US 10,329,275 B2Granted

Compounds and compositions for the inhibition of NAMPT

AssigneesForma Tm, LLC, Genentech, Inc.

InventorsKenneth W. Bair, Timm R. Baumeister, Alexandre J. Buckmelter, Karl H. Clodfelter, Bingsong Han, Jian Lin, Dominic J. Reynolds, Chase C. Smith, Zhongguo Wang, Xiaozhang Zheng, Po-Wai Yuen

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Abstract

The present invention relates to compounds and compositions for the inhibition of NAMPT, their synthesis, applications and antidotes. An embodiment of the invention is the provision of a compound of Formula IIIA.

Claims10

Dependent claims

A compound of Formula IIA:

or a pharmaceutically acceptable salt thereof,
wherein:
Ra is present 1, 2, 3 or 4 times, and each Ra is independently selected from the group consisting of hydrogen, amino, oxo, halo, alkoxy, alkyl, haloalkyl, —N(alkyl)2, —NH(CO)O-alkyl, 1H-pyrazole, 1H-imidazole, and —C(O)NH2;
the pyridine to which Ra is attached can comprise a N-oxide formed with its N atom member;
and
R1 is haloalkyl, cycloalkyl, aryl, heterocycloalkyl, or heteroaryl;
wherein each of said cycloalkyl, heterocycloalkyl, or heteroaryl of R1 is unsubstituted or substituted by one or more halo, nitro, haloalkyl, haloalkoxy, oxo, cyano, alkyl, or alkoxy;
wherein said aryl of R1 is substituted by one or more halo, nitro, haloalkyl, haloalkoxy, oxo, cyano, alkyl, or alkoxy.

5 more elements

A compound selected from the group consisting of:

1-(pyridin-3-ylmethyl)-3-(4-{[2-(trifluoromethoxy)benzene]sulfonyl}phenyl)urea;
3-{4-[(4-bromobenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(4-methoxy-2-methylbenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(2,4-dimethoxybenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
1-[(6-aminopyridin-3-yl)methyl]-3-{4-[(4-fluorobenzene)sulfonyl]phenyl}urea;
3-{4-[(3,5-dimethylbenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(4-methylbenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(2-bromobenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(2-ethoxybenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(3,4-dimethoxybenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
1-(pyridin-3-ylmethyl)-3-(4-{[4-(trifluoromethyl)benzene]sulfonyl}phenyl)urea;
3-{4-[(2,5-dimethylbenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
1-(pyridin-3-ylmethyl)-3-(4-{[3-(trifluoromethoxy)benzene]sulfonyl}phenyl)urea;
3-{4-[(3-bromobenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
1-(pyridin-3-ylmethyl)-3-(4-{[3-(trifluoromethyl)benzene]sulfonyl}phenyl)urea;
3-{4-[(5-fluoro-2-methylbenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(4-chloro-2-methylbenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(2-fluoro-3-methoxybenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(2,3-difluorobenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(2-chloro-6-fluoro-3-methylbenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-(pyridin-3-ylmethyl)-1-[4-(pyrimidine-5-sulfonyl)phenyl]urea;
3-{4-[(3,5-difluorobenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(2,4-dichlorobenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(2,5-difluoro-4-methoxybenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(4-ethylbenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(2-chlorobenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(4-chloro-2-fluorobenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(4-chlorobenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(5-fluoro-2-methoxybenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(2-methoxybenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(4-fluorobenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-[4-(2-methoxynaphthalene-1-sulfonyl)phenyl]-1-(pyridin-3-ylmethyl)urea;
3-{[({4-[(4-chlorobenzene)sulfonyl]phenyl}carbamoyl)amino]methyl}pyridin-1-ium-1-olate;
3-{4-[(3-fluorobenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(3-chlorobenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-(4-{[2-(methoxymethyl)benzene]sulfonyl}phenyl)-1-(pyridin-3-ylmethyl)urea;
3-{4-[(2,3-dichlorobenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(4-fluoro-2-methylbenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-(4-{[3-(propan-2-yl)benzene]sulfonyl}phenyl)-1-(pyridin-3-ylmethyl)urea;
3-{4-[(2,3-dimethylbenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
1-[4-(cyclopentanesulfonyl)phenyl]-3-(pyridin-3-ylmethyl)urea;
3-{4-[(2-fluoro-6-methoxybenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(2,5-dimethoxybenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
1-(pyridin-3-ylmethyl)-3-[4-(trifluoromethane)sulfonylphenyl]urea;
3-{4-[(2-fluoro-4-methoxybenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-[4-(3,5-dimethyl-1,2-oxazole-4-sulfonyl)phenyl]-1-(pyridin-3-ylmethyl)urea;
3-{4-[(4-chloro-3-fluorobenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-(4-{[2-chloro-5-(trifluoromethyl)benzene]sulfonyl}phenyl)-1-(pyridin-3-ylmethyl)urea;
3-{4-[(2-fluorobenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
1-(pyridin-3-ylmethyl)-3-(4-{[2-(trifluoromethyl)benzene]sulfonyl}phenyl)urea;
3-(4-{[4-chloro-3-(trifluoromethyl)benzene]sulfonyl}phenyl)-1-(pyridin-3-ylmethyl)urea;
3-{4-[(2-fluoro-4-methylbenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[2-chloro-6-(propan-2-yl)pyridine-3-sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(2-methoxy-5-methylbenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-(pyridin-3-ylmethyl)-1-[4-(pyridine-4-sulfonyl)phenyl]urea;
3-{4-[(2-chloro-4-fluorobenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(2-ethylbenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(3-fluoro-4-methylbenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(2,5-dichlorobenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-(pyridin-3-ylmethyl)-1-[4-(pyridine-3-sulfonyl)phenyl]urea;
3-{4-[(3-methylbenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(2,4-difluorobenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(2,6-dimethoxybenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
1-(4-{8-oxatricyclo[7.4.0.02,7]trideca-1 (9),2(7),3,5,10,12-hexaene-6-sulfonyl}phenyl)-3-(pyridin-3-ylmethyl)urea;
3-(pyridin-3-ylmethyl)-1-[4-(pyridine-2-sulfonyl)phenyl]urea;
3-{4-[(5-chloro-2-methoxybenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-(4-{[2-methoxy-5-(propan-2-yl)benzene]sulfonyl}phenyl)-1-(pyridin-3-ylmethyl)urea;
3-(4-{[3-(propan-2-yloxy)benzene]sulfonyl}phenyl)-1-(pyridin-3-ylmethyl)urea;
1-(pyridin-3-ylmethyl)-3-{4-[(2,4,6-trimethylbenzene)sulfonyl]phenyl}urea;
3-{4-[(3-fluoro-4-methoxybenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(2-methylbenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(2,4-dimethylbenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(2,5-difluorobenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(2-fluoro-5-methylbenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
1-(pyridin-3-ylmethyl)-3-(4-{[4-(trifluoromethoxy)benzene]sulfonyl}phenyl)urea;
3-[4-(1-methyl-1H-pyrazole-4-sulfonyl)phenyl]-1-(pyridin-3-ylmethyl)urea;
3-[4-(5-methylthiophene-2-sulfonyl)phenyl]-1-(pyridin-3-ylmethyl)urea;
3-{4-[(3,4-difluorobenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(2,6-dimethylbenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-[4-(2-methoxypyrimidine-5-sulfonyl)phenyl]-1-(pyridin-3-ylmethyl)urea;
3-{4-[(2R)-2-(methoxymethyl)pyrrolidine-1-sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-(4-{[3-fluoro-5-(2,2,2-trifluoroethoxy)benzene]sulfonyl}phenyl)-1-(pyridin-3-ylmethyl)urea;
3-{4-[(3-fluoro-4-propoxybenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-(4-{[4-fluoro-3-(trifluoromethyl)benzene]sulfonyl}phenyl)-1-(pyridin-3-ylmethyl)urea;
1-[4-(3,5-dimethylpiperidine-1-sulfonyl)phenyl]-3-(pyridin-3-ylmethyl)urea;
3-[4-(1-methyl-1H-indole-2-sulfonyl)phenyl]-1-(pyridin-3-ylmethyl)urea;
3-{[4-(piperidine-1-sulfonyl)phenyl]methyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(3-ethoxy-4-fluorobenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[3-(2-methoxyethyl)piperidine-1-sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-[4-(1-methyl-1H-indazole-7-sulfonyl)phenyl]-1-(pyridin-3-ylmethyl)urea;
3-{4-[(4-methoxybenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(4-methoxy-3,5-dimethylbenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-(4-{[2-methyl-4-(trifluoromethyl)benzene]sulfonyl}phenyl)-1-(pyridin-3-ylmethyl)urea;
3-(4-{[3-chloro-5-(trifluoromethyl)benzene]sulfonyl}phenyl)-1-(pyridin-3-ylmethyl)urea;
1-[4-(piperidine-1-sulfonyl)phenyl]-3-(pyridin-3-ylmethyl)urea;
1-{4-[(3 S)-3-cyanopiperidine-1-sulfonyl]phenyl}-3-(pyridin-3-ylmethyl)urea;
3-{4-[(2 S)-2-(methoxymethyl)pyrrolidine-1-sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-[4-(3-methylpiperidine-1-sulfonyl)phenyl]-1-(pyridin-3-ylmethyl)urea;
3-{4-[(3-chloro-5-methylbenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-(4-{[4-(ethoxymethyl)benzene]sulfonyl}phenyl)-1-(pyridin-3-ylmethyl)urea;
1-(pyridin-3-ylmethyl)-3-{4-[3-(trifluoromethyl)piperidine-1-sulfonyl]phenyl}urea;
3-{4-[(3,4-dichlorobenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-(pyridin-3-ylmethyl)-1-[4-(quinoline-6-sulfonyl)phenyl]urea;
3-[(5-chloropyridin-3-yl)methyl]-1-[4-(piperidine-1-sulfonyl)phenyl]urea;
1-(pyridin-3-ylmethyl)-3-[4-(1H-pyrrole-1-sulfonyl)phenyl]urea;
3-(pyridin-3-ylmethyl)-1-[4-(thiomorpholine-4-sulfonyl)phenyl]urea;
3-(pyridin-3-ylmethyl)-1-[4-(pyrrolidine-1-sulfonyl)phenyl]urea;
1-[4-(phenoxathiine-4-sulfonyl)phenyl]-3-(pyridin-3-ylmethyl)urea;
3-(pyridin-3-ylmethyl)-1-[4-(quinoline-8-sulfonyl)phenyl]urea;
3-[4-(4-methylpiperidine-1-sulfonyl)phenyl]-1-(pyridin-3-ylmethyl)urea;
3-(pyridin-3-ylmethyl)-1-[4-(quinoline-3-sulfonyl)phenyl]urea;
3-(4-{[3-fluoro-5-(2-methylpropoxy)benzene]sulfonyl}phenyl)-1-(pyridin-3-ylmethyl)urea;
1-{4-[(3-cyanobenzene)sulfonyl]phenyl}-3-(pyridin-3-ylmethyl)urea;
3-[(5-fluoropyridin-3-yl)methyl]-1-[4-(piperidine-1-sulfonyl)phenyl]urea;
1-[4-(isoquinoline-4-sulfonyl)phenyl]-3-(pyridin-3-ylmethyl)urea;
1-(4-{3-azaspiro[5.5]undecane-3-sulfonyl}phenyl)-3-(pyridin-3-ylmethyl)urea;
3-[4-(6-methoxypyridine-3-sulfonyl)phenyl]-1-(pyridin-3-ylmethyl)urea;
3-{4-[(3-propoxybenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
1-(pyridin-3-ylmethyl)-3-{4-[4-(trifluoromethyl)piperidine-1-sulfonyl]phenyl}urea;
3-(4-{[4-(propan-2-yloxy)benzene]sulfonyl}phenyl)-1-(pyridin-3-ylmethyl)urea;
3-{4-[(4-ethoxybenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
1-[4-(4,4-difluoropiperidine-1-sulfonyl)phenyl]-3-(pyridin-3-ylmethyl)urea;
3-[4-(1-methyl-1H-indazole-4-sulfonyl)phenyl]-1-(pyridin-3-ylmethyl)urea;
1-[4-(piperazine-1-sulfonyl)phenyl]-3-(pyridin-3-ylmethyl)urea;
1-(pyridin-3-ylmethyl)-3-{4-[(3 S)-3-(trifluoromethyl)piperidine-1-sulfonyl]phenyl}urea;
1-[4-(2,3-dihydro-1-benzofuran-7-sulfonyl)phenyl]-3-(pyridin-3-ylmethyl)urea;
3-{4-[4-(2-methoxyethyl)piperazine-1-sulfonyl]phenyl)}-1-(pyridin-3-ylmethyl)urea;
1-[4-(2,3-dihydro-1,4-benzodioxine-6-sulfonyl)phenyl]-3-(pyridin-3-ylmethyl)urea;
3-{4-[4-(propan-2-yl)piperazine-1-sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-[4-(2-methyl-3-oxopiperazine-1-sulfonyl)phenyl]-1-(pyridin-3-ylmethyl)urea;
3-{4-[(3-ethoxybenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
1-[4-(1H-indole-4-sulfonyl)phenyl]-3-(pyridin-3-ylmethyl)urea;
3-{4-[(4-chlorobenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-[4-(1-methyl-1H-indazole-6-sulfonyl)phenyl]-1-(pyridin-3-ylmethyl)urea;
3-(4-{[3-fluoro-4-(trifluoromethoxy)benzene]sulfonyl}phenyl)-1-(pyridin-3-ylmethyl)urea;
3-{4-[(3-chloro-4-methoxybenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-(4-{[4-fluoro-3-(2,2,2-trifluoroethoxy)benzene]sulfonyl}phenyl)-1-(pyridin-3-ylmethyl)urea;
1-[4-(morpholine-4-sulfonyl)phenyl]-3-(pyridin-3-ylmethyl)urea;
1-(4-{3-azatricyclo[7.3.1.05,13]trideca-1(13),5,7,9,11-pentaene-3-sulfonyl}phenyl)-3-(pyridin-3-ylmethyl)urea;
3-[(6-chloropyridin-3-yl)methyl]-1-[4-(piperidine-1-sulfonyl)phenyl]urea;
1-(pyridin-3-ylmethyl)-3-[4-(3,3,5-trimethylazepane-1-sulfonyl)phenyl]urea;
3-[4-(1-propyl-1H-pyrazole-4-sulfonyl)phenyl]-1-(pyridin-3-ylmethyl)urea;
3-(4-{[3-fluoro-5-(trifluoromethyl)benzene]sulfonyl}phenyl)-1-(pyridin-3-ylmethyl)urea;
3-(4-{[3-fluoro-4-(2,2,2-trifluoroethoxy)benzene]sulfonyl}phenyl)-1-(pyridin-3-ylmethyl)urea;
1-[4-(4-cyanopiperidine-1-sulfonyl)phenyl]-3-(pyridin-3-ylmethyl)urea;
1-(4-{3-oxa-8-azabicyclo[3.2.1]octane-8-sulfonyl}phenyl)-3-(pyridin-3-ylmethyl)urea;
tert-butyl N-{5-[({[4-(piperidine-1-sulfonyl)phenyl]carbamoyl}amino)methyl]pyridin-2-yl}carbamate;
3-{4-[(4-chloro-3-methoxybenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
rel-3-{4-[(2R,6S)-2,6-dimethylmorpholine-4-sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
1-[4-(decahydroquinoline-1-sulfonyl)phenyl]-3-(pyridin-3-ylmethyl)urea;
3-{4-[(3-chloro-4-methylbenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-(4-{[3-fluoro-4-(trifluoromethyl)benzene]sulfonyl}phenyl)-1-(pyridin-3-ylmethyl)urea;
3-{4-[(4-fluoro-3-methylbenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-[4-(2-methylpyridine-3-sulfonyl)phenyl]-1-(pyridin-3-ylmethyl)urea;
3-{4-[(3-fluoro-5-methoxybenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
rel-3-{4-[(4aR,8aS)-decahydroisoquinoline-2-sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-(4-{[3-(2-methylpropoxy)benzene]sulfonyl}phenyl)-1-(pyridin-3-ylmethyl)urea;
3-[4-(1-methyl-1H-indazole-5-sulfonyl)phenyl]-1-(pyridin-3-ylmethyl)urea;
3-{4-[(4-ethoxy-3-fluorobenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(3,5-dichlorobenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(3-methoxy-4-methylbenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-[4-(6-methylpyridine-3-sulfonyl)phenyl]-1-(pyridin-3-ylmethyl)urea;
3-(pyridin-3-ylmethyl)-1-[4-(5,6,7,8-tetrahydro-1,6-naphthyridine-6-sulfonyl)phenyl]urea;
3-[4-(2,4-dimethoxypyrimidine-5-sulfonyl)phenyl]-1-(pyridin-3-ylmethyl)urea;
3-[(6-aminopyridin-3-yl)methyl]-1-[4-(piperidine-1-sulfonyl)phenyl]urea;
3-{4-[(4-fluoro-3-methoxybenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
1-[4-(3,4-dihydro-2H-1,4-benzoxazine-4-sulfonyl)phenyl]-3-(pyridin-3-ylmethyl)urea;
3-{4-[(3 S)-3-methylpiperidine-1-sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-[4-(azepane-1-sulfonyl)phenyl]-1-(pyridin-3-ylmethyl)urea;
3-(4-{[3-chloro-4-(trifluoromethyl)benzene]sulfonyl}phenyl)-1-(pyridin-3-ylmethyl)urea;
3-[4-(piperidine-1-sulfonyl)phenyl]-1-{[6-(trifluoromethyl)pyridin-3-yl]methyl}urea;
3-[4-(5-fluoropyridine-3-sulfonyl)phenyl]-1-(pyridin-3-ylmethyl)urea;
3-{4-[4-(methoxymethyl)piperidine-1-sulfonyl]phenyl)}-1-(pyridin-3-ylmethyl)urea;
3-{4-[2-(dimethylamino)pyrimidine-5-sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(3-chloro-4-propoxybenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-(4-{[3-(methoxymethyl)benzene]sulfonyl}phenyl)-1-(pyridin-3-ylmethyl)urea;
3-(4-{[2-methoxy-5-(trifluoromethyl)benzene]sulfonyl}phenyl)-1-(pyridin-3-ylmethyl)urea;
1-[4-(2,6-dimethylpiperidine-1-sulfonyl)phenyl]-3-(pyridin-3-ylmethyl)urea;
1-(pyridin-3-ylmethyl)-3-{4-[6-(trifluoromethyl)pyridine-3-sulfonyl]phenyl}urea;
3-{4-[4-(2-methylpropyl)piperazine-1-sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
5-[({[4-(piperidine-1-sulfonyl)phenyl]carbamoyl}amino)methyl]pyridine-2-carboxamide;
3-[4-(azetidine-1-sulfonyl)phenyl]-1-(pyridin-3-ylmethyl)urea;
3-{4-[(3-ethylbenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-[4-(5-chloropyridine-3-sulfonyl)phenyl]-1-(pyridin-3-ylmethyl)urea;
3-{4-[(3-fluoro-5-methylbenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-[4-(3,3-difluoroazetidine-1-sulfonyl)phenyl]-1-(pyridin-3-ylmethyl)urea;
1-(4-{8-azabicyclo[3.2.1]octane-8-sulfonyl}phenyl)-3-(pyridin-3-ylmethyl)urea;
1-(4-{8-oxa-3-azabicyclo[3.2.1]octane-3-sulfonyl}phenyl)-3-(pyridin-3-ylmethyl)urea;
1-(4-{[3-(cyclopropylmethoxy)benzene]sulfonyl}phenyl)-3-(pyridin-3-ylmethyl)urea;
1-(4-{2-azabicyclo[2.2.1]heptane-2-sulfonyl}phenyl)-3-(pyridin-3-ylmethyl)urea;
3-[4-(2,3-dihydro-1H-indole-1-sulfonyl)phenyl]-1-(pyridin-3-ylmethyl)urea;
3-(4-{[4-(propan-2-yl)benzene]sulfonyl}phenyl)-1-(pyridin-3-ylmethyl)urea;
3-{4-[(2R,6 S)-2,6-dimethylmorpholine-4-sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(4-fluoro-2-methoxybenzene)sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
3-{4-[(2S)-2-ethylpiperidine-1-sulfonyl]phenyl}-1-(pyridin-3-ylmethyl)urea;
and
1-{4-[(4-cyanobenzene)sulfonyl]phenyl}-3-(pyridin-3-ylmethyl)urea;
or a pharmaceutically acceptable salt thereof.

195 more elements

Dependencies are inferred from the claim text.

Facts

Application: 16/008,378Filed 14 Jun 2018 · continuation
Priority: 3 Sep 2010
Published: US 2018/0291000 A111 Oct 2018
Granted: 25 Jun 2019
Term ends: Not estimatedThe source records don’t support an estimate.

Classification40 codes

C07D 401/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links
A61K 31/437
Ortho- or peri-condensed with heterocyclic ring systems: the heterocyclic ring system containing a five-membered ring having nitrogen as a ring…
A61K 31/44
Having six-membered rings with one nitrogen as the only ring hetero atom: non condensed pyridines; Hydrogenated derivatives thereof
A61K 31/4406
Non condensed pyridines; Hydrogenated derivatives thereof: only substituted in position 3, e.g. zimeldine

Family

Application61/379,812Us provisional application · filed 3 Sep 2010
Application61/379,819Us provisional application · filed 3 Sep 2010
Application61/386,037Us provisional application · filed 24 Sep 2010
Application61/386,044Us provisional application · filed 24 Sep 2010
Application61/478,995Us provisional application · filed 26 Apr 2011
Application61/480,423Us provisional application · filed 29 Apr 2011
PCT/US2011/050320Parent of this continuation · filed 2 Sep 2011
US 2018/0291000 A1Pre-grant publication · published 11 Oct 2018
Application13/820,496Parent of this continuation
US 2013/0273034 A1Published application
US 10,329,275 B2This patent

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

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Abstract

Facts

Application

16/008,378Filed 14 Jun 2018 · continuation

Priority

3 Sep 2010

Published

US 2018/0291000 A111 Oct 2018

Granted

25 Jun 2019

Term ends

Not estimatedThe source records don’t support an estimate.

Classification40 codes

C07D 401/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links
A61K 31/437
Ortho- or peri-condensed with heterocyclic ring systems: the heterocyclic ring system containing a five-membered ring having nitrogen as a ring…
A61K 31/44
Having six-membered rings with one nitrogen as the only ring hetero atom: non condensed pyridines; Hydrogenated derivatives thereof
A61K 31/4406
Non condensed pyridines; Hydrogenated derivatives thereof: only substituted in position 3, e.g. zimeldine

Family

Application61/379,812Us provisional application · filed 3 Sep 2010

Application61/379,819Us provisional application · filed 3 Sep 2010

Application61/386,037Us provisional application · filed 24 Sep 2010

Application61/386,044Us provisional application · filed 24 Sep 2010

Application61/478,995Us provisional application · filed 26 Apr 2011

Application61/480,423Us provisional application · filed 29 Apr 2011

PCT/US2011/050320Parent of this continuation · filed 2 Sep 2011

US 2018/0291000 A1Pre-grant publication · published 11 Oct 2018

Application13/820,496Parent of this continuation

US 2013/0273034 A1Published application

US 10,329,275 B2This patent

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