BR112016026951B1 - Imidazo[1,2-a]pirazin-1-il-benzamida, seu uso, e composições farmacêuticas - Google Patents

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Publication number

BR112016026951B1

BR112016026951B1 BR112016026951-9A BR112016026951A BR112016026951B1 BR 112016026951 B1 BR112016026951 B1 BR 112016026951B1 BR 112016026951 A BR112016026951 A BR 112016026951A BR 112016026951 B1 BR112016026951 B1 BR 112016026951B1

Authority

BR

Brazil

Prior art keywords

pyrazin

methylimidazo

benzamide

fluoro

hydrogen

Prior art date

2014-06-25

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• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 14
• 150000001875 compounds Chemical class 0.000 claims abstract description 176
• 208000002320 spinal muscular atrophy Diseases 0.000 claims abstract description 83
• 150000003839 salts Chemical class 0.000 claims abstract description 49
• 239000003814 drug Substances 0.000 claims abstract description 16
• 239000001257 hydrogen Substances 0.000 claims description 85
• 229910052739 hydrogen Inorganic materials 0.000 claims description 85
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 75
• 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 48
• -1 methoxy-azetidinyl Chemical group 0.000 claims description 41
• 125000001424 substituent group Chemical group 0.000 claims description 31
• 238000002360 preparation method Methods 0.000 claims description 27
• 125000005843 halogen group Chemical group 0.000 claims description 19
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 18
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 15
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
• 229910052757 nitrogen Inorganic materials 0.000 claims description 14
• 239000011737 fluorine Chemical group 0.000 claims description 10
• 229910052731 fluorine Inorganic materials 0.000 claims description 10
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
• 229940079593 drug Drugs 0.000 claims description 9
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 9
• 230000002265 prevention Effects 0.000 claims description 8
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
• WDGBKOBMXBXRIU-UHFFFAOYSA-N 4-(1,4-diazepan-1-yl)-2-ethoxy-N-(2-methylimidazo[1,2-a]pyrazin-6-yl)benzamide Chemical compound CCOC1=C(C=CC(=C1)N1CCCNCC1)C(=O)NC1=CN2C=C(C)N=C2C=N1 WDGBKOBMXBXRIU-UHFFFAOYSA-N 0.000 claims description 6
• 125000003545 alkoxy group Chemical group 0.000 claims description 6
• DHIBFVAQRICJIC-CQSZACIVSA-N 2-ethoxy-N-(2-methylimidazo[1,2-a]pyrazin-6-yl)-4-[(3R)-3-methylpiperazin-1-yl]benzamide Chemical compound CCOC1=C(C=CC(=C1)N1CCN[C@H](C)C1)C(=O)NC1=CN2C=C(C)N=C2C=N1 DHIBFVAQRICJIC-CQSZACIVSA-N 0.000 claims description 5
• DHIBFVAQRICJIC-AWEZNQCLSA-N 2-ethoxy-N-(2-methylimidazo[1,2-a]pyrazin-6-yl)-4-[(3S)-3-methylpiperazin-1-yl]benzamide Chemical compound CCOC1=C(C=CC(=C1)N1CCN[C@@H](C)C1)C(=O)NC1=CN2C=C(C)N=C2C=N1 DHIBFVAQRICJIC-AWEZNQCLSA-N 0.000 claims description 5
• GWRNMNNQLRDJPU-LLVKDONJSA-N 2-fluoro-4-[(3R)-3-methylpiperazin-1-yl]-N-[2-methyl-8-(trifluoromethyl)imidazo[1,2-a]pyrazin-6-yl]benzamide Chemical compound C[C@@H]1CN(CCN1)C1=CC(F)=C(C=C1)C(=O)NC1=CN2C=C(C)N=C2C(=N1)C(F)(F)F GWRNMNNQLRDJPU-LLVKDONJSA-N 0.000 claims description 5
• WHQCEMHIHGHYDM-QGZVFWFLSA-N 2-fluoro-N-(2-methylimidazo[1,2-a]pyrazin-6-yl)-4-[(3R)-3-pyrrolidin-1-ylpyrrolidin-1-yl]benzamide Chemical compound CC1=CN2C=C(NC(=O)C3=C(F)C=C(C=C3)N3CC[C@H](C3)N3CCCC3)N=CC2=N1 WHQCEMHIHGHYDM-QGZVFWFLSA-N 0.000 claims description 5
• KDXPPKRHNSAFKF-UHFFFAOYSA-N 4-(4,7-diazaspiro[2.5]octan-7-yl)-2-fluoro-N-(2-methylimidazo[1,2-a]pyrazin-6-yl)benzamide Chemical compound CC1=CN2C=C(NC(=O)C3=C(F)C=C(C=C3)N3CCNC4(CC4)C3)N=CC2=N1 KDXPPKRHNSAFKF-UHFFFAOYSA-N 0.000 claims description 5
• FWJHZBXJJJTEFO-CQSZACIVSA-N 4-[(3R)-3-ethylpiperazin-1-yl]-2-fluoro-N-(2-methylimidazo[1,2-a]pyrazin-6-yl)benzamide Chemical compound CC[C@@H]1CN(CCN1)C1=CC(F)=C(C=C1)C(=O)NC1=CN2C=C(C)N=C2C=N1 FWJHZBXJJJTEFO-CQSZACIVSA-N 0.000 claims description 5
• FWJHZBXJJJTEFO-AWEZNQCLSA-N 4-[(3S)-3-ethylpiperazin-1-yl]-2-fluoro-N-(2-methylimidazo[1,2-a]pyrazin-6-yl)benzamide Chemical compound CC[C@H]1CN(CCN1)C1=CC(F)=C(C=C1)C(=O)NC1=CN2C=C(C)N=C2C=N1 FWJHZBXJJJTEFO-AWEZNQCLSA-N 0.000 claims description 5
• AEEHPSUYILWGOX-BETUJISGSA-N 4-[(3S,5R)-3,5-dimethylpiperazin-1-yl]-2-fluoro-N-(2-methylimidazo[1,2-a]pyrazin-6-yl)benzamide Chemical compound C[C@H]1CN(C[C@@H](C)N1)C1=CC(F)=C(C=C1)C(=O)NC1=CN2C=C(C)N=C2C=N1 AEEHPSUYILWGOX-BETUJISGSA-N 0.000 claims description 5
• PIAWRWGSLNIFRY-MRXNPFEDSA-N 4-[(8aR)-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-2-yl]-2-fluoro-N-(2-methylimidazo[1,2-a]pyrazin-6-yl)benzamide Chemical compound CC1=CN2C=C(NC(=O)C3=C(F)C=C(C=C3)N3CCN4CCC[C@@H]4C3)N=CC2=N1 PIAWRWGSLNIFRY-MRXNPFEDSA-N 0.000 claims description 5
• ZTNXTCLGPBTYAG-SFHVURJKSA-N 4-[(8aS)-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-2-yl]-2-ethoxy-N-(2-methylimidazo[1,2-a]pyrazin-6-yl)benzamide Chemical compound CCOC1=C(C=CC(=C1)N1CCN2CCC[C@H]2C1)C(=O)NC1=CN2C=C(C)N=C2C=N1 ZTNXTCLGPBTYAG-SFHVURJKSA-N 0.000 claims description 5
• PIAWRWGSLNIFRY-INIZCTEOSA-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]pyrazin-6-yl)benzamide Chemical compound CC1=CN2C=C(NC(=O)C3=C(F)C=C(C=C3)N3CCN4CCC[C@H]4C3)N=CC2=N1 PIAWRWGSLNIFRY-INIZCTEOSA-N 0.000 claims description 5
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 5
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
• AMHOJAFTOMHDEG-GASCZTMLSA-N 4-[(3R,5S)-3,5-dimethylpiperazin-1-yl]-2-ethoxy-N-(2-methylimidazo[1,2-a]pyrazin-6-yl)benzamide Chemical compound CCOC1=C(C=CC(=C1)N1C[C@H](C)N[C@H](C)C1)C(=O)NC1=CN2C=C(C)N=C2C=N1 AMHOJAFTOMHDEG-GASCZTMLSA-N 0.000 claims description 4
• ZTNXTCLGPBTYAG-GOSISDBHSA-N 4-[(8aR)-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-2-yl]-2-ethoxy-N-(2-methylimidazo[1,2-a]pyrazin-6-yl)benzamide Chemical compound CCOC1=C(C=CC(=C1)N1CCN2CCC[C@@H]2C1)C(=O)NC1=CN2C=C(C)N=C2C=N1 ZTNXTCLGPBTYAG-GOSISDBHSA-N 0.000 claims description 4
• IVOQGSPXWCKSAJ-UHFFFAOYSA-N N-(2,8-dimethylimidazo[1,2-a]pyrazin-6-yl)-2-fluoro-4-(4-pyrrolidin-1-ylpiperidin-1-yl)benzamide Chemical compound CC1=CN2C=C(NC(=O)C3=C(F)C=C(C=C3)N3CCC(CC3)N3CCCC3)N=C(C)C2=N1 IVOQGSPXWCKSAJ-UHFFFAOYSA-N 0.000 claims description 4
• 239000013543 active substance Substances 0.000 claims description 4
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 4
• LYOXXWWGQVUGJN-UHFFFAOYSA-N 2,3-difluoro-N-(2-methylimidazo[1,2-a]pyrazin-6-yl)-4-(3-methylpiperazin-1-yl)benzamide Chemical compound CC1CN(CCN1)C1=C(F)C(F)=C(C=C1)C(=O)NC1=CN2C=C(C)N=C2C=N1 LYOXXWWGQVUGJN-UHFFFAOYSA-N 0.000 claims description 3
• PINDEFOBZXFREY-UHFFFAOYSA-N 2,5-difluoro-N-(2-methylimidazo[1,2-a]pyrazin-6-yl)-4-(3-methylpiperazin-1-yl)benzamide Chemical compound CC1CN(CCN1)C1=CC(F)=C(C=C1F)C(=O)NC1=CN2C=C(C)N=C2C=N1 PINDEFOBZXFREY-UHFFFAOYSA-N 0.000 claims description 3
• TYUALYRYQGTGPC-UHFFFAOYSA-N 2-chloro-6-fluoro-N-(2-methylimidazo[1,2-a]pyrazin-6-yl)-4-piperazin-1-ylbenzamide Chemical compound CC1=CN2C=C(NC(=O)C3=C(Cl)C=C(C=C3F)N3CCNCC3)N=CC2=N1 TYUALYRYQGTGPC-UHFFFAOYSA-N 0.000 claims description 3
• FVQIKWGKFNLGTQ-UHFFFAOYSA-N 2-fluoro-N-(2-methylimidazo[1,2-a]pyrazin-6-yl)-4-(3-propan-2-ylpiperazin-1-yl)benzamide Chemical compound CC(C)C1CN(CCN1)C1=CC(F)=C(C=C1)C(=O)NC1=CN2C=C(C)N=C2C=N1 FVQIKWGKFNLGTQ-UHFFFAOYSA-N 0.000 claims description 3
• IEEIXDPCJFPOBG-GFCCVEGCSA-N 2-fluoro-N-(2-methylimidazo[1,2-a]pyrazin-6-yl)-4-[(3R)-3-methylpiperazin-1-yl]benzamide Chemical compound C[C@@H]1CN(CCN1)C1=CC(F)=C(C=C1)C(=O)NC1=CN2C=C(C)N=C2C=N1 IEEIXDPCJFPOBG-GFCCVEGCSA-N 0.000 claims description 3
• WHQCEMHIHGHYDM-KRWDZBQOSA-N 2-fluoro-N-(2-methylimidazo[1,2-a]pyrazin-6-yl)-4-[(3S)-3-pyrrolidin-1-ylpyrrolidin-1-yl]benzamide Chemical compound CC1=CN2C=C(NC(=O)C3=C(F)C=C(C=C3)N3CC[C@@H](C3)N3CCCC3)N=CC2=N1 WHQCEMHIHGHYDM-KRWDZBQOSA-N 0.000 claims description 3
• FVVCSOZESOXQEY-UHFFFAOYSA-N 2-fluoro-N-(2-methylimidazo[1,2-a]pyrazin-6-yl)-4-piperazin-1-ylbenzamide Chemical compound CC1=CN2C=C(NC(=O)C3=C(F)C=C(C=C3)N3CCNCC3)N=CC2=N1 FVVCSOZESOXQEY-UHFFFAOYSA-N 0.000 claims description 3
• AVDARZNYXWSMBW-CYBMUJFWSA-N 2-methoxy-N-(2-methylimidazo[1,2-a]pyrazin-6-yl)-4-[(3R)-3-methylpiperazin-1-yl]benzamide Chemical compound COC1=C(C=CC(=C1)N1CCN[C@H](C)C1)C(=O)NC1=CN2C=C(C)N=C2C=N1 AVDARZNYXWSMBW-CYBMUJFWSA-N 0.000 claims description 3
• UIZHZCXMDBXBJI-GOSISDBHSA-N 2-methoxy-N-(2-methylimidazo[1,2-a]pyrazin-6-yl)-4-[(3R)-3-pyrrolidin-1-ylpyrrolidin-1-yl]benzamide Chemical compound COC1=C(C=CC(=C1)N1CC[C@H](C1)N1CCCC1)C(=O)NC1=CN2C=C(C)N=C2C=N1 UIZHZCXMDBXBJI-GOSISDBHSA-N 0.000 claims description 3
• SFJQSEPKNUHNLT-UHFFFAOYSA-N 2-methoxy-N-(2-methylimidazo[1,2-a]pyrazin-6-yl)-6-piperazin-1-ylpyridine-3-carboxamide Chemical compound COC1=NC(=CC=C1C(=O)NC1=CN2C=C(C)N=C2C=N1)N1CCNCC1 SFJQSEPKNUHNLT-UHFFFAOYSA-N 0.000 claims description 3
• ZAZQPCDYGFOJFM-UHFFFAOYSA-N 4-(3,3-dimethylpiperazin-1-yl)-2-fluoro-N-(2-methylimidazo[1,2-a]pyrazin-6-yl)benzamide Chemical compound CC1=CN2C=C(NC(=O)C3=C(F)C=C(C=C3)N3CCNC(C)(C)C3)N=CC2=N1 ZAZQPCDYGFOJFM-UHFFFAOYSA-N 0.000 claims description 3
• FGJNELIJLHRFHC-UHFFFAOYSA-N 4-(3,3-dimethylpiperazin-1-yl)-2-methoxy-N-(2-methylimidazo[1,2-a]pyrazin-6-yl)benzamide Chemical compound COC1=C(C=CC(=C1)N1CCNC(C)(C)C1)C(=O)NC1=CN2C=C(C)N=C2C=N1 FGJNELIJLHRFHC-UHFFFAOYSA-N 0.000 claims description 3
• MQDAQOOBNOLPEZ-UHFFFAOYSA-N 4-(4,7-diazaspiro[2.5]octan-7-yl)-2-methoxy-N-(2-methylimidazo[1,2-a]pyrazin-6-yl)benzamide Chemical compound COC1=C(C=CC(=C1)N1CCNC2(CC2)C1)C(=O)NC1=CN2C=C(C)N=C2C=N1 MQDAQOOBNOLPEZ-UHFFFAOYSA-N 0.000 claims description 3
• VRPFGWHBJMTQFJ-OAHLLOKOSA-N 4-[(3R)-3-ethylpiperazin-1-yl]-2-methoxy-N-(2-methylimidazo[1,2-a]pyrazin-6-yl)benzamide Chemical compound CC[C@@H]1CN(CCN1)C1=CC(OC)=C(C=C1)C(=O)NC1=CN2C=C(C)N=C2C=N1 VRPFGWHBJMTQFJ-OAHLLOKOSA-N 0.000 claims description 3
• IEPXGTUCNPNFAS-OKILXGFUSA-N 4-[(3S,5R)-3,5-dimethylpiperazin-1-yl]-2-methoxy-N-(2-methylimidazo[1,2-a]pyrazin-6-yl)benzamide Chemical compound COC1=C(C=CC(=C1)N1C[C@H](C)N[C@H](C)C1)C(=O)NC1=CN2C=C(C)N=C2C=N1 IEPXGTUCNPNFAS-OKILXGFUSA-N 0.000 claims description 3
• LQGAVCQHJUKHDN-CQSZACIVSA-N 6-[(3R)-3-ethylpiperazin-1-yl]-2-methoxy-N-(2-methylimidazo[1,2-a]pyrazin-6-yl)pyridine-3-carboxamide Chemical compound CC[C@@H]1CN(CCN1)C1=CC=C(C(=O)NC2=CN3C=C(C)N=C3C=N2)C(OC)=N1 LQGAVCQHJUKHDN-CQSZACIVSA-N 0.000 claims description 3
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
• 239000005977 Ethylene Substances 0.000 claims description 3
• LFFWHLSGBCASGM-UHFFFAOYSA-N N-(2,8-dimethylimidazo[1,2-a]pyrazin-6-yl)-2-ethoxy-4-[4-(3-methoxyazetidin-1-yl)piperidin-1-yl]benzamide Chemical compound CCOC1=C(C=CC(=C1)N1CCC(CC1)N1CC(C1)OC)C(=O)NC1=CN2C=C(C)N=C2C(C)=N1 LFFWHLSGBCASGM-UHFFFAOYSA-N 0.000 claims description 3
• GNHKESFRUVVVDP-GFCCVEGCSA-N N-(2,8-dimethylimidazo[1,2-a]pyrazin-6-yl)-2-fluoro-4-[(3R)-3-methylpiperazin-1-yl]benzamide Chemical compound C[C@@H]1CN(CCN1)C1=CC(F)=C(C=C1)C(=O)NC1=CN2C=C(C)N=C2C(C)=N1 GNHKESFRUVVVDP-GFCCVEGCSA-N 0.000 claims description 3
• QMVMAXKUMAVPHI-LLVKDONJSA-N N-[8-(difluoromethyl)-2-methylimidazo[1,2-a]pyrazin-6-yl]-2-fluoro-4-[(3R)-3-methylpiperazin-1-yl]benzamide Chemical compound C[C@@H]1CN(CCN1)C1=CC(F)=C(C=C1)C(=O)NC1=CN2C=C(C)N=C2C(=N1)C(F)F QMVMAXKUMAVPHI-LLVKDONJSA-N 0.000 claims description 3
• 230000007812 deficiency Effects 0.000 claims description 3
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
• JJPQQHAKHZDRMW-GOSISDBHSA-N 4-[(8aR)-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-2-yl]-N-(8-cyclopropyl-2-methylimidazo[1,2-a]pyrazin-6-yl)-2-fluorobenzamide Chemical compound CC1=CN2C=C(NC(=O)C3=C(F)C=C(C=C3)N3CCN4CCC[C@@H]4C3)N=C(C3CC3)C2=N1 JJPQQHAKHZDRMW-GOSISDBHSA-N 0.000 claims description 2
• JJPQQHAKHZDRMW-SFHVURJKSA-N 4-[(8aS)-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-2-yl]-N-(8-cyclopropyl-2-methylimidazo[1,2-a]pyrazin-6-yl)-2-fluorobenzamide Chemical compound CC1=CN2C=C(NC(=O)C3=C(F)C=C(C=C3)N3CCN4CCC[C@H]4C3)N=C(C3CC3)C2=N1 JJPQQHAKHZDRMW-SFHVURJKSA-N 0.000 claims description 2
• HMBZJNDXYKQSGR-KRWDZBQOSA-N 4-[(8aS)-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-2-yl]-N-(8-ethyl-2-methylimidazo[1,2-a]pyrazin-6-yl)-2-fluorobenzamide Chemical compound CCC1=NC(NC(=O)C2=C(F)C=C(C=C2)N2CCN3CCC[C@H]3C2)=CN2C=C(C)N=C12 HMBZJNDXYKQSGR-KRWDZBQOSA-N 0.000 claims description 2
• JWZMRCXDMBZULO-LLVKDONJSA-N N-(2,8-dimethylimidazo[1,2-a]pyrazin-6-yl)-2,6-difluoro-4-[(3R)-3-methylpiperazin-1-yl]benzamide Chemical compound C[C@@H]1CN(CCN1)C1=CC(F)=C(C(=O)NC2=CN3C=C(C)N=C3C(C)=N2)C(F)=C1 JWZMRCXDMBZULO-LLVKDONJSA-N 0.000 claims description 2
• FBIZCTYODIRDAC-CQSZACIVSA-N N-(2,8-dimethylimidazo[1,2-a]pyrazin-6-yl)-2-ethoxy-4-[(3R)-3-methylpiperazin-1-yl]benzamide Chemical compound CCOC1=C(C=CC(=C1)N1CCN[C@H](C)C1)C(=O)NC1=CN2C=C(C)N=C2C(C)=N1 FBIZCTYODIRDAC-CQSZACIVSA-N 0.000 claims description 2
• QIPDXSZJDJPZEG-SFHVURJKSA-N N-(2,8-dimethylimidazo[1,2-a]pyrazin-6-yl)-2-fluoro-4-[(3S)-3-pyrrolidin-1-ylpyrrolidin-1-yl]benzamide Chemical compound CC1=CN2C=C(NC(=O)C3=C(F)C=C(C=C3)N3CC[C@@H](C3)N3CCCC3)N=C(C)C2=N1 QIPDXSZJDJPZEG-SFHVURJKSA-N 0.000 claims description 2
• WWYKGEYMAPFRKA-BETUJISGSA-N N-(2,8-dimethylimidazo[1,2-a]pyrazin-6-yl)-4-[(3R,5S)-3,5-dimethylpiperazin-1-yl]-2-fluorobenzamide Chemical compound C[C@H]1CN(C[C@@H](C)N1)C1=CC(F)=C(C=C1)C(=O)NC1=CN2C=C(C)N=C2C(C)=N1 WWYKGEYMAPFRKA-BETUJISGSA-N 0.000 claims description 2
• DATZOOGTKZQOOH-UHFFFAOYSA-N N-(2-methylimidazo[1,2-a]pyrazin-6-yl)-4-piperazin-1-ylbenzamide Chemical compound CC1=CN2C=C(NC(=O)C3=CC=C(C=C3)N3CCNCC3)N=CC2=N1 DATZOOGTKZQOOH-UHFFFAOYSA-N 0.000 claims description 2
• UWMKOBPHVIUAEC-CYBMUJFWSA-N N-(8-cyclopropyl-2-methylimidazo[1,2-a]pyrazin-6-yl)-2-fluoro-4-[(3R)-3-methylpiperazin-1-yl]benzamide Chemical compound C[C@@H]1CN(CCN1)C1=CC(F)=C(C=C1)C(=O)NC1=CN2C=C(C)N=C2C(=N1)C1CC1 UWMKOBPHVIUAEC-CYBMUJFWSA-N 0.000 claims description 2
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