Heterocyclic amines having central nervous system activity

Abstract

Tricyclic nitrogen containing compounds, having anxiolytic and anti-depressant activity and central nervous system activity of the following structural formula: and pharmaceutically acceptable salts thereof wherein R 1 and R 2 are independently hydrogen, C 1-6 alkyl or R 1 and R 2 are joined to form pyrrolidiae, piperidine, morpholine or imidazole. X is OCH 3 , SO 2 R 3 , SO 2 CF 3 or CN where R 3 is C 1-6 alkyl or an Aryl; and Y is hydrogen, Cl, Br, F, CN, CONR 1 R 2 , CF 3 , OCH 3 , SO 2 NR 1 R 2 . These new compounds are suitable for treating anxiolytic disorder, schizophrenia, Parkinson's disease, anxiety, depression or as compounds for lowering blood pressure or treating migraine headaches in patients in need of such treatment.

1. A compound of the following structural formula: 
                   
       and pharmaceutically acceptable salts thereof wherein,
 R 1  and R 2  are independently hydrogen, C 1-6  alkyl or R 1  and R 2  are joined to form pyrrolidine, piperidine, morpholine or imidazole;  
 X is OCH 3 , SO 2 R 3 , SO 2 CF 3  or CN;  
 R 3  is C 1-6  alkyl or a C 5-10  aromatic ring (optionally substituted with a halogen, hydroxyl or C 1-6  alkyl (optionally substituted with halogen or hydroxyl); and  
 Y is hydrogen, Cl, Br, F, CN, CONR 1 R 2 , CF 3 , OCH 3 , SO 2 NR 1 R 2 .  
 
     
     
       2. The compound of  claim 1  wherein R 1  and R 2  are each propyl. 
     
     
       3. The compound of  claim 1  wherein R 1  and R 2  are each methyl. 
     
     
       4. The compound of  claim 1  wherein X is —OCH 3 . 
     
     
       5. The compound of  claim 1  wherein Y is hydrogen. 
     
     
       6. The compound of  claim 1  which is
 a) (R)-5-Methylamino-1-methoxy-5,6-dihydro-4H-imidazo[4,5,1-ij]-quinolin-2(1H)-one,    b) (R)-5-Dimethylamino-1-methoxy-5,6-dihydro-4H-imidazo[4,5,1-ij]-quinolin-2(1H)-one,    c) (R)-5-Propylamino-1-methoxy-5,6-dihydro-4H-imidazo[4,5,1-ij]-quinolin-2(1H)-one, or    d) (R)-5-Dipropylamino-1-methoxy-5,6-dihydro-4H-imidazo[4,5,1-ij]-quinolin-2(1H)-one.    
     
     
       7. A method for treating anxiolylic disorders in animal or human hosts comprising the administration of a pharmaceutically effective amount of a compound of Formula I as set forth in  claim 1 . 
     
     
       8. The method of  claim 7  wherein said compound is orally administered in an amount of from about 10 mg to about 1200 mg per day. 
     
     
       9. ( R )-   3   - Methylamino -   1 , 2 , 3 , 4   - tetrahydroquinoline maleate.   
     
     
       10. ( R )- Methyl -(   1 , 2 , 3 , 4   - tetrahydro -   3   - quinolinyl )  carbamic acid, phenylmethyl ester.   
     
     
       11. ( R )- Methyl - [ 1 , 2 , 3 , 4   - tetrahydro -   1   - [methoxyamino ) carbonyl] -   3   - quinolinyl]carbamic acid, phenylmethyl ester.