54748-06-0

Upstream product

• 153901-48-5 RL 236 
• 153901-56-5 RL 218 
• 111-96-6 diethylene glycol dimethyl ether 
• 1068-57-1 acetic acid hydrazide 
• 69754-68-3 7-chloro-3,5-dihydro-2-methoxy-5-phenyl-4H-1,5-benzodiazepin-4-one 
• 36985-42-9 7-chloro-2-methylamino-5-phenyl-4H-3,5-dihydro-1,5-benzodiazepin-4-one 
• 22316-55-8 N-desmethylclobazam 
• 36985-45-2 8-chloro-4-(dimethylamino)-1,3-dihydro-1-phenyl-2H-1,5-benzodiazepin-2-one 
• 1483-73-4 diphenyliodonium bromide 

Downstream Products

• 55151-44-5 4-(2-Dimethylaminoethyl)-1-methyl-8-chloro-6-phenyl-4H-s-triazolo[4,3-a] [1,5]benzodiazepin-5-one 
• 153901-56-5 RL 218 
• 153901-48-5 RL 236 
• 153901-55-4 8-Chloro-1-methyl-5-morpholin-4-yl-6-phenyl-6H-2,3,6,10b-tetraaza-benzo[e]azulene 
• 153901-45-2 8-Chloro-1-methyl-5-methylsulfanyl-6-phenyl-6H-2,3,6,10b-tetraaza-benzo[e]azulene 
• 153901-41-8 8-chloro-1-methyl-6-phenyl-4H-<1,2,4>triazolo<4,3-a><1,5>benzodiazepine-5(6H)-thione 

Relevant academic research and scientific papers

Acid-catalysed hydrolysis and benzodiazepine-like properties of 5-(dialkylamino)- and 5-(alkylthio)-substituted 8-chloro-6-phenyl-6H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepines in mice

The in-vitro and in-vivo hydrolysis of two benzodiazepine compounds has been studied to evaluate their in-vivo activity in mice. Compounds RL 218 and RL 236, selected as representative examples of N,N-dialkyl-8-chloro-6-phenyl-6H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepin-5 -amines (1) and of their 5(alkylthio) substituted analogues (2), were rapidly hydrolysed to the corresponding 8-chloro-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepin-5(6H)-one 3 (RL 214) in aqueous acidic solution at pH 1.5. This reaction also occurred extensively in mice when compounds RL 218 and RL 236 were given orally but not intraperitoneally. Both compounds were active against pentylenetetrazole-induced lethal convulsions in mice only when administered orally. After administration of pharmacologically effective oral doses (ED50, the dose protecting 50% of mice), at the time of assessment of the antipentylenetetrazole activity, mean brain concentrations of RL 218 and RL 236 were below the limits of sensitivity of the analytical procedure whereas brain concentrations of their metabolite RL 214 were comparable with that present after an oral equiactive dose of this compound itself. RL 214 but not RL 218 or RL 236 had in-vitro affinity for brain benzodiazepine receptors. These results indicate that the anticonvulsant activity of RL 218 and RL 236 in mice depends essentially on their in-vivo transformation into the common active metabolite RL 214 which most probably arises as a result of acid catalysed hydrolysis in the gastric juice.

1,5-Benzodiazepines XI. 5-(Dialkylamino) or 5-(alkylthio) substituted 8-chloro-6-phenyl-6H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepines with anticonvulsant activity

The cyclocondensation of (dimethylamino)benzodiazepinones 3a,b with hydrazides yielded triazolobenzodiazepinones 4 which were treated with Lawesson's reagent to give thiolactams 5. The phase-transfer catalyzed (TEBA) alkylation of compounds 5 with suitabl

4H-S-Triazolo[4,3-2][1,5]benzodiazepin-5-ones

Compounds of the following formula STR1 are useful as central nervous system depressants, tranquilizers, sedatives, growth promotors, anti-convulsants and muscle relaxants in mammalian species.

1,5-Benzodiazepin-4-ones

Novel 1,5-benzodiazepin-4-one derivatives, bearing between the 1,2-positions a triazolo ring, as disclosed. These 1,2-triazolo-1,5-benzodiazepin-4-ones are useful as muscle-relaxant, anti-convulsant and sedative agents.

S-triazolo-1,5-benzodiazpine-4-ones

A s-triazolo-1,5-benzodiazepin-4-one selected from the group of compounds of the formulae: STR1 wherein Ro is hydrogen, alkyl of 1 to 3 carbon atoms, inclusive, hydroxy, hydroxymethyl, and STR2 in which R" and R'" are hydrogen or alkyl defined as above, or together STR3 is selected from the group consisting of pyrrolidino, piperidino, morpholino, and N-methylpiperazino; wherein R is hydrogen, alkyl of 1 to 3 carbon atoms, inclusive and STR4 in which R" and R'" are hydrogen or alkyl as defined above or together STR5 is defined as above; wherein R1 is hydrogen or methyl; wherein R2, R3, R4, and R5 are selected from the group consisting of hydrogen, alkyl alkyl defined as above, halogen, nitro, trifluoromethyl, and alkylthio in which alkyl is defined as above are produced from the corresponding 4-hydrazino-2H-1,5-benzodiazepines-2-ones of the formula (11A) STR6 wherein R1, R2, R3, R4, and R5 have the significance of above, with an acetic acid chloride or if Ro is hydrogen with ethyl ortho-formate, and heating to an elevated temperature to give the corresponding 4H-s-triazolo[4,3-a][1,5]benzodiazepin-5(6H)-one which by additional procedures can be converted to the various compounds presented by formula 111A. Compounds of formula 111B are best obtained by reacting a 4-thio-1H-1,5-benzodiazepine-2,4-(3H,5H)-dione (1A) STR7 with a selected carbazate, followed by heating to an elevated level. Additional steps are necessary to synthesize the various compounds presented by formula 111B. The new compounds of formula 111A and 111B have tranquilizing and sedative activity.