Synthesis of 3,3′-dimethyl-1,1′-azobenzimidazolium salts

Studies of Anti‐HIV Transcription Inhibitor Quinolones: Identification of Potent N1‐Vinyl Derivatives

“…Ethyl 1‐amino‐7‐chloro‐6‐nitro‐4‐oxo‐1,4‐dihydroquinoline‐3‐carboxylate (26) : 9 NaH (0.04 g, 1.68 mmol) was added to a suspension of 22 10 (0.50 g, 1.68 mmol) in DMF (3 mL), and the mixture was maintained at RT for 3 h. The reaction mixture was then cooled to 0 °C and a solution of freshly prepared TSH ( 25 )11 (0.31 g, 1.68 mmol) in CH 2 Cl 2 (3 mL) was added. The mixture was maintained at this temperature for 10 min, then at RT for 21 h. The resulting precipitate was removed and the filtrate evaporated to dryness to afford a residue that was dissolved in CH 2 Cl 2 and washed with saturated aq NaHCO 3 solution.…”

“…An alternative approach, which enabled the amino group to be introduced at the N1 position, involved amination of synthon 22 ,10 using freshly prepared O ‐ p ‐tolylsulfonylhydroxylamine (TSH) 25 ,11 in the presence of sodium hydride in dimethylformamide (DMF) (Scheme ). The 1‐amino derivative 26 ,9 obtained by this alternative route, was combined with selected arylpiperazines to give compounds 29 a–c .…”

Proceedings of the British Pharmacological Society

“…It has been possible to obtain neuromuscular blocking drugs which are short-acting in animals, e.g. y-oxalolaudonium (Brittain, Collier & D'Arcy, 1961), AH 8165 (Brittain & Tyers, 1973) and stercuronium (Hespe & Wieriks, 1971), but these drugs have a much more prolonged action in man (Blogg, Savege, Simpson, Ross & Simpson, 1973;Admiraal, 1973 (Glover, Rowbottom & Bishop, 1973), has now been shown to be a short-acting, competitive, neuromuscular blocking drug in both animals and human beings. We wish to report the pharmacology of this compound and to discuss the basis for its brevity of action.…”

Pharmacological and Certain Chemical Properties of Ah 10407, an Unusually Short‐acting, Competitive Neuromuscular Blocking Drug, and Some Related Compounds

“…Many compounds expected to be easily susceptible to enzymatic degradation have been made in attempts to find a competitive neuromuscular blocking (NMB) drug with a short duration of action in man (Bruce, 1956;Haining, Johnston & Smith, 1960;Brittain, Collier & D'Arcy, 1961;Savarese, Nakamura & Kitz, 1970;Savarese, Ginsburg, Lee & Kitz, 1973) but only succinylcholine, a depolarizing agent, has proved satisfactory in this respect. An alternative, novel approach to the desired short-acting, competitive NMB drug in man was identified during the pharmacological and physico-chemical examination of 1,1 '-azobis[3-methyl-2-phenylbenzimidazolinium] dimethanesulphonate (AH 10407; Blogg, Brittain, Simpson & Tyers, 1975;Tyers, 1975), one of a series of azobisbenzimidazolinium salts (Glover, Bishop & Rowbottom, 1973). AH 10407 (la) is a competitive, neuromuscular blocking drug with an ultra-short duration of action in animals and in man.…”

“…An alternative, novel approach to the desired short-acting, competitive NMB drug in man was identified during the pharmacological and physico-chemical examination of 1,1 '-azobis[3-methyl-2-phenylbenzimidazolinium] dimethanesulphonate (AH 10407; Blogg, Brittain, Simpson & Tyers, 1975;Tyers, 1975), one of a series of azobisbenzimidazolinium salts (Glover, Bishop & Rowbottom, 1973). AH 10407 (la) is a competitive, neuromuscular blocking drug with an ultra-short duration of action in animals and in man.…”