Patent EP-0271443-B1 (EP)
IPC: C07C275/16
Filed: 1987-12-03
Granted: 1990-10-17
Abstract: 1. Claims for the Contracting States : AT, BE, CH, DE, FR, GB, IT, LI, LU, NL, SE A compound of the formula I   see diagramm : EP0271443,P21,F1   in which B represents a carbamoyl radical of the partial formula -CO-NH-Alk-CO-O-R**1 a (II) in which R**1 a represents C1 -C4 -alkyl or C2 -C4 -alkenyl and Alk represents C1 -C7 -alkylene that is unsubstituted or substituted by hydroxy, C1 -C4 -alkanoyloxy, amino, C1 -C4 -alkoxycarbonyl, carbamoyl, phenyl, hydroxyphenyl, methoxyphenyl or by indolyl, and each of the symbols A**1 , A**2 and A**3 , independently of the others, represents hydrogen, an acyl radical Ac derived from a carboxylic acid, or an above-defined carbamoyl radical of the partial formula II, or a salt of such a compound having salt-forming properties. 1. Claims for the Contracting States : ES, GR A process for the manufacture of a compound of the formula I   see diagramm : EP0271443,P23,F2   in which B represents a carbamoyl radical of the partial formula -CO-NH-Alk-CO-O-R**1 a represents C1 -C4 -alkyl or C2 -C4 -alkenyl and Alk represents C1 -C7 -alkylene that is unsubstituted or substituted by hydroxy, C1 -C4 -alkanoyloxy, amino, C1 -C4 -alkoxycarbonyl, carbamoyl, phenyl, hydroxyphenyl, methoxyphenyl or by indolyl, and each of the symbols A**1 , A**2 and A**3 , independently of the others, represents hydrogen, an acyl radical Ac derived from a carboxylic acid, or an above-defined carbamoyl radical of the partial formula II, or a salt of such a compound having salt-forming properties, characterised in that a) a derivative of desferrioxamine B of the formula IV   see diagramm : EP0271443,P24,F1   in which BO represents hydrogen or an organic silyl group Sil and each of the symbols A**1 O , A**2 O and A**3 O , independently of the others, represents hydrogen, an organic silyl group Sil or an above-defined acyl radical Ac, is reacted with an isocyanatocarboxylic acid ester of the formula III O=C=N-Alk-CO-O-Ra-1 in which Alk and R**1 a have the meanings given above and in which an additional amino group that may be present in the radical Alk is in protected form, or b) a derivative of desferrioxamine B of the formula V   see diagramm : EP0271443,P24,F2   in which W is chlorine or 1-imidazolyl, and in which each of the symbols A**1 O , A**2 O and A**3 O , independently of the others, represents hydrogen, an organic silyl group Sil or an above-defined acyl radical Ac, is reacted with an amino acid ester of the formula H2 N-Alk-CO-O-Ra-1 in which Alk and R**1 a have the meanings given above and in which an additional amino group that may be present in the radical Alk is in protected form, and, if desired, any silyl groups and/or amino-protecting groups that may be present are removed to free the corresponding hydroxy and amino groups, respectively, and, if desired, a resulting compound of the formula I in which at least one of the symbols A**1 , A**2 and A**3 is hydrogen is acylated to a compound of the formula I in which the corresponding symbols represent Ac or a carbamoyl radical of the partial formula II and/or, if desired, a resulting free compound of the formula I having salt-forming properties is converted into a salt and/or a compound of the formula I is freed from such a salt.