- Synthetic studies connected with the preparation of H+/K +-ATPase inhibitors rabeprazole and lansoprazole
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Synthesis of lansoprazole and rabeprazole using common intermediates is devised. The common intermediates, 2-[(4-nitro-3-methylpyridin-2-yl) methanesulfanyl]-1H-benzoimidazole and 2-[(4-chloro-3-methyl-pyridin-2-yl) methanesulfanyl]-1H-benzoimidazole, were prepared in several ways.
- Radl, Stanislav,Klecan, Ondrej,Havlicek, Jaroslav
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- Identification and synthesis of potential impurities of rabeprazole sodium
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Rabeprazole sodium (1, Achiphex) is a gastric proton pump inhibitor. It causes dose-dependent inhibition of acid secretion and is useful as an anti-ulcer agent. In the process for the preparation of 1, two potential unknown impurities were identified in HPLC at levels ranging from 0.05-0.8%. Based on mass spectral data vide LC-MS, the two impurities were characterized as 2-{[(4-chloro-3-methyl-2-pyridinyl) methyl] sulfinyl}-1H-bezimidazole (2, chloro analogue of rabeprazole) and 2-[{(4-methoxy-3-methyl-2-pyridinyl)methyl} sulfinyl]-1H-benzimidazole (3, methoxy analogue of rabeprazole). The structures were unambiguously established by independently synthesizing them and co-injecting in HPLC. To our knowledge, the compounds 2 and 3 have not been reported as process impurities elsewhere.
- Pingili, R. Reddy,Jambula, M. Reddy,Ganta, M. Reddy,Ghanta, M. Reddy,Sajja,Sundaram,Boluggdu, V. Bhaskar
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p. 814 - 818
(2007/10/03)
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