BR112015030288B1 - Compostos e seu uso no tratamento de atrofia muscular espinhal - Google Patents

Info

Publication number

BR112015030288B1

BR112015030288B1 BR112015030288-2A BR112015030288A BR112015030288B1 BR 112015030288 B1 BR112015030288 B1 BR 112015030288B1 BR 112015030288 A BR112015030288 A BR 112015030288A BR 112015030288 B1 BR112015030288 B1 BR 112015030288B1

Authority

BR

Brazil

Prior art keywords

fluoro

pyridin

methylimidazo

nicotinamide

methylpiperazin

Prior art date

2013-06-25

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 242
• 208000002320 spinal muscular atrophy Diseases 0.000 title claims abstract description 90
• 150000003839 salts Chemical class 0.000 claims abstract description 45
• 239000003814 drug Substances 0.000 claims abstract description 17
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
• -1 imidazo[1,2-a]pyrazin-2-yl Chemical group 0.000 claims description 110
• 239000001257 hydrogen Substances 0.000 claims description 51
• 229910052739 hydrogen Inorganic materials 0.000 claims description 51
• 238000002360 preparation method Methods 0.000 claims description 46
• 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 32
• 125000005843 halogen group Chemical group 0.000 claims description 32
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 29
• 229910052757 nitrogen Inorganic materials 0.000 claims description 21
• 125000001153 fluoro group Chemical group F* 0.000 claims description 19
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 14
• KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 13
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
• 230000002265 prevention Effects 0.000 claims description 10
• 229940079593 drug Drugs 0.000 claims description 9
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
• RYUGODUJAWWBFU-UHFFFAOYSA-N n-(8-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)-6-(1,2,3,6-tetrahydropyridin-4-yl)pyridine-3-carboxamide Chemical compound C1=C(F)C2=NC(C)=CN2C=C1NC(=O)C(C=N1)=CC=C1C1=CCNCC1 RYUGODUJAWWBFU-UHFFFAOYSA-N 0.000 claims description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
• ONYFYCFGMPJTJH-UHFFFAOYSA-N 2-ethoxy-n-(8-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)-6-piperazin-1-ylpyridine-3-carboxamide Chemical compound C=1C=C(C(=O)NC2=CN3C=C(C)N=C3C(F)=C2)C(OCC)=NC=1N1CCNCC1 ONYFYCFGMPJTJH-UHFFFAOYSA-N 0.000 claims description 7
• WXDSFKVEUQARAL-UHFFFAOYSA-N 2-fluoro-n-(8-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)-4-(1,2,3,6-tetrahydropyridin-4-yl)benzamide Chemical compound C1=C(F)C2=NC(C)=CN2C=C1NC(=O)C(C(=C1)F)=CC=C1C1=CCNCC1 WXDSFKVEUQARAL-UHFFFAOYSA-N 0.000 claims description 7
• BFPGTMZIXCKHHF-UHFFFAOYSA-N 4-ethoxy-n-(8-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)-6-piperazin-1-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NC2=CN3C=C(C)N=C3C(F)=C2)C(OCC)=CC=1N1CCNCC1 BFPGTMZIXCKHHF-UHFFFAOYSA-N 0.000 claims description 7
• OARKCOYNBVFPCR-UHFFFAOYSA-N 4-fluoro-n-(8-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)-6-piperazin-1-ylpyridine-3-carboxamide Chemical compound C1=C(F)C2=NC(C)=CN2C=C1NC(=O)C(C(=C1)F)=CN=C1N1CCNCC1 OARKCOYNBVFPCR-UHFFFAOYSA-N 0.000 claims description 7
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
• DCECLWBGAPZBRC-UHFFFAOYSA-N n-(8-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)-2-methoxy-6-(3-methylpiperazin-1-yl)pyridine-3-carboxamide Chemical compound C=1C=C(C(=O)NC2=CN3C=C(C)N=C3C(F)=C2)C(OC)=NC=1N1CCNC(C)C1 DCECLWBGAPZBRC-UHFFFAOYSA-N 0.000 claims description 7
• NVKUFDLRQDDJHG-UHFFFAOYSA-N n-(8-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)-4-methoxy-6-(3-methylpiperazin-1-yl)pyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NC2=CN3C=C(C)N=C3C(F)=C2)C(OC)=CC=1N1CCNC(C)C1 NVKUFDLRQDDJHG-UHFFFAOYSA-N 0.000 claims description 7
• 235000005152 nicotinamide Nutrition 0.000 claims description 7
• 239000011570 nicotinamide Substances 0.000 claims description 7
• 229960003966 nicotinamide Drugs 0.000 claims description 7
• YJLUPSHULWHEFR-UHFFFAOYSA-N 2,6-difluoro-n-(8-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)-4-(3-methylpiperazin-1-yl)benzamide Chemical compound C1CNC(C)CN1C(C=C1F)=CC(F)=C1C(=O)NC1=CN2C=C(C)N=C2C(F)=C1 YJLUPSHULWHEFR-UHFFFAOYSA-N 0.000 claims description 6
• BEEFXPXLOVUQJM-UHFFFAOYSA-N 2-fluoro-n-(8-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)-4-(3-methylpiperazin-1-yl)benzamide Chemical compound C1CNC(C)CN1C(C=C1F)=CC=C1C(=O)NC1=CN2C=C(C)N=C2C(F)=C1 BEEFXPXLOVUQJM-UHFFFAOYSA-N 0.000 claims description 6
• BEEFXPXLOVUQJM-GFCCVEGCSA-N 2-fluoro-n-(8-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)-4-[(3r)-3-methylpiperazin-1-yl]benzamide Chemical compound C1CN[C@H](C)CN1C(C=C1F)=CC=C1C(=O)NC1=CN2C=C(C)N=C2C(F)=C1 BEEFXPXLOVUQJM-GFCCVEGCSA-N 0.000 claims description 6
• BEEFXPXLOVUQJM-LBPRGKRZSA-N 2-fluoro-n-(8-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)-4-[(3s)-3-methylpiperazin-1-yl]benzamide Chemical compound C1CN[C@@H](C)CN1C(C=C1F)=CC=C1C(=O)NC1=CN2C=C(C)N=C2C(F)=C1 BEEFXPXLOVUQJM-LBPRGKRZSA-N 0.000 claims description 6
• VGQGGSXEFWCYFA-UHFFFAOYSA-N 2-fluoro-n-(8-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)-4-piperazin-1-ylbenzamide Chemical compound C1=C(F)C2=NC(C)=CN2C=C1NC(=O)C(C(=C1)F)=CC=C1N1CCNCC1 VGQGGSXEFWCYFA-UHFFFAOYSA-N 0.000 claims description 6
• DNFHGKXSXKGDNU-UHFFFAOYSA-N 3-fluoro-n-(8-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)-5-(3-methylpiperazin-1-yl)pyridine-2-carboxamide Chemical compound C1CNC(C)CN1C(C=C1F)=CN=C1C(=O)NC1=CN2C=C(C)N=C2C(F)=C1 DNFHGKXSXKGDNU-UHFFFAOYSA-N 0.000 claims description 6
• YSPXWEDKEUHKNX-SFHVURJKSA-N 4-[(8as)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl]-2-fluoro-n-(2-methylimidazo[1,2-a]pyridin-6-yl)benzamide Chemical compound C1CN2CCC[C@H]2CN1C(C=C1F)=CC=C1C(=O)NC1=CN2C=C(C)N=C2C=C1 YSPXWEDKEUHKNX-SFHVURJKSA-N 0.000 claims description 6
• KKIJUDRQFQKRMV-UHFFFAOYSA-N 6-(3,4-dimethylpiperazin-1-yl)-n-(2-methylimidazo[1,2-a]pyridin-6-yl)pyridine-3-carboxamide Chemical compound C1CN(C)C(C)CN1C1=CC=C(C(=O)NC2=CN3C=C(C)N=C3C=C2)C=N1 KKIJUDRQFQKRMV-UHFFFAOYSA-N 0.000 claims description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
• FEMCGBHYNUREEC-UHFFFAOYSA-N n-(2-methylimidazo[1,2-a]pyridin-6-yl)-6-(1-methylpiperidin-4-yl)pyridine-3-carboxamide Chemical compound C1CN(C)CCC1C1=CC=C(C(=O)NC2=CN3C=C(C)N=C3C=C2)C=N1 FEMCGBHYNUREEC-UHFFFAOYSA-N 0.000 claims description 6
• WBEPIKVPBWIXGM-UHFFFAOYSA-N n-(2-methylimidazo[1,2-a]pyridin-6-yl)-6-(3-methylpiperazin-1-yl)pyridine-3-carboxamide Chemical compound C1CNC(C)CN1C1=CC=C(C(=O)NC2=CN3C=C(C)N=C3C=C2)C=N1 WBEPIKVPBWIXGM-UHFFFAOYSA-N 0.000 claims description 6
• PIXNAEMAWWVCJF-UHFFFAOYSA-N n-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)-4-piperazin-1-ylbenzamide Chemical compound N1=C2C(C)=NC(C)=CN2C=C1NC(=O)C(C=C1)=CC=C1N1CCNCC1 PIXNAEMAWWVCJF-UHFFFAOYSA-N 0.000 claims description 6
• PRBNMVWBWGWHNR-UHFFFAOYSA-N n-(8-chloro-2-methylimidazo[1,2-a]pyridin-6-yl)-2-fluoro-4-(3-methylpiperazin-1-yl)benzamide Chemical compound C1CNC(C)CN1C(C=C1F)=CC=C1C(=O)NC1=CN2C=C(C)N=C2C(Cl)=C1 PRBNMVWBWGWHNR-UHFFFAOYSA-N 0.000 claims description 6
• FUWXZYVIVFQZLW-UHFFFAOYSA-N n-(8-chloro-2-methylimidazo[1,2-a]pyridin-6-yl)-3-fluoro-5-(3-methylpiperazin-1-yl)pyridine-2-carboxamide Chemical compound C1CNC(C)CN1C(C=C1F)=CN=C1C(=O)NC1=CN2C=C(C)N=C2C(Cl)=C1 FUWXZYVIVFQZLW-UHFFFAOYSA-N 0.000 claims description 6
• GNHGIDUPJIFMBG-UHFFFAOYSA-N n-(8-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)-2-methoxy-6-piperazin-1-ylpyridine-3-carboxamide Chemical compound C=1C=C(C(=O)NC2=CN3C=C(C)N=C3C(F)=C2)C(OC)=NC=1N1CCNCC1 GNHGIDUPJIFMBG-UHFFFAOYSA-N 0.000 claims description 6
• PDNBINYXFWGAQJ-UHFFFAOYSA-N n-(8-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)-6-(1-methylpiperidin-4-yl)pyridine-3-carboxamide Chemical compound C1CN(C)CCC1C1=CC=C(C(=O)NC2=CN3C=C(C)N=C3C(F)=C2)C=N1 PDNBINYXFWGAQJ-UHFFFAOYSA-N 0.000 claims description 6
• GBESJSDFWIKMFD-UHFFFAOYSA-N n-(8-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)-6-piperazin-1-ylpyridine-3-carboxamide Chemical compound C1=C(F)C2=NC(C)=CN2C=C1NC(=O)C(C=N1)=CC=C1N1CCNCC1 GBESJSDFWIKMFD-UHFFFAOYSA-N 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
• CDFYPSURDFQWHV-UHFFFAOYSA-N 2-fluoro-n-(2-methylimidazo[1,2-a]pyridin-6-yl)-4-(3-methylpiperazin-1-yl)benzamide Chemical compound C1CNC(C)CN1C(C=C1F)=CC=C1C(=O)NC1=CN2C=C(C)N=C2C=C1 CDFYPSURDFQWHV-UHFFFAOYSA-N 0.000 claims description 5
• ZWYDVEGLPZWOPF-UHFFFAOYSA-N 2-fluoro-n-(4-fluoro-2-methyl-1,3-benzoxazol-6-yl)-4-piperazin-1-ylbenzamide Chemical compound C1=C2OC(C)=NC2=C(F)C=C1NC(=O)C(C(=C1)F)=CC=C1N1CCNCC1 ZWYDVEGLPZWOPF-UHFFFAOYSA-N 0.000 claims description 5
• UVDCWTFXXKSREY-UHFFFAOYSA-N 2-fluoro-n-(8-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)-6-piperazin-1-ylpyridine-3-carboxamide Chemical compound C1=C(F)C2=NC(C)=CN2C=C1NC(=O)C(C(=N1)F)=CC=C1N1CCNCC1 UVDCWTFXXKSREY-UHFFFAOYSA-N 0.000 claims description 5
• FYDXFOSDKWKKCU-UHFFFAOYSA-N 4-(3,5-dimethylpiperazin-1-yl)-n-(4-fluoro-2-methyl-1,3-benzoxazol-6-yl)benzamide Chemical compound C1C(C)NC(C)CN1C1=CC=C(C(=O)NC=2C=C3OC(C)=NC3=C(F)C=2)C=C1 FYDXFOSDKWKKCU-UHFFFAOYSA-N 0.000 claims description 5
• ICCWBBALBHDANM-UHFFFAOYSA-N 6-(3,3-dimethylpiperazin-1-yl)-n-(2-methylimidazo[1,2-a]pyridin-6-yl)pyridine-3-carboxamide Chemical compound C1=CC2=NC(C)=CN2C=C1NC(=O)C(C=N1)=CC=C1N1CCNC(C)(C)C1 ICCWBBALBHDANM-UHFFFAOYSA-N 0.000 claims description 5
• BMNBZFVCCZJSMM-UHFFFAOYSA-N 6-(3,3-dimethylpiperazin-1-yl)-n-(8-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)-2-methoxypyridine-3-carboxamide Chemical compound C=1C=C(C(=O)NC2=CN3C=C(C)N=C3C(F)=C2)C(OC)=NC=1N1CCNC(C)(C)C1 BMNBZFVCCZJSMM-UHFFFAOYSA-N 0.000 claims description 5
• XJSDPQCOSPMJFI-UHFFFAOYSA-N 6-(3,5-dimethylpiperazin-1-yl)-n-[2-methyl-8-(trifluoromethyl)imidazo[1,2-a]pyridin-6-yl]pyridine-3-carboxamide Chemical compound C1C(C)NC(C)CN1C1=CC=C(C(=O)NC2=CN3C=C(C)N=C3C(=C2)C(F)(F)F)C=N1 XJSDPQCOSPMJFI-UHFFFAOYSA-N 0.000 claims description 5
• KNHQMKOYHWRBCO-UHFFFAOYSA-N 6-(3-methylpiperazin-1-yl)-n-[2-methyl-8-(trifluoromethyl)imidazo[1,2-a]pyridin-6-yl]pyridine-3-carboxamide Chemical compound C1CNC(C)CN1C1=CC=C(C(=O)NC2=CN3C=C(C)N=C3C(=C2)C(F)(F)F)C=N1 KNHQMKOYHWRBCO-UHFFFAOYSA-N 0.000 claims description 5
• WUFHTFURPYIBBW-INIZCTEOSA-N 6-[(8as)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl]-n-(4-fluoro-2-methyl-1,3-benzoxazol-6-yl)pyridine-3-carboxamide Chemical compound C1CN2CCC[C@H]2CN1C(N=C1)=CC=C1C(=O)NC1=CC(F)=C2N=C(C)OC2=C1 WUFHTFURPYIBBW-INIZCTEOSA-N 0.000 claims description 5
• KBXAJUVZHXHFOO-KRWDZBQOSA-N 6-[(8as)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl]-n-[2-methyl-8-(trifluoromethyl)imidazo[1,2-a]pyridin-6-yl]pyridine-3-carboxamide Chemical compound C1CN2CCC[C@H]2CN1C(N=C1)=CC=C1C(=O)NC1=CN2C=C(C)N=C2C(C(F)(F)F)=C1 KBXAJUVZHXHFOO-KRWDZBQOSA-N 0.000 claims description 5
• LSUYOXGXTYWMGP-UHFFFAOYSA-N CC1CN(CCN1)c1ccc(cn1)C(=O)Nc1cc(F)c2nc(C)oc2c1 Chemical compound CC1CN(CCN1)c1ccc(cn1)C(=O)Nc1cc(F)c2nc(C)oc2c1 LSUYOXGXTYWMGP-UHFFFAOYSA-N 0.000 claims description 5
• BQNHOHOBKROZBM-UHFFFAOYSA-N n-(2-methylimidazo[1,2-a]pyridin-6-yl)-5-(3-methylpiperazin-1-yl)pyridine-2-carboxamide Chemical compound C1CNC(C)CN1C1=CC=C(C(=O)NC2=CN3C=C(C)N=C3C=C2)N=C1 BQNHOHOBKROZBM-UHFFFAOYSA-N 0.000 claims description 5
• ZFKLECOKAWZOEL-UHFFFAOYSA-N n-(2-methylimidazo[1,2-a]pyridin-6-yl)-6-(1,2,3,6-tetrahydropyridin-4-yl)pyridine-3-carboxamide Chemical compound C1=CC2=NC(C)=CN2C=C1NC(=O)C(C=N1)=CC=C1C1=CCNCC1 ZFKLECOKAWZOEL-UHFFFAOYSA-N 0.000 claims description 5
• ZXPNEDWJSSFQJE-UHFFFAOYSA-N n-(2-methylimidazo[1,2-a]pyridin-6-yl)-6-piperazin-1-ylpyridine-3-carboxamide Chemical compound C1=CC2=NC(C)=CN2C=C1NC(=O)C(C=N1)=CC=C1N1CCNCC1 ZXPNEDWJSSFQJE-UHFFFAOYSA-N 0.000 claims description 5
• QUJOVOYZKLBJOP-UHFFFAOYSA-N n-(4-fluoro-2-methyl-1,3-benzoxazol-6-yl)-4-(3-methylpiperazin-1-yl)benzamide Chemical compound C1CNC(C)CN1C1=CC=C(C(=O)NC=2C=C3OC(C)=NC3=C(F)C=2)C=C1 QUJOVOYZKLBJOP-UHFFFAOYSA-N 0.000 claims description 5
• QNMLZXPESKFTCH-UHFFFAOYSA-N n-(4-fluoro-2-methyl-1,3-benzoxazol-6-yl)-4-piperazin-1-ylbenzamide Chemical compound C1=C2OC(C)=NC2=C(F)C=C1NC(=O)C(C=C1)=CC=C1N1CCNCC1 QNMLZXPESKFTCH-UHFFFAOYSA-N 0.000 claims description 5
• NLPPFOABWIWXNS-UHFFFAOYSA-N n-(4-fluoro-2-methyl-1,3-benzoxazol-6-yl)-6-(4-methylpiperazin-1-yl)pyridine-3-carboxamide Chemical compound C1CN(C)CCN1C1=CC=C(C(=O)NC=2C=C3OC(C)=NC3=C(F)C=2)C=N1 NLPPFOABWIWXNS-UHFFFAOYSA-N 0.000 claims description 5
• JRLZAGGIBGOOCT-UHFFFAOYSA-N n-(4-fluoro-2-methyl-1,3-benzoxazol-6-yl)-6-piperazin-1-ylpyridine-3-carboxamide Chemical compound C1=C2OC(C)=NC2=C(F)C=C1NC(=O)C(C=N1)=CC=C1N1CCNCC1 JRLZAGGIBGOOCT-UHFFFAOYSA-N 0.000 claims description 5
• ZKLAQRFKZCJHJW-UHFFFAOYSA-N n-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)-2-fluoro-4-(3-methylpiperazin-1-yl)benzamide Chemical compound C1CNC(C)CN1C(C=C1F)=CC=C1C(=O)NC1=CN(C=C(C)N=C2C)C2=N1 ZKLAQRFKZCJHJW-UHFFFAOYSA-N 0.000 claims description 5
• YDWAWZDNPJFPGN-UHFFFAOYSA-N n-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)-2-fluoro-4-(4-methylpiperazin-1-yl)benzamide Chemical compound C1CN(C)CCN1C(C=C1F)=CC=C1C(=O)NC1=CN(C=C(C)N=C2C)C2=N1 YDWAWZDNPJFPGN-UHFFFAOYSA-N 0.000 claims description 5
• YTYYMBZTLZDAMO-UHFFFAOYSA-N n-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)-4-(3-methylpiperazin-1-yl)benzamide Chemical compound C1CNC(C)CN1C1=CC=C(C(=O)NC=2N=C3C(C)=NC(C)=CN3C=2)C=C1 YTYYMBZTLZDAMO-UHFFFAOYSA-N 0.000 claims description 5
• YTYYMBZTLZDAMO-ZDUSSCGKSA-N n-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)-4-[(3s)-3-methylpiperazin-1-yl]benzamide Chemical compound C1CN[C@@H](C)CN1C1=CC=C(C(=O)NC=2N=C3C(C)=NC(C)=CN3C=2)C=C1 YTYYMBZTLZDAMO-ZDUSSCGKSA-N 0.000 claims description 5
• XRZLJKSMRBZDDM-UHFFFAOYSA-N n-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)-5-(3-methylpiperazin-1-yl)pyridine-2-carboxamide Chemical compound C1CNC(C)CN1C1=CC=C(C(=O)NC=2N=C3C(C)=NC(C)=CN3C=2)N=C1 XRZLJKSMRBZDDM-UHFFFAOYSA-N 0.000 claims description 5
• VIOPQFXIEDBBAL-UHFFFAOYSA-N n-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)-5-(4-methylpiperazin-1-yl)pyridine-2-carboxamide Chemical compound C1CN(C)CCN1C1=CC=C(C(=O)NC=2N=C3C(C)=NC(C)=CN3C=2)N=C1 VIOPQFXIEDBBAL-UHFFFAOYSA-N 0.000 claims description 5
• HPGTYYVNUPTPJW-UHFFFAOYSA-N n-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)-5-piperazin-1-ylpyridine-2-carboxamide Chemical compound N1=C2C(C)=NC(C)=CN2C=C1NC(=O)C(N=C1)=CC=C1N1CCNCC1 HPGTYYVNUPTPJW-UHFFFAOYSA-N 0.000 claims description 5
• GJKKZMGYNQAZTR-UHFFFAOYSA-N n-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)-6-(3-methylpiperazin-1-yl)pyridine-3-carboxamide Chemical compound C1CNC(C)CN1C1=CC=C(C(=O)NC=2N=C3C(C)=NC(C)=CN3C=2)C=N1 GJKKZMGYNQAZTR-UHFFFAOYSA-N 0.000 claims description 5
• OLFWQPDYWBDNQG-UHFFFAOYSA-N n-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)-6-(4-ethylpiperazin-1-yl)pyridine-3-carboxamide Chemical compound C1CN(CC)CCN1C1=CC=C(C(=O)NC=2N=C3C(C)=NC(C)=CN3C=2)C=N1 OLFWQPDYWBDNQG-UHFFFAOYSA-N 0.000 claims description 5
• KBDRCBZOMWOGER-UHFFFAOYSA-N n-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)-6-(4-methylpiperazin-1-yl)pyridine-3-carboxamide Chemical compound C1CN(C)CCN1C1=CC=C(C(=O)NC=2N=C3C(C)=NC(C)=CN3C=2)C=N1 KBDRCBZOMWOGER-UHFFFAOYSA-N 0.000 claims description 5
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