Nisshin Flour Milling Co., Ltd.

Kunio Nakagawa

Katsura Kogure

Noriyoshi Sueda

Youziro Yoshino

Sizuo Himoto

Hiroyasu Koyama

2-Hydroxy-butenoic acid derivatives of the general formula: ##STR1## are described. These compounds have antiphlogistic activity.

Butenoic and pyruvic acid derivatives

A process for preparing 3-methyl-3-(substituted aryl)-pyruvic acid compounds by treating a glycidic acid ester compound of the formula, ##STR1## wherein R.sup.1 is a 4-biphenylyl, 4-clyclohexylphenyl, 3-phenoxyphenyl, 4'-fluoro-4-biphenylyl, 2-fluoro-4-biphenylyl or 3-benzoylphenyl group and R.sup.2 is a lower alkyl group or its corresponding free acid with a Lewis acid to form a 2-hydroxy-3-(substituted aryl)-3-butenoic acid ester and treating the resulting ester in an alcohol with an alkali metal alcoholate to form the pyruvic acid compounds. If desired, the pyruvic acid compounds can then be saponified to compounds of the formula, ##STR2## wherein R.sup.1 is as previously defined and which compounds are useful as anti-inflammatory agents.

Process for preparing a 2-methyl-(substituted aryl)-pyruvic acid compound

Process for preparing a 2-hydroxy-butenoic acid derivative of the general formula, ##STR1## wherein R.sup.1 is a group selected from aliphatic, alicyclic or aromatic radicals and R.sup.2 is a lower alkyl group by heating a glycidic acid derivative having the general formula, ##STR2## wherein R.sup.1 and R.sup.2 is as defined above or for preparing a pyruvic acid derivative of the general formula, ##STR3## wherein R.sup.1 and R.sup.2 are as defined above by heating the glycidic acid derivative of the above mentioned formula (I) or the 2-hydroxy-butenoic acid derivative of formula (II) in the presence of an electrophilic agent.

Process for producing a 2-hydroxy-3-butenoic acid derivative having the formula ##STR1## wherein R.sup.1 is an aliphatic, alicyclic or aromatic group and R.sup.2 is a lower alkyl group by treating a glycidic acid ester derivative having the formula ##STR2## wherein R.sup.1 and R.sup.2 are as defined above in the presence of an acid.

Process for producing 2-hydroxy-3-butenoic acid derivatives

A new process of producing a 2-(4-alkylphenyl)-propionic acid known as a valuable anti-inflammatory agent is now provided, which comprises treating an alkyl 3-methyl-3-(4-alkylphenyl)-glycidate with an acid to produce 2-(4-alkylphenyl)-propionaldehyde and 3-methyl-3-(4-alkylphenyl)-pyruvic acid through a new reaction, and then oxidising these intermediate products to the desired 2-(4-alkylphenyl)-propionic acid. This new process is operable in a facile way, gives a high yield of the desired product and is suitable for a commercial practice.

Process of producing a 2-(4-alkylphenyl)-propionic acid

A new process for the production of a 2-(4-alkylphenyl)-propionic acid known as a valuable anti-inflammatory agent is now provided, which comprises treating an alkyl 2-hydroxy-3-(4-alkylphenyl)-3-butenoate, a new compound, with an alkali metal alcoholate in an alcohol to give the corresponding alkyl 3-methyl-3-(4-alkylphenyl)-pyruvate, also a new compound, which is then hydrolysed to liberate the corresponding 3-methyl-3-(4-alkylphenyl)-pyruvic acid, and then oxidising the liberated pyruvic acid compound to the desired 2-(4-alkylphenyl)-propionic acid. This new process is operable in a facile way with a high yield of the desired product and is much suitable for a commercial practice than the prior art methods.

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Kawagoe, Japan

Kunio Nakagawa