Method for preparing desferrioxamine B and homologs thereof
AssigneeUniversity of Florida Research Foundation, Inc.
InventorRaymond J. Bergeron, Jr.
Life of this patent
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Abstract
A new and versatile route to N'-[5-[[4-[[5-(acetylhydroxyamino)pentyl]amino]-1,4-dioxobutyl]hydroxyamin o]pentyl]-N-(5-aminopentyl)-N-hydroxybutanediamide, desferrioxamine B (DFO) is described. N-Benzyloxy-1,5-diaminopentane is selectively protected at the primary amino site. The product is reacted at the benzyloxyamine with an anhydride to produce a carboxylic acid which is, in turn, acylated regio-specifically with a diamine at the primary amine to give a benzyloxyamine. The previous two steps are repeated to afford a DFO reagent. Acetylation of the DFO reagent, followed by hydrogenolysis and tert-butoxycarbonyl group removal, furnishes DFO.
Claims6
A method for synthesizing desferrioxamine B or a homolog thereof having the formula:
- ##STR12## wherein:
- each n may be the same or different and is an integer from 1 to 10;
- a and b may be the same or different and are integers from 1 to 6;
- and
- R is an alkyl group having from 1 to 10 carbon atoms or an aryl group,
- comprising:
- (a) condensing a diamine having the formula:
- ##STR13## wherein Z is a hydroxyl protecting group and Q is an amino protecting group, with an anhydride having the formula:
- ##STR14## to produce a carboxylic acid having the formula:
- ##STR15## wherein n is an integer from 2 to 10, (b) condensing the carboxylic acid (8) with an amine having the formula:
- ##STR16## to produce an amide having the formula:
- ##STR17## (c) condensing amide (9) with an anhydride having the formula:
- ##STR18## to produce a carboxylic acid having the formula:
- ##STR19## (d) condensing compound (10) with amine (6) to produce an amide having the formula:
- ##STR20## (e) acylating amide (11) to produce a compound having the formula:
- ##STR21## (f) cleaving Z from compound (12) to produce a compound having the formula:
- ##STR22## (g) cleaving Q from compound (13) to produce said compound of formula (1).
Dependencies are inferred from the claim text.