NO325781B1 - 3-substituert 4-pyrimidonderivater - Google Patents
3-substituert 4-pyrimidonderivater Download PDFInfo
- Publication number
- NO325781B1 NO325781B1 NO20041600A NO20041600A NO325781B1 NO 325781 B1 NO325781 B1 NO 325781B1 NO 20041600 A NO20041600 A NO 20041600A NO 20041600 A NO20041600 A NO 20041600A NO 325781 B1 NO325781 B1 NO 325781B1
- Authority
- NO
- Norway
- Prior art keywords
- group
- ring
- methyl
- pyrimidin
- pyridin
- Prior art date
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- -1 3-substituted 4-pyrimidone Chemical class 0.000 title claims description 240
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 47
- 150000008318 pyrimidones Chemical class 0.000 claims abstract description 46
- 150000003839 salts Chemical class 0.000 claims abstract description 43
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 34
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 30
- 239000012453 solvate Substances 0.000 claims abstract description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 21
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical group C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000001424 substituent group Chemical group 0.000 claims description 36
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 30
- 201000010099 disease Diseases 0.000 claims description 29
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 29
- 239000003814 drug Substances 0.000 claims description 26
- 229940079593 drug Drugs 0.000 claims description 25
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 23
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 18
- 208000024827 Alzheimer disease Diseases 0.000 claims description 17
- 239000004480 active ingredient Substances 0.000 claims description 17
- 125000003277 amino group Chemical group 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 15
- 230000001225 therapeutic effect Effects 0.000 claims description 15
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical group C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 14
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical group C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 claims description 12
- 230000003449 preventive effect Effects 0.000 claims description 12
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical group C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims description 10
- 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 10
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 10
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 9
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 8
- 201000011240 Frontotemporal dementia Diseases 0.000 claims description 8
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 8
- 125000001041 indolyl group Chemical group 0.000 claims description 8
- 208000014674 injury Diseases 0.000 claims description 8
- 230000004770 neurodegeneration Effects 0.000 claims description 8
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 8
- 210000004556 brain Anatomy 0.000 claims description 7
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 6
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical group C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 claims description 6
- AXIIEOPSQHRYCU-UHFFFAOYSA-N 2-methyl-1,3-dihydroisoindole Chemical group C1=CC=C2CN(C)CC2=C1 AXIIEOPSQHRYCU-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 6
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 6
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 6
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
- 208000005145 Cerebral amyloid angiopathy Diseases 0.000 claims description 5
- 206010008111 Cerebral haemorrhage Diseases 0.000 claims description 5
- 201000010374 Down Syndrome Diseases 0.000 claims description 5
- 208000037658 Parkinson-dementia complex of Guam Diseases 0.000 claims description 5
- 108091000080 Phosphotransferase Proteins 0.000 claims description 5
- 208000036757 Postencephalitic parkinsonism Diseases 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 230000000302 ischemic effect Effects 0.000 claims description 5
- 102000020233 phosphotransferase Human genes 0.000 claims description 5
- 208000000170 postencephalitic Parkinson disease Diseases 0.000 claims description 5
- 201000002212 progressive supranuclear palsy Diseases 0.000 claims description 5
- 230000002784 sclerotic effect Effects 0.000 claims description 5
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical group CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims description 4
- AWBOSXFRPFZLOP-UHFFFAOYSA-N 2,1,3-benzoxadiazole Chemical group C1=CC=CC2=NON=C21 AWBOSXFRPFZLOP-UHFFFAOYSA-N 0.000 claims description 4
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical group CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims description 4
- 201000004384 Alopecia Diseases 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
- 208000011990 Corticobasal Degeneration Diseases 0.000 claims description 4
- 208000010412 Glaucoma Diseases 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 208000008589 Obesity Diseases 0.000 claims description 4
- 208000027089 Parkinsonian disease Diseases 0.000 claims description 4
- 206010034010 Parkinsonism Diseases 0.000 claims description 4
- 208000000609 Pick Disease of the Brain Diseases 0.000 claims description 4
- 208000017442 Retinal disease Diseases 0.000 claims description 4
- 206010038923 Retinopathy Diseases 0.000 claims description 4
- 208000024770 Thyroid neoplasm Diseases 0.000 claims description 4
- 201000004810 Vascular dementia Diseases 0.000 claims description 4
- 241000700605 Viruses Species 0.000 claims description 4
- 231100000360 alopecia Toxicity 0.000 claims description 4
- 208000028683 bipolar I disease Diseases 0.000 claims description 4
- 206010014599 encephalitis Diseases 0.000 claims description 4
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical group C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 claims description 4
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 4
- 235000020824 obesity Nutrition 0.000 claims description 4
- 208000033808 peripheral neuropathy Diseases 0.000 claims description 4
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 201000000980 schizophrenia Diseases 0.000 claims description 4
- 210000000278 spinal cord Anatomy 0.000 claims description 4
- 201000002510 thyroid cancer Diseases 0.000 claims description 4
- 230000008733 trauma Effects 0.000 claims description 4
- 230000008736 traumatic injury Effects 0.000 claims description 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 3
- RPMITZJMOPAUMG-UHFFFAOYSA-N 2,3,4,4a-tetrahydro-1H-benzo[7]annulene Chemical group C1=CC=CC2CCCCC2=C1 RPMITZJMOPAUMG-UHFFFAOYSA-N 0.000 claims description 3
- 206010044688 Trisomy 21 Diseases 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 3
- HOXGZVUCAYFWGR-KQQUZDAGSA-N (3e,5e)-octa-1,3,5-triene Chemical group CC\C=C\C=C\C=C HOXGZVUCAYFWGR-KQQUZDAGSA-N 0.000 claims description 2
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical group C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- XXOQJWXDRPURJK-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1-benzoxepine Chemical group O1CCCCC2=CC=CC=C21 XXOQJWXDRPURJK-UHFFFAOYSA-N 0.000 claims description 2
- NXCQEVQGDRISRL-UHFFFAOYSA-N 2-(2-benzoylmorpholin-4-yl)-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound C=1C(=O)N(C)C(N2CC(OCC2)C(=O)C=2C=CC=CC=2)=NC=1C1=CC=NC=C1 NXCQEVQGDRISRL-UHFFFAOYSA-N 0.000 claims description 2
- DXFCUZGJPYQFIU-UHFFFAOYSA-N 2-(3-benzoylpiperidin-1-yl)-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound C=1C(=O)N(C)C(N2CC(CCC2)C(=O)C=2C=CC=CC=2)=NC=1C1=CC=NC=C1 DXFCUZGJPYQFIU-UHFFFAOYSA-N 0.000 claims description 2
- SKSYOLBNGGRQAC-GOSISDBHSA-N 2-[(2s)-2-(2,4-difluoro-6-methoxyphenyl)morpholin-4-yl]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound COC1=CC(F)=CC(F)=C1[C@@H]1OCCN(C=2N(C(=O)C=C(N=2)C=2C=CN=CC=2)C)C1 SKSYOLBNGGRQAC-GOSISDBHSA-N 0.000 claims description 2
- NCPUWAGCDXDIPX-HXUWFJFHSA-N 2-[(2s)-2-(2,4-dimethoxyphenyl)morpholin-4-yl]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound COC1=CC(OC)=CC=C1[C@@H]1OCCN(C=2N(C(=O)C=C(N=2)C=2C=CN=CC=2)C)C1 NCPUWAGCDXDIPX-HXUWFJFHSA-N 0.000 claims description 2
- MBVYGBUUQIDTAQ-HXUWFJFHSA-N 2-[(2s)-2-(2,5-dimethoxyphenyl)morpholin-4-yl]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound COC1=CC=C(OC)C([C@@H]2OCCN(C2)C=2N(C(=O)C=C(N=2)C=2C=CN=CC=2)C)=C1 MBVYGBUUQIDTAQ-HXUWFJFHSA-N 0.000 claims description 2
- MBEKVLSSEYOCSP-QGZVFWFLSA-N 2-[(2s)-2-(2,6-dichlorophenyl)morpholin-4-yl]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound C=1C(=O)N(C)C(N2C[C@@H](OCC2)C=2C(=CC=CC=2Cl)Cl)=NC=1C1=CC=NC=C1 MBEKVLSSEYOCSP-QGZVFWFLSA-N 0.000 claims description 2
- ITAUXPSETNVANZ-LJQANCHMSA-N 2-[(2s)-2-(2,6-dimethoxyphenyl)morpholin-4-yl]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound COC1=CC=CC(OC)=C1[C@@H]1OCCN(C=2N(C(=O)C=C(N=2)C=2C=CN=CC=2)C)C1 ITAUXPSETNVANZ-LJQANCHMSA-N 0.000 claims description 2
- JFCBDPQANHNOJC-GOSISDBHSA-N 2-[(2s)-2-(2-chlorophenyl)morpholin-4-yl]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound C=1C(=O)N(C)C(N2C[C@@H](OCC2)C=2C(=CC=CC=2)Cl)=NC=1C1=CC=NC=C1 JFCBDPQANHNOJC-GOSISDBHSA-N 0.000 claims description 2
- NUWBPSCILGWYJD-GOSISDBHSA-N 2-[(2s)-2-(3-bromophenyl)morpholin-4-yl]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound C=1C(=O)N(C)C(N2C[C@@H](OCC2)C=2C=C(Br)C=CC=2)=NC=1C1=CC=NC=C1 NUWBPSCILGWYJD-GOSISDBHSA-N 0.000 claims description 2
- WYVWRIBBJCVZBU-LJQANCHMSA-N 2-[(2s)-2-(3-methoxyphenyl)morpholin-4-yl]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound COC1=CC=CC([C@@H]2OCCN(C2)C=2N(C(=O)C=C(N=2)C=2C=CN=CC=2)C)=C1 WYVWRIBBJCVZBU-LJQANCHMSA-N 0.000 claims description 2
- PDXVBCFBVCQTFC-GOSISDBHSA-N 2-[(2s)-2-(4-bromophenyl)morpholin-4-yl]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound C=1C(=O)N(C)C(N2C[C@@H](OCC2)C=2C=CC(Br)=CC=2)=NC=1C1=CC=NC=C1 PDXVBCFBVCQTFC-GOSISDBHSA-N 0.000 claims description 2
- RSGNGUPSUUTVML-LJQANCHMSA-N 2-[(2s)-2-(4-fluoro-2-methoxyphenyl)morpholin-4-yl]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound COC1=CC(F)=CC=C1[C@@H]1OCCN(C=2N(C(=O)C=C(N=2)C=2C=CN=CC=2)C)C1 RSGNGUPSUUTVML-LJQANCHMSA-N 0.000 claims description 2
- AMMSSQAWYDICPE-LJQANCHMSA-N 2-[(2s)-2-(4-methoxyphenyl)morpholin-4-yl]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound C1=CC(OC)=CC=C1[C@@H]1OCCN(C=2N(C(=O)C=C(N=2)C=2C=CN=CC=2)C)C1 AMMSSQAWYDICPE-LJQANCHMSA-N 0.000 claims description 2
- SKSYOLBNGGRQAC-UHFFFAOYSA-N 2-[2-(2,4-difluoro-6-methoxyphenyl)morpholin-4-yl]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound COC1=CC(F)=CC(F)=C1C1OCCN(C=2N(C(=O)C=C(N=2)C=2C=CN=CC=2)C)C1 SKSYOLBNGGRQAC-UHFFFAOYSA-N 0.000 claims description 2
- OYTNQXCKJVXNFQ-UHFFFAOYSA-N 2-[2-(2,4-difluorophenyl)morpholin-4-yl]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound C=1C(=O)N(C)C(N2CC(OCC2)C=2C(=CC(F)=CC=2)F)=NC=1C1=CC=NC=C1 OYTNQXCKJVXNFQ-UHFFFAOYSA-N 0.000 claims description 2
- MBVYGBUUQIDTAQ-UHFFFAOYSA-N 2-[2-(2,5-dimethoxyphenyl)morpholin-4-yl]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound COC1=CC=C(OC)C(C2OCCN(C2)C=2N(C(=O)C=C(N=2)C=2C=CN=CC=2)C)=C1 MBVYGBUUQIDTAQ-UHFFFAOYSA-N 0.000 claims description 2
- UUJZZJCEWDZFCY-UHFFFAOYSA-N 2-[2-(2,6-difluorophenyl)morpholin-4-yl]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound C=1C(=O)N(C)C(N2CC(OCC2)C=2C(=CC=CC=2F)F)=NC=1C1=CC=NC=C1 UUJZZJCEWDZFCY-UHFFFAOYSA-N 0.000 claims description 2
- ITAUXPSETNVANZ-UHFFFAOYSA-N 2-[2-(2,6-dimethoxyphenyl)morpholin-4-yl]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound COC1=CC=CC(OC)=C1C1OCCN(C=2N(C(=O)C=C(N=2)C=2C=CN=CC=2)C)C1 ITAUXPSETNVANZ-UHFFFAOYSA-N 0.000 claims description 2
- GXTQJAFEQFYDTA-UHFFFAOYSA-N 2-[2-(2-bromo-4-fluorophenyl)morpholin-4-yl]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound C=1C(=O)N(C)C(N2CC(OCC2)C=2C(=CC(F)=CC=2)Br)=NC=1C1=CC=NC=C1 GXTQJAFEQFYDTA-UHFFFAOYSA-N 0.000 claims description 2
- JHNWKTOHLFPYOV-UHFFFAOYSA-N 2-[2-(2-bromophenyl)morpholin-4-yl]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound C=1C(=O)N(C)C(N2CC(OCC2)C=2C(=CC=CC=2)Br)=NC=1C1=CC=NC=C1 JHNWKTOHLFPYOV-UHFFFAOYSA-N 0.000 claims description 2
- BDBDSBMMKVJRJC-UHFFFAOYSA-N 2-[2-(2-chloro-6-fluorophenyl)morpholin-4-yl]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound C=1C(=O)N(C)C(N2CC(OCC2)C=2C(=CC=CC=2F)Cl)=NC=1C1=CC=NC=C1 BDBDSBMMKVJRJC-UHFFFAOYSA-N 0.000 claims description 2
- JFCBDPQANHNOJC-UHFFFAOYSA-N 2-[2-(2-chlorophenyl)morpholin-4-yl]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound C=1C(=O)N(C)C(N2CC(OCC2)C=2C(=CC=CC=2)Cl)=NC=1C1=CC=NC=C1 JFCBDPQANHNOJC-UHFFFAOYSA-N 0.000 claims description 2
- KVAYRHJOQRDMSZ-UHFFFAOYSA-N 2-[2-(2-methoxybenzoyl)morpholin-4-yl]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound COC1=CC=CC=C1C(=O)C1OCCN(C=2N(C(=O)C=C(N=2)C=2C=CN=CC=2)C)C1 KVAYRHJOQRDMSZ-UHFFFAOYSA-N 0.000 claims description 2
- RXCKTOIDABXJLT-UHFFFAOYSA-N 2-[2-(2-methoxyphenyl)morpholin-4-yl]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound COC1=CC=CC=C1C1OCCN(C=2N(C(=O)C=C(N=2)C=2C=CN=CC=2)C)C1 RXCKTOIDABXJLT-UHFFFAOYSA-N 0.000 claims description 2
- NUWBPSCILGWYJD-UHFFFAOYSA-N 2-[2-(3-bromophenyl)morpholin-4-yl]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound C=1C(=O)N(C)C(N2CC(OCC2)C=2C=C(Br)C=CC=2)=NC=1C1=CC=NC=C1 NUWBPSCILGWYJD-UHFFFAOYSA-N 0.000 claims description 2
- BBNWEEMYFMVCSH-UHFFFAOYSA-N 2-[2-(3-chlorophenyl)morpholin-4-yl]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound C=1C(=O)N(C)C(N2CC(OCC2)C=2C=C(Cl)C=CC=2)=NC=1C1=CC=NC=C1 BBNWEEMYFMVCSH-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/56—One oxygen atom and one sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
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- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2001331675 | 2001-09-21 | ||
JP2001331677 | 2001-09-21 | ||
JP2001331674 | 2001-09-21 | ||
JP2001331678 | 2001-09-21 | ||
PCT/JP2002/009685 WO2003037888A1 (en) | 2001-09-21 | 2002-09-20 | 3-substituted-4-pyrimidone derivatives |
Publications (2)
Publication Number | Publication Date |
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NO20041600L NO20041600L (no) | 2004-06-16 |
NO325781B1 true NO325781B1 (no) | 2008-07-14 |
Family
ID=27482651
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20041600A NO325781B1 (no) | 2001-09-21 | 2004-04-20 | 3-substituert 4-pyrimidonderivater |
Country Status (24)
Country | Link |
---|---|
US (1) | US7427615B2 (zh) |
EP (1) | EP1427720B1 (zh) |
JP (1) | JP4347050B2 (zh) |
KR (1) | KR100881821B1 (zh) |
CN (1) | CN100488958C (zh) |
AT (1) | ATE424393T1 (zh) |
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BR (1) | BR0212892A (zh) |
CA (1) | CA2460121C (zh) |
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IL (2) | IL160700A0 (zh) |
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NO (1) | NO325781B1 (zh) |
NZ (1) | NZ531636A (zh) |
PL (1) | PL368671A1 (zh) |
PT (1) | PT1427720E (zh) |
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AR023052A1 (es) | 1998-09-25 | 2002-09-04 | Mitsuharu Yoshimura Milton | Derivados de pirimidona |
AU2002337498B2 (en) | 2001-09-21 | 2006-08-10 | Mitsubishi Pharma Corporation | 3-substituted-4-pyrimidone derivatives |
EA009027B1 (ru) | 2002-12-16 | 2007-10-26 | Мицубиси Фарма Корпорейшн | Производные 3-замещенного-4-пиримидона |
CA2518465A1 (en) | 2003-03-25 | 2004-10-14 | Takeda San Diego, Inc. | Dipeptidyl peptidase inhibitors |
TWI357408B (en) * | 2003-03-26 | 2012-02-01 | Mitsubishi Tanabe Pharma Corp | 3-substituted-4-pyrimidone derivatives |
CN1867560A (zh) | 2003-08-13 | 2006-11-22 | 武田药品工株式会社 | 4-嘧啶酮衍生物及其作为肽基肽酶抑制剂的用途 |
EP1699777B1 (en) | 2003-09-08 | 2012-12-12 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
GB0325956D0 (en) | 2003-11-06 | 2003-12-10 | Addex Pharmaceuticals Sa | Novel compounds |
UA85871C2 (uk) | 2004-03-15 | 2009-03-10 | Такеда Фармасьютікал Компані Лімітед | Інгібітори дипептидилпептидази |
AR050865A1 (es) | 2004-09-09 | 2006-11-29 | Sanofi Aventis | Derivados de 2- morfolino-4-pirimidona |
DK1805164T3 (da) * | 2004-09-29 | 2011-05-16 | Mitsubishi Tanabe Pharma Corp | 6-(pyridinyl)-4-pyrimidonderivater som inhibitorer af TAU 1 oroteinkinase |
WO2006041405A1 (en) * | 2004-10-15 | 2006-04-20 | Astrazeneca Ab | Substituted amino-pyrimidones and uses thereof |
JP2008516945A (ja) * | 2004-10-15 | 2008-05-22 | アストラゼネカ・アクチエボラーグ | 置換されたアミノ化合物およびそれらの使用 |
US7872124B2 (en) | 2004-12-21 | 2011-01-18 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
GB0510141D0 (en) * | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds B3 |
GB0510142D0 (en) * | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds A1 |
NZ566799A (en) | 2005-09-14 | 2011-04-29 | Takeda Pharmaceutical | Dipeptidyl peptidase inhibitors for treating diabetes |
WO2007035629A2 (en) | 2005-09-16 | 2007-03-29 | Takeda Pharmaceutical Company Limited | Process for the preparation of pyrimidinedione derivatives |
TW200813015A (en) * | 2006-03-15 | 2008-03-16 | Mitsubishi Pharma Corp | 2-(cyclic amino)-pyrimidone derivatives |
KR20090052884A (ko) * | 2006-08-23 | 2009-05-26 | 화이자 프로덕츠 인크. | Gsk-3 억제제로서의 피리미돈 화합물 |
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TW200838536A (en) | 2006-11-29 | 2008-10-01 | Takeda Pharmaceutical | Polymorphs of succinate salt of 2-[6-(3-amino-piperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethy]-4-fluor-benzonitrile and methods of use therefor |
AR064660A1 (es) * | 2006-12-26 | 2009-04-15 | Mitsubishi Tanabe Pharma Corp | Derivados de pirimidinona 6-heterociclica 2-sustituida, medicamentos que los contienen y usos para prevenir y/o tratar enfermedades neurodegenerativas entre otras |
US8093236B2 (en) | 2007-03-13 | 2012-01-10 | Takeda Pharmaceuticals Company Limited | Weekly administration of dipeptidyl peptidase inhibitors |
CA2698819A1 (en) | 2007-09-14 | 2009-03-19 | Mitsubishi Tanabe Pharma Corporation | 6-pyrimidinyl-pyrimid-2-one derivative |
MX2010002766A (es) * | 2007-09-14 | 2010-05-19 | Sanofi Aventis | 3-metil-2-((2s)-2-(4-(3-metil-l, 2, 4-oxadiazol-5-il-) fenil) morfolino) -6- (pirimidin-4-il) pirimidin-4 (3h) -ona como inhibidor de tau proteina cinasa. |
AR076014A1 (es) * | 2009-04-02 | 2011-05-11 | Sanofi Aventis | Derivados de 3- (1,4) oxazepan -4-pirimidona |
US8940738B2 (en) | 2009-08-13 | 2015-01-27 | Mitsubishi Tanabe Pharma Corporation | Pyrimidone compounds |
US9006232B2 (en) | 2009-08-13 | 2015-04-14 | Mitsubishi Tanabe Pharma Corporation | Pyrimidone derivatives |
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AR023052A1 (es) | 1998-09-25 | 2002-09-04 | Mitsuharu Yoshimura Milton | Derivados de pirimidona |
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EP1136482A1 (en) * | 2000-03-23 | 2001-09-26 | Sanofi-Synthelabo | 2-Amino-3-(alkyl)-pyrimidone derivatives as GSK3beta inhibitors |
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Also Published As
Publication number | Publication date |
---|---|
SI1427720T1 (sl) | 2009-08-31 |
CY1110317T1 (el) | 2015-01-14 |
CN1556804A (zh) | 2004-12-22 |
US20050090490A1 (en) | 2005-04-28 |
TWI265164B (en) | 2006-11-01 |
EA007576B1 (ru) | 2006-12-29 |
EP1427720B1 (en) | 2009-03-04 |
DE60231414D1 (de) | 2009-04-16 |
CA2460121C (en) | 2010-11-02 |
WO2003037888A1 (en) | 2003-05-08 |
CN100488958C (zh) | 2009-05-20 |
PT1427720E (pt) | 2009-04-27 |
BR0212892A (pt) | 2004-08-03 |
US7427615B2 (en) | 2008-09-23 |
HUP0401900A3 (en) | 2005-08-29 |
EP1427720A1 (en) | 2004-06-16 |
JP4347050B2 (ja) | 2009-10-21 |
HUP0401900A2 (hu) | 2004-12-28 |
NZ531636A (en) | 2005-11-25 |
ES2323576T3 (es) | 2009-07-21 |
KR20040054689A (ko) | 2004-06-25 |
AU2002337499B2 (en) | 2007-08-23 |
KR100881821B1 (ko) | 2009-02-03 |
IL160700A (en) | 2009-09-22 |
NO20041600L (no) | 2004-06-16 |
CA2460121A1 (en) | 2003-05-08 |
IL160700A0 (en) | 2004-08-31 |
DK1427720T3 (da) | 2009-05-04 |
JP2005510506A (ja) | 2005-04-21 |
MXPA04002662A (es) | 2004-11-22 |
EA200400453A1 (ru) | 2004-08-26 |
PL368671A1 (en) | 2005-04-04 |
ATE424393T1 (de) | 2009-03-15 |
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