Novel pyrimidine alkynyl phenyl ureas as potent Tie-2 inhibitors

MEDI 369

Clifford D Jones, cliff.jones@astrazeneca.com, Kevin Blades, Matthew Box, Leonie Campbell, Paula Daunt, Richard Grant, Alison Griffen, Lorraine Hassall, Barry Hayter, Keith Johnson, Darren Jones, Jane Kendrew, Kieran Lennon, Richard WA. Luke, William McCoull, Linette Ruston, Michael L. Swain, Andy Wright, and John A. Stawpert. Cancer and Infection Research, AstraZeneca UK, Mereside, Alderley Park, Macclesfield, SK10 4TG, United Kingdom
The receptor tyrosine kinase Tie-2 is involved in the maturation and maintenance of blood vessels and acts in a complementary and coordinated fashion with VEGF receptor signalling. Inhibition of Tie-2 signalling is expected to prevent vessel differentiation, maturation and persistence and impair the capability for further tumour growth. Screening of the AstraZeneca compound collection identified a novel diaminopyrimidine alkynyl phenyl urea that inhibited the phosphorylation of Tie-2 in cells and was a suitable start point for further elaboration. Initial efforts focussed on the optimisation of the potency and pharmacokinetic (PK) parameters of the series. Issues encountered with a lack of photostability and poor oral bioavailability led to the development of a 2-aminopyrimidine alkyne phenyl urea series with much improved properties. The synthesis and structure-activity relationships (SAR) of both of these classes of kinase inhibitors will be described.
 

Poster Session
7:00 PM-9:00 PM, Wednesday, August 22, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Medicinal Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007