Crystalline forms of thienopyrimidine compound

Patent metadata

Field	Value
Publication number	US-10464946-B2
Application number	US-201616066341-A
Country	US
Kind code	B2
Filing date	Dec 30, 2016
Priority date	Dec 31, 2015
Publication date	Nov 5, 2019
Grant date	Nov 5, 2019

Abstract

The present invention relates to crystalline forms of N-(3-(2-(4-(4-methylpiperazin-1-yl)phenylamino)thieno[3,2-d]pyrimidin-4-yloxy)phenyl)acrylamide, and pharmaceutical compositions containing the same. The crystalline forms can be easily used for the preparation of a pharmaceutical composition containing the same as an active ingredient.

First claim

The invention claimed is:

1. A crystalline form of the compound of Formula 1 shown below, wherein the crystalline form is a dihydrate crystalline form having an X-ray powder diffraction (XRPD) pattern comprising peaks at diffraction angle 2θ values of 8.6°±0.2°, 16.0°+0.2° and 17.2°+0.2° when irradiated with a Cu-Kα light source:

2. The crystalline form of claim 1 , wherein the crystalline form further comprises peaks at diffraction angle 2θ values of 9.4°±0.2°, 10.3°+±0.2°, 13.7°±0.2°, 17.9°±0.2°, 19.7°±0.2°, 22.1°±0.2°, 23.6°±0.2°, and 26.4°±0.2° when irradiated with a Cu-Kα light source.

3. A crystalline form of the compound of Formula 1 shown below, wherein the crystalline form is a trihydrate crystalline form having an X-ray powder diffraction pattern comprising peaks at diffraction angle 2θ values of 5.3°±0.2° and 16.20°±0.2° when irradiated with a Cu-Kα light source:

4. The crystalline form of claim 3 , wherein the crystalline form further comprises peaks at diffraction angle 2θ values of 20.7°±0.2°, 25.4°±0.2°, and 28.5°±0.2° when irradiated with a Cu-Kα light source.

5. A crystalline form of the compound of Formula 1 shown below, wherein the crystalline form is an anhydrous crystalline form having an X-ray powder diffraction pattern comprising peaks at diffraction angle 2° values of 3.8θ±0.2° and 11.6°±0.2° when irradiated with a Cu-Kα light source:

6. The crystalline form of claim 5 , wherein the crystalline form further comprises peaks at diffraction angle 2θ values of 9.8°±0.2°, 16.9°±0.2°, and 19.8°±0.2° when irradiated with a Cu-Kα light source.

7. A crystalline form of the compound of Formula 1 shown below, wherein the crystalline form is an anhydrous crystalline form having an X-ray powder diffraction pattern comprising peaks at diffraction angle 2θ values of 11.1°±0.2°, 20.3°±0.2° and 20.8°±0.2° when irradiated with a Cu-Kα light source:

8. The crystalline form of claim 7 , wherein the crystalline form further comprises peaks at diffraction angle 2θ values of 14.6°±0.2°, 15.5°±0.2°, 21.0°±0.2°, and 22.2°±0.2° when irradiated with a Cu-Kα light source.

9. The crystalline form of claim 1 , wherein the crystalline form is substantially pure.

10. A pharmaceutical composition comprising a crystalline form according to claim 1 and at least one pharmaceutically acceptable carrier or diluent.

11. The pharmaceutical composition of claim 10 , wherein the pharmaceutical composition is used for treating cancer induced by epidermal growth factor receptor tyrosine kinase or a mutant thereof.

12. The crystalline form of claim 2 , wherein the crystalline form is substantially pure.

13. The crystalline form of claim 3 , wherein the crystalline form is substantially pure.

14. The crystalline form of claim 4 , wherein the crystalline form is substantially pure.

15. The crystalline form of claim 5 , wherein the crystalline form is substantially pure.

16. The crystalline form of claim 6 , wherein the crystalline form is substantially pure.

17. The crystalline form of claim 7 , wherein the crystalline form is substantially pure.

18. The crystalline form of claim 8 , wherein the crystalline form is substantially pure.

Assignees

• Hanmi Pharm Ind Co Ltd

Inventors

• Jung Jae Hyuk
• Baek Jong Ouk
• Jung Sun Young
• Kwak Eun Joo
• Kim Hee Cheol
• Ha Tae Hee

Classifications

• C07D495/04 Primary

  Ortho-condensed systems · CPC title

• A61K31/55

  having seven-membered rings, e.g. azelastine, pentylenetetrazole · CPC title

• A61P35/00

  Antineoplastic agents · CPC title

• C07B2200/13

  Crystalline forms, e.g. polymorphs · CPC title

• A61K39/395

  Antibodies (agglutinins A61K38/36 {; as drug carriers A61K47/50}); Immunoglobulins; Immune serum, e.g. antilymphocytic serum · CPC title