An improved process for the production of lansoprazole: Investigation of key parameters that influence the water content in final API

Organic Process Research and Development

Volumn 14, Issue 1, 2010, Pages 229-233

  Gangula, Srinivas ^a   Elati, Chandrasekhar R ^a   Neredla, Anitha ^a   Baddam, Sudhakar R ^a   Neelam, Uday Kumar ^a   Bandichhor, Rakeshwar ^a   Dongamanti, Ashok ^b  

^a DR REDDY'S LABORATORIES LTD   (India)

^b OSMANIA UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77149163003     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op900258b     Document Type: Article

References (35)

1. (a) Prous, J. R. Drugs News Perspect. 1988,1, 38.
2. (b) Barradell, L. B.; Faulds, D.; Mc Tavish, D. Drugs 1992, 44, 225.
3. (c) Sachs, G.; Shin, J. M.; Howden, C. W. A. Pharmacol Ther. 2006, 23, 2-8.
4. For reviews, see: (a) Akira, N.; Yoshitaka, M. U.S. Patent 4, 628, 098, 1986.
5. (b) Kohl, B.; Sturm, E.; Rainer, G. U.S. Patent 4, 758, 579, 1988.
6. (a) Unsal, S. WO/2003/062223, 2003.
7. (b) Brandstr0m, A. E. WO/ 1991/18895, 1991.
8. (c) Cosme Gomez, A.; Fau de Casa-Juana Munoz, M.; Gelpi Vintro, J. M.; Molina Ponce, A. WO/2001/004109, 2001.
9. Ahm, K. H.; Kim, H.; Kim, J. R.; Jeong, S. C.; Kang, T. S.; Shin, H. T.; Lim, G. J. Bull. Korean Chem. Soc. 2002, 23, 4.
10. (a) Kato, M.; Yoshio, T.; Iwano, N. U.S. Patent 5, 578, 732, 1996.
11. (b) Avrutov, I.; Mendelovici, M. U.S. Pat. Appl. 2008/0091024 A1, 2008.
12. (a) Arulmoli, T.; Rao, S. M.; Peraka, K. S.; Selvan, A. S. WO/2008/ 035189, 2008.
13. (b) Singer, C.; Liberman, A.; Veinberg, I.; Finkelstein, N.; Nidam, T. U.S. Pat. Appl. 2005/0165060 A1, 2005.
14. (c) Della Greca, M.; Iesce, M. R.; Previtera, L.; Rubino, M.; Temussi, F.; Brigante, M. Chemosphere 2006, 63, 1087-1093.
15. (a) Moon, Y.-H.; Lee, K.-I.; Lee, G.-S. U.S. Patent 6, 423, 846, 2002.
16. Slemon, C.; Macel, B. U.S. Patent 5, 374, 730, 1994.
17. For reviews, see: (a) Mathad, V. T.; Govindan, S.; Kolla, N. K.; Maddipatla, M.; Sajja, E.; Sundaram, V. Org. process Res. Dev 2004, 8, 266-270.
18. (b) Kotagiri, V. K.; Vankawala, P. J.; Neelam, U. K.; Baddam, S. R.; Elati, R. R. C.; Kolla, N. K.; Dayabhai, J. L.; Pingili, R. R.; Gangula, S.; Jonalagadda, V. R.; Thakur, P.; Neredla, A.; Kammili, V. R. WO/2008/045777, 2008.
19. (a) Available at the following: http://www.lenntech.com/processes/ disinfection/chemical/disinfectants-sodium-hypochlorite.htm.
20. (b) Kowalski, P.; Mitkaa, K.; Ossowskab, K.; Kolarska, Z. Tetrahedron 2005, 67,1933-1953.
21. (c) Donohoe, T. J. Oxidation and Reduction in Organic Synthesis; Oxford University Press: New York, 2000.
22. (d) Xu, W. L. Z.; Zhang, Q. S.; Zhu, H. S. Synthesis 2004, 227.
23. For all these reactions, commercially available 12.0% aq sodium hypochlorite was used.
24. For reviews, see: (a) The United States Pharmacopeia: USP 28: NF 23, 28th rev. of The Pharmacopeia of the U.S., 23rd ed. of The National Formulary; United States Pharmacopeial Convention; Rockville, MD, 2005; Lansoprazole, p 1110.
25. (b) http://www.usp.org.
26. (c) Robinson, D. Org. Process Res. Dev. 2007, 11 (5), 797-801.
27. (d) Butters, M.; Catterick, D.; Craig, A.; Curzons, A.; Dale, D.; Gilmore, A.; Green, S. P.; Marziano, I.; Sherlock, J.-P.; White, W. Chem. Rev. 2006, 106, 3002-3027.
28. (e) International Conference on Harmonization of Technical Requirements for Registration of Pharmaceuticals for Human Use (ICH) Q3C (R3): Impurities: Guidelines for Residual Solvents; International Conference on Harmonisation, 1997.
29. Ludescher, J.; Khan, R. A. R.; Das, T. C. WO/2007/017244 A2, 2007.
30. Attempts were made to reduce water/THF levels with the following input sample: water content 0.5% /THF 1300 ppm. Experimental results: (a) Hot water slurry 1.0%/850 ppm.
31. (b) THF slurry: 0.5%/ 850 ppm.
32. (c) Drying in rotavapor/air tray drier/vacuum tray drier at 50-55 °C for 20-25 h samples displayed ∼0.18-0.2%/750-800 ppm, respectively.
33. Purity of compound 1 has been determined by RSHPLC analysis [Column YMC-PAK ODS-A 100 mm × 4.6 mm, 3 μ or equivalent, 15 pL; flow rate 1.0 mL/min and injection load 15 μLwithaUV detector at 285 nm]. Mobile phase - A: water (100%); mobile phase - B: acetonitrile/water/triethylamine, pH 7.0 [160:40:1 (v/v)]. Diluents preparation: acetonitrile/water/triethylamine, pH 10.5 by o-phosphoric acid [40:60:1 (v/v)].
34. 10a (2.0 gm of lansoprazole and pyridine/ethylene glycol, 8:2 ratios).
35. Residual solvent analysis of 1 was determined by gas chromatography. [Column AT-Wax, 30 mm × 0.53 mm i.d., 1 μm film thickness, injection volume: 1.0 μL, injector temperature 160 °C, and detector temperature 260 °C, injection mode/ratio: split/1.5. Carrier gas flow used 2.5 psi (Helium). Column initially held at 40 °C for 10 min, then rose to 140 °C at a rate of 10 °C for 1 min, held for 10 min, and then raised to 250 °C at a rate of 45 °C/min and held for 16 min. Headspace conditions: oven temperature maintained at 80 °C, vial equilibration kept for 30 min, loop temperature was 100 °C, and transfer line temperature 110 °C, pressurization for 0.5 min].