Anti-spasmodic agents having a heterocyclic ring

Abstract

A new class of anti-spasmodic thioester compounds having a heterocyclic ring containing the nitrogen atom of a secondary or tertiary amine or a bicycloheterocyclic ring system containing the nitrogen atom of a secondary or tertiary amine. These compounds have the general formula I ##STR1## wherein: =n is an integer from 0 to 2; R 1 is aryl or cycloalkyl; =R 2 is hydrogen or hydroxyl; and R 3 is selected from the group consisting of heterocyclic containing the nitrogen atom of a secondary or tertiary amine to which an alkyl group having from 0 to 3 carbon atoms is bonded and no other hetero atoms are present in the ring structure; heterocyclic containing the nitrogen atom of a secondary or tertiary amine to which an alkyl group having from 0 to 3 carbon atoms is bonded and one or more hetero atoms selected from the group consisting of N, O and S are present in the ring structure; bicycloheterocyclic ring system containing the nitrogen atom of a secondary or tertiary amine to which an alkyl group having from 0 to 3 carbon atoms is bonded and no other hetero atoms are present in the ring system; and bicycloheterocyclic ring system containing the nitrogen atom of a secondary or tertiary amine to which an alkyl group having from 0 to 3 carbon atoms is bonded and one or more hetero atoms selected from the group consisting of N, O and S are present in the ring system.

I claim: .[.1. An antispasmodic agent having the formula.]. ##STR7## .[.wherein: 
     
        4-n-propyl-1,2,4-triazolyl, 4-iso-propyl-1,2,4-triazolyl..]. .[.2.  An antispasmodic agent having a formula selected from the group consisting of .]. ##STR8## .[.where n is an integer from 0-2, R 1  is H or OH and R 2  is 
     
     
        methyl, ethyl, n-propyl or isopropyl..]. .Iadd.3.  An antispasmodic agent having the formula .Iaddend. ##STR9## .Iadd.wherein: n is an integer from 0 to 2;   R 1  is aryl or cycloalkyl;   R 3  is a heterocyclic nitrogen ring and is selected from the group consisting of 1-methyl-imidazolinyl, 1-ethyl-imidazolinyl, 1-n-propyl-imidazolinyl, 1-iso-propyl-imidazolinyl, 1-methyl-imidazolyl, 1-ethyl-imidazolyl, 1-n-propyl-imidazolyl, 1-iso-propylimidazolyl, 1-methyl-morpholinyl, 1-ethyl-morpholinyl, 1-n-propyl-morpholinyl, 1-iso-propylmorpholinyl, 1-methylpiperazinyl, 1-ethyl-piperazinyl, 1-n-propyl-piperazinyl, 1-iso-propyl-piperazinyl, 1-methyl-piperidinyl, 1-ethyl-piperidinyl, 1-n-propyl-piperidinyl, 1-iso-propyl-piperidinyl, 1-methylpyrazolyl, 1-ethyl-pyrazolyl, 1-n-propyl-pyrazolyl, 1-iso-propylpyrazolyl, 1-methyl-pyrrolidinyl, 1-ethyl-pyrrolidinyl, 1-n-propyl-pyrrolidinyl, 1-iso-propylpyrrolidinyl, 1-methyl-3-pyrrolinyl, 1-ethyl-3-pyrrolinyl, 1-n-propyl-3-pyrrolinyl, 1-iso-propyl-3-pyrrolinyl, 1-methylthiomorpholinyl, 1-ethylthiomorpholinyl, 1-n-propylthiomorpholinyl, 1-isopropylthiomorpholinyl, 4-methyl-1,2,4-triazolyl, 4-ethyl-1,2,4-triazolyl, 4-n-propyl-1,2,4-triazolyl, 4-iso-propyl-1,2,4-triazolyl..Iaddend.   
     
     
        .Iadd.    An antispasmodic agent having the formula .Iaddend. ##STR10## .Iadd.wherein m is an integer from 0 to 2, R 1  is aryl or cycloalkyl, R 2  is hydrogen or hydroxyl, and   R 3  is a heterocyclic or bicycloheterocyclic ring connected via carbon linkage to the main chain and is selected from the group consisting of imidazolinyl, imidazolyl, morpholinyl, thiomorpholinyl, pyrazolyl,   
     
     
        1,2,4-triazolyl, tropanyl and quinuclidyl..Iaddend. .Iadd.5.  An antispasmodic agent having the formula .Iaddend. ##STR11## .Iadd.wherein: m is an integer from 0 to 2;   R 1  is aryl or cycloalkyl;   R 2  is hydrogen or hydroxyl; and   R 3  is a heterocyclic or bicycloheterocyclic ring selected from the group consisting of 1-methyl-imidazolinyl, 1-ethyl-imidazolinyl, 1-n-propyl-imidazolinyl, 1-iso-propyl-imidazolinyl, 1-methyl-imidazolyl, 1-ethyl-imidazolyl, 1-n-propyl-imidazolyl, 1-isopropyl-imidazolyl, 1-methyl-morpholinyl, 1-ethyl-morpholinyl, 1-n-propyl-morpholinyl, 1-iso-propyl-morpholinyl, 1-methylpyrazolyl, 1-ethyl-pyrazolyl, 1-n-propyl-pyrazolyl, 1-isopropylpyrazolyl, 1-methyl-3-pyrrolinyl, 1-ethyl-3-pyrrolinyl, 1-n-propyl-3-pyrrolinyl, 1-isopropyl-3-pyrrolinyl, 1-methyl-thiomorpholinyl, 1-ethylthiomorpholinyl, 1-n-propylthiomorpholinyl, 1-iso-propylthiomorpholinyl, 4-methyl-1,2,4-triazolyl, 4-ethyl-1,2,4-triazolyl, 4-n-propyl-1,2,4-triazolyl, 4-iso-propyl-1,2,4-triazolyl, .Iaddend. ##STR12##   
     
     
         .Iadd.6.  An antispasmodic agent having a formula selected from the group consisting of .Iaddend. ##STR13## .Iadd.where n is an integer from 0-2, R, is H or OH and R 2  is methyl, ethyl, n-propyl or isopropyl..Iaddend.