JP2012514631A5 - - Google Patents
Download PDFInfo
- 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
Links
- 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
- ZBSMUXWSTOCQNY-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-[6-(trifluoromethyl)pyridin-3-yl]quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(C(F)(F)F)N=C1 ZBSMUXWSTOCQNY-UHFFFAOYSA-N 0.000 claims 1
- RWIAATVZTPFKFH-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-pyridin-3-ylquinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=CN=C1 RWIAATVZTPFKFH-UHFFFAOYSA-N 0.000 claims 1
- HOKHPQSUTVJSDN-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-2-pyrimidin-5-ylquinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CN=CN=C1 HOKHPQSUTVJSDN-UHFFFAOYSA-N 0.000 claims 1
- HKKXQLSOJYIMFU-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-6-fluoro-2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC(F)=CC=C2N=C1C1=CC(C)=C(OCCO)C(C)=C1 HKKXQLSOJYIMFU-UHFFFAOYSA-N 0.000 claims 1
- HGGZQMKJVJLMPN-UHFFFAOYSA-N 3-(4-butan-2-ylphenyl)-7-fluoro-2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]quinazolin-4-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=CC=C(F)C=C2N=C1C1=CC(C)=C(OCCO)C(C)=C1 HGGZQMKJVJLMPN-UHFFFAOYSA-N 0.000 claims 1
- QZVBTXWUPXBSQP-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-(1-methylindol-5-yl)quinazolin-4-one Chemical compound C=1C=C2N(C)C=CC2=CC=1C1=NC2=CC=CC=C2C(=O)N1C1=CC=C(Cl)C=C1 QZVBTXWUPXBSQP-UHFFFAOYSA-N 0.000 claims 1
- KVZNCXGALLAQMW-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-(1h-indol-4-yl)quinazolin-4-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=CC2=C1C=CN2 KVZNCXGALLAQMW-UHFFFAOYSA-N 0.000 claims 1
- TZMGOYQZLRMXIC-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-(1h-indol-5-yl)quinazolin-4-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(NC=C2)C2=C1 TZMGOYQZLRMXIC-UHFFFAOYSA-N 0.000 claims 1
- HCOKOYSPWRDAQH-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-(1h-indol-6-yl)quinazolin-4-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(C=CN2)C2=C1 HCOKOYSPWRDAQH-UHFFFAOYSA-N 0.000 claims 1
- MKJPWROAUIBBJU-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-(1h-indol-7-yl)quinazolin-4-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=CC2=C1NC=C2 MKJPWROAUIBBJU-UHFFFAOYSA-N 0.000 claims 1
- PAGDMOSDIOJUTP-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-(5-phenylpyridin-3-yl)quinazolin-4-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CN=CC(C=2C=CC=CC=2)=C1 PAGDMOSDIOJUTP-UHFFFAOYSA-N 0.000 claims 1
- DIADEZHWQHCNID-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-(6-chloropyridin-3-yl)quinazolin-4-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(Cl)N=C1 DIADEZHWQHCNID-UHFFFAOYSA-N 0.000 claims 1
- BLNSFSINSRHDNB-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-(6-methylpyridin-3-yl)quinazolin-4-one Chemical compound C1=NC(C)=CC=C1C1=NC2=CC=CC=C2C(=O)N1C1=CC=C(Cl)C=C1 BLNSFSINSRHDNB-UHFFFAOYSA-N 0.000 claims 1
- WJXGJFUIZLPDBG-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-(6-phenoxypyridin-3-yl)quinazolin-4-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C(C=N1)=CC=C1OC1=CC=CC=C1 WJXGJFUIZLPDBG-UHFFFAOYSA-N 0.000 claims 1
- AMJNDIFCBMOIPD-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-(6-piperidin-1-ylpyridin-3-yl)quinazolin-4-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(N2CCCCC2)N=C1 AMJNDIFCBMOIPD-UHFFFAOYSA-N 0.000 claims 1
- JRYHINPLIQGNHE-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-[1-(4-fluorophenyl)sulfonylpyrrolo[2,3-b]pyridin-5-yl]quinazolin-4-one Chemical compound C1=CC(F)=CC=C1S(=O)(=O)N1C2=NC=C(C=3N(C(=O)C4=CC=CC=C4N=3)C=3C=CC(Cl)=CC=3)C=C2C=C1 JRYHINPLIQGNHE-UHFFFAOYSA-N 0.000 claims 1
- LYDCAPKQOYWSIO-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-[1-(4-methoxyphenyl)sulfonylpyrrolo[2,3-b]pyridin-5-yl]quinazolin-4-one Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C2=NC=C(C=3N(C(=O)C4=CC=CC=C4N=3)C=3C=CC(Cl)=CC=3)C=C2C=C1 LYDCAPKQOYWSIO-UHFFFAOYSA-N 0.000 claims 1
- YDYFMJSHICXTNW-UHFFFAOYSA-N 3-(4-chlorophenyl)-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(Cl)=CC=2)=C1 YDYFMJSHICXTNW-UHFFFAOYSA-N 0.000 claims 1
- FTYQJMQPDRGGRH-UHFFFAOYSA-N 3-(4-chlorophenyl)-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(Cl)=CC=2)=C1 FTYQJMQPDRGGRH-UHFFFAOYSA-N 0.000 claims 1
- WUEOQIZUURPEJD-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-[5-(diethylamino)pyridin-3-yl]quinazolin-4-one Chemical compound CCN(CC)C1=CN=CC(C=2N(C(=O)C3=CC=CC=C3N=2)C=2C=CC(Cl)=CC=2)=C1 WUEOQIZUURPEJD-UHFFFAOYSA-N 0.000 claims 1
- TZHIGQZVCZGIBD-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-[6-(diethylamino)pyridin-3-yl]quinazolin-4-one Chemical compound C1=NC(N(CC)CC)=CC=C1C1=NC2=CC=CC=C2C(=O)N1C1=CC=C(Cl)C=C1 TZHIGQZVCZGIBD-UHFFFAOYSA-N 0.000 claims 1
- RNMRPENFUBUXDT-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-[6-(trifluoromethyl)pyridin-3-yl]quinazolin-4-one Chemical compound C1=NC(C(F)(F)F)=CC=C1C1=NC2=CC=CC=C2C(=O)N1C1=CC=C(Cl)C=C1 RNMRPENFUBUXDT-UHFFFAOYSA-N 0.000 claims 1
- HLXCFUFGTUUCJE-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-quinolin-3-ylquinazolin-4-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CN=C(C=CC=C2)C2=C1 HLXCFUFGTUUCJE-UHFFFAOYSA-N 0.000 claims 1
- ZYONEZWBPCJRII-UHFFFAOYSA-N 3-(4-cyclohexylphenyl)-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(=CC=2)C2CCCCC2)=C1 ZYONEZWBPCJRII-UHFFFAOYSA-N 0.000 claims 1
- FFMWFPPYPOGKAU-UHFFFAOYSA-N 3-(4-cyclopentylphenyl)-2-(1h-indol-5-yl)quinazolin-4-one Chemical compound C=1C=C2NC=CC2=CC=1C1=NC2=CC=CC=C2C(=O)N1C(C=C1)=CC=C1C1CCCC1 FFMWFPPYPOGKAU-UHFFFAOYSA-N 0.000 claims 1
- WKJLEHOBDGTEEC-UHFFFAOYSA-N 3-(4-cyclopentylphenyl)-2-(6-methylpyridin-3-yl)quinazolin-4-one Chemical compound C1=NC(C)=CC=C1C1=NC2=CC=CC=C2C(=O)N1C1=CC=C(C2CCCC2)C=C1 WKJLEHOBDGTEEC-UHFFFAOYSA-N 0.000 claims 1
- ZKDJBSSPAFZLGC-UHFFFAOYSA-N 3-(4-cyclopropylphenyl)-2-(6-methylpyridin-3-yl)quinazolin-4-one Chemical compound C1=NC(C)=CC=C1C1=NC2=CC=CC=C2C(=O)N1C1=CC=C(C2CC2)C=C1 ZKDJBSSPAFZLGC-UHFFFAOYSA-N 0.000 claims 1
- IQABTAQYLOGSPP-UHFFFAOYSA-N 3-(4-fluorophenyl)-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(F)=CC=2)=C1 IQABTAQYLOGSPP-UHFFFAOYSA-N 0.000 claims 1
- RPLJQAZHANXHFM-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-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(=CC=2)C(C)(C)C)=C1 RPLJQAZHANXHFM-UHFFFAOYSA-N 0.000 claims 1
- DKBBMKIZLVSGMX-UHFFFAOYSA-N 3-[4-(dimethylamino)phenyl]-2-(1h-indol-5-yl)quinazolin-4-one Chemical compound C1=CC(N(C)C)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(NC=C2)C2=C1 DKBBMKIZLVSGMX-UHFFFAOYSA-N 0.000 claims 1
- MMUSZUHFAUDSKR-UHFFFAOYSA-N 3-[4-(dimethylamino)phenyl]-2-(6-methylpyridin-3-yl)quinazolin-4-one Chemical compound C1=CC(N(C)C)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC=C(C)N=C1 MMUSZUHFAUDSKR-UHFFFAOYSA-N 0.000 claims 1
- RJFWYLQWEYURCM-UHFFFAOYSA-N 3-[4-(dimethylamino)phenyl]-2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]quinazolin-4-one Chemical compound C1=CC(N(C)C)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC(C)=C(OCCO)C(C)=C1 RJFWYLQWEYURCM-UHFFFAOYSA-N 0.000 claims 1
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims 1
- 102000018616 Apolipoproteins B Human genes 0.000 claims 1
- 108010027006 Apolipoproteins B Proteins 0.000 claims 1
- 208000034826 Genetic Predisposition to Disease Diseases 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 230000003143 atherosclerotic effect Effects 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- UVVICCNROUXIMN-UHFFFAOYSA-N cyclopropyl hypochlorite Chemical compound ClOC1CC1 UVVICCNROUXIMN-UHFFFAOYSA-N 0.000 claims 1
- 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000002068 genetic effect Effects 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 230000003902 lesion Effects 0.000 claims 1
- 230000037356 lipid metabolism Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- QVHOSRRKZUEHIH-UHFFFAOYSA-N methyl 4-[2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]-4-oxoquinazolin-3-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC(C)=C(OCCO)C(C)=C1 QVHOSRRKZUEHIH-UHFFFAOYSA-N 0.000 claims 1
- 125000006217 methyl sulfide group Chemical group [H]C([H])([H])S* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- DZPRXCUYJUSBLM-UHFFFAOYSA-N n-[4-[2-(6-methylpyridin-3-yl)-4-oxoquinazolin-3-yl]phenyl]methanesulfonamide Chemical compound C1=NC(C)=CC=C1C1=NC2=CC=CC=C2C(=O)N1C1=CC=C(NS(C)(=O)=O)C=C1 DZPRXCUYJUSBLM-UHFFFAOYSA-N 0.000 claims 1
- DYEKMRZSOXNYHL-UHFFFAOYSA-N n-[4-[2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]-4-oxoquinazolin-3-yl]phenyl]-2-methylpropanamide Chemical compound C1=CC(NC(=O)C(C)C)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC(C)=C(OCCO)C(C)=C1 DYEKMRZSOXNYHL-UHFFFAOYSA-N 0.000 claims 1
- VAIACDKPQXPTID-UHFFFAOYSA-N n-[4-[2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]-4-oxoquinazolin-3-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC(C)=C(OCCO)C(C)=C1 VAIACDKPQXPTID-UHFFFAOYSA-N 0.000 claims 1
- HGZRIMCWFYYKDH-UHFFFAOYSA-N n-[4-[2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]-4-oxoquinazolin-3-yl]phenyl]benzenesulfonamide Chemical compound CC1=C(OCCO)C(C)=CC(C=2N(C(=O)C3=CC=CC=C3N=2)C=2C=CC(NS(=O)(=O)C=3C=CC=CC=3)=CC=2)=C1 HGZRIMCWFYYKDH-UHFFFAOYSA-N 0.000 claims 1
- ZHKPASTWADEESO-UHFFFAOYSA-N n-[4-[2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]-4-oxoquinazolin-3-yl]phenyl]formamide Chemical compound CC1=C(OCCO)C(C)=CC(C=2N(C(=O)C3=CC=CC=C3N=2)C=2C=CC(NC=O)=CC=2)=C1 ZHKPASTWADEESO-UHFFFAOYSA-N 0.000 claims 1
- XFNAFDUFISCMNF-UHFFFAOYSA-N n-[4-[2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]-4-oxoquinazolin-3-yl]phenyl]methanesulfonamide Chemical compound CC1=C(OCCO)C(C)=CC(C=2N(C(=O)C3=CC=CC=C3N=2)C=2C=CC(NS(C)(=O)=O)=CC=2)=C1 XFNAFDUFISCMNF-UHFFFAOYSA-N 0.000 claims 1
- KQMYKFRYTCHDOI-UHFFFAOYSA-N n-[4-[2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]-4-oxoquinazolin-3-yl]phenyl]propane-2-sulfonamide Chemical compound C1=CC(NS(=O)(=O)C(C)C)=CC=C1N1C(=O)C2=CC=CC=C2N=C1C1=CC(C)=C(OCCO)C(C)=C1 KQMYKFRYTCHDOI-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14327609P | 2009-01-08 | 2009-01-08 | |
| US61/143,276 | 2009-01-08 | ||
| PCT/IB2010/000159 WO2010079431A2 (en) | 2009-01-08 | 2010-01-08 | Compounds for the prevention and treatment of cardiovascular disease |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012514631A JP2012514631A (ja) | 2012-06-28 |
| JP2012514631A5 true JP2012514631A5 (enExample) | 2013-02-28 |
| JP5635535B2 JP5635535B2 (ja) | 2014-12-03 |
Family
ID=42104685
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011544946A Expired - Fee Related JP5635535B2 (ja) | 2009-01-08 | 2010-01-08 | 心血管疾患の予防および治療のための化合物 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8952021B2 (enExample) |
| EP (2) | EP2382194B1 (enExample) |
| JP (1) | JP5635535B2 (enExample) |
| AU (1) | AU2010204106B2 (enExample) |
| CA (1) | CA2747417C (enExample) |
| ES (2) | ES2542835T3 (enExample) |
| NZ (1) | NZ594332A (enExample) |
| WO (1) | WO2010079431A2 (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7846915B2 (en) | 2004-10-20 | 2010-12-07 | Resverlogix Corporation | Stilbenes and chalcones for the prevention and treatment of cardiovascular diseases |
| US8410109B2 (en) * | 2005-07-29 | 2013-04-02 | Resverlogix Corp. | Pharmaceutical compositions for the prevention and treatment of complex diseases and their delivery by insertable medical devices |
| JP2010505811A (ja) * | 2006-10-04 | 2010-02-25 | ファイザー・プロダクツ・インク | カルシウム受容体アンタゴニストとしてのピリド［４，３−ｄ］ピリミジン−４（３Ｈ）−オン誘導体 |
| MX2009008099A (es) | 2007-02-01 | 2009-12-14 | Resverlogix Corp | Compuestos para la prevencion y tratamiento de enfermedades cardiovasculares. |
| KR101629356B1 (ko) | 2008-06-26 | 2016-06-13 | 리스버로직스 코퍼레이션 | 퀴나졸리논 유도체의 제조방법 |
| AU2009265813B2 (en) * | 2008-07-02 | 2014-04-10 | F. Hoffmann-La Roche Ag | Novel phenylpyrazinones as kinase inhibitors |
| KR101913109B1 (ko) | 2009-03-18 | 2018-10-31 | 리스버로직스 코퍼레이션 | 신규한 소염제 |
| DK2421533T3 (en) | 2009-04-22 | 2019-01-07 | Resverlogix Corp | Hitherto unknown anti-inflammatory agents |
| WO2013033270A2 (en) | 2011-08-29 | 2013-03-07 | Coferon, Inc. | Bromodomain ligands capable of dimerizing in an aqueous solution, and methods of using same |
| WO2013033269A1 (en) | 2011-08-29 | 2013-03-07 | Coferon, Inc. | Bioorthogonal monomers capable of dimerizing and targeting bromodomains and methods of using same |
| LT2773354T (lt) | 2011-11-01 | 2019-08-12 | Resverlogix Corp. | Geriamosios greitai atsipalaiduojančios pakeistų chinozolinų vaisto formos |
| 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 |
| KR101532570B1 (ko) | 2012-10-15 | 2015-06-30 | 리스버로직스 코퍼레이션 | 벤즈아미드 화합물의 합성에 유용한 화합물 |
| US9073878B2 (en) | 2012-11-21 | 2015-07-07 | Zenith Epigenetics Corp. | Cyclic amines as bromodomain inhibitors |
| WO2014080291A2 (en) | 2012-11-21 | 2014-05-30 | Rvx Therapeutics Inc. | Biaryl derivatives as bromodomain inhibitors |
| WO2014096965A2 (en) | 2012-12-21 | 2014-06-26 | Rvx Therapeutics Inc. | Novel heterocyclic compounds as bromodomain inhibitors |
| JP6903585B2 (ja) | 2015-03-13 | 2021-07-14 | レスバーロジックス コーポレイション | 補体関連疾患の治療のための組成物および治療方法 |
| EP3558950B1 (en) * | 2016-12-20 | 2023-05-10 | Oligomerix, Inc. | Novel quinazolinones that inhibit the formation of tau oligomers and their method of use |
| 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 |
| MX2020013608A (es) | 2018-06-13 | 2021-03-09 | Worg Pharmaceuticals Hangzhou Co Ltd | Preparacion de derivados de triazepina condensados y su uso como inhibidores de bet. |
| US20230053152A1 (en) * | 2019-11-26 | 2023-02-16 | Benobio Co., Ltd. | Novel Quercetin Redox Derivative And Use Thereof As BET Inhibitor |
| JP7630801B2 (ja) * | 2020-07-13 | 2025-02-18 | 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 |
| WO2025137575A1 (en) * | 2023-12-22 | 2025-06-26 | Arrakis Therapeutics, Inc. | Quinazoline compounds and methods of use thereof for treating myc-mediated diseases |
Family Cites Families (215)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2065593A (en) | 1936-12-29 | Water-soluble diazoimino com | ||
| FR472489A (fr) | 1914-02-20 | 1914-12-08 | Stas Motor Ges M B H | Bague de garniture métallique pour pistons |
| FR803619A (fr) | 1935-03-23 | 1936-10-05 | Ig Farbenindustrie Ag | Acide du type dihydroxystilbène-dicarboxylique et son procédé de préparation |
| US2065900A (en) | 1935-03-23 | 1936-12-29 | Gen Aniline Works Inc | Dihydroxystilbene-dicarboxylic acid and a process of preparing it |
| DE637259C (de) | 1935-03-24 | 1936-10-27 | I G Farbenindustrie Akt Ges | Verfahren zur Darstellung einer Dioxystilbendicarbonsaeure |
| FR803201A (fr) | 1935-07-08 | 1936-09-25 | Ste Ind Chim Bale | Préparation d'acides sulfoniques |
| US2071329A (en) | 1935-08-22 | 1937-02-23 | Solvay Process Co | Method of recovering phthalic anhydride |
| DE652772C (de) | 1935-11-07 | 1937-11-08 | I G Farbenindustrie Akt Ges | Verfahren zur Herstellung von N-Dihydroazinen der Anthrachinonreihe |
| GB728767A (en) | 1951-10-12 | 1955-04-27 | Wander Ag Dr A | 2-substituted chromone compounds, and a method of making same |
| US3251837A (en) | 1962-09-14 | 1966-05-17 | Pfizer & Co C | Derivatives of 1, 2, 4-benzothiadiazine-1, 1-dioxides |
| GB1179019A (en) | 1967-05-23 | 1970-01-28 | Produits Chimique Soc Et | Polynicotinic Esters of Flavonoids |
| FR6928M (enExample) | 1967-11-24 | 1969-05-05 | ||
| US3600394A (en) | 1968-05-17 | 1971-08-17 | Searle & Co | 2-aminoalkyl-3-arylisocarbostyrils |
| US3773946A (en) | 1969-09-02 | 1973-11-20 | Parke Davis & Co | Triglyceride-lowering compositions and methods |
| US3930024A (en) | 1969-09-02 | 1975-12-30 | Parke Davis & Co | Pharmaceutical compositions and methods |
| FR2244493A1 (en) | 1973-08-09 | 1975-04-18 | Pluripharm | Flavonoid amino-acid salts - for treatment of haemorrhage, circulatory disorders and atherosclerosis |
| DE2349024A1 (de) | 1973-09-26 | 1975-04-10 | Schering Ag | 6beta,7beta-epoxy-1alpha,2alphamethylen-d-homo-4-pregnen-3,20-dione |
| US5098903A (en) | 1980-03-07 | 1992-03-24 | Board Of Regents Of The University Of Oklahoma | Diphenylcyclopropyl analogs as antiestrogenic and antitumor agents |
| IL64542A0 (en) | 1981-12-15 | 1982-03-31 | Yissum Res Dev Co | Long-chain alpha,omega-dicarboxylic acids and derivatives thereof and pharmaceutical compositions containing them |
| JPS60136512A (ja) | 1983-12-26 | 1985-07-20 | Eisai Co Ltd | 脂質代謝改善剤 |
| DE3423166A1 (de) | 1984-06-22 | 1986-01-02 | Epis S.A., Zug | Alpha-, omega-dicarbonsaeuren, verfahren zu ihrer herstellung und arzneimittel, die diese verbindungen enthalten |
| CA1281720C (en) | 1984-11-08 | 1991-03-19 | Makoto Sunagawa | Carbapenem compounds and production thereof |
| DE3515882A1 (de) * | 1985-05-03 | 1986-11-06 | Dr. Karl Thomae Gmbh, 7950 Biberach | Arzneimittel, enthaltend pyridinone mit antithrombotischen wirkungen und verfahren zu ihrer herstellung |
| DE3532279A1 (de) | 1985-09-11 | 1987-03-12 | Bayer Ag | 1,4-benzoxathiin-derivate |
| DE3601417A1 (de) | 1986-01-20 | 1987-07-23 | Nattermann A & Cie | 2'-alkyl-(alkenyl-) substituierte quercetine |
| US4825005A (en) | 1986-08-29 | 1989-04-25 | Ciba-Geigy Corporation | Process for the preparation of aromatic ether and thioether compounds |
| ES2053508T3 (es) | 1986-11-24 | 1994-08-01 | Fujisawa Pharmaceutical Co | Compuestos de acidos 3-pirrolidinil-tio-1-azabiciclo(3.2.0)hept-2-eno-2-carboxilicos. |
| GB8804058D0 (en) | 1988-02-22 | 1988-03-23 | Fujisawa Pharmaceutical Co | 3-alkenyl-1-azabicyclo(3 2 0)hept-2-ene-2-carboxylic acid compounds |
| US4925838A (en) | 1988-03-18 | 1990-05-15 | Fujisawa Pharmaceutical Company, Ltd. | 3-pyrrolidinylthio-1-azabicyclo[3.2.0]-hept-2-ene-2-carboxylic acid compounds |
| US4963544A (en) | 1988-05-23 | 1990-10-16 | Fujisawa Pharmaceutical Company, Ltd. | 3-pyrrolidinylthio-1-azabicyclo[3.2.0]-hept-2-ene-2-carboxylic acid compounds |
| GB8926981D0 (en) | 1988-12-23 | 1990-01-17 | Ici Plc | Heterocyclic derivatives |
| IE902465A1 (en) | 1989-07-07 | 1991-02-13 | Schering Corp | Pharmaceutically active compounds |
| FR2649612A1 (fr) | 1989-07-17 | 1991-01-18 | Rhone Poulenc Sante | Medicaments a base de derives de 1h-benzoxadiazine-4,1,2 nouveaux derives et leurs procedes de preparation |
| IE64358B1 (en) | 1989-07-18 | 1995-07-26 | Ici Plc | Diaryl ether heterocycles |
| GB9018134D0 (en) | 1989-09-29 | 1990-10-03 | Ici Plc | Heterocyclic derivatives |
| CA2224047A1 (en) | 1990-06-05 | 1991-12-06 | Toray Industries, Inc. | Indole derivatives |
| JP2999579B2 (ja) | 1990-07-18 | 2000-01-17 | 武田薬品工業株式会社 | Ｄｎａおよびその用途 |
| GB9025832D0 (en) | 1990-11-28 | 1991-01-09 | Ashwell Geoffrey J | Novel films for nonlinear optical applications |
| IE913866A1 (en) | 1990-11-28 | 1992-06-03 | Ici Plc | Aryl derivatives |
| US5126351A (en) | 1991-01-24 | 1992-06-30 | Glaxo Inc. | Antitumor compounds |
| MX9200299A (es) | 1991-02-07 | 1992-12-01 | Roussel Uclaf | Nuevos derivados biciclicos nitrogenados, su procedimiento de preparacion los nuevos compuestos intermedios obtenidos su aplicacion como medicamentos y las composiciones farmaceuticas que los contienen. |
| AU1746392A (en) | 1991-04-10 | 1992-11-17 | Octamer, Inc. | A method for inhibition of retroviral replication |
| US5480883A (en) | 1991-05-10 | 1996-01-02 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Bis mono- and bicyclic aryl and heteroaryl compounds which inhibit EGF and/or PDGF receptor tyrosine kinase |
| AU658646B2 (en) | 1991-05-10 | 1995-04-27 | Rhone-Poulenc Rorer International (Holdings) Inc. | Bis mono-and bicyclic aryl and heteroaryl compounds which inhibit EGF and/or PDGF receptor tyrosine kinase |
| US5124337A (en) | 1991-05-20 | 1992-06-23 | Schering Corporation | N-acyl-tetrahydroisoquinolines as inhibitors of acyl-coenzyme a:cholesterol acyl transferase |
| US5223506A (en) | 1991-06-04 | 1993-06-29 | Glaxo Inc. | Cyclic antitumor compounds |
| PT100905A (pt) | 1991-09-30 | 1994-02-28 | Eisai Co Ltd | Compostos heterociclicos azotados biciclicos contendo aneis de benzeno, ciclo-hexano ou piridina e de pirimidina, piridina ou imidazol substituidos e composicoes farmaceuticas que os contem |
| US5250679A (en) | 1991-10-18 | 1993-10-05 | Genentech, Inc. | Nonpeptidyl platelet aggregation inhibitors having specificity for the GPIIb III.sub. receptor |
| US5474994A (en) | 1992-05-26 | 1995-12-12 | Recordati S.A., Chemical And Pharmaceutical Company | Bicyclic heterocyclic derivatives having α1 -adrenergic and 5HT1A |
| FR2689127B1 (fr) | 1992-03-31 | 1994-05-06 | Adir Cie | Nouvelles 3', 5' -ditertbutyl-4'-hydroxy flavones, leur procede de preparation et les compositions pharmaceutiques les renfermant. |
| DE4215588A1 (de) | 1992-05-12 | 1993-11-18 | Bayer Ag | Biphenylmethyl-substituierte Pyridone |
| DE4215587A1 (de) | 1992-05-12 | 1993-11-18 | Bayer Ag | Sulfonylbenzyl-substituierte Benzo- und Pyridopyridone |
| GB9218334D0 (en) | 1992-08-28 | 1992-10-14 | Ici Plc | Heterocyclic compounds |
| JPH0680656A (ja) | 1992-09-03 | 1994-03-22 | Mitsui Petrochem Ind Ltd | 光学活性エポキシドの製造方法 |
| WO1994014763A1 (en) | 1992-12-23 | 1994-07-07 | Procept, Inc. | Novel agents for inhibition of hiv infectivity and use therefor |
| JPH0741442A (ja) | 1993-05-21 | 1995-02-10 | Sumitomo Chem Co Ltd | アセチレンアルコール誘導体およびその製造法 |
| JPH0761942A (ja) | 1993-06-17 | 1995-03-07 | Sumitomo Chem Co Ltd | フェノール誘導体およびその製造法 |
| JPH0725761A (ja) | 1993-07-09 | 1995-01-27 | Kureha Chem Ind Co Ltd | 軟骨保護剤 |
| US5756763A (en) | 1993-07-23 | 1998-05-26 | Zaidan Hojin Biseibutsu Kagaku Kenkyukai | Pyrrolidine derivatives |
| US5707547A (en) | 1993-08-03 | 1998-01-13 | Sumitomo Chemical Company, Limited | Trans-olefin compounds, method for production thereof, liquid crystal composition containing the same as active ingredient, and liquid crystal element using said composition |
| JPH07118241A (ja) | 1993-09-01 | 1995-05-09 | Sumitomo Chem Co Ltd | フェノール誘導体およびその製造法 |
| JPH07179380A (ja) | 1993-12-22 | 1995-07-18 | Sumitomo Chem Co Ltd | アルコール誘導体およびその製造法 |
| JPH07233109A (ja) | 1994-02-24 | 1995-09-05 | Sumitomo Chem Co Ltd | 光学活性なアルコール誘導体およびその製造法 |
| US5707987A (en) | 1994-02-25 | 1998-01-13 | Banyu Pharmaceutical Co., Ltd. | Carbapenem derivatives |
| WO1995024410A1 (en) * | 1994-03-08 | 1995-09-14 | Otsuka Pharmaceutical Factory, Inc. | Phosphonic diester derivative |
| JPH07247289A (ja) | 1994-03-11 | 1995-09-26 | Mitsui Petrochem Ind Ltd | クロメンオキシド類の製造方法 |
| FR2718329B1 (fr) | 1994-03-21 | 2002-09-20 | Rhone Poulenc Rorer Sa | Lapin transgénique sensibilisé aux dyslipoprotéinémies. |
| US6048903A (en) | 1994-05-03 | 2000-04-11 | Robert Toppo | Treatment for blood cholesterol with trans-resveratrol |
| US6168776B1 (en) | 1994-07-19 | 2001-01-02 | University Of Pittsburgh | Alkyl, alkenyl and alkynyl Chrysamine G derivatives for the antemortem diagnosis of Alzheimer's disease and in vivo imaging and prevention of amyloid deposition |
| GB2292149A (en) | 1994-08-09 | 1996-02-14 | Ferring Res Ltd | Peptide inhibitors of pro-interleukin-1beta converting enzyme |
| RU2191188C2 (ru) | 1994-11-14 | 2002-10-20 | Варнер-Ламберт Компани | Производные 6-арилпиридо[2,3-d]-пиримидины и -нафтиридины, фармацевтическая композиция, обладающая ингибирующим действием клеточной пролиферации, вызываемой протеиновой тирозинкиназой, и способ ингибирования клеточной пролиферации |
| IL115256A0 (en) | 1994-11-14 | 1995-12-31 | Warner Lambert Co | 6-Aryl pyrido (2,3-d) pyrimidines and naphthyridines and their use |
| US5446071A (en) | 1994-11-18 | 1995-08-29 | Eli Lilly And Company | Methods for lowering serum cholesterol |
| JP4140981B2 (ja) | 1994-12-26 | 2008-08-27 | 東菱薬品工業株式会社 | 再狭窄症及び動脈硬化症治療薬 |
| US5648387A (en) | 1995-03-24 | 1997-07-15 | Warner-Lambert Company | Carboxyalkylethers, formulations, and treatment of vascular diseases |
| WO1996031206A2 (en) | 1995-04-07 | 1996-10-10 | Warner-Lambert Company | Flavones and coumarins as agents for the treatment of atherosclerosis |
| ES2180702T3 (es) | 1995-06-07 | 2003-02-16 | Lilly Co Eli | Tratamiento de patologias por la induccion del factor de transcripcion bef-1. |
| WO1997008153A1 (en) | 1995-08-30 | 1997-03-06 | Otsuka Pharmaceutical Factory, Inc. | Process for producing quinazolin-4-one derivatives |
| WO1997010221A1 (en) | 1995-09-15 | 1997-03-20 | Torrey Pines Institute For Molecular Studies | Synthesis of quinazolinone libraries |
| US5783577A (en) | 1995-09-15 | 1998-07-21 | Trega Biosciences, Inc. | Synthesis of quinazolinone libraries and derivatives thereof |
| HUP9802319A3 (en) | 1995-10-23 | 1999-12-28 | Zymogenetics Inc Seattle | Pharmaceutical compositions for treatment of bone deficit conditions |
| HU224225B1 (hu) | 1995-12-01 | 2005-06-28 | Sankyo Co. Ltd. | Tachikinin receptor antagonista hatású heterociklusos vegyületek, ezek előállítási eljárása és alkalmazásuk gyógyszerkészítmények előállítására |
| US5756736A (en) | 1996-01-26 | 1998-05-26 | Syntex (U.S.A.) Inc. | Process for preparing a 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl)methoxy-1,3-propanediol derivative |
| US5739330A (en) | 1996-02-05 | 1998-04-14 | Hoechst Celanese Corporation | Process for preparing quinazolones |
| WO1997028118A1 (en) | 1996-02-05 | 1997-08-07 | Hoechst Celanese Corporation | Process for preparing anthranilic acids |
| US5763608A (en) | 1996-02-05 | 1998-06-09 | Hoechst Celanese Corporation | Process for preparing pyrimidine derivatives |
| KR19990082488A (ko) | 1996-02-12 | 1999-11-25 | 루트거스, 더 스테이트 유니버시티 오브 뉴 저지 | 토포이소머라제 억제제로서의 코르알린 동족체 |
| BR9711805A (pt) | 1996-06-20 | 2002-01-15 | Regents The Univesity Of Texas | Compostos e métodos para providenciar preparações farmacologicamente ativas e uso dos mesmos |
| US5854264A (en) | 1996-07-24 | 1998-12-29 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| KR100213895B1 (ko) | 1996-10-14 | 1999-08-02 | 박원훈 | 감귤류 과피 추출물, 이로부터 분리 정제된 헤스페리딘 또는 나린진을 포함하는 심혈관 질환 예방및 치료제 조성물 |
| DE19651099A1 (de) | 1996-12-09 | 1998-06-10 | Consortium Elektrochem Ind | Mehrkomponentensystem zum Verändern, Abbau oder Bleichen von Lignin, ligninhaltigen Materialien oder ähnlichen Stoffen sowie Verfahren zu seiner Anwendung |
| IL119971A (en) | 1997-01-07 | 2003-02-12 | Yissum Res Dev Co | Pharmaceutical compositions containing dicarboxylic acids and derivatives thereof and some novel dicarboxylic acids |
| JPH10287678A (ja) | 1997-04-11 | 1998-10-27 | Kyowa Hakko Kogyo Co Ltd | ピラノアジン誘導体 |
| AR012634A1 (es) | 1997-05-02 | 2000-11-08 | Sugen Inc | Compuesto basado en quinazolina, composicion famaceutica que lo comprende, metodo para sintetizarlo, su uso, metodos de modulacion de la funcion deserina/treonina proteinaquinasa con dicho compuesto y metodo in vitro para identificar compuestos que modulan dicha funcion |
| US5908861A (en) | 1997-05-13 | 1999-06-01 | Octamer, Inc. | Methods for treating inflammation and inflammatory disease using pADPRT inhibitors |
| EP1009404A4 (en) | 1997-05-13 | 2009-07-01 | Octamer Inc | PROCESS FOR TREATING INFLAMMATION OR INFLAMMATORY DISEASES USING POLY-ADP RIBOSE POLYMERASE INHIBITORS |
| DE69807222T2 (de) | 1997-06-02 | 2003-04-17 | Janssen Pharmaceutica N.V., Beerse | (imidazol-5-yl)methyl-2-quinolinone derivativen als inhibitoren von proliferation der glatten muskelzellen |
| IL121165A0 (en) | 1997-06-26 | 1997-11-20 | Yissum Res Dev Co | Pharmaceutical compositions containing carboxylic acids and derivatives thereof |
| AU8885498A (en) | 1997-08-29 | 1999-03-22 | Takeda Chemical Industries Ltd. | Triazine derivatives, their production and use |
| US6635642B1 (en) | 1997-09-03 | 2003-10-21 | Guilford Pharmaceuticals Inc. | PARP inhibitors, pharmaceutical compositions comprising same, and methods of using same |
| US6239114B1 (en) | 1997-09-26 | 2001-05-29 | Kgk Synergize | Compositions and methods for treatment of neoplastic diseases with combinations of limonoids, flavonoids and tocotrienols |
| WO1999018077A1 (en) | 1997-10-02 | 1999-04-15 | Eisai Co., Ltd. | Fused pyridine derivatives |
| JP2001520992A (ja) | 1997-10-28 | 2001-11-06 | コリア インスティテュート オブ サイエンス アンド テクノロジー | アシルｃｏａ−コレステロール−ｏ−アシルトランスフェラーゼ抑制剤、動脈壁上でのマクロファージ−脂質複合体蓄積の抑制剤および肝疾患予防または治療剤としてのナリンジンおよびナリンゲニン |
| GB9725782D0 (en) | 1997-12-05 | 1998-02-04 | Pfizer Ltd | Therapeutic agents |
| DE19756388A1 (de) | 1997-12-18 | 1999-06-24 | Hoechst Marion Roussel De Gmbh | Substituierte 2-Aryl-4-amino-chinazoline |
| US6512161B1 (en) | 1998-01-08 | 2003-01-28 | Aventis Pharmaceuticals, Inc. | Transgenic rabbit that expresses a functional human lipoprotein (a) |
| US6414037B1 (en) | 1998-01-09 | 2002-07-02 | Pharmascience | Pharmaceutical formulations of resveratrol and methods of use thereof |
| US6022901A (en) | 1998-05-13 | 2000-02-08 | Pharmascience Inc. | Administration of resveratrol to prevent or treat restenosis following coronary intervention |
| KR20010079922A (ko) | 1998-09-24 | 2001-08-22 | 미우라 아키라 | 하이드록시플라본 유도체 |
| CN1148188C (zh) | 1998-10-19 | 2004-05-05 | 卫材株式会社 | 镇痛剂 |
| CN1327384A (zh) | 1998-10-20 | 2001-12-19 | 韩国科学技术研究院 | 作为血浆高密度脂蛋白浓度增高剂的生物类黄酮 |
| AU2190700A (en) | 1998-12-17 | 2000-07-03 | Tularik Inc. | Tubulin-binding agents |
| US6291456B1 (en) | 1998-12-30 | 2001-09-18 | Signal Pharmaceuticals, Inc. | Compounds and methods for modulation of estrogen receptors |
| US6399633B1 (en) | 1999-02-01 | 2002-06-04 | Aventis Pharmaceuticals Inc. | Use of 4-H-1-benzopryan-4-one derivatives as inhibitors of smooth muscle cell proliferation |
| TR200102522T2 (tr) | 1999-03-15 | 2001-12-21 | Abbott Laboratories | Antibakteryel etkinliğe sahip olan 6-0-ikameli makrolidler. |
| US6969720B2 (en) | 1999-03-17 | 2005-11-29 | Amr Technology, Inc. | Biaryl substituted purine derivatives as potent antiproliferative agents |
| US6054435A (en) | 1999-03-19 | 2000-04-25 | Abbott Laboratories | 6-O-substituted macrolides having antibacterial activity |
| EP1177187B1 (en) | 1999-04-28 | 2007-07-25 | Sanofi-Aventis Deutschland GmbH | Di-aryl acid derivatives as ppar receptor ligands |
| US6835755B1 (en) | 1999-06-24 | 2004-12-28 | University Of Pretoria | Naphthoquinone derivatives and their use in the treatment and control of tuberculosis |
| DE19934799B4 (de) | 1999-07-28 | 2008-01-24 | Az Electronic Materials (Germany) Gmbh | Chiral-smektische Flüssigkristallmischung und ihre Verwendung in Aktivmatrix-Displays mit hohen Kontrastwerten |
| JP2001131151A (ja) | 1999-11-02 | 2001-05-15 | Shionogi & Co Ltd | オレフィン誘導体の新規用途 |
| JP5278983B2 (ja) | 1999-11-17 | 2013-09-04 | 塩野義製薬株式会社 | アミド化合物の新規用途 |
| CA2393297C (en) | 1999-12-06 | 2010-10-05 | Welichem Biotech Inc. | Polyhydroxystilbenes as antipsoriatic agents and protein kinase inhibitors |
| FR2804679B1 (fr) | 2000-02-07 | 2002-04-26 | Clariant France Sa | Nouveaux composes phenoliques derives des dialcoxyethanals, leur procede de preparation et leur application |
| ATE272600T1 (de) | 2000-02-17 | 2004-08-15 | Appleton Paper Inc | Verfahren zur herstellung von alkoxy- oder arylmethoxy-aroxyethanen |
| CN100345830C (zh) | 2000-04-27 | 2007-10-31 | 安斯泰来制药有限公司 | 稠合杂芳基衍生物 |
| WO2001082916A2 (en) | 2000-05-03 | 2001-11-08 | Tularik Inc. | Combination therapeutic compositions and methods of use |
| US6548694B2 (en) | 2000-05-23 | 2003-04-15 | Hoffman-La Roche Inc. | N-(4-carbamimidoyl-phenyl)-glycine derivatives |
| JP2001335476A (ja) | 2000-05-29 | 2001-12-04 | Shionogi & Co Ltd | 三環化合物の新規用途 |
| US6479499B1 (en) | 2000-06-28 | 2002-11-12 | National Science Council | 2-phenyl-4-quinazolinone compounds, 2-phenyl-4-alkoxy-quinazoline compounds and their pharmaceutical compositions |
| US20020025301A1 (en) | 2000-07-04 | 2002-02-28 | Sylke Haremza | Novel flavonoids and their use in cosmetic and dermatological preparations |
| US6541522B2 (en) | 2000-08-16 | 2003-04-01 | Insmed Incorporated | Methods of using compositions containing hypotriglyceridemically active stilbenoids |
| AU2002214546A1 (en) * | 2000-09-29 | 2002-04-08 | Cor Therapeutics, Inc. | Bicyclic pyrimidin-4-one based inhibitors of factor xa |
| CA2356544C (en) | 2000-10-03 | 2006-04-04 | Warner-Lambert Company | Pyridotriazines and pyridopyridazines |
| WO2002028835A1 (en) | 2000-10-05 | 2002-04-11 | Fujisawa Pharmaceutical Co., Ltd. | Benzamide compounds as apo b secretion inhibitors |
| AU2002211667A1 (en) | 2000-10-11 | 2002-04-22 | Esperion Therapeutics, Inc. | Sulfoxide and bis-sulfoxide compounds and compositions for cholesterol management and related uses |
| EP1363879A2 (en) | 2000-10-11 | 2003-11-26 | Esperion Therapeutics Inc. | Sulfide and disulfide compounds and compositions for cholesterol management and related uses |
| SK4772003A3 (en) | 2000-10-19 | 2003-08-05 | Merck & Co Inc | Estrogen receptor modulators |
| AU2002222566A1 (en) | 2000-11-30 | 2002-06-11 | Canon Kabushiki Kaisha | Luminescent element and display |
| WO2002046172A2 (en) | 2000-12-07 | 2002-06-13 | Cv Therapeutics, Inc. | Substituted 1, 3, 5-triazines and pyrimidines as abca-1 elevating compounds against coronary artery disease or atherosclerosis |
| KR100472694B1 (ko) | 2000-12-30 | 2005-03-07 | 한국생명공학연구원 | 플라바논 유도체 및 이를 포함하는 혈중 지질 농도 관련질환의 예방 및 치료용 조성물 |
| JP2002249483A (ja) | 2001-02-21 | 2002-09-06 | Koei Chem Co Ltd | アリール置換複素環式化合物の製造法 |
| JP4256679B2 (ja) | 2001-03-16 | 2009-04-22 | ノボゲン リサーチ ピーティーワイ リミテッド | 再狭窄の治療方法 |
| EP1385501A2 (en) | 2001-04-11 | 2004-02-04 | Atherogenics, Inc. | Probucol monoesters and their use to increase plasma hdl cholesterol levels and improve hdl functionality |
| EP1397137B1 (en) | 2001-05-25 | 2009-10-14 | Bristol-Myers Squibb Company | Hydantion derivatives as inhibitors of matrix metalloproteinases |
| WO2003007959A1 (en) | 2001-07-16 | 2003-01-30 | Fujisawa Pharmaceutical Co., Ltd. | Quinoxaline derivatives which have parp inhibitory action |
| US7173128B2 (en) | 2001-08-13 | 2007-02-06 | Ciba Specialty Chemicals Corporation | Ultraviolet light absorbers |
| EP1419770A4 (en) | 2001-08-24 | 2005-08-03 | Shionogi & Co | AGENT ACC L RATION OF THE EXPRESSION OF APO AI |
| EP1426046A4 (en) | 2001-09-14 | 2005-11-02 | Shionogi & Co | NEW USE OF TRICYCLIC COMPOUNDS |
| US7429593B2 (en) | 2001-09-14 | 2008-09-30 | Shionogi & Co., Ltd. | Utilities of amide compounds |
| US8124625B2 (en) | 2001-09-14 | 2012-02-28 | Shionogi & Co., Ltd. | Method of enhancing the expression of apolipoprotein AI using olefin derivatives |
| US6835469B2 (en) | 2001-10-17 | 2004-12-28 | The University Of Southern California | Phosphorescent compounds and devices comprising the same |
| US7166368B2 (en) | 2001-11-07 | 2007-01-23 | E. I. Du Pont De Nemours And Company | Electroluminescent platinum compounds and devices made with such compounds |
| US7250512B2 (en) | 2001-11-07 | 2007-07-31 | E. I. Du Pont De Nemours And Company | Electroluminescent iridium compounds having red-orange or red emission and devices made with such compounds |
| US6541045B1 (en) | 2002-01-04 | 2003-04-01 | Nutraceutical Corporation | Herbal composition and method for combating inflammation |
| US8367824B2 (en) | 2002-01-28 | 2013-02-05 | Ube Industries Ltd. | Process for producing quinazolin-4-one derivative |
| JP2005529850A (ja) | 2002-02-19 | 2005-10-06 | ファルマシア・イタリア・エス・ピー・エー | 三環系ピラゾール誘導体、その製造方法および抗腫瘍剤としてのその使用 |
| MY140680A (en) | 2002-05-20 | 2010-01-15 | Bristol Myers Squibb Co | Hepatitis c virus inhibitors |
| TW200401770A (en) | 2002-06-18 | 2004-02-01 | Sankyo Co | Fused-ring pyrimidin-4(3H)-one derivatives, processes for the preparation and uses thereof |
| KR20040001144A (ko) | 2002-06-27 | 2004-01-07 | 김대경 | 신규한 적혈구 세포질형 포스포리파아제 에이 투 효소,그에 대한 항체, 이들의 용도 및 제조 방법 |
| US20040033480A1 (en) | 2002-08-15 | 2004-02-19 | Wong Norman C.W. | Use of resveratrol to regulate expression of apolipoprotein A1 |
| US20050080021A1 (en) | 2002-08-15 | 2005-04-14 | Joseph Tucker | Nitric oxide donating derivatives of stilbenes, polyphenols and flavonoids for the treatment of cardiovascular disorders |
| US20050080024A1 (en) | 2002-08-15 | 2005-04-14 | Joseph Tucker | Nitric oxide donating derivatives for the treatment of cardiovascular disorders |
| AU2003265659A1 (en) | 2002-08-23 | 2004-03-11 | University Of Connecticut | Novel biphenyl and biphenyl-like cannabinoids |
| WO2004019933A1 (en) | 2002-08-30 | 2004-03-11 | Pharmacia & Upjohn Company | Method of preventing or treating atherosclerosis or restenosis |
| EP1398032A1 (en) | 2002-09-10 | 2004-03-17 | PheneX Pharmaceuticals AG | 4-Oxo-quinazolines as LXR nuclear receptor binding compounds |
| EP1407774A1 (en) | 2002-09-10 | 2004-04-14 | LION Bioscience AG | 2-Amino-4-quinazolinones as LXR nuclear receptor binding compounds |
| AU2003284001A1 (en) | 2002-10-07 | 2004-05-04 | Bristol-Myers Squibb Company | Triazolone and triazolethione derivatives |
| WO2004037176A2 (en) * | 2002-10-21 | 2004-05-06 | Bristol-Myers Squibb Company | Quinazolinones and derivatives thereof as factor xa inhibitors |
| WO2004039795A2 (en) | 2002-10-29 | 2004-05-13 | Fujisawa Pharmaceutical Co., Ltd. | Amide compounds for the treatment of hyperlipidemia |
| EP1418164A1 (en) | 2002-11-07 | 2004-05-12 | Institut National De La Sante Et De La Recherche Medicale (Inserm) | New stilbene derivatives and their use as aryl hydrocarbon receptor ligand antagonists |
| ATE427951T1 (de) | 2002-11-18 | 2009-04-15 | Hoffmann La Roche | Diazinopyrimidine und ihre verwendung als proteinkinaseinhibitoren |
| AU2003293006A1 (en) | 2002-11-22 | 2004-06-18 | Japan Tobacco Inc. | Fused bicyclic nitrogen-containing heterocycles |
| MXPA05006124A (es) | 2002-12-13 | 2005-08-16 | Hoffmann La Roche | Derivados de 3-quinazolin-4-ona. |
| ITRM20020629A1 (it) | 2002-12-19 | 2004-06-20 | Sigma Tau Ind Farmaceuti | Uso di acidi alfa-feniltiocarbossilici e alfa-fenilossicarbossilici ad attivita' ipoglicemizzante e/o ipolipidemizzante. |
| ATE496893T1 (de) * | 2002-12-20 | 2011-02-15 | X Ceptor Therapeutics Inc | Isochinolinonderivate und deren verwendung als medikamente |
| JP2004203751A (ja) | 2002-12-24 | 2004-07-22 | Pfizer Inc | 置換６，６−ヘテロ二環式誘導体 |
| WO2004058682A1 (ja) | 2002-12-26 | 2004-07-15 | Eisai Co., Ltd. | 選択的エストロゲン受容体モジュレーター |
| WO2004065392A1 (en) | 2003-01-24 | 2004-08-05 | Smithkline Beecham Corporation | Condensed pyridines and pyrimidines and their use as alk-5 receptor ligands |
| WO2004072042A2 (en) | 2003-02-12 | 2004-08-26 | Carex S.A. | Quinoline derivative and their use for modulation of lxr activity |
| US7547794B2 (en) | 2003-04-03 | 2009-06-16 | Vertex Pharmaceuticals Incorporated | Compositions useful as inhibitors of protein kinases |
| JP4895806B2 (ja) | 2003-04-09 | 2012-03-14 | エクセリクシス， インク． | Ｔｉｅ−２モジュレータと使用方法 |
| JP2004307440A (ja) | 2003-04-10 | 2004-11-04 | Kyorin Pharmaceut Co Ltd | ２−アミノ‐１，３‐プロパンジオール誘導体とその付加塩 |
| EP1629000B1 (en) | 2003-04-16 | 2009-02-18 | Bristol-Myers Squibb Company | Macrocyclic isoquinoline peptide inhibitors of hepatitis c virus |
| EP1631295B1 (en) | 2003-06-06 | 2010-03-03 | Arexis AB | Use of condensed heterocyclic compounds as scce inhibitors for the treatment of skin diseases |
| US7314939B2 (en) | 2003-06-17 | 2008-01-01 | Millennium Pharmaceuticals, Inc. | Compositions and methods for inhibiting TGF-β |
| WO2004113307A1 (ja) | 2003-06-18 | 2004-12-29 | Ube Industries, Ltd. | ピリミジン−４−オン化合物の製造方法 |
| US20050043300A1 (en) | 2003-08-14 | 2005-02-24 | Pfizer Inc. | Piperazine derivatives |
| KR20060120101A (ko) | 2003-10-10 | 2006-11-24 | 리스버로직스 코퍼레이션 | Ｅｇｒ-1 인핸서 요소와 관련된 질환의 치료 |
| EP1678157A4 (en) | 2003-10-28 | 2009-03-18 | Reddy Us Therapeutics Inc | Heterocyclic compounds and process for their preparation and use |
| WO2005065183A2 (en) | 2003-12-19 | 2005-07-21 | Merck & Co., Inc. | Mitotic kinesin inhibitors |
| US20080188527A1 (en) | 2003-12-23 | 2008-08-07 | Cashman John R | Synthetic Compounds and Derivatives as Modulators of Smoking or Nicotine Ingestion and Lung Cancer |
| TW200536830A (en) | 2004-02-06 | 2005-11-16 | Chugai Pharmaceutical Co Ltd | 1-(2H)-isoquinolone derivative |
| WO2005115993A1 (ja) | 2004-05-31 | 2005-12-08 | Banyu Pharmaceutical Co., Ltd. | キナゾリン誘導体 |
| WO2006012577A2 (en) | 2004-07-22 | 2006-02-02 | Bayer Pharmaceuticals Corporation | Quinazolinone derivatives useful for the regulation of glucose homeostasis and food intake |
| US20070218155A1 (en) | 2004-08-20 | 2007-09-20 | Kuhrts Eric H | Methods and compositions for treating dyslipidaemia |
| US7846915B2 (en) | 2004-10-20 | 2010-12-07 | Resverlogix Corporation | Stilbenes and chalcones for the prevention and treatment of cardiovascular diseases |
| JP2008526734A (ja) | 2004-12-31 | 2008-07-24 | エスケー ケミカルズ カンパニー リミテッド | 糖尿及び肥満治療予防に有効なキナゾリン誘導体 |
| CR9465A (es) | 2005-03-25 | 2008-06-19 | Surface Logix Inc | Compuestos mejorados farmacocineticamente |
| US8410109B2 (en) | 2005-07-29 | 2013-04-02 | Resverlogix Corp. | Pharmaceutical compositions for the prevention and treatment of complex diseases and their delivery by insertable medical devices |
| EP1944301A4 (en) | 2005-10-27 | 2012-01-04 | Msd Kk | NEW BENZOXATHIIN DERIVATIVES |
| WO2007071055A1 (en) | 2005-12-21 | 2007-06-28 | Painceptor Pharma Corporation | Compositions and methods for modulating gated ion channels |
| CL2008000252A1 (es) * | 2007-01-29 | 2008-03-14 | Xenon Pharmaceuticals Inc | Compuestos derivados de quinazolinona o pirimidinona; composicion farmaceutica que comprende a dichos compuestos; y su uso para tratar enfermedades mediadas por los canales de calcio, tales como dolor, depresion, enfermedades cardiovasculares, respir |
| MX2009008099A (es) | 2007-02-01 | 2009-12-14 | Resverlogix Corp | Compuestos para la prevencion y tratamiento de enfermedades cardiovasculares. |
| EP2005941A3 (de) | 2007-06-01 | 2009-04-01 | Henkel AG & Co. KGaA | Zellverjüngende Zusammensetzungen |
| WO2008152471A1 (en) | 2007-06-12 | 2008-12-18 | Coley Pharmaceutical Group, Inc. | Quinazoline derivative useful as toll-like receptor antagonist |
| KR101629356B1 (ko) | 2008-06-26 | 2016-06-13 | 리스버로직스 코퍼레이션 | 퀴나졸리논 유도체의 제조방법 |
| EP2324022A1 (de) | 2008-08-05 | 2011-05-25 | Boehringer Ingelheim International GmbH | Substituierte naphthyridine und ihre verwendung als arzneimittel |
| AU2009302473A1 (en) | 2008-10-06 | 2010-04-15 | Carolus Therapeutics, Inc. | Methods of treating inflammation |
| EP2403844A1 (en) | 2009-03-06 | 2012-01-11 | F. Hoffmann-La Roche AG | Heterocyclic antiviral compounds |
| KR101913109B1 (ko) | 2009-03-18 | 2018-10-31 | 리스버로직스 코퍼레이션 | 신규한 소염제 |
| DK2421533T3 (en) | 2009-04-22 | 2019-01-07 | Resverlogix Corp | Hitherto unknown anti-inflammatory agents |
| DE102010048800A1 (de) | 2010-10-20 | 2012-05-10 | Merck Patent Gmbh | Chinoxalinderivate |
| LT2773354T (lt) | 2011-11-01 | 2019-08-12 | Resverlogix Corp. | Geriamosios greitai atsipalaiduojančios pakeistų chinozolinų vaisto formos |
| KR101532570B1 (ko) | 2012-10-15 | 2015-06-30 | 리스버로직스 코퍼레이션 | 벤즈아미드 화합물의 합성에 유용한 화합물 |
-
2010
- 2010-01-08 CA CA2747417A patent/CA2747417C/en not_active Expired - Fee Related
- 2010-01-08 ES ES13175561.3T patent/ES2542835T3/es active Active
- 2010-01-08 WO PCT/IB2010/000159 patent/WO2010079431A2/en not_active Ceased
- 2010-01-08 JP JP2011544946A patent/JP5635535B2/ja not_active Expired - Fee Related
- 2010-01-08 US US13/143,757 patent/US8952021B2/en not_active Expired - Fee Related
- 2010-01-08 EP EP10704977.7A patent/EP2382194B1/en not_active Not-in-force
- 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
- 2010-01-08 AU AU2010204106A patent/AU2010204106B2/en not_active Ceased
- 2010-01-08 ES ES10704977.7T patent/ES2463097T3/es active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2012514631A5 (enExample) | ||
| FI3932919T3 (fi) | Jak-inhibiittoriyhdiste ja sen käyttö | |
| CA2817317C (en) | Aminoalcohol substituted 2,3-dihydroimidazo[1,2-c]quinazoline derivatives useful for treating hyper-proliferative disorders and diseases associated with angiogenesis | |
| JP2015516392A5 (enExample) | ||
| CN104797582B (zh) | 作为mknk 激酶抑制剂的取代的吡咯并嘧啶基氨基-苯并噻唑酮 | |
| JP2012512887A5 (enExample) | ||
| JP2011507854A5 (enExample) | ||
| JP2014139226A5 (enExample) | ||
| JP2011518856A5 (enExample) | ||
| JP2012532131A5 (enExample) | ||
| AU2015274626A1 (en) | Quinazolinone derivatives as phosphatidylinositol 3-kinase inhibitors | |
| KR20160132130A (ko) | 폐의 비소세포 암종 및 난소암을 치료하기 위한 디안하이드로갈락티톨 및 이의 유사체 또는 유도체 | |
| JP5940078B2 (ja) | アリールアミノアルコール−置換２，３−ジヒドロイミダゾ［１，２−ｃ］キノリン | |
| EA016527B1 (ru) | Триазолопиридазиновые модуляторы протеинкиназ | |
| JP2016537384A5 (enExample) | ||
| CA2891644A1 (en) | Aminoimidazopyridazines | |
| WO2019071147A1 (en) | INHIBITORS OF KINASE P38 REDUCING EXPRESSION OF DUX4 GENE AND DOWNSTREAM GENES FOR THE TREATMENT OF FSHD | |
| JP2011513364A (ja) | Ｅｇｆｒ依存性疾患またはｅｇｆｒファミリーメンバーを標的とする薬剤に対して耐性を獲得した疾患を治療するためのピリミジン誘導体の使用 | |
| JP2013518904A5 (enExample) | ||
| ES2401822T3 (es) | Utilización de imidazoquinolinas para el tratamiento de enfermedades dependientes de EGFR o enfermedades que han adquirido resistencia a agentes que tienen como objetivo mienbros de la familia de EGFR | |
| JP2018522852A5 (enExample) | ||
| JP2011506466A5 (enExample) | ||
| CN104837841A (zh) | 用于治疗过度增殖性疾病的取代的吲唑-吡咯并嘧啶 | |
| JP6165058B2 (ja) | アルコキシ−置換２，３−ジヒドロイミダゾ［１，２−ｃ］キナゾリン | |
| WO2014048894A1 (en) | Substituted indazol-pyrrolopyrimidines useful in the treatment of hyperfoliferative disorders |