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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| EA020588B1 (ru) * | 2009-12-29 | 2014-12-30 | Поксел | ТИЕНО[2,3-b]ПИРИДИНДИОНОВЫЕ АКТИВАТОРЫ АМФК И ИХ ТЕРАПЕВТИЧЕСКОЕ ПРИМЕНЕНИЕ |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| 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 |
| 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 |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| WO2018002215A1 (en) | 2016-06-30 | 2018-01-04 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods and pharmaceutical compositions for the treatment of cardiomyopathies |
| ES2970120T3 (es) * | 2018-11-16 | 2024-05-27 | Poxel | Sal de potasio monohidratada de un derivado de tienopiridona y su proceso de preparación |
| 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 |
| WO2021191435A1 (en) | 2020-03-26 | 2021-09-30 | Poxel | Use of a thienopyridone derivative in the treatment of adrenoleukodystrophy or adrenomyeloneuropathy |
| US12310949B2 (en) * | 2020-04-02 | 2025-05-27 | Poxel | Use of a thienopyridone derivative in the treatment of autosomal dominant polycystic kidney disease (ADPKD) |
| 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 |
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 |
| MY158994A (en) | 2008-02-04 | 2016-11-30 | Mercury Therapeutics Inc | Ampk modulators |
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