GB966816A - New guanidines and process for their preparation - Google Patents

Abstract

The invention comprises 2-R-benzoylguanidines in which R is a free amino group or an amino group substituted by one or two hydrocarbon groups or by an acyl group and in which the benzene nucleus is unsubstituted or contains one or more substituents selected from alkyl, trifluoromethyl, alkoxy, nitro, amino and acylamino groups and halogen atoms, and in which the guanidino group is unsubstituted or substituted by one or more alkyl groups and/or the amino group of the guanidino group is part of a saturated heterocyclic ring; and salts thereof and their preparation by reacting a suitable 2-R-benzoic acid or a corresponding 2-nitro-compound, or functional derivatives thereof, with a suitable guanidine, and, when required, reducing the nitro group, and, if desired, acylating a 2-amino product or hydrolysing a 2-acylamino product. A lactone of a 2-acylamino-benzoic acid may be used as starting material. Nitro groups at other positions in the nucleus may also be reduced. Suitable acyl groups are alkanoyl, benzoyl and carbamoyl groups. Examples are given and a list of salt-forming organic and inorganic acids is provided. 2-Methyl -4- oxo -7- nitrobenzo-3, 1-oxazine is prepared by heating 4-nitro-anthranilic acid with acetic anhydride. The compounds of the invention, which are stated to have anti-inflammatory, anti-pyretic and anti-allergic action, may be made up into pharmaceutical compositions with suitable carriers. They may take the form of tablets, dragees, capsules, solutions, suspensions or emulsions and may contain preserving, stabilizing, wetting or emulsifying agents, salts for varying the osmotic pressure or buffers.