Patent GB-972968-A (GB)
Title: Benzodiazepine derivatives
IPC: C07C237/00
Filed: 1960-12-09
Abstract: The invention comprises compounds of the general formulae <FORM:0972968/C1/1> and <FORM:0972968/C1/2> (wherein R represents an alkyl, alkenyl, hydroxy, alkyl or aralkyl group, R1 represents an alkyl, alkoxyalkyl, aryl, hydroxyaralkyl, alkylthioalkyl or hydroxyalkyl group, R2 represents an alkyl, alkoxy or trifluoromethyl group or a halogen atom, R3 represents a trifluoromethyl, alkyl, alkoxy, alkylthio, hydroxyalkylthio, nitro, amino, alkylsulphinyl, alkylsulphonyl, hydroxy or acylamino group or a halogen atom and R4, which can only be present if R3 is other than a trifluoromethyl group, represents any of the values of R3 except the latter value and wherein the broken lines denote that the R- substituents and hydroxyl group attached thereby are optional and the double headed arrow signifies that, in the absence of the hydroxy substituent on the nitrogen atom in the 4-position, the optional bond indicated thereby may exist as an additional bond in the 4, 5-position) and acid addition salts of those compounds which are basic. They are prepared by the processes of Specifications 972,961, 972,962, 972,963, 972,964, 972,965, 972,966 and 972,967.  The following intermediates are prepared from the starting materials indicated in parentheses: 2-amino-3, 5-dimethylbenzophenone (2- benzamido-3, 5-dimethylbenzophenone); 2-amino-3, 5-dichlorobenzophenone (2-acetamido -5- chlorobenzophenone, via 2-acetamido-3, 5-dichlorobenzophenone); 2-(a -bromopropionamido)-5-chlorobenzophenone (2-amino -5- chlorobenzophenone); 2-amino -4- trifluoromethylbenzophenone (2-nitro -4- trifluoromethylbenzonitrile, via 4-trifluoromethylanthranilamide, 4-trifluoromethylanthranilic acid and 2-methyl -7- trifluoromethyl-4H-3, 1-benzoxazinone-(4)); 2-amino -5-chloro -3- methylmercaptobenzophenone (2-amino -5- chlorobenzophenone or 2-aminobenzophenone hydrochloride, via 4-benzoyl -6- chloro2, 3, 1-benzothiazathiolium chloride); 6-methylmercapto -2- chloromethyl -4- phenylquinazoline 3-oxide (2-amino-5-methylmercaptobenzophenone, via 2-amino -5- methylmercaptobenzophenone oxime); 2-amino -41- chlorobenzophenone (2-(N,N-dimethylformamidino)-benzoic acid hydrochloride); 2-bromoacetamido -4- nitrobenzophenone (2-amino -4- nitrobenzophenone); 2-amino-6-chlorobenzophenone (2-acetamido -6-chlorobenzoic acid, via 5-chloro-2-methyl-4H-3,1-benzoxazinone-(4) and 2-acetamido -6- chlorobenzophenone); 7-chloro -5- (21-chlorophenyl)-2-methylamino -3H-1, 4-benzodiazepine 4-oxide and its hydrochloride (2-amino-21, 5-dichlorobenzophenone, via 2-amino-21, 5-dichlorobenzophenone oxime and 6-chloro-2-chloromethyl-4-(21-chlorophenyl) -quinazoline 3-oxide); 2-amino -5- chloro -21- methylbenzophenone (o-toluoyl chloride and p-chloroaniline); 2-amino-5-chloro -31-fluorobenzophenone (m-fluorobenzoyl chloride and p-chloroaniline); 2-amino -5- bromo- -21-fluorobenzophenone (o-fluorobenzoyl chloride and p-bromoaniline); 2-bromoacetamido -3- nitrobenzophenone (2-amino -3- nitrobenzophenone); 2-chloromethyl -4- phenyl -6- nitroquinazoline 3-oxide (2-amino -5- nitrobenzophenone, via 2-amino -5- nitrobenzophenone oxime); 2-amino -5- hydroxybenzophenone (2-methyl -5- methoxy -4H-3, 1- benzoxazinone-(4), via 2-amino -5- methoxybenzophenone); 2-bromoacetamido -5- chloro -21- methoxybenzophenone (6-chloro-2-methyl -4H-3, 1-benzoxazinone-(4), via 2-acetamido -5- chloro -21- methoxybenzophenone and 2-amino -5- chloro -21- methoxybenzophenone); 2-bromoacetamido -5- chloro -31- methoxybenzophenone (6-chloro -2- methyl -4H-3, 1-benzoxazinone-(4), via 2-acetamido -5- chloro -31- methoxybenzophenone); 2-bromoacetamido -5- chloro -41- methoxybenzophenone (2-acetamido-5-chloro -41- methoxybenzophenone, via 2-amino -5- chloro -41- methoxybenzophenone); 2-amino -4- chlorobenzophenone (4-chloroanthranilic acid, via 2-methyl -7- chloro-4H-3, 1-benzoxazinone-(4)); 2-amino -41- trifluoromethylbenzophenone (2-methyl -4H-3, 1-benzoxazinone-(4) and p-trifluoromethylphenyl magnesium bromide); 2-amino -31- trifluoromethylbenzophenone (2-methyl -4H- 3, 1-benzoxazinone-(4) and m-trifluoromethylphenyl magnesium bromide); and 2-(2-bromo-N-allylacetamido) -5- chlorobenzophenone (2-allylamino -5- chlorobenzophenone).  The compounds of the invention are sedatives, muscle relaxants and anticonvulsants, and may also be used for the relief of tension. They may be administered in the form of pharmaceutical preparations (e.g. elixirs, suspensions, capsules, tablets and powders) containing the active ingredient and a liquid or solid vehicle.  Specifications 864,824, 864,825, 932,495, 932,496, 972,969, 972,971, 972,972, 972,973 and 972,975 also are referred to.