Synthesis of Montelukast (MK-0476) metabolic oxidation products

Journal of Organic Chemistry

Volumn 61, Issue 24, 1996, Pages 8518-8525

  Dufresne, Claude ^a   Gallant, Michel ^a   Gareau, Yves ^a   Ruel, Réjean ^a   Trimble, Laird ^a   Labelle, Marc ^a  

^a MERCK FROSST CENTRE FOR THERAPEUTIC RESEARCH   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG METABOLITE; MONTELUKAST;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029907397     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9615817     Document Type: Article

References (13)

1. Labelle, M.; Belley, M.; Gareau, Y.; Gauthier, J. Y.; Guay, D.; Gordon, R.; Grossman, S. G.; Jones, T. R.; Leblanc, Y.; McAuliffe, M.; McFarlane, C.; Masson, P.; Metters, K. M.; Ouimet, N.; Patrick, D. H.; Piechuta, H.; Rochette, C.; Sawyer, N.; Xiang, Y. B.; Pickett; C. B.; Ford-Hutchinson, A. W.; Zamboni, R. J.; Young, R. N. Bioorg. Med. Chem. Lett. 1995, 5, 293.
2. Schoors, D. F.; De Smet, M.; Reiss, T.; Margolskee, D.; Cheng, H.; Larson, P.; Amin, R.; Somers, G. Brit. J. Clin. Pharmacol. 1995, 40, 277.
3. Chauret, N.; Yergey, J.; Trimble, L.; Nicoll-Griffith, D. Presented at the 10th International Symposium on Microsomes & Drug Oxidations, Toronto, Canada, July 18-21, 1994.
4. (a) Labelle, M.; Belley, M.; Champion, E.; Gordon, R.; Hoogsteen, K.; Jones, T. R.; Leblanc, Y.; Lord, A.; McAuliffe, M.; McFarlane, C.; Masson, P.; Metters, K. M.; Nicoll-Griffith, D.; Ouimet, N.; Piechuta, H.; Rochette, C.; Sawyer, N.; Xiang, Y. B.; Ford-Hutchinson, A. W.; Pickett, C. B.; Zamboni, R. J.; Young, R. N. Biorg. Med. Chem. Lett. 1994, 4, 463-468.
5. (b) Nicoll-Griffith, D.; Yergey, J.; Trimble, L.; Williams, H.; Rasori, R.; Zamboni, R. Drug Metab. Dispos. 1992, 20, 383-389.
6. Syper, L. Tetrahedron Lett. 1966, 37, 4493.
7. Rabjohn, N. Org. React. 1976, 24, 261.
8. Lee, H.; Harvey, R. G. J. Org. Chem. 1988, 53, 4587.
9. Imamoto, T.; Takiyama, N.; Nakamura, K.; Hatajima, T.; Kamiya, Y. J. Am. Chem. Soc. 1989, 111, 4392.
10. VanRheenen, V.; Kelly, R. C.; Cha, D. Y. Tetrahedron Lett. 1976, 23, 1973.
11. Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K. S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768.
12. King, A. O.; Corley, E. G.; Anderson, R. K.; Larsen, R. D.; Verheoven, T. R.; Reider, P. J.; Xiang, Y. B.; Belley, M.; Leblanc, Y.; Labelle, M.; Prasit, P.; Zamboni, R. J. J. Org. Chem. 1993, 58, 3731-3735.
13. Johnson, C. R.; Medich, J. R. J. Org. Chem. 1988, 53, 4131.