GB788868A - New heterocyclic derivatives and processes for their preparation - Google Patents

Abstract

The invention comprises compounds of the general formula: <FORM:0788868/IV (b)/1> (wherein A represents a saturated divalent aliphatic group which may carry one or more phenyl substituents, B a straight or branched saturated divalent aliphatic chain, and R an alkyl group of 1-4 carbon atoms) and their acid addition and quaternary ammonium salts, and the preparation of the free bases by reacting an imide of the general formula: <FORM:0788868/IV (b)/2> with an ester of the general formula: <FORM:0788868/IV (b)/3> (wherein Z represents the acid residue of a reactive ester, e.g. a halogen atom or a sulphonic or sulphuric grouping). The products may be converted into acid addition salts by treatment with mineral or organic acids, or into quaternary ammonium salts by treatment with alkyl esters. Alternatively the quarternary ammonium salts may be prepared directly by replacing compound (III) by a corresponding quaternary ammonium salt or compound (II) by a corresponding compound in which the nitrogen atom is tertiary. The products are useful in human or veterinary medicine as ganglionblocking agents, hypotensors, spasmolytics, and potentiators of an esthetics and analgesics. In examples: (1) 3 : 3-diphenylpyrrolidine-2 : 5-dione is refluxed with 1-(g -chloropropyl)-4-methylpiperazine in dimethylformamide in the presence of potassium ethoxide to produce 1-(g - 41 - methyl - 11 - piperazinglypropyl)-3 : 3-diphenylpyrrolidine-2 : 5-dione, the hydrochloride of which is described; (2) the product of (1) is refluxed with methyl iodide in acetone to form its dimethiodide. The Provisional Specification refers broadly to compounds of the general formula: <FORM:0788868/IV (b)/4> (wherein A represents a saturated or unsaturated aliphatic or an aromatic divalent hydrocarbon group, such as vinylene, alkylene or o-phenylene, which may be substituted by one or more halogen atoms or lower (1-4 C) alkyl or aryl groups, B is as defined above, X1 and X2 each represent a straight or branched saturated divalent aliphatic chain of not more than 4 carbon atoms and together contain not less than 3 carbon atoms, and R represents hydrogen or a lower alkyl or acyl group), and describes the following further methods of preparation: (i) reaction of an imide of the general formula: <FORM:0788868/IV (b)/5> with a compound of the general formula: <FORM:0788868/IV (b)/6> (ii) (when R is lower alkyl or acyl) alkylation or acylation of the corresponding compounds in which R=H; (iii) reaction of a diacid of the general formula; <FORM:0788868/IV (b)/7> or a derivative (e.g. halide, ester or anhydride) thereof, with a compound of the general formula: <FORM:0788868/IV (b)/8> (iv) (when B is -CH2-) reaction of compound (II) with compound (C) in the presence of formaldehyde.