Aryl- and heteroaryl-substituted tetrahydrobenzo-1,4-diazepines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin
First Claim
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1. A compound of formulae I(A-D) having the following structure:
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Abstract
The aryl- and heteroaryl-substituted tetrahydrobenzo-1,4-diazepine derivative compounds of the present invention are represented by formulae 1(A-D) having the following structure: where the substituents X and R1-R8 are as defined herein.
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Citations
21 Claims
- 1. A compound of formulae I(A-D) having the following structure:
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19. A compound selected from the group consisting of:
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1-(1-fluoronaphthalen-2-yl)-4-methyl-7-(pyridazin-3-yl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine; 4-methyl-1-(4-(methylsulfonyl)phenyl)-7-(pyridazin-3-yl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine; 1-(3,5-difluorophenyl)-4-methyl-7-(pyridazin-3-yl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine; 1-(2,4-difluorophenyl)-4-methyl-7-(pyridazin-3-yl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine; 4-methyl-7-(pyridazin-3-yl)-1-(3-(trifluoromethyl)phenyl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine; 1-(5-fluoronaphthalen-2-yl)-4-methyl-7-(pyridazin-3-yl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine; 1-(4-fluoronaphthalen-2-yl)-4-methyl-7-(pyridazin-3-yl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine; 3-(4-methyl-7-(pyridazin-3-yl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-1-yl)benzonitrile; 1-(benzo[d][1,3]dioxol-5-yl)-4-methyl-7-(pyridazin-3-yl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine; 4-methyl-1-(naphthalen-1-yl)-7-(pyridazin-3-yl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine; 4-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine; 1-(3,4-difluorophenyl)-4-methyl-7-(pyridazin-3-yl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine; 1-(3-fluorophenyl)-4-methyl-7-(pyridazin-3-yl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine; 4-methyl-1-(naphthalen-2-yl)-7-(pyridazin-3-yl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine; 1-(3,4-dichlorophenyl)-4-methyl-7-(pyridazin-3-yl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine; 1-(2-fluorophenyl)-4-methyl-7-(pyridazin-3-yl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine; 1-(3-chlorophenyl)-4-methyl-7-(pyridazin-3-yl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine; 4-methyl-1-phenyl-7-(pyridazin-3-yl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine; 1-(1-(4-chlorophenyl)-4-methyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-7-yl)pyridin-2(1H)-one; 1-(4-chlorophenyl)-4-methyl-7-(pyridazin-3-yl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine; 1-(4-fluorophenyl)-4-methyl-7-(pyridazin-3-yl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine; 4-methyl-7-(6-methylpyridazin-3-yl)-1-phenyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine; 1-(4-fluorophenyl)-4-methyl-7-(6-(trifluoromethyl)pyridazin-3-yl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine; 1-(4-methyl-1-(naphthalen-2-yl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-7-yl)pyridin-2(1H)one; 7-(4-(ethylsulfonyl)piperazin-1-yl)-4-methyl-1-(naphthalen-2-yl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine; 4-methyl-1-(naphthalen-2-yl)-7-(pyridin-3-yl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine; 4-methyl-1-(naphthalen-2-yl)-N-(pyrimidin-2-yl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-7-amine; 4-methyl-1-(naphthalen-2-yl)-7-(pyrazin-2-yl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine; 4-methyl-7-(4-(methanesulfonyl)phenyl)-1-(naphthalen-2-yl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine; 4-methyl-1-(naphthalen-2-yl)-7-(1H-pyrazol-1-yl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine; 4-methyl-7-(6-methylpyridazin-3-yl)-1-(naphthalen-2-yl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine; 7-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-4-methyl-1-(naphthalen-2-yl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine; 7-([1,2,4]triazolo[4,3-a]pyridin-6-yl)-4-methyl-1-(naphthalen-2-yl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine; 4-methyl-1-(naphthalen-2-yl)-7-(pyrimidin-5-yl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine; 4-methyl-1-(naphthalen-2-yl)-7-(pyrimidin-2-yl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine; 1-(4-chlorophenyl)-4-methyl-7-(pyrazin-2-yl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine; 1-(4-chlorophenyl)-4-methyl-7-(4-(methylsulfonyl)phenyl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine; 1-(4-chlorophenyl)-4-methyl-7-(pyrimidin-5-yl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine; 1-(4-chlorophenyl)-4-methyl-7-(pyrimidin-2-yl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine; 4-(1-(4-chlorophenyl)-4-methyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-7-yl)benzamide; 7-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-1-(4-chlorophenyl)-4-methyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine; 7-([1,2,4]triazolo[4,3-a]pyridin-6-yl)-1-(4-chlorophenyl)-4-methyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine; and 6-(1-(4-chlorophenyl)-4-methyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-7-yl)pyridazin-3-amine. - View Dependent Claims (20)
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Specification