# US 10,946,016 B2 · Solid forms of an epidermal growth factor receptor kinase inhibitor > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,946,016 B2 - Document ID: US10946016B2 - Status: Granted - Kind: B2 - Application number: 16/015,645 - Filed: 2018-06-22 - Published: 2019-05-23 - Granted: 2021-03-16 - Earliest claimed: 2012-03-15 - Assignees: Celgene CAR LLC - Applicants: Celgene CAR LLC - Inventors: Mei Lai - Web page: https://patentgrep.com/patent/US10946016B2 ## CPC - A61K 31/506: not condensed and containing further heterocyclic rings - A61P 35/00: Antineoplastic agents - A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 - C07D 239/48: Two nitrogen atoms - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) - A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) ## Abstract The present invention provides a solid form and compositions thereof, which are useful as an inhibitor of EGFR kinases and which exhibit desirable characteristics for the same. ## Claims ### Claim 1 A process for preparing a crystalline solid form of Compound 1: comprising combining Compound 1 with a suitable solvent to provide a mixture; and isolating the crystalline solid form of Compound 1 from the mixture, wherein: the crystalline solid form of Compound 1 is unsolvated and is Form A, characterized by having one or more peaks in its X-ray powder diffraction pattern selected from those at about 6.73, about 18.30, about 18.96 and about 25.48 degrees 2-theta; or the crystalline solid form of Compound 1 is unsolvated and is Form B, characterized by having one or more peaks in its X-ray powder diffraction pattern selected from those at about 10.67, about 12.21, about 18.11, about 19.24 and about 21.53 degrees 2-theta; or the crystalline solid form of Compound 1 is a dimethylformamide solvate and is Form C, characterized by having one or more peaks in its X-ray powder diffraction pattern selected from those at about 16.32, about 18.82, about 20.26, about 22.58 and about 25.36 degrees 2-theta; or the crystalline solid form of Compound 1 is a 1,4-dioxane solvate and is Form D, characterized by having one or more peaks in its X-ray powder diffraction pattern selected from those at about 18.40, about 19.31, about 20.14, about 20.53 and about 25.25 degrees 2-theta; or the crystalline solid form of Compound 1 is a methyl ethyl ketone solvate and is Form E, characterized by having one or more peaks in its X-ray powder diffraction pattern selected from those at about 5.78, about 12.57, about 15.34, about 19.10 and about 24.80 degrees 2-theta; or the crystalline solid form of Compound 1 is a N-methyl-2-pyrrolidone solvate and is Form F, characterized by having one or more peaks in its X-ray powder diffraction pattern selected from those at about 15.51, about 16.86, about 18.80, about 20.97 and about 23.32 degrees 2-theta; or the crystalline solid form of Compound 1 is a N-methyl-2-pyrrolidone solvate and is Form G, characterized by having one or more peaks in its X-ray powder diffraction pattern selected from those at about 6.79, about 17.86, about 19.43, about 19.98 and about 22.35 degrees 2-theta; or the crystalline solid form of Compound 1 is a hydrate and is Form H, characterized by having one or more peaks in its X-ray powder diffraction pattern selected from those at about 10.82, about 11.08, about 18.45, about 22.85 and about 25.06 degrees 2-theta; or the crystalline solid form of Compound 1 is a hydrate and is Form I, characterized by having one or more peaks in its X-ray powder diffraction pattern selected from those at about 6.13, about 12.22, about 15.91, about 18.35, about 18.88, and about 21.90 degrees 2-theta. ### Claim 2 (depends on 1) The process of claim 1, wherein the crystalline solid form of Compound 1 is Form A, characterized by having one or more peaks in its X-ray powder diffraction pattern selected from those at about 6.73, about 18.30, about 18.96 and about 25.48 degrees 2-theta. ### Claim 3 (depends on 1) The process of claim 1, wherein the crystalline solid form of Compound 1 is Form B, characterized by having one or more peaks in its X-ray powder diffraction pattern selected from those at about 10.67, about 12.21, about 18.11, about 19.24 and about 21.53 degrees 2-theta. ### Claim 4 (depends on 1) The process of claim 1, wherein the suitable solvent comprises dimethylformamide. ### Claim 5 (depends on 4) The process of claim 4, wherein the crystalline solid form of Compound 1 is a dimethylformamide solvate and is Form C, characterized by having one or more peaks in its X-ray powder diffraction pattern selected from those at about 16.32, about 18.82, about 20.26, about 22.58 and about 25.36 degrees 2-theta. ### Claim 6 (depends on 1) The process of claim 1, wherein the suitable solvent comprises 1,4-dioxane. ### Claim 7 (depends on 6) The process of claim 6, wherein the crystalline solid form of Compound 1 is a 1,4-dioxane solvate and is Form D, characterized by having one or more peaks in its X-ray powder diffraction pattern selected from those at about 18.40, about 19.31, about 20.14, about 20.53 and about 25.25 degrees 2-theta. ### Claim 8 (depends on 1) The process of claim 1, wherein the suitable solvent comprises methyl ethyl ketone. ### Claim 9 (depends on 8) The process of claim 8, wherein the crystalline solid form of Compound 1 is a methyl ethyl ketone solvate and is Form E, characterized by having one or more peaks in its X-ray powder diffraction pattern selected from those at about 5.78, about 12.57, about 15.34, about 19.10 and about 24.80 degrees 2-theta. ### Claim 10 (depends on 1) The process of claim 1, wherein the suitable solvent comprises N-methyl 2 pyrrolidone. ### Claim 11 (depends on 10) The process of claim 10, wherein the crystalline solid form of Compound 1 is a N-methyl 2 pyrrolidone solvate and is Form F, characterized by having one or more peaks in its X-ray powder diffraction pattern selected from those at about 15.51, about 16.86, about 18.80, about 20.97 and about 23.32 degrees 2-theta. ### Claim 12 (depends on 10) The process of claim 10, wherein the crystalline solid form of Compound 1 is a N-methyl 2 pyrrolidone solvate and is Form G, characterized by having one or more peaks in its X-ray powder diffraction pattern selected from those at about 6.79, about 17.86, about 19.43, about 19.98 and about 22.35 degrees 2-theta. ### Claim 13 (depends on 1) The process of claim 1, wherein the suitable solvent comprises acetone and water. ### Claim 14 (depends on 1) The process of claim 1, wherein the crystalline solid form of Compound 1 is Form H, characterized by having one or more peaks in its X-ray powder diffraction pattern selected from those at about 10.82, about 11.08, about 18.45, about 22.85 and about 25.06 degrees 2-theta. ### Claim 15 (depends on 1) The process of claim 1, wherein the crystalline solid form of Compound 1 is Form I, characterized by having one or more peaks in its X-ray powder diffraction pattern selected from those at about 6.13, about 12.22, about 15.91, about 18.35, about 18.88, and about 21.90 degrees 2-theta. ### Claim 16 (depends on 1) The process of claim 1, wherein the suitable solvent comprises acetonitrile. ### Claim 17 (depends on 1) The process of claim 1, wherein the suitable solvent comprises tetrahydrofuran.