GB1480374A - Aminocyclitol-aminoglycoside antibiotics and process for their preparation - Google Patents

Abstract

1480374 Mutamicins SCHERICO Ltd 1 Aug 1974 [6 Aug 1973] 33967/74 Heading C2C Novel mutamicins (I) and their acid addition salts and oxazolidene derivatives in which V 5 is hydrogen and W 5 is hydrogen, hydroxy or C 1-8 alkoxy or W 5 is hydrogen and V 5 is hydrogen, hydroxy, amino or C 1-8 alkoxy and one of V 2 and W 2 is hydrogen and the other is hydrogen or hydroxy with the proviso that when W 5 , V 2 and W 2 are hydrogen then V 2 is not hydroxy are prepared by fermentation of a mutant of Micromonospora inyoensis (preferably strain 15505-IG; NRRL 5742) in an aqueous nutrient medium containing a compound II until antibiotic activity is imparted to the medium followed by isolation of the mutamicin produced and, if desired, formation of the acid addition salt or oxazolidine derivative. Compounds I (V 2 = W<SP>2</SP> = V 5 = W 5 = H; V 2 = W 2 = V 5 = H, W 5 = OH; V 2 = W 2 = W 5 = H, W 2 = OH; V 2 = W 2 = W 5 = H, W 2 = NH 2 ; W 2 = W 5 = H, V 2 = V 5 = OH) are prepared. 2 - Dioxy - myoinosa - 1,3,5 - triamine is prepared by hydrolysis of the corresponding 3,5 di - N - acetyl derivative, 2 - deoxy - 5 - epistreptamine is prepared by hydrolysis of a corresponding 1,3,4,6-tetraacyl derivative. 2,5- Dideoxy streptamine may be prepared by reaction of the dicarbamate of 2-deoxy streptamine with iodomethyl - triphenylphosphorane to form the 5-iodo derivative followed by hydrogenolysis and hydrolysis. 5-O-methyl-2-deoxystreptamine may be prepared by methylating the dicarbamate of 2-deoxystreptamine and hydrolysis. 5-Amino-2,5-dideoxystreptamine may be prepared by periodate cleavage of an N,N- deacyl 2-deoxystreptamine and treatment with nitromethane under basic conditions to give 5-nitro-2,5-dideozystreptamine which is reduced. Compounds I are anti-bacterial agents and form a pharmaceutical composition. They may be used as disinfecting agents combined with detergents.