ES2540996T3 - Compuestos de N-(1H-indazol-4-il)imidazo[1,2-a]piridin-3-carboxamida sustituidos como inhibidores de tirosina cinasa del receptor de tipo III - Google Patents

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Publication number

ES2540996T3

ES2540996T3 ES11808427.6T ES11808427T ES2540996T3 ES 2540996 T3 ES2540996 T3 ES 2540996T3 ES 11808427 T ES11808427 T ES 11808427T ES 2540996 T3 ES2540996 T3 ES 2540996T3

Authority

ES

Spain

Prior art keywords

methyl

indazol

imidazo

carboxamide

pyridin

Prior art date

2010-12-13

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 388
• 229940127361 Receptor Tyrosine Kinase Inhibitors Drugs 0.000 title description 5
• 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
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 122
• 125000001424 substituent group Chemical group 0.000 claims abstract description 84
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 74
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 60
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 48
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 48
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 40
• 150000003839 salts Chemical class 0.000 claims abstract description 36
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 34
• 229910052731 fluorine Inorganic materials 0.000 claims abstract description 33
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 32
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 31
• 150000002367 halogens Chemical class 0.000 claims abstract description 30
• 229910052801 chlorine Inorganic materials 0.000 claims abstract description 29
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 29
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 29
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 26
• 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims abstract description 17
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 17
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 16
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 16
• 125000005113 hydroxyalkoxy group Chemical group 0.000 claims abstract description 16
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 15
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims abstract description 14
• 125000004990 dihydroxyalkyl group Chemical group 0.000 claims abstract description 13
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 12
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims abstract description 10
• 229910052794 bromium Inorganic materials 0.000 claims abstract description 9
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 8
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 8
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims abstract description 8
• CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims abstract description 6
• 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
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
• 125000006413 ring segment Chemical group 0.000 claims abstract description 5
• 229910003827 NRaRb Inorganic materials 0.000 claims abstract description 4
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 4
• 229910052701 rubidium Inorganic materials 0.000 claims abstract description 3
• -1 1 - ((6-isopropylpyridin-2-yl) methyl) -3-methyl-1H-indazol-4-yl Chemical group 0.000 claims description 369
• 238000002360 preparation method Methods 0.000 claims description 289
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 102
• 201000010099 disease Diseases 0.000 claims description 74
• 238000000034 method Methods 0.000 claims description 74
• 238000011282 treatment Methods 0.000 claims description 62
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 54
• 206010028980 Neoplasm Diseases 0.000 claims description 44
• 210000000988 bone and bone Anatomy 0.000 claims description 38
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 37
• 201000011510 cancer Diseases 0.000 claims description 37
• 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
• 241000124008 Mammalia Species 0.000 claims description 34
• 239000002585 base Substances 0.000 claims description 34
• 208000002193 Pain Diseases 0.000 claims description 32
• 206010016654 Fibrosis Diseases 0.000 claims description 28
• 208000035475 disorder Diseases 0.000 claims description 28
• 230000004761 fibrosis Effects 0.000 claims description 27
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 26
• 208000027866 inflammatory disease Diseases 0.000 claims description 26
• 229920006395 saturated elastomer Polymers 0.000 claims description 18
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 15
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 15
• 239000002253 acid Substances 0.000 claims description 13
• 229910052799 carbon Inorganic materials 0.000 claims description 13
• 150000003857 carboxamides Chemical class 0.000 claims description 13
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 12
• 230000008878 coupling Effects 0.000 claims description 12
• 238000010168 coupling process Methods 0.000 claims description 12
• 238000005859 coupling reaction Methods 0.000 claims description 12
• 229910052763 palladium Inorganic materials 0.000 claims description 12
• 125000004429 atom Chemical group 0.000 claims description 11
• 239000003153 chemical reaction reagent Substances 0.000 claims description 11
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 11
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 10
• 239000003054 catalyst Substances 0.000 claims description 10
• 239000003638 chemical reducing agent Substances 0.000 claims description 9
• UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 9
• 239000003446 ligand Substances 0.000 claims description 9
• 229910052760 oxygen Inorganic materials 0.000 claims description 9
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
• 150000001721 carbon Chemical group 0.000 claims description 6
• QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 6
• 230000008569 process Effects 0.000 claims description 6
• 125000006239 protecting group Chemical group 0.000 claims description 6
• PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 claims description 6
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 4
• 150000001723 carbon free-radicals Chemical class 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• MSZGXBOIMNUSNZ-UHFFFAOYSA-N n-(1-benzyl-3-methylindazol-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(C)=N2)=CC=CC=1N2CC1=CC=CC=C1 MSZGXBOIMNUSNZ-UHFFFAOYSA-N 0.000 claims description 4
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
• 150000003254 radicals Chemical class 0.000 claims description 4
• 125000004434 sulfur atom Chemical group 0.000 claims description 4
• 125000006273 (C1-C3) alkyl group Chemical group 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 3
• GSZCBMFOSHKWOI-UHFFFAOYSA-N 7-(2,3-dihydroxypropoxy)-n-[3-methyl-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(OCC(O)CO)=CC4=NC=3)=C2C(C)=NN1CC1=CC=CC(C)=N1 GSZCBMFOSHKWOI-UHFFFAOYSA-N 0.000 claims description 3
• UKXAXKQYJOEJHK-UHFFFAOYSA-N 7-fluoro-n-[3-methyl-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(F)=CC4=NC=3)=C2C(C)=NN1CC1=CC=CC(C)=N1 UKXAXKQYJOEJHK-UHFFFAOYSA-N 0.000 claims description 3
• VRYZDEAVUJFOIL-UHFFFAOYSA-N C=1N=C2C=C(O)C=CN2C=1C(=O)NC(C=1C=N2)=CC=CC=1N2CC1=CC=CC=C1 Chemical compound C=1N=C2C=C(O)C=CN2C=1C(=O)NC(C=1C=N2)=CC=CC=1N2CC1=CC=CC=C1 VRYZDEAVUJFOIL-UHFFFAOYSA-N 0.000 claims description 3
• 230000001363 autoimmune Effects 0.000 claims description 3
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 3
• 239000007822 coupling agent Substances 0.000 claims description 3
• IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 3
• 229940095102 methyl benzoate Drugs 0.000 claims description 3
• UVPCNXAFSUJXGZ-UHFFFAOYSA-N n-(1-benzylindazol-4-yl)-7-(2-morpholin-4-ylethoxy)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C=1N=C2C=C(OCCN3CCOCC3)C=CN2C=1C(=O)NC(C=1C=N2)=CC=CC=1N2CC1=CC=CC=C1 UVPCNXAFSUJXGZ-UHFFFAOYSA-N 0.000 claims description 3
• UNEBOQFCIQVXLS-UHFFFAOYSA-N n-[3-methyl-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(C)=NN1CC1=CC=CC(C)=N1 UNEBOQFCIQVXLS-UHFFFAOYSA-N 0.000 claims description 3
• PNEAFHNKKWCATH-UHFFFAOYSA-N n-[3-methyl-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(C)=NN1CC1=CC=C(C)N=C1 PNEAFHNKKWCATH-UHFFFAOYSA-N 0.000 claims description 3
• 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 claims description 2
• 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 2
• ALPTZPFVGLVIKK-UHFFFAOYSA-N 2-methyl-2,6-diazaspiro[3.3]heptane Chemical compound C1N(C)CC11CNC1 ALPTZPFVGLVIKK-UHFFFAOYSA-N 0.000 claims description 2
• XBNCEMAQEYTQHZ-UHFFFAOYSA-N 6-cyano-n-[3-methyl-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=C(C=CC4=NC=3)C#N)=C2C(C)=NN1CC1=CC=CC(C)=N1 XBNCEMAQEYTQHZ-UHFFFAOYSA-N 0.000 claims description 2
• MWPOANXKDIXRKH-UHFFFAOYSA-N 7-[2-(dimethylamino)ethoxy]-n-[3-methyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C=1N=C2C=C(OCCN(C)C)C=CN2C=1C(=O)NC(C=1C(C)=N2)=CC=CC=1N2CC1=CC=CC(C)=N1 MWPOANXKDIXRKH-UHFFFAOYSA-N 0.000 claims description 2
• JEUBGROKTGOCSX-UHFFFAOYSA-N 7-[2-(dimethylamino)ethyl]-n-[3-methyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C=1N=C2C=C(CCN(C)C)C=CN2C=1C(=O)NC(C=1C(C)=N2)=CC=CC=1N2CC1=CC=CC(C)=N1 JEUBGROKTGOCSX-UHFFFAOYSA-N 0.000 claims description 2
• VPJJVXVLGDVRMM-UHFFFAOYSA-N 7-acetyl-n-[3-methyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C=1N=C2C=C(C(=O)C)C=CN2C=1C(=O)NC(C=1C(C)=N2)=CC=CC=1N2CC1=CC=CC(C)=N1 VPJJVXVLGDVRMM-UHFFFAOYSA-N 0.000 claims description 2
• 229940125773 compound 10 Drugs 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 claims description 2
• KSBHQGGOSZPQOE-UHFFFAOYSA-N n-(1-benzylindazol-4-yl)-7-(2,3-dihydroxypropoxy)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C=1N=C2C=C(OCC(O)CO)C=CN2C=1C(=O)NC(C=1C=N2)=CC=CC=1N2CC1=CC=CC=C1 KSBHQGGOSZPQOE-UHFFFAOYSA-N 0.000 claims description 2
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 2
• 239000007800 oxidant agent Substances 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
• 235000005152 nicotinamide Nutrition 0.000 claims 2
• 239000011570 nicotinamide Substances 0.000 claims 2
• 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
• JUQWFONZRDXAAB-UHFFFAOYSA-N 1-methyl-1-oxidopiperazin-1-ium Chemical compound C[N+]1([O-])CCNCC1 JUQWFONZRDXAAB-UHFFFAOYSA-N 0.000 claims 1
• QKXUBXSICMMQTD-UHFFFAOYSA-N 3-n-(1-benzylindazol-4-yl)imidazo[1,2-a]pyridine-3,6-dicarboxamide Chemical compound N12C=C(C(=O)N)C=CC2=NC=C1C(=O)NC(C=1C=N2)=CC=CC=1N2CC1=CC=CC=C1 QKXUBXSICMMQTD-UHFFFAOYSA-N 0.000 claims 1
• NBVSVINKCPUZOG-UHFFFAOYSA-N 7-(2-methoxyethoxy)-n-[1-[(3-phenylmethoxyphenyl)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=N2)=CC=CC=1N2CC(C=1)=CC=CC=1OCC1=CC=CC=C1 NBVSVINKCPUZOG-UHFFFAOYSA-N 0.000 claims 1
• AFFFKKYYLVVAAP-UHFFFAOYSA-N 7-(2-methoxyethoxy)-n-[1-[[3-(methylcarbamoyl)phenyl]methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound CNC(=O)C1=CC=CC(CN2C3=CC=CC(NC(=O)C=4N5C=CC(OCCOC)=CC5=NC=4)=C3C=N2)=C1 AFFFKKYYLVVAAP-UHFFFAOYSA-N 0.000 claims 1
• AZMSFGSBEXZSQD-UHFFFAOYSA-N N-[2-(4-methylpiperazin-1-yl)ethoxy]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound N=1C=C(N2C=1C=CC=C2)C(=O)NOCCN1CCN(CC1)C AZMSFGSBEXZSQD-UHFFFAOYSA-N 0.000 claims 1
• 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
• GDSVZPUBMGOHCE-UHFFFAOYSA-N n-(1-benzylindazol-4-yl)-6-(1,2-dihydroxyethyl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound N12C=C(C(O)CO)C=CC2=NC=C1C(=O)NC(C=1C=N2)=CC=CC=1N2CC1=CC=CC=C1 GDSVZPUBMGOHCE-UHFFFAOYSA-N 0.000 claims 1
• IQSLRRLZPUWMAU-UHFFFAOYSA-N n-(1-benzylindazol-4-yl)-6-bromoimidazo[1,2-a]pyridine-3-carboxamide Chemical compound N12C=C(Br)C=CC2=NC=C1C(=O)NC(C=1C=N2)=CC=CC=1N2CC1=CC=CC=C1 IQSLRRLZPUWMAU-UHFFFAOYSA-N 0.000 claims 1
• NWPHHXOYPCIZRC-UHFFFAOYSA-N n-(1-benzylindazol-4-yl)-6-fluoroimidazo[1,2-a]pyridine-3-carboxamide Chemical compound N12C=C(F)C=CC2=NC=C1C(=O)NC(C=1C=N2)=CC=CC=1N2CC1=CC=CC=C1 NWPHHXOYPCIZRC-UHFFFAOYSA-N 0.000 claims 1
• XZYXERAAWGRITM-UHFFFAOYSA-N n-(1-benzylindazol-4-yl)-6-methoxyimidazo[1,2-a]pyridine-3-carboxamide Chemical compound N12C=C(OC)C=CC2=NC=C1C(=O)NC(C=1C=N2)=CC=CC=1N2CC1=CC=CC=C1 XZYXERAAWGRITM-UHFFFAOYSA-N 0.000 claims 1
• LHFFRHAIRHXUEO-UHFFFAOYSA-N n-(1-benzylindazol-4-yl)-7-(1,2-dihydroxyethyl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C=1N=C2C=C(C(O)CO)C=CN2C=1C(=O)NC(C=1C=N2)=CC=CC=1N2CC1=CC=CC=C1 LHFFRHAIRHXUEO-UHFFFAOYSA-N 0.000 claims 1
• JGYCMBPHJUCSOV-UHFFFAOYSA-N n-(1-benzylindazol-4-yl)-7-(1-hydroxyethyl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C=1N=C2C=C(C(O)C)C=CN2C=1C(=O)NC(C=1C=N2)=CC=CC=1N2CC1=CC=CC=C1 JGYCMBPHJUCSOV-UHFFFAOYSA-N 0.000 claims 1
• MKECQTBPRUFEEF-UHFFFAOYSA-N n-(1-benzylindazol-4-yl)-7-(1-morpholin-4-ylethyl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=CN2C(C(=O)NC=3C=4C=NN(CC=5C=CC=CC=5)C=4C=CC=3)=CN=C2C=C1C(C)N1CCOCC1 MKECQTBPRUFEEF-UHFFFAOYSA-N 0.000 claims 1
• KRVICMRESFVIOW-UHFFFAOYSA-N n-(1-benzylindazol-4-yl)-7-(1h-pyrazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C=1N=C2C=C(C3=CNN=C3)C=CN2C=1C(=O)NC(C=1C=N2)=CC=CC=1N2CC1=CC=CC=C1 KRVICMRESFVIOW-UHFFFAOYSA-N 0.000 claims 1
• VGGHDOVGJGYKFL-UHFFFAOYSA-N n-(1-benzylindazol-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=N2)=CC=CC=1N2CC1=CC=CC=C1 VGGHDOVGJGYKFL-UHFFFAOYSA-N 0.000 claims 1
• GWZWSVFLHNNSSQ-UHFFFAOYSA-N n-(1-benzylindazol-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=NN(CC=5C=CC=CC=5)C=4C=CC=3)N2C=C1 GWZWSVFLHNNSSQ-UHFFFAOYSA-N 0.000 claims 1
• KHNVWNQXNVDANJ-UHFFFAOYSA-N n-(1-benzylindazol-4-yl)-7-bromoimidazo[1,2-a]pyridine-3-carboxamide Chemical compound C=1N=C2C=C(Br)C=CN2C=1C(=O)NC(C=1C=N2)=CC=CC=1N2CC1=CC=CC=C1 KHNVWNQXNVDANJ-UHFFFAOYSA-N 0.000 claims 1
• FAAFDOGSFJDJRV-UHFFFAOYSA-N n-(1-benzylindazol-4-yl)-7-cyanoimidazo[1,2-a]pyridine-3-carboxamide Chemical compound C=1N=C2C=C(C#N)C=CN2C=1C(=O)NC(C=1C=N2)=CC=CC=1N2CC1=CC=CC=C1 FAAFDOGSFJDJRV-UHFFFAOYSA-N 0.000 claims 1
• JSWRJPHTFSRVNU-UHFFFAOYSA-N n-(1-benzylindazol-4-yl)-7-ethoxyimidazo[1,2-a]pyridine-3-carboxamide Chemical compound C=1N=C2C=C(OCC)C=CN2C=1C(=O)NC(C=1C=N2)=CC=CC=1N2CC1=CC=CC=C1 JSWRJPHTFSRVNU-UHFFFAOYSA-N 0.000 claims 1
• BXTGSZAUHVHTTN-UHFFFAOYSA-N n-(1-benzylindazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C=1N=C2C=CC=CN2C=1C(=O)NC(C=1C=N2)=CC=CC=1N2CC1=CC=CC=C1 BXTGSZAUHVHTTN-UHFFFAOYSA-N 0.000 claims 1
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• MZCNCDLKMBOASH-UHFFFAOYSA-N n-[1-(pyridin-2-ylmethyl)indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C=1N=C2C=CC=CN2C=1C(=O)NC(C=1C=N2)=CC=CC=1N2CC1=CC=CC=N1 MZCNCDLKMBOASH-UHFFFAOYSA-N 0.000 claims 1
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