GB1001667A - Ring-nitrogen compounds and preparation thereof - Google Patents

Abstract

The invention comprises compounds of the formula <FORM:1001667/C2/1> (wherein the groups R, which may be the same or different, are hydrogen atoms, hydroxy groups, or alkoxy or alkyl groups of at most 5 carbon atoms, or together are a methylene-dioxy group; R1 is an amino, mono- or dialkylamino, aralkylamino which may be halogen or alkyl substituted, picolinylamino, butidinylamino, collidinylamino, anilino, p-toluidino, p-anisidino, pyridylamino, N-alkyl-N-phenyl-amino, pyrrolyl, pyrrolidino, piperidino, 2-methylpiperidino, morpholino, piperazino or N1 - methyl - piperazino group, each alkyl group in R1 containing at most 4 carbon atoms; and Z is a carbonyl or hydroxy-methylene group) and their acid-addition salts and quaternary ammonium derivatives; and their preparation by reacting an unsubstituted or an appropriately substituted 2-oxo-3-carbo-alkoxy - 1,2,3,4,6,7 - hexahydro - 11b - H-benzopyridocoline with at least an equimolar amount of ammonia or the appropriate amine R1H to give products wherein Z is carbonyl and then, if desired, reducing these to give products wherein Z is hydroxymethylene. The last-named products may be separated into their isomeric forms by chromatography. Examples are given and a list of salt-forming organic and inorganic acids and quaternizing agents is provided. The benzopyridocolines of the invention, which are stated to be of use as tranquilizers, sedatives, hypotensive and cardiovascular agents, may be made up into pharmaceutical compositions with suitable carriers. Tablets, capsules, lozenges, troches, hard candies, powders, sprays, aqueous suspensions, injection solutions, elixirs and syrups are referred to, and these may contain sweetening or flavouring agents, emulsifying and/or suspending agents, buffers, and salts for rendering them isotonic.