Solid state forms of fused heteroaromatic pyrrolidinones

Abstract

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.

What is claimed is: 
     
         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.