100924-68-3

Usage

Chemical structure

Benzimidazole derivative containing a sulfoxide functional group

Function

Proton pump inhibitor

Mechanism of action

Inhibits the enzyme responsible for the final step in the production of gastric acid

Uses

Treatment of conditions such as gastroesophageal reflux disease (GERD), ulcers, and Zollinger-Ellison syndrome

InChI:InChI=1/C16H17N3OS/c1-19(2)15-10-6-3-7-12(15)11-21(20)16-17-13-8-4-5-9-14(13)18-16/h3-10H,11H2,1-2H3,(H,17,18)

Upstream product

• 144-55-8 sodium hydrogencarbonate 
• 104340-38-7 2-[(1H-Benzimidazol-2-yl)thiomethyl]-N,N-dimethylbenzenamine 
• 106771-59-9 2-(chloromethyl)-N,N-dimethylaniline 
• 134469-07-1 Benzimidazol-2-thiol 

Relevant academic research and scientific papers

2-?(1H-benzimidazol-2-ylsulfinyl)methyl!benzenamines

This invention relates to 2-?(1H-benzimidazol-2-ylsulfinyl)methyl!benzenamines that are useful in the treatment and prevention of ulcers.

METHOD OF USING (H+/K+)ATPASE INHIBITORS AS ANTIVIRAL AGENTS

A class of compounds which are (H+/K+) ATPase inhibitors can be used for the treatment of viral infections. Compounds of particular interest are defined by Formula III: wherein D is N or CH; wherein R7 is one or more radicals selected from hydrido, alkoxy, amino, cyano, nitro, hydroxyl, alkyl, halo, haloalkyl, carboxyl, alkanoyl, nitro, amino, alkylamino, aminocarbonyl , aminosulfonyl , alkylaminocarbonyl, alkylcarbonylamino, alkoxycarbonyl, alkylaminosulfonyl, alkylsulfonylamino, alkylthio, alkyl-sulfinyl and alkylsulfonyl; wherein R8 is selected from hydrido, alkyl and cycloalkyl; wherein R9 is one or more radicals selected from hydrido, alkoxy, amino, alkyl, halo, cyano, nitro, hydroxyl, haloalkyl, nitro, carboxyl, alkanoyl, amino, alkylamino, dialkylamino, aminocarbonyl , alkylaminocarbonyl, alkylcarbonylamino, aminosulfonyl, alkylaminosulfonyl, alkylsulfonylamino, alkoxycarbonyl, alkylthio, alkylsulfinyl and alkylsulfonyl; and wherein R10 and R11 are independently selected from hydrido, alkyl, aryl, alkylcarbonyl and arylcarbonyl wherein the aryl ring may be further substituted with one or more radicals selected from alkyl, halo, hydrazidylcarbonyl, aminocarbonyl and alkoxy; or wherein R10 and R11 together with the nitrogen atom form a heterocyclic ring

Stabilized benzimidazole derivative and composition

A stabilized physiologically active benzimidazole derivative having the formula (I): STR1 wherein R1 is hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a fluoroalkyl group having 1 to 6 carbon atoms, a cycloalkyl group, phenyl group or an aralkyl group, R2 is hydrogen atom or a lower alkyl group, or R1 and R2 together with the adjacent nitrogen atom form a ring, and each of R3a, R3b, R4a, R4b and R4c independently is hydrogen atom, a halogen atom, a fluoroalkyl group having 1 to 6 carbon atoms, a lower alkyl group, a lower alkoxy group, a lower alkoxycarbonyl group or an amino group. The stabilized benzimidazole derivative is in amorphous form or present in contact with a basic material.

Method of protecting gastrointestinal tract

A method of protecting gastrointestinal tract in a mammal from the untoward, non-gastric-acid-induced effects of exposure to gastrointestinally injuruous agents, which comprises administering orally to said mammal a non-antisecretory amount of a benzimidazole derivative having the formula (I): STR1 wherein R1 is the hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group, phenyl group or aralkyl group, R2 is the hydrogen atom or a lower alkyl group, or R1 and R2 together with the adjacent nitrogen atom forms a ring, and each of R3 and R4 independently is the hydrogen atom, a halogen atom, the trifluoromethyl group, a lower alkyl group, a lower alkoxy group, a lower alkoxycarbonyl group or an amino group.

Substituted 2-anilines as Potential Inhibitors of H+/K+ ATPase

A series of substituted 2-anilines were synthesized as potential inhibitors of the acid secretory enzyme H+/K+ ATPase.Substitutions on the aniline nitrogen atom resulted in potent enzyme inhibition in vitro but weak activity in gastric fistula dogs.Electron-donating substituents on the aniline ring enhanced in vitro and in vivo potency relative to the unubstituted analogue.The potency showed a correlation to the calculated pKa of the aniline nitrogen atom.Substitutions on the aniline and benzimidazole rings did not further enhance potency.Di- and trisubstituted aniline derivatives were potent inhibitors of the enzyme system.The preferred combination of substituents were a methoxy group on the benzimidazole ring and a single alkyl group on the aniline ring.One such compound, 76, was an effective inhibitor of acid secretion in the dog and was selected for further pharmacological study.