881674-01-7

Usage

Structure

Ethyl ester derivative of 1H-Pyrrole-3-carboxylic acid with a chloro group at the 2 position and a fluorophenyl group at the 5 position

Pharmaceutical applications

Has potential pharmaceutical applications and is of interest in medicinal chemistry research

Synthesis

May be used as a building block in the synthesis of novel compounds with biological activity or as a precursor in the development of pharmaceutical drugs

Specific properties

The presence of the chloro and fluorophenyl groups may affect its chemical and physical properties, such as solubility, stability, and reactivity. Further study and exploration are needed to fully understand its properties and potential applications.

Upstream product

• 881673-98-9 ethyl 2-cyano-4-(2-fluorophenyl)-4-oxobutanoate 
• 655-15-2 2-bromo-2'-fluoroacetophenone 
• 105-56-6 ethyl 2-cyanoacetate 
• 445-27-2 2'-Fluoroacetophenone 

Downstream Products

• 881674-06-2 5-(2-fluorophenyl)-1H-pyrrole-3-carboxylic acid ethyl ester 
• 2098974-13-9 1-[5-(2-fluorophenyl)-1-(pyridine-3-sulfonyl)-1H-pyrrole-3-yl]-N-methylmethylamine fumaric acid salt 
• 881681-00-1 1-(5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-yl)-N-methylmethanamine 
• 881674-58-4 (5-(2-fluorophenyl)-1H-pyrrol-3-yl)methanol 
• 881674-56-2 5-(2-fluorophenyl)-1H-pyrrole-3-carboxaldehyde 
• 881677-11-8 5‐(2-fluorophenyl)‐1‐(pyridine-3-sulfonyl)-1H-pyrrole-3-carbaldehyde 
• 881677-02-7 5-(2-fluorophenyl)-1-{[3-(methylsulfonyl)phenyl]sulfonyl}-1H-pyrrole-3-carbaldehyde 
• 881677-04-9 1-{[3-(ethylsulfonyl)phenyl]sulfonyl}-5-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde 
• 881677-06-1 2-{[2-(2-fluorophenyl)-4-formyl-1H-pyrrol-1-yl]sulfonyl}benzonitrile 
• 881677-08-3 4-{[2-(2-fluorophenyl)-4-formyl-1H-pyrrol-1-yl]sulfonyl}benzonitrile 
• 881677-09-4 5-(2-fluorophenyl)-1-[(2-fluorophenyl)sulfonyl]-1H-pyrrole-3-carbaldehyde 

Relevant academic research and scientific papers

Identification, characterization, synthesis of major metabolites biotransformed from vonoprazan fumarate

A first synthetic research concerning four observed metabolites and their deuterium-labeled analogues of reflux esophagitis drug vonoprazan fumarate is reported. Among which the synthetic methods of three metabolites M ? I, M-III, M-IV-Sul, and four stable isotop labeled analogues M-I-d4, M-II-d4, M-III-d4, M-IV-Sul-d4 have not yet been reported before. The structures of these compounds were elucidated on the basis of MS and NMR spectroscopy.

Identification of a novel fluoropyrrole derivative as a potassium-competitive acid blocker with long duration of action

With the aim to find a novel long-lasting potassium-competitive acid blocker (P-CAB) that would perfectly overcome the limitations of proton pump inhibitors (PPIs), we tried various approaches based on pyrrole derivative 1b as a lead compound. As part of

Proton pump inhibitors

A proton pump inhibitor containing a compound represented by the formula (I) wherein X and Y are the same or different and each is a bond or a spacer having 1 to 20 carbon atoms in the main chain, R 1 is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group, R 2 , R 3 and R 4 are the same or different and each is a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted thienyl group, an optionally substituted benzo[b]thienyl group, an optionally substituted furyl group, an optionally substituted pyridyl group, an optionally substituted pyrazolyl group, an optionally substituted pyrimidinyl group, an acyl group, a halogen atom, a cyano group or a nitro group, R 5 and R 6 are the same or different and each is a hydrogen atom or an optionally substituted hydrocarbon group, which has a superior proton pump action and shows an antiulcer activity and the like after conversion to a proton pump inhibitor in the body, or a salt thereof. or a prodrug thereof is provided.

Discovery of a novel pyrrole derivative 1-[5-(2-fluorophenyl)-1-(pyridin-3- ylsulfonyl)-1 H -pyrrol-3-yl]- n -methylmethanamine fumarate (tak-438) as a Potassium-Competitive Acid Blocker (P-CAB)

In our pursuit of developing a novel and potent potassium-competitive acid blocker (P-CAB), we synthesized pyrrole derivatives focusing on compounds with low log"‰D and high ligand-lipophilicity efficiency (LLE) values. Among the compounds synthesized, the compound 13e exhibited potent H +,K+-ATPase inhibitory activity and potent gastric acid secretion inhibitory action in vivo. Its maximum efficacy was more potent and its duration of action was much longer than those of proton pump inhibitors (PPIs). Therefore, compound 13e (1-[5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)- 1H-pyrrol-3-yl]-N-methylmethanamine fumarate, TAK-438) was selected as a drug candidate for the treatment of gastroesophageal reflux disease (GERD), peptic ulcer, and other acid-related diseases.

PROTON PUMP INHIBITORS

A proton pump inhibitor containing a compound represented by the formula (I) wherein X and Y are the same or different and each is a bond or a spacer having 1 to 20 carbon atoms in the main chain, R1 is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group, R2, R3 and R4 are the same or different and each is a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted thienyl group, an optionally substituted benzo[b]thienyl group, an optionally substituted furyl group, an optionally substituted pyridyl group, an optionally substituted pyrazolyl group, an optionally substituted pyrimidinyl group, an acyl group, a halogen atom, a cyano group or a nitro group, R5 and R6 are the same or different and each is a hydrogen atom or an optionally substituted hydrocarbon group, which has a superior proton pump action and shows an antiulcer activity and the like after conversion to a proton pump inhibitor in the body, or a salt thereof. or a prodrug thereof is provided.

Acid secretion inhibitor

The present invention provides a compound having a superior acid secretion inhibitory effect and showing an antiulcer activity and the like. The present invention provides a compound represented by the formula (I) wherein R1 is a nitrogen-containing monocyclic heterocyclic group optionally condensed with a benzene ring or a heterocycle, the nitrogen-containing monocyclic heterocyclic group optionally condensed with a benzene ring or a heterocycle optionally has substituent(s), R2 is an optionally substituted C6-14 aryl group, an optionally substituted thienyl group or an optionally substituted pyridyl group, R3 and R4 are each a hydrogen atom, or one of R3 and R4 is a hydrogen atom and the other is an optionally substituted lower alkyl group, an acyl group, a halogen atom, a cyano group or a nitro group, and R5 is an alkyl group or a salt thereof.

PROTON PUMP INHIBITORS

Proton pump inhibitors which have excellent proton pumping activity and which can be converted in vivo into proton pump inhibitors to exhibit antiulcer effect and so on, containing compounds represented by the general formula (I) or salts thereof or prodrugs of the same: (I) wherein X and Y are each independently a free valency or a spacer whose main chain has 1 to 20 carbon atoms; R1 is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group; R2, R3 and R4 are each independently hydrogen, an optionally substituted hydrocarbon group, optionally substituted thienyl, optionally substituted benzo[b]thienyl, optionally substituted furyl, optionally substituted pyridyl, optionally substituted pyrazolyl, optionally substituted pyrimidinyl, acyl, halogeno, cyano, or nitro; and R5 and R6 are each independently hydrogen or an optionally substituted hydrocarbon group.