NZ531244A - Substituted 2-pyrimidinyl-6,7,8,9-tetrahydropyrimido[1,2-A]pyrimidin-4-one and 7-pyrimidinyl-2,3-dihydroimidazo [1,2-A]pyrimidin-5(1H)one derivatives for neurodegenerative disorders - Google Patents

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Publication number

NZ531244A

NZ531244A NZ531244A NZ53124402A NZ531244A NZ 531244 A NZ531244 A NZ 531244A NZ 531244 A NZ531244 A NZ 531244A NZ 53124402 A NZ53124402 A NZ 53124402A NZ 531244 A NZ531244 A NZ 531244A

Authority

NZ

New Zealand

Prior art keywords

pyrimidin

tetrahydro

pyrimido

ethyl

phenyl

Prior art date

2001-09-21

Links

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• Global Dossier
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• 208000015122 neurodegenerative disease Diseases 0.000 title claims description 17
• JOQYRATWFVJNPN-UHFFFAOYSA-N 2-pyrimidin-2-yl-1,6,7,8-tetrahydropyrimido[1,2-a]pyrimidin-4-one Chemical class N1=C2NCCCN2C(=O)C=C1C1=NC=CC=N1 JOQYRATWFVJNPN-UHFFFAOYSA-N 0.000 title 1
• BUOYBEPCJMUPNV-UHFFFAOYSA-N 7-pyrimidin-2-yl-3,8-dihydro-2h-imidazo[1,2-a]pyrimidin-5-one Chemical class N1=C2NCCN2C(=O)C=C1C1=NC=CC=N1 BUOYBEPCJMUPNV-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 73
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 46
• 101150053721 Cdk5 gene Proteins 0.000 claims abstract description 36
• 239000003814 drug Substances 0.000 claims abstract description 32
• 150000008318 pyrimidones Chemical class 0.000 claims abstract description 25
• 230000000694 effects Effects 0.000 claims abstract description 20
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 19
• 201000010099 disease Diseases 0.000 claims abstract description 18
• 230000002159 abnormal effect Effects 0.000 claims abstract description 14
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 8
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 7
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 6
• 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims abstract description 6
• 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims abstract description 6
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
• 125000001424 substituent group Chemical group 0.000 claims abstract description 5
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 5
• DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims description 110
• 239000000203 mixture Substances 0.000 claims description 65
• 150000003839 salts Chemical class 0.000 claims description 48
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 27
• -1 methylendioxy group Chemical group 0.000 claims description 27
• LCKCIHLNWFCXLK-UHFFFAOYSA-N 1,4,7,8-tetrahydropyrimido[1,2-a]pyrimidin-6-one Chemical compound N1C=CCN2C(=O)CCN=C21 LCKCIHLNWFCXLK-UHFFFAOYSA-N 0.000 claims description 23
• 238000000034 method Methods 0.000 claims description 23
• 239000004480 active ingredient Substances 0.000 claims description 19
• 238000002360 preparation method Methods 0.000 claims description 18
• 230000003449 preventive effect Effects 0.000 claims description 16
• SOQCSKKKURIFCX-UHFFFAOYSA-N pyrimido[1,2-a]pyrimidin-6-one Chemical compound N1=CC=CN2C(=O)C=CN=C21 SOQCSKKKURIFCX-UHFFFAOYSA-N 0.000 claims description 16
• 230000001225 therapeutic effect Effects 0.000 claims description 16
• 125000003545 alkoxy group Chemical group 0.000 claims description 15
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
• 125000005843 halogen group Chemical group 0.000 claims description 15
• 230000004770 neurodegeneration Effects 0.000 claims description 15
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
• 239000012453 solvate Substances 0.000 claims description 14
• 239000000126 substance Substances 0.000 claims description 14
• 239000011780 sodium chloride Substances 0.000 claims description 13
• 208000024827 Alzheimer disease Diseases 0.000 claims description 12
• 208000014674 injury Diseases 0.000 claims description 12
• 239000003112 inhibitor Substances 0.000 claims description 11
• QMJBSXGXBOBMPC-UHFFFAOYSA-N 1,6,7,8-tetrahydropyrimido[1,2-a]pyrimidin-4-one Chemical compound N1CCCN2C(=O)C=CN=C21 QMJBSXGXBOBMPC-UHFFFAOYSA-N 0.000 claims description 10
• 206010028980 Neoplasm Diseases 0.000 claims description 10
• 208000006011 Stroke Diseases 0.000 claims description 10
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 10
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 9
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
• 208000034799 Tauopathies Diseases 0.000 claims description 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
• 230000002401 inhibitory effect Effects 0.000 claims description 7
• 101000983970 Conus catus Alpha-conotoxin CIB Proteins 0.000 claims description 6
• 210000004556 brain Anatomy 0.000 claims description 6
• 239000007924 injection Substances 0.000 claims description 6
• 238000002347 injection Methods 0.000 claims description 6
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
• 230000008733 trauma Effects 0.000 claims description 6
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
• 201000004384 Alopecia Diseases 0.000 claims description 5
• 208000010412 Glaucoma Diseases 0.000 claims description 5
• 208000008589 Obesity Diseases 0.000 claims description 5
• 208000018737 Parkinson disease Diseases 0.000 claims description 5
• 206010038923 Retinopathy Diseases 0.000 claims description 5
• 201000004810 Vascular dementia Diseases 0.000 claims description 5
• 231100000360 alopecia Toxicity 0.000 claims description 5
• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 5
• 125000001769 aryl amino group Chemical group 0.000 claims description 5
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
• 206010015037 epilepsy Diseases 0.000 claims description 5
• PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical group C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims description 5
• 125000001624 naphthyl group Chemical group 0.000 claims description 5
• 235000020824 obesity Nutrition 0.000 claims description 5
• 201000000980 schizophrenia Diseases 0.000 claims description 5
• 230000005586 smoking cessation Effects 0.000 claims description 5
• 210000000278 spinal cord Anatomy 0.000 claims description 5
• CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical group C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 5
• 230000008736 traumatic injury Effects 0.000 claims description 5
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 5
• JQFIEMVIUQQBST-UHFFFAOYSA-N 2-pyrimidin-4-yl-1,6,7,8-tetrahydropyrimido[1,2-a]pyrimidin-4-one Chemical compound N1=C2NCCCN2C(=O)C=C1C1=CC=NC=N1 JQFIEMVIUQQBST-UHFFFAOYSA-N 0.000 claims description 4
• 208000004736 B-Cell Leukemia Diseases 0.000 claims description 4
• 206010006187 Breast cancer Diseases 0.000 claims description 4
• 208000026310 Breast neoplasm Diseases 0.000 claims description 4
• 102000001267 GSK3 Human genes 0.000 claims description 4
• 108060006662 GSK3 Proteins 0.000 claims description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
• 208000000389 T-cell leukemia Diseases 0.000 claims description 4
• 208000028530 T-cell lymphoblastic leukemia/lymphoma Diseases 0.000 claims description 4
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
• 208000024770 Thyroid neoplasm Diseases 0.000 claims description 4
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 4
• 125000003277 amino group Chemical group 0.000 claims description 4
• 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 4
• 208000028683 bipolar I disease Diseases 0.000 claims description 4
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
• 125000002883 imidazolyl group Chemical group 0.000 claims description 4
• NFVJNJQRWPQVOA-UHFFFAOYSA-N n-[2-chloro-5-(trifluoromethyl)phenyl]-2-[3-(4-ethyl-5-ethylsulfanyl-1,2,4-triazol-3-yl)piperidin-1-yl]acetamide Chemical compound CCN1C(SCC)=NN=C1C1CN(CC(=O)NC=2C(=CC=C(C=2)C(F)(F)F)Cl)CCC1 NFVJNJQRWPQVOA-UHFFFAOYSA-N 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
• 208000027232 peripheral nervous system disease Diseases 0.000 claims description 4
• 208000033808 peripheral neuropathy Diseases 0.000 claims description 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
• 125000003375 sulfoxide group Chemical group 0.000 claims description 4
• 201000002510 thyroid cancer Diseases 0.000 claims description 4
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
• BQVGJTBFGJUZQT-UHFFFAOYSA-N 2,2-dimethyl-1-phenacyl-8-pyrimidin-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=N1 BQVGJTBFGJUZQT-UHFFFAOYSA-N 0.000 claims description 3
• UPABIKMQIWDQRX-OAHLLOKOSA-N 3-chloro-9-[(2s)-2-hydroxy-2-phenylethyl]-2-pyrimidin-4-yl-7,8-dihydro-6h-pyrimido[1,2-a]pyrimidin-4-one Chemical compound C([C@@H](O)C=1C=CC=CC=1)N1CCCN(C(C=2Cl)=O)C1=NC=2C1=CC=NC=N1 UPABIKMQIWDQRX-OAHLLOKOSA-N 0.000 claims description 3
• RSSUFAPBPBUNGT-UHFFFAOYSA-N 8-ethyl-9-phenacyl-2-pyrimidin-4-yl-7,8-dihydro-6h-pyrimido[1,2-a]pyrimidin-4-one Chemical compound C=1C=CC=CC=1C(=O)CN1C(CC)CCN(C(C=2)=O)C1=NC=2C1=CC=NC=N1 RSSUFAPBPBUNGT-UHFFFAOYSA-N 0.000 claims description 3
• 241000700605 Viruses Species 0.000 claims description 3
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
• 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 3
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
• 239000007901 soft capsule Substances 0.000 claims description 3
• AXHBGCGWHQUDHP-UHFFFAOYSA-N 1-(2-hydroxy-2-phenylethyl)-7-pyrimidin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5-one Chemical compound C=1C=CC=CC=1C(O)CN1CCN(C(C=2)=O)C1=NC=2C1=CC=NC=N1 AXHBGCGWHQUDHP-UHFFFAOYSA-N 0.000 claims description 2
• QGHYEHIBWTVYKP-LJQANCHMSA-N 1-[(2s)-2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]-2,2-dimethyl-8-pyrimidin-4-yl-3,4-dihydropyrimido[1,2-a]pyrimidin-6-one Chemical compound COC1=CC=C(OC)C([C@H](O)CN2C(CCN3C(=O)C=C(N=C32)C=2N=CN=CC=2)(C)C)=C1 QGHYEHIBWTVYKP-LJQANCHMSA-N 0.000 claims description 2
• PKDKBIAEYAWCPS-GOSISDBHSA-N 1-[(2s)-2-(3-fluorophenyl)-2-hydroxyethyl]-2,2-dimethyl-8-pyrimidin-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=N1 PKDKBIAEYAWCPS-GOSISDBHSA-N 0.000 claims description 2
• KBCLTIQEDJXGOE-LJQANCHMSA-N 1-[(2s)-2-hydroxy-2-(4-methoxyphenyl)ethyl]-2,2-dimethyl-8-pyrimidin-4-yl-3,4-dihydropyrimido[1,2-a]pyrimidin-6-one Chemical compound C1=CC(OC)=CC=C1[C@H](O)CN1C(C)(C)CCN2C(=O)C=C(C=3N=CN=CC=3)N=C21 KBCLTIQEDJXGOE-LJQANCHMSA-N 0.000 claims description 2
• MTEGVLTYGHZTFA-GOSISDBHSA-N 1-[(2s)-2-hydroxy-2-phenylethyl]-2,2-dimethyl-8-pyrimidin-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=N1 MTEGVLTYGHZTFA-GOSISDBHSA-N 0.000 claims description 2
• MQLUOXJDZPMJKY-UHFFFAOYSA-N 1-[2-(3-fluorophenyl)-2-oxoethyl]-2,2-dimethyl-8-pyrimidin-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=N1 MQLUOXJDZPMJKY-UHFFFAOYSA-N 0.000 claims description 2
• UAWXTXTYLDSPNE-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-2,2-dimethyl-8-pyrimidin-4-yl-3,4-dihydropyrimido[1,2-a]pyrimidin-6-one Chemical compound C=1C=C(F)C=CC=1CCN1C(C)(C)CCN(C(C=2)=O)C1=NC=2C1=CC=NC=N1 UAWXTXTYLDSPNE-UHFFFAOYSA-N 0.000 claims description 2
• IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims description 2
• HWIFLBROPOSOCD-UHFFFAOYSA-N 1-phenacyl-7-pyrimidin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5-one Chemical compound C=1C=CC=CC=1C(=O)CN1CCN(C(C=2)=O)C1=NC=2C1=CC=NC=N1 HWIFLBROPOSOCD-UHFFFAOYSA-N 0.000 claims description 2
• DTXZPAWYSXZQEI-UHFFFAOYSA-N 2,2-dimethyl-1-(naphthalen-1-ylmethyl)-8-pyrimidin-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=N1 DTXZPAWYSXZQEI-UHFFFAOYSA-N 0.000 claims description 2
• OFQHQZIOQYYEKD-UHFFFAOYSA-N 2,2-dimethyl-1-[2-(4-methylphenyl)-2-oxoethyl]-8-pyrimidin-4-yl-3,4-dihydropyrimido[1,2-a]pyrimidin-6-one Chemical compound C1=CC(C)=CC=C1C(=O)CN1C(C)(C)CCN2C(=O)C=C(C=3N=CN=CC=3)N=C21 OFQHQZIOQYYEKD-UHFFFAOYSA-N 0.000 claims description 2
• HHRCYLBOIIEQND-UHFFFAOYSA-N 7,7-difluoro-9-phenacyl-2-pyrimidin-4-yl-6,8-dihydropyrimido[1,2-a]pyrimidin-4-one Chemical compound C12=NC(C=3N=CN=CC=3)=CC(=O)N2CC(F)(F)CN1CC(=O)C1=CC=CC=C1 HHRCYLBOIIEQND-UHFFFAOYSA-N 0.000 claims description 2
• UPDIVRDFFIHGMC-UHFFFAOYSA-N 7,7-dimethyl-2-pyrimidin-4-yl-9-[2-[2-(trifluoromethoxy)phenyl]ethyl]-6,8-dihydropyrimido[1,2-a]pyrimidin-4-one Chemical compound C12=NC(C=3N=CN=CC=3)=CC(=O)N2CC(C)(C)CN1CCC1=CC=CC=C1OC(F)(F)F UPDIVRDFFIHGMC-UHFFFAOYSA-N 0.000 claims description 2
• NODAAAHZMPLSNI-UHFFFAOYSA-N 7,7-dimethyl-9-[2-(2-methylphenyl)ethyl]-2-pyrimidin-4-yl-6,8-dihydropyrimido[1,2-a]pyrimidin-4-one Chemical compound CC1=CC=CC=C1CCN1C2=NC(C=3N=CN=CC=3)=CC(=O)N2CC(C)(C)C1 NODAAAHZMPLSNI-UHFFFAOYSA-N 0.000 claims description 2
• ONFKNLUAHBLFES-UHFFFAOYSA-N 7,7-dimethyl-9-[2-(4-nitrophenyl)ethyl]-2-pyrimidin-4-yl-6,8-dihydropyrimido[1,2-a]pyrimidin-4-one Chemical compound C12=NC(C=3N=CN=CC=3)=CC(=O)N2CC(C)(C)CN1CCC1=CC=C([N+]([O-])=O)C=C1 ONFKNLUAHBLFES-UHFFFAOYSA-N 0.000 claims description 2
• UAGOWXXTSLUWJG-LRTDYKAYSA-N 8-ethyl-9-[(2s)-2-hydroxy-2-phenylethyl]-2-pyrimidin-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(CC)CCN(C(C=2)=O)C1=NC=2C1=CC=NC=N1 UAGOWXXTSLUWJG-LRTDYKAYSA-N 0.000 claims description 2
• DVGBDDAYLMRVKH-UHFFFAOYSA-N 8-methyl-9-(naphthalen-1-ylmethyl)-2-pyrimidin-4-yl-7,8-dihydro-6h-pyrimido[1,2-a]pyrimidin-4-one Chemical compound C=1C=CC2=CC=CC=C2C=1CN1C(C)CCN(C(C=2)=O)C1=NC=2C1=CC=NC=N1 DVGBDDAYLMRVKH-UHFFFAOYSA-N 0.000 claims description 2
• LRABFKHJBUBRRB-UHFFFAOYSA-N 9-(1-hydroxy-1-phenylpropan-2-yl)-2-pyrimidin-4-yl-7,8-dihydro-6h-pyrimido[1,2-a]pyrimidin-4-one Chemical compound C1CCN(C(C=C(N=2)C=3N=CN=CC=3)=O)C=2N1C(C)C(O)C1=CC=CC=C1 LRABFKHJBUBRRB-UHFFFAOYSA-N 0.000 claims description 2
• ZBLKRFQQDZIFKI-UHFFFAOYSA-N 9-(1-oxo-1-phenylpropan-2-yl)-2-pyrimidin-4-yl-7,8-dihydro-6h-pyrimido[1,2-a]pyrimidin-4-one Chemical compound C=1C=CC=CC=1C(=O)C(C)N1CCCN(C(C=2)=O)C1=NC=2C1=CC=NC=N1 ZBLKRFQQDZIFKI-UHFFFAOYSA-N 0.000 claims description 2
• RPOOVWZKUDZTBV-UHFFFAOYSA-N 9-(2-phenylsulfanylethyl)-2-pyrimidin-4-yl-7,8-dihydro-6h-pyrimido[1,2-a]pyrimidin-4-one Chemical compound C1CCN2C(=O)C=C(C=3N=CN=CC=3)N=C2N1CCSC1=CC=CC=C1 RPOOVWZKUDZTBV-UHFFFAOYSA-N 0.000 claims description 2
• RECOUFVINZDODV-UHFFFAOYSA-N 9-(3-hydroxy-3-phenylpropyl)-2-pyrimidin-4-yl-7,8-dihydro-6h-pyrimido[1,2-a]pyrimidin-4-one Chemical compound C=1C=CC=CC=1C(O)CCN1CCCN(C(C=2)=O)C1=NC=2C1=CC=NC=N1 RECOUFVINZDODV-UHFFFAOYSA-N 0.000 claims description 2
• JYHMMTLLSOAYSW-UHFFFAOYSA-N 9-(3-oxo-3-phenylpropyl)-2-pyrimidin-4-yl-7,8-dihydro-6h-pyrimido[1,2-a]pyrimidin-4-one Chemical compound C=1C=CC=CC=1C(=O)CCN1CCCN(C(C=2)=O)C1=NC=2C1=CC=NC=N1 JYHMMTLLSOAYSW-UHFFFAOYSA-N 0.000 claims description 2
• OZITZBLPTIRHMN-KRWDZBQOSA-N 9-[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]-2-pyrimidin-4-yl-7,8-dihydro-6h-pyrimido[1,2-a]pyrimidin-4-one Chemical compound C([C@H](O)C=1C=C(Cl)C=CC=1)N1CCCN(C(C=2)=O)C1=NC=2C1=CC=NC=N1 OZITZBLPTIRHMN-KRWDZBQOSA-N 0.000 claims description 2
• LYWFCKAUWKCCIH-JOCHJYFZSA-N 9-[(2s)-2-(cyclopropylmethoxy)-2-phenylethyl]-7,7-dimethyl-2-pyrimidin-4-yl-6,8-dihydropyrimido[1,2-a]pyrimidin-4-one Chemical compound O([C@H](CN1CC(CN2C(=O)C=C(N=C21)C=1N=CN=CC=1)(C)C)C=1C=CC=CC=1)CC1CC1 LYWFCKAUWKCCIH-JOCHJYFZSA-N 0.000 claims description 2
• PCFMMISULNYZQC-HXUWFJFHSA-N 9-[(2s)-2-ethoxy-2-phenylethyl]-7,7-dimethyl-2-pyrimidin-4-yl-6,8-dihydropyrimido[1,2-a]pyrimidin-4-one Chemical compound C([C@@H](OCC)C=1C=CC=CC=1)N1CC(C)(C)CN(C(C=2)=O)C1=NC=2C1=CC=NC=N1 PCFMMISULNYZQC-HXUWFJFHSA-N 0.000 claims description 2
• ACQRNHAWOMSYDY-UHFFFAOYSA-N 9-[2-(2-chlorophenyl)ethyl]-7,7-dimethyl-2-pyrimidin-4-yl-6,8-dihydropyrimido[1,2-a]pyrimidin-4-one Chemical compound C12=NC(C=3N=CN=CC=3)=CC(=O)N2CC(C)(C)CN1CCC1=CC=CC=C1Cl ACQRNHAWOMSYDY-UHFFFAOYSA-N 0.000 claims description 2
• NESJZLRWAKVWJS-UHFFFAOYSA-N 9-[2-(2-methoxyphenyl)ethyl]-8-methyl-2-pyrimidin-4-yl-7,8-dihydro-6h-pyrimido[1,2-a]pyrimidin-4-one Chemical compound COC1=CC=CC=C1CCN1C2=NC(C=3N=CN=CC=3)=CC(=O)N2CCC1C NESJZLRWAKVWJS-UHFFFAOYSA-N 0.000 claims description 2
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• OZITZBLPTIRHMN-UHFFFAOYSA-N 9-[2-(3-chlorophenyl)-2-hydroxyethyl]-2-pyrimidin-4-yl-7,8-dihydro-6h-pyrimido[1,2-a]pyrimidin-4-one Chemical compound C=1C=CC(Cl)=CC=1C(O)CN1CCCN(C(C=2)=O)C1=NC=2C1=CC=NC=N1 OZITZBLPTIRHMN-UHFFFAOYSA-N 0.000 claims description 2
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