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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 47, 2017 - Issue 14
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SYNTHETIC COMMUNICATIONS REVIEWS

Overview of the synthetic routes to sildenafil and its analogues

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Pages 1269-1300 | Received 28 Jan 2017, Published online: 08 May 2017

References

  • Terrett, N. K.; Bell, A. S.; Brown, D.; Ellis, P. Bioorg. Med. Chem. Lett. 1996, 6, 1819.
  • Rotella, D. P. Nat. Rev. Drug Dis. 2002, 1, 674.
  • Pissarnitski, D. Med. Res. Rev. 2006, 26, 369.
  • Bunnage, M. E.; Levett, P. C.; Thomson, N. M. Patent, WO, 2001098303; Chem. Abst. 2002, 136, 53761.
  • O’Neil, M. J. (ed.) The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biological, Cambridge, UK, Royal Society, 2013, p. 1581.
  • US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.11. Nov, 2012. Available from, as of June 12, 2014. http://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
  • Nahata, M. C.; Morosco, R. S.; Brady, M. T. Extemporaneous sildenafil citrate oral suspensions for the treatment of pulmonary hypertension in children. Am J Health Syst Pharm. 2006, 63(3), 254.
  • Nichols, D. J.; Muirhead, G. J.; Harness, J. A. Br. J. Clin. Pharmacol. 2002, 53, 5S.
  • Milligan, P. A.; Marshall, S. F.; Karlsson, M. O. A population pharmacokinetic analysis of sildenafil citrate in patients with erectile dysfunction. Br. J. Clin. Pharmacol. 2002, 53, 455.
  • Gingell, C.; Sultana, S. R.; Wulff, M. B.; Gepi-Attee, S. J. Sex. Med. 2004, 1, 179.
  • Wawer, I.; Pisklak, M.; Chilmonczyk, Z. J. Pharm. Biomed. 2005, 38, 865.
  • Reddy, A. V. R.; Srinivas, G.; Takshinamoorthy, C.; Peruri, B. G.; Naidu, A. Sci. Pharm. 2016, 84, 447.
  • Ping, G.; Lixin, W.; Huaming, Z.; Yanling, S. Shenyang Yaoke Daxue Xuebao 2002, 19, 173.
  • Xu, B.; Zhao, A.; Wu, Q. New procedure for synthesis of Sildenafil. Huaxue Yanjiu Yu Yingyong, 2002, 14(5), 605–607.
  • Piazza, G. A.; Pamukcu, R. Preparation of phenyl purinone derivatives for the treatment of precancerous lesions, U.S, 6200980, 2001.
  • Dale, D. J.; Dunn, P. J.; Golightly, C.; Hughes, M. L.; Levett, P. C.; Pearce, A. K.; Searle, P. M.; Ward, G.; Wood, A. S. Org. Process Res. Dev. 2000, 4, 17.
  • Dunn, P. J.; Levett, P. C. Preparation of pyrazolo[4,3-d]pyrimidin-7-ones, European Patent Applications, 994115, 2000.
  • Pang, B. H.; Wang, N.; Wang, X.; Xi, S.; Fu, H. Method for preparing sildenafil via base catalyzed cyclization of a benzamidopyrazole carboxamide using salts of phenols, thiophenols, and thiols. Mexican Patent Applications, 2006013505, 2009.
  • Muller, N.; Matzke, M. Method for preparing 1-alkyl-pyrazol-5-carboxylic acid esters III. U.S. Patent, 6,444,828, 2002.
  • Muller, N.; Matzke, M. Method of preparing 1-alkyl-pyrazol-5-carboxylic acid esters I, U.S. Patent, 6,297,386, 2001.
  • Heuer, L.; Muller, N.; Steffan, G. European Patent, EP 0 819 678, in German, same authors U.S. Patent 5,969,152, and U.S. Patent 6,025,499, in English, 1999.
  • Murlidhar, A. R.; Bhaskar, B. S.; Kant, S. T.; Kantibhai, A. K.; Hussain, H. A novel process for the preparation of sildenafil citrate. Indian Patent Applications, 2008MU01502, 2010.
  • Khan, K. M.; Maharvi, G. M.; Khan, M. T. H.; Perveen, S. M. I.; Choudhary, R. A. Mol. Divers. 2005, 9(1–3), 15.
  • Baxendale, I. R.; Ley, S. V. Bioorg. Med. Chem. Lett. 2000, 10, 1983.
  • Toque, H. A. F.; Priviero, F. B. M.; Teixeira, C. E.; Perissutti, E.; Fiorino, Severino, F. B.; Frecentese, F.; Lorenzetti, R.; Baracat, J. S.; Santagada, V.; Caliendo, G.; Antunes, E.; de Nucci, G. J. Med. Chem. 2008, 51, 2807.
  • Tian, G.; Zhu, Y.; Liu, Z.; Wang, Z.; Shen, J.; Bombek, S.; Stropnik, T. Synthesis and pharmacological evaluations of sildenafil analogues for treatment of erectile dysfunction, WO 2008/074512, 2008.
  • Dunn, P. J.; Wood, A. S. Process for the preparation of sildenafil, EP 0 812 845A1, 1997.
  • Liu, H.; He, X.; Choi, H-S.; Yang, K.; Woodmansee, D.; Wang, Z.; Ellis, D. A.; Wu, B.; He, Y.; Nguyen, T. N. Compounds and compositions as inhibitors of cannabinoid receptor 1 activity, WO2006047516A2, 2006.
  • Antilla, J. C., Baskin, J. M., Barder, T. E., Buchwald, S. L. J. Org. Chem. 2004, 69, 5578.
  • Wang, C.; Ashton, T. D.; Gustafson, A.; Bland, N. D.; Ochiana, S. O.; Campbell, R. K.; Pollastri, M. P. Bioorg. Med. Chem. Lett. 2012, 22, 2579.
  • DeWald, H. A.; Beeson, N. W.; Hershenson, F. M.; Wise, L. D.; Downs, D. A.; Heffner, T. G.; Coughenour, L. L.; Pugsley, T. A. J. Med. Chem. 1988, 31, 454.
  • Yuan, J.; Gulianello, M.; de Lombaert, S.; Brodbeck, R.; Kieltyka, A.; Hodgetts, K. J. Bioorg. Med. Chem. Lett. 2002, 12, 2133.
  • Fletcher, S. R.; Menet, C. J. M.; Dykes, G. J.; Merayo, M. N.; Schmitt, B. A. Novel compounds useful for the treatment of degenerative & inflammatory diseases, WO2008071650A2, 2008.
  • Qi, Y.; Zhao, Y.; Qi, Y. Process for preparation of sildenafil. Faming Zhuanli Shenqing, CN102690273, 2012.
  • Murphy, R.; Kung, H. F.; Kung, M.; Billings, J. J. Med. Chem. 1990, 33, 171.
  • Okumura, K.; Inoue, I. J. Pharm. Soc. Jpn. 1960, 81, 453.
  • Stanetty, P.; Koller, H.; Purstinger, G. Monatsche. Chem. 1990, 121, 883.
  • Perkin, W. H.; Trikojus, V. M. J. Chem. Soc. 1926, CCCLXXXIX, 2925.
  • Fuson, R. C.; Gaertner, R.; Chadwick, D. H. J. Org. Chem. 1948, 13, 489.
  • Kim, D.-K.; Lee, N.; Lee, J. Y.; Ryu, D. H.; Kim, J.-S.; Lee, S.-H.; Choi, J.-Y.; Chang, K.; Kim, Y.-W.; Im, G.-J.; Choi, W.-S.; Kim, T.-K.; Ryu, J.-H.; Kim, N.-H.; Lee, K. Bioorg. Med. Chem. 2001, 9, 1609.
  • Ramanjaneyulu, S.; Bhandari, M.; Indukuri, V. S. K.; Simhadri, S. Nove process for the preparation of sildenafil citrate, WO2007141805, 2007.
  • Kumar, I. V. S.; Ramanjaneyulu, G. S.; Bindu, V. H. Lett. Org. Chem. 2011, 8(9), 668.
  • Yang, D.; Wang, H.; Shi, H. Chinese Patent CN 99–111153, 2001 (Chem. Abs. 2001, 135, 242238).
  • Yang, D.; Wang, H.; Shi, H. Preparation of sildenafil, Chinese Patent CN 109345, 2001 (Chem. Abs. 2001, 135, 107334).
  • Achmatowicz, O.; Balicki, R.; Chmielowiec, U.; Zaworska, A.; Szelejewki, W.; Magielka, S.; Glowacka, A.; Wysoczynska, M.; Dzikowska, J.; Bober, L.; Landsberg, J.; Falkowski, C.; Roznerski, Z.; Marczak, B.; Kempa, A. World Patent, WO/22918, 2001.
  • Ha, M. C.; Kim, H. G. Imine compound and method for the preparation of sildenafil therefrom. Repub. Korea patent 2012, 1127814.
  • Liu, Y.; Zhang, Z. Preparation of 5- [2-ethoxy-5- (4-methyl-1-piperazinylsulfonyl) phenyl] -1-methyl-3-propyl-1,6-dihydro-7H-benzo [4, 3-d] pyrimidin-7-one, Faming Zhuanli Shenqing Gongkai Shuomingshu, CN1406939, 2003.
  • Balicki, R.; Chmielowiec, U. Przem. Chem. 2006, 85, 351.
  • Sawant, S. D.; Reddy, G. L.; Dar, I. M.; Srinivas, M.; Gupta, G.; Sahu, P. K.; Mahajan, P.; Singh, S.; Sharma, S. C.; Tikoo, M.; Singh, G. D.; Nargotra, A.; Vishwakarma, R. A.; Syed, S. H. Bioorg. Med. Chem. 2015, 23, 2121.
  • Braude, V.; Aronhime, J.; Shabat, S. Methods for the production of sildenafil base and citrate salt, WO 2005067936 A3, 2005.
  • Lin, M-C.; Liu, Y-C.; Lin, Y-L.; Lin, J-H. J. Food Drug Anal. 2008, 16, 15.
  • Dunn, P. J.; Dunne, C. Process for the preparation of pyrazolopyrimidinones, WO2001098284 A1, 2001.
  • Shavnya, A.; Coffey, S. B.; Smith, A. C.; Mascitti, V. Org. Lett. 2013, 15, 6226.
  • Cantos, L. C.; Comely, A. C.; Rafecas Jane, L.; Tesson, N. Process for the preparation of inhibitor of phosphodiesterase type 5 sildenafil, and analogs and intermediates thereof, using Suzuki coupling as key step. PCT International Applications, 2008152177, 2008.
  • Lu, Y.-F.; Antczak, C.; Tao, Y.; Oudenes, J. The preparation of 1-[[3-(4,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulfonyl]-4-methylpiperazine. Braz. Pedido PI, 9803911, 2000.
  • Kankan, R. N. R.; Rao, D. R. A novel process for the synthesis of sildenafilcitrate. PCT Int. Appl., 2001019827, 2001.
  • Kim, D-K.; Lee, J. Y.; Park, H-J.; Thai, K. M. Bioorg. Med. Chem. Lett. 2004, 14, 2099.
  • Piazza, G. A. Method of treating a patient having precancerous lesions with phenyl purinone derivatives, Highlands Ranch Patent N0. US 6,200,980 B1, 2001.
  • Mojzych, M.; Karczmarzyk, Z.; Wysocki, W.; Ceruso, M.; Supuran, C. T.; Kryštof, V.; Urbańczyk-Lipkowska, Z.; Kalicki, P. Bioorg. Med. Chem. 2015, 23, 1421.
  • Mojzych, M.; Rykowski, A. Polish J. Chem. 2003, 77, 1797.
  • Mojzych, M.; Rykowski, A. J. Heterocycl. Chem. 2007, 44, 1003.
  • Mojzych, M. J. Chem. Soc. Pak. 2011, 33, 123.
  • Alphonse, F. A.; Suzenet, F.; Keromnes, A.; Lebret, B.; Guillaumet, G. Synlett 2002, 447.
  • Mojzych, M.; Dolashki, A.; Voelter, W. Bioorg. Med. Chem. 2014, 22, 6616.
  • Poraj-Kobielska, M.; Kinney, M.; Ulrich, R.; Scheibner, K.; Kayser, G.; Hammel, K. E.; Hofrichter, M. Biochem. Pharmacol. 2011, 82, 789.
  • Savanna, M.; Satyanarayana, B.; Pratapreddy, P. Chem. Biol. Interface 2011, 1, 177.
  • Dugar, S.; Hollinger, P. F.; Mahajan, D. Substituted methylformyl reagents and method of using same to modify physicochemical and/or pharmacokinetic properties of compounds, WO 2012137225 A1, 2012.
  • Macro, W. D. Artificially synthesized antigen of sildenafil and derivatives thereof as well as preparation method and application of antigen, CN 102161662 A, 2011.
  • Butrous, G. S.; Lukas, T.; Machin, I. Treatment of pulmonary hyper-tension with sildenafil or other phosphodiesterase Vinhibitor, European Patent Applications, 1097711, 2001.
  • Del, S. P. Nitrate salts of antihypertensive medicines, WO 1999067231 A1, 1999.
  • Stepanovs, D.; Jure, M.; Mishnev, A. Mendeleev Commun. 2015, 25, 49.
  • Qi, Y. Phenylsulfonyl-piperazine derivatives and their preparation, pharmaceutical compositions and use in the treatment of male erectile dysfunction. Faming Zhuanli Shenqing, 101870699, 2010.
  • Yan, S.; Duan, B. Preparation of pyrazolopyrimidine–thione derivatives for treatment of male erectile dysfunction, Faming Zhuanli Shenqing, 101343275, 2009.
  • Kim, J-H.; Kim, Y.; Choi, K.; Kim, D. H.; Nam, G.; Seo, J. H. Novel pyrazolopyrimidinethione derivatives. Preparation methods thereof and their use as therapeutics for erectile dysfunction, WO 2002102802 A1, 2002.

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