GB1117068A — S-triazole-[4,3-a]-pyridine derivatives and processes for their preparation

USPTO Abstract

Novel compounds having tranquilizing, hypotensive and analgesic action of the general formula <FORM:1117068/C2/1> wherein R is H or CH3 and R1 is alkyl containing 1-4 carbon atoms, alkoxy containing 1-4 carbon atoms or halogen, and the non-toxic salts thereof with organic or inorganic acids are prepared by reacting an s-triazolo(4,3-a)-pyridine-3-one of the general formula <FORM:1117068/C2/2> or its sodium salt with an N-aryl-N1-o -halo-propyl -piperazine of the general formula <FORM:1117068/C2/3> or treating a 2-o -halopropyl-s-triazolo-(4,-3-a) -pyridine - 3 - one of the general formula <FORM:1117068/C2/4> with a suitable N-aryl-piperazine; or reacting a 2-o -morpholinopropyl-s-triazolo-(4,3-a)-pyridine-3-one of the general formula <FORM:1117068/C2/5> with a suitably substituted aniline; or reacting a b ,b 1-dichloroethyl-aniline of the general formula <FORM:1117068/C2/6> with a 2-o -aminopropyl-s-triazolo-(4,3-a)-pyridine-3-one of the general formula <FORM:1117068/C2/7> The starting material 2-o -chloropropyl-s-triazolo - (4,3-a) - pyridine - 3 - one is prepared by treating s-triazolo(4,3-a)-pyridine-3-one with sodium hydride in dioxan solution and then adding 1-bromo-3-chloropropane. 2-o -morpholinopropyl -s-triazolo(4,3-a)-pyridine-3-one hydrochloride is prepared by refluxing s-triazolo-(4,3 - a) - pyridine - 3 - one, sodamide and N - a - chloropropyl - morpholine, basifying, extracting, and precipitating the product with ethereal hydrochloric acid. 2-o -aminopropyl-s-triazolo(4,3-a) -pyridine-3-one is prepared by heating 2-a -chloropropyl-s-triazolo(4,3-a)-pyridine-3-one and saturated alcoholic ammonia solution in a sealed tube.