Patent GB-978855-A (GB)
Title: 1,1-(alkylene)bis(5-arylbiguanides), acid-addition salts thereof, and disinfecting oranitizing compositions containing same
IPC: C07C317/42
Filed: 1961-04-12
Abstract: The invention comprises compounds of the general formula <FORM:0978855/C1/1> (wherein CnH2n represents a bivalent alkylene bridge in which the free valence bonds are on two different carbon atoms and n is an integer from 2 to 12, and Q and Q1 each represent substituted phenyl having the formula <FORM:0978855/C1/2> wherein Y is hydrogen, halogen, trifluoromethyl, nitro, C1- 6 alkyl-O-, C1- 6 alkyl-S-, C1- 6 alkyl-SO- or C1- 6 alkyl-SO2-, Z is hydrogen, halogen, nitro, C1- 6 alkyl or C1- 6 alkyl-O-, R is alkyl, halo-C1- 6 alkyl, C2- 6 alkenyl, benzyl, ar-halobenzyl, ar-nitrobenzyl, ar-C1- 6 alkylbenzyl, ar-C1- 6 alkoxybenzyl, cyclohexyl, phenyl, C1- 6 alkylphenyl, nitrophenyl, C1- 6 alkoxyphenyl, halophenyl or, when neither Y nor Z is nitro, ar-aminobenzyl or aminophenyl, and X is -S-, -SO- or -SO2-) and acid addition salts thereof (including those with acidic resins-see Division C3), and their preparation by (a) reacting a 1,11(alkylene) bis (3-cyanoguanidine) of the formula <FORM:0978855/C1/3> with approximately two molecular proportions of an arylamine, preferably as an acid addition salt, of the formula <FORM:0978855/C1/4> (wherein R1 represents any of the values of R except ar-aminobenzyl or aminophenyl), or (b) reacting an alkylenediamine, as an acid addition salt, of the formula <FORM:0978855/C1/5> with approximately two molecular proportions of a 1-aryl-3-cyanoguanidine of the formula <FORM:0978855/C1/6> optionally followed in either case by (a) reduction of a compound wherein R1 is ar-nitrobenzyl or nitrophenyl and neither Y nor Z is nitro to the corresponding ar-aminobenzyl or aminophenyl compound, (b) oxidation of a compound wherein X is -S- or -SO- to the corresponding compound wherein X is -SO- or -SO2-, respectively, and/or (c) salt formation or conversion of a salt to the free base.  The 1-aryl-3-cyanoguanidine starting materials are prepared by reacting approximately equimolecular amounts of a corresponding arylamine acid addition salt and an alkali metal dicyanamide. 4-n-Propylsulphinyl-3-chloroaniline is prepared by oxidizing 4-n-propylmercapto-3-chloroaniline hydrochloride with hydrogen peroxide in aqueous acetic acid, and is converted to the hydrochloride.  The compounds of the invention have bactericidal, bacteriostatic, fungicidal and fungistatic activity, some of them have antiviral activity and others have amebacidal activity (see Division A5). Reference is made to the treatment with them of various disorders in animals.ALSO:The invention comprises addition salts of compounds of the general formula <FORM:0978855/C3/1> (wherein CnH2n represents a bivalent alkylene bridge in which the free valence bonds are on two different carbon atoms and n is an integer from 2 to 12, and Q and Q1 each represent substituted phenyl having the formula <FORM:0978855/C3/2> wherein Y is hydrogen, halogen, trifluoromethyl, nitro, C1-6 alkyl -O-, C1-6 alkyl-S-, C1-6 alkyl-SO- or C1-6 alkyl-SO2, Z is hydrogen, halogen, nitro, C1-6 alkyl or C1-6 alkyl-O-, R is alkyl, halo-C1-6 alkyl, C2-6 alkenyl, benzyl, ar-halobenzyl, ar-nitrobenzyl, ar-C1-6 alkylbenzyl, ar-C1-6 alkoxybenzyl, cyclohexyl, phenyl, C1-6 alkylphenyl, nitrophenyl, C1-6 alkoxyphenyl, halophenyl or, when neither Y nor Z is nitro, ar-aminobenzyl or aminophenyl, and X is -S-, -SO- or -SO2-) with acidic resins, e.g. sulphonated polystyrene.ALSO:The invention comprises disinfecting and sanitizing compositions containing a compound of the general formula <FORM:0978855/A5-A6/1> (wherein CnH2n represents a bivalent alkylene bridge in which the free valence bonds are on two different carbon atoms and n is an integer from 2 to 12, and Q and Q1 each represent substituted phenyl having the formula <FORM:0978855/A5-A6/2> wherein Y is hydrogen, halogen, trifluoromethyl, nitro, C1-6 alkyl-O-, C1-6 alkyl-S-, C1-6 alkyl-SO- or C1-6 alkyl-SO2-, Z is hydrogen, halogen, nitro, C1-6 alkyl or C1-6 alkyl-O-, R is alkyl, halo-C1-6 alkyl, C2-6 alkenyl, benzyl, ar-halobenzyl, ar-nitrobenzyl, ar-C1-6 alkylbenzyl, ar-C1-6 alkoxybenzyl, cyclohexyl, phenyl, C1-6 alkylphenyl, nitrophenyl, C1-6 alkoxyphenyl, halophenyl or, when neither Y or Z is nitro, ar-aminobenzyl or aminophenyl, and X is -S-, -SO- or -SO2-), or an acid addition salt thereof (including those with acidic resins), many are specified, and a carrier.  The active ingredients may be used in soap solution or sulfonate detergent solution to treat cotton cloth.