Hoffmann-la Roche Inc.

Leo Henryk Sternbach

Rodney I Fryer

James Valentine Earley

Michael Edward Derieg

Armin Walser

Werner Metlesics

George F Field

Robert Ye-Fong Ning

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.

1,5-Benzodiazepin-4-ones

Tricyclic benzodiazepine derivatives (A) bearing a hydroxylower alkyl substituent in the 1-position and a heterocyclic ring joined between positions 4 and 5 of the benzodiazepine moiety are described. The heterocyclic ring will contain the nitrogen atom appearing at position 4 of the benzodiazepine ring as well as the hetero atom, which may be either oxygen or nitrogen, attached to the carbon atom at the 5-position of the benzodiazepine ring. A bearing an oxygen atom in the new heterocyclic ring may be formed from the corresponding 4,5-unsaturated benzodiazepines by treatment with an epoxide compound in the presence of an acid catalyst. A bearing either a nitrogen or an oxygen atom in the new heterocyclic ring may be prepared by cyclization of the corresponding open compound. A are useful as sedative, muscle relaxant and anti-convulsant agents.

Tricyclic benzodiazepines

Tricyclic benzodiazepine derivatives ('A') bearing a hydroxylower alkyl substituent in the 1-position and a heterocyclic ring joined between positions 4 and 5 of the benzodiazepine moiety are described. The heterocyclic ring will contain the nitrogen atom appearing at position 4 of the benzodiazepine ring as well as the hetero atom, which may be either oxygen or nitrogen, attached to the carbon atom at the 5-position of the benzodiazepine ring. 'A' bearing an oxygen atom in the new heterocyclic ring may be formed from the corresponding 4,5-unsaturated benzodiazepines by treatment with an epoxide compound in the presence of an acid catalyst. 'A' bearing either a nitrogen or an oxygen atom in the new heterocyclic ring may be prepared by cyclization of the corresponding open compound. 'A' are useful as sedative, muscle relaxant and anti-convulsant agents.

Novel preparations of triazolobenzodiazepines are disclosed. Novel 6-pyridyl-4H-triazolo[4,3-a]-1,4-benzodiazepines and novel intermediates are also disclosed which are useful as anticonvulsants, muscle relaxants and sedative agents.

Preparation of triazolo benzodiazepines and novel compounds

Novel 2[2-(1,3-diazacycloalk-2-enyl)]benzophenone compounds and novel 1,3-diazacycloalkenyl[2,1-a]isoindole compounds having useful analgesic and psychostimulant properties are prepared inter alia by condensation of o-benzoylbenzaldehydes with aliphatic diamines.

Process for the preparation of certain hydroperoxy derivatives

Intermediates for the production of tricyclic benzodiazepines

Tricyclic benzodiazepine derivatives ('A') bearing a hydroxylower alkyl substituent in the 1-position and a heterocyclic ring joined between positions 4 and 5 of the benzodiazepine moiety are described. The heterocyclic ring will contain the nitrogen atom appearing at position 4 of the benzodiazepine ring as well as the hetero atom, which may be either oxygen or nitrogen, attached to the carbon atom at the 5-position of the benzodiazepine ring. A bearing an oxygen atom in the new heterocyclic ring may be formed from the corresponding 4,5-unsaturated benzodiazepines by treatment with an epoxide compound in the presence of an acid catalyst. A bearing either a nitrogen or an oxygen atom in the new heterocyclic ring may be prepared by cyclization of the corresponding open compound. A are useful as sedative, muscle relaxant and anti-convulsant agents.

Derivatives of 7H-indolo[2,3-c]quinolin-6(5H)-one and 7H-indolo[2,3-c]quinoline, prepared, inter alia, from the corresponding 3-azido-4-phenylcarbostyrils or corresponding N-(lower alkylamino)-3-(2-fluorophenyl)-indole-2-carboxamides, are described. The end products of the invention are useful as anti-tumor agents, i.e., they inhibit the growth of transplantable tumors.

Indoloquinolines, intermediates and processes

Intermediates in the production of tricyclic benzodiazepines

Tricyclic benzodiazepine derivatives (A) bearing a hydroxylower alkyl substituent in the 1-position and a heterocyclic ring joined between positions 4 and 5 of the benzodiazepine moiety are described. The heterocyclic ring will contain the nitrogen atom appearing at position 4 of the benzodiazepine ring as well as the hetero atom, which may be either oxygen or nitrogen, attached to the carbon atom at the 5-position of the benzodiazepine ring. 'A' bearing an oxygen atom in the new heterocyclic ring may be formed from the corresponding 4,5-unsaturated benzodiazepines by treatment with an epoxide compound in the presence of an acid catalyst. 'A' bearing either a nitrogen or an oxygen atom in the new heterocyclic ring may be prepared by cyclization of the corresponding open compound. 'A' are useful as sedative, muscle relaxant and anti-convulsant agents.

Preparation of triazolo benzodiazepines

Intermediates for tricyclic benzodiazepines

Novel pyrazino-1,4-diazepines are disclosed together with processes for their preparation and novel intermediates used in these processes. These novel diazepines are useful as sedatives, muscle-relaxants and anti-convulsants.

2-Aroyl-3-amino pyrazines and the 3(-2haloacetamide derivatives thereof

Novel preparations of triazolobenzodiazepines are disclosed. Novel 6-pyridyl-4H-triazolo[4,3-a]-1,4-benzodiazepines and novel intermediates are also disclosed which are useful as anti-convulsants, muscle relaxants and sedative agents.

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Upper Montclair, NJ, United States of America

Leo Henryk Sternbach