WHICH IN THE FREE FROM OR IN THE FORM OF THEIR SALTS HAVE BLOOD SUGAR LOWERING PROPERTIES AND ARE DISTINGUISHED BY A STRONG AND LONG-LASTING HYPOGLYCEMIC ACTION. IN THE FORMULA X REPRESENTS (R-O-),Z-PHENYL OR 3-(R-O-),5-Z''-THIEN-2-YL WHEREIN R STANDS FOR AN ALKYL GROUP HAVING 1 TO 4 CARBON ATOMS, Z STANDS FOR A HALOGEN ATOM, AN ALKYL OR ALKOXY GROUP BOTH HAVING 1 TO 4 CARBON ATOMS, AND Z'' STANDS FOR A HALOGEN ATOM OR AN ALKYL GROUP HAVING 1 TO 4 CARBON ATOMS.
Abstract:
Benzene-sulfonyl semicarbazides having hypoglycemic properties and corresponding to the general formula
WHEREIN R represents A. PHENYL WHICH MAY BE SUBSTITUTED ONCE OR TWICE BY SUBSTITUENTS OF THE GROUP LOWER ALKYL, ALKENYL, ALKOXY ALKENOXY, ALKOXYALKOXY, ACYL, HALOGEN, OR TRIFLUOROMETHYL, OR BY THE METHYLENE-DIOXY GROUP, B. THIENYL WHICH MAY BE SUBSTITUTED ONCE OR TWICE BY SUBSTITUENTS OF THE GROUP HALOGEN, LOWER ALKYL, ALKOXY, ALKENYLOXY, ALKOXYALKOXY, PHENALKOXY, OR ARYL, OR BY A POLYMETHYLENE CHAIN LINKED AT ITS TWO ENDS TO THE THIENYL GROUP, WHICH CHAIN CONTAINS FROM 3 TO 4 CARBON ATOMS; Y represents -CH2-CH2-, -CH2-CH-(CH3)- or -CH(CH3)-CH2; R1 represents A N-3-azaspiro-(5,5)-undecane AND SALTS THEREOF FORMED FROM PHARMACEUTICALLY ACCEPTABLE BASES.
Abstract:
BENZENESULFONYL-UREAS HAVING HYPOGLYCEMIC ACTIVITIES CORRESPONDING TO THE FORMULA
1-(R1-NH-CO-NH-SO2-),4-(X-CO-NH-Y-)BENZENE
WHEREIN R1 IS (A) NOCRARAN-7-YL, BICYCLO- 3,1,0!-HEXYL, BICYCLO- 5, 1,0!-OCTYL, OR BICYCLO- 6,1,0!-NONYL; (B) 4,7-ENDOMETHYLENE - PERHYDROINDAN-5-YL; 4,7ENDOMETHYLENE-6-CHLORO-PERHYROINDAN-5-YL; 4,7ENDOMETHYLENE-PERHYDROINDAN - 2 YL; 2,6-ENDOMETHYLENECYCLOHEPTYL; 2,5-ENDOCYCLOBUTYLENE-1,2CYCLOHEXYL; EXO-TRICYCLO-(3,2,1,02,4)-OCTANYL; (C) SPIRO-(2-CYCLOPROPANE) - CYCLOPETYL; SPIRO-(2CYCLOBUTANE)-CYCLOPENTYL; SPIRO-(2-CYCLOPETANE)CYCLOPENTYL; SPIRO-(2-CYLOHEXANE)-CYCLOPENTYL; OR SPIRO-(5,5)-UNDECYL-3; X IS
A,A1-PHENYL OR 3-B,5-A1-THIEN-2-YL
IN WHICH A STANDS FOR HYDROGEN, HALOGEN, RIFLUOROMETHYL, PHENOXY, LOWER ALKYL OR LOWER ALKOXY BOTH HAVING 1-4 CARBON ATOMS, A1 STANDS FOR HYDROGEN, HALOGEN OR LOWER ALKYL OF 1-4 CARBON ATOMS AND B STANDS FOR HYDROGEN OR LOWER ALKOXY HOF 1-4 CARBON ATOMS Y IS A HYDROCARBON CHAIN OF 1-3 CARBON ATOMS OR A PHYSIOLOGICALLY TOLERABLE SALT THEREOF.
Abstract:
1. A BENZENE-SULFONYL SEMICARBAZIDE OF THE FORMULA 1-(R-CO-NH-Y-),4-(R1-NH-CO-NH-SO2-)BENZENE WHEREIN R REPRESENTS (A) PHENYL WHICH MAY CARRY ONE OR TWO SUBSTITUENTS SELECTED FROM THE GROUP CONSISTING OF LOWER ALKYL, LOWER ALKENYL, LOWER ALKOXY, LOWER ALKENOXY, LOWER ALKOXYALKOXY, ACETYL, HALOGEN, TRIFLUORO-METHYL, OR THE METHYLENE-DIOXY GROUP, (B) THIENYL WHICH MAY CARRY ONE OR TWO SUBSTITUENTS SELECTED FROM THE GROUP CONSISTING OF HALOGEN, LOWER ALKYL, LOWER ALKOXY LOWER ALKENYLOXY LOWER ALKOXYALKOXY, PHEN-LOWERALKOXY, OR POLYMETHYLENE CHAIN CONTAINING FROM 3 TO 4 CARBON ATOMS, LINKED AT ITS TWO ENDS TO THE THIENYL GROUP, Y REPRESENTS -CH2-CH2-, -CH2-CH-(CH3)OR -CH-(CH3)-CH2-, R1 REPRESENTS 4,7-ENDOALKYLENE-HEXAHYDRO-ISO-INDOLINE OR 4,7-ENDOALKYLENE-TETRAHYDRO-ISO-INDOLINE, HAVING 1 TO 2 CARBON ATOMS IN THE ENDOALKYLENE GROUP, IN THE CASE OF TETRAHYDROCOMPOUNDS THE DOUBLE LINKAGE DEING IN 5,6-POSITION; 4,7-ENDOCYCLOBUTYLENE-HEXAHYDROISO-INDOLINE; 4,7-ENDOCYCLOBUTYLENE-&5-TETRAHYDRO-ISOINDOLINE; 4,7-ENDOCYCLOBUTYLENE-&5 -TETRAHYDRO-SIOINDOLINE; OR 4,7-ENDOCYCLOPROPYLENE-HEXAHYDRO-ISOINDOLINE; AND SALTS THEREOF FORMED FROM PHARMACEUTICALLY ACCEPTABLE BASES.
Abstract:
N-(4-(B-BENZAMIDO-ETHYL)-BENZENESULFONYL) -N''(ENDOALKYLENECYCLOHEXYL- OR CYCLOHEXENYL)-UREAS BEING SUBSTITUTED AT THE BENZAMIDO GROUP AND HAVING HYPOGLYCEMIC ACTIVITY AND USEFUL FOR PREPARING PHARMACEUTICAL COMPOSITIONS AND USED IN A METHOD FOR LOWERING BLOOD SUGAR LEVEL IN THE TREATMENT OF DIABETES MELLITUS.
Abstract:
BENZENESULFONYL UREA COMPOUNDS THAT ARE EFFECTIVE AS ORAL ANTIDIABETIC AGENTS ARE DISCLOSED TO HAVE THE FORMULA
(4-(X-N(-X1)-CO-NH-Y-)PHENYL)-SO2-NH-CO-NH-R
WHEREIN R IS (A) ALKYL OR ALKENYL OF 3-6 CARBON ATOMS, (B) ENDOALKYLENE-CYCLOHEXYL, ENDOALKYLENE-CYCLOHEXENYL, ENDOALKYLENE-CYCLOHEXYLMETHYL OR ENDOALKYLENE-CYCLOHEXENYLMETHYL OF 1-2 ENDOALKYLENE CARBON ATOMS, (C) BENZYL, PHENYLETHYL, (D) CYCLOHEXYL METHYL, (E) LOWER ALKYL CYCLOHEXYL OR DIALKYL CYCLOHEXYL, METHYL CYCLOPENTYL, (F) CYCLOALKYL OF 5-8 CARBON ATOMS IN THE RING (G) CYCLOHEXENYL, CYCLOHEXENYL-METHYL, METHYLCYCLOHEXENYL, OR (H) NORTRICYCLYL,
X-N(-X1)-
IS INDOLINO OR TETRAHYDROQUINOLINO, AND Y IS ALKYLENE OF 1 TO 3 CARBON ATOMS.
IN WHICH X REPRESENTS HYDROGEN, CHLORINE, BROMINE, METHYL, METHOXY Y REPRESENTS -CH(CH3)-CH2-, OR, PREFERABLY,
-CH2-CH2-
R REPRESENTS HYDROGEN OR, TOGETHER WITH Y, A BRIDGE OF 3 OR 4 CARBON ATOMS, R'' REPRESENTS ALKYL, CYCLOALKYL, CYCLOALKYLALKYL, ARYL, ARALKYL, ALKOXY, CYCLOALKOXY, ALKOXYALKYL, ALKOXYALKOXY, ALKYLMERCAPTO, ALKYLMERCAPTOALKYL, THE ALKLY CONTAINING, IN ANY CASE FROM 1 TO 4 CARBON ATOMS AND THE CYCLOALKYL, IN ANY CASE, 5 TO 8 CARBON ATOMS, R" REPRESENTS HYDROGEN, LOWER ALKYL, R" AND R'' TOGETHER BEING ABLE TO FORM A RING OF FROM 3 TO 5 METHYL GROUPS, AND PHYSIOLOGICALLY TOLERABLE SALTS THEREOF AND PROCESSES FOR THEIR PREPARATION.
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.