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filingDate 1989-02-28-04:00^^<http://www.w3.org/2001/XMLSchema#date>
grantDate 1990-08-14-04:00^^<http://www.w3.org/2001/XMLSchema#date>
inventor http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_218cd8927570f238b956c37446eb1f75
http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_674ae1aeea3ba0fe2313e7f4ea9548a3
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publicationDate 1990-08-14-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber US-4948898-A
titleOfInvention Process for the manufacture of 1-sulpho-2-oxoazetidine derivatives
abstract The manufacture of 1-sulpho-2-oxazetidine derivatives of the formula <IMAGE> I in which Het is an optionally amino-substituted, 5- or 6-membered, aromatic heterocycle containing 1 or 2 nitrogen atoms and optionally also an oxygen or sulphur atom, R1 is hydrogen, lower alkyl, phenyl-lower alkyl, lower alkanoyl, lower alkoxycarbonyl, lower alkenyl-lower alkyl, lower alkoxycarbonyl-lower alkyl, phenyl-lower-alkoxycarbonyl-lower alkyl, nitrophenyl-lower-alkoxycarbonyl-lower alkyl or carboxy-lower alkyl and R2 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, lower alkoxycarbonyl, lower alkanoyloxy-lower alkyl, lower alkoxycarbonyl-lower alkenyl, hydroxyiminomethyl, lower alkoxyiminomethyl, carbamoyl, carbamoyl-lower alkenyl or carbamoyloxy-lower alkyl, the group =NOR1 being present at least partially in the syn-form, in racemic form or in the form of the 3S-enantiomer, and of readily hydrolyzable esters and pharmaceutically compatible salts of these compounds, by acylating a compound of the formula <IMAGE> II in which R20 equals R2 or can also represent a 2,2-dimethyl-1,3-dioxolan-4-yl group and R3 is hydrogen or sulpho, or a salt thereof with a thioester of the formula <IMAGE> III in which Het is as above and R10 has any of the values of R1 except carboxy-lower alkyl, and can also represent a tri-lower alkyl-silyl-lower-alkoxycarbonyl-lower alkyl group or a carboxy-lower alkyl group converted into a readily hydrolyzable ester group, and the group =NOR10 is present at least partially in the syn-form, and carrying out subsequent steps (N-sulphonation, conversion of R20 into R2, R10 into R1), some of which are optional. The invention also provides certain novel products of formula I and benzthiazolyl thioesters of formula III per se and the preparation of the benzthiazolyl thioesters by esterifying corresponding carboxylic acids. Finally, the invention provides a process for the preparation of carboxylic acids in which R1 is t-alkoxycarbonylmethyl. The compounds of formula I have antimicrobial activity.
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priorityDate 1982-06-03-04:00^^<http://www.w3.org/2001/XMLSchema#date>
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Total number of triples: 1195.