IP Library › Granted Patent US 9,403,807
Granted Patent B2
US 9,403,807 · App. 14/557,980 · Granted Aug 2, 2016

Mineralocorticoid receptor antagonists

Inventors: Alejandro Crespo (Edison, NJ); Ping Lan (Dayton, NJ); Rudrajit Mal (Edison, NJ); Anthony Ogawa (Mountainside, NJ); Hong Shen (Shanghai, CN); Peter J. Sinclair (Doylestown, PA); Zhongxiang Sun (Edison, NJ); Ellen K. Vande Bunte (Hawthorne, NJ); Zhicai Wu (Montvale, NJ); Kun Liu (Boston, MA); Robert J. DeVita (Westfield, NJ); Dong-Ming Shen (Edison, NJ); Min Shu (Greenbrook, NJ); John Qiang Tan (Westfield, NJ); Changhe Qi (Shanghai, CN); Yuguang Wang (Shanghai, CN); Richard Beresis (Shanghai, CN)
Assignee: Merck Sharp & Dohme Corp.
C07D413/06A61K31/404A61K31/405A61K31/4045A61K31/416A61K31/4196A61K31/422A61K31/4245A61K45/06C07D209/08C07D209/10C07D231/56C07D403/04C07D403/06C07D405/06
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Quick Facts
Patent No.
US 9,403,807
App. No.
14/557,980
Granted
Aug 2, 2016
Kind
B2
Abstract

The present invention is directed to compounds of the Formula I as well as pharmaceutically acceptable salts thereof, that are useful for treating aldosterone-mediated diseases. The invention furthermore relates to processes for preparing compounds of the Formula I, to their use for the therapy and prophylaxis of the abovementioned diseases and for preparing pharmaceuticals for this purpose, and to pharmaceutical compositions which comprise compounds of the Formula I.

Claims (166)

1. A compound selected from

methyl (4-chlorophenyl)(4-nitro-1H-indol-1-yl)acetate;

methyl (2-chloro-4-fluorophenyl)(4-nitro-1H-indol-1-yl)acetate;

methyl (2,4-dichlorophenyl)(4-nitro-1H-indol-1-yl)acetate;

methyl (3-bromophenyl)(4-nitro-1H-indol-1-yl)acetate;

methyl (4-methoxyphenyl)(4-nitro-1H-indol-1-yl)acetate;

methyl (2-chloro-4-fluorophenyl)(1H-indol-1-yl)acetate;

methyl (2-chloro-4-fluorophenyl)(4-cyano-1H-indol-1-yl)acetate;

ethyl 1-[1-(2-chloro-4-fluorophenyl)-2-methoxy-2-oxoethyl]-1H-indole-4-carboxylate;

methyl (2-chloro-4-fluorophenyl)(4-chloro-1H-indol-1-yl)acetate;

methyl (2-chloro-4-fluorophenyl)(4-fluoro-1H-indol-1-yl)acetate;

methyl (2-chloro-4-fluorophenyl)(5-cyano-1H-indol-1-yl)acetate;

methyl (2-chloro-4-fluorophenyl)(5-chloro-1H-indol-1-yl)acetate;

methyl (2-chloro-4-fluorophenyl)(5-fluoro-1H-indol-1-yl)acetate;

methyl (2-chloro-4-fluorophenyl)(6-chloro-1H-indol-1-yl)acetate;

methyl (2-chloro-4-fluorophenyl)(7-fluoro-1H-indol-1-yl)acetate;

methyl[7-(benzyloxy)-1H-indol-1-yl](2-chloro-4-fluorophenyl)acetate;

methyl (4-chlorophenyl){4-[(methylsulfonyl)amino]-1H-indol-1-yl}acetate;

tert-butyl(4-chlorophenyl){4-[(methylsulfonyl)amino]-1H-indol-1-yl}acetate;

methyl (2-chloro-4-fluorophenyl)(4-{[(trifluoromethyl)sulfonyl]amino}-1H-indol-1-yl)acetate;

methyl {4-[(methylsulfonyl)amino]-1H-indol-1-yl}(phenyl)acetate;

methyl (2-chloro-4-fluorophenyl){4-[(methylsulfonyl)amino]-1H-indol-1-yl}acetate;

methyl (2,4-dichlorophenyl){4-[(methylsulfonyl)amino]-1H-indol-1-yl}acetate;

methyl (4-bromophenyl){4-[(methylsulfonyl)amino]-1H-indol-1-yl}acetate;

methyl 2-(4-chlorophenyl)-2-{4-[(methylsulfonyl)amino]-1H-indol-1-yl}butanoate;

(R)-methyl 2-(4-chlorophenyl)-2-{4-[(methylsulfonyl)amino]-1H-indol-1-yl}butanoate;

(S)-methyl 2-(4-chlorophenyl)-2-{4-[(methylsulfonyl)amino]-1H-indol-1-yl}butanoate;

tert-Butyl 2-(4-chlorophenyl)-2-{4-[(methylsulfonyl)amino]-1H-indol-1-yl}butanoate;

tert-Butyl 2-(4-chlorophenyl)-3-cyano-2-{4-[(methylsulfonyl)amino]-1H-indol-1-yl}propanoate;

Methyl 2-(4-chlorophenyl)-2-{4-[(methylsulfonyl)amino]-1H-indol-1-yl}propanoate;

Methyl 2-(2,4-dichlorophenyl)-2-{4-[(methylsulfonyl)amino]-1H-indol-1-yl}propanoate;

Methyl 2-(2,4-dichlorophenyl)-2-{4-[(methylsulfonyl)amino]-1H-indol-1-yl}butanoate;

Methyl 2-(2-chloro-4-fluorophenyl)-2-{4-[(methylsulfonyl)amino]-1H-indol-1-yl}butanoate;

Methyl 2-(4-chlorophenyl)-2-{4-[(methylsulfonyl)amino]-1H-indol-1-yl}pent-4-enoate;

Methyl 2-(4-chlorophenyl)-2-{4-[(methylsulfonyl)amino]-1H-indol-1-yl}-3-phenylpropanoate;

Dimethyl 2-(4-chlorophenyl)-2-{4-[(methylsulfonyl)amino]-1H-indol-1-yl}butanedioate;

Methyl 2-(4-chlorophenyl)-3-cyano-2-{4-[(methylsulfonyl)amino]-1H-indol-1-yl}propanoate;

Methyl 2-(4-chlorophenyl)-3-methoxy-2-{4-[(methylsulfonyl)amino]-1H-indol-1-yl}propanoate;

Methyl 2-(4-chlorophenyl)-3-cyclopropyl-2-{4-[(methylsulfonyl)amino]-1H-indol-1-yl}propanoate;

(R)-2-(4-chlorophenyl)-N-methyl-2-{4-[(methylsulfonyl)amino]-1H-indol-1-yl}butanamide;

(R)-2-(4-chlorophenyl)-2-{4-[(methylsulfonyl)amino]-1H-indol-1-yl}butanamide;

(R)-2-(4-chlorophenyl)-N-cyclopropyl-2-{4-[(methylsulfonyl)amino]-1H-indol-1-yl}butanamide;

2-(4-chlorophenyl)-N-(2-methoxyethyl)-2-{4-[(methylsulfonyl)amino]-1H-indol-1-yl}butanamide;

(R)—N-benzyl-2-(4-chlorophenyl)-2-{4-[(methylsulfonyl)amino]-1H-indol-1-yl}butanamide;

(R)-2-(4-chlorophenyl)-N-(1-methylethyl)-2-{4-[(methylsulfonyl)amino]-1H-indol-1-yl}butanamide;

(R)—N-tert-butyl-2-(4-chlorophenyl)-2-{4-[(methylsulfonyl)amino]-1H-indol-1-yl}butanamide;

2-(4-chlorophenyl)-N-ethyl-2-{4-[(methylsulfonyl)amino]-1H-indol-1-yl}butanamide;

(R)-2-(4-chlorophenyl)-2-{4-[(methylsulfonyl)amino]-1H-indol-1-yl}-N-(2,2,2-trifluoroethyl)butanamide;

2-(4-chlorophenyl)-N-(2-cyanoethyl)-2-{4-[(methylsulfonyl)amino]-1H-indol-1-yl}butanamide;

2-(4-chlorophenyl)-N-(2-fluoroethyl)-2-{4-[(methylsulfonyl)amino]-1H-indol-1-yl}butanamide;

2-(4-chlorophenyl)-2-{4-[(methylsulfonyl)amino]-1H-indol-1-yl}-N-(2-phenylethyl)butanamide;

(R)-2-(4-chlorophenyl)-N-(cyanomethyl)-2-{4-[(methylsulfonyl)amino]-1H-indol-1-yl}butanamide;

methyl N-[2-(4-chlorophenyl)-2-{4-[(methylsulfonyl)amino]-1H-indol-1-yl}butanoyl]glycinate;

2-(4-chlorophenyl)-3-cyano-N-methyl-2-{4-[(methylsulfonyl)amino]-1H-indol-1-yl}propanamide;

N-benzyl-2-(4-chlorophenyl)-3-cyano-2-{4-[(methylsulfonyl)amino]-1H-indol-1-yl}propanamide;

2-(4-chlorophenyl)-3-cyano-2-{4-[(methylsulfonyl)amino]-1H-indol-1-yl}-N-(2,2,2-trifluoroethyl)propanamide;

2-(4-chlorophenyl)-3-cyclopropyl-N-methyl-2-{4-[(methylsulfonyl)amino]-1H-indol-1-yl}propanamide;

(R)-methyl N-{1-[1-(4-chlorophenyl)-1-(5-methyl-1,2,4-oxadiazol-3-yl)propyl]-1H-indol-4-yl}methanesulfonamide;

(R)—N-{1-[1-(4-chlorophenyl)-1-(5-phenyl-1,2,4-oxadiazol-3-yl)propyl]-1H-indol-4-yl}methanesulfonamide;

(R)—N-(1-{1-(4-chlorophenyl)-1-[5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl]propyl}-1H-indol-4-yl)methanesulfonamide;

(R)—N-(1-{1-(4-chlorophenyl)-1-[5-(4-chlorophenyl)-1,2,4-oxadiazol-3-yl]propyl}-1H-indol-4-yl)methanesulfonamide;

(R)—N-(1-{1-(4-chlorophenyl)-1-[5-(4-methoxyphenyl)-1,2,4-oxadiazol-3-yl]propyl}-1H-indol-4-yl)methanesulfonamide;

(R)—N-{1-[1-(4-chlorophenyl)-1-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)propyl]-1H-indol-4-yl}methanesulfonamide;

N-{1-[(4-chlorophenyl)(3-phenyl-1,2,4-oxadiazol-5-yl)methyl]-1H-indol-4-yl}methanesulfonamide;

(R)—N-{1-[1-(4-chlorophenyl)-1-(3-phenyl-1H-1,2,4-triazol-5-yl)propyl]-1H-indol-4-yl}methanesulfonamide;

(R)—N-{1-[1-(4-chlorophenyl)-1-(5-methyl-4H-1,2,4-triazol-3-yl)propyl]-1H-indol-4-yl}methanesulfonamide;

(R)—N-(1-{1-(4-chlorophenyl)-1-[5-(trifluoromethyl)-4H-1,2,4-triazol-3-yl]propyl}-1H-indol-4-yl)methanesulfonamide;

(R)—N-{1-[1-(4-chlorophenyl)-1-(5-cyclopropyl-1,3,4-oxadiazol-2-yl)propyl]-1H-indol-4-yl}methanesulfonamide;

N-{1-[1-(4-chlorophenyl)-1-(5-methyl-1,3,4-oxadiazol-2-yl)propyl]-1H-indol-4-yl}methanesulfonamide;

N-(1-{1-(4-chlorophenyl)-1-[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]propyl}-1H-indol-4-yl)methanesulfonamide;

(R)—N-{1-[1-(4-chlorophenyl)-1-(5-phenyl-1,3,4-oxadiazol-2-yl)propyl]-1H-indol-4-yl}methanesulfonamide;

(R)—N-(1-{1-(4-chlorophenyl)-1-[5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl]propyl}-1H-indol-4-yl)methanesulfonamide;

(R)—N-(1-{1-(4-chlorophenyl)-1-[5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl]propyl}-1H-indol-4-yl)methanesulfonamide;

(R)—N-{1-[1-(4-chlorophenyl)-1-{5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-yl}propyl]-1H-indol-4-yl}methanesulfonamide;

(R)—N-(1-{1-(4-chlorophenyl)-1-[5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]propyl}-1H-indol-4-yl)methanesulfonamide;

(R)—N-(1-{1-(4-chlorophenyl)-1-[5-(3,5-difluorophenyl)-1,3,4-oxadiazol-2-yl]propyl}-1H-indol-4-yl)methanesulfonamide;

N-{1-[1-(4-chlorophenyl)-2-cyano-1-(5-phenyl-1,3,4-oxadiazol-2-yl)ethyl]-1H-indol-4-yl}methanesulfonamide;

N-{1-[1-(4-chlorophenyl)-1-(4-phenyl-1,3-oxazol-2-yl)propyl]-1H-indol-4-yl}methanesulfonamide;

methyl 2-(3′-methoxybiphenyl-3-yl)-2-{4-[(methylsulfonyl)amino]-1H-indol-1-yl}butanoate;

Methyl (2′-chlorobiphenyl-3-yl){4-[(methylsulfonyl)amino]-1H-indol-1-yl}acetate;

Methyl {4-[(methylsulfonyl)amino]-1H-indol-1-yl}[2′-(trifluoromethoxy)biphenyl-3-yl]acetate;

Methyl {4-[(methylsulfonyl)amino]-1H-indol-1-yl}[4′-(trifluoromethoxy)biphenyl-3-yl]acetate;

N-{1-[(2R)-2-(4-chlorophenyl)-1-hydroxybutan-2-yl]-1H-indol-4-yl}methanesulfonamide;

N-{1-[(2S)-2-(4-chlorophenyl)-1-hydroxybutan-2-yl]-1H-indol-4-yl}methanesulfonamide;

methyl 2-(4-chlorophenyl)-3-cyano-2-{4-[(methylsulfonyl)amino]-1H-indol-1-yl}propanoate;

N-{1-[3-(4-chlorophenyl)-2-oxopyrrolidin-3-yl]-1H-indol-4-yl}methanesulfonamide;

N-(1-(2-(4-chlorophenyl)-1-hydroxybutan-2-yl)-6-fluoro-1H-indol-4-yl)methanesulfonamide;

N-(1-(2-(2,4-dichlorophenyl)-1-hydroxybutan-2-yl)-1H-indol-4-yl)methanesulfonamide;

N-(1-(3-(4-chlorophenyl)-2-hydroxy-2-methylpentan-3-yl)-6-fluoro-1H-indol-4-yl)methane sulfonamide;

N-(1-(2-(4-chlorophenyl)-1-methoxybutan-2-yl)-1H-indol-4-yl)methanesulfonamide;

N-(1-(3-(4-chlorophenyl)-2-oxopentan-3-yl)-6-fluoro-1H-indol-4-yl)methanesulfonamide;

N-(1-(3-(4-chlorophenyl)-2-oxopentan-3-yl)-1H-indol-4-yl)methanesulfonamide;

N-(1-(2-oxo-3-(4-(trifluoromethyl)phenyl)pentan-3-yl)-1H-indol-4-yl)methanesulfonamide;

N-(1-(3-(4-chlorophenyl)-2-hydroxypentan-3-yl)-1H-indol-4-yl)methanesulfonamide;

N-(1-(3-(4-chlorophenyl)-2-hydroxypentan-3-yl)-1H-indol-4-yl)methanesulfonamide

N-(1-(3-(2,4-dichlorophenyl)-2-hydroxypentan-3-yl)-1H-indol-4-yl)methanesulfonamide;

N-(1-(3-(4-chlorophenyl)-2-hydroxypentan-3-yl)-6-fluoro-1H-indol-4-yl)methanesulfonamide;

N-(1-(2-hydroxy-3-(4-(trifluoromethyl)phenyl)pentan-3-yl)-1H-indol-4-yl)methanesulfonamide;

N-(1-(2-(4-chlorophenyl)-1-cyanobutan-2-yl)-1H-indol-4-yl)methanesulfonamide;

N-(1-(2-(4-chlorophenyl)-1-cyanobutan-2-yl)-6-fluoro-1H-indol-4-yl)methanesulfonamide;

N-(1-(2-(4-chlorophenyl)-1-cyanobutan-2-yl)-6-fluoro-1H-indol-4-yl)methanesulfonamide;

N-(1-(1-cyano-2-(4-(trifluoromethyl)phenyl)butan-2-yl)-1H-indol-4-yl)methanesulfonamide;

(E)-N-(1-(3-(4-chlorophenyl)-1-cyanopent-1-en-3-yl)-1H-indol-4-yl)methanesulfonamide;

(E)-N-(1-(1-cyano-3-(4-methoxyphenyl)pent-1-en-3-yl)-1H-indol-4-yl)methanesulfonamide;

N-(1-(3-(4-chlorophenyl)-5-cyanohex-4-en-3-yl)-1H-indol-4-yl)methanesulfonamide;

N-(1-(3-(4-Chlorophenyl)-1-cyano-2-methylpent-1-en-3-yl)-1H-indol-4-yl)methanesulfonamide;

N-(1-(1-cyano-3-(4-methoxyphenyl)pentan-3-yl)-1H-indol-4-yl)methanesulfonamide;

N-(1-(3-(4-chlorophenyl)-1-cyanopentan-3-yl)-1H-indol-4-yl)methanesulfonamide;

N-(1-(3-(4-chlorophenyl)-1-cyanopentan-3-yl)-6-fluoro-1H-indol-4-yl)methanesulfonamide;

N-(1-(1-(4-Chlorophenyl)-1-(3-cyano-4,5-dihydrofuran-2-yl)propyl)-1H-indol-4-yl)methanesulfonamide;

N-(2-chloroethyl)-2-(4-chlorophenyl)-2-(4-(methylsulfonamido)-1H-indol-1-yl)butanamide;

2-(4-chlorophenyl)-N-(cyanomethyl)-2-(4-(methylsulfonamido)-1H-indol-1-yl)butanamide;

N-(1-(1-(4-chlorophenyl)-1-(3-ethyl-1,2,4-oxadiazol-5-yl)propyl)-1H-indol-4-yl)methanesulfonamide;

N-(1-(1-(4-chlorophenyl)-1-(3-ethyl-1,2,4-oxadiazol-5-yl)propyl)-1H-indol-4-yl)methanesulfonamide;

N-(1-(1-(4-chlorophenyl)-1-(2-ethyl-2H-1,2,3-triazol-4-yl)propyl)-1H-indol-4-yl)methanesulfonamide;

Methyl 2-(4-chlorophenyl)-2-(4-(2-(methylsulfonyl)ethyl)-1H-indol-1-yl)butanoate;

N-(1-(1-(4-chlorophenyl)-1-(1-hydroxycyclopropyl)propyl)-1H-indol-4-yl)methanesulfonamide;

methyl 2-(4-chlorophenyl)-4-fluoro-2-(4-(methylsulfonamido)-1H-indol-1-yl)butanoate;

N-(1-(3-(4-Chlorophenyl)-1-hydroxypentan-3-yl)-1H-indol-4-yl)methanesulfonamide;

N-(1-(3-(4-Chlorophenyl)-1-hydroxypentan-3-yl)-1H-indol-4-yl)methanesulfonamide

N-(1-(3-(4-Chlorophenyl)-1-fluoropentan-3-yl)-1H-indol-4-yl)methanesulfonamide;

N-(1-(3-(4-Chlorophenyl)-1-fluoropentan-3-yl)-1H-indol-4-yl)methanesulfonamide;

3-(4-Chlorophenyl)-3-(4-(methylsulfonamido)-1H-indol-1-yl)pentyl methanesulfonate;

N-(1-(3-(4-Chlorophenyl)-1-methoxypentan-3-yl)-1H-indol-4-yl)methanesulfonamide;

N-(1-(3-(4-chlorophenyl)-1-(methylthio)pentan-3-yl)-1H-indol-4-yl)methanesulfonamide;

methyl 4-(4-amino-1H-indol-1-yl)-4-(4-chlorophenyl)hexanoate;

N-(1-(3-(4-chlorophenyl)-6-hydroxyhexan-3-yl)-1H-indol-4-yl)methanesulfonamide;

N-(1-(3-(4-chlorophenyl)-6-fluorohexan-3-yl)-1H-indol-4-yl)methanesulfonamide;

N-(1-(3-(4-chlorophenyl)-2-hydroxy-1-methoxypentan-3-yl)-1H-indol-4-yl)methane sulfonamide;

N-(1-(3-(4-chlorophenyl)pentan-3-yl)-1H-indol-4-yl)methanesulfonamide;

N-(1-(3-(4-chlorophenyl)pent-1-en-3-yl)-1H-indol-4-yl)methanesulfonamide;

N-(1-(2-amino-3-(4-chlorophenyl)pentan-3-yl)-1H-indol-4-yl)methanesulfonamide;

N-(1-(1-amino-2-(4-chlorophenyl)butan-2-yl)-1H-indol-4-yl)methanesulfonamide;

N-(1-(1-(4-chlorophenyl)-1-cyanopropyl)-1H-indol-4-yl)ethanesulfonamide;

N-(1-(1-(4-chlorophenyl)-1-(2-ethyl-2H-tetrazol-5-yl)propyl)-1H-indol-4-yl)methane sulfonamide;

N-(1-(3-(4-chlorophenyl)-6,6,6-trifluorohexan-3-yl)-1H-indol-4-yl)methanesulfonamide; and

N-(1-(3-(4-chlorophenyl)-1-cyanopent-1-yn-3-yl)-1H-indol-4-yl)methanesulfonamide;

or a pharmaceutically acceptable salt thereof.

2. The compound of claim 1 selected from

(R)—N-{1-[(2R)-2-(4-chlorophenyl)-1-hydroxybutan-2-yl]-1H-indol-4-yl}methanesulfonamide;

N-(1-(1-(4-chlorophenyl)-1-(3-ethyl-1,2,4-oxadiazol-5-yl)propyl)-1H-indol-4-yl)methanesulfonamide;

N-(1-(1-(4-chlorophenyl)-1-(1-hydroxycyclopropyl)propyl)-1H-indol-4-yl)methanesulfonamide;

N-(1-(3-(4-chlorophenyl)-2-hydroxypentan-3-yl)-6-fluoro-1H-indol-4-yl)methanesulfonamide;

N-(1-(2-(4-chlorophenyl)-1-hydroxybutan-2-yl)indolin-4-yl)methanesulfonamide;

N-(1-(2-amino-3-(4-chlorophenyl)pentan-3-yl)-1H-indol-4-yl)methanesulfonamide;

methyl 4-[(methylsulfonyl)amino]-1H-indol-1-yl}(phenyl)acetate;

N-(1-(3-(4-chlorophenyl)-2-hydroxy-2-methylpentan-3-yl)-6-fluoro-1H-indol-4-yl)methane sulfonamide;

N-(1-(3-(4-chlorophenyl)-2-hydroxy-2-methylpentan-3-yl)-1H-indol-4-yl)methanesulfonamide;

N-(1-(2-(4-chlorophenyl)-1-methoxybutan-2-yl)-1H-indol-4-yl)methanesulfonamide;

N-(1-(1-cyano-3-(4-methoxyphenyl)pentan-3-yl)-1H-indol-4-yl)methanesulfonamide;

N-(1-(3-(4-chlorophenyl)-1-cyanopentan-3-yl)-1H-indol-4-yl)methanesulfonamide;

N-(1-(3-(4-chlorophenyl)-1-cyanopentan-3-yl)-6-fluoro-1H-indol-4-yl)methanesulfonamide;

N-(1-(3-(4-Chlorophenyl)-1-hydroxypentan-3-yl)-1H-indol-4-yl)methanesulfonamide;

N-(1-(3-(4-chlorophenyl)-6-hydroxyhexan-3-yl)-1H-indol-4-yl)methanesulfonamide; and

N-(1-(3-(4-chlorophenyl)pentan-3-yl)-1H-indol-4-yl)methanesulfonamide;

or a pharmaceutically acceptable salt thereof.

3. The compound of claim 2 selected from

(R)—N-{1-[(2R)-2-(4-chlorophenyl)-1-hydroxybutan-2-yl]-1H-indol-4-yl}methanesulfonamide;

N-(1-(1-(4-chlorophenyl)-1-(3-ethyl-1,2,4-oxadiazol-5-yl)propyl)-1H-indol-4-yl)methanesulfonamide;

N-(1-(1-(4-chlorophenyl)-1-(1-hydroxycyclopropyl)propyl)-1H-indol-4-yl)methanesulfonamide;

N-(1-(3-(4-chlorophenyl)-2-hydroxypentan-3-yl)-6-fluoro-1H-indol-4-yl)methanesulfonamide;

N-(1-(2-(4-chlorophenyl)-1-hydroxybutan-2-yl)indolin-4-yl)methanesulfonamide;

N-(1-(2-amino-3-(4-chlorophenyl)pentan-3-yl)-1H-indol-4-yl)methanesulfonamide; and

or a pharmaceutically acceptable salt thereof.

4. A pharmaceutical composition comprising the compound of claim 1 and a pharmaceutically acceptable carrier.

5. The pharmaceutical composition of claim 4 further comprising one or more pharmaceutically active agents.

Assignments (1)
MERGER Recorded Aug 8, 2022
From: MERCK SHARP & DOHME CORP.
To: MERCK SHARP & DOHME LLC
Reel/Frame 061102/0145 →
Continuity (3)
Division 13979875
Provisional Application 61434543 · Jan 20, 2011
Related Publication 20150284376A1 · Oct 8, 2015