Pharmaceutical compositions containing phthalimidine derivatives

The invention relates to phthalimidine derivatives of formula wherein R is hydrogen or an acyl radical derived from a monocarboxylic acid and wherein ring B may be optionally substituted by one or more radicals selected from halogen, alkyl, amino, acylamino and alkoxy. It comprises as novel compounds those phthalimidines in which ring B is substituted by a single chlorine, bromine or fluorine atom and a process for making those phthalimidines in which R is hydrogen which comprises reacting a compound with ammonia under reducing conditions, e.g. in the presence of hydrogen and a hydrogenation catalyst. The compounds in which R is hydrogen may also be prepared by reducing 4-aryl-1-keto-2,3-benzoxazines with zinc and acetic acid or by reducing 1-arylphthalaz-4-ones with zinc and hydrochloric acid. The compounds in which R is acyl are made by acylating the corresponding compounds where-in R is hydrogen. Examples describe the preparation of pthalimidines in which R is hydrogen and the ring B is phenyl, 2,3-, 2,5- or 3,4-dimethylphenyl, 3,4 - dimethoxyphenyl, 4-chlorophenyl, 4-bromophenyl, 4-fluorophenyl, and 2-aminophenyl, the latter being then acetylated to give 3-(2-acetaminophenyl) phthalimidine. 2-Propionyl-3-phenylphthalimidine is also prepared and the corresponding 2-acetyl compound referred to. 4-Aryl-1-keto-2,3-benzoxazine starting materials in which the aryl group is 2,3-, 2,5- or 3,4-dimethylphenyl, 3,4 - dimethoxyphenyl, 4-chlorophenyl, 4-bromophenyl and 4-fluorophenyl by reacting the corresponding substituted 2-benzoylbenzoic acids with hydroxylamine hydrochloride in the presence of barium carbonate.ALSO:Pharmaceutical compositions having analgesic, antipyretic or anticonvulsant activity comprise as active ingredient phthalimidines of formula where R is hydrogen or the acyl radical of a monocarboxylic acid and ring B may optionally be substituted by one or more radicals selected from halogen, alkyl, amino, acylamino and alkoxy. They may be administered orally, e.g. as tablets, capsules, aqueous or oily suspensions, dispersible powders or granules, emulsions, syrups or elixirs, parenterally in aqueous or non-aqueous medium, or as suppositories. Other specified active ingredients are acetylsalicylic acid, codeine, salicylamide, p-acetamidophenol, phenacetin, primidone and diphenylhydantoin.