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Song W.,Shandong University | Zhou Y.,Shandong University | Zhou Y.,Dalian University of Technology | Fu Y.,Shouguang Fukang Pharmaceutical Co. | Xu W.,Shandong University
Tetrahedron Asymmetry | Year: 2013

(R)-Lansoprazole, (S)-pantoprazole, and (R)-rabeprazole are commonly used drugs for peptic ulcers. The self-disproportionation of the enantiomers of these prazoles in regular column chromatography is described herein. When non-racemic mixtures of the prazoles were eluted under achiral, gravity-driven silica gel column chromatography conditions, enantiomeric enrichment occurred in the first fractions, while enantiomeric depletion occurred in the last fractions. The pure enantiomers of all prazoles can be prepared from non-racemic starting materials using a simple procedure (achiral chromatography). Thus, a new method for obtaining a sample with very high enantiomeric purity was established. These results suggested that caution is required to avoid enantiomer fractionation during the purification of the asymmetric synthesis products by chromatography. © 2013 Elsevier Ltd. All rights reserved.


Song W.,Shandong University | Song W.,Shouguang Fukang Pharmaceutical Co. | Dong L.,Shouguang Fukang Pharmaceutical Co. | Zhou Y.,Shouguang Fukang Pharmaceutical Co. | And 3 more authors.
Synthetic Communications | Year: 2015

An efficient synthesis of esomeprazole via catalytic asymmetric oxidation of 1H-benzimidazolyl pyridinylmethyl sulfide by a titanium complex with a hexa-aza-triphenolic macrocycle ligand is described. Esomeprazole was prepared with 99.6% ee, which meets the high requirement of the European Pharmacopeia on enantiomeric purity. © 2015 Taylor & Francis Group, LLC.


Song W.-G.,Shandong University | Song W.-G.,Shouguang Fukang Pharmaceutical Co. | Xu W.-F.,Shandong University | Yang D.-W.,Shouguang Fukang Pharmaceutical Co. | And 2 more authors.
Chinese Journal of New Drugs | Year: 2013

Objective: To optimize the synthetic route of revaprazan hydrochloride. Methods: The target compound (1) was synthesized from guanidine nitrate (2) as the starting material, by ring-closure with ethyl 2-methylacetoacetate, chlorination, condensation with 1-methyl-1, 2, 3, 4-tetrahydroisoquinoline yielding 2-amino-4- [3, 4-dihydro-1-methyl-2-(1H)-isoquinolinyl]-5, 6-dimethylpyrimidine (5); subsequently, acetylation of 5, condensation with 4-bromofluorobenzene and deacetylation, and then salification with dry HCl gas. Results: The structure of the target compound was confirmed by mp, 1H-NMR and MS. Conclusion: This improved method has the advantage of simpler operation and increases total yield from 60% to 71%, thus it can be applied in industrialized production.


Song W.,Shandong University | Song W.,Shouguang Fukang Pharmaceutical Co. | Zhang X.,Biomedical Science and Technology Industrial Park of Weifang Hi Technology Zone | Li S.,Shouguang Fukang Pharmaceutical Co. | Xu W.,Shandong University
Chemical Biology and Drug Design | Year: 2015

Acid-related diseases of the upper gastrointestinal tract, especially gastroesophageal reflux disease (GERD), remain a widespread problem worldwide. In this paper, we reported the design, synthesis, and preliminary gastric antisecretory activity evaluation of novel pyrimidine derivatives as acid pump antagonists. The gastric antisecretory activity assay results showed that all compounds displayed potent gastric antisecretory activity when gastric secretion was stimulated by histamine. The most potent compound 5g exhibited even similar gastric antisecretory activity compared with the control revaprazan, and the relative inhibition rate was 93.0%, which was worthy of further investigation. © 2014 John Wiley & Sons A/S.

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