JP2016500671A5

JP2016500671A5 -

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Publication number: JP2016500671A5
Authority: JP; Japan
Prior art keywords: pyridin; fluoro; methylphenyl; pyridine; imidazo
Prior art date: 2013-10-04
Legal status : Granted

Application number

JP2015535846A

Other languages

English (en)

Japanese (ja)

Other versions

JP2016500671A (ja

JP6457942B2 (ja

Filing date

2013-10-04

Publication date

2016-11-17

2013-10-04 Application filed filed Critical

2013-10-04 Priority claimed from PCT/US2013/063585 external-priority patent/WO2014055955A1/en

2016-01-14 Publication of JP2016500671A publication Critical patent/JP2016500671A/ja

2016-11-17 Publication of JP2016500671A5 publication Critical patent/JP2016500671A5/ja

2019-01-23 Application granted granted Critical

2019-01-23 Publication of JP6457942B2 publication Critical patent/JP6457942B2/ja

Status Expired - Fee Related legal-status Critical Current

2033-10-04 Anticipated expiration legal-status Critical

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-1 3- (3- (imidazo [1,2-a] pyridin-6-yl) pyridin-2-yl) phenyl Chemical group 0.000 claims description 214
125000000217 alkyl group Chemical group 0.000 claims description 163
125000000623 heterocyclic group Chemical group 0.000 claims description 67
125000001072 heteroaryl group Chemical group 0.000 claims description 63
150000001875 compounds Chemical class 0.000 claims description 61
150000003839 salts Chemical class 0.000 claims description 60
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 59
125000003118 aryl group Chemical group 0.000 claims description 58
229910052736 halogen Inorganic materials 0.000 claims description 44
150000002367 halogens Chemical class 0.000 claims description 44
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 35
229910052739 hydrogen Inorganic materials 0.000 claims description 34
239000001257 hydrogen Substances 0.000 claims description 34
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 32
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 32
150000003857 carboxamides Chemical class 0.000 claims description 28
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
208000035475 disorder Diseases 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
201000010099 disease Diseases 0.000 claims description 15
125000004093 cyano group Chemical group *C#N 0.000 claims description 14
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 12
238000004895 liquid chromatography mass spectrometry Methods 0.000 claims description 12
229910052757 nitrogen Inorganic materials 0.000 claims description 12
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 10
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 8
241000124008 Mammalia Species 0.000 claims description 8
125000000392 cycloalkenyl group Chemical group 0.000 claims description 8
UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
239000008194 pharmaceutical composition Substances 0.000 claims description 8
125000004429 atom Chemical group 0.000 claims description 6
210000003205 muscle Anatomy 0.000 claims description 6
JVOGPCAZHXALIS-UHFFFAOYSA-N pyrazolo[1,5-a]pyridine-3-carboxamide Chemical compound C1=CC=CC2=C(C(=O)N)C=NN21 JVOGPCAZHXALIS-UHFFFAOYSA-N 0.000 claims description 6
125000004076 pyridyl group Chemical group 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
210000000988 bone and bone Anatomy 0.000 claims description 5
125000005842 heteroatom Chemical group 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
HZRPZQRIOGFQRU-UHFFFAOYSA-N 3-[3-(4-methoxyquinazolin-6-yl)pyridin-2-yl]phenol Chemical compound C1=C2C(OC)=NC=NC2=CC=C1C1=CC=CN=C1C1=CC=CC(O)=C1 HZRPZQRIOGFQRU-UHFFFAOYSA-N 0.000 claims description 4
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
FVWXUABIXHJYHA-UHFFFAOYSA-N 4-[[6-[2-(3-methylphenyl)pyridin-3-yl]imidazo[1,2-a]pyridin-3-yl]methyl]morpholine Chemical compound CC1=CC=CC(C=2C(=CC=CN=2)C2=CN3C(CN4CCOCC4)=CN=C3C=C2)=C1 FVWXUABIXHJYHA-UHFFFAOYSA-N 0.000 claims description 4
BPKGAZKEONIIQT-UHFFFAOYSA-N 4-methoxy-6-[2-(3-methylphenyl)pyridin-3-yl]quinazoline Chemical compound C1=C2C(OC)=NC=NC2=CC=C1C1=CC=CN=C1C1=CC=CC(C)=C1 BPKGAZKEONIIQT-UHFFFAOYSA-N 0.000 claims description 4
BAYKEGYFQTTWRP-UHFFFAOYSA-N 6-[2-(3-chloro-4-fluorophenyl)pyridin-3-yl]-1h-benzimidazole Chemical compound C1=C(Cl)C(F)=CC=C1C1=NC=CC=C1C1=CC=C(N=CN2)C2=C1 BAYKEGYFQTTWRP-UHFFFAOYSA-N 0.000 claims description 4
BFHTVDQJGJPIHY-UHFFFAOYSA-N 6-[2-(3-chloro-4-fluorophenyl)pyridin-3-yl]quinazolin-4-amine Chemical compound C1=C2C(N)=NC=NC2=CC=C1C1=CC=CN=C1C1=CC=C(F)C(Cl)=C1 BFHTVDQJGJPIHY-UHFFFAOYSA-N 0.000 claims description 4
PDXVNVJKLHUQDR-UHFFFAOYSA-N 6-[2-(3-methylphenyl)pyridin-3-yl]isoquinoline Chemical compound CC1=CC=CC(C=2C(=CC=CN=2)C=2C=C3C=CN=CC3=CC=2)=C1 PDXVNVJKLHUQDR-UHFFFAOYSA-N 0.000 claims description 4
MBWCMBNYLSFYRH-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]isoquinoline Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3C=CN=CC3=CC=2)=C1 MBWCMBNYLSFYRH-UHFFFAOYSA-N 0.000 claims description 4
CEBTWJXRPPONAC-UHFFFAOYSA-N 6-[2-(5-chloro-2,4-difluorophenyl)pyridin-3-yl]quinazolin-4-amine Chemical compound C1=C2C(N)=NC=NC2=CC=C1C1=CC=CN=C1C1=CC(Cl)=C(F)C=C1F CEBTWJXRPPONAC-UHFFFAOYSA-N 0.000 claims description 4
WMZNHTCLHJHMEY-UHFFFAOYSA-N 6-[2-(5-chloro-2-fluorophenyl)pyridin-3-yl]quinazolin-4-amine Chemical compound C1=C2C(N)=NC=NC2=CC=C1C1=CC=CN=C1C1=CC(Cl)=CC=C1F WMZNHTCLHJHMEY-UHFFFAOYSA-N 0.000 claims description 4
VLMSVHZRXNKSFR-UHFFFAOYSA-N CC1=CC=CC(C=2C(=CC=CN=2)C=2C=C3N=CC=NC3=CC=2)=C1.C1CC1C1=CC=CC(C=2C(=CC=CN=2)C=2C=C3N=CC=NC3=CC=2)=C1 Chemical compound CC1=CC=CC(C=2C(=CC=CN=2)C=2C=C3N=CC=NC3=CC=2)=C1.C1CC1C1=CC=CC(C=2C(=CC=CN=2)C=2C=C3N=CC=NC3=CC=2)=C1 VLMSVHZRXNKSFR-UHFFFAOYSA-N 0.000 claims description 4
AJKBIZVJPTZBSR-UHFFFAOYSA-N CC1=CCC2=CC(=CC=C12)C1=NC=CC=C1C1=CC=NC=C1.N1=C(C(=CC=C1)C1=CC=NC=C1)C=1C=C2CCC(C2=CC1)=O Chemical compound CC1=CCC2=CC(=CC=C12)C1=NC=CC=C1C1=CC=NC=C1.N1=C(C(=CC=C1)C1=CC=NC=C1)C=1C=C2CCC(C2=CC1)=O AJKBIZVJPTZBSR-UHFFFAOYSA-N 0.000 claims description 4
208000021642 Muscular disease Diseases 0.000 claims description 4
DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 4
208000001132 Osteoporosis Diseases 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
ZMBYQTGAXZOMOO-UHFFFAOYSA-N imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=CC=CN2C(C(=O)N)=CN=C21 ZMBYQTGAXZOMOO-UHFFFAOYSA-N 0.000 claims description 4
201000000585 muscular atrophy Diseases 0.000 claims description 4
201000006938 muscular dystrophy Diseases 0.000 claims description 4
XFSRXSAFMFOIGF-GOTSBHOMSA-N n-[(1s,2s)-2-aminocyclohexyl]-5-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]indazole-1-carboxamide Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3C=NN(C3=CC=2)C(=O)N[C@@H]2[C@H](CCCC2)N)=C1 XFSRXSAFMFOIGF-GOTSBHOMSA-N 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
125000004043 oxo group Chemical group O=* 0.000 claims description 4
125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
208000011580 syndromic disease Diseases 0.000 claims description 4
208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 4
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 3
XXOLUVYFIRRYSW-UHFFFAOYSA-N 7-[2-(2-fluoro-5-methylphenyl)pyridin-3-yl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound CC1=CC=C(F)C(C=2C(=CC=CN=2)C2=CC3=NC=NN3C=C2)=C1 XXOLUVYFIRRYSW-UHFFFAOYSA-N 0.000 claims description 3
UXVSJCQENXSRCT-HSZRJFAPSA-N (2R)-1-[7-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]imidazo[1,5-a]pyridin-1-yl]-3-(1H-indol-3-yl)propan-2-amine Chemical compound N[C@@H](CC=1N=CN2C=1C=C(C=C2)C=1C(=NC=CC=1)C1=CC(=C(C=C1)F)C)CC1=CNC2=CC=CC=C12 UXVSJCQENXSRCT-HSZRJFAPSA-N 0.000 claims description 2
UPVTZOFWHYKCKH-NHFJDJAPSA-N (NE)-N-[5-[3-(4-aminoquinazolin-6-yl)pyridin-2-yl]-2,3-dihydroinden-1-ylidene]hydroxylamine Chemical compound C1=C2\C(=N\O)CCC2=CC(C2=NC=CC=C2C2=CC=C3N=CN=C(C3=C2)N)=C1 UPVTZOFWHYKCKH-NHFJDJAPSA-N 0.000 claims description 2
JKKKDKDPFBBHPC-UHFFFAOYSA-N 1-(3-ethoxypropyl)-6-[2-(3-methylphenyl)pyridin-3-yl]benzimidazole Chemical compound C1=C2N(CCCOCC)C=NC2=CC=C1C1=CC=CN=C1C1=CC=CC(C)=C1 JKKKDKDPFBBHPC-UHFFFAOYSA-N 0.000 claims description 2
FEFRIEYXIAPAES-UHFFFAOYSA-N 1-(3-ethoxypropyl)-6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]benzimidazole Chemical compound C1=C2N(CCCOCC)C=NC2=CC=C1C1=CC=CN=C1C1=CC=C(F)C(C)=C1 FEFRIEYXIAPAES-UHFFFAOYSA-N 0.000 claims description 2
IISJSKVLFKCEJP-UHFFFAOYSA-N 1-[3-[6-[2-(3-chloro-4-fluorophenyl)pyridin-3-yl]quinazolin-4-yl]oxypropyl]pyrrolidin-2-one Chemical compound C1=C(Cl)C(F)=CC=C1C1=NC=CC=C1C1=CC=C(N=CN=C2OCCCN3C(CCC3)=O)C2=C1 IISJSKVLFKCEJP-UHFFFAOYSA-N 0.000 claims description 2
CBLHFAKFQMDRGU-UHFFFAOYSA-N 1-[3-[6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]quinazolin-4-yl]oxypropyl]pyrrolidin-2-one Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3C(OCCCN4C(CCC4)=O)=NC=NC3=CC=2)=C1 CBLHFAKFQMDRGU-UHFFFAOYSA-N 0.000 claims description 2
HYCAEVUWIBUHPW-UHFFFAOYSA-N 1-[5-(1h-indazol-5-yl)-6-(3-methylphenyl)pyridin-3-yl]-3-propan-2-ylurea Chemical compound C=1C=C2NN=CC2=CC=1C1=CC(NC(=O)NC(C)C)=CN=C1C1=CC=CC(C)=C1 HYCAEVUWIBUHPW-UHFFFAOYSA-N 0.000 claims description 2
BQRZZVCPEORZHF-UHFFFAOYSA-N 1-[6-(3-cyclopropylphenyl)-5-(1h-indazol-5-yl)pyridin-3-yl]-3-propan-2-ylurea Chemical compound C=1C=C2NN=CC2=CC=1C1=CC(NC(=O)NC(C)C)=CN=C1C(C=1)=CC=CC=1C1CC1 BQRZZVCPEORZHF-UHFFFAOYSA-N 0.000 claims description 2
BOBWAIOLLORWRZ-UHFFFAOYSA-N 1-[6-(4-fluoro-3-methylphenyl)-5-quinoxalin-6-ylpyridin-3-yl]-n,n-dimethylmethanamine Chemical compound C=1C=C2N=CC=NC2=CC=1C1=CC(CN(C)C)=CN=C1C1=CC=C(F)C(C)=C1 BOBWAIOLLORWRZ-UHFFFAOYSA-N 0.000 claims description 2
UTHPRRZRYUMQEH-UHFFFAOYSA-N 1-[6-[2-(3-chloro-4-fluorophenyl)pyridin-3-yl]imidazo[1,2-a]pyridin-3-yl]ethanone Chemical compound C=1N2C(C(=O)C)=CN=C2C=CC=1C1=CC=CN=C1C1=CC=C(F)C(Cl)=C1 UTHPRRZRYUMQEH-UHFFFAOYSA-N 0.000 claims description 2
NNHLFUNIWRDYNM-UHFFFAOYSA-N 1-[6-[2-(3-chlorophenyl)pyridin-3-yl]imidazo[1,2-a]pyridin-3-yl]ethanone Chemical compound C=1N2C(C(=O)C)=CN=C2C=CC=1C1=CC=CN=C1C1=CC=CC(Cl)=C1 NNHLFUNIWRDYNM-UHFFFAOYSA-N 0.000 claims description 2
DHLMMEAXPLQFOJ-UHFFFAOYSA-N 1-[6-[2-(3-cyclopropylphenyl)pyridin-3-yl]imidazo[1,2-a]pyridin-3-yl]ethanone Chemical compound C=1N2C(C(=O)C)=CN=C2C=CC=1C1=CC=CN=C1C(C=1)=CC=CC=1C1CC1 DHLMMEAXPLQFOJ-UHFFFAOYSA-N 0.000 claims description 2
IAWADFZOVHFGHH-UHFFFAOYSA-N 1-[6-[2-(3-methylphenyl)pyridin-3-yl]imidazo[1,2-a]pyridin-3-yl]ethanone Chemical compound C=1N2C(C(=O)C)=CN=C2C=CC=1C1=CC=CN=C1C1=CC=CC(C)=C1 IAWADFZOVHFGHH-UHFFFAOYSA-N 0.000 claims description 2
JWKHZEAPAQKJIM-UHFFFAOYSA-N 1-[6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]imidazo[1,2-a]pyridin-3-yl]ethanone Chemical compound C=1N2C(C(=O)C)=CN=C2C=CC=1C1=CC=CN=C1C1=CC=C(F)C(C)=C1 JWKHZEAPAQKJIM-UHFFFAOYSA-N 0.000 claims description 2
IAWADFZOVHFGHH-FIBGUPNXSA-N 1-[6-[2-[3-(trideuteriomethyl)phenyl]pyridin-3-yl]imidazo[1,2-a]pyridin-3-yl]ethanone Chemical compound [2H]C([2H])([2H])C1=CC=CC(C=2C(=CC=CN=2)C2=CN3C(C(C)=O)=CN=C3C=C2)=C1 IAWADFZOVHFGHH-FIBGUPNXSA-N 0.000 claims description 2
BTJZSYCEACPWIN-UHFFFAOYSA-N 1-[6-[2-[3-(trifluoromethyl)phenyl]pyridin-3-yl]imidazo[1,2-a]pyridin-3-yl]ethanone Chemical compound C=1N2C(C(=O)C)=CN=C2C=CC=1C1=CC=CN=C1C1=CC=CC(C(F)(F)F)=C1 BTJZSYCEACPWIN-UHFFFAOYSA-N 0.000 claims description 2
SAEHEKFWEPJSJO-UHFFFAOYSA-N 1-ethyl-3-[6-(4-fluoro-3-methylphenyl)-5-imidazo[1,2-a]pyridin-6-ylpyridin-3-yl]urea Chemical compound C1=CC2=NC=CN2C=C1C1=CC(NC(=O)NCC)=CN=C1C1=CC=C(F)C(C)=C1 SAEHEKFWEPJSJO-UHFFFAOYSA-N 0.000 claims description 2
ZSEDKWJMLSUEOW-UHFFFAOYSA-N 1-ethyl-5-[2-(3-methylphenyl)pyridin-3-yl]indazole Chemical compound C=1C=C2N(CC)N=CC2=CC=1C1=CC=CN=C1C1=CC=CC(C)=C1 ZSEDKWJMLSUEOW-UHFFFAOYSA-N 0.000 claims description 2
UTSOQFDWXIGMQI-UHFFFAOYSA-N 1-ethyl-5-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]indazole Chemical compound C=1C=C2N(CC)N=CC2=CC=1C1=CC=CN=C1C1=CC=C(F)C(C)=C1 UTSOQFDWXIGMQI-UHFFFAOYSA-N 0.000 claims description 2
XSTOHZFRXXKMEI-UHFFFAOYSA-N 1-ethyl-6-[2-(3-methylphenyl)pyridin-3-yl]benzimidazole Chemical compound C1=C2N(CC)C=NC2=CC=C1C1=CC=CN=C1C1=CC=CC(C)=C1 XSTOHZFRXXKMEI-UHFFFAOYSA-N 0.000 claims description 2
YLGUTHKLLZOHMG-UHFFFAOYSA-N 1-ethyl-6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]benzimidazole Chemical compound C1=C2N(CC)C=NC2=CC=C1C1=CC=CN=C1C1=CC=C(F)C(C)=C1 YLGUTHKLLZOHMG-UHFFFAOYSA-N 0.000 claims description 2
SLXOGPCNRCOSBB-UHFFFAOYSA-N 1-methyl-5-[2-(3-methylphenyl)pyridin-3-yl]benzimidazole Chemical compound CC1=CC=CC(C=2C(=CC=CN=2)C=2C=C3N=CN(C)C3=CC=2)=C1 SLXOGPCNRCOSBB-UHFFFAOYSA-N 0.000 claims description 2
WPCJXQQVSWJICK-UHFFFAOYSA-N 1-methyl-5-[2-(3-methylphenyl)pyridin-3-yl]indazole Chemical compound CC1=CC=CC(C=2C(=CC=CN=2)C=2C=C3C=NN(C)C3=CC=2)=C1 WPCJXQQVSWJICK-UHFFFAOYSA-N 0.000 claims description 2
RTUHVRNRGJMATA-UHFFFAOYSA-N 1-methyl-6-[2-(3-methylphenyl)pyridin-3-yl]benzimidazole Chemical compound CC1=CC=CC(C=2C(=CC=CN=2)C=2C=C3N(C)C=NC3=CC=2)=C1 RTUHVRNRGJMATA-UHFFFAOYSA-N 0.000 claims description 2
MWIJIIQKLRIMEQ-UHFFFAOYSA-N 1-methyl-6-[2-(3-methylphenyl)pyridin-3-yl]indazole Chemical compound CC1=CC=CC(C=2C(=CC=CN=2)C=2C=C3N(C)N=CC3=CC=2)=C1 MWIJIIQKLRIMEQ-UHFFFAOYSA-N 0.000 claims description 2
VZEAYYKTBNOASV-UHFFFAOYSA-N 2,3-bis(4-fluorophenyl)pyridine Chemical compound C1=CC(F)=CC=C1C1=CC=CN=C1C1=CC=C(F)C=C1 VZEAYYKTBNOASV-UHFFFAOYSA-N 0.000 claims description 2
YYCYJRRWJMQAOI-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-3-(6-methylpyridin-2-yl)pyridine Chemical compound CC1=CC=CC(C=2C(=NC=CC=2)C=2C=C3OCOC3=CC=2)=N1 YYCYJRRWJMQAOI-UHFFFAOYSA-N 0.000 claims description 2
SEXNZTIMVAPDLO-UHFFFAOYSA-N 2-(2,3-dihydro-1h-inden-5-yl)-3-pyridin-4-ylpyridine Chemical compound C1=C2CCCC2=CC=C1C1=NC=CC=C1C1=CC=NC=C1 SEXNZTIMVAPDLO-UHFFFAOYSA-N 0.000 claims description 2
KZABZAUNHFVHOM-UHFFFAOYSA-N 2-(2-fluorophenyl)-3-(4-fluorophenyl)pyridine Chemical compound C1=CC(F)=CC=C1C1=CC=CN=C1C1=CC=CC=C1F KZABZAUNHFVHOM-UHFFFAOYSA-N 0.000 claims description 2
MGABNKRLGZRVSQ-UHFFFAOYSA-N 2-(2-fluorophenyl)-3-pyridin-4-ylpyridine Chemical compound FC1=CC=CC=C1C1=NC=CC=C1C1=CC=NC=C1 MGABNKRLGZRVSQ-UHFFFAOYSA-N 0.000 claims description 2
VDVZQWZSXNLONM-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-3-(4-fluorophenyl)pyridine Chemical compound C1=CC(F)=CC=C1C1=CC=CN=C1C1=CC=C(F)C(F)=C1 VDVZQWZSXNLONM-UHFFFAOYSA-N 0.000 claims description 2
PCEPJZFQNMGIHY-UHFFFAOYSA-N 2-(3-fluorophenyl)-3-(4-fluorophenyl)pyridine Chemical compound C1=CC(F)=CC=C1C1=CC=CN=C1C1=CC=CC(F)=C1 PCEPJZFQNMGIHY-UHFFFAOYSA-N 0.000 claims description 2
OUUDVARCMNAOHM-UHFFFAOYSA-N 2-(4-fluoro-3-methylphenyl)-3-(4-fluorophenyl)pyridine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=CC(F)=CC=2)=C1 OUUDVARCMNAOHM-UHFFFAOYSA-N 0.000 claims description 2
NSEVIHMNHKDJAY-UHFFFAOYSA-N 2-[2-(3-chloro-4-fluorophenyl)pyridin-3-yl]-1,5-naphthyridine Chemical compound C1=C(Cl)C(F)=CC=C1C1=NC=CC=C1C1=CC=C(N=CC=C2)C2=N1 NSEVIHMNHKDJAY-UHFFFAOYSA-N 0.000 claims description 2
DIRVDBAXXPVHAS-UHFFFAOYSA-N 2-[2-(3-cyclopropyl-4-fluorophenyl)pyridin-3-yl]-1,5-naphthyridine Chemical compound FC1=CC=C(C=2C(=CC=CN=2)C=2N=C3C=CC=NC3=CC=2)C=C1C1CC1 DIRVDBAXXPVHAS-UHFFFAOYSA-N 0.000 claims description 2
NLLQUXPFDMKJJB-UHFFFAOYSA-N 2-[2-(3-cyclopropylphenyl)pyridin-3-yl]-1,5-naphthyridine Chemical compound C1CC1C1=CC=CC(C=2C(=CC=CN=2)C=2N=C3C=CC=NC3=CC=2)=C1 NLLQUXPFDMKJJB-UHFFFAOYSA-N 0.000 claims description 2
UNAPBIXNPYNURR-UHFFFAOYSA-N 2-[2-(3-cyclopropylphenyl)pyridin-3-yl]-1,6-naphthyridine Chemical compound C1CC1C1=CC=CC(C=2C(=CC=CN=2)C=2N=C3C=CN=CC3=CC=2)=C1 UNAPBIXNPYNURR-UHFFFAOYSA-N 0.000 claims description 2
VIHJLSYVIGWEKM-UHFFFAOYSA-N 2-[2-(3-methylphenyl)pyridin-3-yl]-1,5-naphthyridine Chemical compound CC1=CC=CC(C=2C(=CC=CN=2)C=2N=C3C=CC=NC3=CC=2)=C1 VIHJLSYVIGWEKM-UHFFFAOYSA-N 0.000 claims description 2
AIDAWLQMWZSYAI-UHFFFAOYSA-N 2-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-1,5-naphthyridine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2N=C3C=CC=NC3=CC=2)=C1 AIDAWLQMWZSYAI-UHFFFAOYSA-N 0.000 claims description 2
NWEUUHBKQWIJTJ-UHFFFAOYSA-N 2-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-1,6-naphthyridine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2N=C3C=CN=CC3=CC=2)=C1 NWEUUHBKQWIJTJ-UHFFFAOYSA-N 0.000 claims description 2
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HQKNTEXLBNYDGR-UHFFFAOYSA-N 4-[2-(2,3-dihydro-1h-inden-5-yl)pyridin-3-yl]-1h-quinolin-2-one Chemical compound C12=CC=CC=C2NC(=O)C=C1C1=CC=CN=C1C1=CC=C(CCC2)C2=C1 HQKNTEXLBNYDGR-UHFFFAOYSA-N 0.000 claims description 2
AEOBCTJDOOYWHA-UHFFFAOYSA-N 4-[2-(2-fluoro-5-methylphenyl)pyridin-3-yl]-1h-quinolin-2-one Chemical compound CC1=CC=C(F)C(C=2C(=CC=CN=2)C=2C3=CC=CC=C3NC(=O)C=2)=C1 AEOBCTJDOOYWHA-UHFFFAOYSA-N 0.000 claims description 2
NXTDBYZIOREQDU-UHFFFAOYSA-N 4-[2-(2-fluorophenyl)pyridin-3-yl]-1h-quinolin-2-one Chemical compound FC1=CC=CC=C1C1=NC=CC=C1C1=CC(=O)NC2=CC=CC=C12 NXTDBYZIOREQDU-UHFFFAOYSA-N 0.000 claims description 2
NGAGSPSYQWXXBX-UHFFFAOYSA-N 4-[2-(3,4-difluorophenyl)pyridin-3-yl]-1h-quinolin-2-one Chemical compound C1=C(F)C(F)=CC=C1C1=NC=CC=C1C1=CC(=O)NC2=CC=CC=C12 NGAGSPSYQWXXBX-UHFFFAOYSA-N 0.000 claims description 2
UCJDEBIMAAZCOO-UHFFFAOYSA-N 4-[2-(3-fluorophenyl)pyridin-3-yl]-1h-quinolin-2-one Chemical compound FC1=CC=CC(C=2C(=CC=CN=2)C=2C3=CC=CC=C3NC(=O)C=2)=C1 UCJDEBIMAAZCOO-UHFFFAOYSA-N 0.000 claims description 2
LEENGCLCEZVXOJ-UHFFFAOYSA-N 4-[2-(3-methylphenyl)pyridin-3-yl]quinoline Chemical compound CC1=CC=CC(C=2C(=CC=CN=2)C=2C3=CC=CC=C3N=CC=2)=C1 LEENGCLCEZVXOJ-UHFFFAOYSA-N 0.000 claims description 2
ARSAAXMGBAGOKJ-UHFFFAOYSA-N 4-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-2-methoxypyrimidine Chemical compound COC1=NC=CC(C=2C(=NC=CC=2)C=2C=C(C)C(F)=CC=2)=N1 ARSAAXMGBAGOKJ-UHFFFAOYSA-N 0.000 claims description 2
JOPFMIJBKRWFSE-UHFFFAOYSA-N 4-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-n-(3,4,5-trimethoxyphenyl)pyrimidin-2-amine Chemical compound COC1=C(OC)C(OC)=CC(NC=2N=C(C=CN=2)C=2C(=NC=CC=2)C=2C=C(C)C(F)=CC=2)=C1 JOPFMIJBKRWFSE-UHFFFAOYSA-N 0.000 claims description 2
MBDFYITUEFUNKH-UHFFFAOYSA-N 4-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-n-(3-morpholin-4-ylphenyl)pyrimidin-2-amine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2N=C(NC=3C=C(C=CC=3)N3CCOCC3)N=CC=2)=C1 MBDFYITUEFUNKH-UHFFFAOYSA-N 0.000 claims description 2
FCEFXMBOMKLBLE-UHFFFAOYSA-N 4-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-n-(4-morpholin-4-ylphenyl)pyrimidin-2-amine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2N=C(NC=3C=CC(=CC=3)N3CCOCC3)N=CC=2)=C1 FCEFXMBOMKLBLE-UHFFFAOYSA-N 0.000 claims description 2
CPCJUBVNKIULRW-UHFFFAOYSA-N 4-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-n-(4-piperazin-1-ylphenyl)pyrimidin-2-amine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2N=C(NC=3C=CC(=CC=3)N3CCNCC3)N=CC=2)=C1 CPCJUBVNKIULRW-UHFFFAOYSA-N 0.000 claims description 2
QWWIEIPWNSDEPM-UHFFFAOYSA-N 4-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-n-(6-piperazin-1-ylpyridin-3-yl)pyrimidin-2-amine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2N=C(NC=3C=NC(=CC=3)N3CCNCC3)N=CC=2)=C1 QWWIEIPWNSDEPM-UHFFFAOYSA-N 0.000 claims description 2
UTJHDFJCEVWKRA-UHFFFAOYSA-N 4-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]pyrimidin-2-amine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2N=C(N)N=CC=2)=C1 UTJHDFJCEVWKRA-UHFFFAOYSA-N 0.000 claims description 2
XKQLAELNVCGHFD-UHFFFAOYSA-N 4-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]quinoline Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C3=CC=CC=C3N=CC=2)=C1 XKQLAELNVCGHFD-UHFFFAOYSA-N 0.000 claims description 2
AFFIRYDEQYLFAY-UHFFFAOYSA-N 4-[2-(4-fluorophenyl)pyridin-3-yl]quinoline Chemical compound C1=CC(F)=CC=C1C1=NC=CC=C1C1=CC=NC2=CC=CC=C12 AFFIRYDEQYLFAY-UHFFFAOYSA-N 0.000 claims description 2
BUBCLILLGYRAIK-UHFFFAOYSA-N 4-[2-[6-[2-(3-methylphenyl)pyridin-3-yl]benzimidazol-1-yl]ethyl]morpholine Chemical compound CC1=CC=CC(C=2C(=CC=CN=2)C=2C=C3N(CCN4CCOCC4)C=NC3=CC=2)=C1 BUBCLILLGYRAIK-UHFFFAOYSA-N 0.000 claims description 2
AZZMRAKBRBTBIG-UHFFFAOYSA-N 4-[2-[6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]benzimidazol-1-yl]ethyl]morpholine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3N(CCN4CCOCC4)C=NC3=CC=2)=C1 AZZMRAKBRBTBIG-UHFFFAOYSA-N 0.000 claims description 2
HLRWIUQESKORBR-UHFFFAOYSA-N 4-[2-[6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]quinazolin-4-yl]oxyethyl]morpholine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3C(OCCN4CCOCC4)=NC=NC3=CC=2)=C1 HLRWIUQESKORBR-UHFFFAOYSA-N 0.000 claims description 2
ZQUCUYWDAOAKLQ-UHFFFAOYSA-N 4-[3-(1H-indazol-5-yl)pyridin-2-yl]-2-methylphenol Chemical compound C1=C(O)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3C=NNC3=CC=2)=C1 ZQUCUYWDAOAKLQ-UHFFFAOYSA-N 0.000 claims description 2
SDWWLMXQQJJNSE-UHFFFAOYSA-N 4-[3-(1H-indazol-5-yl)pyridin-2-yl]phenol Chemical compound C1=CC(O)=CC=C1C1=NC=CC=C1C1=CC=C(NN=C2)C2=C1 SDWWLMXQQJJNSE-UHFFFAOYSA-N 0.000 claims description 2
JFAYHZRSZOBJBH-UHFFFAOYSA-N 4-[3-(1h-indazol-5-yl)pyridin-2-yl]-2-methylaniline Chemical compound C1=C(N)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3C=NNC3=CC=2)=C1 JFAYHZRSZOBJBH-UHFFFAOYSA-N 0.000 claims description 2
FRPNPKRBZHZILD-UHFFFAOYSA-N 4-[3-(1h-indazol-5-yl)pyridin-2-yl]-n,n,2-trimethylaniline Chemical compound C1=C(C)C(N(C)C)=CC=C1C1=NC=CC=C1C1=CC=C(NN=C2)C2=C1 FRPNPKRBZHZILD-UHFFFAOYSA-N 0.000 claims description 2
PQUUYFGHYOZCRA-UHFFFAOYSA-N 4-[3-(1h-indazol-5-yl)pyridin-2-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=NC=CC=C1C1=CC=C(NN=C2)C2=C1 PQUUYFGHYOZCRA-UHFFFAOYSA-N 0.000 claims description 2
PZZYAQVOBXCWGV-UHFFFAOYSA-N 4-[3-(1h-indazol-5-yl)pyridin-2-yl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=NC=CC=C1C1=CC=C(NN=C2)C2=C1 PZZYAQVOBXCWGV-UHFFFAOYSA-N 0.000 claims description 2
ASYSAHKEUUYTDV-UHFFFAOYSA-N 4-[3-[6-[2-(3-methylphenyl)pyridin-3-yl]benzimidazol-1-yl]propyl]morpholine Chemical compound CC1=CC=CC(C=2C(=CC=CN=2)C=2C=C3N(CCCN4CCOCC4)C=NC3=CC=2)=C1 ASYSAHKEUUYTDV-UHFFFAOYSA-N 0.000 claims description 2
XLLDVMFCPZVQHP-UHFFFAOYSA-N 4-[3-[6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]quinazolin-4-yl]oxyphenyl]morpholine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3C(OC=4C=C(C=CC=4)N4CCOCC4)=NC=NC3=CC=2)=C1 XLLDVMFCPZVQHP-UHFFFAOYSA-N 0.000 claims description 2
NSYQYIZLHIWDCU-UHFFFAOYSA-N 4-[6-[2-(3-cyclopropylphenyl)pyridin-3-yl]imidazo[1,2-a]pyridin-3-yl]morpholine Chemical compound C1CC1C1=CC=CC(C=2C(=CC=CN=2)C2=CN3C(N4CCOCC4)=CN=C3C=C2)=C1 NSYQYIZLHIWDCU-UHFFFAOYSA-N 0.000 claims description 2
YWOMCMYVIDZLNR-UHFFFAOYSA-N 4-[6-[2-(3-cyclopropylphenyl)pyridin-3-yl]quinazolin-4-yl]morpholine Chemical compound C1CC1C1=CC=CC(C=2C(=CC=CN=2)C=2C=C3C(N4CCOCC4)=NC=NC3=CC=2)=C1 YWOMCMYVIDZLNR-UHFFFAOYSA-N 0.000 claims description 2
JJGPOABRKMSHNU-UHFFFAOYSA-N 4-[6-[2-(3-cyclopropylphenyl)pyridin-3-yl]quinolin-4-yl]morpholine Chemical compound C1CC1C1=CC=CC(C=2C(=CC=CN=2)C=2C=C3C(N4CCOCC4)=CC=NC3=CC=2)=C1 JJGPOABRKMSHNU-UHFFFAOYSA-N 0.000 claims description 2
CHAXVFWAYVQFAV-UHFFFAOYSA-N 4-[6-[2-(3-methylphenyl)pyridin-3-yl]imidazo[1,2-a]pyridin-3-yl]morpholine Chemical compound CC1=CC=CC(C=2C(=CC=CN=2)C2=CN3C(N4CCOCC4)=CN=C3C=C2)=C1 CHAXVFWAYVQFAV-UHFFFAOYSA-N 0.000 claims description 2
OBTNHHMTGGLXPZ-UHFFFAOYSA-N 4-[6-[2-(3-methylphenyl)pyridin-3-yl]quinolin-4-yl]morpholine Chemical compound CC1=CC=CC(C=2C(=CC=CN=2)C=2C=C3C(N4CCOCC4)=CC=NC3=CC=2)=C1 OBTNHHMTGGLXPZ-UHFFFAOYSA-N 0.000 claims description 2
PJUDEAPLIRINCZ-UHFFFAOYSA-N 4-[6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]imidazo[1,2-a]pyridin-3-yl]benzenesulfonamide Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C2=CN3C(C=4C=CC(=CC=4)S(N)(=O)=O)=CN=C3C=C2)=C1 PJUDEAPLIRINCZ-UHFFFAOYSA-N 0.000 claims description 2
CZCOVNZUKDLGRO-UHFFFAOYSA-N 4-[6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]imidazo[1,2-a]pyridin-3-yl]morpholine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C2=CN3C(N4CCOCC4)=CN=C3C=C2)=C1 CZCOVNZUKDLGRO-UHFFFAOYSA-N 0.000 claims description 2
DUTVNLCOXPRWGX-UHFFFAOYSA-N 4-[6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]quinazolin-4-yl]morpholine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3C(N4CCOCC4)=NC=NC3=CC=2)=C1 DUTVNLCOXPRWGX-UHFFFAOYSA-N 0.000 claims description 2
ACBSAOAUZXQDNO-UHFFFAOYSA-N 4-[6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]quinazolin-4-yl]oxybenzonitrile Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3C(OC=4C=CC(=CC=4)C#N)=NC=NC3=CC=2)=C1 ACBSAOAUZXQDNO-UHFFFAOYSA-N 0.000 claims description 2
PFLSKHKIYKWCNX-UHFFFAOYSA-N 4-[6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]quinolin-4-yl]morpholine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3C(N4CCOCC4)=CC=NC3=CC=2)=C1 PFLSKHKIYKWCNX-UHFFFAOYSA-N 0.000 claims description 2
SPOUYESBZGYZHY-UHFFFAOYSA-N 4-[6-[2-[3-(trifluoromethyl)phenyl]pyridin-3-yl]imidazo[1,2-a]pyridin-3-yl]morpholine Chemical compound FC(F)(F)C1=CC=CC(C=2C(=CC=CN=2)C2=CN3C(N4CCOCC4)=CN=C3C=C2)=C1 SPOUYESBZGYZHY-UHFFFAOYSA-N 0.000 claims description 2
CIKYYZIRDXXMDT-UHFFFAOYSA-N 4-[6-[2-[3-(trifluoromethyl)phenyl]pyridin-3-yl]quinolin-4-yl]morpholine Chemical compound FC(F)(F)C1=CC=CC(C=2C(=CC=CN=2)C=2C=C3C(N4CCOCC4)=CC=NC3=CC=2)=C1 CIKYYZIRDXXMDT-UHFFFAOYSA-N 0.000 claims description 2
JLPSGCNECGGZBA-UHFFFAOYSA-N 4-[[4-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2N=C(NC=3C=CC(=CC=3)S(N)(=O)=O)N=CC=2)=C1 JLPSGCNECGGZBA-UHFFFAOYSA-N 0.000 claims description 2
BGZYYHIZLXOTMI-UHFFFAOYSA-N 4-[[6-(4-fluoro-3-methylphenyl)-5-quinoxalin-6-ylpyridin-3-yl]methyl]morpholine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC(CN3CCOCC3)=CN=2)C=2C=C3N=CC=NC3=CC=2)=C1 BGZYYHIZLXOTMI-UHFFFAOYSA-N 0.000 claims description 2
DRNWLKICRPNVMH-UHFFFAOYSA-N 4-[[6-[2-(3-cyclopropylphenyl)pyridin-3-yl]imidazo[1,2-a]pyridin-3-yl]methyl]morpholine Chemical compound C=1N=C2C=CC(C=3C(=NC=CC=3)C=3C=C(C=CC=3)C3CC3)=CN2C=1CN1CCOCC1 DRNWLKICRPNVMH-UHFFFAOYSA-N 0.000 claims description 2
GVZUMUDEPBMQGA-UHFFFAOYSA-N 4-[[6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]imidazo[1,2-a]pyridin-3-yl]methyl]morpholine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C2=CN3C(CN4CCOCC4)=CN=C3C=C2)=C1 GVZUMUDEPBMQGA-UHFFFAOYSA-N 0.000 claims description 2
OFUXPBVWCDRBTE-UHFFFAOYSA-N 4-[[6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]quinazolin-4-yl]amino]benzamide Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3C(NC=4C=CC(=CC=4)C(N)=O)=NC=NC3=CC=2)=C1 OFUXPBVWCDRBTE-UHFFFAOYSA-N 0.000 claims description 2
AQRZQXJSWPADGQ-UHFFFAOYSA-N 4-[[6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]quinazolin-4-yl]amino]benzonitrile Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3C(NC=4C=CC(=CC=4)C#N)=NC=NC3=CC=2)=C1 AQRZQXJSWPADGQ-UHFFFAOYSA-N 0.000 claims description 2
XWYIFOJMSTVGQF-UHFFFAOYSA-N 4-[[6-[2-[3-(trifluoromethyl)phenyl]pyridin-3-yl]imidazo[1,2-a]pyridin-3-yl]methyl]morpholine Chemical compound FC(F)(F)C1=CC=CC(C=2C(=CC=CN=2)C2=CN3C(CN4CCOCC4)=CN=C3C=C2)=C1 XWYIFOJMSTVGQF-UHFFFAOYSA-N 0.000 claims description 2
OFIDECFVNPLLPA-UHFFFAOYSA-N 4-[[[5-(1,3-benzothiazol-6-yl)-6-(4-fluoro-3-methylphenyl)pyridin-3-yl]amino]methyl]-2,6-dimethoxyphenol Chemical compound COC1=C(O)C(OC)=CC(CNC=2C=C(C(C=3C=C(C)C(F)=CC=3)=NC=2)C=2C=C3SC=NC3=CC=2)=C1 OFIDECFVNPLLPA-UHFFFAOYSA-N 0.000 claims description 2
HLXMGEDQQWRDPA-UHFFFAOYSA-N 4-[[[5-(1,3-benzothiazol-6-yl)-6-(4-fluoro-3-methylphenyl)pyridin-3-yl]amino]methyl]-2-(trifluoromethoxy)phenol Chemical compound C1=C(F)C(C)=CC(C=2C(=CC(NCC=3C=C(OC(F)(F)F)C(O)=CC=3)=CN=2)C=2C=C3SC=NC3=CC=2)=C1 HLXMGEDQQWRDPA-UHFFFAOYSA-N 0.000 claims description 2
XYMKDIDOFBQGRN-UHFFFAOYSA-N 4-[[[5-(1,3-benzothiazol-6-yl)-6-(4-fluoro-3-methylphenyl)pyridin-3-yl]amino]methyl]-2-(trifluoromethyl)phenol Chemical compound C1=C(F)C(C)=CC(C=2C(=CC(NCC=3C=C(C(O)=CC=3)C(F)(F)F)=CN=2)C=2C=C3SC=NC3=CC=2)=C1 XYMKDIDOFBQGRN-UHFFFAOYSA-N 0.000 claims description 2
LFPYAARQSGTBNL-UHFFFAOYSA-N 4-[[[5-(1,3-benzothiazol-6-yl)-6-(4-fluoro-3-methylphenyl)pyridin-3-yl]amino]methyl]benzene-1,2-diol Chemical compound C1=C(F)C(C)=CC(C=2C(=CC(NCC=3C=C(O)C(O)=CC=3)=CN=2)C=2C=C3SC=NC3=CC=2)=C1 LFPYAARQSGTBNL-UHFFFAOYSA-N 0.000 claims description 2
VRRAVJXMIWYBDX-UHFFFAOYSA-N 4-[[[5-(1,3-benzothiazol-6-yl)-6-(4-fluoro-3-methylphenyl)pyridin-3-yl]amino]methyl]benzonitrile Chemical compound C1=C(F)C(C)=CC(C=2C(=CC(NCC=3C=CC(=CC=3)C#N)=CN=2)C=2C=C3SC=NC3=CC=2)=C1 VRRAVJXMIWYBDX-UHFFFAOYSA-N 0.000 claims description 2
QMHHVSJVMFJAJI-UHFFFAOYSA-N 4-[[[6-(4-fluoro-3-methylphenyl)-5-quinoxalin-6-ylpyridin-3-yl]amino]methyl]benzonitrile Chemical compound C1=C(F)C(C)=CC(C=2C(=CC(NCC=3C=CC(=CC=3)C#N)=CN=2)C=2C=C3N=CC=NC3=CC=2)=C1 QMHHVSJVMFJAJI-UHFFFAOYSA-N 0.000 claims description 2
GWUIIWBRDKUPTD-UHFFFAOYSA-N 4-amino-6-[2-[3-(dimethylsulfamoylamino)phenyl]pyridin-3-yl]quinazoline Chemical compound CN(C)S(=O)(=O)NC1=CC=CC(C=2C(=CC=CN=2)C=2C=C3C(N)=NC=NC3=CC=2)=C1 GWUIIWBRDKUPTD-UHFFFAOYSA-N 0.000 claims description 2
HSVNSFHWHFYKFI-UHFFFAOYSA-N 5-(1,3-benzothiazol-6-yl)-6-(3-cyclopropylphenyl)pyridin-2-amine Chemical compound N=1C(N)=CC=C(C=2C=C3SC=NC3=CC=2)C=1C(C=1)=CC=CC=1C1CC1 HSVNSFHWHFYKFI-UHFFFAOYSA-N 0.000 claims description 2
NWKKFWQYCBGHRJ-UHFFFAOYSA-N 5-(1,3-benzothiazol-6-yl)-6-(3-cyclopropylphenyl)pyridin-3-amine Chemical compound C=1C=C2N=CSC2=CC=1C1=CC(N)=CN=C1C(C=1)=CC=CC=1C1CC1 NWKKFWQYCBGHRJ-UHFFFAOYSA-N 0.000 claims description 2
FTLKSXAYUKBTMQ-UHFFFAOYSA-N 5-(1,3-benzothiazol-6-yl)-6-(3-methylphenyl)pyridin-2-amine Chemical compound CC1=CC=CC(C=2C(=CC=C(N)N=2)C=2C=C3SC=NC3=CC=2)=C1 FTLKSXAYUKBTMQ-UHFFFAOYSA-N 0.000 claims description 2
OFJFSADCLKHCRW-UHFFFAOYSA-N 5-(1,3-benzothiazol-6-yl)-6-(3-methylphenyl)pyridin-3-amine Chemical compound CC1=CC=CC(C=2C(=CC(N)=CN=2)C=2C=C3SC=NC3=CC=2)=C1 OFJFSADCLKHCRW-UHFFFAOYSA-N 0.000 claims description 2
LNJIIAVYIPWHBD-UHFFFAOYSA-N 5-(1,3-benzothiazol-6-yl)-6-(4-fluoro-3-methylphenyl)-n-(1,3-thiazol-2-ylmethyl)pyridin-3-amine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC(NCC=3SC=CN=3)=CN=2)C=2C=C3SC=NC3=CC=2)=C1 LNJIIAVYIPWHBD-UHFFFAOYSA-N 0.000 claims description 2
PCUDSUIBIFWPIV-UHFFFAOYSA-N 5-(1,3-benzothiazol-6-yl)-6-(4-fluoro-3-methylphenyl)-n-(1,3-thiazol-5-ylmethyl)pyridin-3-amine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC(NCC=3SC=NC=3)=CN=2)C=2C=C3SC=NC3=CC=2)=C1 PCUDSUIBIFWPIV-UHFFFAOYSA-N 0.000 claims description 2
MZCFYQUMKVLWFO-UHFFFAOYSA-N 5-(1,3-benzothiazol-6-yl)-6-(4-fluoro-3-methylphenyl)-n-(1h-imidazol-5-ylmethyl)pyridin-3-amine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC(NCC=3NC=NC=3)=CN=2)C=2C=C3SC=NC3=CC=2)=C1 MZCFYQUMKVLWFO-UHFFFAOYSA-N 0.000 claims description 2
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DDHVLUOQKGRPKT-UHFFFAOYSA-N 5-(1,3-benzothiazol-6-yl)-6-(4-fluoro-3-methylphenyl)-n-[(3-methylimidazo[4,5-b]pyridin-6-yl)methyl]pyridin-3-amine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC(NCC=3C=C4N=CN(C)C4=NC=3)=CN=2)C=2C=C3SC=NC3=CC=2)=C1 DDHVLUOQKGRPKT-UHFFFAOYSA-N 0.000 claims description 2
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QFWOAKPUXDIKOU-UHFFFAOYSA-N 5-(1,3-benzothiazol-6-yl)-6-(4-fluoro-3-methylphenyl)-n-[(4-morpholin-4-ylphenyl)methyl]pyridin-3-amine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC(NCC=3C=CC(=CC=3)N3CCOCC3)=CN=2)C=2C=C3SC=NC3=CC=2)=C1 QFWOAKPUXDIKOU-UHFFFAOYSA-N 0.000 claims description 2
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XEDNWCPVPYCEHW-UHFFFAOYSA-N 5-(1,3-benzothiazol-6-yl)-6-(4-fluoro-3-methylphenyl)-n-[(6-methoxypyridin-3-yl)methyl]pyridin-3-amine Chemical compound C1=NC(OC)=CC=C1CNC(C=C1C=2C=C3SC=NC3=CC=2)=CN=C1C1=CC=C(F)C(C)=C1 XEDNWCPVPYCEHW-UHFFFAOYSA-N 0.000 claims description 2
FYIKTPFASPMWAU-UHFFFAOYSA-N 5-(1,3-benzothiazol-6-yl)-6-(4-fluoro-3-methylphenyl)-n-[(6-methylpyridin-3-yl)methyl]pyridin-3-amine Chemical compound C1=NC(C)=CC=C1CNC(C=C1C=2C=C3SC=NC3=CC=2)=CN=C1C1=CC=C(F)C(C)=C1 FYIKTPFASPMWAU-UHFFFAOYSA-N 0.000 claims description 2
RGCSPWCZNPSJRX-UHFFFAOYSA-N 5-(1,3-benzothiazol-6-yl)-6-(4-fluoro-3-methylphenyl)-n-[(6-pyridin-3-ylpyridin-3-yl)methyl]pyridin-3-amine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC(NCC=3C=NC(=CC=3)C=3C=NC=CC=3)=CN=2)C=2C=C3SC=NC3=CC=2)=C1 RGCSPWCZNPSJRX-UHFFFAOYSA-N 0.000 claims description 2
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CEJHLQIEERKIEH-UHFFFAOYSA-N 5-(1,3-benzothiazol-6-yl)-6-(4-fluoro-3-methylphenyl)pyridin-3-amine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC(N)=CN=2)C=2C=C3SC=NC3=CC=2)=C1 CEJHLQIEERKIEH-UHFFFAOYSA-N 0.000 claims description 2
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CMEVISYCWFJHNX-UHFFFAOYSA-N 5-(1h-indazol-5-yl)-6-(3-propan-2-ylphenyl)pyridin-3-amine Chemical compound CC(C)C1=CC=CC(C=2C(=CC(N)=CN=2)C=2C=C3C=NNC3=CC=2)=C1 CMEVISYCWFJHNX-UHFFFAOYSA-N 0.000 claims description 2
SHBONCAQTOMZQC-UHFFFAOYSA-N 5-(3-pyridin-4-ylpyridin-2-yl)-2,3-dihydro-1h-inden-1-ol Chemical compound C=1C=C2C(O)CCC2=CC=1C1=NC=CC=C1C1=CC=NC=C1 SHBONCAQTOMZQC-UHFFFAOYSA-N 0.000 claims description 2
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WAMPOWFLQJVHGY-UHFFFAOYSA-N 5-[2-(3-chloro-4-fluorophenyl)pyridin-3-yl]-1h-indazol-3-amine Chemical compound C1=C2C(N)=NNC2=CC=C1C1=CC=CN=C1C1=CC=C(F)C(Cl)=C1 WAMPOWFLQJVHGY-UHFFFAOYSA-N 0.000 claims description 2
BVVCNVPDCHOVIY-UHFFFAOYSA-N 5-[2-(3-chloro-4-fluorophenyl)pyridin-3-yl]-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound N1=C2SC(N)=NC2=CC=C1C1=CC=CN=C1C1=CC=C(F)C(Cl)=C1 BVVCNVPDCHOVIY-UHFFFAOYSA-N 0.000 claims description 2
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IELHJZBNASAQBH-UHFFFAOYSA-N 5-[2-(3-cyclopentylphenyl)pyridin-3-yl]-1h-pyrazolo[3,4-b]pyridine Chemical compound C1CCCC1C1=CC=CC(C=2C(=CC=CN=2)C=2C=C3C=NNC3=NC=2)=C1 IELHJZBNASAQBH-UHFFFAOYSA-N 0.000 claims description 2
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WLCWUXJLJFRPPH-UHFFFAOYSA-N 5-[2-(3-cyclopropylphenyl)pyridin-3-yl]-1-methylbenzimidazole Chemical compound C=1C=C2N(C)C=NC2=CC=1C1=CC=CN=C1C(C=1)=CC=CC=1C1CC1 WLCWUXJLJFRPPH-UHFFFAOYSA-N 0.000 claims description 2
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AWAOBTKFNDVTEW-UHFFFAOYSA-N 5-[2-(3-cyclopropylphenyl)pyridin-3-yl]pyrazolo[1,5-a]pyrimidine Chemical compound C1CC1C1=CC=CC(C=2C(=CC=CN=2)C2=NC3=CC=NN3C=C2)=C1 AWAOBTKFNDVTEW-UHFFFAOYSA-N 0.000 claims description 2
RJPUDGJCJHXNMF-UHFFFAOYSA-N 5-[2-(3-ethylphenyl)pyridin-3-yl]-1h-indazole Chemical compound CCC1=CC=CC(C=2C(=CC=CN=2)C=2C=C3C=NNC3=CC=2)=C1 RJPUDGJCJHXNMF-UHFFFAOYSA-N 0.000 claims description 2
HDCKDTDPIGTHCF-UHFFFAOYSA-N 5-[2-(3-ethylphenyl)pyridin-3-yl]-1h-pyrazolo[3,4-b]pyridine Chemical compound CCC1=CC=CC(C=2C(=CC=CN=2)C=2C=C3C=NNC3=NC=2)=C1 HDCKDTDPIGTHCF-UHFFFAOYSA-N 0.000 claims description 2
YJAXVVWZXIPEOZ-UHFFFAOYSA-N 5-[2-(3-fluoro-4-methylphenyl)pyridin-3-yl]-1h-indazole Chemical compound C1=C(F)C(C)=CC=C1C1=NC=CC=C1C1=CC=C(NN=C2)C2=C1 YJAXVVWZXIPEOZ-UHFFFAOYSA-N 0.000 claims description 2
CPFOKDRNNBEREQ-UHFFFAOYSA-N 5-[2-(3-fluoro-4-methylphenyl)pyridin-3-yl]-1h-pyrazolo[3,4-b]pyridine Chemical compound C1=C(F)C(C)=CC=C1C1=NC=CC=C1C1=CN=C(NN=C2)C2=C1 CPFOKDRNNBEREQ-UHFFFAOYSA-N 0.000 claims description 2
QRXXBDMXTIIJPU-UHFFFAOYSA-N 5-[2-(3-fluorophenyl)pyridin-3-yl]-1h-indazole Chemical compound FC1=CC=CC(C=2C(=CC=CN=2)C=2C=C3C=NNC3=CC=2)=C1 QRXXBDMXTIIJPU-UHFFFAOYSA-N 0.000 claims description 2
MAPHUWPBQHIFMC-UHFFFAOYSA-N 5-[2-(3-methoxy-4-methylphenyl)pyridin-3-yl]-1h-indazole Chemical compound C1=C(C)C(OC)=CC(C=2C(=CC=CN=2)C=2C=C3C=NNC3=CC=2)=C1 MAPHUWPBQHIFMC-UHFFFAOYSA-N 0.000 claims description 2
VGEWSRLGENQQNB-UHFFFAOYSA-N 5-[2-(3-methoxy-4-phenylmethoxyphenyl)pyridin-3-yl]-1h-indazole Chemical compound COC1=CC(C=2C(=CC=CN=2)C=2C=C3C=NNC3=CC=2)=CC=C1OCC1=CC=CC=C1 VGEWSRLGENQQNB-UHFFFAOYSA-N 0.000 claims description 2
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HRCPBNILNOFCII-UHFFFAOYSA-N 5-[2-(3-methoxyphenyl)pyridin-3-yl]-1h-pyrazolo[3,4-b]pyridine Chemical compound COC1=CC=CC(C=2C(=CC=CN=2)C=2C=C3C=NNC3=NC=2)=C1 HRCPBNILNOFCII-UHFFFAOYSA-N 0.000 claims description 2
OISXVAXXDRJPQO-UHFFFAOYSA-N 5-[2-(3-methylphenyl)pyridin-3-yl]-1,3-benzothiazole Chemical compound CC1=CC=CC(C=2C(=CC=CN=2)C=2C=C3N=CSC3=CC=2)=C1 OISXVAXXDRJPQO-UHFFFAOYSA-N 0.000 claims description 2
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VVSSWAZEWVGFSQ-UHFFFAOYSA-N 5-[2-(3-methylphenyl)pyridin-3-yl]-1h-pyrazolo[3,4-b]pyridine Chemical compound CC1=CC=CC(C=2C(=CC=CN=2)C=2C=C3C=NNC3=NC=2)=C1 VVSSWAZEWVGFSQ-UHFFFAOYSA-N 0.000 claims description 2
IPJPKXYHTMTGGK-UHFFFAOYSA-N 5-[2-(3-methylphenyl)pyridin-3-yl]-[1,3]thiazolo[5,4-b]pyridine Chemical compound CC1=CC=CC(C=2C(=CC=CN=2)C=2N=C3SC=NC3=CC=2)=C1 IPJPKXYHTMTGGK-UHFFFAOYSA-N 0.000 claims description 2
FLORZVQLNDNLDJ-UHFFFAOYSA-N 5-[2-(3-methylphenyl)pyridin-3-yl]pyrazolo[1,5-a]pyridine Chemical compound CC1=CC=CC(C=2C(=CC=CN=2)C2=CC3=CC=NN3C=C2)=C1 FLORZVQLNDNLDJ-UHFFFAOYSA-N 0.000 claims description 2
YZRYUBYJTSIJJA-UHFFFAOYSA-N 5-[2-(3-methylphenyl)pyridin-3-yl]pyrazolo[1,5-a]pyrimidine Chemical compound CC1=CC=CC(C=2C(=CC=CN=2)C2=NC3=CC=NN3C=C2)=C1 YZRYUBYJTSIJJA-UHFFFAOYSA-N 0.000 claims description 2
KCEQPCYNUZKCRB-UHFFFAOYSA-N 5-[2-(3-propan-2-ylphenyl)pyridin-3-yl]-1h-pyrazolo[3,4-b]pyridine Chemical compound CC(C)C1=CC=CC(C=2C(=CC=CN=2)C=2C=C3C=NNC3=NC=2)=C1 KCEQPCYNUZKCRB-UHFFFAOYSA-N 0.000 claims description 2
QXPJXEDTOBUHJW-UHFFFAOYSA-N 5-[2-(3-tert-butylphenyl)pyridin-3-yl]-1h-pyrazolo[3,4-b]pyridine Chemical compound CC(C)(C)C1=CC=CC(C=2C(=CC=CN=2)C=2C=C3C=NNC3=NC=2)=C1 QXPJXEDTOBUHJW-UHFFFAOYSA-N 0.000 claims description 2
HZXRJGGXRVQPQK-UHFFFAOYSA-N 5-[2-(4-cyclopropylphenyl)-6-methylpyridin-3-yl]-1h-indazole Chemical compound N=1C(C)=CC=C(C=2C=C3C=NNC3=CC=2)C=1C(C=C1)=CC=C1C1CC1 HZXRJGGXRVQPQK-UHFFFAOYSA-N 0.000 claims description 2
YUQKBGQHSGKGQR-UHFFFAOYSA-N 5-[2-(4-fluoro-3-methoxyphenyl)pyridin-3-yl]-1h-indazole Chemical compound C1=C(F)C(OC)=CC(C=2C(=CC=CN=2)C=2C=C3C=NNC3=CC=2)=C1 YUQKBGQHSGKGQR-UHFFFAOYSA-N 0.000 claims description 2
CBYCEFHMWIKSEY-UHFFFAOYSA-N 5-[2-(4-fluoro-3-methylphenyl)-5-(propan-2-ylcarbamoylamino)pyridin-3-yl]-n-propan-2-ylindazole-1-carboxamide Chemical compound C=1C=C2N(C(=O)NC(C)C)N=CC2=CC=1C1=CC(NC(=O)NC(C)C)=CN=C1C1=CC=C(F)C(C)=C1 CBYCEFHMWIKSEY-UHFFFAOYSA-N 0.000 claims description 2
HGHGIFUCVNWHIH-UHFFFAOYSA-N 5-[2-(4-fluoro-3-methylphenyl)-5-methoxypyridin-3-yl]-1h-indazole Chemical compound C=1C=C2NN=CC2=CC=1C1=CC(OC)=CN=C1C1=CC=C(F)C(C)=C1 HGHGIFUCVNWHIH-UHFFFAOYSA-N 0.000 claims description 2
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VCADAIDXJMUHOV-UHFFFAOYSA-N 5-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-1,2-benzoxazol-3-amine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3C(N)=NOC3=CC=2)=C1 VCADAIDXJMUHOV-UHFFFAOYSA-N 0.000 claims description 2
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GEUCMRYNZRHKAU-UHFFFAOYSA-N 5-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-3-methyl-2h-indazole Chemical compound C1=C2C(C)=NNC2=CC=C1C1=CC=CN=C1C1=CC=C(F)C(C)=C1 GEUCMRYNZRHKAU-UHFFFAOYSA-N 0.000 claims description 2
XIFCWSTUFVXFPJ-UHFFFAOYSA-N 5-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-6-methyl-1h-indazole Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C(=CC=3NN=CC=3C=2)C)=C1 XIFCWSTUFVXFPJ-UHFFFAOYSA-N 0.000 claims description 2
QTOCAPWWXIZWSX-UHFFFAOYSA-N 5-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-7-methyl-1h-indazole Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3C=NNC3=C(C)C=2)=C1 QTOCAPWWXIZWSX-UHFFFAOYSA-N 0.000 claims description 2
CSNHPIACPJAUOL-UHFFFAOYSA-N 5-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-[1,3]thiazolo[5,4-b]pyridine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2N=C3SC=NC3=CC=2)=C1 CSNHPIACPJAUOL-UHFFFAOYSA-N 0.000 claims description 2
WBJGONFBKOGFRA-UHFFFAOYSA-N 5-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-n,n-dimethyl-1h-indazole-7-carboxamide Chemical compound C=1C=2C=NNC=2C(C(=O)N(C)C)=CC=1C1=CC=CN=C1C1=CC=C(F)C(C)=C1 WBJGONFBKOGFRA-UHFFFAOYSA-N 0.000 claims description 2
ZNBVNDJRXGLZHW-UHFFFAOYSA-N 5-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-n-(1,2,2,6,6-pentamethylpiperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide Chemical compound C1C(C)(C)N(C)C(C)(C)CC1NC(=O)C1=C2C=C(C=3C(=NC=CC=3)C=3C=C(C)C(F)=CC=3)C=CN2N=C1 ZNBVNDJRXGLZHW-UHFFFAOYSA-N 0.000 claims description 2
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CLYHCVGFRDNTGR-UHFFFAOYSA-N 5-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-n-(2-hydroxyethyl)pyrazolo[1,5-a]pyridine-3-carboxamide Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C2=CC3=C(C(=O)NCCO)C=NN3C=C2)=C1 CLYHCVGFRDNTGR-UHFFFAOYSA-N 0.000 claims description 2
WJCYNDHKYYBRFD-UHFFFAOYSA-N 5-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-n-(2-pyrrolidin-1-ylethyl)indazole-1-carboxamide Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3C=NN(C3=CC=2)C(=O)NCCN2CCCC2)=C1 WJCYNDHKYYBRFD-UHFFFAOYSA-N 0.000 claims description 2
NJWSVDPDURHBCW-UHFFFAOYSA-N 5-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-n-(3,4,5-trimethoxyphenyl)indazole-1-carboxamide Chemical compound COC1=C(OC)C(OC)=CC(NC(=O)N2C3=CC=C(C=C3C=N2)C=2C(=NC=CC=2)C=2C=C(C)C(F)=CC=2)=C1 NJWSVDPDURHBCW-UHFFFAOYSA-N 0.000 claims description 2
BUXFBKWXMNTJNK-UHFFFAOYSA-N 5-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-n-(3-hydroxypropyl)pyrazolo[1,5-a]pyridine-3-carboxamide Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C2=CC3=C(C(=O)NCCCO)C=NN3C=C2)=C1 BUXFBKWXMNTJNK-UHFFFAOYSA-N 0.000 claims description 2
BLVNVOZCKMJHEP-UHFFFAOYSA-N 5-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-n-(3-morpholin-4-ylpropyl)indazole-1-carboxamide Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3C=NN(C3=CC=2)C(=O)NCCCN2CCOCC2)=C1 BLVNVOZCKMJHEP-UHFFFAOYSA-N 0.000 claims description 2
XRDBBJHKUPUMTG-UHFFFAOYSA-N 5-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-n-(3-piperidin-1-ylpropyl)indazole-1-carboxamide Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3C=NN(C3=CC=2)C(=O)NCCCN2CCCCC2)=C1 XRDBBJHKUPUMTG-UHFFFAOYSA-N 0.000 claims description 2
SZHKLRYDQQXCKI-UHFFFAOYSA-N 5-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-n-[(1-methylpiperidin-4-yl)methyl]pyrazolo[1,5-a]pyridine-3-carboxamide Chemical compound C1CN(C)CCC1CNC(=O)C1=C2C=C(C=3C(=NC=CC=3)C=3C=C(C)C(F)=CC=3)C=CN2N=C1 SZHKLRYDQQXCKI-UHFFFAOYSA-N 0.000 claims description 2
DRUSASRCIOXOMT-UHFFFAOYSA-N 5-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-n-[3-(2-oxopyrrolidin-1-yl)propyl]indazole-1-carboxamide Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3C=NN(C3=CC=2)C(=O)NCCCN2C(CCC2)=O)=C1 DRUSASRCIOXOMT-UHFFFAOYSA-N 0.000 claims description 2
GJMSVQPMLZFJPC-UHFFFAOYSA-N 5-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]pyrazolo[1,5-a]pyridine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C2=CC3=CC=NN3C=C2)=C1 GJMSVQPMLZFJPC-UHFFFAOYSA-N 0.000 claims description 2
DXNGGQJLBREIJS-UHFFFAOYSA-N 5-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]pyrazolo[1,5-a]pyridine-3-carboxylic acid Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C2=CC3=C(C(O)=O)C=NN3C=C2)=C1 DXNGGQJLBREIJS-UHFFFAOYSA-N 0.000 claims description 2
UUNOIFCYEWHACH-UHFFFAOYSA-N 5-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]pyrazolo[1,5-a]pyrimidine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C2=NC3=CC=NN3C=C2)=C1 UUNOIFCYEWHACH-UHFFFAOYSA-N 0.000 claims description 2
TXMFPRJVHWGNFO-UHFFFAOYSA-N 5-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]pyrazolo[1,5-a]pyrimidine-3-carbonitrile Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C2=NC3=C(C#N)C=NN3C=C2)=C1 TXMFPRJVHWGNFO-UHFFFAOYSA-N 0.000 claims description 2
SQWHMUGQWBNIHD-UHFFFAOYSA-N 5-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]pyridin-2-amine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=NC(N)=CC=2)=C1 SQWHMUGQWBNIHD-UHFFFAOYSA-N 0.000 claims description 2
JDPPWOXTDSKNRA-UHFFFAOYSA-N 5-[2-(4-fluorophenyl)pyridin-3-yl]-1h-indazole Chemical compound C1=CC(F)=CC=C1C1=NC=CC=C1C1=CC=C(NN=C2)C2=C1 JDPPWOXTDSKNRA-UHFFFAOYSA-N 0.000 claims description 2
IHLAEFKJTPXBHK-UHFFFAOYSA-N 5-[2-(4-fluorophenyl)pyridin-3-yl]-1h-pyrazolo[3,4-b]pyridine Chemical compound C1=CC(F)=CC=C1C1=NC=CC=C1C1=CN=C(NN=C2)C2=C1 IHLAEFKJTPXBHK-UHFFFAOYSA-N 0.000 claims description 2
SOIFOYIVNZBGLV-UHFFFAOYSA-N 5-[2-(4-methoxyphenyl)pyridin-3-yl]-1h-indazole Chemical compound C1=CC(OC)=CC=C1C1=NC=CC=C1C1=CC=C(NN=C2)C2=C1 SOIFOYIVNZBGLV-UHFFFAOYSA-N 0.000 claims description 2
AJNOWQMKRMCWCU-UHFFFAOYSA-N 5-[2-(4-methylphenyl)pyridin-3-yl]-1h-indazole Chemical compound C1=CC(C)=CC=C1C1=NC=CC=C1C1=CC=C(NN=C2)C2=C1 AJNOWQMKRMCWCU-UHFFFAOYSA-N 0.000 claims description 2
SIEVRRLBNIETMC-UHFFFAOYSA-N 5-[2-(5-chloro-2,4-difluorophenyl)pyridin-3-yl]pyrazolo[1,5-a]pyridine Chemical compound C1=C(Cl)C(F)=CC(F)=C1C1=NC=CC=C1C1=CC2=CC=NN2C=C1 SIEVRRLBNIETMC-UHFFFAOYSA-N 0.000 claims description 2
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DOVZBKSFVJUTOI-UHFFFAOYSA-N 5-[2-(5-chloro-2-fluorophenyl)pyridin-3-yl]pyrazolo[1,5-a]pyridine Chemical compound FC1=CC=C(Cl)C=C1C1=NC=CC=C1C1=CC2=CC=NN2C=C1 DOVZBKSFVJUTOI-UHFFFAOYSA-N 0.000 claims description 2
CIOATLIUKUJXSN-UHFFFAOYSA-N 5-[2-(5-chloro-2-fluorophenyl)pyridin-3-yl]pyrazolo[1,5-a]pyrimidine Chemical compound FC1=CC=C(Cl)C=C1C1=NC=CC=C1C1=NC2=CC=NN2C=C1 CIOATLIUKUJXSN-UHFFFAOYSA-N 0.000 claims description 2
AZFAJDPMNWNYRF-UHFFFAOYSA-N 5-[2-(6-methylpyridin-2-yl)pyridin-3-yl]-1h-indazole Chemical compound CC1=CC=CC(C=2C(=CC=CN=2)C=2C=C3C=NNC3=CC=2)=N1 AZFAJDPMNWNYRF-UHFFFAOYSA-N 0.000 claims description 2
MUOJTWKUGJAOLX-UHFFFAOYSA-N 5-[2-[3-(cyclopenten-1-yl)phenyl]pyridin-3-yl]-1h-pyrazolo[3,4-b]pyridine Chemical compound C1CCC=C1C1=CC=CC(C=2C(=CC=CN=2)C=2C=C3C=NNC3=NC=2)=C1 MUOJTWKUGJAOLX-UHFFFAOYSA-N 0.000 claims description 2
JSOISJBGNUDJTP-UHFFFAOYSA-N 5-[2-[3-(difluoromethoxy)phenyl]pyridin-3-yl]pyrazolo[1,5-a]pyrimidine Chemical compound FC(F)OC1=CC=CC(C=2C(=CC=CN=2)C2=NC3=CC=NN3C=C2)=C1 JSOISJBGNUDJTP-UHFFFAOYSA-N 0.000 claims description 2
YZRYUBYJTSIJJA-FIBGUPNXSA-N 5-[2-[3-(trideuteriomethyl)phenyl]pyridin-3-yl]pyrazolo[1,5-a]pyrimidine Chemical compound [2H]C([2H])([2H])C1=CC=CC(C=2C(=CC=CN=2)C2=NC3=CC=NN3C=C2)=C1 YZRYUBYJTSIJJA-FIBGUPNXSA-N 0.000 claims description 2
GMJMUNRPEIJHRB-UHFFFAOYSA-N 5-[2-[3-(trifluoromethyl)phenyl]pyridin-3-yl]-1h-indazole Chemical compound FC(F)(F)C1=CC=CC(C=2C(=CC=CN=2)C=2C=C3C=NNC3=CC=2)=C1 GMJMUNRPEIJHRB-UHFFFAOYSA-N 0.000 claims description 2
XJTDEHVRYRVZQC-UHFFFAOYSA-N 5-[2-[3-(trifluoromethyl)phenyl]pyridin-3-yl]-1h-pyrazolo[3,4-b]pyridine Chemical compound FC(F)(F)C1=CC=CC(C=2C(=CC=CN=2)C=2C=C3C=NNC3=NC=2)=C1 XJTDEHVRYRVZQC-UHFFFAOYSA-N 0.000 claims description 2
FZPTZHPTWGPCBY-UHFFFAOYSA-N 5-[2-[3-(trifluoromethyl)phenyl]pyridin-3-yl]pyrazolo[1,5-a]pyrimidine Chemical compound FC(F)(F)C1=CC=CC(C=2C(=CC=CN=2)C2=NC3=CC=NN3C=C2)=C1 FZPTZHPTWGPCBY-UHFFFAOYSA-N 0.000 claims description 2
MCSKKTVQPNOEPM-UHFFFAOYSA-N 5-[2-[4-(trifluoromethyl)phenyl]pyridin-3-yl]-1h-indazole Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=NC=CC=C1C1=CC=C(NN=C2)C2=C1 MCSKKTVQPNOEPM-UHFFFAOYSA-N 0.000 claims description 2
ILXSWDZKDBAIAL-UHFFFAOYSA-N 5-[2-[4-fluoro-3-(trifluoromethyl)phenyl]pyridin-3-yl]-1h-indazole Chemical compound C1=C(C(F)(F)F)C(F)=CC=C1C1=NC=CC=C1C1=CC=C(NN=C2)C2=C1 ILXSWDZKDBAIAL-UHFFFAOYSA-N 0.000 claims description 2
QOZPQAJXXYQXAL-UHFFFAOYSA-N 5-[2-[6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]quinazolin-4-yl]oxyethyl]-4-methyl-1,3-thiazole Chemical compound N1=CSC(CCOC=2C3=CC(=CC=C3N=CN=2)C=2C(=NC=CC=2)C=2C=C(C)C(F)=CC=2)=C1C QOZPQAJXXYQXAL-UHFFFAOYSA-N 0.000 claims description 2
QJTSVGFPVNGSGY-UHFFFAOYSA-N 5-[3-(4-aminoquinazolin-6-yl)pyridin-2-yl]-2,3-dihydroinden-1-one Chemical compound C1=C2C(=O)CCC2=CC(C2=NC=CC=C2C2=CC=C3N=CN=C(C3=C2)N)=C1 QJTSVGFPVNGSGY-UHFFFAOYSA-N 0.000 claims description 2
GHODCCKTVWBBMO-UHFFFAOYSA-N 5-[3-(4-aminoquinazolin-6-yl)pyridin-2-yl]-2-fluorobenzonitrile Chemical compound C1=C2C(N)=NC=NC2=CC=C1C1=CC=CN=C1C1=CC=C(F)C(C#N)=C1 GHODCCKTVWBBMO-UHFFFAOYSA-N 0.000 claims description 2
ANJQAQFYPXOUAC-UHFFFAOYSA-N 5-[3-(6-methylpyridin-2-yl)pyridin-2-yl]-1,3-dihydrobenzimidazol-2-one Chemical compound CC1=CC=CC(C=2C(=NC=CC=2)C=2C=C3NC(=O)NC3=CC=2)=N1 ANJQAQFYPXOUAC-UHFFFAOYSA-N 0.000 claims description 2
FMTQJEQESBTCOE-UHFFFAOYSA-N 5-[3-(6-methylpyridin-2-yl)pyridin-2-yl]-1h-indazole Chemical compound CC1=CC=CC(C=2C(=NC=CC=2)C=2C=C3C=NNC3=CC=2)=N1 FMTQJEQESBTCOE-UHFFFAOYSA-N 0.000 claims description 2
RMIKAKOEGPPRSS-UHFFFAOYSA-N 5-[5-chloro-2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-1h-indazole Chemical compound C1=C(F)C(C)=CC(C=2C(=CC(Cl)=CN=2)C=2C=C3C=NNC3=CC=2)=C1 RMIKAKOEGPPRSS-UHFFFAOYSA-N 0.000 claims description 2
VPAOPHOXRAOUQD-UHFFFAOYSA-N 5-[5-ethoxy-2-(2-fluorophenyl)pyridin-3-yl]-1h-indazole Chemical compound C=1C=C2NN=CC2=CC=1C1=CC(OCC)=CN=C1C1=CC=CC=C1F VPAOPHOXRAOUQD-UHFFFAOYSA-N 0.000 claims description 2
IBYBSACKXSPFFN-UHFFFAOYSA-N 5-[5-ethoxy-2-(3-fluorophenyl)pyridin-3-yl]-1h-indazole Chemical compound C=1C=C2NN=CC2=CC=1C1=CC(OCC)=CN=C1C1=CC=CC(F)=C1 IBYBSACKXSPFFN-UHFFFAOYSA-N 0.000 claims description 2
NXKCJPQGGYKBLV-UHFFFAOYSA-N 5-[5-ethoxy-2-(3-methylphenyl)pyridin-3-yl]-1h-indazole Chemical compound C=1C=C2NN=CC2=CC=1C1=CC(OCC)=CN=C1C1=CC=CC(C)=C1 NXKCJPQGGYKBLV-UHFFFAOYSA-N 0.000 claims description 2
FYFFCPRLMLJUKT-UHFFFAOYSA-N 5-[5-ethoxy-2-(4-fluoro-2-propan-2-yloxyphenyl)pyridin-3-yl]-1h-indazole Chemical compound C=1C=C2NN=CC2=CC=1C1=CC(OCC)=CN=C1C1=CC=C(F)C=C1OC(C)C FYFFCPRLMLJUKT-UHFFFAOYSA-N 0.000 claims description 2
XOYJYKHQAVSOHJ-UHFFFAOYSA-N 5-[5-ethoxy-2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-1h-indazole Chemical compound C=1C=C2NN=CC2=CC=1C1=CC(OCC)=CN=C1C1=CC=C(F)C(C)=C1 XOYJYKHQAVSOHJ-UHFFFAOYSA-N 0.000 claims description 2
BRODUGYEINOMIY-UHFFFAOYSA-N 5-[5-ethoxy-2-(4-fluorophenyl)pyridin-3-yl]-1h-indazole Chemical compound C=1C=C2NN=CC2=CC=1C1=CC(OCC)=CN=C1C1=CC=C(F)C=C1 BRODUGYEINOMIY-UHFFFAOYSA-N 0.000 claims description 2
RXUMGBUQNAPJNJ-UHFFFAOYSA-N 5-[5-fluoro-2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-1h-indazole Chemical compound C1=C(F)C(C)=CC(C=2C(=CC(F)=CN=2)C=2C=C3C=NNC3=CC=2)=C1 RXUMGBUQNAPJNJ-UHFFFAOYSA-N 0.000 claims description 2
QUDJBEJJICTANA-UHFFFAOYSA-N 5-[6-methyl-2-(3-propan-2-ylphenyl)pyridin-3-yl]-1h-indazole Chemical compound CC(C)C1=CC=CC(C=2C(=CC=C(C)N=2)C=2C=C3C=NNC3=CC=2)=C1 QUDJBEJJICTANA-UHFFFAOYSA-N 0.000 claims description 2
XNIVJEDUJDGYGM-UHFFFAOYSA-N 5-[[[5-(1,3-benzothiazol-6-yl)-6-(4-fluoro-3-methylphenyl)pyridin-3-yl]amino]methyl]-2,3-dimethoxyphenol Chemical compound OC1=C(OC)C(OC)=CC(CNC=2C=C(C(C=3C=C(C)C(F)=CC=3)=NC=2)C=2C=C3SC=NC3=CC=2)=C1 XNIVJEDUJDGYGM-UHFFFAOYSA-N 0.000 claims description 2
FHLHDNGZAGSFDY-UHFFFAOYSA-N 6-(2-phenylpyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C=1N2N=CN=C2C=CC=1C1=CC=CN=C1C1=CC=CC=C1 FHLHDNGZAGSFDY-UHFFFAOYSA-N 0.000 claims description 2
STPJPKFGOHJYJL-UHFFFAOYSA-N 6-(3-cyclopropylphenyl)-5-(1h-indazol-5-yl)pyridin-2-amine Chemical compound N=1C(N)=CC=C(C=2C=C3C=NNC3=CC=2)C=1C(C=1)=CC=CC=1C1CC1 STPJPKFGOHJYJL-UHFFFAOYSA-N 0.000 claims description 2
MVDHUXRNHPUUCX-UHFFFAOYSA-N 6-(3-cyclopropylphenyl)-5-(1h-indazol-5-yl)pyridin-3-amine Chemical compound C=1C=C2NN=CC2=CC=1C1=CC(N)=CN=C1C(C=1)=CC=CC=1C1CC1 MVDHUXRNHPUUCX-UHFFFAOYSA-N 0.000 claims description 2
AJNHGBKRDVQCEC-UHFFFAOYSA-N 6-(4-fluoro-3-methylphenyl)-1-methyl-7-quinolin-6-yl-2,3-dihydropyrido[2,3-b][1,4]oxazine Chemical compound C=1C=C2N=CC=CC2=CC=1C=1C=C2N(C)CCOC2=NC=1C1=CC=C(F)C(C)=C1 AJNHGBKRDVQCEC-UHFFFAOYSA-N 0.000 claims description 2
VPKORKSDDHVFPV-UHFFFAOYSA-N 6-(4-fluoro-3-methylphenyl)-5-(1h-indazol-5-yl)pyridin-2-amine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=C(N)N=2)C=2C=C3C=NNC3=CC=2)=C1 VPKORKSDDHVFPV-UHFFFAOYSA-N 0.000 claims description 2
VSDWPOSVKXLQCT-UHFFFAOYSA-N 6-(4-fluoro-3-methylphenyl)-5-(1h-indazol-5-yl)pyridin-3-amine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC(N)=CN=2)C=2C=C3C=NNC3=CC=2)=C1 VSDWPOSVKXLQCT-UHFFFAOYSA-N 0.000 claims description 2
CZWFPDLAKBFMFG-UHFFFAOYSA-N 6-(4-fluoro-3-methylphenyl)-5-quinoxalin-6-ylpyridin-3-amine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC(N)=CN=2)C=2C=C3N=CC=NC3=CC=2)=C1 CZWFPDLAKBFMFG-UHFFFAOYSA-N 0.000 claims description 2
BBMQKPRHPSDKQY-UHFFFAOYSA-N 6-(4-fluoro-3-methylphenyl)-5-quinoxalin-6-ylpyridine-3-carboxylic acid Chemical compound C1=C(F)C(C)=CC(C=2C(=CC(=CN=2)C(O)=O)C=2C=C3N=CC=NC3=CC=2)=C1 BBMQKPRHPSDKQY-UHFFFAOYSA-N 0.000 claims description 2
OSGFBCQGPSIOOE-UHFFFAOYSA-N 6-(4-fluoro-3-methylphenyl)-7-(1h-indazol-5-yl)-1-methyl-2,3-dihydropyrido[2,3-b][1,4]oxazine Chemical compound C=1C=C2NN=CC2=CC=1C=1C=C2N(C)CCOC2=NC=1C1=CC=C(F)C(C)=C1 OSGFBCQGPSIOOE-UHFFFAOYSA-N 0.000 claims description 2
CADYXSFDUBZECG-UHFFFAOYSA-N 6-(4-fluoro-3-methylphenyl)-7-quinolin-6-yl-1h-pyrido[2,3-b][1,4]oxazin-2-one Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=3NC(=O)COC=3N=2)C=2C=C3C=CC=NC3=CC=2)=C1 CADYXSFDUBZECG-UHFFFAOYSA-N 0.000 claims description 2
QFLLWYHNYUPDCR-UHFFFAOYSA-N 6-(4-fluoro-3-methylphenyl)-n-(1-methylpiperidin-4-yl)-5-quinoxalin-6-ylpyridin-3-amine Chemical compound C1CN(C)CCC1NC(C=C1C=2C=C3N=CC=NC3=CC=2)=CN=C1C1=CC=C(F)C(C)=C1 QFLLWYHNYUPDCR-UHFFFAOYSA-N 0.000 claims description 2
KKOXTVPWPWQOCU-UHFFFAOYSA-N 6-(4-fluoro-3-methylphenyl)-n-(pyridin-2-ylmethyl)-5-quinoxalin-6-ylpyridin-3-amine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC(NCC=3N=CC=CC=3)=CN=2)C=2C=C3N=CC=NC3=CC=2)=C1 KKOXTVPWPWQOCU-UHFFFAOYSA-N 0.000 claims description 2
GETPIRFYIFXOOB-UHFFFAOYSA-N 6-(4-fluoro-3-methylphenyl)-n-(pyridin-3-ylmethyl)-5-quinoxalin-6-ylpyridin-3-amine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC(NCC=3C=NC=CC=3)=CN=2)C=2C=C3N=CC=NC3=CC=2)=C1 GETPIRFYIFXOOB-UHFFFAOYSA-N 0.000 claims description 2
CIXIHZUWHUFXDJ-UHFFFAOYSA-N 6-(4-fluoro-3-methylphenyl)-n-propan-2-yl-5-quinoxalin-6-ylpyridin-3-amine Chemical compound C=1C=C2N=CC=NC2=CC=1C1=CC(NC(C)C)=CN=C1C1=CC=C(F)C(C)=C1 CIXIHZUWHUFXDJ-UHFFFAOYSA-N 0.000 claims description 2
VQRWNJBKKGAQHJ-UHFFFAOYSA-N 6-[2-(1,3-benzodioxol-5-yl)pyridin-3-yl]-1,3-benzothiazole Chemical compound C1=C2N=CSC2=CC(C2=CC=CN=C2C2=CC=C3OCOC3=C2)=C1 VQRWNJBKKGAQHJ-UHFFFAOYSA-N 0.000 claims description 2
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SCABGDMDSKCMGX-UHFFFAOYSA-N 6-[2-(2,3-difluorophenyl)pyridin-3-yl]-1,3-benzothiazole Chemical compound FC1=CC=CC(C=2C(=CC=CN=2)C=2C=C3SC=NC3=CC=2)=C1F SCABGDMDSKCMGX-UHFFFAOYSA-N 0.000 claims description 2
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LFWNBNWEYPFAQD-UHFFFAOYSA-N 6-[2-(2,3-dihydro-1h-inden-5-yl)pyridin-3-yl]quinoxaline Chemical compound N1=CC=NC2=CC(C3=CC=CN=C3C3=CC=C4CCCC4=C3)=CC=C21 LFWNBNWEYPFAQD-UHFFFAOYSA-N 0.000 claims description 2
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FULMWGYVLRCWDM-UHFFFAOYSA-N 6-[2-(2,4,5-trifluorophenyl)pyridin-3-yl]pyrido[2,3-b]pyrazine Chemical compound C1=C(F)C(F)=CC(F)=C1C1=NC=CC=C1C1=CC=C(N=CC=N2)C2=N1 FULMWGYVLRCWDM-UHFFFAOYSA-N 0.000 claims description 2
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RTICXGBOHZESEF-UHFFFAOYSA-N 6-[2-(2,4-dichloro-5-fluorophenyl)pyridin-3-yl]quinazolin-4-amine Chemical compound C1=C2C(N)=NC=NC2=CC=C1C1=CC=CN=C1C1=CC(F)=C(Cl)C=C1Cl RTICXGBOHZESEF-UHFFFAOYSA-N 0.000 claims description 2
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NBNNBAWTDXCQSA-UHFFFAOYSA-N 6-[2-(2-chloro-5-fluorophenyl)pyridin-3-yl]quinazolin-4-amine Chemical compound C1=C2C(N)=NC=NC2=CC=C1C1=CC=CN=C1C1=CC(F)=CC=C1Cl NBNNBAWTDXCQSA-UHFFFAOYSA-N 0.000 claims description 2
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JPIRDOATFPGDQE-UHFFFAOYSA-N 6-[2-(2-fluoro-5-methoxyphenyl)pyridin-3-yl]quinazolin-4-amine Chemical compound COC1=CC=C(F)C(C=2C(=CC=CN=2)C=2C=C3C(N)=NC=NC3=CC=2)=C1 JPIRDOATFPGDQE-UHFFFAOYSA-N 0.000 claims description 2
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KPGGGZGPDFIIQY-UHFFFAOYSA-N 6-[2-(3-methylphenyl)pyridin-3-yl]-1-[3-(4-methylpiperazin-1-yl)propyl]benzimidazole Chemical compound C1CN(C)CCN1CCCN1C2=CC(C=3C(=NC=CC=3)C=3C=C(C)C=CC=3)=CC=C2N=C1 KPGGGZGPDFIIQY-UHFFFAOYSA-N 0.000 claims description 2
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DWQTWDAYKMAQBE-UHFFFAOYSA-N 6-[2-(3-methylphenyl)pyridin-3-yl]-3-pyrrolidin-1-ylimidazo[1,2-a]pyridine Chemical compound CC1=CC=CC(C=2C(=CC=CN=2)C2=CN3C(N4CCCC4)=CN=C3C=C2)=C1 DWQTWDAYKMAQBE-UHFFFAOYSA-N 0.000 claims description 2
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HZKDJUAQINODMC-UHFFFAOYSA-N 6-[2-(3-methylphenyl)pyridin-3-yl]-[1,2,4]triazolo[4,3-a]pyridine Chemical compound CC1=CC=CC(C=2C(=CC=CN=2)C2=CN3C=NN=C3C=C2)=C1 HZKDJUAQINODMC-UHFFFAOYSA-N 0.000 claims description 2
ICBWNDSZVNXIIG-UHFFFAOYSA-N 6-[2-(3-methylphenyl)pyridin-3-yl]imidazo[1,2-a]pyridine Chemical compound CC1=CC=CC(C=2C(=CC=CN=2)C2=CN3C=CN=C3C=C2)=C1 ICBWNDSZVNXIIG-UHFFFAOYSA-N 0.000 claims description 2
FICBMEYLHNDEQU-UHFFFAOYSA-N 6-[2-(3-methylphenyl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound CC1=CC=CC(C=2C(=CC=CN=2)C2=CN3C(C#N)=CN=C3C=C2)=C1 FICBMEYLHNDEQU-UHFFFAOYSA-N 0.000 claims description 2
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WGFFJRVUJGDAIJ-UHFFFAOYSA-N 6-[2-(3-methylphenyl)pyridin-3-yl]quinazolin-2-amine Chemical compound CC1=CC=CC(C=2C(=CC=CN=2)C=2C=C3C=NC(N)=NC3=CC=2)=C1 WGFFJRVUJGDAIJ-UHFFFAOYSA-N 0.000 claims description 2
DMJJDPVULMNXCM-UHFFFAOYSA-N 6-[2-(3-methylphenyl)pyridin-3-yl]quinazoline Chemical compound CC1=CC=CC(C=2C(=CC=CN=2)C=2C=C3C=NC=NC3=CC=2)=C1 DMJJDPVULMNXCM-UHFFFAOYSA-N 0.000 claims description 2
XCNVMHHYEZIFDC-UHFFFAOYSA-N 6-[2-(3-methylphenyl)pyridin-3-yl]quinoline Chemical compound CC1=CC=CC(C=2C(=CC=CN=2)C=2C=C3C=CC=NC3=CC=2)=C1 XCNVMHHYEZIFDC-UHFFFAOYSA-N 0.000 claims description 2
SPEZQIMYTWFASQ-UHFFFAOYSA-N 6-[2-(3-morpholin-4-ylphenyl)pyridin-3-yl]quinazolin-4-amine Chemical compound C1=C2C(N)=NC=NC2=CC=C1C1=CC=CN=C1C(C=1)=CC=CC=1N1CCOCC1 SPEZQIMYTWFASQ-UHFFFAOYSA-N 0.000 claims description 2
UYYNWBGRYWQBRK-UHFFFAOYSA-N 6-[2-(3-propan-2-yloxyphenyl)pyridin-3-yl]quinazolin-4-amine Chemical compound CC(C)OC1=CC=CC(C=2C(=CC=CN=2)C=2C=C3C(N)=NC=NC3=CC=2)=C1 UYYNWBGRYWQBRK-UHFFFAOYSA-N 0.000 claims description 2
WIRXLHMGVUQZCX-UHFFFAOYSA-N 6-[2-(3-propan-2-ylphenyl)pyridin-3-yl]-1h-benzimidazole Chemical compound CC(C)C1=CC=CC(C=2C(=CC=CN=2)C=2C=C3NC=NC3=CC=2)=C1 WIRXLHMGVUQZCX-UHFFFAOYSA-N 0.000 claims description 2
GPULTXFIYLIUQH-UHFFFAOYSA-N 6-[2-(3-propan-2-ylphenyl)pyridin-3-yl]quinazolin-4-amine Chemical compound CC(C)C1=CC=CC(C=2C(=CC=CN=2)C=2C=C3C(N)=NC=NC3=CC=2)=C1 GPULTXFIYLIUQH-UHFFFAOYSA-N 0.000 claims description 2
RFWUKCLXPZZSFB-UHFFFAOYSA-N 6-[2-(4-fluoro-2-methylphenyl)pyridin-3-yl]quinazolin-4-amine Chemical compound CC1=CC(F)=CC=C1C1=NC=CC=C1C1=CC=C(N=CN=C2N)C2=C1 RFWUKCLXPZZSFB-UHFFFAOYSA-N 0.000 claims description 2
QWSUAQRKWKGCLH-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methoxyphenyl)pyridin-3-yl]-1h-pyrazolo[4,3-b]pyridine Chemical compound C1=C(F)C(OC)=CC(C=2C(=CC=CN=2)C=2C=C3NN=CC3=NC=2)=C1 QWSUAQRKWKGCLH-UHFFFAOYSA-N 0.000 claims description 2
RZPNPAWPYSLVOT-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methoxyphenyl)pyridin-3-yl]quinazolin-4-amine Chemical compound C1=C(F)C(OC)=CC(C=2C(=CC=CN=2)C=2C=C3C(N)=NC=NC3=CC=2)=C1 RZPNPAWPYSLVOT-UHFFFAOYSA-N 0.000 claims description 2
MSBHSYIYMZMZQA-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)-5-(1h-pyrazol-4-yl)pyridin-3-yl]-1,3-benzothiazole Chemical compound C1=C(F)C(C)=CC(C=2C(=CC(=CN=2)C2=CNN=C2)C=2C=C3SC=NC3=CC=2)=C1 MSBHSYIYMZMZQA-UHFFFAOYSA-N 0.000 claims description 2
KERWCLAEHYKADC-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)-5-(4-methylpiperazin-1-yl)pyridin-3-yl]-1,3-benzothiazole Chemical compound C1CN(C)CCN1C(C=C1C=2C=C3SC=NC3=CC=2)=CN=C1C1=CC=C(F)C(C)=C1 KERWCLAEHYKADC-UHFFFAOYSA-N 0.000 claims description 2
DSKMNXFSVOMSGO-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)-5-(methoxymethyl)pyridin-3-yl]quinoxaline Chemical compound C=1C=C2N=CC=NC2=CC=1C1=CC(COC)=CN=C1C1=CC=C(F)C(C)=C1 DSKMNXFSVOMSGO-UHFFFAOYSA-N 0.000 claims description 2
VNTGNNCVHHSBFX-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)-5-[(4-methylpiperazin-1-yl)methyl]pyridin-3-yl]quinoxaline Chemical compound C1CN(C)CCN1CC(C=C1C=2C=C3N=CC=NC3=CC=2)=CN=C1C1=CC=C(F)C(C)=C1 VNTGNNCVHHSBFX-UHFFFAOYSA-N 0.000 claims description 2
YQVXLUCLLGMSSU-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)-5-pyrazol-1-ylpyridin-3-yl]-1,3-benzothiazole Chemical compound C1=C(F)C(C)=CC(C=2C(=CC(=CN=2)N2N=CC=C2)C=2C=C3SC=NC3=CC=2)=C1 YQVXLUCLLGMSSU-UHFFFAOYSA-N 0.000 claims description 2
ZVMSMPKJCDWBJJ-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-1,2-benzoxazol-3-amine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3ON=C(N)C3=CC=2)=C1 ZVMSMPKJCDWBJJ-UHFFFAOYSA-N 0.000 claims description 2
RFTIZVKDPKJYKW-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-1,3-benzothiazole Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3SC=NC3=CC=2)=C1 RFTIZVKDPKJYKW-UHFFFAOYSA-N 0.000 claims description 2
VFXVITAJMUJISB-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-1,3-benzoxazole Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3OC=NC3=CC=2)=C1 VFXVITAJMUJISB-UHFFFAOYSA-N 0.000 claims description 2
FNFUIUNTBKUKQD-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-1-(1-methylpiperidin-4-yl)benzimidazole Chemical compound C1CN(C)CCC1N1C2=CC(C=3C(=NC=CC=3)C=3C=C(C)C(F)=CC=3)=CC=C2N=C1 FNFUIUNTBKUKQD-UHFFFAOYSA-N 0.000 claims description 2
ADIKGLCFCNTEIF-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-1-(oxan-4-yl)benzimidazole Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3N(C4CCOCC4)C=NC3=CC=2)=C1 ADIKGLCFCNTEIF-UHFFFAOYSA-N 0.000 claims description 2
NNLFZGSOMWMTBE-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-1-[2-(4-methylpiperazin-1-yl)ethyl]benzimidazole Chemical compound C1CN(C)CCN1CCN1C2=CC(C=3C(=NC=CC=3)C=3C=C(C)C(F)=CC=3)=CC=C2N=C1 NNLFZGSOMWMTBE-UHFFFAOYSA-N 0.000 claims description 2
LAHGBDQTKZDLTH-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-1-[3-(4-methylpiperazin-1-yl)propyl]benzimidazole Chemical compound C1CN(C)CCN1CCCN1C2=CC(C=3C(=NC=CC=3)C=3C=C(C)C(F)=CC=3)=CC=C2N=C1 LAHGBDQTKZDLTH-UHFFFAOYSA-N 0.000 claims description 2
HUDCAXITODBYGW-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-1-methylbenzimidazole Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3N(C)C=NC3=CC=2)=C1 HUDCAXITODBYGW-UHFFFAOYSA-N 0.000 claims description 2
WPBPHNZXMASLEP-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-1-methylindazol-3-amine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3N(C)N=C(N)C3=CC=2)=C1 WPBPHNZXMASLEP-UHFFFAOYSA-N 0.000 claims description 2
LPXMAAVBNVQISN-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-1h-benzimidazole Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3NC=NC3=CC=2)=C1 LPXMAAVBNVQISN-UHFFFAOYSA-N 0.000 claims description 2
BNSHLCCUCUGUKH-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-1h-indazol-3-amine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3NN=C(N)C3=CC=2)=C1 BNSHLCCUCUGUKH-UHFFFAOYSA-N 0.000 claims description 2
DUNPRYBLZZCGCN-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-1h-indazole Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3NN=CC3=CC=2)=C1 DUNPRYBLZZCGCN-UHFFFAOYSA-N 0.000 claims description 2
HXXCUFZVFZBETC-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-1h-pyrazolo[4,3-b]pyridine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3NN=CC3=NC=2)=C1 HXXCUFZVFZBETC-UHFFFAOYSA-N 0.000 claims description 2
MIIRZJSSIPSDKF-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-1h-quinazolin-4-one Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3C(=O)N=CNC3=CC=2)=C1 MIIRZJSSIPSDKF-UHFFFAOYSA-N 0.000 claims description 2
ZZVGJESUHNOALN-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-3-(3,4,5-trimethoxyphenyl)imidazo[1,2-a]pyridine Chemical compound COC1=C(OC)C(OC)=CC(C=2N3C=C(C=CC3=NC=2)C=2C(=NC=CC=2)C=2C=C(C)C(F)=CC=2)=C1 ZZVGJESUHNOALN-UHFFFAOYSA-N 0.000 claims description 2
JYWOBZOSZZNZHG-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-3-(3-methoxyphenyl)imidazo[1,5-a]pyridine Chemical compound COC1=CC=CC(C=2N3C=C(C=CC3=CN=2)C=2C(=NC=CC=2)C=2C=C(C)C(F)=CC=2)=C1 JYWOBZOSZZNZHG-UHFFFAOYSA-N 0.000 claims description 2
MRFVOBAEQORSKK-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-3-(trifluoromethyl)imidazo[1,2-a]pyridine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C2=CN3C(=CN=C3C=C2)C(F)(F)F)=C1 MRFVOBAEQORSKK-UHFFFAOYSA-N 0.000 claims description 2
RLVIECAJYXKXLI-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-3-methylimidazo[1,2-a]pyridine Chemical compound C=1N2C(C)=CN=C2C=CC=1C1=CC=CN=C1C1=CC=C(F)C(C)=C1 RLVIECAJYXKXLI-UHFFFAOYSA-N 0.000 claims description 2
OUJWCSVUHNUFRZ-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-3-methylquinazolin-4-one Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3C(=O)N(C)C=NC3=CC=2)=C1 OUJWCSVUHNUFRZ-UHFFFAOYSA-N 0.000 claims description 2
QFZJNRYCAWUFIX-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-3-pyridin-4-ylimidazo[1,5-a]pyridine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C2=CN3C(C=4C=CN=CC=4)=NC=C3C=C2)=C1 QFZJNRYCAWUFIX-UHFFFAOYSA-N 0.000 claims description 2
KUSIQNPRAZDXCM-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-3-pyrrolidin-1-ylimidazo[1,2-a]pyridine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C2=CN3C(N4CCCC4)=CN=C3C=C2)=C1 KUSIQNPRAZDXCM-UHFFFAOYSA-N 0.000 claims description 2
USPJBEDAZTVUHZ-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-4-(1-pyridin-4-ylpiperidin-4-yl)oxyquinazoline Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3C(OC4CCN(CC4)C=4C=CN=CC=4)=NC=NC3=CC=2)=C1 USPJBEDAZTVUHZ-UHFFFAOYSA-N 0.000 claims description 2
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ICMWMCPUXFWAPZ-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-4-(6-methylpyridin-3-yl)oxyquinazoline Chemical compound C1=NC(C)=CC=C1OC1=NC=NC2=CC=C(C=3C(=NC=CC=3)C=3C=C(C)C(F)=CC=3)C=C12 ICMWMCPUXFWAPZ-UHFFFAOYSA-N 0.000 claims description 2
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SCWMXBNHYJJAPV-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-4-[3-(4-methylpiperazin-1-yl)propoxy]quinazoline Chemical compound C1CN(C)CCN1CCCOC1=NC=NC2=CC=C(C=3C(=NC=CC=3)C=3C=C(C)C(F)=CC=3)C=C12 SCWMXBNHYJJAPV-UHFFFAOYSA-N 0.000 claims description 2
AQRXUHPWLMJRGH-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-4-methoxyquinazoline Chemical compound C1=C2C(OC)=NC=NC2=CC=C1C1=CC=CN=C1C1=CC=C(F)C(C)=C1 AQRXUHPWLMJRGH-UHFFFAOYSA-N 0.000 claims description 2
KXSKEDRWWAWAFL-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-4-methoxyquinoline Chemical compound C1=C2C(OC)=CC=NC2=CC=C1C1=CC=CN=C1C1=CC=C(F)C(C)=C1 KXSKEDRWWAWAFL-UHFFFAOYSA-N 0.000 claims description 2
RTEMSRBDQFEAOE-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-4-pyridin-3-yloxyquinazoline Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3C(OC=4C=NC=CC=4)=NC=NC3=CC=2)=C1 RTEMSRBDQFEAOE-UHFFFAOYSA-N 0.000 claims description 2
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NMEVHAPFJUYMBB-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-5-methyl-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C2=C(N3N=CN=C3C=C2)C)=C1 NMEVHAPFJUYMBB-UHFFFAOYSA-N 0.000 claims description 2
XWICVKZOABWFFG-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-7-methyl-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C(=CC3=NC=NN3C=2)C)=C1 XWICVKZOABWFFG-UHFFFAOYSA-N 0.000 claims description 2
ITCPVTUUUPPPQK-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-7-methylimidazo[1,2-a]pyridine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C(=CC3=NC=CN3C=2)C)=C1 ITCPVTUUUPPPQK-UHFFFAOYSA-N 0.000 claims description 2
CEFAHVUWJPTPKU-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C2=CN3N=CN=C3C=C2)=C1 CEFAHVUWJPTPKU-UHFFFAOYSA-N 0.000 claims description 2
GBLUBYHNOSZFQR-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C2=CN3N=CN=C3N=C2)=C1 GBLUBYHNOSZFQR-UHFFFAOYSA-N 0.000 claims description 2
LBIIQBPDVJQSPM-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-[1,2,4]triazolo[4,3-a]pyridine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C2=CN3C=NN=C3C=C2)=C1 LBIIQBPDVJQSPM-UHFFFAOYSA-N 0.000 claims description 2
MAXFYXBNXNMDRV-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-n,n-dimethylimidazo[1,2-a]pyridin-3-amine Chemical compound C=1N2C(N(C)C)=CN=C2C=CC=1C1=CC=CN=C1C1=CC=C(F)C(C)=C1 MAXFYXBNXNMDRV-UHFFFAOYSA-N 0.000 claims description 2
KMEMPZGSQMUBNF-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-n-(1,2,2,6,6-pentamethylpiperidin-4-yl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1C(C)(C)N(C)C(C)(C)CC1NC(=O)C1=CN=C2N1C=C(C=1C(=NC=CC=1)C=1C=C(C)C(F)=CC=1)C=C2 KMEMPZGSQMUBNF-UHFFFAOYSA-N 0.000 claims description 2
INFOEUXLSOYIBG-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-n-(1-methylpiperidin-4-yl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1CN(C)CCC1NC(=O)C1=CN=C2N1C=C(C=1C(=NC=CC=1)C=1C=C(C)C(F)=CC=1)C=C2 INFOEUXLSOYIBG-UHFFFAOYSA-N 0.000 claims description 2
DKBNUMLAYOTIHS-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-n-(2-hydroxyethyl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C2=CN3C(C(=O)NCCO)=CN=C3C=C2)=C1 DKBNUMLAYOTIHS-UHFFFAOYSA-N 0.000 claims description 2
FAANDJQHEOSLNB-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-n-(2-pyridin-3-ylethyl)quinazolin-4-amine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3C(NCCC=4C=NC=CC=4)=NC=NC3=CC=2)=C1 FAANDJQHEOSLNB-UHFFFAOYSA-N 0.000 claims description 2
IPPVKRPLSKHHKM-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-n-(3,4,5-trimethoxyphenyl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound COC1=C(OC)C(OC)=CC(NC(=O)C=2N3C=C(C=CC3=NC=2)C=2C(=NC=CC=2)C=2C=C(C)C(F)=CC=2)=C1 IPPVKRPLSKHHKM-UHFFFAOYSA-N 0.000 claims description 2
TWCWKIKRQMTCIP-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-n-(3-hydroxypropyl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C2=CN3C(C(=O)NCCCO)=CN=C3C=C2)=C1 TWCWKIKRQMTCIP-UHFFFAOYSA-N 0.000 claims description 2
LRIMRMVANPPKKG-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-n-(3-morpholin-4-ylpropyl)quinazolin-4-amine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3C(NCCCN4CCOCC4)=NC=NC3=CC=2)=C1 LRIMRMVANPPKKG-UHFFFAOYSA-N 0.000 claims description 2
POBZKAYHCOWYKG-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-n-(3-sulfamoylphenyl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C2=CN3C(C(=O)NC=4C=C(C=CC=4)S(N)(=O)=O)=CN=C3C=C2)=C1 POBZKAYHCOWYKG-UHFFFAOYSA-N 0.000 claims description 2
NRYKERBFKMMFBZ-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-n-(4-methoxyphenyl)quinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1NC1=NC=NC2=CC=C(C=3C(=NC=CC=3)C=3C=C(C)C(F)=CC=3)C=C12 NRYKERBFKMMFBZ-UHFFFAOYSA-N 0.000 claims description 2
YWRUJXKGQPZODW-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-n-(4-morpholin-4-ylphenyl)quinazolin-4-amine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3C(NC=4C=CC(=CC=4)N4CCOCC4)=NC=NC3=CC=2)=C1 YWRUJXKGQPZODW-UHFFFAOYSA-N 0.000 claims description 2
SLGKYXMDMMMRKB-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-n-(4-sulfamoylphenyl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C2=CN3C(C(=O)NC=4C=CC(=CC=4)S(N)(=O)=O)=CN=C3C=C2)=C1 SLGKYXMDMMMRKB-UHFFFAOYSA-N 0.000 claims description 2
NFSVHCRJKGDAJB-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-n-(pyridin-3-ylmethyl)quinazolin-4-amine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3C(NCC=4C=NC=CC=4)=NC=NC3=CC=2)=C1 NFSVHCRJKGDAJB-UHFFFAOYSA-N 0.000 claims description 2
PAGVENBPEASHTF-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-n-(pyridin-4-ylmethyl)quinazolin-4-amine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3C(NCC=4C=CN=CC=4)=NC=NC3=CC=2)=C1 PAGVENBPEASHTF-UHFFFAOYSA-N 0.000 claims description 2
YAUOESUFLFAERV-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-n-[(1-methylpiperidin-4-yl)methyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1CN(C)CCC1CNC(=O)C1=CN=C2N1C=C(C=1C(=NC=CC=1)C=1C=C(C)C(F)=CC=1)C=C2 YAUOESUFLFAERV-UHFFFAOYSA-N 0.000 claims description 2
AMPOYTVHANDXKJ-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-n-[(1-methylpiperidin-4-yl)methyl]quinazolin-4-amine Chemical compound C1CN(C)CCC1CNC1=NC=NC2=CC=C(C=3C(=NC=CC=3)C=3C=C(C)C(F)=CC=3)C=C12 AMPOYTVHANDXKJ-UHFFFAOYSA-N 0.000 claims description 2
RBEHQDIAHQGDEL-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-n-[2-(1-methylpiperidin-4-yl)ethyl]quinazolin-4-amine Chemical compound C1CN(C)CCC1CCNC1=NC=NC2=CC=C(C=3C(=NC=CC=3)C=3C=C(C)C(F)=CC=3)C=C12 RBEHQDIAHQGDEL-UHFFFAOYSA-N 0.000 claims description 2
VCINEMFHNVJAGQ-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-n-methylimidazo[1,2-a]pyridine-3-carboxamide Chemical compound C=1N2C(C(=O)NC)=CN=C2C=CC=1C1=CC=CN=C1C1=CC=C(F)C(C)=C1 VCINEMFHNVJAGQ-UHFFFAOYSA-N 0.000 claims description 2
XPRCMVJIGXMIRK-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-n-propan-2-ylquinazolin-4-amine Chemical compound C1=C2C(NC(C)C)=NC=NC2=CC=C1C1=CC=CN=C1C1=CC=C(F)C(C)=C1 XPRCMVJIGXMIRK-UHFFFAOYSA-N 0.000 claims description 2
NGJLSDRVXIUUMC-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-n-propylimidazo[1,2-a]pyridine-3-carboxamide Chemical compound C=1N2C(C(=O)NCCC)=CN=C2C=CC=1C1=CC=CN=C1C1=CC=C(F)C(C)=C1 NGJLSDRVXIUUMC-UHFFFAOYSA-N 0.000 claims description 2
GVQPNEGVDRYECL-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]-n-propylquinazolin-4-amine Chemical compound C1=C2C(NCCC)=NC=NC2=CC=C1C1=CC=CN=C1C1=CC=C(F)C(C)=C1 GVQPNEGVDRYECL-UHFFFAOYSA-N 0.000 claims description 2
ICPIXNXPCXAYKP-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]imidazo[1,2-a]pyridine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C2=CN3C=CN=C3C=C2)=C1 ICPIXNXPCXAYKP-UHFFFAOYSA-N 0.000 claims description 2
NLINLEVHYVNUDZ-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C2=CN3C(C#N)=CN=C3C=C2)=C1 NLINLEVHYVNUDZ-UHFFFAOYSA-N 0.000 claims description 2
QGLDCTOTCQGGQJ-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carboxylic acid Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C2=CN3C(C(O)=O)=CN=C3C=C2)=C1 QGLDCTOTCQGGQJ-UHFFFAOYSA-N 0.000 claims description 2
BTZUMZMEZGTKSD-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]imidazo[1,2-a]pyrimidine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C2=CN3C=CN=C3N=C2)=C1 BTZUMZMEZGTKSD-UHFFFAOYSA-N 0.000 claims description 2
KSKNGEFXTFXADQ-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]imidazo[1,2-b]pyridazine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C2=NN3C=CN=C3C=C2)=C1 KSKNGEFXTFXADQ-UHFFFAOYSA-N 0.000 claims description 2
YNDVOTINDINELW-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C2=NN3C(C#N)=CN=C3C=C2)=C1 YNDVOTINDINELW-UHFFFAOYSA-N 0.000 claims description 2
CRYHQZHATOYBNR-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]imidazo[1,5-a]pyridin-3-amine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C2=CN3C(N)=NC=C3C=C2)=C1 CRYHQZHATOYBNR-UHFFFAOYSA-N 0.000 claims description 2
ISXLLBFOXFYKJY-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]imidazo[1,5-a]pyridine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C2=CN3C=NC=C3C=C2)=C1 ISXLLBFOXFYKJY-UHFFFAOYSA-N 0.000 claims description 2
PDUNPKHLAFPZRW-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]imidazo[1,5-a]pyridine-3-carboxylic acid Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C2=CN3C(C(O)=O)=NC=C3C=C2)=C1 PDUNPKHLAFPZRW-UHFFFAOYSA-N 0.000 claims description 2
VCUYSBGFTOIFBC-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]pyrido[2,3-b]pyrazine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2N=C3N=CC=NC3=CC=2)=C1 VCUYSBGFTOIFBC-UHFFFAOYSA-N 0.000 claims description 2
RIGSJLJSIORNAU-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]pyrido[2,3-d]pyrimidin-4-amine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3C(N)=NC=NC3=NC=2)=C1 RIGSJLJSIORNAU-UHFFFAOYSA-N 0.000 claims description 2
WERMAPCKIJFDEF-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]quinazolin-2-amine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3C=NC(N)=NC3=CC=2)=C1 WERMAPCKIJFDEF-UHFFFAOYSA-N 0.000 claims description 2
JWHNBOWQWCJRRX-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]quinazolin-4-amine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3C(N)=NC=NC3=CC=2)=C1 JWHNBOWQWCJRRX-UHFFFAOYSA-N 0.000 claims description 2
XJVIALWTEOQRGJ-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]quinazoline Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3C=NC=NC3=CC=2)=C1 XJVIALWTEOQRGJ-UHFFFAOYSA-N 0.000 claims description 2
DSHPZTWXDGWPHW-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]quinolin-2-amine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3C=CC(N)=NC3=CC=2)=C1 DSHPZTWXDGWPHW-UHFFFAOYSA-N 0.000 claims description 2
FMJVDBGGOZMMRT-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]quinolin-4-amine Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3C(N)=CC=NC3=CC=2)=C1 FMJVDBGGOZMMRT-UHFFFAOYSA-N 0.000 claims description 2
JLDICMJUCNNUNK-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]quinoline Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3C=CC=NC3=CC=2)=C1 JLDICMJUCNNUNK-UHFFFAOYSA-N 0.000 claims description 2
MRKVPTMSFRUKIE-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]quinoline-2-carbonitrile Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3C=CC(=NC3=CC=2)C#N)=C1 MRKVPTMSFRUKIE-UHFFFAOYSA-N 0.000 claims description 2
CYGWIULFNZJBLG-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]quinoline-4-carboxamide Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3C(C(N)=O)=CC=NC3=CC=2)=C1 CYGWIULFNZJBLG-UHFFFAOYSA-N 0.000 claims description 2
JPKADPPMYXMDRL-UHFFFAOYSA-N 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]quinoxaline Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C=2C=C3N=CC=NC3=CC=2)=C1 JPKADPPMYXMDRL-UHFFFAOYSA-N 0.000 claims description 2
QMOVWKFHGZLJRV-UHFFFAOYSA-N 6-[2-(4-fluorophenyl)pyridin-3-yl]-1,3-benzothiazole Chemical compound C1=CC(F)=CC=C1C1=NC=CC=C1C1=CC=C(N=CS2)C2=C1 QMOVWKFHGZLJRV-UHFFFAOYSA-N 0.000 claims description 2
KYRTWAOFBOQPCH-UHFFFAOYSA-N 6-[2-(4-fluorophenyl)pyridin-3-yl]-1h-indazole Chemical compound C1=CC(F)=CC=C1C1=NC=CC=C1C1=CC=C(C=NN2)C2=C1 KYRTWAOFBOQPCH-UHFFFAOYSA-N 0.000 claims description 2
YPCKJURUMAVIOC-UHFFFAOYSA-N 6-[2-(4-fluorophenyl)pyridin-3-yl]-3-methylquinazolin-4-one Chemical compound C1=C2C(=O)N(C)C=NC2=CC=C1C1=CC=CN=C1C1=CC=C(F)C=C1 YPCKJURUMAVIOC-UHFFFAOYSA-N 0.000 claims description 2
BWQCYDUWGCAJDE-UHFFFAOYSA-N 6-[2-(4-fluorophenyl)pyridin-3-yl]imidazo[1,2-a]pyridine Chemical compound C1=CC(F)=CC=C1C1=NC=CC=C1C1=CN2C=CN=C2C=C1 BWQCYDUWGCAJDE-UHFFFAOYSA-N 0.000 claims description 2
LGMYGTHFJCCFDF-UHFFFAOYSA-N 6-[2-(4-fluorophenyl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound C1=CC(F)=CC=C1C1=NC=CC=C1C1=CN2C(C#N)=CN=C2C=C1 LGMYGTHFJCCFDF-UHFFFAOYSA-N 0.000 claims description 2
OKOOJSVXZJJRAM-UHFFFAOYSA-N 6-[2-(4-methoxyphenyl)pyridin-3-yl]imidazo[1,2-a]pyridine Chemical compound C1=CC(OC)=CC=C1C1=NC=CC=C1C1=CN2C=CN=C2C=C1 OKOOJSVXZJJRAM-UHFFFAOYSA-N 0.000 claims description 2
OZWWZBZVHVBGJK-UHFFFAOYSA-N 6-[2-(5-chloro-2,4-difluorophenyl)pyridin-3-yl]-1,3-benzothiazole Chemical compound C1=C(Cl)C(F)=CC(F)=C1C1=NC=CC=C1C1=CC=C(N=CS2)C2=C1 OZWWZBZVHVBGJK-UHFFFAOYSA-N 0.000 claims description 2
CKIBFHFQUPUPTB-UHFFFAOYSA-N 6-[2-(5-chloro-2,4-difluorophenyl)pyridin-3-yl]-1-methylbenzimidazole Chemical compound C1=C2N(C)C=NC2=CC=C1C1=CC=CN=C1C1=CC(Cl)=C(F)C=C1F CKIBFHFQUPUPTB-UHFFFAOYSA-N 0.000 claims description 2
IWUWOXCFEXZAFC-UHFFFAOYSA-N 6-[2-(5-chloro-2,4-difluorophenyl)pyridin-3-yl]-1h-quinazolin-4-one Chemical compound C1=C(Cl)C(F)=CC(F)=C1C1=NC=CC=C1C1=CC=C(N=CNC2=O)C2=C1 IWUWOXCFEXZAFC-UHFFFAOYSA-N 0.000 claims description 2
TWJQDCSSXKEOTQ-UHFFFAOYSA-N 6-[2-(5-chloro-2,4-difluorophenyl)pyridin-3-yl]-3-methylimidazo[1,2-a]pyridine Chemical compound C=1N2C(C)=CN=C2C=CC=1C1=CC=CN=C1C1=CC(Cl)=C(F)C=C1F TWJQDCSSXKEOTQ-UHFFFAOYSA-N 0.000 claims description 2
PJWBNTGBNHMACF-UHFFFAOYSA-N 6-[2-(5-chloro-2,4-difluorophenyl)pyridin-3-yl]-4-methoxyquinazoline Chemical compound C1=C2C(OC)=NC=NC2=CC=C1C1=CC=CN=C1C1=CC(Cl)=C(F)C=C1F PJWBNTGBNHMACF-UHFFFAOYSA-N 0.000 claims description 2
DHYFIUYORFFIGP-UHFFFAOYSA-N 6-[2-(5-chloro-2,4-difluorophenyl)pyridin-3-yl]-4-methoxyquinoline Chemical compound C1=C2C(OC)=CC=NC2=CC=C1C1=CC=CN=C1C1=CC(Cl)=C(F)C=C1F DHYFIUYORFFIGP-UHFFFAOYSA-N 0.000 claims description 2
PKBDVTFSFHMIDG-UHFFFAOYSA-N 6-[2-(5-chloro-2,4-difluorophenyl)pyridin-3-yl]-5-methyl-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C1=CC2=NC=NN2C(C)=C1C1=CC=CN=C1C1=CC(Cl)=C(F)C=C1F PKBDVTFSFHMIDG-UHFFFAOYSA-N 0.000 claims description 2
SMGIZDGQICMINO-UHFFFAOYSA-N 6-[2-(5-chloro-2,4-difluorophenyl)pyridin-3-yl]-7-methyl-[1,2,4]triazolo[1,5-a]pyridine Chemical compound CC1=CC2=NC=NN2C=C1C1=CC=CN=C1C1=CC(Cl)=C(F)C=C1F SMGIZDGQICMINO-UHFFFAOYSA-N 0.000 claims description 2
CFMSMYYXAJJYGT-UHFFFAOYSA-N 6-[2-(5-chloro-2,4-difluorophenyl)pyridin-3-yl]-7-methylimidazo[1,2-a]pyridine Chemical compound CC1=CC2=NC=CN2C=C1C1=CC=CN=C1C1=CC(Cl)=C(F)C=C1F CFMSMYYXAJJYGT-UHFFFAOYSA-N 0.000 claims description 2
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QDBLORDFPAHJPE-UHFFFAOYSA-N 6-[2-(5-chloro-2,4-difluorophenyl)pyridin-3-yl]-[1,2,4]triazolo[1,5-b]pyridazine Chemical compound C1=C(Cl)C(F)=CC(F)=C1C1=NC=CC=C1C1=NN2N=CN=C2C=C1 QDBLORDFPAHJPE-UHFFFAOYSA-N 0.000 claims description 2
LQOFGAKMTPLZBQ-UHFFFAOYSA-N 6-[2-(5-chloro-2,4-difluorophenyl)pyridin-3-yl]-n-(1-methylpiperidin-4-yl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1CN(C)CCC1NC(=O)C1=CN=C2N1C=C(C=1C(=NC=CC=1)C=1C(=CC(F)=C(Cl)C=1)F)C=C2 LQOFGAKMTPLZBQ-UHFFFAOYSA-N 0.000 claims description 2
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COLMGBNCHGRIMS-UHFFFAOYSA-N 6-[2-(5-chloro-2,4-difluorophenyl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound C1=C(Cl)C(F)=CC(F)=C1C1=NC=CC=C1C1=CN2C(C#N)=CN=C2C=C1 COLMGBNCHGRIMS-UHFFFAOYSA-N 0.000 claims description 2
ARMCKOXPFCXRPP-UHFFFAOYSA-N 6-[2-(5-chloro-2,4-difluorophenyl)pyridin-3-yl]imidazo[1,2-b]pyridazine Chemical compound C1=C(Cl)C(F)=CC(F)=C1C1=NC=CC=C1C1=NN2C=CN=C2C=C1 ARMCKOXPFCXRPP-UHFFFAOYSA-N 0.000 claims description 2
CVZRJLFZEAXCLS-UHFFFAOYSA-N 6-[2-(5-chloro-2,4-difluorophenyl)pyridin-3-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound C1=C(Cl)C(F)=CC(F)=C1C1=NC=CC=C1C1=NN2C(C#N)=CN=C2C=C1 CVZRJLFZEAXCLS-UHFFFAOYSA-N 0.000 claims description 2
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NUYNTCFFNRCFFB-UHFFFAOYSA-N 6-[2-(5-chloro-2-fluorophenyl)pyridin-3-yl]-1,3-benzothiazole Chemical compound FC1=CC=C(Cl)C=C1C1=NC=CC=C1C1=CC=C(N=CS2)C2=C1 NUYNTCFFNRCFFB-UHFFFAOYSA-N 0.000 claims description 2
QVRBUXQIZBHOMP-UHFFFAOYSA-N 6-[2-(5-chloro-2-fluorophenyl)pyridin-3-yl]-1-methylbenzimidazole Chemical compound C1=C2N(C)C=NC2=CC=C1C1=CC=CN=C1C1=CC(Cl)=CC=C1F QVRBUXQIZBHOMP-UHFFFAOYSA-N 0.000 claims description 2
PFOJKCCJWWOEPT-UHFFFAOYSA-N 6-[2-(5-chloro-2-fluorophenyl)pyridin-3-yl]-1h-quinazolin-4-one Chemical compound FC1=CC=C(Cl)C=C1C1=NC=CC=C1C1=CC=C(N=CNC2=O)C2=C1 PFOJKCCJWWOEPT-UHFFFAOYSA-N 0.000 claims description 2
WIIKWEGZWHTRCO-UHFFFAOYSA-N 6-[2-(5-chloro-2-fluorophenyl)pyridin-3-yl]-3-methylimidazo[1,2-a]pyridine Chemical compound C=1N2C(C)=CN=C2C=CC=1C1=CC=CN=C1C1=CC(Cl)=CC=C1F WIIKWEGZWHTRCO-UHFFFAOYSA-N 0.000 claims description 2
AIUUZFNFTLPSSR-UHFFFAOYSA-N 6-[2-(5-chloro-2-fluorophenyl)pyridin-3-yl]-4-methoxyquinazoline Chemical compound C1=C2C(OC)=NC=NC2=CC=C1C1=CC=CN=C1C1=CC(Cl)=CC=C1F AIUUZFNFTLPSSR-UHFFFAOYSA-N 0.000 claims description 2
KQHGNRIKFYHRLR-UHFFFAOYSA-N 6-[2-(5-chloro-2-fluorophenyl)pyridin-3-yl]-4-methoxyquinoline Chemical compound C1=C2C(OC)=CC=NC2=CC=C1C1=CC=CN=C1C1=CC(Cl)=CC=C1F KQHGNRIKFYHRLR-UHFFFAOYSA-N 0.000 claims description 2
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XPBPXWVBNOIXFW-UHFFFAOYSA-N 6-[2-(5-chloro-2-fluorophenyl)pyridin-3-yl]-8-fluoro-[1,2,4]triazolo[1,5-a]pyridine Chemical compound FC1=CC=C(Cl)C=C1C1=NC=CC=C1C1=CN2N=CN=C2C(F)=C1 XPBPXWVBNOIXFW-UHFFFAOYSA-N 0.000 claims description 2
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NUMWUHVOGZKCKV-UHFFFAOYSA-N 6-[2-(5-chloro-2-methylphenyl)pyridin-3-yl]quinazolin-4-amine Chemical compound CC1=CC=C(Cl)C=C1C1=NC=CC=C1C1=CC=C(N=CN=C2N)C2=C1 NUMWUHVOGZKCKV-UHFFFAOYSA-N 0.000 claims description 2
CYHVWQGLIBRNLR-UHFFFAOYSA-N 6-[2-(5-fluoro-2-methylphenyl)pyridin-3-yl]quinazolin-4-amine Chemical compound CC1=CC=C(F)C=C1C1=NC=CC=C1C1=CC=C(N=CN=C2N)C2=C1 CYHVWQGLIBRNLR-UHFFFAOYSA-N 0.000 claims description 2
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VMOVZDJVNSIEPQ-UHFFFAOYSA-N 6-[2-[3-(2,2,2-trifluoroethoxy)phenyl]pyridin-3-yl]quinazolin-4-amine Chemical compound C1=C2C(N)=NC=NC2=CC=C1C1=CC=CN=C1C1=CC=CC(OCC(F)(F)F)=C1 VMOVZDJVNSIEPQ-UHFFFAOYSA-N 0.000 claims description 2
KEYNXAZRXRMSTQ-UHFFFAOYSA-N 6-[2-[3-(2-methoxyethoxy)phenyl]pyridin-3-yl]quinazolin-4-amine Chemical compound COCCOC1=CC=CC(C=2C(=CC=CN=2)C=2C=C3C(N)=NC=NC3=CC=2)=C1 KEYNXAZRXRMSTQ-UHFFFAOYSA-N 0.000 claims description 2
ZRPHTTKOSLJTCO-UHFFFAOYSA-N 6-[2-[3-(cyclopropylmethoxy)phenyl]pyridin-3-yl]quinazolin-4-amine Chemical compound C1=C2C(N)=NC=NC2=CC=C1C1=CC=CN=C1C(C=1)=CC=CC=1OCC1CC1 ZRPHTTKOSLJTCO-UHFFFAOYSA-N 0.000 claims description 2
YRGPRYKHCMEFDI-UHFFFAOYSA-N 6-[2-[3-(difluoromethoxy)phenyl]pyridin-3-yl]-1,3-benzothiazole Chemical compound FC(F)OC1=CC=CC(C=2C(=CC=CN=2)C=2C=C3SC=NC3=CC=2)=C1 YRGPRYKHCMEFDI-UHFFFAOYSA-N 0.000 claims description 2
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ATZUYVFECYACDL-UHFFFAOYSA-N 6-[2-[3-(difluoromethoxy)phenyl]pyridin-3-yl]quinoxaline Chemical compound FC(F)OC1=CC=CC(C=2C(=CC=CN=2)C=2C=C3N=CC=NC3=CC=2)=C1 ATZUYVFECYACDL-UHFFFAOYSA-N 0.000 claims description 2
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DGAQVMYXGOKRNB-UHFFFAOYSA-N 6-[2-[3-(trifluoromethoxy)phenyl]pyridin-3-yl]quinazolin-4-amine Chemical compound C1=C2C(N)=NC=NC2=CC=C1C1=CC=CN=C1C1=CC=CC(OC(F)(F)F)=C1 DGAQVMYXGOKRNB-UHFFFAOYSA-N 0.000 claims description 2
WJOBVOSBCIKHJP-UHFFFAOYSA-N 6-[2-[3-(trifluoromethyl)phenyl]pyridin-3-yl]-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound FC(F)(F)C1=CC=CC(C=2C(=CC=CN=2)C2=CN3N=CN=C3N=C2)=C1 WJOBVOSBCIKHJP-UHFFFAOYSA-N 0.000 claims description 2
ZSEQZTWZOYXLFQ-UHFFFAOYSA-N 6-[2-[3-(trifluoromethyl)phenyl]pyridin-3-yl]-n-(3,4,5-trimethoxyphenyl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound COC1=C(OC)C(OC)=CC(NC(=O)C=2N3C=C(C=CC3=NC=2)C=2C(=NC=CC=2)C=2C=C(C=CC=2)C(F)(F)F)=C1 ZSEQZTWZOYXLFQ-UHFFFAOYSA-N 0.000 claims description 2
ZFRGWMOLMCHMLU-UHFFFAOYSA-N 6-[2-[3-(trifluoromethyl)phenyl]pyridin-3-yl]imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound FC(F)(F)C1=CC=CC(C=2C(=CC=CN=2)C2=CN3C(C#N)=CN=C3C=C2)=C1 ZFRGWMOLMCHMLU-UHFFFAOYSA-N 0.000 claims description 2
KLCSXHBBLIRFLA-UHFFFAOYSA-N 6-[2-[3-(trifluoromethyl)phenyl]pyridin-3-yl]imidazo[1,2-a]pyrimidine Chemical compound FC(F)(F)C1=CC=CC(C=2C(=CC=CN=2)C2=CN3C=CN=C3N=C2)=C1 KLCSXHBBLIRFLA-UHFFFAOYSA-N 0.000 claims description 2
SVGOJWBWUSGTRD-UHFFFAOYSA-N 6-[2-[3-(trifluoromethyl)phenyl]pyridin-3-yl]quinoxaline Chemical compound FC(F)(F)C1=CC=CC(C=2C(=CC=CN=2)C=2C=C3N=CC=NC3=CC=2)=C1 SVGOJWBWUSGTRD-UHFFFAOYSA-N 0.000 claims description 2
IWAHFLBXMKCLCH-UHFFFAOYSA-N 6-[2-[4-fluoro-3-(trifluoromethyl)phenyl]pyridin-3-yl]quinazolin-4-amine Chemical compound C1=C2C(N)=NC=NC2=CC=C1C1=CC=CN=C1C1=CC=C(F)C(C(F)(F)F)=C1 IWAHFLBXMKCLCH-UHFFFAOYSA-N 0.000 claims description 2
GBGSIRDBYKZTTO-UHFFFAOYSA-N 6-[3-(6-methylpyridin-2-yl)pyridin-2-yl]-1h-benzimidazole Chemical compound CC1=CC=CC(C=2C(=NC=CC=2)C=2C=C3NC=NC3=CC=2)=N1 GBGSIRDBYKZTTO-UHFFFAOYSA-N 0.000 claims description 2
JKRXRHAKBCDLKE-UHFFFAOYSA-N 6-[3-(6-methylpyridin-2-yl)pyridin-2-yl]quinoxaline Chemical compound CC1=CC=CC(C=2C(=NC=CC=2)C=2C=C3N=CC=NC3=CC=2)=N1 JKRXRHAKBCDLKE-UHFFFAOYSA-N 0.000 claims description 2
FJHHTVFCCQPZMT-UHFFFAOYSA-N 6-[5-(ethoxymethyl)-2-(4-fluoro-3-methylphenyl)pyridin-3-yl]quinoxaline Chemical compound C=1C=C2N=CC=NC2=CC=1C1=CC(COCC)=CN=C1C1=CC=C(F)C(C)=C1 FJHHTVFCCQPZMT-UHFFFAOYSA-N 0.000 claims description 2
BNZFCWBUKZWMLW-UHFFFAOYSA-N 6-methyl-5-[2-(3-methylphenyl)pyridin-3-yl]-1h-indazole Chemical compound CC1=CC=CC(C=2C(=CC=CN=2)C=2C(=CC=3NN=CC=3C=2)C)=C1 BNZFCWBUKZWMLW-UHFFFAOYSA-N 0.000 claims description 2
WIWKIHVLWQLBKC-UHFFFAOYSA-N 7-(1,3-benzothiazol-6-yl)-6-(4-fluoro-3-methylphenyl)-1-methyl-2,3-dihydropyrido[2,3-b][1,4]oxazine Chemical compound C=1C=C2N=CSC2=CC=1C=1C=C2N(C)CCOC2=NC=1C1=CC=C(F)C(C)=C1 WIWKIHVLWQLBKC-UHFFFAOYSA-N 0.000 claims description 2
IYHIADZTYCUVHT-UHFFFAOYSA-N 7-(1,3-benzothiazol-6-yl)-6-(4-fluoro-3-methylphenyl)-1h-pyrido[2,3-b][1,4]oxazin-2-one Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=3NC(=O)COC=3N=2)C=2C=C3SC=NC3=CC=2)=C1 IYHIADZTYCUVHT-UHFFFAOYSA-N 0.000 claims description 2
QRPNLIBENATHHK-UHFFFAOYSA-N 7-[2-(2,4,5-trifluorophenyl)pyridin-3-yl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C1=C(F)C(F)=CC(F)=C1C1=NC=CC=C1C1=CC2=NC=NN2C=C1 QRPNLIBENATHHK-UHFFFAOYSA-N 0.000 claims description 2
CJIJRUJIUQOLTE-UHFFFAOYSA-N 7-[2-(2,5-dichlorophenyl)pyridin-3-yl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound ClC1=CC=C(Cl)C(C=2C(=CC=CN=2)C2=CC3=NC=NN3C=C2)=C1 CJIJRUJIUQOLTE-UHFFFAOYSA-N 0.000 claims description 2
BNOHGGDQPIVKJN-UHFFFAOYSA-N 7-[2-(2-chloro-5-methylphenyl)pyridin-3-yl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound CC1=CC=C(Cl)C(C=2C(=CC=CN=2)C2=CC3=NC=NN3C=C2)=C1 BNOHGGDQPIVKJN-UHFFFAOYSA-N 0.000 claims description 2
YHJHPIANKNNDNW-UHFFFAOYSA-N 7-[2-(3,4,5-trifluorophenyl)pyridin-3-yl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound FC1=C(F)C(F)=CC(C=2C(=CC=CN=2)C2=CC3=NC=NN3C=C2)=C1 YHJHPIANKNNDNW-UHFFFAOYSA-N 0.000 claims description 2
UNAZHBKRNGCIOK-UHFFFAOYSA-N 7-[2-(3-chloro-4-fluorophenyl)-5-fluoropyridin-3-yl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C1=CN2N=CN=C2C=C1C1=CC(F)=CN=C1C1=CC=C(F)C(Cl)=C1 UNAZHBKRNGCIOK-UHFFFAOYSA-N 0.000 claims description 2
VPPSBOOWFMBCCP-UHFFFAOYSA-N 7-[2-(3-chloro-4-fluorophenyl)-5-methylpyridin-3-yl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C1=CN2N=CN=C2C=C1C1=CC(C)=CN=C1C1=CC=C(F)C(Cl)=C1 VPPSBOOWFMBCCP-UHFFFAOYSA-N 0.000 claims description 2
FFGGGQPNJJLSRL-UHFFFAOYSA-N 7-[2-(3-chloro-4-fluorophenyl)pyridin-3-yl]-1-methylquinoxalin-2-one Chemical compound C=1C=C2N=CC(=O)N(C)C2=CC=1C1=CC=CN=C1C1=CC=C(F)C(Cl)=C1 FFGGGQPNJJLSRL-UHFFFAOYSA-N 0.000 claims description 2
KGGBXKKTBLHJMO-UHFFFAOYSA-N 7-[2-(3-chloro-4-fluorophenyl)pyridin-3-yl]-1h-quinoxalin-2-one Chemical compound C1=C(Cl)C(F)=CC=C1C1=NC=CC=C1C1=CC=C(N=CC(=O)N2)C2=C1 KGGBXKKTBLHJMO-UHFFFAOYSA-N 0.000 claims description 2
XDSIUNAKPJLOFK-UHFFFAOYSA-N 7-[2-(3-chloro-4-fluorophenyl)pyridin-3-yl]-2-methyl-1$l^{6},2,4-benzothiadiazine 1,1-dioxide Chemical compound C1=C2S(=O)(=O)N(C)C=NC2=CC=C1C1=CC=CN=C1C1=CC=C(F)C(Cl)=C1 XDSIUNAKPJLOFK-UHFFFAOYSA-N 0.000 claims description 2
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BYLZZISVCIALTP-UHFFFAOYSA-N 7-[2-(3-chloro-4-fluorophenyl)pyridin-3-yl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C1=C(Cl)C(F)=CC=C1C1=NC=CC=C1C1=CC2=NC=NN2C=C1 BYLZZISVCIALTP-UHFFFAOYSA-N 0.000 claims description 2
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DNGNXQBVLAURSG-UHFFFAOYSA-N 7-[2-(3-chlorophenyl)-5-methoxypyridin-3-yl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C1=CN2N=CN=C2C=C1C1=CC(OC)=CN=C1C1=CC=CC(Cl)=C1 DNGNXQBVLAURSG-UHFFFAOYSA-N 0.000 claims description 2
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FBJVQBKZNYCJNQ-UHFFFAOYSA-N 7-[2-(3-methylphenyl)pyridin-3-yl]imidazo[1,5-a]pyridine Chemical compound CC1=CC=CC(C=2C(=CC=CN=2)C2=CC3=CN=CN3C=C2)=C1 FBJVQBKZNYCJNQ-UHFFFAOYSA-N 0.000 claims description 2
ZETYQGWELRYLMS-UHFFFAOYSA-N 7-[2-(3-methylphenyl)pyridin-3-yl]isoquinoline Chemical compound CC1=CC=CC(C=2C(=CC=CN=2)C=2C=C3C=NC=CC3=CC=2)=C1 ZETYQGWELRYLMS-UHFFFAOYSA-N 0.000 claims description 2
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ATDONOBDUFWPEW-UHFFFAOYSA-N ethyl 5-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]pyrazolo[1,5-a]pyridine-3-carboxylate Chemical compound C=1C2=C(C(=O)OCC)C=NN2C=CC=1C1=CC=CN=C1C1=CC=C(F)C(C)=C1 ATDONOBDUFWPEW-UHFFFAOYSA-N 0.000 claims description 2
LQDZUBGXRIAHCK-UHFFFAOYSA-N ethyl 5-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]pyrazolo[1,5-a]pyrimidine-3-carboxylate Chemical compound N=1C2=C(C(=O)OCC)C=NN2C=CC=1C1=CC=CN=C1C1=CC=C(F)C(C)=C1 LQDZUBGXRIAHCK-UHFFFAOYSA-N 0.000 claims description 2
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OPAHOWSYOZEWMV-UHFFFAOYSA-N methyl 6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carboxylate Chemical compound C=1N2C(C(=O)OC)=CN=C2C=CC=1C1=CC=CN=C1C1=CC=C(F)C(C)=C1 OPAHOWSYOZEWMV-UHFFFAOYSA-N 0.000 claims description 2
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QSVMFAJNGDIUII-UHFFFAOYSA-N n,n-dimethyl-6-[2-[3-(trifluoromethyl)phenyl]pyridin-3-yl]imidazo[1,2-a]pyridin-3-amine Chemical compound C=1N2C(N(C)C)=CN=C2C=CC=1C1=CC=CN=C1C1=CC=CC(C(F)(F)F)=C1 QSVMFAJNGDIUII-UHFFFAOYSA-N 0.000 claims description 2
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UVGKCFOYLJHICK-UHFFFAOYSA-N n-(2,3-dihydroxypropyl)-6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C2=CN3C(C(=O)NCC(O)CO)=CN=C3C=C2)=C1 UVGKCFOYLJHICK-UHFFFAOYSA-N 0.000 claims description 2
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KUIMEKTWXKDPJQ-VXKWHMMOSA-N n-[(1s,2s)-2-aminocyclohexyl]-6-[2-(4-fluoro-3-methylphenyl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=C(F)C(C)=CC(C=2C(=CC=CN=2)C2=CN3C(C(=O)N[C@@H]4[C@H](CCCC4)N)=CN=C3C=C2)=C1 KUIMEKTWXKDPJQ-VXKWHMMOSA-N 0.000 claims description 2
QVSRTBSGOJHAHA-UHFFFAOYSA-N n-[(2-ethyl-1h-imidazol-5-yl)methyl]-6-(4-fluoro-3-methylphenyl)-5-imidazo[1,2-a]pyridin-6-ylpyridin-3-amine Chemical compound N1C(CC)=NC=C1CNC(C=C1C2=CN3C=CN=C3C=C2)=CN=C1C1=CC=C(F)C(C)=C1 QVSRTBSGOJHAHA-UHFFFAOYSA-N 0.000 claims description 2
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JP2015535846A 2012-10-05 2013-10-04 Ｇｄｆ−８阻害剤 Expired - Fee Related JP6457942B2 (ja)