EP0302699A2 — Improvements relating to n-substituted benzamides

USPTO Abstract

Compounds of the general formula: wherein R¹ represents hydrogen, a C₁₋₆ alkyl group or an acetyl group; R² represents halogen; R³ represents a group of the formula: wherein R⁵ represents hydrogen or a phenyl or non-aromatic cyclic ether group and n is 2 or 3; R⁴ represents a C₃₋₆ cycloalkyl, cyclohexenyl, C₁₋₆ alkoxy, trifluoromethyl, tetrahydrofuryl, 1,3-dioxolanyl or phenoxy group; m is 0, 1, 2, 3 or 4 with the proviso that when m is 0, R⁴ is only a C₃₋₆ cycloalkyl or tetrahydrofuryl group; and pharmacologically acceptable acid addition salts, quaternary ammonium salts and N-oxides thereof have pharmacological properties rendering them useful as antiematic agents with reduced undesirable side-effects. Various methods are described for their preparation involving formation of the amide link, etherification of the 2-hydroxy derivative, introducing the R⁵CH₂ group on the N-unsubstituted azabicyclooctane or nonane or, for 4-amino compounds, by hydrolysing a 4-acylamino derivative.