US 11,590,116 B2Granted

Substituted pyridines and methods of use

AssigneeTheravance Biopharma R&D IP, LLC

InventorsChristina Owens, Svitlana Kulyk, Steven D. E. Sullivan, Paul Allegretti, Mandy Loo, Jennifer Kozak, Erik Fenster, Adam D. Hughes

Life of this patent

Estimating the term…

Abstract

The present disclosure provides inhibitors of activin receptor-like kinase 5 (ALK5). Also disclosed are methods to modulate the activity of ALK5 and methods of treatment of disorders mediated by ALK5.

Claims25

Dependent claims

A compound of Formula (I-A):

or a pharmaceutically acceptable salt thereof, wherein:
W is CH;
R1 is R10;
L1 is absent;
or selected from C1-6 alkylene, C2-6 alkenylene, C2-6 alkynylene, C3-12 carbocycle, and 3- to 12-membered heterocycle, each of which is optionally substituted with one or more R10;
L2 is selected from absent, —O—, —S—, —N(R11)—, —C(O)—, —C(O)O—, —OC(O)—, —OC(O)O—, —C(O)N(R11)—, —C(O)N(R11)C(O)—, —C(O)N(R11)C(O)N(R11)—, —N(R11)C(O)—, —N(R11)C(O)N(R11)—, —N(R11)C(O)O—, —OC(O)N(R11)—, —C(NR11)—, —N(R11)C(NR11)—, —C(NR11)N(R11)—, —N(R11)C(NR11)N(R11)—, —S(O)2—, —OS(O)—, —S(O)O—, —S(O)—, —OS(O)2, —S(O)2O—, —N(R11)S(O)2—, —S(O)2N(R11)—, —N(R11)S(O)—, —S(O)N(R11)—, —N(R11)S(O)2N(R11)—, and —N(R11)S(O)N(R11)—;
R2 is R10;
R10 is independently selected at each occurrence from:
halogen, —NO2, —CN, —OR12, —SR12, —N(R12)2, —NR13R14, —S(═O)R12, —S(═O)2R12, —S(═O)2N(R12)2, —S(═O)2NR13R14, —NR12S(═O)2R12, —NR12S(═O)2N(R12)2, —NR12S(═O)2NR13R14, —C(O)R12, —C(O)OR12, —OC(O)R12, —OC(O)OR12, —OC(O)N(R12)2, —OC(O)NR13R14, —NR12C(O)R12, —NR12C(O)OR12, —NR12C(O)N(R12)2, —NR12C(O)NR13R14, —C(O)N(R12)2, —C(O)NR13R14, —P(O)(OR12)2, —P(O)(R12)2, ═O, ═S, ═N(R12);
C1-10 alkyl, C2-10 alkenyl, and C2-10 alkynyl, each of which is independently optionally substituted at each occurrence with one or more substituents selected from halogen, —NO2, —CN, —OR12, —SR12, —N(R12)2, —NR13R14, —S(═O)R12, —S(═O)2R12, —S(═O)2N(R12)2, —S(═O)2NR13R14, —NR12S(═O)2R12, —NR12S(═O)2N(R12)2, —NR12S(═O)2NR13R14, —C(O)R12, —C(O)OR12, —OC(O)R12, —OC(O)OR12, —OC(O)N(R12)2, —OC(O)NR13R14, —NR12C(O)R12, —NR12C(O)OR12, —NR12C(O)N(R12)2, —NR12C(O)NR13R14, —C(O)N(R12)2, —C(O)NR13R14, —P(O)(OR12)2, —P(O)(R12)2, ═O, ═S, ═N(R12), C3-12 carbocycle, and 3- to 12-membered heterocycle;
and
C3-12 carbocycle and 3- to 12-membered heterocycle,
wherein each C3-12 carbocycle and 3- to 12-membered heterocycle in R10 is independently optionally substituted with one or more substituents selected from halogen, —NO2, —CN, —OR12, —SR12, —N(R12)2, —NR13R14, —S(═O)R12, —S(═O)2R12, —S(═O)2N(R12)2, —S(═O)2NR13R14, —NR12S(═O)2R12, —NR12S(═O)2N(R12)2, —NR12S(═O)2NR13R14, —C(O)R12, —C(O)OR12, —OC(O)R12, —OC(O)OR12, —OC(O)N(R12)2, —OC(O)NR13R14, —NR12C(O)R12, —NR12C(O)OR12, —NR12C(O)N(R12)2, —NR12C(O)NR13R14, —C(O)N(R12)2, —C(O)NR13R14, —P(O)(OR12)2, —P(O)(R12)2, ═O, ═S, ═N(R12), R12, C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl, and C2-6 alkynyl;
R11 is independently selected at each occurrence from:
hydrogen, —C(O)R12, —C(O)OR12, —C(O)N(R12)2, —C(O)NR13R14;
C1-6 alkyl, C2-6 alkenyl, and C2-6 alkynyl, each of which is independently optionally substituted at each occurrence with one or more substituents selected from halogen, —NO2, —CN, —OR12, —SR12, —N(R12)2, —NR13R14, —S(═O)R12, —S(═O)2R12, —S(═O)2N(R12)2, —S(═O)2NR13R14, —NR12S(═O)2R12, —NR12S(═O)2N(R12)2, —NR12S(═O)2NR13R14, —C(O)R12, —C(O)OR12, —OC(O)R12, —OC(O)OR12, —OC(O)N(R12)2, —OC(O)NR13R14, —NR12C(O)R12, —NR12C(O)OR12, —NR12C(O)N(R12)2, —NR12C(O)NR13R14, —C(O)N(R12)2, —C(O)NR13R14, —P(O)(OR12)2, —P(O)(R12)2, ═O, ═S, ═N(R12), C3-12 carbocycle, and 3- to 12-membered heterocycle;
and
C3-12 carbocycle and 3- to 12-membered heterocycle,
wherein each C3-12 carbocycle and 3- to 12-membered heterocycle in R11 is independently optionally substituted with one or more substituents selected from halogen, —NO2, —CN, —OR12, —SR12, —N(R12)2, —NR13R14, —S(═O)R12, —S(═O)2R12, —S(═O)2N(R12)2, —S(═O)2NR13R14, —NR12S(═O)2R12, —NR12S(═O)2N(R12)2, —NR12S(═O)2NR13R14, —C(O)R12, —C(O)OR12, —OC(O)R12, —OC(O)OR12, —OC(O)N(R12)2, —OC(O)NR13R14, —NR12C(O)R12, —NR12C(O)OR12, —NR12C(O)N(R12)2, —NR12C(O)NR13R14, —C(O)N(R12)2, —C(O)NR13R14, —P(O)(OR12)2, —P(O)(R12)2, ═O, ═S, ═N(R12), R12, C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl, and C2-6 alkynyl;
R12 is independently selected at each occurrence from hydrogen;
and C1-10 alkyl, C2-10 alkenyl, C2-10 alkynyl, 1- to 6-membered heteroalkyl, C3-12 carbocycle, and 3- to 12-membered heterocycle, each of which is optionally substituted by halogen, —CN, —NO2, —NH2, —NHCH3, —NHCH2CH3, ═O, —OH, —OCH3, —OCH2CH3, —CH3, —CH2CH3, —CH(CH3)2, —C(CH3)3, C3-12 carbocycle, or 3- to 6-membered heterocycle;
and
R13 and R14 are taken together with the nitrogen atom to which they are attached to form a heterocycle, optionally substituted with one or more R12.

20 more elements

A compound selected from:

N-(azetidin-3-ylmethyl)-N-methyl-6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinolin-3-amine;
3-[(2R,6R)-2,6-dimethyl-1,2,3,6-tetrahydropyridin-4-yl]-6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline;
N-(azetidin-3-ylmethyl)-6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinolin-3-amine;
(3R)-1-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyrrolidin-3-amine;
3-(1-methyl-2,5-dihydropyrrol-3-yl)-6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline;
N-methyl-2-[4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyrazol-1-yl]ethanamine;
isopropyl 2-[4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]piperazin-2-yl]acetate;
N-[4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]cyclohex-3-en-1-yl]acetamide;
6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-N-(2-pyrrolidin-1-ylethyl)quinolin-3-amine;
azetidin-3-ylmethyl 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]cyclohex-3-ene-1-carboxylate;
N-[2-[(3R)-3-(methoxymethyl)piperazin-1-yl]ethyl]-6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinolin-3-amine;
[(3R)-pyrrolidin-3-yl] 1-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]piperidine-4-carboxylate;
[(3R)-pyrrolidin-3-yl] 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]cyclohex-3-ene-1-carboxylate;
N-(azetidin-3-yl)-6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinolin-3-amine;
N-[2-(2,2-dimethylpyrrolidin-1-yl)ethyl]-6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinolin-3-amine;
methyl 2-[4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]piperazin-2-yl]acetate;
[1-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]azetidin-3-yl]methanamine;
3-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]-5,6,7,8-tetrahydro-1,6-naphthyridine;
(1R)-4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]cyclohex-3-en-1-amine;
N-[4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]cyclohex-3-en-1-yl]-2-(2-oxotetrahydrofuran-3-yl)sulfanyl-acetamide;
4-piperidyl 5-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyridine-2-carboxylate;
N-[2-(azetidin-3-yl)ethyl]-6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinolin-3-amine;
6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-N-(2-piperazin-1-ylethyl)quinolin-3-amine;
N-(7-isopropyl-6,8-dihydro-5H-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)-6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinolin-3-amine;
3-(2,6-diazaspiro[3.3]heptan-2-yl)-6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline;
3-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]cyclohex-2-en-1-amine;
3-(cyclohexen-1-yl)-6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline;
3-[(3R,5S)-3,5-dimethylpiperazin-1-yl]-6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline;
[(3R)-1-methylpyrrolidin-3-yl] 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]benzoate;
3-(2,8-diazaspiro[3.5]nonan-2-yl)-6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline;
2-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]-2,8-diazaspiro[4.5]decane;
5-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]indan-2-amine;
ethyl 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]cyclohex-3-ene-1-carboxylate;
(1S)-4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]cyclohex-3-en-1-amine;
3-(2,7-diazaspiro[3.5]nonan-2-yl)-6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline;
6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-N-pyrrolidin-3-yl-quinolin-3-amine;
rac-(1R,2R)-2-[3-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyrazol-1-yl]cyclohexanamine;
4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]cyclohex-3-en-1-amine;
azetidin-3-yl 3-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]benzoate;
3-(2,7-diazaspiro[3.5]nonan-7-yl)-6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline;
(3S)-1-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyrrolidin-3-amine;
6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-N-[2-(3-piperidyl)ethyl]quinolin-3-amine;
4-piperidyl 3-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]benzoate;
3-[2-[[1-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyrrolidin-3-yl]amino]ethylsulfanyl]tetrahydrofuran-2-one;
azetidin-3-ylmethyl 3-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]benzoate;
3-(1-benzyl-2,5-dihydropyrrol-3-yl)-6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline;
N-benzyl-4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]cyclohex-3-en-1-amine;
6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-[1-(piperazin-1-ylmethyl)vinyl]quinoline;
6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-(1,2,3,6-tetrahydropyridin-5-yl)quinoline;
[(3R)-1-methylpyrrolidin-3-yl] 5-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyridine-2-carboxylate;
5-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]indan-1-amine;
6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-(1,2,3,4-tetrahydroisoquinolin-6-yl)quinoline;
3-(2-azaspiro[3.5]non-6-en-7-yl)-6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline;
4-piperidyl 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]benzoate;
N-[2-[(3R,5S)-3,5-dimethylpiperazin-1-yl]ethyl]-6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinolin-3-amine;
3-(1-isopropyl-2,5-dihydropyrrol-3-yl)-6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline;
N-methyl-1-[5-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]-3-pyridyl]methanamine;
N-[5-(4-isopropylpiperazin-1-yl)-2-pyridyl]-6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinolin-3-amine;
6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-(2-pyridyl)quinoline;
N-[(1S)-4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]cyclohex-3-en-1-yl]acetamide;
3-(2,7-diazaspiro[4.4]nonan-2-yl)-6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline;
9-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]-3-azaspiro[5.5]undec-9-ene;
[(3R)-1-methylpyrrolidin-3-yl] 5-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyridine-3-carboxylate;
1-[3-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]phenyl]azetidin-3-amine;
6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-[1-(3-piperidyl)pyrazol-4-yl]quinoline;
6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-piperazin-1-yl-quinoline;
(2S)—N-[(1R)-4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]cyclohex-3-en-1-yl]pyrrolidine-2-carboxamide;
3-(2,5-dihydro-1H-pyrrol-3-yl)-6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline;
6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-(1H-pyrazol-4-yl)quinoline;
4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]cyclohex-3-en-1-ol;
3-[1-(azetidin-3-yl)pyrazol-4-yl]-6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline;
1-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]piperidin-4-amine;
N-[5-(4-methylpiperazin-1-yl)-2-pyridyl]-6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinolin-3-amine;
3-(6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-3-yl)-6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline;
4-piperidyl 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]cyclohex-3-ene-1-carboxylate;
(1R,2R)-2-[4-[6-[4-(6-methyl-2-pyridyl)-1H-imidazol-5-yl]-3-quinolyl]pyrazol-1-yl]cyclohexanamine;
6-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]-N-(4-piperidyl)pyridin-2-amine;
3-[(2R,6S)-2,6-dimethyl-1,2,3,6-tetrahydropyridin-4-yl]-6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline;
3-[[[4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]cyclohex-3-en-1-yl]amino]methyl]tetrahydrofuran-2-one;
1-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]azetidin-3-amine;
4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]cyclohex-3-ene-1-carboxylic acid;
N-[2-(4-isopropylpiperazin-1-yl)ethyl]-6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinolin-3-amine;
6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-(1,2,3,6-tetrahydropyridin-4-yl)quinoline;
N-[2-(3-aminoazetidin-1-yl)ethyl]-6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinolin-3-amine;
N-methyl-2-[3-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyrazol-1-yl]ethanamine;
6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-N-[2-(4-piperidyl)ethyl]quinolin-3-amine;
[(3S)-1-methylpyrrolidin-3-yl] 3-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]benzoate;
3-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]cyclohex-3-en-1-amine;
N-isopropyl-4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]cyclohex-3-en-1-amine;
[(3S)-1-methylpyrrolidin-3-yl] 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]benzoate;
2-[4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyrazol-1-yl]ethanamine;
6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-(3-piperazin-1-ylphenyl)quinoline;
5-[[[4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]cyclohex-3-en-1-yl]amino]methyl]tetrahydrofuran-2-one;
6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinolin-3-amine;
[(3R)-1-methylpyrrolidin-3-yl] 3-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]benzoate;
6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-(1,2,3,4-tetrahydroisoquinolin-7-yl)quinoline;
N-methyl-1-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]azetidin-3-amine;
azetidin-3-yl 5-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyridine-2-carboxylate;
2-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]-2-azaspiro[3.3]heptan-6-amine;
N,N-dimethyl-4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]cyclohex-3-en-1-amine;
3-isoindolin-4-yl-6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline;
N,N-dimethyl-1-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]azetidin-3-amine;
azetidin-3-ylmethyl 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]benzoate;
(1S,2S)-2-[4-[6-[4-(6-methyl-2-pyridyl)-1H-imidazol-5-yl]-3-quinolyl]pyrazol-1-yl]cyclohexanamine;
azetidin-3-yl 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]benzoate;
N-[3-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]phenyl]piperidin-4-amine;
isobutyl 2-[4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]piperazin-2-yl]acetate;
N-[(1R)-4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]cyclohex-3-en-1-yl]acetamide;
3-isoindolin-5-yl-6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline;
azetidin-3-ylmethyl 6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline-3-carboxylate;
[(3R)-1-methylpyrrolidin-3-yl] 1-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]piperidine-4-carboxylate;
N-[2-(2,8-diazaspiro[4.5]decan-2-yl)ethyl]-6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinolin-3-amine;
[(3S)-1-methylpyrrolidin-3-yl] 5-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyridine-3-carboxylate;
methyl (2R)-1-[2-[[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]amino]ethyl]piperidine-2-carboxylate;
[(3S)-pyrrolidin-3-yl] 3-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]benzoate;
N-[2-(2,6-diazaspiro[3.3]heptan-2-yl)ethyl]-6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinolin-3-amine;
[(3R)-1-methylpyrrolidin-3-yl] 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]cyclohex-3-ene-1-carboxylate;
4-pyrrolidin-1-ylbutyl 6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline-3-carboxylate;
[(3R)-pyrrolidin-3-yl] 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]benzoate;
methyl (2S)-4-[2-[[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]amino]ethyl]piperazine-2-carboxylate;
[(3S)-pyrrolidin-3-yl] 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]benzoate;
3-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]-5,6,7,8-tetrahydro-1,7-naphthyridine;
[(3S)-1-methylpyrrolidin-3-yl] 5-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyridine-2-carboxylate;
[(3R)-pyrrolidin-3-yl] 5-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyridine-3-carboxylate;
6-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]indan-1-amine;
2-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]-4,5,6,7-tetrahydrothiazolo[4,5-c]pyridine;
methyl (3R)-1-[2-[[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]amino]ethyl]piperidine-3-carboxylate;
methyl (3R)-1-[2-[[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]amino]ethyl]pyrrolidine-3-carboxylate;
N-[2-[(3R)-3-amino-1-piperidyl]ethyl]-6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinolin-3-amine;
methyl 6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline-3-carboxylate;
3-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]-6,7-dihydro-5H-cyclopenta[b]pyridin-7-amine;
[(3R)-pyrrolidin-3-yl] 3-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]benzoate;
3-pyrrolidin-1-ylpropyl 6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline-3-carboxylate;
azetidin-3-yl 6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline-3-carboxylate;
4-piperidyl 6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline-3-carboxylate;
4-piperidylmethyl 6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline-3-carboxylate;
4-piperidyl 2-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiazole-4-carboxylate;
[(3R)-pyrrolidin-3-yl] 2-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiazole-4-carboxylate;
[(3R)-1-methylpyrrolidin-3-yl] 2-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiazole-4-carboxylate;
azetidin-3-yl 2-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiazole-4-carboxylate;
azetidin-3-ylmethyl 2-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiazole-4-carboxylate;
[(3S)-1-methylpyrrolidin-3-yl] 2-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiazole-4-carboxylate;
[(3S)-pyrrolidin-3-yl] 2-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiazole-4-carboxylate;
[(3R)-pyrrolidin-3-yl] 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiophene-2-carboxylate;
[(3R)-1-methylpyrrolidin-3-yl] 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiophene-2-carboxylate;
4-piperidyl 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiophene-2-carboxylate;
azetidin-3-yl 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiophene-2-carboxylate;
azetidin-3-ylmethyl 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiophene-2-carboxylate;
[(3S)-pyrrolidin-3-yl] 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiophene-2-carboxylate;
[(3S)-1-methylpyrrolidin-3-yl] 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiophene-2-carboxylate;
2-piperazin-1-ylethyl 6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline-3-carboxylate;
(3-aminocyclobutyl) 6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline-3-carboxylate;
(4-aminocyclohexyl) 6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline-3-carboxylate;
(4-aminocyclohexyl)methyl 6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline-3-carboxylate;
[rac-(1R,3R)-3-aminocyclopentyl] 6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline-3-carboxylate;
[rac-(1R,3 S)-3-aminocyclohexyl]methyl 6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline-3-carboxylate;
(4-amino-4-methyl-cyclohexyl) 6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline-3-carboxylate;
[rac-(1S,3S)-3-aminocyclohexyl]methyl 6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline-3-carboxylate;
(4-aminocyclohexyl)methyl 6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline-3-carboxylate;
(4-amino-4-methyl-cyclohexyl) 6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline-3-carboxylate;
[(3S)-3-piperidyl]methyl 6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline-3-carboxylate;
azepan-3-yl 6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline-3-carboxylate;
(2S)—N-[(1S)-4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]cyclohex-3-en-1-yl]pyrrolidine-2-carboxamide;
(2R)—N-[(1R)-4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]cyclohex-3-en-1-yl]pyrrolidine-2-carboxamide;
(2R)—N-[(1S)-4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]cyclohex-3-en-1-yl]pyrrolidine-2-carboxamide;
[4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]-3,6-dihydro-2H-pyridin-1-yl]-(4-piperidyl)methanone;
[4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]-3,6-dihydro-2H-pyridin-1-yl]-[(2S)-pyrrolidin-2-yl]methanone;
(3-aminocyclobutyl) 6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline-3-carboxylate;
(R)-piperidin-3-ylmethyl 6-(5-(6-methylpyridin-2-yl)-1H-imidazol-4-yl)quinoline-3-carboxylate;
(S)-piperidin-3-yl 6-(5-(6-methylpyridin-2-yl)-1H-imidazol-4-yl)quinoline-3-carboxylate;
[(3S)-pyrrolidin-3-yl] 5-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiophene-3-carboxylate;
2-((3S,5R)-3,5-dimethylpiperazin-1-yl)ethyl 6-(5-(6-methylpyridin-2-yl)-1H-imidazol-4-yl)quinoline-3-carboxylate;
2-(piperidin-1-yl)ethyl 6-(5-(6-methylpyridin-2-yl)-1H-imidazol-4-yl)quinoline-3-carboxylate;
3-(piperazin-1-yl)propyl 6-(5-(6-methylpyridin-2-yl)-1H-imidazol-4-yl)quinoline-3-carboxylate;
3-((3S,5R)-3,5-dimethylpiperazin-1-yl)propyl 6-(5-(6-methylpyridin-2-yl)-1H-imidazol-4-yl)quinoline-3-carboxylate;
azetidin-3-yl 5-(6-(5-(6-methylpyridin-2-yl)-1H-imidazol-4-yl)quinolin-3-yl)thiophene-2-carboxylate;
azetidin-3-ylmethyl 5-(6-(5-(6-methylpyridin-2-yl)-1H-imidazol-4-yl)quinolin-3-yl)thiophene-2-carboxylate;
(S)-1-methylpyrrolidin-3-yl 5-(6-(5-(6-methylpyridin-2-yl)-1H-imidazol-4-yl)quinolin-3-yl)thiophene-2-carboxylate;
(R)-1-methylpyrrolidin-3-yl 5-(6-(5-(6-methylpyridin-2-yl)-1H-imidazol-4-yl)quinolin-3-yl)thiophene-2-carboxylate;
piperidin-4-yl 5-(6-(5-(6-methylpyridin-2-yl)-1H-imidazol-4-yl)quinolin-3-yl)thiophene-2-carboxylate;
azetidin-3-yl 2-(6-(5-(6-methylpyridin-2-yl)-1H-imidazol-4-yl)quinolin-3-yl)thiazole-5-carboxylate;
[(3S)-pyrrolidin-3-yl] 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiazole-2-carboxylate;
2-piperazin-1-ylethyl 6-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyridine-3-carboxylate;
6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-[6-(piperazin-1-ylmethyl)-3-pyridyl]quinoline;
azetidin-3-yl 6-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyridine-3-carboxylate;
5-[[(3S,5R)-3,5-dimethylpiperazin-1-yl]methyl]-2-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiazole;
4-(2,5-dihydro-1H-pyrrol-3-yl)-2-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiazole;
6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-[6-[[rac-(3 S,5R)-3,5-dimethylpiperazin-1-yl]methyl]-3-pyridyl]quinoline;
azetidin-3-yl 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiazole-2-carboxylate;
2-(4-piperidyl)ethyl 6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline-3-carboxylate;
2-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]-4-(1,2,3,6-tetrahydropyridin-4-yl)thiazole;
2-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]-5-(piperazin-1-ylmethyl)thiazole;
(1S)-5-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]indan-1-amine;
azetidin-3-yl 5-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiophene-3-carboxylate;
[(3S)-pyrrolidin-3-yl] 2-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyridine-4-carboxylate;
4-piperidyl 6-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyridine-2-carboxylate;
azetidin-3-yl 2-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyrimidine-5-carboxylate;
2-(3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-2-yl)ethyl 6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline-3-carboxylate;
2-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine;
azetidin-3-ylmethyl 5-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiophene-3-carboxylate;
azetidin-3-yl 2-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyridine-4-carboxylate;
[(3R)-pyrrolidin-3-yl] 2-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyrimidine-5-carboxylate;
2-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]-5-(1,2,3,6-tetrahydropyridin-4-yl)thiazole;
[(3R)-pyrrolidin-3-yl] 2-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyridine-4-carboxylate;
2-piperazin-1-ylethyl 5-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiophene-2-carboxylate;
[(3S)-pyrrolidin-3-yl] 6-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyridine-2-carboxylate;
4-piperidyl 6-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyridine-3-carboxylate;
2-piperazin-1-ylethyl 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiazole-2-carboxylate;
6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-(6-piperazin-1-yl-2-pyridyl)quinoline;
4-piperidyl 2-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyrimidine-5-carboxylate;
azetidin-3-ylmethyl 6-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyridine-3-carboxylate;
[(3R)-pyrrolidin-3-yl] 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiazole-2-carboxylate;
[(3R)-pyrrolidin-3-yl] 5-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiophene-3-carboxylate;
3-[5-[[(3 S,5R)-3,5-dimethylpiperazin-1-yl]methyl]-3-pyridyl]-6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline;
[(3R)-pyrrolidin-3-yl] 6-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyridine-3-carboxylate;
4-piperidyl 2-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyridine-4-carboxylate;
6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-[5-(piperazin-1-ylmethyl)-3-pyridyl]quinoline;
5-(2,5-dihydro-1H-pyrrol-3-yl)-2-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiazole;
[(3S)-pyrrolidin-3-yl] 6-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyridine-3-carboxylate;
2-piperazin-1-ylethyl 2-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyridine-4-carboxylate;
2-piperazin-1-ylethyl 2-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyrimidine-5-carboxylate;
[(3R)-pyrrolidin-3-yl] 6-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyridine-2-carboxylate;
azetidin-3-yl 6-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyridine-2-carboxylate;
[4-(methylamino)cyclohexyl] 6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline-3-carboxylate;
3-(4-piperidyl)propyl 6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline-3-carboxylate;
4-piperidyl 5-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiophene-3-carboxylate;
2-piperazin-1-ylethyl 5-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiophene-3-carboxylate;
azetidin-3-ylmethyl 2-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyrimidine-5-carboxylate;
2-piperazin-1-ylethyl 2-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiazole-4-carboxylate;
4-piperidyl 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiazole-2-carboxylate;
azetidin-3-ylmethyl 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiazole-2-carboxylate;
[4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]-3,6-dihydro-2H-pyridin-1-yl]-(3-piperidyl)methanone;
4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiazole-2-carboxylic acid;
2-pyrrolidin-3-ylethyl 6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline-3-carboxylate;
(1R)-5-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]indan-1-amine;
azetidin-3-ylmethyl 2-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyridine-4-carboxylate;
[(3S)-pyrrolidin-3-yl] 2-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyrimidine-5-carboxylate;
[(3S)-pyrrolidin-3-yl] 2-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiazole-5-carboxylate;
[(2S)-pyrrolidin-2-yl]methyl 6-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyridine-3-carboxylate;
[(2S)-2-piperidyl]methyl 6-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyridine-3-carboxylate;
[(3R)-pyrrolidin-3-yl] 2-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiazole-5-carboxylate;
2-[(3R)-3-aminopyrrolidin-1-yl]ethyl 6-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyridine-3-carboxylate;
2-[rac-(3S,5R)-3,5-dimethylpiperazin-1-yl]ethyl 6-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyridine-3-carboxylate;
2-(azetidin-3-yl)ethyl 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiophene-2-carboxylate;
[(2R)-pyrrolidin-2-yl]methyl 6-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyridine-3-carboxylate;
(4-aminocyclohexyl)methyl 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiophene-2-carboxylate;
2-[(3R)-3-amino-1-piperidyl]ethyl 6-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyridine-3-carboxylate;
2-[(3R)-3-amino-1-piperidyl]ethyl 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiophene-2-carboxylate;
[(2S)-pyrrolidin-2-yl]methyl 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiophene-2-carboxylate;
2-piperazin-1-ylethyl 2-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiazole-5-carboxylate;
3-bromo-6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]quinoline;
[rac-(1R,3 S)-3-aminocyclohexyl]methyl 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiophene-2-carboxylate;
(4-amino-4-methyl-cyclohexyl) 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiophene-2-carboxylate;
9-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]-3-azaspiro[5.5]undec-9-en-4-one;
[(2R)-2-piperidyl]methyl 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiophene-2-carboxylate;
2-(3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-2-yl)ethyl 6-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyridine-3-carboxylate;
[(2S)-2-piperidyl]methyl 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiophene-2-carboxylate;
2-[(3 S)-3-amino-1-piperidyl]ethyl 6-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyridine-3-carboxylate;
[rac-(1R,3R)-3-aminocyclohexyl]methyl 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiophene-2-carboxylate;
[(2R)-pyrrolidin-2-yl]methyl 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiophene-2-carboxylate;
2-[(3R)-3-aminopyrrolidin-1-yl]ethyl 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiophene-2-carboxylate;
2-[(3 S,5R)-3,5-dimethylpiperazin-1-yl]ethyl 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiophene-2-carboxylate;
[(3S)-3-piperidyl]methyl 6-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyridine-3-carboxylate;
2-[(3R,5S)-3,5-dimethylpiperazin-1-yl]ethyl 2-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiazole-4-carboxylate;
methyl 2-[[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]amino]acetate;
(4-amino-4-methyl-cyclohexyl) 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiophene-2-carboxylate;
2-(azetidin-3-ylamino)ethyl 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiophene-2-carboxylate;
azetidin-3-ylmethyl 2-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiazole-5-carboxylate;
2-(3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-2-yl)ethyl 2-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiazole-4-carboxylate;
2-piperazin-1-ylethyl 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiophene-2-carboxylate;
(3-aminocyclobutyl) 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiophene-2-carboxylate;
[(2R)-2-piperidyl]methyl 6-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]pyridine-3-carboxylate;
(4-aminocyclohexyl)methyl 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiophene-2-carboxylate;
2-[(3R)-3-amino-1-piperidyl]ethyl 2-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiazole-4-carboxylate;
and
[(3S)-3-piperidyl]methyl 4-[6-[5-(6-methyl-2-pyridyl)-1H-imidazol-4-yl]-3-quinolyl]thiophene-2-carboxylate;
or a pharmaceutically acceptable salt thereof.

274 more elements

Dependencies are inferred from the claim text.

Facts

Application: 16/949,915Filed 20 Nov 2020 · us provisional application
Priority: 22 Nov 2019
Published: US 2021/0154179 A127 May 2021
Granted: 28 Feb 2023
Term ends: Not estimatedThe source records don’t support an estimate.

Classification24 codes

A61K 31/444
Containing further heterocyclic ring systems: containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
A61K 9/0073
Pulmonary tract; Aromatherapy: sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
A61K 31/4709
Quinolines; Isoquinolines: non-condensed quinolines and containing further heterocyclic rings
A61K 31/496
Having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines: non-condensed piperazines…

Family

Application62/939,186Us provisional application · filed 22 Nov 2019
Application63/035,100Us provisional application · filed 5 Jun 2020
Application63/198,637Us provisional application · filed 30 Oct 2020
US 2021/0154179 A1Pre-grant publication · published 27 May 2021
US 11,590,116 B2This patent

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

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Abstract

A compound of Formula (I-A):

or a pharmaceutically acceptable salt thereof, wherein:
W is CH;
R1 is R10;
L1 is absent;
or selected from C1-6 alkylene, C2-6 alkenylene, C2-6 alkynylene, C3-12 carbocycle, and 3- to 12-membered heterocycle, each of which is optionally substituted with one or more R10;
L2 is selected from absent, —O—, —S—, —N(R11)—, —C(O)—, —C(O)O—, —OC(O)—, —OC(O)O—, —C(O)N(R11)—, —C(O)N(R11)C(O)—, —C(O)N(R11)C(O)N(R11)—, —N(R11)C(O)—, —N(R11)C(O)N(R11)—, —N(R11)C(O)O—, —OC(O)N(R11)—, —C(NR11)—, —N(R11)C(NR11)—, —C(NR11)N(R11)—, —N(R11)C(NR11)N(R11)—, —S(O)2—, —OS(O)—, —S(O)O—, —S(O)—, —OS(O)2, —S(O)2O—, —N(R11)S(O)2—, —S(O)2N(R11)—, —N(R11)S(O)—, —S(O)N(R11)—, —N(R11)S(O)2N(R11)—, and —N(R11)S(O)N(R11)—;
R2 is R10;
R10 is independently selected at each occurrence from:
halogen, —NO2, —CN, —OR12, —SR12, —N(R12)2, —NR13R14, —S(═O)R12, —S(═O)2R12, —S(═O)2N(R12)2, —S(═O)2NR13R14, —NR12S(═O)2R12, —NR12S(═O)2N(R12)2, —NR12S(═O)2NR13R14, —C(O)R12, —C(O)OR12, —OC(O)R12, —OC(O)OR12, —OC(O)N(R12)2, —OC(O)NR13R14, —NR12C(O)R12, —NR12C(O)OR12, —NR12C(O)N(R12)2, —NR12C(O)NR13R14, —C(O)N(R12)2, —C(O)NR13R14, —P(O)(OR12)2, —P(O)(R12)2, ═O, ═S, ═N(R12);
C1-10 alkyl, C2-10 alkenyl, and C2-10 alkynyl, each of which is independently optionally substituted at each occurrence with one or more substituents selected from halogen, —NO2, —CN, —OR12, —SR12, —N(R12)2, —NR13R14, —S(═O)R12, —S(═O)2R12, —S(═O)2N(R12)2, —S(═O)2NR13R14, —NR12S(═O)2R12, —NR12S(═O)2N(R12)2, —NR12S(═O)2NR13R14, —C(O)R12, —C(O)OR12, —OC(O)R12, —OC(O)OR12, —OC(O)N(R12)2, —OC(O)NR13R14, —NR12C(O)R12, —NR12C(O)OR12, —NR12C(O)N(R12)2, —NR12C(O)NR13R14, —C(O)N(R12)2, —C(O)NR13R14, —P(O)(OR12)2, —P(O)(R12)2, ═O, ═S, ═N(R12), C3-12 carbocycle, and 3- to 12-membered heterocycle;
and
C3-12 carbocycle and 3- to 12-membered heterocycle,
wherein each C3-12 carbocycle and 3- to 12-membered heterocycle in R10 is independently optionally substituted with one or more substituents selected from halogen, —NO2, —CN, —OR12, —SR12, —N(R12)2, —NR13R14, —S(═O)R12, —S(═O)2R12, —S(═O)2N(R12)2, —S(═O)2NR13R14, —NR12S(═O)2R12, —NR12S(═O)2N(R12)2, —NR12S(═O)2NR13R14, —C(O)R12, —C(O)OR12, —OC(O)R12, —OC(O)OR12, —OC(O)N(R12)2, —OC(O)NR13R14, —NR12C(O)R12, —NR12C(O)OR12, —NR12C(O)N(R12)2, —NR12C(O)NR13R14, —C(O)N(R12)2, —C(O)NR13R14, —P(O)(OR12)2, —P(O)(R12)2, ═O, ═S, ═N(R12), R12, C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl, and C2-6 alkynyl;
R11 is independently selected at each occurrence from:
hydrogen, —C(O)R12, —C(O)OR12, —C(O)N(R12)2, —C(O)NR13R14;
C1-6 alkyl, C2-6 alkenyl, and C2-6 alkynyl, each of which is independently optionally substituted at each occurrence with one or more substituents selected from halogen, —NO2, —CN, —OR12, —SR12, —N(R12)2, —NR13R14, —S(═O)R12, —S(═O)2R12, —S(═O)2N(R12)2, —S(═O)2NR13R14, —NR12S(═O)2R12, —NR12S(═O)2N(R12)2, —NR12S(═O)2NR13R14, —C(O)R12, —C(O)OR12, —OC(O)R12, —OC(O)OR12, —OC(O)N(R12)2, —OC(O)NR13R14, —NR12C(O)R12, —NR12C(O)OR12, —NR12C(O)N(R12)2, —NR12C(O)NR13R14, —C(O)N(R12)2, —C(O)NR13R14, —P(O)(OR12)2, —P(O)(R12)2, ═O, ═S, ═N(R12), C3-12 carbocycle, and 3- to 12-membered heterocycle;
and
C3-12 carbocycle and 3- to 12-membered heterocycle,
wherein each C3-12 carbocycle and 3- to 12-membered heterocycle in R11 is independently optionally substituted with one or more substituents selected from halogen, —NO2, —CN, —OR12, —SR12, —N(R12)2, —NR13R14, —S(═O)R12, —S(═O)2R12, —S(═O)2N(R12)2, —S(═O)2NR13R14, —NR12S(═O)2R12, —NR12S(═O)2N(R12)2, —NR12S(═O)2NR13R14, —C(O)R12, —C(O)OR12, —OC(O)R12, —OC(O)OR12, —OC(O)N(R12)2, —OC(O)NR13R14, —NR12C(O)R12, —NR12C(O)OR12, —NR12C(O)N(R12)2, —NR12C(O)NR13R14, —C(O)N(R12)2, —C(O)NR13R14, —P(O)(OR12)2, —P(O)(R12)2, ═O, ═S, ═N(R12), R12, C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl, and C2-6 alkynyl;
R12 is independently selected at each occurrence from hydrogen;
and C1-10 alkyl, C2-10 alkenyl, C2-10 alkynyl, 1- to 6-membered heteroalkyl, C3-12 carbocycle, and 3- to 12-membered heterocycle, each of which is optionally substituted by halogen, —CN, —NO2, —NH2, —NHCH3, —NHCH2CH3, ═O, —OH, —OCH3, —OCH2CH3, —CH3, —CH2CH3, —CH(CH3)2, —C(CH3)3, C3-12 carbocycle, or 3- to 6-membered heterocycle;
and
R13 and R14 are taken together with the nitrogen atom to which they are attached to form a heterocycle, optionally substituted with one or more R12.

20 more elements

Facts

Application

16/949,915Filed 20 Nov 2020 · us provisional application

Priority

22 Nov 2019

Published

US 2021/0154179 A127 May 2021

Granted

28 Feb 2023

Term ends

Not estimatedThe source records don’t support an estimate.

Classification24 codes

A61K 31/444
Containing further heterocyclic ring systems: containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
A61K 9/0073
Pulmonary tract; Aromatherapy: sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
A61K 31/4709
Quinolines; Isoquinolines: non-condensed quinolines and containing further heterocyclic rings
A61K 31/496
Having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines: non-condensed piperazines…

Family

Application62/939,186Us provisional application · filed 22 Nov 2019

Application63/035,100Us provisional application · filed 5 Jun 2020

Application63/198,637Us provisional application · filed 30 Oct 2020

US 2021/0154179 A1Pre-grant publication · published 27 May 2021

US 11,590,116 B2This patent

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