5-arylalkyl-4-alkoxy-2(5H)-furanones, intermediates and processe

Details 5-arylalkyl-4-alkoxy-2(5H)-furanones, intermediates and processe 5-arylalkyl-4-alkoxy-2(5H)-furanones, intermediates and processe

1987-05-04

1989-08-08

Hollrah, Glennon H.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

549313, 560104, 562470, A61K 3134, C07D30732

Patent

active

048553204

ABSTRACT:
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.

REFERENCES:
patent: 4585789 (1986-04-01), Okamoto et al.
patent: 4613613 (1986-09-01), Oguri et al.
Hansel, R. et al., "Behavior of 5-Hydroxykawain Derivatives under Mild Alkaline Conditions", Z. Naturforsch, 33b, pp. 1020-1025 (1978).
Pelter et al, "The Synthesis of Piperolide and Related Cmpds," Tetrahedron Letters, No. 18, pp. 1627-1630, 1979.

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