Design of concise, scalable route to a cholecystokinin 1 (CCK 1) receptor antagonist

Journal of Organic Chemistry

Volumn 72, Issue 22, 2007, Pages 8243-8250

  Liang, Jimmy T ^a   Mani, Neelakandha S ^a   Jones, Todd K ^a  

^a JOHNSON AND JOHNSON PHARMACEUTICAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENIC KETONES; CRYSTALLINE SODIUM; PROPIONIC ACIDS; RECEPTOR ANTAGONIST;

ENZYME ACTIVITY; HYDRAZINE; HYDROLYSIS; KETONES; POLYPEPTIDES; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

HORMONES;

3 [5 (3,4 DICHLOROPHENYL) 1 (4 METHOXYPHENYL) 1H PYRAZOL 3 YL] 2 (3 TOLYL PROPIONIC ACID; ACETYLENIC KETONE; CHOLECYSTOKININ A RECEPTOR ANTAGONIST; HYDRAZINE; KETENE DERIVATIVE; KETONE DERIVATIVE; LACTIC ACID ETHYL ESTER; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; HYDROLYSIS; STEREOCHEMISTRY;

ALKYNES; DRUG DESIGN; ESTERS; HYDROLYSIS; KINETICS; LACTATES; MOLECULAR STRUCTURE; PROPIONIC ACIDS; PYRAZOLES; RECEPTOR, CHOLECYSTOKININ A; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 35548948991     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo071166m     Document Type: Article

References (49)

1. (a) Ivy, A. C.; Oldberg, E. Am. J. Physiol. 1928, 86, 599-613.
2. (b) Mutt, V.; Jorpes, E. Biochem. J. 1971, 125, 57-58.
3. de Tullio, P.; Delarge, J; Pirotte, B. Exp. Opin. Invest. Drugs 2000, 9, pp 129-146; Patent WO 2004/007463 A1.
4. (a) McClure, K.; Hack, M.; Huang, L.; Sehon, C.; Morton, M.; Li, L.; Barrett, T. D.; Shankley, N.; Breitenbucher, J. G. Bioorg. Med. Chem. Lett. 2006, 16, 72-76.
5. (b) Sehon, C.; McClure, K.; Hack, M.; Morton, M.; Li, L.; Barrett, T. D.; Shankley, N.; Breitenbucher, J. G. Bioorg. Med. Chem. Lett. 2006, 16, 77-80.
6. See Supporting Information for details of this route.
7. (a) Evans, D. A.; Ennis, M. D.; Mathre, D. J. J. Am. Chem. Soc. 1982, 104, 1737-1739.
8. (b) Evans, D. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, pp 1-110.
9. (c) Ghosh, A. K.; Duong, T. T.; McKee, S. P. J. Chem. Soc., Chem. Commun. 1992, 1673-1674.
10. (d) Evans, D. A.; Britton, T. C.; Ellman, J. A.; Dorow, R. L. J. Am. Chem. Soc. 1990, 112, 4011-4030.
11. (e) Evans, D. A.; Britton, T. C.; Ellman, J. A. Tetrahedron Lett. 1987, 28, 6141-6144.
12. (a) Kost, A. N.; Grandberg, I. I. Adv. Heterocycl. Chem. 1966, 6, 347-429.
13. (b) Elguero, J. Pyrazoles. In Comprehensive Heterocyclic Chemistry; Potts, K. T., Ed.; Pergamon: Oxford, 1984; Vol. 5, pp 167-303.
14. (c) Elguero, J. Pyrazoles. In Comprehensive Heterocyclic Chemistry; Shinkai, I., Ed.; Pergamon: Oxford, 1996; Vol. 3, pp 1-75.
15. (d) Murray, W.; Wachter, M. J. Heterocycl. Chem. 1989, 26, 1389-1392.
16. (a) Moureu, Ch.; Delange, R. Bull. Soc. Chim. Fr. 1901, 25, 302-313;
17. Ann. Chim. Phys. 1902, 25, 239.
18. (b) Claisen, L. Ber. Dtsch. Chem. Ges. 1903, 36, 3664-3674.
19. (a) Chowdhury, C.; Kundu, N. G. Tetrahedron 1999, 55, 7011-7016.
20. (b) Grotjahn, D. B.; Van, S.; Combs, D.; Lev, D. A.; Schneider, C.; Rideout, M.; Meyer, C.; Hernandez, G.; Mejorado, L. J. Org. Chem. 2002, 67, 9200-9209.
21. (a) Cabarrocas, G.; Ventura, M.; Maestro, M.; Mahia, J.; Villalgordo, J. M. Tetrahedron: Asymmetry 2000, 11, 2483-2493.
22. (b) Miller, R. D.; Reiser, O. J. Heterocycl. Chem. 1993, 30, 755-763.
23. Bishop, B. C.; Brands, K. M. J.; Gibb, A. D.; Kennedy, D. J. Synthesis 2004, 1, 43-52.
24. (a) Acetylenic Compounds in Organic Synthesis; Accademic Press: New York, 1995.
25. (b) The Chemistry of Carbon-Carbon Triple Bond, Part 1; John Wiley and Sons: New York, 1978; Chapter 10, pp 381-445.
26. Trost, B. M.; Schmidt, T. J. Am. Chem. Soc. 1988, 110, 2301-2303 and references cited therein.
27. (a) Carey, J. S.; Laffan, D.; Thomson, C.; Williams, M. T. Org. Biomol. Chem. 2006, 4, 2337-2347.
28. (b) Armstrong, J. D., III; Martinelli, M. J.; Senanayake, C. S. Tetrahedron: Asymmetry 2003, 14, 3425-3426.
29. (c) Kataoka, M.; Shimizu, K.; Sakamoto, K; Yamada, H.; Shimizu, S. Appl. Microbiol. Biotechnol. 1995, 43, 974-977.
30. (d) Shimizu, S.; Kataoka, M.; Shimizu, K; Hirakata, M.; Sakamoto, K.; Yamada, H. Eur. J. Biochem. 1992, 209, 383-390.
31. (e) Shimizu, S.; Kataoka, M. Ann. N.Y. Acad. Sci. 1996, 799, 650-659.
32. Two screening test kits were purchased. Screening kit ChiroScreen-EH containing 30 enzymes was purchased from Altus Biologics Inc., 625 Putnam Ave., Cambridge, MA 02139-4211. Web site: www.Altus.com. Tel: 1-888-258-2532. Fax: 1-617-299-2999. Screening set CHIRAZYME Lipases & Esterases containing 24 enzymes were purchased from BioCatalytics, 129 Hill Ave., Suite 103, Pasadena, CA 91106-1955. Tel: (626) 585-9797. Fax: (626) 356-3999. Both enzyme sets are suited for hydrolysis and transesterification reactions.
33. (a) Lubell, W. D.; Rapoport, H. J. Am. Chem. Soc. 1988, 110, 7447-7455.
34. (b) Castaldi, G.; Cavicchioli, S.; Giordano, C.; Uggeri, F. J. Org. Chem. 1987, 52, 3018-3027.
35. (c) Honda, Y.; Ori, A.; Tsuchihashi, G. Bull. Chem. Soc. Jpn. 1987, 60, 1027-1036.
36. (d) Ando, A.; Shioiri, T. J. Chem. Soc., Chem. Commun. 1987, 656-658.
37. (e) Rieu, J.-P.; Boucherle, A.; Cousse, H.; Mouzin, G. Tetrahedron 1986, 42, 4095-4131.
38. (f) Piccolo, O.; Spreafico, F.; Visentin, G. J. Org. Chem. 1985, 50, 3945-3946.
39. (a) Weiss, R. Mh. Chem. 1919, 40, 391;
40. Anders, E.; Ruch, E. Angew. Chem., Int. Ed. Engl. 1973, 12, 25-29.
41. (b) Jaehme, J.; Ruechardt, C. Angew. Chem., Int. Ed. Engl. 1981, 20, 885-886.
42. (c) Salz, U.; Ruechardt, C. Tetrahedron Lett. 1982, 23, 4017-4020.
43. (d) Bellucci, G.; Berti, G.; Bianchini, R.; Vecchiani, S. Gazz. Chim. Ital. 1988, 118, 451-456.
44. (e) Buschmann, H.; Scharf, H.-D.; Hoffmann, N.; Esser, P. Angew. Chem. 1991, 103, 490-518.
45. (f) Fehr, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2567-2587.
46. (g) Donohoe, G.; Satchell, D. P. N.; Satchell, R. S. J. Chem. Soc., Perkin Trans. 2 1990, 1671-1674.
47. (h) Hodous, B. L.; Ruble, J. C.; Fu, G. C. J. Am. Chem. Soc. 1999, 121, 2637-2638.
48. Larsen, R. D.; Corley, E. G.; Davis, P.; Reider, P. J.; Grabowski, E. J. J. J. Am. Chem. Soc. 1989, 111, 7650-7651.
49. -1.