An efficient, scalable synthesis of the HIV reverse transcriptase inhibitor Ziagen® (1592U89)

Nucleosides, Nucleotides and Nucleic Acids

Volumn 19, Issue 1-2, 2000, Pages 297-327

  Daluge, Susan M ^a   Martin, Michael T ^a   Sickles, Barry R ^a   Livingston, Douglas A ^a,b  

^a GLAXOSMITHKLINE   (United States)

^b Novartis Inst for Funct Genomics   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ABACAVIR; RNA DIRECTED DNA POLYMERASE INHIBITOR;

ANTIVIRAL ACTIVITY; ARTICLE; BIOAVAILABILITY; DRUG SYNTHESIS; ENZYME INHIBITION; HYDROGENATION; HYDROLYSIS; STEREOCHEMISTRY;

EID: 0034110180     PISSN: 15257770     EISSN: None     Source Type: Journal    
DOI: 10.1080/15257770008033011     Document Type: Article

References (51)

1. Shealy, Y. F.; Clayton, J. D. J. Am. Chem. Soc., 1966, 88, 3885-3887; 1969, 91, 3075-3083.
2. Shealy, Y. F.; Clayton, J. D. J. Am. Chem. Soc., 1966, 88, 3885-3887; 1969, 91, 3075-3083.
3. (a) Marquez, V. E., Advances in Antiviral Drug Design, 1996, 2, 89-146;
4. (b) Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron, 1994, 50, 10611-10670;
5. (c) Koszalka, G. W.; Daluge, S. M.; Boyd, L. F. Annual Reports in Med. Chem., 1998, 33, 163-171.
6. Daluge, S. M.; Good, S. S.; Faletto, M. B.; Miller, W. H.; St. Clair, M. H.; Boone, L. R.; Tisdale, M.; Parry, N. R.; Reardon, J. E.; Dornsife, R. E.; Averett, D. R; Krenitsky, T. A., Antimicrob. Agents Chemother., 1997, 41, 1082-1093.
7. Daluge, S. M.; LaFon, S. W.; Good, S. S.; St. Clair, M. H.; Livingston, D. A.; Martin, M. T. Antiviral Res., 1996, 30, A17.
8. th ACS National Meeting, Publisher American Chemical Society, Washington, D.C. 1997, 488765.
9. Vince, R.; Hua, M.; Brownell, J.; Daluge, S. M.; Lee, F. C.; Shannon, W. M.; Lavelle, G. C.; Qualls, J.; Weislow, O.S.; Kiser, R.; Canonico, P. G.; Schultz, R. H.; Narayanan, V. L.; Mayo, J. G.; Shoemaker, R. H.; Boyd, M. R. Biochem. Biophys. Res. Commun., 1988, 156, 1046-1053.
10. Trennery, P; Ayers, K. M., Medicines Safety Evaluation, Glaxo Wellcome Inc., personal communications.
11. Matsumura, Y.; Morisawa, Y., Yasuda, A., Uchida, K., Japanese Patent Application 64-22,853; January, 1989.
12. Faletto, M. B.; Miller, W. H.; Garvey, E. P.; St. Clair, M. H.; Daluge, S. M.; Good, S. S. Antimicrob. Agents Chemother., 1997, 41, 1099-1107.
13. (a) Daluge, S. M.; Good, S. S.; Martin, M. T.; Tibbels, S. R.; Miller, W. H.; Averett, D. R.; St. Clair, M. H.; Ayers, K. M. Abstracts of the 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, American Society for Mirobiology, Orlando, FL., 1994, abstr., 16, 7;
14. (b) Tisdale, M.; Parry, N. R.; Cousens, D.; St. Clair, M. H.; Boone, L. R., abstr. 182, 92;
15. (c) Faletto, M. B.; Miller, W. H.; Garvey, E. P.; Reardon, J. E.; Good, S. S., abstr. 184, 92;
16. (d) Good, S. S.; Owens, B. S.; Faletto, M. B.; Mahony, W. B.; Domin, B. A., abstr. 186, 92;
17. (e) Ching, S. V., Ayers, K. M.; Dornsife, R. E.; Lewis, D.; Grebe, G. L.; Howard, J. L., abstr. 188, 92.
18. Foster, R. H.; Faulds, D. Drugs, 1998, 55, 729-736.
19. Trost, B. M.; Kuo, G.-H.; Benneche, T. J. Am. Chem. Soc., 1988, 770, 621-622.
20. Crimmins, M. T. Tetrahedron, 1998, 54, 9229-9272 and references therein.
21. Crimmins, M. T.; King, B. W. J. Org. Chem., 1996, 67, 4192-4193.
22. O'Mahony, R., Glaxo Wellcome Chemical Development Division, personal communication.
23. 10e
24. Vince, R.; Hua, M. J. Med. Chem., 1990, 33, 17-21; U. S. Patent 4,916,224, April 1990.
25. Daluge, S. M. European patent 349242, January 1990.
26. (a) Jagt, J. C.; Van Leusen, A. M. Red. Trav. Chim. Pays-Bas, 1973, 92, 1343-1354;
27. (b) J. Org. Chem., 1974, 39, 564-566.
28. Daluge, S. M.; Vince, R. J. Org. Chem., 1978, 43, 2311-2320.
29. Montgomery, J. A.; Temple, Jr., C. J. Am. Chem. Soc., 1957, 79, 5238-5245.
30. Shealy, Y. F.; Clayton, J. D. J. Pharm. Sci., 1973, 62, 1432-1434.
31. Taylor, S. J. C.; Sutherland, A. G.; Lee, C.; Wisdom, R.; Thomas, S.; Roberts, S. M.; Evans, C., J. Chem. Soc. Chem. Commun., 1990, 1120-1121.
32. Griffiths, G. J.; Previdoli, F. E. J. Org. Chem., 1993, 58, 6129-6131.
33. The grade of calcium chloride was a critical factor, with technical grade resulting in better rates than reagent grade, possibly correlating with HCl content.
34. 50 15 ± 3 and 39 ± 10 μM, respectively, n = 15 marrows).
35. Sickles, B. R.; Locklear, M. J. Abstr. Ninth International IUPAC Conf. on Organic Synthesis, Montréal, Québec, 1992, MW-46, 163; manuscript in preparation.
36. House, H. O., "Modern Synthetic Reactions," Second Edition, W. A. Benjamin, Inc., Menlo Park, CA, 1972, p. 52.
37. Yamamoto, H; Maruoka, K. J. Am. Chem. Soc., 1981, 103, 4186-4194.
38. Daluge, S. M.; Livingston, D. A. International Patent WO 93/17020, September 1993.
39. W. H. Miller, manuscript in preparation.
40. Daluge, S. M., U. S. Patent 5,206,435, April 1993.
41. W. E. Weiser, personal communication; analysis of cyclopentenyl amines is an adaptation of methods described by: Brückner, H.; Wittner. R.; Godel, H. J. Chrom., 1989, 476, 73-82,
42. and Brückner, H.; Wittner, R.; Hausch, M.; Godel, H. Fresenius Z. Anal. Chem., 1989, 333, 775-776.
43. Katagiri, N.; Muto, M.; Kaneko, C. Tetrahedron Lett., 1989, 30, 1645-1648.
44. Taylor, S. J. C.; McCague, R.; Wisdom, R.; Lee, C.; Dickson, K.; Ruecroft, G.; O'Brien, F.; Littlechild, J.; Bevan, J.; Roberts, S. M.; Evans, C. T. Tetrahedron: Asymetry 1993, 4, 1117-1128.
45. Legraverend, M.; Boumchita, H.; Bisagni, E. Synthesis, 1990, 587-589.
46. Harnden, M. R.; Wyatt, P. G.; Boyd, M. R.; Sutton, D. J. Med. Chem., 1990, 33, 187-196.
47. (a) Hanson, J. C. U. S. Patent 5,216,161, June 1993. (b) International Patent WO 91/01310, February 1991.
48. Daluge, S. M.; Martin, M. T. U. S. Patent 5,917,041 and 5,917,042, June 1999.
49. Daluge, S. M.; Martin, M. T., manuscript in preparation.
50. Toyota, A.; Habutani, C.; Katagiri, N.; Kaneko, C. Tetrahedron Lett., 1994, 31, 5665-5668.
51. Temple, Jr., C.; Smith, B. H.; Montgomery. J. A. J. Org. Chem., 1975, 40, 3141-3142.