Described is an improved process for the preparation of highly pure Bosentan monohydrate (>99.8% HPLC purity) 1 with pyrimidinone 8 and the dimer 9 impurities to less than 0.10% of HPLC analysis. The present work also provides processes for the preparation of pyrimidinone 8 and dimer 9 impurities.
| Published in |
Science Journal of Chemistry (Volume 2, Issue 6-1)
This article belongs to the Special Issue Green Chemistry: Synthesis and Its Uses |
| DOI | 10.11648/j.sjc.s.2014020601.12 |
| Page(s) | 9-15 |
| Creative Commons |
This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited. |
| Copyright |
Copyright © The Author(s), 2024. Published by Science Publishing Group |
Bosentan monohydrate, highly pure, Pulmonary artery hypertension
| [1] | (a) M. Hoeper, N. Taha, A. Bekjarova, R. Gatzke, E. Spiekerkoetter, “Bosentan treatment in patients with primary pulmonary hypertension receiving nonparenteral prostanoids,” Eup. Respir. J.2003, 22, 330. (b) J.M. Pearl, S.A. wellmann, J.L, Mcnamara, J.P. Lombardi, C.J. Wager, J.L. Raake, D.P. Nelson,’ Bosentan prevents hypoxia-reoxygenation-induced pulmonary hypertension and improves pulmonary function,” Ann Thorac. Surg. 1999, 68, 1714 (c) W.K. Kenneth, M.N. Jean, “Bosentan for the treatment of pulmonary arterial hypertension,” Ann Pharmacother 2003 Jul-Aug; 37 (7-8):1055-62 |
| [2] | B. Kaspar, C. Martin, F. Walter, H. Georges, L. Bernd-Michael, N. Werner, R. Henri, “Sulfonamides,” U.S. Patent 5,292,740, 1994. |
| [3] | (a) P.J. Harrington, H.N. Khatri, B.S. Dehoff, “Preparation of sulfonamides.” U.S. Patent 6,136,971, 2000. (b) P.J. Harrington, H.N. Khatri, B.S. Dehoff, M.R. Guinin, M.A. Boehler, K.A. Glaser, “Research and development of a second-generation process for bosentan, an endothelin receptor antagonist,” Org. Process Res. Dev. 2002, 6, 120 |
| [4] | (a) C.N. Navnath, M.J. Kunal T.G. Chandrashekhar, N.J. Madhukar, T.M. Vijayavittal, “Facile one-pot process for large-scale production of highly pure bosentan monohydrate, an endothelin receptor antagonist,” Org. Process Res. Dev. 2011, 15, 1382 (b), C.N.Navkanth, M.J. Kunal, T.G. Chandrashekhar, N.J. Madhukar, T.M. Vijayavittal, “ A novel process for preparation of Bosentan,” WO2012/020421 |
| [5] | (a) B. Volker, B. Kaspar, C. Jean-Marie, C. Martine, H. Georges, L. Bernd-Michael, M. Marcel, N. Werner, R. Henri, “Sulfonylaminopyrimidines,” U.S.Patent 5,541,186, 1996.(b) A. Gaitonde, B. Manojkumar, S. Mekde, V. Padalkar, H. Mande, .”Process for preparing Bosentan,” WO2009/098517, 2009 (c)M. Satyanarayanareddy, S. Eswaraiah, G. Venkatreddy, “Improved and novel process for the preparation of Bosentan,” WO2009/095933 (d) K. Sata, B. Pandey, “Process for preparation of Bosentan,” WO/2010/032261(e) D. Rao, K. Ramachandra N.P. Rajendra, S.S. Manjinder, A. Ashwini, “Method of synthesis of Bosentan, its polymorphic forms and its salts,” WO2009/083739 (g) G. Biffi, L. Feliciani, E. Viscardi, “Process for the preparation of Bosentan,” WO2010/103362, (h) G. Dixit, N. Gaikwad, H. ;Naidu, P. Prasad S. Nitin, J. Valgeirsson, “Process for the preparation of Bosentan and related compounds,” WO2009/112954(i) J.V. Raman, S. Patel, S. Mistry, B. Parmar, M. Timbadiya, M. Madam, “An improved process for preparing Bosentan,” WO2012/073135 (j) B. Giancarlo, F. Lazzaro, V. Enrico, “Process for the preparation of Bosentan’” U.S. Patent 2012/0041200 (k) T. Maurizio, N. Diletta, A. Pietro, R. Gabriele, M. Simone, “Process for the preparation of Bosentan” U.S. Patent 2009/0156811(l) V. Gore, M. Bindu, D. Shinde, D. Kokane, S. Ghrat, R.Dandala, “Process for the preparation of Bosentan,” WO2012/056468. |
| [6] | K. Amala, K. Srinivasu, B. VeeraSwamy, K. Subash, AKS. Bhujanga Rao, N. VenkaiahChowdary, “Process for the preparation of B osentan monohydrate,” US2013/245259. |
APA Style
Amala Kompella, Srinivasu Kasa, Veera Swami Balina, Subhash Kusumba, Bhujanga Rao Kalisatya Adibhatla, et al. (2014). Large Scale Process to Prepare Highly Pure Bosentan Monohydrate. Science Journal of Chemistry, 2(6-1), 9-15. https://doi.org/10.11648/j.sjc.s.2014020601.12
ACS Style
Amala Kompella; Srinivasu Kasa; Veera Swami Balina; Subhash Kusumba; Bhujanga Rao Kalisatya Adibhatla, et al. Large Scale Process to Prepare Highly Pure Bosentan Monohydrate. Sci. J. Chem. 2014, 2(6-1), 9-15. doi: 10.11648/j.sjc.s.2014020601.12
Share This Article
Twitter
Linked In
Facebook
Copy
Download@article{10.11648/j.sjc.s.2014020601.12,
author = {Amala Kompella and Srinivasu Kasa and Veera Swami Balina and Subhash Kusumba and Bhujanga Rao Kalisatya Adibhatla and Pulla Reddy Muddasani},
title = {Large Scale Process to Prepare Highly Pure Bosentan Monohydrate},
journal = {Science Journal of Chemistry},
volume = {2},
number = {6-1},
pages = {9-15},
doi = {10.11648/j.sjc.s.2014020601.12},
url = {https://doi.org/10.11648/j.sjc.s.2014020601.12},
eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.sjc.s.2014020601.12},
abstract = {Described is an improved process for the preparation of highly pure Bosentan monohydrate (>99.8% HPLC purity) 1 with pyrimidinone 8 and the dimer 9 impurities to less than 0.10% of HPLC analysis. The present work also provides processes for the preparation of pyrimidinone 8 and dimer 9 impurities.},
year = {2014}
}
TY - JOUR T1 - Large Scale Process to Prepare Highly Pure Bosentan Monohydrate AU - Amala Kompella AU - Srinivasu Kasa AU - Veera Swami Balina AU - Subhash Kusumba AU - Bhujanga Rao Kalisatya Adibhatla AU - Pulla Reddy Muddasani Y1 - 2014/09/23 PY - 2014 N1 - https://doi.org/10.11648/j.sjc.s.2014020601.12 DO - 10.11648/j.sjc.s.2014020601.12 T2 - Science Journal of Chemistry JF - Science Journal of Chemistry JO - Science Journal of Chemistry SP - 9 EP - 15 PB - Science Publishing Group SN - 2330-099X UR - https://doi.org/10.11648/j.sjc.s.2014020601.12 AB - Described is an improved process for the preparation of highly pure Bosentan monohydrate (>99.8% HPLC purity) 1 with pyrimidinone 8 and the dimer 9 impurities to less than 0.10% of HPLC analysis. The present work also provides processes for the preparation of pyrimidinone 8 and dimer 9 impurities. VL - 2 IS - 6-1 ER -
Information
Email: