IP Library › Granted Patent US 10,071,957
Granted Patent B2
US 10,071,957 · App. 14/413,218 · Granted Sep 11, 2018

N-substituted benzamides and methods of use thereof

Inventors: Christoph Martin Dehnhardt (Burnaby, CA); Sultan Chowdhury (Burnaby, CA); Thilo Focken (Burnaby, CA); Michael Edward Grimwood (Burnaby, CA); Ivan William Hemeon (Burnaby, CA); Brian Safina (South San Francisco, CA); Daniel P. Sutherlin (South San Francisco, CA)
Assignees: GENENTECH, INC.; XENON PHARMACEUTICALS INC.
C07C307/06C07D205/04C07D209/08C07D213/63C07D213/64C07D213/69C07D213/74C07D215/20C07D217/02C07D231/56C07D277/24C07D277/34C07D277/62C07D305/08C07D401/12C07D405/12C07D413/12C07C2601/04
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Quick Facts
Patent No.
US 10,071,957
App. No.
14/413,218
Granted
Sep 11, 2018
Kind
B2
Abstract

The invention provides novel compounds having the general formula (I) and pharmaceutically acceptable salts thereof, wherein the variables RA, subscript n, ring A, X 2 , L, subscript m, X 1 , ring D, R 1 , and R N have the meaning as described herein, and compositions containing such compounds and methods for using such compounds and compositions.

Claims (70)

1. A compound selected from the group consisting of:

5-chloro-4-((5-chloro-6- isobutoxypyridin-3-yl)oxy)-2- fluoro-N-sulfamoylbenzamide

5-chloro-4-((5-chloro-6- isobutoxypyridin-3-yl)oxy)-2- fluoro-N-(N- methylsulfamoyl)benzamide

5-chloro-4-(4-chloro-3- (trifluoromethyl)phenoxy)-2- fluoro-N-sulfamoylbenzamide

5-chloro-4-(4-chloro-3- (trifluoromethyl)phenoxy)-2- fluoro-N-(N- methylsulfamoyl)benzamide

5-chloro-4-(3-chloro-4- (trifluoromethoxy)phenoxy)-2- fluoro-N-sulfamoylbenzamide

5-chloro-4-(3-chloro-4- (trifluoromethoxy)phenoxy)-2- fluoro-N-(N- methylsulfamoyl)benzamide

5-chloro-4-((5-chloro-6- isobutoxypyridin-3-yl)oxy)-N- (N,N-dibutylsulfamoyl)-2- fluorobenzamide

5-chloro-4-((5-chloro-6- isobutoxypyridin-3-yl)oxy)-2- fluoro-N-(pyrrolidin-1- ylsulfonyl) benzamide

5-chloro-4-((5-chloro-6- isobutoxypyridin-3-yl)oxy)-2- fluoro-N-(piperidin-1- ylsulfonyl)benzamide

N-(azepan-1-ylsulfonyl)-5- chloro-4-((5-chloro-6- isobutoxypyridin-3-yl)oxy)-2- fluorobenzamide

5-chloro-4-((5-chloro-6- isobutoxypyridin-3-yl)oxy)-2- fluoro-N-(N-isopropyl-N- methylsulfamoyl) benzamide

N-(N-benzylsulfamoyl)-5-chloro- 4-((5-chloro-6-isobutoxypyridin- 3-yl)oxy)-2-fluorobenzamide

N-(N-benzyl-N- methylsulfamoyl)-5-chloro-4- ((5-chloro-6-isobutoxypyridin-3- yl)oxy)-2-fluorobenzamide

5-chloro-4-((5-chloro-6- isobutoxypyridin-3-yl)oxy)-2- fluoro-N-(N-(pyridin-2- ylmethyl)sulfamoyl)benzamide 2,2,2-trifluoroacetate

5-chloro-4-((5-chloro-6- isobutoxypyridin-3-yl)oxy)-N-(N- (4-cyanophenyl)sulfamoyl)-2- fluorobenzamide

5-chloro-4-((5-chloro-6- isobutoxypyridin-3-yl)oxy)-2- fluoro-N-(N-(pyridin-3- ylmethyl)sulfamoyl)benzamide 2,2,2-trifluoroacetate

5-chloro-4-((3,4- dichlorobenzyl)oxy)-N-(N,N- dimethylsulfamoyl)-2- fluorobenzamide

5-chloro-4-((5-chloro-6- isobutoxypyridin-3-yl)oxy)-2- fluoro-N-((1-methyl-1H- imidazol-4- yl)sulfonyl)benzamide

5-chloro-4-((5-chloro-6- isobutoxypyridin-3-yl)oxy)-2- fluoro-N-(indolin-1- ylsulfonyl)benzamide

N-((1H-imidazol-4-yl)sulfonyl)-5- chloro-4-((5-chloro-6- isobutoxypyridin-3-yl)oxy)-2- fluorobenzamide

1-(N-(5-chloro-4-((5-chloro-6- isobutoxypyridin-3-yl)oxy)-2- fluorobenzoyl)sulfamoyl)piperidine- 4-carboxylate

5-chloro-4-((5-chloro-6- isobutoxypyridin-3-yl)oxy)-2- fluoro-N-(pyridin-3- ylsulfonyl)benzamide

tert-butyl N-(5-chloro-4-((5- chloro-6-isobutoxypyridin-3- yl)oxy)-2- fluorobenzoyl)sulfamoylcarbamate

4-(3-chloro-4- (trifluoromethoxy)phenoxy)-N- (N,N-dimethylsulfamoyl)-2,5- difluorobenzamide

N-(N,N-dimethylsulfamoyl)-4- fluoro-6-((5-methyl-3- phenylisoxazol-4- yl)methoxy)nicotinamide

5-chloro-4-((5-chloro-6-(2,2,3,3- tetrafluoropropoxy)pyridin-3- yl)oxy)-2-fluoro-N-(N- methylsulfamoyl)benzamide

5-chloro-4-((5,6- dichloropyridin-3-yl)oxy)-2- fluoro-N-sulfamoylbenzamide

5-chloro-4-((5,6- dichloropyridin-3-yl)oxy)-N- (N,N-dimethylsulfamoyl)-2- fluorobenzamide

5-chloro-4-(((5-chloro-6- (2,2,3,3- tetrafluoropropoxy)pyridin-3- yl)oxy)methyl)-2-fluoro-N- sulfamoylbenzamide

5-chloro-4-((5-chloro-6-(2,2,3,3- tetrafluoropropoxy)pyridin-3- yl)oxy)-2-fluoro-N- sulfamoylbenzamide

5-chloro-4-((5,6- dichloropyridin-3-yl)oxy)-2- fluoro-N-(N- methylsulfamoyl)benzamide

5-chloro-N-(N,N- dimethylsulfamoyl)-2-fluoro-4- ((6-isobutoxy-5- (trifluoromethyl)pyridin-3- yl)oxy)benzamide

tert-butyl 4-(N-(5-chloro-4-((5- chloro-6-isobutoxypyridin-3- yl)oxy)-2- fluorobenzoyl)sulfamoyl)piperazine- 1-carboxylate

5-chloro-4-((5-chloro-6- isobutoxypyridin-3-yl)oxy)-2- fluoro-N-(piperazin-1- ylsulfonyl)benzamide

5-chloro-4-(4-cyanophenoxy)-N- (N,N-dimethylsulfamoyl)-2- fluorobenzamide

5-chloro-N-(N,N- dimethylsulfamoyl)-2-fluoro-4- (4-(thiazol-2- yl)phenoxy)benzamide

5-chloro-4-(3-chloro-4- (trifluoromethoxy)phenoxy)-N- (N-cyclobutylsulfamoyl)-2- fluorobenzamide

N-(azetidin-1-ylsulfonyl)-5- chloro-4-((5-chloro-6- isobutoxypyridin-3-yl)oxy)-2- fluorobenzamide

5-chloro-N-(N,N- dimethylsulfamoyl)-2-fluoro-4- (naphthalen-2-yloxy)benzamide

5-chloro-2-fluoro-4- (naphthalen-2-yloxy)-N- sulfamoylbenzamide

5-chloro-4-(3,4- difluorophenoxy)-N-(N,N- dimethylsulfamoyl)-2- fluorobenzamide

5-chloro-4-(3,4- difluorophenoxy)-2-fluoro-N- sulfamoylbenzamide

5-chloro-N-(N,N- dimethylsulfamoyl)-2-fluoro-4- (2-phenoxyethoxy)benzamide

5-chloro-N-(N,N- dimethylsulfamoyl)-2-fluoro-4- (naphthalen-1-yloxy)benzamide

5-chloro-2-fluoro-4- (naphthalen-1-yloxy)-N- sulfamoylbenzamide

4-((1H-indol-5-yl)oxy)-5-chloro- N-(N,N-dimethylsulfamoyl)-2- fluorobenzamide

4-((1H-indol-4-yl)oxy)-5-chloro- N-(N,N-dimethylsulfamoyl)-2- fluorobenzamide

4-((1H-indol-6-yl)oxy)-5-chloro- N-(N,N-dimethylsulfamoyl)-2- fluorobenzamide

5-chloro-N-(N,N- dimethylsulfamoyl)-2-fluoro-4- (4- methoxyphenethoxy)benzamide

5-chloro-N-(N,N- dimethylsulfamoyl)-2-fluoro-4- phenethoxybenzamide

5-chloro-N-(N,N- dimethylsulfamoyl)-2-fluoro-4- ((2-methyl-1H-indol-5- yl)oxy)benzamide

5-chloro-N-(N,N- dimethylsulfamoyl)-2-fluoro-4- (isoquinolin-5-yloxy)benzamide

5-chloro-N-(N,N- dimethylsulfamoyl)-2-fluoro-4- (4- (methylsulfonyl)phenoxy)benzamide

5-chloro-N-(N,N- dimethylsulfamoyl)-2-fluoro-4- ((1-methyl-1H-indazol-6- yl)oxy)benzamide

5-chloro-4-((5-chloro-6- (piperidin-1-yl)pyridin-3-yl)oxy)- N-(N,N-dimethylsulfamoyl)-2- fluorobenzamide

5-chloro-N-(N,N- dimethylsulfamoyl)-2-fluoro-4- ((2-methylbenzo[d]thiazol-6- yl)oxy)benzamide

4-((5-chloro-6-isobutoxypyridin- 3-yl)oxy)-5-cyano-N-(N,N- dimethylsulfamoyl)-2- fluorobenzamide

5-chloro-4-((5-chloro-6-(2,2,3,3- tetrafluoropropoxy)pyridin-3- yl)oxy)-2-fluoro-N-(pyrrolidin-1- ylsulfonyl)benzamide

5-chloro-4-((5-chloro-6-(2,2,3,3- tetrafluoropropoxy)pyridin-3- yl)oxy)-2-fluoro-N- (morpholinosulfonyl)benzamide

5-chloro-4-((5-chloro-6- isobutoxypyridin-3-yl)oxy)-2- fluoro-N- (morpholinosulfonyl)benzamide

5-chloro-4-((5-chloro-6-(2,2,3,3- tetrafluoropropoxy)pyridin-3- yl)oxy)-2-fluoro-N-(pyridin-3- ylsulfonyl)benzamide

5-chloro-N-(N,N- dimethylsulfamoyl)-2-fluoro-4- (2-fluoro-5- (trifluoromethoxyphenoxy)benzamide

5-chloro-N-(N,N- dimethylsulfamoyl)-2-fluoro-4- (quinolin-5-yloxy)benzamide

5-chloro-N-(N,N- dimethylsulfamoyl)-2-fluoro-4- (quinolin-6-yloxy)benzamide

5-chloro-N-(N,N- dimethylsulfamoyl)-2-fluoro-4- (isoquinolin-7-yloxy)benzamide

5-chloro-4-(4-cyano-3,5- dimethylphenoxy)-N-(N,N- dimethylsulfamoyl)-2- fluorobenzamide, and

4-((5-chloro-6-isobutoxypyridin- 3-yl)oxy)-5-cyano-2-fluoro-N- sulfamoylbenzamide

or a pharmaceutically acceptable salt thereof.

2. A pharmaceutical composition comprising a compound as described in claim 1 or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 4, 2016
From: SAFINA, BRIAN; SUTHERLIN, DANIEL P.
To: GENENTECH, INC.
Reel/Frame 037402/0753 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 4, 2016
From: DEHNHARDT, CHRISTOPH MARTIN; CHOWDHURY, SULTAN; FOCKEN, THILO; GRIMWOOD, MICHAEL EDWARD; HEMEON, IVAN WILLIAM
To: XENON PHARMACEUTICALS INC.
Reel/Frame 037402/0841 →
Continuity (2)
Provisional Application 61668951 · Jul 6, 2012
Related Publication 20150322002A1 · Nov 12, 2015