TWI471326B - 作為ｃＦＭＳ抑制劑之經取代之Ｎ－（１Ｈ－吲唑－４－基）咪唑［１，２－ａ］吡啶－３－羧醯胺化合物 - Google Patents

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Publication number

TWI471326B

TWI471326B TW99145074A TW99145074A TWI471326B TW I471326 B TWI471326 B TW I471326B TW 99145074 A TW99145074 A TW 99145074A TW 99145074 A TW99145074 A TW 99145074A TW I471326 B TWI471326 B TW I471326B

Authority

TW

Taiwan

Prior art keywords

methyl

ethyl

pyridine

indazol

imidazo

Prior art date

2009-12-21

Links

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• -1 N-(1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide compound Chemical class 0.000 title claims description 272
• 239000003112 inhibitor Substances 0.000 title description 21
• 125000000217 alkyl group Chemical group 0.000 claims description 336
• 150000001875 compounds Chemical class 0.000 claims description 292
• 125000003545 alkoxy group Chemical group 0.000 claims description 265
• RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 231
• 125000001424 substituent group Chemical group 0.000 claims description 163
• 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 129
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 116
• 230000002829 reductive effect Effects 0.000 claims description 112
• 150000002460 imidazoles Chemical class 0.000 claims description 89
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 75
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 65
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 62
• 150000003839 salts Chemical class 0.000 claims description 62
• 229910052739 hydrogen Inorganic materials 0.000 claims description 60
• 235000005152 nicotinamide Nutrition 0.000 claims description 58
• 239000011570 nicotinamide Substances 0.000 claims description 58
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 55
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 49
• 238000000034 method Methods 0.000 claims description 49
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 48
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 46
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 44
• 229910052757 nitrogen Inorganic materials 0.000 claims description 44
• 125000005842 heteroatom Chemical group 0.000 claims description 42
• 206010028980 Neoplasm Diseases 0.000 claims description 40
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 38
• 210000000988 bone and bone Anatomy 0.000 claims description 37
• 238000011282 treatment Methods 0.000 claims description 37
• 201000010099 disease Diseases 0.000 claims description 36
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 32
• 201000011510 cancer Diseases 0.000 claims description 29
• 229910052736 halogen Inorganic materials 0.000 claims description 27
• 125000004076 pyridyl group Chemical group 0.000 claims description 27
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 25
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 23
• 229920006395 saturated elastomer Polymers 0.000 claims description 23
• 150000002367 halogens Chemical class 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 21
• 125000004429 atom Chemical group 0.000 claims description 20
• 241000124008 Mammalia Species 0.000 claims description 19
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
• 229910052731 fluorine Inorganic materials 0.000 claims description 19
• 239000003054 catalyst Substances 0.000 claims description 18
• 230000008878 coupling Effects 0.000 claims description 18
• 238000010168 coupling process Methods 0.000 claims description 18
• 238000005859 coupling reaction Methods 0.000 claims description 18
• 229910052763 palladium Inorganic materials 0.000 claims description 18
• 125000004414 alkyl thio group Chemical group 0.000 claims description 16
• 229910052794 bromium Inorganic materials 0.000 claims description 16
• 229910052740 iodine Inorganic materials 0.000 claims description 16
• 229910052760 oxygen Inorganic materials 0.000 claims description 16
• 150000001412 amines Chemical class 0.000 claims description 15
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 15
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 14
• PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims description 14
• 125000003277 amino group Chemical group 0.000 claims description 13
• 229910052801 chlorine Inorganic materials 0.000 claims description 13
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
• 229910017051 nitrogen difluoride Inorganic materials 0.000 claims description 13
• 229910052717 sulfur Inorganic materials 0.000 claims description 13
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 12
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 12
• 125000005843 halogen group Chemical group 0.000 claims description 12
• LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims description 12
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
• 239000003638 chemical reducing agent Substances 0.000 claims description 11
• 239000003446 ligand Substances 0.000 claims description 11
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 11
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 10
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 10
• 239000007822 coupling agent Substances 0.000 claims description 9
• 239000003814 drug Substances 0.000 claims description 8
• 125000006413 ring segment Chemical group 0.000 claims description 8
• PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 claims description 8
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 7
• 229940079593 drug Drugs 0.000 claims description 7
• 125000000623 heterocyclic group Chemical group 0.000 claims description 7
• 125000006239 protecting group Chemical group 0.000 claims description 7
• 238000002560 therapeutic procedure Methods 0.000 claims description 7
• 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
• 239000002253 acid Substances 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
• 125000001072 heteroaryl group Chemical group 0.000 claims description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 5
• 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 4
• NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 claims description 4
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
• 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 4
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 4
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
• 238000006467 substitution reaction Methods 0.000 claims description 4
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
• RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims description 3
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 3
• 239000012190 activator Substances 0.000 claims description 3
• 239000007800 oxidant agent Substances 0.000 claims description 3
• 230000009467 reduction Effects 0.000 claims description 3
• 125000000446 sulfanediyl group Chemical group *S* 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
• 125000004122 cyclic group Chemical group 0.000 claims description 2
• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 2
• 238000004519 manufacturing process Methods 0.000 claims description 2
• 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 2
• MFKOCGITFPBMOA-UHFFFAOYSA-N n-[3-cyclopropyl-1-[(1-ethylpyrazol-3-yl)methyl]indazol-4-yl]-7-[2-(4-methylpiperazin-1-yl)ethoxy]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound CCN1C=CC(CN2C3=CC=CC(NC(=O)C=4N5C=CC(OCCN6CCN(C)CC6)=CC5=NC=4)=C3C(C3CC3)=N2)=N1 MFKOCGITFPBMOA-UHFFFAOYSA-N 0.000 claims description 2
• 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
• 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 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
• 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
• 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
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 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
• FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 claims description 2
• WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims 2
• FLNMQGISZVYIIK-UHFFFAOYSA-N 1-ethylpyrazole Chemical compound CCN1C=CC=N1 FLNMQGISZVYIIK-UHFFFAOYSA-N 0.000 claims 1
• JWHJIWJSWRIZOS-UHFFFAOYSA-N 1-methyl-4-(2-pyridin-2-yloxyethyl)piperazine Chemical compound C1CN(C)CCN1CCOC1=CC=CC=N1 JWHJIWJSWRIZOS-UHFFFAOYSA-N 0.000 claims 1
• VZWOXDYRBDIHMA-UHFFFAOYSA-N 2-methyl-1,3-thiazole Chemical compound CC1=NC=CS1 VZWOXDYRBDIHMA-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• GGGKCVZNBSKLMB-UHFFFAOYSA-N 7-(2,3-dihydroxypropoxy)-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(O)CO)=CC4=NC=3)=C2C(CC)=NN1CC1=CC=CC(C)=N1 GGGKCVZNBSKLMB-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• VCKAOEGYVCZMMB-UHFFFAOYSA-N 7-[2-(dimethylamino)ethyl]-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(CCN(C)C)=CC4=NC=3)=C2C(CC)=NN1CC1=CC=CC(C)=N1 VCKAOEGYVCZMMB-UHFFFAOYSA-N 0.000 claims 1
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
• 238000003776 cleavage reaction Methods 0.000 claims 1
• 230000002526 effect on cardiovascular system Effects 0.000 claims 1
• 230000002757 inflammatory effect Effects 0.000 claims 1
• 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
• 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 1
• ZNDRBXGELSYPCL-UHFFFAOYSA-N n-[3-cyclopropyl-1-[(1-propan-2-ylpyrazol-3-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(CC5=NN(C=C5)C(C)C)C=4C=CC=3)N2C=C1 ZNDRBXGELSYPCL-UHFFFAOYSA-N 0.000 claims 1
• ATYXRXQIWBNAQW-UHFFFAOYSA-N n-[3-cyclopropyl-1-[(5-hydroxy-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(O)=CC=5)C=4C=CC=3)N2C=C1 ATYXRXQIWBNAQW-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
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