http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-1299232-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_4acae202b6a15394281949545e70d2f6 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C255-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D513-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D501-46 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D271-04 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D271-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D501-46 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D513-04 |
| filingDate | 1970-10-22-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1972-12-13-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-1299232-A |
| titleOfInvention | Derivatives of cephalosporin |
| abstract | 1299232 Cephalosporin-y-lactams, acetic acid derivatives ROUSSEL-UCLAF 22 Oct 1970 [22 Oct 1969] 50184/70 Addition to 1155493 Headings C2A and C2C Novel 7 - acylamino - 3 - aminomethylcephalosporanic acid - γ - lactams having the Formula I<SP>1</SP> wherein R is hydrogen, phenyl or nitro- or amino-substituted phenyl and salts thereof, are prepared by reacting a 4 - R<SP>1</SP> - substitutedsydnone-3-acetic acid of Formula II wherein R<SP>1</SP> is hydrogen, phenyl or nitrophenyl, or an N-acylating derivative thereof, with 7-amino-3-aminomethyl-cephalosporanic acid-γ-lactam, and if required reducing the product in which R<SP>1</SP> is -NO 2 by catalytic hydrogenation to give the corresponding aminophenyl compound. The reaction preferably employs the acid anhydride as the acylating agent, formed in situ by using the acid in the presence of a condensing agent (e.g. dicyclohexyl carbodiimide). The hydrogenation is effected in the presence of palladinised charcoal. The compounds of Formula I<SP>1</SP> may alternatively be prepared by lactamisation of a corresponding 7 - (41 - R - sydnone - 3<SP>1</SP> - acetamido) - 3 - aminomethyl-cephalosporanic acid or an ester thereof wherein R is as defined above. The inventive compounds may be in either racemic or optically active forms. N-nitroso-imino-diacetic acids of Formula III wherein R<SP>1</SP> is phenyl or nitro -phenyl are prepared either (1) by reacting benzaldehyde or a nitrobenzaldehyde with ethyl glycocollate hydrochloride and KCN to give an ethyl - N- (α - phenyl - α - nitrilomethyl) - glycocollate hydrochloride of Formula V where R<SP>2</SP> is H or NO 2 , and hydrolysing this compound with an acid to a di-acid of Formula VI which is treated with NaNO 2 to give the said nitroso-derivative (III); or (2) reacting α-bromophenylacetic acid or α-bromo-nitrophenylacetic acid with ethyl glycocollate hydrochloride to give an α - ethoxycarbonyl - methylaminophenyl-acetic acid of Formula VIII where R<SP>2</SP> is H or NO 2 , and saponifying this compound with an alkali to a di-acid of Formula IX which is treated with alkali metal nitrite to give the nitroso-derivative (III). 4-substituted sydnone acetic acids of Formula II above wherein R<SP>1</SP> is phenyl or nitrophenyl are prepared by cyclizing, by means of a dehydrating agent, an N-nitroso-imino-diacetic acid of Formula III above. Pharmaceutical compositions having antibiotic activity against gram-positive and -negative bacteria comprise a cephalosporanic acid- γ-lactam of Formula I<SP>1</SP> or a therapeutically acceptable salt thereof together with a pharmaceutical carrier. The compositions may be in the form of tablets, capsules, pills, powders, oral or injectable liquid forms, topically applicable forms or suppositories. |
| priorityDate | 1969-10-22-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 37.