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Allisartan Isoproxil

Allisartan Isoproxil Basic information
Product Name:Allisartan Isoproxil
Synonyms:Allisartan Isoproxil;1H-Imidazole-5-carboxylic acid, 2-butyl-4-chloro-1-[[2'-(2H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-, [[(1-methylethoxy)carbonyl]oxy]methyl ester;Losartan Impurity 19（Allisartan Isoproxil）;Allisartan;Losartan Impurity N9
CAS:947331-05-7
MF:C27H29ClN6O5
MW:553.01
EINECS:
Product Categories:
Mol File:947331-05-7.mol
Allisartan Isoproxil Structure
Allisartan Isoproxil Chemical Properties
Boiling point 745.0±70.0 °C(Predicted)
density 1.35±0.1 g/cm3(Predicted)
pka4.16±0.10(Predicted)
form Solid
color White to off-white
Safety Information
MSDS Information
Allisartan Isoproxil Usage And Synthesis
Clinical UseAllisartan isoproxil, a member of a new class of selective angiotensin II-1 receptor antagonists, was approved by the Chinese Food and Drug Administration (CFDA) for the treatment of hypertension in July 2012.19 At time of publication, there is no trade name associated with this drug. Allisartan was discovered and developed by the Chinese biomedical company Allist Pharmaceuticals. Allisartan isoproxil is a prodrug which is readily hydrolyzed to active metabolite EXP3174, which is also the active metabolite of losartan (des-triphenylmethyl-9).
SynthesisAlthough several synthetic routes have been reported within two patents, the most likely scalable process route is described in the scheme. Commercial 2-butyl-4-chloro-5-(hydroxymethyl)-imidazole (7) was alkylated with Ntriphenylmethyl- 5-(4'-bromomethylbiphenyl-2-yl)tetrazole (8) under basic conditions in warm DMF, providing alcohol 9 in 90% yield. This alcohol was then oxidized to the corresponding carboxylic acid 10 with KMnO4 in 88% yield. Etherification of acid 10 with isopropyl chloromethyl carbonate (11) followed by de-tritylation of the tetrazole group under acidic contidions gave allisartan isoproxil (II) in 69% yield.

Synthesis_947331-05-7
Tag:Allisartan Isoproxil(947331-05-7) Related Product Information
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