IP Library Granted Patent US 12,122,804
Granted Patent B2
US 12,122,804 · App. 17/426,951 · Granted Oct 22, 2024

γ-aminobutyric acid modulator crystal form X, preparation method and application thereof

Inventors: Guobin Ren (Shenzhen, CN); Weijie Ji (Shenzhen, CN); Dongxu Yi (Shenzhen, CN); Jiajun Huang (Shenzhen, CN)
Assignee: SHENZHEN RENTAI PHARMATECH LTD.
C07J7/009C07B2200/13C07J43/003
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Quick Facts
Patent No.
US 12,122,804
App. No.
17/426,951
Granted
Oct 22, 2024
Kind
B2
Abstract

A crystal form X of 3α-hydroxy-3β-methyl-21-(4-cyano-1H-pyrazol-1′-yl)-19-nor-5β-pregnan-20-one, a preparation method of said crystal form and an application thereof in preparing a drug for treatment of central nervous system disease.

Claims (226)

1. A crystal form X of γ-aminobutyric acid modulator, wherein, the γ-aminobutyric acid modulator is 3α-hydroxy-3β-methyl-21-(4-cyano-1H-pyrazol-1′-yl)-19-nor-5β-pregnan-20-one, and the crystal form X has characteristic peaks at 2θ diffraction angles of 9.582°±0.2°, 9.916°±0.2°, 11.638°±0.2°, 13.399°±0.2°, 13.861°±0.2°, 16.739°±0.2°, 18.661°±0.2°, 19.198°±0.2°, 19.919°±0.2°, 20.78°±0.2°, 21.217°±0.2°, 21.943°±0.2°, 23.082°±0.2° and 23.437°±0.2° in X-ray powder diffraction pattern.

2. The crystal form X of claim 1 , wherein, the crystal form X has characteristic peaks at 2θ diffraction angles of 24.96°±0.2°, 26.157°±0.2°, 26.539°±0.2° and 27.439°±0.2° in X-ray powder diffraction pattern.

3. The crystal form X of claim 1 , wherein, the crystal form X has following characteristic peaks in X-ray powder diffraction pattern:

No. of Peaks

2θ (°)

Relative intensity (%)

1

9.582

10.5

2

9.916

5.2

3

11.638

72.9

4

13.399

26.1

5

13.861

54.3

6

16.739

100

7

18.661

17

8

19.198

49.9

9

19.919

18.4

10

20.78

14.9

11

21.217

12.9

12

21.943

24.4

13

23.082

38.7

14

23.437

20.2.

4. The crystal form X of claim 1 , wherein, the crystal form X has following characteristic peaks in X-ray powder diffraction pattern:

No. of Peaks

2θ (°)

Relative intensity (%)

1

9.582

10.5

2

9.916

5.2

3

11.638

72.9

4

13.399

26.1

5

13.861

54.3

6

16.739

100

7

18.661

17

8

19.198

49.9

9

19.919

18.4

10

20.78

14.9

11

21.217

12.9

12

21.943

24.4

13

23.082

38.7

14

23.437

20.2

15

24.96

5

16

26.157

7.9

17

26.539

8.7

18

27.439

7.7.

5. The crystal form X of claim 1 , wherein, the crystal form X has a X-ray powder diffraction pattern as shown in FIG. 7 .

6. The crystal form X of claim 1 , wherein, the crystal form X has a characteristic absorption peak at 212.9±2° C. in differential scanning calorimetry curve.

7. The crystal form X of claim 1 , wherein, the crystal form X has a differential scanning calorimetry curve as shown in FIG. 9 .

8. The crystal form X of claim 1 , wherein, the crystal form X has a weight loss of 0.03% before a temperature of 200° C. in thermal gravimetric analysis curve.

9. The crystal form X of claim 1 , wherein, the crystal form X has a thermal gravimetric analysis curve as shown in FIG. 10 .

10. A method for preparing the crystal form X of claim 1 , comprising the following steps:

adding a proper amount of water into a crystal form K to suspend the crystal form K in water at a temperature of 40° C. to 80° C. for 20 h to 25 h to obtain a suspension, filtering the suspension and drying the filter cake to obtain a white solid which is a crystal form X.

11. The method of claim 10 , wherein, a ratio of the crystal form K to water is (40 to 60)mg:(1 to 2) mL.

12. A method for preparing the crystal form X of claim 1 , comprising the following steps:

placing a crystal form K in an environment having a humidity of 75% RH to 92.5% RH and a temperature of 25° C. to 40° C. for 3 days to 7 days to obtain a white powder which is a crystal form X.

13. A pharmaceutical composition, comprising the crystal form X of claim 1 and a pharmaceutically acceptable excipient.

14. A method for treating central nervous system diseases, comprising administering the crystal form X of claim 1 to a subject in need.

15. The method of claim 14 , wherein, the central nervous system diseases is are selected from the group consisting of sleep disorder, mood disorder, schizophrenia spectrum disorder, spasticity disorder, memory disorder, cognitive disorder, dyskinesia, personality disorder, autism spectrum disorder, pain, traumatic brain injury, vascular disease, substance abuse disorder, withdrawal syndrome, or tinnitus, and any combination thereof.

16. The method of claim 14 , wherein, the crystal form X is administered orally, parenterally, intradermally, intrathecally, intramuscularly, subcutaneously, vaginally, buccally, sublingually, rectally, topically, by inhalation, intranasally or transdermally.

17. A method for treating sleep disorder, mood disorder, schizophrenia spectrum disorder, spasticity disorder, memory disorder, cognitive disorder, dyskinesia, personality disorder, autism spectrum disorder, pain, traumatic brain injury, vascular disease, substance abuse disorder and/or withdrawal syndrome or tinnitus, comprising a step of administering a pharmaceutically effective amount of the pharmaceutical composition of claim 13 to a subject.

18. The crystal form X of claim 2 , wherein, the crystal form X has following characteristic peaks in X-ray powder diffraction pattern:

No. of Peaks

2θ (°)

Relative intensity (%)

1

9.582

10.5

2

9.916

5.2

3

11.638

72.9

4

13.399

26.1

5

13.861

54.3

6

16.739

100

7

18.661

17

8

19.198

49.9

9

19.919

18.4

10

20.78

14.9

11

21.217

12.9

12

21.943

24.4

13

23.082

38.7

14

23.437

20.2.

19. The crystal form X of claim 2 , wherein, the crystal form X has following characteristic peaks in X-ray powder diffraction pattern:

No. of Peaks

2θ (°)

Relative intensity (%)

1

9.582

10.5

2

9.916

5.2

3

11.638

72.9

4

13.399

26.1

5

13.861

54.3

6

16.739

100

7

18.661

17

8

19.198

49.9

9

19.919

18.4

10

20.78

14.9

11

21.217

12.9

12

21.943

24.4

13

23.082

38.7

14

23.437

20.2

15

24.96

5

16

26.157

7.9

17

26.539

8.7

18

27.439

7.7.

20. The crystal form X of claim 2 , wherein, the crystal form X has a X-ray powder diffraction pattern as shown in FIG. 7 .

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 26, 2024
From: SHENZHEN RENTAI PHARMATECH LTD
To: SHENZHEN JINGTAI TECHNOLOGY CO., LTD
Reel/Frame 068395/0203 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 2, 2021
From: REN, GUOBIN; JI, WEIJIE; YI, DONGXU; HUANG, JIAJUN
To: SHENZHEN RENTAI PHARMATECH LTD.
Reel/Frame 057049/0564 →
Continuity (1)
Related Publication 20220098230A1 · Mar 31, 2022