Basic information Safety Supplier Related

Zatebradine

Basic information Safety Supplier Related

Zatebradine Basic information

Product Name:
Zatebradine
Synonyms:
  • Zatebradine
  • UL-FS-49 free base
  • UL-FS-49CL free base
  • 2H-3-Benzazepin-2-one, 3-[3-[[2-(3,4-dimethoxyphenyl)ethyl]methylamino]propyl]-1,3,4,5-tetrahydro-7,8-dimethoxy-
  • 3-(3-((3,4-Dimethoxyphenethyl)(methyl)amino)propyl)-7,8-dimethoxy-4,5-dihydro-1H-benzo[d]azepin-2(3H)-one
  • Zatebradine (UL-FS-49
CAS:
85175-67-3
MF:
C26H36N2O5
MW:
456.58
Mol File:
85175-67-3.mol
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Zatebradine Chemical Properties

Boiling point:
612.5±55.0 °C(Predicted)
Density 
1.115±0.06 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
DMSO : ≥ 50 mg/mL (109.51 mM)
pka
8.99±0.50(Predicted)
form 
Oil
color 
Light brown to brown
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Zatebradine Usage And Synthesis

Originator

ZATEBRADINE HYDROCHLORIDE,Boenhringer Ingelheim

Definition

ChEBI: 3-[3-[2-(3,4-dimethoxyphenyl)ethyl-methylamino]propyl]-7,8-dimethoxy-2,5-dihydro-1H-3-benzazepin-4-one is a benzazepine.

Manufacturing Process

A suspension of 1-[7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-on-3-yl]-3- (N-benzylmethylamino)propane and 10% palladium-on-charcoal in glacial acetic acid was hydrogenated at 50°C and at a hydrogen pressure of 5 bar. After the catalyst had been filtered off, the solvent was evaporated in vacuum, and the residue was taken up in methylene chloride. After the solution had been extracted with an aqueous sodium bicarbonate solution and washed with water, it was dried over magnesium sulfate, evaporated and purified over silica gel with methylene chloride and then with increasing amounts of methanol (up to 10%). The N-[3-(7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3- benzazepin-2-one-3-yl)propyl]methylamine hydrochloride. Yield: 87% of theory. Melting point: 110°C (dec.).
1.26 g (20 mmols) of sodium cyanoborohydride were added to a solution of 3.29 g (10 mmols) of N-[3-(7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3- benzazepin-2-one-3-yl)propyl]methylamine hydrochloride and 1.8 g (10 mmol) of 2-(3,4-dimethoxyphenyl)acetaldehyde in 40 ml of ethanol, while maintaining a pH of 6-7 by the addition of 2 N hydrochloric acid, and stirring was continued for 48 h at room temperature. After evaporating the solution in vacuum, the residue was taken up in dilute hydrochloric acid and extracted twice with ether. Subsequently, the aqueous phase was made alkaline and extracted three times with methylene chloride, and the organic phase was evaporated and purified on silica gel. The 1-[7,8-dimethoxy-1,3,4,5- tetrahydro-2H-3-benzazepin-2-on-3-yl]-3-[N-methyl-N-(2-{3,4- dimethoxyphenyl}ethyl)amino]propane was obtained.

Therapeutic Function

Bradycardic

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