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classificationCPCInventive http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D213-80
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filingDate 1973-12-12-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationDate 1975-12-31-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber GB-1419856-A
titleOfInvention Antibacterial 1,2-dihydro-2-oxonicotinamides and process for producing the same
abstract 1419856 Penicillin and cephalosporin derivatives PARKE DAVIS & CO 12 Dec 1973 [15 Dec 1972] 57693/73 Heading C2C [Also in Division C3] Novel penicillin and cephalosporin derivatives of the formula wherein R 1 is cyclopentylmethyl, cyclopentenylmethyl, cyclohexyl, cyclohexylmethyl, benzyl, phenethyl, adamantyl, methoxybenzyl, hydroxybenzyl, chlorobenzyl, furfuryl, 3-furylmethyl, thenyl, pyridyl, furyl or thienyl, R 2 is hydrogen or together with R 1 represents R 3 is H or CH 3 ; and Z is and pharmaceutically acceptable salts thereof are prepared by reacting ampicillin, cephalexin or cephaloglycin or acid salts or silylated derivatives thereof with the appropriate 1-R 3 -5-R 2 -6- R 1 -1,2-dihydro-2-oxonicotinic acids or reactive derivatives thereof or by reacting 6-aminopenicillanic acid, 7-aminocephalosporanic acid or 7 - amino - 3 - methyl - ceph - 3 - em - 4- carboxylic acid, or salts or silylated derivatives thereof with the corresponding N-(1-R 3 -5-R 2 -6- R 1 - 1,2 - dihydro - 2 - oxonicotinoyl) - 2 - phenylglycines or reactive derivatives thereof. 5 - R 2 - 6 - R 1 - 1,2 - Dihydro - 2 - oxonicotinic acids are prepared by hydrolysing the corresponding nitriles resulting from the reaction between 2-cyanoacetamide and the sodium salts of the appropiate #-oxoaldehydes. 6 - Benzyl - 1,2 - dihydro - 1 - methyl - 2 - oxonicotinic acid is obtained by hydrolysing the corresponding nitrile resulting from the methylation of 6 - benzyl - 1,2 - dihydro - 2 - oxonicotinonitrile. 6 - p - Hydroxybenzyl - 1,2 - dihydro - 2 - oxonicotinic acid is obtained by treating 6-p-methoxybenzyl - 1,2 - dihydro - 2 - oxonicotinic acid with hydrobromic acid. D - N - (6 - benzyl - 1,2 - dihydro - 2 - oxonicotinoyl) - 2 - phenylglycine and D - N - (6 - cyclohexylmethyl - 1,2 - dihydro - 2 - oxonicotinoyl) - 2- phenylglycine are obtained by reacting D-N- (trimethylsilyl) - 2 - phenylglycine trimethylsilyl ester with the appropriate 1,2-dihydro-2- oxonicotinoyl chlorides, obtained by reacting the corresponding nicotinic acid with thionyl chloride.
priorityDate 1972-12-15-04:00^^<http://www.w3.org/2001/XMLSchema#date>
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