Oxazolidinediones and process for preparation

摘要

The invention comprises pyridylethylated oxazolidine-2 : 4 diones of the general formula (wherein Py represents a 2- or 4-pyridyl or methyl- or ethyl-substituted 2-pyridyl radical, and R1 and R2 each represent hydrogen or a C1-7 alkyl, C3-6 cycloalkyl, C7-8 aralkyl, pheny or substituted phenyl radical or jointly form a C4-6 alkylene chain which may be methyl-substituted) and their acid addition and quaternary ammonium salts, and the preparation thereof by reacting an oxazolidine-2 : 4-dione of the general formula with a vinylpyridine CH2=CHPy. The products may be combined with a non-toxic pharmaceutical carrier for oral administration as anticonvulsant, analgesic, hypnotic, ganglion blocking or central nervous system activity depressing agents or for prolonging barbiturate sleeping time (see Group VI). p 3-Unsubstituted oxazolidine-2 : 4-diones of the second general formula above are prepared by condensing diethyl carbonate, in methanolic sodium methoxide solution, with the appropriate a -hydroxycarboxylic acid amides obtainable from the corresponding ketone cyanhydrins by conversion to imido-ester hydrochlorides and pyrolysis of the latter. 5 - Cyclohexyl - 5 - methyloxazolidine - 2 : 4 - dione is prepared by condensing urea, in ethanol sodium ethoxide solution, with ethyl a -cyclohexyl-actate, obtained by reacting ethyl pyruvate with cyclohexyl magnesium chloride.ALSO:Oxazolidine-2 : 4-diones of the general formula (wherein Py represents a 2- or 4-pyridyl or methyl- or ethyl-substituted 2-pyridyl radical, and R1 and R2 each represent hydrogen or a C1-7 alkyl, C3-6 cycloalkyl, C7-8 aralkyl, phenyl or substituted phenyl radical or jointly form a C4-6 alkylene chain which may be methyl-substituted), or their acid addition or quaternary ammonium salts, are combined with a non-toxic pharmaceutical carrier for oral administration as anticonvulsant, analgesic, hypnotic, ganglion blocking or central nervous system activity depressing agents or for prolonging barbiturate sleeping time. Reference is also made to tablets, sterile solutions and suppositories. The salts may be the hydrochloride, nitrate, sulphate, lactate, citrate, tartrate or glycolate.