Enantiomers of 8-hydroxyquinoline derivatives and the synthesis thereof

Abstract

Our invention relates to novel enantiomer derivatives of 8-hydroxyquinoline derivatives with general formula (I) and (II) and the synthesis thereof and pharmaceutically acceptable salts and metal complexes thereof, and the medicinal and/or pharmaceutical compositions comprising these compounds. The essence of the subject matter of the invention relates to the fact that prior art discloses the biological effect and characteristics only of the racemic products, the novel enantiomer derivatives according to the invention appear in our application for the first. The subject matter of the invention furthermore relates to a novel, stereoselective synthesis for the preparation of the novel enantiomer derivatives according to the invention. The novel medicinal and/or pharmaceutical compositions comprising these enantiomers are suitable for the treatment of the named diseases, and the enanatiomers are used for manufacture of these compositions. These applications for manufacture of the compositions are also the subject matters of the invention. The compounds according to the invention can be used preferably as cytoprotective, neuroprotective, cardioprotective, anxiolytic and antidepressant agent for treatment of neuropsychiatric and neurologic diseases and diseases in connections with transplantations and with ischemia and reperfusion injuries thereof, and inhibition of organ, advantageously skin graft rejection. According to our studies the R-enantiomer has either sole or high biological effect in some cases.