JP5739448B2 - ｃＦＭＳ阻害剤としての置換Ｎ−（１Ｈ−インダゾール−４−イル）イミダゾ［１，２−ａ］ピリジン−３−カルボキサミド化合物 - Google Patents

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Publication number

JP5739448B2

JP5739448B2 JP2012546120A JP2012546120A JP5739448B2 JP 5739448 B2 JP5739448 B2 JP 5739448B2 JP 2012546120 A JP2012546120 A JP 2012546120A JP 2012546120 A JP2012546120 A JP 2012546120A JP 5739448 B2 JP5739448 B2 JP 5739448B2

Authority

JP

Japan

Prior art keywords

methyl

pyridine

indazol

imidazo

ethyl

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.)

Expired - Fee Related

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• 239000003112 inhibitor Substances 0.000 title description 21
• 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 3
• 125000000217 alkyl group Chemical group 0.000 claims description 449
• 150000001875 compounds Chemical class 0.000 claims description 387
• 125000003545 alkoxy group Chemical group 0.000 claims description 344
• -1 pyridinonyl Chemical group 0.000 claims description 337
• 239000000203 mixture Substances 0.000 claims description 197
• 125000001424 substituent group Chemical group 0.000 claims description 137
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 111
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 75
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 69
• 229910052739 hydrogen Inorganic materials 0.000 claims description 67
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 66
• DFPAKSUCGFBDDF-UHFFFAOYSA-N nicotinic acid amide Natural products NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 65
• 229910052757 nitrogen Inorganic materials 0.000 claims description 64
• 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 57
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 47
• 125000005842 heteroatom Chemical group 0.000 claims description 47
• 206010028980 Neoplasm Diseases 0.000 claims description 42
• 229910052736 halogen Inorganic materials 0.000 claims description 42
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 41
• 150000003839 salts Chemical class 0.000 claims description 41
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 39
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 36
• 230000008878 coupling Effects 0.000 claims description 35
• 238000010168 coupling process Methods 0.000 claims description 35
• 238000005859 coupling reaction Methods 0.000 claims description 35
• 235000005152 nicotinamide Nutrition 0.000 claims description 35
• 239000011570 nicotinamide Substances 0.000 claims description 35
• 125000000623 heterocyclic group Chemical group 0.000 claims description 34
• 210000000988 bone and bone Anatomy 0.000 claims description 33
• 201000010099 disease Diseases 0.000 claims description 32
• 150000002367 halogens Chemical class 0.000 claims description 30
• 229910052760 oxygen Inorganic materials 0.000 claims description 30
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 30
• 201000011510 cancer Diseases 0.000 claims description 28
• 125000004076 pyridyl group Chemical group 0.000 claims description 27
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 26
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 25
• 125000004429 atom Chemical group 0.000 claims description 24
• 239000003054 catalyst Substances 0.000 claims description 24
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
• 229910052763 palladium Inorganic materials 0.000 claims description 24
• 208000002193 Pain Diseases 0.000 claims description 23
• 229920006395 saturated elastomer Polymers 0.000 claims description 22
• 229910052717 sulfur Inorganic materials 0.000 claims description 21
• 241000124008 Mammalia Species 0.000 claims description 20
• PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims description 19
• 229910017051 nitrogen difluoride Inorganic materials 0.000 claims description 19
• 229910052731 fluorine Inorganic materials 0.000 claims description 18
• 208000027866 inflammatory disease Diseases 0.000 claims description 18
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 18
• 125000004414 alkyl thio group Chemical group 0.000 claims description 17
• 229910052801 chlorine Inorganic materials 0.000 claims description 16
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 15
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 15
• 239000003153 chemical reaction reagent Substances 0.000 claims description 15
• 239000003638 chemical reducing agent Substances 0.000 claims description 15
• 229910052740 iodine Inorganic materials 0.000 claims description 15
• 208000023275 Autoimmune disease Diseases 0.000 claims description 14
• 239000003446 ligand Substances 0.000 claims description 14
• UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 14
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 14
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 13
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 13
• 125000006413 ring segment Chemical group 0.000 claims description 12
• 125000006239 protecting group Chemical group 0.000 claims description 11
• 229910052799 carbon Inorganic materials 0.000 claims description 10
• PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 claims description 10
• 229910052794 bromium Inorganic materials 0.000 claims description 8
• 125000004990 dihydroxyalkyl group Chemical group 0.000 claims description 8
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 8
• 150000003254 radicals Chemical class 0.000 claims description 8
• 238000002560 therapeutic procedure Methods 0.000 claims description 8
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 7
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 7
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
• 230000009467 reduction Effects 0.000 claims description 7
• 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 6
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 6
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 6
• 125000001072 heteroaryl group Chemical group 0.000 claims description 6
• 239000008194 pharmaceutical composition Substances 0.000 claims description 6
• 238000007363 ring formation reaction Methods 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
• 239000012190 activator Substances 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• 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 5
• 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 5
• 229910052700 potassium Inorganic materials 0.000 claims description 5
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
• 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 4
• 150000001723 carbon free-radicals Chemical class 0.000 claims description 4
• 239000007822 coupling agent Substances 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 4
• 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 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
• 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 4
• 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 4
• 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 4
• 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 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
• POOPWPIOIMBTOH-UHFFFAOYSA-N 8-oxa-3-azabicyclo[3.2.1]octane Chemical compound C1NCC2CCC1O2 POOPWPIOIMBTOH-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 claims description 3
• 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 3
• 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 3
• 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 3
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 3
• 239000007800 oxidant agent Substances 0.000 claims description 3
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 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
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[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
• STUHQDIOZQUPGP-UHFFFAOYSA-N morpholin-4-ium-4-carboxylate Chemical compound OC(=O)N1CCOCC1 STUHQDIOZQUPGP-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
• 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
• 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 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
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• 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
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