Chemical Compounds

Abstract

The present invention relates to new sulfonamide URAT-1 inhibitor compounds of formula (I) or a pharmaceutically acceptable salt thereof: to compositions containing them, to processes for their preparation and to intermediates used in such processes, and to methods of treatment, wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are as defined in the description.

1 - 16 . (canceled) 
     
     
         17 . A compound of formula (I) 
       
         
           
           
               
               
           
         
       
       or a pharmaceutically acceptable salt thereof, wherein:
 R 1  is a ‘C-linked’ 6-membered heteroaryl containing one, two or three nitrogen atoms wherein said heteroaryl is optionally substituted by one, two or, valency permitting, three X 1 ; 
 each X 1  is independently selected from: F; Cl; CN; (C 1 -C 4 )alkyl optionally substituted by one, two or three F; and (C 1 -C 4 )alkyloxy optionally substituted by one two or three F; 
 one of R 2 , R 3 , R 4  and R 5  is either halogen or CN, and the remainder thereof are independently selected from: H; halogen; or CN; 
 R 6  is phenyl substituted by one, two or three X 2 ; or a ‘C-linked’ 6-membered heteroaryl containing one or two nitrogen atoms wherein said heteroaryl is optionally substituted by one, two or three X 2 ; 
 each X 2  is independently selected from: F; Cl; CN; —S(C 1 -C 4 )alkyl; —NR 7 R 8 ; (C 1 -C 6 )alkyloxy optionally substituted by one, two or three F; (C 3 -C 6 )cycloalkyloxy; (C 1 -C 6 )alkyl optionally substituted by one, two or three F; and (C 1 -C 6 )alkyl substituted by OH; and 
 each R 7  and R 8  is independently H or (C 1 -C 4 )alkyl or, together with the nitrogen atom to which they are attached, form a saturated 4- to 6-membered nitrogen containing monocycle. 
 
     
     
         18 . A compound according to  claim 17 , wherein R 1  is a ‘C-linked’ 6-membered heteroaryl containing one or two nitrogen atoms, wherein said heteroaryl is optionally substituted by one or two X 1 . 
     
     
         19 . A compound according to  claim 17 , wherein R 1  is a ‘C-linked’ 6-membered heteroaryl containing one or two nitrogen atoms, wherein said heteroaryl is optionally substituted by X 1 . 
     
     
         20 . A compound according to  claim 17 , wherein R 1  is a ‘C-linked’ pyridinyl optionally substituted by X 1 . 
     
     
         21 . A compound according to  claim 17 , wherein R 1  is a ‘C-linked’ pyridinyl substituted by X 1 . 
     
     
         22 . A compound according to  claim 17 , wherein X 1  is F. 
     
     
         23 . A compound according to  claim 17 , wherein R 4  is either halogen or CN, and R 2 , R 3  and R 5  are independently selected from: H; halogen; or CN. 
     
     
         24 . A compound according to  claim 23 , wherein R 4  is CN; and each of R 2 , R 3  and R 5  are H. 
     
     
         25 . A compound according to  claim 17 , wherein R 6  is phenyl substituted by one, two or three X 2 . 
     
     
         26 . A compound according to  claim 25 , wherein R 6  is phenyl substituted by two or three X 2 . 
     
     
         27 . A compound according to  claim 17 , wherein R 6  is a ‘C-linked’ 6-membered heteroaryl containing one or two nitrogen atoms, wherein said heteroaryl is optionally substituted by one, two or three X 2 . 
     
     
         28 . A compound according to  claim 27 , wherein R 6  is a ‘C-linked’ 6-membered heteroaryl containing one or two nitrogen atoms, wherein said heteroaryl is substituted by one or two X 2 . 
     
     
         29 . A compound according to  claim 17 , wherein each X 2  is independently selected from: F; Cl; CN; —S(C 1 -C 3 )alkyl; (C 1 -C 4 )alkyloxy optionally substituted by one, two or three F; and (C 1 -C 4 )alkyl optionally substituted by one, two or three F. 
     
     
         30 . A compound according to  claim 29 , wherein each X 2  is independently selected from: F; Cl; CN; (C 1 -C 3 )alkyloxy; and (C 1 -C 3 )alkyl. 
     
     
         31 . A compound according to  claim 30 , wherein each X 2  is independently selected from: F: Cl; CN; methoxy; and methyl. 
     
     
         32 . A compound according to  claim 17 , which is:
 4-[3-chloro-4-(hydroxymethyl)phenoxy]-3-cyano-N-(5-fluoropyridin-2-yl)benzenesulfonamide;   4-{[5-chloro-6-(hydroxymethyl)pyridin-3-yl]oxy}-2-fluoro-N-(5-fluoropyridin-2-yl)benzenesulfonamide;   4-(3-chloro-4-cyanophenoxy)-3-cyano-N-(5-fluoropyridin-2-yl)benzenesulfonamide;   4-[(5-chloropyridin-3-yl)oxy]-3-cyano-N-(5-fluoropyridin-2-yl)benzenesulfonamide;   4-[(6-amino-5-chloropyridin-3-yl)oxy]-3-cyano-N-(5-fluoropyridin-2-yl)benzenesulfonamide;   3-cyano-4-(3,5-dichloro-4-cyanophenoxy)-N-(5-fluoropyridin-2-yl)benzenesulfonamide;   4-(3-chloro-4-cyanophenoxy)-3-cyano-N-(4-fluoropyridin-2-yl)benzenesulfonamide;   4-(3-chloro-4-cyano-5-fluorophenoxy)-3-cyano-N-(5-fluoropyridin-2-yl)benzenesulfonamide;   4-(3-chloro-4-cyanophenoxy)-N-(5-chloropyridin-2-yl)-3-cyanobenzenesulfonamide; or   3-cyano-4-(4-cyano-3,5-dimethylphenoxy)-N-(5-fluoropyridin-2-yl)benzenesulfonamide; or a pharmaceutically acceptable salt thereof.   
     
     
         33 . 4-[3-chloro-4-(hydroxymethyl)phenoxy]-3-cyano-N-(5-fluoropyridin-2-yl)benzenesulfonamide, or a pharmaceutically acceptable salt thereof. 
     
     
         34 . 4-(3-chloro-4-cyanophenoxy)-3-cyano-N-(4-fluoropyridin-2-yl)benzenesulfonamide, or a pharmaceutically acceptable salt thereof. 
     
     
         35 . 4-(3-chloro-4-cyanophenoxy)-N-(5-chloropyridin-2-yl)-3-cyanobenzenesulfonamide, or a pharmaceutically acceptable salt thereof. 
     
     
         36 . 3-cyano-4-(3,5-dichloro-4-cyanophenoxy)-N-(5-fluoropyridin-2-yl)benzenesulfonamide, or a pharmaceutically acceptable salt thereof.