GB1473733A — Pseudotrisaccharides and methods for their production

USPTO Abstract

1473733 Pseudo trisaccharides SCHERICO Ltd 1 Aug 1974 [6 Aug 1973 19 March 1974 (2)] 33968/74 Heading C2C The invention comprises 1-N substituted derivatives of the 4,5-di-(aminoglycosyl)-1,3- diaminocyclitols gentamicin A, gentamicin B, gentamicin B 1 , gentamicin C 1 , gentamicin C 1a , gentamicin C 2 , gentamicin C 2a , gentamicin C 2b , gentamicin X 2 , sisomicin, vendamicin, tobramycin, Antibiotic G-418, Antibiotic 66-40B, Antibiotic 66-40D, Antibiotic J1-20A, Antibiotic J1-20B, Antibiotic G-52, mutamicin 1, mutamicin 2, mutamicin 4, mutamicin 5 and mutamicin 6, where the substituent is -CH 2 X with X being hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, hydroxyalkyl, aminoalkyl, N-alkylaminoalkyl, aminohydroxyalkyl, N-alkylaminohydroxyalkyl, phenyl, benzyl or tolyl, said aliphatic radicals having up to seven carbon atoms and, if substituted by amino and hydroxy, bearing the substituents on different C atoms and pharmaceutically acceptable acid addition salts thereof. The compounds of the invention may be prepared by treating one of the above named 4,6-di-(aminoglycosyl)-1,3- diaminocyclitols which may have aminoprotecting groups at any position other than position 1, with an aldehyde of formula X<SP>1</SP>-CHO, with X<SP>1</SP> being a group as defined for X above wherein any amino or hydroxy group present may be protected in the presence of a hydride donor and reducing agent and, if required, removing all protecting groups present in the molecule the last process step being followed by isolating the derivative as such or as a pharmaceutically acceptable acid addition salt.