JP2012514631A5 - - Google Patents
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- Publication number
- JP2012514631A5 JP2012514631A5 JP2011544946A JP2011544946A JP2012514631A5 JP 2012514631 A5 JP2012514631 A5 JP 2012514631A5 JP 2011544946 A JP2011544946 A JP 2011544946A JP 2011544946 A JP2011544946 A JP 2011544946A JP 2012514631 A5 JP2012514631 A5 JP 2012514631A5
- Authority
- JP
- Japan
- Prior art keywords
- quinazolin
- stereoisomer
- hydrate
- tautomer
- pharmaceutically acceptable
- 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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- 150000003839 salts Chemical class 0.000 claims 50
- 150000001875 compounds Chemical class 0.000 claims 45
- 229910052739 hydrogen Inorganic materials 0.000 claims 42
- 239000001257 hydrogen Substances 0.000 claims 42
- 150000002431 hydrogen Chemical class 0.000 claims 34
- 229910052731 fluorine Inorganic materials 0.000 claims 23
- -1 is selected NMe 2 Chemical group 0.000 claims 20
- 239000000460 chlorine Substances 0.000 claims 18
- 239000008194 pharmaceutical composition Substances 0.000 claims 15
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 14
- 229910052794 bromium Inorganic materials 0.000 claims 14
- 229910052799 carbon Inorganic materials 0.000 claims 14
- 229910052801 chlorine Inorganic materials 0.000 claims 14
- 239000011737 fluorine Substances 0.000 claims 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 11
- 229910052757 nitrogen Inorganic materials 0.000 claims 9
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 8
- 229910005965 SO 2 Inorganic materials 0.000 claims 8
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 229910052740 iodine Inorganic materials 0.000 claims 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 5
- 102000005666 Apolipoprotein A-I Human genes 0.000 claims 4
- 108010059886 Apolipoprotein A-I Proteins 0.000 claims 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 4
- 239000008280 blood Substances 0.000 claims 4
- 210000004369 blood Anatomy 0.000 claims 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims 3
- 235000012000 cholesterol Nutrition 0.000 claims 3
- 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 3
- 150000002632 lipids Chemical class 0.000 claims 3
- QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical compound C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 claims 2
- XCUAIINAJCDIPM-XVFCMESISA-N N(4)-hydroxycytidine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=NO)C=C1 XCUAIINAJCDIPM-XVFCMESISA-N 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- FBQICEIXZHCUSF-UHFFFAOYSA-N 2-(1h-indol-5-yl)-3-(4-propan-2-ylphenyl)quinazolin-4-one Chemical compound C1=CC(C(C)C)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(NC=C2)C2=C1 FBQICEIXZHCUSF-UHFFFAOYSA-N 0.000 claims 1
- JWQKBRRBNLSXCT-UHFFFAOYSA-N 2-(1h-indol-5-yl)-3-[4-(trifluoromethoxy)phenyl]quinazolin-4-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(NC=C2)C2=C1 JWQKBRRBNLSXCT-UHFFFAOYSA-N 0.000 claims 1
- DHFPRDLXYFACHV-UHFFFAOYSA-N 2-(5-bromopyridin-3-yl)-3-(4-butan-2-ylphenyl)quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CN=CC(Br)=C1 DHFPRDLXYFACHV-UHFFFAOYSA-N 0.000 claims 1
- OZUGFQKQFWHVPE-UHFFFAOYSA-N 2-(5-bromopyridin-3-yl)-3-(4-chlorophenyl)quinazolin-4-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CN=CC(Br)=C1 OZUGFQKQFWHVPE-UHFFFAOYSA-N 0.000 claims 1
- YHIZKXPNEDFRCG-UHFFFAOYSA-N 2-(6-bromopyridin-3-yl)-3-(4-butan-2-ylphenyl)quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(Br)N=C1 YHIZKXPNEDFRCG-UHFFFAOYSA-N 0.000 claims 1
- DFPDROFHDIFMKK-UHFFFAOYSA-N 2-(6-bromopyridin-3-yl)-3-(4-chlorophenyl)quinazolin-4-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(Br)N=C1 DFPDROFHDIFMKK-UHFFFAOYSA-N 0.000 claims 1
- UGALAJRSLYKETA-UHFFFAOYSA-N 2-(6-chloropyridin-3-yl)-3-(4-cyclopropylphenyl)quinazolin-4-one Chemical compound C1=NC(Cl)=CC=C1C1=NC2=CC=CC=C2C(=O)N1C1=CC=C(C2CC2)C=C1 UGALAJRSLYKETA-UHFFFAOYSA-N 0.000 claims 1
- MSHZYSBUIBCCQR-UHFFFAOYSA-N 2-(6-methylpyridin-3-yl)-3-(4-methylsulfanylphenyl)quinazolin-4-one Chemical compound C1=CC(SC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(C)N=C1 MSHZYSBUIBCCQR-UHFFFAOYSA-N 0.000 claims 1
- UHBJGOGLEGXENZ-UHFFFAOYSA-N 2-(6-methylpyridin-3-yl)-3-(4-propan-2-ylphenyl)quinazolin-4-one Chemical compound C1=CC(C(C)C)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(C)N=C1 UHBJGOGLEGXENZ-UHFFFAOYSA-N 0.000 claims 1
- FJJFYFXQPFKOGS-UHFFFAOYSA-N 2-[1-(benzenesulfonyl)pyrrolo[2,3-b]pyridin-5-yl]-3-(4-chlorophenyl)quinazolin-4-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CN=C(N(C=C2)S(=O)(=O)C=3C=CC=CC=3)C2=C1 FJJFYFXQPFKOGS-UHFFFAOYSA-N 0.000 claims 1
- RKAJCRHQYCQUIJ-UHFFFAOYSA-N 2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]-3-(4-iodophenyl)quinazolin-4-one Chemical compound CC1=C(OCCO)C(C)=CC(C=2N(C(=O)C3=CC=CC=C3N=2)C=2C=CC(I)=CC=2)=C1 RKAJCRHQYCQUIJ-UHFFFAOYSA-N 0.000 claims 1
- BCHCHJNQUJRDGT-UHFFFAOYSA-N 2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]-3-(4-morpholin-4-ylphenyl)quinazolin-4-one Chemical compound CC1=C(OCCO)C(C)=CC(C=2N(C(=O)C3=CC=CC=C3N=2)C=2C=CC(=CC=2)N2CCOCC2)=C1 BCHCHJNQUJRDGT-UHFFFAOYSA-N 0.000 claims 1
- DBZKIEKURBHGOQ-UHFFFAOYSA-N 2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]-3-(4-propan-2-ylphenyl)quinazolin-4-one Chemical compound C1=CC(C(C)C)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC(C)=C(OCCO)C(C)=C1 DBZKIEKURBHGOQ-UHFFFAOYSA-N 0.000 claims 1
- KDNWYRLSNWUQHB-UHFFFAOYSA-N 2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]-3-[4-(trifluoromethyl)phenyl]quinazolin-4-one Chemical compound CC1=C(OCCO)C(C)=CC(C=2N(C(=O)C3=CC=CC=C3N=2)C=2C=CC(=CC=2)C(F)(F)F)=C1 KDNWYRLSNWUQHB-UHFFFAOYSA-N 0.000 claims 1
- CMBCIGQSOTZAJG-UHFFFAOYSA-N 3-(4-aminophenyl)-2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]quinazolin-4-one Chemical compound CC1=C(OCCO)C(C)=CC(C=2N(C(=O)C3=CC=CC=C3N=2)C=2C=CC(N)=CC=2)=C1 CMBCIGQSOTZAJG-UHFFFAOYSA-N 0.000 claims 1
- AOUBRIJJTDSEFP-UHFFFAOYSA-N 3-(4-bromophenyl)-2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]-6-methoxyquinazolin-4-one Chemical compound C=1C=C(Br)C=CC=1N1C(=O)C2=CC(OC)=CC=C2N=C1C1=CC(C)=C(OCCO)C(C)=C1 AOUBRIJJTDSEFP-UHFFFAOYSA-N 0.000 claims 1
- YCTVTSSLGLSZAR-UHFFFAOYSA-N 3-(4-bromophenyl)-2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]-8-methoxyquinazolin-4-one Chemical compound COC1=CC=CC(C(N2C=3C=CC(Br)=CC=3)=O)=C1N=C2C1=CC(C)=C(OCCO)C(C)=C1 YCTVTSSLGLSZAR-UHFFFAOYSA-N 0.000 claims 1
- MHHKKQCBXMYTBT-UHFFFAOYSA-N 3-(4-bromophenyl)-2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]quinazolin-4-one Chemical compound CC1=C(OCCO)C(C)=CC(C=2N(C(=O)C3=CC=CC=C3N=2)C=2C=CC(Br)=CC=2)=C1 MHHKKQCBXMYTBT-UHFFFAOYSA-N 0.000 claims 1
- RMZSWYMBNQXQBT-UHFFFAOYSA-N 3-(4-bromophenyl)-2-[4-(2-hydroxyethoxy)-3-methylphenyl]quinazolin-4-one Chemical compound C1=C(OCCO)C(C)=CC(C=2N(C(=O)C3=CC=CC=C3N=2)C=2C=CC(Br)=CC=2)=C1 RMZSWYMBNQXQBT-UHFFFAOYSA-N 0.000 claims 1
- OPIXKJHACSNHAB-UHFFFAOYSA-N 3-(4-bromophenyl)-8-chloro-2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]quinazolin-4-one Chemical compound CC1=C(OCCO)C(C)=CC(C=2N(C(=O)C3=CC=CC(Cl)=C3N=2)C=2C=CC(Br)=CC=2)=C1 OPIXKJHACSNHAB-UHFFFAOYSA-N 0.000 claims 1
- OKRYXQFBDRWPGY-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-(1h-indazol-5-yl)quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(NN=C2)C2=C1 OKRYXQFBDRWPGY-UHFFFAOYSA-N 0.000 claims 1
- VVNDNZSFPSYQEI-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-(1h-indol-5-yl)quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(NC=C2)C2=C1 VVNDNZSFPSYQEI-UHFFFAOYSA-N 0.000 claims 1
- LJMLPZCMCCQTLT-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-(1h-indol-6-yl)quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(C=CN2)C2=C1 LJMLPZCMCCQTLT-UHFFFAOYSA-N 0.000 claims 1
- FIIGJZVHSNKSIU-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-(1h-indol-7-yl)quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=CC2=C1NC=C2 FIIGJZVHSNKSIU-UHFFFAOYSA-N 0.000 claims 1
- YKQANQSXCDWCKY-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-(5-fluoropyridin-3-yl)quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CN=CC(F)=C1 YKQANQSXCDWCKY-UHFFFAOYSA-N 0.000 claims 1
- LJZHVNARCITLDT-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-(5-phenylpyridin-3-yl)quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CN=CC(C=2C=CC=CC=2)=C1 LJZHVNARCITLDT-UHFFFAOYSA-N 0.000 claims 1
- CHJRJWBDMODIIS-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-(6-chloropyridin-3-yl)quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(Cl)N=C1 CHJRJWBDMODIIS-UHFFFAOYSA-N 0.000 claims 1
- FCNKYBTWDSZWIF-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-(6-fluoropyridin-3-yl)quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(F)N=C1 FCNKYBTWDSZWIF-UHFFFAOYSA-N 0.000 claims 1
- WHIOZSKENDJXSA-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-(6-methoxypyridin-3-yl)quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(OC)N=C1 WHIOZSKENDJXSA-UHFFFAOYSA-N 0.000 claims 1
- MMHJYVUBDAYCHP-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-(6-methylpyridin-3-yl)quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(C)N=C1 MMHJYVUBDAYCHP-UHFFFAOYSA-N 0.000 claims 1
- NODCZFRSJFGEAB-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-(6-morpholin-4-ylpyridin-3-yl)quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(N2CCOCC2)N=C1 NODCZFRSJFGEAB-UHFFFAOYSA-N 0.000 claims 1
- MAADFZNOPLSTHR-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-(6-phenoxypyridin-3-yl)quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C(C=N1)=CC=C1OC1=CC=CC=C1 MAADFZNOPLSTHR-UHFFFAOYSA-N 0.000 claims 1
- YBRBUVMFJBWOLH-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-(6-phenylpyridin-3-yl)quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(C=2C=CC=CC=2)N=C1 YBRBUVMFJBWOLH-UHFFFAOYSA-N 0.000 claims 1
- XEIBCRVYNCEUOP-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-(6-piperidin-1-ylpyridin-3-yl)quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(N2CCCCC2)N=C1 XEIBCRVYNCEUOP-UHFFFAOYSA-N 0.000 claims 1
- CJQOSNRWGMURNH-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-[2-(hydroxymethyl)-1h-indol-5-yl]quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(NC(CO)=C2)C2=C1 CJQOSNRWGMURNH-UHFFFAOYSA-N 0.000 claims 1
- UBJYLRRBBMGOJX-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-[2-(hydroxymethyl)-3h-benzimidazol-5-yl]quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(N=C(CO)N2)C2=C1 UBJYLRRBBMGOJX-UHFFFAOYSA-N 0.000 claims 1
- VSQCFAVZPFEZSL-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]-6-methoxyquinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC(OC)=CC=C2N=C1C1=CC(C)=C(OCCO)C(C)=C1 VSQCFAVZPFEZSL-UHFFFAOYSA-N 0.000 claims 1
- LVQNHQOUQNMLEP-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]-6-methylsulfonylquinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC(S(C)(=O)=O)=CC=C2N=C1C1=CC(C)=C(OCCO)C(C)=C1 LVQNHQOUQNMLEP-UHFFFAOYSA-N 0.000 claims 1
- VMENXQKOUGXXQB-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]-7-methylsulfonylquinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=C(S(C)(=O)=O)C=C2N=C1C1=CC(C)=C(OCCO)C(C)=C1 VMENXQKOUGXXQB-UHFFFAOYSA-N 0.000 claims 1
- KAMDXLPPEHVTBH-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]-8-methoxyquinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC(OC)=C2N=C1C1=CC(C)=C(OCCO)C(C)=C1 KAMDXLPPEHVTBH-UHFFFAOYSA-N 0.000 claims 1
- LNSFWGANTMLKFH-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]pyrido[4,3-d]pyrimidin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CN=CC=C2N=C1C1=CC(C)=C(OCCO)C(C)=C1 LNSFWGANTMLKFH-UHFFFAOYSA-N 0.000 claims 1
- QRQNMYJLPBKCGF-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC(C)=C(OCCO)C(C)=C1 QRQNMYJLPBKCGF-UHFFFAOYSA-N 0.000 claims 1
- INMSMJGRAMYTHH-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-[4-(2-hydroxyethoxy)-3-methylphenyl]quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(OCCO)C(C)=C1 INMSMJGRAMYTHH-UHFFFAOYSA-N 0.000 claims 1
- QNAKGEGVMUTASP-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-[4-(2-hydroxyethoxy)phenyl]quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(OCCO)C=C1 QNAKGEGVMUTASP-UHFFFAOYSA-N 0.000 claims 1
- NLLASDGHSCUILA-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-[5-(diethylamino)pyridin-3-yl]quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CN=CC(N(CC)CC)=C1 NLLASDGHSCUILA-UHFFFAOYSA-N 0.000 claims 1
- GQUONRMVMIROAV-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-[6-(diethylamino)pyridin-3-yl]quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(N(CC)CC)N=C1 GQUONRMVMIROAV-UHFFFAOYSA-N 0.000 claims 1
- SEJZRPRKEXKOKZ-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-[6-(hydroxymethyl)pyridin-3-yl]quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(CO)N=C1 SEJZRPRKEXKOKZ-UHFFFAOYSA-N 0.000 claims 1
- KGUGHRUYZKGKRN-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-[6-(morpholin-4-ylmethyl)pyridin-3-yl]quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C(C=N1)=CC=C1CN1CCOCC1 KGUGHRUYZKGKRN-UHFFFAOYSA-N 0.000 claims 1
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| PT2118074E (pt) | 2007-02-01 | 2014-03-20 | Resverlogix Corp | Compostos para a prevenção e tratamento de doenças cardiovasculares |
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| US9452973B2 (en) | 2012-05-04 | 2016-09-27 | The United States Of America, As Represented By The Secretary Department Of Health And Human Services | Modulators of the relaxin receptor 1 |
| PT2906531T (pt) | 2012-10-15 | 2018-02-06 | Resverlogix Corp | Compostos úteis na síntese de compostos de benzamida |
| US9765039B2 (en) | 2012-11-21 | 2017-09-19 | Zenith Epigenetics Ltd. | Biaryl derivatives as bromodomain inhibitors |
| US9073878B2 (en) | 2012-11-21 | 2015-07-07 | Zenith Epigenetics Corp. | Cyclic amines as bromodomain inhibitors |
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| US10111885B2 (en) | 2015-03-13 | 2018-10-30 | Resverlogix Corp. | Compositions and therapeutic methods for the treatment of complement-associated diseases |
| EP3562483B1 (en) | 2016-12-20 | 2025-09-03 | Oligomerix, Inc. | Novel benzofuran, benzothiophene, and indole analogs that inhibit the formation of tau oligomers and their method of use |
| EP4252856A3 (en) * | 2016-12-20 | 2024-01-24 | Oligomerix, Inc. | Novel quinazolinones that inhibit the formation of tau oligomers and their method of use |
| AU2019284971A1 (en) | 2018-06-13 | 2020-12-03 | Worg Pharmaceuticals (Zhejiang) Co., Ltd. | Preparation of condensed triazepine derivatives and their use as BET inhibitors |
| US20230053152A1 (en) * | 2019-11-26 | 2023-02-16 | Benobio Co., Ltd. | Novel Quercetin Redox Derivative And Use Thereof As BET Inhibitor |
| WO2022014433A1 (ja) * | 2020-07-13 | 2022-01-20 | 国立大学法人富山大学 | Ｎｒ４ａ１拮抗薬を用いた鎮痛薬 |
| RU2763022C1 (ru) * | 2021-07-05 | 2021-12-24 | Федеральное государственное автономное образовательное учреждение высшего образования "Пермский государственный национальный исследовательский университет" (ПГНИУ) | Способ получения 6-арил-5-(3-оксо-4-фенил-3,4-дигидрохиноксалин-2-ил)-2,3-дигидро-4Н-1,3-оксазин-4-онов |
| JP2025540768A (ja) * | 2022-11-30 | 2025-12-16 | ヘルムホルツ・ツェントルム・ミュンヘン・ドイチェス・フォーシュンクスツェントルム・フュア・ゲズントハイト・ウント・ウンベルト・ゲーエムベーハー | 新規抗がん治療としての３－フェニルキノアゾリノン類 |
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-
2010
- 2010-01-08 US US13/143,757 patent/US8952021B2/en not_active Expired - Fee Related
- 2010-01-08 AU AU2010204106A patent/AU2010204106B2/en not_active Ceased
- 2010-01-08 JP JP2011544946A patent/JP5635535B2/ja not_active Expired - Fee Related
- 2010-01-08 CA CA2747417A patent/CA2747417C/en not_active Expired - Fee Related
- 2010-01-08 WO PCT/IB2010/000159 patent/WO2010079431A2/en not_active Ceased
- 2010-01-08 ES ES10704977.7T patent/ES2463097T3/es active Active
- 2010-01-08 EP EP10704977.7A patent/EP2382194B1/en not_active Not-in-force
- 2010-01-08 ES ES13175561.3T patent/ES2542835T3/es active Active
- 2010-01-08 NZ NZ594332A patent/NZ594332A/xx not_active IP Right Cessation
- 2010-01-08 EP EP20130175561 patent/EP2660238B1/en not_active Not-in-force
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