Site selective syntheses of [3H]omeprazole using hydrogen isotope exchange chemistry

Journal of Labelled Compounds and Radiopharmaceuticals

Volumn 58, Issue 11-12, 2015, Pages 433-441

  Pollack, Scott R ^a   Schenk, David J ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

esomeprazole; hydrogen isotope exchange; Nexium; omeprazole; Prilosec; tritium

Indexed keywords

DIAGNOSIS; HYDROGEN;

ESOMEPRAZOLE; HYDROGEN ISOTOPE EXCHANGE; IT FUNCTIONS; MEDICAL CONDITIONS; NEXIUM; OMEPRAZOLE; PRILOSEC; PROTON-PUMP INHIBITORS; SELECTIVE SYNTHESIS; SITE SELECTIVE;

TRITIUM;

4 METHOXY 3,5 DIMETHYLPYRIDIN 2 YL)METHANOL H 3; 5 METHOXY 1H BENZO[D]IMIDAZOLE 2 THIOL H 3; 5 METHOXY 2 [[(4 METHOXY 3,5 DIMETHYLPYRIDIN 2 YL)METHYL]SULFINYL] 1H BENZO[D]IMIDAZOLE H 3; 5 METHOXY 2 [[(4 METHOXY 3,5 DIMETHYLPYRIDIN 2 YL)METHYL]THIO] 1H BENZO[D]IMIDAZOLE H 3; N (2 AMINO 4 METHOXYPHENYL)ACETAMIDE H 3; N (4 METHOXY 2 NITROPHENYL)ACETAMIDE H 3; N (5 METHOXY 2 NITROPHENYL)ACETAMIDE H 3; OMEPRAZOLE DERIVATIVE; TRACER; UNCLASSIFIED DRUG; OMEPRAZOLE; PROTON PUMP INHIBITOR; RADIOPHARMACEUTICAL AGENT; TRITIUM;

ALKYLATION; ARTICLE; DESULFURIZATION; DRUG SYNTHESIS; ENANTIOMER; HALOGENATION; ISOTOPE LABELING; OXIDATION; RACEMIC MIXTURE; RADIOCHEMISTRY; SITE SELECTIVE SYNTHESIS;

OMEPRAZOLE; PROTON PUMP INHIBITORS; RADIOPHARMACEUTICALS; TRITIUM;

EID: 84947046635     PISSN: 03624803     EISSN: 10991344     Source Type: Journal    
DOI: 10.1002/jlcr.3346     Document Type: Article

References (23)

1. a) U. K. Jungren, S. E. Sjöstrand, Euro. Pat. Appl. EP 5129 A1 19791031, 1979;
2. b) E. Fellenius, T. Berglindh, G. Sachs, L. Olbe, B. Elander, S. E. Sjöstrand, B. Wallmark, Nature 1981, 290, 159.
3. X.-Q. Li, T. B. Andersson, M. Ahlstrom, L. Weidolf, Drug Metab. Disp. 2004, 32, 821.
4. E. M. Isin, C. S. Elmore, G. N. Nilsson, R. A. Thompson, L. Weidolf, Chem. Res. Toxicol. 2012, 25, 532.
5. A. Abelo, T. B. Andersson, M. Antonsson, A. K. Naudot, I. Skanberg, L. Weidolf, Drug Metab. Disp. 2000, 28, 966.
6. A. M. Crowe, R. J. Ife, M. B. Mitchell, D. Saunders, J. Label. Compd. Radiopharm. 1986, 23, 21.
7. a) L. Weidolf, K.-E. Karlsson, I. Nilsson, Drug Metab.& Disp. 1992, 20, 262;
8. b) J. E. Sjöström, J. Fryklund, T. Kühler, H. Larsson, Antimicrob. Agents Chemo. 1996, 40, 621.
9. R. Voges, J. R. Heys, T. Moenius, Preparation of Compounds Labeled With Tritium and Carbon-14. J. Wiley & Sons, Chichester, 2009.
10. a) R. Salter, J. Label. Compd. Radiopharm. 2010, 53, 645;
11. b) W. J. S. Lockley, D. Hesk, J. Label. Compd. Radiopharm. 2010, 53, 704.
12. B. Kohl, E. Sturm, J. Senn-Bilfinger, W. A. Simon, U. Krueger, H. Schaefer, G. Rainer, V. Figala, K. Klemm, J. Med. Chem. 1992, 35, 1049.
13. a) N. H. Milac, D. Jereb, PCT Int. Appl. WO 2000/002876, 2000;
14. b) H. Cotton, T. Elebring, M. Larsson, L. Li, H. Sörensen, S. von Unge, Tetrahedon Asymmetry 2000, 11, 3819.
15. P. S. Bonato, F. O. Paias, J. Braz. Chem Soc. 2004, 15, 318.
16. V. Bindal, K. Jain, R. N. Handa, H. K. Pujari, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1986, 25B, 807.
17. Y. S. Tang, W. Liu, A. Chaudhary, D. Melillo, D. C. Dean, in Synthesis and Applications of Isotopically Labelled Compounds, Vol. 8, (Eds:, D. C. Dean, C. N. Filer, K. E. McCarthy,), Wiley & Sons, Ltd., Chichester, 2004, pp. 71.
18. a) S. S. Mahajan, R. E. Nandre, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2006; 45B, 1756;
19. b) K. D. Vyas, D. Singh, S. Nandavadekar, S. Bhise, A. Jadhav, H. Desai, PCT Int. Appl. WO 2004/092142, 2004, 9-10.
20. R. Crabtree, Acc. Chem. Res. 1979, 12, 331.
21. a) E. J. Brnardic, A. Converso, M. E. Fraley, R. M. Garbaccio, S. Y. Huang, PCT Int. Appl. WO 2009/140163, 2009;
22. b) S. Darvesh, R. S. McDonald, K. V. Darvesh, D. Mataija, S. Mothana, H. Cook, K. M. Carneiro, N. Richard, R. Walsh, E. Martin, Bioorg. Med. Chem. 2006, 14, 4586.
23. W. D. Lehmann, F. M. Kaspersen, J. Label. Compd. Radiopharm. 1984, 21, 455.