Process of making benzodiazepine derivatives

A process of making benzodiazepine derivatives of the formula ##STR23## wherein R represents halogen, hydroxy, lower alkoxy, or an amino group corresponding to the formula ##STR24## wherein R.sup.6 and R.sup.7 together form a piperidino group;

• R.sup.1 represents hydrogen or lower alkyl;
• R.sup.3 represents phenyl or phenyl substituted at least once with a group selected from halogen, nitro, trifluoromethyl, lower alkyl, and lower alkoxy;
• R.sup.4 represents hydrogen, halogen, nitro, trifluoromethyl, lower alkyl or lower alkoxy;
• and
• R.sup.5 represents hydrogen,
• or a pharmaceutically acceptable acid addition salt thereof, said process comprising subjecting a benzodiazocine corresponding to the formula ##STR25## or an acid addition salt thereof wherein R.sup.1, R.sup.3, R.sup.4 and R.sup.5 have the same meanings as above and R.sup.2 represents (i) halogen, or (ii) hydroxy, in the case of (i) to thermal treatment in an inert solvent or in the case of (i) to thermal treatment in an inert solvent in the presence of a nucleophilic agent which produces a hydroxy, lower alkoxy, or an amino residue ##STR26## wherein R.sup.6 and R.sup.7 have the same meaning as above, or in the case of (ii) to thermal treatment with thionyl chloride in an inert solvent,
• whereby the benzodiazocine compound undergoes rearrangement and ring contraction.

A process of making benzodiazepine derivatives of the formula ##STR27## wherein R represents halogen, hydroxy, lower alkoxy or an amino group corresponding to the formula ##STR28## wherein R.sup.6 and R.sup.7 together form a piperidino group;

• R.sup.1 represents lower alkyl;
• R.sup.3 represents phenyl or phenyl substituted at least once with halogen;
• R.sup.4 represents hydrogen or halogen;
• and
• R.sup.5 represents hydrogen, or a pharmaceutically acceptable acid addition salt thereof, said process comprising subjecting a benzodiazocine compound corresponding to the formula ##STR29## or an acid addition salt thereof wherein R.sup.1, R.sup.3, R.sup.4 and R.sup.5 have the same meanings as above and R.sup.2 represents (i) halogen or (ii) hydroxy, in the case of (i) to thermal treatment in an inert solvent, or in the case of (i) to thermal treatment in an inert solvent in the presence of a nucleophilic agent which produces a hydroxy, lower alkoxy or amino residue ##STR30## wherein R.sup.6 and R.sup.7 have the same meaning as above, or in the case of (ii) to thermal treatment with a halogenating Lewis acid in a solvent,
• whereby the benzodiazocine compound undergoes rearrangement and ring contraction.