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Details for Patent: 4,376,074

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Details for Patent: 4,376,074

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:06/242,851
Claims:1. A compound of the formula ##STR85## wherein A is ##STR86## R.sub.1 is selected from the group consisting of hydrogen, lower alkyl, hydroxy lower alkyl, ##STR87## lower alkyl, 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, chlorophenyl or tolyl substituted amino lower alkyl, pyridyl, benzyl and the group ##STR88## 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, C.sub.1 to C.sub.7 acyloxy lower alkyl, C.sub.1 to C.sub.7 alkoxy lower alkyl, halo lower alkyl, cyano, cyano lower alkyl, mono- or di-C.sub.1 to C.sub.7 alkyl or phenyl, chlorophenyl or tolyl substituted amino lower alkyl, amino lower alkyl, mono- or di-C.sub.1 to C.sub.7 alkyl or phenyl, chlorophenyl or tolyl substituted amino, the group COOR where R is hydrogen or lower alkyl, the group ##STR89## where R is hydrogen or lower alkyl, or the group R-C.dbd.N-R' wherein R' is hydrogen, lower alkyl, hydroxy, phenyl, alkoxy, amino, mono or di-alkylamino and arylamino and R is hydrogen or lower alkyl, the group ##STR90## (where R.sup.85, R.sup.86 are hydrogen, lower alkyl, aryl, hydroxy lower alkyl, lower alkenyl, or together R.sup.85 and R.sup.86 with the nitrogen atom may 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), the group ##STR91## where R.sup.10, R.sup.11, R.sup.12 are hydrogen or 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 the limitation that where R.sup.10, R.sup.11 or R.sup.12 is (CH.sub.2).sub.n NR.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.5 is hydrogen; R.sub.6 is selected from the group consisting of phenyl, mono R.sub.6 is selected from the group consisting of phenyl, mono-halo or mononitro substituted phenyl, di-halo or halo-nitro substituted phenyl, pyridyl and mono-halo or mono-nitro substituted pyridyl, R.sup.20 is C.sub.1 to C.sub.6 or hydrogen; and ##STR92## wherein T is hydrogen or lower alkyl and the pharmaceutically acceptable salts thereof.

2. A compound of the formula ##STR93## wherein R.sub.1 is selected from the group consisting of hydrogen, lower alkyl, hydroxy lower alkyl, ##STR94## lower alkyl, phenyl, alkoxy lower alkyl, halo lower alkyl, amino lower alkyl, mono- or di-C.sub.1 to C.sub.7 alkyl or phenyl or tolyl substituted amino lower alkyl, mono halo substituted phenyl, pyridyl, tolyl-lower alkyl and the groups ##STR95## wherein R.sup.65 is hydrogen or lower alkyl or COOR.sup.66 wherein R.sup.66 is lower alkyl; R is selected from the group consisting of hydrogen and lower alkyl; 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 and R.sup.20 is C.sub.1 to C.sub.6 or hydrogen.

3. A compound as in claim 2 where R.sub.1 is methyl.
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