SOLID STATE FORMS OF FUSED HETEROAROMATIC PYRROLIDINONES
Disclosed are chemical entities which are inhibitors of spleen tyrosine kinase (SYK), namely, chemical entities comprising 6-((1R,2S)-2-aminocyclohexylamino)-7-fluoro-4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,4-c]pyridine-3(2H)-one and certain solid state forms thereof. Also disclosed are methods of using the chemical entities to treat disorders such as a cancer.
1 . A compound which is 6-((1R,2S)-2-aminocyclohexylamino)-7-fluoro-4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,4-c]pyridine-3(2H)-one citrate.
2 . The compound of claim 1 , which is substantially crystalline.
3 - 7 . (canceled)
8 . A pharmaceutical composition comprising the compound of claim 1 and one or more pharmaceutically acceptable carriers.
9 - 11 . (canceled)
12 . A method of treating a cancer comprising administering to a subject having a cancer a compound of claim 1 .
13 - 14 . (canceled)
15 . The method of claim 12 , wherein the cancer is selected from indolent non-Hodgkin’s lymphoma (iNHL), peripheral T-cell lymphoma (PTCL), diffuse large B-cell lymphoma (DLBCL), follicular lymphoma (FL), mantle cell lymphoma (MCL), chronic lymphocytic leukemia (CLL), acute myeloid leukemia (AML), myelodysplastic syndrome (MDS), nasopharyngeal carcinoma, gastric carcinoma, breast cancer, ovarian cancer, lung cancer and a post-transplant lymphoproliferative disorder (PT-LPD).
16 - 26 . (canceled)
27 . A method of making 6-((1R,2S)-2-aminocyclohexylamino)-7-fluoro-4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,4-c]pyridine-3(2H)-one or a pharmaceutically acceptable salt thereof, comprising deprotecting a compound of Formula VI
or a pharmaceutically acceptable salt thereof, wherein R
3 and R 4 are each independently protecting groups or R 3 and R 4 together are a protecting group and R 5 and R 6 are each independently a protecting group, under deprotecting conditions.
28 . A compound of Formula VI
or a pharmaceutically acceptable salt thereof or a pharmaceutically acceptable salt thereof, wherein R
3 and R 4 are each independently protecting groups or R 3 and R 4 together are a protecting group and R 5 and R 6 are each independently a protecting group.