US 2016/0355507 A1Published application

4-hydroxy-3-(heteroaryl)pyridine-2-one apj agonists

AssigneeBristol-Myers Squibb Company

InventorsJames A. Johnson, Soong-Hoon Kim, R. Michael Lawrence, Michael C. Myers, Hannguang J. Chao, Monique Phillips, Ji Jiang

Life of this patent

Estimating the term…

Abstract

The present invention provides compounds of Formula (I): wherein all variables are as defined in the specification, and compositions comprising any of such novel compounds. These compounds are APJ agonists which may be used as medicaments.

Claims14

Dependent claims

A compound of Formula (I):

or a stereoisomer, a tautomer, or a pharmaceutically acceptable salt thereof, wherein:
alk is C1-6 alkyl substituted with 0-5 Re;
ring A is independently selected from:
ring B is independently selected from:
and 6-membered heteroaryl;
R1 is independently selected from:
H, halogen, NO2, —(CH2)nORb, (CH2)nS(O)pRc, —(CH2)nC(═O)Rb, —(CH2)nNRaRa, —(CH2)nCN, —(CH2)nC(═O)NRaRa, —(CH2)nNRaC(═O)Rb, —(CH2)nNRaC(═O)NRaRa, —(CH2)nNRaC(═O)ORb, —(CH2)nOC(═O)NRaRa, —(CH2)nC(═O)ORb, —(CH2)nS(O)pNRaRa, —(CH2)nNRaS(O)pNRaRa, —(CH2)nNRaS(O)pRc, C1-4 alkyl substituted with 0-3 Re, (CH2)n—C3-6 carbocyclyl substituted with 0-3 Re, and —(CH2)n-heterocyclyl substituted with 0-3 Re;
R2 is independently selected from:
C1-5 alkyl substituted with 0-3 Re;
C1-5 alkenyl substituted with 0-3 Re, and C1-6 cycloalkyl substituted with 0-3 Re;
provided when R2 is C1-5 alkyl, the carbon atom except the one attached directly to the pyridine ring may be replaced by O, N, and S;
R3 is independently selected from:
(1) —(CR4R4)rC(═O)OC1-4 alkyl substituted with 0-5 Re,
(2) —(CR4R4)rNRaRa,
(3) —(CR4R4)rC(═O)NRaRa,
(4) —(CR4R4)rNRaC(═O)C1-4alkyl substituted with 0-5 Re,
(5) —(CR4R4)rNRaC(═O)(CR4R4)nOC1-4alkyl substituted with 0-5 Re,
(6) —(CR4R4)r—R5,
(7) —(CR4R4)r—OR5,
(8) —(CR4R4)rNRaC(═O)(CR4R4)nR5, and
(9) —(CR4R4)rC(═O)NRa(CR4R4)nR5;
R4 is independently selected from:
H, halogen, NRaRa, OC1-4 alkyl, and C1-4 alkyl;
or R4 and R4 together with the carbon atom to which they are both attached form C3-6 cycloalkyl substituted with 0-5 Re;
R5 is independently selected from:
—(CH2)n—C3-10 carbocycle and —(CH2)n-heterocycle, each substituted with 0-3 R6;
R6 is independently selected from:
H, halogen, ═O, —(CH2)nORb, (CH2)nS(O)pRc, —(CH2)nC(═O)Rb, —(CH2)nNRaRa, —(CH2)nCN, —(CH2)nC(═O)NRaRa, —(CH2)nNRaC(═O)Rb, —(CH2)nNRaC(═O)NRaRa, —(CH2)nNRaC(═O)ORb, —(CH2)n OC(═O)NRaRa, —(CH2)nC(═O)ORb, —(CH2)nS(O)pNRaRa, —(CH2)nNRaS(O)pNRaRa, —(CH2)nNRaS(O)pRc, C1-5 alkyl substituted with 0-3 Re, (CH2)n—C3-6 carbocyclyl substituted with 0-3 Re, and —(CH2)n-heterocyclyl substituted with 0-3 Re;
Ra is independently selected from H, C1-6 alkyl substituted with 0-5 Re, C2-6 alkenyl substituted with 0-5 Re, C2-6 alkynyl substituted with 0-5 Re, —(CH2)n—C3-10 carbocyclyl substituted with 0-5 Re, and —(CH2)n-heterocyclyl substituted with 0-5 Re;
or Ra and Ra together with the nitrogen atom to which they are both attached form a heterocyclic ring substituted with 0-5 Re;
Rb is independently selected from H, C1-6 alkyl substituted with 0-5 Re, C2-6 alkenyl substituted with 0-5 Re, C2-6 alkynyl substituted with 0-5 Re, —(CH2)n—C3-10 carbocyclyl substituted with 0-5 Re, and —(CH2)n-heterocyclyl substituted with 0-5 Re;
Rc is independently selected from C1-6 alkyl substituted with 0-5 Re, C2-6alkenyl substituted with 0-5 Re, C2-6alkynyl substituted with 0-5 Re, C3-6carbocyclyl, and heterocyclyl;
Rd is independently selected from H and C1-4alkyl substituted with 0-5 Re;
Re is independently selected from C1-6 alkyl substituted with 0-5 Rf, C2-6 alkenyl, C2-6 alkynyl, —(CH2)n—C3-6 cycloalkyl, —(CH2)n—C4-6 heterocyclyl, —(CH2)n-aryl, —(CH2)n-heteroaryl, F, Cl, Br, CN, NO2, ═O, CO2H, —(CH2)nORf, S(O)pRf, C(═O)NRfRf, NRfC(═O)Rf, S(O)pNRfRf, NRfS(O)pRf, NRfC(═O)ORf, OC(═O)NRfRf and —(CH2)nNRfRf,
Rf is independently selected from H, F, Cl, Br, CN, OH, C1-5alkyl (optimally substituted with halogen and OH), C3-6 cycloalkyl, and phenyl, or Rf and Rf together with the nitrogen atom to which they are both attached form a heterocyclic ring optionally substituted with C1-4alkyl;
n is independently selected from zero, 1, 2, and 3;
r is independently selected from zero, 1, 2, and 3;
and
p is independently selected from zero, 1, and 2.

36 more elements

A compound selected from the group consisting of:

3-(5-benzyl-1,3,4-oxadiazol-2-yl)-6-butyl-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
3-(5-benzyl-1,3,4-oxadiazol-2-yl)-6-butyl-5-(2,6-dimethoxy-4-methylphenyl)pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-[5-(pyridin-4-ylmethyl)-1,3,4-oxadiazol-2-yl]pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-[5-(2-phenyl ethyl)-1,3,4-oxadiazol-2-yl]pyridine-2,4-diol,
6-butyl-3-{5-[(2-chlorophenyl)methyl]-1,3,4-oxadiazol-2-yl}-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-{5-[(2-methoxyphenyl)methyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-{5-[(3-methoxyphenyl)methyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
6-butyl-3-{5-[(4-chlorophenyl)methyl]-1,3,4-oxadiazol-2-yl}-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-{5-[(4-methoxyphenyl)methyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
6-butyl-3-[5-(3-chiorophenyl)-1,3,4-oxadiazol-2-yl]-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
6-butyl-3-[5-(2-chiorophenyl)-1,3,4-oxadiazol-2-yl]-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-[5-(pyrazin-2-yl)-1,3,4-oxadiazol-2-yl]pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-[5-(1-phenylcyclopropyl)-1,3,4-oxadiazol-2-yl]pyridine-2,4-diol,
6-butyl-3-(5-cyclopropyl-1,3,4-oxadiazol-2-yl)-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-[5-(2-phenylpropan-2-yl)-1,3,4-oxadiazol-2-yl]pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-[5-(pyridin-3-yl)-1,3,4-oxadiazol-2-yl]pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-[5-(phenoxymethyl)-1,3,4-oxadiazol-2-yl]pyridine-2,4-diol,
3-(5-benzyl-1,3,4-oxadiazol-2-yl)-6-(but-3-en-1-yl)-5-(2, 6-dimethoxyphenyl)pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-[5-(5-methyl-1H-pyrazol-3-yl)-1,3,4-oxadiazol-2-yl]pyridine-2,4-diol,
3-[5-(1,2-benzoxazol-3-ylmethyl)-1,3,4-oxadiazol-2-yl]-6-butyl-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-[5-(pyrazin-2-ylmethyl)-1,3,4-oxadiazol-2-yl]pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-[5-(pyrimidin-5-ylmethyl)-1,3,4-oxadiazol-2-yl]pyridine-2,4-diol,
6-butyl-3-{5-[(3-chlorophenyl)methyl]-1,3,4-oxadiazol-2-yl}-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
6-butyl-3-{5-[difluoro(phenyl)methyl]-1,3,4-oxadiazol-2-yl}-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
3-[5-(1,3-benzoxazol-2-ylmethyl)-1,3,4-oxadiazol-2-yl]-6-butyl-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
3-[5-(1,2-benzoxazol-3-ylmethyl)-1,3,4-oxadiazol-2-yl]-6-butyl-5-(2,6-dimethoxy-4-methylphenyl)pyridine-2,4-diol,
3-[5-(1,2-benzoxazol-3-ylmethyl)-1,3,4-oxadiazol-2-yl]-6-(but-3-en-1-yl)-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-{5-[2-(5-phenyl-1,3-oxazol-2-yl)ethyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-{5-[2-(1-methyl-1H-imidazol-2-yl)ethyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
6-butyl-3-{5-[(6-chloropyridin-3-yl)methyl]-1,3,4-oxadiazol-2-yl}-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
6-butyl-3-{5-[2-(4-chlorophenyl)propan-2-yl]-1,3,4-oxadiazol-2-yl}-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-{5-[(4-fluorophenyl)methyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
6-butyl-3-{5-[(3,4-dichlorophenyl)methyl]-1,3,4-oxadiazol-2-yl}-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-(5-{[4-fluoro-3-(trifluoromethyl)phenyl]methyl}-1,3,4-oxadiazol-2-yl)pyridine-2,4-diol,
6-butyl-3-{5-[(2,4-dichlorophenyl)methyl]-1,3,4-oxadiazol-2-yl}-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-{5-[(3,5-dimethyl-1H-pyrazol-4-yl)methyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
4-({5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}methyl)benzonitrile,
6-butyl-3-{5-[(3,4-difluorophenyl)methyl]-1,3,4-oxadiazol-2-yl}-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
6-butyl-3-(5-{[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}-1,3,4-oxadiazol-2-yl)-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
6-butyl-3-{5-[1-(4-chlorophenyl)ethyl]-1,3,4-oxadiazol-2-yl}-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-{5-[(4-methyl-1,2,5-oxadiazol-3-yl)methyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-[5-(4-fluorophenoxymethyl)-1,3,4-oxadiazol-2-yl]pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-[5-(1H-indazol-3-ylmethyl)-1,3,4-oxadiazol-2-yl]pyridine-2,4-diol,
4-({5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}methyl)-1,2-dihydrophthalazin-1-one,
6-butyl-5-(2,6-dimethoxyphenyl)-3-{5-[methoxy(phenyl)methyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-{5-[(2-phenyl-1,3-thiazol-4-yl)methyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
3-{5-[2-(1,3-benzoxazol-2-yl)ethyl]-1,3,4-oxadiazol-2-yl}-6-butyl-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-{5-[(4-fluoro-3-methoxyphenyl)methyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-[5-(1,3-thiazol-5-ylmethyl)-1,3,4-oxadiazol-2-yl]pyridine-2,4-diol,
6-butyl-3-[5-(3,4-dichlorophenoxymethyl)-1,3,4-oxadiazol-2-yl]-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-{5-[(3-methyl-1,2-oxazol-5-yl)methyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-(5-{2-[3-(pyrazin-2-yl)-1,2,4-oxadiazol-5-yl]ethyl}-1,3,4-oxadiazol-2-yl)pyridine-2,4-diol,
6-butyl-3-[5-(4-chlorophenoxymethyl)-1,3,4-oxadiazol-2-yl]-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
6-butyl-3-{5-[2-(4-chlorophenyl)-2-methylpropyl]-1,3,4-oxadiazol-2-yl}-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-(5-{[3-(pyridin-2-yl)-1,2,4-oxadiazol-5-yl]methyl}-1,3,4-oxadiazol-2-yl)pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-(5-{[4-(trifluoromethoxy)phenyl]methyl})-1,3,4-oxadiazol-2-yl)pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-(5-{[3-fluoro-5-(trifluoromethyl)phenyl]methyl}-1,3,4-oxadiazol-2-yl)pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-{5-[2-(1-methyl-1H-1,3-benzodiazol-2-yl)ethyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
6-butyl-3-{5-[(2-chloropyridin-4-yl)methyl]-1,3,4-oxadiazol-2-yl}-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-(5-{2-[3-(4-methoxyphenyl)-1,2,4-oxadiazol-5-yl]ethyl}-1,3,4-oxadiazol-2-yl)pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-[5-(1,2,3,4-tetrahydroisoquinolin-1-yl)-1,3,4-oxadiazol-2-yl]pyridine-2,4-diol,
6-butyl-3-{5-[2-(3,4-dichlorophenyl)propan-2-yl]-1,3,4-oxadiazol-2-yl})-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-{5-[(2-methyl-2H-1,2,3,4-tetrazol-5-yl)methyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-[5-(2-methyl-1-phenylpropan-2-yl)-1,3,4-oxadiazol-2-yl]pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-{5-[4-(trifluoromethyl)phenoxymethyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-{5-[(5-phenyl-4H-1,2,4-triazol-3-yl)methyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
6-butyl-3-[5-(cyclohexylmethyl)-1,3,4-oxadiazol-2-yl]-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
6-butyl-3-{5-[2-(4-chlorophenyl)ethyl]-1,3,4-oxadiazol-2-yl}-5-(2, 6-dimethoxyphenyl)pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-[5-(oxan-4-ylmethyl)-1,3,4-oxadiazol-2-yl]pyridine-2,4-diol,
6-butyl-3-{5-[(3-chloro-4-fluorophenyl)methyl]-1,3,4-oxadiazol-2-yl}-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
6-butyl-3-{5-[(4-chloro-3-fluorophenyl)methyl]-1,3,4-oxadiazol-2-yl}-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-{5-[2-(1,3-thiazol-2-yl)ethyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-(5-{[3-(trifluoromethyl)phenyl]methyl}-1,3,4-oxadiazol-2-yl)pyridine-2,4-diol,
6-butyl-3-{5-[2-(3,4-difluorophenyl)ethyl]-1,3,4-oxadiazol-2-yl}-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-(5-{2-[4-(trifluoromethyl)phenyl]ethyl}-1,3,4-oxadiazol-2-yl)pyridine-2,4-diol,
6-butyl-3-[5-(3,4-difluorophenoxymethyl)-1,3,4-oxadiazol-2-yl]-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-{5-[2-(3-phenyl-1,2,4-oxadiazol-5-yl)ethyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-{5-[(1-phenyl-1H-pyrazol-4-yl)methyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-{5-[(2-methyl-1,3-thiazol-4-yl)methyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-(5-{[4-(trifluoromethyl)phenyl]methyl}-1,3,4-oxadiazol-2-yl)pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-{5-[2-(pyrimidin-2-yl)ethyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
3-{5-[2-(1,3-benzothiazol-2-yl)ethyl]-1,3,4-oxadiazol-2-yl}-6-butyl-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-(5-{2-[3-(pyridin-2-yl)-1,2,4-oxadiazol-5-yl]ethyl}-1,3,4-oxadiazol-2-yl)pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-{5-[(5-methyl-2-phenyl-1,3-thiazol-4-yl)methyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
6-butyl-3-{5-[2-(3,4-dichlorophenyl)ethyl]-1,3,4-oxadiazol-2-yl}-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
3-[5-(1,2-benzoxazol-3-ylmethyl)-1,3,4-oxadiazol-2-yl]-6-butyl-5-(2,6-dichlorophenyl)pyridine-2,4-diol,
6-butyl-3-{5-[(4-chlorophenyl)methyl]-1,3,4-oxadiazol-2-yl}-5-(2,6-dichlorophenyl)pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-{5-[(dimethylamino)(4-fluorophenyl)methyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
3-[5-(1,2-benzoxazol-3-ylmethyl)-1,3,4-oxadiazol-2-yl]-5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)pyridine-2,4-diol,
3-{5-[(4-chlorophenyl)methyl]-1,3,4-oxadiazol-2-yl}-5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-{5-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
3-[5-(1,2-benzoxazol-3-ylmethyl)-1,3,4-oxadiazol-2-yl]-6-cyclopropyl-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
3-{5-[(4-chlorophenyl)methyl]-1,3,4-oxadiazol-2-yl}-6-cyclopropyl-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
6-cyclopropyl-5-(2,6-dimethoxyphenyl)-3-{5-[(2-methyl-1,3-thiazol-4-yl)methyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
6-cyclopropyl-5-(2,6-dimethoxyphenyl)-3-(5-{[3-(pyridin-2-yl)-1,2,4-oxadiazol-5-yl]methyl}-1,3,4-oxadiazol-2-yl)pyridine-2,4-diol,
ethyl 2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}acetate,
6-butyl-5-(2,6-dimethoxyphenyl)-3-{5-[(1,3-dimethyl-1H-pyrazol-5-yl)methyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
3-({5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}methyl)-1-methylimidazolidine-2,4-dione,
6-butyl-5-(2,6-dimethoxyphenyl)-3-{5-[(3-fluorophenyl)methyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-[5-(piperidin-1-ylmethyl)-1,3,4-oxadiazol-2-yl]pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-(5-{[3-(pyridin-3-yl)-1,2,4-oxadiazol-5-yl]methyl}-1,3,4-oxadiazol-2-yl)pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-{5-[(1-methyl-1H-pyrazol-4-yl)methyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
6-butyl-3-{5-[(4-chloro-2-fluorophenyl)methyl]-1,3,4-oxadiazol-2-yl}-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-(5-{[3-(pyridin-4-yl)-1,2,4-oxadiazol-5-yl]methyl}-1,3,4-oxadiazol-2-yl)pyridine-2,4-diol,
1-({5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}methyl)pyrrolidin-2-one,
5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-3-{5-[(2-methyl-1,3-thiazol-4-yl)methyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-3-(5-{[5-(pyridin-2-yl)-1,2,4-oxadiazol-3-yl]methyl}-1,3,4-oxadiazol-2-yl)pyridine-2,4-diol,
3-{5-[(3-benzyl-1,2,4-oxadiazol-5-yl)methyl]-1,3,4-oxadiazol-2-yl}-6-butyl-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
6-butyl-3-{5-[(3-cyclopropyl-1,2,4-oxadiazol-5-yl)methyl]-1,3,4-oxadiazol-2-yl}-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
3-{5-[(6-chloropyridin-3-yl)methyl]-1,3,4-oxadiazol-2-yl}-5-(2, 6-dimethoxyphenyl)-6-(ethoxymethyl)pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-{5-[(3-phenyl-1,2,4-oxadiazol-5-yl)methyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
1-({5-[5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}methyl)pyrrolidin-2-one,
3-({5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}methyl)imidazolidine-2,4-dione,
1-({5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}methyl)-1,2-dihydropyridin-2-one,
6-butyl-5-(2,6-dimethoxyphenyl)-3-[5-(1H-imidazol-1-ylmethyl)-1,3,4-oxadiazol-2-yl]pyridine-2,4-diol,
3-({5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}methyl)-1,3-oxazolidin-2-one,
4-({5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}methyl)morpholin-3-one,
tert-butyl 2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}acetate,
1-({5-[5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl})methyl)-1,2-dihydropyridin-2-one,
tert-butyl N-({5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}methyl)carbamate,
tert-butyl N-({5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}methyl)-N-methylcarbamate,
3-{5-[(4-chloro-3-fluorophenyl)methyl]-1,3,4-oxadiazol-2-yl}-5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)pyridine-2,4-diol,
3-{5-[(4-chloro-2-fluorophenyl)methyl]-1,3,4-oxadiazol-2-yl}-5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)pyridine-2,4-diol,
5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-3-{5-[(5-fluoropyridin-2-yl)methyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-3-[5-(1H-imidazol-1-ylmethyl)-1,3,4-oxadiazol-2-yl]pyridine-2,4-diol,
5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-3-{5-[(3-fluoro-4-methylphenyl)methyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
3-{5-[(5-chloropyridin-2-yl)methyl]-1,3,4-oxadiazol-2-yl}-5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)pyridine-2,4-diol,
5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-3-{5-[(3-phenyl-1H-pyrazol-1-yl)methyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-3-(5-{[3-(trifluoromethyl)-1H-pyrazol-1-yl]methyl}-1,3,4-oxadiazol-2-yl)pyridine-2,4-diol,
5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-3-{5-[(1-methyl-1H-pyrazol-4-yl)methyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-3-{5-[(6-fluoropyridin-3-yl)methyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-3-[5-(1H-indazol-3-ylmethyl)-1,3,4-oxadiazol-2-yl]pyridine-2,4-diol,
3-[5-(1H-1,2,3-benzotriazol-1-ylmethyl)-1,3,4-oxadiazol-2-yl]-5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)pyridine-2,4-diol,
5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-3-[5-(1H-indazol-1-ylmethyl)-1,3,4-oxadiazol-2-yl]pyridine-2,4-diol,
5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-3-{5-[(4-fluorophenyl)methyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-3-[5-(1H-indol-1-ylmethyl)-1,3,4-oxadiazol-2-yl]pyridine-2,4-diol,
6-butyl-5-(3-ethylphenyl)-4-hydroxy-3-{5-[(2-methyl-1,3-thiazol-4-yl)methyl]-1,3,4-oxadiazol-2-yl}-1,2-dihydropyridin-2-one,
3-[5-(1,2-benzoxazol-3-ylmethyl)-1,3,4-oxadiazol-2-yl]-6-butyl-5-phenylpyridine-2,4-diol,
6-butyl-3-{5-[(3,4-difluorophenyl)methyl]-1,3,4-oxadiazol-2-yl}-5-(3-methoxyphenyl)pyridine-2,4-diol,
6-butyl-3-{5-[(3,4-difluorophenyl)methyl]-1,3,4-oxadiazol-2-yl}-5-(3-ethylphenyl)pyridine-2,4-diol,
6-butyl-3-{5-[(3,4-difluorophenyl)methyl]-1,3,4-oxadiazol-2-yl}-5-[3-(trifluoromethoxy)phenyl]pyridine-2,4-diol,
5-[3-(benzyloxy)phenyl]-6-butyl-3-{5-[(3,4-difluorophenyl)methyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
6-butyl-3-{5-[(3,4-difluorophenyl)methyl]-1,3,4-oxadiazol-2-yl}-5-[3-(hydroxymethyl)phenyl]pyridine-2,4-diol,
6-butyl-5-(cyclohex-1-en-1-yl)-3-{5-[(3,4-difluorophenyl)methyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
6-butyl-3-{5-[(3,4-difluorophenyl)methyl]-1,3,4-oxadiazol-2-yl}-5-[3-(propan-2-yl)phenyl]pyridine-2,4-diol,
6-butyl-3-{5-[(3,4-difluorophenyl)methyl]-1,3,4-oxadiazol-2-yl}-5-[3-(methoxymethyl)phenyl]pyridine-2,4-diol,
3-(2-butyl-5-{5-[(3,4-difluorophenyl)methyl]-1,3,4-oxadiazol-2-yl}-4,6-dihydroxypyridin-3-yl)-N-(propan-2-yl)benzamide,
6-butyl-4-hydroxy-3-{5-[(2-methyl-1,3-thiazol-4-yl)methyl]-1,3,4-oxadiazol-2-yl}-5-[3-(propan-2-yl)phenyl]-1,2-dihydropyridin-2-one,
3-(2-butyl-4-hydroxy-5-{5-[(2-methyl-1,3-thiazol-4-yl)methyl]-1,3,4-oxadiazol-2-yl}-6-oxo-1,6-dihydropyridin-3-yl)-N-(propan-2-yl)benzamide,
6-butyl-5-(3-cyclopropylphenyl)-4-hydroxy-3-{5-[(2-methyl-1,3-thiazol-4-yl)methyl]-1,3,4-oxadiazol-2-yl}-1,2-dihydropyridin-2-one,
6-butyl-4-hydroxy-5-(3-methoxyphenyl)-3-{5-[(2-methyl-1,3-thiazol-4-yl)methyl]-1,3,4-oxadiazol-2-yl}-1,2-dihydropyridin-2-one,
6-butyl-4-hydroxy-5-[3-(hydroxymethyl)phenyl]-3-{5-[(2-methyl-1,3-thiazol-4-yl)methyl]-1,3,4-oxadiazol-2-yl}-1,2-dihydropyridin-2-one,
6-butyl-4-hydroxy-3-{5-[(2-methyl-1,3-thiazol-4-yl)methyl]-1,3,4-oxadiazol-2-yl}-5-[3-(pyrrolidin-1-yl)phenyl]-1,2-dihydropyridin-2-one,
6-butyl-5-(2,6-dimethoxyphenyl)-3-{5-[(methylamino)methyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
N-({5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}methyl)-N-methyl-2-phenylacetamide,
N-({5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}methyl)-3-chloro-N-methylbenzamide,
N-({5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}methyl)-N-methylpyridine-2-carb oxamide,
N-({5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}methyl)-2-methoxyacetamide,
N-({5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}methyl)-N-methylpyridine-4-carb oxamide,
N-({5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}methyl)pyridine-3-carboxamide,
N-({5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}methyl)-2-chloro-N-methylbenzamide,
N-({5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}methyl)-3-chlorobenzamide,
N-({5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}methyl)-4-chlorobenzamide,
N-({5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}methyl)pyridine-4-carboxamide,
N-({5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}methyl)-N-methylpyridine-3-carb oxamide,
N-({5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}methyl)-2-phenyl acetamide,
N-({5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}methyl)-2,2-dimethylpropanamide,
N-({5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}methyl)pyridine-2-carboxamide,
N-({5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}methyl)-N,2,2-trimethylpropanamide,
3-[5-(aminomethyl)-1,3,4-oxadiazol-2-yl]-6-butyl-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
N-({5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}methyl)benzamide,
N-({5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}methyl)-N-methylbenzamide,
N-({5-[5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}methyl)benzamide,
N-({5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}methyl)-3-methylbutanamide,
N-({5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}methyl)acetamide,
N-({5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}methyl)-2,2,2-trifluoroacetamide,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-N,N-diethyl acetamide,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-N-(pyridin-2-ylmethyl)acetamide,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-N-methylacetamide,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}acetamide,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-N-(propan-2-yl)acetamide,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-N,N-dimethylacetamide,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-N-(4-methoxyphenyl)acetamide,
4-(2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}acetyl)piperazin-2-one,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-1-(4-methylpiperazin-1-yl)ethan-1-one,
N-benzyl-2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}acetamide,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-N-ethylacetamide,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-N-cyclopropylacetamide,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-N-propylacetamide,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-N-(2-fluoroethyl)acetamide,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-N-(2,2-difluoroethyl)acetamide,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-N-(2,2,2-trifluoroethyl)acetamide,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-N-(2-methoxyethyl)acetamide,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-1-(pyrrolidin-1-yl)ethan-1-one,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-1-(piperidin-1-yl)ethan-1-one,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-1-(morpholin-4-yl)ethan-1-one,
N-butyl-2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}acetamide,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-N-pentylacetamide,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-1-(3-fluoroazetidin-1-yl)ethan-1-one,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-1-(3,3-difluoroazetidin-1-yl)ethan-1-one,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-N-(1,3-thiazol-2-yl)acetamide,
3-(3-benzyl-1,2,4-oxadiazol-5-yl)-6-butyl-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
6-butyl-3-{3-[(4-chlorophenyl)methyl]-1,2,4-oxadiazol-5-yl}-5-(2, 6-dimethoxyphenyl)pyridine-2,4-diol,
3-(5-benzyl-4H-1,2,4-triazol-3-yl)-6-butyl-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
6-butyl-3-(5-{[5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl]methyl}-1,3,4-oxadiazol-2-yl)-S-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-(5-{[5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl]methyl}-1,3,4-oxadiazol-2-yl)pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-(5-{[5-(pyridin-2-yl)-1,3,4-oxadiazol-2-yl]methyl}-1,3,4-oxadiazol-2-yl)pyridine-2,4-diol,
6-butyl-3-(5-{[5-(2-chlorophenyl)-1,3,4-oxadiazol-2-yl]methyl}-1,3,4-oxadiazol-2-yl)-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
3-{5-[(5-benzyl-1,3,4-oxadiazol-2-yl)methyl]-1,3,4-oxadiazol-2-yl}-6-butyl-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
6-butyl-3-(5-{[5-(3-chiorophenyl)-1,3,4-oxadiazol-2-yl]methyl}-1,3,4-oxadiazol-2-yl)-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-(5-{[5-(pyridin-3-yl)-1,3,4-oxadiazol-2-yl]methyl}-1,3,4-oxadiazol-2-yl)pyridine-2,4-diol,
1-({5-[6-(ethoxymethyl)-5-(4-fluoro-2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}methyl)-1,2-dihydropyridin-2-one,
3-[5-(1,2-benzoxazol-3-ylmethyl)-1,3,4-oxadiazol-2-yl]-6-(ethoxymethyl)-5-(4-fluoro-2,6-dimethoxyphenyl)pyridine-2,4-diol,
3-{5-[(4-chlorophenyl)methyl]-1,3,4-oxadiazol-2-yl}-6-(ethoxymethyl)-5-(4-fluoro-2,6-dimethoxyphenyl)pyridine-2,4-diol,
1-({5-[6-(ethoxymethyl)-5-(4-fluoro-2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}methyl)pyrrolidin-2-one,
3-{5-[(6-chloropyridin-3-yl)methyl]-1,3,4-oxadiazol-2-yl}-6-(ethoxymethyl)-5-(4-fluoro-2,6-dimethoxyphenyl)pyridine-2,4-diol,
3-{5-[(4-chlorophenyl)methyl]-1,3,4-oxadiazol-2-yl}-5-(3,5-dimethoxypyridin-4-yl)-6-(ethoxymethyl)pyridine-2,4-diol,
6-butyl-3-{5-[(4-chlorophenyl)methyl]-1,3,4-oxadiazol-2-yl}-5-(3-fluoro-2,6-dimethoxyphenyl)pyridine-2,4-diol,
3-[5-(1,2-benzoxazol-3-ylmethyl)-1,3,4-oxadiazol-2-yl]-6-butyl-5-(3-fluoro-2,6-dimethoxyphenyl)pyridine-2,4-diol,
3-{5-[(4-chlorophenyl)methyl]-1,3,4-oxadiazol-2-yl}-6-(ethoxymethyl)-5-(2-hydroxy-6-methoxyphenyl)pyridine-2,4-diol,
3-[5-(1,2-benzoxazol-3-ylmethyl)-1,3,4-oxadiazol-2-yl]-6-butyl-5-(2,6-dimethylphenyl)pyridine-2,4-diol,
3-[5-(1,2-benzoxazol-3-ylmethyl)-1,3,4-oxadiazol-2-yl]-6-butyl-5-(2,4,6-trimethylphenyl)pyridine-2,4-diol,
3-[5-(1,2-benzoxazol-3-ylmethyl)-1,3,4-oxadiazol-2-yl]-6-butyl-5-(2,6-diethylphenyl)pyridine-2,4-diol,
6-butyl-5-(2,6-dimethoxyphenyl)-3-(5-{[1,2]oxazolo[4,5-b]pyridin-3-ylmethyl}-1,3,4-oxadiazol-2-yl)pyridine-2,4-diol,
5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-3-(5-{[1,2]oxazolo[4,5-b]pyridin-3-ylmethyl}-1,3,4-oxadiazol-2-yl)pyridine-2,4-diol,
3-{5-[(4-chlorophenyl)methyl]-1,3,4-oxadiazol-2-yl}-5-(2,6-dihydroxyphenyl)-6-(ethoxymethyl)pyridine-2,4-diol,
3-{5-[(5-chloropyridin-2-yl)methyl]-1,3,4-oxadiazol-2-yl}-5-(2, 6-dimethoxyphenyl)-6-[(ethyl amino)methyl]pyridine-2,4-diol,
3-{5-[(1,2-benzoxazol-3-yl)methyl]-1,3,4-thiadiazol-2-yl}-5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)pyridine-2,4-diol,
3-{5-[(5-chloropyridin-2-yl)methyl]-1,3,4-thiadiazol-2-yl}-5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)pyridine-2,4-diol,
3-{5-[(5-chloropyridin-2-yl)methyl]-1,3,4-thiadiazol-2-yl}-6-cyclopentyl-5-(2, 6-dimethoxyphenyl)pyridine-2,4-diol,
3-{5-[(4-chlorophenyl)methyl]-1,3,4-thiadiazol-2-yl}-5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)pyridine-2,4-diol,
N-({5-[5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-thiadiazol-2-yl}methyl)pyridine-2-carboxamide,
6-butyl-3-{5-[(5-chloro-3-fluoropyridin-2-yl)methyl]-1,3,4-oxadiazol-2-yl}-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
3-{5-[(5-chloro-3-fluoropyridin-2-yl)methyl]-1,3,4-oxadiazol-2-yl}-5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)pyridine-2,4-diol,
3-{5-[(5-chloropyridin-2-yl)methyl]-1,3,4-oxadiazol-2-yl}-6-cyclopentyl-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
3-{5-[(4-chlorophenyl)methyl]-1,3,4-oxadiazol-2-yl}-6-cyclopentyl-5-(2,6-dimethoxyphenyl)pyridine-2,4-diol,
3-{5-[(5-chloropyridin-2-yl)methyl]-1,3,4-oxadiazol-2-yl}-5-(2,6-dimethoxyphenyl)-6-[(2-methoxyethoxy)methyl]pyridine-2,4-diol,
3-{5-[(1,2-benzoxazol-3-yl)methyl]-1,3,4-oxadiazol-2-yl}-5-(2,6-dimethoxyphenyl)-6-[(2-methoxyethoxy)methyl]pyridine-2,4-diol,
5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-3-{5-[(phenylamino)methyl]-1,3,4-oxadiazol-2-yl}pyridine-2,4-diol,
3-{5-[(4-chlorophenyl)methyl]-1,3,4-oxadiazol-2-yl}-5-(2,6-dimethoxyphenyl)-6-[(2-methoxyethoxy)methyl]pyridine-2,4-diol,
N-({5-[6-butyl-5-(2, 5-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}methyl)benzamide,
N-[(5-{6-butyl-2,4-dihydroxy-5-[2-methoxy-5-(propan-2-yl)phenyl]pyridin-3-yl}-1,3,4-oxadiazol-2-yl)methyl]benzamide,
3-{5-[(1,2-benzoxazol-3-yl)methyl]-1,3,4-oxadiazol-2-yl}-6-(ethoxymethyl)-5-(2-methoxyphenyl)pyridine-2,4-diol,
3-{5-[(4-chlorophenyl)methyl]-1,3,4-oxadiazol-2-yl}-6-(ethoxymethyl)-5-(2-methoxyphenyl)pyridine-2,4-diol,
N-({5-[6-butyl-5-(2,3-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}methyl)benzamide,
N-({5-[6-(ethoxymethyl)-2,4-dihydroxy-5-(2-methoxyphenyl)pyridin-3-yl]-1,3,4-oxadiazol-2-yl}methyl)benzamide,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-N-(pyridin-3-yl)acetamide,
2-{5-[5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-N-(1,3-thiazol-2-yl)acetamide,
N-[(1,3-benzothiazol-2-yl)methyl]-2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}acetamide,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-N-[(pyridin-3-yl)methyl]acetamide,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-N-[(1,3-oxazol-2-yl)methyl]acetamide,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-N-[2-(4-sulfamoylphenyl)ethyl]acetamide,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-N-[2-(2-chlorophenyl)ethyl]acetamide,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-N-[(3-chlorophenyl)methyl]acetamide,
N-benzyl-2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-N-methylacetamide,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-N-methyl-N-(2-phenyl ethyl)acetamide,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-N-(prop-2-yn-1-yl)acetamide,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-N-(3-methyl-1H-pyrazol-5-yl)acetamide,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-N-[(2-methylphenyl)methyl]acetamide,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-N-[(2-chlorophenyl)methyl]acetamide,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-N-[(4-chlorophenyl)methyl]acetamide,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-N-[2-(4-chlorophenyl)ethyl]acetamide,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-N-[(pyridin-4-yl)methyl]acetamide,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-N-[(4-methoxyphenyl)methyl]acetamide,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-N-{[4-(dimethylamino)phenyl]methyl}acetamide,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl)}-N-[(5-methyl-1,3,4-oxadiazol-2-yl)methyl]acetamide, 271
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-N-{[3-(propan-2-yl)-1,2-oxazol-5-yl]methyl}acetamide,
2-{5-[6-butyl-5-(2,6-dimethoxyphenyl)-2,4-dihydroxypyridin-3-yl]-1,3,4-oxadiazol-2-yl}-N-[(4-sulfamoylphenyl)methyl]acetamide,
3-{5-[(5-chloropyridin-2-yl)methyl]-1,3,4-oxadiazol-2-yl}-6-(ethoxymethyl)-5-(2-hydroxy-6-methoxyphenyl)pyridine-2,4-diol,
3-{5-[(5-chloropyridin-2-yl)methyl]-1,3,4-oxadiazol-2-yl}-6-(ethoxymethyl)-5-(2-hydroxy-6-methoxyphenyl)pyridine-2,4-diol, and
3-{5-[(5-chloropyridin-2-yl)methyl]-1,3,4-oxadiazol-2-yl}-5-(2,6-dihydroxyphenyl)-6-(ethoxymethyl)pyridine-2,4-diol.

268 more elements

Dependencies are inferred from the claim text.

Facts

Application: 15/171,276Filed 2 Jun 2016
Priority: 3 Jun 2015
Published: 8 Dec 2016
Term ends: Not estimatedThe source records don’t support an estimate.

Classification12 codes

C07D 413/04
Containing two hetero rings: directly linked by a ring-member-to-ring-member bond
A61P 9/00
Drugs for disorders of the cardiovascular system
A61P 9/04
Drugs for disorders of the cardiovascular system: inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
A61P 9/10
Drugs for disorders of the cardiovascular system: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary…

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Application62/170,215Us provisional application · filed 3 Jun 2015
US 10,011,594 B2Related patent
US 2016/0355507 A1This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

A compound of Formula (I):

or a stereoisomer, a tautomer, or a pharmaceutically acceptable salt thereof, wherein:
alk is C1-6 alkyl substituted with 0-5 Re;
ring A is independently selected from:
ring B is independently selected from:
and 6-membered heteroaryl;
R1 is independently selected from:
H, halogen, NO2, —(CH2)nORb, (CH2)nS(O)pRc, —(CH2)nC(═O)Rb, —(CH2)nNRaRa, —(CH2)nCN, —(CH2)nC(═O)NRaRa, —(CH2)nNRaC(═O)Rb, —(CH2)nNRaC(═O)NRaRa, —(CH2)nNRaC(═O)ORb, —(CH2)nOC(═O)NRaRa, —(CH2)nC(═O)ORb, —(CH2)nS(O)pNRaRa, —(CH2)nNRaS(O)pNRaRa, —(CH2)nNRaS(O)pRc, C1-4 alkyl substituted with 0-3 Re, (CH2)n—C3-6 carbocyclyl substituted with 0-3 Re, and —(CH2)n-heterocyclyl substituted with 0-3 Re;
R2 is independently selected from:
C1-5 alkyl substituted with 0-3 Re;
C1-5 alkenyl substituted with 0-3 Re, and C1-6 cycloalkyl substituted with 0-3 Re;
provided when R2 is C1-5 alkyl, the carbon atom except the one attached directly to the pyridine ring may be replaced by O, N, and S;
R3 is independently selected from:
(1) —(CR4R4)rC(═O)OC1-4 alkyl substituted with 0-5 Re,
(2) —(CR4R4)rNRaRa,
(3) —(CR4R4)rC(═O)NRaRa,
(4) —(CR4R4)rNRaC(═O)C1-4alkyl substituted with 0-5 Re,
(5) —(CR4R4)rNRaC(═O)(CR4R4)nOC1-4alkyl substituted with 0-5 Re,
(6) —(CR4R4)r—R5,
(7) —(CR4R4)r—OR5,
(8) —(CR4R4)rNRaC(═O)(CR4R4)nR5, and
(9) —(CR4R4)rC(═O)NRa(CR4R4)nR5;
R4 is independently selected from:
H, halogen, NRaRa, OC1-4 alkyl, and C1-4 alkyl;
or R4 and R4 together with the carbon atom to which they are both attached form C3-6 cycloalkyl substituted with 0-5 Re;
R5 is independently selected from:
—(CH2)n—C3-10 carbocycle and —(CH2)n-heterocycle, each substituted with 0-3 R6;
R6 is independently selected from:
H, halogen, ═O, —(CH2)nORb, (CH2)nS(O)pRc, —(CH2)nC(═O)Rb, —(CH2)nNRaRa, —(CH2)nCN, —(CH2)nC(═O)NRaRa, —(CH2)nNRaC(═O)Rb, —(CH2)nNRaC(═O)NRaRa, —(CH2)nNRaC(═O)ORb, —(CH2)n OC(═O)NRaRa, —(CH2)nC(═O)ORb, —(CH2)nS(O)pNRaRa, —(CH2)nNRaS(O)pNRaRa, —(CH2)nNRaS(O)pRc, C1-5 alkyl substituted with 0-3 Re, (CH2)n—C3-6 carbocyclyl substituted with 0-3 Re, and —(CH2)n-heterocyclyl substituted with 0-3 Re;
Ra is independently selected from H, C1-6 alkyl substituted with 0-5 Re, C2-6 alkenyl substituted with 0-5 Re, C2-6 alkynyl substituted with 0-5 Re, —(CH2)n—C3-10 carbocyclyl substituted with 0-5 Re, and —(CH2)n-heterocyclyl substituted with 0-5 Re;
or Ra and Ra together with the nitrogen atom to which they are both attached form a heterocyclic ring substituted with 0-5 Re;
Rb is independently selected from H, C1-6 alkyl substituted with 0-5 Re, C2-6 alkenyl substituted with 0-5 Re, C2-6 alkynyl substituted with 0-5 Re, —(CH2)n—C3-10 carbocyclyl substituted with 0-5 Re, and —(CH2)n-heterocyclyl substituted with 0-5 Re;
Rc is independently selected from C1-6 alkyl substituted with 0-5 Re, C2-6alkenyl substituted with 0-5 Re, C2-6alkynyl substituted with 0-5 Re, C3-6carbocyclyl, and heterocyclyl;
Rd is independently selected from H and C1-4alkyl substituted with 0-5 Re;
Re is independently selected from C1-6 alkyl substituted with 0-5 Rf, C2-6 alkenyl, C2-6 alkynyl, —(CH2)n—C3-6 cycloalkyl, —(CH2)n—C4-6 heterocyclyl, —(CH2)n-aryl, —(CH2)n-heteroaryl, F, Cl, Br, CN, NO2, ═O, CO2H, —(CH2)nORf, S(O)pRf, C(═O)NRfRf, NRfC(═O)Rf, S(O)pNRfRf, NRfS(O)pRf, NRfC(═O)ORf, OC(═O)NRfRf and —(CH2)nNRfRf,
Rf is independently selected from H, F, Cl, Br, CN, OH, C1-5alkyl (optimally substituted with halogen and OH), C3-6 cycloalkyl, and phenyl, or Rf and Rf together with the nitrogen atom to which they are both attached form a heterocyclic ring optionally substituted with C1-4alkyl;
n is independently selected from zero, 1, 2, and 3;
r is independently selected from zero, 1, 2, and 3;
and
p is independently selected from zero, 1, and 2.

36 more elements

Facts

Application

15/171,276Filed 2 Jun 2016

Priority

3 Jun 2015

Published

8 Dec 2016

Term ends

Not estimatedThe source records don’t support an estimate.

Classification12 codes

C07D 413/04
Containing two hetero rings: directly linked by a ring-member-to-ring-member bond
A61P 9/00
Drugs for disorders of the cardiovascular system
A61P 9/04
Drugs for disorders of the cardiovascular system: inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
A61P 9/10
Drugs for disorders of the cardiovascular system: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary…