EP3694854A1 — Crystalline forms

USPTO Abstract

The invention relates to a compound of formula I-IV and pharmaceutically acceptable salts thereof which exhibit inhibition of rearranged kinase during transfection (RET). In particular, the invention relates to novel crystalline forms of 4- (6- (4 - ((6-methoxypyridin-3-yl) methyl) piperazin-1-yl) pyridin-3-yl) -6- (1- methyl-1H-pyrazol-4-yl) pyrazolo [1,5-a] pyridine-3-carbonitrile (formula I), 6- (2-hydroxy-2-methylpropoxy) -4- (6- (6- ( (6-Methoxypyridin-3-yl) methyl) -3,6-diazabicyclo [3.1.1] heptan-3-yl) pyridin-3-yl) pyrazolo [1,5-a] pyridine-3-carbonitrile (Formula II) ), 6- (2-hydroxy-2-methylpropoxy) -4- (6- (6- (6-methoxynicotinoyl) -3,6-diazabicyclo [3.1.1] heptan-3-yl) pyridin-3-yl pyrazolo [1,5-a] pyridine-3-carbonitrile (formula III), 6- (2-hydroxy-2-methylpropoxy) -4- (6- (4-hydroxy-4- (pyridin-2-yl) methyl) piperidin-1-yl) pyridin-3-yl) pyrazolo [1,5-a] pyridine-3-carbonitrile (formula IV), and pharmaceutically acceptable salts thereof, pharmaceutical compositions comprising the compounds methods of making the compounds, and the use of the compounds in therapy. More particularly, the invention relates to novel crystalline forms of Formula I-IV and pharmaceutically acceptable salts thereof, useful in the treatment and prevention of diseases that can be treated with a RET kinase inhibitor, including diseases. and disorders associated with RET.