CA2785338C - Substituted n-(1h-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide compounds as cfms inhibitors - Google Patents

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Publication number

CA2785338C

CA2785338C CA2785338A CA2785338A CA2785338C CA 2785338 C CA2785338 C CA 2785338C CA 2785338 A CA2785338 A CA 2785338A CA 2785338 A CA2785338 A CA 2785338A CA 2785338 C CA2785338 C CA 2785338C

Authority

CA

Canada

Prior art keywords

methyl

indazol

imidazo

pyridine

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.)

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• 239000003112 inhibitor Substances 0.000 title abstract description 23
• 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
• 150000001875 compounds Chemical class 0.000 claims abstract description 306
• 238000011282 treatment Methods 0.000 claims abstract description 50
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 47
• 150000003839 salts Chemical class 0.000 claims abstract description 42
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 40
• 210000000988 bone and bone Anatomy 0.000 claims abstract description 36
• 201000010099 disease Diseases 0.000 claims abstract description 32
• 201000011510 cancer Diseases 0.000 claims abstract description 28
• 208000002193 Pain Diseases 0.000 claims abstract description 22
• 208000027866 inflammatory disease Diseases 0.000 claims abstract description 17
• 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 16
• 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 16
• 125000000217 alkyl group Chemical group 0.000 claims description 326
• 125000003545 alkoxy group Chemical group 0.000 claims description 262
• 238000002360 preparation method Methods 0.000 claims description 144
• 125000001424 substituent group Chemical group 0.000 claims description 107
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 96
• -1 hetCyc10- Chemical group 0.000 claims description 96
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 91
• 229910052757 nitrogen Inorganic materials 0.000 claims description 69
• 229910052739 hydrogen Inorganic materials 0.000 claims description 61
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 54
• 235000005152 nicotinamide Nutrition 0.000 claims description 49
• 239000011570 nicotinamide Substances 0.000 claims description 49
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 48
• 239000002585 base Substances 0.000 claims description 47
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 46
• 238000000034 method Methods 0.000 claims description 45
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 42
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 41
• 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 35
• 125000005842 heteroatom Chemical group 0.000 claims description 33
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
• 230000008878 coupling Effects 0.000 claims description 32
• 238000010168 coupling process Methods 0.000 claims description 32
• 238000005859 coupling reaction Methods 0.000 claims description 32
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 32
• 229910052736 halogen Inorganic materials 0.000 claims description 31
• 150000002367 halogens Chemical class 0.000 claims description 27
• 125000000623 heterocyclic group Chemical group 0.000 claims description 26
• 125000004076 pyridyl group Chemical group 0.000 claims description 24
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 22
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 20
• 125000004429 atom Chemical group 0.000 claims description 19
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
• 239000003054 catalyst Substances 0.000 claims description 18
• 229910052763 palladium Inorganic materials 0.000 claims description 18
• 208000003076 Osteolysis Diseases 0.000 claims description 15
• IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 15
• 208000029791 lytic metastatic bone lesion Diseases 0.000 claims description 15
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 15
• 229910052731 fluorine Inorganic materials 0.000 claims description 14
• PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims description 14
• 229910017051 nitrogen difluoride Inorganic materials 0.000 claims description 14
• 229920006395 saturated elastomer Polymers 0.000 claims description 14
• 229910052794 bromium Inorganic materials 0.000 claims description 13
• 239000003153 chemical reaction reagent Substances 0.000 claims description 13
• 229910052740 iodine Inorganic materials 0.000 claims description 13
• 239000003638 chemical reducing agent Substances 0.000 claims description 12
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 11
• 229910052799 carbon Inorganic materials 0.000 claims description 11
• 229910052801 chlorine Inorganic materials 0.000 claims description 11
• 239000003446 ligand Substances 0.000 claims description 11
• 229910052760 oxygen Inorganic materials 0.000 claims description 11
• 125000004414 alkyl thio group Chemical group 0.000 claims description 10
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 10
• UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 10
• 229910052717 sulfur Inorganic materials 0.000 claims description 10
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 8
• 230000008569 process Effects 0.000 claims description 8
• 125000006413 ring segment Chemical group 0.000 claims description 8
• 238000002560 therapeutic procedure Methods 0.000 claims description 8
• 208000001132 Osteoporosis Diseases 0.000 claims description 7
• 125000006239 protecting group Chemical group 0.000 claims description 7
• 150000003254 radicals Chemical class 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
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
• 125000004990 dihydroxyalkyl group Chemical group 0.000 claims description 6
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 6
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
• 210000001519 tissue Anatomy 0.000 claims description 6
• 206010027476 Metastases Diseases 0.000 claims 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 description 5
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
• 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 5
• 230000009401 metastasis Effects 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
• 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 5
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
• 230000009467 reduction Effects 0.000 claims description 5
• NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 claims description 4
• 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 4
• 206010065687 Bone loss Diseases 0.000 claims description 4
• 208000002250 Hematologic Neoplasms Diseases 0.000 claims description 4
• 206010035226 Plasma cell myeloma Diseases 0.000 claims description 4
• 239000002253 acid Substances 0.000 claims description 4
• 125000002618 bicyclic heterocycle 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
• 125000001072 heteroaryl group Chemical group 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
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
• 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 3
• 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 3
• 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 3
• 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims description 3
• 208000010191 Osteitis Deformans Diseases 0.000 claims description 3
• 208000027868 Paget disease Diseases 0.000 claims description 3
• 239000007822 coupling agent Substances 0.000 claims description 3
• 208000027202 mammary Paget disease Diseases 0.000 claims description 3
• 201000001441 melanoma Diseases 0.000 claims description 3
• 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 3
• 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 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
• 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
• 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 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
• 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 3
• 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 3
• ULWIAWOTDYHSPR-UHFFFAOYSA-N n-[3-ethyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-(2-morpholin-4-ylethoxy)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(OCCN5CCOCC5)=CC4=NC=3)=C2C(CC)=NN1CC1=CC=CC(C)=N1 ULWIAWOTDYHSPR-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
• 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
• 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
• 239000007800 oxidant agent Substances 0.000 claims description 3
• 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 3
• 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 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
• 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
• NIKIYEZYAGVZBN-UHFFFAOYSA-N 7-(1,4-diazepan-1-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)N3CCNCCC3)=C2C(CC)=NN1CC1=CC=CC(C)=N1 NIKIYEZYAGVZBN-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
• CFIIFDUJSFTZCM-UHFFFAOYSA-N 7-(3-amino-2,2-difluoropropoxy)-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(OCC(F)(F)CN)=CC4=NC=3)=C2C(CC)=NN1CC1=CC=CC(C)=N1 CFIIFDUJSFTZCM-UHFFFAOYSA-N 0.000 claims description 2
• KKFRWLUQPBFUNW-UHFFFAOYSA-N 7-(azetidin-3-yloxy)-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(OC5CNC5)=CC4=NC=3)=C2C(CC)=NN1CC1=CC=CC(C)=N1 KKFRWLUQPBFUNW-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
• SQYKGTPWRZMMIK-UHFFFAOYSA-N 7-[2-(azetidin-1-yl)ethoxy]-n-[3-cyclopropyl-1-[(1-methyl-2-oxopyridin-3-yl)methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound O=C1N(C)C=CC=C1CN1C2=CC=CC(NC(=O)C=3N4C=CC(OCCN5CCC5)=CC4=NC=3)=C2C(C2CC2)=N1 SQYKGTPWRZMMIK-UHFFFAOYSA-N 0.000 claims description 2
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• WAEULDKXPICBAH-UHFFFAOYSA-N n-[3-cyclopropyl-1-[(5-methyl-1,3,4-thiadiazol-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=5SC(C)=NN=5)C=4C=CC=3)N2C=C1 WAEULDKXPICBAH-UHFFFAOYSA-N 0.000 claims description 2
• RHDXUUDHWYWTHB-UHFFFAOYSA-N n-[3-cyclopropyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-(1-methylpiperidin-4-yl)oxyimidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1CN(C)CCC1OC1=CC2=NC=C(C(=O)NC=3C=4C(C5CC5)=NN(CC=5N=C(C)C=CC=5)C=4C=CC=3)N2C=C1 RHDXUUDHWYWTHB-UHFFFAOYSA-N 0.000 claims description 2
• CAXKGVJOTNGAST-UHFFFAOYSA-N n-[3-cyclopropyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-(2-piperazin-1-ylethoxy)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound CC1=CC=CC(CN2C3=CC=CC(NC(=O)C=4N5C=CC(OCCN6CCNCC6)=CC5=NC=4)=C3C(C3CC3)=N2)=N1 CAXKGVJOTNGAST-UHFFFAOYSA-N 0.000 claims description 2
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• BHFTXSHRWAYEKY-UHFFFAOYSA-N n-[3-cyclopropyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-[2-(2-hydroxyethoxy)ethoxy]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound CC1=CC=CC(CN2C3=CC=CC(NC(=O)C=4N5C=CC(OCCOCCO)=CC5=NC=4)=C3C(C3CC3)=N2)=N1 BHFTXSHRWAYEKY-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
• 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
• 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
• KNUUYJCYOBIOEC-UHFFFAOYSA-N n-[3-cyclopropyl-1-[(6-methylpyridin-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=NC(C)=CC=5)C=4C=CC=3)N2C=C1 KNUUYJCYOBIOEC-UHFFFAOYSA-N 0.000 claims description 2
• KLSUKMJBPGUGJF-UHFFFAOYSA-N n-[3-ethyl-1-(1,3-thiazol-2-ylmethyl)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=CS1 KLSUKMJBPGUGJF-UHFFFAOYSA-N 0.000 claims description 2
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• JRCPYNSPYPUPII-UHFFFAOYSA-N n-[3-ethyl-1-[(1-ethylpyrazol-3-yl)methyl]indazol-4-yl]-7-(1,2,4-triazol-1-yl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(=CC4=NC=3)N3N=CN=C3)=C2C(CC)=NN1CC=1C=CN(CC)N=1 JRCPYNSPYPUPII-UHFFFAOYSA-N 0.000 claims description 2
• SNVCSOILDYSSCA-UHFFFAOYSA-N n-[3-ethyl-1-[(1-ethylpyrazol-3-yl)methyl]indazol-4-yl]-7-(1-methylpiperidin-4-yl)oxyimidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(OC5CCN(C)CC5)=CC4=NC=3)=C2C(CC)=NN1CC=1C=CN(CC)N=1 SNVCSOILDYSSCA-UHFFFAOYSA-N 0.000 claims description 2
• VYAWSTQXFZRJEY-UHFFFAOYSA-N n-[3-ethyl-1-[(1-ethylpyrazol-3-yl)methyl]indazol-4-yl]-7-(2-morpholin-4-ylethoxy)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(OCCN5CCOCC5)=CC4=NC=3)=C2C(CC)=NN1CC=1C=CN(CC)N=1 VYAWSTQXFZRJEY-UHFFFAOYSA-N 0.000 claims description 2
• DLURWSDCNVGXGS-UHFFFAOYSA-N n-[3-ethyl-1-[(1-ethylpyrazol-3-yl)methyl]indazol-4-yl]-7-(2-pyrrolidin-1-ylethoxy)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(OCCN5CCCC5)=CC4=NC=3)=C2C(CC)=NN1CC=1C=CN(CC)N=1 DLURWSDCNVGXGS-UHFFFAOYSA-N 0.000 claims description 2
• OAIHCGHCJBYTAV-UHFFFAOYSA-N n-[3-ethyl-1-[(1-ethylpyrazol-3-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)=NN1CC=1C=CN(CC)N=1 OAIHCGHCJBYTAV-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
• OYSJUNNZMYPPDD-UHFFFAOYSA-N n-[3-ethyl-1-[(2-methyl-1,3-thiazol-4-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=CSC(C)=N1 OYSJUNNZMYPPDD-UHFFFAOYSA-N 0.000 claims description 2
• FYLCAOZAZWECHN-UHFFFAOYSA-N n-[3-ethyl-1-[(2-propan-2-yl-1,3-thiazol-4-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=CSC(C(C)C)=N1 FYLCAOZAZWECHN-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
• AEJSXLHXQILYJV-UHFFFAOYSA-N n-[3-ethyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-(1,2,4-triazol-1-yl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(=CC4=NC=3)N3N=CN=C3)=C2C(CC)=NN1CC1=CC=CC(C)=N1 AEJSXLHXQILYJV-UHFFFAOYSA-N 0.000 claims description 2
• DPFMSWIHNGFWRO-UHFFFAOYSA-N n-[3-ethyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-(2-hydroxyethoxy)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(OCCO)=CC4=NC=3)=C2C(CC)=NN1CC1=CC=CC(C)=N1 DPFMSWIHNGFWRO-UHFFFAOYSA-N 0.000 claims description 2
• VIIPUMFRADEZHH-UHFFFAOYSA-N n-[3-ethyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-(2-piperazin-1-ylethoxy)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(OCCN5CCNCC5)=CC4=NC=3)=C2C(CC)=NN1CC1=CC=CC(C)=N1 VIIPUMFRADEZHH-UHFFFAOYSA-N 0.000 claims description 2
• LWUFSZFCFWDIQR-UHFFFAOYSA-N n-[3-ethyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-(3-methyl-1,2,4-triazol-1-yl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(=CC4=NC=3)N3N=C(C)N=C3)=C2C(CC)=NN1CC1=CC=CC(C)=N1 LWUFSZFCFWDIQR-UHFFFAOYSA-N 0.000 claims description 2
• FUHLOTZJQWQYRJ-UHFFFAOYSA-N n-[3-ethyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-(3-oxopiperazin-1-yl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(=CC4=NC=3)N3CC(=O)NCC3)=C2C(CC)=NN1CC1=CC=CC(C)=N1 FUHLOTZJQWQYRJ-UHFFFAOYSA-N 0.000 claims description 2
• MJHDJRGWGGAQRJ-UHFFFAOYSA-N n-[3-ethyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-(4-ethylpiperazin-1-yl)imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1CN(CC)CCN1C1=CC2=NC=C(C(=O)NC=3C=4C(CC)=NN(CC=5N=C(C)C=CC=5)C=4C=CC=3)N2C=C1 MJHDJRGWGGAQRJ-UHFFFAOYSA-N 0.000 claims description 2
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