GB1185273A - Derivatives of Phthalimidines - Google Patents

Abstract

1,185,273. Isoindoline derivatives. CHEMIE GRUNENTHAL G.m.b.H. 11 June, 1968 [1 July, 1967], No. 27734/68. Heading C2C. Novel compounds I wherein R 1 signifies a hydrogen atom or an optionally substituted C 1-6 alkyl, C 1-6 alkenyl, aralkyl, cycloalkyl or aryl radical (if R 1 is an alkyl radical substituted by an amino group the nitrogen atom may be part of a 5 or 6 membered heterocyclio radical; thus R 1 includes, for example, pyrrolidinomethyl, piperidinomethyl and morpholinomethyl radicals) and m and n each represents 0, 1 or 2, the sum of m and n being 1 or 2, are obtained: (a) by reacting a corresponding isoindolinone-dicarboxylic acid (derived from the corresponding phthalimido compound by reducing one of the carbonyl groups to a -CH 2 - group) or a functional derivative thereof with an amine of the general formula, R 1 NH 2 , or with a compound able to form such an amine under the reaction conditions, e.g., salts thereof or ureas, thioureas or carbonic acid amides of such amines; (b) by reacting a compound I in which R 1 is a hydrogen atom with a compound of the general formula R 2 R 3 NH, or a salt thereof, in the presence of formaldehyde (R 2 and R 3 , which may be the same or different each signify H, alkyl, aryl or aralkyl, which may be substituted, or together with the adjacent nitrogen atom signify a 5 or 6 membered heterocyclic radical optionally containing a further hetero atom) or with a compound of the general formula R 2 R 3 N-CH 2 .X, wherein X signifies halogen, hydroxy or esterified hydroxy; or (c) by reacting a compound related to the compound I such that in place of R 1 there is a -CH 2 .X group {X as defined in (b) above} with a compound of the general formula R 2 R 3 NH (or salt thereof). 1 - Methylol - 4 - phthalimidino - piperidin - 2,6 - dione is prepared by the interaction of 4 - phthalimidino - piperidin - 2,6 - dione and formaldehyde. α- and #-Phthalimidino-glutaric acid anhydrides are obtained by reacting the free acids with acetic anhydride in the presence of thionyl chloride; phthalimidino-succinic acid anhydride is similarly obtained. α- and #-Phthalimidino glutaric acid monoamides are derived from the corresponding anhydrides by treatment with ammonia and α- and #-phthalimidino-glutaric acid-N-ethylamides from the anhydrides utilizing ethylamine. Pharmaceutical preparations possessing immunosuppressive and neuro-endocrine properties and showing a sedative effect contain as active ingredient compounds I.