An improved and single-pot process for the production of pantoprazole substantially free from sulfone impurity

Organic Process Research and Development

Volumn 8, Issue 2, 2004, Pages 266-270

  Mathad, Vijayavitthal T ^a   Govindan, Shanmugam ^a   Kolla, Naveen Kumar ^a   Maddipatla, Madhavi ^a   Sajja, Eswaraiah ^a   Sundaram, Venkataraman ^a  

^a DR REDDY'S LABORATORIES LTD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

PANTOPRAZOLE; PROTON PUMP INHIBITOR; SULFONE;

ARTICLE; DRUG PURIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; STOMACH PH; STRUCTURE ANALYSIS; TECHNIQUE;

EID: 1842611021     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op034157y     Document Type: Article

References (13)

1. (a) Kormer, W.; Postius, S.; Riedel, R.; Simon, W. A.; Hanauer, G.; Brand, U.; Goenne, S.; Parsons, M. E. J. Pharmacol. Exp. Ther. 1990 1, 254.
2. (b) Bernhard, K.; Ernst, S.; Joerg, S. B.; Alexander, W. S.; Uwe, K.; Hartmann, S.; Georg, R.; Volker, F.; Kurt, K. J. Med. Chem. 1992, 35, 1049.
3. Kohl, B.; Sturm, E.; Rainer, G. U.S. Patent 4758579, 1985; EP Patent 166287, 1985.
4. (a) Kormer, W.; Kohl, B. Drugs Future 1990, 15, 801.
5. (b) Bekhazi, M.; Zoghbi, M.; WO 97/29103, 1997.
6. (c) Brennan, J. P.; Turner, A. T. WO 99/47514 A1, 1999.
7. (d) Cheng, M.; Wang, Q.; Pan, L. Faming zhuanli gongkai shuomingshu, 1, 102, 411 (Cl. COID4501/12), 10 May 1995.
8. Adnan, A. B.; Lina, N. N.; Al Omari, M. M.; Nidal, H. D.; Mahmoud, K. A. ; Ahmad, M. A.; Jaber, A. M. Y. Anal. Profiles Drug Subst. Excipients 2002, 29, 213.
9. Alan, E. M.; Daniel, P. B.; Daniel, L. F.; Hui, L.; Clara, I. V. U.S. Patent 5,945,425, 1999.
10. Ilya, A.; Marioara, M. U.S. Patent 0036554 A1, 2003.
11. Broeckx, R.; Laurent, M.; De Smaele, D.; Leurs, S.; Marcel, H. WO 03/008406 A1.
12. Peracetic acid is an effective oxidizing agent having an immense affinity to release nascent oxygen. The product may gradually lose some of its oxidizing power over time. It may get decomposed at elevated temperatures, possibly leading to a hazardous condition. Further, the reagent has mild ill effects on the health of the personnel handling it. It is an irritant and causes strong nasal burns if exposure is not mitigated. Appropriate precautions were taken during its handling in the plant. The substance was stored in a cool and dry location to reduce the chances of exposure to temperature. The reagent was transferred into the reaction mass in a closed system, and general safety measures were taken.
13. The percent yields of 1 were calculated by considering 70% conversion of the in situ obtained 4 into 1, as we are using 0.7 mol equiv of peracetic acid with respect to 4 for oxidation.