Abstract: Compounds of formula IV: ##STR1## wherein R and R.sub.2 are hydrogen or methyl; wherein R.sub.1 is --COOH, --COOR' in which R' is alkyl of 1 to 3 carbon atoms, inclusive, --(CnH.sub.2 n)A in which n is an integer of 1 to 3 and A is fluoro, chloro, bromo, trifluoromethyl, hydroxy, alkoxy, in which the alkyl group is defined as above, or ##STR2## in which R" and R'" are hydrogen or alkyl as defined above or together ##STR3## is pyrrolidino, piperidino, morpholino, 4-methylpiperazino, 4-(2-hydroxyethyl)-piperazino; wherein R.sub.3 is hydrogen, fluoro, chloro, bromo, trifluoromethyl, or nitro; and wherein Ar is phenyl, o-chlorophenyl, o-fluorophenyl, 2,6-difluorophenyl, or 2-pyridyl, are produced.The compounds of formula IV of this invention are sedatives, tranquilizers and muscle-relaxants and can be used for such purposes in mammals and birds.

Abstract: Compounds of the formula II: ##STR1## wherein R is cyclopropyl, cyclopropylmethyl, or allyl; wherein R', R", and R.sub.1 are hydrogen or alkyl of 1 to 3 carbon atoms inclusive; and wherein R.sub.2, R.sub.3, and R.sub.4 are hydrogen, alkyl as defined above, fluoro, chloro, bromo, nitro, trifluoromethyl, or alkylthio in which alkyl is defined as above, are prepared by reacting a compound of the formula I. ##STR2## wherein R", R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are defined as above, and wherein X is chlorine or bromine, with an amine of the formula ##STR3## wherein R and R' are defined as above. The compounds of formula II and the pharmacologically acceptable acid salts thereof have tranquilizing, sedative, antianxiety, and anticonvulsant activity and can be used in animals and birds.

Abstract: 6-(o-halophenyl)-1-methyl-4H-s-triazolo[4,3-a][1,4]-benzodiazepines of the following formula: ##STR1## wherein the substituent "Hal" is either of the halogens having an atomic number up to 35, inclusive, i.e., fluoro, chloro or bromo, and their pharmacologically acceptable acid addition salts which are especially useful as muscle relaxing and anxiolylic agents.

Abstract: Compounds of the formula IV: ##STR1## wherein R.sub.o is hydrogen, alkyl of 1 to 3 carbon atoms, inclusive, --C.sub.n H.sub.2n OR in which n is an integer of 1 to 3, inclusive, and R is hydrogen or methyl, ##STR2## in which n is defined as above, and R.sub.6 and R.sub.7 are hydrogen or alkyl as defined above, or together ##STR3## is pyrrolidino, piperidino, morpholino or ##STR4## in which R.sub.8 is methyl, ethyl, or 2-hydroxyethyl, ##STR5## in which m is an integer of 0 to 3, inclusive, and R.sub.9 is hydrogen, lower alkyl of from 1 to 3 carbon atoms, inclusive, wherein R.sub.1 is hydrogen or methyl; wherein R.sub.2 is phenyl, o-chlorophenyl, o-fluorophenyl, 2,6-difluorophenyl, or 2-pyridyl; and wherein R.sub.3 is hydrogen, fluoro, chloro, bromo, trifluoromethyl, or nitro.

Abstract: Compounds of formula IV: ##STR1## wherein R and R.sub.1 are hydrogen or alkyl of 1 to 3 carbon atoms, inclusive; wherein R.sub.2 is hydrogen or methyl; wherein R.sub.3 is hydrogen, fluoro, chloro, bromo, trifluoromethyl or nitro; and wherein Ar is phenyl, o-chlorophenyl, o-fluorophenyl, 2,6-difluorophenyl or 2-pyridyl, are produced by reacting a hydrazino compound of the formula I ##STR2## wherein R.sub.2, R.sub.3, and Ar are defined as above, with a carbonyl reagent of the formula II: ##STR3## wherein R and R.sub.1 are defined as above and Y is chloro, bromo, iodo or--O--SO.sub.2 --R.sub.4in which R.sub.4 is alkyl, defined as above, phenyl, or tolyl, to give the compound III: ##STR4## wherein R, R.sub.1, R.sub.2, R.sub.3, Ar, and Y are defined as above and heating compound III, in an inert organic solvent, to give compound IV above.

Abstract: Compounds of the formula: ##STR1## wherein R is hydrogen, methyl, or ethyl; wherein R' and R" are hydrogen, alkyl of 1 to 3 carbon atoms, inclusive, wherein R.sub.1 is hydrogen or methyl defined as above; wherein R.sub.2, R.sub.3, R.sub.4, and R.sub.5 are selected from the group consisting of hydrogen, alkyl defined as above, halogen, nitro, trifluoromethyl, and alkoxy and alkylthio, in which the carbon chain moieties are of 1 to 3 carbon atoms, inclusive; and wherein the 5 to 6 nitrogen-carbon linkage is selected from the group consisting of double bonds and single bonds, are produced by a variety of multistep processes.The new compounds of formula X above and the pharmacologically acceptable acid addition salts thereof have oral and parenteral sedative and tranquilizing activity, and anti-depressant activity and can be employed for tranquilizing mammals as well as combating anxiety and depressions.

Abstract: Compounds of the formula I: ##STR1## wherein R.sub.1 is hydroxymethyl, or -CH.sub.2 NR.sub.6 R.sub.7, in which R.sub.6 is -CH.sub.2 -C.tbd.CH, -CH.sub.2 -CH=CH.sub.2, ##STR2## or alkyl of 1 to 3 carbon atoms, inclusive; R.sub.7 is hydrogen or alkyl of 1 to 3 carbon atoms, or together ##STR3## is pyrrolidino, piperidino or morpholino; wherein R.sub.2 is hydrogen, chlorine or fluorine; wherein R.sub.3 is hydrogen, or fluorine if R.sub.2 is fluorine; wherein R.sub.4 is hydrogen, fluorine, chlorine, bromine, nitro, or trifluoromethyl; and wherein R.sub.5 is hydrogen, methyl or ethyl. These compounds, except those in which R.sub.7 is hydrogen, are produced by heating a compound of formula II: ##STR4## wherein R.sub.2, R.sub.3, R.sub.4, and R.sub.5 are defined as hereinabove, and wherein R'.sub.1 is the same as R.sub.1 except that in defining R'.sub.1,R.sub.7 may not be hydrogen, with aqueous formaldehyde in formic acid solution at reflux temperature (about 100.degree. C.).Compounds in which R.sub.

Abstract: Compounds of the formula: ##STR1## wherein R'o and R"o are hydrogen or alkyl of 1 to 3 carbon atoms, inclusive; R.sub.1 is hydrogen, fluoro, chloro, bromo, nitro, trifluoromethyl, or alkylthio in which the alkyl moiety is of 1 to 3 carbon atoms, inclusive; R.sub.2 is phenyl, o-chlorophenyl, 0-fluorophenyl, 2,6-difluorophenyl and 2-pyridyl are prepared by multistep reactions from compounds of formula I: ##STR2## wherein R.sub.1 and R.sub.2 are defined as above and X is chlorine or bromine.Compounds of formula III, intermediates in the preparation thereof, Schiff's bases of compounds IIIA (III in which R'o and R"o are hydrogen), and the pharmacologically acceptable acid addition salts are useful in birds and mammals, including man, as sedatives, antianxiety, antidepressant, anticonvulsive, and muscular relaxing agents.

Abstract: Compounds of the formula III ##STR1## wherein R.sub.1 is hydrogen or methyl; wherein R.sub.2 is hydrogen, fluoro, chloro, bromo, trifluoromethyl, or nitro; and wherein Ar is phenyl, o-chlorophenyl, o-fluorophenyl, o,o-difluorophenyl, or 2-pyridyl, are produced by a two-step process. The compounds of formula III as well as their pharmacologically acceptable acid addition salts thereof are antidepressant agents possessing additionally antianxiety activity. Thus these compounds III are useful in the treatment of anxieties in mammals and birds, and also as anti-depressants in man.

Abstract: A process for the preparation of 1-[(dimethylamino)methyl]-6-substituted-4H-s-triazolo[4,3-a][1,4]benzodiaz epine which comprises the reaction of a 4H-s-triazolo[4,3-a][1,4]benzodiazepine with the reagent ##STR1## wherein X.sup.- signifies the anion of a monovalent acid.

Abstract: A process for the preparation of 1-[(dimethylamino)-methyl]-6-substituted-4H-imidazo[1,2-a][1,4]benzodiazep ine which comprises the reaction of a 6-phenyl-4H-imidazo-[1,2-a][1,4]benzodiazepine with the reagent ##STR1## wherein X.sup.- signifies the anion of a monovalent acid.

Abstract: Intermediates of the formula VI: ##STR1## wherein R is hydrogen or alkyl of 1 to 3 carbon atoms, inclusive, wherein R.sub.2 is hydrogen, fluoro, or chloro; wherein R.sub.3 is hydrogen or fluoro with the proviso that R.sub.3 is not fluoro, if R.sub.2 is chloro; wherein R.sub.4 is hydrogen, fluoro, chloro, bromo, trifluoromethyl, or nitro; and wherein X is chloro, bromo, or iodo, are produced by a multistep process. The compounds VI serve as intermediates for final compounds which are tranquilizers and sedatives and as such useful in mammals and birds.

Abstract: Intermediates of the formula IV: ##STR1## wherein R is selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms, inclusive; and wherein R.sub.2, R.sub.3, and R.sub.4 are selected from the group consisting of hydrogen, fluoro, chloro, bromo, nitro, and trifluoromethyl are produced by a multistep synthesis. The final compounds are tranquilizers and sedatives and can be used in mammals, including man, and in birds.

Abstract: 1-Piperazino-6-(2-pyridyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepines of the formula II: ##SPC1##wherein R is hydrogen, alkyl of 1 to 3 carbon atoms, inclusive, or .beta.-hydroxyethyl; wherein R.sub.1 is hydrogen or alkyl defined as above; and wherein R.sub.2 and R.sub.3 are hydrogen, alkyl as defined above, fluoro, chloro, bromo, nitro or trifluoromethyl, are obtained by reacting a compound of the formula I: ##SPC2##wherein R.sub.1, R.sub.2, and R.sub.3 are defined as above and wherein X is chloro or bromo with a piperazine of the formula: ##SPC3##Wherein R is defined as above.The compounds of the formula II and their pharmacologically acceptable acid addition salts thereof, have tranquilizing, sedative and anti-depressant effects, and are useful for suppression of anxiety and depression in mammals and birds.

Abstract: A process for the production of compounds of the formula III: ##SPC1##wherein ring A is unsubstituted or substituted by fluoro, chloro, bromo, trifluoromethyl, or nitro, and wherein Ar is phenyl, o-chlorophenyl, o-fluorophenyl, or 2-pyridyl, is claimed in which the starting compound is the corresponding 1-methyl-6-substituted-4H-s-triazolo[4,3-a][1,4]-benzodiazepine. Compound III is converted to compoud IV or V, the corresponding 1-(2-aminoethyl)-6-substituted-4H-s-triazolo[4,3-a][1,4]benzodiazepines, which are known antidepressant and anti-anxiety agents.

Abstract: A process for the production of known compounds of the formula IV ##SPC1##wherein R.sub.1 is hydrogen or alkyl of 1 to 3 carbon atoms, inclusive; wherein R.sub.2 is hydrogen, chloro, or fluoro; wherein R.sub.3 is hydrogen, or fluoro with the proviso that R.sub.3 is not fluoro if R.sub.2 is chloro; wherein R.sub.4 is hydrogen, chloro, fluoro, bromo, nitro, and trifluoromethyl, which comprises: treating a compound of the formula I: ##SPC2##wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 have the same significance as above, in formic acid solution with aqueous formaldehyde; treating the resulting compound with phthalimide, triphenylphosphine and then diethyl azodicarboxylate to give a compound which when heated with hydrazine, gives compound IV above.The compounds of formula IV above are known useful antidepressant, tranquilizing, sedative and anti-convulsant agents. The intermediates have also activity in the sedative-tranquilizing area and these compounds can be used in mammals and birds for tranquilization.

Abstract: A process to make 6-phenyl-4H-s-triazolo[4,3-a][1,4]-benzodiazepines by converting 2-[3-(hydroxymethyl)-4H-1,2,4-triazol-4-yl]benzophenones to 2-[3-[(phthalimido or methanesulfonyl)methyl]-4H-1,2,4-triazol-4-yl]benzophenones and converting these compounds to the highly active 6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines useful as tranquilizers and sedatives.

Abstract: Compounds of the formulae IV and V: ##SPC1##wherein R.sub.0 and R.sub.1 are hydrogen or alkyl of 1 to 3 carbon atoms, inclusive; wherein R.sub.2 is hydrogen, fluoro, chloro, or trifluoromethyl; wherein R.sub.3 is hydrogen or fluoro with the proviso that R.sub.3 cannot be fluoro, if R.sub.2 is chloro or trifluoromethyl; and wherein R.sub.4 is hydrogen, fluoro, chloro, bromo, trifluoromethyl, or nitro, are obtained by a multi-step reaction from the corresponding .alpha.-(phenyl)-o-toluidine of the formula I: ##SPC2##wherein R.sub.2, R.sub.3, and R.sub.4 are defined as above, by treating I in sequence with an alkyl ester of orthoformic acid the resulting product with 2-alkyl-2-(aminoalkyl)-1,3-dioxolane or a 2-amino-alkanone dialkyl ketal and finally with titanium tetrachloride to obtain compound IV, and oxidizing compound IV to obtain the corresponding compound V.Compounds IV and V have minor tranquilizing activity which can be utilized to calm mammals or birds.

Abstract: Phthalimides of the Formula ##SPC1##Wherein X is NH.sub.2, N(CH.sub.3).sub.2, Cl or Br and R.sub.0 and R.sub.1 are hydrogen, methyl or ethyl are disclosed as intermediates in the preparation of benzodiazepines.

Abstract: 8-Bromo-1-[(dimethylamino)methyl]-6-(2-pyridyl)-4H-imidazo[1,2-a][1,4]benzo diazepine of the formula: ##SPC1##Is prepared, which compound has anti-depressant, anti-convulsant, and anti-anxiety activities and is particularly useful in mammals to combat depression and anxieties.