Patent GB-990887-A (GB)
Title: Carbamic acid derivatives
IPC: C07D285/30
Filed: 1962-09-14
Abstract: The invention comprises compounds of formulae <FORM:0990887/C2/1> <FORM:0990887/C2/2> <FORM:0990887/C2/3> wherein R1 is a hydrogen atom, an alkyl group having 1 to 7 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a cycloalkyl-alkyl group having 3 to 8 carbon atoms in the ring and 1 to 3 carbon atoms in the alkyl moiety, or a phenyl-alkyl group wherein the alkyl group has 1 to 3 carbon atoms, R2 is a hydrogen or halogen atom, an alkyl group having 1 to 4 carbon atoms or a trifluoromethyl group, R3 is a halogen atom, an alkyl group having 1 to 4 carbon atoms or a trifluoromethyl group, R4 is an alkyl group having 1 to 7 carbon atoms, Z1 and Z2 are alkyl groups having up to 7 carbon atoms, and Y1 is a hydrogen atom or an alkyl group having 1 to 7 carbon atoms, alkali metal salts thereof, and their preparation by (a) reacting a compound of formula <FORM:0990887/C2/4> or a salt thereof, wherein at least one of the symbols Y11 and R41 represents a hydrogen atom and the other may have any of the values of Y1 or R4 respectively, with an isocyanate of formula O=C=N-Z1 or a metal derivative thereof; (b) reacting a compound of formula <FORM:0990887/C2/5> wherein R411 represents R4 or the group -CONHZ1 and Y111 represents Y1 or the group -CONHZ1, at least one of R411 and Y111 representing the group -CONHZ1, with an aldehyde of formula O=CH-R1 or (c) reacting a compound of formula <FORM:0990887/C2/6> with an aldehyde of formula O=CH-R1 and a reducing agent. The compounds of the invention have pharmaceutical properties (see Division A5).  Compounds of formulae <FORM:0990887/C2/7> <FORM:0990887/C2/8> are prepared by carbamylation of one or two sulphonamide groups, using for example an isocyanate.ALSO:Pharmaceutical compositions having diuretic, saliuretic or antihypertensive activity comprise compounds of formul <FORM:0990887/A5-A6/1> wherein R1 is a hydrogen atom, an alkyl group having 1 to 7 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a cycloalkyl-alkyl group having 3 to 8 carbon atoms in the ring and 1 to 3 carbon atoms in the alkyl group, or a phenyl-alkyl group wherein the alkyl group has 1 to 3 carbon atoms, R2 is a hydrogen or halogen atom, an alkyl group having 1 to 4 carbon atoms or a trifluoromethyl group, R3 is a halogen atom, an alkyl group having 1 to 4 carbon atoms or a trifluoromethyl group, R4 is an alkyl group having 1 to 7 carbon atoms, Z1 and Z2 are alkyl groups having up to 7 carbon atoms, and Y1 is a hydrogen atom or an alkyl group having 1 to 7 carbon atoms, or an alkali metal salt thereof, in combination with a pharmaceutical carrier, and may be in forms suitable for oral or parenteral administration, for example tablets, capsules, dragees, solutions, suspensions or emulsions.  Other pharmaceutically active substances may be present, for example antihypertensive agents, such as Rauwalfia alkaloids, for example reserpine, rescinnamine or deserpicine, similar compounds, for example syrosingopine, veratum alkaloids, for example germine or protoveratrine, synthetic antihypertensives, for example hydralazine, dihydralazine or guanethidine, and ganglion blockers, for example chlorisondamine.