http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-1429573-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_d202e9e866984fe229f6facc38f1d740 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07F9-568 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07F9-4006 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D501-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D501-18 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07F9-568 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07F9-40 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D501-16 |
| filingDate | 1973-12-10-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1976-03-24-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-1429573-A |
| titleOfInvention | Cephalosporines |
| abstract | 1429573 Epimerization of 7α-amino-cephalosporins; preparing phosphonate ester and other intermediates; organolithium compound MERCK & CO Inc 10 Dec 1973 [12 Dec 1972] 57162/73 Headings C2C C2P and C2J [Also in Division A5] 7α-Amino-cephalosporins of the general formula wherein R 1 is a blocking group, R<SP>1</SP> is a C 2-6 alkanoyl group and R 5 is a C 1-3 alkyl group, are epimerized by reacting them with an aromatic aldehyde, treating the resulting novel 7α-iminocephalosporin of the general formula wherein R 2 is an arylmethylene radical, with a strong base, e.g. phenyllithium, which forms the corresponding 7-Li derivative, in the presence of an aprotic solvent and a dipolar aprotic cosolvent, followed by acidification and reacting the resulting novel 7#-imino-cephalosporin of the general formula with an acid in the presence of an amine or with p-toluenesulphonic acid in ethereal solution to give the desired 7#-amino-cephalosporin, which may subsequently be N-acylated, hydrolysed and salified to give an antibacterial 7#-acylamino-3-cephem-4-carboxylic acid salt. 7α-Amino-cephalosporins of the first general formula above are prepared by reacting compounds of the general formulµ and wherein R is an aryl or C 1-6 alkyl group and X is a halogen atom or leaving group, treating the resulting phosphonoacetate of the general formula with a base, reacting the resulting thiazine of the general formula with azidoacetyl chloride in the presence of an acid scavenger and reducing the resulting 7α- azido-cephalosporin of the general formula 1 - Chloro - 3 - acetoxy - butan - 2 - one is prepared by treating 2-acetoxypropionyl chloride with diazomethane, followed by hydrochloric acid. p - Methoxybenzyl α - thioformamido - diethyl phosphonoacetate is prepared by reacting benzylamine with formaldehyde and diethyl phosphite, hydrogenating the resulting diethyl N-benzylaminomethylphosphonate (optionally isolated as the hydrochloride), treating the resulting diethyl aminomethylphosphonate hydrochloride with benzaldehyde, reacting the resulting diethyl N- benzylidene - aminomethyl - phosphonate with phenyllithium and p-methoxybenzyl chloroformate, treating the resulting p-methoxybenzyl N - benzylidene - α - amino - diethylphosphonoacetate with p-toluenesulphonic acid in ether and reacting the resulting p-methoxybenzyl α-aminodiethylphosphonoacetate with ethyl thioformate in the presence of liquid hydrogen sulphide. |
| priorityDate | 1972-12-12-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
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