IL28401A - Arylsulfonyl ureas,their manufacture and pharmaceutical compositions containing them - Google Patents

Description

Arylsulfonyl their manufacture and pharmaceutical compositions containing them SPARAMEDICA This invention to novel sulfonamides and to a process for the manufactwe In one the novel sulfonamides of the invention are sul onylurea derivatives of the general formul 1 2 wherei represents hydroge R represents 1 or R and R taken together represent represents a phenyl radical bearing one or lower lower o lower ethyl or a or containing heterocyclic and n is 3 or The compounds of the invention may be manufactured by a process comprising reacting a reactive derivative of a sulfonylcarbamlc acid of the general ormula o a sulfonylisocyanate of the general formula solvents which do not contain hydroxy such as halogenated hydrocarbons such as or In a preferred embodiment of process variant there is used a compound of the general formula in which Z presents the a sulfonamide as an alkali is reacted with zole in a suitable anhydrous organic solvent of the kind tioned The acid imidazolide which is formed is allowed to react in situ with r or When a cyclic is the keto group in the reaction product obtained can be subsequently reduced to the hydroxyl This can be effected in a manner known per for by treatment with a complex metal hydride such as sodium isomers obtained in the reduction can if be separated according to methods known per se by crystallization by On the other a hydroxy group contained in the reaction product can be to the keto group in a manner known per se by means of chromic ί The starting compounds of the above formula IV can be by reaoting a sulfonylcarbamio acid derivative o a sulfonylisocyanate with a or 50 ml of treated at with g of The reaction mixture was at for a further 20 minutes then treated with g cls The reaction was allowed to warm up to room stirred for a further 2 hours and evaporated in The residue taken up in 60 ml of caustic soda and the solution was with The ethereal was extracted 40 ml of caustic soda and the combined aqueous j were made with hydrochloric The solution was extracted with acetic ester and working up of ester extract yielded melting point Example 2 Following a similar procedure to that described in Example 1 from acid zolide in situ from and there was tained melting point Example 3 Following a similar prooedure to that described in Example from and melting Exam le 4 A mixture of 7 8 g of acid ethyl g of and ml of absolute pyridine was heated at for hours in the absence of The oily reaction product was dissolved 100 ml of caustic soda and after extraction with aqueous phase was saturated with C02 and The i jfiltrate was acidified with acetic acid and the which separated out crystallized on standing and was recrystallized ester The product decomposed above ί Example 5 i j 8 g of oxazolidinone in 150 ml of caustic soda were heated to reflux for about After the reaction solution was acidified with hydrochloric The reaction which separated out as an oil crystallized on standing and i reprecipitated by dissolving in soda solution and ί fication of the solution with hydrochloric The 1 t melted at The starting material was manufactured as melting Example 10 A solution of g of in 400 ml of acetone was treated with an aqueous chromic acid solution g of per 100 up to the positive The mixture was then treated with about 500 ml of water in order to dissolve the chromium salt and acetone was evaporated in The aqueous residue was with and extract washed with salt dried and evaporated There was obtained oluenesulfonyl melting point Example 11 j To a solution of 5 75 S of trans 50 ml of absolute after the addition of ml of there were slowly with and 17 ml of standing for 2 days at room the solvent evaporated the residue dissolved in ml of On saturation of the solution with there was precipitated a brown resin from which the mother liquor was After extraction with the aqueous solution was insufficientOCRQuality

Claims (1)

1. A compound of the general formula 1 wherein R represents hydroge R represents o taken together represent R represents phenyl radical bearing one or more lowe alkylthio or lower ethyl or a or heterocyclic grou and n is 3 or urea 16 A process for the manufacture of hovel sulfonamides the general formula I in Claim wherein a reactive derivative sulfonylearbamic acid the general formula or a sulfonylisocyanate of the general formula in which formulae has the same meaning in Claim is acted with cyclohexanone or A process according to Claim wherein a pound of general formula wherein has the same meaning as in 1 and is lower lower or is used as a reactive earbamic acid A rocess accordin to Claim 1 or 1 where n 18 which formulae and n have the same meaning as in Claim is treated with an Process for the preparation of sulfonamides I in 1 as hereinbefore particularly especially with to the Process for the manufacture of preparations having sugar depressing characterized in that a amide of genera formula I is as active s with therapeuticall compatible olid or liquid used in blood sugar depressant containin a sulfonamide of the general formula I in Claim and a A compound of the general formula I in Claim 1 whenever prepared by a process according to any one of Claims 13 to 20 by an obvious ohemical equivalent whenever prepared by a process according to any one of Claims 13 to or by an obvious chemical equivalent insufficientOCRQuality