An alternative synthesis of Azilsartan: an angiotensin II receptor blocker

• Authors: Srinivas Garaga , Nimesh C. Misra , Ambati V. Raghava Reddy , Koilpillai Joseph Prabahar , Chandiran Takshinamoorthy , Paul Douglas Sanasi , Raghubabu Korupolu
• Languages of publication: EN

Abstracts

EN

This paper provides a description of an alternative, novel and commercially viable process which has been developed for the preparation of Azilsartan, a pro-drug of Azilsartan medoxomil, an angiotensin II receptor blocker. The present work also provides a primary account of the synthesis and characterization of the novel intermediates (6, 7 & 10) of Azilsartan, with their spectral data.

Keywords

EN

Azilsartan; novel intermediates; synthesis and characterization

• Publisher: De Gruyter Open
• Journal: Current Issues in Pharmacy and Medical Sciences
• Year: 2015
• Volume: 28
• Issue: 2
• Pages: 72-76

Dates

published

1 - 6 - 2015

received

14 - 11 - 2014

online

16 - 7 - 2015

accepted

27 - 3 - 2015

Contributors

author

Srinivas Garaga

• Chemical Research and Development Department, Aurobindo Pharma Ltd, Survey No: 71&72, Indrakaran Village, Sangareddy Mandal, Medak district, Hyderabad – 502329, Andhra Pradesh, India
• Department of Engineering Chemistry, A. U. College of Engineering (A), Andhra University, Visakhapatnam – 530003, Andhra Pradesh, India

author

Nimesh C. Misra

• Chemical Research and Development Department, Aurobindo Pharma Ltd, Survey No: 71&72, Indrakaran Village, Sangareddy Mandal, Medak district, Hyderabad – 502329, Andhra Pradesh, India

author

Ambati V. Raghava Reddy

• Chemical Research and Development Department, Aurobindo Pharma Ltd, Survey No: 71&72, Indrakaran Village, Sangareddy Mandal, Medak district, Hyderabad – 502329, Andhra Pradesh, India

author

Koilpillai Joseph Prabahar

• Chemical Research and Development Department, Aurobindo Pharma Ltd, Survey No: 71&72, Indrakaran Village, Sangareddy Mandal, Medak district, Hyderabad – 502329, Andhra Pradesh, India

author

Chandiran Takshinamoorthy

• Chemical Research and Development Department, Aurobindo Pharma Ltd, Survey No: 71&72, Indrakaran Village, Sangareddy Mandal, Medak district, Hyderabad – 502329, Andhra Pradesh, India

author

Paul Douglas Sanasi

• Department of Engineering Chemistry, A. U. College of Engineering (A), Andhra University, Visakhapatnam – 530003, Andhra Pradesh, India

author

Raghubabu Korupolu

• Department of Engineering Chemistry, A. U. College of Engineering (A), Andhra University, Visakhapatnam – 530003, Andhra Pradesh, India

References

• 1. Aulakh G.K., Sodhi R. K., Singh M.: An update on non-peptide angiotensin receptor antagonists and related RAAS modulators. J. Life Sci. 2007, 81, 615-639.[WoS]
• 2. Miura S., Karnik S. S., Saku K.: Ability of the new AT1 receptor blocker azilsartan to block angiotensin II-induced AT1 receptor activation after wash-out. J Renin Angiotensin Aldosterone Syst. 2011, 12, 1-7.[Crossref][WoS]
• 3. Naka T. K., Inada. Y.: Compound which is an angiotensin antagonist. U.S.Patent No.5,243,054.
• 4. Kuroita T., Sakamoto H., Ojima, M.: Benzimidazole derivative and use thereof. U.S.Patent No.7,157,584.
• 5. Bansal D. et al.: An improved process for the preparation of azilsartan medoxomil. WO/2012/107814, 2012.
• 6. Radl S., Stach J.: A method of preparing 2-ethoxy-1-((2’-(5-oxo-4,5- dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1H-benzo[d] imidazole-7-carboxylates and conversion thereof to azilsartan. WO/2012/139535. 2012.
• 7. Jo N. et al.: A manufacturing method for azilsartan WO/2012/ 157980, 2012.
• 8. Kshirsagar P.B. et al.: The process for the preparation of azilsartan medoxomil, WO/2013/042066, 2013.
• 9. Kohara Y. et al.: A new class of angiotensin II receptor antagonists with a novel acidic bioisostere. Bioorg. Med. Chem. Lett. 1995, 5, 1903-1908.[Crossref]
• 10. Kohara Y. et al.: Synthesis and Angiotensin II Receptor Antagonistic Activities of Benzimidazole Derivatives Bearing Acidic Heterocycles as Novel Tetrazole Bioisosteres. J. Med. Chem. 1996, 39, 5228-5235.
• 11. Kubo K. et al.: Nonpeptide angiotensin II receptor antagonists. Synthesis and biological activity of benzimidazolecarboxylic acids. J. Med. Chem. 1993, 36, 2182-2195.
• 12. Stanislav R., Josef C., Jan S., Zuzana G.: Improved Process for Azilsartan Medoxomil: A New Angiotensin Receptor Blocker. Org. Process Res. Dev. 2013, 17, 77-86.[WoS]
• 13. Raghava Reddy A.V. et al.: A novel process for the preparation of Azilsartan medoxomil. Indian patent App. No. 4226/CHE/2012A.
• 14. Dubey S.K. et al.: Indian patent Appl. No. IN2011DE01901 A 20131004.
• 15. Aldo S., Renato C.: Preparation of olmesartan medoxomil. U.S.Pat. No.6,111,114.
• 16. Hideo H., Tadashi H., Masaayasu K.: Production method of aminobenzene compound. U.S.Pat. No. 6,177,587 B1
• 17. Srinivas G. et al.: Commercial Synthesis of Azilsartan Kamedoxomil: An Angiotensin II Receptor Blocker. Org. Process Res. Dev., 2015, 19 (4), 514-519.[WoS]

Identifiers

DOI

10.1515/cipms-2015-0047