http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-1496750-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_9f9afcd0369d6402247555a4656c0917 |
| classificationCPCAdditional | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/Y02P20-55 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D317-60 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D501-20 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D317-60 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D501-20 |
| filingDate | 1976-06-30-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1977-12-30-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-1496750-A |
| titleOfInvention | 7-(alpha-amino-omega-(2,3-and 3,4-methylenedioxyphenyl)acylamido)-cephalosporanic acid derivatives |
| abstract | 1496750 7 - (α - Amino - # - (2,3 - and 3,4- methylenedioxyphenyl)acylamido]cephalosporins RICHARDSON-MERRELL Inc 30 June 1976 [22 July 1975] 26432/76 Heading C2C Compounds of the formulµ where Z is a single bond, methylene or ethylene, R 1 is hydrogen, hydroxy, acetoxy, pyridinium or -S-R 2 , R 2 is an unsubstituted or methyl or ethyl mono- or di-substituted heterocycle selected from pyrazolyl, imidazolyl, triazolyl, tetrazolyl, thiazolyl, isothiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, oxadiazole, pyrimidinyl, pyrazinyl, and pyridazinyl, and R 3 is hydrogen, formyloxymethyl or C 1-5 alkanoyl oxymethyl, and pharmaceutically acceptable salts thereof, may be prepared by condensing an α-amino-#- (2,3- or 3,4-methylenedioxyphenyl)alkanoic acid of the formula with a 7-aminocephalosporanic acid of the formula where B is a blocking group selected from tbutyloxycarbonyl, benzyloxycarbonyl, carbomethoxypropen-2-yl, trifluoroacetyl, trichloroethoxycarbonyl, p-methoxycarbobenzoxy, pnitrocarbobenzoxy and the hydrochloric acid salt. The alkanoic acid of Formula (III) or (IV) may be employed in the form of a functional equivalent as an acylating agent and the coupling reaction is generally effected in a solvent at - 30 C. to 100 C. for a period of from 15 minutes to 36 hours. Compounds wherein the radical R 1 represents the -SR 2 group may be obtained by reacting 7-aminocephalosporanic acid with the appropriate thiol in aqueous solution at 25-150 C. for a period of from 15 minutes to 24 hours in the presence of a mild base such as sodium bicarbonate. The protecting groups may be removed, and compounds of Formula (I) and (II) may be modified to form other compounds of Formulae (I) and (II), by conventional methods. 2 - (2,3 - Methylenedioxyphenyl) - acetaldehyde and -propionaldehyde are obtained by reacting 2,3-methylenedioxybenzaldehyde or -acetaldehyde with phenyllithium and triphenylmethoxymethyl phosphonium chloride and treating the product with perchloric acid. The unprotected amino acids of Formulµ (III) and (IV) may be obtained by hydrolysis of the corresponding hydantoin; the products may be racemized or converted to the acid chloride. The protecting group B in Formulµ (III) and (IV) may be introduced, for example, by reacting the free amino acid with t-butyloxy carbonyl azide. The products of Formulµ (I) and (II) possess antibacterial properties. |
| priorityDate | 1975-07-22-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 47.