Synthesis of 2-[[(4-fluoroalkoxy-2-pyridyl)methyl]sulfinyl]-1H- benzimidazoles as antiulcer agents.
Many 2-[[(4-fluoroalkoxy-2-pyridyl)methyl]sulfinyl]-1H-benzimidazoles were synthesized and tested for anti-secretory, antiulcer, and cytoprotective activities. Most of these compounds were superior to omeprazole in anti-secretory and antiulcer potencies, and especially in protecting the gastric mucosa from ethanol-induced damage. Among these compounds, 2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfinyl] - 1H-benzimidazole, AG-1749 (lansoprazole) (6f), was selected for further development and clinical evaluation.
Kubo
K
K
Research and Development Division, Takeda Chemical Industries, Ltd., Osaka, Japan.
Oda
K
K
Kaneko
T
T
Satoh
H
H
Nohara
A
A
D053799:2-Pyridinylmethylsulfinylbenzimidazoles; D000818:Animals; D000897:Anti-Ulcer Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002470:Cell Survival / Q000187:drug effects; D005753:Gastric Mucosa / Q000187:drug effects / Q000378:metabolism; D007101:Immersion; D064747:Lansoprazole; D008297:Male; D009853:Omeprazole / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D051381:Rats; D011919:Rats, Inbred Strains; D013276:Stomach Ulcer / Q000209:etiology / Q000517:prevention & control*
D053799:2-Pyridinylmethylsulfinylbenzimidazoles; D000897:Anti-Ulcer Agents; D064747:Lansoprazole; D009853:Omeprazole