Studies on antidiabetic agents. VI. Asymmetric transformation of (.+-.)-5-(4-(1-methylcyclohexylmethoxy)benzyl)-2,4-thiazolidinedione(ciglitazone) with optically active 1-phenylethylamines.

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Abstract
Optical resolution of a new antidiabetic agent, (.+-.)-5-[4-(1-methylcyclohexylmethoxy)benzyl]-2,4-thiazolidinedione (1, ciglitazone) with (-)- and (+)-1-phenylethylamine (PEA) in ethyl acetate resulted in almost complete asymmetric transformation to give the salts, (-)-1.cntdot.(-)-PEA and (+)-1.cntdot.(+)-PEA, respectively, in up to quantitative yields. Optical purities of (-)- and (+)-1 obtained from the salts were determined by NMR and their absolute configurations were confirmed chemically. The optical isomers showed essentially the same antidiabetic and hypolipidemic activities.