IP Library › Granted Patent US 10,766,862
Granted Patent B2
US 10,766,862 · App. 16/337,874 · Granted Sep 8, 2020

Crystal form and salt form of and preparation method for tyrosine kinase inhibitor

Inventors: Chaofeng Long (Shanghai, CN); Zhengxia Chen (Shanghai, CN); Xiaoxin Chen (Shanghai, CN); Yang Zhang (Shanghai, CN); Zhuowei Liu (Shanghai, CN); Shuhui Chen (Shanghai, CN); Jian Li (Shanghai, CN)
Assignee: Guangdong Raynovent Biotech Co., Ltd.
C07D215/233C07B2200/13
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Quick Facts
Patent No.
US 10,766,862
App. No.
16/337,874
Granted
Sep 8, 2020
Kind
B2
Abstract

Disclosed are a crystal form and a salt form of and a preparation method for a tyrosine kinase inhibitor.

Claims (43)

1. A crystal form of Compound 1 comprising a crystal form A, a crystal form B, a crystal form C, a crystal form D or a crystal form E,

wherein,

the crystal form A has an X-ray powder diffraction pattern with characteristic diffraction peaks at angles 2θ of: 4.47±0.2°, 7.80±0.2°, 12.61±0.2°, 13.25±0.2°, 16.32±0.2°;

the crystal form B has an X-ray powder diffraction pattern with characteristic diffraction peaks at angles 2θ of: 13.55±0.2°, 15.94±0.2°, 17.36±0.2°, 22.41±0.2°, 24.16±0.2°, 24.78±0.2°;

the crystal form C has an X-ray powder diffraction pattern with characteristic diffraction peaks at angles 2θ of: 13.29±0.2°, 15.58±0.2°, 16.21±0.2°, 19.84±0.2°, 24.95±0.2°;

the crystal form D has an X-ray powder diffraction pattern with characteristic diffraction peaks at angles 2θ of: 6.70±0.2°, 11.30±0.2°, 11.76±0.2°, 15.52±0.2°, 16.35±0.2°;

the crystal form E has an X-ray powder diffraction pattern with characteristic diffraction peaks at angles 2θ of: 4.51±0.2°, 6.68±0.2°, 11.79±0.2°, 13.62±0.2°.

2. The crystal form of Compound 1 according to claim 1 , wherein

the crystal form A further has an X-ray powder diffraction pattern with characteristic diffraction peaks at angles 2θ of: 4.47±0.2°, 7.80±0.2°, 8.87±0.2°, 12.61±0.2°, 13.25±0.2°, 16.32±0.2°, 19.03±0.2°, 26.66±0.2°;

the crystal form B further has an X-ray powder diffraction pattern with characteristic diffraction peaks at angles 2θ of: 13.55±0.2°, 15.94±0.2°, 17.36±0.2°, 22.41±0.2°, 24.16±0.2°, 24.78±0.2°, 25.19±0.2°;

the crystal form C further has an X-ray powder diffraction pattern with characteristic diffraction peaks at angles 2θ of: 13.29±0.2°, 15.58±0.2°, 16.21±0.2°, 19.84±0.2°, 24.32±0.2°, 24.95±0.2°, 28.13±0.2°;

the crystal form D further has an X-ray powder diffraction pattern with characteristic diffraction peaks at angles 2θ of: 6.70±0.2°, 11.30±0.2°, 11.76±0.2°, 15.52±0.2°, 16.35±0.2°, 27.26±0.2°;

the crystal form E further has an X-ray powder diffraction pattern with characteristic diffraction peaks at angles 2θ of: 4.51±0.2°, 6.68±0.2°, 11.79±0.2°, 13.62±0.2°, 15.51±0.2°.

3. The crystal form of Compound 1 according to claim 2 , wherein

the crystal form A has an XRPD pattern as shown in FIG. 1 ;

the crystal form B has an XRPD pattern as shown in FIG. 3 ;

the crystal form C has an XRPD pattern as shown in FIG. 6 ;

the crystal form D has an XRPD pattern as shown in FIG. 9 ;

the crystal form E has an XRPD pattern as shown in FIG. 12 .

4. A hydrochloride salt of Formula (I) comprising a crystal form F having an X-ray powder diffraction pattern with characteristic diffraction peaks at angles 2θ of: 11.64±0.2°, 13.32±0.2°, 14.02±0.2°, 20.06±0.2°, 24.22±0.2°

5. The hydrochloride salt of Formula (I) according to claim 4 , wherein the crystal form F further has an X-ray powder diffraction pattern with characteristic diffraction peaks at angles 2θ of: 11.64±0.2°, 13.32±0.2°, 14.02±0.2°, 16.78±0.2°, 20.06±0.2°, 24.22±0.2°, 25.02±0.2°.

6. The hydrochloride salt of Formula (I) according to claim 5 , wherein the crystal form F has an XRPD pattern as shown in FIG. 15 .

7. A p-toluenesulfonate salt of Formula (II) comprising a crystal form G having an X-ray powder diffraction pattern with characteristic diffraction peaks at angles 2θ of: 4.84±0.2°, 9.93±0.2°, 15.43±0.2°, 19.48±0.2°, 19.93±0.2°

8. The p-toluenesulfonate salt of Formula (II) according to claim 7 , wherein the crystal form G further has an X-ray powder diffraction pattern with characteristic diffraction peaks at angles 2θ of: 4.84±0.2°, 9.93±0.2°, 15.43±0.2°, 19.48±0.2°, 19.93±0.2°, 20.56±0.2°, 24.20±0.2°, 24.89±0.2°.

9. The p-toluenesulfonate salt of Formula (II) according to claim 8 , wherein the crystal form G has an XRPD pattern as shown in FIG. 18 .

10. An ethanesulfonate salt of Formula (III) comprising a crystal form H having an X-ray powder diffraction pattern with characteristic diffraction peaks at angles 2θ of: 7.80±0.2°, 12.53±0.2°, 13.11±0.2°, 17.78±0.2°, 21.90±0.2°

11. The ethanesulfonate salt of Formula (III) according to claim 10 , wherein the crystal form H further has an X-ray powder diffraction pattern with characteristic diffraction peaks at angles 2θ of: 7.80±0.2°, 12.53±0.2°, 13.11±0.2°, 14.86±0.2°, 17.78±0.2°, 20.11±0.2°, 21.90±0.2°.

12. The ethanesulfonate salt of Formula (III) according to claim 11 , wherein the crystal form H has an XRPD pattern as shown in FIG. 21 .

13. A methanesulfonate salt of Formula (IV) comprising a crystal form J, a crystal form K, a crystal form L or a crystal form M, wherein,

the crystal form J has an X-ray powder diffraction pattern with characteristic diffraction peaks at angles 2θ of: 7.88±0.2°, 12.58±0.2°, 15.02±0.2°, 21.28±0.2°, 22.00±0.2°, 27.35±0.2°;

the crystal form K has an X-ray powder diffraction pattern with characteristic diffraction peaks at angles 2θ of: 8.02±0.2°, 16.52±0.2°, 18.10±0.2°, 20.35±0.2°, 22.10±0.2°, 23.27±0.2°;

the crystal form L has an X-ray powder diffraction pattern with characteristic diffraction peaks at angle 2θ of: 18.06±0.2°, 21.35±0.2°, 22.05±0.2°, 24.94±0.2°;

the crystal form M has an X-ray powder diffraction pattern with characteristic diffraction peaks at angles 2θ of: 9.68±0.2°, 20.78±0.2°, 23.15±0.2°, 29.82±0.2°.

14. The methanesulfonate salt of Formula (IV) according to claim 13 , wherein,

the crystal form J further has an X-ray powder diffraction pattern with characteristic diffraction peaks at angles 2θ of: 7.88±0.2°, 12.58±0.2°, 15.02±0.2°, 16.42±0.2°, 20.41±0.2°, 21.28±0.2°, 22.00±0.2°, 27.35±0.2°;

the crystal form K further has an X-ray powder diffraction pattern with characteristic diffraction peaks at angles 2θ of: 8.02±0.2°, 15.14±0.2°, 16.52±0.2°, 18.10±0.2°, 20.35±0.2°, 21.36±0.2°, 22.10±0.2°, 23.27±0.2°;

the crystal form L further has an X-ray powder diffraction pattern with characteristic diffraction peaks at angles 2θ of: 8.00±0.2°, 15.10±0.2°, 16.49±0.2°, 18.06±0.2°, 20.49±0.2°, 21.35±0.2°, 22.05±0.2°, 24.94±0.2°;

the crystal form M further has an X-ray powder diffraction pattern with characteristic diffraction peaks at angles 2θ of: 9.68±0.2°, 17.37±0.2°, 18.24±0.2°, 20.19±0.2°, 20.78±0.2°, 22.10±0.2°, 22.74±0.2°, 23.15±0.2°, 29.82±0.2°.

15. The methanesulfonate salt of Formula (IV) according to claim 14 , wherein

the crystal form J has an XRPD pattern as shown in FIG. 24 ;

the crystal form K has an XRPD pattern as shown in FIG. 27 ;

the crystal form L has an XRPD pattern as shown in FIG. 29 ;

the crystal form M has an XRPD pattern as shown in FIG. 31 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 1, 2019
From: LONG, CHAOFENG; CHEN, ZHENGXIA; CHEN, XIAOXIN; ZHANG, YANG; LIU, ZHUOWEI; CHEN, SHUHUI; LI, JIAN
To: GUANGDONG RAYNOVENT BIOTECH CO., LTD.
Reel/Frame 048757/0399 →
Priority Claims (1)
CN 2016 1 0871081 · Sep 30, 2016 · national
Continuity (1)
Related Publication 20200024235A1 · Jan 23, 2020