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84379-13-5 9H-Imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylicacid, 8-bromo-11,12,13,13a-tetrahydro-9-oxo-, 1,1-dimethylethyl ester, (13aS)-
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84379-13-5 Usage

Biological Activity

Partial agonist at the GABA A benzodiazepine site (EC 50 = 10 nM at α 1 β 1 γ 2 receptors). Displays anticonvulsive activity in vivo .

Originator

Bretazenil,Hoffman-La Roche, Inc.

Therapeutic Function

Anxiolytic

Uses

Anti-anxiety agent.Bretazenil potentiated GABA responses on α4β3γ2 cells. Bretazenil is a partial benzodiazepine receptor agonist.

Manufacturing Process

50.6 mmol of 6-bromoisatoic acid anhydride are stirred at 110°C for 2 hours with 50.6 mmol of L-proline in 80 ml of dimethyl sulphoxide. The solution is evaporated and the residue is crystallized from ethyl acetate. There is obtained (S)-6-bromo-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1- c][1,4]benzodiazepine-5,11(10H)-dione. A suspension of 29.8 mmol of sodium hydride (55 percent oil dispersion) in 40 ml of dry dimethylformamide is treated at 20-30°C with 27.1 mmol of (S)-6- bromo-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)- dione, the mixture is stirred in the above temperature range for 45 min and then at -35°C 27.1 mmol of diethylchlorophosphate are added dropwise thereto. Separately, 3.0 g (27.1 mmol) of potassium t-butylate are dissolved in 9.0 ml of dry dimethylformamide, cooled in an acetone/dry-ice bath, treated with 3.9 g (27.1 mmol) of t-butyl isocyanoacetate and the solution obtained is added dropwise at -15°C to the mixture obtained according to the preceding paragraph. The mixture is warmed to 15°C, neutralized with 1.5 ml of glacial acetic acid, poured into 100 ml of water and extracted four times with methylene chloride. The methylene chloride solution is washed twice with water, dried over magnesium sulfate, evaporated and the crude product obtained is chromatographed on silica gel using ethyl acetate for the elution. By recrystallization from ethyl acetate/n-hexane there is obtained 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.
InChI:InChI=1/C19H20BrN3O3/c1-19(2,3)26-18(25)15-16-13-8-5-9-22(13)17(24)14-11(20)6-4-7-12(14)23(16)10-21-15/h4,6-7,10,13H,5,8-9H2,1-3H3/t13-/m0/s1

84379-13-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name Bretazenil

1.2 Other means of identification

Product number -
Other names Ro-16-6028

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

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