Solid form of compound

Abstract

Provided is a solid form of a compound of formula (I) or a salt thereof, or a solvate thereof, or a solvate of a salt thereof, or a mixture thereof.

1 - 47 . (canceled) 
     
     
         48 . A solid form, including a solid form of a compound of formula (I) or a salt thereof, or a solvate thereof, or a solvate of a salt thereof, or a mixture thereof: 
       
         
           
           
               
               
           
         
         wherein it is a crystalline form. 
       
     
     
         49 . The solid form of  claim 48 , which is crystalline form A of the free base of the compound of formula (I), characterized by data selected from one or more of the following:
 (a) X-ray powder diffraction (XRPD) including peaks at 10.979, 19.26, 21.581 and 24.801 degrees 2θ;   (b) X-ray powder diffraction (XRPD) including peaks at 4.781, 10.979, 19.26, 21.581, 22.26 and 24.801 degrees 2θ;   (c) X-ray powder diffraction (XRPD) including peaks at 4.781, 9.58, 10.979, 11.459, 14.678, 17.402, 19.26, 21.581, 22.26, 22.54, 24.801 and 29.219 degrees 2θ;   (d) X-ray powder diffraction (XRPD) including peaks at 4.781, 7.361, 7.619, 9.58, 10.54, 10.979, 11.459, 12.34, 12.96, 13.278, 14.678, 17.402, 18.54, 19.26, 19.918, 21.581, 22.26, 22.54, 23.521, 24.217, 24.801, 25.181, and 29.219 degrees 2θ; and   (e) an XRPD pattern substantially as shown in  FIG.  1   .   
     
     
         50 . The solid form of  claim 48 , which is crystalline form I of the tartrate salt of the compound of formula (I), characterized by data selected from one or more of the following:
 (a) X-ray powder diffraction (XRPD) including peaks at 10.34, 17.981, 18.281 and 21.901 degrees 2θ;   (b) X-ray powder diffraction (XRPD) including peaks at 4.627, 10.34, 17.981, 18.281, 21.901 and 23.121 degrees 2θ;   (c) X-ray powder diffraction (XRPD) including peaks at 4.627, 10.34, 13.019, 17.981, 18.281, 21.2, 21.901, 23.121, 27.299, 27.541 and 29.879 degrees 2θ;   (d) X-ray powder diffraction (XRPD) including peaks at 4.627, 10.34, 13.019, 15.76, 16.54, 17.159, 17.981, 18.281, 20.538, 21.2, 21.901, 23.121, 24.721, 25.659, 27.299, 27.541, 29.879, 32.277, and 41.821 degrees 2θ; and   (e) an XRPD pattern substantially as shown in  FIG.  3   .   
     
     
         51 . The solid form of  claim 48 , which is crystalline form I of the phosphate salt of the compound of formula (I), characterized by data selected from one or more of the following:
 (a) X-ray powder diffraction (XRPD) including peaks at 13.76, 19.08, 20.581 and 22.319 degrees 2θ;   (b) X-ray powder diffraction (XRPD) including peaks at 13.76, 15.941, 19.08, 20.581, 22.319, and 24.642 degrees 2θ;   (c) X-ray powder diffraction (XRPD) including peaks at 13.76, 14.52, 15.941, 19.08, 20.581, 22.319, 23.381, 23.818, 24.642, and 28.219 degrees 2θ;   (d) X-ray powder diffraction (XRPD) including peaks at 9.121, 10.082, 12.6, 13.76, 14.52, 15.941, 18.581, 19.08, 19.781, 20.581, 22.319, 23.381, 23.818, 24.642, 25.66, 26.537, 28.219, 29.419 and 33.98 degrees 2θ; and   (e) an XRPD pattern substantially as shown in  FIG.  10   .   
     
     
         52 . The solid form of  claim 48 , which is crystalline form I of the maleate salt of the compound of formula (I), characterized by data selected from one or more of the following:
 (a) X-ray powder diffraction (XRPD) including peaks at 18.459, 20.237, 22.185, and 24.12 degrees 2θ;   (b) X-ray powder diffraction (XRPD) including peaks at 10.32, 15.998, 18.459, 20.237, 22.185, and 24.12 degrees 2θ;   (c) X-ray powder diffraction (XRPD) including peaks at 6.801, 10.32, 15.998, 18.459, 19.761, 20.237, 22.185, 24.12, 25.599, and 35.258 degrees 2θ;   (d) X-ray powder diffraction (XRPD) including peaks at 6.801, 9.575, 10.32, 13.258, 13.662, 15.041, 15.998, 18.459, 19.761, 20.237, 20.781, 21.498, 21.78, 22.185, 24.12, 25.599, 27.062, 28.203 and 35.258 degrees 2θ; and   (e) an XRPD pattern substantially as shown in  FIG.  12   .   
     
     
         53 . The solid form of  claim 48 , which is crystalline form I of the benzoate salt of the compound of formula (I), characterized by data selected from one or more of the following:
 (a) X-ray powder diffraction (XRPD) including peaks at 6.639, 8.461, 20.16, and 21.699 degrees 2θ;   (b) X-ray powder diffraction (XRPD) including peaks at 6.639, 8.461, 12.119, 14.52, 20.16, and 21.699 degrees 2θ;   (c) X-ray powder diffraction (XRPD) including peaks at 3.981, 6.639, 8.461, 12.119, 14.52, 15.441, 20.16, 20.639, 21.699, and 24.659 degrees 2θ;   (d) X-ray powder diffraction (XRPD) including peaks at 3.981, 6.639, 8.461, 9.6, 12.119, 12.602, 14.52, 15.441, 16.882, 18.12, 18.941, 20.16, 20.639, 21.699, 23.378, 23.719, 24.659, 28.418 and 29.259 degrees 2θ; and   (e) an XRPD pattern substantially as shown in  FIG.  18   .   
     
     
         54 . The solid form of  claim 48 , which is used as a FAK inhibitor. 
     
     
         55 . A pharmaceutical composition, comprising the solid form of  claim 48 . 
     
     
         56 . The pharmaceutical composition of  claim 55 , wherein the solid form is crystalline form A of the free base of the compound of formula (I), characterized by data selected from one or more of the following:
 (a) X-ray powder diffraction (XRPD) including peaks at 10.979, 19.26, 21.581 and 24.801 degrees 2θ;   (b) X-ray powder diffraction (XRPD) including peaks at 4.781, 10.979, 19.26, 21.581, 22.26 and 24.801 degrees 2θ;   (c) X-ray powder diffraction (XRPD) including peaks at 4.781, 9.58, 10.979, 11.459, 14.678, 17.402, 19.26, 21.581, 22.26, 22.54, 24.801 and 29.219 degrees 2θ;   (d) X-ray powder diffraction (XRPD) including peaks at 4.781, 7.361, 7.619, 9.58, 10.54, 10.979, 11.459, 12.34, 12.96, 13.278, 14.678, 17.402, 18.54, 19.26, 19.918, 21.581, 22.26, 22.54, 23.521, 24.217, 24.801, 25.181, and 29.219 degrees 2θ; and   (e) an XRPD pattern substantially as shown in  FIG.  1   .   
     
     
         57 . The pharmaceutical composition of  claim 55 , wherein the solid form is crystalline form I of the tartrate salt of the compound of formula (I), characterized by data selected from one or more of the following:
 (a) X-ray powder diffraction (XRPD) including peaks at 10.34, 17.981, 18.281 and 21.901 degrees 2θ;   (b) X-ray powder diffraction (XRPD) including peaks at 4.627, 10.34, 17.981, 18.281, 21.901 and 23.121 degrees 2θ;   (c) X-ray powder diffraction (XRPD) including peaks at 4.627, 10.34, 13.019, 17.981, 18.281, 21.2, 21.901, 23.121, 27.299, 27.541 and 29.879 degrees 2θ;   (d) X-ray powder diffraction (XRPD) including peaks at 4.627, 10.34, 13.019, 15.76, 16.54, 17.159, 17.981, 18.281, 20.538, 21.2, 21.901, 23.121, 24.721, 25.659, 27.299, 27.541, 29.879, 32.277, and 41.821 degrees 2θ; and   (e) an XRPD pattern substantially as shown in  FIG.  3   .   
     
     
         58 . The pharmaceutical composition of  claim 55 , wherein the solid form is crystalline form I of the phosphate salt of the compound of formula (I), characterized by data selected from one or more of the following:
 (a) X-ray powder diffraction (XRPD) including peaks at 13.76, 19.08, 20.581 and 22.319 degrees 2θ;   (b) X-ray powder diffraction (XRPD) including peaks at 13.76, 15.941, 19.08, 20.581, 22.319, and 24.642 degrees 2θ;   (c) X-ray powder diffraction (XRPD) including peaks at 13.76, 14.52, 15.941, 19.08, 20.581, 22.319, 23.381, 23.818, 24.642, and 28.219 degrees 2θ;   (d) X-ray powder diffraction (XRPD) including peaks at 9.121, 10.082, 12.6, 13.76, 14.52, 15.941, 18.581, 19.08, 19.781, 20.581, 22.319, 23.381, 23.818, 24.642, 25.66, 26.537, 28.219, 29.419 and 33.98 degrees 2θ; and   (e) an XRPD pattern substantially as shown in  FIG.  10   .   
     
     
         59 . The pharmaceutical composition of  claim 55 , wherein the solid form is crystalline form I of the maleate salt of the compound of formula (I), characterized by data selected from one or more of the following:
 (a) X-ray powder diffraction (XRPD) including peaks at 18.459, 20.237, 22.185, and 24.12 degrees 2θ;   (b) X-ray powder diffraction (XRPD) including peaks at 10.32, 15.998, 18.459, 20.237, 22.185, and 24.12 degrees 2θ;   (c) X-ray powder diffraction (XRPD) including peaks at 6.801, 10.32, 15.998, 18.459, 19.761, 20.237, 22.185, 24.12, 25.599, and 35.258 degrees 2θ;   (d) X-ray powder diffraction (XRPD) including peaks at 6.801, 9.575, 10.32, 13.258, 13.662, 15.041, 15.998, 18.459, 19.761, 20.237, 20.781, 21.498, 21.78, 22.185, 24.12, 25.599, 27.062, 28.203 and 35.258 degrees 2θ; and   (e) an XRPD pattern substantially as shown in  FIG.  12   .   
     
     
         60 . The pharmaceutical composition of  claim 55 , wherein the solid form is crystalline form I of the benzoate salt of the compound of formula (I), characterized by data selected from one or more of the following:
 (a) X-ray powder diffraction (XRPD) including peaks at 6.639, 8.461, 20.16, and 21.699 degrees 2θ;   (b) X-ray powder diffraction (XRPD) including peaks at 6.639, 8.461, 12.119, 14.52, 20.16, and 21.699 degrees 2θ;   (c) X-ray powder diffraction (XRPD) including peaks at 3.981, 6.639, 8.461, 12.119, 14.52, 15.441, 20.16, 20.639, 21.699, and 24.659 degrees 2θ;   (d) X-ray powder diffraction (XRPD) including peaks at 3.981, 6.639, 8.461, 9.6, 12.119, 12.602, 14.52, 15.441, 16.882, 18.12, 18.941, 20.16, 20.639, 21.699, 23.378, 23.719, 24.659, 28.418 and 29.259 degrees 2θ; and   (e) an XRPD pattern substantially as shown in  FIG.  18   .   
     
     
         61 . The pharmaceutical composition of  claim 55 , which is used as a FAK inhibitor. 
     
     
         62 . A method of treating Hodgkin's lymphoma, non-Hodgkin's lymphoma, lung cancer, liver cancer, bile duct cancer, myelodysplastic syndrome, leukemia, thyroid cancer, glioma, colon cancer, rectal cancer, colorectal cancer, ovarian cancer, bladder cancer, prostate cancer, breast cancer, sarcoma, neuroblastoma, renal cell carcinoma, head and neck cancer, gastric cancer, esophageal cancer, gastroesophageal junction cancer, thymus cancer, pancreatic cancer, uterine cancer, testicular cancer, melanoma, skin cancer, mesothelioma, thymoma, germinoma, glioblastoma, nasopharyngeal cancer, oropharyngeal cancer, or laryngeal cancer; especially non-small cell lung cancer, small cell lung cancer, colorectal cancer, pancreatic cancer, leukemia, bladder cancer, cervical cancer, bile duct cancer, esophageal cancer, gastric cancer, glioblastoma, liver cancer, melanoma, mesothelioma, ovarian cancer, prostate cancer, kidney cancer, sarcoma, thyroid cancer, testicular cancer, thymoma, or uterine cancer in a subject in need thereof, comprising administering to the subject an effective amount of the solid form of  claim 48 . 
     
     
         63 . The method of  claim 62 , wherein the solid form is crystalline form A of the free base of the compound of formula (I), characterized by data selected from one or more of the following:
 (a) X-ray powder diffraction (XRPD) including peaks at 10.979, 19.26, 21.581 and 24.801 degrees 2θ;   (b) X-ray powder diffraction (XRPD) including peaks at 4.781, 10.979, 19.26, 21.581, 22.26 and 24.801 degrees 2θ;   (c) X-ray powder diffraction (XRPD) including peaks at 4.781, 9.58, 10.979, 11.459, 14.678, 17.402, 19.26, 21.581, 22.26, 22.54, 24.801 and 29.219 degrees 2θ;   (d) X-ray powder diffraction (XRPD) including peaks at 4.781, 7.361, 7.619, 9.58, 10.54, 10.979, 11.459, 12.34, 12.96, 13.278, 14.678, 17.402, 18.54, 19.26, 19.918, 21.581, 22.26, 22.54, 23.521, 24.217, 24.801, 25.181, and 29.219 degrees 2θ; and   (e) an XRPD pattern substantially as shown in  FIG.  1   .   
     
     
         64 . The method of  claim 62 , wherein the solid form is crystalline form I of the tartrate salt of the compound of formula (I), characterized by data selected from one or more of the following:
 (a) X-ray powder diffraction (XRPD) including peaks at 10.34, 17.981, 18.281 and 21.901 degrees 2θ;   (b) X-ray powder diffraction (XRPD) including peaks at 4.627, 10.34, 17.981, 18.281, 21.901 and 23.121 degrees 2θ;   (c) X-ray powder diffraction (XRPD) including peaks at 4.627, 10.34, 13.019, 17.981, 18.281, 21.2, 21.901, 23.121, 27.299, 27.541 and 29.879 degrees 2θ;   (d) X-ray powder diffraction (XRPD) including peaks at 4.627, 10.34, 13.019, 15.76, 16.54, 17.159, 17.981, 18.281, 20.538, 21.2, 21.901, 23.121, 24.721, 25.659, 27.299, 27.541, 29.879, 32.277, and 41.821 degrees 2θ; and   (e) an XRPD pattern substantially as shown in  FIG.  3   .   
     
     
         65 . The method of  claim 62 , wherein the solid form is crystalline form I of the phosphate salt of the compound of formula (I), characterized by data selected from one or more of the following:
 (a) X-ray powder diffraction (XRPD) including peaks at 13.76, 19.08, 20.581 and 22.319 degrees 2θ;   (b) X-ray powder diffraction (XRPD) including peaks at 13.76, 15.941, 19.08, 20.581, 22.319, and 24.642 degrees 2θ;   (c) X-ray powder diffraction (XRPD) including peaks at 13.76, 14.52, 15.941, 19.08, 20.581, 22.319, 23.381, 23.818, 24.642, and 28.219 degrees 2θ;   (d) X-ray powder diffraction (XRPD) including peaks at 9.121, 10.082, 12.6, 13.76, 14.52, 15.941, 18.581, 19.08, 19.781, 20.581, 22.319, 23.381, 23.818, 24.642, 25.66, 26.537, 28.219, 29.419 and 33.98 degrees 2θ; and   (e) an XRPD pattern substantially as shown in  FIG.  10   .   
     
     
         66 . The method of  claim 62 , wherein the solid form is crystalline form I of the maleate salt of the compound of formula (I), characterized by data selected from one or more of the following:
 (a) X-ray powder diffraction (XRPD) including peaks at 18.459, 20.237, 22.185, and 24.12 degrees 2θ;   (b) X-ray powder diffraction (XRPD) including peaks at 10.32, 15.998, 18.459, 20.237, 22.185, and 24.12 degrees 2θ;   (c) X-ray powder diffraction (XRPD) including peaks at 6.801, 10.32, 15.998, 18.459, 19.761, 20.237, 22.185, 24.12, 25.599, and 35.258 degrees 2θ;   (d) X-ray powder diffraction (XRPD) including peaks at 6.801, 9.575, 10.32, 13.258, 13.662, 15.041, 15.998, 18.459, 19.761, 20.237, 20.781, 21.498, 21.78, 22.185, 24.12, 25.599, 27.062, 28.203 and 35.258 degrees 2θ; and   (e) an XRPD pattern substantially as shown in  FIG.  12   .   
     
     
         67 . The method of  claim 62 , wherein the solid form is crystalline form I of the benzoate salt of the compound of formula (I), characterized by data selected from one or more of the following:
 (a) X-ray powder diffraction (XRPD) including peaks at 6.639, 8.461, 20.16, and 21.699 degrees 2θ;   (b) X-ray powder diffraction (XRPD) including peaks at 6.639, 8.461, 12.119, 14.52, 20.16, and 21.699 degrees 2θ;   (c) X-ray powder diffraction (XRPD) including peaks at 3.981, 6.639, 8.461, 12.119, 14.52, 15.441, 20.16, 20.639, 21.699, and 24.659 degrees 2θ;   (d) X-ray powder diffraction (XRPD) including peaks at 3.981, 6.639, 8.461, 9.6, 12.119, 12.602, 14.52, 15.441, 16.882, 18.12, 18.941, 20.16, 20.639, 21.699, 23.378, 23.719, 24.659, 28.418 and 29.259 degrees 2θ; and   (e) an XRPD pattern substantially as shown in  FIG.  18   .