1260141-27-2 Usage
Description
TAK-438, also known as Vonoprazan Fumarate, is a selective, reversible, and potassium-competitive proton pump inhibitor developed by Takeda and Otsuka. It has a unique mechanism of action that competitively inhibits the binding of potassium ions to H+, K+-ATPase in gastric parietal cells, without affecting Na+, K+-ATPase activity. TAK-438 is indicated for the treatment of gastric ulcer, duodenal ulcer, and reflux esophagitis.
Uses
Used in Pharmaceutical Industry:
TAK-438 is used as a treatment for acid-related diseases, such as gastric ulcer, duodenal ulcer, and reflux esophagitis, due to its ability to inhibit gastric acid secretion in a selective and reversible manner. Its unique mechanism of action allows it to maintain its inhibitory effect in both weakly acidic and neutral conditions, making it an effective treatment option for these conditions.
Synthesis
Commercially
available 2-fluoroacetophenone (283) was brominated to yield
a-bromo-acetophenone derivative 284. This compound was
treated with ethyl 2-cyanoacetate (285) under basic conditions
to provide ketoester 286 in essentially quantitative yield. Next,
intramolecular condensation of 286 upon treatment of 4 M HCl
furnished the tri-substituted pyrrole 287 in 53% yield. Reduction
of the chloride under hydrogenolytic conditions facilitated arrival
at pyrrole 288, albeit in just 18% yield. Subsequent diisobutylaluminium
hydride (DIBAL) reduction, followed by the oxidation with
tetrapropylammonium perruthenate (TPAP) and 4-methylmorpholine
N-oxide (NMMO) afforded the corresponding aldehyde 290 in 60% yield across the 2 steps. Next, N-pyrrole substitution with pyridine-
3-sulfonyl chloride 291 gave rise to N-sulfonylpyrrole 292 in
82% yield. Reductive amination of 292 afforded amine 293, which
was treated with fumaric acid (294) via co-crystallization to provide
vonoprazan fumarate (XXXVI) in 74% for the two steps.
references
[1]. yasunobu hori, jun matsukawa, toshiyuki takeuchi, et al. a study comparing the antisecretory effect of tak-438, a novel potassium-competitive acid blocker, with lansoprazole in animals. journal of pharmacology and experimental therapeutics, 2011, 337:797-804.[2]. jun matsukawa, yasunobu hori, haruyuki nishida, et al. a comparative study on the modes of action of tak-438, a novel potassium-competitive acid blocker, and lansoprazole in primary cultured rabbit gastric glands. biochemical pharmacology, 2011, 81:1145-1151.
Check Digit Verification of cas no
The CAS Registry Mumber 1260141-27-2 includes 10 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 7 digits, 1,2,6,0,1,4 and 1 respectively; the second part has 2 digits, 2 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 1260141-27:
(9*1)+(8*2)+(7*6)+(6*0)+(5*1)+(4*4)+(3*1)+(2*2)+(1*7)=102
102 % 10 = 2
So 1260141-27-2 is a valid CAS Registry Number.
