http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-1383431-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_2ca2e4410855da087e11bf3eea8933fa |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07F9-65611 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07F9-65613 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D499-00 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D501-20 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D501-16 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D499-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07F9-6561 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D501-12 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D499-18 |
| filingDate | 1972-01-10-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1974-02-12-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-1383431-A |
| titleOfInvention | Pentavalent phosphorus amides of cephalosporins |
| abstract | 1383431 Phosphorus amides of cephalosporins ELI LILLY & CO 10 Jan 1972 [11 Jan 1971] 1095/72 Headings C2C and C2P Novel phosphorus amides of cephalosporins, having the general Formula (I) wherein each of R 1 and R 2 is a C 1-15 hydrocarbon 'or O-hydrocarbon radical which is free of aliphatic unsaturation; m is 1, 2 or 3; R 3 is -H or -OCH 3 ; R 4 is a group of formula in which R 5 is hydrogen, an alkali metal cation, an ammonium or amine cation, a negative charge or an ester group, and R 6 is hydrogen, O-(C 1-4 alkyl), S-(C 1-4 alkyl), where n and m are independently 1, 2 or 3, pyridyl, amino-pyridyl, where R 1 and R 2 are as defined above, or and Y is a group of formula in which M is H, an alkali metal cation or a group forming a C 1-4 alkyl mixed carbonic anhydride with the carboxylic group; R 10 is NH 2 or NH 3 <SP>(+)</SP>, or may be hydrogen when there is an amino group in another part of Y or the group R 4 , and the phenyl ring may be substituted with Cl, OH, NH 2 , #-amino-C 2-3 alkyl or NO 2 ; and cyclohexylamine salts thereof, are prepared by reacting a phosphorus compound of formula with a primary amino group-containing cephalosporin of Formula (II) wherein R 1 , R 2 , R 3 , R 4 and Y are as defined above and X is Cl or Br, in a liquid reaction medium at a pH of 7À5 to 12. The phosphorus amides may be decomposed to give the cephalosporin starting material (II) by allowing to stand in solution in cyclohexanone, when the said cephalosporin precipitates. This property provides a further aspect of the invention whereby cephalosporins of Formula (II) may be recovered from their impure solutions by conversion to the phosphorus amide (I) by the reaction described above, extracting with cyclohexanone and allowing the extract to stand at room temperature to precipitate the original cephalosporin (II). Alternatively, the cyclohexanone solution may be treated with cyclohexylamine to precipitate the cyclohexylamine salt of the cephalosporin phosphorus amide. This salt may be subjected to a conventional de-amidation procedure (e.g. reaction with PCl 5 , then methanol followed by hydrolysis) to give 7-aminocephalosporanic acid. |
| priorityDate | 1971-01-11-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
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