Process development of a dual MMP/TNF inhibitor (SDZ 242-484)

Organic Process Research and Development

Volumn 6, Issue 5, 2002, Pages 652-659

  Koch, Guido ^a   Kottirsch, Georg ^a   Wietfeld, Bernhard ^a   Küsters, Ernst ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BENZYL DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; ENZYME INHIBITOR; HYDROXAMIC ACID; HYDROXAMIC ACID DERIVATIVE; LEWIS ACID; MATRIX METALLOPROTEINASE; N 4 (2,2 DIMETHYL 1 METHYLCARBAMOYLPROPYL) N 1 HYDROXY 2 HYDROXYMETHYL 3 (4 METHOXYPHENYL)SUCCINAMIDE; OSMIUM TETRAOXIDE; PHENETHYLAMINE; SDZ 242 484; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; CHIRALITY; CHROMATOGRAPHY; CLAISEN IRELAND REARRANGEMENT; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOMER; HYDROGENATION; OXIDATION; PROCESS DEVELOPMENT; STEREOCHEMISTRY; SYNTHESIS;

EID: 0036747146     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op025536e     Document Type: Article

References (25)

1. (a) Kottirsch, G.; Neumann, U.; Feifel, R.; Koch, G. J. Med. Chem. 2002. In press
2. (b) Kottirsch, G.; Neumann, U. WO 9814424 A1.
3. Boger, D. L.; Palanki, M. S. S. J. Am. Chem. Soc. 1992, 114, 9318.
4. (a) Harding, K. E.; Hollingsworth, D. R. Tetrahedron Lett. 1988, 29, 3789.
5. (b) Kurth, M. J.; Decker, O. H. W. J. Org. Chem. 1985, 50, 5769.
6. (c) Kizil, M.; Murpy, J. A. Tetrahedron 1997, 53, 16847.
7. Neises, B.; Steglich, W. Angew. Chem. 1978, 90, 556.
8. For reviews see: (a) Fraenrath, H. Methods of Organic Chemistry (Houben-Weyl), 4th ed.; G. Thieme: Stuttgart, 1952 and 1995; Vol. E21d, p 3301.
9. (b) Schubert, P.; Srebnik, M. Aldrichimica Acta 1993, 26, 17.
10. (c) Wipf, P. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991, Vol. 5, 827.
11. Koch, G.; Kottirsch, G.; Wietfeld, B.; Küsters, E. Tetrahedron Lett. 2002, in press.
12. For a review see: Juaristi, E.; Escalante, E.; León-Romo, J. L.; Reyes, A. Tetrahedron: Asymmetry 1998, 9, 715.
13. (a) Boissonnas, R. A. Helv. Chim. Acta 1951, 34, 874; Helv. Chim. Acta 1952, 35, 2229 and 2237.
14. (a) Boissonnas, R. A. Helv. Chim. Acta 1951, 34, 874; Helv. Chim. Acta 1952, 35, 2229 and 2237.
15. (b) Wieland, T.; Bernhard, H. Liebigs Ann. 1951, 572, 190.
16. (a) Staab, H. A.; Lüking, M.; Dürr, F. H. Chem. Ber. 1962, 95, 1275.
17. (b) Staab, H. A. Angew. Chem. 1962, 74, 407.
18. Kaminsky, Z. J.; Paneth, P.; Rudzinsky, J. J. Org. Chem. 1998, 63, 4248.
19. Bosshard, H. H.; Zollinger, H. C. H. Angew. Chem. 1959, 71, 375.
20. VanRheenen, V.; Kelly, R. C.; Cha, D. Y. Tetrahedron Lett. 1976, 17, 1973.
21. (a) Erdik, E.; Kahya, D.; Daskapan, T. Synth. Commun. 1998, 28, 1.
22. (b) Oishi, T.; Hirama, M. Tetrahedron Lett. 1992, 33, 639.
23. For a review see: Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
24. Lemieux, R. U.; von Rudloff, E. Can. J. Chem. 1955, 33, 1701, 1710. von Rudloff, E. Can. J. Chem. 1965, 43, 1784.
25. Lemieux, R. U.; von Rudloff, E. Can. J. Chem. 1955, 33, 1701, 1710. von Rudloff, E. Can. J. Chem. 1965, 43, 1784.