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Generated: June 20, 2018

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Details for Patent: 4,377,523

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Title: Imidazodiazepines and processes therefor
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
Application Number:06/243,092
Claims:1. A process for producing a compound of the formula ##STR74## R.sub.1 is selected from the group consisting of hydrogen, lower alkyl, phenyl, pyridyl, tolyl, and alkoxy lower alkyl; R.sub.2 is hydrogen; R.sub.3 is selected from the group consisting of hydrogen and lower alkyl; R.sub.4 is selected from the group consisting of hydrogen, halogen, trifluoromethyl, lower alkyl, and lower alkanoyl; R.sub.6 is selected from the group consisting of phenyl, mono-halo or mono-nitro substituted phenyl, di-halo or halo-nitro substituted phenyl, pyridyl and mono-halo or mono-nitro substituted pyridyl which comprises the following steps in combination

(a) reacting a compound selected from the group consisting of ##STR75## and R.sub.3, R.sub.4 and R.sub.6 are as above with nitromethane in the presence of a strong base;

(b) catalytically hydrogenating with Raney nickel in the presence of hydrogen the product from (a);

(c) acylating the product from (b) with an acid halide or an acid anhydride of the formulas R.sub.1 COX or (R.sub.1 CO).sub.2 O respectively wherein R.sub.1 is as above;

(d) cyclizing the product from (c) with a dehydrating agent selected from the group consisting of phosphorous pentoxide, polyphosphoric acid or an acid catalyst;

(e) dehydrogenating the cyclized product of (d) with a compound selected from the group consisting of manganese dioxide, potassium permanganate or palladium on carbon.

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Serving hundreds of leading biopharmaceutical companies globally:

US Army
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