US 6,503,727 B1Granted

Process for the preparation of an antibiotic

AssigneeGist-Brocades N.V.

InventorsWilhelmus H. J. Boesten, Wilhelmus J. J. Van Den Tweel, Rocus M. Dekkers

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Abstract

The invention relates to a process for the preparation of an antibiotic, in particular cefalexin, ampicillin, amoxicillin, cefaclor, cefradin, cefadroxil, cefotaxim and the like, wherein a beta-lactam core is acylated, the antibiotic is recovered from the reaction mixture, the remaining mother liquor is subjected to a hydrolysis reaction in which the antibiotic present in the mother liquor is decomposed into its initial compounds, in particular the beta-lactam core, and the acylation agent is hydrolized. The beta-lactam core can then be recovered virtually quantitatively or recycled to the acylation reaction. This is because it has been found that the solubility of the beta-lactam core is unexpectedly high at relatively high concentrations of acylation agent and antibiotic.

Claims18

Dependent claims

A process for preparing a β-lactam antibiotic and forming a cephalosporanic or penicillanic acid, comprising:

(i) preparing a β-lactam antibiotic by acylating, in a reaction mixture,
(a) a cephalosporanic or penicillanic acid compound selected from the group consisting of 6-amino-penicillanic acid, 7-amino-cephalosporanic acid, 7-amino-desacetoxy-cephalosporanic acid, and 7-amino-3-chloro-cephalosporanic acid with
(b) an acylating agent;
(ii) removing a portion of the β-lactam antibiotic prepared in step (i) from said reaction mixture;
and
(iii) re-forming an amount of the cephalosporanic or penicillanic acid compound by hydrolyzing
(a) β-lactam antibiotic remaining in the reaction mixture after step (ii) with
(b) a hydrolyzing enzyme;
and
(iv) recovering the re-formed cephalosporanic or penicillanic acid compound from said reaction mixture.

7 more elements

Dependencies are inferred from the claim text.

Facts

Application: 09/077,727Filed 5 Jun 1998
Priority: BE 95010158 Dec 1995
Granted: 7 Jan 2003
Term ends: Not estimatedThe source records don’t support an estimate.

Classification5 codes

C12P 37/06
Preparation of compounds having a 4-thia-1-azabicyclo [3.2.0] heptane ring system, e.g. penicillin: by desacylation of the substituent in the 6…
C07D 501/00
Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a
C12P 35/02
Preparation of compounds having a 5-thia-1-azabicyclo [4.2.0] octane ring system, e.g. cephalosporin: by desacylation of the substituent in the 7…
C12P
Fermentation or enzyme-using processes to synthesise a desired chemical compound or composition