DK2262500T3 - THIENOPYRIDON DERIVATIVES AS AMP-ACTIVATED PROTEINKINASE (AMPK) ACTIVATORS - Google Patents

Info

Publication number

DK2262500T3

DK2262500T3 DK09731265.6T DK09731265T DK2262500T3 DK 2262500 T3 DK2262500 T3 DK 2262500T3 DK 09731265 T DK09731265 T DK 09731265T DK 2262500 T3 DK2262500 T3 DK 2262500T3

Authority

DK

Denmark

Prior art keywords

hydroxy

pyridin

chloro

phenyl

thieno

Prior art date

2008-04-11

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• 108010011376 AMP-Activated Protein Kinases Proteins 0.000 title description 44
• 102000014156 AMP-Activated Protein Kinases Human genes 0.000 title description 44
• 239000012190 activator Substances 0.000 title description 10
• -1 2-hydroxyphenyl Chemical group 0.000 claims description 132
• 150000001875 compounds Chemical class 0.000 claims description 121
• 150000003839 salts Chemical class 0.000 claims description 63
• 239000000203 mixture Substances 0.000 claims description 49
• 238000011282 treatment Methods 0.000 claims description 34
• 206010012601 diabetes mellitus Diseases 0.000 claims description 25
• 238000000034 method Methods 0.000 claims description 22
• 239000002253 acid Substances 0.000 claims description 18
• 239000003814 drug Substances 0.000 claims description 17
• 125000004432 carbon atom Chemical group C* 0.000 claims description 14
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
• 125000001624 naphthyl group Chemical group 0.000 claims description 12
• 206010028980 Neoplasm Diseases 0.000 claims description 11
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
• 125000000217 alkyl group Chemical group 0.000 claims description 10
• 208000001145 Metabolic Syndrome Diseases 0.000 claims description 9
• 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 9
• 201000011510 cancer Diseases 0.000 claims description 9
• 230000008569 process Effects 0.000 claims description 9
• 239000012453 solvate Substances 0.000 claims description 9
• WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 7
• 208000008589 Obesity Diseases 0.000 claims description 7
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
• 235000020824 obesity Nutrition 0.000 claims description 7
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
• 238000002360 preparation method Methods 0.000 claims description 7
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
• 125000002950 monocyclic group Chemical group 0.000 claims description 6
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
• 125000004434 sulfur atom Chemical group 0.000 claims description 6
• 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 description 5
• JZGNNEVNFNRILW-UHFFFAOYSA-N 2-chloro-4-hydroxy-3-(3-methoxyphenyl)-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound COC1=CC=CC(C=2C=3C(O)=C(C=4C=CC=CC=4)C(=O)NC=3SC=2Cl)=C1 JZGNNEVNFNRILW-UHFFFAOYSA-N 0.000 claims description 4
• 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 description 4
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
• 206010061218 Inflammation Diseases 0.000 claims description 4
• 239000002671 adjuvant Substances 0.000 claims description 4
• KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 4
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
• 230000004054 inflammatory process Effects 0.000 claims description 4
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
• 125000002541 furyl group Chemical group 0.000 claims description 3
• 125000002883 imidazolyl group Chemical group 0.000 claims description 3
• 125000001041 indolyl group Chemical group 0.000 claims description 3
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 125000002971 oxazolyl group Chemical group 0.000 claims description 3
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
• 125000004076 pyridyl group Chemical group 0.000 claims description 3
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
• 125000000335 thiazolyl group Chemical group 0.000 claims description 3
• 125000001544 thienyl group Chemical group 0.000 claims description 3
• 125000001425 triazolyl group Chemical group 0.000 claims description 3
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 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 description 2
• XNKAQENMUMOQKE-UHFFFAOYSA-N 2-chloro-4-hydroxy-3-(2-hydroxy-4-methylphenyl)-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(C)C=C1O XNKAQENMUMOQKE-UHFFFAOYSA-N 0.000 claims description 2
• RQBCLBVIOWGBJR-UHFFFAOYSA-N 2-chloro-4-hydroxy-3-(2-hydroxy-4-methylphenyl)-5-pyridin-3-yl-7h-thieno[2,3-b]pyridin-6-one Chemical compound OC1=CC(C)=CC=C1C1=C(Cl)SC2=C1C(O)=C(C=1C=NC=CC=1)C(=O)N2 RQBCLBVIOWGBJR-UHFFFAOYSA-N 0.000 claims description 2
• VKYBPTRGTISQOV-UHFFFAOYSA-N 2-chloro-4-hydroxy-3-(2-hydroxyphenyl)-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound OC1=CC=CC=C1C1=C(Cl)SC2=C1C(O)=C(C=1C=CC=CC=1)C(=O)N2 VKYBPTRGTISQOV-UHFFFAOYSA-N 0.000 claims description 2
• YNHCLVLJLSXVKW-UHFFFAOYSA-N 2-chloro-4-hydroxy-3-(2-methoxy-3,4-dimethylphenyl)-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound COC1=C(C)C(C)=CC=C1C1=C(Cl)SC2=C1C(O)=C(C=1C=CC=CC=1)C(=O)N2 YNHCLVLJLSXVKW-UHFFFAOYSA-N 0.000 claims description 2
• PFKOAPHDDFHQAM-UHFFFAOYSA-N 2-chloro-4-hydroxy-3-(2-methoxyphenyl)-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound COC1=CC=CC=C1C1=C(Cl)SC2=C1C(O)=C(C=1C=CC=CC=1)C(=O)N2 PFKOAPHDDFHQAM-UHFFFAOYSA-N 0.000 claims description 2
• SYXIXZOXHDWMRO-UHFFFAOYSA-N 2-chloro-4-hydroxy-3-[2-(2-hydroxy-4,5-dimethylphenyl)phenyl]-5-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound C1=C(C)C(C)=CC(O)=C1C1=CC=CC=C1C1=C(Cl)SC2=C1C(O)=C(C=1C=CC=CC=1)C(=O)N2 SYXIXZOXHDWMRO-UHFFFAOYSA-N 0.000 claims description 2
• LHAASRBODGNGKU-UHFFFAOYSA-N 2-chloro-4-hydroxy-3-phenyl-5-[3-(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=CC(C(F)(F)F)=C1 LHAASRBODGNGKU-UHFFFAOYSA-N 0.000 claims description 2
• JSURPJLNEIKMAW-UHFFFAOYSA-N 2-chloro-4-hydroxy-3-phenyl-5-pyridin-3-yl-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=CN=C1 JSURPJLNEIKMAW-UHFFFAOYSA-N 0.000 claims description 2
• YSVFZRFKNDTCEY-UHFFFAOYSA-N 2-chloro-4-hydroxy-3-phenyl-5-thiophen-2-yl-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=CS1 YSVFZRFKNDTCEY-UHFFFAOYSA-N 0.000 claims description 2
• UPPWFDHMKDQFBQ-UHFFFAOYSA-N 2-chloro-4-hydroxy-5-(2-methylphenyl)-3-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound CC1=CC=CC=C1C(C(N1)=O)=C(O)C2=C1SC(Cl)=C2C1=CC=CC=C1 UPPWFDHMKDQFBQ-UHFFFAOYSA-N 0.000 claims description 2
• OTLVACAYSYVMDC-UHFFFAOYSA-N 2-chloro-4-hydroxy-5-(3-methanehydrazonoylphenyl)-3-phenyl-7H-thieno[2,3-b]pyridin-6-one hydrochloride Chemical compound Cl.ClC1=C(C2=C(NC(C(=C2O)C2=CC(=CC=C2)C=NN)=O)S1)C1=CC=CC=C1 OTLVACAYSYVMDC-UHFFFAOYSA-N 0.000 claims description 2
• GEBSWAHJESXUSG-UHFFFAOYSA-N 2-chloro-4-hydroxy-5-(3-methoxyphenyl)-3-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound COC1=CC=CC(C=2C(NC=3SC(Cl)=C(C=3C=2O)C=2C=CC=CC=2)=O)=C1 GEBSWAHJESXUSG-UHFFFAOYSA-N 0.000 claims description 2
• NVWCTSORLLWFQD-UHFFFAOYSA-N 2-chloro-4-hydroxy-5-(3-methylphenyl)-3-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound CC1=CC=CC(C=2C(NC=3SC(Cl)=C(C=3C=2O)C=2C=CC=CC=2)=O)=C1 NVWCTSORLLWFQD-UHFFFAOYSA-N 0.000 claims description 2
• LZVMVHNYKUQCCF-UHFFFAOYSA-N 2-chloro-4-hydroxy-5-(3-methylsulfonylphenyl)-3-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound CS(=O)(=O)C1=CC=CC(C=2C(NC=3SC(Cl)=C(C=3C=2O)C=2C=CC=CC=2)=O)=C1 LZVMVHNYKUQCCF-UHFFFAOYSA-N 0.000 claims description 2
• VYJIXCILLHNFIA-UHFFFAOYSA-N 2-chloro-4-hydroxy-5-(4-methylphenyl)-3-phenyl-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=CC=C1 VYJIXCILLHNFIA-UHFFFAOYSA-N 0.000 claims description 2
• WAXGHBDGOOEVNQ-UHFFFAOYSA-N 2-chloro-4-hydroxy-5-(4-methylsulfonylphenyl)-3-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(C(N1)=O)=C(O)C2=C1SC(Cl)=C2C1=CC=CC=C1 WAXGHBDGOOEVNQ-UHFFFAOYSA-N 0.000 claims description 2
• LXZBIHDSKNKNTL-UHFFFAOYSA-N 2-chloro-4-hydroxy-5-(6-methoxypyridin-3-yl)-3-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound C1=NC(OC)=CC=C1C(C(N1)=O)=C(O)C2=C1SC(Cl)=C2C1=CC=CC=C1 LXZBIHDSKNKNTL-UHFFFAOYSA-N 0.000 claims description 2
• ICNJSMIWODAXLD-UHFFFAOYSA-N 2-chloro-4-hydroxy-5-phenyl-3-(4-propan-2-ylphenyl)-7h-thieno[2,3-b]pyridin-6-one Chemical compound C1=CC(C(C)C)=CC=C1C1=C(Cl)SC2=C1C(O)=C(C=1C=CC=CC=1)C(=O)N2 ICNJSMIWODAXLD-UHFFFAOYSA-N 0.000 claims description 2
• CYOOMGNIFXGEOZ-UHFFFAOYSA-N 2-chloro-4-hydroxy-5-phenyl-3-(4-propylphenyl)-7h-thieno[2,3-b]pyridin-6-one Chemical compound C1=CC(CCC)=CC=C1C1=C(Cl)SC2=C1C(O)=C(C=1C=CC=CC=1)C(=O)N2 CYOOMGNIFXGEOZ-UHFFFAOYSA-N 0.000 claims description 2
• MFVXSECIJNJKOT-UHFFFAOYSA-N 2-chloro-5-(2-fluorophenyl)-4-hydroxy-3-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=CC=C1F MFVXSECIJNJKOT-UHFFFAOYSA-N 0.000 claims description 2
• ALCJJDSHRUPCAB-UHFFFAOYSA-N 2-chloro-5-(3,4-dimethoxyphenyl)-4-hydroxy-3-phenyl-7h-thieno[2,3-b]pyridin-6-one Chemical compound C1=C(OC)C(OC)=CC=C1C(C(N1)=O)=C(O)C2=C1SC(Cl)=C2C1=CC=CC=C1 ALCJJDSHRUPCAB-UHFFFAOYSA-N 0.000 claims description 2
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