JP2011516510A5 - - Google Patents
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- JP2011516510A5 JP2011516510A5 JP2011503353A JP2011503353A JP2011516510A5 JP 2011516510 A5 JP2011516510 A5 JP 2011516510A5 JP 2011503353 A JP2011503353 A JP 2011503353A JP 2011503353 A JP2011503353 A JP 2011503353A JP 2011516510 A5 JP2011516510 A5 JP 2011516510A5
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- pyridin
- 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 15
- 150000003839 salts Chemical class 0.000 claims 14
- 239000000203 mixture Substances 0.000 claims 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 9
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 8
- -1 COA Chemical group 0.000 claims 6
- 125000001624 naphthyl group Chemical group 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- JSTHDAGKIAAARF-UHFFFAOYSA-N 2-chloro-4-hydroxy-3-(3-hydroxy-4-methylphenyl)-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound C1=C(O)C(C)=CC=C1C1=C(Cl)SC2=C1C(O)=C(C=1C=CC=CC=1)C(=O)N2 JSTHDAGKIAAARF-UHFFFAOYSA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 125000002950 monocyclic 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
- GMPLDZNTWUFKON-UHFFFAOYSA-N 2-chloro-3-(3,4-difluoro-2-hydroxyphenyl)-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound OC1=C(F)C(F)=CC=C1C1=C(Cl)SC2=C1C(O)=C(C=1C=CC=CC=1)C(=O)N2 GMPLDZNTWUFKON-UHFFFAOYSA-N 0.000 claims 2
- DSMWJSPOHZRWQF-UHFFFAOYSA-N 2-chloro-3-(3-fluoro-2-hydroxy-4-methylphenyl)-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound OC1=C(F)C(C)=CC=C1C1=C(Cl)SC2=C1C(O)=C(C=1C=CC=CC=1)C(=O)N2 DSMWJSPOHZRWQF-UHFFFAOYSA-N 0.000 claims 2
- UFRIIHUVCCCFAS-UHFFFAOYSA-N 2-chloro-3-(3-fluoro-2-hydroxy-4-methylphenyl)-5-(4-fluorophenyl)-4-hydroxy-7h-thieno[2,3-b]pyridin-6-one Chemical compound OC1=C(F)C(C)=CC=C1C1=C(Cl)SC2=C1C(O)=C(C=1C=CC(F)=CC=1)C(=O)N2 UFRIIHUVCCCFAS-UHFFFAOYSA-N 0.000 claims 2
- PWPSLBBDPFKVJK-UHFFFAOYSA-N 2-chloro-3-(4,5-difluoro-2-hydroxyphenyl)-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound OC1=CC(F)=C(F)C=C1C1=C(Cl)SC2=C1C(O)=C(C=1C=CC=CC=1)C(=O)N2 PWPSLBBDPFKVJK-UHFFFAOYSA-N 0.000 claims 2
- BWUIWUXDYJRFGT-UHFFFAOYSA-N 2-chloro-3-(4-ethyl-2-hydroxyphenyl)-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound OC1=CC(CC)=CC=C1C1=C(Cl)SC2=C1C(O)=C(C=1C=CC=CC=1)C(=O)N2 BWUIWUXDYJRFGT-UHFFFAOYSA-N 0.000 claims 2
- GPPPTVDDPVPRNQ-UHFFFAOYSA-N 2-chloro-3-(4-fluoro-2-hydroxyphenyl)-4-hydroxy-5-(4-methoxyphenyl)-7h-thieno[2,3-b]pyridin-6-one Chemical compound C1=CC(OC)=CC=C1C(C(N1)=O)=C(O)C2=C1SC(Cl)=C2C1=CC=C(F)C=C1O GPPPTVDDPVPRNQ-UHFFFAOYSA-N 0.000 claims 2
- PHVCJHNWFQBRCC-UHFFFAOYSA-N 2-chloro-3-(5-fluoro-2-hydroxyphenyl)-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound OC1=CC=C(F)C=C1C1=C(Cl)SC2=C1C(O)=C(C=1C=CC=CC=1)C(=O)N2 PHVCJHNWFQBRCC-UHFFFAOYSA-N 0.000 claims 2
- FFNQJCFHTYLNSR-UHFFFAOYSA-N 2-chloro-4-hydroxy-3-(1-hydroxynaphthalen-2-yl)-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound O=C1NC=2SC(Cl)=C(C=3C(=C4C=CC=CC4=CC=3)O)C=2C(O)=C1C1=CC=CC=C1 FFNQJCFHTYLNSR-UHFFFAOYSA-N 0.000 claims 2
- SLXAUDWKLZUWEE-UHFFFAOYSA-N 2-chloro-4-hydroxy-3-(2-hydroxy-3,4-dimethylphenyl)-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound OC1=C(C)C(C)=CC=C1C1=C(Cl)SC2=C1C(O)=C(C=1C=CC=CC=1)C(=O)N2 SLXAUDWKLZUWEE-UHFFFAOYSA-N 0.000 claims 2
- SBBOSHWKVWYCJT-UHFFFAOYSA-N 2-chloro-4-hydroxy-3-(3-methoxy-4-methylphenyl)-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound C1=C(C)C(OC)=CC(C=2C=3C(O)=C(C=4C=CC=CC=4)C(=O)NC=3SC=2Cl)=C1 SBBOSHWKVWYCJT-UHFFFAOYSA-N 0.000 claims 2
- JBUDNJIDKXRJBT-UHFFFAOYSA-N 2-chloro-4-hydroxy-3-phenyl-5-[4-(trifluoromethyl)phenyl]-7h-thieno[2,3-b]pyridin-6-one Chemical compound O=C1NC=2SC(Cl)=C(C=3C=CC=CC=3)C=2C(O)=C1C1=CC=C(C(F)(F)F)C=C1 JBUDNJIDKXRJBT-UHFFFAOYSA-N 0.000 claims 2
- HFMONUMSUAMBCV-UHFFFAOYSA-N 3-(2-chloro-4-hydroxy-6-oxo-5-phenyl-7h-thieno[2,3-b]pyridin-3-yl)benzoic acid Chemical compound OC(=O)C1=CC=CC(C=2C=3C(O)=C(C=4C=CC=CC=4)C(=O)NC=3SC=2Cl)=C1 HFMONUMSUAMBCV-UHFFFAOYSA-N 0.000 claims 2
- PLGHBLSUXABEHT-UHFFFAOYSA-N 3-(3-fluoro-2-hydroxy-4-methylphenyl)-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound OC1=C(F)C(C)=CC=C1C1=CSC2=C1C(O)=C(C=1C=CC=CC=1)C(=O)N2 PLGHBLSUXABEHT-UHFFFAOYSA-N 0.000 claims 2
- GPLBXSIDUXQNHR-UHFFFAOYSA-N 3-(3-fluoro-2-methoxy-4-methylphenyl)-5-(4-fluorophenyl)-4-hydroxy-7h-thieno[2,3-b]pyridin-6-one Chemical compound COC1=C(F)C(C)=CC=C1C1=CSC2=C1C(O)=C(C=1C=CC(F)=CC=1)C(=O)N2 GPLBXSIDUXQNHR-UHFFFAOYSA-N 0.000 claims 2
- GTVMOIAZBRMKLK-UHFFFAOYSA-N 3-(4-bromo-2-hydroxyphenyl)-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound OC1=CC(Br)=CC=C1C1=CSC2=C1C(O)=C(C=1C=CC=CC=1)C(=O)N2 GTVMOIAZBRMKLK-UHFFFAOYSA-N 0.000 claims 2
- ZNPIJSKIKWCLTC-UHFFFAOYSA-N 3-(4-fluoro-2-hydroxyphenyl)-4-hydroxy-5-(4-methoxyphenyl)-7h-thieno[2,3-b]pyridin-6-one Chemical compound C1=CC(OC)=CC=C1C(C(N1)=O)=C(O)C2=C1SC=C2C1=CC=C(F)C=C1O ZNPIJSKIKWCLTC-UHFFFAOYSA-N 0.000 claims 2
- XXPFKSFEYKJDQE-UHFFFAOYSA-N 3-[2-chloro-3-(4-fluorophenyl)-4-hydroxy-6-oxo-7h-thieno[2,3-b]pyridin-5-yl]benzonitrile Chemical compound O=C1NC=2SC(Cl)=C(C=3C=CC(F)=CC=3)C=2C(O)=C1C1=CC=CC(C#N)=C1 XXPFKSFEYKJDQE-UHFFFAOYSA-N 0.000 claims 2
- AWEJMHVEZSBDGY-UHFFFAOYSA-N 3-[4-hydroxy-3-(2-hydroxy-4-methylphenyl)-6-oxo-7h-thieno[2,3-b]pyridin-5-yl]benzonitrile Chemical compound OC1=CC(C)=CC=C1C1=CSC2=C1C(O)=C(C=1C=C(C=CC=1)C#N)C(=O)N2 AWEJMHVEZSBDGY-UHFFFAOYSA-N 0.000 claims 2
- RPEIUDNCZPYUNL-UHFFFAOYSA-N 4-hydroxy-3-(1-hydroxynaphthalen-2-yl)-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound O=C1NC=2SC=C(C=3C(=C4C=CC=CC4=CC=3)O)C=2C(O)=C1C1=CC=CC=C1 RPEIUDNCZPYUNL-UHFFFAOYSA-N 0.000 claims 2
- ZAYQTNBNDDRWNU-UHFFFAOYSA-N 4-hydroxy-3-(2-hydroxy-4-methylphenyl)-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound OC1=CC(C)=CC=C1C1=CSC2=C1C(O)=C(C=1C=CC=CC=1)C(=O)N2 ZAYQTNBNDDRWNU-UHFFFAOYSA-N 0.000 claims 2
- OLBOUYBHMSHDSP-UHFFFAOYSA-N 4-hydroxy-3-(2-hydroxy-5-methoxyphenyl)-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound COC1=CC=C(O)C(C=2C=3C(O)=C(C=4C=CC=CC=4)C(=O)NC=3SC=2)=C1 OLBOUYBHMSHDSP-UHFFFAOYSA-N 0.000 claims 2
- OCJTZTJHSBXLBP-UHFFFAOYSA-N 4-hydroxy-3-(3-hydroxy-4-methylphenyl)-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound C1=C(O)C(C)=CC=C1C1=CSC2=C1C(O)=C(C=1C=CC=CC=1)C(=O)N2 OCJTZTJHSBXLBP-UHFFFAOYSA-N 0.000 claims 2
- CXNQAIQLRJAXQL-UHFFFAOYSA-N 4-hydroxy-5-(3-methoxyphenyl)-3-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound COC1=CC=CC(C=2C(NC=3SC=C(C=3C=2O)C=2C=CC=CC=2)=O)=C1 CXNQAIQLRJAXQL-UHFFFAOYSA-N 0.000 claims 2
- JVGFZQKHBAVBRI-UHFFFAOYSA-N 4-hydroxy-6-oxo-3,5-diphenyl-7h-thieno[2,3-b]pyridine-2-carbonitrile Chemical compound O=C1NC=2SC(C#N)=C(C=3C=CC=CC=3)C=2C(O)=C1C1=CC=CC=C1 JVGFZQKHBAVBRI-UHFFFAOYSA-N 0.000 claims 2
- IXLCFMXSJWKPGW-UHFFFAOYSA-N ClC1=C(C2=C(NC(C(=C2O)C2=CC=CC=C2)=O)S1)C1=C(C=C(C(=C1)C)C)O Chemical compound ClC1=C(C2=C(NC(C(=C2O)C2=CC=CC=C2)=O)S1)C1=C(C=C(C(=C1)C)C)O IXLCFMXSJWKPGW-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- BPNNEAVIVQOCOD-UHFFFAOYSA-N 2-bromo-4-hydroxy-3,5-diphenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound O=C1NC=2SC(Br)=C(C=3C=CC=CC=3)C=2C(O)=C1C1=CC=CC=C1 BPNNEAVIVQOCOD-UHFFFAOYSA-N 0.000 claims 1
- MWZWDVLWLPGEIY-UHFFFAOYSA-N 2-chloro-3,5-bis(4-fluorophenyl)-4-hydroxy-7h-thieno[2,3-b]pyridin-6-one Chemical compound O=C1NC=2SC(Cl)=C(C=3C=CC(F)=CC=3)C=2C(O)=C1C1=CC=C(F)C=C1 MWZWDVLWLPGEIY-UHFFFAOYSA-N 0.000 claims 1
- NKRHDEMOKVRCTM-UHFFFAOYSA-N 2-chloro-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound O=C1NC=2SC(Cl)=C(C=3C=C4OCCOC4=CC=3)C=2C(O)=C1C1=CC=CC=C1 NKRHDEMOKVRCTM-UHFFFAOYSA-N 0.000 claims 1
- PUDYDIYRWDFHFL-UHFFFAOYSA-N 2-chloro-3-(2,4-difluorophenyl)-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound O=C1NC=2SC(Cl)=C(C=3C(=CC(F)=CC=3)F)C=2C(O)=C1C1=CC=CC=C1 PUDYDIYRWDFHFL-UHFFFAOYSA-N 0.000 claims 1
- NOLTVZKROKWOAG-UHFFFAOYSA-N 2-chloro-3-(2,6-difluorophenyl)-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound O=C1NC=2SC(Cl)=C(C=3C(=CC=CC=3F)F)C=2C(O)=C1C1=CC=CC=C1 NOLTVZKROKWOAG-UHFFFAOYSA-N 0.000 claims 1
- MDLUBEHAYZGVOU-UHFFFAOYSA-N 2-chloro-3-(2-chlorophenyl)-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound O=C1NC=2SC(Cl)=C(C=3C(=CC=CC=3)Cl)C=2C(O)=C1C1=CC=CC=C1 MDLUBEHAYZGVOU-UHFFFAOYSA-N 0.000 claims 1
- FEXOBQAOLIUVKE-UHFFFAOYSA-N 2-chloro-3-(2-fluoro-4-hydroxyphenyl)-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound FC1=CC(O)=CC=C1C1=C(Cl)SC2=C1C(O)=C(C=1C=CC=CC=1)C(=O)N2 FEXOBQAOLIUVKE-UHFFFAOYSA-N 0.000 claims 1
- BFLWPCIURIUSPD-UHFFFAOYSA-N 2-chloro-3-(2-fluoro-4-methoxyphenyl)-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound FC1=CC(OC)=CC=C1C1=C(Cl)SC2=C1C(O)=C(C=1C=CC=CC=1)C(=O)N2 BFLWPCIURIUSPD-UHFFFAOYSA-N 0.000 claims 1
- RRXGAEYSXOVKCL-UHFFFAOYSA-N 2-chloro-3-(2-fluorophenyl)-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound O=C1NC=2SC(Cl)=C(C=3C(=CC=CC=3)F)C=2C(O)=C1C1=CC=CC=C1 RRXGAEYSXOVKCL-UHFFFAOYSA-N 0.000 claims 1
- VZIRHEJVPGXNAE-UHFFFAOYSA-N 2-chloro-3-(3,4-difluorophenyl)-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound O=C1NC=2SC(Cl)=C(C=3C=C(F)C(F)=CC=3)C=2C(O)=C1C1=CC=CC=C1 VZIRHEJVPGXNAE-UHFFFAOYSA-N 0.000 claims 1
- NDSHUOLVSBNICH-UHFFFAOYSA-N 2-chloro-3-(3,4-dimethoxyphenyl)-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=C(Cl)SC2=C1C(O)=C(C=1C=CC=CC=1)C(=O)N2 NDSHUOLVSBNICH-UHFFFAOYSA-N 0.000 claims 1
- WPLBHHQLZHRGDN-UHFFFAOYSA-N 2-chloro-3-(3,4-dimethylphenyl)-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound C1=C(C)C(C)=CC=C1C1=C(Cl)SC2=C1C(O)=C(C=1C=CC=CC=1)C(=O)N2 WPLBHHQLZHRGDN-UHFFFAOYSA-N 0.000 claims 1
- YUMBAHWYBOSNNC-UHFFFAOYSA-N 2-chloro-3-(3-ethoxyphenyl)-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound CCOC1=CC=CC(C=2C=3C(O)=C(C(=O)NC=3SC=2Cl)C=2C=CC=CC=2)=C1 YUMBAHWYBOSNNC-UHFFFAOYSA-N 0.000 claims 1
- KAMMKGQLUFZNDE-UHFFFAOYSA-N 2-chloro-3-(3-fluoro-2-methoxy-4-methylphenyl)-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound COC1=C(F)C(C)=CC=C1C1=C(Cl)SC2=C1C(O)=C(C=1C=CC=CC=1)C(=O)N2 KAMMKGQLUFZNDE-UHFFFAOYSA-N 0.000 claims 1
- GUDNAWOHNVDXST-UHFFFAOYSA-N 2-chloro-3-(3-fluoro-4-hydroxyphenyl)-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound C1=C(F)C(O)=CC=C1C1=C(Cl)SC2=C1C(O)=C(C=1C=CC=CC=1)C(=O)N2 GUDNAWOHNVDXST-UHFFFAOYSA-N 0.000 claims 1
- YERINDNNXUDMKO-UHFFFAOYSA-N 2-chloro-3-(3-fluoro-4-methoxyphenyl)-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound C1=C(F)C(OC)=CC=C1C1=C(Cl)SC2=C1C(O)=C(C=1C=CC=CC=1)C(=O)N2 YERINDNNXUDMKO-UHFFFAOYSA-N 0.000 claims 1
- GJGPWQLKSIFVGG-UHFFFAOYSA-N 2-chloro-3-(3-fluorophenyl)-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound O=C1NC=2SC(Cl)=C(C=3C=C(F)C=CC=3)C=2C(O)=C1C1=CC=CC=C1 GJGPWQLKSIFVGG-UHFFFAOYSA-N 0.000 claims 1
- BRXDNZRYVSDNKV-UHFFFAOYSA-N 2-chloro-3-(4-chlorophenyl)-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound O=C1NC=2SC(Cl)=C(C=3C=CC(Cl)=CC=3)C=2C(O)=C1C1=CC=CC=C1 BRXDNZRYVSDNKV-UHFFFAOYSA-N 0.000 claims 1
- AUMAOJVEUUCJOL-UHFFFAOYSA-N 2-chloro-3-(4-ethylphenyl)-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound C1=CC(CC)=CC=C1C1=C(Cl)SC2=C1C(O)=C(C=1C=CC=CC=1)C(=O)N2 AUMAOJVEUUCJOL-UHFFFAOYSA-N 0.000 claims 1
- KZNWKHQDIHOZOY-UHFFFAOYSA-N 2-chloro-3-(4-fluoro-2-hydroxyphenyl)-4-hydroxy-5-(4-methylphenyl)-7h-thieno[2,3-b]pyridin-6-one Chemical compound C1=CC(C)=CC=C1C(C(N1)=O)=C(O)C2=C1SC(Cl)=C2C1=CC=C(F)C=C1O KZNWKHQDIHOZOY-UHFFFAOYSA-N 0.000 claims 1
- HKXJRAXVNZHPKP-UHFFFAOYSA-N 2-chloro-3-(4-fluoro-2-hydroxyphenyl)-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound OC1=CC(F)=CC=C1C1=C(Cl)SC2=C1C(O)=C(C=1C=CC=CC=1)C(=O)N2 HKXJRAXVNZHPKP-UHFFFAOYSA-N 0.000 claims 1
- LXSNLFBLBILZPS-UHFFFAOYSA-N 2-chloro-3-(4-fluoro-2-hydroxyphenyl)-5-(4-fluorophenyl)-4-hydroxy-7h-thieno[2,3-b]pyridin-6-one Chemical compound OC1=CC(F)=CC=C1C1=C(Cl)SC2=C1C(O)=C(C=1C=CC(F)=CC=1)C(=O)N2 LXSNLFBLBILZPS-UHFFFAOYSA-N 0.000 claims 1
- VCCVWQOGBMPZHP-UHFFFAOYSA-N 2-chloro-3-(4-fluoro-2-methoxyphenyl)-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound COC1=CC(F)=CC=C1C1=C(Cl)SC2=C1C(O)=C(C=1C=CC=CC=1)C(=O)N2 VCCVWQOGBMPZHP-UHFFFAOYSA-N 0.000 claims 1
- OAOCTRZECSMFFF-UHFFFAOYSA-N 2-chloro-3-(4-fluoro-2-phenylmethoxyphenyl)-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound O=C1NC=2SC(Cl)=C(C=3C(=CC(F)=CC=3)OCC=3C=CC=CC=3)C=2C(O)=C1C1=CC=CC=C1 OAOCTRZECSMFFF-UHFFFAOYSA-N 0.000 claims 1
- ZRBYBZXURFMCIR-UHFFFAOYSA-N 2-chloro-3-(4-fluorophenyl)-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound O=C1NC=2SC(Cl)=C(C=3C=CC(F)=CC=3)C=2C(O)=C1C1=CC=CC=C1 ZRBYBZXURFMCIR-UHFFFAOYSA-N 0.000 claims 1
- SENWWPIXZMBGCX-UHFFFAOYSA-N 2-chloro-3-(5-chloro-1-hydroxynaphthalen-2-yl)-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound O=C1NC=2SC(Cl)=C(C=3C(=C4C=CC=C(Cl)C4=CC=3)O)C=2C(O)=C1C1=CC=CC=C1 SENWWPIXZMBGCX-UHFFFAOYSA-N 0.000 claims 1
- LYLZADDOROGHMF-UHFFFAOYSA-N 2-chloro-3-(5-fluoro-2-methoxyphenyl)-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound COC1=CC=C(F)C=C1C1=C(Cl)SC2=C1C(O)=C(C=1C=CC=CC=1)C(=O)N2 LYLZADDOROGHMF-UHFFFAOYSA-N 0.000 claims 1
- CMOBNHCDZQVHKM-UHFFFAOYSA-N 2-chloro-3-(5-fluoro-2-phenylmethoxyphenyl)-4-hydroxy-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound O=C1NC=2SC(Cl)=C(C=3C(=CC=C(F)C=3)OCC=3C=CC=CC=3)C=2C(O)=C1C1=CC=CC=C1 CMOBNHCDZQVHKM-UHFFFAOYSA-N 0.000 claims 1
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| CA2784553C (en) * | 2009-12-29 | 2014-08-19 | Poxel | Thieno [2,3-b] pyridinedione activators of ampk and therapeutic uses thereof |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US20130085169A1 (en) | 2010-04-02 | 2013-04-04 | Inserm (Institut National De La Sante Et De La Recherche Medicale) | 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 |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| 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 |
| CA2830706A1 (en) * | 2011-03-07 | 2012-09-13 | Glaxosmithkline Llc | Quinolinone derivatives |
| 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 |
| JP6064062B2 (ja) | 2013-03-15 | 2017-01-18 | ファイザー・インク | Ａｍｐｋを活性化させるインダゾール化合物 |
| US9827222B2 (en) | 2013-07-01 | 2017-11-28 | Emory University | Treating or preventing nephrogenic diabetes insipidus |
| US10143703B2 (en) | 2014-01-02 | 2018-12-04 | Massachusetts Eye And Ear Infirmary | Treating ocular neovascularization |
| CN104892569A (zh) * | 2015-06-23 | 2015-09-09 | 佛山市赛维斯医药科技有限公司 | 末端取代的硝苯六甲苯黄原酸酯类的化合物、制备方法及用途 |
| CN104945370A (zh) * | 2015-06-23 | 2015-09-30 | 佛山市赛维斯医药科技有限公司 | 含卤代噻吩和硝苯六甲苯结构的黄原酸酯类化合物、制备方法及用途 |
| CN104892568A (zh) * | 2015-06-23 | 2015-09-09 | 佛山市赛维斯医药科技有限公司 | 一种含六甲基苯环和腈基苯结构的黄原酸酯类化合物、其制备方法及用途 |
| CN105037321A (zh) * | 2015-06-23 | 2015-11-11 | 佛山市赛维斯医药科技有限公司 | 含六甲基苯环的黄原酸酯类的ampk激活剂、制备方法及用途 |
| CN104945369A (zh) * | 2015-06-23 | 2015-09-30 | 佛山市赛维斯医药科技有限公司 | 一种含六甲基苯环和硝基苯结构的黄原酸酯类化合物、其制备方法及用途 |
| CN105037322A (zh) * | 2015-06-23 | 2015-11-11 | 佛山市赛维斯医药科技有限公司 | 含六甲基苯环和烷氧苯结构的黄原酸酯类化合物、其制备方法及用途 |
| CN104926757A (zh) * | 2015-06-24 | 2015-09-23 | 佛山市赛维斯医药科技有限公司 | 含烷氧苯基的双酰基苄胺类ampk激活剂、其制备方法及用途 |
| CN104926755A (zh) * | 2015-06-24 | 2015-09-23 | 佛山市赛维斯医药科技有限公司 | 硝苯双酰基苄胺类ampk激活剂、其制备方法及用途 |
| CN105001181A (zh) * | 2015-06-24 | 2015-10-28 | 佛山市赛维斯医药科技有限公司 | 一类双酰基苄胺类的ampk激活剂、其制备方法及用途 |
| CN105001194A (zh) * | 2015-06-24 | 2015-10-28 | 佛山市赛维斯医药科技有限公司 | 一种含氨基噻吩以及六甲苯结构的黄原酸酯类化合物、制备方法及用途 |
| CN104945371A (zh) * | 2015-06-24 | 2015-09-30 | 佛山市赛维斯医药科技有限公司 | 一种含腈基噻吩以及六甲苯结构的黄原酸酯类化合物、制备方法及用途 |
| CN104926756A (zh) * | 2015-06-24 | 2015-09-23 | 佛山市赛维斯医药科技有限公司 | 一类含腈基苯的双酰基苄胺类化合物、其制备方法及用途 |
| CN105037296A (zh) * | 2015-06-24 | 2015-11-11 | 佛山市赛维斯医药科技有限公司 | 一类卤代苯双酰基苄胺类的ampk激活剂、其制备方法及用途 |
| CN104945372A (zh) * | 2015-06-24 | 2015-09-30 | 佛山市赛维斯医药科技有限公司 | 一种含二硝基以及六甲苯结构的黄原酸酯类化合物、制备方法及用途 |
| RS61919B1 (sr) | 2015-06-25 | 2021-06-30 | Univ Health Network | Inhibitori hpk1 i postupci za njihovo korišćenje |
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| WO2020099678A1 (en) * | 2018-11-16 | 2020-05-22 | Poxel | Monohydrate potassium salt of a thienopyridone derivative and its preparation process |
| WO2020201263A1 (en) | 2019-04-01 | 2020-10-08 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods and pharmaceutical compositions for the treatment and prevention of cardiac remodeling |
| KR20220160030A (ko) | 2020-03-26 | 2022-12-05 | 폭셀 | 부신백색질형성장애증 또는 부신척수신경병증의 치료에 있어서의 티에노피리돈 유도체의 용도 |
| MX2022012350A (es) * | 2020-04-02 | 2022-10-27 | Poxel | Uso de un derivado de tienopiridona en el tratamiento de poliquistosis renal autosomica dominante (adpkd). |
| WO2021236617A1 (en) | 2020-05-19 | 2021-11-25 | Kallyope, Inc. | Ampk activators |
| CA3183575A1 (en) | 2020-06-26 | 2021-12-30 | Iyassu Sebhat | Ampk activators |
| 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 |
| JP2024540522A (ja) | 2021-11-19 | 2024-10-31 | ザ・ブロード・インスティテュート・インコーポレイテッド | キナーゼを標的結合部分で標識するための二官能性キメラ分子及びその使用方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU626418B2 (en) | 1989-05-16 | 1992-07-30 | Merrell Pharmaceuticals Inc. | Excitatory amino acid antagonists |
| DE4444815A1 (de) | 1994-12-15 | 1996-06-20 | Merck Patent Gmbh | Thienopyridone |
| GB0214268D0 (en) | 2002-06-20 | 2002-07-31 | Celltech R&D Ltd | Chemical compounds |
| US7119205B2 (en) * | 2003-05-16 | 2006-10-10 | Abbott Laboratories | Thienopyridones as AMPK activators for the treatment of diabetes and obesity |
| EP1754483A1 (en) * | 2005-08-18 | 2007-02-21 | Merck Sante | Use of thienopyridone derivatives as AMPK activators and pharmaceutical compositions containing them |
| MX2010008376A (es) | 2008-02-04 | 2011-02-22 | Mercury Therapeutics Inc | Moduladores ampk. |
-
2009
- 2009-03-17 MY MYPI2010004711A patent/MY155836A/en unknown
- 2009-03-17 WO PCT/EP2009/001937 patent/WO2009124636A1/en not_active Ceased
- 2009-03-17 AU AU2009235784A patent/AU2009235784B2/en not_active Ceased
- 2009-03-17 HR HRP20160907TT patent/HRP20160907T1/hr unknown
- 2009-03-17 MX MX2010011047A patent/MX2010011047A/es active IP Right Grant
- 2009-03-17 BR BRPI0910439A patent/BRPI0910439B8/pt not_active IP Right Cessation
- 2009-03-17 CN CN200980112692.6A patent/CN101998853B/zh not_active Expired - Fee Related
- 2009-03-17 US US12/937,147 patent/US8563729B2/en not_active Expired - Fee Related
- 2009-03-17 EA EA201001585A patent/EA017756B1/ru unknown
- 2009-03-17 ES ES09731265.6T patent/ES2584278T3/es active Active
- 2009-03-17 HU HUE09731265A patent/HUE027857T2/en unknown
- 2009-03-17 PT PT97312656T patent/PT2262500T/pt unknown
- 2009-03-17 CA CA2721025A patent/CA2721025C/en active Active
- 2009-03-17 PL PL09731265.6T patent/PL2262500T3/pl unknown
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- 2009-03-17 NZ NZ589136A patent/NZ589136A/en not_active IP Right Cessation
- 2009-03-17 UA UAA201013392A patent/UA103321C2/ru unknown
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- 2009-03-17 KR KR1020107025218A patent/KR101630466B1/ko not_active Expired - Fee Related
- 2009-03-17 DK DK09731265.6T patent/DK2262500T3/en active
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- 2010-10-07 CO CO10124423A patent/CO6300954A2/es not_active Application Discontinuation
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