http://rdf.ncbi.nlm.nih.gov/pubchem/patent/PL-94240-B1
Outgoing Links
| Predicate | Object |
|---|---|
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/B01J23-44 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D209-48 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D303-48 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C255-00 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/A61K31-545 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D501-08 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D501-22 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D501-24 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D501-18 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D501-20 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D303-48 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/B01J23-44 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D209-48 |
| filingDate | 1972-12-28-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1977-07-30-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | PL-94240-B1 |
| titleOfInvention | Substituted cephene-4-carboxylates and their method of preparation[us3962223a] |
| abstract | 1423741 Cephem compounds ROUSSEL-UCLAF 1 Jan 1973 [31 Dee 1971 (5) 7 Sept 1972] 114/73 Heading C2C Novel 7-tritylamino-cephem compounds of Formula (X) wherein A 1 is C 2 -C 5 alkyl, C 3 -C 7 cycloalkyl or C 3 -C 7 heterocyclyl and R<SP>1</SP> 2 is the residue of an ester grouping, are prepared according to the following reaction scheme in which the reactions and intermediate compounds are as follows: (Ia) A 2-halo-2,3-epoxybutanoate (III) in which A 2 is methyl or A 1 as defined above and Hal is Cl or Br, is dehydrohalogenated to give a 2-oxo-but-3-enoate (IV). (Ib) A #-amino-propenoate (XIII) wherein Z is a cyclic imido group which may be substituted, a benzoylamino group or a thiobenzoylamino group, and R<SP>11</SP> 2 is C 1 -C 10 alkyl or C 7 -C 15 aralkyl, is reacted with H 2 S in the presence of an acid HX where X is halogen, sulphate or sulphonate, to give a corresponding thioaminal (V). (2) The butenoate (IV) is condensed with the thiominal (V) in the presence of tert amine to give either a 2-substituted - methyl - 4 - hydroxy - 1,3 - thiazane (VI) or a 2-substituted methyl-2,3-dihydro-1,3- thiazine (VI<SP>1</SP>), according to the reaction conditions. (3) The thiazane (VI) or the thiazine (VI<SP>1</SP>) is then treated with hydrazine or hydrogenolysed, followed by acid hydrolysis, to give a corresponding 2 - aminomethyl - 2,3 - dihydro- 1,3-thiazine (VII). Alternatively, when Z in the compound (VI) or (VI<SP>1</SP>) is benzoylamino or thiobenzoylamino, the compound may be alkylated to the corresponding 2-(α-alkoxybenzylaminomethyl) derivative which is then subjected to acid hydrolysis and dehydration to give the required compound (VII). (4) The compound (VII) is selectively saponified to a corresponding 2-(α-amino-α-carboxy)methyl-2,3- dihydro-1,3-thiazine (VIII), which is then tritylated to a 2-(α-tritylamino-α-carboxy)methyl- 2,3-dihydro-1,3-thiazine (IX). (5) The compound (IX) is cyclized by treatment with a lactamisation agent (e.g. a carbodiimide) to give the cephem compound (X). The 7-tritylamino-cephem compounds (X) may be subjected to mild acid hydrolysis to give 7-amino-cephem carboxylic esters of Formula (XI), or to more severe acid hydrolysis to give the corresponding 7 - amino - cephem - carboxylic acids (XI<SP>1</SP>), these esters and acids being novel compounds when A 1 is not an ethyl group.n[GB1423741A] |
| priorityDate | 1971-12-31-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
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Total number of triples: 171.