Crystal form a of (5-amino-8-(2-methyl-6-(trifluoromethyl)pyridin-4-yl)-7-phenyl-[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)methanol (compound 1)

Patent metadata

Field	Value
Publication number	US-11649239-B2
Application number	US-201917044127-A
Country	US
Kind code	B2
Filing date	Apr 28, 2019
Priority date	Apr 28, 2018
Publication date	May 16, 2023
Grant date	May 16, 2023

Abstract

Disclosed in the present invention are a crystal form of a [1,2,4]triazolo[1,5-c]pyrimidine compound and a preparation method thereof. Further disclosed is a use of the crystal form in the preparation of a medicament for treating A 2A receptor related diseases.

First claim

What is claimed is:

1. A crystal form A of (5-amino-8-(2-methyl-6-(trifluoromethyl)pyridin-4-yl)-7-phenyl-[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)methanol (Compound 1) of the following formula:

wherein the crystal form A is characterized by an X-ray powder diffraction pattern comprising characteristic diffraction peaks (° 2θ) at the following angles of 11.30°±0.2° 2θ, 16.90°±0.2° 2θ, and 22.52°±0.2° 2θ.

2. The crystal form A according to claim 1 , wherein the crystal form A is further characterized by an X-ray powder diffraction pattern further comprising additional characteristic diffraction peaks (° 2θ) at the following angles of 8.08°±0.2° 2θ, 14.00°±0.2° 2θ, 18.30°±0.2° 2θ, 23.15°±0.2° 2θ, and 25.26°±0.2° 2θ.

3. The crystal form A according to claim 2 , wherein the crystal form A is further characterized by an X-ray powder diffraction pattern as shown in FIG. 1 .

4. The crystal form A according to claim 1 , wherein the crystal form A is further characterized by a differential scanning calorimetry curve having a starting point of the endothermic peak at 198.61° C.±2° C.

5. The crystal form A according to claim 4 , wherein the crystal form A is further characterized by a differential scanning calorimetry curve as shown in FIG. 2 .

6. The crystal form A according to claim 1 , wherein the crystal form A is further characterized by a thermogravimetric analysis curve having a weight loss in the range of 0.0% to 0.4423% at 199.80° C.±3° C.

7. The crystal form A according to claim 4 , wherein the crystal form A is further characterized by a thermogravimetric analysis curve having a weight loss in the range of 0.0% to 0.4423% at 199.80° C.±3° C.

8. The crystal form A according to claim 6 , wherein the crystal form A is further characterized by a thermogravimetric analysis curve as shown in FIG. 3 .

9. The crystal form A according to claim 7 , wherein the crystal form A is further characterized by a thermogravimetric analysis curve as shown in FIG. 3 .

10. A method for inhibiting the activity of an adenosine A 2A receptor in a subject in need thereof, wherein the method comprises administering to the subject the crystal form A according to claim 1 .

11. The method according to claim 10 , wherein the subject has a disease related to the adenosine A 2A receptor, and wherein the disease related to the adenosine A 2A receptor is colon cancer or rectal cancer.

12. The method according to claim 11 , wherein the disease related to the adenosine A 2A receptor is colorectal cancer.

Assignees

• Medshine Discovery Inc

Inventors

• Chen Kevin X
• Yu Yanxin
• Chen Xinde
• Zhang Li
• Chen Zhaoguo
• Xie Cheng

Classifications

• C07D487/04 Primary

  Ortho-condensed systems · CPC title

• A61P35/00

  Antineoplastic agents · CPC title

• C07B2200/13

  Crystalline forms, e.g. polymorphs · CPC title

• A61P25/16

  Anti-Parkinson drugs · CPC title