Discovery of a novel benzophenone as a next generation HIV-1 NNRTI agent

ORGN 660

Andy Freeman, Andy.A.Freeman@gsk.com, Medicinal Chemistry, GlaxoSmithKline, 5 Moore Dr, Durham, NC 27709
Treatment of HIV infection simultaneously with multiple antiviral agents known as Highly Active Antiretroviral Therapy (HAART) results in sustained control of virus replication. HIV-1 nonnucleoside reverse transcriptase inhibitors (NNRTIs) are an integral part of some HAART treatment regimes. An effective next generation NNRTI agent should include potent and selective activity against viruses with single and double mutations known to limit the usefulness of the currently approved NNRTI agents. Exploration of the SAR of a set of benzophenones encompassed molecular modeling, protein crystallography and classical medicinal chemistry. Potent and selective benzophenones have been discovered which inhibit the replication of both wild type virus and a wide range of mutant viruses at low nanomolar IC50s. A prodrug strategy significantly increased oral bioavailability of the investigational compound and demonstrated favorable pharmacokinetics in rats, monkeys and humans. In a 7-day study in HIV-1 infected patients with documented NNRTI-resistance, GW 695634 prodrug of parent compound GW 678248 demonstrated potent antiviral.