Patent GB-944533-A (GB)
Title: 2-amino-5-nitrothiazole derivatives, their preparation and therapeutic compositions containing them
IPC: C07D277/58
Filed: 1962-03-15
Abstract: The invention comprises compounds (antiprotozoal, antibacterial and antifungal agents) of the general formula: <FORM:0944533/C2/1> (wherein n is 1 or 2 and R is C1-4 alkyl, benzyl, halobenzyl, nitrobenzyl, (C1-4 alkyl) benzyl, (C1-4 alkoxy) benzyl, phenyl, halophenyl, nitrophenyl, (C1-4 alkyl) phenyl or (C1-4 alkoxy) phenyl, provided that when R is a substituted benzyl or substituted phenyl group there may be more than one substituent of the kind set forth), and their preparation by reacting 2-amino-5-nitrothiazole with RS(CH2)nCOX (wherein X is a halogen atom) in the presence of a base. The starting materials RS(CH2)nCOX are prepared by reacting the parent acids with thionyl chloride.  The preparation of the following acids, from the materials indicated in parentheses, is described: p-nitrobenzyl-mercaptoacetic acid (p-nitrobenzyl chloride and thioglycollic acid); n-butylmercaptoacetic acid (butyl mercaptan and chloroacetic acid); b -methyl-mercaptopropionic acid (b -mercaptopropionic acid and methyl iodide); p-chlorobenzylmercapto-acetic acid (sodium thiosulphate, chloroacetic acid and p-chlorobenzyl chloride); p-chlorophenyl-mercaptoacetic acid (p-chlorothiophenol and chloroacetic acid); b -(p-chlorobenzylmercapto) propionic acid (p-chlorobenzyl chloride and b -mercaptopropionic acid); and phenylmercapto-acetic acid (thiophenol and chloroacetic acid).ALSO:Pharmaceutical preparations (e.g. ointments, creams, suppositories, capsules, oral and vaginal tablets, and water-miscible and water-dispersible preparations) for use in the treatment of protozoal, bacterial and fungal infections comprise a compound of the general formula <FORM:0944533/A5-A6/1> (wherein n is 1 or 2 and R is C1-4 alkyl, benzyl, halobenzyl, nitrobenzyl, (C1-4 alkyl) benzyl, (C1-4 alkoxy) benzyl, phenyl, halophenyl, nitrophenyl, (C1-4 alkyl) phenyl or (C1-4 alkoxy) phenyl, provided that when R is a substituted benzyl or substituted phenyl group there may be more than one substituent of the kind set forth) and a vehicle therefor.  The above compounds may also be used to protect plants and trees against fungus rot.ALSO:The formation and growth of slime in paper-making operations may be controlled by means of compounds of the general formula <FORM:0944533/D1-D2/1> (wherein n is 1 or 2 and R is C1-4 alkyl, benzyl, halobenzyl, nitrobenzyl, (C1-4 alkyl) benzyl, (C1-4 alkoxy) benzyl, phenyl, halophenyl, nitrophenyl, (C1-4 alkyl) phenyl or (C1-4 alkoxy) phenyl, provided that when R is a substituted benzyl or substituted phenyl group there may be more than one substituent of the kind set forth).ALSO:Citrus fruits, plants, trees, wood, paper and textiles are protected against fungus rot by compounds of formula <FORM:0944533/A1-A3/1> (wherein n is 1 or 2 and R is C1-4 alkyl, benzyl, halobenzyl, nitrobenzyl, (C1-4 alkyl) benzyl, (C1-4 alkoxy) benzyl, phenyl, halophenyl, nitrophenyl, (C1-4 alkyl) phenyl or (C1-4 alkoxy) phenyl, (when R is substituted benzyl or substituted phenyl there may be more than one of the substituents), application being by spraying, painting or dipping.