NOVEL 1-BENZOYLOXY-2-LOWER ALKYLAMINO-BENZOCYCLOALKANE DERIVATIVES

1360119 Benzoyloxy alkylamino benzocycloalkane derivatives YAMANOUCHI PHARMACEUTICAL CO Ltd 7 June 1972 [22 June 1971 6 Dec 1971 10 Dec 1971] 26607/72 Heading C2C Novel compounds of Formula IIIa and salts thereof wherein R1 represents hydrogen atom or a lower alkyl group; R2 represents a lower alkyl group; R3, R4 and R5 are same or different from each other and each represents hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, phenyl group, amino group, a lower alkylamino group, an acylamino group, or nitro group; n is an integer of 1-3; and lower indicates groups of up to 5 carbon atoms are prepared by one of the following methods; (a) a compound of Formula I is reacted with a compound of Formula II or a reactive derivative thereof; (b) a compound of Formula IV is alkylated at the amino group; or (c) a compound of Formula IV above or a compound of Formula V is heated with formaldehyde/formic acid, also amino substituted compounds may be obtained by reduction of the corresponding nitro compound and salts may be formed and compounds separated into their isomers. Intermediates of Formula I above are prepared by alkylation of the free amine or, e.g. 2-methyl-3a,4,5,9b-tetrahydronaphtho-[2, 1d]oxazole obtained by reaction of 2 - acetamide - 1 - hydroxy tetralin with SOCl 2 or of cis - 2 - phenyl - 3,4,5,9b - tetrahydro - [2,1d] oxazole or of 2 - phenyl - 3a,4,5,9b - tetrahydronaphtho-[2,1d]oxazole which is prepared by action of c.nc. H 2 SO 4 on trans-2-benzoylamino- 1-hydroxytetralin obtained by reduction of the 2-benzoylaminotetralone prepared by benzoyation of 2-amino-1-tetralone hydrochloride. Pharmaceutical compositions in conventional forms for oral administration and having local anaesthetic action, e.g. for relief of pain from ulcers, comprises an above novel compound and a carrier therefor.