37115-31-4

Upstream product

• 37115-34-7 N,N-Didemethyladinazolam 
• 75-07-0 acetaldehyde 
• 18091-89-9 7-chloro-2-hydrazino-5-phenyl-3H-1,4-benzodiazepine 
• 39479-72-6 8-chloro-1-(chloromethyl)-6-phenyl-4H-s-triazolo<4,3-a><1,4>benzodiazepine 
• 109-89-7 diethylamine 

Relevant academic research and scientific papers

1-(Aminoalkyl)-6-aryl;-4H-s-triazole[4,3-a][1,4]benzodiazepines with antianxiety and antidepressant activity

A series of 1-(Aminoalkyl)-6-aryl;-4H-s-triazole[4,3-a][1,4]benzodiazepines has been prepared and evaluated for central nervous system activity. The authors have found that members of this series have activity in pharmacological test systems designed to detect both anxiolytic and antidepressant activity. Each type of activity could be varied independently by appropriate substituent selections.

1-Halomethyl-6-phenyl-4H-s-[4,3-a][1,4]benzodiazepines

1-Substituted-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines of the formula II: STR1 wherein R0 is selected from the group consisting of hydrogen, methyl, ethyl, fluorine, chlorine, and bromine, and X is selected from fluorine, chlorine, and bromine; wherein R1 is selected from the group consisting of hydrogen, alkyl of 1 to 3 carbon atoms inclusive; wherein R2, R3, R4, and R5 are selected from the group consisting of hydrogen, alkyl, as defined above, halogen, nitro, cyano, trifluoromethyl, and alkoxy, alkylthio, alkylsulfinyl, and alkylsulfonyl, in which the carbon chain moieties are of 1 to 3 carbon atoms, inclusive, are prepared by reacting a compound of the formula: STR2 wherein R1, R2, R3 R4, and R5 are defined as above, with an haloacyl chloride or haloacyl bromide of the formula STR3 wherein Ro and X are defined as above and X' is chlorine or bromine. The new products of formula II including their pharmacologically acceptable acid addition salts are useful as sedatives, tranquilizers and muscle relaxants in mammals and birds, and if X=X"=Cl or Br they are useful as intermediates for cyano, alkylthio and dialkylamino products of high sedative and tranquilizing activity.

Intermediates and process for the production of certain triazolobenzodiazepines

A multi-step process for the preparation of 1-[(amino - or substituted amino)methyl]-6-phenyl-4H-s-triazolo-[4,3-a][1,4]benzodiazepines of the formula VI: SPC1 wherein R' is hydrogen or alkyl of 1 to 3 carbon atoms, inclusive, and wherein the rings A and B are unsubstituted or substituted by one or two substituents selected from the group consisting of chloro, fluoro, bromo, nitro, and trifluoromethyl, which comprises: treating a compound of the formula I: SPC2 wherein rings A and B are defined as above, with acetic anhydride and formic acid to obtain compound II: SPC3 wherein A and B rings have the significance as above, treating compound II with sufficient formaldehyde to produce compound III, the 3,5-bis(hydroxymethyl)derivative of II; treating III with phthalimide, triphenylphosphine and diethyl azodicarboxylate to give compound IV, the 3,5-bis(phthalimidomethyl) derivative of II; and treating IV with hydrazine hydrate to obtain a compound of formula V SPC4 wherein rings A and B are defined, as herein above. Compound V can then be alkylated in known manner to give those compounds of formula VIa which corresponds to formula VI when R' is desired to be alkyl. The compounds of formula VI have antidepressant and antianxiety effects in mammals and birds.

Process for the production of 1-aminomethyl-6-phenyl-4h-s-triazolo-[4,3-a][1]benzodiazepines and intermediates

A multistep process for the production of a compound of the formula V: SPC1 wherein R' and R" are alkyl of 1 to 3 carbon atoms, inclusive or together EQU1 is pyrrolidino, piperidino, 4-methylpiperazino or morpholino; and wherein the rings A and B are unsubstituted, or substituted by one or more substituents selected from the group consisting of fluoro, chloro, bromo, nitro and trifluoromethyl, which comprises treating an equivalent of a compound of formula 1: SPC2 Wherein rings A and B are defined as above, with 2 equivalents of an α-phthalimido acetyl halide in an inert organic solvent to obtain a 1,3-dioxo-2-isoindolineacetic acid, [[N-(2-benzoylphenyl)-1,3-dioxo-2-isoindolineacetamido]methylene]hydrazide II which when treated with trifluoroacetic acid gives compound III; treating compound III with a dialkylmethyleneammonium chloride in an inert organic solvent to obtain a 2-[3-(dialkylamino)methyl-5-(phthalimidomethyl)-4H-1,2,4-triazol-4-yl]benzophenone IV and treating IV with hydrazine in an alkanol to obtain a compound V above. Also claimed are the intermediates II and IV. The 1-aminomethyltriazolobenzodiazepine compounds (V) are used for treatment of anxieties and/or depressions in mammals and birds.