US 10,246,469 B2Granted

Biaryl kinase inhibitors

AssigneesBristol-Myers Squibb Company, Syngene International Limited

InventorsJoanne J. Bronson, Ling Chen, Jonathan L. Ditta, Carolyn Diane Dzierba, Prasada Rao Jalagam, Guanglin Luo, John E. Macor, Tarun Kumar Maishal, Susheel Jethanand Nara, Ramkumar Rajamani, Ramesh Kumar Sistla, Soodamani Thangavel

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Abstract

The present disclosure is directed to biaryl compounds of formula (I) which can inhibit AAK1 (adaptor associated kinase 1), compositions comprising such compounds and their use for treating e.g. pain, Alzheimer's disease, Parkinson's disease and schizophrenia.

Claims8

Dependent claims

A compound of formula (I)

or a pharmaceutically acceptable salt thereof, wherein:
A is selected from
wherein “” denotes the point of attachment to B;
B is selected from
wherein “*” indicates the point of attachment to R5 and “**” indicates the point of attachment to ring A;
R1 is selected from hydrogen, amino, —CO2H, cyclopropyl, difluoromethyl, ethyl, halo, hydroxymethyl, methoxy, methoxymethyl, methyl, —NHC(O)CH3, —NHCO2CH3, trifluoromethoxy, trifluoromethyl,
wherein Ra is selected from hydrogen, halo and methyl;
R2 is selected from hydrogen, cyano, —CH2OH, halo, and methyl;
R3 is selected from hydrogen, cyano, cyclopropyl, difluoromethyl, fluoromethyl, halo, hydroxymethyl, methoxy, methyl, methylsulfonyl, trifluoromethoxy, trifluoromethyl, —CH2N(CH3)2, and a five-membered aromatic ring containing one, two, or three heteroatoms selected from nitrogen, oxygen, and sulfur;
R4 is selected from hydrogen, halo, and methyl;
R5 is selected from
R6 is selected from hydrogen, ethyl, fluoromethyl, difluoromethyl, methyl, and trifluoromethyl;
provided that when A is
then B is
R1 is selected from
cyclopropyl, methoxymethyl,
R5 is selected from

14 more elements

A compound selected from

(S)-1-(4-(3,5-dimethyl-1H-pyrazol-4-yl)-2-fluorophenoxy)-2,4-dimethylpentan-2-amine;
(S)-2-((2-amino-2,4-dimethylpentyl)oxy)-5-(2,3-dimethylpyrido[2,3-b]pyrazin-8-yl)benzonitrile;
(S)-1-(2-fluoro-4-(pyrido[2,3-b]pyrazin-8-yl)phenoxy)-2,4-dimethylpentan-2-amine
(S)-2-((2-amino-2,4-dimethylpentyl)oxy)-5-(2-amino-3H-imidazo [4,5-b]pyridin-7-yl)benzonitrile;
(S)-7-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-(trifluoromethyl)phenyl)-3H-imidazo[4,5-b]pyridin-2-amine;
(S)—N-(4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-(trifluoromethyl)phenyl)pyridin-2-yl)thiazol-2-amine;
(S)—N-(4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-chlorophenyl)pyridin-2-yl)thiazol-2-amine;
(S)—N-(4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-(trifluoromethyl)phenyl)pyridin-2-yl)thiazole-2-carboxamide;
(S)-7-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-methylphenyl)-3H-imidazo [4,5-b]pyridin-2-amine;
(S)—N-(4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-chlorophenyl)pyridin-2-yl)thiazole-2-carboxamide;
(S)—N-(4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-cyanophenyl)pyridin-2-yl)thiazole-2-carboxamide;
(S)—N-(4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-chlorophenyl)pyridin-2-yl)-4-methylthiazol-2-amine;
(R)-2,4-dimethyl-1-((3-methyl-5-(pyrazolo[1,5-a]pyrimidin-7-yl)pyridin-2-yl)oxy)pentan-2-amine;
(R)-1-((3-chloro-5-(pyrazolo[1,5-a]pyrimidin-7-yl)pyridin-2-yl)oxy)-2,4-dimethylpentan-2-amine;
(R)-1-((5-(2-cyclopropylpyrazolo[1,5-a]pyrimidin-7-yl)-3-methylpyridin-2-yl)oxy)-2,4-dimethylpentan-2-amine;
(S)-2,4-dimethyl-1-((7-(2-methylpyridin-4-yl)benzo[d]thiazol-4-yl)oxy)pentan-2-amine;
(S)-methyl (4-(4-((2-amino-2,4-dimethylpentyl)oxy)benzo [d]thiazol-7-yl)pyridin-2-yl)carbamate;
(S)-2,4-dimethyl-1-(4-(2-methylthiazolo [5,4-d]pyrimidin-7-yl)-2-(trifluoromethyl)phenoxy)pentan-2-amine;
(S)-2-((2-amino-2,4-dimethylpentyl)oxy)-5-(2-methylthiazolo[5,4-d]pyrimidin-7-yl)benzonitrile;
(S)-1-((3-chloro-5-(pyrazolo[1,5-a]pyrimidin-7-yl)pyridin-2-yl)oxy)-2,4-dimethylpentan-2-amine;
(S)-2,4-dimethyl-1-((3-methyl-5-(pyrazolo[1,5-a]pyrimidin-7-yl)pyridin-2-yl)oxy)pentan-2-amine;
(S)-1-((2-(fluoromethyl)-6-(pyrazolo[1,5-a]pyrimidin-7-yl)pyridin-3-yl)oxy)-2,4-dimethylpentan-2-amine
2-amino-2-(((2′,4-bis(difluoromethyl)-[2,4′-bipyridin]-5-yl)oxy)methyl)-4-methylpentan-1-ol;
(S)-1-(4-(imidazo[1,2-b]pyridazin-8-yl)phenoxy)-2,4-dimethylpentan-2-amine;
(S)-1-(2-chloro-4-(2-methyl-3H-imidazo[4,5-b]pyridin-7-yl)phenoxy)-2,4-dimethylpentan-2-amine;
(S)-1-(4-(imidazo[1,2-b]pyridazin-8-yl)-2-(trifluoromethyl)phenoxy)-2,4-dimethylpentan-2-amine;
(S)-1-(2-chloro-4-(1H-pyrazolo[3,4-b]pyridin-4-yl)phenoxy)-2,4-dimethylpentan-2-amine;
(S)-2-((2-amino-2,4-dimethylpentyl)oxy)-5-(6-chloroimidazo[1,2-b]pyridazin-8-yl)benzonitrile;
(S)-2-((2-amino-2,4-dimethylpentyl)oxy)-5-(imidazo[1,2-b]pyridazin-8-yl)benzonitrile;
(S)-1-(2-fluoro-4-(1H-pyrazolo[3,4-b]pyridin-4-yl)phenoxy)-2,4-dimethylpentan-2-amine;
(S)-1-(2-fluoro-4-(1-methyl-1H-pyrazolo[3,4-b]pyridin-4-yl)phenoxy)-2,4-dimethylpentan-2-amine
2,4-dimethyl-1-(4-(2-methyl-3H-imidazo[4,5-b]pyridin-7-yl)-2-(trifluoromethyl)phenoxy)pentan-2-amine;
(S)-1-(4-(1H-pyrazolo[3,4-b]pyridin-4-yl)-2-(trifluoromethyl)phenoxy)-2,4-dimethylpentan-2-amine;
(S)-2-((2-amino-2,4-dimethylpentyl)oxy)-5-(2-methyl-3H-imidazo [4,5-b]pyridin-7-yl)benzonitrile;
(S)-2,4-dimethyl-1-(2-methyl-4-(2-methyl-3H-imidazo[4,5-b]pyridin-7-yl)phenoxy)pentan-2-amine;
(S)-1-(4-(2-(methoxymethyl)-3H-imidazo [4,5-b]pyridin-7-yl)-2-(trifluoromethyl)phenoxy)-2,4-dimethylpentan-2-amine;
(S)-1-(4-(2-(methoxymethyl)-3H-imidazo[4,5-b]pyridin-7-yl)-2-methylphenoxy)-2,4-dimethylpentan-2-amine;
(S)-2-((2-amino-2,4-dimethylpentyl)oxy)-5-(2-oxo-2,3-dihydro-1H-pyrrolo [2,3-b]pyridin-4-yl)benzonitrile;
(S)-4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-(trifluoromethyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-2(3H)-one
2-methyl-1-((2-methyl-6-(2-methylpyrimidin-4-yl)pyridin-3-yl)oxy)propan-2-amine;
(S)-1-((2-(difluoromethyl)-6-(pyrazolo[1,5-a]pyrimidin-7-yl)pyridin-3-yl)oxy)-2,4-dimethylpentan-2-amine;
(S)-1-(2-chloro-4-(pyrazolo [,5-a]pyridin-3-yl)phenoxy)-2,4-dimethylpentan-2-amine (S)-2,4-dimethyl-1-(2-methyl-4-(pyrazolo[1,5-a]pyridin-3-yl)phenoxy)pentan-2-amine 4-(4-(((S)-2-amino-2,4-dimethylpentyl)oxy)-3-chlorophenyl)-N-(3-fluorocyclopentyl)pyridin-2-amine;
(S)-1-(2-fluoro-4-(2-(trifluoromethyl) pyrazolo[1,5-a]pyrimidin-7-yl)phenoxy)-2,4-dimethylpentan-2-amine;
(S)-1-(2-chloro-4-(2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-7-yl)phenoxy)-2,4-dimethylpentan-2-amine
4-(4-(((S)-2-amino-2,4-dimethylpentyl)oxy)-3-chlorophenyl)-N-(tetrahydro-2H-pyran-3-yl)pyridin-2-amine
4-(4-(((S)-2-amino-2,4-dimethylpentyl)oxy)-3-chlorophenyl)-N-(tetrahydro-2H-pyran-3-yl)pyridin-2-amine
4-(4-(((S)-2-amino-2,4-dimethylpentyl)oxy)-3-chlorophenyl)-N-(tetrahydro-2H-pyran-3-yl)pyridin-2-amine;
(S)-2,4-dimethyl-1-((7-(pyrazolo[1,5-a]pyrimidin-7-yl)benzo [d]thiazol-4-yl)oxy)pentan-2-amine;
(S)-2,4-dimethyl-1-((7-(2-methylpyrimidin-4-yl)benzo [d]thiazol-4-yl)oxy)pentan-2-amine
4-(4-(((S)-2-amino-2,4-dimethylpentyl)oxy)-3-chlorophenyl)-N-(tetrahydrofuran-3-yl)pyridin-2-amine
4-(4-(((S)-2-amino-2,4-dimethylpentyl)oxy)-3-methylphenyl)-N-(tetrahydrofuran-3-yl)pyridin-2-amine
1-(((3-methyl-5-(2-methylpyrimidin-4-yl)pyridin-2-yl)oxy)methyl)cyclobutanamine;
(S)-1-(2-(difluoromethyl)-4-(pyrazolo[1,5-a]pyrimidin-7-yl)phenoxy)-2,4-dimethylpentan-2-amine;
(S)-1-(2-(fluoromethyl)-4-(pyrazolo[1,5-a]pyrimidin-7-yl)phenoxy)-2,4-dimethylpentan-2amine;
(S)-2,4-dimethyl-1-(5-methyl-2-(pyridin-4-yl)thiazol-4-yloxy)pentan-2-amine
6-(4-(((S)-2-amino-2,4-dimethylpentyl)oxy)-3-(trifluoromethyl)phenyl)-N-(tetrahydro-2H-pyran-3-yl)pyrimidin-4-amine;
(S)-1-(2-chloro-4-(7H-pyrrolo [2,3-d]pyrimidin-4-yl)phenoxy)-2,4-dimethylpentan-2-amine;
(S)-2-((2-amino-2,4-dimethylpentyl)oxy)-5-(7H-pyrrolo [2,3-d]pyrimidin-4-yl)benzonitrile;
(S)-1-(4-(7H-pyrrolo [2,3-d]pyrimidin-4-yl)-2-(trifluoromethyl)phenoxy)-2,4-dimethylpentan-2-amine;
(S)-2-((2-amino-2,4-dimethylpentyl)oxy)-5-(7-methyl-7H-pyrrolo [2,3-d]pyrimidin-4-yl)benzonitrile;
(S)-1-(2-fluoro-4-(7-methyl-7H-pyrrolo [2,3-d]pyrimidin-4-yl)phenoxy)-2,4-dimethylpentan-2-amine;
(S)-2,4-dimethyl-1-(4-(7-methyl-7H-pyrrolo [2,3-d]pyrimidin-4-yl)-2-(trifluoromethyl)phenoxy)pentan-2-amine;
(S)—N-(4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-methylphenyl)pyrimidin-2-yl)thiazol-2-amine;
(S)-4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-methylphenyl)-N-cyclopropylpyrimidin-2-amine;
(S)—N-(4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-(trifluoromethyl)phenyl)pyrimidin-2-yl)thiazol-2-amine;
(S)—N-(4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-(trifluoromethyl)phenyl)pyrimidin-2-yl)-4-methylthiazol-2-amine;
(S)-4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-(trifluoromethyl)phenyl)-N-cyclopentylpyrimidin-2-amine;
(S)-2-((2-amino-2,4-dimethylpentyl)oxy)-5-(2-((4-methylthiazol-2-yl)amino)pyrimidin-4-yl)benzonitrile;
(S)—N-(4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-methylphenyl)pyrimidin-2-yl)-4-methylthiazol-2-
(S)—N-(4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-(trifluoromethyl)phenyl)pyridin-2-yl)cyclopropanecarboxamide;
(S)—N-(4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-(trifluoromethyl)phenyl)pyridin-2-yl)cyclobutanecarboxamide
(S)—N-(4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-(trifluoromethyl)phenyl)pyridin-2-yl)cyclopentanecarboxamide
(S)—N-(4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-(trifluoromethyl)phenyl)pyridin-2-yl)-2-cyclopentylacetamide;
(S)—N-(4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-(trifluoromethyl)phenyl)pyridin-2-yl)-3-cyclopentylpropanamide;
(S)—N-(4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-(trifluoromethyl)phenyl)pyridin-2-yl)-2-cyclohexylacetamide
N-(4-(4-(((S)-2-amino-2,4-dimethylpentyl)oxy)-3-(trifluoromethyl)phenyl)pyridin-2-yl)tetrahydrofuran-2-carboxamide;
(S)—N-(4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-(trifluoromethyl)phenyl)pyridin-2-yl)-2-cycloheptylacetamide
(S)—N-(4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-(trifluoromethyl)phenyl)pyridin-2-yl)furan-2-carboxamide
(S)—N-(4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-(trifluoromethyl)phenyl)pyridin-2-yl)-5-bromofuran-2-carboxamide;
(S)-2-acetamido-N-(4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-(trifluoromethyl)phenyl)pyridin-2-yl)acetamide;
(S)—N-(4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-(trifluoromethyl)phenyl)pyridin-2-yl)thiophene-2-carboxamide;
(S)—N-(4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-(trifluoromethyl)phenyl)pyridin-2-yl)pyrazine-2-carboxamide;
(S)—N-(4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-(trifluoromethyl)phenyl)pyridin-2-yl)-2-methylnicotinamide;
(S)—N-(4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-(trifluoromethyl)phenyl)pyridin-2-yl)-1H-1,2,3-triazole-5-carboxamide
(S)—N-(4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-(trifluoromethyl)phenyl)pyridin-2-yl)-6-oxo-1,4,5,6-tetrahydropyridazine-3-carboxamide
(S)—N-(4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-(trifluoromethyl)phenyl)pyridin-2-yl)-5-methylisoxazole-3-carboxamide
(S)—N-(4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-(trifluoromethyl)phenyl)pyridin-2-yl)-5-isopropyl-1H-pyrazole-3-carboxamide
(S)-4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-(trifluoromethyl)phenyl)-N-(pyridin-3-ylmethyl)pyridin-2-amine;
(S)-4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-(trifluoromethyl)phenyl)-N-(furan-2-ylmethyl)pyridin-2-amine;
(S)-4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-(trifluoromethyl)phenyl)-N-(benzo[d][1,3]dioxol-5-yl)pyridin-2-amine;
(S)-4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-fluorophenyl)-6-methyl-6,7-dihydro-5H-pyrrolo [3,4-b]pyridin-5-one;
(S)-2-((2-amino-2,4-dimethylpentyl)oxy)-5-(6-methyl-5-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-4-yl)benzonitrile;
(S)-2-((2-amino-2,4-dimethylpentyl)oxy)-5-(5-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-4-yl)benzonitrile;
(S)-4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-fluorophenyl)-6,7-dihydro-5H-pyrrolo [3,4-b]pyridin-5-one;
(S)-4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-chlorophenyl)-6,7-dihydro-5H-pyrrolo [3,4-b]pyridin-5-one;
(S)-4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-(trifluoromethyl)phenyl)-6-ethyl-6,7-dihydro-5H-pyrrolo [3,4-b]pyridin-5-one;
(S)-4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-fluorophenyl)-6-ethyl-6,7-dihydro-5H-pyrrolo [3,4-b]pyridin-5-one;
(S)-1-(2-fluoro-4-(1H-pyrrolo[3,2-b]pyridin-7-yl)phenoxy)-2,4-dimethylpentan-2-amine;
(S)-2-((2-amino-2,4-dimethylpentyl)oxy)-5-(1H-pyrrolo[3,2-b]pyridin-7-yl)benzonitrile;
(S)-2-((2-amino-2,4-dimethylpentyl)oxy)-5-(1-methyl-1H-pyrrolo[3,2-b]pyridin-7-yl)benzonitrile;
(S)-1-(4-(1H-pyrrolo[3,2-b]pyridin-7-yl)-2-(trifluoromethyl)phenoxy)-2,4-dimethylpentan-2-amine;
(S)-4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-(trifluoromethyl)phenyl)-6,7-dihydro-5H-pyrrolo [3,4-b]pyridin-5-one;
(S)-4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-(trifluoromethyl)phenyl)-6-methyl-6,7-dihydro-5H-pyrrolo [3,4-b]pyridin-5-one;
(S)-2,4-dimethyl-1-(2-methyl-4-(1-methyl-1H-pyrrolo[3,2-b]pyridin-7-yl)phenoxy)pentan-2-amine;
(S)-4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-methylphenyl)-6,7-dihydro-5H-pyrrolo [3,4-b]pyridin-5-one;
(S)-4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-chlorophenyl)-6-methyl-6,7-dihydro-5H-pyrrolo [3,4-b]pyridin-5-one;
(S)-4-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-methylphenyl)-6-methyl-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one
6-(4-(((S)-2-amino-2,4-dimethylpentyl)oxy)-3-(trifluoromethyl)phenyl)-N-(tetrahydrofuran-3-yl)pyrimidin-4-amine
6-(6-(((S)-2-amino-2,4-dimethylpentyl)oxy)-5-chloropyridin-3-yl)-N-(tetrahydrofuran-3-yl)pyrimidin-4-amine;
(S)-2,4-dimethyl-1-((2-methyl-6-(2-methylimidazo [1,2-b]pyridazin-8-yl)pyridin-3-yl)oxy)pentan-2-amine;
(S)-1-((2-(difluoromethyl)-6-(2-methylimidazo[1,2-b]pyridazin-8-yl)pyridin-3-yl)oxy)-2,4-dimethylpentan-2-amine;
(S)-7-(4-((2-amino-2,4-dimethylpentyl)oxy)-2-fluorophenyl)pyrazolo[1,5-a]pyrimidin-5-amine;
(S)-1-(2-chloro-4-(pyrazolo [1,5-a]pyrimidin-7-yl)phenoxy)-2,4-dimethylpentan-2-amine;
(S)-7-(4-((2-amino-2,4-dimethylpentyl) oxy)-3-fluorophenyl)pyrazolo[1,5-a]pyrimidin-5-amine;
(S)-1-(2-chloro-4-(2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-yl)phenoxy)-2,4-dimethylpentan-2-amine;
(S)-2-((2-amino-2,4-dimethylpentyl)oxy)-5-(pyrazolo[1,5-a]pyrimidin-7-yl)benzonitrile;
(S)-1-(2-fluoro-4-(pyrazolo [1,5-a]pyrimidin-7-yl)phenoxy)-2,4-dimethylpentan-2-amine;
(S)—N-(7-(4-((2-amino-2,4-dimethylpentyl) oxy)-3-fluorophenyl) pyrazolo [1,5-a]pyrimidin-5-yl) acetamide;
(S)-2-((2-amino-2,4-dimethylpentyl)oxy)-5-(2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-yl)benzonitrile;
(S)-2-(2-amino-2,4-dimethylpentyloxy)-5-(2-(piperidin-4-ylamino) pyridin-4-yl) benzonitrile;
(S)-2,4-dimethyl-1-(4-(pyrazolo[1,5-a]pyrimidin-7-yl)-2-(trifluoromethyl)phenoxy)pentan-2-amine;
(S)-2-(2-amino-2,4-dimethylpentyloxy)-5-(2-(tetrahydro-2H-pyran-4-ylamino)pyridin-4yl)benzonitrile;
(S)-4-(4-(2-amino-2,4-dimethylpentyloxy)-3-(trifluoromethyl)phenyl)-N-(piperidin-4-yl)pyridin-2-amine;
(S)-1-(4-(6,7-difluoroquinazolin-4-yl)-2-(trifluoromethyl)phenoxy)-2,4-dimethylpentan-2-amine;
(S)-2,4-dimethyl-1-(2-methyl-4-(pyrazolo [1,5-a]pyrimidin-7-yl)phenoxy)pentan-2-amine;
(S)-2,4-dimethyl-1-(4-(pyrazolo[1,5-a]pyrimidin-3-yl)-2-(trifluoromethyl)phenoxy)pentan-2-amine
4-(4-((5)-2-amino-2,4-dimethylpentyloxy)-3-(trifluoromethyl)phenyl)-N-(tetrahydro-2H-pyran-3-yl)pyridin-2-amine
4-(4-(((5)-2-amino-2,4-dimethylpentyl)oxy)-3-(trifluoromethyl)phenyl)-N-(tetrahydro-2H-pyran-3-yl)pyridin-2-amine
4-(4-(((5)-2-amino-2,4-dimethylpentyl)oxy)-3-(trifluoromethyl)phenyl)-N-(tetrahydro-2H-pyran-3-yl)pyridin-2-amine;
(S)-3-(5-((2-amino-2,4-dimethylpentyl)oxy)-6-methylpyridin-2-yl)pyrazolo [1,5-a]pyrimidine-6-carbonitrile;
(S)-2,4-dimethyl-1-(4-(2-methylthieno [2,3-d]pyrimidin-4-yl)-2-(trifluoromethyl)phenoxy)pentan-2-amine;
(S)-1-(2-chloro-4-(2-cyclopropylpyrazolo [1,5-a]pyrimidin-7-yl)phenoxy)-2,4-dimethylpentan-2-amine;
(S)-1-(4-(2-Cyclopropylpyrazolo [1,5-a]pyrimidin-7-yl)-2-(trifluoromethyl)phenoxy)-2,4-dimethylpentan-2-amine;
(S)-2-((2-amino-2,4-dimethylpentyl)oxy)-5-(2-(trifluoromethyl)pyrazolo [1,5-a]pyrimidin-7-yl)benzonitrile;
(S)-5-((2-amino-2,4-dimethylpentyl)oxy)-2-(pyrazolo [1,5-a]pyrimidin-7-yl)isonicotinonitrile;
(S)-2,4-dimethyl-1-((2-methyl-6-(pyrazolo [1,5-a]pyrimidin-7-yl)pyridin-3-yl)oxy)pentan-2-amine;
(S)-1-(2,5-difluoro-4-(pyrazolo[1,5-a]pyrimidin-7-yl)phenoxy)-2,4-dimethylpentan-2-amine
1,1,1-trifluoro-4-methyl-2-(((2-methyl-6-(pyrazolo [1,5-a]pyrimidin-7-yl)pyridin-3-yl)oxy)methyl)pentan-2-amine;
(S)-2-((2-amino-2,4-dimethylpentyl)oxy)-5-(2-methylimidazo [1,2-b]pyridazin-8-yl)benzonitrile
(S)-1-(4-(2-cyclopropylimidazo [1,2-b]pyridazin-8-yl)-2-fluorophenoxy)-2,4-dimethylpentan-2-amine;
(S)-2-((2-amino-2,4-dimethylpentyl)oxy)-5-(6-chloro-2-cyclopropylimidazo[1,2-b]pyridazin-8-yl)benzonitrile;
(S)-1-(4-(6-chloro-2-methylimidazo [1,2-b]pyridazin-8-yl)-2-(trifluoromethyl)phenoxy)-2,4-dimethylpentan-2-amine;
(S)-1-(4-(6-chloro-2-cyclopropylimidazo [1,2-b]pyridazin-8-yl)-2-(trifluoromethyl)phenoxy)-2,4-dimethylpentan-2-amine;
(S)-1-(2-fluoro-4-(2-methylimidazo[1,2-b]pyridazin-8-yl)phenoxy)-2,4-dimethylpentan-2-amine;
(S)-2,4-dimethyl-1-(4-(2-methylimidazo [1,2-b]pyridazin-8-yl)-2-(trifluoromethyl)phenoxy)pentan-2-amine;
(S)-2-((2-amino-2,4-dimethylpentyl)oxy)-5-(2-cyclopropylimidazo[1,2-b]pyridazin-8-yl)benzonitrile;
(S)-2,4-dimethyl-1-(2-methyl-4-(2-(trifluoromethyl)imidazo [1,2-b]pyridazin-8-yl)phenoxy)pentan-2-amine;
(S)-2,4-dimethyl-1-(4-(2-(trifluoromethyl)imidazo [1,2-b]pyridazin-8-yl)phenoxy)pentan-2-amine;
(S)-1-(4-(imidazo[1,2-b]pyridazin-3-yl)-2-methylphenoxy)-2,4-dimethylpentan-2-amine;
(S)-1-(2-chloro-4-(imidazo [1,2-b]pyridazin-3-yl)phenoxy)-2,4-dimethylpentan-2-amine;
(R)-2,4-dimethyl-1-((3-methyl-5-(2-(trifluoromethyl)imidazo[1,2-b]pyridazin-8-yl)pyridin-2-yl)oxy)pentan-2-amine;
and
(S)-6-(4-((2-amino-2,4-dimethylpentyl)oxy)-3-chlorophenyl)pyrimidin-4(3H)-one;
or a pharmaceutically acceptable salt thereof.

151 more elements

Dependencies are inferred from the claim text.

Facts

Application: 15/763,281Filed 29 Sep 2016
Priority: IN 3169/DEL/20151 Oct 2015
Published: US 2019/0040080 A17 Feb 2019
Granted: 2 Apr 2019
Term ends: Not estimatedThe source records don’t support an estimate.

Classification35 codes

C07D 513/04
In which the condensed system contains two hetero rings: ortho-condensed systems
A61K 31/44
Having six-membered rings with one nitrogen as the only ring hetero atom: non condensed pyridines; Hydrogenated derivatives thereof
A61K 31/4427
Non condensed pyridines; Hydrogenated derivatives thereof: containing further heterocyclic ring systems
A61K 31/50
Having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines: pyridazines; Hydrogenated…

Family

US 2019/0040080 A1Pre-grant publication · published 7 Feb 2019
US 10,246,469 B2This patent

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

Timeline

Citations

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