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]benzodiazepine.
- 3. A compound of claim 1: methyl-8-chloro-5,6-dihydro-1-methyl-6-phenyl-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate.
- 4. A compound of claim 1: 8-chloro-5,6-dihydro-1-methyl-6-phenyl-4H-imidazo[1,5-a][1,4]benzodiazepine-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]benzodiazepine dipicrate.
Parent Case Info
This is a continuation, of application Ser. No. 243,091 filed Mar. 12, 1981, now abandoned, which is a divisional of Ser. No. 905,820, filed May 15, 1978 now U.S. Pat. No. 4,280,957, which is a continuation of Ser. No. 663,660 filed Mar. 4, 1976 now abandoned, which is a continuation-in-part of Ser. No. 602,691, filed Aug. 7, 1975 now abandoned, which is a continuation in part U.S. patent application Ser. No. 504,924, filed Sept. 11, 1974 and now abandoned.
Non-Patent Literature Citations (1)
Entry |
Coffen et al, J. Organic Chem. 39, 167-172 (1974). |
Divisions (1)
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Number |
Date |
Country |
Parent |
905820 |
May 1978 |
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Continuations (2)
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Number |
Date |
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Parent |
243091 |
Mar 1981 |
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Parent |
663660 |
Mar 1976 |
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Continuation in Parts (2)
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Number |
Date |
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Parent |
602691 |
Aug 1975 |
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Parent |
504924 |
Sep 1974 |
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