Cyano acetic acid anilide derivatives, process for their manufacture and compositions containing these compounds
AssigneeHoechst Aktiengesellschaft
InventorsHartmut Ertel, Gunther Heubach, Erhard Wolf
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Abstract
A 2-hydroxyethylidene-cyano acetic acid anilide is prepared by heating an acetoacetic acid anilide with an orthoformic acid ester and acetic anhydride, isolating the resulting 2-alkoxymethylene-acetoacetic acid anilide and treating it with hydroxylamine and the isoxazole so obtained with a base, and optionally reacting the resulting alkali metal or ammonium salt with a mineral acid or a strong organic acid. The compounds of the invention have anti-inflammatory and analgesic activity.
Claims8
A 2-hydroxyethylidene-cyano acetic acid aniline of the formula ##STR20## wherein each of R.sup.1, R.sup.2 and R.sup.3 , is alkyl of from 1 to 3 carbon atoms, alkoxy of from 1 to 3 carbon atoms, alkylthio of from 1 to 3 carbon atoms;
- said alkyl, alkoxy or alkylthio substituted in the alkyl moiety by halogen;
- halogen;
- nitro;
- cyano or alkoxycarbonyl of 1 to 3 carbon atoms in the alkyl moiety;
- also wherein either or both of R.sup.1 and R.sup.2 are hydrogen, and R.sup.3 additionally is phenyl;
- phenyl substituted by one or two fluorine, chlorine, bromine or iodine atoms, alkyl of from 1 to 3 carbon atoms or alkoxy of from 1 to 3 carbon atoms;
- phenoxy;
- or phenoxy substituted by one or two fluorine, chlorine, bromine or iodine atoms, alkyl of from 1 to 3 carbon atoms or alkoxy of from 1 to 3 carbon atoms;
- but R.sup.3 is not methyl when both R.sup.1 and R.sup.2 are hydrogen;
- or R.sup.1 is hydrogen, and R.sup.2 and R.sup.3 together are methylene-dioxy or, together with the phenyl ring to which they are linked, naphthalene;
- and M is hydrogen, an alkali metal or ammonium.
Dependencies are inferred from the claim text.