Abstract:
R1 represents hydrogen, lower molecular alkyl, acyl, phenyl, R2 is hydrogen, lower molecular alkyl, R3 is alkyl having 3 to 6 carbon atoms, cycloalkyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkenyl, alkylcycloalkenyl having each 5 to 9 carbon atoms, cyclohexenylmethyl, chlorocyclohexyl, bicycloheptenylmethyl, bicycloheptylmethyl, bicycloheptenyl, bicycloheptyl, nortricyclyl, adamantyl, benzyl, phenylethyl, which as substance or in the form of their salts have pypoglycemic properties and which are distinguished by a strong and continuous lowering of the blood sugar level; processes for preparing them as well as pharmaceutical preparations containing the sulfonyl-ureas as an active substance.
IN WHICH X represents hydrogen, chlorine, bromine, methoxy or methyl, Y represents -CH(CH3)-CH2-, -CH2-CH(CH3)-or preferably -CH2-CH2-, Z represents hydrogen or together with Y and the phenylene radical the radical
WHEREIN X IS HYDROGEN, CHLORINE, BROMINE, METYL OR METHOXY, Y IS -CH(CH3)-CH3-, PREFERABLY
-CH2-CH2-,
Z IS HYDROGEN OR A HYDROCARBON RADICAL OF 1 OR 2 CARBON ATOMS, WHICH FORMS TOGETHER WITH A 5- OR 6-MEMBERED RING, R IS ALKYLENE-IMINO OF 3 TO 7 CARBON ATOMS IN THE RING WHICH MAY BE UNSATURATED OR SUBSTITUTED BY 1 OR 2 METHYL OR LOWER ALKYL OR METHOXY, PENTAMETHYLENIMINO SUBSTITUTED BY ENDOALKYLENE OF 1 TO 3 CARBON ATOMS, HEXAMETHYLENE-IMINO SUBSTITUTED BY ENDOETHYLENE IN B-EPOSITIONS, TETRAHYDRO-ISO-INDOLINE, 4,7 - ENDOALKYLENE-HEXAHYDRO- OR -TETRAHYDRO-ISO-INDOLINE, THE ENDOALKYLENE CONTAINING 1 OR 2 CARBON ATOMS AND THE DOUBLE BOND OF THE TETRAHYDRO COMPOUND BEING IN 5,6 POSITION, AND THE SALTS THEREOF.
WHEREIN X IS HYDROGEN, CHLORINE, BROMINE, METHOXY OR METHYL, Y IS -CH(CH3)-CH2-, -CH2-CH(CH3)OR -CH2CH2-, R IS ALKYL OF 3 TO 6 CARBON ATOMS, CYCLOALKYL OF 5 TO 8 CARBON ATOMS, WHICH MAY BE SUBSTITUTED BY 1 OR 2 ALKYL OF UP TO 3 CARBON ATOMS OR BY CHLORINE, CYCLOALKENYL OF 5 TO 8 CARBON ATOMS, WHICH MAY BE SUBSTITUTED BY 1 TO 2 ALKYL OF UP TO 3 CARBON ATOMS, BICYCLOALKYL OR BICYCLOALKENYL OF 7 OR 8 CARBON ATOMS, NORTRICYCLYL, SPIRO(2,4)-HEPTYL, Z IS HYDROGEN OR A HYDROCARBON RADICAL OF 1 OR 2 CARBON ATOMS WHICH FORMS WITH Y A 5- OR 6-MEMBERED RING, OR THE SALTS THEREOF AS WELL AS A PROCESS FOR THEIR MANUFACTURE.
Abstract:
1335913 Sulphonyl-ureas FARBWERKE HOECHST AG 7 June 1971 [6 June 1970 26 April 1971] 19306/71 Heading C2C Novel compounds (I) (including salts thereof) where X is H, Cl, Br, MeO or Me, Y is or R is C 3 to C 6 alkyl, C 5 to C 8 cycloalkyl optionally substituted by 1 or 2 alkyls of up to 3 carbon atoms in total or by Cl, C 5 to C 8 cycloalkenyl optionally substituted by 1 or 2 alkyls of up to 3 carbon atoms in total, C 7 or C 8 bicyclo-alkyl or -alkenyl, nortricyclyl, spiro[2,4]heptyl, alkylene-imino of 3 to 7 carbons in the ring which may be unsaturated and/or substituted by 1 or 2 methyls or by a C 1 to C 4 alkyl or by a MeO, pentamethylene-imino substituted by C 1 to C 3 endoalkylene, hexamethylene-imino substituted by endoethylene in #,#-position, or tetrahydroisoindoline, 4,7 - endoalkylene - hexahydro- or -tetrahydro-isoindoline the endoalkylene group containing 1 or 2 carbons and the double bond of the tetrahydro-compound being in 5,6-position, are made by standard methods. The following compounds are also prepared: N - [4 - (# - quinolino - 8 - carboxamidoethyl)- benzenesulphonyl] - N 1 - cyclohexyl - thioureaisourea methyl ether and -isothiourea methyl ether. Pharmaceutical preparations suitable for lowering the blood sugar level in the treatment of diabetes mellitus contain (I) as active ingredient; administration is orally.