ES2494590T3 - Compuestos de N-(1H-Indazol-4-il)imidazo[1,2-a]piridin-3-carboxamida sustituida como inhibidores de cFMS - Google Patents

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Publication number

ES2494590T3

ES2494590T3 ES10798683.8T ES10798683T ES2494590T3 ES 2494590 T3 ES2494590 T3 ES 2494590T3 ES 10798683 T ES10798683 T ES 10798683T ES 2494590 T3 ES2494590 T3 ES 2494590T3

Authority

ES

Spain

Prior art keywords

methyl

indazol

imidazo

ethyl

carboxamide

Prior art date

2009-12-21

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.)

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 428
• 239000003112 inhibitor Substances 0.000 title description 29
• AYAOSDNSSUARDZ-UHFFFAOYSA-N n-(1h-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide Chemical class C1=CC=CN2C(C(NC=3C=4C=NNC=4C=CC=3)=O)=CN=C21 AYAOSDNSSUARDZ-UHFFFAOYSA-N 0.000 title description 4
• -1 R'R "NC ( > = O) - Chemical group 0.000 claims abstract description 311
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 117
• 125000001424 substituent group Chemical group 0.000 claims abstract description 110
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 82
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 72
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 69
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 62
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 57
• 150000003839 salts Chemical class 0.000 claims abstract description 47
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 39
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 37
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 32
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 31
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 31
• 125000004076 pyridyl group Chemical group 0.000 claims abstract description 30
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 28
• 150000002367 halogens Chemical class 0.000 claims abstract description 27
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 25
• 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims abstract description 24
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 24
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 22
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 19
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 18
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 17
• 229910052794 bromium Inorganic materials 0.000 claims abstract description 15
• IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 15
• 229910052801 chlorine Inorganic materials 0.000 claims abstract description 14
• 125000005113 hydroxyalkoxy group Chemical group 0.000 claims abstract description 13
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 13
• 229910052740 iodine Inorganic materials 0.000 claims abstract description 12
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims abstract description 10
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims abstract description 10
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims abstract description 8
• 125000002431 aminoalkoxy group Chemical group 0.000 claims abstract description 8
• 125000004990 dihydroxyalkyl group Chemical group 0.000 claims abstract description 7
• 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 5
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 5
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract description 4
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 146
• 239000002585 base Substances 0.000 claims description 145
• 238000000034 method Methods 0.000 claims description 75
• 238000011282 treatment Methods 0.000 claims description 74
• 206010028980 Neoplasm Diseases 0.000 claims description 66
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 52
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 48
• 201000010099 disease Diseases 0.000 claims description 47
• 210000000988 bone and bone Anatomy 0.000 claims description 45
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 44
• 125000004429 atom Chemical group 0.000 claims description 40
• 238000002360 preparation method Methods 0.000 claims description 40
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
• 208000002193 Pain Diseases 0.000 claims description 33
• 230000036407 pain Effects 0.000 claims description 33
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 32
• 201000011510 cancer Diseases 0.000 claims description 30
• 239000003054 catalyst Substances 0.000 claims description 30
• 229910052763 palladium Inorganic materials 0.000 claims description 30
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 28
• 150000003254 radicals Chemical class 0.000 claims description 25
• 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 24
• 230000008878 coupling Effects 0.000 claims description 23
• 238000010168 coupling process Methods 0.000 claims description 23
• 238000005859 coupling reaction Methods 0.000 claims description 23
• 208000027866 inflammatory disease Diseases 0.000 claims description 23
• 208000023275 Autoimmune disease Diseases 0.000 claims description 22
• 239000003153 chemical reaction reagent Substances 0.000 claims description 22
• 239000003638 chemical reducing agent Substances 0.000 claims description 18
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 18
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
• 125000006239 protecting group Chemical group 0.000 claims description 17
• 241000124008 Mammalia Species 0.000 claims description 16
• 229910052799 carbon Inorganic materials 0.000 claims description 16
• 229910052731 fluorine Inorganic materials 0.000 claims description 16
• 239000003446 ligand Substances 0.000 claims description 16
• 238000002560 therapeutic procedure Methods 0.000 claims description 12
• UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 11
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 10
• PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 claims description 10
• 229920006395 saturated elastomer Polymers 0.000 claims description 9
• 239000003795 chemical substances by application Substances 0.000 claims description 8
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 8
• 230000009467 reduction Effects 0.000 claims description 8
• 150000003857 carboxamides Chemical class 0.000 claims description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims description 7
• 230000008569 process Effects 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
• 230000003213 activating effect Effects 0.000 claims description 6
• 239000003085 diluting agent Substances 0.000 claims description 6
• NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 claims description 5
• 239000007822 coupling agent Substances 0.000 claims description 5
• 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
• 239000007800 oxidant agent Substances 0.000 claims description 5
• 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 5
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
• 150000001723 carbon free-radicals Chemical class 0.000 claims description 4
• DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 4
• 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 description 4
• 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 description 4
• 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 claims description 3
• JUQWFONZRDXAAB-UHFFFAOYSA-N 1-methyl-1-oxidopiperazin-1-ium Chemical compound C[N+]1([O-])CCNCC1 JUQWFONZRDXAAB-UHFFFAOYSA-N 0.000 claims description 3
• 238000010306 acid treatment Methods 0.000 claims description 3
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 3
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
• 125000001072 heteroaryl group Chemical group 0.000 claims description 3
• 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 3
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 3
• 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
• 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
• 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 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
• POOPWPIOIMBTOH-UHFFFAOYSA-N 8-oxa-3-azabicyclo[3.2.1]octane Chemical compound C1NCC2CCC1O2 POOPWPIOIMBTOH-UHFFFAOYSA-N 0.000 claims description 2
• 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 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
• MFKOCGITFPBMOA-UHFFFAOYSA-N n-[3-cyclopropyl-1-[(1-ethylpyrazol-3-yl)methyl]indazol-4-yl]-7-[2-(4-methylpiperazin-1-yl)ethoxy]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound CCN1C=CC(CN2C3=CC=CC(NC(=O)C=4N5C=CC(OCCN6CCN(C)CC6)=CC5=NC=4)=C3C(C3CC3)=N2)=N1 MFKOCGITFPBMOA-UHFFFAOYSA-N 0.000 claims description 2
• OTOOTNLPTXHFGT-UHFFFAOYSA-N n-[3-cyclopropyl-1-[(1-propan-2-ylpyrazol-3-yl)methyl]indazol-4-yl]-7-[2-(4-methylpiperazin-1-yl)ethoxy]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound CC(C)N1C=CC(CN2C3=CC=CC(NC(=O)C=4N5C=CC(OCCN6CCN(C)CC6)=CC5=NC=4)=C3C(C3CC3)=N2)=N1 OTOOTNLPTXHFGT-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
• 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
• 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 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
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