Table 6. N-1 Pyrazolopyrimidine Optimizations.

No.	R	BTK (IC50, nM)	PI3Kδ (IC50, nM)
27	2-indanyl	104	35
(±)-30	2-tetralinyl	NDa	NDb
(±)-31	2-(5-F-indanyl)	NDc	NDd
(+)-32	2-(5-NH2-indanyl)	24	47
(−)-32	2-(5-NH2-indanyl)	32	16
(+)-33	2-(7-NH2-tetralinyl)	176	55
(−)-33	2-(7-NH2-tetralinyl)	19	72

^aIC₅₀ not determined; inhibition of BTK was 34% at 100 nM (±)-30.

^bIC₅₀ not determined; inhibition of PI3Kδ was 52% at 100 nM (±)-30.

^cIC₅₀ not determined; inhibition of BTK was 6.6% at 100 nM (±)-31.

^dIC₅₀ not determined; inhibition of PI3Kδ was 26% at 100 nM (±)-31.