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US 11,021,448 B2Granted
1,3-dihydro-1,4-benzodiazepine-2-thiones for the treatment of CNS related diseases
AssigneeHoffmann-La Roche Inc.
InventorAlexander Flohr
Life of this patent
Estimating the term…
Abstract
The present invention provides compounds that are muscarinic M1 receptor positive allosteric modulators (PAM) and useful in the treatment of diseases, mediated by the muscarinic M1 receptor, such as Alzheimer's disease, cognitive impairment, schizophrenia, pain or sleep disorders, their manufacture, pharmaceutical compositions containing them and their use as therapeutically active substances.
Claims4
A compound of formula I, selected from the group consisting of:
- (3R)-3-benzyl-7-chloro-5-phenyl-1,3-dihydro-1,4-benzodiazepine-2-thione,
- (3R)-7-chloro-3-(2-methylsulfanylethyl)-5-phenyl-1,3-dihydro-1,4-benzodiazepine-2-thione,
- (3R)-7-chloro-3-isopropyl-5-phenyl-1,3-dihydro-1,4-benzodiazepine-2-thione,
- (3R)-7-chloro-5-(2-fluorophenyl)-3-(trifluoromethyl)-1,3-dihydro-1,4-benzodiazepine-2-thione,
- (3R)-7-chloro-5-(2-fluorophenyl)-3-isopropyl-1,3-dihydro-1,4-benzodiazepine-2-thione,
- (3S)-3-benzyl-7-chloro-5-phenyl-1,3-dihydro-1,4-benzodiazepine-2-thione,
- (3S)-3-isopropyl-5,7-diphenyl-1,3-dihydro-1,4-benzodiazepine-2-thione,
- (3S)-3-isopropyl-5-phenyl-7-(trifluoromethoxy)-1,3-dihydro-1,4-benzodiazepine-2-thione,
- (3S)-3-isopropyl-5-phenyl-7-(trifluoromethyl)-1,3-dihydro-1,4-benzodiazepine-2-thione,
- (3S)-3-isopropyl-7-methoxy-5-phenyl-1,3-dihydro-1,4-benzodiazepine-2-thione,
- (3S)-5-(2-fluorophenyl)-3-isopropyl-7-methyl-1,3-dihydro-1,4-benzodiazepine-2-thione,
- (3S)-7-bromo-3-isopropyl-5-(2-pyridyl)-1,3-dihydro-1,4-benzodiazepine-2-thione,
- (3S)-7-bromo-3-isopropyl-5-(3-pyridyl)-1,3-dihydro-1,4-benzodiazepine-2-thione,
- (3S)-7-chloro-3-(2-methylsulfanylethyl)-5-phenyl-1,3-dihydro-1,4-benzodiazepine-2-thione,
- (3S)-7-chloro-3-(cyclopropylmethyl)-5-phenyl-1,3-dihydro-1,4-benzodiazepine-2-thione,
- (3S)-7-chloro-3-cyclopropyl-5-phenyl-1,3-dihydro-1,4-benzodiazepine-2-thione,
- (3S)-7-chloro-3-ethyl-5-phenyl-1,3-dihydro-1,4-benzodiazepine-2-thione,
- (3S)-7-chloro-3-isobutyl-5-phenyl-1,3-dihydro-1,4-benzodiazepine-2-thione,
- (3S)-7-chloro-3-isopropyl-5-phenyl-1,3-dihydro-1,4-benzodiazepine-2-thione,
- (3S)-7-chloro-3-methyl-5-phenyl-3-propyl-1H-1,4-benzodiazepine-2-thione,
- (3S)-7-chloro-5-(2-fluorophenyl)-3-(trifluoromethyl)-1,3-dihydro-1,4-benzodiazepine-2-thione,
- (3S)-7-chloro-5-(2-fluorophenyl)-3-isobutyl-1,3-dihydro-1,4-benzodiazepine-2-thione,
- (3S)-7-chloro-5-(2-fluorophenyl)-3-isopropyl-1,3-dihydro-1,4-benzodiazepine-2-thione,
- (3S)-7-chloro-5-(2-fluorophenyl)-3-phenyl-1,3-dihydro-1,4-benzodiazepine-2-thione,
- (3S)-7-chloro-5-(3-chlorophenyl)-3-isopropyl-1,3-dihydro-1,4-benzodiazepine-2-thione,
- (3S)-7-chloro-5-cyclohexyl-3-isopropyl-1,3-dihydro-1,4-benzodiazepine-2-thione,
- (3S)-7-chloro-5-phenyl-3-(2,2,2-trifluoroethyl)-1,3-dihydro-1,4-benzodiazepine-2-thione,
- (3S)-7-chloro-5-phenyl-3-propyl-1,3-dihydro-1,4-benzodiazepine-2-thione,
- (3S)-8-chloro-5-(2-fluorophenyl)-3-isopropyl-1,3-dihydro-1,4-benzodiazepine-2-thione,
- [7-chloro-5-(2-fluorophenyl)-2-thioxo-1,3-dihydro-1-benzazepin-3-yl] acetate,
- (3S)-5-(4-fluorophenyl)-3-isopropyl-7-(trifluoromethoxy)-1,3-dihydro-1,4-benzodiazepine-2-thione,
- 3-[(3,4-dichlorophenyl)methyl]-5-phenyl-1,3-dihydro-1,4-benzodiazepine-2-thione,
- 3-methyl-5-phenyl-1,3-dihydro-1,4-benzodiazepine-2-thione,
- 3-methyl-7-nitro-5-phenyl-1,3-dihydro-1,4-benzodiazepine-2-thione,
- 7-amino-3-ethyl-5-(2-fluorophenyl)-1,3-dihydro-1,4-benzodiazepine-2-thione,
- 7-chloro-3-(1-hydroxy-1-methyl-ethyl)-5-phenyl-1,3-dihydro-1,4-benzodiazepine-2-thione,
- 7-chloro-3-(1-methoxyethyl)-5-phenyl-1,3-dihydro-1,4-benzodiazepine-2-thione,
- 7-chloro-3,5-diphenyl-1,3-dihydro-1,4-benzodiazepine-2-thione, and
- 7-chloro-3-isopropyl-5-phenyl-1,3-dihydro-1,4-benzodiazepine-2-thione,
- or a pharmaceutically acceptable salt thereof.
37 more elements
A compound selected from the group consisting of 5-cyclohexyl-7-(trifluoromethyl)-1,3-dihydro-1,4-benzodiazepine-2-thione, 7-chloro-5-propyl-1,3-dihydro-1,4-benzodiazepine-2-thione, or a pharmaceutically acceptable salt thereof.
Dependencies are inferred from the claim text.