US2015224071A1PendingUtilityA1
N-substituted benzamides and methods of use thereof
Est. expiryMay 22, 2032(~5.9 yrs left)· nominal 20-yr term from priority
Inventors:Sultan ChowdhuryChristoph Martin DehnhardtThilo FockenMichael Edward GrimwoodIvan William HemeonQi JiaDaniel Fred OrtwineBrian SafinaShaoyi SunDaniel P. SutherlinAlla Yurevna Zenova
A61P 35/00A61P 9/10A61P 9/00A61P 43/00A61P 25/18A61P 25/08A61P 25/06A61P 25/04A61P 25/02A61P 25/24A61P 25/22A61P 29/00A61P 1/04A61P 13/10A61P 11/00A61P 21/00A61P 25/00A61P 19/02A61P 17/04A61K 31/18C07D 207/46C07D 405/12C07C 2603/68C07C 2602/10C07D 307/12C07C 2601/18C07D 205/04C07B 2200/05A61K 31/41C07C 2601/08C07C 311/51C07D 311/70C07D 307/18C07D 309/08C07C 307/06C07D 403/12C07C 2602/50C07C 2602/42A61K 31/445C07C 2602/44C07D 233/84A61K 31/40C07D 295/26C07C 2602/20C07D 213/64C07D 311/72C07C 2603/74C07D 207/48C07C 2601/02C07C 2602/18C07D 209/52C07C 2601/14A61K 31/397C07D 213/82C07C 2603/66A61K 31/4164C07D 311/58C07D 265/30C07D 257/04C07D 211/22C07D 491/107C07D 295/192A61K 31/44C07D 451/02C07D 471/08A61K 31/5375C07D 207/08C07D 211/96C07C 2601/04C07D 413/12C07C 2601/16
64
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Claims
Abstract
The invention provides novel compounds having the general formula: and pharmaceutically acceptable salts thereof, wherein the variables R A , subscript n, ring A, X 2 , L, subscript m, X 1 , B, R 1 , R 2 , R 3 , R 4 , R 5 and R N have the meaning as described herein, and compositions containing such compounds and methods for using such compounds and compositions.
Claims
exact text as granted — not AI-modified1 - 37 . (canceled)
38 . A method of treating pruritus in a mammal, wherein the method comprises administering to the mammal in need thereof a therapeutically effective amount of a compound of Formula I or a pharmaceutically acceptable salt thereof:
wherein in Formula I:
R 1 is C 1-8 alkyl, C 1-8 haloalkyl, C 1-8 alkoxy, C 3-12 cycloalkyl, C-linked C 2-11 heterocycloalkyl, heteroaryl, or —NR 1A R 1B , wherein R 1A and R 1B are each independently selected from the group consisting of hydrogen, C 1-8 alkyl, C 1-8 alkoxy, (6-10 membered aryl)-(X R1 ) 0-1 —, (5-10 membered heteroaryl)-(X R1 ) 0-1 —, and wherein R 1A and R 1B are optionally combined to form a 3 to 8 membered heterocyclic ring optionally comprising 1 additional heteroatom selected from N, O and S as ring vertex and optionally fused thereto is a benzene or pyridine ring; X R1 is selected from the group consisting of C 1-4 alkylene, C 1-4 heteroalkylene, C 2-4 alkenylene, C 2-4 alkynylene; and wherein the aliphatic and aromatic portions of R 1 are optionally substituted with from 1 to 5R R1 substituents selected from the group consisting of C 1-8 alkyl, C 1-8 haloalkyl, F, Cl, Br, I, —OH, —CN, —NO 2 , ═O, —(X 1R ) 0-1 NR R1a R R1b , (X 1R ) 0-1 OR R1a , —(X 1R ) 0-1 SR R1a , —(X 1R ) 0-1 N(R R1a )C(═O)OR R1c , —(X 1R ) 0-1 OC(═O)N(R R1a )(OR R1b ), —(X 1R ) 0-1 N(R R1a )C(═O)N(R R1a )(R R1b ), —(X 1R ) 0-1 C(═O)N(R R1a )(R R1b ), —(X 1R ) 0-1 N(R R1a )C(═O)R R1b , —(X 1R ) 0-1 C(═O)OR R1a , —(X 1R ) 0-1 OC(═O)R R1a , —(X 1R ) 0-1 —P(═)(OR R1a )(OR R1b ), —(X R1 ) 0-1 S(O) 1-2 R R1c , —(X 1R ) 0-1 S(O) 1-2 N(R R1a )(R R1b ), —(X 1R ) 0-1 N(R R1a )S(O) 1-2 N(R R1a )(R R1b ) and —(X 1R ) 0-1 N(R R1a )S(O) 1-2 (R R1c ), wherein X 1R is selected from the group consisting of C 1-4 alkylene, C 1-4 heteroalkylene, C 2-4 alkenylene and C 2-4 alkynylene; wherein R R1a and R R1b are independently selected from the group consisting of hydrogen, C 1-8 alkyl, C 1-8 haloalkyl, C 3-8 cycloalkyl, phenyl, benzyl, heteroaryl, and C 2-7 heterocycloalkyl; R R1c is selected from the group consisting of C 1-8 alkyl, C 1-8 haloalkyl, C 3-8 cycloalkyl, phenyl, benzyl, heteroaryl, and C 2-7 heterocycloalkyl;
R N is hydrogen, C 1-4 alkyl or C 1-4 haloalkyl;
B is C or N;
R 2 , R 3 and R 4 are each independently selected from the group consisting of H, F, Cl, Br, I, —CN, C 1-8 alkyl, C 1-8 haloalkyl and C 1-8 alkoxy, and R 3 is absent when B is nitrogen;
R 5 is selected from the group consisting of H, F, Cl, Br, I, —CN, C 1-8 alkyl, C 1-8 haloalkyl, C 1-8 alkoxy, C 3-8 cycloalkyl, C 2-7 heterocycloalkyl, phenyl and 5-6 membered heteroaryl comprising 1 to 3 heteroatoms selected from N, O and S, wherein said 5-6 membered heteroaryl is further optionally substituted with from 1 to 3 R 5 substituents selected from F, Cl, Br, I, —CN, C 1-4 alkyl, C 1-4 haloalkyl and C 1-4 alkoxy;
L is a linker selected from the group consisting of C 1-4 alkylene, C 2-4 alkenylene, C 2-4 alkynylene, and C 1-4 heteroalkylene, wherein L is optionally substituted with from 1 to 3 R L substituents selected from the group consisting of ═O, C 1-4 alkyl, C 1-4 haloalkyl and C 1-4 acyl; the subscript m represents the integer 0 or 1;
X 1 and X 2 are each independently selected from the group consisting of absent, —O—, —S(O)—, —S(O) 2 — and —N(R X )— wherein R x is H, C 1-8 alkyl, C 1-8 acyl or —S(O) 2 (C 1-8 alkyl), and wherein if the subscript m is 0 then one of X 1 or X 2 is absent; and
A-(R A ) n is selected from the group consisting of:
39 . The method of claim 38 wherein:
R 1 is C 1-8 alkyl, C 1-8 haloalkyl, C 1-8 alkoxy, C 3-12 cycloalkyl, C-linked C 2-11 heterocycloalkyl or —NR 1A R 1B , wherein R 1A and R 1B are each independently selected from the group consisting of hydrogen, C 1-8 alkyl, C 1-8 alkoxy, (6-10 membered aryl)-(X R1 ) 0-1 —, (5-10 membered heteroaryl)-(X R1 ) 0-1 —, and wherein R 1A and R 1B are optionally combined to form a 3 to 8 membered heterocyclic ring optionally comprising 1 additional heteroatoms selected from N, O and S as ring vertex and optionally fused thereto is a benzene or pyridine ring; X R1 is selected from the group consisting of C 1-4 alkylene, C 1-4 heteroalkylene, C 2-4 alkenylene, C 2-4 alkynylene; and wherein the aliphatic and aromatic portions of R 1 are optionally substituted with from 1 to 5 R R1 substituents selected from the group consisting of C 1-8 alkyl, C 1-8 haloalkyl, F, Cl, Br, I, —OH, —CN, —NO 2 , —(X 1R ) 0-1 NR R1a R R1b , —(X 1R ) 0-1 OR R1a , —(X 1R ) 0-1 SR R1a , (X R1 ) 0-1 N(R R1a )C(═O)OR R1c , — (X 1R ) 0-1 C(═ 0 ) N(R R1a )(R R1b ), —(X 1R ) 0-1 N(R R1a )C(═O)N(R R1a )(R R1b ), —(X 1R ) 0-1 C(═O)N(R R1a )(R R1b ), —(X 1R ) 0-1 N(R R1a )C(═O)R R1b , —(X 1R ) 0-1 C(═O)OR R1a , —(X 1R ) 0-1 C(═O)R R1a , —(X 1R ) 0-1 —P(═O)(OR R1a )(OR R1b ), —(X 1R ) 0-1 S(O) 1-2 R R1c , —(X 1R ) 0-1 S(O) 1-2 N(R R1a )(R R1b ), —(X 1R ) 0-1 N(R R1a )S(O) 1-2 N(R R1a )(R R1b ) and —(X 1R ) 0-1 N(R R1a )S(O) 1-2 (R R1C ), wherein X 1R is selected from the group consisting of C 1-4 alkylene, C 1-4 heteroalkylene, C 2-4 alkenylene and C 2-4 alkynylene; wherein R R1a and R R1b are independently selected from the group consisting of hydrogen, C 1-8 alkyl, C 1-8 haloalkyl, C 3-8 cycloalkyl, phenyl, benzyl, C 5-6 heteroaryl and C 2-7 heterocycloalkyl; R R1c is selected from the group consisting of C 1-8 alkyl, C 1-8 haloalkyl, C 3-8 cycloalkyl, phenyl, benzyl, C 5-6 heteroaryl and C 2-7 heterocycloalkyl;
R N is hydrogen, C 1-4 alkyl or C 1-4 haloalkyl;
B is C or N;
R 2 , R 3 and R 4 are each independently selected from the group consisting of H, F, Cl, Br, I, —CN, C 1-8 alkyl, C 1-8 haloalkyl and C 1-8 alkoxy, and R 3 is absent when B is nitrogen;
R 5 is selected from the group consisting of H, F, Cl, Br, I, —CN, C 1-8 alkyl, C 1-8 haloalkyl, C 1-8 alkoxy, C 3-8 cycloalkyl, C 2-7 heterocycloalkyl, phenyl and 5-6 membered heteroaryl comprising 1 to 3 heteroatoms selected from N, O and S, wherein said 5-6 membered heteroaryl is further optionally substituted with from 1 to 3 R 5 substituents selected from F, Cl, Br, I, —CN, C 1-4 alkyl, C 1-4 haloalkyl and C 1-4 alkoxy;
L is a linker selected from the group consisting of C 1-4 alkylene, C 2-4 alkenylene, C 2-4 alkynylene, and C 1-4 heteroalkylene, wherein L is optionally substituted with from 1 to 3 R L substituents selected from the group consisting of ═O, C 1-4 alkyl, C 1-4 haloalkyl and C 1-4 acyl;
the subscript m represents the integer 0 or 1;
X 1 and X 2 are each independently selected from the group consisting of absent, —O—, —S(O)—, —S(O) 2 — and —N(R X )— wherein R x is C 1-8 alkyl, C 1-8 acyl or —S(O) 2 (C 1-8 alkyl), and wherein if the subscript m is 0 then one of X 1 or X 2 is absent.
40 . The method of claim 38 , wherein the compound has the formula
41 . The method of claim 38 wherein B is N and R 3 is absent.
42 . The method of claim 38 wherein B is C.
43 . The method of claim 38 wherein R 2 , R 3 and R 4 are each independently selected from H, F, or Cl.
44 . The method of claim 38 wherein R 2 is H, F or Cl; R 3 and R 4 are each H; and R 5 is an optionally substituted group selected from the group consisting of H, F, Cl, Br, I, —CN, C 1-8 alkyl, C 1-8 haloalkyl and C 1-8 alkoxy.
45 . The method of claim 38 wherein R 1 is C 1-8 alkyl, C 1-8 haloalkyl, C 3-10 cycloalkyl or —NR 1A R 1B .
46 . The method of claim 38 , wherein R 1 is selected from the group consisting of methyl, ethyl, propyl, trifluoromethyl, difluoromethyl, monofluoromethyl, isopropyl and cyclopropyl.
47 . The method of claim 38 , wherein R 1 is selected from the group consisting of: —NH(CH 3 ), —N(CH 3 ) 2 ,
48 . The method of claim 38 wherein R 1 is selected from the group consisting of: methyl, ethyl, tert-butyl, dimethylamino, methylamino, amino, morpholino, azetidino, imidazolyl, 3-hydroxyazetidino, 3-fluoroazetidino, cyclopropyl, pyrrolidinyl, 3,3-difluoroazetidino, tert-butyl, ethyl, 2-methoxyethyl, 3-methoxyazetidino, 2-hydroxyethyl, 3-hydroxypyrrolidinyl, and N-methylimidazolyl.
49 . The method of claim 38 wherein X 1 is —O— or —N(H)—; X 2 is absent; the subscript m is 1; and -(L)- is an optionally substituted group selected from the group consisting of C 1-4 alkylene, C 2-4 alkenylene and C 2-4 alkynylene.
50 . The method of claim 38 , wherein X 1 is —O— or —N(H)—; X 2 is absent; the subscript m is 1; and -(L)- is selected from the group consisting of —CH 2 —, —C(═O)—, —C(H)(CH 3 )—, —CH 2 —CH 2 —, —CH 2 —C(H)(CH 3 )—, —C(H)(CH 3 )—C(H 2 )—, —CH 2 CH 2 CH 2 —, —CH 2 —C(H)(CH 3 )—CH 2 — and —CH 2 CH 2 CH 2 CH 2 —.
51 . The method of claim 38 , wherein X 1 is —O—; the subscript m is 1 and -(L)- is —CH 2 — or —CH 2 —CH 2 —.
52 . The method of claim 38 wherein X 1 is absent; X 2 is —O— or —N(H)—; the subscript m is 1; and -(L)- is selected from the group consisting of —C(H) 2 —, —C(═O)—, —C(H)(CH 3 )—, —CH 2 —CH 2 —, —CH 2 —C(H)(CH 3 )—, —C(H)(CH 3 )—C(H 2 )—, —CH 2 CH 2 CH 2 —, —CH 2 —C(H)(CH 3 )—CH 2 — and —CH 2 CH 2 CH 2 CH 2 —.
53 . The method of claim 38 wherein X 1 and X 2 is absent; the subscript m is 1; and -(L)- is selected from the group consisting of —C(H) 2 —, —C(═O)—, —C(H)(CH 3 )—, —CH 2 —CH 2 —, —CH 2 —C(H)(CH 3 )—, —C(H)(CH 3 )—C(H 2 )—, —CH 2 CH 2 CH 2 —, —CH 2 —C(H)(CH 3 )—CH 2 — and —CH 2 CH 2 CH 2 CH 2 —.
54 . The method of claim 38 wherein X 1 and X 2 is absent; the subscript m is 1; and -(L)- is an optionally substituted C 1-4 heteroalkylene.
55 . The method of claim 38 wherein m is 0; X 1 is selected from —O—, and —N(H)—; and X 2 is absent.
56 . A method of treating pruritus in a mammal, wherein the method comprises administering to the mammal in need thereof a therapeutically effective amount of a compound selected from:
Structure
Name
4-((adamantan-1-ylmethoxy)-2,5- difluoro-N- (methylsulfonyl)benzamide
4-(adamantan-1-ylmethoxy)-5- chloro-2-fluoro-N- (methylsulfonyl)benzamide
5-chloro-4-(((1S,2S,5S)-6,6- dimethylbicyclo[3.1.1]heptan-2- yl)methoxy)-2-fluoro-N- (methylsulfonyl)benzamide
4-(adamantan-2-yloxy)-5-chloro-2- fluoro-N-(methylsulfonyl)benzamide
5-chloro-2-fluoro-N- (methylsulfonyl)-4-(((1R,2R,3R,5S)- 2,6,6-trimethylbicyclo[3.1.1]heptan- 3-yl)oxy)benzamide
4-(2-(adamantan-1-yl)ethoxy)-5- chloro-2-fluoro-N- (methylsulfonyl)benzamide
5-chloro-2-fluoro-N- (methylsulfonyl)-4-(((1S,2R,4S)- 1,7,7-trimethylbicyclo[2.2.1]heptan- 2-yl)oxy)benzamide
5-chloro-2-fluoro-N- (methylsulfonyl)-4-((exo-1,7,7- trimethylbicyclo[2.2.1]heptan-2- yl)oxy)benzamide
5-chloro-2-fluoro-N- (methylsulfonyl)-4-(((1S,2S,3S,5R)- 2,6,6-trimethylbicyclo[3.1.1]heptan- 3-yl)oxy)benzamide
5-chloro-2-fluoro-4-((3- fluoroadamantan-1-yl)methoxy)-N- (methylsulfonyl)benzamide
4-(((3s,5s,7s)-adamantan-1- ylamino)methyl)-3-chloro-N- (methylsulfonyl)benzamide
4-((-adamantan-1-ylmethyl)amino)- 5-chloro-2-fluoro-N- (methylsulfonyl)benzamide
4-(adamantan-1-ylmethoxy)-3- chloro-N-(methylsulfonyl)benzamide
4-(2-(adamantan-1-yl)ethoxy)-3- chloro-N-(methylsulfonyl)benzamide
6-(adamantan-1-ylmethoxy)-5- chloro-N-methanesulfonylpyridine- 3-carboxamide
5-chloro-4-((-3,5- dimethyladamantan-1-yl)methoxy)- 2-fluoro-N- (methylsulfonyl)benzamide
3-chloro-4-(((1r,3s,5R,7S)-3- hydroxyadamantan-1-yl)methoxy)- N-(methylsulfonyl)benzamide
5-chloro-2-fluoro-N- (methylsulfonyl)-4-(((1R,2S,4R)- 1,7,7-trimethylbicyclo[2.2.1]heptan- 2-yl)oxy)benzamide
4-(adamantan-1-ylmethoxy)-5- chloro-N-(N,N-dimethylsulfamoyl)- 2-fluorobenzamide
N1-((3s,5s,7s)-adamantan-1-yl)-2- chloro-5-fluoro-N4- (methylsulfonyl)terephthalamide
5-chloro-2-fluoro-4-((3- hydroxyadamantan-1-yl)methoxy)- N-(methylsulfonyl)benzamide
4-(1-(adamantan-1-yl)ethoxy)-5- chloro-2-fluoro-N- (methylsulfonyl)benzamide
4-(adamantan-2-yloxy)-5-chloro-N- (N,N-dimethylsulfamoyl)-2- fluorobenzamide
5-chloro-4-(((1S,2S,5S)-6,6- dimethylbicyclo[3.1.1]heptan-2- yl)methoxy)-N-(N,N- dimethylsulfamoyl)-2- fluorobenzamide
4-(((3s,5s,7s)-adamantan-1- yl(methyl)amino)methyl)-3-chloro- N-(methylsulfonyl)benzamide
N1-((3s,5s,7s)-adamantan-1-yl)-2- chloro-5-fluoro-N1-methyl-N4- (methylsulfonyl)terephthalamide
5-chloro-2-fluoro-4-((3- methoxyadamantan-1-yl)methoxy)- N-(methylsulfonyl)benzamide
5-chloro-2-fluoro-N- (methylsulfonyl)-4-((4- pentylbicyclo[2.2.2]octan-1- yl)methoxy)benzamide
5-chloro-4-(((1R,2s,3S,5s,7s)-5- chloroadamantan-2-yl)oxy)-2-fluoro- N-(methylsulfonyl)benzamide
5-chloro-4-(((1R,2r,3S,5s,7s)-5- chloroadamantan-2-yl)oxy)-2-fluoro- N-(methylsulfonyl)benzamide
6-(1-adamantylmethoxy)-5- cyclopropyl-N-methylsulfonyl- pyridine-3-carboxamide
4-(2-adamantyloxymethyl)-5- cyclopropyl-2-fluoro-N- methylsulfonylbenzamide
4-(1-adamantylmethoxy)-5-ethyl-2- fluoro-N-methylsulfonylbenzamide
4-(1-adamantylmethoxy)-N- (azetidin-1-ylsulfonyl)-5-ethyl-2- fluoro-benzamide
4-(1-adamantylmethoxy)-5- cyclopropyl-2-fluoro-N-(3- hydroxyazetidin-1-yl)sulfonyl- benzamide
4-(1-adamantylmethoxy)-5- cyclopropyl-2-fluoro-N-(2- hydroxyethylsulfonyl)benzamide
4-(1-adamantylmethoxy)-5- cyclopropyl-2-fluoro-N-(2- methoxyethylsulfonyl)benzamide
4-(1-adamantylmethoxy)-3- cyclobutyl-N- methylsulfonylbenzamide
4-(2-adamantyloxymethyl)-5-chloro- 2-fluoro-N- methylsulfonylbenzamide
4-(1-adamantylmethoxy)-N- (azetidin-1-ylsulfonyl)-3- (trifluoromethyl)-benzamide
5-chloro-4-[[(1R,2R,5R)-6,6- dimethylnorpinan-2-yl]methoxy]-2- fluoro-N-methylsulfonylbenzamide
4-(2-adamantylmethoxy)-3- cyclopropyl-N-methylsulfonyl- benzamide
4-(1-adamantylmethoxy)-5-chloro-2- methoxy-N- methylsulfonylbenzamide
4-(1-adamantylmethoxy)-5- cyclopropyl-2-fluoro-N- methylsulfonylbenzamide
4-(1-adamantylmethoxy)-3-bromo- N-methylsulfonylbenzamide
4-(1-adamantylmethoxy)-N- methylsulfonyl-3- (trifluoromethyl)benzamide
4-(1-adamantylmethoxy)-5- cyclopropyl-2-fluoro-N- (methylsulfamoyl)benzamide
4-(1-adamantylmethoxy)-N- (azetidin-1-ylsulfonyl)-5- cyclopropyl-2-fluoro-benzamide
4-(1-adamantylmethoxy)-5-chloro-2- fluoro-N-(2-hydroxyethylsulfonyl)- benzamide
4-(1-adamantylmethoxy)-2,5- dichloro-N- methylsulfonylbenzamide
4-(1-adamantylmethoxy)-5-chloro-2- fluoro-N- (methylsulfamoyl)benzamide
4-(1-adamantylmethoxy)-N- (azetidin-1-ylsulfonyl)-5-chloro-2- fluoro-benzamide
4-(1-adamantylmethoxy)-5-chloro-2- fluoro-N-(1-methylimidazol-4- yl)sulfonylbenzamide
4-(1-adamantylmethoxy)-5-chloro-2- fluoro-N-(2-methoxyethylsulfonyl)- benzamide
4-(1-adamantylmethoxy)-5-chloro-2- fluoro-N-(1H-imidazol-4- ylsulfonyl)benzamide
4-(1-adamantylmethoxy)-5-chloro-2- fluoro-N-morpholinosulfonyl- benzamide
5-chloro-2-fluoro-N-methylsulfonyl- 4-[[3-(5-methyltetrazol-2-yl)-1- adamantyl]methoxy]benzamide
5-chloro-N-(dimethylsulfamoyl)-2- fluoro-4-[(1-pentyl-4-bicyclo[2.2.2]- octanyl)methoxy]benzamide
5-chloro-4-[(3-chloro-1- adamantyl)methoxy]-N- (dimethylsulfamoyl)-2-fluoro- benzamide
4-(1-adamantylmethoxy)-3- cyclopropyl-N-(dimethylsulfamoyl)- benzamide
4-(1-adamantyloxymethyl)-5-chloro- 2-fluoro-N- methylsulfonylbenzamide
4-(1-adamantylmethoxy)-3- cyclopropyl-N-methylsulfonyl- benzamide
5-chloro-N-(dimethylsulfamoyl)-2- fluoro-4-[(3-fluoro-1- adamantyl)methoxy]benzamide
5-chloro-4-[(4,4-difluoro-1- adamantyl)methoxy]-N- (dimethylsulfamoyl)-2-fluoro- benzamide
5-chloro-2-fluoro-N-methylsulfonyl- 4-[[4-(trifluoromethyl)cyclohexyl]- methoxy]benzamide
5-chloro-4-[[(1S,2S,5S)-6,6- dimethylnorpinan-2-yl]methoxy]-2- fluoro-N-sulfamoylbenzamide
5-chloro-4-[[(1S,2R,5S)-6,6- dimethylnorpinan-2-yl]methoxy]-N- (dimethylsulfamoyl)-2-fluoro- benzamide
4-(2-adamantylmethoxy)-5-chloro- N-(dimethylsulfamoyl)-2-fluoro- benzamide
5-chloro-4-[(3-chloro-1- adamantyl)methoxy]-2-fluoro-N- methylsulfonylbenzamide
5-chloro-2-fluoro-N-methylsulfonyl- 4-[[4-(trifluoromethyl)cyclohexyl]- methoxy]benzamide
5-chloro-4-[[(1S,2R,5S)-6,6- dimethylnorpinan-2-yl]methoxy]-2- fluoro-N-methylsulfonylbenzamide
4-(1-adamantylmethoxy)-3-(2- methoxy-3-pyridyl)-N- methylsulfonyl-benzamide
4-(2-adamantylmethoxy)-5-chloro-2- fluoro-N-methylsulfonylbenzamide
5-chloro-2-fluoro-N-methylsulfonyl- 4-[(1-pentyl-4- bicyclo[2.2.2]octanyl)- methoxy]benzamide
5-chloro-2-fluoro-N-methylsulfonyl- 4-[(1R,2R,4S)-1,3,3- trimethylnorbornan-2- yl]oxybenzamide
5-chloro-4-(3,3- dimethylcyclohexoxy)-2-fluoro-N- methylsulfonylbenzamide
5-chloro-N-(dimethylsulfamoyl)-2- fluoro-4-[(1S,2R,4S)-1,7,7- trimethylnorbornan-2-yl]oxy- benzamide
5-chloro-2-fluoro-N-methylsulfonyl- 4-[4-(trifluoromethyl)cyclohexoxy]- benzamide
5-chloro-2-fluoro-N-methylsulfonyl- 4-[4-(trifluoromethyl)cyclohexoxy]- benzamide
5-chloro-4-[(5-chloro-2- adamantyl)oxy]-N- (dimethylsulfamoyl)-2-fluoro- benzamide
5-chloro-4-[(5-chloro-2- adamantyl)oxy]-N- (dimethylsulfamoyl)-2-fluoro- benzamide
5-chloro-N-(dimethylsulfamoyl)-2- fluoro-4-[4-(trifluoromethyl)- cyclohexoxy]benzamide
5-chloro-N-(dimethylsulfamoyl)-2- fluoro-4-[4-(trifluoromethyl)- cyclohexoxy]benzamide
4-[2-(1-adamantyl)ethoxy]-5-chloro- N-(dimethylsulfamoyl)-2-fluoro- benzamide
4-(1-adamantylmethoxy)-5-chloro- N-cyclopropylsulfonyl-2-fluoro- benzamide
4-(1-adamantylmethoxy)-5- cyclopropyl-2-fluoro-N-[(3S)-3- hydroxypyrrolidin-1-yl]sulfonyl- benzamide
4-(1-adamantylmethoxy)-5- cyclopropyl-N-cyclopropylsulfonyl- 2-fluorobenzamide
4-(1-adamantylmethoxy)-5-chloro-2- fluoro-N-[(3S)-3-hydroxypyrrolidin- 1-yl]sulfonylbenzamide
4-(1-adamantylmethoxy)-5- cyclopropyl-2-fluoro-N-(3- fluoroazetidin-1-yl)sulfonyl- benzamide
4-(1-adamantylmethoxy)-5-chloro-2- fluoro-N-(3-fluoroazetidin-1- yl)sulfonylbenzamide
5-chloro-4-[(4,4-difluoro-1- adamantyl)methoxy]-2-fluoro-N- methylsulfonylbenzamide
5-cyclopropyl-4-[(4,4-difluoro-1- adamantyl)methoxy]-2-fluoro-N- methylsulfonylbenzamide
4-(1-adamantylmethoxy)-5- cyclopropyl-2-fluoro-N-pyrrolidin-1- ylsulfonylbenzamide
4-(1-adamantylmethoxy)-5- cyclopropyl-2-fluoro-N- morpholinosulfonylbenzamide
5-cyclopropyl-2-fluoro-4-[(3-fluoro- 1-adamantyl)methoxy]-N- methylsulfonylbenzamide
5-cyclopropyl-2-fluoro-4-[(3- methoxy-1-adamantyl)methoxy]-N- methylsulfonyl-benzamide
4-(1-adamantylmethoxy)-5- cyclopropyl-N-(3,3-difluoroazetidin- 1-yl)sulfonyl-2-fluoro-benzamide
2-fluoro-4-[(3-fluoro-1- adamantyl)methoxy]-N- methylsulfonylbenzamide
4-(1-adamantylmethoxy)-2-fluoro-5- methyl-N-methylsulfonyl-benzamide
4-1-adamantylmethoxy)-N- (azetidin-1-ylsulfonyl)-2-fluoro-5- methyl-benzamide
4-(1-adamantylmethoxy)-5- cyclopropyl-N-ethylsulfonyl-2- fluoro-benzamide
4-(1-adamantylmethoxy)-N-tert- butylsulfonyl-5-cyclopropyl-2- fluoro-benzamide
4-(1-adamantylmethoxy)-5- cyclopropyl-2-fluoro-N-(2- methoxyethylsulfamoyl)benzamide
4-(1-adamantylmethoxy)-5- cyclopropyl-2-fluoro-N-(3- hydroxypropylsulfamoyl)benzamide
4-(1-adamantylmethoxy)-5- cyclopropyl-2-fluoro-N-(3- methoxyazetidin-1-yl)sulfonyl- benzamide
Azetidine-1-sulfonic acid 5- cyclopropyl-4-(4,4-difluoro- adamantan-1-ylmethoxy)-2-fluoro- benzoylamide
Cyclopropanesulfonic acid 4- (bicyclo[4.1.0]hept-1-ylmethoxy)-5- cyclopropyl-2-fluorobenzoylamide
and the pharmaceutically acceptable salts thereof.
57 . The method of claim 38 wherein the compound has the formula:
58 . The method of claim 38 wherein the compound has the formula:
59 . The method of claim 38 wherein the compound has the formula:
60 . The method of claim 38 wherein the compound is 4-(adamantan-1-ylmethoxy)-5-chloro-2-fluoro-N-(methylsulfonyl)benzamide or a pharmaceutically acceptable salt thereof.
61 . The method of claim 38 wherein the compound is 4-(1-adamantylmethoxy)-3-cyclopropyl-N-methylsulfonyl-benzamide or a pharmaceutically acceptable salt thereof.
62 . The method of claim 38 wherein the compound is 4-(1-adamantylmethoxy)-5-cyclopropyl-2-fluoro-N-(2-methoxyethylsulfonyl)benzamide or a pharmaceutically acceptable salt thereof.
63 . The method of claim 38 wherein the compound is 4-(1-adamantylmethoxy)-5-cyclopropyl-2-fluoro-N-(3-fluoroazetidin-1-yl)sulfonyl-benzamide or a pharmaceutically acceptable salt thereof.
64 . The method of claim 38 wherein the compound is 4-(1-Adamantylmethoxy)-N-(azetidin-1-ylsulfonyl)-5-cyclopropyl-2-fluoro-benzamide or a pharmaceutically acceptable salt thereof.
65 . The method of claim 38 wherein the compound is 4-(2-adamantyloxymethyl)-5-chloro-2-fluoro-N-methylsulfonyl-benzamide or a pharmaceutically acceptable salt thereof.
66 . The method of claim 38 wherein the compound is 4-(1-adamantylmethoxy)-5-cyclopropyl-2-fluoro-N-morpholinosulfonylbenzamide or a pharmaceutically acceptable salt thereof.
67 . The method of claim 38 wherein the compound is 4-(1-adamantylmethoxy)-5-cyclopropyl-N-ethylsulfonyl-2-fluoro-benzamide or a pharmaceutically acceptable salt thereof.
68 . The method of claim 38 wherein the compound is cyclopropanesulfonic acid 4-(bicyclo[4.1.0]hept-1-ylmethoxy)-5-cyclopropyl-2-fluorobenzoylamide or a pharmaceutically acceptable salt thereof.Cited by (0)
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