6-dimethylaminomethyl-1-phenyl-cyclohexane compounds as pharmaceutical active ingredients

Abstract

6-dimethylaminomethyl-1-phenyl-cyclohexane compounds, methods of preparing them and the use of these compounds in drugs are described.

We claim:  
     
       1. A 6-dimethylaminomethyl-1-phenyl-cyclohexane compound corresponding to formula I:                    
       wherein 
       R 1  represents H, OH, Cl or F;  
       R 2  represents benzyl, CF 3 , OH, OCH 2 -C 6 H 5 , O—C 1-4 -alkyl, Cl or F,  
       R 3  represents H,  
       R 4  represents H, CH 3 , PO(OC 1-4 -alkyl) 2 , CO(OC 1-5 -alkyl), CO—NH—C 6 H 4 -C 1-3 -alkyl CO—C 6 H 4 -R 5 , CO—C 1-5 -alkyl CO—CHR 6 -NHR 7  or an unsubstituted or substituted pyridyl thienyl, thiazoyl or phenyl group;  
       R 5  represents OC(O)C 1-3 -alkyl in the ortho position or CH 2 -N(R 8 ) 2  in the meta or para position, wherein R 8  represents C 1-4  alkyl or both groups R 8  together with N constitute a 4-morpholino radical, and  
       R 6  and R 7  are each independently selected from H and C 1-6  alkyl,  
       or a pharmaceutically acceptable acid addition salt thereof. 
     
     
       2. A 6-dimethylaminomethyl-1-phenyl-cyclohexane compound according to claim  1 , wherein R 1  is H, OH or F. 
     
     
       3. A 6-dimethylaminomethyl-1-phenyl-cyclohexane compound according to claim  1 , wherein the compound has the configuration of formula Ia:                    
     
     
       4. A pharmaceutical composition comprising a 6-dimethylaminomethyl-1-phenyl-cyclohexane compound according to claim  1 , and at least one pharmaceutical carrier or diluent. 
     
     
       5. A method of relieving pain in a mammal comprising administering to said mammal an effective pain relieving amount of a 6-dimethylaminomethyl-1-phenyl-cyclohexane compound according to claim  1 . 
     
     
       6. A  6 - dimethylaminomethyl -   1   - phenyl - cyclohexane compound corresponding to formula I:                      
       
         wherein  
       
       
         R 
         1  
         represents H, OH, Cl or F;  
       
         R   2    represents benzyl, CF   3   , OH, OCH   2 - C   6   H   5   , O—C   1-4 - alkyl, Cl or F, or if R   1    and R   4    are H, R   2    may also be H,    
       
         R 
         3  
         represents H,  
       
         R   4    represents H, CH   3   , PO ( OC   1-4 - alkyl ) 2   , CO ( OC   1-5 - alkyl ),  CO—NH—C   6   H   4 - C   1-3 - alkyl, CO—C   6   H   4 - R   5   , CO—C   1-5 - alkyl, CO—CHR   6 - NHR   7    or an unsubstituted or substituted pyridyl, thienyl, thiazoyl or phenyl group;    
         R   5    represents OC ( O ) C   1-3 - alkyl in the ortho position or CH   2 - N ( R   8 ) 2    in the meta or para position, wherein R   8    represents C   1-4    alkyl or both groups R   8    together with N constitute a  4   - morpholino radical, and    
       
         R 
         6  
         and R 
         7  
         are each independently selected from H and C 
         1-6  
         alkyl,  
       
       
         or a pharmaceutically acceptable acid addition salt thereof. 
       
     
     
       7. ( − )-(   1 R, 2 S )-   3   -(   2   - dimethylaminomethyl - cyclohexyl )- phenol or a pharmaceutically acceptable acid addition salt thereof.