Patent GB-788855-A (GB)
Title: Improvements in or relating to mandelo-nitrile-glucuronosides and method of making the same
IPC: C07H15/203
Filed: 1954-06-25
Abstract: The invention comprises l-mandelo-nitrile-beta-glucuronoside acid and derivatives thereof of the general formula: <FORM:0788855/IV (b)/1> wherein R1 represents hydrogen, a metal or hydrocarbon radical, and wherein the benzene ring may be substituted by a hydroxyl, methyl or nitro radical, preferablyin the para-position, and the preparation of the above compounds where R1 represents hydrogen by oxidizing an aqueous solution of an l-mandelo-nitrile-glucoside of the general formula: <FORM:0788855/IV (b)/2> in which the benzene ring may be substituted by a hydroxyl, methyl or nitro group, with molecular oxygen in the presence of platinum black, by condensing the required l-mandelo-nitrile with beta-glucuronic acid, or by hydrolysing a compound of the formula: <FORM:0788855/IV (b)/3> in which the benzene ring may be substituted by a hydroxyl, methyl or nitro group, by treatment with brewer's yeast, and oxidizing the resulting l-mandelo-nitrile-beta-glucoside with molecular oxygen in the presence of palladium black.  The esters and metal salts are formed by usual methods, suitable esters being the ethyl, n- and iso-propyl and various butyl esters, and suitable salts being the sodium and potassium salts.  The above processes using the l-mandelo-nitrile-beta-glucoside may be modified in that the l-mandelo-nitrile-beta-glucoside is prepared by condensing the required l-mandelo-nitrile with beta-glucose.  The racemic form of mandelo-nitrile may be used in place of l-mandelo-nitrile in processes referred to above, and d-mandelo-nitrile-beta-glucoside or the d-mandelo-nitrile-beta-glucuronoside acid may then be selectively destroyed in or removed from the resulting mixture of d- and l-mandelo-nitrile-beta-glucuside or d- and l-mandelo-nitrile-beta-glucuronoside acid respectively, e.g. by the use of a specific enzyme.  In the example, l-mandelo-nitrile-beta-glucuronoside acid and the sodium salt thereof are prepared from l-mandelo-nitrile-beta-glucoside which is obtained by the hydrolysis of amygdalin with yeast.ALSO:A therapeutic composition having bactericidal activity contains as the active ingredient l - mandelo - nitrile - beta - glucuronoside acid or a derivative thereof represented by the general formula <FORM:0788855/VI/1> wherein R1 represents hydrogen, a hydrocarbon radical or a metal such as sodium or potassium, and wherein the benzene ring may be substituted by a hydroxyl, methyl or nitro radical.  The diluent may be a solid extender suitable for oral administration, or may be an isotonic solution suitable for parenteral administration.  The active ingredient may be present in an amount from about 1/4 to 2 per cent by weight of the composition. The solid extender is preferably an alkaline extender, e.g. magnesium carbonate, magnesium oxide, brewer's yeast or rice bran.  Suitable isotonic solutions are Ringer's isotonic solution, Ringer-Tyrode's solution, and sodium chloride solutions.  A suitable compoition is 100 mgs. of active ingredient, e.g. sodium l-mandelonitrile-betaglucuronate, in about 3 to 5 c.c. of isotonic solution.