Betamimetics with a prolonged duration of activity, processes for preparing them, and their use as pharmaceutical compositions

Abstract

A compound of formula 1 wherein: R 1 is C 1 -C 4 -alkyl; R 2 is C 1 -C 4 -alkyl; and R 3 is C 1 -C 4 -alkyl or phenyl, each optionally mono- or polysubstituted, or R 2 and R 3 together are —CH 2 —CH 2 — or —CH 2 —CH 2 —CH 2 —, or the corresponding acid addition salt with a pharmacologically acceptable acid, processes for preparing such compounds, pharmaceutical compositions containing such compounds, and their use in the treatment of inflammatory and obstructive respiratory diseases.

1 . A compound of formula 1 
     
       
         
         
             
             
         
       
     
     wherein: 
 R 1  is C 1 -C 4 -alkyl;  
 R 2  is C 1 -C 4 -alkyl; and  
 R 3  is C 1 -C 4 -alkyl or phenyl, each optionally mono- or polysubstituted, or R 2  and R 3  together are —CH 2 —CH 2 — or —CH 2 —CH 2 —CH 2 —,  
 or the corresponding acid addition salt with a pharmacologically acceptable acid.  
 
   
   
       2 . The compound of formula 1 according to  claim 1 , wherein: 
 R 3  is C 1 -C 4 -alkyl or phenyl, each optionally mono-, di-, tri-, or tetrasubstituted by one or more groups selected from C 1 -C 3 -alkyl, CF 3 , methoxy, ethoxy, hydroxy, fluorine, chlorine, bromine, —OCF 3 , —CHF 2 , —NHCOCH 3 , and —NHSO 2 CH 3 , or R 2  and R 3  together are —CH 2 —CH 2 — or —CH 2 —CH 2 —CH 2 —,    or the corresponding acid addition salt with a pharmacologically acceptable acid.    
   
   
       3 . The compound of formula 1 according to  claim 1 , wherein: 
 R 3  is C 1 -C 4 -alkyl or phenyl, each optionally mono-, di-, tri-, or tetrasubstituted by one or more groups selected from methyl, ethyl, CF 3 , methoxy, ethoxy, and hydroxy, or R 2  and R 3  together are —CH 2 —CH 2 — or —CH 2 —CH 2 —CH 2 —,    or the corresponding acid addition salt with a pharmacologically acceptable acid.    
   
   
       4 . The compound of formula 1 according to  claim 1 , wherein: 
 R 3  is C 1 -C 4 -alkyl or phenyl, each optionally mono-, di-, tri-, or tetrasubstituted by one or more groups selected from methyl, CF 3 , methoxy, and hydroxy, or R 2  and R 3  together are —CH 2 —CH 2 —,    or the corresponding acid addition salt with a pharmacologically acceptable acid.    
   
   
       5 . A compound of formula 1 according to  claim 1 , wherein: 
 R 1  is methyl or ethyl;    R 2  is methyl; and    R 3  is methyl, ethyl, or phenyl, each optionally mono-, di-, tri-, or tetrasubstituted by one or more groups selected from methyl, CF 3 , methoxy, and hydroxy, or R and R 3  together are —CH 2 —CH 2 —,    or the corresponding acid addition salt with a pharmacologically acceptable acid.    
   
   
       6 . The compound of formula 1 according to  claim 1 , wherein: 
 R 1  is methyl;    R 2  is methyl; and    R 3  is methyl or phenyl, each optionally mono-, di-, or trisubstituted by one or more groups selected from methyl, ethyl, and hydroxy, or R 2  and R 3  together are —CH 2 —CH 2 — or the corresponding acid addition salt with a pharmacologically acceptable acid.    
   
   
       7 . The compound of general formula 1 according to  claim 1 , wherein: 
 R 1  is methyl;    R 2  is methyl; and    R 3  is methyl or phenyl, or R and R 3  together are —CH 2 —CH 2 —,    or the corresponding acid addition salt with a pharmacologically acceptable acid.    
   
   
       8 . A pharmaceutical composition comprising the compound of formula 1 according to one of  claims 1  to  7  and a physiologically acceptable excipient.  
   
   
       9 . A method for treatment of a disease which is responsive to a betamimetic in a patient, the method comprising administering to the patient in need thereof an effective amount of a compound of general formula 1 according to one of  claims 1  to  7 .  
   
   
       10 . (canceled)  
   
   
       11 . (canceled)  
   
   
       12 . (canceled)  
   
   
       13 . (canceled)  
   
   
       14 . (canceled)  
   
   
       15 . (canceled)  
   
   
       16 . (canceled)