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classificationCPCAdditional http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/Y02P20-55
classificationCPCInventive http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D499-00
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filingDate 1971-06-09-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationDate 1975-04-16-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber GB-1390754-A
titleOfInvention Penicillin and cephalosporin esters
abstract 1390754 Penicillins and cephalosporins BEECHAM GROUP Ltd 23 June 1972 [9 June 1971] 05345/74 Divided out of 1377817 Heading C2C Novel compounds of Formula I and pharmaceutically acceptable acid addition salts of those compounds which contain a basic nitrogen atom wherein X and Y are the same or different and each represents oxygen or sulphur, Z represents a straight or branched, saturated or unsaturated divalent hydrocarbon radical which may be interrupted by a hetero atom, R represents hydrogen or an alkyl, alkenyl, alkynyl, aryl or aralkyl group or a functional substituent, A represents a group of Formula II or III wherein B represents hydrogen or an acetoxy group and R<SP>1</SP> is an organic acylamino group may be prepared (1) by reacting a compound of Formula IX or a reactive esterifying derivative thereof, in which formula A is as defined with respect to Formula I, with a compound of Formula X or a reactive esterifying derivative thereof, in which X, Y, Z and R are as above defined or (2) by reacting a compound of Formula XIII or a silyl derivative thereof wherein H 2 NQ- represents a 6-amino penam-3, a 7-amino-3- methylceph-3-em-4 or a 7-amino-3-acetoxymethylceph-3-em-4 radical and R, X, Y and Z are as above defined with a reactive N-acylating derivative of a compound of Formula XIV wherein R<SP>1</SP>a is an organic acyl group which may carry a protected amino group, removing the silyl group, if present, by hydrolysis or alcoholysis, and if a protected amino group is present, optionally converting it to a free amino group under acid or neutral conditions. The esters of Formula XIII are stated to be novel and may be prepared by reacting 6-aminopenicillanic acid, 7-aminocephalosporanic or 7-aminodesacetoxycephalosporanic acid or N- protected derivatives thereof with the appropriate 3-bromolactone and thereafter removing the protecting group, if present. Crotoriolactone and 3-chloro-3-methyl butyrolactone are prepared by known methods. 3-Bromocrotonolactone is prepared by reacting crotonolactone with N-bromo succinimide and azoisobutyronitrile. Pharmaceutical compositions having antibacterial activity, preferably for oral administration, comprise the compounds of Formula I and a pharmaceutically acceptable carrier.
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