A structure-Permeability study of small drug-like molecules

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 4, 2003, Pages 719-722

  Fichert, Thomas ^a   Yazdanian, Mehran ^a   Proudfoot, John R ^a  

^a BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TETRAZOLE DERIVATIVE;

ARTICLE; BIODIVERSITY; DRUG PENETRATION;

EID: 0037292994     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(02)01035-1     Document Type: Article

References (37)

1. (a) Balimane P.V., Chong S., Morrison R.A. J. Pharm. Tox. Meth. 44:2000;301
2. (b) Bailey C.A., Bryla P., Malick A.W. Adv. Drug Deliv. Rev. 22:1996;85
3. (c) Lee C.-P., de Vrueh R.L.A., Smith P.L. Adv. Drug Deliv. Rev. 23:1997;47
4. (d) Quaroni A., Hochman J. Adv. Drug Deliv. Rev. 22:1996;3
5. (e) Artursson P., Palm K., Luthman K. Adv. Drug Deliv. Rev. 22:1996;67
6. (f) Yee S. Pharm. Res. 14:1997;763
7. (g) Stewart B.H., Chan O.H., Lu R.H., Reyner E.L., Schmid H.L., Hamilton H.W., Steinbaugh B.A., Taylor M.D. Pharm. Res. 12:1995;693.
8. (a) Yazdanian M., Glynn S.L., Wright J.L., Hawi A. Pharm. Res. 15:1998;1490
9. (b) Lipinski C.A., Lombardo F., Dominy B.W., Feeney P.J. Adv. Drug Deliv. Rev. 46:2001;3
10. (c) Stenberg P., Norinder U., Luthman K., Artursson P. J. Med. Chem. 44:2001;1927.
11. Proudfoot J.R., Betageri I., Cardozo M., Gilmore T.A., Glynn S., Hickey E.R., Jakes S., Kabcenell A., Kirrane T.M., Tibolla A.K., Lukas S., Patel U.R., Sharma R., Yazdanian M., Moss N., Beaulieu P.L., Cameron D.R., Ferland J.-M., Gauthier J., Gillard J., Gorys V., Poirier M., Rancourt J., Wernic D., Llinas-Brunet M. J. Med. Chem. 44:2001;2421.
12. (a) Sugano K., Yoshida S., Takaku M., Haramura M., Saitoh R., Nabuchi Y., Ushio H. Bioorg. Med. Chem. Lett. 10:2000;1939
13. (b) Papageorgiou C., Camenisch G., Borer X. Bioorg. Med. Chem. Lett. 11:2001;1549
14. (c) Conradi R.A., Hilgers A.R., Ho N.F.H., Burton P.S. Pharm. Res. 9:1992;435
15. (d) Conradi R.A., Hilgers A.R., Ho N.F.H., Burton P.S. Pharm. Res. 8:1991;1453.
16. Based on the computational approach to evaluate the drug-like character of novel compounds developed by Xu and Stevenson, the compounds in this study are highly drug-like. Xu J., Stevenson J. J. Chem. Inf. Comput. Sci. 40:2000;1177 (a) Lipinski C.A. J. Pharm. Tox. Meth. 44:2000;235 (b) Hörter D., Dressman J.B. Adv. Drug Deliv. Rev. 46:2001;75.
17. Based on the computational approach to evaluate the drug-like character of novel compounds developed by Xu and Stevenson, the compounds in this study are highly drug-like. Xu J., Stevenson J. J. Chem. Inf. Comput. Sci. 40:2000;1177 (a) Lipinski C.A. J. Pharm. Tox. Meth. 44:2000;235 (b) Hörter D., Dressman J.B. Adv. Drug Deliv. Rev. 46:2001;75.
18. Based on the computational approach to evaluate the drug-like character of novel compounds developed by Xu and Stevenson, the compounds in this study are highly drug-like. Xu J., Stevenson J. J. Chem. Inf. Comput. Sci. 40:2000;1177 (a) Lipinski C.A. J. Pharm. Tox. Meth. 44:2000;235 (b) Hörter D., Dressman J.B. Adv. Drug Deliv. Rev. 46:2001;75.
19. 1H NMR, MS and elemental analysis or HRMS.
20. (a) Yee Y.K., Bernstein P.R., Adams E.J., Brown F.J., Cronk L.A., Hebbel K.C., Vacek E.P., Krell R.D., Snyder D.W. J. Med. Chem. 33:1990;2437
21. (b) Blangey L., Fierz-David H., Stamm G. Helv. Chim. Acta. 25:1942;1162.
22. Krapcho A.P., Gallagher C.E., Hammach A., Hacker M.P., Menta E., Oliva A., Di Domenico R., Da Re G., Lotto A., Spinelli S. J. Heterocyclic Chem. 35:1998;895.
23. (a) Krapcho A.P., Gallagher C.E., Hammach A., Ellis M., Menta E., Olivia A. J. Heterocyclic Chem. 34:1997;27
24. (b) Negishi E. Acc. Chem. Res. 15:1982;340.
25. Tao B., Huang T.L., Zhang Q., Jackson L., Queener S.F., Donkor I.O. Eur. J. Med. Chem. 34:1999;531.
26. Ellingboe J.W., Antane M., Nguyen T.T., Collini M.D., Antane S., Bender R., Hartupee D., White V., McCallum J., Park C.H., Russo A., Osler M.B., Wojdan A., Dinish J., Ho D.M., Bagli J.F. J. Med. Chem. 37:1994;542.
27. Schwarz M.K., Tumelty D., Gallop M. J. Org. Chem. 64:1999;2219.
28. Due to the hydrolytic instability of methyl ester 3 under the assay conditions, no data was generated for this or for the other methyl esters 10, 17, 21 and 22. The nitriles 7 and 9 were not tested since nitriles 2 and 8 displayed essentially the same permeability as the unsubstituted core structures 1 and 6.
29. Liang E., Proudfoot J., Yazdanian M. Pharm. Res. 17:2000;1168.
30. (a) Flynn G.L., Yalkowski S.H., Roseman T.J. J. Pharm. Sci. 63:1974;479
31. (b) Gao J., Murase O., Schowen R.L., Aube J., Borchardt R.T. Pharm. Res. 2001;171.
32. Newkome G.R., Paudler W.W. Contemporary Heterocyclic Chemistry. 1982;John Wiley and Sons, New York. p 404.
33. Patani G., LaVoie E.J. Chem. Rev. 96:1996;3147.
34. (a) Zhang Y., Benet L.Z. Clin. Pharmacokinet. 40:2001;159
35. (b) Tsuji A., Takanaga H., Tamai I., Terasaki T. Pharm. Res. 11:1994;30
36. (c) Seelig A. Eur. J. Biochem. 251:1998;254
37. (d) Takanaga H., Tamai I., Tsuji A. J. Pharm. Pharmacol. 46:1994;567.