US 7,119,205 B2Granted

Thienopyridones as AMPK activators for the treatment of diabetes and obesity

AssigneeAbbott Laboratories

InventorsRajesh R. Iyengar, Andrew S. Judd, Gang Zhao, Philip R. Kym, Hing L. Sham, Yugui Gu, Gang Liu, Mei Liu, Hongyu Zhao, Richard F. Clark, Ernst U. Frevert, Barbara L. Cool, Tianyuan Zhang, Robert F. Keyes, Todd M. Hansen, Zhili Xin

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Abstract

The present invention relates to compounds that activate AMP-activated protein kinase (AMPK), including the preparation of the compounds, compositions containing the compounds and the use of the compounds in the prevention or treatment of disorders such as diabetes, metabolic syndrome, and obesity.

Claims14

Dependent claims

A compound of formula (I):

or a therapeutically suitable salt, ester or prodrug thereof, wherein
R1 is selected from the group consisting of hydrogen, alkoxy, alkoxycarbonyl, alkyl, alkenyl, alkynyl, carboxy, carboxyalkyl, cyano, cyanoalkyl, halogen, haloalkyl, trihaloalkyl, heterocycle, hydroxyalkyl, RaRbN—, RaRbNalkyl, and RcRdNC(O)—, wherein alkyl may be optionally substituted with O═ and Rt—N═;
R2 is selected from the group consisting of RfO—, HO—, RfS—, and HS—;
R3 is selected from the group consisting of alkoxycarbonyl, substituted aryl, arylalkyl, arylalkenyl, arylalkynyl, cycloalkyl, carboxy, carboxylalkyl, halogen, heteroaryl, heterocycle, heterocyclealkyl, RgRjN—, and RgRjNalkyl, wherein cycloalkyl may be fused to an aryl ring as defined herein;
R4 is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, arylalkyl, arylcarbonyl, aryloxycarbonyl, carboxy, carboxyalkyl, carboxyalkynyl, halogen, haloalkyl, heteroaryl, heterocycle, heterocyclealkyl, heterocyclecarbonyl, heterocycleoxycarbonyl, hydroxyalkyl, HO—N═CH—(CH2)u—, and RmRnN—;
u is 0, 1 or 2;
Ra and Rb are each individually selected from the group consisting of hydrogen, alkyl, alkylcarbonyl, alkoxylcarbonyl, aryl, arylalkyl, arylcarbonyl, arylalkyloxycarbonyl, heteroaryl, heterocycle, heterocyclealkyl, heterocyclecarbonyl, and heterocycleoxycarbonyl;
Rc and Rd are each independently selected from the group consisting of hydrogen, alkyl, aryl, arylalkyl, haloalkyl, hydroxyalkyl, and heterocycle;
Rf is selected from the group consisting of alkyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkylthioalkyl, and haloalkyl;
Rg and Rj are each independently selected from the group consisting of hydrogen, alkyl, alkoxycarbonyl, aryl, arylalkyl, arylcarbonyl, aryloxycarbonyl, heteroaryl, heterocycle, heterocyclealkyl, heterocyclecarbonyl, heterocycleoxycarbonyl, and haloalkyl;
Rm and Rn are each independently selected from the group consisting of hydrogen, alkyl, alkoxycarbonyl, aryl, arylalkyl, heteroaryl, heterocycle, heterocyclealkyl, and haloalkyl;
and
Rt is selected from the group consisting of hydrogen, alkyl and HO—.

10 more elements

A compound of formula (II)

or a therapeutically suitable salt, ester or prodrug thereof, wherein
R1 is selected from the group consisting of hydrogen, alkyl, alkoxy, alkoxycarbonyl, alkynyl, carboxy, cyano, halogen, heterocycle, and hydroxyalkyl, wherein alkyl may be optionally substituted with O═ and Rt—N═;
R2 is selected from the group consisting of RfO—, and HO—;
R4 is selected from the group consisting of hydrogen, alkyl, carboxyalkynyl, halogen, haloalkyl, heteroaryl, heterocycle, heterocyclealkyl, and HO—N═CH—(CH2)u—;
R5 is selected from the group consisting of alkenyl, alkenyloxy, alkoxy, alkoxyalkoxy, alkoxycarbonyl, alkyl, alkylcarbonyl, alkoxycarbonylalkoxy, alkynyl, aryl, aryloxy, carboxy, carboxyalkyl, carboxyalkoxy, cyano, cycloalkylalkoxy, formyl, halo, haloalkyl, trihaloalkyl, trihaloalkoxy, heteroaryl, heterocycle, hydroxy, hydroxyalkyl, hydroxyalkoxy, dihydroxyalkoxy, nitro, RpRqN—, RrRsNC(O)alkoxy, and RrRsNSO2alkoxy;
R6 and R7 are each individually selected from the group consisting of hydrogen, alkenyl, alkenyloxy, alkoxy, alkoxyalkoxy, alkoxycarbonyl, alkoxyalkynyl, alkyl, alkylcarbonyl, alkoxycarbonylalkoxy, alkynyl, aryl, aryloxy, carboxy, carboxyalkyl, carboxyalkoxy, carboxyalkynyl, cyano, cyanoalkoxy, cyanoalkynyl, cycloalkenylalkoxy, formyl, halo, haloalkyl, trihaloalkyl, trihaloalkoxy, heteroaryl, heterocycle, heterocyclealkenyl, heterocyclealkoxy, heterocycleoxyalkynyl, hydroxy, hydroxyalkenyl, hydroxyalkyl, hydroxyalkoxy, hydroxyalkynyl, dihydroxyalkoxy, nitro, RpRqN—, RrRsNC(O)alkoxy, RrRsNC(O)alkynyl, and RrRsNSO2alkoxy, Rw—O—N═CH—, and RxRyN-alkynyl or R6 and R7 together with the atoms to which they are attached form a ring selected from the group consisting of cycloalkyl and heterocycle;
u is 0, 1 or 2;
Rf is selected from the group consisting of alkyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkylthioalkyl, and haloalkyl;
Rp is selected from the group consisting of hydrogen, alkenyl, alkenylcarbonyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkoxycarbonylalkylcarbonyl, alkyl, alkylcarbonyl, alkynyl, aryl, arylalkenyl, arylalkyl, arylcarbonyl, haloalkyl, haloalkylcarbonyl, heteroaryl, heterocycle, heterocyclealkenyl, heterocyclealkyl, heterocyclealkylcarbonyl, heterocyclecarbonyl, trihaloalkyl, trihaloalkylcarbonyl, hydroxyalkyl, and hydroxyalkylcarbonyl;
Rq are each independently selected from the group consisting of hydrogen, alkyl, alkenyl;
Rr and Rs are each independently selected from the group consisting of hydrogen, alkyl, arylalkyl, hydroxyalkyl, heterocyclealkyl;
Rt is selected from the group consisting of hydrogen, alkyl and HO—;
Rw is selected from the group consisting of hydrogen, alkylcarbonyl-NH-alkyl-NHC(O)-alkyl, alkyl, alkyl(alkyl)N-alkyl-NHC(O)-alkyl, hydroxyalkyl-NHC(O)-alkyl, heterocyclealkyl-NHC(O)-alkyl, heterocycle-NHC(O)-alkyl, heteroarylalkyl-NHC(O)-alkyl;
and
Rx and Ry are each individually selected fro the group consisting of hydrogen, alkyl and alkylsulfonyl.

12 more elements

A compound of formula (III)

or a therapeutically suitable salt, ester or prodrug thereof, wherein
R1 is selected from the group consisting of hydrogen, alkyl, alkoxy, alkoxycarbonyl, alkynyl, carboxy, cyano, halogen, heterocycle, and hydroxyalkyl, wherein alkyl may be optionally substituted with O═ and Rt—N═;
R2 is selected from the group consisting of RfO—, and HO—;
R4 is selected from the group consisting of hydrogen, alkyl, carboxyalkynyl, halogen, haloalkyl, heteroaryl, heterocycle, heterocyclealkyl, and HO—N═CH—(CH2)u—;
R6 and R7 are each individually selected from the group consisting of hydrogen, alkenyl, alkenyloxy, alkoxy, alkoxyalkoxy, alkoxycarbonyl, alkoxyalkynyl, alkyl, alkylcarbonyl, alkoxycarbonylalkoxy, alkynyl, aryl, aryloxy, carboxy, carboxyalkyl, carboxyalkoxy, carboxyalkynyl, cyano, cyanoalkoxy, cyanoalkynyl, cycloalkenylalkoxy, formyl, halo, haloalkyl, trihaloalkyl, trihaloalkoxy, heteroaryl, heterocycle, heterocyclealkenyl, heterocyclealkoxy, heterocycleoxyalkynyl, hydroxy, hydroxyalkenyl, hydroxyalkyl, hydroxyalkoxy, hydroxyalkynyl, dihydroxyalkoxy, nitro, RpRqN—, RrRsNC(O)alkoxy, RrRsNC(O)alkynyl, and RrRsNSO2alkoxy, Rw—O—N═CH—, and RxRyNH-alkynyl or R6 and R7 together with the atoms to which they are attached form a ring selected from the group consisting of cycloalkyl and heterocycle;
R8, R9 and R10 are each individually selected from the group consisting of hydrogen, alkenyl, alkenyloxy, alkoxy, alkoxyalkoxy, alkoxycarbonyl, alkoxyalkynyl, alkyl, alkylcarbonyl, alkylSO2—, alkoxycarbonylalkoxy, alkynyl, arylalkynyl, aryloxy, carboxy, carboxyalkyl, carboxyalkynyl, carboxyalkoxy, cyano, formyl, halo, haloalkyl, heterocyclealkoxy, heterocycleoxyalkynyl, trihaloalkyl, trihaloalkoxy, hydroxy, hydroxyalkyl, hydroxyalkenyl, hydroxyalkynyl, hydroxyalkoxy, dihydroxyalkoxy, nitro, RuRvN—, RuRvNalkyl-, RuRvN—C(O)-alkyl-, RuRvNalkynyl-, RuRvN-C(O)alkynyl-, RrRsNSO2—, or R8 and R9 taken together with the atoms to which they are attached form a 1,3-dioxolyl ring;
u is 0, 1 or 2;
Rf is selected from the group consisting of alkyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkylthioalkyl, and haloalkyl;
Rp is selected from the group consisting of hydrogen, alkenyl, alkenylcarbonyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkoxycarbonylalkylcarbonyl, alkyl, alkylcarbonyl, alkynyl, aryl, arylalkenyl, arylalkyl, arylcarbonyl, haloalkyl, haloalkylcarbonyl, heteroaryl, heterocycle, heterocyclealkenyl, heterocyclealkyl, heterocyclealkylcarbonyl, heterocyclecarbonyl, trihaloalkyl, trihaloalkylcarbonyl, hydroxyalkyl, and hydroxyalkylcarbonyl;
Rq are each independently selected from the group consisting of hydrogen, alkyl;
Rr and Rs are each independently selected from the group consisting of hydrogen, alkyl, arylalkyl, hydroxyalkyl, heterocyclealkyl;
Rt is selected from the group consisting of hydrogen, alkyl and HO—;
Ru and Rv are each individually selected from the group consisting of hydrogen, alkylcarbonyl, alkyl, alkylSO2—, alkenyl, arylalkyl,
Rw is selected from the group consisting of hydrogen, alkylcarbonyl-NH-alkyl-NHC(O)-alkyl, alkyl, alkyl(alkyl)N-alkyl-NHC(O)-alkyl, hydroxyalkyl-NHC(O)-alkyl, heterocyclealkyl-NHC(O)-alkyl, heterocycle-NHC(O)-alkyl, heteroarylalkyl-NHC(O)-alkyl;
and
Rx and Ry are each individually selected fro the group consisting of hydrogen, alkyl and alkylsulfonyl.

13 more elements

The compound that is selected from the group consisting of

3-(3,5-dimethylphenyl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-(4-fluorophenyl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-(4-chlorophenyl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-6-oxo-3-[4-(trifluoromethyl)phenyl]-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-bromo-3-(4-chlorophenyl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-bromo-4-hydroxy-6-oxo-3-[4-(trifluoromethyl)phenyl]-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-(4-bromophenyl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-bromo-3-(4-fluorophenyl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-(4′-fluoro-1,1′-biphenyl-4-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-6-oxo-3-[4′-(trifluoromethyl)-1,1′-biphenyl-4-yl]-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-[4-(1,3-benzodioxol-5-yl)phenyl]-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2,5-dibromo-3-(4-chlorophenyl)-4-hydroxythieno[2,3-b]pyridin-6(7H)-one;
2,5-dichloro-3-(4-chlorophenyl)-4-hydroxythieno[2,3-b]pyridin-6(7H)-one;
4-hydroxy-3-(4-nitrophenyl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-bromo-4-hydroxy-3-(4-nitrophenyl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-(1,1′-biphenyl-4-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-3-(2′-methyl-1,1′-biphenyl-4-yl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-3-(3′-methyl-1,1′-biphenyl-4-yl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-3-(2′-hydroxy-1,1′-biphenyl-4-yl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-3-(3′-hydroxy-1,1′-biphenyl-4-yl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-3-(2′-methoxy-1,1′-biphenyl-4-yl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-3-(3′-methoxy-1,1′-biphenyl-4-yl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-3-(4′-methoxy-1,1′-biphenyl-4-yl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-(2′-fluoro-1,1′-biphenyl-4-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-(3′-fluoro-1,1′-biphenyl-4-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-(2′-chloro-1,1′-biphenyl-4-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-(3′-chloro-1,1′-biphenyl-4-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-(4′-chloro-1,1′-biphenyl-4-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-(4′-cyano-1,1′-biphenyl-4-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-(3′-acetyl-1,1′-biphenyl-4-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-[4′-(dimethylamino)-1,1′-biphenyl-4-yl]-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-6-oxo-3-(4′-phenoxy-1,1′-biphenyl-4-yl)-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-(4′-acetyl-1,1′-biphenyl-4-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-(2′,3′-dimethyl-1,1′-biphenyl-4-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-6-oxo-3-[4′-(trifluoromethoxy)-1,1′-biphenyl-4-yl]-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-(3′,4′-dimethyl-1,1′-biphenyl-4-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-(2′,3′-dichloro-1,1′-biphenyl-4-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-(2′,4′-dichloro-1,1′-biphenyl-4-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-bromo-3-(4′-fluoro-1,1′-biphenyl-4-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-(4-aminophenyl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-chloro-4-hydroxy-6-oxo-3-[4-(trifluoromethyl)phenyl]-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-3-(4′-hydroxy-1,1′-biphenyl-4-yl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-(4′-acetyl-1,1′-biphenyl-4-yl)-2-bromo-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-bromo-4-hydroxy-3-(2′-hydroxy-1,1′-biphenyl-4-yl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-bromo-3-(4′-cyano-1,1′-biphenyl-4-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-chloro-4-hydroxy-3-(2′-hydroxy-1,1′-biphenyl-4-yl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-bromo-3-(5′-bromo-2′-hydroxy-1,1′-biphenyl-4-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-3-[2′-(hydroxymethyl)-1,1′-biphenyl-4-yl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-3-[4-(methoxymethoxy)phenyl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-6-oxo-3-{2′-[({2-[4-(trifluoromethyl)phenyl]ethyl}amino)methyl]-1,1′-biphenyl-4-yl}-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-3-[2′-({[2-(4-hydroxy-3,5-dimethoxyphenyl)ethyl]amino}methyl)-1,1′-biphenyl-4-yl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-[4-(2-formylthien-3-yl)phenyl]-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-(2′-amino-1,1′-biphenyl-4-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-3-(4-hydroxyphenyl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-bromo-3-(3-bromo-4-hydroxyphenyl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-chloro-3-(2′-chloro-1,1′-biphenyl-4-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
N-[4′-(2-chloro-5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)-1,1′-biphenyl-3-yl]acetamide;
2-chloro-3-(4′-chloro-1,1′-biphenyl-4-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
{[4′-(5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)-1,1′-biphenyl-2-yl]oxy}acetic acid;
2-bromo-4-hydroxy-3-(4-hydroxyphenyl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-bromo-3-(3,5-dibromo-4-hydroxyphenyl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-(3-bromophenyl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-chloro-4-hydroxy-3-(2′-methyl-1,1′-biphenyl-4-yl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-chloro-4-hydroxy-3-(3′-hydroxy-1,1′-biphenyl-4-yl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-{4-[bis(3,3-dimethylbutyl)amino]phenyl}-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2,5-dichloro-3-(3,5-dichloro-4-hydroxyphenyl)-4-hydroxythieno[2,3-b]pyridin-6(7H)-one;
3-(2′,6′-dihydroxy-1,1′-biphenyl-4-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-[5-(4-aminophenyl)thien-2-yl]-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
N-{4-[5-(2-chloro-5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)thien-2-yl]phenyl}methanesulfonamide;
2-bromo-3-(3,5-dibromo-4-hydroxyphenyl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-(2′,3′-dihydroxy-1,1′-biphenyl-4-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2,5-dibromo-3-(3,5-dibromo-4-hydroxyphenyl)-4-hydroxythieno[2,3-b]pyridin-6(7H)-one;
3-(2′,4′-dihydroxy-1,1′-biphenyl-4-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
N-{4-[5-(5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)thien-2-yl]phenyl}methanesulfonamide;
4-hydroxy-3-[5-(4-hydroxyphenyl)thien-2-yl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-chloro-3-[4-(2,3-dihydroxypropoxy)phenyl]-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-[5-(5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)thien-2-yl]benzenesulfonamide;
3-(2′-amino-1,1′-biphenyl-4-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-6-oxo-3-(5-pyridin-4-ylthien-2-yl)-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-chloro-4-hydroxy-3-[5-(4-hydroxyphenyl)thien-2-yl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-3-{5-[4-(hydroxymethyl)phenyl]thien-2-yl}-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-chloro-4-hydroxy-3-{4-[(1-hydroxycyclopent-3-en-1-yl)methoxy]phenyl}-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-chloro-4-hydroxy-3-(4-hydroxyphenyl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-3-{5-[4-(methylsulfonyl)phenyl]thien-2-yl}-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
N-{4-[5-(5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)thien-2-yl]phenyl}acetamide;
4-hydroxy-6-oxo-3-(5-phenylthien-2-yl)-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-(2,2′-bithien-5-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-(3′-fluoro-2′-hydroxy-1,1′-biphenyl-4-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-[5-(2-aminophenyl)thien-2-yl]-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-[5-(4-fluorophenyl)thien-2-yl]-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-[5-(2,4-difluorophenyl)thien-2-yl]-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-6-oxo-3-(4-thien-3-ylphenyl)-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-3-[5-(3-methoxyprop-1-ynyl)-4-methylthien-2-yl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-3-(4-hydroxyphenyl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-bromo-3-(3-bromo-4-hydroxyphenyl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2,5-dichloro-4-hydroxy-3-(4-hydroxyphenyl)thieno[2,3-b]pyridin-6(7H)-one;
methyl 4-[5-(5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)thien-2-yl]phenylcarbamate;
2-chloro-4-hydroxy-3-[4-(2-hydroxy-2-methylpropoxy)phenyl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-chloro-4-hydroxy-3-{4-[(1-hydroxycyclopentyl)methoxy]phenyl}-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-bromo-4-hydroxy-3-(4-hydroxyphenyl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-chloro-4-hydroxy-3-[4-(hydroxymethyl)phenyl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-3-[5-(4-methoxyphenyl)thien-2-yl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-2-methyl-6-oxo-3-(phenylethynyl)-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-chloro-3-{4-[(1-ethyl-4-hydroxypiperidin-4-yl)methoxy]phenyl}-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-3-[5-(3-methoxyprop-1-ynyl)thien-2-yl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-3-[5-(5-hydroxypent-1-ynyl)thien-2-yl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-{4-[(1-acetyl-4-hydroxypiperidin-4-yl)methoxy]phenyl}-2-chloro-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-bromo-4-hydroxy-3-[4-(4-hydroxybut-1-ynyl)phenyl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-3-[5-(3-hydroxyprop-1-ynyl)thien-2-yl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-chloro-4-hydroxy-3-{4-[(4-hydroxy-1-isobutylpiperidin-4-yl)methoxy]phenyl}-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-3-{4-[(1E)-4-hydroxybut-1-enyl]phenyl}-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-6-oxo-3-[5-(1,2,3,6-tetrahydropyridin-4-yl)thien-2-yl]-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-6-oxo-3-(5-phenyl-4-pyridin-3-ylthien-2-yl)-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-[4-(allyloxy)phenyl]-2-chloro-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
7-[4-(5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)phenyl]-N,N-diethylhept-6-ynamide;
4-hydroxy-6-oxo-3-[5-(2-oxo-2,3-dihydro-1H-indol-5-yl)thien-2-yl]-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-[5-(4-cyanophenyl)thien-2-yl]-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-chloro-3-{4-[(1-cyclopropyl-4-hydroxypiperidin-4-yl)methoxy]phenyl}-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-(4′-fluoro-2′-hydroxy-1,1′-biphenyl-4-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-3-[4-(methoxymethoxy)phenyl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-[5-(5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)thien-2-yl]benzoic acid;
3-[5-(3-aminophenyl)thien-2-yl]-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-3-(2′-hydroxy-1,1′-biphenyl-4-yl)thieno[2,3-b]pyridin-6(7H)-one;
methyl 4-(2-chloro-5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)benzoate;
2-chloro-4-hydroxy-6-oxo-3-(2-phenylcyclopropyl)-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-[5-(4-acetylphenyl)thien-2-yl]-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-6-oxo-3-(4-vinylphenyl)-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-[5-(2,4-dihydroxyphenyl)thien-2-yl]-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-[3-(allyloxy)phenyl]-2-bromo-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-{5-[3-(dimethylamino)prop-1-ynyl]thien-2-yl}-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-3-[2′-(hydroxymethyl)-1,1′-biphenyl-4-yl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-(4-bromophenyl)-2-chloro-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-3-[4-(4-hydroxybut-1-ynyl)phenyl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-6-oxo-3-(5-pyridin-2-ylthien-2-yl)-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-3-(2′-hydroxy-1,1′-biphenyl-4-yl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbaldehyde oxime;
3-[3-(allyloxy)phenyl]-2-chloro-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-(5′-bromo-2′,4′-dihydroxy-1,1′-biphenyl-4-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-3-(2′-hydroxy-4′,6′-dimethyl-1,1′-biphenyl-4-yl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
N-{4-[5-(5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)thien-2-yl]-2-fluorophenyl}acetamide;
2-[({(1E)-[4-(5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)phenyl]methylene}amino)oxy]-N-(pyridin-2-ylmethyl)acetamide;
2-chloro-4-hydroxy-3-(5-methyl-2-furyl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-3-(3-hydroxyphenyl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-chloro-3-{4-[(1-cyclopentyl-4-hydroxypiperidin-4-yl)methoxy]phenyl}-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-(2′,5′-dihydroxy-1,1′-biphenyl-4-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-(2′-formyl-1,1′-biphenyl-4-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-[4-(2,3-dihydroxypropoxy)phenyl]-4-hydroxy-2-methyl-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-[4-(allyloxy)phenyl]-2-bromo-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-[5-(1-acetyl-1,2,3,6-tetrahydropyridin-4-yl)thien-2-yl]-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-{5-[4-(allyloxy)phenyl]thien-2-yl}-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
7-[3-(5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)phenyl]hept-6-ynoic acid;
4-hydroxy-3-[5-(3-methoxyprop-1-ynyl)-4-vinylthien-2-yl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-(2′-chloro-6′-hydroxy-1,1′-biphenyl-4-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-chloro-4-hydroxy-3-(3′-hydroxy-1,1′-biphenyl-4-yl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-chloro-3-{4-[(1-cyclobutyl-4-hydroxypiperidin-4-yl)methoxy]phenyl}-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
7-[4-(5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)phenyl]hept-6-ynoic acid;
3-(3,5-dichloro-4-hydroxyphenyl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-[({(1E)-[4-(5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)phenyl]methylene}amino)oxy]-N-[(2S)-2,3-dihydroxypropyl]acetamide;
4-hydroxy-6-oxo-3-[4-(1H-pyrazol-3-yl)phenyl]-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-{5-[4-(2,3-dihydroxypropoxy)phenyl]thien-2-yl}-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-bromo-4-hydroxy-3-[4-(5-hydroxypent-1-ynyl)phenyl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-6-oxo-3-(5,6,7,8-tetrahydronaphthalen-2-yl)-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-[({(1E)-[4-(5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)phenyl]methylene}amino)oxy]-N-[2-(4-methylpiperazin-1-yl)ethyl]acetamide;
N-{3-chloro-4-[5-(5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)thien-2-yl]phenyl}acetamide;
4-hydroxy-3-[4-(5-hydroxypent-1-ynyl)phenyl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-[4-bromo-5-(3-methoxyprop-1-ynyl)thien-2-yl]-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-[4-(2-chloro-5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)phenoxy]-N-(3-hydroxypropyl)acetamide;
2-chloro-3-[4-(cyanomethoxy)phenyl]-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-3-[4-(3-methoxyprop-1-ynyl)phenyl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-6-oxo-3-{4-[(1E)-4-pyrrolidin-1-ylbut-1-enyl]phenyl}-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
tert-butyl 4-[5-(5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)thien-2-yl]phenylcarbamate;
4-hydroxy-3-[5-(4-hydroxyphenyl)-4-methylthien-2-yl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-chloro-3-[4-(diallylamino)phenyl]-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-3-[5-(1H-indol-5-yl)thien-2-yl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-bromo-3-(5′-bromo-2′-hydroxy-1,1′-biphenyl-4-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-[4-(5-cyanopent-1-ynyl)phenyl]-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-[4-(2-chloro-5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)phenoxy]acetamide;
2-[({(1E)-[4-(5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)phenyl]methylene}amino)oxy]-N-(2-pyridin-2-ylethyl)acetamide;
2-chloro-4-hydroxy-3-{4-[(4-hydroxypiperidin-4-yl)methoxy]phenyl}-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-(2′-amino-1,1′-biphenyl-4-yl)-2-chloro-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-6-oxo-3-(1,2,3,4-tetrahydronaphthalen-2-yl)-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-(5-bromothien-2-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-3-[5-(4-nitrophenyl)thien-2-yl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
6-[4-(5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)phenyl]hex-5-ynoic acid;
3-[4-(4-cyanobut-1-ynyl)phenyl]-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-[({(1E)-[4-(5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)phenyl]methylene}amino)oxy]-N-(pyridin-3-ylmethyl)acetamide;
3-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
N-{4-[5-(5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)-2-phenylthien-3-yl]phenyl}methanesulfonamide;
4-hydroxy-6-oxo-3-(5-vinylthien-2-yl)-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-6-oxo-3-(5-pyrazin-2-ylthien-2-yl)-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-[({(1E)-[4-(5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)phenyl]methylene}amino)oxy]-N-[(1R)-1-(hydroxymethyl)-3-methylbutyl]acetamide;
3-[4-(2-formylthien-3-yl)phenyl]-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-3-{4-[(E)-({2-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]-2-oxoethoxy}imino)methyl]phenyl}-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-(2,3-dihydro-1H-inden-5-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-3-[5-(4-hydroxybut-1-ynyl)thien-2-yl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-[({(1E)-[4-(5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)phenyl]methylene}amino)oxy]-N-[3-(dimethylamino)propyl]acetamide;
2-[4-(2-chloro-5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)phenoxy]-N-methylacetamide;
3-[4-(allyloxy)phenyl]-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
{[4′-(5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)-1,1′-biphenyl-2-yl]oxy}acetic acid;
4-hydroxy-3-(4-methylthien-2-yl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
N-{4-[5-(5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)-3-methylthien-2-yl]phenyl}methanesulfonamide;
4-hydroxy-3-[4-(3-hydroxy-3-methylbut-1-ynyl)phenyl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
N-[2-(acetylamino)ethyl]-2-[({(1E)-[4-(5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)phenyl]methylene}amino)oxy]acetamide;
2-[({(1E)-[4-(5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)phenyl]methylene}amino)oxy]-N-(pyrimidin-4-ylmethyl)acetamide;
4-hydroxy-3-(5-iodo-4-methylthien-2-yl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
5-(5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)-N-[2-(dimethylamino)ethyl]thiophene-2-carboxamide;
4-hydroxy-3-{4-[3-(methylamino)prop-1-ynyl]phenyl}-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-[({(1E)-[4-(5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)phenyl]methylene}amino)oxy]-N-[3-(1H-imidazol-1-yl)propyl]acetamide;
3-{5-[(1E)-N-ethoxyethanimidoyl]thien-2-yl}-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-6-oxo-3-(5-pyridin-3-ylthien-2-yl)-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
7-(5-cyano-4-hydroxy-6-oxo-3-phenyl-6,7-dihydrothieno[2,3-b]pyridin-2-yl)hept-6-ynoic acid;
3-[4-(allyloxy)phenyl]-4-hydroxy-2-methyl-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-[4-(2-chloro-5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)phenoxy]-N-[3-(2-oxopyrrolidin-1-yl)propyl]acetamide;
4-hydroxy-3-[4-(4-hydroxyphenyl)-5-phenylthien-2-yl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-(3,5-dibromo-4-hydroxyphenyl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-[({(1E)-[4-(5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)phenyl]methylene}amino)oxy]-N-[2-(1-methylpyrrolidin-2-yl)ethyl]acetamide;
4-hydroxy-6-oxo-3-{4-[3-(tetrahydrofuran-3-yloxy)prop-1-ynyl]phenyl}-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
2-[4-(2-chloro-5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)phenoxy]-N-[3-(1H-imidazol-1-yl)propyl]acetamide;
3-(1,3-benzodioxol-5-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
5-ethanimidoyl-4-hydroxy-3-(2′-hydroxy-1,1′-biphenyl-4-yl)thieno[2,3-b]pyridin-6(7H)-one;
4-hydroxy-3-{5-[(1E)-N-hydroxyethanimidoyl]thien-2-yl}-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-3-(3-methyl-1-benzothien-2-yl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-6-oxo-3-[(E)-2-phenylvinyl]-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-6-oxo-3-(phenylethynyl)-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
N-{3-[4-(5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)phenyl]prop-2-ynyl}methanesulfonamide;
4-hydroxy-3-[4-(4-hydroxybutyl)phenyl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
3-[4-(4-azidobut-1-ynyl)phenyl]-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
4-hydroxy-3-[4-(5-hydroxypentyl)phenyl]-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile;
ethyl 4-hydroxy-3-(2′-hydroxy-1,1′-biphenyl-4-yl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carboxylate;
and
3-(2′-fluoro-6′-hydroxy-1,1′-biphenyl-4-yl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile.

227 more elements

Dependencies are inferred from the claim text.