Copyright (c) 2016 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
A Simple and Efficient Procedure for Synthesis of Agomelatine
Corresponding Author(s) : R. Madhusudhan Raju
Asian Journal of Chemistry,
Vol. 28 No. 6 (2016): Vol 28 Issue 6
Abstract
A simple and efficient process for the large scale preparation of agomelatine, an antidepressant drug is described. Agomelatine was synthesized from 7-methoxy-1-tetralone in five steps. The route reported employs readily, commercially viable starting materials, reagents and potentially be utilized for the process of synthesis of agomelatine.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- WHO, World Suicide Prevention Day (2015).
- A.D. Lopez and C.C.J.L. Murray, Nat. Med., 4, 1241 (1998); doi:10.1038/3218.
- J.A. Mico, D. Ardid, E. Berrocoso and A. Eschalier, Trends Pharmacol. Sci., 27, 348 (2006); doi:10.1016/j.tips.2006.05.004.
- M. Zheng, C. Liu, F. Pan, D. Shi, F. Ma, Y. Zhang and Y. Zhang, Cell. Mol. Biol., 31, 421 (2011).
- (a) M.H. Trivedi, A.J. Rush, S.R. Wisniewski, A.A. Nierenberg, D. Warden, L. Ritz, G. Norquist, R.H. Howland, B. Lebowitz and P.J. McGrath, Am. J. Physiol., 163, 28 (2006); (b) V. Srinivasan, D. de Berardis, S.D. Shillcutt and A. Brzezinski, Expert Opin. Investig. Drugs, 21, 1503 (2012); doi:10.1517/13543784.2012.711314.
- European Marketing Authorization, Valdoxan (Agomelatine): Summary of Product Characteristics, (2009).
- H. Loo, A. Hale and H. Dhaene, Int. Clin. Psychopharmacol., 17, 239 (2002); doi:10.1097/00004850-200209000-00004.
- A. Hale, R.-M. Corral, C. Mencacci, J.S. Ruiz, C.A. Severo and V. Gentil, Int. Clin. Psychopharmacol., 25, 305 (2010); doi:10.1097/YIC.0b013e32833a86aa.
- S. Kasper, G. Hajak, K. Wulff, W.J.G. Hoogendijk, A.L. Montejo, E. Smeraldi, J.K. Rybakowski, M.-A. Quera-Salva, A.M. Wirz-Justice, F. Picarel-Blanchot and F.J. Baylé, J. Clin. Psychiatry, 71, 109 (2010); doi:10.4088/JCP.09m05347blu.
- P. Lemoine, C. Guilleminault and E.J. Alvarez, Ann. Clin. Psychiatry, 68, 1723 (2007); doi:10.4088/JCP.v68n1112.
- S.H. Kennedy, S. Rizvi, K.J. Fulton and A.J. Rasmussen, Clin. Psychopharmacol., 28, 329 (2008); doi:10.1097/JCP.0b013e318172b48c.
- S.H. Kennedy and S.J. Rizvi, CNS Drugs, 24, 479 (2010); doi:10.2165/11534420-000000000-00000.
- A. Montejo, N. Prieto, A. Terleira, J. Matias, S. Alonso, G. Paniagua, S. Naval, D. Parra, C. Gabriel, E. Mocaer and A. Portoles, Psychopharmacol., 24, 111 (2010); doi:10.1177/0269881108096507.
- S. Yous, J. Andrieux, H.E. Howell, P.J. Morgan, P. Renard, B. Pfeiffer, D. Lesieur and B. Guardiola-Lemaitre, Med. Chem., 35, 1484 (1992); doi:10.1021/jm00086a018.
- (a) J.C. Souvie, I.G. Blanco, G. Thominot, G. Chapuis, S. Horvath and G. Damien, US Patent 7250531,B2 (2007); (b) J.C. Souvie and I.G. Blanco, US Patent 7999129,B2 (2011).
- (a) C. Hardouin and J.P. Lecouve, PCT Int. Appl. WO 2010015746 (2010); (b) C. Markl and D.P. Zlotos, Synthesis, 79 (2011); doi:10.1055/s-0030-1258968.
- (a) S. Zhou, F.F. Jian and S.Q. Zhuanli, CN Patent 101759591 (2010); (b) W. Hu, Q. Xu, L.F. Yang, and S.Q. Zhuanli, CN 101792400 (2010); (c) C. Hardouin, J.P. Lecouve and N. Bragnier, PCT Int. Appl. WO2010015745 (2010); (d) P. Bontempelli, X. Jalenques, J.-B. Starck and J.P. Sery, PCT Int. Appl. WO 2010015744 (2010).
References
WHO, World Suicide Prevention Day (2015).
A.D. Lopez and C.C.J.L. Murray, Nat. Med., 4, 1241 (1998); doi:10.1038/3218.
J.A. Mico, D. Ardid, E. Berrocoso and A. Eschalier, Trends Pharmacol. Sci., 27, 348 (2006); doi:10.1016/j.tips.2006.05.004.
M. Zheng, C. Liu, F. Pan, D. Shi, F. Ma, Y. Zhang and Y. Zhang, Cell. Mol. Biol., 31, 421 (2011).
(a) M.H. Trivedi, A.J. Rush, S.R. Wisniewski, A.A. Nierenberg, D. Warden, L. Ritz, G. Norquist, R.H. Howland, B. Lebowitz and P.J. McGrath, Am. J. Physiol., 163, 28 (2006); (b) V. Srinivasan, D. de Berardis, S.D. Shillcutt and A. Brzezinski, Expert Opin. Investig. Drugs, 21, 1503 (2012); doi:10.1517/13543784.2012.711314.
European Marketing Authorization, Valdoxan (Agomelatine): Summary of Product Characteristics, (2009).
H. Loo, A. Hale and H. Dhaene, Int. Clin. Psychopharmacol., 17, 239 (2002); doi:10.1097/00004850-200209000-00004.
A. Hale, R.-M. Corral, C. Mencacci, J.S. Ruiz, C.A. Severo and V. Gentil, Int. Clin. Psychopharmacol., 25, 305 (2010); doi:10.1097/YIC.0b013e32833a86aa.
S. Kasper, G. Hajak, K. Wulff, W.J.G. Hoogendijk, A.L. Montejo, E. Smeraldi, J.K. Rybakowski, M.-A. Quera-Salva, A.M. Wirz-Justice, F. Picarel-Blanchot and F.J. Baylé, J. Clin. Psychiatry, 71, 109 (2010); doi:10.4088/JCP.09m05347blu.
P. Lemoine, C. Guilleminault and E.J. Alvarez, Ann. Clin. Psychiatry, 68, 1723 (2007); doi:10.4088/JCP.v68n1112.
S.H. Kennedy, S. Rizvi, K.J. Fulton and A.J. Rasmussen, Clin. Psychopharmacol., 28, 329 (2008); doi:10.1097/JCP.0b013e318172b48c.
S.H. Kennedy and S.J. Rizvi, CNS Drugs, 24, 479 (2010); doi:10.2165/11534420-000000000-00000.
A. Montejo, N. Prieto, A. Terleira, J. Matias, S. Alonso, G. Paniagua, S. Naval, D. Parra, C. Gabriel, E. Mocaer and A. Portoles, Psychopharmacol., 24, 111 (2010); doi:10.1177/0269881108096507.
S. Yous, J. Andrieux, H.E. Howell, P.J. Morgan, P. Renard, B. Pfeiffer, D. Lesieur and B. Guardiola-Lemaitre, Med. Chem., 35, 1484 (1992); doi:10.1021/jm00086a018.
(a) J.C. Souvie, I.G. Blanco, G. Thominot, G. Chapuis, S. Horvath and G. Damien, US Patent 7250531,B2 (2007); (b) J.C. Souvie and I.G. Blanco, US Patent 7999129,B2 (2011).
(a) C. Hardouin and J.P. Lecouve, PCT Int. Appl. WO 2010015746 (2010); (b) C. Markl and D.P. Zlotos, Synthesis, 79 (2011); doi:10.1055/s-0030-1258968.
(a) S. Zhou, F.F. Jian and S.Q. Zhuanli, CN Patent 101759591 (2010); (b) W. Hu, Q. Xu, L.F. Yang, and S.Q. Zhuanli, CN 101792400 (2010); (c) C. Hardouin, J.P. Lecouve and N. Bragnier, PCT Int. Appl. WO2010015745 (2010); (d) P. Bontempelli, X. Jalenques, J.-B. Starck and J.P. Sery, PCT Int. Appl. WO 2010015744 (2010).