JP2013515070A5 - - Google Patents
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- Publication number
- JP2013515070A5 JP2013515070A5 JP2012546120A JP2012546120A JP2013515070A5 JP 2013515070 A5 JP2013515070 A5 JP 2013515070A5 JP 2012546120 A JP2012546120 A JP 2012546120A JP 2012546120 A JP2012546120 A JP 2012546120A JP 2013515070 A5 JP2013515070 A5 JP 2013515070A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- pyridine
- indazol
- imidazo
- carboxamide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims description 217
- 150000001875 compounds Chemical class 0.000 claims description 213
- -1 pyridinonyl Chemical group 0.000 claims description 181
- 125000003545 alkoxy group Chemical group 0.000 claims description 159
- 125000001424 substituent group Chemical group 0.000 claims description 58
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 52
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 43
- 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 36
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
- 125000005842 heteroatom Chemical group 0.000 claims description 28
- DFPAKSUCGFBDDF-UHFFFAOYSA-N nicotinic acid amide Natural products NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 26
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 125000000623 heterocyclic group Chemical group 0.000 claims description 21
- 230000008878 coupling Effects 0.000 claims description 20
- 238000010168 coupling process Methods 0.000 claims description 20
- 238000005859 coupling reaction Methods 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 235000005152 nicotinamide Nutrition 0.000 claims description 16
- 239000011570 nicotinamide Substances 0.000 claims description 16
- 125000004076 pyridyl group Chemical group 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 229910052763 palladium Inorganic materials 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims description 10
- 229910017051 nitrogen difluoride Inorganic materials 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 8
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 8
- 239000003638 chemical reducing agent Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 8
- 125000006413 ring segment Chemical group 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 239000003446 ligand Substances 0.000 claims description 6
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 6
- 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 125000004990 dihydroxyalkyl group Chemical group 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 238000007363 ring formation reaction Methods 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- LBXXOGDHNJALPH-UHFFFAOYSA-N n-[3-ethyl-1-[(1-ethylpyrazol-3-yl)methyl]indazol-4-yl]-7-(1-methylpyrazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(=CC4=NC=3)C3=CN(C)N=C3)=C2C(CC)=NN1CC=1C=CN(CC)N=1 LBXXOGDHNJALPH-UHFFFAOYSA-N 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 claims description 2
- 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 claims description 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 2
- JUQWFONZRDXAAB-UHFFFAOYSA-N 1-methyl-1-oxidopiperazin-1-ium Chemical compound C[N+]1([O-])CCNCC1 JUQWFONZRDXAAB-UHFFFAOYSA-N 0.000 claims description 2
- 125000000586 2-(4-morpholinyl)ethoxy group Chemical group [H]C([H])(O*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 2
- OVWQDUPSSYKQGP-UHFFFAOYSA-N 3-n-[3-ethyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-n,7-n-dimethylimidazo[1,2-a]pyridine-3,7-dicarboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(=CC4=NC=3)C(=O)N(C)C)=C2C(CC)=NN1CC1=CC=CC(C)=N1 OVWQDUPSSYKQGP-UHFFFAOYSA-N 0.000 claims description 2
- GXEOVLLINHXMNO-UHFFFAOYSA-N 3-n-[3-ethyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-n-(1-methylpyrrolidin-3-yl)imidazo[1,2-a]pyridine-3,7-dicarboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(=CC4=NC=3)C(=O)NC3CN(C)CC3)=C2C(CC)=NN1CC1=CC=CC(C)=N1 GXEOVLLINHXMNO-UHFFFAOYSA-N 0.000 claims description 2
- PODIAAIBRDQLDK-UHFFFAOYSA-N 3-n-[3-ethyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-n-methylimidazo[1,2-a]pyridine-3,7-dicarboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(=CC4=NC=3)C(=O)NC)=C2C(CC)=NN1CC1=CC=CC(C)=N1 PODIAAIBRDQLDK-UHFFFAOYSA-N 0.000 claims description 2
- SKNVXLIQXHNREQ-UHFFFAOYSA-N 3-n-[3-ethyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-n-pyrrolidin-3-ylimidazo[1,2-a]pyridine-3,7-dicarboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(=CC4=NC=3)C(=O)NC3CNCC3)=C2C(CC)=NN1CC1=CC=CC(C)=N1 SKNVXLIQXHNREQ-UHFFFAOYSA-N 0.000 claims description 2
- GMVHJGPRWKGHNF-UHFFFAOYSA-N 7-(2,3-dimethylimidazol-4-yl)-n-[3-ethyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(=CC4=NC=3)C=3N(C(C)=NC=3)C)=C2C(CC)=NN1CC1=CC=CC(C)=N1 GMVHJGPRWKGHNF-UHFFFAOYSA-N 0.000 claims description 2
- VBCOTGUQEBOJLR-UHFFFAOYSA-N 7-(2-acetamidoethylsulfanyl)-n-[3-ethyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(SCCNC(C)=O)=CC4=NC=3)=C2C(CC)=NN1CC1=CC=CC(C)=N1 VBCOTGUQEBOJLR-UHFFFAOYSA-N 0.000 claims description 2
- SBSRNDXXOQZCEZ-UHFFFAOYSA-N 7-(2-methoxyethoxy)-n-[3-methoxy-1-[(6-methylpyridin-3-yl)methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C=1N=C2C=C(OCCOC)C=CN2C=1C(=O)NC(C=1C(OC)=N2)=CC=CC=1N2CC1=CC=C(C)N=C1 SBSRNDXXOQZCEZ-UHFFFAOYSA-N 0.000 claims description 2
- MBVYQQZVACAOHH-UHFFFAOYSA-N 7-[(dimethylamino)methyl]-n-[3-ethyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(CN(C)C)=CC4=NC=3)=C2C(CC)=NN1CC1=CC=CC(C)=N1 MBVYQQZVACAOHH-UHFFFAOYSA-N 0.000 claims description 2
- HUKITRXOTUDTJK-UHFFFAOYSA-N 7-[5-[(dimethylamino)methyl]furan-2-yl]-n-[1-[(1,5-dimethylpyrazol-3-yl)methyl]-3-ethylindazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(=CC4=NC=3)C=3OC(CN(C)C)=CC=3)=C2C(CC)=NN1CC=1C=C(C)N(C)N=1 HUKITRXOTUDTJK-UHFFFAOYSA-N 0.000 claims description 2
- KAFOGPUHXJUEJA-UHFFFAOYSA-N 7-bromo-n-[3-cyclopropyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound CC1=CC=CC(CN2C3=CC=CC(NC(=O)C=4N5C=CC(Br)=CC5=NC=4)=C3C(C3CC3)=N2)=N1 KAFOGPUHXJUEJA-UHFFFAOYSA-N 0.000 claims description 2
- WZNXBTYYIBKDNY-UHFFFAOYSA-N 7-chloro-n-[3-cyclopropyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound CC1=CC=CC(CN2C3=CC=CC(NC(=O)C=4N5C=CC(Cl)=CC5=NC=4)=C3C(C3CC3)=N2)=N1 WZNXBTYYIBKDNY-UHFFFAOYSA-N 0.000 claims description 2
- POOPWPIOIMBTOH-UHFFFAOYSA-N 8-oxa-3-azabicyclo[3.2.1]octane Chemical compound C1NCC2CCC1O2 POOPWPIOIMBTOH-UHFFFAOYSA-N 0.000 claims description 2
- 208000023275 Autoimmune disease Diseases 0.000 claims description 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 claims description 2
- 208000002193 Pain Diseases 0.000 claims description 2
- 239000012190 activator Substances 0.000 claims description 2
- 210000000988 bone and bone Anatomy 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 150000001723 carbon free-radicals Chemical class 0.000 claims description 2
- 239000007822 coupling agent Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- BOWAPXSQNSVVRX-UHFFFAOYSA-N ethyl 3-[[3-ethyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]carbamoyl]imidazo[1,2-a]pyridine-7-carboxylate Chemical compound C=1N=C2C=C(C(=O)OCC)C=CN2C=1C(=O)NC(C=1C(CC)=N2)=CC=CC=1N2CC1=CC=CC(C)=N1 BOWAPXSQNSVVRX-UHFFFAOYSA-N 0.000 claims description 2
- 208000027866 inflammatory disease Diseases 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- STUHQDIOZQUPGP-UHFFFAOYSA-N morpholin-4-ium-4-carboxylate Chemical compound OC(=O)N1CCOCC1 STUHQDIOZQUPGP-UHFFFAOYSA-N 0.000 claims description 2
- TZOZWWBEANSCHO-UHFFFAOYSA-N n-(1-benzyl-5-chloro-3-ethylindazol-4-yl)-7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=C(Cl)C(NC(=O)C=3N4C=CC(OCCOC)=CC4=NC=3)=C2C(CC)=NN1CC1=CC=CC=C1 TZOZWWBEANSCHO-UHFFFAOYSA-N 0.000 claims description 2
- IQUITEGKUMROTP-UHFFFAOYSA-N n-[1-[(1,5-dimethylpyrazol-3-yl)methyl]-3-ethylindazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC=CC4=NC=3)=C2C(CC)=NN1CC=1C=C(C)N(C)N=1 IQUITEGKUMROTP-UHFFFAOYSA-N 0.000 claims description 2
- KMTQJFVXUZNLJB-UHFFFAOYSA-N n-[1-[(1,6-dimethyl-2-oxopyridin-3-yl)methyl]-3-ethylindazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC=CC4=NC=3)=C2C(CC)=NN1CC1=CC=C(C)N(C)C1=O KMTQJFVXUZNLJB-UHFFFAOYSA-N 0.000 claims description 2
- OLGIGQBWLWENEI-UHFFFAOYSA-N n-[1-[(6-ethoxypyridin-2-yl)methyl]-3-ethylindazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound CCOC1=CC=CC(CN2C3=CC=CC(NC(=O)C=4N5C=CC=CC5=NC=4)=C3C(CC)=N2)=N1 OLGIGQBWLWENEI-UHFFFAOYSA-N 0.000 claims description 2
- TXWIDKJIHCZZPC-UHFFFAOYSA-N n-[1-[[1-(cyclopropylmethyl)pyrazol-4-yl]methyl]-3-ethylindazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC=CC4=NC=3)=C2C(CC)=NN1CC(=C1)C=NN1CC1CC1 TXWIDKJIHCZZPC-UHFFFAOYSA-N 0.000 claims description 2
- WTSHRQHQDOBZTF-UHFFFAOYSA-N n-[1-[[2-(2,3-dihydroxypropyl)pyrazol-3-yl]methyl]-3-ethylindazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC=CC4=NC=3)=C2C(CC)=NN1CC1=CC=NN1CC(O)CO WTSHRQHQDOBZTF-UHFFFAOYSA-N 0.000 claims description 2
- CWLAWXOXPOZUCS-UHFFFAOYSA-N n-[1-[[6-(2,3-dihydroxypropoxy)pyridin-2-yl]methyl]-3-ethylindazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC=CC4=NC=3)=C2C(CC)=NN1CC1=CC=CC(OCC(O)CO)=N1 CWLAWXOXPOZUCS-UHFFFAOYSA-N 0.000 claims description 2
- GXXWGDNJTAQYRE-UHFFFAOYSA-N n-[1-[[6-(2-aminoethoxy)pyridin-2-yl]methyl]-3-ethylindazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC=CC4=NC=3)=C2C(CC)=NN1CC1=CC=CC(OCCN)=N1 GXXWGDNJTAQYRE-UHFFFAOYSA-N 0.000 claims description 2
- ARZVFJGPRSELGZ-UHFFFAOYSA-N n-[1-[[6-(3-aminopropoxy)pyridin-2-yl]methyl]-3-ethylindazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC=CC4=NC=3)=C2C(CC)=NN1CC1=CC=CC(OCCCN)=N1 ARZVFJGPRSELGZ-UHFFFAOYSA-N 0.000 claims description 2
- MTDIXALCKOOUHU-UHFFFAOYSA-N n-[1-[[6-(4-aminopiperidin-1-yl)pyridin-2-yl]methyl]-3-ethylindazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC=CC4=NC=3)=C2C(CC)=NN1CC(N=1)=CC=CC=1N1CCC(N)CC1 MTDIXALCKOOUHU-UHFFFAOYSA-N 0.000 claims description 2
- KCHPECAOGIUMIJ-UHFFFAOYSA-N n-[1-[[6-[3-(dimethylamino)propoxy]pyridin-2-yl]methyl]-3-ethylindazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC=CC4=NC=3)=C2C(CC)=NN1CC1=CC=CC(OCCCN(C)C)=N1 KCHPECAOGIUMIJ-UHFFFAOYSA-N 0.000 claims description 2
- MXKIRYLRJYOWKO-UHFFFAOYSA-N n-[3-cyclopropyl-1-[(1-methyl-2-oxopyridin-3-yl)methyl]indazol-4-yl]-7-[2-(4-methylpiperazin-1-yl)ethoxy]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1CN(C)CCN1CCOC1=CC2=NC=C(C(=O)NC=3C=4C(C5CC5)=NN(CC=5C(N(C)C=CC=5)=O)C=4C=CC=3)N2C=C1 MXKIRYLRJYOWKO-UHFFFAOYSA-N 0.000 claims description 2
- NQLXMWXWXOIRRR-UHFFFAOYSA-N n-[3-cyclopropyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-[2-(2-ethenoxyethoxy)ethoxy]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound CC1=CC=CC(CN2C3=CC=CC(NC(=O)C=4N5C=CC(OCCOCCOC=C)=CC5=NC=4)=C3C(C3CC3)=N2)=N1 NQLXMWXWXOIRRR-UHFFFAOYSA-N 0.000 claims description 2
- MJSXGOGSMMWYMH-UHFFFAOYSA-N n-[3-cyclopropyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-[2-(4-methyl-4-oxidopiperazin-4-ium-1-yl)ethoxy]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound CC1=CC=CC(CN2C3=CC=CC(NC(=O)C=4N5C=CC(OCCN6CC[N+](C)([O-])CC6)=CC5=NC=4)=C3C(C3CC3)=N2)=N1 MJSXGOGSMMWYMH-UHFFFAOYSA-N 0.000 claims description 2
- JUPOTOIJLKDAPF-UHFFFAOYSA-N n-[3-cyclopropyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-[2-(4-methylpiperazin-1-yl)ethoxy]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1CN(C)CCN1CCOC1=CC2=NC=C(C(=O)NC=3C=4C(C5CC5)=NN(CC=5N=C(C)C=CC=5)C=4C=CC=3)N2C=C1 JUPOTOIJLKDAPF-UHFFFAOYSA-N 0.000 claims description 2
- AXUOVBRFGFHGLX-UHFFFAOYSA-N n-[3-cyclopropyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-[2-(4-propan-2-ylpiperazin-1-yl)ethoxy]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1CN(C(C)C)CCN1CCOC1=CC2=NC=C(C(=O)NC=3C=4C(C5CC5)=NN(CC=5N=C(C)C=CC=5)C=4C=CC=3)N2C=C1 AXUOVBRFGFHGLX-UHFFFAOYSA-N 0.000 claims description 2
- PPLJRDUWNJIQBH-UHFFFAOYSA-N n-[3-cyclopropyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-fluoroimidazo[1,2-a]pyridine-3-carboxamide Chemical compound CC1=CC=CC(CN2C3=CC=CC(NC(=O)C=4N5C=CC(F)=CC5=NC=4)=C3C(C3CC3)=N2)=N1 PPLJRDUWNJIQBH-UHFFFAOYSA-N 0.000 claims description 2
- FTZFXXAIYXWZLT-UHFFFAOYSA-N n-[3-cyclopropyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-methylsulfanylimidazo[1,2-a]pyridine-3-carboxamide Chemical compound C=1N=C2C=C(SC)C=CN2C=1C(=O)NC(C=1C(C2CC2)=N2)=CC=CC=1N2CC1=CC=CC(C)=N1 FTZFXXAIYXWZLT-UHFFFAOYSA-N 0.000 claims description 2
- QFZNCPMBKQTTQX-UHFFFAOYSA-N n-[3-cyclopropyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-oxo-1h-imidazo[1,2-a]pyridine-3-carboxamide Chemical compound CC1=CC=CC(CN2C3=CC=CC(NC(=O)C=4N5C=CC(=O)C=C5NC=4)=C3C(C3CC3)=N2)=N1 QFZNCPMBKQTTQX-UHFFFAOYSA-N 0.000 claims description 2
- LQJAVRMAFKSBPD-UHFFFAOYSA-N n-[3-cyclopropyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-phenylmethoxyimidazo[1,2-a]pyridine-3-carboxamide Chemical compound CC1=CC=CC(CN2C3=CC=CC(NC(=O)C=4N5C=CC(OCC=6C=CC=CC=6)=CC5=NC=4)=C3C(C3CC3)=N2)=N1 LQJAVRMAFKSBPD-UHFFFAOYSA-N 0.000 claims description 2
- ATFKHOBVIQGTKH-UHFFFAOYSA-N n-[3-ethyl-1-(1,3-thiazol-2-ylmethyl)indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC=CC4=NC=3)=C2C(CC)=NN1CC1=NC=CS1 ATFKHOBVIQGTKH-UHFFFAOYSA-N 0.000 claims description 2
- NDWDFOHNAPAFJC-UHFFFAOYSA-N n-[3-ethyl-1-[(1-ethyl-6-oxopyridin-2-yl)methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC=CC4=NC=3)=C2C(CC)=NN1CC1=CC=CC(=O)N1CC NDWDFOHNAPAFJC-UHFFFAOYSA-N 0.000 claims description 2
- SCMASSPGIAAGHN-UHFFFAOYSA-N n-[3-ethyl-1-[(1-ethylpyrazol-3-yl)methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC=CC4=NC=3)=C2C(CC)=NN1CC=1C=CN(CC)N=1 SCMASSPGIAAGHN-UHFFFAOYSA-N 0.000 claims description 2
- MWFNPRQEFCHCNY-UHFFFAOYSA-N n-[3-ethyl-1-[(1-ethylpyrazol-4-yl)methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC=CC4=NC=3)=C2C(CC)=NN1CC=1C=NN(CC)C=1 MWFNPRQEFCHCNY-UHFFFAOYSA-N 0.000 claims description 2
- XWABRABCHYJPNA-UHFFFAOYSA-N n-[3-ethyl-1-[(1-methyl-6-oxopyridin-2-yl)methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC=CC4=NC=3)=C2C(CC)=NN1CC1=CC=CC(=O)N1C XWABRABCHYJPNA-UHFFFAOYSA-N 0.000 claims description 2
- LOEBIRUSICDDGW-UHFFFAOYSA-N n-[3-ethyl-1-[(1-methylpyrazol-3-yl)methyl]indazol-4-yl]-7-[2-(4-methylpiperazin-1-yl)ethoxy]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(OCCN5CCN(C)CC5)=CC4=NC=3)=C2C(CC)=NN1CC=1C=CN(C)N=1 LOEBIRUSICDDGW-UHFFFAOYSA-N 0.000 claims description 2
- YHDAGLLBTBFMNG-UHFFFAOYSA-N n-[3-ethyl-1-[(1-methylpyrazol-3-yl)methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC=CC4=NC=3)=C2C(CC)=NN1CC=1C=CN(C)N=1 YHDAGLLBTBFMNG-UHFFFAOYSA-N 0.000 claims description 2
- YZQBDBRJSKLRTN-UHFFFAOYSA-N n-[3-ethyl-1-[(2-ethylpyrazol-3-yl)methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC=CC4=NC=3)=C2C(CC)=NN1CC1=CC=NN1CC YZQBDBRJSKLRTN-UHFFFAOYSA-N 0.000 claims description 2
- RLORZIBXBXALAU-UHFFFAOYSA-N n-[3-ethyl-1-[(2-methoxy-6-methylpyridin-3-yl)methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC=CC4=NC=3)=C2C(CC)=NN1CC1=CC=C(C)N=C1OC RLORZIBXBXALAU-UHFFFAOYSA-N 0.000 claims description 2
- UUBIFSFENVYIKI-UHFFFAOYSA-N n-[3-ethyl-1-[(4-methyl-1,3-thiazol-2-yl)methyl]indazol-4-yl]-7-[2-(4-methylpiperazin-1-yl)ethoxy]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(OCCN5CCN(C)CC5)=CC4=NC=3)=C2C(CC)=NN1CC1=NC(C)=CS1 UUBIFSFENVYIKI-UHFFFAOYSA-N 0.000 claims description 2
- VBWSYUAKXRZVQI-UHFFFAOYSA-N n-[3-ethyl-1-[(5-fluoropyridin-2-yl)methyl]indazol-4-yl]-7-[2-(4-methylpiperazin-1-yl)ethoxy]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(OCCN5CCN(C)CC5)=CC4=NC=3)=C2C(CC)=NN1CC1=CC=C(F)C=N1 VBWSYUAKXRZVQI-UHFFFAOYSA-N 0.000 claims description 2
- YHBYPXGRBVLGCM-UHFFFAOYSA-N n-[3-ethyl-1-[(6-ethylpyridin-2-yl)methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC=CC4=NC=3)=C2C(CC)=NN1CC1=CC=CC(CC)=N1 YHBYPXGRBVLGCM-UHFFFAOYSA-N 0.000 claims description 2
- WQNUKROXRQRGPR-UHFFFAOYSA-N n-[3-ethyl-1-[(6-methoxypyridin-2-yl)methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC=CC4=NC=3)=C2C(CC)=NN1CC1=CC=CC(OC)=N1 WQNUKROXRQRGPR-UHFFFAOYSA-N 0.000 claims description 2
- ANEIMXYWFGGHQX-UHFFFAOYSA-N n-[3-ethyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-(1,3,4-oxadiazol-2-yl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(=CC4=NC=3)C=3OC=NN=3)=C2C(CC)=NN1CC1=CC=CC(C)=N1 ANEIMXYWFGGHQX-UHFFFAOYSA-N 0.000 claims description 2
- NKLTZWLOVVGENN-UHFFFAOYSA-N n-[3-ethyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-(1,3,4-thiadiazol-2-yl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(=CC4=NC=3)C=3SC=NN=3)=C2C(CC)=NN1CC1=CC=CC(C)=N1 NKLTZWLOVVGENN-UHFFFAOYSA-N 0.000 claims description 2
- PDCHDFDIHIMEBF-UHFFFAOYSA-N n-[3-ethyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(=CC4=NC=3)C=3N4CCNCC4=NC=3)=C2C(CC)=NN1CC1=CC=CC(C)=N1 PDCHDFDIHIMEBF-UHFFFAOYSA-N 0.000 claims description 2
- NZFBIERVOBGSPS-UHFFFAOYSA-N n-[3-ethyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-(7-methyl-6,8-dihydro-5h-imidazo[1,2-a]pyrazin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(=CC4=NC=3)C=3N4CCN(C)CC4=NC=3)=C2C(CC)=NN1CC1=CC=CC(C)=N1 NZFBIERVOBGSPS-UHFFFAOYSA-N 0.000 claims description 2
- SQSFILYXDVLRJJ-UHFFFAOYSA-N n-[3-ethyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-(piperazin-1-ylmethyl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(CN5CCNCC5)=CC4=NC=3)=C2C(CC)=NN1CC1=CC=CC(C)=N1 SQSFILYXDVLRJJ-UHFFFAOYSA-N 0.000 claims description 2
- OABJXDGOWMDYPB-JWQCQUIFSA-N n-[3-ethyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-[(3r,4r)-4-hydroxypyrrolidin-3-yl]oxyimidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(O[C@H]5[C@@H](CNC5)O)=CC4=NC=3)=C2C(CC)=NN1CC1=CC=CC(C)=N1 OABJXDGOWMDYPB-JWQCQUIFSA-N 0.000 claims description 2
- OABJXDGOWMDYPB-DQEYMECFSA-N n-[3-ethyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-[(3s,4s)-4-hydroxypyrrolidin-3-yl]oxyimidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(O[C@@H]5[C@H](CNC5)O)=CC4=NC=3)=C2C(CC)=NN1CC1=CC=CC(C)=N1 OABJXDGOWMDYPB-DQEYMECFSA-N 0.000 claims description 2
- ULKSYLSNHQPJQA-UHFFFAOYSA-N n-[3-ethyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-[(4-methylpiperazin-1-yl)methyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(CN5CCN(C)CC5)=CC4=NC=3)=C2C(CC)=NN1CC1=CC=CC(C)=N1 ULKSYLSNHQPJQA-UHFFFAOYSA-N 0.000 claims description 2
- RXCLCKGTMFDLIP-UHFFFAOYSA-N n-[3-ethyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-[2-(3-fluoroazetidin-1-yl)ethyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(CCN5CC(F)C5)=CC4=NC=3)=C2C(CC)=NN1CC1=CC=CC(C)=N1 RXCLCKGTMFDLIP-UHFFFAOYSA-N 0.000 claims description 2
- QZCFZIARGAMFJH-UHFFFAOYSA-N n-[3-ethyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-[2-(3-methoxyazetidin-1-yl)ethyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(CCN5CC(C5)OC)=CC4=NC=3)=C2C(CC)=NN1CC1=CC=CC(C)=N1 QZCFZIARGAMFJH-UHFFFAOYSA-N 0.000 claims description 2
- ORWFYKVVNFEZBW-UHFFFAOYSA-N n-[3-ethyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-[2-(4-methyl-4-oxidopiperazin-4-ium-1-yl)ethoxy]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(OCCN5CC[N+](C)([O-])CC5)=CC4=NC=3)=C2C(CC)=NN1CC1=CC=CC(C)=N1 ORWFYKVVNFEZBW-UHFFFAOYSA-N 0.000 claims description 2
- MTMQYQXOCXQCHZ-UHFFFAOYSA-N n-[3-ethyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-[2-(4-methylpiperazin-1-yl)ethoxy]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(OCCN5CCN(C)CC5)=CC4=NC=3)=C2C(CC)=NN1CC1=CC=CC(C)=N1 MTMQYQXOCXQCHZ-UHFFFAOYSA-N 0.000 claims description 2
- DOTOQJJAWOWHQF-UHFFFAOYSA-N n-[3-ethyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-[2-(4-methylpiperazin-1-yl)ethyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(CCN5CCN(C)CC5)=CC4=NC=3)=C2C(CC)=NN1CC1=CC=CC(C)=N1 DOTOQJJAWOWHQF-UHFFFAOYSA-N 0.000 claims description 2
- AHOPDFDFRKFFHI-UHFFFAOYSA-N n-[3-ethyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-[2-(4-propan-2-ylpiperazin-1-yl)ethoxy]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(OCCN5CCN(CC5)C(C)C)=CC4=NC=3)=C2C(CC)=NN1CC1=CC=CC(C)=N1 AHOPDFDFRKFFHI-UHFFFAOYSA-N 0.000 claims description 2
- CFVIPSXMZCYEBV-UHFFFAOYSA-N n-[3-ethyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-[3-(4-methylpiperazin-1-yl)propyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(CCCN5CCN(C)CC5)=CC4=NC=3)=C2C(CC)=NN1CC1=CC=CC(C)=N1 CFVIPSXMZCYEBV-UHFFFAOYSA-N 0.000 claims description 2
- CRXRSSSMXFMZGM-UHFFFAOYSA-N n-[3-ethyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-morpholin-4-ylimidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(=CC4=NC=3)N3CCOCC3)=C2C(CC)=NN1CC1=CC=CC(C)=N1 CRXRSSSMXFMZGM-UHFFFAOYSA-N 0.000 claims description 2
- SPLHYZQGBUXFFW-UHFFFAOYSA-N n-[3-ethyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-piperazin-1-ylimidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(=CC4=NC=3)N3CCNCC3)=C2C(CC)=NN1CC1=CC=CC(C)=N1 SPLHYZQGBUXFFW-UHFFFAOYSA-N 0.000 claims description 2
- DTTFSEPKXCAWIX-UHFFFAOYSA-N n-[3-ethyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-pyrimidin-5-ylimidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(=CC4=NC=3)C=3C=NC=NC=3)=C2C(CC)=NN1CC1=CC=CC(C)=N1 DTTFSEPKXCAWIX-UHFFFAOYSA-N 0.000 claims description 2
- FRCSWNZVLDOHOS-UHFFFAOYSA-N n-[3-ethyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC=CC4=NC=3)=C2C(CC)=NN1CC1=CC=CC(C)=N1 FRCSWNZVLDOHOS-UHFFFAOYSA-N 0.000 claims description 2
- JMNQZEVFQQRSQH-UHFFFAOYSA-N n-[3-ethyl-1-[(6-methylpyridin-3-yl)methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC=CC4=NC=3)=C2C(CC)=NN1CC1=CC=C(C)N=C1 JMNQZEVFQQRSQH-UHFFFAOYSA-N 0.000 claims description 2
- ZOCGXBBRKRAKLQ-UHFFFAOYSA-N n-[3-ethyl-1-[(6-piperazin-1-ylpyridin-2-yl)methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC=CC4=NC=3)=C2C(CC)=NN1CC(N=1)=CC=CC=1N1CCNCC1 ZOCGXBBRKRAKLQ-UHFFFAOYSA-N 0.000 claims description 2
- APZMSBZXHGTGIE-UHFFFAOYSA-N n-[3-ethyl-1-[(6-piperidin-4-yloxypyridin-2-yl)methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC=CC4=NC=3)=C2C(CC)=NN1CC(N=1)=CC=CC=1OC1CCNCC1 APZMSBZXHGTGIE-UHFFFAOYSA-N 0.000 claims description 2
- RFDRRTBJCGOYRX-UHFFFAOYSA-N n-[3-ethyl-1-[[1-(2-hydroxyethyl)pyrazol-4-yl]methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC=CC4=NC=3)=C2C(CC)=NN1CC=1C=NN(CCO)C=1 RFDRRTBJCGOYRX-UHFFFAOYSA-N 0.000 claims description 2
- BQSDJUKRUZPTCH-UHFFFAOYSA-N n-[3-ethyl-1-[[1-(2-piperazin-1-ylethyl)pyrazol-3-yl]methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC=CC4=NC=3)=C2C(CC)=NN1CC(=N1)C=CN1CCN1CCNCC1 BQSDJUKRUZPTCH-UHFFFAOYSA-N 0.000 claims description 2
- NMPMPLYJILKKEJ-UHFFFAOYSA-N n-[3-ethyl-1-[[1-[(4-methoxyphenyl)methyl]pyrazol-4-yl]methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC=CC4=NC=3)=C2C(CC)=NN1CC(=C1)C=NN1CC1=CC=C(OC)C=C1 NMPMPLYJILKKEJ-UHFFFAOYSA-N 0.000 claims description 2
- QLLLSYAAVOVZPW-UHFFFAOYSA-N n-[3-ethyl-1-[[6-(2-piperazin-1-ylethoxy)pyridin-2-yl]methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC=CC4=NC=3)=C2C(CC)=NN1CC(N=1)=CC=CC=1OCCN1CCNCC1 QLLLSYAAVOVZPW-UHFFFAOYSA-N 0.000 claims description 2
- KYKZEZAPVYZWFT-UHFFFAOYSA-N n-[3-ethyl-1-[[6-(piperazin-1-ylmethyl)pyridin-2-yl]methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC=CC4=NC=3)=C2C(CC)=NN1CC(N=1)=CC=CC=1CN1CCNCC1 KYKZEZAPVYZWFT-UHFFFAOYSA-N 0.000 claims description 2
- SCVCVCIZOKLMNU-NTKDMRAZSA-N n-[3-ethyl-1-[[6-[(3r,4r)-3-fluoropiperidin-4-yl]oxypyridin-2-yl]methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC=CC4=NC=3)=C2C(CC)=NN1CC(N=1)=CC=CC=1O[C@@H]1CCNC[C@H]1F SCVCVCIZOKLMNU-NTKDMRAZSA-N 0.000 claims description 2
- WHNAGZDKIGOAKE-IBGZPJMESA-N n-[3-ethyl-1-[[6-[(3s)-pyrrolidin-3-yl]oxypyridin-2-yl]methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC=CC4=NC=3)=C2C(CC)=NN1CC(N=1)=CC=CC=1O[C@H]1CCNC1 WHNAGZDKIGOAKE-IBGZPJMESA-N 0.000 claims description 2
- VRDNGVPKSWEAFY-RPBOFIJWSA-N n-[3-ethyl-1-[[6-[[(2r,3s)-3-hydroxy-1-methylpyrrolidin-2-yl]methoxy]pyridin-2-yl]methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC=CC4=NC=3)=C2C(CC)=NN1CC(N=1)=CC=CC=1OC[C@@H]1[C@@H](O)CCN1C VRDNGVPKSWEAFY-RPBOFIJWSA-N 0.000 claims description 2
- IWOVKSXLDXEFJZ-QPPBQGQZSA-N n-[3-ethyl-1-[[6-[[(2r,3s)-3-hydroxypyrrolidin-2-yl]methoxy]pyridin-2-yl]methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC=CC4=NC=3)=C2C(CC)=NN1CC(N=1)=CC=CC=1OC[C@H]1NCC[C@@H]1O IWOVKSXLDXEFJZ-QPPBQGQZSA-N 0.000 claims description 2
- JYJSLERSUMRWQZ-UHFFFAOYSA-N n-[3-iodo-1-[(2-methyl-1,3-thiazol-5-yl)methyl]indazol-4-yl]-7-[2-(4-methylpiperazin-1-yl)ethoxy]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1CN(C)CCN1CCOC1=CC2=NC=C(C(=O)NC=3C=4C(I)=NN(CC=5SC(C)=NC=5)C=4C=CC=3)N2C=C1 JYJSLERSUMRWQZ-UHFFFAOYSA-N 0.000 claims description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- QYCDIIUTYOXKLV-UHFFFAOYSA-N tert-butyl n-[3-[3-[[3-ethyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]carbamoyl]imidazo[1,2-a]pyridin-7-yl]oxy-2,2-difluoropropyl]carbamate Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(OCC(F)(F)CNC(=O)OC(C)(C)C)=CC4=NC=3)=C2C(CC)=NN1CC1=CC=CC(C)=N1 QYCDIIUTYOXKLV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims 2
- QTMXTKJOEMDYEF-UHFFFAOYSA-N 7-[2-(azetidin-1-yl)ethoxy]-n-[3-cyclopropyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound CC1=CC=CC(CN2C3=CC=CC(NC(=O)C=4N5C=CC(OCCN6CCC6)=CC5=NC=4)=C3C(C3CC3)=N2)=N1 QTMXTKJOEMDYEF-UHFFFAOYSA-N 0.000 claims 1
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- 229910052794 bromium Inorganic materials 0.000 claims 1
- RNDSNACPDQNWRG-UHFFFAOYSA-N n-(1-benzyl-3-cyclopropylindazol-4-yl)-7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C=1N=C2C=C(OCCOC)C=CN2C=1C(=O)NC(C=1C(C2CC2)=N2)=CC=CC=1N2CC1=CC=CC=C1 RNDSNACPDQNWRG-UHFFFAOYSA-N 0.000 claims 1
- XOVQCTKJBWAVEC-UHFFFAOYSA-N n-(1-benzyl-3-ethylindazol-4-yl)-7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(OCCOC)=CC4=NC=3)=C2C(CC)=NN1CC1=CC=CC=C1 XOVQCTKJBWAVEC-UHFFFAOYSA-N 0.000 claims 1
- BHFHDPVAKGLLLD-UHFFFAOYSA-N n-(1-benzyl-3-iodoindazol-4-yl)-7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C=1N=C2C=C(OCCOC)C=CN2C=1C(=O)NC(C=1C(I)=N2)=CC=CC=1N2CC1=CC=CC=C1 BHFHDPVAKGLLLD-UHFFFAOYSA-N 0.000 claims 1
- VKJMREAAUAJFPB-UHFFFAOYSA-N n-[3-ethyl-1-[[6-[2-(4-methylpiperazin-1-yl)ethoxy]pyridin-2-yl]methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC=CC4=NC=3)=C2C(CC)=NN1CC(N=1)=CC=CC=1OCCN1CCN(C)CC1 VKJMREAAUAJFPB-UHFFFAOYSA-N 0.000 claims 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 0 CC(C*C=O)C(*)c1cc2ncc(C(Nc3c(*)ccc4c3c(*)n[n]4*)=O)[n]2cc1* Chemical compound CC(C*C=O)C(*)c1cc2ncc(C(Nc3c(*)ccc4c3c(*)n[n]4*)=O)[n]2cc1* 0.000 description 5
- 238000000034 method Methods 0.000 description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- IIGLROACUDOVTQ-UHFFFAOYSA-N C1(CC1)C1=NN(C2=CC=CC(=C12)NC(=O)C1=CN=C2N1C=CC=C2)CC1=NC(=CC=C1)C Chemical compound C1(CC1)C1=NN(C2=CC=CC(=C12)NC(=O)C1=CN=C2N1C=CC=C2)CC1=NC(=CC=C1)C IIGLROACUDOVTQ-UHFFFAOYSA-N 0.000 description 1
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- GZSYWOPKRWMDTP-UHFFFAOYSA-N N=1C=C(N2C=1C=CC=C2)C(=O)NC=1OC(=NN=1)C Chemical compound N=1C=C(N2C=1C=CC=C2)C(=O)NC=1OC(=NN=1)C GZSYWOPKRWMDTP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- SPIPWDGHGPNYDD-UHFFFAOYSA-N n-[3-ethyl-1-[(1-ethylpyrazol-3-yl)methyl]indazol-4-yl]-7-fluoroimidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(F)=CC4=NC=3)=C2C(CC)=NN1CC=1C=CN(CC)N=1 SPIPWDGHGPNYDD-UHFFFAOYSA-N 0.000 description 1
- QIGBEHIZQCAKMK-WIYYLYMNSA-N n-[3-ethyl-1-[[1-[(3r,4r)-3-fluoropiperidin-4-yl]pyrazol-4-yl]methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC=CC4=NC=3)=C2C(CC)=NN1CC(=C1)C=NN1[C@@H]1CCNC[C@H]1F QIGBEHIZQCAKMK-WIYYLYMNSA-N 0.000 description 1
- 150000002829 nitrogen Chemical group 0.000 description 1
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| BR112012002854B1 (pt) | 2009-08-10 | 2020-02-18 | Samumed, Llc | Composto ou sal farmaceuticamente aceitável, composição farmacêutica e uso dos mesmos |
| US8450340B2 (en) | 2009-12-21 | 2013-05-28 | Samumed, Llc | 1H-pyrazolo[3,4-b]pyridines and therapeutic uses thereof |
| SG181861A1 (en) * | 2009-12-21 | 2012-07-30 | Array Biopharma Inc | Substituted n-(1h-indazol-4-yl)imidazo[1, 2-a]pyridine-3- carboxamide compounds as cfms inhibitors |
| UA112425C2 (uk) * | 2010-12-13 | 2016-09-12 | Еррей Біофарма Інк. | ЗАМІЩЕНІ N-(1H-ІНДАЗОЛ-4-ІЛ)ІМІДАЗО[1,2-a]ПІРИДИН-3-КАРБОКСАМІДНІ СПОЛУКИ ЯК ІНГІБІТОРИ РЕЦЕПТОРНОЇ ТИРОЗИНКІНАЗИ ІІІ ТИПУ |
| ES2711777T3 (es) | 2011-09-14 | 2019-05-07 | Samumed Llc | Indazol-3-carboxamidas y su uso como inhibidores de la ruta de señalización de Wnt/b-catenina |
| PH12017500997A1 (en) | 2012-04-04 | 2018-02-19 | Samumed Llc | Indazole inhibitors of the wnt signal pathway and therapeutic uses thereof |
| CA2872147A1 (en) | 2012-05-02 | 2013-11-07 | Kansas State University Research Foundation | Macrocyclic and peptidomimetic compounds as broad-spectrum antivirals against 3c or 3c-like proteases of picornaviruses, caliciviruses and coronaviruses |
| SI2770994T1 (sl) | 2012-05-04 | 2020-02-28 | Samumed, Llc | 1H-pirazolo(3,4-B)piridini in njihove terapevtske uporabe |
| WO2014110086A2 (en) | 2013-01-08 | 2014-07-17 | Samumed, Llc | 3-(benzoimidazol-2-yl)-indazole inhibitors of the wnt signaling pathway and therapeutic uses thereof |
| KR101756934B1 (ko) | 2014-07-08 | 2017-07-12 | 연세대학교 산학협력단 | 피롤로[1,2-a]피라진 유도체, 이의 약학적으로 허용가능한 염, 이들 화합물의 제조방법 및 이를 유효성분으로 함유하는 골다공증 치료 또는 예방용 약학조성물 |
| WO2016040184A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 3-(3h-imidazo[4,5-b]pyridin-2-yl)-1h-pyrazolo[3,4-c]pyridine and therapeutic uses thereof |
| WO2016040181A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 3-(1h-imidazo[4,5-c]pyridin-2-yl)-1h-pyrazolo[3,4-c]pyridine and therapeutic uses thereof |
| WO2016040190A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 3-(3h-imidazo[4,5-b]pyridin-2-yl)-1h-pyrazolo[3,4-b]pyridine and therapeutic uses thereof |
| WO2016040188A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 3-(3h-imidazo[4,5-c]pyridin-2-yl)-1h-pyrazolo[3,4-c]pyridine and therapeutic uses thereof |
| WO2016040182A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 2-(1h-indazol-3-yl)-1h-imidazo[4,5-c]pyridine and therapeutic uses thereof |
| WO2016040193A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 3-(1h-imidazo[4,5-c]pyridin-2-yl)-1h-pyrazolo[3,4-b]pyridine and therapeutic uses thereof |
| WO2016040180A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 3-(1h-benzo[d]imidazol-2-yl)-1h-pyrazolo[3,4-c]pyridine and therapeutic uses thereof |
| WO2016040185A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 2-(1h-indazol-3-yl)-3h-imidazo[4,5-b]pyridine and therapeutic uses thereof |
| BR112017013111A2 (pt) | 2014-12-22 | 2018-05-15 | Five Prime Therapeutics Inc | métodos de tratamento de um distúrbio e de tratamento da sinovite, uso de um anticorpo e anticorpo |
| CN204833440U (zh) | 2015-07-29 | 2015-12-02 | 山东新北洋信息技术股份有限公司 | 识读组件及纸币清分机 |
| WO2017023972A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc. | 3-(1h-imidazo[4,5-c]pyridin-2-yl)-1h-pyrazolo[4,3-b]pyridines and therapeutic uses thereof |
| WO2017024026A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc | 3-(1h-indol-2-yl)-1h-pyrazolo[3,4-c]pyridines and therapeutic uses thereof |
| WO2017023980A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc. | 3-(1h-pyrrolo[2,3-b]pyridin-2-yl)-1h-pyrazolo[3,4-c]pyridines and therapeutic uses thereof |
| WO2017023989A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc. | 3-(1h-benzo[d]imidazol-2-yl)-1h-pyrazolo[4,3-b]pyridines and therapeutic uses thereof |
| US10383861B2 (en) | 2015-08-03 | 2019-08-20 | Sammumed, LLC | 3-(1H-pyrrolo[2,3-C]pyridin-2-yl)-1H-pyrazolo[3,4-C]pyridines and therapeutic uses thereof |
| WO2017023993A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc. | 3-(1h-indol-2-yl)-1h-pyrazolo[4,3-b]pyridines and therapeutic uses thereof |
| WO2017023987A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc. | 3-(1h-pyrrolo[3,2-c]pyridin-2-yl)-1h-pyrazolo[3,4-b]pyridines and therapeutic uses thereof |
| WO2017024021A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc | 3-(1h-pyrrolo[2,3-b]pyridin-2-yl)-1h-indazoles and therapeutic uses thereof |
| US10463651B2 (en) | 2015-08-03 | 2019-11-05 | Samumed, Llc | 3-(1H-pyrrolo[3,2-C]pyridin-2-YL)-1H-indazoles and therapeutic uses thereof |
| US10329309B2 (en) | 2015-08-03 | 2019-06-25 | Samumed, Llc | 3-(3H-imidazo[4,5-B]pyridin-2-yl)-1H-pyrazolo[4,3-B]pyridines and therapeutic uses thereof |
| WO2017024025A1 (en) | 2015-08-03 | 2017-02-09 | Sunil Kumar Kc | 3-(1h-pyrrolo[2,3-c]pyridin-2-yl)-1h-pyrazolo[4,3-b]pyridines and therapeutic uses thereof |
| WO2017024003A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc | 3-(1h-pyrrolo[3,2-c]pyridin-2-yl)-1h-pyrazolo[4,3-b]pyridines and therapeutic uses thereof |
| WO2017023988A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc. | 3-(3h-imidazo[4,5-c]pyridin-2-yl)-1h-pyrazolo[4,3-b]pyridines and therapeutic uses thereof |
| WO2017023984A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc. | 3-(1h-pyrrolo[3,2-c]pyridin-2-yl)-1h-pyrazolo[3,4-c]pyridines and therapeutic uses thereof |
| US10604512B2 (en) | 2015-08-03 | 2020-03-31 | Samumed, Llc | 3-(1H-indol-2-yl)-1H-indazoles and therapeutic uses thereof |
| US10285983B2 (en) | 2015-08-03 | 2019-05-14 | Samumed, Llc | 3-(1H-pyrrolo[2,3-B]pyridin-2-yl)-1H-pyrazolo[3,4-B] pyridines and therapeutic uses thereof |
| US10206909B2 (en) | 2015-08-03 | 2019-02-19 | Samumed, Llc | 3-(1H-pyrrolo[2,3-B]pyridin-2-yl)-1H-pyrazolo[4,3-B]pyridines and therapeutic uses thereof |
| CN108473491A (zh) | 2015-11-06 | 2018-08-31 | 萨穆梅德有限公司 | 2-(1h-吲唑-3-基)-3h-咪唑并[4,5-c]吡啶以及其抗炎用途 |
| AR108325A1 (es) | 2016-04-27 | 2018-08-08 | Samumed Llc | Isoquinolin-3-il carboxamidas y preparación y uso de las mismas |
| MX390577B (es) | 2016-06-01 | 2025-03-20 | Samumed Llc | Proceso de preparación de n-(5-(3-(7-(3-fluorofenil)-3h-imidazo[4,5-c]piridin-2-il)-1h-indazol-5-il)piridin-3-il)-3-metilbutanamida. |
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| UA112425C2 (uk) * | 2010-12-13 | 2016-09-12 | Еррей Біофарма Інк. | ЗАМІЩЕНІ N-(1H-ІНДАЗОЛ-4-ІЛ)ІМІДАЗО[1,2-a]ПІРИДИН-3-КАРБОКСАМІДНІ СПОЛУКИ ЯК ІНГІБІТОРИ РЕЦЕПТОРНОЇ ТИРОЗИНКІНАЗИ ІІІ ТИПУ |
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2012
- 2012-06-21 CL CL2012001699A patent/CL2012001699A1/es unknown
- 2012-06-21 IL IL220544A patent/IL220544A/en active IP Right Grant
- 2012-07-19 CO CO12122160A patent/CO6561821A2/es unknown
- 2012-07-20 CR CR20120389A patent/CR20120389A/es unknown
- 2012-07-20 ZA ZA2012/05505A patent/ZA201205505B/en unknown
-
2014
- 2014-09-30 SM SM201400142T patent/SMT201400142B/xx unknown
-
2015
- 2015-01-22 JP JP2015010346A patent/JP2015107999A/ja not_active Withdrawn
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