http://rdf.ncbi.nlm.nih.gov/pubchem/patent/ES-348510-A1
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_6b6fc801b5bfe5304ffa40d938db6e09 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C311-54 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C51-60 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07C51-60 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07C311-54 |
| filingDate | 1967-12-21-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1969-03-01-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | ES-348510-A1 |
| titleOfInvention | PROCEDURE FOR THE PREPARATION OF N'-SUBSTITUTED N-ARYLSULFONYLUREAS. |
| abstract | Novel compounds I (including salts thereof) of the general formula wherein R 1 signifies H, F, Cl, Br, NH 2 , alkyl, alkoxy, alkylthio or alkanoyl, R 2 signifies H or R 1 R 2 signifies -(CH 2 ) 3 - or -(CH 2 ) 4 -, are prepared: (a) by reacting octahydro-1,2,4- methenopentalene-5-amine (obtained by hydrolysis of the corresponding 5-acetamido compound via the hydrochloride) with an appropriate substituted benzenesulphonyl isocyanate or with a reactive derivative of an appropriately substituted benzenesulphonyl carbamic acid (the substituents include, in addition to those listed under R 1 , R 2 and R 1 R 1 substituents which can be converted into the amino group by hydrolysis, reduction or reductive cleavage) (b) by reacting isocyanic acid-(octahydro-1,2,4- methenopentalen-5-yl ester) (obtained by treating octahydro - 1,2,4 - methenopentalene - 5 - carbonyl chloride, derived from the acid, with sodium azide with heating) or a reactive functional derivative of [octahydro-l,2,4-methenopentalen-5-yl)-carbamic acid with the appropriate benzenesulphonamide {substituents as in (a)} or (c) by desulphurizing corresponding thioureas {substituents as in (a)} the products obtained from methods (a), (b) and (c) may, if necessary, be hydrolysed or reduced. N - (Octahydro - 1,2,4 - methenopentalen - 5 - yl)- acetamide is prepared from the foregoing isocyanic acid ester by boiling with a mixture of glacial acetic acid and acetic anhydride. (Octahydro - 1,2,4 - methenopentalen - 5 - yl) carbamic acid methyl ester is obtained by heating the foregoing isocyanic acid ester with methanol while refluxing the carbamic acid ester may be converted to the 5-amine referred to in (a) by boiling with aqueous potassium hydroxide. Octahydro - 1,2,4 - methenopentalen - 5 - carboxamide, obtained from the corresponding 5-carboxylic acid ethyl ester by treatment with 26% aqueous ammonia, also affords the carbamic acid methyl ester by treatment with sodium methylate/methanol followed by bromine. (Octahydro - 1,2,4 - methenopentalen - 5 - yl)- urea is prepared from the foregoing isocyanic acid ester by reaction with ammonia in tetrahydrofuran the use of methylamine or dimethylamine in place of ammonia affords corresponding urea derivatives. 1 - (p - Tolylsulphonyl) - 3 - (octahydro - 1,2,4- methenopentalen - 5 - yl) - thiourea is produced by the interaction of p-tolylsulphonyl isothiocyanate and octahydro-1,2,4-methenopentalen- 5-amine or by interacting p-tolylsulphonamide and octahydro-1,2,4-methenopentalen-5-yl-isothiocyanate. Pharmaceutical preparations having hypoglycaemic action contain as active ingredient compounds I administration is preferably orally. |
| priorityDate | 1966-12-22-04:00^^<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: 60.