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AssigneeDr. Willmar Schwabe GmbH & Co.
InventorsShyam S. Chatterjee, Klaus Klessing
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The present invention provides 5-arylalkyl-4-alkoxy-2(5H)-furanones of the formula: ##STR1## wherein the oxygen atoms on C-5 and C-.alpha., relative to one another, are in the threo-position, with the exclusion of those compounds of the formula (I) wherein R.sup.2 is H or CH.sub.3 when n=0 or 2, R.sup.o =H, R.sup.1 =CH.sub.3, R.sup.3 =H and R.sup.4 =H. The present invention also provides processes for their preparation, as well as new 3-alkoxy-5-(subst.)-phenyl-2(E), 4(E)-pentadienoates as reactive intermediates for the preparation of the new furanone derivatives. The new furanone derivatives of the threo series are active as anticonvulsives/anti-epileptics. Therefore, the present invention also provides medicaments which contain these new furanone derivatives, as well as known furanones, the anticonvulsive/anti-epileptic effectiveness of which has been found for the first time.
5-Arylalkyl-4-alkoxy-2(5H)-furanones of the formula:
4-Methoxy-5-phenylhydroxymethyl-2(5H)-furanones of the formula:
4-Methoxy-5-phenylhydroxymethyl-2(5H)-furanones of the formula (II), wherein the oxygen atoms on C-5 and C-.alpha., relative to one another, are in the threo-position and wherein one of the two symbols R.sup.3 and R.sup.4 signifies a fluorine, chlorine or bromine atom or a trifluoromethyl radical, in each case in the 2'-position, and the other signifies a chlorine or bromine atom or a trifluoromethyl radical, in each case in the 4'-, 5'- or 6'-position.
threo-5-(2'-Chlorophenylhydroxymethyl)-4-methoxy-2(5H)-furanone.
threo-5-(2'-Bromophenylhydroxymethyl)-4-methoxy-2(5H)-furanone.
threo-5-(2'-Fluorophenylhydroxymethyl)-4-methoxy-2(5H)-furanone.
threo-5-(2'-Trifluoromethylphenylhydroxymethyl)-4-methoxy-2(5H)- furanone.
threo-5-(2',5'-Dichlorophenyl)hydroxymethyl-4-methoxy-2(5H)-furanone.
threo-5-(2',4'-Dichlorophenyl)hydroxymethyl-4-methoxy-2(5H)-furanone.
threo-4-Methoxy-5-[methoxymethoxy-(2'-chlorophenyl)-methyl]-2(5H)-furan one.
threo-4-Methoxy-5-[methoxymethoxy-(2'-bromophenyl)-methyl]-2(5H)-furanone.
threo-4-Methoxy-5-[methoxymethoxy-(2'-fluorophenyl)-methyl]-2(5H)-furan one.
threo-4-Methoxy-5-[methoxymethoxy-(2'-trifluoromethylphenyl)-methyl]-2(5H)- furanone.
threo-4-Methoxy-5-[methoxy-(2'-chlorophenyl)-methyl]-2(5H)-furanone.
Dependencies are inferred from the claim text.