Benzenesulfonanilide compounds suitable for treating disorders that respond to modulation of the serotonin 5-ht6 receptor

Abstract

The present invention relates to novel benzenesulfonanilide compounds of the formulae I and I′ and physiologically tolerated acid addition salts and the N-oxides thereof. The compounds possess valuable therapeutic properties and are particularly suitable, for treating diseases that respond to modulation of the serotonin 5-HT 6 receptor. wherein R 1 is hydrogen or methyl R 2 is hydrogen or methyl R 3 hydrogen, fluorine C 1 -C 2 alkoxy or fluorinated C 1 -C 2 alkoxy; R 4 is hydrogen, C 1 -C 4 alkyl or fluorinated C 1 -C 4 alkyl; R 5 is hydrogen, fluorine, C 1 -C 2 alkyl, fluorinated C 1 -C 2 alkyl, C 1 -C 2 alkoxy or fluorinated C 1 -C 2 alkoxy; and R 6 is hydrogen, fluorine and chlorine.

1 . Benzenesulfonanilide compounds of formulae I and I′ 
       
         
           
           
               
               
           
         
         wherein 
         R 1  is hydrogen or methyl; 
         R 2  is hydrogen or methyl; 
         R 3  hydrogen, fluorine C 1 -C 2  alkoxy or fluorinated C 1 -C 2  alkoxy; 
         R 4  is hydrogen or C 1 -C 4  alkyl or fluorinated C 1 -C 4  alkyl 
         R 5  is hydrogen, fluorine, C 1 -C 2  alkyl, fluorinated C 1 -C 2  alkyl, C 1 -C 2  alkoxy or fluorinated C 1 -C 2  alkoxy; and 
         R 6  is hydrogen, fluorine or chlorine; 
         and physiologically tolerated acid addition salts and the N-oxides thereof. 
       
     
     
         2 . The compounds of  claim 1 , wherein R 1  is hydrogen. 
     
     
         3 . The compounds of  claim 1 , wherein R 2  is hydrogen and methyl. 
     
     
         4 . (canceled) 
     
     
         5 . The compounds of  claim 1 , wherein the carbon atom that carries R 2  has S-configuration and R-configuration. 
     
     
         6 . (canceled) 
     
     
         7 . The compounds of  claim 1 , wherein R 3  is methoxy, hydrogen, or fluorine. 
     
     
         8 . (canceled) 
     
     
         9 . The compounds of  claim 1 , wherein R 4  is hydrogen or C 1 -C 2  alkyl. 
     
     
         10 . (canceled) 
     
     
         11 . The compounds of  claim 1 , wherein R 5  is hydrogen, methoxy, or difluoromethoxy. 
     
     
         12 - 13 . (canceled) 
     
     
         14 . The compounds of  claim 1 , wherein R 5  and R 6  are hydrogen, R 3  is selected from the group consisting of C 1 -C 2  alkoxy and fluorinated C 1 -C 2  alkoxy and R 4  is selected from the group consisting of hydrogen or C 1 -C 2  alkyl. 
     
     
         15 . The compounds of  claim 1 , wherein one or more of the following provisos a), b), c) or d) are met:
 a) R 5  is selected from the group consisting of fluorine, C 1 -C 2  alkyl, fluorinated C 1 -C 2  alkyl, C 1 -C 2  alkoxy or fluorinated C 1 -C 2  alkoxy;   b) R 6  is fluorine or chlorine;   c) R 3  is hydrogen or fluorine; and/or   d) R 4  is C 3 -C 4 -alkyl or fluorinated C 1 -C 4 -alkyl;   
     
     
         16 . The compounds of  claim 15 , wherein R 6  is fluorine or chlorine or hydrogen, which is located in the 5-position or 6-position of the benzene ring. 
     
     
         17 . (canceled) 
     
     
         18 . The compounds of  claim 15 , wherein R 3  is hydrogen and methoxy. 
     
     
         19 - 20 . (canceled) 
     
     
         21 . The compounds of  claim 1 , wherein the OCHF 2 -radical in formula I is located on the benzene ring in the ortho-position, meta-position, and para-position with respect to the sulfonyl group. 
     
     
         22 - 24 . (canceled) 
     
     
         25 . The compounds of  claim 1  for use in a medicament, for treating a medical disorder selected from diseases of the central nervous system, addiction diseases or obesity. 
     
     
         26 . A pharmaceutical composition comprising at least one compound of  claim 1 , optionally together with at least one physiologically acceptable carrier or auxiliary substance. 
     
     
         27 . A method for treating a medical disorder selected from diseases of the central nervous system, addiction diseases or obesity, said method comprising administering an effective amount of at least one compound of  claim 1  to a subject in need thereof. 
     
     
         28 . The method of  claim 27 , wherein the medical disorder is a disease of the central nervous system. 
     
     
         29 . The method of  claim 28 , for treating cognitive dysfunctions, cognitive dysfunctions associated with Alzheimer's disease, and cognitive dysfunctions associated with schizophrenia. 
     
     
         30 - 33 . (canceled) 
     
     
         34 . The method of a compound of  claim 1  for preparing a pharmaceutical composition. 
     
     
         35 . The method of the compounds of formulae I and I′ for preparing a pharmaceutical composition for the treatment of a medical disorder as defined in  claim 27 .