JP2005504810A5 - - Google Patents
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- Publication number
- JP2005504810A5 JP2005504810A5 JP2003530704A JP2003530704A JP2005504810A5 JP 2005504810 A5 JP2005504810 A5 JP 2005504810A5 JP 2003530704 A JP2003530704 A JP 2003530704A JP 2003530704 A JP2003530704 A JP 2003530704A JP 2005504810 A5 JP2005504810 A5 JP 2005504810A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- pyrimido
- tetrahydro
- ethyl
- pyrimidin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 hydroxyiminomethylene group Chemical group 0.000 description 20
- 125000000217 alkyl group Chemical group 0.000 description 11
- 239000008194 pharmaceutical composition Substances 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 239000012453 solvate Substances 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 239000003814 drug Substances 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 150000008318 pyrimidones Chemical class 0.000 description 6
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 5
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 102000019058 Glycogen Synthase Kinase 3 beta Human genes 0.000 description 4
- 108010051975 Glycogen Synthase Kinase 3 beta Proteins 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 3
- PNHZWBOOHNVDGO-UHFFFAOYSA-N 9-(2-hydroxy-2-phenylpropyl)-7,7-dimethyl-2-pyridin-4-yl-6,8-dihydropyrimido[1,2-a]pyrimidin-4-one Chemical compound C=1C=CC=CC=1C(O)(C)CN1CC(C)(C)CN(C(C=2)=O)C1=NC=2C1=CC=NC=C1 PNHZWBOOHNVDGO-UHFFFAOYSA-N 0.000 description 3
- VNHNILNXYRRAKL-XCWJXAQQSA-N 9-[(2s)-2-hydroxy-2-phenylethyl]-8-methyl-2-pyridin-4-yl-7,8-dihydro-6h-pyrimido[1,2-a]pyrimidin-4-one Chemical compound C([C@@H](O)C=1C=CC=CC=1)N1C(C)CCN(C(C=2)=O)C1=NC=2C1=CC=NC=C1 VNHNILNXYRRAKL-XCWJXAQQSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical group C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 2
- FZDHCRBEMRHGEU-UHFFFAOYSA-N 3-fluoro-9-(2-hydroxy-2-phenylpropyl)-7,7-dimethyl-2-pyridin-4-yl-6,8-dihydropyrimido[1,2-a]pyrimidin-4-one Chemical compound C=1C=CC=CC=1C(O)(C)CN1CC(C)(C)CN(C(C=2F)=O)C1=NC=2C1=CC=NC=C1 FZDHCRBEMRHGEU-UHFFFAOYSA-N 0.000 description 2
- VNZBIFYIYRGIGE-KRWDZBQOSA-N 3-fluoro-9-[(2r)-2-methoxy-2-phenylethyl]-2-pyridin-4-yl-7,8-dihydro-6h-pyrimido[1,2-a]pyrimidin-4-one Chemical compound C([C@H](OC)C=1C=CC=CC=1)N1CCCN(C(C=2F)=O)C1=NC=2C1=CC=NC=C1 VNZBIFYIYRGIGE-KRWDZBQOSA-N 0.000 description 2
- MVRWSFBOEQCLFY-UHFFFAOYSA-N 9-(2,3-dihydroxypropyl)-7,7-dimethyl-2-pyridin-4-yl-6,8-dihydropyrimido[1,2-a]pyrimidin-4-one Chemical compound C=1C(=O)N2CC(C)(C)CN(CC(O)CO)C2=NC=1C1=CC=NC=C1 MVRWSFBOEQCLFY-UHFFFAOYSA-N 0.000 description 2
- DGCAXSVJCHKYKL-UHFFFAOYSA-N 9-(2-hydroxy-2,2-diphenylethyl)-7,7-dimethyl-2-pyridin-4-yl-6,8-dihydropyrimido[1,2-a]pyrimidin-4-one Chemical compound C12=NC(C=3C=CN=CC=3)=CC(=O)N2CC(C)(C)CN1CC(O)(C=1C=CC=CC=1)C1=CC=CC=C1 DGCAXSVJCHKYKL-UHFFFAOYSA-N 0.000 description 2
- VUBGURPABXJCEQ-UHFFFAOYSA-N 9-(2-hydroxy-2-phenylethyl)-7,7-dimethyl-2-pyridin-4-yl-6,8-dihydropyrimido[1,2-a]pyrimidin-4-one Chemical compound C12=NC(C=3C=CN=CC=3)=CC(=O)N2CC(C)(C)CN1CC(O)C1=CC=CC=C1 VUBGURPABXJCEQ-UHFFFAOYSA-N 0.000 description 2
- CLGGXXZHSXCCCD-UHFFFAOYSA-N 9-(2-hydroxy-2-phenylethyl)-7-methyl-2-pyridin-4-yl-7,8-dihydro-6h-pyrimido[1,2-a]pyrimidin-4-one Chemical compound C12=NC(C=3C=CN=CC=3)=CC(=O)N2CC(C)CN1CC(O)C1=CC=CC=C1 CLGGXXZHSXCCCD-UHFFFAOYSA-N 0.000 description 2
- 101150053721 Cdk5 gene Proteins 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 2
- 125000004658 aryl carbonyl amino group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 2
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 230000004770 neurodegeneration Effects 0.000 description 2
- 208000015122 neurodegenerative disease Diseases 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- SOQCSKKKURIFCX-UHFFFAOYSA-N pyrimido[1,2-a]pyrimidin-6-one Chemical compound N1=CC=CN2C(=O)C=CN=C21 SOQCSKKKURIFCX-UHFFFAOYSA-N 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000003375 sulfoxide group Chemical group 0.000 description 2
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical group C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 1
- GCKUUGPSDVVKQF-UHFFFAOYSA-N 1-(2-hydroxy-2-phenylethyl)-2,2-dimethyl-7-pyridin-4-yl-3h-imidazo[1,2-a]pyrimidin-5-one Chemical compound C=1C=CC=CC=1C(O)CN1C(C)(C)CN(C(C=2)=O)C1=NC=2C1=CC=NC=C1 GCKUUGPSDVVKQF-UHFFFAOYSA-N 0.000 description 1
- STXSSZGQOQDZAX-LJQANCHMSA-N 1-[(2s)-2-(2,4-dichlorophenyl)-2-hydroxyethyl]-2,2-dimethyl-8-pyridin-4-yl-3,4-dihydropyrimido[1,2-a]pyrimidin-6-one Chemical compound C([C@@H](O)C=1C(=CC(Cl)=CC=1)Cl)N1C(C)(C)CCN(C(C=2)=O)C1=NC=2C1=CC=NC=C1 STXSSZGQOQDZAX-LJQANCHMSA-N 0.000 description 1
- AZPXHIKRAWMQPU-LJQANCHMSA-N 1-[(2s)-2-(3,4-dichlorophenyl)-2-hydroxyethyl]-2,2-dimethyl-8-pyridin-4-yl-3,4-dihydropyrimido[1,2-a]pyrimidin-6-one Chemical compound C([C@@H](O)C=1C=C(Cl)C(Cl)=CC=1)N1C(C)(C)CCN(C(C=2)=O)C1=NC=2C1=CC=NC=C1 AZPXHIKRAWMQPU-LJQANCHMSA-N 0.000 description 1
- GLMIQONSAMBPKR-LJQANCHMSA-N 1-[(2s)-2-(3-bromophenyl)-2-hydroxyethyl]-2,2-dimethyl-8-pyridin-4-yl-3,4-dihydropyrimido[1,2-a]pyrimidin-6-one Chemical compound C([C@@H](O)C=1C=C(Br)C=CC=1)N1C(C)(C)CCN(C(C=2)=O)C1=NC=2C1=CC=NC=C1 GLMIQONSAMBPKR-LJQANCHMSA-N 0.000 description 1
- CVHRUWUPYMNLQV-LJQANCHMSA-N 1-[(2s)-2-(3-fluorophenyl)-2-hydroxyethyl]-2,2-dimethyl-8-pyridin-4-yl-3,4-dihydropyrimido[1,2-a]pyrimidin-6-one Chemical compound C([C@@H](O)C=1C=C(F)C=CC=1)N1C(C)(C)CCN(C(C=2)=O)C1=NC=2C1=CC=NC=C1 CVHRUWUPYMNLQV-LJQANCHMSA-N 0.000 description 1
- AHMTVEZDCPQIOF-LJQANCHMSA-N 1-[(2s)-2-(4-chlorophenyl)-2-hydroxyethyl]-2,2-dimethyl-8-pyridin-4-yl-3,4-dihydropyrimido[1,2-a]pyrimidin-6-one Chemical compound C([C@@H](O)C=1C=CC(Cl)=CC=1)N1C(C)(C)CCN(C(C=2)=O)C1=NC=2C1=CC=NC=C1 AHMTVEZDCPQIOF-LJQANCHMSA-N 0.000 description 1
- YTNAXSLQYJSLNO-LJQANCHMSA-N 1-[(2s)-2-(4-fluorophenyl)-2-hydroxyethyl]-2,2-dimethyl-8-pyridin-4-yl-3,4-dihydropyrimido[1,2-a]pyrimidin-6-one Chemical compound C([C@@H](O)C=1C=CC(F)=CC=1)N1C(C)(C)CCN(C(C=2)=O)C1=NC=2C1=CC=NC=C1 YTNAXSLQYJSLNO-LJQANCHMSA-N 0.000 description 1
- WQPXEAJCRZYRBN-HXUWFJFHSA-N 1-[(2s)-2-hydroxy-2-(3-methoxyphenyl)ethyl]-2,2-dimethyl-8-pyridin-4-yl-3,4-dihydropyrimido[1,2-a]pyrimidin-6-one Chemical compound COC1=CC=CC([C@H](O)CN2C(CCN3C(=O)C=C(N=C32)C=2C=CN=CC=2)(C)C)=C1 WQPXEAJCRZYRBN-HXUWFJFHSA-N 0.000 description 1
- ZNWZLYFCWYHOON-HXUWFJFHSA-N 1-[(2s)-2-hydroxy-2-(4-methylphenyl)ethyl]-2,2-dimethyl-8-pyridin-4-yl-3,4-dihydropyrimido[1,2-a]pyrimidin-6-one Chemical compound C1=CC(C)=CC=C1[C@H](O)CN1C(C)(C)CCN2C(=O)C=C(C=3C=CN=CC=3)N=C21 ZNWZLYFCWYHOON-HXUWFJFHSA-N 0.000 description 1
- QYBOQUKCLGAHOV-RUZDIDTESA-N 1-[(2s)-2-hydroxy-2-(4-phenylphenyl)ethyl]-2,2-dimethyl-8-pyridin-4-yl-3,4-dihydropyrimido[1,2-a]pyrimidin-6-one Chemical compound C([C@@H](O)C=1C=CC(=CC=1)C=1C=CC=CC=1)N1C(C)(C)CCN(C(C=2)=O)C1=NC=2C1=CC=NC=C1 QYBOQUKCLGAHOV-RUZDIDTESA-N 0.000 description 1
- KSDJBRKKADSAEJ-LJQANCHMSA-N 1-[(2s)-2-hydroxy-2-phenylethyl]-2,2-dimethyl-8-pyridin-4-yl-3,4-dihydropyrimido[1,2-a]pyrimidin-6-one Chemical compound C([C@@H](O)C=1C=CC=CC=1)N1C(C)(C)CCN(C(C=2)=O)C1=NC=2C1=CC=NC=C1 KSDJBRKKADSAEJ-LJQANCHMSA-N 0.000 description 1
- JRPRRFDQCPRIDD-UHFFFAOYSA-N 1-[1-(7-methoxy-1,3-benzodioxol-5-yl)-1-oxopropan-2-yl]-2,2-dimethyl-7-pyridin-4-yl-3h-imidazo[1,2-a]pyrimidin-5-one Chemical compound C=1C=2OCOC=2C(OC)=CC=1C(=O)C(C)N(C(CN1C(=O)C=2)(C)C)C1=NC=2C1=CC=NC=C1 JRPRRFDQCPRIDD-UHFFFAOYSA-N 0.000 description 1
- AZPXHIKRAWMQPU-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenyl)-2-hydroxyethyl]-2,2-dimethyl-8-pyridin-4-yl-3,4-dihydropyrimido[1,2-a]pyrimidin-6-one Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(O)CN1C(C)(C)CCN(C(C=2)=O)C1=NC=2C1=CC=NC=C1 AZPXHIKRAWMQPU-UHFFFAOYSA-N 0.000 description 1
- GQRHZFVCOMJVOU-UHFFFAOYSA-N 1-[2-(3-bromophenyl)-2-oxoethyl]-2,2-dimethyl-8-pyridin-4-yl-3,4-dihydropyrimido[1,2-a]pyrimidin-6-one Chemical compound C=1C=CC(Br)=CC=1C(=O)CN1C(C)(C)CCN(C(C=2)=O)C1=NC=2C1=CC=NC=C1 GQRHZFVCOMJVOU-UHFFFAOYSA-N 0.000 description 1
- AOCMWFYPWGCXGQ-UHFFFAOYSA-N 1-[2-(3-fluorophenyl)-2-oxoethyl]-2,2-dimethyl-8-pyridin-4-yl-3,4-dihydropyrimido[1,2-a]pyrimidin-6-one Chemical compound C=1C=CC(F)=CC=1C(=O)CN1C(C)(C)CCN(C(C=2)=O)C1=NC=2C1=CC=NC=C1 AOCMWFYPWGCXGQ-UHFFFAOYSA-N 0.000 description 1
- RWDKFQPGXYHJQT-UHFFFAOYSA-N 1-[2-(3-methoxyphenyl)-2-oxoethyl]-2,2-dimethyl-7-pyridin-4-yl-3h-imidazo[1,2-a]pyrimidin-5-one Chemical compound COC1=CC=CC(C(=O)CN2C(CN3C(=O)C=C(N=C32)C=2C=CN=CC=2)(C)C)=C1 RWDKFQPGXYHJQT-UHFFFAOYSA-N 0.000 description 1
- IHMJQMBTNMPCAE-UHFFFAOYSA-N 1-[2-(3-methoxyphenyl)-2-oxoethyl]-2,2-dimethyl-8-pyridin-4-yl-3,4-dihydropyrimido[1,2-a]pyrimidin-6-one Chemical compound COC1=CC=CC(C(=O)CN2C(CCN3C(=O)C=C(N=C32)C=2C=CN=CC=2)(C)C)=C1 IHMJQMBTNMPCAE-UHFFFAOYSA-N 0.000 description 1
- AGNIHDIIYUFISY-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)-2-oxoethyl]-2,2-dimethyl-7-pyridin-4-yl-3h-imidazo[1,2-a]pyrimidin-5-one Chemical compound C=1C=C(Cl)C=CC=1C(=O)CN1C(C)(C)CN(C(C=2)=O)C1=NC=2C1=CC=NC=C1 AGNIHDIIYUFISY-UHFFFAOYSA-N 0.000 description 1
- STYSMRNYBVGWCB-UHFFFAOYSA-N 1-[2-(4-fluoro-2-methoxyphenyl)ethyl]-2,2-dimethyl-8-pyridin-4-yl-3,4-dihydropyrimido[1,2-a]pyrimidin-6-one Chemical compound COC1=CC(F)=CC=C1CCN1C(C)(C)CCN2C(=O)C=C(C=3C=CN=CC=3)N=C21 STYSMRNYBVGWCB-UHFFFAOYSA-N 0.000 description 1
- DEHUABWNDZALHV-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)-2-oxoethyl]-2,2-dimethyl-7-pyridin-4-yl-3h-imidazo[1,2-a]pyrimidin-5-one Chemical compound C=1C=C(F)C=CC=1C(=O)CN1C(C)(C)CN(C(C=2)=O)C1=NC=2C1=CC=NC=C1 DEHUABWNDZALHV-UHFFFAOYSA-N 0.000 description 1
- DTHWETGQWDYWJS-UHFFFAOYSA-N 1-[3-(2-fluorophenyl)propyl]-2,2-dimethyl-7-pyridin-4-yl-3h-imidazo[1,2-a]pyrimidin-5-one Chemical compound C=1C=CC=C(F)C=1CCCN1C(C)(C)CN(C(C=2)=O)C1=NC=2C1=CC=NC=C1 DTHWETGQWDYWJS-UHFFFAOYSA-N 0.000 description 1
- ZOCUUTDWFLKCDA-UHFFFAOYSA-N 2,2-dimethyl-1-(2-naphthalen-2-yl-2-oxoethyl)-7-pyridin-4-yl-3h-imidazo[1,2-a]pyrimidin-5-one Chemical compound C=1C=C2C=CC=CC2=CC=1C(=O)CN1C(C)(C)CN(C(C=2)=O)C1=NC=2C1=CC=NC=C1 ZOCUUTDWFLKCDA-UHFFFAOYSA-N 0.000 description 1
- DMNDGFMEMXFZJL-UHFFFAOYSA-N 2,2-dimethyl-1-(6-oxo-4-phenylcyclohexa-2,4-dien-1-yl)-7-pyridin-4-yl-3h-imidazo[1,2-a]pyrimidin-5-one Chemical compound C1=CC(C=2C=CC=CC=2)=CC(=O)C1N1C(C)(C)CN(C(C=2)=O)C1=NC=2C1=CC=NC=C1 DMNDGFMEMXFZJL-UHFFFAOYSA-N 0.000 description 1
- HZCFJXRUCLMQSC-UHFFFAOYSA-N 2,2-dimethyl-1-(naphthalen-1-ylmethyl)-8-pyridin-4-yl-3,4-dihydropyrimido[1,2-a]pyrimidin-6-one Chemical compound C=1C=CC2=CC=CC=C2C=1CN1C(C)(C)CCN(C(C=2)=O)C1=NC=2C1=CC=NC=C1 HZCFJXRUCLMQSC-UHFFFAOYSA-N 0.000 description 1
- BDIWMRJHLMZART-KRWDZBQOSA-N 2,2-dimethyl-1-[(2r)-2-phenylpropyl]-8-pyridin-4-yl-3,4-dihydropyrimido[1,2-a]pyrimidin-6-one Chemical compound C([C@H](C)C=1C=CC=CC=1)N(C(CCN1C(=O)C=2)(C)C)C1=NC=2C1=CC=NC=C1 BDIWMRJHLMZART-KRWDZBQOSA-N 0.000 description 1
- BDIWMRJHLMZART-QGZVFWFLSA-N 2,2-dimethyl-1-[(2s)-2-phenylpropyl]-8-pyridin-4-yl-3,4-dihydropyrimido[1,2-a]pyrimidin-6-one Chemical compound C([C@@H](C)C=1C=CC=CC=1)N(C(CCN1C(=O)C=2)(C)C)C1=NC=2C1=CC=NC=C1 BDIWMRJHLMZART-QGZVFWFLSA-N 0.000 description 1
- TZJIBXFNUKACEO-UHFFFAOYSA-N 2,2-dimethyl-1-[2-(4-methylphenyl)-2-oxoethyl]-7-pyridin-4-yl-3h-imidazo[1,2-a]pyrimidin-5-one Chemical compound C1=CC(C)=CC=C1C(=O)CN1C(C)(C)CN2C(=O)C=C(C=3C=CN=CC=3)N=C21 TZJIBXFNUKACEO-UHFFFAOYSA-N 0.000 description 1
- LNOAYBRKNOFTMC-UHFFFAOYSA-N 2,2-dimethyl-1-phenacyl-7-pyridin-4-yl-3h-imidazo[1,2-a]pyrimidin-5-one Chemical compound C=1C=CC=CC=1C(=O)CN1C(C)(C)CN(C(C=2)=O)C1=NC=2C1=CC=NC=C1 LNOAYBRKNOFTMC-UHFFFAOYSA-N 0.000 description 1
- MCUHBUUHPAZBNA-UHFFFAOYSA-N 2,2-dimethyl-1-phenacyl-8-pyridin-4-yl-3,4-dihydropyrimido[1,2-a]pyrimidin-6-one Chemical compound C=1C=CC=CC=1C(=O)CN1C(C)(C)CCN(C(C=2)=O)C1=NC=2C1=CC=NC=C1 MCUHBUUHPAZBNA-UHFFFAOYSA-N 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
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| EP02290489A EP1340761A1 (en) | 2002-02-28 | 2002-02-28 | Substituted 2-pyridinyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one and 7-pyridinyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)one derivatives |
| PCT/EP2002/011128 WO2003027116A2 (en) | 2001-09-21 | 2002-09-19 | Substituted 2-pyridinyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one and 7-pyridinyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1h)one derivatives |
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| TW201041580A (en) | 2001-09-27 | 2010-12-01 | Alcon Inc | Inhibitors of glycogen synthase kinase-3 (GSK-3) for treating glaucoma |
| EP1454909B1 (en) * | 2003-03-07 | 2008-08-20 | Sanofi Aventis | 8'-pyridinyl-dihydrospiro- (cycloalkyl) -pyrimido (1,2-a) pyrimidin-6-one and 8'-pyrimidinyl-dihydrospiro (cycloalkyl) -pyrimido (1,2-a) pyrimidin-6-one derivatives and their use against neurodegenerative diseases |
| EP1454900A1 (en) * | 2003-03-07 | 2004-09-08 | Sanofi-Synthelabo | Process for the preparation of pyridinyl and pyrimidinyl mono-fluorinated beta keto-esters |
| EP1557417B1 (en) * | 2003-12-19 | 2007-03-07 | Sanofi-Aventis | Substituted 8'-pyri(mi)dinyl-dihydrospiro-[cycloalkylamine]-pyrimido[1,2-a] pyrimidin-6-one derivatives |
| WO2005070932A2 (en) | 2004-01-22 | 2005-08-04 | Amgen Inc. | Substituted heterocyclic compounds and methods of use |
| EP2258358A3 (en) | 2005-08-26 | 2011-09-07 | Braincells, Inc. | Neurogenesis with acetylcholinesterase inhibitor |
| EP2275095A3 (en) | 2005-08-26 | 2011-08-17 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation |
| EP1940389A2 (en) | 2005-10-21 | 2008-07-09 | Braincells, Inc. | Modulation of neurogenesis by pde inhibition |
| AU2006308889A1 (en) | 2005-10-31 | 2007-05-10 | Braincells, Inc. | GABA receptor mediated modulation of neurogenesis |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| EP2382975A3 (en) | 2006-05-09 | 2012-02-29 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| US20100184806A1 (en) | 2006-09-19 | 2010-07-22 | Braincells, Inc. | Modulation of neurogenesis by ppar agents |
| CN101735211B (zh) * | 2008-11-04 | 2012-11-14 | 复旦大学 | 2,3-二氢[1,5]苯并噻氮杂*类化合物或其盐在制备GSK-3β抑制剂中的用途 |
| WO2010099217A1 (en) | 2009-02-25 | 2010-09-02 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
| FR2947550B1 (fr) * | 2009-07-02 | 2012-05-18 | Sanofi Aventis | Nouveaux derives de 2,3-dihydro-1h-imidazo{1,2-a}pyrimidin-5-one, leur preparation et leur utilisation pharmaceutique comme inhibiteurs de phosphorylation d'akt (pkb) |
| FR2947551B1 (fr) * | 2009-07-02 | 2012-05-18 | Sanofi Aventis | Nouveaux derives de 1,2,3,4-tetrahydro-pyrimido{1,2-a)pyrimidin-6-one, leur preparation et leur utilisation pharmaceutique comme inhibiteurs de phosphorylation d'akt (pkb) |
| CN102482286B (zh) * | 2009-07-02 | 2015-07-15 | 赛诺菲 | 新型1,2,3,4-四氢嘧啶并{1,2-a}嘧啶-6-酮衍生物、其制备以及其医药用途 |
| HUE034503T2 (en) | 2009-07-02 | 2018-02-28 | Sanofi Sa | 2,3-Dihydro-1-imidazo [1,2-a] pyrimidin-5-one derivatives, their preparation process and their use in medicine |
| DK2655375T3 (en) | 2010-12-23 | 2015-03-09 | Sanofi Sa | PYRIMIDINON DERIVATIVES, PREPARATION AND PHARMACEUTICAL USE THEREOF |
| FR2992314B1 (fr) | 2012-06-22 | 2015-10-16 | Sanofi Sa | Nouveaux derives de 2,3-dihydro-1h-imidazo{1,2-a}pyrimidin-5-one et 1,2,3,4-tetrahydro-pyrimido{1,2-a}pyrimidin-6-one comportant une morpholine substituee, leur preparation et leur utilisation pharmaceutique |
| CA2945263A1 (en) | 2014-04-09 | 2015-10-15 | Christopher Rudd | Use of gsk-3 inhibitors or activators which modulate pd-1 or t-bet expression to modulate t cell immunity |
| CN109836427B (zh) * | 2017-11-29 | 2022-04-15 | 暨南大学 | 嘧啶并嘧啶酮类化合物及其应用 |
| CN114957246B (zh) * | 2021-02-19 | 2025-11-11 | 苏州恩华生物医药科技有限公司 | 5,6,7,8-四氢吡啶并[4,3-d]嘧啶-4（3H）-酮衍生物及其应用 |
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| EP0948496A2 (en) * | 1996-12-05 | 1999-10-13 | Amgen inc. | Substituted pyrimidinone and pyridone compounds and methods of use |
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| AR023052A1 (es) * | 1998-09-25 | 2002-09-04 | Mitsuharu Yoshimura Milton | Derivados de pirimidona |
| JP2000264888A (ja) * | 1999-01-11 | 2000-09-26 | Sagami Chem Res Center | 双環性ピリミジン誘導体、それらの製造中間体及びそれらの製造方法、並びにそれらを有効成分とする除草剤 |
| BR0010652A (pt) * | 1999-03-22 | 2002-07-16 | Ortho Mcneil Pharm Inc | Processo de preparação de ácido [s-(r*,s*)]-beta-[[[1-[1-oxo-3-(4-piperidinil)propil]-3-piperi dinil]carbonil]amino]-3-piridinapropanóico e derivados |
| WO2001042224A1 (en) * | 1999-12-09 | 2001-06-14 | Mitsubishi Pharma Corporation | Carboxyamido derivatives |
| CN100335479C (zh) * | 1999-12-17 | 2007-09-05 | 希龙公司 | 糖元合成酶激酶3的双环抑制剂 |
| AR030587A1 (es) * | 2000-09-01 | 2003-08-27 | Sanofi Aventis | Derivados de 2-piridinil-6,7,8,9-tetrahidropirimido[1,2-a]pirimidin-4-ona y 7-piridinil-2,3-dihidroimidazo[1,2-a]pirimidin-5(1h)-ona |
| CA2457965C (en) * | 2001-09-21 | 2010-06-01 | Sanofi-Synthelabo | Substituted 2-pyridinyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one and 7-pyridinyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1h)one derivatives |
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2002
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2004
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2007
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2008
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2010
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