http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-835753-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_fcbc1de8801460caf80ad76627ae20b0 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D275-03 |
| classificationIPCAdditional | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D275-02 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D275-03 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D277-52 |
| filingDate | 1956-07-12-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| inventor | http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_0b37b43c1f0cd1aa5143bb050371476e http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_dc96f1b6c678f0da810ca5d92d46f8e1 |
| publicationDate | 1960-05-25-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-835753-A |
| titleOfInvention | Improvements in or relating to heterocyclic sulphonamide compounds |
| abstract | The invention comprises compounds of the formula <FORM:0835753/IV (b)/1> and salts thereof such as the alkali-metal or alkaline-earth metal salts, where R1 is hydrogen or methyl, and of R2 and R3, one is hydrogen and the other is a p-aminobenzenesulphonamido group, with the proviso that when R1 is hydrogen, the sulphanilamido group is in the 4-position, and their o-carboxybenzoyl and b -carboxypropionyl derivatives. The compounds are prepared by the usual methods for N1-heterocyclic sulphanilamides, for example by the reaction of a p-substituted benzenesulphonyl halide wherein the p-substituent is a group convertible into an amino group (e.g. acylamino) with the appropriate 4- or 5-amino-isothiazole followed by conversion of the p-substituent (e.g. by hydrolysis) into an amino group. The reaction is preferably carried out in an organic solvent in the presence of a basic condensing agent. Suitably the condensing agent may also be the solvent, for example pyridine. Examples describe the preparation of (1) 4-sulphanilamido-isothiazole; (2) 5-sulphanilamido-3-methyl-isothiazole and (5) 4-sulphanilamido-3-methyl-isothiazole, by hydrolysis of the intermediate acetyl derivative obtained by the action of p-acetylaminobenzenesulphonyl chloride on the amino-isothiazole; the preparation of the mono-succinoyl and phthaloyl derivatives of (2) is described. 4-Amino-isothiazole is made by oxidizing 5-aminobenz-1 : 2-isothiazole with permanganate, decarboxylating the resulting iso-thiazole-4 : 5-dicarboxylic acid, converting the isothiazole-4-carboxylic acid to its methyl ester, degrading via the carboxyhydrazide and azide to the benzyl urethane and treating with hydrogen bromide in acetic acid. (The ethyl urethane is described in the Provisional Specification.) 5 - Amino - 3 - methyl - isothiazole is made by cyclizing b -iminothiobutyramide. 4-Amino-3-methyl-isothiazole is made by di-azotizing 5-amino-3-methyl-isothiazole, reacting with cuprous bromide, heating the resulting 5-bromo-3-methyl-isothiazole with cuprous cyanide to give 5-cyano-3-methyl-isothiazole, hydrolysing to 3-methyl-isothiazole-5-carboxylic acid, heating to give 3-methyl-isothiazole, nitrating to 3-methyl-4-nitro-isothiazole and reducing with ferrous sulphate. |
| isCitedBy | http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-3186999-A |
| priorityDate | 1956-07-12-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 67.