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Last Updated: December 13, 2025

Claims for Patent: 10,434,103

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Summary for Patent: 10,434,103

Title:	Crystal of 3,5-disubstituted benzene alkynyl compound
Abstract:	An object of the present invention is to provide a crystal of (S)-1-(3-(4-amino-3-((3,5-dimethoxyphenyl)ethynyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-pyrrolidinyl)-2-propen-1-one, which is useful as an antitumor agent, the crystal being stable, excellent in oral absorbability, highly chemically pure, and suitable for mass production. The present invention provides a crystal of (S)-1-(3-(4-amino-3-((3,5-dimethoxyphenyl)ethynyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-pyrrolidinyl)-2-propen-1-one that exhibits an X-ray powder diffraction spectrum containing at least three characteristic peaks at diffraction angles (2θ±0.2°) selected from 9.5°, 14.3°, 16.7°, 19.1°, 20.8°, 21.9°, and 25.2°. The present invention also provides a crystal of (S)-1-(3-(4-amino-3-((3,5-dimethoxyphenyl)ethynyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-pyrrolidinyl)-2-propen-1-one that exhibits an X-ray powder diffraction spectrum containing at least seven characteristic peaks at diffraction angles (2θ±0.2°) selected from 13.5°, 17.9°, 19.5°, 20.6°, 22.0°, 22.6°, 23.3°, 23.7°, and 24.2°.
Inventor(s):	Kosuke Egami
Assignee:	Taiho Pharmaceutical Co Ltd
Application Number:	US15/562,455
Patent Claims:	1. A crystal of (S)-1-(3-(4-amino-3-((3,5-dimethoxyphenyl)ethynyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-pyrrolidinyl)-2-propen-1-one, the crystal exhibiting an X-ray powder diffraction spectrum containing at least three characteristic peaks at diffraction angles (2θ±0.2°) selected from 9.5°, 14.3°, 16.7°, 19.1°, 20.8°, 21.9°, and 25.2°. 2. The crystal according to claim 1, which exhibits an X-ray powder diffraction spectrum containing at least five characteristic peaks at diffraction angles (2θ±0.2°) selected from 9.5°, 14.3°, 16.7°, 19.1°, 20.8°, 21.9°, and 25.2°. 3. The crystal according to claim 1, which exhibits an X-ray powder diffraction spectrum containing characteristic peaks at diffraction angles (2θ±0.2°) of 9.5°, 14.3°, 16.7°, 19.1°, 20.8°, 21.9°, and 25.2°. 4. The crystal according to claim 1, which exhibits an endothermic peak (the highest peak value) in the vicinity of 166° C. in differential scanning calorimetry measurement. 5. A pharmaceutical composition comprising the crystal according to claim 1. 6. A pharmaceutical composition for oral administration, the composition comprising the crystal according to claim 1. 7. A crystal of (S)-1-(3-(4-amino-3-((3,5-dimethoxyphenyl)ethynyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-pyrrolidinyl)-2-propen-1-one, the crystal exhibiting an X-ray powder diffraction spectrum containing at least seven characteristic peaks at diffraction angles (2θ±0.2°) selected from 13.5°, 17.9°, 19.5°, 20.6°, 22.0°, 22.6°, 23.3°, 23.7°, and 24.2°. 8. The crystal according to claim 7, which exhibits an X-ray powder diffraction spectrum containing characteristic peaks at diffraction angles (2θ±0.2°) of 13.5°, 17.9°, 19.5°, 20.6°, 22.0°, 22.6°, 23.3°, 23.7°, and 24.2°. 9. The crystal according to claim 7, which exhibits an endothermic peak (the highest peak value) in the vicinity of 169° C. in differential scanning calorimetry measurement. 10. A pharmaceutical composition comprising the crystal according to claim 7. 11. A pharmaceutical composition for oral administration, the composition comprising the crystal according to claim 7. 12. A method for reducing scaling of a crystal of (S)-1-(3-(4-amino-3-((3,5-dimethoxyphenyl)ethynyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-pyrrolidinyl)-2-propen-1-one, the method comprising step (1) of adding (S)-1-(3-(4-amino-3-((3,5-dimethoxyphenyl)ethynyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-pyrrolidinyl)-2-propen-1-one to a solvent selected from the group consisting of water, C1-4 alcohols, C3-5 aliphatic carboxylic acid esters, C3-6 ketones, C2-5 aprotic polar organic solvents, and mixtures of these solvents, and step (2) of stirring the solvent to which (S)-1-(3-(4-amino-3-((3,5-dimethoxyphenyl)ethynyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-pyrrolidinyl)-2-propen-1-one has been added in step (1) to crystallize (S)-1-(3-(4-amino-3-((3,5-dimethoxyphenyl)ethynyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-pyrrolidinyl)-2-propen-1-one.

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