Patent GB-781479-A (GB)
Title: New polyureas and process for making them
IPC: C08L75/02
Filed: 1954-08-27
Abstract: The invention comprises polyureas of the formula (-R-NH-CO-NH-)n, wherein R is -Ph- or -Ph-X-Phin which -Ph-is a phenylene residue substituted by a free or esterified sulphonic acid group, X is a bridge member and in which the two residues bound by X may also be connected by a C-C bond in ortho position to X, and n is an integer such that the molecular weight of the compound is greater than 4000, and wherein the free valency of every residue R is bound to a further grouping -NH-CO-NH- or to a free amino group, and also salts of these polyureas.  Examples of bridge members X are -C­C-, -CH = CH-, -CH2CH2-, -NH-, -S-and -SO2-.  The products may be prepared by reacting a diamine H2N-R-NH2 or H2N-(R-NHCONH-)n-R-NH2 with a carbonic acid dihalide, e.g. phosgene, preferably in aqueous acidic medium. Mixtures of amines may be used yielding products having different residues R in the same molecule.  The compounds have pharmaceutical properties and may be mixed with carriers, e.g. water, gelatine, lactose, starches, magnesium stearate, talc, oils, benzyl alcohols, gums, glycols, cholesterol and petroleum jelly, for application.  In the examples: (1) phosgene is introduced into an aqueous solution of sodium 4,41-diaminostilbene-2,21-disulphonate and the product is washed with acetone, dialysed and further purified with acid and basic ion-exchangers, to give a mixture of polyureas containing the grouping: <FORM:0781479/IV (a)/1> with average molecular weights of 14,000, 124,000 and 440,000. (2) Phosgene is introduced into an aqueous solution of 4,41-diamino-dibenzyl-2,21-disulphonic acid and sodium acetate to give a mixture of polyureas of the formula: <FORM:0781479/IV (a)/2> (3) 4,41-Diamino-tolane-2,21-disulphonic acid is reacted with phosgene to give: <FORM:0781479/IV (a)/3> (4) Sodium 4,41-diamino-diphenylamine-2-sulphonate is reacted with phosgene to give: <FORM:0781479/IV (a)/4> from which the soluble ammonium salt is prepared.  (5) p-Phenylene diamine-2-sulphonic acid and phosgene yield: <FORM:0781479/IV (a)/5> (6) 4,41-diamino-diphenyl sulphide-2,21-disulphonic acid is neutralized and reacted with phosgene to give: <FORM:0781479/IV (a)/6> the ammonium salt of which is water-soluble.  (7) The product of Example (1) is esterified with diazomethane to give: <FORM:0781479/IV (a)/7> (8) The product of Example (1) is also prepared using bis - 4,4 - (41 - aminostilbene - 2,21 - disulphonic acid) - urea and phosgene.  (9) 2,7-diamino - dibenzo - thiophene dioxide - 3,6 - disulphonic acid is neutralized and reacted with phosgene to give: <FORM:0781479/IV (a)/8> from which the soluble ammonium salt is obtained.ALSO:Bis - 4,4 - (41 - aminostilbene - 2,21 - disulphonic acid)-urea <FORM:0781479/IV (a)/1> is prepared by introducing phosgene into a neutralized aqueous solution of 4-amino-41-nitrostilbene-2, 21-disulphonic acid and reducing the product, bis-4,4-(41-nitrostilbene-2,21-disulphonic acid)-urea, in ammoniacal solution with hydrogen sulphide at the boil.ALSO:Medicaments having anti-virus properties comprise a carrier and a polyurea of the formula <FORM:0781479/VI/1> wherein R is-Ph or -Ph-X-Phin which -Phis a phenylene residue substituted by a free or esterified sulphonic acid group, X is a bridge member and in which the two residues bound by X may also be connected by a C-C bond in ortho position to X, and n is an integer such that the molecular weight of the compound is greater than 4000, and wherein the free valency of every residue R is bound to a further grouping -NHCONH- or to a free amino group, or a salt of such a polyurea.  Suitable carriers are water, gelatine, lactose, starches, magnesium stearate, talc, vegetable oils, benzyl alcohols, gums, polyalkylene glycols, cholesterol and the material known under the Registered Trade Mark "Vaseline". The medicaments may be in the form of of tablets, dragees, salves and creams, or in liquid form as solutions, suspensions or dispersions.  They may be sterilized and may contain additives such as preserving, stabilizing and wetting agents, and salts for regulating osmotic pressure or buffers.  Other therapeutic substances may also be added.