Patent GB-946029-A (GB)
Title: Salicylic acid derivatives and compositions containing them
Inventor: BRUNNER MATTHEW JOSEPH
IPC: A61Q17/04
Filed: 1961-04-17
Abstract: The invention comprises compounds of the formula: <FORM:0946029/C2/1> (wherein X is hydrogen, acetyl, amino or allyl, Y is hydrogen, alkyl of at most 5 carbon atoms, or acyl of at most 5 carbon atoms, and Z is carboxy, carbaltoxy of at most 6 carbon atoms, carbaryloxy, b -dimethylaminoethoxycarbonyl, b -tertiary-butylaminoethoxycarbonyl, b -morpholinoethoxycarbonyl, trifluoromethylmethoxycarbonyl, o-aminophenylcarbamoyl, or 2-benzimidazolyl, with the limitations that when X is hydrogen and Z is carboxy, Y is not hydrogen, methyl or acetyl, and that when X and Y are both hydrogen, Z is not carbomethoxy) and acid-addition salts of the amino compounds; and the preparation of the compounds in which Z is b  - dimethylaminoethoxycarbonyl, b  - tertiary -butylaminoethoxycarbonyl or b -morpholinoethoxycarbonyl and X and Y are hydrogen by reacting a lower alkyl ester of 5-phenylsalicylic acid with the appropriate secondary or tertiary amino alcohol.  In examples (1) 2-acetoxy-5-phenyl-benzoic acid is heated in nitrobenzene with aluminium chloride to give 3-acetyl-5-phenyl-salicylic acid; (2) 5-phenyl-salicylic acid is nitrated to 3-nitro-5-phenyl-salicylic acid and this is reduced to 3-amino-5-phenyl-salicylic acid; (3) methyl 5-phenyl-salicylate and allyl bromide give methyl 3-allyl-5-phenylsalicylate and other esters are prepared similarly; (4) methyl 5-phenyl-salicylate and dimethyl sulphate give methyl 2-methoxy-5-phenylbenzoate and other esters are prepared similarly; (5) methyl 5-phenyl-salicylate is acetylated to give methyl 2-acetoxy-5-phenylbenzoate and other 2-esters are prepared similarly; (6) 5-phenylsalicylic acid and phenol in the presence of phosphorus oxychloride give phenyl 5-phenylsalicylate; (7) 5-phenylsalicylic acid and n-butanol give butyl 5-phenyl-salicylate and other alkyl esters are prepared similarly; 5-phenylsalicyloyl chloride and trifluoroethanol give trifluoroethyl 5-phenylsalicylate; (8) 5-phenylsalicylic acid and o-phenylenediamine give N-(o-aminophenyl)-5-phenylsalicylamide; and (9) the starting materials of (8) heated for a prolonged time give 21-(2-hydroxy-5-phenyl)-phenylbenzimidazole. Other examples describe esterifications with aminoalcohols as referred to above.  Salts with organic and inorganic acids are described or referred to.ALSO:Dermatological compositions comprise an acceptable dermatological base and 0.001% to about 10% by weight of a 5-phenyl-salicylic acid derivative of the formula <FORM:0946029/A5-A6/1> (wherein X is hydrogen, acetyl, amino or allyl, Y is hydrogen, alkyl of at most 5 carbon atoms, or aryl of at most 5 carbon atoms, and Z is carboxy, carbalkoxy of at most 6 carbon atoms, carbaryloxy, b  - dimethylaminoethoxycarbonyl, b  - tertiarybutyl aminoethoxycarbonyl, b  - morpholinoethoxycarbonyl, trifluoromethylmethoxycarbonyl, o - aminophenylcarbamoyl, or 2 - benzimidazolyl) or an acid-addition salt of the amino compounds. They may take the form of ointments, lotions, pastes, jellies or powders, and may include local or topical anaesthetic, antibacterials, antibiotics, antiseptics, emulsifying agents, solvents, antioxidants, preservatives, buffers, perfumes and bodying materials.  Examples are given.  The compositions may be used for the prevention and treatment of sunburn.