Glutaramide diuretic agents

A compound of the formula:

• ##STR213## or a pharmaceutically acceptable salt thereof, wherein:
• A completes a 5- or 6-membered saturated or monounsaturated carbocyclic ring which is optionally fused to another 5- or 6-membered saturated carbocyclic ring or is optionally benzofused;
• B is --(CH.sub.2).sub.m -- wherein m is an integer of from one to two;
• R and R.sup.4 are each independently hydrogen, C.sub.1 -C.sub.6 alkyl or benzyl, or they represent a biolabile ester-forming group other than C.sub.1 -C.sub.6 alkyl or benzyl;
• R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl;
• R.sup.2 and R.sup.3 are each independently hydrogen, hydroxy, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy;
• and
• R.sup.5 is C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.3 -C.sub.7 cycloalkenyl, aryl(C.sub.2 -C.sub.6 alkynyl), --NR.sup.6 R.sup.7, --NR.sup.8 COR.sup.9, --NR.sup.8 SO.sub.2 R.sup.9, tetrahydrofuranyl or homodioxanyl;
• or C.sub.1 -C.sub.6 alkyl substituted by halogen, hydroxy, C.sub.1 -C.sub.6 alkoxy, C.sub.2 -C.sub.6 hydroxyalkoxy, C.sub.1 -C.sub.6 alkoxy(C.sub.1 -C.sub.6 alkoxy), C.sub.3 -C.sub.7 cycloalkyl, C.sub.3 -C.sub.7 cycloalkenyl, aryl, aryloxy, aryloxy(C.sub.1 -C.sub.6 alkoxy), heterocyclyl, heterocyclyloxy, --NR.sup.6 R.sup.7, --NR.sup.8 COR.sup.9, --NR.sup.8 SO.sub.2 R.sup.9, --CONR.sup.6 R.sup.7, --SH, --S(O).sub.p R.sup.10, --COR.sup.11 or --COOR.sup.12 ;
• wherein
• R.sup.6 and R.sup.7 are each independently hydrogen, C.sub.1 -C.sub.4 alkyl, aryl, aryl(C.sub.1 -C.sub.4 alkyl), C.sub.2 -C.sub.6 alkoxyalkyl, heterocyclyl or C.sub.3 -C.sub.7 cycloalkyl optionally substituted by hydroxy or C.sub.1 -C.sub.4 alkoxy;
• R.sup.6 and R.sup.7, when taken together with the nitrogen atom to which they are attached, form a pyrrolidinyl, piperidino, morpholino, piperazinyl or N-(C.sub.1 -C.sub.4 alkyl)piperazinyl group;
• R.sup.8 is hydrogen or C.sub.1 -C.sub.4 alkyl;
• R.sup.9 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, trifluoromethyl, aryl, aryl(C.sub.1 -C.sub.4 alkyl), aryl(C.sub.1 -C.sub.4 alkoxy), heterocyclyl or --NR.sup.6 R.sup.7 ;
• R.sup.10 is C.sub.1 -C.sub.4 alkyl, aryl, heterocyclyl or --NR.sup.6 R.sup.7 ;
• R.sup.11 is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.7 cycloalkyl, aryl or heterocyclyl;
• R.sup.12 is hydrogen or C.sub.1 -C.sub.4 alkyl;
• and
• p is zero, one or two;
• said biolabile ester-forming group other than C.sub.1 -C.sub.6 alkyl or benzyl in the definition of R and R.sup.4 being selected from C.sub.1 -C.sub.8 alkanoyloxy(C.sub.1 -C.sub.8 alkyl), and the C.sub.1 -C.sub.8 alkyl and C.sub.3 -C.sub.7 cycloalkyl-substituted derivatives thereof and the aryl-substituted derivatives thereof, aroyloxy(C.sub.1 -C.sub.8 alkyl), aryl, aryl(C.sub.1 -C.sub.8 alkyl) and halo(C.sub.1 -C.sub.8 alkyl), wherein said aryl groups are phenyl, naphthyl or indanyl with said aryl groups being optionally substituted with halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy groups;
• said aryl groups in the definition of R.sup.5. R.sup.6, R.sup.9, R.sup.10 and R.sup.11 having up to ten carbon atoms the nuclear ring, with said groups being optionally substituted with halogen, hydroxy, cyano, trifluoromethyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, carbamoyl, amino, mono- or di(C.sub.1 -C.sub.4 alkyl)amino or C.sub.1 -C.sub.4 alkanoylamino groups;
• and
• said heterocyclyl groups in the definition of R.sup.5 being pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, furanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, indolyl, isoindolinyl, quinolyl, quinoxalinyl, quinazolinyl and benzimidazolinyl, with said groups being optionally substituted with halogen, hydroxy, oxo, C.sub.1 -C.sub.4 alkyl, benzyl, carbamoyl, amino, mono- or di(C.sub.1 -C.sub.4 alkyl)amino or C.sub.1 -C.sub.4 alkanoylamino groups.