RU2562977C2 - СОЕДИНЕНИЯ ЗАМЕЩЕННОГО N-(1Н-ИНДАЗОЛ-4-ИЛ)ИМИДАЗОЛ[1,2-a]ПИРИДИН-3-КАРБОКСАМИДА КАК ИНГИБИТОРЫ cFMS - Google Patents

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Publication number

RU2562977C2

RU2562977C2 RU2012131129/04A RU2012131129A RU2562977C2 RU 2562977 C2 RU2562977 C2 RU 2562977C2 RU 2012131129/04 A RU2012131129/04 A RU 2012131129/04A RU 2012131129 A RU2012131129 A RU 2012131129A RU 2562977 C2 RU2562977 C2 RU 2562977C2

Authority

RU

Russia

Prior art keywords

methyl

indazol

imidazo

ethyl

carboxamide

Prior art date

2009-12-21

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 229
• 239000003112 inhibitor Substances 0.000 title abstract description 27
• FYGOVURIVUJKKF-UHFFFAOYSA-N N1N=CC2=C1C=CC=C2N1C=CN=C1 Chemical class N1N=CC2=C1C=CC=C2N1C=CN=C1 FYGOVURIVUJKKF-UHFFFAOYSA-N 0.000 title description 3
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 255
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 246
• 125000001424 substituent group Chemical group 0.000 claims abstract description 111
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 81
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 59
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 57
• 238000000034 method Methods 0.000 claims abstract description 50
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 47
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 39
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 38
• 150000003839 salts Chemical class 0.000 claims abstract description 37
• 150000002367 halogens Chemical class 0.000 claims abstract description 34
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 33
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 28
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 23
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 21
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 20
• 208000020084 Bone disease Diseases 0.000 claims abstract description 19
• 125000004076 pyridyl group Chemical group 0.000 claims abstract description 19
• 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 16
• 229910052740 iodine Inorganic materials 0.000 claims abstract description 16
• IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 16
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 16
• PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims abstract description 15
• 229910052794 bromium Inorganic materials 0.000 claims abstract description 13
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims abstract description 12
• 229910052801 chlorine Inorganic materials 0.000 claims abstract description 12
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 12
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims abstract description 9
• 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 8
• 125000004990 dihydroxyalkyl group Chemical group 0.000 claims abstract description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
• 230000000694 effects Effects 0.000 claims abstract description 5
• 125000005843 halogen group Chemical group 0.000 claims abstract description 4
• -1 difluoroamino Chemical group 0.000 claims description 447
• 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 64
• 229910052739 hydrogen Inorganic materials 0.000 claims description 63
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 41
• 229920006395 saturated elastomer Polymers 0.000 claims description 25
• 241000124008 Mammalia Species 0.000 claims description 20
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 19
• 229910052731 fluorine Inorganic materials 0.000 claims description 15
• 229910017051 nitrogen difluoride Inorganic materials 0.000 claims description 14
• 230000003993 interaction Effects 0.000 claims description 9
• 230000015572 biosynthetic process Effects 0.000 claims description 7
• 125000006239 protecting group Chemical group 0.000 claims description 7
• 238000002560 therapeutic procedure Methods 0.000 claims description 7
• 108091000080 Phosphotransferase Proteins 0.000 claims description 5
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
• 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 5
• 102000020233 phosphotransferase Human genes 0.000 claims description 5
• 125000004434 sulfur atom Chemical group 0.000 claims description 5
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 4
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 4
• 239000007822 coupling agent Substances 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• 125000001072 heteroaryl group Chemical group 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
• 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 4
• 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 4
• 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 4
• 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 3
• 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 3
• 125000005330 8 membered heterocyclic group Chemical group 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
• 230000005764 inhibitory process Effects 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 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 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
• 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
• 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 3
• 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 3
• 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 3
• 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 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
• 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 3
• 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
• 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
• 208000018084 Bone neoplasm Diseases 0.000 claims description 2
• XNOAZHOQBMLGOO-UHFFFAOYSA-N CC1=CC=CC(CN2C3=CC=CC(NC(=O)C=4N5C=CC(O)=CC5=NC=4)=C3C(C3CC3)=N2)=N1 Chemical compound CC1=CC=CC(CN2C3=CC=CC(NC(=O)C=4N5C=CC(O)=CC5=NC=4)=C3C(C3CC3)=N2)=N1 XNOAZHOQBMLGOO-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
• 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
• 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
• 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
• 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
• 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
• YHBYPXGRBVLGCM-UHFFFAOYSA-N n-[3-ethyl-1-[(6-ethylpyridin-2-yl)methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC=CC4=NC=3)=C2C(CC)=NN1CC1=CC=CC(CC)=N1 YHBYPXGRBVLGCM-UHFFFAOYSA-N 0.000 claims description 2
• ULKSYLSNHQPJQA-UHFFFAOYSA-N n-[3-ethyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-[(4-methylpiperazin-1-yl)methyl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(CN5CCN(C)CC5)=CC4=NC=3)=C2C(CC)=NN1CC1=CC=CC(C)=N1 ULKSYLSNHQPJQA-UHFFFAOYSA-N 0.000 claims description 2
• ORWFYKVVNFEZBW-UHFFFAOYSA-N n-[3-ethyl-1-[(6-methylpyridin-2-yl)methyl]indazol-4-yl]-7-[2-(4-methyl-4-oxidopiperazin-4-ium-1-yl)ethoxy]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC(OCCN5CC[N+](C)([O-])CC5)=CC4=NC=3)=C2C(CC)=NN1CC1=CC=CC(C)=N1 ORWFYKVVNFEZBW-UHFFFAOYSA-N 0.000 claims description 2
• 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
• JMNQZEVFQQRSQH-UHFFFAOYSA-N n-[3-ethyl-1-[(6-methylpyridin-3-yl)methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC=CC4=NC=3)=C2C(CC)=NN1CC1=CC=C(C)N=C1 JMNQZEVFQQRSQH-UHFFFAOYSA-N 0.000 claims description 2
• ZOCGXBBRKRAKLQ-UHFFFAOYSA-N n-[3-ethyl-1-[(6-piperazin-1-ylpyridin-2-yl)methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC=CC4=NC=3)=C2C(CC)=NN1CC(N=1)=CC=CC=1N1CCNCC1 ZOCGXBBRKRAKLQ-UHFFFAOYSA-N 0.000 claims description 2
• APZMSBZXHGTGIE-UHFFFAOYSA-N n-[3-ethyl-1-[(6-piperidin-4-yloxypyridin-2-yl)methyl]indazol-4-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C12=CC=CC(NC(=O)C=3N4C=CC=CC4=NC=3)=C2C(CC)=NN1CC(N=1)=CC=CC=1OC1CCNCC1 APZMSBZXHGTGIE-UHFFFAOYSA-N 0.000 claims description 2
• 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
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