US 11,731,954 B2Granted

Histone demethylase inhibitors

OwnerYoung K. Chen, Michael Brennan Wallaceinventors

Life of this patent

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Abstract

The present disclosure relates generally to compositions and methods for treating cancer and neoplastic disease. Provided herein are substituted pyridine derivative compounds, and compositions (including pharmaceutical compositions) that include these compounds. The subject compounds and compositions are useful for inhibition of at least one histone demethylase. Furthermore, the subject compounds and compositions are useful for the treatment of cancer or neoplastic disease, such as prostate cancer, breast cancer, bladder cancer, lung cancer, melanoma, retinoblastoma, or multiple endocrine neoplasia type 1.

Claims14

Dependent claims

A method of treating esophageal cancer in a subject in need thereof, comprising administering to the subject a therapeutically effective dose of a compound of Formula 1:

wherein a compound of Formula 1 includes isomers and pharmaceutically acceptable salts thereof, and wherein:
n is 0 or 1
R4 is hydrogen or optionally substituted C1-C6 alkyl;
R6 is hydrogen or X—Y, wherein
X is a bond, O, S, N(R), C(O), N(R)C(O), C(O)N(R), or optionally substituted C1-C3 alkyl, wherein
R is hydrogen or optionally substituted C1-C6 alkyl, and
Y is optionally substituted alkyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl;
and
R5, R7, and R8 are each independently selected from hydrogen, halogen, hydroxyl, cyanyl, N(R1)(R2), or optionally substituted C1-C6 alkyl, C1-C6 alkynyl, C1-C6 alkenyl, C1-C6 alkoxy, C3-C7 carbocyclyl, C3-C7 carbocyclyloxy, C4-C12 carbocyclylalkyl, C4-C12 carbocyclylalkoxy, C6-C10 aryl, C6-C10 aryloxy, C6-C10 aryl-S, C6-C10 aryl-SO2, C7-C14 aralkoxy, heteroaryl, heteroaryloxy, heterocyclyl, heterocyclyloxy, heterocyclylalkyl, heterocyclylalkoxy or heteroaryl-S, wherein
R1 is hydrogen or optionally substituted C1-C6 alkyl, and
R2 is optionally substituted alkyl, aryl, heteroaryl, heterocyclyl, cycloalkyl, cycloalkylalkyl, aryl-CO, heteroaryl-CO, cycloalkyl-CO, or alkyl-CO.

8 more elements

A method of treating esophageal cancer in a subject in need thereof, comprising administering to the subject a therapeutically effective dose of a compound, or a pharmaceutically acceptable salt thereof, selected from the group consisting of:

3-[({(1S)-6-[methyl(4-methylphenyl) amino]-1,2,3,4-tetrahydroisoquinolyl}methyl)amino]pyridine-4-carboxylic acid;
3-[({(1R)-6-[methyl(4-methylphenyl) amino]-1,2,3,4-tetrahydroisoquinolyl methyl)amino]pyridine-4-carboxylic acid;
3-[({(1S)-6-[2-methyl-4-(2,2,2-trifluoro-ethoxy)phenyl]-1,2,3,4-tetrahydro-isoquinolyl]methyl)amino]pyridine-4-carboxylic acid;
3-[({(1R)-6-[2-methyl-4-(2,2,2-trifluoroethoxy)phenyl]-1,2,3,4-tetrahydroisoquinolyl} methyl) amino]pyridine-4-carboxylic acid;
3-{[((1S)-6-{methyl[4-isopropyl phenyl]amino}-1,2,3,4-tetrahydroisoquinolyl)methyl]amino}pyridine-4-carboxylic acid;
3-{[((1R)-6-{methyl[4-isopropylphenyl]amino}-1,2,3,4-tetrahydroisoquinolyl) methyl]amino}pyridine-4-carboxylic acid;
3-[({(1S)-6-[4-(cyclopropylmethoxy)-2-methylphenyl]-1,2,3,4-tetrahydro-isoquinolyl]methyl)amino]pyridine-4-carboxylic acid;
3-[({(1R)-6-[4-(cyclopropylmethoxy)-2-methylphenyl]-1,2,3,4-tetrahydroiso-quinolyl[methyl)amino]pyridine-4-carboxylic acid;
3-[({(1S)-5-[methyl(4-tolyl)amino]isoindolinyl}methyl)amino]pyridine-4-carboxylic acid;
3-[({(1R)-5-[methyl(4-tolyl)amino]isoindolinyl}methyl)amino]pyridine-4-carboxylic acid;
3-{[((1S)-5-{methyl[4-isopropylphenyl]amino} isoindolinyl)methyl]amino} pyridine-4-carboxylic acid;
3-{[((1R)-5-{methyl[4-isopropylphenyl]amino} isoindolinyl)methyl]amino} pyridine-4-carboxylic acid;
3-[({(1S)-5-[2-methyl-4-(2,2,2-trifluoro-ethoxy)phenyl]isoindolinyl}methyl) amino]pyridine-4-carboxylic acid;
3-[({(1R)-5-[2-methyl-4-(2,2,2-trifluoro-ethoxy)phenyl]isoindolinyl}methyl)amino]pyridine-4-carboxylic acid;
(R)-3-(((6-((4-ethylphenyl)(methyl) amino)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino)isonicotinic acid;
(S)-3-(((6-((4-ethylphenyl)(methyl) amino)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((2-methyl-6-(methyl(p-tolyl) amino)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino)isonicotinic acid;
(S)-3-(((2-methyl-6-(methyl(p-tolyl) amino)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((2-methyl-6-(o-tolyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl) amino)isonicotinic acid;
(S)-3-(((2-methyl-6-(o-tolyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl) amino)isonicotinic acid;
(R)-3-(((6-((4-ethylphenyl)(methyl) amino)-2-methyl-1,2,3,4-tetrahydro-isoquinolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((6-((4-ethylphenyl)(methyl) amino)-2-methyl-1,2,3,4-tetrahydro-isoquinolin-1-yl) methyl)amino) isonicotinic acid;
(R)-3-(((2-methyl-6-(methyl (4-propylphenyl) amino)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((2-methyl-6-(methyl (4-propylphenyl) amino)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((6-(2-ethylphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((6-(2-ethylphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((6-(2-isopropylphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((6-(2-isopropylphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((6-(2,6-dimethylphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((6-(2,6-dimethylphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((2-methyl-5-(methyl(p-tolyl) amino)isoindolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((2-methyl-5-(methyl(p-tolyl) amino)isoindolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((5-((4-ethylphenyl)(methyl) amino)-2-methylisoindolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((5-((4-ethylphenyl)(methyl) amino)-2-methylisoindolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((2-methyl-5-(methyl (4-propylphenyl)amino)isoindolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((2-methyl-5-(methyl (4-propylphenyl)amino)isoindolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((2-methyl-5-(o-tolyl)isoindolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((2-methyl-5-(o-tolyl)isoindolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((5-(2-ethylphenyl)-2-methyl-isoindolin-1-yl) methyl)amino) isonicotinic acid;
(S)-3-(((5-(2-ethylphenyl)-2-methyl-isoindolin-1-yl) methyl)amino) isonicotinic acid;
3-({[(1R)-6-(thiol-3-yl)-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl} amino)pyridine-4-carboxylic acid;
3-({[(1S)-6-(thiol-3-yl)-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl} amino)pyridine-4-carboxylic acid;
3-({[(1R)-6-[2-fluoro-4-(2,2,2-trifluoro-ethoxy)phenyl]-1,2,3,4-tetrahydroiso-quinolin-1-yl] methyl} amino)pyridine-4-carboxylic acid;
3-({[(1S)-6-[2-fluoro-4-(2,2,2-trifluoro-ethoxy)phenyl]-1,2,3,4-tetrahydroiso-quinolin-1-yl] methyl} amino)pyridine-4-carboxylic acid;
3-({[(1R)-6-(2,4-difluorophenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl} amino)pyridine-4-carboxylic acid;
3-({[(1S)-6-(2,4-difluorophenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl} amino)pyridine-4-carboxylic acid;
(R)-3-(((6-(4-chloro-2-fluorophenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl) amino)isonicotinic acid;
(S)-3-(((6-(4-chloro-2-fluorophenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((6-(4-isopropoxy-2-methylphenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((6-(4-isopropoxy-2-methylphenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((6-(4-isopropyl-2-methylphenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((6-(4-isopropyl-2-methylphenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((6-(4-(difluoromethoxy)-2-methylphenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino)isonicotinic acid;
(S)-3-(((6-(4-(difluoromethoxy)-2-methylphenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino)isonicotinic acid;
(R)-3-(((6-(2-methyl-4-propoxyphenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((6-(2-methyl-4-propoxyphenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((6-(4-chloro-3-fluorophenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((6-(4-chloro-3-fluorophenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((6-(2-fluoro-6-methoxyphenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((6-(2-fluoro-6-methoxyphenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((6-(2-methyl-4-(3,4-dihydroquinolin-1(2H)-yl)phenyl)-1,2,3,4-tetrahydro-isoquinolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((6-(2-methyl-4-(3,4-dihydroquinolin-1(2H)-yl)phenyl)-1,2,3,4-tetrahydro-isoquinolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((6-(2-methyl-4-(3,4-dihydroisoquinolin-2(1H)-yl)phenyl)-1,2,3,4-tetrahydro-isoquinolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((6-(2-methyl-4-(3,4-dihydroisoquinolin-2(1H)-yl)phenyl)-1,2,3,4-tetrahydro-isoquinolin-1-yl) methyl)amino) isonicotinic acid;
(R)-3-(((6-(4-isopropyl-2-methoxy-phenyl)-1,2,3,4-tetrahydro-isoquinolin-1-yl) methyl)amino) isonicotinic acid;
(S)-3-(((6-(4-isopropyl-2-methoxy-phenyl)-1,2,3,4-tetrahydro-isoquinolin-1-yl) methyl)amino) isonicotinic acid;
(R)-3-(((6-(2-methyl-4-(6-methyl-indolin-1-yl)phenyl)-1,2,3,4-tetrahydroiso-quinolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((6-(2-methyl-4-(6-methyl-indolin-1-yl)phenyl)-1,2,3,4-tetrahydroiso-quinolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((6-((4-cyclopropylphenyl) (methyl)amino)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((6-((4-cyclopropylphenyl) (methyl)amino)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((6-(methyl(4-propylphenyl)amino)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((6-(methyl(4-propylphenyl)amino)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((6-((4-isobutylphenyl) (methyl)amino)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((6-((4-isobutylphenyl) (methyl)amino)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((6-((4-hexylphenyl)(methyl) amino)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino)isonicotinic acid;
(S)-3-(((6-((4-hexylphenyl)(methyl) amino)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino)isonicotinic acid;
(R)-3-(((6-((4-(cyclopropylmethyl) phenyl)(methyl)amino)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((6-((4-(cyclopropylmethyl) phenyl)(methyl)amino)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((6-(methyl(4-(2,2,2-trifluoroethoxy)phenyl)amino)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl) amino)isonicotinic acid;
(S)-3-(((6-(methyl(4-(2,2,2-trifluoroethoxy)phenyl)amino)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl) amino)isonicotinic acid;
(R)-3-(((6-(2-methyl-4-(pyrrolidin-1-yl) phenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((6-(2-methyl-4-(pyrrolidin-1-yl) phenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino)isonicotinic acid;
(R)-3-(((6-((4-isopropoxyphenyl) (methyl)amino)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((6-((4-isopropoxyphenyl) (methyl)amino)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((6-(methyl(4-(2,2,2-trifluoro-ethyl)phenyl)amino)-1,2,3,4-tetrahydro-isoquinolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((6-(methyl(4-(2,2,2-trifluoro-ethyl)phenyl)amino)-1,2,3,4-tetrahydro-isoquinolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((6-((4-chlorophenyl)(methyl) amino)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino)isonicotinic acid;
(S)-3-(((6-((4-chlorophenyl)(methyl) amino)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino)isonicotinic acid;
(R)-3-(((6-(2-ethylphenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((6-(2-ethylphenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((6-(2-isopropylphenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl) amino)isonicotinic acid;
(S)-3-(((6-(2-isopropylphenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl) amino)isonicotinic acid;
(R)-3-(((6-(2,6-dimethyl-4-(2,2,2-trifluoroethoxy)phenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((6-(2,6-dimethyl-4-(2,2,2-trifluoroethoxy)phenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((6-(2-(2,2,2-trifluoroethoxy) phenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino)isonicotinic acid;
(S)-3-(((6-(2-(2,2,2-trifluoroethoxy) phenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino)isonicotinic acid;
(R)-3-(((6-(2,6-dimethylphenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl) amino)isonicotinic acid;
(S)-3-(((6-(2,6-dimethylphenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl) amino)isonicotinic acid;
(R)-3-(((6-(2-cyclopropylphenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((6-(2-cyclopropylphenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((6-((4-(dimethylamino)phenyl) (methyl)amino)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((6-((4-(dimethyl amino) phenyl) (methyl)amino)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((6-((4-cyclohexylphenyl)(methyl) amino)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino)isonicotinic acid;
(S)-3-(((6-((4-cyclohexylphenyl) (methyl)amino)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((6-(methyl(4-(tetrahydro-2H-pyran-4-yl)phenyl)amino)-1,2,3,4-tetrahydro-isoquinolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((6-(methyl(4-(tetrahydro-2H-pyran-4-yl)phenyl)amino)-1,2,3,4-tetra-hydroisoquinolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((6-(methyl(4-(3,3,3-trifluoropropyl)phenyl)amino)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((6-(methyl (4-(3,3,3-trifluoropropyl)phenyl)amino)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((6-((4-(2-cyclopropylethyl) phenyl)(methyl)amino)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((6-((4-(2-cyclopropylethyl) phenyl) (methyl)amino)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((6-((4-cyclobutylphenyl)(methyl) amino)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino)isonicotinic acid;
(S)-3-(((6-((4-cyclobutylphenyl)(methyl) amino)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino)isonicotinic acid;
(R)-3-(((6-((4-cyclopentylphenyl) (methyl)amino)-1,2,3,4-tetrahydro-isoquinolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((6-((4-cyclopentylphenyl) (methyl)amino)-1,2,3,4-tetrahydro-isoquinolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((6-((4-(cyclobutylmethyl)phenyl) (methyl)amino)-1,2,3,4-tetrahydro-isoquinolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((6-((4-(cyclobutylmethyl)phenyl) (methyl)amino)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((6-(6-methyl-2,3-dihydrobenzofuran-5-yl)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((6-(6-methyl-2,3-dihydrobenzofuran-5-yl)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((6-(5-methyl-2,3-dihydrobenzofuran-4-yl)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((6-(5-methyl-2,3-dihydrobenzofuran-4-yl)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((5-(2-fluoro-4-(2,2,2-trifluoroethoxy)phenyl)isoindolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((5-(2-fluoro-4-(2,2,2-trifluoroethoxy)phenyl)isoindolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((5-(o-tolyl)isoindolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((5-(o-tolyl)isoindolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((5-((4-isopropylphenyl)(methyl) amino)isoindolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((5-((4-isopropylphenyl)(methyl) amino)isoindolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((5-(4-isopropyl-2-methylphenyl)isoindolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((5-(4-isopropyl-2-methylphenyl)isoindolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((5-((4-cyclopropylphenyl) (methyl)amino)isoindolin-1-yl)methyl) amino)isonicotinic acid;
(S)-3-(((5-((4-cyclopropylphenyl) (methyl)amino)isoindolin-1-yl)methyl) amino)isonicotinic acid;
(R)-3-(((5-((4-ethylphenyl)(methyl) amino)isoindolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((5-((4-ethylphenyl)(methyl) amino)isoindolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((5-(methyl(4-propylphenyl) amino) isoindolin-1-yl)methyl) amino)isonicotinic acid;
(S)-3-(((5-(methyl(4-propylphenyl) amino)isoindolin-1-yl)methyl) amino)isonicotinic acid;
(R)-3-(((5-(2-methyl-4-(pyrrolidin-1-yl) phenyl)isoindolin-1-yl)methyl) amino)isonicotinic acid;
(S)-3-(((5-(2-methyl-4-(pyrrolidin-1-yl) phenyl)isoindolin-1-yl)methyl) amino)isonicotinic acid;
(R)-3-(((5-(2-ethylphenyl)isoindolin-1-yl)methyl)amino)isonicotinic acid;
(S)-3-(((5-(2-ethylphenyl)isoindolin-1-yl)methyl)amino)isonicotinic acid;
(R)-3-(((5-(2-isopropylphenyl)isoindolin-1-yl)methyl)amino)isonicotinic acid;
(S)-3-(((5-(2-isopropylphenyl)isoindolin-1-yl)methyl)amino)isonicotinic acid;
(R)-3-(((5-(2-cyclopropylphenyl) isoindolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((5-(2-cyclopropylphenyl) isoindolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((6-(thiol-3-yl)-1,2,3,4-tetrahydroiso-quinolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((6-(thiol-3-yl)-1,2,3,4-tetrahydroiso-quinolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((6-(o-tolyl)-1,2,3,4-tetrahydroiso-quinolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((6-(o-tolyl)-1,2,3,4-tetrahydroiso-quinolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((6-(4-(difluoromethyl)-2-methylphenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((6-(4-(difluoromethyl)-2-methyl-phenyl)-1,2,3,4-tetrahydroisoquinolin-1-methyl)amino)isonicotinic acid;
(S)-3-(((6-(3,4-dihydroquinolin-1(2H)-yl)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((6-(3,4-dihydroquinolin-1(2H)-yl)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((6-(5-methylindolin-1-yl)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((6-(5-methylindolin-1-yl)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((1′,2′,3,3′,4,4′-hexahydro-1H-[2,6′-bi-isoquinolin]-1′-yl)methyl)amino) isonicotinic acid;
(R)-3-(((1′,2′,3,3′,4,4′-hexahydro-1H-[2,6′-bi-isoquinolin]-1′-yl)methyl)amino) isonicotinic acid;
(S)-3-(((6-(4-chloro-3,5-difluorophenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((6-(4-chloro-3,5-difluorophenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-((6-(methyl(p-tolyl)amino)-1,2,3,4-tetra-hydroisoquinolin-1-yl)methoxy) isonicotinic acid;
(R)-3-((6-(methyl(p-tolyl)amino)-1,2,3,4-tetra-hydroisoquinolin-1-yl)methoxy)isonicotinic acid;
(S)-3-((6-((4-isopropylphenyl)(methyl) amino)-1,2,3,4-tetrahydroisoquinolin-1-yl)methoxy) isonicotinic acid;
(R)-3-((6-((4-isopropylphenyl)(methyl) amino)-1,2,3,4-tetrahydroisoquinolin-1-yl)methoxy) isonicotinic acid;
(S)-3-((6-(2-methyl-4-(2,2,2-trifluoroethoxy) phenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl) methoxy)isonicotinic acid;
(R)-3-((6-(2-methyl-4-(2,2,2-trifluoroethoxy) phenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl) methoxy)isonicotinic acid;
(S)-3-(((6-(p-tolyloxy)-1,2,3,4-tetrahydroiso-quinolin-1-yl)methyl)amino)isonicotinic acid;
(R)-3-(((6-(p-tolyloxy)-1,2,3,4-tetrahydroiso-quinolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((6-(o-tolyloxy)-1,2,3,4-tetrahydroiso-quinolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((6-(o-tolyloxy)-1,2,3,4-tetrahydro-isoquinolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((6-(4-fluorophenoxy)-1,2,3,4-tetrahydro-isoquinolin-1-yl)methyl)amino)isonicotinic acid;
(R)-3-(((6-(4-fluorophenoxy)-1,2,3,4-tetrahydro-isoquinolin-1-yl)methyl)amino)isonicotinic acid;
(S)-3-(((6-(2-fluorophenoxy)-1,2,3,4-tetrahydro-isoquinolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((6-(2-fluorophenoxy)-1,2,3,4-tetrahydro-isoquinolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((6-(p-tolylthio)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((6-(p-tolylthio)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((6-(o-tolylthio)-1,2,3,4-tetrahydroiso-quinolin-1-yl)methyl)amino)isonicotinic acid;
(R)-3-(((6-(o-tolylthio)-1,2,3,4-tetrahydroiso-quinolin-1-yl)methyl)amino)isonicotinic acid;
(S)-3-(((6-((4-fluorophenyl)thio)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((6-((4-fluorophenyl)thio)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((6-((2-fluorophenyl)thio)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((6-((2-fluorophenyl)thio)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((6-(2-methyl-4-phenoxyphenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((6-(2-methyl-4-phenoxyphenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((5-(2,4-difluorophenyl)isoindolin-1-yl)methyl)amino)isonicotinic acid;
(R)-3-(((5-(2,4-difluorophenyl)isoindolin-1-yl)methyl)amino)isonicotinic acid;
(S)-3-(((5-(4-chloro-2-fluorophenyl)isoindolin-1-yl)methyl)amino)isonicotinic acid;
(R)-3-(((5-(4-chloro-2-fluorophenyl)isoindolin-1-yl)methyl)amino)isonicotinic acid;
(S)-3-(((5-(2-methyl-4-phenoxyphenyl)isoindolin-1-yl)methyl)amino)isonicotinic acid;
(R)-3-(((5-(2-methyl-4-phenoxyphenyl)isoindolin-1-yl)methyl)amino)isonicotinic acid;
(S)-3-(((7-(methyl(p-tolyl)amino)-2,3,4,5-tetrahydro-1H-benzo[c]azepin-1-yl)methyl) amino)isonicotinic acid;
(R)-3-(((7-(methyl(p-tolyl)amino)-2,3,4,5-tetrahydro-1H-benzo[c]azepin-1-yl)methyl) amino)isonicotinic acid;
(S)-3-(((7-((4-isopropylphenyl)(methyl)amino)-2,3,4,5-tetrahydro-1H-benzo[c]azepin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((7-((4-isopropylphenyl)(methyl)amino)-2,3,4,5-tetrahydro-1H-benzo[c]azepin-1-yl) methyl)amino) isonicotinic acid;
(S)-3-(((7-(2-methyl-4-(2,2,2-trifluoroethoxy) phenyl)-2,3,4,5-tetrahydro-1H-benzo[c]azepin-1-yl)methyl)amino)isonicotinic acid;
(R)-3-(((7-(2-methyl-4-(2,2,2-trifluoroethoxy)phenyl)-2,3,4,5-tetrahydro-1H-benzo[c]azepin-1-yl)methyl) amino)isonicotinic acid;
3-[({(1S)-6-[4-(cyclopropylmethoxy)-2-methyl-phenyl]-1,2,3,4-tetrahydroisoquinol-yl}methyl) amino]pyridine-4-carboxylic acid;
3-[(1 (1R)-6-[4-(cyclopropylmethoxy)-2-methyl-phenyl]-1,2,3,4-tetrahydroisoquinol-yl}methyl) amino]pyridine-4-carboxylic acid;
(R)-3-(((5-(2-fluoro-4-(2,2,2-trifluoroethoxy) phenyl)-2-methylisoindolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((5-(2-fluoro-4-(2,2,2-trifluoroethoxy) phenyl)-2-methylisoindolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((5-((4-isopropylphenyl)methyl)amino-2-methylisoindolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((5-((4-isopropylphenyl)methyl)amino-2-methylisoindolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((5-((4-isopropyl-2-methylphenyl)-2-methylisoindolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((5-((4-isopropyl-2-methylphenyl)-2-methylisoindolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((5-((4-cyclopropylphenyl)(methyl)amino)-2-methylisoindolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((5-((4-cyclopropylphenyl)(methyl)amino)-2-methylisoindolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((2-methyl-5-(2-methyl-4-(pyrrolidin-1-yl) phenyl)isoindolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((2-methyl-5-(2-methyl-4-(pyrrolidin-1-yl) phenyl)isoindolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((5-(2-isopropylphenyl)-2-methyl-isoindolin-1-yl)methyl) amino)isonicotinic acid;
(S)-3-(((5-(2-isopropylphenyl)-2-methyl-isoindolin-1-yl)methyl) amino)isonicotinic acid;
(R)-3-(((5-(2-cyclopropylphenyl)-2-methyl-isoindolin-1-yl)methyl) amino)isonicotinic acid;
(S)-3-(((5-(2-cyclopropylphenyl)-2-methyl-isoindolin-1-yl)methyl) amino)isonicotinic acid;
(R)-3-(((5-(4-fluoro-2-methylphenyl)-2-methyliso-indolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((5-(4-fluoro-2-methylphenyl)-2-methyl-isoindolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-4(5-(2-methoxyphenyl)-2-methyliso-indolin-1-yl)methyl) amino)isonicotinic acid;
(S)-3-(((5-(2-methoxyphenyl)-2-methyliso-indolin-1-yl)methyl) amino)isonicotinic acid;
(R)-3-(((5-(2-fluorophenyl)-2-methyliso-indolin-1-yl)methyl)amino)isonicotinic acid;
(S)-3-(((5-(2-fluorophenyl)-2-methyliso-indolin-1-yl)methyl)amino)isonicotinic acid;
(R)-3-(((5-(2,4-difluorophenyl)-2-methyliso-indolin-1-yl)methyl) amino)isonicotinic acid;
(S)-3-(((5-(2,4-difluorophenyl)-2-methyliso-indolin-1-yl)methyl) amino)isonicotinic acid;
(R)-3-(((5-(4-cyclopropylmethoxy)-2-fluoro-phenyl)-2-methylisoindolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((5-(4-cyclopropylmethoxy)-2-fluoro-phenyl)-2-methylisoindolin-1-yl) methyl)amino) isonicotinic acid;
(R)-3-(((5-(2-fluoro-4-methoxyphenyl)-2-methyl-isoindolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((5-(2-fluoro-4-methoxyphenyl)-2-methyl-isoindolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((5-(4-methoxyphenyl-2-methylphenyl)-2-methylisoindolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((5-(4-methoxyphenyl-2-methylphenyl)-2-methylisoindolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((5-(4-(dimethylamino)-2-methylphenyl)-2-methylisoindolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((5-(4-(dimethylamino)-2-methylphenyl)-2-methylisoindolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((5-(4-(azetidin-1-yl)-2-methylphenyl)-2-methylisoindolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((5-(4-(azetidin-1-yl)-2-methylphenyl)-2-methylisoindolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((2-ethyl-5-(o-tolyl)isoindolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((2-ethyl-5-(o-tolyl)isoindolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((2-ethyl-5-(2-fluorophenyl)isoindolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((2-ethyl-5-(2-fluorophenyl)isoindolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((2-isopropyl-5-(o-tolyl)isoindolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((2-isopropyl-5-(o-tolyl)isoindolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((2-cyclopropyl-5-(o-tolyl)isoindolin-1-yl) methyl)amino)isonicotinic acid;
(S)-3-(((2-cyclopropyl-5-(o-tolyl)isoindolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((2-cyclopropyl-5-(2-fluorophenyl) isoindolin-1-yl)methyl)amino)isonicotinic acid;
(S)-3-(((2-cyclopropyl-5-(2-fluorophenyl) isoindolin-1-yl)methyl)amino)isonicotinic acid;
(R)-3-(((5-(2-fluorophenyl)-2-isopropyliso-indolin-1-yl)methyl)amino)isonicotinic acid;
(S)-3-(((5-(2-fluorophenyl)-2-isopropyliso-indolin-1-yl)methyl)amino)isonicotinic acid;
(R)-3-(((2-(cyclopropylmethyl)-5-(2-fluorophenyl) isoindolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((2-(cyclopropylmethyl)-5-(2-fluorophenyl) isoindolin-1-yl) methyl)amino) isonicotinic acid;
(R)-3-(((2-methyl-5-(2-pyrrolidin-1-yl)phenyl) isoindolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((2-methyl-5-(2-pyrrolidin-1-yl)phenyl) isoindolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((5-(2-dimethylamino)phenyl)isoindolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((5-(2-dimethylamino)phenyl)isoindolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((5-(4-isopropyl-2-methoxyphenyl)-2-methylisoindolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((5-(4-isopropyl-2-methoxyphenyl)-2-methylisoindolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((2-methyl-5-(p-tolyloxy)isoindolin-1-yl) methyl)amino) isonicotinic acid;
(S)-3-(((2-methyl-5-(p-tolyloxy)isoindolin-1-yl) methyl)amino) isonicotinic acid;
(R)-3-(((2-methyl-5-(p-tolylthio)isoindolin-1-yl) methyl)amino) isonicotinic acid;
(S)-3-(((2-methyl-5-(p-tolylthio)isoindolin-1-yl) methyl)amino) isonicotinic acid;
(R)-3-(((5-ethyl(p-tolyl)amino)-2-methyliso-indolin-1-yl)methyl) amino) isonicotinic acid;
(S)-3-(((5-ethyl(p-tolyl)amino)-2-methyliso-indolin-1-yl)methyl) amino) isonicotinic acid;
(R)-3-(((2-methyl-5-(p-tolyl(2,2,2-trifluoro-ethyl)amino)isoindolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((2-methyl-5-(p-tolyl(2,2,2-trifluoro-ethyl)amino)isoindolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((5-(cyclopropylmethyl)(p-tolyl)amino)-2-methylisoindolin-1-yl)methyl) amino) isonicotinic acid;
(S)-3-(((5-(cyclopropylmethyl)(p-tolyl)amino)-2-methylisoindolin-1-yl)methyl) amino) isonicotinic acid;
(R)-3-(((2-methyl-6-(thiophen-3-yl)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((2-methyl-6-(thiophen-3-yl)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((6-(2-fluoro-4-(2,2,2-trifluroethoxy) phenyl)-2-methyl)-1,2,3,4-tetrahydroiso-quinolin yl)methyl)amino) isonicotinic acid;
(S)-3-(((6-(2-fluoro-4-(2,2,2-trifluroethoxy) phenyl)-2-methyl)-1,2,3,4-tetrahydroiso-quinolin yl)methyl)amino) isonicotinic acid;
(R)-3-(((6-(2,4-difluorophenyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((6-(2,4-difluorophenyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((6-(4-chloro-2-fluorophenyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((6-(4-chloro-2-fluorophenyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((6-(4-isopropoxy-2-methylphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino) isonicotinic acid;
(S)-3-(((6-(4-isopropoxy-2-methylphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino) isonicotinic acid;
(R)-3-(((6-(4-isopropyl-2-methylphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((6-(4-isopropyl-2-methylphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((6-(4-(difluoromethoxy)-2-methylphenyl)-2-methyl-1,2,3,4-tetrahydro-isoquinolin-1-yl) methyl)amino) isonicotinic acid;
(S)-3-(((6-(4-(difluoromethoxy)-2-methylphenyl)-2-methyl-1,2,3,4-tetrahydro-isoquinolin-1-yl) methyl)amino) isonicotinic acid;
(R)-3-(((2-methyl-6-(2-methyl-4-propoxyphenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((2-methyl-6-(2-methyl-4-propoxyphenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((6-(4-chloro-3-fluorophenyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((6-(4-chloro-3-fluorophenyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((6-(2-fluoro-6-methoxyphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino)isonicotinic acid;
(S)-3-(((6-(2-fluoro-6-methoxyphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((6-(4-isopropyl-2-methoxyphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl) amino) isonicotinic acid;
(S)-3-(((6-(4-isopropyl-2-methoxyphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl) amino) isonicotinic acid;
(R)-3-(((6-(4-cyclopropylphenyl)(methyl) amino)-2-methyl-1,2,3,4-tetrahydroiso-quinolin-1-yl) methyl)amino) isonicotinic acid;
(S)-3-(((6-(4-cyclopropylphenyl)(methyl) amino)-2-methyl-1,2,3,4-tetrahydroiso-quinolin-1-yl) methyl)amino)isonicotinic acid;
(R)-3-(((6-(4-isobutylphenyl)(methyl) amino)-2-methyl-1,2,3,4-tetrahydro-isoquinolin-1-yl) methyl)amino) isonicotinic acid;
(S)-3-(((6-(4-isobutylphenyl)(methyl) amino)-2-methyl-1,2,3,4-tetrahydro-isoquinolin-1-yl) methyl)amino) isonicotinic acid;
(R)-3-(((6-(4-cyclopropylmethyl)phenyl)(methyl) amino)-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((6-(4-cyclopropylmethyl)phenyl)(methyl) amino)-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((2-methyl-6-(methyl(4-(2,2,2-trifluoro-ethoxy)phenyl)amino)-1,2,3,4,-tetrahydroiso-quinolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((2-methyl-6-(methyl(4-(2,2,2-trifluoro-ethoxy)phenyl)amino)-1,2,3,4,-tetrahydroiso-quinolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((2-methyl-6-(2-methyl-4-(pyrrolidin-1-yl) phenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl) amino) isonicotinic acid;
(S)-3-(((2-methyl-6-(2-methyl-4-(pyrrolidin-1-yl) phenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino) isonicotinic acid;
(R)-3-(((6-(4-isopropoxyphenyl)(methyl)amino)-2-methyl-1,2,3,4-tetrahydro-isoquinolin-1-yl) methyl)amino) isonicotinic acid;
(S)-3-(((6-(4-isopropoxyphenyl)(methyl)amino)-2-methyl-1,2,3,4-tetrahydro-isoquinolin-1-yl) methyl)amino) isonicotinic acid;
(R)-3-(((2-methyl-6-(methyl(4-(2,2,2-trifluroethyl) phenyl)amino)-1,2,3,4,-tetrahydroisoquinolin-1-yl) methyl)amino) isonicotinic acid;
(S)-3-(((2-methyl-6-(methyl(4-(2,2,2-trifluroethyl) phenyl)amino)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino) isonicotinic acid;
(R)-3-(((6-((4-chlorophenyl)(methyl)amino)-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl) amino) isonicotinic acid;
(S)-3-(((6-((4-chlorophenyl)(methyl)amino)-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl) amino) isonicotinic acid;
(R)-3-(((6-(2,6-dimethyl-4-(2,2,2-trifluroethoxy) phenyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((6-(2,6-dimethyl-4-(2,2,2-trifluroethoxy) phenyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl) amino)isonicotinic acid;
(R)-3-(((6-(2-methyl-6-(2-(2,2,2-trifluroethoxy) phenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl) amino) isonicotinic acid;
(S)-3-(((6-(2-methyl-6-(2-(2,2,2-trifluroethoxy) phenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino) isonicotinic acid;
(R)-3-(((6-(2-cyclopropylphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl) amino) isonicotinic acid;
(S)-3-(((6-(2-cyclopropylphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl) amino) isonicotinic acid;
(R)-3-(((6-(4-dimethylamino)phenyl)(methyl) amino)-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((6-(4-dimethylamino)phenyl)(methyl) amino)-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((2-methyl-6-(methyl(4-(tetrahydro-2H-pyran-4-yl)phenyl)amino)-1,2,3,4-tetrahydro-isoquinolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((2-methyl-6-(methyl(4-(tetrahydro-2H-pyran-4-yl)phenyl)amino)-1,2,3,4-tetrahydro-isoquinolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((2-methyl-6-(methyl(4-(3,3,3-trifluoro-propyl)phenyl)amino)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((2-methyl-6-(methyl(4-(3,3,3-trifluoro-propyl)phenyl)amino)-1,2,3,4-tetrahydroiso-quinolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((6-(4-(2-cyclopropylethyl)phenyl)(methyl) amino)-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((6-(4-(2-cyclopropylethyl)phenyl)(methyl) amino)-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl) amino) isonicotinic acid;
(R)-3-(((6-((4-cyclobutylphenyl)(methyl)amino)-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl) amino) isonicotinic acid;
(S)-3-(((6-((4-cyclobutylphenyl)(methyl)amino)-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl) amino) isonicotinic acid;
(R)-3-(((6-((4-cyclopentylphenyl)(methyl)amino)-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino) isonicotinic acid;
(S)-3-(((6-((4-cyclopentylphenyl)(methyl)amino)-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino) isonicotinic acid;
(R)-3-(((6-((4-cyclobutylmethyl)phenyl) (methyl)amino)-2-methyl-1,2,3,4-tetrahydro-isoquinolin-1-yl)methyl)amino) isonicotinic acid;
(S)-3-(((6-((4-cyclobutylmethyl)phenyl) (methyl)amino)-2-methyl-1,2,3,4-tetrahydro-isoquinolin-1-yl)methyl)amino) isonicotinic acid;
(R)-3-(((2-methyl-6-(6-methyl-2,3-dihydrobenzo-furan-5-yl)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino) isonicotinic acid;
(S)-3-(((2-methyl-6-(6-methyl-2,3-dihydrobenzo-furan-5-yl)-1,2,3,4-tetrahydroisoquinolin-1-yl) methyl)amino) isonicotinic acid;
(R)-3-(((2-methyl-6-(5-methyl-2,3-dihydro-benzofuran-4-yl)-1,2,3,4-tetrahydroiso-quinolin-1-yl) methyl)amino) isonicotinic acid;
(S)-3-(((2-methyl-6-(5-methyl-2,3-dihydro-benzofuran-4-yl)-1,2,3,4-tetrahydroiso-quinolin-1-yl) methyl)amino) isonicotinic acid;
(R)-3-(((2-methyl-6-(phenylthio)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino) isonicotinic acid;
and
(S)-3-(((2-methyl-6-(phenylthio)-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)amino) isonicotinic acid.

318 more elements

Dependencies are inferred from the claim text.

Facts

Application: 17/227,570Filed 12 Apr 2021 · continuation
Priority: 28 Dec 2015
Published: US 2021/0238161 A15 Aug 2021
Granted: 22 Aug 2023
Term ends: Not estimatedThe source records don’t support an estimate.

Classification12 codes

C07D 401/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links
A61P 35/00
Antineoplastic agents
C07D 401/14
Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a…:…
C07D 405/14
Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having…:…

Family

Application62/271,654Us provisional application · filed 28 Dec 2015
Application62/438,435Us provisional application · filed 22 Dec 2016
Application15/391,773Parent of this continuation · filed 27 Dec 2016
Application16/040,402Parent of this continuation · filed 19 Jul 2018
US 10,059,687 B2Parent of this continuation · filed 28 Aug 2018
Application16/751,432Parent of this continuation · filed 24 Jan 2020
US 10,597,379 B2Parent of this continuation · filed 24 Mar 2020
US 2021/0238161 A1Pre-grant publication · published 5 Aug 2021
US 11,001,568 B2Parent of this continuation
US 2017/0183325 A1Published application
US 2018/0319769 A1Published application
US 2020/0157077 A1Published application
US 11,731,954 B2This patent

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

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Abstract

Facts

Application

17/227,570Filed 12 Apr 2021 · continuation

Priority

28 Dec 2015

Published

US 2021/0238161 A15 Aug 2021

Granted

22 Aug 2023

Term ends

Not estimatedThe source records don’t support an estimate.

Classification12 codes

C07D 401/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links
A61P 35/00
Antineoplastic agents
C07D 401/14
Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a…:…
C07D 405/14
Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having…:…

Family

Application62/271,654Us provisional application · filed 28 Dec 2015

Application62/438,435Us provisional application · filed 22 Dec 2016

Application15/391,773Parent of this continuation · filed 27 Dec 2016

Application16/040,402Parent of this continuation · filed 19 Jul 2018

US 10,059,687 B2Parent of this continuation · filed 28 Aug 2018

Application16/751,432Parent of this continuation · filed 24 Jan 2020

US 10,597,379 B2Parent of this continuation · filed 24 Mar 2020

US 2021/0238161 A1Pre-grant publication · published 5 Aug 2021

US 11,001,568 B2Parent of this continuation

US 2017/0183325 A1Published application

US 2018/0319769 A1Published application

US 2020/0157077 A1Published application

US 11,731,954 B2This patent

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