|Title:||Process for producing imidazodiazepines|
|Abstract:||Novel Imidazobenzodiazepines and their analogs are useful as anticonvulsants, muscle relaxant, anxiolytic and sedative agents. Preferred compounds of this class belong to the imidazo[1,5-a][1,4]diazepine series which may have a very wide variety of organic substituents. An especially preferred genus included within the purview of the invention encompasses a compound of the formula ##STR1## wherein R.sub.1 is hydrogen and lower alkyl preferably methyl; R.sub.3 and R.sub.5 are hydrogen; R.sub.4 is hydrogen, nitro and halogen, most preferably, chlorine, and in a most preferred embodiment when positioned on the fused benzo portion of the imidazobenzodiazepine is in the 8-position thereof, R.sub.6 is phenyl or halo, nitro, or lower alkyl-substituted phenyl, preferably, halo, with fluorine being the preferred halogen, the substituted fluoro being positioned in the 2-position of the phenyl moiety and R.sub.2 is hydrogen and lower alkyl.|
|Inventor(s):||Walser; Armin (West Caldwell, NJ), Fryer; Rodney I. (North Caldwell, NJ)|
|Assignee:||Hoffmann-La Roche Inc. (Nutley, NJ)|
|Filing Date:||Mar 12, 1981|
|Claims:||1. A process to produce a compound of the formula ##STR83## wherein A is ##STR84## R.sub.3 is selected from the group consisting of hydrogen and lower alkyl; R is lower alkyl; R.sub.1 is selected from the group consisting of hydrogen, lower alkyl C.sub.1 to C.sub.7 acyloxy lower alkyl, phenyl, C.sub.1 to C.sub.7 alkoxy lower alkyl, halo lower alkyl, mono- or di-C.sub.1 to C.sub.7 alkyl or phenyl, chlorophenyl or tolyl substituted amino lower alkyl, pyridyl, tolyl, hydroxy lower alkyl and the group ROOC wherein R is lower alkyl; R.sub.4 is selected from the group consisting of hydrogen, halogen, nitro, cyano, trifluoromethyl, lower alkyl, mono-or di-C.sub.1 to C.sub.7 alkyl or phenyl, chlorophenyl or tolyl substituted amino, amino, hydroxy lower alkyl and lower alkanoyl; R.sub.6 is selected from the group consisting of phenyl, mono-halo or mono-nitro substituted phenyl, dihalo or halo-nitro substituted phenyl, pyridyl and mono-halo or mono-nitro substituted pyridyl; and ##STR85## is selected from the group consisting of ##STR86## which comprises the stepwise reaction of a compound of the formula ##STR87## wherein R.sub.3 is hydrogen or lower alkyl; R is lower alkyl; A is ##STR88## R.sub.4, R.sub.6 and ##STR89## are as above (a) with an aldehyde of the formula |
wherein R.sub.1 is as above;
(b) oxidizing the product of (a) to form the final product.
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