Synthesis of commercial phosphodiesterase(V) inhibitors

Organic Process Research and Development

Volumn 9, Issue 1, 2005, Pages 88-97

  Dunn, Peter J ^a  

^a PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHODIESTERASE V INHIBITOR; SILDENAFIL; TADALAFIL; VARDENAFIL;

AMMONOLYSIS; CHIRALITY; CYCLIZATION; DRUG INHIBITION; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; FRIEDEL CRAFTS REACTION; HYDROGENATION; METHYLATION; REVIEW; RING CLOSING METATHESIS; SCALE UP; STRUCTURE ACTIVITY RELATION;

EID: 13844272010     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op040019c     Document Type: Review

References (48)

1. Boolell, M.; Allen, M. J.; Ballard, S. A.; Gepi-Attee, S.; Muirhead, G. J.; Naylor, A. M.; Osterloh, I. H.; Gingell, J. C. Int. J. Impot. Res. 1996, 8, 47-52.
2. Wilkens, H.; Guth, A.; Konig, J.; Forestier, N.; Cremers, B.; Hennen, B.; Bohm, M.; Sybrecht, G. W. Effect of inhaled iloprost plus sildenafil in patients with primary pulmonary hypertension. Circulation 2001, 104, 1218-1222.
3. Figures for sildenafil and tadalafil are taken from sales figures released by Pfizer and Lily/ICOS, respectively. Figures for vardenafil are based upon estimates provided by Wood Mackenzie. The 2004 figures are estimates.
4. 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, 17-22. See also Dunn, P. J.; Wood, A. S. European Patent, EP 0 812 845.
5. 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, 17-22. See also Dunn, P. J.; Wood, A. S. European Patent, EP 0 812 845.
6. Dunn, P. J.; Galvin, S.; Hettenbach, K. Green Chemistry 2004, 6, 43-48.
7. Bunnage, M. E.; Levett, P. C.; Thomson, N. M. World Patent, WO 01/ 98303.
8. 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 01/22918.
9. Dunn, P. J.; Dunne, C. World Patent, WO 01/98284.
10. Dunn, P. J. Unpublished results.
11. Dumaitre, B.; Dodic, N. J. Med. Chem. 1996, 39, 1635-1644.
12. Yang, D.; Wang, H.; Shi, H. Chinese Patent CN 99-111153, 2001 (Chem. Abs. 2001, 135, 242238) and Yang, D.; Wang, H.; Shi, H. Chinese Patent CN-109345 (Chem. Abs. 2001, 135, 107334).
13. Yang, D.; Wang, H.; Shi, H. Chinese Patent CN 99-111153, 2001 (Chem. Abs. 2001, 135, 242238) and Yang, D.; Wang, H.; Shi, H. Chinese Patent CN-109345 (Chem. Abs. 2001, 135, 107334).
14. Chaudhari, D. T.; Deshpande, P. B.; Khan, R. A. R. European Patent, EP 1 002 798.
15. Dunn, P. J.; Levett, P. C. European Patent, EP 0 994 115.
16. Lu, Y.-F.; Antczak, C.; Tao, Y.; Oudenes, J. Canadian Patent 2 235 642.
17. Matier, W. L.; Comer, W. T.; Deitchman, D. J. Med. Chem. 1972, 15, 538-541.
18. Chaudhari, D. T.; Deshpande, P. B.; Khan, R. A. R. European Patent, EP 1 077 214.
19. Bell, A. S.; Brown, A. S.; Terrett, N. K. European Patent, EP 0 463 756, 1991. Terrett, N. K.; Bell, A. S.; Brown, D.; Ellis, P. Bioorg. Med. Chem. Lett. 1996, 6, 1819-1824.
20. Bell, A. S.; Brown, A. S.; Terrett, N. K. European Patent, EP 0 463 756, 1991. Terrett, N. K.; Bell, A. S.; Brown, D.; Ellis, P. Bioorg. Med. Chem. Lett. 1996, 6, 1819-1824.
21. Kankan, R. N. R.; Rao, D. R. World Patent, WO 01/19827.
22. th March, 2001.
23. Lednicer, D. In The Organic Chemistry of Drug Synthesis; Wiley-Interscience: New York; Vol. 6, p 180 [ISBN 0-471-24510-10 (v6)].
24. Lourdes, I.; Concepcion, F.-F.; Rosa, M. C.; Concepcion, L.; Jagerovic, N.; Elguero, J. Heterocycles 1999, 50, 227-242.
25. Kopp, M.; Lancelot, J.-C.; Dallemange, P.; Rault, S. J. Heterocycl. Chem. 2001, 38, 1045-1050.
26. Muller, N.; Matzke, M. U.S. Patent 6,444,828 (note under certain conditions the regiochemistry for the methylhydrazine reaction can be 13:1).
27. Muller, N.; Matzke, M. U.S. Patent 6,297,386.
28. Heuer, L.; Muller, N.; Steffan, G. European Patent, EP 0 819 678, in German, same authors U.S. Patent 5,969,152, 1999 and U.S. Patent 6,025,499, in English.
29. Baxendale, I. R.; Ley, S. V. Bioorg. Med. Chem. Lett. 2000, 10, 1983-1986.
30. Haning, H.; Niewohner, U.; Schenke, T.; Es-Sayed, M.; Schmidt, G.; Lampe, T.; Bischoff, E. Bioorg. Med. Chem. Lett. 2002, 12, 865-868. Niewohner, U.; Es-Sayed, M.; Haning, H.; Schenke, T.; Schlemmer, K.-H.; Keldenich, J.; Bischoff, E.; Perzborn, E.; Dembowsky, K.; Serno, P.; Nowakowski, M. U.S. Patent 6,362,178 (see also Sorbera, L. A.; Martin, L.; Rabasseda, X.; Castaner, J. Drugs Future 2001, 26(2), 141-144).
31. Haning, H.; Niewohner, U.; Schenke, T.; Es-Sayed, M.; Schmidt, G.; Lampe, T.; Bischoff, E. Bioorg. Med. Chem. Lett. 2002, 12, 865-868. Niewohner, U.; Es-Sayed, M.; Haning, H.; Schenke, T.; Schlemmer, K.-H.; Keldenich, J.; Bischoff, E.; Perzborn, E.; Dembowsky, K.; Serno, P.; Nowakowski, M. U.S. Patent 6,362,178 (see also Sorbera, L. A.; Martin, L.; Rabasseda, X.; Castaner, J. Drugs Future 2001, 26(2), 141-144).
32. Haning, H.; Niewohner, U.; Schenke, T.; Es-Sayed, M.; Schmidt, G.; Lampe, T.; Bischoff, E. Bioorg. Med. Chem. Lett. 2002, 12, 865-868. Niewohner, U.; Es-Sayed, M.; Haning, H.; Schenke, T.; Schlemmer, K.-H.; Keldenich, J.; Bischoff, E.; Perzborn, E.; Dembowsky, K.; Serno, P.; Nowakowski, M. U.S. Patent 6,362,178 (see also Sorbera, L. A.; Martin, L.; Rabasseda, X.; Castaner, J. Drugs Future 2001, 26(2), 141-144).
33. Isabel, C.; Latham, D. W. S.; Hartley, D.; Oxford, A. W.; Scopes, D. I. C. J. Chem. Soc., Perkin Trans. 1 1980, 1139-1146.
34. Marshall, D. R. Chem. Ind. 1983, 331-335.
35. Garigipati, R. S. Tetrahedron Lett. 1990, 31, 1969-1972.
36. Levin, J. I.; Turos, E.; Weinreb, S. M. Synth. Commun. 1982, 12(13), 989-993.
37. Nowakowski, M.; Gehring, R.; Heilman, W.; Wahl, K.-H. World Patent, WO 02/50076.
38. Nowakowski, M.; Vetter, A. World Patent, WO 02/50075.
39. Saxena, A. K.; Padam, C. J.; Anand, N.; Dua, R. R. J. Med. Chem. 1973, 16, 560-564 (see also Madrigal, A.; Grande, M.; Avendano, C. J. Org. Chem. 1998, 63, 2724-2727).
40. Saxena, A. K.; Padam, C. J.; Anand, N.; Dua, R. R. J. Med. Chem. 1973, 16, 560-564 (see also Madrigal, A.; Grande, M.; Avendano, C. J. Org. Chem. 1998, 63, 2724-2727).
41. Sorbera, L. A.; Martin, L.; Leeson, P. A.; Castaner, J. Drugs Future 2001, 26(1), 15-19.
42. Daugan, A. C.-M. European Patent, EP 0740 668.
43. Daugan, A.; Grondin, P.; Ruault, C.; Le Monnier de Gouville, A.-C.; Coste, H.; Kirilovsky, J.; Hyafil, F.; Labaudiniere, R. J. Med. Chem. 2003, 46, 4525-4532.
44. Orme, M. W.; Sawyer, J. C.; Schultze, L. M. World Patent, WO 02/036593.
45. Orme, M. W.; Martinelli, M. J.; Doecke, C. W.; Pawlak, J. M. World Patent, WO 04/011463.
46. Daugan, A. C.-M. U.S. Patent 5,859,006.
47. Cava, M. P.; Levinson, M. I. Tetrahedron 1985, 41, 5061-5087.
48. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259-281.