PATENT CLAIM ANALYSIS

Application Number: 16040402
Application Type: Utility
Filing Date: 2018-07
Publication Date: 2018-11
Patent Classification: ["546", "112000"]

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.

Claim (Index 3):
A compound, or a pharmaceutically acceptable salt thereof, selected from the group consisting of:\n (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-yl)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\u2032,2\u2032,3,3\u2032,4,4\u2032-hexahydro-1H-[2,6\u2032-bi-isoquinolin]-1\u2032-yl)methyl)amino)isonicotinic acid; (R)-3-(((1\u2032,2\u2032,3,3\u2032,4,4\u2032-hexahydro-1H-[2,6\u2032-bi-isoquinolin]-1\u2032 -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-[({(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-(((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-1-yl)methyl)amino)isonicotinic acid; (S)-3-(((6-(2-fluoro-4-(2,2,2-trifluroethoxy) phenyl)-2-methyl)-1,2,3,4-tetrahydroiso-quinolin-1-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-tetrahydroisoquino-lin-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.

Metadata:
- Claim Count in Document: 3.0
- Percentile: 95.0
- Lexical Diversity: 1.69643
- Patent Class: 546.0
- Transitional Phrase Type: closed
- Component Type: 1
- Foreign Priority: False
- Related Applications: ['15391773', '15792570', '15402100', '13060426', '15971749']

Analysis Scores:
- 35 USC 101 Eligibility (BERT): 0.8364493217900442
- 35 USC 102 Novelty (BERT): 0.5326105968856556
- Combined Prediction Score: 0.8060654492996053
- Mean Citation Score: 327.9455440000001
- Max Citation Score: 382.30826
- Similarity Product: 281.944758120575

Labels:
- Claim Label 101: 1
- Claim Label 102: 1
- Claim Label 103: 1
- Claim Label 112: 1
- Combined Label: 1
- Label 101 Adjusted: 1

Dataset: test