Synthesis and stability of two indomethacin prodrugs

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 7, 2006, Pages 1874-1879

  Chandrasekaran, Shyamala ^a   Al Ghananeem, Abeer M ^a   Riggs, Robert M ^a   Crooks, Peter A ^a  

^a University of Kentucky   (United States)

Author keywords

Indomethacin; Prodrug; Stability

Indexed keywords

1 [1 3 [(4 CHLOROBENZOYL) 5 METHOXY 2 METHYLINDOL ACETAMIDO]] 3,6 DIOXAOCTANE; 1 [1 3 [(4 CHLOROBENZOYL) 5 METHOXY 2 METHYLINDOL ACETOXY]] 3,6 DIOXAOCTANE; AMIDE; ESTER DERIVATIVE; INDOMETACIN DERIVATIVE; PRODRUG; UNCLASSIFIED DRUG;

ARTICLE; CONJUGATION; DEGRADATION; DRUG SYNTHESIS; HYDROLYSIS;

ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HYDROGEN-ION CONCENTRATION; INDOMETHACIN; MAGNETIC RESONANCE SPECTROSCOPY; PRODRUGS; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 33144489030     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.01.003     Document Type: Article

References (23)

1. F.E. Bruckner, and A.P. Randle Ann. Phys. Med. 13 1965 100
2. T. Ogawa, K. Ohara, H. Shimizu, T. Terai, and N. Watanabo Jap. J. Ophthalmol. 39 1995 353
3. O.M. Durrani, N.N. Tehrani, J.E. Marr, P. Moradi, P. Stavrou, and P.I. Murray Br. J. Ophthalmol. 88 2004 1159
4. L.A. Lobes Jr., and M.G. Grand Arch. Ophthalmol. 98 1980 1230
5. F.L. Ferris 3rd, and A. Patz Surv. Ophthalmol. 28 1984 452
6. R.M. Klein, H.M. Katzin, and L.A. Yannuzzi Am. J. Ophthalmol. 87 1979 487
7. L.A. Yannuzzi, R.M. Klein, R.H. Wallyn, N. Cohen, and I. Katz Am. J. Ophthalmol. 84 1977 517
8. D.B. Sholiton, W.J. Reinhart, and K.E. Frank J. Am. Intra-Ocular Implant Soc. 5 1979 137
9. G.A. Peyman, and J.A. Schulman Jap. J. Ophthalmol. 33 1989 392
10. I.M. Katz Ophthalmology 88 1987 455
11. P. Ashton, K. Walters, K.R. Brian, and J. Hadgraft Int. J. Pharm. 87 1992 256
12. D.D. Tang-Liu, and S. Liu J. Pharm. Biopharm. 15 1987 387
13. S. Riegelman, and W. Crowell J. Am. Pharm. Assoc. 47 1958 123
14. K.A. Walters, P.H. Dugart, and A.T. Florence J. Pharm. Pharmacol. 33 1981 207
15. T. Nishiyama, Y. Iwata, K. Nakajima, and T. Mitsui J. Soc. Cosmet. Chem. 34 1973 263
16. V.S. Chadwich, S.F. Philips, and A.F. Hofmann Gastroenterology 73 1977 241
17. V.S. Chadwich, S.F. Philips, and A.F. Hofmann Gastroenterology 73 1977 247
18. R.T. Blickenstaff J. Am. Chem. Soc. 82 1960 3673
19. J.M. Harris, E.C. Struck, M.G. Case, M.S. Paley, Van A.J. Yalpani, and D.D. Brooks J. Polymer Sci. 22 1984 341
20. R.C. Reynolds, P.A. Crooks, W.B. Parker, J.A. Maddry, J.A. Montgomery, and J.A. Secrist III J. Pharm. Sci. 2 1991 195
21. S. Hanessian, and P. Lavalle Can. J. Chem. 53 1975 2975
22. A.H. Kahns, P.B. Jenson, N. Mork, and H. Bundgaard Acta Pharm. Nord. 6 1989 327
23. 3); 6.18 (1H, t, NH); 6.64-6.68 (1H, m, 6′-CH); 6.82-6.85 (1H, apparent d, 7′-CH); 6.86-6.88 (1H, apparent d, 4′-CH); 7.42-7.51 (2H, apparent d, 2″, 6″-CH's); 7.62-7.64 (2H, apparent d, 3′, 5′-CH's). Elemental analysis: theoretical C, 61.41; H, 5.98; N, 5.73; found: C, 61.66; H, 6.04; N, 5.66 %.