Synthesis, antiviral activity and pharmacokinetics of P1/P1′ substituted 3-aminoindazole cyclic urea HIV protease inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 4, 2003, Pages 605-608

  Kaltenbach III, Robert F ^a   Patel, Mona ^a   Waltermire, Robert E ^a   Harris, Gregory D ^a   Stone, Benjamin R P ^a   Klabe, Ronald M ^a   Garber, Sena ^a   Bacheler, Lee T ^a   Cordova, Beverly C ^a   Logue, Kelly ^a   Wright, Matthew R ^a   Erickson Viitanen, Susan ^a   Trainor, George L ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 (3 AMINO 5 INDAZOLYL) 4,7 DIBENZYL 3 BUTYL 2,3,4,5,6,7 HEXAHYDRO 5,6 DIHYDROXY 2H 1,3 DIAZEPIN 2 ONE; DMP 850; PROTEINASE INHIBITOR; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG BINDING; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG POTENCY; DRUG SYNTHESIS; HUMAN IMMUNODEFICIENCY VIRUS; IC 50; LIPOPHILICITY; NONHUMAN; SITE DIRECTED MUTAGENESIS; STEREOCHEMISTRY; SUBSTITUTION REACTION; VIRUS RESISTANCE;

EID: 0037292983     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(02)01064-8     Document Type: Article

References (17)

1. (a) Vacca J.P., Condra J.H. Drug Discov. Today. 2:1997;261
2. (b) Danner S.A., Carr A., Leonard J.M., Leman L.M., Gudiol F., Gonzales J., Raventos A., Rubio R., Bouza E., Pintado V., Aguado A.G., De Lomas J.G., Delgado R., Borleffs J.C.C., Hsu A., Valdes J.M., Boucher C.A.B., Cooper D.A. N. Engl. J. Med. 333:1995;1528.
3. (c) Markowitz M., Saag M., Powderly W.G., Hurley A.M., Hsu A., Valdes J.M., Henry D., Sattler F., La Marca A., Leonard J.M., Ho D.D. N. Eng. J. Med. 333:1995;1534
4. (d) Kitchen V.S., Skinner C., Ariyoshi K., Lane E.A., Duncan I.B., Burckhardt J., Burger H.U., Bragman K., Pinching A.J., Weber J.N. Lancet. 345:1995;952.
5. Rodgers J.D., Lam P.Y.S., Johnson B.L., Wang H., Ko S.S., Seitz S.P., Trainor G.L., Anderson P.S., Klabe R.M., Bacheler L.T., Cordova B.C., Garber S., Reid C., Wright M.R., Chang C.-H., Erickson-Viitanen S. Chem. Biol. 5:1998;597.
6. Rodgers J.D., Johnson B.L., Wang H., Erickson-Viitanen S., Klabe R.M., Bacheler L., Cordova B.C., Chang C.H. Bioorg. Med. Chem. Lett. 8:1998;715.
7. Kaltenbach R.F. III, Klabe R.M., Cordova B.C., Seitz S.P. Bioorg. Med. Chem. Lett. 9:1999;2259.
8. Computer generated Clog P was calculated using MedChem Software Release 3.32, Pomona College, Claremont, CA, USA.
9. Nugiel D.A., Jacobs K., Worley T., Patel M., Kaltenbach R.F. III, Meyer D.T., Jadhav P.K., DeLucca G.V., Smyser T.E., Klabe R.M., Bacheler L.T., Rayner M.M., Seitz S.P. J. Med. Chem. 39:1996;2156.
10. Rossano L.T., Lo Y.S., Anzalone L., Lee Y.-C., Meloni D.J., Moore J.R., Gale T.M., Arnett J.F. Tetrahedron Lett. 36:1995;4967.
11. Erickson-Viitanen S., Klabe R.M., Cawood P.G., O'Neal P.L., Meek J.L. Antimicrob. Agents Chemother. 38:1994;1628.
12. Bacheler L.T., Paul M., Jadhav P.K., Otto M., Stone B., Miller J. Antiviral Chem. Chemother. 5:1994;111.
13. Otto M.J., Reid C., Garber S., Lam P.Y.S., Scaranti H., Bacheler L.T., Rayner M.M., Winslow D. Antimicrob. Chemother. 37:1993;2606.
14. (a) King R.W., Garber S., Winslow D.L., Reid C., Bacheler L.T., Anton E., Otto M.J. Antiviral Chem. Chemother. 6:1995;80.
15. (b) Jadhav P.K., Ala P., Woerner F.J., Chang C.-H., Garber S.S., Anton E.D., Bacheler L.T. J. Med. Chem. 40:1997;181.
16. Ala P.J., Huston E.E., Klabe R.M., Jadhav P.K., Lam P.Y.S., Chang C.-H. Biochemistry. 37:1998;15042.
17. Partaledis J.A., Yamaguchi K., Tisdale M., Blair E.E., Falcione C., Maschera B., Myers R.E., Pazhanisamy S., Futer O., Cullinan A.B., Stuver C.M., Byrn R.A., Livingston D.J. J. Virol. 69:1995;5228.