EA029542B1 - ПРОИЗВОДНЫЕ 4Н-ПИРИДО[1,2-а]ПИРИМИДИН-4-ОНА ДЛЯ ЛЕЧЕНИЯ СПИНАЛЬНОЙ МЫШЕЧНОЙ АТРОФИИ - Google Patents

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Publication number

EA029542B1

EA029542B1 EA201491505A EA201491505A EA029542B1 EA 029542 B1 EA029542 B1 EA 029542B1 EA 201491505 A EA201491505 A EA 201491505A EA 201491505 A EA201491505 A EA 201491505A EA 029542 B1 EA029542 B1 EA 029542B1

Authority

EA

Eurasian Patent Office

Prior art keywords

pyrido

pyrimidin

pyrazin

methyl

pyrimidine

Prior art date

2012-02-10

Links

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• 208000002320 spinal muscular atrophy Diseases 0.000 title claims abstract description 13
• NYJWYCAHJRGKMI-UHFFFAOYSA-N pyrido[1,2-a]pyrimidin-4-one Chemical class C1=CC=CN2C(=O)C=CN=C21 NYJWYCAHJRGKMI-UHFFFAOYSA-N 0.000 title claims description 34
• 150000001875 compounds Chemical class 0.000 claims abstract description 1039
• -1 1,2,5,6-tetrahydropyridinyl Chemical group 0.000 claims description 1074
• 108090000623 proteins and genes Proteins 0.000 claims description 441
• 108020004999 messenger RNA Proteins 0.000 claims description 415
• 125000000217 alkyl group Chemical group 0.000 claims description 258
• 238000000034 method Methods 0.000 claims description 154
• DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims description 143
• 125000001424 substituent group Chemical group 0.000 claims description 57
• 125000000623 heterocyclic group Chemical group 0.000 claims description 46
• 239000008194 pharmaceutical composition Substances 0.000 claims description 46
• 150000003839 salts Chemical class 0.000 claims description 46
• 125000003545 alkoxy group Chemical group 0.000 claims description 45
• 102000004169 proteins and genes Human genes 0.000 claims description 43
• 210000005260 human cell Anatomy 0.000 claims description 39
• 125000004076 pyridyl group Chemical group 0.000 claims description 39
• 125000003282 alkyl amino group Chemical group 0.000 claims description 36
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 36
• 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 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 35
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 34
• 229910052736 halogen Inorganic materials 0.000 claims description 28
• 125000001072 heteroaryl group Chemical group 0.000 claims description 28
• 238000011282 treatment Methods 0.000 claims description 28
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 27
• 230000002708 enhancing effect Effects 0.000 claims description 26
• 150000002367 halogens Chemical class 0.000 claims description 26
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 22
• 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 20
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
• 125000002950 monocyclic group Chemical group 0.000 claims description 19
• 125000003118 aryl group Chemical group 0.000 claims description 17
• 230000001965 increasing effect Effects 0.000 claims description 16
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 15
• 239000003085 diluting agent Substances 0.000 claims description 15
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 15
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 14
• 239000003937 drug carrier Substances 0.000 claims description 14
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 13
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 13
• 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
• 125000004432 carbon atom Chemical group C* 0.000 claims description 11
• 229910052739 hydrogen Inorganic materials 0.000 claims description 11
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
• 125000003386 piperidinyl group Chemical group 0.000 claims description 11
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 11
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
• 239000001257 hydrogen Substances 0.000 claims description 10
• 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 10
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
• 125000002883 imidazolyl group Chemical group 0.000 claims description 9
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
• 125000004429 atom Chemical group 0.000 claims description 8
• 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
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
• 125000004193 piperazinyl group Chemical group 0.000 claims description 8
• 125000001544 thienyl group Chemical group 0.000 claims description 8
• 125000004414 alkyl thio group Chemical group 0.000 claims description 7
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 7
• 125000002757 morpholinyl group Chemical group 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
• 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims description 7
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 6
• 125000005605 benzo group Chemical group 0.000 claims description 6
• 125000002619 bicyclic 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
• 125000001041 indolyl group Chemical group 0.000 claims description 6
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 6
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
• 125000002971 oxazolyl group Chemical group 0.000 claims description 6
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 6
• 229920006395 saturated elastomer Polymers 0.000 claims description 6
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 5
• 125000003342 alkenyl group Chemical group 0.000 claims description 5
• 125000002393 azetidinyl group Chemical group 0.000 claims description 5
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
• 125000002837 carbocyclic group Chemical group 0.000 claims description 5
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
• 125000005842 heteroatom Chemical group 0.000 claims description 5
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 5
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 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
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
• 125000002541 furyl group Chemical group 0.000 claims description 4
• 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 4
• 125000003566 oxetanyl group Chemical group 0.000 claims description 4
• 125000004043 oxo group Chemical group O=* 0.000 claims description 4
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 4
• CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 claims description 3
• 125000005955 1H-indazolyl 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
• 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 3
• 125000002632 imidazolidinyl group Chemical group 0.000 claims description 3
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 3
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 3
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000004306 triazinyl group Chemical group 0.000 claims description 3
• UUZJJNBYJDFQHL-UHFFFAOYSA-N 1,2,3-triazolidine Chemical compound C1CNNN1 UUZJJNBYJDFQHL-UHFFFAOYSA-N 0.000 claims description 2
• CZSRXHJVZUBEGW-UHFFFAOYSA-N 1,2-thiazolidine Chemical compound C1CNSC1 CZSRXHJVZUBEGW-UHFFFAOYSA-N 0.000 claims description 2
• OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims description 2
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 2
• WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims description 2
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 2
• DTHHUAXKOMWYBI-UHFFFAOYSA-N oxadiazolidine Chemical compound C1CONN1 DTHHUAXKOMWYBI-UHFFFAOYSA-N 0.000 claims description 2
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
• 125000000466 oxiranyl group Chemical group 0.000 claims description 2
• 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 2
• ZYXWYDDFNXBTFO-UHFFFAOYSA-N tetrazolidine Chemical compound C1NNNN1 ZYXWYDDFNXBTFO-UHFFFAOYSA-N 0.000 claims description 2
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
• RLTPJVKHGBFGQA-UHFFFAOYSA-N thiadiazolidine Chemical compound C1CSNN1 RLTPJVKHGBFGQA-UHFFFAOYSA-N 0.000 claims description 2
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
• 125000001425 triazolyl group Chemical group 0.000 claims description 2
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 42
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 30
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 29
• 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 25
• 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 20
• 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 19
• 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 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
• DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims 4
• 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 3
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 3
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 3
• WGCYRFWNGRMRJA-UHFFFAOYSA-N 1-ethylpiperazine Chemical compound CCN1CCNCC1 WGCYRFWNGRMRJA-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
• FDHKKONFMFSISP-UHFFFAOYSA-N 2-(2-methylimidazo[1,2-a]pyridin-6-yl)-7-piperidin-4-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=CC2=NC(C)=CN2C=C1C(N=C1C=C2)=CC(=O)N1C=C2C1CCNCC1 FDHKKONFMFSISP-UHFFFAOYSA-N 0.000 claims 2
• 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 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
• 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
• SLAXPYIFNUFCHC-UHFFFAOYSA-N 2-(6-methylpyrazolo[1,5-a]pyrazin-2-yl)-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C2C=NC(C)=CN2N=C1C(N=C1C=C2)=CC(=O)N1C=C2N1CCNCC1 SLAXPYIFNUFCHC-UHFFFAOYSA-N 0.000 claims 2
• VFMCUTPRJLZEEW-UHFFFAOYSA-N 4h-pyrido[1,2-a]pyrimidine Chemical compound C1=CC=CN2CC=CN=C21 VFMCUTPRJLZEEW-UHFFFAOYSA-N 0.000 claims 2
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims 2
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 2
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
• 125000006308 propyl amino group Chemical group 0.000 claims 2
• DNPOBJJJVSVMRF-UHFFFAOYSA-N 2-(1,7-dimethylindazol-5-yl)-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C=1C=2C=NN(C)C=2C(C)=CC=1C(N=C1C=C2)=CC(=O)N1C=C2N1CCNCC1 DNPOBJJJVSVMRF-UHFFFAOYSA-N 0.000 claims 1
• YXBPUSVLQVUDIN-UHFFFAOYSA-N 2-(1,7-dimethylindazol-5-yl)-7-piperidin-4-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C=1C=2C=NN(C)C=2C(C)=CC=1C(N=C1C=C2)=CC(=O)N1C=C2C1CCNCC1 YXBPUSVLQVUDIN-UHFFFAOYSA-N 0.000 claims 1
• YCHNCDXYQQTKAD-UHFFFAOYSA-N 2-(1-methylindazol-5-yl)-7-(1,2,3,6-tetrahydropyridin-4-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C=1C=C2N(C)N=CC2=CC=1C(N=C1C=C2)=CC(=O)N1C=C2C1=CCNCC1 YCHNCDXYQQTKAD-UHFFFAOYSA-N 0.000 claims 1
• OFLROASHFWNJAF-UHFFFAOYSA-N 2-(1-methylindazol-5-yl)-7-(1-methylpiperidin-4-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(C)CCC1C1=CN2C(=O)C=C(C=3C=C4C=NN(C)C4=CC=3)N=C2C=C1 OFLROASHFWNJAF-UHFFFAOYSA-N 0.000 claims 1
• OIEODKLCQKICSR-UHFFFAOYSA-N 2-(1-methylindazol-5-yl)-7-(4-methylpiperazin-1-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(C)CCN1C1=CN2C(=O)C=C(C=3C=C4C=NN(C)C4=CC=3)N=C2C=C1 OIEODKLCQKICSR-UHFFFAOYSA-N 0.000 claims 1
• QBRNCBNTRPRWCD-UHFFFAOYSA-N 2-(1-methylindazol-5-yl)-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C=1C=C2N(C)N=CC2=CC=1C(N=C1C=C2)=CC(=O)N1C=C2N1CCNCC1 QBRNCBNTRPRWCD-UHFFFAOYSA-N 0.000 claims 1
• NDUSIHOSIIHOHQ-UHFFFAOYSA-N 2-(1-methylindazol-5-yl)-7-piperidin-4-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C=1C=C2N(C)N=CC2=CC=1C(N=C1C=C2)=CC(=O)N1C=C2C1CCNCC1 NDUSIHOSIIHOHQ-UHFFFAOYSA-N 0.000 claims 1
• PALSGIBUTLGLFO-UHFFFAOYSA-N 2-(1-methylpyrazol-4-yl)-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=NN(C)C=C1C1=CC(=O)N(C=C(C=C2)N3CCNCC3)C2=N1 PALSGIBUTLGLFO-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
• VMNMYDOKZSGHTP-UHFFFAOYSA-N 2-(1h-indol-6-yl)-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C=1N2C(=O)C=C(C=3C=C4NC=CC4=CC=3)N=C2C=CC=1N1CCNCC1 VMNMYDOKZSGHTP-UHFFFAOYSA-N 0.000 claims 1
• SULOUUDHFLVZLW-UHFFFAOYSA-N 2-(2,3-dimethylimidazo[1,2-a]pyridin-6-yl)-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C=1N2C(C)=C(C)N=C2C=CC=1C(N=C1C=C2)=CC(=O)N1C=C2N1CCNCC1 SULOUUDHFLVZLW-UHFFFAOYSA-N 0.000 claims 1
• REVJKKNKCZBLOQ-UHFFFAOYSA-N 2-(2,7-dimethylindazol-5-yl)-7-(1-ethylpiperidin-4-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(CC)CCC1C1=CN2C(=O)C=C(C3=CC4=CN(C)N=C4C(C)=C3)N=C2C=C1 REVJKKNKCZBLOQ-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
• BPNJIDDZIZJYIH-UHFFFAOYSA-N 2-(2,7-dimethylindazol-5-yl)-7-(4-methylpiperazin-1-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(C)CCN1C1=CN2C(=O)C=C(C3=CC4=CN(C)N=C4C(C)=C3)N=C2C=C1 BPNJIDDZIZJYIH-UHFFFAOYSA-N 0.000 claims 1
• PNMVXXPKWDWUIC-UHFFFAOYSA-N 2-(2,7-dimethylindazol-5-yl)-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C=1C2=CN(C)N=C2C(C)=CC=1C(N=C1C=C2)=CC(=O)N1C=C2N1CCNCC1 PNMVXXPKWDWUIC-UHFFFAOYSA-N 0.000 claims 1
• UEXQDDNAEPVMHC-UHFFFAOYSA-N 2-(2,7-dimethylindazol-5-yl)-7-piperidin-4-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C=1C2=CN(C)N=C2C(C)=CC=1C(N=C1C=C2)=CC(=O)N1C=C2C1CCNCC1 UEXQDDNAEPVMHC-UHFFFAOYSA-N 0.000 claims 1
• QVBZQYHLZGOLKW-UHFFFAOYSA-N 2-(2-ethyl-1,3-benzoxazol-6-yl)-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C2OC(CC)=NC2=CC=C1C(N=C1C=C2)=CC(=O)N1C=C2N1CCNCC1 QVBZQYHLZGOLKW-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
• KLPKGCBAANJRGL-UHFFFAOYSA-N 2-(2-methyl-1,3-benzothiazol-5-yl)-7-(4-methylpiperazin-1-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(C)CCN1C1=CN2C(=O)C=C(C=3C=C4N=C(C)SC4=CC=3)N=C2C=C1 KLPKGCBAANJRGL-UHFFFAOYSA-N 0.000 claims 1
• GCQUXVHGFYDUQN-UHFFFAOYSA-N 2-(2-methyl-1,3-benzothiazol-5-yl)-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C=1C=C2SC(C)=NC2=CC=1C(N=C1C=C2)=CC(=O)N1C=C2N1CCNCC1 GCQUXVHGFYDUQN-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
• IBYKBQHLBILGGZ-UHFFFAOYSA-N 2-(2-methyl-1,3-benzothiazol-6-yl)-7-(1-methylpiperidin-4-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(C)CCC1C1=CN2C(=O)C=C(C=3C=C4SC(C)=NC4=CC=3)N=C2C=C1 IBYKBQHLBILGGZ-UHFFFAOYSA-N 0.000 claims 1
• MTWPUCLOKHAHPN-UHFFFAOYSA-N 2-(2-methyl-1,3-benzothiazol-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=C4SC(C)=NC4=CC=3)N=C2C=C1 MTWPUCLOKHAHPN-UHFFFAOYSA-N 0.000 claims 1
• XDIALJXYYNVFHY-UHFFFAOYSA-N 2-(2-methyl-1,3-benzothiazol-6-yl)-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C2SC(C)=NC2=CC=C1C(N=C1C=C2)=CC(=O)N1C=C2N1CCNCC1 XDIALJXYYNVFHY-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
• WBRJOPVYWAPMFR-UHFFFAOYSA-N 2-(2-methyl-1,3-benzothiazol-6-yl)-7-piperidin-4-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C2SC(C)=NC2=CC=C1C(N=C1C=C2)=CC(=O)N1C=C2C1CCNCC1 WBRJOPVYWAPMFR-UHFFFAOYSA-N 0.000 claims 1
• SMZYOSDVJFFEES-UHFFFAOYSA-N 2-(2-methyl-1,3-benzoxazol-5-yl)-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C=1C=C2OC(C)=NC2=CC=1C(N=C1C=C2)=CC(=O)N1C=C2N1CCNCC1 SMZYOSDVJFFEES-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
• LQZHLQQZRZUDQR-UHFFFAOYSA-N 2-(2-methyl-3h-benzimidazol-5-yl)-7-(4-methylpiperazin-1-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(C)CCN1C1=CN2C(=O)C=C(C=3C=C4NC(C)=NC4=CC=3)N=C2C=C1 LQZHLQQZRZUDQR-UHFFFAOYSA-N 0.000 claims 1
• STBQDINWEFFVNY-UHFFFAOYSA-N 2-(2-methylimidazo[1,2-a]pyridin-6-yl)-7-(1-propylpiperidin-4-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(CCC)CCC1C1=CN2C(=O)C=C(C3=CN4C=C(C)N=C4C=C3)N=C2C=C1 STBQDINWEFFVNY-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
• 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
• BXLXSLNLMZSTCS-UHFFFAOYSA-N 2-(2-methylindazol-5-yl)-7-(1,2,3,6-tetrahydropyridin-4-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=CC2=NN(C)C=C2C=C1C(N=C1C=C2)=CC(=O)N1C=C2C1=CCNCC1 BXLXSLNLMZSTCS-UHFFFAOYSA-N 0.000 claims 1
• AJIWYWAXZKGDDP-UHFFFAOYSA-N 2-(2-methylindazol-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=C3)N=C2C=C1 AJIWYWAXZKGDDP-UHFFFAOYSA-N 0.000 claims 1
• UCQHRGSESUKHMK-UHFFFAOYSA-N 2-(2-methylindazol-5-yl)-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=CC2=NN(C)C=C2C=C1C(N=C1C=C2)=CC(=O)N1C=C2N1CCNCC1 UCQHRGSESUKHMK-UHFFFAOYSA-N 0.000 claims 1
• CVLSQAZYSNXZSM-UHFFFAOYSA-N 2-(2-methylindazol-5-yl)-7-piperidin-4-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=CC2=NN(C)C=C2C=C1C(N=C1C=C2)=CC(=O)N1C=C2C1CCNCC1 CVLSQAZYSNXZSM-UHFFFAOYSA-N 0.000 claims 1
• XAQKAHOEQHLDEV-UHFFFAOYSA-N 2-(4,5-dimethoxypyridin-2-yl)-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C(OC)C(OC)=CN=C1C1=CC(=O)N(C=C(C=C2)N3CCNCC3)C2=N1 XAQKAHOEQHLDEV-UHFFFAOYSA-N 0.000 claims 1
• RLCIAKBVBACJOD-UHFFFAOYSA-N 2-(4,6-dimethylpyrazolo[1,5-a]pyrazin-2-yl)-7-(1-ethyl-3,6-dihydro-2h-pyridin-4-yl)-9-methylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1N(CC)CCC(C2=CN3C(=O)C=C(N=C3C(C)=C2)C2=NN3C=C(C)N=C(C)C3=C2)=C1 RLCIAKBVBACJOD-UHFFFAOYSA-N 0.000 claims 1
• VSLHYXCWTJCRJE-UHFFFAOYSA-N 2-(4,6-dimethylpyrazolo[1,5-a]pyrazin-2-yl)-7-[4-(2-hydroxyethylamino)-4-methylpiperidin-1-yl]pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C2C(C)=NC(C)=CN2N=C1C(N=C1C=C2)=CC(=O)N1C=C2N1CCC(C)(NCCO)CC1 VSLHYXCWTJCRJE-UHFFFAOYSA-N 0.000 claims 1
• XKPRICSCPQHOET-UHFFFAOYSA-N 2-(4,6-dimethylpyrazolo[1,5-a]pyrazin-2-yl)-7-[4-(2-hydroxyethylamino)piperidin-1-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=C2N1CCC(NCCO)CC1 XKPRICSCPQHOET-UHFFFAOYSA-N 0.000 claims 1
• XNPWDUOAVQKZCO-UHFFFAOYSA-N 2-(4,6-dimethylpyrazolo[1,5-a]pyrazin-2-yl)-7-[4-[2-hydroxyethyl(methyl)amino]piperidin-1-yl]-9-methylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1CC(N(CCO)C)CCN1C1=CN2C(=O)C=C(C3=NN4C=C(C)N=C(C)C4=C3)N=C2C(C)=C1 XNPWDUOAVQKZCO-UHFFFAOYSA-N 0.000 claims 1
• TUDSFAOBSUZNRX-UHFFFAOYSA-N 2-(4-ethyl-6-methylpyrazolo[1,5-a]pyrazin-2-yl)-7-(2,2,6,6-tetramethyl-1,3-dihydropyridin-4-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C2C(CC)=NC(C)=CN2N=C1C(N=C1C=C2)=CC(=O)N1C=C2C1=CC(C)(C)NC(C)(C)C1 TUDSFAOBSUZNRX-UHFFFAOYSA-N 0.000 claims 1
• WMGIQXYMZKSCGJ-UHFFFAOYSA-N 2-(4-fluoro-2-methyl-1,3-benzoxazol-6-yl)-7-(4-propylpiperazin-1-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(CCC)CCN1C1=CN2C(=O)C=C(C=3C=C4OC(C)=NC4=C(F)C=3)N=C2C=C1 WMGIQXYMZKSCGJ-UHFFFAOYSA-N 0.000 claims 1
• 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
• FSHWOSSUZXYOIJ-UHFFFAOYSA-N 2-(4-methyl-1,3-thiazol-2-yl)-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound CC1=CSC(C=2N=C3C=CC(=CN3C(=O)C=2)N2CCNCC2)=N1 FSHWOSSUZXYOIJ-UHFFFAOYSA-N 0.000 claims 1
• ZTIAVYUOJXJYMU-UHFFFAOYSA-N 2-(4-methylimidazol-1-yl)-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=NC(C)=CN1C1=CC(=O)N(C=C(C=C2)N3CCNCC3)C2=N1 ZTIAVYUOJXJYMU-UHFFFAOYSA-N 0.000 claims 1
• BGMCWVPTRAQUCE-UHFFFAOYSA-N 2-(5,7-dimethylfuro[2,3-c]pyridin-2-yl)-7-(4-ethylpiperazin-1-yl)pyrido[1,2-a]pyrimidin-4-one Chemical compound C1CN(CC)CCN1C1=CN2C(=O)C=C(C=3OC4=C(C)N=C(C)C=C4C=3)N=C2C=C1 BGMCWVPTRAQUCE-UHFFFAOYSA-N 0.000 claims 1
• DPKMIGHNWPEEHP-UHFFFAOYSA-N 2-(5,7-dimethylfuro[2,3-c]pyridin-2-yl)-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound O1C=2C(C)=NC(C)=CC=2C=C1C(N=C1C=C2)=CC(=O)N1C=C2N1CCNCC1 DPKMIGHNWPEEHP-UHFFFAOYSA-N 0.000 claims 1
• SQMDAWOZIWGFAJ-UHFFFAOYSA-N 2-(5-chloro-6-methoxypyridin-3-yl)-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C(Cl)C(OC)=NC=C1C1=CC(=O)N(C=C(C=C2)N3CCNCC3)C2=N1 SQMDAWOZIWGFAJ-UHFFFAOYSA-N 0.000 claims 1
• GCXUQWVITKDCET-UHFFFAOYSA-N 2-(5-chloropyridin-3-yl)-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound ClC1=CN=CC(C=2N=C3C=CC(=CN3C(=O)C=2)N2CCNCC2)=C1 GCXUQWVITKDCET-UHFFFAOYSA-N 0.000 claims 1
• JIKCPPWCTGKHNK-UHFFFAOYSA-N 2-(5-fluoro-6-methoxypyridin-3-yl)-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C(F)C(OC)=NC=C1C1=CC(=O)N(C=C(C=C2)N3CCNCC3)C2=N1 JIKCPPWCTGKHNK-UHFFFAOYSA-N 0.000 claims 1
• LNFJYJHAKGLNLI-UHFFFAOYSA-N 2-(5-fluoropyridin-3-yl)-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound FC1=CN=CC(C=2N=C3C=CC(=CN3C(=O)C=2)N2CCNCC2)=C1 LNFJYJHAKGLNLI-UHFFFAOYSA-N 0.000 claims 1
• VOUWDRYIBSKWPK-UHFFFAOYSA-N 2-(5-methoxypyridin-3-yl)-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound COC1=CN=CC(C=2N=C3C=CC(=CN3C(=O)C=2)N2CCNCC2)=C1 VOUWDRYIBSKWPK-UHFFFAOYSA-N 0.000 claims 1
• TUYAYLPCPVPDRJ-UHFFFAOYSA-N 2-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound N1=C2C(C)=NC(C)=CN2C=C1C(N=C1C=C2)=CC(=O)N1C=C2N1CCNCC1 TUYAYLPCPVPDRJ-UHFFFAOYSA-N 0.000 claims 1
• RIBJIKHFCCWECK-UHFFFAOYSA-N 2-(6-methoxypyridin-2-yl)-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound COC1=CC=CC(C=2N=C3C=CC(=CN3C(=O)C=2)N2CCNCC2)=N1 RIBJIKHFCCWECK-UHFFFAOYSA-N 0.000 claims 1
• LKYJFLMFWXVTQY-UHFFFAOYSA-N 2-(6-methoxypyridin-3-yl)-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=NC(OC)=CC=C1C1=CC(=O)N(C=C(C=C2)N3CCNCC3)C2=N1 LKYJFLMFWXVTQY-UHFFFAOYSA-N 0.000 claims 1
• LRUVWYLKRMAYPJ-UHFFFAOYSA-N 2-(6-methyl-4-propylpyrazolo[1,5-a]pyrazin-2-yl)-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C2C(CCC)=NC(C)=CN2N=C1C(N=C1C=C2)=CC(=O)N1C=C2N1CCNCC1 LRUVWYLKRMAYPJ-UHFFFAOYSA-N 0.000 claims 1
• RBDDVGLFLMOZBZ-UHFFFAOYSA-N 2-(6-methylimidazo[1,2-a]pyrazin-2-yl)-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound N1=C2C=NC(C)=CN2C=C1C(N=C1C=C2)=CC(=O)N1C=C2N1CCNCC1 RBDDVGLFLMOZBZ-UHFFFAOYSA-N 0.000 claims 1
• QNVBVNUNRFVOIF-UHFFFAOYSA-N 2-(6-methylimidazo[1,2-a]pyridin-2-yl)-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C=1N2C=C(C)C=CC2=NC=1C(N=C1C=C2)=CC(=O)N1C=C2N1CCNCC1 QNVBVNUNRFVOIF-UHFFFAOYSA-N 0.000 claims 1
• 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
• VVFNYAGQIFOJLF-UHFFFAOYSA-N 2-imidazo[1,2-a]pyridin-6-yl-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C=1N2C(=O)C=C(C3=CN4C=CN=C4C=C3)N=C2C=CC=1N1CCNCC1 VVFNYAGQIFOJLF-UHFFFAOYSA-N 0.000 claims 1
• FHVWJIJXRFRWCJ-UHFFFAOYSA-N 2-imidazo[1,2-a]pyridin-7-yl-7-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound C=1N2C(=O)C=C(C3=CC4=NC=CN4C=C3)N=C2C=CC=1N1CCNCC1 FHVWJIJXRFRWCJ-UHFFFAOYSA-N 0.000 claims 1
• YMZVMQZXOZLAIX-UHFFFAOYSA-N 2-piperazin-1-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound N1=C2C=CC=CN2C(=O)C=C1N1CCNCC1 YMZVMQZXOZLAIX-UHFFFAOYSA-N 0.000 claims 1
• PUQIQRMJPOVWNG-UHFFFAOYSA-N 2-piperidin-4-ylpyrido[1,2-a]pyrimidin-4-one Chemical compound N1=C2C=CC=CN2C(=O)C=C1C1CCNCC1 PUQIQRMJPOVWNG-UHFFFAOYSA-N 0.000 claims 1
• LDQQHJUCGWMZKB-UHFFFAOYSA-N 7-(1,4-diazepan-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=C2N1CCCNCC1 LDQQHJUCGWMZKB-UHFFFAOYSA-N 0.000 claims 1
• PCVMROPDDQTTKD-UHFFFAOYSA-N 7-(1,4-diazepan-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=C2N1CCCNCC1 PCVMROPDDQTTKD-UHFFFAOYSA-N 0.000 claims 1
• GLDFDNKWWTYFRS-UHFFFAOYSA-N 7-(1,4-diazepan-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=C2N1CCCNCC1 GLDFDNKWWTYFRS-UHFFFAOYSA-N 0.000 claims 1
• 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
• JBUAQQHFSPAZEQ-UHFFFAOYSA-N 7-(1-cyclopropyl-3,6-dihydro-2h-pyridin-4-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=C2C(CC1)=CCN1C1CC1 JBUAQQHFSPAZEQ-UHFFFAOYSA-N 0.000 claims 1
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