Patent GB-519661-A (GB)
Title: Improvements in sulphonamide compounds and methods for making same
IPC: C07C311/37
Filed: 1938-09-30
Abstract: 519,661. Sulphonamide compounds. MEYER, F. Sept. 30, 1938. Nos. 28526 and 28527. Convention dates, Nov. 20, 1937, and July 28, 1938. [Class 2 (iii)] Water soluble polyhydroxy-alkyl amino aromatic sulphonamides are prepared by reacting an amino aromatic sulphonamide with an aldose particularly aldoses having abnormal ether linkages. This type of aldose is defined as an aldose which contains an ether linkage connecting other carbon atoms than a first and a fourth carbon atom of the chain such as galactose, xylose, glucosan, laevo-glucosan, and polyoses containing them such as lactose. Polyoses containing exclusively glucosic ether linkages and an ether linkage between the carbonyl atoms of the monose radicals of the polyose are excluded. The reaction between the amide and the aldose may be effected by beating the components to temperatures below their decomposition point in the dry state or in an aqueous or preferably in an organic solvent such as alcohol. Other suitable . solvents mentioned include methyl alcohol, or mixtures of methyl and ethyl alcohols with higher alcohols such as propyl alcohol, or dioxane. The preferred modification is to heat the components in a closed vessel under pressure to a temperature preferably above the boiling point of the solvent used but below the decomposition temperature of the reactant. The pressure may be obtained by the introduction of neutral gases such as carbon dioxide, nitrogen, or preferably steam. The products of the invention are valuable in diseases caused by streptococci, especially of the hemolytic type as found in septicemia, peritonitis, erysipelas, scarlet fever, mastoiditis, septic sore throat and meningitis. They are easily soluble in water, physiological salt solutions, and aqueous solutions of enzymes ferments or in sera. In examples (1) Commercial galactose and commercial sulphanilic acid are dissolved in ethyl alcohol and refluxed for six hours. The reaction may be shortened by the addition of a small amount of ammonian chloride ; (2) Lactose and sulphanilic acid amide are refluxed in 95 per cent. ethyl alcohol for five hours; (3) Xylose and sulphanilic acid amide are refluxed in 95 per cent. ethyl alcohol for three hours, and excess of alcohol then distilled off when the condensation product crystallizes ; (4) Sulphanilic acid amide, and galactose are heated in ethyl alcohol solution in a closed tube in the presence of a small amount of glycerol under a steam pressure of 10 lbs. per sq. inch. The reaction mixture which is a yellow syrup is treated with pyridine and then ethyl alcohol added to give a crystalline precipitate of the desired condensation product; (5) Sulphanilamide, xylose and glycerol are treated with live steam at 10-15 1bs. per sq. inch pressure in ethyl alcohol solution. The reaction product is crystallized from alcohol. The Specification as open to inspection under Sect. 91 also. describes the hydrogenation of the,product by passing hydrogen through the reaction mixture after adding a mild hydrogenation catalyst such as pure, superficially activated nickel or alloys thereof with copper. Reference is also made to the condensations of sulphanylp-aminobenzene-sulphonamide with galactose in presence of glycerol. This subject-matter does not appear in the Specification as accepted.