EA037123B1 - Соединения для лечения спинальной мышечной атрофии - Google Patents

Info

Publication number

EA037123B1

EA037123B1 EA201792465A EA201792465A EA037123B1 EA 037123 B1 EA037123 B1 EA 037123B1 EA 201792465 A EA201792465 A EA 201792465A EA 201792465 A EA201792465 A EA 201792465A EA 037123 B1 EA037123 B1 EA 037123B1

Authority

EA

Eurasian Patent Office

Prior art keywords

pyrido

pyrimidin

dimethoxyphenyl

methoxyphenyl

fluoro

Prior art date

2012-02-10

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 507
• 208000002320 spinal muscular atrophy Diseases 0.000 title claims description 122
• 102100021947 Survival motor neuron protein Human genes 0.000 claims abstract description 154
• 238000000034 method Methods 0.000 claims abstract description 151
• 101000617738 Homo sapiens Survival motor neuron protein Proteins 0.000 claims abstract description 136
• 108020004999 messenger RNA Proteins 0.000 claims abstract description 110
• 150000003839 salts Chemical class 0.000 claims abstract description 74
• 101150081851 SMN1 gene Proteins 0.000 claims abstract description 64
• 101150015954 SMN2 gene Proteins 0.000 claims abstract description 64
• 101100203482 Drosophila melanogaster Smn gene Proteins 0.000 claims abstract description 45
• 101150069235 Snrpn gene Proteins 0.000 claims abstract description 45
• 239000002253 acid Substances 0.000 claims abstract description 35
• 230000001965 increasing effect Effects 0.000 claims abstract description 19
• 230000002708 enhancing effect Effects 0.000 claims abstract description 16
• 239000012458 free base Substances 0.000 claims abstract description 15
• -1 1,2,5,6-tetrahydropyridinyl Chemical group 0.000 claims description 575
• DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims description 220
• 125000000217 alkyl group Chemical group 0.000 claims description 201
• 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 158
• 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 94
• NYJWYCAHJRGKMI-UHFFFAOYSA-N pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=CC=CN2C(=O)C=CN=C21 NYJWYCAHJRGKMI-UHFFFAOYSA-N 0.000 claims description 72
• 239000002904 solvent Substances 0.000 claims description 54
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 43
• 125000001424 substituent group Chemical group 0.000 claims description 41
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 39
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 35
• 125000003545 alkoxy group Chemical group 0.000 claims description 34
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 30
• 125000003282 alkyl amino group Chemical group 0.000 claims description 30
• 125000000623 heterocyclic group Chemical group 0.000 claims description 30
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 28
• 210000005260 human cell Anatomy 0.000 claims description 28
• GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 26
• 125000002950 monocyclic group Chemical group 0.000 claims description 25
• 125000004076 pyridyl group Chemical group 0.000 claims description 21
• 229910052736 halogen Inorganic materials 0.000 claims description 20
• 150000002367 halogens Chemical class 0.000 claims description 19
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 17
• 125000003118 aryl group Chemical group 0.000 claims description 16
• 210000003205 muscle Anatomy 0.000 claims description 16
• 229910052739 hydrogen Inorganic materials 0.000 claims description 15
• 239000001257 hydrogen Substances 0.000 claims description 15
• 229920006395 saturated elastomer Polymers 0.000 claims description 15
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 14
• 125000004432 carbon atom Chemical group C* 0.000 claims description 14
• 210000004027 cell Anatomy 0.000 claims description 13
• 229910052757 nitrogen Inorganic materials 0.000 claims description 13
• 241000699670 Mus sp. Species 0.000 claims description 12
• 125000002619 bicyclic group Chemical group 0.000 claims description 12
• 125000002837 carbocyclic group Chemical group 0.000 claims description 12
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
• 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
• 210000004556 brain Anatomy 0.000 claims description 11
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 10
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 10
• 229910052717 sulfur Inorganic materials 0.000 claims description 10
• 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 9
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
• 125000005842 heteroatom Chemical group 0.000 claims description 9
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 9
• 229910052760 oxygen Inorganic materials 0.000 claims description 9
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
• 125000001072 heteroaryl group Chemical group 0.000 claims description 8
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 8
• 210000000278 spinal cord Anatomy 0.000 claims description 8
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
• 125000003342 alkenyl group Chemical group 0.000 claims description 7
• 125000004414 alkyl thio group Chemical group 0.000 claims description 7
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
• 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
• SSJXIUAHEKJCMH-WDSKDSINSA-N (1s,2s)-cyclohexane-1,2-diamine Chemical compound N[C@H]1CCCC[C@@H]1N SSJXIUAHEKJCMH-WDSKDSINSA-N 0.000 claims description 6
• 125000002393 azetidinyl group Chemical group 0.000 claims description 6
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 6
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
• 125000004193 piperazinyl group Chemical group 0.000 claims description 6
• 125000003386 piperidinyl group Chemical group 0.000 claims description 6
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
• 125000005960 1,4-diazepanyl group Chemical group 0.000 claims description 5
• 125000005877 1,4-benzodioxanyl group Chemical group 0.000 claims description 4
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
• GXWNSJYVSIJRLS-UHFFFAOYSA-N 6-bromo-8-methylimidazo[1,2-a]pyrazine Chemical compound CC1=NC(Br)=CN2C=CN=C12 GXWNSJYVSIJRLS-UHFFFAOYSA-N 0.000 claims description 4
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
• GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims description 4
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 4
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 4
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 4
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 4
• 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 125000002632 imidazolidinyl group Chemical group 0.000 claims description 4
• 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 claims description 4
• 125000003965 isoxazolidinyl group Chemical group 0.000 claims description 4
• 125000002757 morpholinyl 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
• 125000000160 oxazolidinyl group Chemical group 0.000 claims description 4
• 125000003566 oxetanyl group Chemical group 0.000 claims description 4
• 125000000466 oxiranyl group Chemical group 0.000 claims description 4
• 125000001984 thiazolidinyl group Chemical group 0.000 claims description 4
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 4
• SQVFRQZTEIHSTF-UHFFFAOYSA-N 2-(2,4-dimethoxyphenyl)-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound COC1=CC(OC)=CC=C1C1=CC(=O)N(C=C(C=C2)N3CCNCC3)C2=N1 SQVFRQZTEIHSTF-UHFFFAOYSA-N 0.000 claims description 3
• AOVGDJOUMSWBFU-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-7-(1-ethyl-3,6-dihydro-2h-pyridin-4-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1N(CC)CCC(C2=CN3C(=O)C=C(N=C3C=C2)C=2C=C(OC)C(OC)=CC=2)=C1 AOVGDJOUMSWBFU-UHFFFAOYSA-N 0.000 claims description 3
• JCYVXNQUQQXTIO-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-7-(1-methyl-3,6-dihydro-2h-pyridin-4-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(=O)N(C=C(C=C2)C=3CCN(C)CC=3)C2=N1 JCYVXNQUQQXTIO-UHFFFAOYSA-N 0.000 claims description 3
• OKUVHVOFNUEEPO-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-7-(1-propyl-3,6-dihydro-2h-pyridin-4-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1N(CCC)CCC(C2=CN3C(=O)C=C(N=C3C=C2)C=2C=C(OC)C(OC)=CC=2)=C1 OKUVHVOFNUEEPO-UHFFFAOYSA-N 0.000 claims description 3
• KSQCNIQLFPPXGQ-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-7-(4-ethylpiperazin-1-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(CC)CCN1C1=CN2C(=O)C=C(C=3C=C(OC)C(OC)=CC=3)N=C2C=C1 KSQCNIQLFPPXGQ-UHFFFAOYSA-N 0.000 claims description 3
• AJTLSSXMMRHLBL-IYBDPMFKSA-N 2-(3,4-dimethoxyphenyl)-7-[(3r,5s)-3,5-dimethylpiperazin-1-yl]-9-methylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(=O)N(C=C(C=C2C)N3C[C@@H](C)N[C@@H](C)C3)C2=N1 AJTLSSXMMRHLBL-IYBDPMFKSA-N 0.000 claims description 3
• LJVAWMVTLGXKSU-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-7-[1-(2-hydroxyethyl)piperidin-4-yl]pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(=O)N(C=C(C=C2)C3CCN(CCO)CC3)C2=N1 LJVAWMVTLGXKSU-UHFFFAOYSA-N 0.000 claims description 3
• QRBFDUOCGUHAJG-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-7-[4-(dimethylamino)piperidin-1-yl]-9-methylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(=O)N(C=C(C=C2C)N3CCC(CC3)N(C)C)C2=N1 QRBFDUOCGUHAJG-UHFFFAOYSA-N 0.000 claims description 3
• BJAUQRQXBDTEQC-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-9-ethyl-7-(1,2,3,6-tetrahydropyridin-4-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound CCC1=CC(C=2CCNCC=2)=CN(C(C=2)=O)C1=NC=2C1=CC=C(OC)C(OC)=C1 BJAUQRQXBDTEQC-UHFFFAOYSA-N 0.000 claims description 3
• VNJJMCNLQJCHBL-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-9-methoxy-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(=O)N(C=C(C=C2OC)N3CCNCC3)C2=N1 VNJJMCNLQJCHBL-UHFFFAOYSA-N 0.000 claims description 3
• FPNUDKKNMNBDHQ-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-9-methyl-7-[4-(propylamino)piperidin-1-yl]pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CC(NCCC)CCN1C1=CN2C(=O)C=C(C=3C=C(OC)C(OC)=CC=3)N=C2C(C)=C1 FPNUDKKNMNBDHQ-UHFFFAOYSA-N 0.000 claims description 3
• QQUQNSZQCLVURZ-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-9-methyl-7-piperidin-4-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(=O)N(C=C(C=C2C)C3CCNCC3)C2=N1 QQUQNSZQCLVURZ-UHFFFAOYSA-N 0.000 claims description 3
• UZDVCWMNLDRDHE-UHFFFAOYSA-N 2-(3-fluoro-4-hydroxyphenyl)-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C(F)C(O)=CC=C1C1=CC(=O)N(C=C(C=C2)N3CCNCC3)C2=N1 UZDVCWMNLDRDHE-UHFFFAOYSA-N 0.000 claims description 3
• AMQAXVJHDSEBCO-UHFFFAOYSA-N 2-(4-methoxyphenyl)-7-(4-methyl-1,4-diazepan-1-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=CC(OC)=CC=C1C1=CC(=O)N(C=C(C=C2)N3CCN(C)CCC3)C2=N1 AMQAXVJHDSEBCO-UHFFFAOYSA-N 0.000 claims description 3
• AYTRANKELKCTKG-LBPRGKRZSA-N 2-[3-(difluoromethoxy)-4-hydroxyphenyl]-7-[(3s)-3-methylpiperazin-1-yl]pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN[C@@H](C)CN1C1=CN2C(=O)C=C(C=3C=C(OC(F)F)C(O)=CC=3)N=C2C=C1 AYTRANKELKCTKG-LBPRGKRZSA-N 0.000 claims description 3
• GVZOFDYLTMTLHI-ZDUSSCGKSA-N 2-[3-(difluoromethoxy)-4-methoxyphenyl]-7-[(3s)-3-methylpiperazin-1-yl]pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C(OC(F)F)C(OC)=CC=C1C1=CC(=O)N(C=C(C=C2)N3C[C@H](C)NCC3)C2=N1 GVZOFDYLTMTLHI-ZDUSSCGKSA-N 0.000 claims description 3
• CDGUTFPGJHNMKR-UHFFFAOYSA-N 2-[3-fluoro-4-(2,2,2-trifluoroethoxy)phenyl]-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C(OCC(F)(F)F)C(F)=CC(C=2N=C3C=CC(=CN3C(=O)C=2)N2CCNCC2)=C1 CDGUTFPGJHNMKR-UHFFFAOYSA-N 0.000 claims description 3
• DORQVVZGPQSHKH-UHFFFAOYSA-N 2-[4-(dimethylamino)phenyl]-9-fluoro-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=CC(N(C)C)=CC=C1C1=CC(=O)N(C=C(C=C2F)N3CCNCC3)C2=N1 DORQVVZGPQSHKH-UHFFFAOYSA-N 0.000 claims description 3
• GXWLXKCYVWRTNW-ZDUSSCGKSA-N 2-[4-methoxy-3-(trifluoromethoxy)phenyl]-7-[(3s)-3-methylpiperazin-1-yl]pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C(OC(F)(F)F)C(OC)=CC=C1C1=CC(=O)N(C=C(C=C2)N3C[C@H](C)NCC3)C2=N1 GXWLXKCYVWRTNW-ZDUSSCGKSA-N 0.000 claims description 3
• ZNCSJQMTDRRLQW-UHFFFAOYSA-N 2-phenyl-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C=1N2C(=O)C=C(C=3C=CC=CC=3)N=C2C=CC=1N1CCNCC1 ZNCSJQMTDRRLQW-UHFFFAOYSA-N 0.000 claims description 3
• KSWRUNMYCSFYKD-UHFFFAOYSA-N 3-(4-oxo-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-2-yl)benzonitrile Chemical compound C=1N2C(=O)C=C(C=3C=C(C=CC=3)C#N)N=C2C=CC=1N1CCNCC1 KSWRUNMYCSFYKD-UHFFFAOYSA-N 0.000 claims description 3
• PFFDRTAKYKQIJP-OAHLLOKOSA-N 7-[(3r)-3-(dimethylamino)pyrrolidin-1-yl]-2-(3-fluoro-4-methoxyphenyl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C(F)C(OC)=CC=C1C1=CC(=O)N(C=C(C=C2)N3C[C@@H](CC3)N(C)C)C2=N1 PFFDRTAKYKQIJP-OAHLLOKOSA-N 0.000 claims description 3
• AICVMNGCMJPODZ-UHFFFAOYSA-N 7-[4-(cyclopropylamino)piperidin-1-yl]-2-(3,4-dimethoxyphenyl)-9-methylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(=O)N(C=C(C=C2C)N3CCC(CC3)NC3CC3)C2=N1 AICVMNGCMJPODZ-UHFFFAOYSA-N 0.000 claims description 3
• ILSVMUXCCOPWJW-UHFFFAOYSA-N 7-[4-(dimethylamino)piperidin-1-yl]-2-(3-fluoro-4-methoxyphenyl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C(F)C(OC)=CC=C1C1=CC(=O)N(C=C(C=C2)N3CCC(CC3)N(C)C)C2=N1 ILSVMUXCCOPWJW-UHFFFAOYSA-N 0.000 claims description 3
• ZEUSNYANSXSDPZ-UHFFFAOYSA-N COc1ccc(cc1OC)-c1cc(=O)n2cc(cc(C)c2n1)C1=CCN(CCO)CC1 Chemical compound COc1ccc(cc1OC)-c1cc(=O)n2cc(cc(C)c2n1)C1=CCN(CCO)CC1 ZEUSNYANSXSDPZ-UHFFFAOYSA-N 0.000 claims description 3
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 3
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
• 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims description 3
• 125000004043 oxo group Chemical group O=* 0.000 claims description 3
• 125000003367 polycyclic group Chemical group 0.000 claims description 3
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
• WVCHJLPEYZRYCE-UHFFFAOYSA-N 2-(1,2,3,6-tetrahydropyridin-4-yl)pyrazino[1,2-a]pyrimidin-4-one Chemical compound N1=C2C=NC=CN2C(=O)C=C1C1=CCNCC1 WVCHJLPEYZRYCE-UHFFFAOYSA-N 0.000 claims description 2
• LKOZDQMVHOIMEG-ZDUSSCGKSA-N 2-(2-fluoro-4,5-dimethoxyphenyl)-7-[(3s)-3-methylpiperazin-1-yl]pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C(OC)C(OC)=CC(F)=C1C1=CC(=O)N(C=C(C=C2)N3C[C@H](C)NCC3)C2=N1 LKOZDQMVHOIMEG-ZDUSSCGKSA-N 0.000 claims description 2
• SGMVEALTIPWMIZ-UHFFFAOYSA-N 2-(2-fluoro-4,5-dimethoxyphenyl)-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C(OC)C(OC)=CC(F)=C1C1=CC(=O)N(C=C(C=C2)N3CCNCC3)C2=N1 SGMVEALTIPWMIZ-UHFFFAOYSA-N 0.000 claims description 2
• QLWZLZJHKNDLLO-UHFFFAOYSA-N 2-(3,4-difluoro-5-methoxyphenyl)-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound FC1=C(F)C(OC)=CC(C=2N=C3C=CC(=CN3C(=O)C=2)N2CCNCC2)=C1 QLWZLZJHKNDLLO-UHFFFAOYSA-N 0.000 claims description 2
• VTBWSXZPSUMDFU-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-7-(1-ethylpiperidin-4-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(CC)CCC1C1=CN2C(=O)C=C(C=3C=C(OC)C(OC)=CC=3)N=C2C=C1 VTBWSXZPSUMDFU-UHFFFAOYSA-N 0.000 claims description 2
• ISCXMZWCEQDWHN-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-7-(1-methylpiperidin-4-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(=O)N(C=C(C=C2)C3CCN(C)CC3)C2=N1 ISCXMZWCEQDWHN-UHFFFAOYSA-N 0.000 claims description 2
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