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Details for Patent: 4,440,685

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Details for Patent: 4,440,685

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 with 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 or 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:Jun 16, 1983
Application Number:06/504,999
Claims:1. A compound of the formula ##STR82## R.sub.1 is selected from the group consisting of hydrogen, lower alkyl, hydroxy lower alkyl, ##STR83## phenyl, C.sub.1 to C.sub.7 alkoxy lower alkyl, halo lower alkyl, amino lower alkyl, mono- or di- C.sub.1 to C.sub.7 alkyl or phenyl or chlorophenyl or tolyl substituted amino lower alkyl, pyridyl benzyl and the group R.sup.65 CO wherein R.sup.65 is hydrogen or lower alkyl R.sub.2 is selected from the group consisting of hydrogen, lower alkyl, hydroxy lower alkyl ##STR84## lower alkyl, C.sub.1 to C.sub.7 alkoxy lower alkyl, halo-lower alkyl, amino or mono- or di- C.sub.1 to C.sub.7 alkyl or phenyl or chlorophenyl or tolyl substituted amino lower alkyl, cyano, cyano lower alkyl, mono- or di- C.sub.1 to C.sub.7 alkyl or phenyl or chlorophenyl or tolyl substituted amino, the grooup -COOR where R is hydrogen or lower alkyl, the group ##STR85## where R is hydrogen or lower alkyl, or the group ##STR86## wherein R' is hydrogen, lower alkyl hydroxy, phenyl, C.sub.1 to C.sub.7 alkoxy, amino, mono or di-alkylamino and arylamino and R is hydrogen or lower alkyl, the group ##STR87## (where R.sup.85, R.sup.86 are hydrogen, lower alkyl, hydroxy lower alkyl, lower alkenyl, aryl or together R.sup.85 and R.sup.86 with the nitrogen atom form a part of a 5- or 6-membered heterocyclic ring selected from the group consisting of morpholino, piperazino, piperidino and pyrrolidino and the group (CH.sub.2).sub.n NR.sup.95 R.sup.96 where R.sup.95 and R.sup.96 are hydrogen, lower alkyl, hydroxy lower alkyl, lower alkenyl, aryl, or together R.sup.95 and R.sup.96 with the nitrogen atom form a part of a 5- or 6-membered heterocyclic ring selected from the group consisting of morpholino, piperazino, piperidino and pyrrolidino) or the group ##STR88## where R.sup.10, R.sup.11, R.sup.12 are hydrogen, lower alkyl or the group (CH.sub.2).sub.n NR.sup.13 R.sup.14 where n is 1 to 4 and R.sup.13, R.sup.14 are hydrogen or lower alkyl with limitation that where R.sup.10, R.sup.11 or R.sup.12 l is (CH.sub.2).sub.n R.sup.13 R.sup.14 then the remaining substituents are hydrogen or lower alkyl; R.sub.3 is selected from the group consisting of hydrogen or lower alkyl; R.sub.4 is selected from the group consisting of hydrogen, halogen, cyano, trifluoromethyl, lower alkyl, mono- or di- C.sub.1 to C.sub.7 alkyl or phenyl or chlorphenyl or tolyl substituted amino, amino, hydroxy lower alkyl and lower alkanoyl; R.sup.20 is hydrogen or C.sub.1 to C.sub.6 alkyl; R.sub.6 is selected from the group consisting of phenyl, mono-halo substituted phenyl, di-halo substituted phenyl, pyridyl and mono-halo or mono-nitro substituted pyridyl with the limitation that phenyl is not nitro substituted; and ##STR89## is selected from the group consisting of ##STR90## and the pharmaceutically acceptable salts thereof.

2. A compound of claim 1: 8-chloro-5,6-dihydro-6-(2-fluorophenyl)-1-methyl-4H-imidazo[1,5-a][1,4]ben zodiazepine.

3. A compound of claim 1: methyl-8-chloro-5,6-dihydro-1-methyl-6-phenyl-4H-imidazo[1,5-a][1,4]benzod iazepine-3-carboxylate.

4. A compound of claim 1: 8-chloro-5,6-dihydro-1-methyl-6-phenyl-4H-imidazo[1,5-a][1,4]benzodiazepin e-3-carboxylic acid hydrazide.

5. A compound of claim 1: 8-(1-hydroxyethyl)-6-phenyl-1-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]ben zodiazepine dipicrate.
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