Quaternary salts as hypoglycemic agents

DETAILED DESCRIPTION OF THE INVENTION The hypoglycemic agents of the present invention are synthesized by the reaction of a suitable halide with the appropriate heterocyclic ring system, depicted as follows: ##STR6## wherein R, R.
sub.
2, R.
sub.
1, R.
sub.
3, R.
sub.
4, R.
sub.
5, R.
sub.
6, Q, Y, Z and X are as previously described.
Transformation of the above-mentioned heterocyclic compounds to quaternary salts is effected by reacting with a halide where X is preferably chloro, bromo or iodo.
Said reaction can be conducted between equimolar amounts of the two reagents either neat or in the presence of a suitable reaction-inert solvent.
When conducted neat a large excess of the halide can be employed, acting under these conditions as both a reactant and solvent.
By a reaction-inert solvent is meant one which does not react to any appreciable degree with the product or reactants under the conditions of said reaction.
Solvents suitable for the solublizing of the reactants leading to the quaternary compounds can be of a varied nature, and can include (lower)alkanols, (lower)alkylnitriles, di(lower)alkyl ketones, cyclic- and di(lower)alkyl ethers and liquid aromatic hydrocarbons.
The preferred solvent for this reaction is acetonitrile.
Reaction time is not critical, and depends on temperature, concentration and inherent reactivity of the reagents.
When steam bath temperatures are employed, completion of the reaction usually requires overnight heating.
The product is isolated by cooling the reaction mixture to induce crystallization, or initial concentration of the reaction mixture followed by cooling and addition of a second solvent to induce crystallization.
Further purification of the final product is facilitated by trituration or recrystallization from an appropriate solvent.
As mentioned previously, quaternary salt formation is preferably effected wherein X of the alkylating agent is bromo, chloro, or iodo.
Following isolation of these salts the nature of the X variable can be altered by initially treating an aqueous solution of quaternary halide with an equivalent of silver oxide, followed by separation of the precipitated silver halide and treatment of the aqueous solution of the quaternary base with at least an equivalent of an appropriate acid HX