Patent GB-1427471-A (GB)
Title: Amino-glycosides, preocesses for their preparation and composi tions thereof
IPC: A61P31/04
Filed: 1974-05-08
Abstract: 1427471 Streptamine derivatives ROUSSELUCLAF 8 May 1974 [10 May 1973 5 March 1974] 20188/74 Heading C2C Novel 4 - 0 - [2<SP>1</SP>,6<SP>1</SP> - diamino - 2<SP>1</SP>,6<SP>1</SP> - didesoxy - α,D - glucopyranosyl] - 6 - 0 - [3<SP>11</SP> - methylamino - 3<SP>11</SP>,4<SP>11</SP>,6<SP>11</SP> - tridesoxy - α,D - xylohexopyranosyl] - 2 - desoxystreptamine (I) and its mineral and organic acid addition salts are prepared by reacting ethyl 2-0-ethoxycarbonyl - 3 - (N - methyl - N - ethoxycarbonyl)- amino - 3,4,6 - tridesoxy - D - xylohexopyranoside with an alkaline agent at ambient temperature, treating the resulting ethyl 3-(N- methyl - N - ethoxycarbonyl)amino - 3,4,6 - tridesoxy - D - xylohexopyranoside with benzyl halide in the presence of an alkaline agent, treating the resulting ethyl 2-0-benzyl-3-(N- methyl - N - ethoxycarbonyl)amino - 3,4,6 - tridesoxy - D - xylohexopyranoside with acetic anhydride in acetic acid, in the presence of a strong acid, treating the resulting 1-0-acetyl-2-0- benzyl - 3 - (N - methyl - N - ethoxycarbonyl)- amino - 3,4,6 - tridesoxy - D - xylohexopyranose with anhydrous HCl in the presence of acetyl chloride and an organic solvent, condensing the resulting 1 - chloro - 2 - 0 - benzyl - 3 - (N- methyl - N - ethoxycarbonyl)amino - 1,3,4,6- tetradesoxy - D - xylohexopyranose with 4 - 0- [2<SP>1</SP> - (N - benzoxycarbonyl) - amino - 2<SP>1</SP> - desoxy - 3<SP>1</SP> - 0 - benzyl - 4<SP>1</SP>,6<SP>1</SP> - 0 - isopropylidene- α,D - glucopyranosyl] - N<SP>1</SP>,N<SP>11</SP> - dibenzoxycarbonyl - 2 - desoxy - streptamine in the presence of a catalyst and separating the α-anomer from the obtained mixture of α- and #-anomers, treating the resulting 4-0-[2<SP>1</SP>-(N-benzoxycarbonyl)amino - 2<SP>1</SP> - desoxy - 3<SP>1</SP> - 0 - benzyl - 4<SP>1</SP>,6<SP>1</SP>- 0 - isopropylidene - α,D - glucopyranosyl] - 6 - 0- [2<SP>11</SP> - 0 - benzyl - 3<SP>11</SP> - (N - methyl - N - ethoxycarbonyl) - amino - 31<SP>1</SP>,4<SP>11</SP>,6<SP>11</SP> - tridesoxy - α,D- xylohexopyranosyl) - N<SP>1</SP>,N<SP>11</SP> - dibenzoxycarbonyl- 2-desoxy-streptamine with dilute acid, treating the resulting novel 4 - 0 - [2<SP>1</SP> - (N - benzoxycarbonyl)amino - 2<SP>1</SP> - desoxy - 31 - 0 - benzyl- α,D - glucopyranosyl] - 6 - 0 - [2<SP>11</SP> - 0 - benzyl- 3<SP>11</SP> - (N - methyl - N - ethoxycarbonyl)amino- 3<SP>11</SP>,4<SP>11</SP>,6<SP>11</SP> - tridesoxy - α,D - xylohexopyranosyl]- N<SP>1</SP>,N<SP>11</SP> - dibenzoxy - carbonyl - 2 - desoxystreptamine with tosyl chloride in the presence of a tertiary organic base, reacting the resulting 4 - 0 - [21 - (N - benzoxycarbonyl) - amino - 2<SP>1</SP>- desoxy - 3<SP>1</SP> - 0 - benzyl - 6<SP>1</SP> - 0 - tosyl - α,D- gluco - pyranosyl] - 6 - 0 - [2<SP>11</SP> - 0 - benzyl- 3<SP>11</SP> - (N - methyl - N - ethoxy - carbonyl)amino- 3<SP>11</SP>, 4<SP>11</SP>, 6<SP>11</SP> - tridesoxy - α,D - xylohexo - pyranosyl] - N<SP>1</SP>,N<SP>11</SP> - dibenzoxycarbonyl - 2 - desoxystreptamine with sodium azide, reducing the resulting 4 - 0 - [21 - (N - benzoxycarbonyl)- amino - 6<SP>1</SP> - azido - 3<SP>1 </SP>- 0 - benzyl - 2<SP>1</SP>,6<SP>1</SP> - didesoxy - α,D - glucopyranosyl] - 6 - 0 - [2<SP>11</SP> - 0- benzyl - 311 - (N - methyl - N - ethoxycarbonyl)- amino - 3<SP>11</SP>, 4<SP>11</SP>, 6<SP>11</SP> - tridesoxy - α,D - xylohexopyranosyl] - N,N<SP>11</SP> - dibenzoxycarbonyl - 2 - desoxystreptamine with hydrogen in the presence of a catalyst and treating the resulting 4-0- [2<SP>1</SP>,6<SP>1</SP> - diamino - 2<SP>1</SP>,6<SP>1</SP> - didesoxy - α,D - glucopyranosyl] - 6 - 0 - [3<SP>11</SP> - (N - methyl - N- ethoxycarbonyl)amino - 3<SP>11</SP>,4<SP>11</SP>,6<SP>11</SP> - tridesoxy- α,D - xylohexopyranosyl] - 2 - desoxy - streptamine with an alkaline reagent (to liberate the 3<SP>11</SP>-methylamino group), followed optionally by salification. Pharmaceutical compositions having antibiotic activity comprise, as active ingredient, the compound I or a therapeutically acceptable mineral or organic acid addition salt thereof, in association with a suitable pharmaceutical vehicle.