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HomeProduct name listETHYL LOFLAZEPATE

ETHYL LOFLAZEPATE

  • CAS NO.:29177-84-2
  • Empirical Formula: C18H14ClFN2O3
  • Molecular Weight: 360.77
  • MDL number: MFCD00868159
  • EINECS: 249-489-4
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2023-05-04 17:34:37
ETHYL LOFLAZEPATE Structural

What is ETHYL LOFLAZEPATE?

Originator

Victan,Clin Midy,France,1982

The Uses of ETHYL LOFLAZEPATE

A new benzodiazepine derivative as a new anti-anxiety drug. Ethyl Loflazepate and its metabolite were compared with those of Diazepam (D416855), Nitrazepam (N490140) and Lorazepam (L469850). The anticonflict effect of Ethyl Loflazepate was slightly more potent than that of Diazepam and much more potent than that of Lorazepam. Controlled substance.

Definition

ChEBI: Ethyl loflazepate is an organic molecular entity.

Manufacturing Process

(A) 1-(2-Amino-5-chlorophenyl)-1-(2-fluorophenyl)-2-aza-buty1-en-4-ol: A mixture of 40 g of 2-methylimidazole hydrochloride and of 90 g of 2-amino-5- chloro-2'-fluoro-benzophenone in 240 ml of ethanolamine is heated at 135°C for 2 hours. After cooling, the reaction mixture is poured into an aqueous sodium bicarbonate solution. The mixture is extracted with ether, the organic phase is washed repeatedly with water and is dried over sodium sulfate, and the solvent is evaporated to dryness. The residual oil is chromatographed on a silica column, elution being carried out with a 50/50 mixture of cyclohexane and ethyl acetate.
88 g of the expected amine are thus isolated. Melting point: 105°C to 110°C.
(B)1-(2-Amino-5-chlorophenyl)-1-(2-fluorophenyl)-3,3-bis-(ethoxycarbonyl)-2- aza-prop-1-ene: A mixture of 88 g of the product obtained above, 300 g of ethyl aminomalonate hydrochloride and 60 ml of acetic acid in 2.3 liters of absolute ethanol is heated to the reflux temperature for 6 hours. The alcohol and the acetic acid are evaporated in vacuo and the residue is taken up in ether. The solution is washed with a dilute sodium bicarbonate solution and then with water and is dried over sodium sulfate. The solvent is evaporated and the residue is then chromatographed on a silica column, using a 90/10 mixture of chloroform and ethyl acetate for the elution. An oil (64g) is thus obtained, and is used, without further treatment, for the cyclization.
A sample recrystallized from isopropyl ether has a melting point of 119°C.
(C) Compound of Code No. CM 6912: 25 g of the imine obtained under (B), dissolved in 400 ml of acetic acid, are heated at the reflux temperature for 1 hour. After evaporating the solvent in vacuo, the residue is taken up in methylene chloride. The solution is washed with a dilute sodium bicarbonate solution and then with water. After evaporating the solvent, the residue is chromatographed on silica, elution being carried out with an 80/20 mixture of ether and ethyl acetate. 9 g of benzodiazepine are thus obtained. Melting point: 196°C.

Therapeutic Function

Tranquilizer

Properties of ETHYL LOFLAZEPATE

Melting point: 193-194°
Boiling point: 507.7±50.0 °C(Predicted)
Density  1.3609 (estimate)
solubility  DMF: 30 mg/ml; DMSO: 30 mg/ml; DMSO:PBS (pH 7.2) (1:1): 0.5 mg/ml; Ethanol: 10 mg/ml; Methanol: 1 mg/ml
form  A crystalline solid
pka 10.56±0.70(Predicted)

Safety information for ETHYL LOFLAZEPATE

Computed Descriptors for ETHYL LOFLAZEPATE

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