NZ542136A - Substituted 2-(diaza-bicyclo-alkyl)-pyrimidone derivatives - Google Patents
Substituted 2-(diaza-bicyclo-alkyl)-pyrimidone derivativesInfo
- Publication number
- NZ542136A NZ542136A NZ542136A NZ54213604A NZ542136A NZ 542136 A NZ542136 A NZ 542136A NZ 542136 A NZ542136 A NZ 542136A NZ 54213604 A NZ54213604 A NZ 54213604A NZ 542136 A NZ542136 A NZ 542136A
- Authority
- NZ
- New Zealand
- Prior art keywords
- diaza
- bicyclo
- methyl
- hept
- group
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 92
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- 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 15
- 239000003112 inhibitor Substances 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 39
- 239000003814 drug Substances 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 23
- 230000000694 effects Effects 0.000 claims description 21
- 239000004480 active ingredient Substances 0.000 claims description 18
- 239000012453 solvate Substances 0.000 claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 claims description 16
- WVQAFJQNWCNJIJ-UHFFFAOYSA-N 2-pyrimidin-2-yl-1h-pyrimidin-6-one Chemical compound N1C(=O)C=CN=C1C1=NC=CC=N1 WVQAFJQNWCNJIJ-UHFFFAOYSA-N 0.000 claims description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 201000010099 disease Diseases 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- 230000003449 preventive effect Effects 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 15
- 230000001225 therapeutic effect Effects 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 14
- 230000002159 abnormal effect Effects 0.000 claims description 13
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- NLFRUPSAGIMPEK-UHFFFAOYSA-N 2-pyridin-4-yl-1h-pyrimidin-6-one Chemical compound OC1=CC=NC(C=2C=CN=CC=2)=N1 NLFRUPSAGIMPEK-UHFFFAOYSA-N 0.000 claims description 10
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 206010028980 Neoplasm Diseases 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 208000014674 injury Diseases 0.000 claims description 9
- 208000024827 Alzheimer disease Diseases 0.000 claims description 8
- 150000004677 hydrates Chemical class 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- ZIPAVCNJGNCTNM-UHFFFAOYSA-N 6-pyrimidin-4-yl-1h-pyrimidin-4-one Chemical compound N1=CNC(=O)C=C1C1=CC=NC=N1 ZIPAVCNJGNCTNM-UHFFFAOYSA-N 0.000 claims description 7
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- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 239000007924 injection Substances 0.000 claims description 6
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- 125000003545 alkoxy group Chemical group 0.000 claims description 5
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 4
- 208000000389 T-cell leukemia Diseases 0.000 claims description 4
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- 210000004556 brain Anatomy 0.000 claims description 4
- 239000004615 ingredient Substances 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
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- 208000027232 peripheral nervous system disease Diseases 0.000 claims description 4
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- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical group C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 claims description 4
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 4
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- 125000001424 substituent group Chemical group 0.000 claims description 4
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- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 4
- FAWDKMSZMOVGMP-KIYNQFGBSA-N (1s)-5-(1-methyl-6-oxo-4-pyridin-4-ylpyrimidin-2-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylic acid Chemical compound C=1C(=O)N(C)C(N2C3C[C@H](N(C3)C(O)=O)C2)=NC=1C1=CC=NC=C1 FAWDKMSZMOVGMP-KIYNQFGBSA-N 0.000 claims description 3
- 241000700605 Viruses Species 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 3
- 238000007911 parenteral administration Methods 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 239000007901 soft capsule Substances 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 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
- ATRRAVJMDWFGEO-ZVAWYAOSSA-N 2-[(4s)-2-(3-methoxybenzoyl)-2,5-diazabicyclo[2.2.1]heptan-5-yl]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound C([C@]1(CN2C(=O)C=3C=C(OC)C=CC=3)[H])C2CN1C(N(C(=O)C=1)C)=NC=1C1=CC=NC=C1 ATRRAVJMDWFGEO-ZVAWYAOSSA-N 0.000 claims description 2
- JUAVVYUEKJVPSV-LYKKTTPLSA-N 2-[(4s)-2-(4-bromobenzoyl)-2,5-diazabicyclo[2.2.1]heptan-5-yl]-3-methyl-6-pyrimidin-4-ylpyrimidin-4-one Chemical compound C([C@]1(CN2C(=O)C=3C=CC(Br)=CC=3)[H])C2CN1C(N(C(=O)C=1)C)=NC=1C1=CC=NC=N1 JUAVVYUEKJVPSV-LYKKTTPLSA-N 0.000 claims description 2
- JMDZZWMKHMIQKN-ZVAWYAOSSA-N 3-methyl-2-[(1s)-5-(2-phenylethyl)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-6-pyrimidin-4-ylpyrimidin-4-one Chemical compound C([C@]1(CN2CCC=3C=CC=CC=3)[H])C2CN1C(N(C(=O)C=1)C)=NC=1C1=CC=NC=N1 JMDZZWMKHMIQKN-ZVAWYAOSSA-N 0.000 claims description 2
- FDPFRZVNFJGCCX-GGYWPGCISA-N 3-methyl-2-[(1s)-5-(4-methylphenyl)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-6-pyridin-4-ylpyrimidin-4-one Chemical compound C([C@]1(CN2C=3C=CC(C)=CC=3)[H])C2CN1C(N(C(=O)C=1)C)=NC=1C1=CC=NC=C1 FDPFRZVNFJGCCX-GGYWPGCISA-N 0.000 claims description 2
- IBKRDHTYZXPDKN-DJNXLDHESA-N 3-methyl-6-pyridin-4-yl-2-[(1s)-5-pyridin-3-yl-2,5-diazabicyclo[2.2.1]heptan-2-yl]pyrimidin-4-one Chemical compound C([C@]1(CN2C=3C=NC=CC=3)[H])C2CN1C(N(C(=O)C=1)C)=NC=1C1=CC=NC=C1 IBKRDHTYZXPDKN-DJNXLDHESA-N 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims description 2
- 239000000787 lecithin Substances 0.000 claims description 2
- 235000010445 lecithin Nutrition 0.000 claims description 2
- 229940067606 lecithin Drugs 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims 2
- NOWZZRHWUMMVLE-ZVAWYAOSSA-N 2-[(1s)-5-(3-fluorophenyl)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound C([C@]1(CN2C=3C=C(F)C=CC=3)[H])C2CN1C(N(C(=O)C=1)C)=NC=1C1=CC=NC=C1 NOWZZRHWUMMVLE-ZVAWYAOSSA-N 0.000 claims 1
- FEAOXJSSWSVUGC-ZVAWYAOSSA-N 2-[(1s)-5-(4-fluorophenyl)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound C([C@]1(CN2C=3C=CC(F)=CC=3)[H])C2CN1C(N(C(=O)C=1)C)=NC=1C1=CC=NC=C1 FEAOXJSSWSVUGC-ZVAWYAOSSA-N 0.000 claims 1
- MAYJPXVVRDKBEU-LYKKTTPLSA-N 2-[(1s)-5-(4-fluorophenyl)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-3-methyl-6-pyrimidin-4-ylpyrimidin-4-one Chemical compound C([C@]1(CN2C=3C=CC(F)=CC=3)[H])C2CN1C(N(C(=O)C=1)C)=NC=1C1=CC=NC=N1 MAYJPXVVRDKBEU-LYKKTTPLSA-N 0.000 claims 1
- DFGWLALTMJBIIQ-KIYNQFGBSA-N 2-[(1s)-5-(6-chloropyridazin-3-yl)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-3-methyl-6-pyrimidin-4-ylpyrimidin-4-one Chemical compound C([C@]1(CN2C=3N=NC(Cl)=CC=3)[H])C2CN1C(N(C(=O)C=1)C)=NC=1C1=CC=NC=N1 DFGWLALTMJBIIQ-KIYNQFGBSA-N 0.000 claims 1
- OYZNNDPBMLIFFC-GGYWPGCISA-N 2-[(1s)-5-benzyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound C([C@]1(CN2CC=3C=CC=CC=3)[H])C2CN1C(N(C(=O)C=1)C)=NC=1C1=CC=NC=C1 OYZNNDPBMLIFFC-GGYWPGCISA-N 0.000 claims 1
- JIDOEWRJIIHGMQ-DJNXLDHESA-N 2-[(1s)-5-benzyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]-3-methyl-6-pyrimidin-4-ylpyrimidin-4-one Chemical compound C([C@]1(CN2CC=3C=CC=CC=3)[H])C2CN1C(N(C(=O)C=1)C)=NC=1C1=CC=NC=N1 JIDOEWRJIIHGMQ-DJNXLDHESA-N 0.000 claims 1
- IBNIKJLJNZHPIX-LYKKTTPLSA-N 2-[(4s)-2-(3-methoxybenzoyl)-2,5-diazabicyclo[2.2.1]heptan-5-yl]-3-methyl-6-pyrimidin-4-ylpyrimidin-4-one Chemical compound C([C@]1(CN2C(=O)C=3C=C(OC)C=CC=3)[H])C2CN1C(N(C(=O)C=1)C)=NC=1C1=CC=NC=N1 IBNIKJLJNZHPIX-LYKKTTPLSA-N 0.000 claims 1
- KIHYWWISRZTDRX-ZVAWYAOSSA-N 2-[(4s)-2-(4-chlorobenzoyl)-2,5-diazabicyclo[2.2.1]heptan-5-yl]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound C([C@]1(CN2C(=O)C=3C=CC(Cl)=CC=3)[H])C2CN1C(N(C(=O)C=1)C)=NC=1C1=CC=NC=C1 KIHYWWISRZTDRX-ZVAWYAOSSA-N 0.000 claims 1
- HMNOKCAOZXVMMP-LYKKTTPLSA-N 2-[(4s)-2-(4-chlorobenzoyl)-2,5-diazabicyclo[2.2.1]heptan-5-yl]-3-methyl-6-pyrimidin-4-ylpyrimidin-4-one Chemical compound C([C@]1(CN2C(=O)C=3C=CC(Cl)=CC=3)[H])C2CN1C(N(C(=O)C=1)C)=NC=1C1=CC=NC=N1 HMNOKCAOZXVMMP-LYKKTTPLSA-N 0.000 claims 1
- POIOEYCEMOUFNZ-ZVAWYAOSSA-N 2-[(4s)-2-(4-fluorobenzoyl)-2,5-diazabicyclo[2.2.1]heptan-5-yl]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound C([C@]1(CN2C(=O)C=3C=CC(F)=CC=3)[H])C2CN1C(N(C(=O)C=1)C)=NC=1C1=CC=NC=C1 POIOEYCEMOUFNZ-ZVAWYAOSSA-N 0.000 claims 1
- AVVOVRHAFLFAKS-LYKKTTPLSA-N 2-[(4s)-2-(4-methoxybenzoyl)-2,5-diazabicyclo[2.2.1]heptan-5-yl]-3-methyl-6-pyrimidin-4-ylpyrimidin-4-one Chemical compound C([C@]1(CN2C(=O)C=3C=CC(OC)=CC=3)[H])C2CN1C(N(C(=O)C=1)C)=NC=1C1=CC=NC=N1 AVVOVRHAFLFAKS-LYKKTTPLSA-N 0.000 claims 1
- FPWJFFISLAYAPL-DJNXLDHESA-N 3-methyl-2-[(1s)-5-(4-methylphenyl)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-6-pyrimidin-4-ylpyrimidin-4-one Chemical compound C([C@]1(CN2C=3C=CC(C)=CC=3)[H])C2CN1C(N(C(=O)C=1)C)=NC=1C1=CC=NC=N1 FPWJFFISLAYAPL-DJNXLDHESA-N 0.000 claims 1
- XCQYDCJZDNOHPD-LBAQZLPGSA-N 3-methyl-2-[(1s)-5-(5-phenylpyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-6-pyrimidin-4-ylpyrimidin-4-one Chemical compound C([C@]1(CN2C=3C=C(C=NC=3)C=3C=CC=CC=3)[H])C2CN1C(N(C(=O)C=1)C)=NC=1C1=CC=NC=N1 XCQYDCJZDNOHPD-LBAQZLPGSA-N 0.000 claims 1
- ZYVBULGXUHSMET-KZUDCZAMSA-N 3-methyl-2-[(1s)-5-pyridin-2-yl-2,5-diazabicyclo[2.2.1]heptan-2-yl]-6-pyrimidin-4-ylpyrimidin-4-one Chemical compound C([C@]1(CN2C=3N=CC=CC=3)[H])C2CN1C(N(C(=O)C=1)C)=NC=1C1=CC=NC=N1 ZYVBULGXUHSMET-KZUDCZAMSA-N 0.000 claims 1
- KJENINYPWYJVJR-LOACHALJSA-N 3-methyl-2-[(1s)-5-pyridin-4-yl-2,5-diazabicyclo[2.2.1]heptan-2-yl]-6-pyrimidin-4-ylpyrimidin-4-one Chemical compound C([C@]1(CN2C=3C=CN=CC=3)[H])C2CN1C(N(C(=O)C=1)C)=NC=1C1=CC=NC=N1 KJENINYPWYJVJR-LOACHALJSA-N 0.000 claims 1
- VUCAOFJVFOGGRO-GGYWPGCISA-N 3-methyl-2-[(4s)-2-(3-methylbenzoyl)-2,5-diazabicyclo[2.2.1]heptan-5-yl]-6-pyridin-4-ylpyrimidin-4-one Chemical compound C([C@]1(CN2C(=O)C=3C=C(C)C=CC=3)[H])C2CN1C(N(C(=O)C=1)C)=NC=1C1=CC=NC=C1 VUCAOFJVFOGGRO-GGYWPGCISA-N 0.000 claims 1
- ODRRWDAYULBGQD-DJNXLDHESA-N 3-methyl-2-[(4s)-2-(3-methylbenzoyl)-2,5-diazabicyclo[2.2.1]heptan-5-yl]-6-pyrimidin-4-ylpyrimidin-4-one Chemical compound C([C@]1(CN2C(=O)C=3C=C(C)C=CC=3)[H])C2CN1C(N(C(=O)C=1)C)=NC=1C1=CC=NC=N1 ODRRWDAYULBGQD-DJNXLDHESA-N 0.000 claims 1
- JWMWRKTXLQBDAA-DJNXLDHESA-N 3-methyl-2-[(4s)-2-(4-methylbenzoyl)-2,5-diazabicyclo[2.2.1]heptan-5-yl]-6-pyrimidin-4-ylpyrimidin-4-one Chemical compound C([C@]1(CN2C(=O)C=3C=CC(C)=CC=3)[H])C2CN1C(N(C(=O)C=1)C)=NC=1C1=CC=NC=N1 JWMWRKTXLQBDAA-DJNXLDHESA-N 0.000 claims 1
- GFZGQXFNCYAOLA-VYRBHSGPSA-N 3-methyl-2-[(4s)-2-(4-methylphenyl)sulfonyl-2,5-diazabicyclo[2.2.1]heptan-5-yl]-6-pyrimidin-4-ylpyrimidin-4-one Chemical compound C([C@]1(CN2S(=O)(=O)C=3C=CC(C)=CC=3)[H])C2CN1C(N(C(=O)C=1)C)=NC=1C1=CC=NC=N1 GFZGQXFNCYAOLA-VYRBHSGPSA-N 0.000 claims 1
- WVZPWGMLPHMICI-ZVAWYAOSSA-N 3-methyl-6-pyridin-4-yl-2-[(4s)-2-[4-(trifluoromethyl)benzoyl]-2,5-diazabicyclo[2.2.1]heptan-5-yl]pyrimidin-4-one Chemical compound C([C@]1(CN2C(=O)C=3C=CC(=CC=3)C(F)(F)F)[H])C2CN1C(N(C(=O)C=1)C)=NC=1C1=CC=NC=C1 WVZPWGMLPHMICI-ZVAWYAOSSA-N 0.000 claims 1
- XHXXHHAUOOJDJL-ZVAWYAOSSA-N 3-methyl-6-pyrimidin-4-yl-2-[(1s)-5-quinolin-3-yl-2,5-diazabicyclo[2.2.1]heptan-2-yl]pyrimidin-4-one Chemical compound C([C@]1(CN2C=3C=C4C=CC=CC4=NC=3)[H])C2CN1C(N(C(=O)C=1)C)=NC=1C1=CC=NC=N1 XHXXHHAUOOJDJL-ZVAWYAOSSA-N 0.000 claims 1
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- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 108010061506 tau-protein kinase Proteins 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
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Classifications
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
-
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
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- A—HUMAN NECESSITIES
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4995—Pyrazines or piperazines forming part of bridged ring systems
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
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- A—HUMAN NECESSITIES
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- A61P25/16—Anti-Parkinson drugs
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- 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
- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Psychiatry (AREA)
- Ophthalmology & Optometry (AREA)
- Cardiology (AREA)
- Hematology (AREA)
- Heart & Thoracic Surgery (AREA)
- Epidemiology (AREA)
- Obesity (AREA)
- Psychology (AREA)
- Vascular Medicine (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Dermatology (AREA)
- Urology & Nephrology (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP20030290571 EP1454908B1 (en) | 2003-03-07 | 2003-03-07 | Substituted pyridinyl-2-(diaza-bicyclo-alkyl)-pyrimidinone derivatives |
| EP03290570A EP1454910A1 (en) | 2003-03-07 | 2003-03-07 | Substituted pyrimidinyl-2-(diaza-bicyclo-alkyl)-pyrimidone derivatives |
| PCT/EP2004/003050 WO2004078759A1 (en) | 2003-03-07 | 2004-03-05 | Substituted 2-(diaza-bicyclo-alkyl)-pyrimidone derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ542136A true NZ542136A (en) | 2008-07-31 |
Family
ID=32963795
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ542136A NZ542136A (en) | 2003-03-07 | 2004-03-05 | Substituted 2-(diaza-bicyclo-alkyl)-pyrimidone derivatives |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US7211581B2 (enExample) |
| EP (1) | EP1603910B1 (enExample) |
| JP (1) | JP4778890B2 (enExample) |
| KR (1) | KR101072159B1 (enExample) |
| AR (1) | AR043486A1 (enExample) |
| AT (1) | ATE440844T1 (enExample) |
| AU (1) | AU2004218249B2 (enExample) |
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| CA (1) | CA2516934C (enExample) |
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| DE (1) | DE602004022784D1 (enExample) |
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| EA (1) | EA008595B1 (enExample) |
| ES (1) | ES2332132T3 (enExample) |
| IL (1) | IL170468A (enExample) |
| MX (1) | MXPA05009575A (enExample) |
| NO (1) | NO20054141L (enExample) |
| NZ (1) | NZ542136A (enExample) |
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| PT (1) | PT1603910E (enExample) |
| SI (1) | SI1603910T1 (enExample) |
| WO (1) | WO2004078759A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200813015A (en) | 2006-03-15 | 2008-03-16 | Mitsubishi Pharma Corp | 2-(cyclic amino)-pyrimidone derivatives |
| EP1992620A1 (en) | 2007-05-16 | 2008-11-19 | Sanofi-Aventis | Arylamide pyrimidone derivatives for the treatment of neurodegenerative diseases |
| EP1992625A1 (en) | 2007-05-16 | 2008-11-19 | Sanofi-Aventis | Arylamide pyrimidone compounds |
| EP1992624A1 (en) | 2007-05-16 | 2008-11-19 | Sanofi-Aventis | Heteroarylamide pyrimidone compounds |
| EP1992621A1 (en) * | 2007-05-16 | 2008-11-19 | Sanofi-Aventis | Heteroarylamide-substituted pyrimidone derivatives for the treatment of neurodegenerative diseases |
Family Cites Families (5)
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| US4994460A (en) * | 1989-06-01 | 1991-02-19 | Bristol-Myers Squibb Co. | Agents for treatment of brain ischemia |
| US5883254A (en) * | 1996-11-08 | 1999-03-16 | Hoffmann-La Roche Inc. | Process for making pyrimidine derivatives |
| EP1136483A1 (en) * | 2000-03-23 | 2001-09-26 | Sanofi-Synthelabo | 2-[Piperazinyl]pyrimidone derivatives |
| AU2001262150A1 (en) * | 2000-03-23 | 2001-10-03 | Mitsubishi Pharma Corporation | 2-(nitrogen-heterocyclic)pyrimidone derivatives |
| ES2250883T3 (es) * | 2002-02-28 | 2006-04-16 | Sanofi-Aventis | Derivados de 2-piridinil y 2-pirimidinil-6,7,8,9-tetrahidropirimido(1,2-a)pirimidin-4-ona sustituidos con heteroarilo. |
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2004
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- 2004-03-05 DK DK04717644T patent/DK1603910T3/da active
- 2004-03-05 ES ES04717644T patent/ES2332132T3/es not_active Expired - Lifetime
- 2004-03-05 DE DE602004022784T patent/DE602004022784D1/de not_active Expired - Lifetime
- 2004-03-05 WO PCT/EP2004/003050 patent/WO2004078759A1/en not_active Ceased
- 2004-03-05 PT PT04717644T patent/PT1603910E/pt unknown
- 2004-03-05 MX MXPA05009575A patent/MXPA05009575A/es active IP Right Grant
- 2004-03-05 NZ NZ542136A patent/NZ542136A/en not_active IP Right Cessation
- 2004-03-05 CA CA2516934A patent/CA2516934C/en not_active Expired - Fee Related
- 2004-03-05 EA EA200501243A patent/EA008595B1/ru not_active IP Right Cessation
- 2004-03-05 JP JP2006504812A patent/JP4778890B2/ja not_active Expired - Fee Related
- 2004-03-05 AU AU2004218249A patent/AU2004218249B2/en not_active Ceased
- 2004-03-05 EP EP04717644A patent/EP1603910B1/en not_active Expired - Lifetime
- 2004-03-05 SI SI200431263T patent/SI1603910T1/sl unknown
- 2004-03-05 AT AT04717644T patent/ATE440844T1/de active
- 2004-03-05 BR BRPI0408186-2A patent/BRPI0408186A/pt not_active IP Right Cessation
- 2004-03-05 PL PL04717644T patent/PL1603910T3/pl unknown
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2005
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- 2005-09-06 NO NO20054141A patent/NO20054141L/no not_active Application Discontinuation
- 2005-09-06 KR KR1020057016636A patent/KR101072159B1/ko not_active Expired - Fee Related
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2007
- 2007-03-29 US US11/693,345 patent/US7452897B2/en not_active Expired - Fee Related
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2009
- 2009-10-26 CY CY20091101113T patent/CY1111132T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR101072159B1 (ko) | 2011-10-10 |
| EP1603910B1 (en) | 2009-08-26 |
| US20070167455A1 (en) | 2007-07-19 |
| AU2004218249A1 (en) | 2004-09-16 |
| CA2516934A1 (en) | 2004-09-16 |
| MXPA05009575A (es) | 2006-05-19 |
| JP2006519813A (ja) | 2006-08-31 |
| US7452897B2 (en) | 2008-11-18 |
| US20060025417A1 (en) | 2006-02-02 |
| EP1603910A1 (en) | 2005-12-14 |
| NO20054141D0 (no) | 2005-09-06 |
| CY1111132T1 (el) | 2015-06-11 |
| JP4778890B2 (ja) | 2011-09-21 |
| NO20054141L (no) | 2005-12-07 |
| ATE440844T1 (de) | 2009-09-15 |
| KR20050113218A (ko) | 2005-12-01 |
| AR043486A1 (es) | 2005-08-03 |
| BRPI0408186A (pt) | 2006-04-04 |
| PL1603910T3 (pl) | 2010-02-26 |
| ES2332132T3 (es) | 2010-01-27 |
| IL170468A (en) | 2010-12-30 |
| PT1603910E (pt) | 2009-10-30 |
| US7211581B2 (en) | 2007-05-01 |
| WO2004078759A1 (en) | 2004-09-16 |
| CA2516934C (en) | 2011-09-20 |
| SI1603910T1 (sl) | 2009-12-31 |
| DE602004022784D1 (de) | 2009-10-08 |
| DK1603910T3 (da) | 2009-11-23 |
| AU2004218249B2 (en) | 2009-04-30 |
| EA008595B1 (ru) | 2007-06-29 |
| HK1085742A1 (zh) | 2006-09-01 |
| EA200501243A1 (ru) | 2006-04-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RENW | Renewal (renewal fees accepted) | ||
| PSEA | Patent sealed | ||
| RENW | Renewal (renewal fees accepted) | ||
| LAPS | Patent lapsed |