Nonpeptidic HIV protease inhibitors: 6-Alkyl-5, 6-dihydropyran-2-ones possessing achiral 3-(4-amino/carboxamide-2-t-butyl, 5-methylphenyl thio) moiety: Antiviral activities and pharmacokinetic properties

Bioorganic and Medicinal Chemistry Letters

Volumn 9, Issue 11, 1999, Pages 1481-1486

  Vara Prasad, J V N ^a   Boyer, Fred E ^a   Domagala, John M ^a   Ellsworth, Edmund L ^a   Gajda, Christopher ^a   Hagen, Susan E ^a   Markoski, Larry J ^a   Tait, Bradley D ^a   Lunney, Elizabeth A ^a   Tummino, Peter J ^a   Ferguson, Donna ^a   Holler, Tod ^a   Hupe, Donald ^a   Nouhan, Carolyn ^a   Gracheck, Stephen J ^a   VanderRoest, Steven ^a   Saunders, James ^a   Iyer, Krishna ^a   Sinz, Michael ^a   Brodfuehrer, Joanne ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5,6 DIHYDROPYRAN 2 ONE DERIVATIVE; 6 [2 (4 AMINOPHENYL)ETHYL] 3 (2 TERT BUTYL 4 HYDROXY 5 METHYLPHENYLTHIO) 5,6 DIHYDRO 4 HYDROXY 6 ISOPROPYL 2 PYRANONE; AMIDE; CYTOCHROME P450 ISOENZYME; PD 178392; PROTEINASE INHIBITOR; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANTIVIRAL ACTIVITY; ARTICLE; DRUG BIOAVAILABILITY; DRUG SYNTHESIS; ENANTIOMER; ENZYME INACTIVATION; HUMAN IMMUNODEFICIENCY VIRUS; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; MOUSE; NONHUMAN; ORAL DRUG ADMINISTRATION; STRUCTURE ACTIVITY RELATION;

ANIMALIA; HUMAN IMMUNODEFICIENCY VIRUS;

EID: 0033532648     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(99)00237-1     Document Type: Article

References (13)

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8. A similar approach using sulfonamide and carboxamides was done, see: Skulnick, H. I.; Johnson, P. D.; Aristoff, P. A.; Morris, J. K.; Lovasz, K. D.; Howe, W. J.; Watenpaugh, K. D.; Janakiraman, M. N.; Anderson, D. J.; Reischer, R. J.; Schwartz, T. M.; Banitt, L. S.; Tomich, P. K.; Lynn, J. C.; Horng, M-M.; Chong, K-T.; Hinshaw, R. R.; Dolak, L. A.; Seest, E. P.; Schwende, F. J.; Rush, B. D.; Howard, G. M.; Toth, L. N.; Wilkinson, K. R.; Kakuk, T. J.; Johnson, C. W.; Cole, S. L.; Zaya, R. M.; Zipp, G. L.; Possert, P. L.; Dalga, R. J.; Zhong, W-Z.; Williams, M. G.; Romines, K. R. J. Med. Chem. 1997, 40, 1149, and references therein.
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10. 1H NMR, IR, MS, and CHN and are in agreement with the structure.
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12. Molecular modeling was performed using SYBYL Molecular Modeling Software, commercially available from Tripos Inc., 1699 Hanley Road, Suite 303, St. Louis, MO 63144-2913.
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