# US 12,215,109 B2 · Crystal of pyrazolo[3,4-d]pyrimidine

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- Number: US 12,215,109 B2
- Document ID: US12215109B2
- Status: Granted
- Kind: B2
- Application number: 17/271,424
- Filed: 2019-08-28
- Published: 2021-10-28
- Granted: 2025-02-04
- Earliest claimed: 2018-08-29
- Assignees: Taiho Pharmaceutical Co., Ltd.
- Applicants: Taiho Pharmaceutical Co., Ltd.
- Inventors: Tadashi Shimamura; Hiromi Oshiumi
- Web page: https://patentgrep.com/patent/US12215109B2

## CPC

- C07D 487/04: Ortho-condensed systems
- A61P 35/00: Antineoplastic agents
- C07B 2200/13: Crystalline forms, e.g. polymorphs
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

An object of the invention is to provide a crystal of (R)-1-(1-acryloylpiperidin-3-yl)-4-amino-N-(4-(2-(dimethylamino)-2-oxoethyl)-2,3-dimethylphenyl)-1H-pyrazolo[3,4-d]pyrimidine-3-carboxamide which is excellent in stability and preferable from the viewpoint of manufacturing and formulation. The present invention provides a crystal having an X-ray powder diffraction spectrum having characteristic peaks at diffraction angles (2θ±0.2°) of 6.0°, 7.7°, 8.9°, 10.6°, 12.1°, 13.1°, 14.0°, 14.7°, 15.5°, 15.8°, 16.8°, 17.7°, 18.1°, 18.4°, 19.4°, 23.4°, 24.1°, 24.7°, 25.1° and 25.7°.

## Claims

### Claim 1

A crystal of (R)-1-(1-acryloylpiperidin-3-yl)-4-amino-N-(4-(2-(dimethylamino)-2-oxoethyl)-2,3-dimethylphenyl)-1H-pyrazolo[3,4-d]pyrimidine-3-carboxamide having an X-ray powder diffraction spectrum having at least six peaks at diffraction angles (2θ±0.2°) selected from the group consisting of 6.0°, 7.7°, 8.9°, 10.6°, 12.1°, 13.1°, 14.0°, 14.7°, 15.5°, 15.8°, 16.8°, 17.7°, 18.1°, 18.4°, 19.4°, 23.4°, 24.1°, 24.7°, 25.1° and 25.7°.

### Claim 2 (depends on 1)

The crystal according to claim 1, wherein the crystal has an X-ray powder diffraction spectrum having peaks at diffraction angles (2θ±0.2°) of 6.0°, 7.7°, 8.9°, 10.6°, 12.1°, 13.1°, 14.0°, 14.7°, 15.5°, 15.8°, 16.8°, 17.7°, 18.1°, 18.4°, 19.4°, 23.4°, 24.1°, 24.7°, 25.1° and 25.7°.

### Claim 3 (depends on 1)

The crystal according to claim 1, wherein an endothermic peak is present at a peak temperature of around 200° ° C. in thermogravimetric-differential thermal simultaneous measurement (TG-DTA measurement).

### Claim 4 (depends on 1)

The crystal according of claim 1, wherein the crystal has the following crystal data in single-crystal analysis:
crystal system: single-crystal system
space group: P21
lattice constant:
a=11.5696(2) Å
b=7.47792(14) Å
c=14.6722(3) Å
β=100.674(7)°
Volume of unit lattice: V=1247.43(5) Å3.

### Claim 5 (depends on 1)

A pharmaceutical composition comprising the crystal of claim 1.

### Claim 6 (depends on 1)

A pharmaceutical composition for oral administration, comprising the crystal of claim 1.

### Claim 7 (depends on 1)

A method for treating a malignant tumor with excessive expression of HER2, amplification of HER2 gene or mutation of HER2, comprising administering an effective amount of the crystal of claim 1 to a patient in need thereof.

### Claim 8 (depends on 1)

A method of manufacturing a pharmaceutical composition comprising combining the crystal of claim 1 with one or more pharmaceutically acceptable excipients.