http://rdf.ncbi.nlm.nih.gov/pubchem/patent/IE-41864-B1
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_2ca2e4410855da087e11bf3eea8933fa |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D501-14 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P31-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D501-57 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D501-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D501-57 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D501-60 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D501-59 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D501-14 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D501-20 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D501-18 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D501-26 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D501-16 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/A61K31-546 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/A61K31-545 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/A61P31-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D- |
| filingDate | 1975-10-03-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1980-04-09-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | IE-41864-B1 |
| titleOfInvention | Cephalosporin derivatives |
| abstract | 1525739 3-Substituted 2- or 3-cephem derivatives ELI LILLY & CO 27 Nov 1975 [4 Dec 1974] 48753/75 Heading C2C Novel 3-substituted 2- or 3-cephem derivatives of the general formula wherein the dotted line represents a single carbon-carbon bond at the #3 or #2 position; R 2 and R 3 are each hydrogen or taken together form the group =C=O, or wherein R 2 taken singly is hydrogen and R 3 taken singly is:- (a) a group of the formula -COOR 4 wherein R 4 is C 1-6 alkyl, C 3-6 alkenyl, C 1-6 haloalkyl, 2,2,2-tri-haloethyl, methoxybenzyl, nitrobenzyl, benzyl or phenyl; or (b) a group of the formula -COSR 5 wherein R 6 is C 1-6 alkyl, phenyl, or benzyl; or (c) a group of the formula -CONR 6 R 8 wherein R 6 is hydrogen, C 1-6 alkyl, benzyl, phenyl, or tolyl and R 8 is hydrogen, C 1-6 alkyl or benzyl; or wherein R 6 and R 8 and the nitrogen atom to which they are bonded together form a 5 or 6 membered heterocyclic ring; or (d) a group of the formula -COR 7 wherein R 7 is C 1-6 alkyl, di(C 1-3 alkoxycarbonyl)- methyl, benzyl or phenyl; and wherein R is hydrogen or a carboxylic acid protecting ester forming group; R1 1 is hydrogen or methoxy; and wherein R 1 is hydrogen or an acyl group of the formula R1CO- wherein R1 is (a) C 1-7 alkyl, C 3-7 alkenyl, cyanomethyl, halomethyl, 4-amino-4-carboxybutyl or 4-protected amino- 4-protected carboxybutyl; or (b) C 1-6 alkoxy, benzyloxy, 4-nitrobenzyloxy or 4-methoxybenzyloxy; or (c) the group -R11 which is 1,4-cyclohexadienyl, phenyl, or substituted phenyl wherein the substituents are 1-3 halogens, hydroxy, nitro, cyano, trifluoromethyl, C 1-4 alkyl, C 1-4 alkoxy, carboxy, carboxymethyl, hydroxymethyl, aminomethyl, or protected aminoethyl; or (d) an substituted alkyl group of the formula R11-(Y)m-CH 2 - wherein R11 is as defined above, X is O or S, and m is 0 or 1; or (e) a substituted alkyl group of the formula R111CHW- wherein R111 is R11 as defined above, 2-thienyl, or 3-thienyl; W is hydroxy or protected hydroxy, carboxy or protected carboxy, or amino or protected amino; or (f) a heteroarylmethyl group of the formula R1111CH 2 wherein R1111 is 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, 2-thiazolyl, 5-tetrazolyl or 1-tetrazolyl; and when R is hydrogen, the pharmaceutically acceptable non-toxic salts of the acids represented thereby; with the limitations that when R 3 is the double bond is in the #3 position; and when the group is -N=C=O, neither R nor R 1 can be hydrogen, are prepared by heating a 3-azidocarbonyl-2- or 3-cephem derivative of the general formula wherein RE is a carboxylic acid-protecting esterforming group, optionally reacting the resulting 3-isocyanato-2- or 3-cephem with a nucleophilic reagent B : H or a source of anion B : - in which B is R 4 O-, R 5 S-, R 6 R 8 N- or R 7 - to give the corresponding compound in which R 3 is -COOR 4 , -COSR 5 , -CONR 6 R 8 or -COR 7 , optionally reducing the resulting compound in which R 3 is -COOR 4 to give the corresponding compound in which R 3 is H, optionally cleaving the 7-position side chain to give the corresponding 7-amino-cephalosporin, and optionally removing the carboxylic acid-protecting esterforming group to give the corresponding acid. Benzhydryl 7-(2-thienylacetamido)-3-azidocarbonyl-2-cephem-4-carboxylate is prepared by reacting the corresponding 3-formyl derivative with ethylene glycol and p-toluenesulphonic acid, treating the resulting 3-(1,3-dioxolan-2-yl) derivative with N-bromosuccinimide and azobisisobutyronitrile, treating the resulting 3-(2- bromoethoxycarbonyl) derivative with Nal, reacting the resulting 3-(2-iodoethoxycarbonyl) derivative with Zn dust in glacial acetic acid and DMF, treating the resulting 3-carboxy derivative with ethyl chloroformate and reacting the resulting 3-ethoxycarbonyloxycarbonyl derivative with sodium azide. Benzhydryl 7-(2-thienylacetamido)-3-formyl-2- cephem-4-carboxylate is prepared by reacting 7 - (2 thienylacetamido) - 3 -hydroxymethyl -2- cephem - 4 - carboxylic acid with diphenyldiazomethane and oxidizing the resulting benzhydryl ester with chromic acid. Benzhydryl 7 - (2 - thienylacetamido) - 7 - methoxy - 3 - formyl - 2 - cephem - 4 - carboxylate is prepared by treating 7-(2-thienyl-acetamido)-7- methoxy-3-acetoxymethyl-3-cephem-carboxylic acid with acetic anhydride in pyridine, hydrolysing the resulting 2-cephem derivative with NaOH oxidising the resulting 3-hydroxymethyl-2-cephem with chromic acid and esterifying the resulting 3-formyl-2-cephem acid with diphenyldiazomethane. |
| priorityDate | 1974-12-04-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
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