JP2011519876A5 - - Google Patents
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- Publication number
- JP2011519876A5 JP2011519876A5 JP2011507805A JP2011507805A JP2011519876A5 JP 2011519876 A5 JP2011519876 A5 JP 2011519876A5 JP 2011507805 A JP2011507805 A JP 2011507805A JP 2011507805 A JP2011507805 A JP 2011507805A JP 2011519876 A5 JP2011519876 A5 JP 2011519876A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- hydroxy
- thieno
- dihydro
- phenyl
- 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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- 150000001875 compounds Chemical class 0.000 claims 19
- 150000003839 salts Chemical class 0.000 claims 16
- 239000000203 mixture Substances 0.000 claims 13
- 239000012453 solvate Substances 0.000 claims 13
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 8
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 8
- 229910052801 chlorine Inorganic materials 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 229910052731 fluorine Inorganic materials 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- -1 COA Chemical group 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 229910052740 iodine Inorganic materials 0.000 claims 3
- 125000002950 monocyclic group Chemical group 0.000 claims 3
- 125000001624 naphthyl group Chemical group 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims 3
- 125000004434 sulfur atom Chemical group 0.000 claims 3
- HKWQMQBRXWPSSR-UHFFFAOYSA-N 2-chloro-4-hydroxy-3-[4-(2-hydroxyphenyl)phenyl]-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound OC1=CC=CC=C1C1=CC=C(C=2C=3C(O)=C(C=4C=CC=CC=4)C(=O)NC=3SC=2Cl)C=C1 HKWQMQBRXWPSSR-UHFFFAOYSA-N 0.000 claims 2
- HVTRFLDXUYTKMF-UHFFFAOYSA-N 3-[4-(2-fluorophenyl)phenyl]-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound O=C1NC=2SC=C(C=3C=CC(=CC=3)C=3C(=CC=CC=3)F)C=2C(O)=C1C1=CC=CC=C1 HVTRFLDXUYTKMF-UHFFFAOYSA-N 0.000 claims 2
- ZVZONVVWRDQGNE-UHFFFAOYSA-N 3-[4-(2-fluorophenyl)phenyl]-4-hydroxy-5-pyridin-3-yl-7h-thieno[2,3-b]pyridin-6-one Chemical compound O=C1NC=2SC=C(C=3C=CC(=CC=3)C=3C(=CC=CC=3)F)C=2C(O)=C1C1=CC=CN=C1 ZVZONVVWRDQGNE-UHFFFAOYSA-N 0.000 claims 2
- TUNBRRYXMOAFGR-UHFFFAOYSA-N 3-[4-(4-fluorophenyl)phenyl]-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound O=C1NC=2SC=C(C=3C=CC(=CC=3)C=3C=CC(F)=CC=3)C=2C(O)=C1C1=CC=CC=C1 TUNBRRYXMOAFGR-UHFFFAOYSA-N 0.000 claims 2
- XBRXAVIHKNUPSS-UHFFFAOYSA-N 4-[4-(4-hydroxy-6-oxo-5-phenyl-7h-thieno[2,3-b]pyridin-3-yl)phenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C=2C=3C(O)=C(C=4C=CC=CC=4)C(=O)NC=3SC=2)C=C1 XBRXAVIHKNUPSS-UHFFFAOYSA-N 0.000 claims 2
- VYXPVECHTHYTBA-UHFFFAOYSA-N 4-hydroxy-3-(2-hydroxy-4-pyridin-4-ylphenyl)-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound OC1=CC(C=2C=CN=CC=2)=CC=C1C(C=1C=2O)=CSC=1NC(=O)C=2C1=CC=CC=C1 VYXPVECHTHYTBA-UHFFFAOYSA-N 0.000 claims 2
- HRBOTPOUTZIVDY-UHFFFAOYSA-N 4-hydroxy-3-[4-(2-hydroxyphenyl)phenyl]-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound OC1=CC=CC=C1C1=CC=C(C=2C=3C(O)=C(C=4C=CC=CC=4)C(=O)NC=3SC=2)C=C1 HRBOTPOUTZIVDY-UHFFFAOYSA-N 0.000 claims 2
- KQFDGZOTTHQOMD-UHFFFAOYSA-N 4-hydroxy-3-[4-(2-hydroxyphenyl)phenyl]-5-pyridin-3-yl-7h-thieno[2,3-b]pyridin-6-one Chemical compound OC1=CC=CC=C1C1=CC=C(C=2C=3C(O)=C(C=4C=NC=CC=4)C(=O)NC=3SC=2)C=C1 KQFDGZOTTHQOMD-UHFFFAOYSA-N 0.000 claims 2
- ZCZUMSNNMVMMAS-UHFFFAOYSA-N 4-hydroxy-3-[4-(2-hydroxyphenyl)phenyl]-5-pyridin-4-yl-7H-thieno[2,3-b]pyridin-6-one Chemical compound OC1=CC=CC=C1C1=CC=C(C=2C=3C(O)=C(C=4C=CN=CC=4)C(=O)NC=3SC=2)C=C1 ZCZUMSNNMVMMAS-UHFFFAOYSA-N 0.000 claims 2
- ISXUOTBGTHNDDA-UHFFFAOYSA-N 4-hydroxy-3-[4-(4-hydroxyphenyl)phenyl]-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound C1=CC(O)=CC=C1C1=CC=C(C=2C=3C(O)=C(C=4C=CC=CC=4)C(=O)NC=3SC=2)C=C1 ISXUOTBGTHNDDA-UHFFFAOYSA-N 0.000 claims 2
- DTPQCCSCLMZLMM-UHFFFAOYSA-N 4-hydroxy-3-[4-(4-methylphenyl)phenyl]-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound C1=CC(C)=CC=C1C1=CC=C(C=2C=3C(O)=C(C=4C=CC=CC=4)C(=O)NC=3SC=2)C=C1 DTPQCCSCLMZLMM-UHFFFAOYSA-N 0.000 claims 2
- WGOZPEQUBLQTLC-UHFFFAOYSA-N 4-hydroxy-3-[4-(4-methylphenyl)phenyl]-5-pyridin-3-yl-7h-thieno[2,3-b]pyridin-6-one Chemical compound C1=CC(C)=CC=C1C1=CC=C(C=2C=3C(O)=C(C=4C=NC=CC=4)C(=O)NC=3SC=2)C=C1 WGOZPEQUBLQTLC-UHFFFAOYSA-N 0.000 claims 2
- GOSMRIZUTRINQV-UHFFFAOYSA-N 4-hydroxy-3-[4-[3-(hydroxymethyl)phenyl]phenyl]-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound OCC1=CC=CC(C=2C=CC(=CC=2)C=2C=3C(O)=C(C=4C=CC=CC=4)C(=O)NC=3SC=2)=C1 GOSMRIZUTRINQV-UHFFFAOYSA-N 0.000 claims 2
- FSVYOZALIBZRKZ-UHFFFAOYSA-N 4-hydroxy-3-[4-[4-(hydroxymethyl)phenyl]phenyl]-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound C1=CC(CO)=CC=C1C1=CC=C(C=2C=3C(O)=C(C=4C=CC=CC=4)C(=O)NC=3SC=2)C=C1 FSVYOZALIBZRKZ-UHFFFAOYSA-N 0.000 claims 2
- YHTGTTPAZVKQBC-UHFFFAOYSA-N 4-hydroxy-5-phenyl-3-(4-phenylphenyl)-7h-thieno[2,3-b]pyridin-6-one Chemical compound O=C1NC=2SC=C(C=3C=CC(=CC=3)C=3C=CC=CC=3)C=2C(O)=C1C1=CC=CC=C1 YHTGTTPAZVKQBC-UHFFFAOYSA-N 0.000 claims 2
- HZYVPJJDGTUBNS-UHFFFAOYSA-N 4-hydroxy-5-phenyl-3-(4-pyridin-3-ylphenyl)-7h-thieno[2,3-b]pyridin-6-one Chemical compound O=C1NC=2SC=C(C=3C=CC(=CC=3)C=3C=NC=CC=3)C=2C(O)=C1C1=CC=CC=C1 HZYVPJJDGTUBNS-UHFFFAOYSA-N 0.000 claims 2
- YCARLBRXUQWPTN-UHFFFAOYSA-N 4-hydroxy-5-phenyl-3-(4-pyridin-4-ylphenyl)-7h-thieno[2,3-b]pyridin-6-one Chemical compound O=C1NC=2SC=C(C=3C=CC(=CC=3)C=3C=CN=CC=3)C=2C(O)=C1C1=CC=CC=C1 YCARLBRXUQWPTN-UHFFFAOYSA-N 0.000 claims 2
- DJYMHZDZGLVPAE-UHFFFAOYSA-N 4-hydroxy-5-phenyl-3-(6-phenylpyridin-3-yl)-7h-thieno[2,3-b]pyridin-6-one Chemical compound O=C1NC=2SC=C(C=3C=NC(=CC=3)C=3C=CC=CC=3)C=2C(O)=C1C1=CC=CC=C1 DJYMHZDZGLVPAE-UHFFFAOYSA-N 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims 2
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims 1
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims 1
- HTLCUUIJMHNWKW-UHFFFAOYSA-N 2-[4-(4-hydroxy-6-oxo-5-phenyl-7h-thieno[2,3-b]pyridin-3-yl)phenyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=C(C=2C=3C(O)=C(C=4C=CC=CC=4)C(=O)NC=3SC=2)C=C1 HTLCUUIJMHNWKW-UHFFFAOYSA-N 0.000 claims 1
- HPTTXYJXYLWZMP-UHFFFAOYSA-N 2-chloro-4-hydroxy-3-[4-(2-methoxyphenyl)phenyl]-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound COC1=CC=CC=C1C1=CC=C(C=2C=3C(O)=C(C=4C=CC=CC=4)C(=O)NC=3SC=2Cl)C=C1 HPTTXYJXYLWZMP-UHFFFAOYSA-N 0.000 claims 1
- RUETUANXMSSUKN-UHFFFAOYSA-N 3-[3-(1,3-benzodioxol-5-yl)phenyl]-4-hydroxy-5-phenyl-7H-thieno[2,3-b]pyridin-6-one Chemical compound O=C1NC=2SC=C(C=3C=C(C=CC=3)C=3C=C4OCOC4=CC=3)C=2C(O)=C1C1=CC=CC=C1 RUETUANXMSSUKN-UHFFFAOYSA-N 0.000 claims 1
- XRKVCIPNBVUNOM-UHFFFAOYSA-N 3-[4-(2,4-dihydroxyphenyl)phenyl]-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound OC1=CC(O)=CC=C1C1=CC=C(C=2C=3C(O)=C(C=4C=CC=CC=4)C(=O)NC=3SC=2)C=C1 XRKVCIPNBVUNOM-UHFFFAOYSA-N 0.000 claims 1
- PSKVUXBFAOLMEV-UHFFFAOYSA-N 3-[4-(2,4-dimethoxyphenyl)phenyl]-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound COC1=CC(OC)=CC=C1C1=CC=C(C=2C=3C(O)=C(C=4C=CC=CC=4)C(=O)NC=3SC=2)C=C1 PSKVUXBFAOLMEV-UHFFFAOYSA-N 0.000 claims 1
- DKTCYOOIYQCHPU-UHFFFAOYSA-N 3-[4-(3,5-dimethoxyphenyl)phenyl]-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound COC1=CC(OC)=CC(C=2C=CC(=CC=2)C=2C=3C(O)=C(C=4C=CC=CC=4)C(=O)NC=3SC=2)=C1 DKTCYOOIYQCHPU-UHFFFAOYSA-N 0.000 claims 1
- MNNIVGYMKHHKLK-UHFFFAOYSA-N 3-[4-(3-fluorophenyl)phenyl]-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound O=C1NC=2SC=C(C=3C=CC(=CC=3)C=3C=C(F)C=CC=3)C=2C(O)=C1C1=CC=CC=C1 MNNIVGYMKHHKLK-UHFFFAOYSA-N 0.000 claims 1
- DPMPJJRQUVLLNX-UHFFFAOYSA-N 3-[4-(3-fluorophenyl)phenyl]-4-hydroxy-5-pyridin-3-yl-7h-thieno[2,3-b]pyridin-6-one Chemical compound O=C1NC=2SC=C(C=3C=CC(=CC=3)C=3C=C(F)C=CC=3)C=2C(O)=C1C1=CC=CN=C1 DPMPJJRQUVLLNX-UHFFFAOYSA-N 0.000 claims 1
- DYXZTQMFFQSTDS-UHFFFAOYSA-N 3-[4-(4-fluoro-2-hydroxyphenyl)phenyl]-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound OC1=CC(F)=CC=C1C1=CC=C(C=2C=3C(O)=C(C=4C=CC=CC=4)C(=O)NC=3SC=2)C=C1 DYXZTQMFFQSTDS-UHFFFAOYSA-N 0.000 claims 1
- APOWVDDKGUFNPB-UHFFFAOYSA-N 3-[4-(4-fluoro-2-methoxyphenyl)phenyl]-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound COC1=CC(F)=CC=C1C1=CC=C(C=2C=3C(O)=C(C(=O)NC=3SC=2)C=2C=CC=CC=2)C=C1 APOWVDDKGUFNPB-UHFFFAOYSA-N 0.000 claims 1
- YLVCSWFJCLXOGO-UHFFFAOYSA-N 3-[4-(4-fluorophenyl)-3-methoxyphenyl]-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound COC1=CC(C=2C=3C(O)=C(C(=O)NC=3SC=2)C=2C=CC=CC=2)=CC=C1C1=CC=C(F)C=C1 YLVCSWFJCLXOGO-UHFFFAOYSA-N 0.000 claims 1
- BBQKBMPOBKLSQN-UHFFFAOYSA-N 3-[4-(4-fluorophenyl)phenyl]-4-hydroxy-5-pyridin-3-yl-7h-thieno[2,3-b]pyridin-6-one Chemical compound O=C1NC=2SC=C(C=3C=CC(=CC=3)C=3C=CC(F)=CC=3)C=2C(O)=C1C1=CC=CN=C1 BBQKBMPOBKLSQN-UHFFFAOYSA-N 0.000 claims 1
- CLIWKRAIDQNDQU-UHFFFAOYSA-N 3-[4-(4-fluorophenyl)phenyl]-4-hydroxy-5-pyridin-4-yl-7H-thieno[2,3-b]pyridin-6-one Chemical compound O=C1NC=2SC=C(C=3C=CC(=CC=3)C=3C=CC(F)=CC=3)C=2C(O)=C1C1=CC=NC=C1 CLIWKRAIDQNDQU-UHFFFAOYSA-N 0.000 claims 1
- FDLAYOULWSBJHH-UHFFFAOYSA-N 3-[4-(4-hydroxy-6-oxo-5-phenyl-7h-thieno[2,3-b]pyridin-3-yl)phenyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(C=2C=CC(=CC=2)C=2C=3C(O)=C(C=4C=CC=CC=4)C(=O)NC=3SC=2)=C1 FDLAYOULWSBJHH-UHFFFAOYSA-N 0.000 claims 1
- ZEDRAAJXGARDIS-UHFFFAOYSA-N 3-[4-(4-hydroxy-6-oxo-5-phenyl-7h-thieno[2,3-b]pyridin-3-yl)phenyl]benzonitrile Chemical compound O=C1NC=2SC=C(C=3C=CC(=CC=3)C=3C=C(C=CC=3)C#N)C=2C(O)=C1C1=CC=CC=C1 ZEDRAAJXGARDIS-UHFFFAOYSA-N 0.000 claims 1
- HTSCUWYKAYZEFP-UHFFFAOYSA-N 3-[4-(furan-3-yl)phenyl]-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound O=C1NC=2SC=C(C=3C=CC(=CC=3)C3=COC=C3)C=2C(O)=C1C1=CC=CC=C1 HTSCUWYKAYZEFP-UHFFFAOYSA-N 0.000 claims 1
- YWZXPBPGLOHPKN-UHFFFAOYSA-N 3-[4-(furan-3-yl)phenyl]-4-hydroxy-5-pyridin-3-yl-7h-thieno[2,3-b]pyridin-6-one Chemical compound O=C1NC=2SC=C(C=3C=CC(=CC=3)C3=COC=C3)C=2C(O)=C1C1=CC=CN=C1 YWZXPBPGLOHPKN-UHFFFAOYSA-N 0.000 claims 1
- ZBVDTJFDNXUALS-UHFFFAOYSA-N 3-[4-(furan-3-yl)phenyl]-4-hydroxy-5-pyridin-4-yl-7H-thieno[2,3-b]pyridin-6-one Chemical compound O=C1NC=2SC=C(C=3C=CC(=CC=3)C3=COC=C3)C=2C(O)=C1C1=CC=NC=C1 ZBVDTJFDNXUALS-UHFFFAOYSA-N 0.000 claims 1
- MTWIMYMYPYYTRG-UHFFFAOYSA-N 4-[2-hydroxy-4-(4-hydroxy-6-oxo-5-phenyl-7h-thieno[2,3-b]pyridin-3-yl)phenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C=2C=3C(O)=C(C=4C=CC=CC=4)C(=O)NC=3SC=2)C=C1O MTWIMYMYPYYTRG-UHFFFAOYSA-N 0.000 claims 1
- HXNBUOOSTZVERZ-UHFFFAOYSA-N 4-[4-(4-hydroxy-6-oxo-5-phenyl-7h-thieno[2,3-b]pyridin-3-yl)-2-methoxyphenyl]benzoic acid Chemical compound COC1=CC(C=2C=3C(O)=C(C=4C=CC=CC=4)C(=O)NC=3SC=2)=CC=C1C1=CC=C(C(O)=O)C=C1 HXNBUOOSTZVERZ-UHFFFAOYSA-N 0.000 claims 1
- OLEPAMDDNFQSNH-UHFFFAOYSA-N 4-[4-(4-hydroxy-6-oxo-5-phenyl-7h-thieno[2,3-b]pyridin-3-yl)-3-methoxyphenyl]benzoic acid Chemical compound COC1=CC(C=2C=CC(=CC=2)C(O)=O)=CC=C1C(C=1C=2O)=CSC=1NC(=O)C=2C1=CC=CC=C1 OLEPAMDDNFQSNH-UHFFFAOYSA-N 0.000 claims 1
- LFKCDHBCVZVBII-UHFFFAOYSA-N 4-[4-(4-hydroxy-6-oxo-5-phenyl-7h-thieno[2,3-b]pyridin-3-yl)phenyl]benzonitrile Chemical compound O=C1NC=2SC=C(C=3C=CC(=CC=3)C=3C=CC(=CC=3)C#N)C=2C(O)=C1C1=CC=CC=C1 LFKCDHBCVZVBII-UHFFFAOYSA-N 0.000 claims 1
- URQQTAXFDKYCBG-UHFFFAOYSA-N 4-[4-hydroxy-6-oxo-3-(4-phenylphenyl)-7h-thieno[2,3-b]pyridin-5-yl]benzonitrile Chemical compound O=C1NC=2SC=C(C=3C=CC(=CC=3)C=3C=CC=CC=3)C=2C(O)=C1C1=CC=C(C#N)C=C1 URQQTAXFDKYCBG-UHFFFAOYSA-N 0.000 claims 1
- SQZLYUVSATVWOY-UHFFFAOYSA-N 4-hydroxy-3-(3-methoxy-4-phenylphenyl)-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound COC1=CC(C=2C=3C(O)=C(C=4C=CC=CC=4)C(=O)NC=3SC=2)=CC=C1C1=CC=CC=C1 SQZLYUVSATVWOY-UHFFFAOYSA-N 0.000 claims 1
- OKDLJCJWOFSGJV-UHFFFAOYSA-N 4-hydroxy-3-(3-methoxy-4-pyridin-3-ylphenyl)-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound COC1=CC(C=2C=3C(O)=C(C=4C=CC=CC=4)C(=O)NC=3SC=2)=CC=C1C1=CC=CN=C1 OKDLJCJWOFSGJV-UHFFFAOYSA-N 0.000 claims 1
- WWKPQYPBDLZBFP-UHFFFAOYSA-N 4-hydroxy-3-(4-phenylphenyl)-5-pyridin-4-yl-7H-thieno[2,3-b]pyridin-6-one Chemical compound O=C1NC=2SC=C(C=3C=CC(=CC=3)C=3C=CC=CC=3)C=2C(O)=C1C1=CC=NC=C1 WWKPQYPBDLZBFP-UHFFFAOYSA-N 0.000 claims 1
- JCPGZSOUHNRHGE-UHFFFAOYSA-N 4-hydroxy-3-[3-(2-methoxyphenyl)phenyl]-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound COC1=CC=CC=C1C1=CC=CC(C=2C=3C(O)=C(C=4C=CC=CC=4)C(=O)NC=3SC=2)=C1 JCPGZSOUHNRHGE-UHFFFAOYSA-N 0.000 claims 1
- NHERQZNYRZEFLK-UHFFFAOYSA-N 4-hydroxy-3-[3-(3-hydroxyphenyl)phenyl]-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound OC1=CC=CC(C=2C=C(C=CC=2)C=2C=3C(O)=C(C=4C=CC=CC=4)C(=O)NC=3SC=2)=C1 NHERQZNYRZEFLK-UHFFFAOYSA-N 0.000 claims 1
- FLKSQEGHRIBLDA-UHFFFAOYSA-N 4-hydroxy-3-[3-(3-methoxyphenyl)phenyl]-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound COC1=CC=CC(C=2C=C(C=CC=2)C=2C=3C(O)=C(C=4C=CC=CC=4)C(=O)NC=3SC=2)=C1 FLKSQEGHRIBLDA-UHFFFAOYSA-N 0.000 claims 1
- FKZKYHYIDYMOQM-UHFFFAOYSA-N 4-hydroxy-3-[3-(4-hydroxyphenyl)phenyl]-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound C1=CC(O)=CC=C1C1=CC=CC(C=2C=3C(O)=C(C=4C=CC=CC=4)C(=O)NC=3SC=2)=C1 FKZKYHYIDYMOQM-UHFFFAOYSA-N 0.000 claims 1
- BCZPVDFXZAARBY-UHFFFAOYSA-N 4-hydroxy-3-[3-(4-methoxyphenyl)phenyl]-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound C1=CC(OC)=CC=C1C1=CC=CC(C=2C=3C(O)=C(C=4C=CC=CC=4)C(=O)NC=3SC=2)=C1 BCZPVDFXZAARBY-UHFFFAOYSA-N 0.000 claims 1
- FPUQUYIBAYZSAF-UHFFFAOYSA-N 4-hydroxy-3-[3-[4-(hydroxymethyl)phenyl]phenyl]-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound C1=CC(CO)=CC=C1C1=CC=CC(C=2C=3C(O)=C(C=4C=CC=CC=4)C(=O)NC=3SC=2)=C1 FPUQUYIBAYZSAF-UHFFFAOYSA-N 0.000 claims 1
- LQMSUXUHIPMIIL-UHFFFAOYSA-N 4-hydroxy-3-[3-hydroxy-4-(4-methylphenyl)phenyl]-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound C1=CC(C)=CC=C1C1=CC=C(C=2C=3C(O)=C(C=4C=CC=CC=4)C(=O)NC=3SC=2)C=C1O LQMSUXUHIPMIIL-UHFFFAOYSA-N 0.000 claims 1
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| EP2552435A1 (en) | 2010-04-02 | 2013-02-06 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods and compositions comprising ampk activator (metformin/troglitazone) for the treatment of myotonic dystrophy type 1 (dm1) |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| JP5990170B2 (ja) * | 2010-09-01 | 2016-09-07 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 除草活性を有するケトスルタム類及びジケトピリジン類 |
| KR101624020B1 (ko) * | 2011-03-07 | 2016-05-24 | 글락소스미스클라인 엘엘씨 | 퀴놀리논 유도체 |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| EP2760862B1 (en) | 2011-09-27 | 2015-10-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| US8889730B2 (en) | 2012-04-10 | 2014-11-18 | Pfizer Inc. | Indole and indazole compounds that activate AMPK |
| EP2679591A1 (en) | 2012-06-29 | 2014-01-01 | Poxel | Thienopyridone derivatives useful as activators of AMPK |
| CA2905242C (en) | 2013-03-15 | 2016-11-29 | Pfizer Inc. | Indole compounds that activate ampk |
| US10143703B2 (en) | 2014-01-02 | 2018-12-04 | Massachusetts Eye And Ear Infirmary | Treating ocular neovascularization |
| WO2015114663A1 (en) | 2014-01-30 | 2015-08-06 | Council Of Scientific & Industrial Research | Novel thieno [2,3-d]pyrimidin-4(3h)-one compounds with antimycobacterial properties |
| EP3310355B1 (en) | 2015-06-16 | 2020-11-11 | University of Virginia Patent Foundation | Ptp4a3 inhibitor for the treatment of cancer |
| PL3322711T3 (pl) | 2015-06-25 | 2021-10-25 | University Health Network | Inhibitory hpk1 i sposoby ich zastosowania |
| EP3355876A2 (en) | 2015-09-30 | 2018-08-08 | Instituto de Medicina Molecular | Methods for attenuating parasite virulence |
| US11584755B2 (en) | 2017-09-26 | 2023-02-21 | Ideaya Biosciences, Inc. | Dihydrothieno[3,2-b]pyridine compounds |
| WO2019106087A1 (en) * | 2017-11-29 | 2019-06-06 | Syddansk Universitet | Ampk inhibitors |
| JP2023526625A (ja) | 2020-05-19 | 2023-06-22 | キャリーオペ，インク． | Ａｍｐｋアクチベーター |
| CN116390925A (zh) | 2020-06-26 | 2023-07-04 | 卡尔优普公司 | Ampk活化剂 |
| EP4221700A1 (en) | 2020-09-30 | 2023-08-09 | Bioverativ Therapeutics Inc. | Ampk activators and methods of use thereof |
| WO2022106892A1 (en) | 2020-11-17 | 2022-05-27 | Instituto De Medicina Molecular | Anti-malarial compounds |
| US12404348B2 (en) | 2021-11-19 | 2025-09-02 | The Brigham And Women's Hospital, Inc. | Bifunctional chimeric molecules for labeling of kinases with target binding moieties and methods of use thereof |
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| DE4444815A1 (de) * | 1994-12-15 | 1996-06-20 | Merck Patent Gmbh | Thienopyridone |
| AR040123A1 (es) * | 2002-05-31 | 2005-03-16 | Upjohn Co | Compuestos tiofeno, antihelminticos e insecticidas |
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| WO2006093518A2 (en) * | 2004-06-25 | 2006-09-08 | Apath, Llc | Thienyl compounds for treating virus-related conditions |
| US7563813B2 (en) * | 2005-05-13 | 2009-07-21 | Wyeth | Iminothiazolidinone derivatives as SFRP-1 antagonists |
| EP1754483A1 (en) * | 2005-08-18 | 2007-02-21 | Merck Sante | Use of thienopyridone derivatives as AMPK activators and pharmaceutical compositions containing them |
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| MX2010011047A (es) * | 2008-04-11 | 2010-10-26 | Merck Patent Gmbh | Derivados de tienopiridonas como activadores de proteina cinasa activada por amp (ampk). |
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