N-Aromatically Substituted Acid Amides

摘要

1,154,260. N-Aromatically substituted acid amides. DEUTSCHE GOLD-UND SILBERSCHEIDEANSTALT. 16 Nov., 1967 [16 Nov., 1966; 1 Sept., 1967], No. 52312/67. Heading C2C. Novel N-aromatically substituted acid amides of the formula and the acid addition salts of such compounds with basic nitrogen atoms, wherein X represents a nitrogen atom or a CH group; Y represents an NH or CH 2 group; R2 represents a hydrogen atom or a C 1-5 alkyl group; R3 represents a hydrogen or halogen atom or an alkyl or alkoxy radical; R4 and R5, which may be the same or different, represent a hydrogen or halogen atom, a C 1-5 alkyl, nitro, trifluoromethyl, C 1-5 alkoxy, C 1-5 alkylamino, amino or hydroxyl groups; R1 represents an oxygen atom or a hydrogen atom plus a hydroxyl group, in which case the hydroxyl and/or amino groups may be acylated by aliphatic carboxylic acids with 1-5 carbon atoms or by aliphatic carbonic acid semi-esters; and wherein if R1 is oxygen, R2 is hydrogen, X is a CH group and Y is an NH group at least one of R3, R4 and R5 is not a hydrogen atom, are prepared by: (a) reacting the corresponding amine with an appropriate acid of formula CH 3 -C(=R1 1 )CH(R2)-COOH or with a derivative thereof, and optionally alkylating the resulting compound in which R1 is O and R2 is H with alkyl halides of the formula R2Hal, and/or optionally reducing the keto group in compounds in which R1 represents oxygen to a hydroxyl group and optionally acylating any hydroxyl group present by known methods; (b) nitrating a compound of the above general formula in which R5 is a hydrogen atom; or (c) reducing the nitro group introduced as in (b) to an amino group, and optionally acylating it. The products possess analgetic, antiphlogistic, antipyretic and spasmolytic activity.