α-(1H-Imidazol-1-yl)alkyl (IMIDA) carboxylic acid esters as prodrugs of carboxylic acid containing drugs

Tetrahedron Letters

Volumn 48, Issue 26, 2007, Pages 4609-4611

  Majumdar, Susruta ^a   Spaeth, Maren Mueller ^a   Sivendran, Sashikala ^a   Juntunen, Juha ^a   Thomas, Joshua D ^a   Sloan, K B ^a  

^a UNIVERSITY OF FLORIDA   (United States)

Author keywords

Carboxylic acids; IMIDA; Permeability; Prodrugs

Indexed keywords

ALPHA (1H IMIDAZOL 1 YL)CARBOXYLIC ACID ESTER DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BINDING; CHEMICAL COMPOSITION; HYDROLYSIS; PRODUCT RECOVERY; REACTION ANALYSIS; SYNTHESIS;

EID: 34249288959     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.04.121     Document Type: Article

References (18)

1. Bundgard H. In: Krogsgaard-Larsen P., and Bundgard H. (Eds). Design and Application of Prodrugs. In a Textbook of Drug Design and Development (1991), Harwood, Reading, UK 113-191
2. Sloan K.B. In: Sloan K.B. (Ed). Topical and Ocular Drug Delivery (1992), Merkel Dekker, New York 17-116
3. Bonina F.P., Montenegro L., De Caprariis P., Palagiano F., Trapani G., and Liso G. J. Controlled Release 34 (1995) 223-232
4. Bonina F.P., Puglia C., Barbuzzi T., De Caprariis P., Palagiano F., Rimoli M.G., and Saija A. Eur. J. Pharm. Sci. 14 (2001) 123-134
5. Sloan K.B., and Wasdo S. Med. Res. Rev. 23 (2003) 763-793
6. Sloan K.B., Koch S.A.M., and Siver K.G. Int. J. Pharm. 21 (1984) 251-264
7. Sloan K.B. Adv. Drug Delivery Rev. 3 (1989) 67-101
8. Jona J.A., Dittert L.W., Crooks P.A., Milosovich S.M., and Hussain A.A. Int. J. Pharm. 123 (1995) 127-136
9. Milosovich S., Hussain A., Dittert L., Aungst B., and Hussain M. J. Pharm. Sci. 82 (1993) 227-228
10. Rautio J., Nevalainen T., Taipale H., Vepsalainen J., Gynther J., Pederson T., and Jarvinen T. Pharm. Res. 16 (1999) 1172-1178
11. Klixbull U., and Bundgaard H. Arch. Pharm. Chem., Sci. Ed. 11 (1983) 101-110
12. 3): δ 7.37 (s, 1H), 7.06 (s, 1H), 6.91 (s, 1H), 5.4 (s, 2H).
13. Alley P.W. J. Org. Chem. 40 (1975) 1837-1838
14. 3: C, 69.33; H, 5.85; N, 9.03. Found: C, 69.19; H, 5.87; N, 8.85.
15. 3): δ 7.9 (2d, 1H), 7.3-7.6 (m, 5H), 7-6.8 (m, 3H), 6.67 (qq, 1H), 3.99 (2s, 3H), 3.9 (2q, 1H), 1.7-1.8 (2d, 3H), 1.65 (d, 3H).
16. Thomas J.D., and Sloan K.B. Tetrahedron Lett. 47 (2006) 8785-8787
17. t)) versus time.
18. Wasdo S., and Sloan K.B. Pharm. Res. 21 (2004) 940-946 and references cited therein