Patent GB-701209-A (GB)
Title: Improvements in or relating to substituted dicarboxylic acid amides
IPC: C07D295/13
Filed: 1950-05-12
Abstract: The invention comprises compounds of the general formula <FORM:0701209/IV (b)/1> wherein m = 4 or 5 and n = 2-7, and their non-toxic salts (e.g. hydrochlorides).  These compounds, which possess the property of prolonging the curarizing action of succinylcholine, may be prepared by heating b -aminoethyl-piperidine or -pyrrolidine with dimethyl or diethyl esters of the appropriate dicarboxylic acids, and, if desired, neutralizing aqueous solutions of the resulting bases with an acid.  Examples describe the preparation of N:N1-bis-(b -piperidinoethyl) - succinamide, - pimelamide, - glutaramide, -adipamide and -azelä-amide, and N:N1-bis-(b -pyrrolidinoethyl)-succinamide and -adipamide. U.S.A. Specification 2,438,200 is referred to.  The Provisional Specification comprises compounds of the general formulae <FORM:0701209/IV (b)/2> and <FORM:0701209/IV (b)/3> <FORM:0701209/IV (b)/4> wherein R1 and R2 represent methyl or ethyl radicals or NR1R2 represents a piperidino, pyrrolidino or morpholino radical, R3 denotes hydrogen or a methyl, ethyl or benzyl radical, -X denotes an anion derived from a non-toxic acid and n = 1-8.  Additional compounds described are succinic acid bis-b -dimethylaminoethylamide and its bis methiodide, methochloride, ethiodide, ethochloride, metho- and etho-sulphates and benzochloride, malonic and sebacic acid bis-b -dimethylaminoethylamide bis methiodides, glutaric acid bis-b -dimethylaminoethylamide and its bis methiodide, adipic acid bis-b -dimethylaminoethylamide and its bis methiodide and ethiodide, suberic acid bis-b -dimethylaminoethylamide and its bis methiodide and benzochloride, azelaic acid bis-b -dimethylaminoethylamide and its bis methiosulphate and ethiodide, succinic acid bisdiethylaminoethylamide and its bis methiodide, ethiodide and benzochloride, the bis methiodides of succinic acid bis-morpholino- and -piperidino - ethylamides, glutaric acid bispynrolidinoethylamide and its bis methiodide, ethiodide and benzochloride, glutaric acid bisdiethylaminoethylamide bis methiodide, and the bis methiodides of malonic, glutaric and adipic acid bis-morpholinoethylamides.ALSO:The curarizing action of succinyl-choline is prolonged by p  admixing there-with a compound of the general formula <FORM:0701209/VI/1> m = 4 or 5 and n = 2-7), and their non-toxic salts, e.g. N:N1-bis-(b -pipe-rindinoethyl)-succinamide, -pimelamide, -glutaramide, -adipamide or -azel<\>aamide, or N:N1-bis-(b -pyrrolidinoethyl)-succinamide or adipamide. U.S.A. Specification 2,438,200 is referred to.  According to the Provisional Specification, the active curarizing agent may be any compound of the general formula <FORM:0701209/VI/2> (wherein R and R1 represent methyl or ethyl radicals and X the anion of a nontoxic acid), and the agent for prolonging its activity may be any compound of either of the general formulae <FORM:0701209/VI/3> (wherein R1 and R2 represent methyl or ethyl radicals or NR1R2 represents a piperidino, pyrrolidino or morpholino radical, R3 represents hydrogen or a methyl, ethyl or benzyl radical and n = 1-8).