DK2812004T3 - COMPOUNDS FOR TREATMENT OF SPINAL MUSCLE DROPHY - Google Patents

Info

Publication number

DK2812004T3

DK2812004T3 DK13747100.9T DK13747100T DK2812004T3 DK 2812004 T3 DK2812004 T3 DK 2812004T3 DK 13747100 T DK13747100 T DK 13747100T DK 2812004 T3 DK2812004 T3 DK 2812004T3

Authority

DK

Denmark

Prior art keywords

pyrido

pyrimidin

pyrazin

methyl

pyridin

Prior art date

2012-02-10

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• 150000001875 compounds Chemical class 0.000 title claims description 1203
• 210000003205 muscle Anatomy 0.000 title description 13
• -1 halo-C1-6alkyl Chemical group 0.000 claims description 779
• 102100021947 Survival motor neuron protein Human genes 0.000 claims description 346
• 101000617738 Homo sapiens Survival motor neuron protein Proteins 0.000 claims description 342
• 108020004999 messenger RNA Proteins 0.000 claims description 198
• 101150081851 SMN1 gene Proteins 0.000 claims description 152
• 125000001424 substituent group Chemical group 0.000 claims description 128
• 125000000623 heterocyclic group Chemical group 0.000 claims description 127
• 101150015954 SMN2 gene Proteins 0.000 claims description 110
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 97
• 125000001072 heteroaryl group Chemical group 0.000 claims description 92
• 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 82
• 238000000034 method Methods 0.000 claims description 71
• 125000003118 aryl group Chemical group 0.000 claims description 68
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 61
• 101100203482 Drosophila melanogaster Smn gene Proteins 0.000 claims description 54
• 101150069235 Snrpn gene Proteins 0.000 claims description 54
• 239000008194 pharmaceutical composition Substances 0.000 claims description 46
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 40
• 150000003839 salts Chemical class 0.000 claims description 39
• 125000004076 pyridyl group Chemical group 0.000 claims description 37
• 125000000217 alkyl group Chemical group 0.000 claims description 35
• 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 34
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 26
• 229910052736 halogen Inorganic materials 0.000 claims description 24
• 150000002367 halogens Chemical class 0.000 claims description 24
• 230000001965 increasing effect Effects 0.000 claims description 23
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 21
• 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 15
• 239000003085 diluting agent Substances 0.000 claims description 15
• 229910052739 hydrogen Inorganic materials 0.000 claims description 15
• 239000001257 hydrogen Substances 0.000 claims description 15
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 14
• 239000002253 acid Substances 0.000 claims description 13
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
• 239000003937 drug carrier Substances 0.000 claims description 13
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 12
• 125000003386 piperidinyl group Chemical group 0.000 claims description 12
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
• 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 11
• 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 10
• 125000004193 piperazinyl group Chemical group 0.000 claims description 9
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 9
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
• 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 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 8
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 7
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 7
• 125000002393 azetidinyl group Chemical group 0.000 claims description 6
• 125000004613 furo[2,3-c]pyridinyl group Chemical group O1C(=CC=2C1=CN=CC2)* 0.000 claims description 6
• 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 6
• 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims description 6
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 6
• 125000004043 oxo group Chemical group O=* 0.000 claims description 5
• OQHQOOLVQDEIGL-UHFFFAOYSA-N 2-methyl-2,7-diazaspiro[4.4]nonane Chemical compound C1N(C)CCC11CNCC1 OQHQOOLVQDEIGL-UHFFFAOYSA-N 0.000 claims description 4
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 4
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 4
• 239000012458 free base Substances 0.000 claims description 4
• 125000005960 1,4-diazepanyl group Chemical group 0.000 claims description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
• DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims 153
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 28
• 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 24
• 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 16
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 15
• 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 13
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
• 125000003282 alkyl amino group Chemical group 0.000 claims 5
• HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 claims 4
• 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 4
• 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 4
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 3
• DFYQXPGNOPPUGS-UHFFFAOYSA-N 2-(2,8-dimethylimidazo[1,2-a]pyridin-6-yl)-7-(4-ethylpiperazin-1-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(CC)CCN1C1=CN2C(=O)C=C(C3=CN4C=C(C)N=C4C(C)=C3)N=C2C=C1 DFYQXPGNOPPUGS-UHFFFAOYSA-N 0.000 claims 3
• VKBXHPYPNYCDBH-UHFFFAOYSA-N 2-(2,8-dimethylimidazo[1,2-a]pyridin-6-yl)-7-(4-methylpiperazin-1-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(C)CCN1C1=CN2C(=O)C=C(C3=CN4C=C(C)N=C4C(C)=C3)N=C2C=C1 VKBXHPYPNYCDBH-UHFFFAOYSA-N 0.000 claims 3
• 150000002431 hydrogen Chemical class 0.000 claims 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
• UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims 3
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 2
• BDVKAMAALQXGLM-UHFFFAOYSA-N 1-ethylpiperidin-4-one Chemical compound CCN1CCC(=O)CC1 BDVKAMAALQXGLM-UHFFFAOYSA-N 0.000 claims 2
• SBADHNHELWJBMW-UHFFFAOYSA-N 2-(2,8-dimethylimidazo[1,2-a]pyridin-6-yl)-7-(1-ethylpiperidin-4-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(CC)CCC1C1=CN2C(=O)C=C(C3=CN4C=C(C)N=C4C(C)=C3)N=C2C=C1 SBADHNHELWJBMW-UHFFFAOYSA-N 0.000 claims 2
• FOLOAVVSQXMKRV-UHFFFAOYSA-N 2-(2,8-dimethylimidazo[1,2-a]pyridin-6-yl)-7-(1-methylpiperidin-4-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(C)CCC1C1=CN2C(=O)C=C(C3=CN4C=C(C)N=C4C(C)=C3)N=C2C=C1 FOLOAVVSQXMKRV-UHFFFAOYSA-N 0.000 claims 2
• NOJBJWZWMDMEJO-UHFFFAOYSA-N 2-(2,8-dimethylimidazo[1,2-a]pyridin-6-yl)-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C(C)C2=NC(C)=CN2C=C1C(N=C1C=C2)=CC(=O)N1C=C2N1CCNCC1 NOJBJWZWMDMEJO-UHFFFAOYSA-N 0.000 claims 2
• OZUADYGMVLGISR-UHFFFAOYSA-N 2-(2,8-dimethylimidazo[1,2-a]pyridin-6-yl)-7-piperidin-4-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C(C)C2=NC(C)=CN2C=C1C(N=C1C=C2)=CC(=O)N1C=C2C1CCNCC1 OZUADYGMVLGISR-UHFFFAOYSA-N 0.000 claims 2
• VVSQYKQUEZFGBX-AWEZNQCLSA-N 2-(2-methylimidazo[1,2-a]pyridin-6-yl)-7-[(3s)-3-methylpiperazin-1-yl]pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN[C@@H](C)CN1C1=CN2C(=O)C=C(C3=CN4C=C(C)N=C4C=C3)N=C2C=C1 VVSQYKQUEZFGBX-AWEZNQCLSA-N 0.000 claims 2
• IIHMBZPFFIHPBB-UHFFFAOYSA-N 2-(2-methylimidazo[1,2-a]pyridin-7-yl)-7-(4-methylpiperazin-1-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(C)CCN1C1=CN2C(=O)C=C(C3=CC4=NC(C)=CN4C=C3)N=C2C=C1 IIHMBZPFFIHPBB-UHFFFAOYSA-N 0.000 claims 2
• XSTSQNDPWRSAJL-UHFFFAOYSA-N 2-(4,6-dimethylpyrazolo[1,5-a]pyrazin-2-yl)-7-(4-ethylpiperazin-1-yl)-9-methylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(CC)CCN1C1=CN2C(=O)C=C(C3=NN4C=C(C)N=C(C)C4=C3)N=C2C(C)=C1 XSTSQNDPWRSAJL-UHFFFAOYSA-N 0.000 claims 2
• IECPRWYSJTWAQC-CYBMUJFWSA-N 2-(4,6-dimethylpyrazolo[1,5-a]pyrazin-2-yl)-7-[(3r)-3-methylpiperazin-1-yl]pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN[C@H](C)CN1C1=CN2C(=O)C=C(C3=NN4C=C(C)N=C(C)C4=C3)N=C2C=C1 IECPRWYSJTWAQC-CYBMUJFWSA-N 0.000 claims 2
• JLFYUIUFCVPQEI-UHFFFAOYSA-N 2-(4,6-dimethylpyrazolo[1,5-a]pyrazin-2-yl)-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C2C(C)=NC(C)=CN2N=C1C(N=C1C=C2)=CC(=O)N1C=C2N1CCNCC1 JLFYUIUFCVPQEI-UHFFFAOYSA-N 0.000 claims 2
• FLJLWLHOLFRBIL-UHFFFAOYSA-N 2-(4,6-dimethylpyrazolo[1,5-a]pyrazin-2-yl)-9-methyl-7-(1-methylpiperidin-4-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(C)CCC1C1=CN2C(=O)C=C(C3=NN4C=C(C)N=C(C)C4=C3)N=C2C(C)=C1 FLJLWLHOLFRBIL-UHFFFAOYSA-N 0.000 claims 2
• QATKMCTWUDXGKK-UHFFFAOYSA-N 2-(4-ethyl-6-methylpyrazolo[1,5-a]pyrazin-2-yl)-7-(4-ethylpiperazin-1-yl)-9-methylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(CC)CCN1C1=CN2C(=O)C=C(C3=NN4C=C(C)N=C(CC)C4=C3)N=C2C(C)=C1 QATKMCTWUDXGKK-UHFFFAOYSA-N 0.000 claims 2
• CNDGKNQXKNWKEQ-UHFFFAOYSA-N 2-(4-ethyl-6-methylpyrazolo[1,5-a]pyrazin-2-yl)-9-methyl-7-piperidin-4-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C2C(CC)=NC(C)=CN2N=C1C(N=C1C(C)=C2)=CC(=O)N1C=C2C1CCNCC1 CNDGKNQXKNWKEQ-UHFFFAOYSA-N 0.000 claims 2
• AVWJMBZZOAFETI-UHFFFAOYSA-N 2-(6-methyl-4-propylpyrazolo[1,5-a]pyrazin-2-yl)-7-piperidin-4-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C2C(CCC)=NC(C)=CN2N=C1C(N=C1C=C2)=CC(=O)N1C=C2C1CCNCC1 AVWJMBZZOAFETI-UHFFFAOYSA-N 0.000 claims 2
• DMKAKYCYGHVVQX-UHFFFAOYSA-N 2-(8-ethyl-2-methylimidazo[1,2-a]pyridin-6-yl)-7-(1-methylpiperidin-4-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C=1N2C=C(C)N=C2C(CC)=CC=1C(N=C1C=C2)=CC(=O)N1C=C2C1CCN(C)CC1 DMKAKYCYGHVVQX-UHFFFAOYSA-N 0.000 claims 2
• UGTJXXHGRUOQHW-OAHLLOKOSA-N 2-(8-ethyl-2-methylimidazo[1,2-a]pyridin-6-yl)-7-[(3r)-3-methylpiperazin-1-yl]pyrido[1,2-a]pyrimidin-4-one Chemical compound C=1N2C=C(C)N=C2C(CC)=CC=1C(N=C1C=C2)=CC(=O)N1C=C2N1CCN[C@H](C)C1 UGTJXXHGRUOQHW-OAHLLOKOSA-N 0.000 claims 2
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 2
• ICFJWVNLOQWVEG-UHFFFAOYSA-N 7-(1-ethylpiperidin-4-yl)-2-(2-methylimidazo[1,2-a]pyridin-7-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(CC)CCC1C1=CN2C(=O)C=C(C3=CC4=NC(C)=CN4C=C3)N=C2C=C1 ICFJWVNLOQWVEG-UHFFFAOYSA-N 0.000 claims 2
• OMQLYYVDGNEAJF-GASCZTMLSA-N 7-[(3s,5r)-3,5-dimethylpiperazin-1-yl]-2-(2-methylimidazo[1,2-a]pyridin-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1[C@@H](C)N[C@@H](C)CN1C1=CN2C(=O)C=C(C3=CN4C=C(C)N=C4C=C3)N=C2C=C1 OMQLYYVDGNEAJF-GASCZTMLSA-N 0.000 claims 2
• RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims 2
• 125000003545 alkoxy group Chemical group 0.000 claims 2
• 125000000753 cycloalkyl group Chemical group 0.000 claims 2
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 2
• 201000006938 muscular dystrophy Diseases 0.000 claims 2
• DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims 2
• 125000006308 propyl amino group Chemical group 0.000 claims 2
• SSJXIUAHEKJCMH-WDSKDSINSA-N (1s,2s)-cyclohexane-1,2-diamine Chemical compound N[C@H]1CCCC[C@@H]1N SSJXIUAHEKJCMH-WDSKDSINSA-N 0.000 claims 1
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
• 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 1
• SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 claims 1
• QOZOFODNIBQPGN-UHFFFAOYSA-N 2,4-dimethylpiperidine Chemical compound CC1CCNC(C)C1 QOZOFODNIBQPGN-UHFFFAOYSA-N 0.000 claims 1
• ALFBVTXTZONSGK-UHFFFAOYSA-N 2-(1-methylpyrrolo[2,3-b]pyridin-5-yl)-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C=1N=C2N(C)C=CC2=CC=1C(N=C1C=C2)=CC(=O)N1C=C2N1CCNCC1 ALFBVTXTZONSGK-UHFFFAOYSA-N 0.000 claims 1
• OMQRPOFLPXEGEP-UHFFFAOYSA-N 2-(1h-indol-5-yl)-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C=1N2C(=O)C=C(C=3C=C4C=CNC4=CC=3)N=C2C=CC=1N1CCNCC1 OMQRPOFLPXEGEP-UHFFFAOYSA-N 0.000 claims 1
• LBYYCEQBIRGHQM-UHFFFAOYSA-N 2-(2,7-dimethylindazol-5-yl)-7-(1-methylpiperidin-4-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(C)CCC1C1=CN2C(=O)C=C(C3=CC4=CN(C)N=C4C(C)=C3)N=C2C=C1 LBYYCEQBIRGHQM-UHFFFAOYSA-N 0.000 claims 1
• MYUPVYZHSRSOMG-INIZCTEOSA-N 2-(2,7-dimethylindazol-5-yl)-7-[(3s)-3,4-dimethylpiperazin-1-yl]pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(C)[C@@H](C)CN1C1=CN2C(=O)C=C(C3=CC4=CN(C)N=C4C(C)=C3)N=C2C=C1 MYUPVYZHSRSOMG-INIZCTEOSA-N 0.000 claims 1
• IHNXTKFBGKSKPW-UHFFFAOYSA-N 2-(2,8-dimethylimidazo[1,2-a]pyridin-6-yl)-7-(1-propan-2-ylpiperidin-4-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(C(C)C)CCC1C1=CN2C(=O)C=C(C3=CN4C=C(C)N=C4C(C)=C3)N=C2C=C1 IHNXTKFBGKSKPW-UHFFFAOYSA-N 0.000 claims 1
• MRLJEIUGTWPHGC-UHFFFAOYSA-N 2-(2-ethylimidazo[1,2-a]pyridin-6-yl)-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=CC2=NC(CC)=CN2C=C1C(N=C1C=C2)=CC(=O)N1C=C2N1CCNCC1 MRLJEIUGTWPHGC-UHFFFAOYSA-N 0.000 claims 1
• XSUQLWOIPSMMSX-UHFFFAOYSA-N 2-(2-methyl-1,3-benzothiazol-5-yl)-7-(4-methyl-1,4-diazepan-1-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(C)CCCN1C1=CN2C(=O)C=C(C=3C=C4N=C(C)SC4=CC=3)N=C2C=C1 XSUQLWOIPSMMSX-UHFFFAOYSA-N 0.000 claims 1
• GDVOABXZNBIUEI-UHFFFAOYSA-N 2-(2-methyl-1,3-benzothiazol-6-yl)-7-(1,2,3,6-tetrahydropyridin-4-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C2SC(C)=NC2=CC=C1C(N=C1C=C2)=CC(=O)N1C=C2C1=CCNCC1 GDVOABXZNBIUEI-UHFFFAOYSA-N 0.000 claims 1
• SDNWLDOTTZVOAH-UHFFFAOYSA-N 2-(2-methyl-1,3-benzothiazol-6-yl)-7-(1-methyl-3,6-dihydro-2h-pyridin-4-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1N(C)CCC(C2=CN3C(=O)C=C(N=C3C=C2)C=2C=C3SC(C)=NC3=CC=2)=C1 SDNWLDOTTZVOAH-UHFFFAOYSA-N 0.000 claims 1
• ZYLDVYCLFGXFJI-UHFFFAOYSA-N 2-(2-methyl-1,3-benzothiazol-6-yl)-7-(1-propan-2-yl-3,6-dihydro-2h-pyridin-4-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1N(C(C)C)CCC(C2=CN3C(=O)C=C(N=C3C=C2)C=2C=C3SC(C)=NC3=CC=2)=C1 ZYLDVYCLFGXFJI-UHFFFAOYSA-N 0.000 claims 1
• BUQNGCPDYWMHOA-UHFFFAOYSA-N 2-(2-methyl-1,3-benzothiazol-6-yl)-7-piperidin-4-yloxypyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C2SC(C)=NC2=CC=C1C(N=C1C=C2)=CC(=O)N1C=C2OC1CCNCC1 BUQNGCPDYWMHOA-UHFFFAOYSA-N 0.000 claims 1
• WIRNEEAZZNLZFV-UHFFFAOYSA-N 2-(2-methyl-1,3-benzoxazol-6-yl)-7-(1,2,3,6-tetrahydropyridin-4-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C2OC(C)=NC2=CC=C1C(N=C1C=C2)=CC(=O)N1C=C2C1=CCNCC1 WIRNEEAZZNLZFV-UHFFFAOYSA-N 0.000 claims 1
• WASUGDAQGOVUEJ-UHFFFAOYSA-N 2-(2-methyl-1,3-benzoxazol-6-yl)-7-(4-methylpiperazin-1-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(C)CCN1C1=CN2C(=O)C=C(C=3C=C4OC(C)=NC4=CC=3)N=C2C=C1 WASUGDAQGOVUEJ-UHFFFAOYSA-N 0.000 claims 1
• QUKBZJDSZYLWLT-UHFFFAOYSA-N 2-(2-methylimidazo[1,2-a]pyridin-6-yl)-7-(4-methylpiperazin-1-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(C)CCN1C1=CN2C(=O)C=C(C3=CN4C=C(C)N=C4C=C3)N=C2C=C1 QUKBZJDSZYLWLT-UHFFFAOYSA-N 0.000 claims 1
• CGKHUJYUVIXJEU-UHFFFAOYSA-N 2-(2-methylimidazo[1,2-a]pyridin-6-yl)-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=CC2=NC(C)=CN2C=C1C(N=C1C=C2)=CC(=O)N1C=C2N1CCNCC1 CGKHUJYUVIXJEU-UHFFFAOYSA-N 0.000 claims 1
• UVIYXIMQVSSPSU-UHFFFAOYSA-N 2-(2-methylimidazo[1,2-a]pyridin-7-yl)-7-(1-methylpiperidin-4-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(C)CCC1C1=CN2C(=O)C=C(C3=CC4=NC(C)=CN4C=C3)N=C2C=C1 UVIYXIMQVSSPSU-UHFFFAOYSA-N 0.000 claims 1
• ZHHKRPADXSHSSD-UHFFFAOYSA-N 2-(2-methylimidazo[1,2-a]pyridin-7-yl)-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C=1C2=NC(C)=CN2C=CC=1C(N=C1C=C2)=CC(=O)N1C=C2N1CCNCC1 ZHHKRPADXSHSSD-UHFFFAOYSA-N 0.000 claims 1
• RVMFLISZFCHUBW-UHFFFAOYSA-N 2-(2-methylimidazo[1,2-a]pyridin-7-yl)-7-piperidin-4-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C=1C2=NC(C)=CN2C=CC=1C(N=C1C=C2)=CC(=O)N1C=C2C1CCNCC1 RVMFLISZFCHUBW-UHFFFAOYSA-N 0.000 claims 1
• VNGAJULPBJVORU-AWEZNQCLSA-N 2-(2-methylindazol-5-yl)-7-[(3s)-3-methylpiperazin-1-yl]pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN[C@@H](C)CN1C1=CN2C(=O)C=C(C3=CC4=CN(C)N=C4C=C3)N=C2C=C1 VNGAJULPBJVORU-AWEZNQCLSA-N 0.000 claims 1
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• DCLSWIKQWGLODE-UHFFFAOYSA-N 2-(4,6-dimethylpyrazolo[1,5-a]pyrazin-2-yl)-7-(1-methylpiperidin-4-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(C)CCC1C1=CN2C(=O)C=C(C3=NN4C=C(C)N=C(C)C4=C3)N=C2C=C1 DCLSWIKQWGLODE-UHFFFAOYSA-N 0.000 claims 1
• VMDJMSCZABSTOU-UHFFFAOYSA-N 2-(4,6-dimethylpyrazolo[1,5-a]pyrazin-2-yl)-7-(1-propan-2-ylpiperidin-4-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(C(C)C)CCC1C1=CN2C(=O)C=C(C3=NN4C=C(C)N=C(C)C4=C3)N=C2C=C1 VMDJMSCZABSTOU-UHFFFAOYSA-N 0.000 claims 1
• CTRKFPRBODSBDX-UHFFFAOYSA-N 2-(4,6-dimethylpyrazolo[1,5-a]pyrazin-2-yl)-7-(4-ethylpiperazin-1-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(CC)CCN1C1=CN2C(=O)C=C(C3=NN4C=C(C)N=C(C)C4=C3)N=C2C=C1 CTRKFPRBODSBDX-UHFFFAOYSA-N 0.000 claims 1
• AVAZIGQZBSEPJV-UHFFFAOYSA-N 2-(4,6-dimethylpyrazolo[1,5-a]pyrazin-2-yl)-7-(4-methyl-1,4-diazepan-1-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(C)CCCN1C1=CN2C(=O)C=C(C3=NN4C=C(C)N=C(C)C4=C3)N=C2C=C1 AVAZIGQZBSEPJV-UHFFFAOYSA-N 0.000 claims 1
• ZUYOOCCQYSTVKL-UHFFFAOYSA-N 2-(4,6-dimethylpyrazolo[1,5-a]pyrazin-2-yl)-7-(4-methylpiperazin-1-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(C)CCN1C1=CN2C(=O)C=C(C3=NN4C=C(C)N=C(C)C4=C3)N=C2C=C1 ZUYOOCCQYSTVKL-UHFFFAOYSA-N 0.000 claims 1
• VUFIOIJCNAQGFU-KBPBESRZSA-N 2-(4,6-dimethylpyrazolo[1,5-a]pyrazin-2-yl)-7-[(2s,6s)-2,6-dimethyl-1,2,3,6-tetrahydropyridin-4-yl]pyrido[1,2-a]pyrimidin-4-one Chemical compound C[C@@H]1N[C@@H](C)CC(C2=CN3C(=O)C=C(N=C3C=C2)C2=NN3C=C(C)N=C(C)C3=C2)=C1 VUFIOIJCNAQGFU-KBPBESRZSA-N 0.000 claims 1
• IECPRWYSJTWAQC-ZDUSSCGKSA-N 2-(4,6-dimethylpyrazolo[1,5-a]pyrazin-2-yl)-7-[(3s)-3-methylpiperazin-1-yl]pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN[C@@H](C)CN1C1=CN2C(=O)C=C(C3=NN4C=C(C)N=C(C)C4=C3)N=C2C=C1 IECPRWYSJTWAQC-ZDUSSCGKSA-N 0.000 claims 1
• AYAVRUQDEYRJLU-UHFFFAOYSA-N 2-(4,6-dimethylpyrazolo[1,5-a]pyrazin-2-yl)-7-piperidin-4-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C2C(C)=NC(C)=CN2N=C1C(N=C1C=C2)=CC(=O)N1C=C2C1CCNCC1 AYAVRUQDEYRJLU-UHFFFAOYSA-N 0.000 claims 1
• ZENSDMBUHUWTPB-UHFFFAOYSA-N 2-(4,6-dimethylpyrazolo[1,5-a]pyrazin-2-yl)-9-methyl-7-(1-propylpiperidin-4-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(CCC)CCC1C1=CN2C(=O)C=C(C3=NN4C=C(C)N=C(C)C4=C3)N=C2C(C)=C1 ZENSDMBUHUWTPB-UHFFFAOYSA-N 0.000 claims 1
• OHXBTGLLYWHKMH-CQSZACIVSA-N 2-(4,6-dimethylpyrazolo[1,5-a]pyrazin-2-yl)-9-methyl-7-[(3r)-3-methylpiperazin-1-yl]pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN[C@H](C)CN1C1=CN2C(=O)C=C(C3=NN4C=C(C)N=C(C)C4=C3)N=C2C(C)=C1 OHXBTGLLYWHKMH-CQSZACIVSA-N 0.000 claims 1
• XDZMFYNAUKNGDI-UHFFFAOYSA-N 2-(4,6-dimethylpyrazolo[1,5-a]pyrazin-2-yl)-9-methyl-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C2C(C)=NC(C)=CN2N=C1C(N=C1C(C)=C2)=CC(=O)N1C=C2N1CCNCC1 XDZMFYNAUKNGDI-UHFFFAOYSA-N 0.000 claims 1
• INZVBTQELSVJSH-UHFFFAOYSA-N 2-(4,6-dimethylpyrazolo[1,5-a]pyrazin-2-yl)-9-methyl-7-piperidin-4-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C2C(C)=NC(C)=CN2N=C1C(N=C1C(C)=C2)=CC(=O)N1C=C2C1CCNCC1 INZVBTQELSVJSH-UHFFFAOYSA-N 0.000 claims 1
• YNDIHPCBAODJOO-UHFFFAOYSA-N 2-(4-ethyl-6-methylpyrazolo[1,5-a]pyrazin-2-yl)-7-(1-ethylpiperidin-4-yl)-9-methylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(CC)CCC1C1=CN2C(=O)C=C(C3=NN4C=C(C)N=C(CC)C4=C3)N=C2C(C)=C1 YNDIHPCBAODJOO-UHFFFAOYSA-N 0.000 claims 1
• GUAMICLTYHKDFL-UHFFFAOYSA-N 2-(4-ethyl-6-methylpyrazolo[1,5-a]pyrazin-2-yl)-7-(2-morpholin-4-ylethylamino)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C2C(CC)=NC(C)=CN2N=C1C(N=C1C=C2)=CC(=O)N1C=C2NCCN1CCOCC1 GUAMICLTYHKDFL-UHFFFAOYSA-N 0.000 claims 1
• FQGFHDZNYFCYGS-UHFFFAOYSA-N 2-(4-ethyl-6-methylpyrazolo[1,5-a]pyrazin-2-yl)-7-[1-(2-hydroxyethyl)piperidin-4-yl]-9-methylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C2C(CC)=NC(C)=CN2N=C1C(N=C1C(C)=C2)=CC(=O)N1C=C2C1CCN(CCO)CC1 FQGFHDZNYFCYGS-UHFFFAOYSA-N 0.000 claims 1
• QEIBZMAOAFKPSZ-UHFFFAOYSA-N 2-(4-ethyl-6-methylpyrazolo[1,5-a]pyrazin-2-yl)-7-piperidin-4-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C2C(CC)=NC(C)=CN2N=C1C(N=C1C=C2)=CC(=O)N1C=C2C1CCNCC1 QEIBZMAOAFKPSZ-UHFFFAOYSA-N 0.000 claims 1
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• BOBFEZJPFAKZHS-UHFFFAOYSA-N 2-(4-fluoro-2-methyl-1,3-benzoxazol-6-yl)-7-(1-methyl-3,6-dihydro-2h-pyridin-4-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1N(C)CCC(C2=CN3C(=O)C=C(N=C3C=C2)C=2C=C3OC(C)=NC3=C(F)C=2)=C1 BOBFEZJPFAKZHS-UHFFFAOYSA-N 0.000 claims 1
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• WJKKVBMVXUZLLP-UHFFFAOYSA-N 2-(4-fluoro-2-methyl-1,3-benzoxazol-6-yl)-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C2OC(C)=NC2=C(F)C=C1C(N=C1C=C2)=CC(=O)N1C=C2N1CCNCC1 WJKKVBMVXUZLLP-UHFFFAOYSA-N 0.000 claims 1
• JCGBCDPIZLKDNB-LBPRGKRZSA-N 2-(5-fluoro-6-methoxypyridin-3-yl)-7-[(3s)-3-methylpiperazin-1-yl]pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C(F)C(OC)=NC=C1C1=CC(=O)N(C=C(C=C2)N3C[C@H](C)NCC3)C2=N1 JCGBCDPIZLKDNB-LBPRGKRZSA-N 0.000 claims 1
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• NSERVHVSFPIUSO-HNNXBMFYSA-N 2-(8-chloro-2-methylimidazo[1,2-a]pyridin-6-yl)-7-[(3s)-3,4-dimethylpiperazin-1-yl]pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(C)[C@@H](C)CN1C1=CN2C(=O)C=C(C3=CN4C=C(C)N=C4C(Cl)=C3)N=C2C=C1 NSERVHVSFPIUSO-HNNXBMFYSA-N 0.000 claims 1
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• YCRUZUCJHWRHRE-UHFFFAOYSA-N 2-imidazo[1,2-a]pyridin-6-yl-7-(4-methylpiperazin-1-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(C)CCN1C1=CN2C(=O)C=C(C3=CN4C=CN=C4C=C3)N=C2C=C1 YCRUZUCJHWRHRE-UHFFFAOYSA-N 0.000 claims 1
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• ZIFXFWUDPJRGPU-UHFFFAOYSA-N 7-(1,4-diazepan-1-yl)-2-(2-methylimidazo[1,2-a]pyridin-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=CC2=NC(C)=CN2C=C1C(N=C1C=C2)=CC(=O)N1C=C2N1CCCNCC1 ZIFXFWUDPJRGPU-UHFFFAOYSA-N 0.000 claims 1
• GVDQAPRGXLMJBV-UHFFFAOYSA-N 7-(1-cyclobutyl-3,6-dihydro-2h-pyridin-4-yl)-2-(4,6-dimethylpyrazolo[1,5-a]pyrazin-2-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C2C(C)=NC(C)=CN2N=C1C(N=C1C=C2)=CC(=O)N1C=C2C(CC1)=CCN1C1CCC1 GVDQAPRGXLMJBV-UHFFFAOYSA-N 0.000 claims 1
• MTNSTMXHYVWCRU-UHFFFAOYSA-N 7-(1-cyclobutylpiperidin-4-yl)-2-(4-ethyl-6-methylpyrazolo[1,5-a]pyrazin-2-yl)-9-methylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C2C(CC)=NC(C)=CN2N=C1C(N=C1C(C)=C2)=CC(=O)N1C=C2C(CC1)CCN1C1CCC1 MTNSTMXHYVWCRU-UHFFFAOYSA-N 0.000 claims 1
• LVAPLRFZTHTLAL-UHFFFAOYSA-N 7-(1-ethyl-3,6-dihydro-2h-pyridin-4-yl)-2-(4-fluoro-2-methyl-1,3-benzoxazol-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1N(CC)CCC(C2=CN3C(=O)C=C(N=C3C=C2)C=2C=C3OC(C)=NC3=C(F)C=2)=C1 LVAPLRFZTHTLAL-UHFFFAOYSA-N 0.000 claims 1
• JVKXJRATQFXWKQ-UHFFFAOYSA-N 7-(3,3-dimethylpiperazin-1-yl)-2-(2-methyl-1,3-benzothiazol-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C2SC(C)=NC2=CC=C1C(N=C1C=C2)=CC(=O)N1C=C2N1CCNC(C)(C)C1 JVKXJRATQFXWKQ-UHFFFAOYSA-N 0.000 claims 1
• BMCQICWBUORYQO-UHFFFAOYSA-N 7-(3,3-dimethylpiperazin-1-yl)-2-(2-methyl-1,3-benzoxazol-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C2OC(C)=NC2=CC=C1C(N=C1C=C2)=CC(=O)N1C=C2N1CCNC(C)(C)C1 BMCQICWBUORYQO-UHFFFAOYSA-N 0.000 claims 1
• DGNAMSCHFPMZKP-UHFFFAOYSA-N 7-(3,3-dimethylpiperazin-1-yl)-2-(4,6-dimethylpyrazolo[1,5-a]pyrazin-2-yl)-9-methylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C2C(C)=NC(C)=CN2N=C1C(N=C1C(C)=C2)=CC(=O)N1C=C2N1CCNC(C)(C)C1 DGNAMSCHFPMZKP-UHFFFAOYSA-N 0.000 claims 1
• KQHRHYBTTPHNNO-UHFFFAOYSA-N 7-(3,3-dimethylpiperazin-1-yl)-2-(4,6-dimethylpyrazolo[1,5-a]pyrazin-2-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C2C(C)=NC(C)=CN2N=C1C(N=C1C=C2)=CC(=O)N1C=C2N1CCNC(C)(C)C1 KQHRHYBTTPHNNO-UHFFFAOYSA-N 0.000 claims 1
• YOUCOHSDBYVDBC-UHFFFAOYSA-N 7-(4,7-diazaspiro[2.5]octan-7-yl)-2-(2,8-dimethylimidazo[1,2-a]pyridin-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C(C)C2=NC(C)=CN2C=C1C(N=C1C=C2)=CC(=O)N1C=C2N(C1)CCNC21CC2 YOUCOHSDBYVDBC-UHFFFAOYSA-N 0.000 claims 1
• VDHBVLYKOFGPMX-UHFFFAOYSA-N 7-(4-aminopiperidin-1-yl)-2-(2-methyl-1,3-benzothiazol-5-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C=1C=C2SC(C)=NC2=CC=1C(N=C1C=C2)=CC(=O)N1C=C2N1CCC(N)CC1 VDHBVLYKOFGPMX-UHFFFAOYSA-N 0.000 claims 1
• ROMDAPJHOTWIEO-UHFFFAOYSA-N 7-(4-aminopiperidin-1-yl)-2-(2-methyl-1,3-benzoxazol-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C2OC(C)=NC2=CC=C1C(N=C1C=C2)=CC(=O)N1C=C2N1CCC(N)CC1 ROMDAPJHOTWIEO-UHFFFAOYSA-N 0.000 claims 1
• WKVYKUROQXZMJW-UHFFFAOYSA-N 7-(4-cyclopropylpiperazin-1-yl)-2-(4,6-dimethylpyrazolo[1,5-a]pyrazin-2-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C2C(C)=NC(C)=CN2N=C1C(N=C1C=C2)=CC(=O)N1C=C2N(CC1)CCN1C1CC1 WKVYKUROQXZMJW-UHFFFAOYSA-N 0.000 claims 1
• HYHGGJQVCPJLRG-UHFFFAOYSA-N 7-(4-ethylpiperazin-1-yl)-2-(2-methylimidazo[1,2-a]pyridin-7-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(CC)CCN1C1=CN2C(=O)C=C(C3=CC4=NC(C)=CN4C=C3)N=C2C=C1 HYHGGJQVCPJLRG-UHFFFAOYSA-N 0.000 claims 1
• NUBOBCYOSRPERR-UHFFFAOYSA-N 7-(4-methylpiperazin-1-yl)-2-[2-methyl-8-(trifluoromethyl)imidazo[1,2-a]pyridin-6-yl]pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(C)CCN1C1=CN2C(=O)C=C(C3=CN4C=C(C)N=C4C(=C3)C(F)(F)F)N=C2C=C1 NUBOBCYOSRPERR-UHFFFAOYSA-N 0.000 claims 1
• ZDARBZVPKITNFW-KBPBESRZSA-N 7-[(2s,6s)-2,6-dimethylpiperidin-4-yl]-2-(4,6-dimethylpyrazolo[1,5-a]pyrazin-2-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1[C@H](C)N[C@@H](C)CC1C1=CN2C(=O)C=C(C3=NN4C=C(C)N=C(C)C4=C3)N=C2C=C1 ZDARBZVPKITNFW-KBPBESRZSA-N 0.000 claims 1
• UONJSMXRWCNXEB-IYBDPMFKSA-N 7-[(3ar,6as)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrol-5-yl]-2-(2-methyl-1,3-benzoxazol-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=CC2=NC(C3=CC=C4N=C(OC4=C3)C)=CC(=O)N2C=C1N1C[C@H]2CNC[C@H]2C1 UONJSMXRWCNXEB-IYBDPMFKSA-N 0.000 claims 1
• DWXBCQRMKPEUFL-CALCHBBNSA-N 7-[(3ar,6as)-2-methyl-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrol-5-yl]-2-(2-methyl-1,3-benzoxazol-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C2N=C(C)OC2=CC(C=2N=C3C=CC(=CN3C(=O)C=2)N2C[C@@H]3CN(C[C@@H]3C2)C)=C1 DWXBCQRMKPEUFL-CALCHBBNSA-N 0.000 claims 1
• HZQASUJWPLLPKV-CALCHBBNSA-N 7-[(3ar,6as)-2-methyl-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrol-5-yl]-2-(4,6-dimethylpyrazolo[1,5-a]pyrazin-2-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C2C(C)=NC(C)=CN2N=C1C1=CC(=O)N(C=C(N2C[C@@H]3CN(C[C@@H]3C2)C)C=C2)C2=N1 HZQASUJWPLLPKV-CALCHBBNSA-N 0.000 claims 1
• YBXPQFILNBXVQQ-QGZVFWFLSA-N 7-[(3r)-3,4-dimethylpiperazin-1-yl]-2-(4-ethyl-6-methylpyrazolo[1,5-a]pyrazin-2-yl)-9-methylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C2C(CC)=NC(C)=CN2N=C1C(N=C1C(C)=C2)=CC(=O)N1C=C2N1CCN(C)[C@H](C)C1 YBXPQFILNBXVQQ-QGZVFWFLSA-N 0.000 claims 1
• TYTHCZBVCNFCMD-OAHLLOKOSA-N 7-[(3r)-3,4-dimethylpiperazin-1-yl]-2-(8-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(C)[C@H](C)CN1C1=CN2C(=O)C=C(C3=CN4C=C(C)N=C4C(F)=C3)N=C2C=C1 TYTHCZBVCNFCMD-OAHLLOKOSA-N 0.000 claims 1
• YMWCHDDTKRLLPB-OAHLLOKOSA-N 7-[(3r)-3-(aminomethyl)pyrrolidin-1-yl]-2-(4,6-dimethylpyrazolo[1,5-a]pyrazin-2-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C2C(C)=NC(C)=CN2N=C1C(N=C1C=C2)=CC(=O)N1C=C2N1CC[C@H](CN)C1 YMWCHDDTKRLLPB-OAHLLOKOSA-N 0.000 claims 1
• BLONMLZYCNDAHI-GOSISDBHSA-N 7-[(3r)-3-(dimethylamino)pyrrolidin-1-yl]-2-(2,8-dimethylimidazo[1,2-a]pyridin-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1[C@H](N(C)C)CCN1C1=CN2C(=O)C=C(C3=CN4C=C(C)N=C4C(C)=C3)N=C2C=C1 BLONMLZYCNDAHI-GOSISDBHSA-N 0.000 claims 1
• HDQXAZRTORTBKF-MRXNPFEDSA-N 7-[(3r)-3-(dimethylamino)pyrrolidin-1-yl]-2-(2-methyl-1,3-benzothiazol-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1[C@H](N(C)C)CCN1C1=CN2C(=O)C=C(C=3C=C4SC(C)=NC4=CC=3)N=C2C=C1 HDQXAZRTORTBKF-MRXNPFEDSA-N 0.000 claims 1
• LUFJQQZHGNRHFT-MRXNPFEDSA-N 7-[(3r)-3-(dimethylamino)pyrrolidin-1-yl]-2-(4-ethyl-6-methylpyrazolo[1,5-a]pyrazin-2-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C2C(CC)=NC(C)=CN2N=C1C(N=C1C=C2)=CC(=O)N1C=C2N1CC[C@@H](N(C)C)C1 LUFJQQZHGNRHFT-MRXNPFEDSA-N 0.000 claims 1
• VDIRUMKEQOEUGL-QGZVFWFLSA-N 7-[(3r)-3-[(dimethylamino)methyl]pyrrolidin-1-yl]-2-(4,6-dimethylpyrazolo[1,5-a]pyrazin-2-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1[C@@H](CN(C)C)CCN1C1=CN2C(=O)C=C(C3=NN4C=C(C)N=C(C)C4=C3)N=C2C=C1 VDIRUMKEQOEUGL-QGZVFWFLSA-N 0.000 claims 1
• LNZGSQAMRZIZNF-AWEZNQCLSA-N 7-[(3s)-3,4-dimethylpiperazin-1-yl]-2-(2-methyl-1,3-benzoxazol-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(C)[C@@H](C)CN1C1=CN2C(=O)C=C(C=3C=C4OC(C)=NC4=CC=3)N=C2C=C1 LNZGSQAMRZIZNF-AWEZNQCLSA-N 0.000 claims 1
• HKNKQMCTDCTADI-INIZCTEOSA-N 7-[(3s)-3,4-dimethylpiperazin-1-yl]-2-(4,6-dimethylpyrazolo[1,5-a]pyrazin-2-yl)-9-methylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(C)[C@@H](C)CN1C1=CN2C(=O)C=C(C3=NN4C=C(C)N=C(C)C4=C3)N=C2C(C)=C1 HKNKQMCTDCTADI-INIZCTEOSA-N 0.000 claims 1
• YBXPQFILNBXVQQ-KRWDZBQOSA-N 7-[(3s)-3,4-dimethylpiperazin-1-yl]-2-(4-ethyl-6-methylpyrazolo[1,5-a]pyrazin-2-yl)-9-methylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C2C(CC)=NC(C)=CN2N=C1C(N=C1C(C)=C2)=CC(=O)N1C=C2N1CCN(C)[C@@H](C)C1 YBXPQFILNBXVQQ-KRWDZBQOSA-N 0.000 claims 1
• TYTHCZBVCNFCMD-HNNXBMFYSA-N 7-[(3s)-3,4-dimethylpiperazin-1-yl]-2-(8-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(C)[C@@H](C)CN1C1=CN2C(=O)C=C(C3=CN4C=C(C)N=C4C(F)=C3)N=C2C=C1 TYTHCZBVCNFCMD-HNNXBMFYSA-N 0.000 claims 1
• GEKIULWPGKMDRF-IBGZPJMESA-N 7-[(3s)-3-(diethylaminomethyl)pyrrolidin-1-yl]-2-(4,6-dimethylpyrazolo[1,5-a]pyrazin-2-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1[C@H](CN(CC)CC)CCN1C1=CN2C(=O)C=C(C3=NN4C=C(C)N=C(C)C4=C3)N=C2C=C1 GEKIULWPGKMDRF-IBGZPJMESA-N 0.000 claims 1
• BLONMLZYCNDAHI-SFHVURJKSA-N 7-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]-2-(2,8-dimethylimidazo[1,2-a]pyridin-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1[C@@H](N(C)C)CCN1C1=CN2C(=O)C=C(C3=CN4C=C(C)N=C4C(C)=C3)N=C2C=C1 BLONMLZYCNDAHI-SFHVURJKSA-N 0.000 claims 1
• UMYNNCLNFBPMLA-INIZCTEOSA-N 7-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]-2-(2-methyl-1,3-benzoxazol-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1[C@@H](N(C)C)CCN1C1=CN2C(=O)C=C(C=3C=C4OC(C)=NC4=CC=3)N=C2C=C1 UMYNNCLNFBPMLA-INIZCTEOSA-N 0.000 claims 1
• LFVUTSWFZUGHPS-GASCZTMLSA-N 7-[(3s,5r)-3,5-dimethylpiperazin-1-yl]-2-(1-methylpyrrolo[2,3-b]pyridin-5-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1[C@@H](C)N[C@@H](C)CN1C1=CN2C(=O)C=C(C=3C=C4C=CN(C)C4=NC=3)N=C2C=C1 LFVUTSWFZUGHPS-GASCZTMLSA-N 0.000 claims 1
• OLGHUPJFFLRHJS-OKILXGFUSA-N 7-[(3s,5r)-3,5-dimethylpiperazin-1-yl]-2-(2-methyl-1,3-benzoxazol-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1[C@@H](C)N[C@@H](C)CN1C1=CN2C(=O)C=C(C=3C=C4OC(C)=NC4=CC=3)N=C2C=C1 OLGHUPJFFLRHJS-OKILXGFUSA-N 0.000 claims 1
• HMDZWHFITFOZIA-OKILXGFUSA-N 7-[(3s,5r)-3,5-dimethylpiperazin-1-yl]-2-(4,6-dimethylpyrazolo[1,5-a]pyrazin-2-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1[C@@H](C)N[C@@H](C)CN1C1=CN2C(=O)C=C(C3=NN4C=C(C)N=C(C)C4=C3)N=C2C=C1 HMDZWHFITFOZIA-OKILXGFUSA-N 0.000 claims 1
• SDQMYUZJMTUUDF-QGZVFWFLSA-N 7-[(8ar)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl]-2-(4-ethyl-6-methylpyrazolo[1,5-a]pyrazin-2-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN2CCC[C@@H]2CN1C(C=CC1=N2)=CN1C(=O)C=C2C1=NN2C=C(C)N=C(CC)C2=C1 SDQMYUZJMTUUDF-QGZVFWFLSA-N 0.000 claims 1
• WJCJBBJTKSRUGT-QGZVFWFLSA-N 7-[(8ar)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl]-2-(8-chloro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN2CCC[C@@H]2CN1C(C=CC1=N2)=CN1C(=O)C=C2C1=CN2C=C(C)N=C2C(Cl)=C1 WJCJBBJTKSRUGT-QGZVFWFLSA-N 0.000 claims 1
• RXUMTIVZZUJUBN-HXUWFJFHSA-N 7-[(8ar)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl]-2-(8-ethyl-2-methylimidazo[1,2-a]pyridin-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN2CCC[C@@H]2CN1C(C=CC1=N2)=CN1C(=O)C=C2C(C=C1CC)=CN2C1=NC(C)=C2 RXUMTIVZZUJUBN-HXUWFJFHSA-N 0.000 claims 1
• ZRMSACWSMCUDPK-KRWDZBQOSA-N 7-[(8as)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl]-2-(2-methyl-1,3-benzothiazol-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN2CCC[C@H]2CN1C(C=CC1=N2)=CN1C(=O)C=C2C1=CC=C2N=C(C)SC2=C1 ZRMSACWSMCUDPK-KRWDZBQOSA-N 0.000 claims 1
• GODBSPPPPGQMSF-KRWDZBQOSA-N 7-[(8as)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl]-2-(2-methyl-1,3-benzoxazol-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN2CCC[C@H]2CN1C(C=CC1=N2)=CN1C(=O)C=C2C1=CC=C2N=C(C)OC2=C1 GODBSPPPPGQMSF-KRWDZBQOSA-N 0.000 claims 1
• SDQMYUZJMTUUDF-KRWDZBQOSA-N 7-[(8as)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl]-2-(4-ethyl-6-methylpyrazolo[1,5-a]pyrazin-2-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN2CCC[C@H]2CN1C(C=CC1=N2)=CN1C(=O)C=C2C1=NN2C=C(C)N=C(CC)C2=C1 SDQMYUZJMTUUDF-KRWDZBQOSA-N 0.000 claims 1
• JQUQGZRHPKJYIB-INIZCTEOSA-N 7-[(8as)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl]-2-(4-fluoro-2-methyl-1,3-benzoxazol-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN2CCC[C@H]2CN1C(C=CC1=N2)=CN1C(=O)C=C2C1=CC(F)=C2N=C(C)OC2=C1 JQUQGZRHPKJYIB-INIZCTEOSA-N 0.000 claims 1
• WJCJBBJTKSRUGT-KRWDZBQOSA-N 7-[(8as)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl]-2-(8-chloro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN2CCC[C@H]2CN1C(C=CC1=N2)=CN1C(=O)C=C2C1=CN2C=C(C)N=C2C(Cl)=C1 WJCJBBJTKSRUGT-KRWDZBQOSA-N 0.000 claims 1
• RXUMTIVZZUJUBN-FQEVSTJZSA-N 7-[(8as)-3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl]-2-(8-ethyl-2-methylimidazo[1,2-a]pyridin-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN2CCC[C@H]2CN1C(C=CC1=N2)=CN1C(=O)C=C2C(C=C1CC)=CN2C1=NC(C)=C2 RXUMTIVZZUJUBN-FQEVSTJZSA-N 0.000 claims 1
• JJEXWIIJYJSVTM-UHFFFAOYSA-N 7-[1-(2-hydroxyethyl)-3,6-dihydro-2h-pyridin-4-yl]-2-(2-methyl-1,3-benzothiazol-6-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C2SC(C)=NC2=CC=C1C(N=C1C=C2)=CC(=O)N1C=C2C1=CCN(CCO)CC1 JJEXWIIJYJSVTM-UHFFFAOYSA-N 0.000 claims 1
• GUOXEESYNBUSLF-UHFFFAOYSA-N 7-[4-(dimethylamino)piperidin-1-yl]-2-(2-methyl-1,3-benzothiazol-5-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CC(N(C)C)CCN1C1=CN2C(=O)C=C(C=3C=C4N=C(C)SC4=CC=3)N=C2C=C1 GUOXEESYNBUSLF-UHFFFAOYSA-N 0.000 claims 1
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