http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-872102-A
Outgoing Links
Predicate | Object |
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assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_571b8abacacea64d3f7089d0983b8b3b |
classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D295-215 |
classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D295-215 |
filingDate | 1957-10-31-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
inventor | http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_d59e6f6dbf13f100dee8fc147b6407d5 |
publicationDate | 1961-07-05-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
publicationNumber | GB-872102-A |
titleOfInvention | Improvements in and relating to sulphonylureas and the manufacture thereof |
abstract | The invention comprises N-arylsulphonyl -N1-tetramethyleneureas in which the aryl group is a p-methyl-, p-ethyl-, p-n-propyl-, p-isopropyl-, p-methoxy-, p-ethoxy- or p-bromo-benzene radical or a naphthalene-(2) radical, and salts thereof such as the sodium salt and their preparation either by reaction of a reactive carbonic acid derivative of an aryl sulphonamide with pyrrolidine, for example by (a) reaction of an arylsulphonyl isocyanate with pyrrolidine; (b) reaction of an arylsulphonyl carbamyl chloride with pyrrolidine; (c) reaction of an N-alkoxycarbonyl arylsulphonamide with pyrrolidine; (d) reaction of an arylsulphonyl urea with pyrrolidine followed by decomposition of the resulting salt or (e) reaction of an N,N1-bis (arylsulphonyl) urea with pyrrolidine followed by decomposition of the resulting salt; or by reacting an arylsulphonyl chloride with an N - tetra - methylene-O-alkyl isourea followed by acid hydrolysis of the resulting N-arylsulphonyl-N1-tetramethylene-O-alkyl-isourea. Arylsulphonyl isocyanates used as intermediates, i.e. p-methyl-, p-ethyl-, and p-bromo-benzenesulphonyl isocyanate and naphthalene-(2)-isocyanate, are made by the action of silver isocyanate on the appropriate sulphonyl chloride. p-n-Propylbenzenesulphonyl chloride is made by sulphonating n-propylbenzene, isolating the barium salt of the resulting 4-n-propylbenzene-sulphonic acid and reacting with phosphorus pentachloride. Arylsulphonylcarbamic esters, i.e. the ethyl esters of p-methoxy-, p-ethoxy-, p-isopropyl-and p-methyl-benzenesulphonylcarbamic acid are made by the action of ethyl chloroformate on the arylsulphonylamide. Pyrrolidine salts of p-methylbenzenesulphonyl urea and N,N1-bis(p-methylbenzenesulphonyl) urea are made by the action of pyrrolidine on the sulphonyl urea. N - p - Methylbenzenesulphonyl - O -methyl - N1-tetramethyleneisourea is made by treating pyrrolidine with cyanogen bromide, reacting the resulting N-cyanopyrrolidine with sodium methoxide and reacting the O-methyl-N-tetramethyleneisourea obtained with 4 - methyl benzenesulphonyl chloride.ALSO:Pharmaceutical preparations having hypoglycaemic activity, suitable for enteral or parenteral administration, comprise N-arylsulphonyl - N1 : N1 - tetramethyleneureas in which the aryl group is a p-methyl-, p-ethyl-, p-n-propyl-, p-isopropyl-, p-methoxy-, p-ethoxy- or p-bromo-benzene radical or a naphthalene-(2) radical, or a salt (e.g. sodium salt) thereof, together with a suitable carrier. For oral administration, the products may suitably take the form of powders, granules, capsules, cachets, tablets, or liquid preparations such as a draft or drench in water, or a suspension in water or a non-aqueous solvent or in a syrup, an oil or a water/oil emulsion. For parenteral administration, the compounds may be dissolved or suspended in an aqueous medium. Extemporaneous injectable solutions may be prepared from sterile pills, granules or tablets. The compounds may also be administered in suppositories or pessaries. The preparations may contain preserving, suspending, thickening, emulsifying and surface-active agents and antioxidants, buffers, bacteriostats and solubilizing agents as appropriate. In an example, tablets contain N-p-tolylsulphonyl-N1 : N1 tetramethyllene urea, starch, magnesium stearate and polyoxyethylenesorbitan mono-oleate. |
priorityDate | 1957-10-31-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
type | http://data.epo.org/linked-data/def/patent/Publication |
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