GB837008A - Basically substituted butyric acid amides and a process for their manufacture - Google Patents

Abstract

The invention comprises amides of the general formula <FORM:0837008/IV (b)/1> in which R1 represents hydrogen or an alkyl radical containing at most 4 carbon atoms and R2 stands for a phenyl radical which may be substituted by alkyl or alkoxy groups containing up to 2 carbon atoms, or halogen, e.g. chlorine, atoms, or R1 and R2 together with the nitrogen atom may form a heterocyclic ring system. The amides are made by reacting a compound of the general formula <FORM:0837008/IV (b)/2> with formaldehyde in the presence of formic acid or by catalytic hydrogenation in the presence of formaldehyde. Suitable starting materials include the phenetidide, anilide, p-anisidide, N - methyl - p - phenetidide, N-ethylp-phenetidide, m-anisidide, N-isopropylanilide, N - n - butyl - p - anisidide, N - isobutyl - anilide, o-anisidide, p-toluidide, xylidide, N-propyl-p-phenetidide, 1:2:3:4 - tetrahydroquinolide and 1:2:3:4 - tetrahydro - 6 - methoxy - quinolide of a -amino-b -hydroxy-butyric acid. The compounds are used pharmaceutically as analgesics and sedatives. Examples describe the preparation of the phenetidide, 6-methoxy-1:2:3:4 - tetrahydro - quinolide, N - methyl-p-phenetidide, N - n - butyl - p - anisidide, p-chloranilide and 3 - chloro - 4 - methyl anilide of a - dimethylamino - b - hydroxy - butyric acid. a - Amino - b - hydroxy - butyric acid amides used as starting materials are made by treating the corresponding acetoacetic acid amides with nitrous acid and reducing the isonitroso group and the keto group in the resulting compound. Acetoacetic acid amides such as acetoacetic acid - 1:2:3:4 - tetrahydro - 6 - methoxy quinolide, N - methylphenetidide, N - n - butyl-p-anisidide and p-chloranilide are made by reacting the corresponding amine with diketene. Specification 828,694 is referred to.