Diazepine derivatives
AssigneeHoffmann-La Roche Inc.
InventorsWalter Hunkeler, Emilio Kyburz
Life of this patent
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Abstract
There is provided compounds which exhibit pronounced anticonvulsive and anxiolytic activities of the formula ##STR1## wherein A together with the two carbon atoms denoted as .alpha. and .beta. is the group ##STR2## B is dimethylene, trimethylene or propenylene, R.sup.1 is hydrogen, halogen, trifluoromethyl, amino, nitro, cyano or lower alkyl and R.sup.2 is hydrogen, halogen, trifluoromethyl, amino, nitro, cyano, lower alkyl, lower alkoxy, lower alkylthio, lower alkylsulphinyl or lower alkylsulphonyl, and the carbon atom denoted as .gamma. has the (S)--or (R,S)--configuration, and the pharmaceutically acceptable acid addition salts thereof.
Claims21
A compound of the formula ##STR23## wherein A together with the two carbon atoms denoted as .alpha. and .beta. is the group ##STR24## B is dimethylene, trimethylene or propenylene, R.sup.1 is hydrogen, halogen, trifluoromethyl, amino, nitro, cyano or lower alkyl and R.sup.2 is hydrogen, halogen, trifluoromethyl, amino, nitro, cyano, lower alkyl, lower alkoxy, lower alkylthio, lower alkylsulphinyl or lower alkylsulphonyl, and the carbon atom denoted as .gamma. has the (S)-- or (R,S)--configuration,
- and pharmaceutically acceptable acid addition salts thereof.
The compound:
- t-Butyl(S)-12,12a-dihydro-9-oxo-8-trifluoromethyl-9H,11H-azeto [2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxylate.
The compound:
- t-Butyl (S)-12,12a-dihydro-8-methyl-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]be nzodiazepine-1-carboxylate.
The compound:
- t-Butyl (S)-8-chloro-7-fluoro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrro lo[2,1-c][1,4]benzodiazepine-1-carboxylate.
The compound:
- t-Butyl (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c] [1,4]benzodiazepine-1-carboxylate.
The compound:
- t-Butyl (S)-8-ethyl-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo [1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate.
The compound:
- t-Butyl (S)-11,12,13,13a-tetrahydro-9-oxo-8-trifluoromethyl-9H-imidazo[1,5-a]pyrro lo[2,1-c][1,4]-benzodiazepine-1-carboxylate.
The compound:
- t-Butyl (S)-8-bromo-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][ 1,4]benzodiazepine-1-carboxylate.
The compound:
- t-Butyl (S)-11,12,13,13a-tetrahydro-8-iodo-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1 ,4]benzodiazepine-1-carboxylate.
The compound:
- t-Butyl (S)-8-chloro-12,12a-dihydro-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]be nzodiazepine-1-carboxylate.
The compound:
- t-Butyl (S)-11,12,13,13a-tetrahydro-8-methyl-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c] [1,4]benzodiazepine-1-carboxylate.
A compound selected from the group consisting of t-Butyl 8-chloro-11,13a-dihydro-9-oxo-9H-imidazo-[1,5a]pyrrolo[2,1-c][1,4]benzodia zepine-1-carboxylate, t-butyl (S)-10,11,12,12a-tetrahydro-8-oxo-8H-imidazo-[5,1-c]pyrrolo[1,2-a]thieno[3 ,2-e][1,4]diazepine-1-carboxylate,
- t-butyl (S)-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benz odiazepine-1-carboxylate,
- t-butyl (S)-7-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c] [1,4]benzodiazepine-1-carboxylate,
- t-butyl (S)-8-amino-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][ 1,4]benzodiazepine-1-carboxylate,
- t-butyl (S)-11,12,13,13a-tetrahydro-8-nitro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][ 1,4]benzodiazepine-1-carboxylate,
- t-butyl (S)-8-cyano-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][ 1,4]benzodiazepine-1-carboxylate,
- t-butyl (S)-11,12,13,13a-tetrahydro-8-methylthio-9-oxo-9H-imidazo[1,5-a]pyrrolo[2, 1-c][1,4]benzodiazepine-1-carboxylate,
- t-butyl (S)-11,12,13,13a-tetrahydro-8-methylsulphonyl-9-oxo-9H-imidazo[1,5-a]pyrro lo[2,1-c][1,4]benzodiazepine-1-carboxylate,
- t-butyl (S)-7-fluoro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c] [1,4]benzodiazepine-1-carboxylate and
- t-butyl (S)-8-chloro-13,13a-dihydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benz odiazepine-1-carboxylate.
Dependencies are inferred from the claim text.