Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai

Mutsuo Kataoka

Masaji Ohno

Norio Kawabe

New compounds of the formula ##STR1## WHEREIN Ar is selected from the group consisting of phenylethyl, furyl, methylfuryl, thienyl, pyrrolyl, naphthyl, hydroxynaphthyl, and phenyl substituted by at least one member selected from the group consisting of halogen, hydroxyl, cyano, trifluoromethyl, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, carbamoyl, amino of the formula --NR'R', alkoxycarbonyl of the formula --CO--OR' wherein R' and R' are each alkyl of 1-4 carbon atoms, and alkylenedioxy of the formula --O--R''--O-- wherein R'' is alkylene of 1-4 carbon atoms, provided that said substituted phenyl is not 3,4-di-methoxyphenyl, and the addition salts thereof with the cation of an organic or inorganic base inhibit the enzyme activities of tyrosine hydroxylase and dopamine .beta.-hydroxylase and are useful chemotherapeutic agents in the treatment of essential hypertension.

Method and composition for treating hypertension

As new compound, a series of 2-hydrocinnamoyl-1,3-cyclopentanedione derivative of the general formula: ##STR1## WHEREIN Ar stands for a mono-valent aromatic radical, for example, phenyl and 3,4-methylenedioxy-phenyl, substituted or unsubstituted, have been found to have an activity to inhibit the action of tyrosine hydroxylase and to be useful as hypotensive agent. These new compounds may be produced by condensing 2-acetyl-1,3-cyclopentanedione with an aromatic aldehyde of the formula Ar-CHO wherein Ar is as defined, according to Claisen-Schmidt condensation, followed by the hydrogenation of the condensation product obtained, or the new compounds may also be produced by reacting 2-acetyl-1,3-cyclopentanedione with an aromatic halide of the formula Ar-CH.sub.2 X wherein Ar is as defined and X is a halogen, for example, in liquid ammonia and in the presence of an alkali metal amide.

2-Hydrocinnampyl-1,3-cyclopentanediones

New compounds of the formula ##SPC1## Wherein Ar is selected from the group consisting of phenylethyl, furyl, methylfuryl, thienyl, pyrrolyl, naphthyl, hydroxynaphthyl, and phenyl substituted by at least one member selected from the group consisting of halogen, hydroxyl, cyano, trifluoromethyl, akyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, carbamoyl, amino of the formula --NR'R', alkoxycarbonyl of the formula --CO--OR' wherein R'and R'are each alkyl of 1-4 carbon atoms, and alkylenedioxy of the formula --O--R ''--O-- wherein R'' is alkylene of 1-4 carbon atoms, provided that said substituted phenyl is not 3,4-di-methoxyphenyl, and the addition salts thereof with the cation of an organic or inorganic base inhibit the enzyme activities of tyrosine hydroxylase and dopamine .beta.-hydroxylase and are useful chemotherapeutic agents in the treatment of essential hypertension.

Growing community of inventors

Kamakura, Japan

Mutsuo Kataoka