1-methylpiperidin-4-yl)amino]ethoxy]phenyl]pyridine-3-carbonitrile Chemical compound C1CN(C)CCC1NCCOC1=CC=C(C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)C=C1 ZCMFIKVSYHLDQJ-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• JTUGJZFQRMCZQW-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[5-(thiomorpholin-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=C1CN1CCSCC1 JTUGJZFQRMCZQW-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• JNXDDALKPXMKQB-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[5-[(4-methylpiperazin-1-yl)methyl]thiophen-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)S1 JNXDDALKPXMKQB-UHFFFAOYSA-N 0.000 claims 1
• WUWJDRGPTHRZQB-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[5-[(4-methylsulfonylpiperazin-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=2CN1CCN(S(C)(=O)=O)CC1 WUWJDRGPTHRZQB-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• MKBLRGYWLNYGMG-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[5-[(4-pyrrolidin-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)CCC1N1CCCC1 MKBLRGYWLNYGMG-UHFFFAOYSA-N 0.000 claims 1
• QLMSUTGRQCMONA-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[5-[(pyridin-2-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=CC=N1 QLMSUTGRQCMONA-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• ZSQOENYEDBPBAI-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[6-(2-morpholin-4-ylethylamino)pyridin-3-yl]pyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(C=N1)=CC=C1NCCN1CCOCC1 ZSQOENYEDBPBAI-UHFFFAOYSA-N 0.000 claims 1
• LCSZTJNTAVKPBB-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[6-(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=1)=CC=CC=1CN1CCOCC1 LCSZTJNTAVKPBB-UHFFFAOYSA-N 0.000 claims 1
• WFOUQQUYTUIMRU-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[6-(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=N1)=CC=C1CN1CCOCC1 WFOUQQUYTUIMRU-UHFFFAOYSA-N 0.000 claims 1
• OEEISDLLGXIMKM-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[6-(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=1)=CC=CC=1CN1CCNCC1 OEEISDLLGXIMKM-UHFFFAOYSA-N 0.000 claims 1
• QGMYLGRPJSYUJT-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[6-(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=N1)=CC=C1CN1CCNCC1 QGMYLGRPJSYUJT-UHFFFAOYSA-N 0.000 claims 1
• RCKVYOXLMHAPMO-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-[6-[(4-methylpiperazin-1-yl)methyl]pyridin-3-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)C=N1 RCKVYOXLMHAPMO-UHFFFAOYSA-N 0.000 claims 1
• MHUSFLWTKCWFNM-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-pyrimidin-5-ylpyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C1=CN=CN=C1 MHUSFLWTKCWFNM-UHFFFAOYSA-N 0.000 claims 1
• WUTZJWVPWNQHSF-UHFFFAOYSA-N 4-[(4-methyl-1h-indol-5-yl)amino]-5-thiophen-3-ylpyridine-3-carbonitrile Chemical compound C1=CC=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C=1C=CSC=1 WUTZJWVPWNQHSF-UHFFFAOYSA-N 0.000 claims 1
• UOHOMVNTUXAPFC-UHFFFAOYSA-N 4-[(6-methyl-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(=CC=3NC=CC=3C=2)C)C=C1 UOHOMVNTUXAPFC-UHFFFAOYSA-N 0.000 claims 1
• HPVXMUDCQOOGCA-UHFFFAOYSA-N 4-[(6-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(=CC=4NC=CC=4C=3)C)C2=C1 HPVXMUDCQOOGCA-UHFFFAOYSA-N 0.000 claims 1
• MAUYACYALXDLSD-UHFFFAOYSA-N 4-[(7-chloro-4-methyl-1h-indol-5-yl)amino]-5-(3,4-dimethoxyphenyl)pyridine-3-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1C1=CN=CC(C#N)=C1NC1=CC(Cl)=C(NC=C2)C2=C1C MAUYACYALXDLSD-UHFFFAOYSA-N 0.000 claims 1
• JPGYNFPHQRRFAQ-UHFFFAOYSA-N 4-[(7-chloro-4-methyl-1h-indol-5-yl)amino]-5-(5-formyl-1-benzofuran-2-yl)pyridine-3-carbonitrile Chemical compound O=CC1=CC=C2OC(C3=CN=CC(=C3NC3=C(C=4C=CNC=4C(Cl)=C3)C)C#N)=CC2=C1 JPGYNFPHQRRFAQ-UHFFFAOYSA-N 0.000 claims 1
• OETQBMHPQFVXAW-UHFFFAOYSA-N 4-[(7-chloro-4-methyl-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=CNC3=C(Cl)C=2)C)C=C1 OETQBMHPQFVXAW-UHFFFAOYSA-N 0.000 claims 1
• VVNVLPLJLDDHFG-UHFFFAOYSA-N 4-[(7-chloro-4-methyl-1h-indol-5-yl)amino]-5-[4-[2-(dimethylamino)ethoxy]phenyl]pyridine-3-carbonitrile Chemical compound C1=CC(OCCN(C)C)=CC=C1C1=CN=CC(C#N)=C1NC1=CC(Cl)=C(NC=C2)C2=C1C VVNVLPLJLDDHFG-UHFFFAOYSA-N 0.000 claims 1
• RWZFQLVMUUXCFJ-UHFFFAOYSA-N 4-[(7-chloro-4-methyl-1h-indol-5-yl)amino]-5-[5-(piperazin-1-ylmethyl)-1-benzofuran-2-yl]pyridine-3-carbonitrile Chemical compound C1=C(Cl)C=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C(OC1=CC=2)=CC1=CC=2CN1CCNCC1 RWZFQLVMUUXCFJ-UHFFFAOYSA-N 0.000 claims 1
• RIDLVEONPWHFIM-UHFFFAOYSA-N 4-[(7-chloro-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=C(Cl)C=3)C)C2=C1 RIDLVEONPWHFIM-UHFFFAOYSA-N 0.000 claims 1
• YWZLICIDTNNMPC-UHFFFAOYSA-N 4-[3-[5-cyano-4-(1h-indol-4-ylamino)pyridin-3-yl]phenyl]-n-(2-hydroxyethyl)benzamide Chemical compound C1=CC(C(=O)NCCO)=CC=C1C1=CC=CC(C=2C(=C(C#N)C=NC=2)NC=2C=3C=CNC=3C=CC=2)=C1 YWZLICIDTNNMPC-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• BCKOLLULBXVMTD-UHFFFAOYSA-N 4-[3-[5-cyano-4-(1h-indol-5-ylamino)pyridin-3-yl]phenyl]-n-(2-hydroxyethyl)benzamide Chemical compound C1=CC(C(=O)NCCO)=CC=C1C1=CC=CC(C=2C(=C(C#N)C=NC=2)NC=2C=C3C=CNC3=CC=2)=C1 BCKOLLULBXVMTD-UHFFFAOYSA-N 0.000 claims 1
• LXLDKVKWAQJTMQ-UHFFFAOYSA-N 4-[3-[5-cyano-4-(1h-indol-5-ylamino)pyridin-3-yl]phenyl]-n-(2-methoxyethyl)benzamide Chemical compound C1=CC(C(=O)NCCOC)=CC=C1C1=CC=CC(C=2C(=C(C#N)C=NC=2)NC=2C=C3C=CNC3=CC=2)=C1 LXLDKVKWAQJTMQ-UHFFFAOYSA-N 0.000 claims 1
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• QWGSKOQUJFIKBC-UHFFFAOYSA-N 5-[2-(3-chlorophenyl)phenyl]-4-(1h-indol-5-ylamino)pyridine-3-carbonitrile Chemical compound ClC1=CC=CC(C=2C(=CC=CC=2)C=2C(=C(C#N)C=NC=2)NC=2C=C3C=CNC3=CC=2)=C1 QWGSKOQUJFIKBC-UHFFFAOYSA-N 0.000 claims 1
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• FOMOGQDVLVQTNR-UHFFFAOYSA-N 5-[3-(2-chloroethoxy)phenyl]-4-(1h-indol-4-ylamino)pyridine-3-carbonitrile Chemical compound ClCCOC1=CC=CC(C=2C(=C(C#N)C=NC=2)NC=2C=3C=CNC=3C=CC=2)=C1 FOMOGQDVLVQTNR-UHFFFAOYSA-N 0.000 claims 1
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• ZVUUHOWPOXXDSG-UHFFFAOYSA-N 5-[3-(2-methoxyethoxy)phenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound COCCOC1=CC=CC(C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=C1 ZVUUHOWPOXXDSG-UHFFFAOYSA-N 0.000 claims 1
• LPVFMFHBNQUBPA-UHFFFAOYSA-N 5-[3-(3-aminophenyl)phenyl]-4-(1h-indol-5-ylamino)pyridine-3-carbonitrile Chemical compound NC1=CC=CC(C=2C=C(C=CC=2)C=2C(=C(C#N)C=NC=2)NC=2C=C3C=CNC3=CC=2)=C1 LPVFMFHBNQUBPA-UHFFFAOYSA-N 0.000 claims 1
• HZCKXIMFIUTGOQ-UHFFFAOYSA-N 5-[3-(3-chlorophenyl)-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=C1C1=CC=CC(Cl)=C1 HZCKXIMFIUTGOQ-UHFFFAOYSA-N 0.000 claims 1
• JNUBDERZQZHEGQ-UHFFFAOYSA-N 5-[3-(4-chlorobutoxy)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=CC(OCCCCCl)=C1 JNUBDERZQZHEGQ-UHFFFAOYSA-N 0.000 claims 1
• JFONBXJBYBOHIQ-UHFFFAOYSA-N 5-[3-(4-chlorophenyl)-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=C1C1=CC=C(Cl)C=C1 JFONBXJBYBOHIQ-UHFFFAOYSA-N 0.000 claims 1
• FYFXOUOCRIJMKS-UHFFFAOYSA-N 5-[3-(5-acetylthiophen-2-yl)phenyl]-4-(1h-indol-5-ylamino)pyridine-3-carbonitrile Chemical compound S1C(C(=O)C)=CC=C1C1=CC=CC(C=2C(=C(C#N)C=NC=2)NC=2C=C3C=CNC3=CC=2)=C1 FYFXOUOCRIJMKS-UHFFFAOYSA-N 0.000 claims 1
• FMILMGJZIAZTNO-UHFFFAOYSA-N 5-[3-(5-formylthiophen-2-yl)phenyl]-4-(1h-indol-4-ylamino)pyridine-3-carbonitrile Chemical compound S1C(C=O)=CC=C1C1=CC=CC(C=2C(=C(C#N)C=NC=2)NC=2C=3C=CNC=3C=CC=2)=C1 FMILMGJZIAZTNO-UHFFFAOYSA-N 0.000 claims 1
• XCAOSTUYRNECGA-UHFFFAOYSA-N 5-[3-(5-formylthiophen-2-yl)phenyl]-4-(1h-indol-5-ylamino)pyridine-3-carbonitrile Chemical compound S1C(C=O)=CC=C1C1=CC=CC(C=2C(=C(C#N)C=NC=2)NC=2C=C3C=CNC3=CC=2)=C1 XCAOSTUYRNECGA-UHFFFAOYSA-N 0.000 claims 1
• IVAWMHIFKLIIOG-UHFFFAOYSA-N 5-[3-(dimethylamino)phenyl]-4-(1h-indol-4-ylamino)pyridine-3-carbonitrile Chemical compound CN(C)C1=CC=CC(C=2C(=C(C#N)C=NC=2)NC=2C=3C=CNC=3C=CC=2)=C1 IVAWMHIFKLIIOG-UHFFFAOYSA-N 0.000 claims 1
• ICTKQFYIHVQUSM-UHFFFAOYSA-N 5-[3-(dimethylamino)phenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound CN(C)C1=CC=CC(C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)=C1 ICTKQFYIHVQUSM-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• VWJPCDWWCVDRMU-UHFFFAOYSA-N 5-[3-[2-(3-imidazol-1-ylpropylamino)ethoxy]-4-methoxyphenyl]-4-(1h-indol-4-ylamino)pyridine-3-carbonitrile Chemical compound COC1=CC=C(C=2C(=C(C#N)C=NC=2)NC=2C=3C=CNC=3C=CC=2)C=C1OCCNCCCN1C=CN=C1 VWJPCDWWCVDRMU-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• OYMLNBPKKRXUHW-UHFFFAOYSA-N 5-[3-[2-(4-hydroxypiperidin-1-yl)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=C1OCCN1CCC(O)CC1 OYMLNBPKKRXUHW-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• NUNGLIZFFVNNDX-UHFFFAOYSA-N 5-[3-[2-(diethylamino)ethoxy]-4-methoxyphenyl]-4-(1h-indol-5-ylamino)pyridine-3-carbonitrile Chemical compound C1=C(OC)C(OCCN(CC)CC)=CC(C=2C(=C(C#N)C=NC=2)NC=2C=C3C=CNC3=CC=2)=C1 NUNGLIZFFVNNDX-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• OXPRPLHPYQKFJO-UHFFFAOYSA-N 5-[3-[2-(dimethylamino)ethoxy]-4-methoxyphenyl]-4-(1h-indol-5-ylamino)pyridine-3-carbonitrile Chemical compound C1=C(OCCN(C)C)C(OC)=CC=C1C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1 OXPRPLHPYQKFJO-UHFFFAOYSA-N 0.000 claims 1
• TWDXCAVOBPFEQZ-UHFFFAOYSA-N 5-[3-[2-(furan-2-ylmethylamino)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=CO1 TWDXCAVOBPFEQZ-UHFFFAOYSA-N 0.000 claims 1
• BECDHCQOUWFFMC-UHFFFAOYSA-N 5-[3-[2-[2-(1h-imidazol-5-yl)ethylamino]ethoxy]-4-methoxyphenyl]-4-(1h-indol-4-ylamino)pyridine-3-carbonitrile Chemical compound COC1=CC=C(C=2C(=C(C#N)C=NC=2)NC=2C=3C=CNC=3C=CC=2)C=C1OCCNCCC1=CNC=N1 BECDHCQOUWFFMC-UHFFFAOYSA-N 0.000 claims 1
• FWLFTZRHYHGUOA-UHFFFAOYSA-N 5-[3-[2-[bis(2-hydroxyethyl)amino]ethoxy]-4-methoxyphenyl]-4-(1h-indol-5-ylamino)pyridine-3-carbonitrile Chemical compound C1=C(OCCN(CCO)CCO)C(OC)=CC=C1C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1 FWLFTZRHYHGUOA-UHFFFAOYSA-N 0.000 claims 1
• NHDKZQUPLCGLSJ-UHFFFAOYSA-N 5-[3-[2-[di(propan-2-yl)amino]ethoxy]-4-methoxyphenyl]-4-(1h-indol-5-ylamino)pyridine-3-carbonitrile Chemical compound C1=C(OCCN(C(C)C)C(C)C)C(OC)=CC=C1C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1 NHDKZQUPLCGLSJ-UHFFFAOYSA-N 0.000 claims 1
• ZXTXAEUPLLNYJW-UHFFFAOYSA-N 5-[3-[5-[(dimethylamino)methyl]thiophen-2-yl]phenyl]-4-(1h-indol-5-ylamino)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)=C1 ZXTXAEUPLLNYJW-UHFFFAOYSA-N 0.000 claims 1
• ZIBJFTWRUHYYML-UHFFFAOYSA-N 5-[4-(2-chloroethoxy)phenyl]-4-(1h-indol-4-ylamino)pyridine-3-carbonitrile Chemical compound C1=CC(OCCCl)=CC=C1C1=CN=CC(C#N)=C1NC1=CC=CC2=C1C=CN2 ZIBJFTWRUHYYML-UHFFFAOYSA-N 0.000 claims 1
• RZEQPCBVRAGVKR-UHFFFAOYSA-N 5-[4-(2-chloroethoxy)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(OCCCl)C=C1 RZEQPCBVRAGVKR-UHFFFAOYSA-N 0.000 claims 1
• NBIZARMKANKEPM-UHFFFAOYSA-N 5-[4-(2-chloroethoxy)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=C1C1=CC=C(OCCCl)C=C1 NBIZARMKANKEPM-UHFFFAOYSA-N 0.000 claims 1
• LLYSBIOSDOUMOI-UHFFFAOYSA-N 5-[4-(2-chloroethoxy)phenyl]-4-[(7-chloro-4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=C(Cl)C=2NC=CC=2C(C)=C1NC1=C(C#N)C=NC=C1C1=CC=C(OCCCl)C=C1 LLYSBIOSDOUMOI-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• DETDDVLJPHDMGN-UHFFFAOYSA-N 5-[4-(dimethylamino)phenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=CC(N(C)C)=CC=C1C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C DETDDVLJPHDMGN-UHFFFAOYSA-N 0.000 claims 1
• UCHXVTRLGBKONW-QHCPKHFHSA-N 5-[4-[(2s)-2-amino-3-phenylpropoxy]phenyl]-4-(1h-indol-4-ylamino)pyridine-3-carbonitrile Chemical compound C([C@@H](COC=1C=CC(=CC=1)C=1C(=C(C#N)C=NC=1)NC=1C=2C=CNC=2C=CC=1)N)C1=CC=CC=C1 UCHXVTRLGBKONW-QHCPKHFHSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• KIPUCTMKBQJZBQ-UHFFFAOYSA-N 5-[4-[2-(dimethylamino)ethoxy]-3-methoxyphenyl]-4-[(4-methyl-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=CNC3=CC=2)C)=C1 KIPUCTMKBQJZBQ-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• WSAYTXCZBZGZJH-UHFFFAOYSA-N 5-[4-methoxy-3-[2-(3-phenylpropylamino)ethoxy]phenyl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound COC1=CC=C(C=2C(=C(C#N)C=NC=2)NC=2C(=C3C=CNC3=CC=2)C)C=C1OCCNCCCC1=CC=CC=C1 WSAYTXCZBZGZJH-UHFFFAOYSA-N 0.000 claims 1
• YIDWCZSNEAQSEB-UHFFFAOYSA-N 5-[5-(diethylaminomethyl)-1-benzofuran-2-yl]-4-[(6-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C=1C2=CC(CN(CC)CC)=CC=C2OC=1C1=CN=CC(C#N)=C1NC(C(=C1)C)=CC2=C1NC=C2 YIDWCZSNEAQSEB-UHFFFAOYSA-N 0.000 claims 1
• OGFRRHMGGJQLRU-UHFFFAOYSA-N 5-[5-(diethylaminomethyl)furan-2-yl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound O1C(CN(CC)CC)=CC=C1C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C OGFRRHMGGJQLRU-UHFFFAOYSA-N 0.000 claims 1
• IWIQXTZLAYJDRQ-UHFFFAOYSA-N 5-[5-(hydroxymethyl)-1-benzofuran-2-yl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound OCC1=CC=C2OC(C3=CN=CC(=C3NC3=C(C=4C=CNC=4C=C3)C)C#N)=CC2=C1 IWIQXTZLAYJDRQ-UHFFFAOYSA-N 0.000 claims 1
• WHHZZNAGAGSIHM-UHFFFAOYSA-N 5-[5-(hydroxymethyl)-1-benzofuran-2-yl]-4-[(6-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound OCC1=CC=C2OC(C3=CN=CC(=C3NC3=CC=4C=CNC=4C=C3C)C#N)=CC2=C1 WHHZZNAGAGSIHM-UHFFFAOYSA-N 0.000 claims 1
• GANPGLMFFMKRMH-UHFFFAOYSA-N 5-[5-(hydroxymethyl)-1-benzothiophen-2-yl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound OCC1=CC=C2SC(C3=CN=CC(=C3NC3=C(C=4C=CNC=4C=C3)C)C#N)=CC2=C1 GANPGLMFFMKRMH-UHFFFAOYSA-N 0.000 claims 1
• ORSSUJKAEDMACV-UHFFFAOYSA-N 5-[5-[(benzylamino)methyl]-1-benzothiophen-2-yl]-4-(1h-indol-4-ylamino)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=C1 ORSSUJKAEDMACV-UHFFFAOYSA-N 0.000 claims 1
• ANUHNUOCJSHJAS-UHFFFAOYSA-N 5-[5-[(benzylamino)methyl]furan-2-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(O1)=CC=C1CNCC1=CC=CC=C1 ANUHNUOCJSHJAS-UHFFFAOYSA-N 0.000 claims 1
• NEMVIYGSTIBNDD-UHFFFAOYSA-N 5-[5-[(cyclopropylamino)methyl]-1-benzothiophen-2-yl]-4-(1h-indol-4-ylamino)pyridine-3-carbonitrile Chemical compound C=1C=CC=2NC=CC=2C=1NC=1C(C#N)=CN=CC=1C(SC1=CC=2)=CC1=CC=2CNC1CC1 NEMVIYGSTIBNDD-UHFFFAOYSA-N 0.000 claims 1
• FRKUTAUATMNSIK-UHFFFAOYSA-N 5-[5-[(dibutylamino)methyl]furan-2-yl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound O1C(CN(CCCC)CCCC)=CC=C1C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C FRKUTAUATMNSIK-UHFFFAOYSA-N 0.000 claims 1
• MIBXGSZOJGUBEU-UHFFFAOYSA-N 5-[6-[3-(dimethylamino)propoxy]pyridin-3-yl]-4-(1h-indol-4-ylamino)pyridine-3-carbonitrile Chemical compound C1=NC(OCCCN(C)C)=CC=C1C1=CN=CC(C#N)=C1NC1=CC=CC2=C1C=CN2 MIBXGSZOJGUBEU-UHFFFAOYSA-N 0.000 claims 1
• IHIJGMGZNYFVMD-UHFFFAOYSA-N 5-[6-[3-(dimethylamino)propoxy]pyridin-3-yl]-4-[(4-methyl-1h-indol-5-yl)amino]pyridine-3-carbonitrile Chemical compound C1=NC(OCCCN(C)C)=CC=C1C1=CN=CC(C#N)=C1NC1=CC=C(NC=C2)C2=C1C IHIJGMGZNYFVMD-UHFFFAOYSA-N 0.000 claims 1
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