1-Substituted-3-amidopyrrolidines

Abstract

1-Substituted-3-amidopyrrolidines useful as analgetics and anti-depressants are disclosed. The compounds are prepared by acylation of 1-substituted-3-aminopyrrolidines.

What is claimed:  .[.1. A compound selected from 
     
        proviso that when R is lower alkyl, R 1  cannot be hydrogen..]. 2. A compound as defined in claim .[.1.]. .Iadd.19 .Iaddend.which is 
     
     
        1-benzyl-3-(N-phenylpropionamido)pyrrolidine. 3. A compound as defined in claim .[.1.]. .Iadd.17 .Iaddend.which is 
     
     
        1-(2-phenoxyethyl)-3-[N-(2-methoxyphenyl)propionamido]pyrrolidine. 4. .[.A compound as defined in claim 1 which is.]. 
     
     
        1-allyl-3-(N-phenylpropionamido)pyrrolidine. 5. A compound as defined in claim .[.1.]. .Iadd.19 .Iaddend.which is 
     
     
        1-(2-phenylethyl)-3-(N-phenylpropionamido)pyrrolidine. 6. A compound .[.as defined in claim 1.].  which is 
     
     
        1-methyl-3-(N-phenyl-4-chlorobenzamido)pyrrolidine. 7. A compound as defined in claim .[.1.]. .Iadd.17 .Iaddend.which is 
     
     
        1-(2-phenoxyethyl)-3-(N-phenylpropionamido)pyrrolidine. 8. A compound as defined in claim .[.1.]. .Iadd.17 .Iaddend.which is 
     
     
        1-[2-(o-methoxyphenoxy)ethyl]-3-(N-phenylproplonamido) pyrrolidine. 9. A compound .[.as defined in claim 1.]. which is 
     
     
        1-methyl-3-(N-phenylbenzamido)pyrrolidine. 10. A compound .[.as defined in claim 1.]. which is 1-ethyl-3-(N-phenyl-4-chlorobenzamido)pyrrolidine. 
     
     
            A compound .[.as defined in claim 1.]. which is 
     
     
        1-ethyl-3-[N-(3-trifluoromethylphenyl)benzamido]pyrrolidine. 12. A compound .[.as defined in claim 1.]. which is 
     
     
        1-methyl-3-(N-phenyl-3-trifluoromethylbenzamido pyrrolidine. 13. A compound .[.as defined in claim 1.]. which is 
     
     
        1-methyl-3-(N-phenyl-3-chlorobenzamido)pyrrolidine. 14. A compound .[.as defined in claim 1.]. which is 
     
     
        1-methyl-3-(N-phenyl-4-fluorobenzamido)pyrrolidine. 15. A compound .[.as defined in claim 1.]. which is 3-(N-phenylbenzamido)pyrrolidine. .Iadd. 16. A compound selected from (a) 3-amidopyrrolidines having the formula: ##STR5## wherein; R is phenyl,   R 1  is selected from the group consisting of hydrogen, loweralkyl, phenyl, cyclohexyl, lower-alkoxy phenyl, hydroxyphenyl, halophenyl and trifluoromethylphenyl,   R 2  is selected from the group consisting of lower-alkyl, phenyl, nitrophenyl, aminophenyl, halophenyl, lower-alkoxy-phenyl, phenoxy-lower-alkyl, halophenoxy-lower-alkyl, lowwer-alkyl-phenyl and trifluoromethylphenyl, and (b) pharmaceutically acceptable acid addition salts thereof.     
     
     
        .Iaddend..Iadd.7.  A compound selected from (a) 3-amidopyrrolidines having the formula: ##STR6## wherein; R is phenoxy-lower alkyl,   R 1  is selected from the group consisting of hydrogen, lower-alkyl, phenyl, cyclohexyl, lower-alkoxy phenyl, hydroxyphenyl, halophenyl and trifluoromethylphenyl,   R 2  is selected from the group consisting of lower-alkyl, phenyl, nitrophenyl, aminophenyl, halophenyl, lower-alkoxy-phenyl, phenoxy-lower-alkyl, halophenoxy-lower-alkyl, lower-alkylphenyl and trifluoromethylphenyl, and (b) pharmaceutically acceptable acid addition salts thereof.     
     
     
        .Iaddend..Iadd. 18.  A compound selected from (a) 3-amidopyrrolidines having the formula: ##STR7## wherein; R is cyclohexyl,   R 1  is selected from the group consisting of hydrogen, loweralkyl, phenyl, cyclohexyl, lower-alkoxy phenyl, hydroxyphenyl,  halophenyl and trifluoromethylphenyl,   R 2  is selected from the group consisting of lower-alkyl, phenyl, nitrophenyl, aminophenyl, halophenyl, lower-alkoxy-phenyl, phenoxy-lower-alkyl, halophenoxy-lower-alkyl, lower-alkylphenyl and trifluoromethylphenyl, and (b) pharmaceutically acceptable acid addition salts thereof.     
     
     
        .Iaddend..Iadd. 19.  A compound selected from (a) 3-amidopyrrolidines having the formula: ##STR8## wherein; R is phenyllower-alkyl,   R 1  is selected from the group consisting of hydrogen, loweralkyl, phenyl, cyclohexyl, lower-alkoxy phenyl, hydroxyphenyl, halophenyl and trifluoromethylphenyl,   R 2  is selected from the group consisting of lower-alkyl, phenyl, nitrophenyl, aminophenyl, halophenyl, lower-alkoxy-phenyl, phenoxy-lower-alkyl, halophenoxy-lower-alkyl, lower-alkylphenyl and trifluoromethylphenyl, and (b) pharmaceutically acceptable acid addition salts thereof..Iaddend.