SG175355A1

SG175355A1 - Pyridinone antagonists of alpha-4 integrins

Pyridinone antagonists of alpha-4 integrins Download PDF

Info

Publication number: SG175355A1
Authority: SG; Singapore
Prior art keywords: dihydro; inden; dihydropyridine; carboxamide; oxo
Prior art date: 2009-04-27

Application number

SG2011078409A

Other languages

English (en)

Inventor

Ying-Zi Xu

Shendong Yuan

David Wone

Andrei Konradi

Original Assignee

Elan Pharm Inc

Priority date

2009-04-27

Filing date

2010-04-27

Publication date

2011-12-29

2010-04-27 Application filed by Elan Pharm Inc filed Critical Elan Pharm Inc

2011-12-29 Publication of SG175355A1 publication Critical patent/SG175355A1/en

Links

108010044426 integrins Proteins 0.000 title claims description 73
102000006495 integrins Human genes 0.000 title claims description 73
239000005557 antagonist Substances 0.000 title abstract description 6
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 title description 4
101001002508 Homo sapiens Immunoglobulin-binding protein 1 Proteins 0.000 title 1
102100021042 Immunoglobulin-binding protein 1 Human genes 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 272
238000000034 method Methods 0.000 claims abstract description 171
239000000203 mixture Substances 0.000 claims abstract description 163
150000003839 salts Chemical class 0.000 claims abstract description 40
208000011231 Crohn disease Diseases 0.000 claims abstract description 24
239000012453 solvate Substances 0.000 claims abstract description 24
206010009900 Colitis ulcerative Diseases 0.000 claims abstract description 13
201000006704 Ulcerative Colitis Diseases 0.000 claims abstract description 13
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
-1 phenyloxy Chemical group 0.000 claims description 102
125000000217 alkyl group Chemical group 0.000 claims description 87
125000003118 aryl group Chemical group 0.000 claims description 67
125000000753 cycloalkyl group Chemical group 0.000 claims description 58
125000001072 heteroaryl group Chemical group 0.000 claims description 57
125000004404 heteroalkyl group Chemical group 0.000 claims description 52
238000003556 assay Methods 0.000 claims description 47
230000027455 binding Effects 0.000 claims description 35
229910052736 halogen Inorganic materials 0.000 claims description 30
239000003446 ligand Substances 0.000 claims description 30
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
150000002367 halogens Chemical class 0.000 claims description 28
229910052757 nitrogen Inorganic materials 0.000 claims description 22
125000004076 pyridyl group Chemical group 0.000 claims description 21
125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims description 20
125000004429 atom Chemical group 0.000 claims description 18
MGTSRKSZRYSNRG-UHFFFAOYSA-N 1-(4-bromo-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C1CC=2C(Br)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=NC=C1 MGTSRKSZRYSNRG-UHFFFAOYSA-N 0.000 claims description 15
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 15
229910052799 carbon Inorganic materials 0.000 claims description 15
238000000099 in vitro assay Methods 0.000 claims description 14
229910052731 fluorine Inorganic materials 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 12
208000027866 inflammatory disease Diseases 0.000 claims description 12
125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
DLWITLRKVVCPBW-UHFFFAOYSA-N 1-(4-methoxy-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C1CC=2C(OC)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=NC=C1 DLWITLRKVVCPBW-UHFFFAOYSA-N 0.000 claims description 9
102000016359 Fibronectins Human genes 0.000 claims description 9
108010067306 Fibronectins Proteins 0.000 claims description 9
BAAPDTAQLOBDFS-UHFFFAOYSA-N tert-butyl 4-[1-[3-[(4-chlorophenyl)carbamoyl]-2-oxopyridin-1-yl]-2,3-dihydro-1h-inden-4-yl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=CC=CC2=C1CCC2N1C(=O)C(C(=O)NC=2C=CC(Cl)=CC=2)=CC=C1 BAAPDTAQLOBDFS-UHFFFAOYSA-N 0.000 claims description 8
229930192474 thiophene Natural products 0.000 claims description 8
NOXXXWUZNCFIGU-UHFFFAOYSA-N 1-(6-methoxy-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C12=CC(OC)=CC=C2CCC1N(C1=O)C=CC=C1C(=O)NC1=CC=NC=C1 NOXXXWUZNCFIGU-UHFFFAOYSA-N 0.000 claims description 7
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
108010000134 Vascular Cell Adhesion Molecule-1 Proteins 0.000 claims description 6
102100023543 Vascular cell adhesion protein 1 Human genes 0.000 claims description 6
125000002252 acyl group Chemical group 0.000 claims description 6
239000003937 drug carrier Substances 0.000 claims description 6
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
WQZLKGRZMJEWEP-UHFFFAOYSA-N tert-butyl n-[2-[2-[2-[2-[4-[1-[3-[(4-chlorophenyl)carbamoyl]-2-oxopyridin-1-yl]-2,3-dihydro-1h-inden-4-yl]piperazin-1-yl]-2-oxoethoxy]ethoxy]ethoxy]ethyl]carbamate Chemical compound C1CN(C(=O)COCCOCCOCCNC(=O)OC(C)(C)C)CCN1C1=CC=CC2=C1CCC2N1C(=O)C(C(=O)NC=2C=CC(Cl)=CC=2)=CC=C1 WQZLKGRZMJEWEP-UHFFFAOYSA-N 0.000 claims description 5
KGZINKUHIUGADJ-UHFFFAOYSA-N tert-butyl n-[2-[2-[2-[[1-[2-oxo-3-[(4-phenylphenyl)carbamoyl]pyridin-1-yl]-2,3-dihydro-1h-inden-4-yl]oxy]ethoxy]ethoxy]ethyl]carbamate Chemical compound C1CC=2C(OCCOCCOCCNC(=O)OC(C)(C)C)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC(C=C1)=CC=C1C1=CC=CC=C1 KGZINKUHIUGADJ-UHFFFAOYSA-N 0.000 claims description 5
CCKYEVWPJBLGSL-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-1-yl)-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C=1C=CN(C2C3=CC=CC=C3CC2)C(=O)C=1C(=O)NC1=CC=NC=C1 CCKYEVWPJBLGSL-UHFFFAOYSA-N 0.000 claims description 4
WOJIKDNMHKTBQP-UHFFFAOYSA-N 1-(4-bromo-2,3-dihydro-1h-inden-1-yl)-n-(4-chlorophenyl)-2-oxopyridine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)C(C1=O)=CC=CN1C1C(C=CC=C2Br)=C2CC1 WOJIKDNMHKTBQP-UHFFFAOYSA-N 0.000 claims description 4
FNFRZOUOMFBWCP-UHFFFAOYSA-N 1-(4-chloro-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C1CC=2C(Cl)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=NC=C1 FNFRZOUOMFBWCP-UHFFFAOYSA-N 0.000 claims description 4
KPWKCFBQCLGQGD-UHFFFAOYSA-N 1-(4-cyano-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C=1C=CN(C2C3=C(C(=CC=C3)C#N)CC2)C(=O)C=1C(=O)NC1=CC=NC=C1 KPWKCFBQCLGQGD-UHFFFAOYSA-N 0.000 claims description 4
QIUSZEHWTSLBQF-UHFFFAOYSA-N 1-(6-bromo-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C12=CC(Br)=CC=C2CCC1N(C1=O)C=CC=C1C(=O)NC1=CC=NC=C1 QIUSZEHWTSLBQF-UHFFFAOYSA-N 0.000 claims description 4
BGQSTCMBYRTACM-UHFFFAOYSA-N 1-(6-bromo-2,3-dihydro-1h-inden-1-yl)-n-(4-chlorophenyl)-2-oxopyridine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)C(C1=O)=CC=CN1C1C2=CC(Br)=CC=C2CC1 BGQSTCMBYRTACM-UHFFFAOYSA-N 0.000 claims description 4
CCKYEVWPJBLGSL-SFHVURJKSA-N 1-[(1s)-2,3-dihydro-1h-inden-1-yl]-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C=1C=CN([C@@H]2C3=CC=CC=C3CC2)C(=O)C=1C(=O)NC1=CC=NC=C1 CCKYEVWPJBLGSL-SFHVURJKSA-N 0.000 claims description 4
UPUNKRHTHQKKLY-UHFFFAOYSA-N 2-oxo-1-(4-propan-2-yloxy-2,3-dihydro-1h-inden-1-yl)-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C1CC=2C(OC(C)C)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=NC=C1 UPUNKRHTHQKKLY-UHFFFAOYSA-N 0.000 claims description 4
238000012875 competitive assay Methods 0.000 claims description 4
BYQYNXXZYYARKU-UHFFFAOYSA-N 1-(4-morpholin-4-yl-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-phenylpyridine-3-carboxamide Chemical compound C=1C=CN(C2C3=C(C(=CC=C3)N3CCOCC3)CC2)C(=O)C=1C(=O)NC1=CC=CC=C1 BYQYNXXZYYARKU-UHFFFAOYSA-N 0.000 claims description 3
MYVYMEPVMOHNMF-UHFFFAOYSA-N 1-(4-nitro-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C1CC=2C([N+](=O)[O-])=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=NC=C1 MYVYMEPVMOHNMF-UHFFFAOYSA-N 0.000 claims description 3
102000004264 Osteopontin Human genes 0.000 claims description 3
108010081689 Osteopontin Proteins 0.000 claims description 3
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 3
PQXYVIURQPDYJN-UHFFFAOYSA-N n-(4-bromophenyl)-2-oxo-1-(4-piperazin-1-yl-2,3-dihydro-1h-inden-1-yl)pyridine-3-carboxamide Chemical compound C1=CC(Br)=CC=C1NC(=O)C(C1=O)=CC=CN1C1C(C=CC=C2N3CCNCC3)=C2CC1 PQXYVIURQPDYJN-UHFFFAOYSA-N 0.000 claims description 3
HWEOYYUDLJSRQR-UHFFFAOYSA-N n-(4-chlorophenyl)-1-[4-(4-hydroxypiperidin-1-yl)-2,3-dihydro-1h-inden-1-yl]-2-oxopyridine-3-carboxamide Chemical compound C1CC(O)CCN1C1=CC=CC2=C1CCC2N1C(=O)C(C(=O)NC=2C=CC(Cl)=CC=2)=CC=C1 HWEOYYUDLJSRQR-UHFFFAOYSA-N 0.000 claims description 3
FCYVRKSBZJTFJV-UHFFFAOYSA-N n-(4-fluorophenyl)-2-oxo-1-(4-piperazin-1-yl-2,3-dihydro-1h-inden-1-yl)pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1NC(=O)C(C1=O)=CC=CN1C1C(C=CC=C2N3CCNCC3)=C2CC1 FCYVRKSBZJTFJV-UHFFFAOYSA-N 0.000 claims description 3
RJTXLRFGKBANFQ-UHFFFAOYSA-N n-[4-(difluoromethoxy)phenyl]-1-(4-morpholin-4-yl-2,3-dihydro-1h-inden-1-yl)-2-oxopyridine-3-carboxamide Chemical compound C1=CC(OC(F)F)=CC=C1NC(=O)C(C1=O)=CC=CN1C1C(C=CC=C2N3CCOCC3)=C2CC1 RJTXLRFGKBANFQ-UHFFFAOYSA-N 0.000 claims description 3
XIZIAZLMUKPKBK-UHFFFAOYSA-N tert-butyl 4-[1-[3-[(4-fluorophenyl)carbamoyl]-2-oxopyridin-1-yl]-2,3-dihydro-1h-inden-4-yl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=CC=CC2=C1CCC2N1C(=O)C(C(=O)NC=2C=CC(F)=CC=2)=CC=C1 XIZIAZLMUKPKBK-UHFFFAOYSA-N 0.000 claims description 3
XFVUNFLEGLIUBD-UHFFFAOYSA-N 1-(4-acetamido-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C1CC=2C(NC(=O)C)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=NC=C1 XFVUNFLEGLIUBD-UHFFFAOYSA-N 0.000 claims description 2
MDKSZGHWXVNNHA-UHFFFAOYSA-N 1-(4-methoxy-2,3-dihydro-1h-inden-1-yl)-n-[4-(4-methoxyphenoxy)phenyl]-2-oxopyridine-3-carboxamide Chemical compound C1=CC(OC)=CC=C1OC(C=C1)=CC=C1NC(=O)C(C1=O)=CC=CN1C1C(C=CC=C2OC)=C2CC1 MDKSZGHWXVNNHA-UHFFFAOYSA-N 0.000 claims description 2
IQQACCNUSCXUCA-UHFFFAOYSA-N 1-(4-methylsulfanyl-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C1CC=2C(SC)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=NC=C1 IQQACCNUSCXUCA-UHFFFAOYSA-N 0.000 claims description 2
RAWJRBXOODIXOY-UHFFFAOYSA-N 1-(7,8-dihydro-6h-cyclopenta[g][1,3]benzodioxol-6-yl)-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C=1C=CN(C2C3=C(C=4OCOC=4C=C3)CC2)C(=O)C=1C(=O)NC1=CC=NC=C1 RAWJRBXOODIXOY-UHFFFAOYSA-N 0.000 claims description 2
CCKYEVWPJBLGSL-GOSISDBHSA-N 1-[(1r)-2,3-dihydro-1h-inden-1-yl]-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C=1C=CN([C@H]2C3=CC=CC=C3CC2)C(=O)C=1C(=O)NC1=CC=NC=C1 CCKYEVWPJBLGSL-GOSISDBHSA-N 0.000 claims description 2
ZVGZFYUWMIHDJB-UHFFFAOYSA-N 1-[4-(4-acetylpiperazin-1-yl)-2,3-dihydro-1h-inden-1-yl]-n-(4-chlorophenyl)-2-oxopyridine-3-carboxamide Chemical compound C1CN(C(=O)C)CCN1C1=CC=CC2=C1CCC2N1C(=O)C(C(=O)NC=2C=CC(Cl)=CC=2)=CC=C1 ZVGZFYUWMIHDJB-UHFFFAOYSA-N 0.000 claims description 2
NRVCMCNZPQSNPP-UHFFFAOYSA-N 1-[4-(4-hydroxypiperidin-1-yl)-2,3-dihydro-1h-inden-1-yl]-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C1CC(O)CCN1C1=CC=CC2=C1CCC2N1C(=O)C(C(=O)NC=2C=CN=CC=2)=CC=C1 NRVCMCNZPQSNPP-UHFFFAOYSA-N 0.000 claims description 2
MUZKIXYETQBYFS-UHFFFAOYSA-N 1-[4-(dimethylamino)-2,3-dihydro-1h-inden-1-yl]-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C1CC=2C(N(C)C)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=NC=C1 MUZKIXYETQBYFS-UHFFFAOYSA-N 0.000 claims description 2
DOVUJQMOXPYQMQ-UHFFFAOYSA-N 1-[4-(methylcarbamoyl)-2,3-dihydro-1h-inden-1-yl]-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C1CC=2C(C(=O)NC)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=NC=C1 DOVUJQMOXPYQMQ-UHFFFAOYSA-N 0.000 claims description 2
XUWPENNWWFSKNQ-UHFFFAOYSA-N 1-[4-[4-[2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]acetyl]piperazin-1-yl]-2,3-dihydro-1h-inden-1-yl]-n-(4-chlorophenyl)-2-oxopyridine-3-carboxamide Chemical compound C1CN(C(=O)COCCOCCOCCN)CCN1C1=CC=CC2=C1CCC2N1C(=O)C(C(=O)NC=2C=CC(Cl)=CC=2)=CC=C1 XUWPENNWWFSKNQ-UHFFFAOYSA-N 0.000 claims description 2
JTWIFVZROQHSFK-UHFFFAOYSA-N n-(4-bromophenyl)-1-(4-hydroxy-2,3-dihydro-1h-inden-1-yl)-2-oxopyridine-3-carboxamide Chemical compound C1CC=2C(O)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=C(Br)C=C1 JTWIFVZROQHSFK-UHFFFAOYSA-N 0.000 claims description 2
TUYLNPCHEGGGNQ-UHFFFAOYSA-N n-(4-bromophenyl)-1-(4-methoxy-2,3-dihydro-1h-inden-1-yl)-2-oxopyridine-3-carboxamide Chemical compound C1CC=2C(OC)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=C(Br)C=C1 TUYLNPCHEGGGNQ-UHFFFAOYSA-N 0.000 claims description 2
IWSACEXKDIDSSW-UHFFFAOYSA-N n-(4-bromophenyl)-1-[4-(2-hydroxyethoxy)-2,3-dihydro-1h-inden-1-yl]-2-oxopyridine-3-carboxamide Chemical compound C1CC=2C(OCCO)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=C(Br)C=C1 IWSACEXKDIDSSW-UHFFFAOYSA-N 0.000 claims description 2
ZPWCNOMGRYGTHP-UHFFFAOYSA-N n-(4-chlorophenyl)-1-[4-(4-methylpiperazin-1-yl)-2,3-dihydro-1h-inden-1-yl]-2-oxopyridine-3-carboxamide Chemical compound C1CN(C)CCN1C1=CC=CC2=C1CCC2N1C(=O)C(C(=O)NC=2C=CC(Cl)=CC=2)=CC=C1 ZPWCNOMGRYGTHP-UHFFFAOYSA-N 0.000 claims description 2
KFZGMLHEJPJGPF-UHFFFAOYSA-N n-(4-chlorophenyl)-2-oxo-1-(4-piperazin-1-yl-2,3-dihydro-1h-inden-1-yl)pyridine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)C(C1=O)=CC=CN1C1C(C=CC=C2N3CCNCC3)=C2CC1 KFZGMLHEJPJGPF-UHFFFAOYSA-N 0.000 claims description 2
GTPRHPCXFBCGQK-UHFFFAOYSA-N tert-butyl 4-[1-[2-oxo-3-(pyridin-4-ylcarbamoyl)pyridin-1-yl]-2,3-dihydro-1h-inden-4-yl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=CC=CC2=C1CCC2N1C(=O)C(C(=O)NC=2C=CN=CC=2)=CC=C1 GTPRHPCXFBCGQK-UHFFFAOYSA-N 0.000 claims description 2
WFOKKBXIFGWUGP-UHFFFAOYSA-N 1-(4-methoxy-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-(4-phenylphenyl)pyridine-3-carboxamide Chemical compound C1CC=2C(OC)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC(C=C1)=CC=C1C1=CC=CC=C1 WFOKKBXIFGWUGP-UHFFFAOYSA-N 0.000 claims 3
KPLCFCSBJAOAAU-UHFFFAOYSA-N 1-(4-cyclopropyl-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C=1C=CN(C2C3=C(C(=CC=C3)C3CC3)CC2)C(=O)C=1C(=O)NC1=CC=NC=C1 KPLCFCSBJAOAAU-UHFFFAOYSA-N 0.000 claims 1
PQLTUTXADSMBCD-UHFFFAOYSA-N 1-(4-hydroxy-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-(4-phenylphenyl)pyridine-3-carboxamide Chemical compound C1CC=2C(O)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC(C=C1)=CC=C1C1=CC=CC=C1 PQLTUTXADSMBCD-UHFFFAOYSA-N 0.000 claims 1
ZWTIJGFALYXVJT-UHFFFAOYSA-N 1-(4-methoxy-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-phenylpyridine-3-carboxamide Chemical compound C1CC=2C(OC)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=CC=C1 ZWTIJGFALYXVJT-UHFFFAOYSA-N 0.000 claims 1
SNCIYGCAKRMIIC-UHFFFAOYSA-N 1-(4-methoxy-2,3-dihydro-1h-inden-1-yl)-n-[4-(2-methoxyphenyl)phenyl]-2-oxopyridine-3-carboxamide Chemical compound C1CC=2C(OC)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC(C=C1)=CC=C1C1=CC=CC=C1OC SNCIYGCAKRMIIC-UHFFFAOYSA-N 0.000 claims 1
JVBDRUXNLPUACH-UHFFFAOYSA-N 1-(4-methoxy-2,3-dihydro-1h-inden-1-yl)-n-[4-(4-methoxyphenyl)phenyl]-2-oxopyridine-3-carboxamide Chemical compound C1=CC(OC)=CC=C1C(C=C1)=CC=C1NC(=O)C(C1=O)=CC=CN1C1C(C=CC=C2OC)=C2CC1 JVBDRUXNLPUACH-UHFFFAOYSA-N 0.000 claims 1
MSJRPOFHRHBTEH-UHFFFAOYSA-N 1-(4-methylsulfonyl-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-pyridin-4-ylpyridine-3-carboxamide Chemical compound C1CC=2C(S(=O)(=O)C)=CC=CC=2C1N(C1=O)C=CC=C1C(=O)NC1=CC=NC=C1 MSJRPOFHRHBTEH-UHFFFAOYSA-N 0.000 claims 1
FQGJWZPCMJLUFK-UHFFFAOYSA-N 1-(4-morpholin-4-yl-2,3-dihydro-1h-inden-1-yl)-2-oxo-n-(4-phenoxyphenyl)pyridine-3-carboxamide Chemical compound C=1C=CN(C2C3=C(C(=CC=C3)N3CCOCC3)CC2)C(=O)C=1C(=O)NC(C=C1)=CC=C1OC1=CC=CC=C1 FQGJWZPCMJLUFK-UHFFFAOYSA-N 0.000 claims 1
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