IP Library › Granted Patent US 12,319,651
Granted Patent B2
US 12,319,651 · App. 17/604,729 · Granted Jun 3, 2025

Crystalline forms and methods of producing crystalline forms of a compound

Inventors: Lin Zhi (Austin, TX); Henri Sasmor (San Diego, CA)
Assignee: Ligand Pharmaceuticals Incorporated
C07D207/08C07B2200/13
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Quick Facts
Patent No.
US 12,319,651
App. No.
17/604,729
Granted
Jun 3, 2025
Kind
B2
Abstract

Disclosed herein are methods of crystallizing the compound of Formula (I), as well as crystalline forms thereof. Crystalline forms of Formula (I) disclosed include crystalline Form C, crystalline Form E, and Crystalline form B.

Claims (28)

1. A crystalline form of a compound of Formula (I):

or a solvate thereof,

wherein the crystalline form exhibits an X-ray powder diffraction pattern comprising at least one characteristic peak, wherein said characteristic peak is selected from the group consisting of approximately 8.5, 11.8, 12.4, 13.3, 13.7, 15.0, 17.1, 17.5, 18.2, 18.5, 19.5, 21.1, 21.7, 22.1, 26.6, 23.1, 23.7, 24.8, 25.0, 25.5, 26.2, 27.5, and 29.6 degrees 2θ.

2. The crystalline form of claim 1 , wherein the crystalline form exhibits an X-ray powder diffraction pattern comprising at least three characteristic peaks, wherein said characteristic peaks are selected from the group consisting of 8.5, 13.3, 13.7, 15.0, 17.5, 18.2, 18.5, 19.5, 21.1, 23.1, 23.7, 25.5, and 26.2 degrees 2θ.

3. The crystalline form of claim 1 , wherein the crystalline form has a melting point of about 163° C.

4. A crystalline form of a compound of Formula (I):

or a solvate thereof,

wherein the crystalline form exhibits an X-ray powder diffraction pattern comprising at least one characteristic peak, wherein said characteristic peak is selected from the group consisting of approximately 9.6, 11.7, 13.0, 13.9, 14.2, 15.2, 15.8, 17.5, 19.1, 19.4, 21.2, 21.9, 22.6, 23.3, 23.6, 24.7, 25.3, 25.6, 25.9, 26.9, 28.1, and 29.0 degrees 2θ.

5. The crystalline form of claim 4 , wherein the crystalline form exhibits an X-ray powder diffraction pattern comprising at least three characteristic peaks, wherein said characteristic peaks are selected from the group consisting of 9.6, 11.7, 13.0, 13.9, 15.8, 17.5, 19.1, 19.4, 21.2, 21.9, 22.6, 23.3, 23.6, 25.3, and 25.6 degrees 2θ.

6. The crystalline form of claim 4 , wherein the crystalline form has a melting point of about 162° C.

7. A crystalline form of a compound of Formula (I):

or a solvate thereof,

wherein the crystalline form exhibits an X-ray powder diffraction pattern comprising at least one characteristic peak, wherein said characteristic peak is selected from the group consisting of approximately 9.0, 10.3, 11.7, 12.7, 13.3, 14.0, 14.8, 16.0, 17.1, 17.6, 19.2, 19.8, 21.3, 21.9, 22.6, 23.4, 23.7, 24.6, 25.4, 25.7, 26.2, 27.4, 28.3, and 29.2 degrees 2θ.

8. The crystalline form of claim 7 , wherein the crystalline form exhibits an X-ray powder diffraction pattern comprising at least three characteristic peaks, wherein said characteristic peaks are selected from the group consisting of 9.0, 10.3, 11.7, 12.7, 13.3, 16.0, 17.6, 21.3, 21.9, 22.6, 24.6, and 26.2 degrees 2θ.

9. The crystalline form of claim 7 , wherein the crystalline form has a melting point of about 162° C.

10. The crystalline form of claim 1 , wherein the crystalline form is unsolvated.

11. A composition comprising the crystalline form of claim 1 , wherein the total weight of the compound of Formula (I) in the composition comprises greater than 80% by weight of the crystalline form.

12. The composition of claim 11 , wherein the crystalline form is crystalline Form C.

13. A method of treating a disease or disorder comprising administering to a subject a therapeutically effective amount of a composition comprising the crystalline form of claim 1 , wherein the disease or disorder is selected from the group consisting of: aging skin; Alzheimer's disease; anemias; anorexia; arthritis; arteriosclerosis; atherosclerosis; bone disease; distraction osteogenesis; reduced bone mass, density or growth; bone weakening; musculoskeletal impairment; cachexia; cancer; cardiac dysfunction; catabolic side effects of glucocorticoids; Crohn's disease; growth retardation in connection with Crohn's disease; short bowel syndrome; irritable bowel syndrome; inflammatory bowel disease; ulcerative colitis; cognitive decline and impairment; dementia; short term memory loss; contraception (male and female); chronic obstructive pulmonary disease (COPD); chronic bronchitis; decreased pulmonary function; emphysema; decreased libido in both men and women; depression; nervousness, irritability and/or stress; reduced mental energy and low self-esteem; dyslipidemia; erectile dysfunction; frailty; age-related functional decline (“ARFD”) in the elderly; growth hormone deficiency; hematopoietic disorders; hormone replacement (male and female); hyper-cholesterolemia; hyperinsulinemia; hyperlipidemia; hypertension; hyperandrogenemia; hypogonadism; hypothermia; impotence; insulin resistance; type 2 diabetes; lipodystrophy; male menopause; metabolic syndrome (syndrome X); loss of muscle strength and/or function; muscular dystrophies; muscle loss following surgery; muscular atrophy; neurodegenerative diseases; neuromuscular disease; decreased platelet count; platelet aggregation disorders; obesity; osteoporosis; osteopenia; glucocorticoid-induced osteoporosis; osteochondro-dysplasias; periodontal disease; premenstrual syndrome; postmenopausal symptoms in women; Reaven's syndrome; rheumatological disease; sarcopenia; male and female sexual dysfunction; physiological short stature; tooth damage; thrombocytopenia; vaginal dryness; atrophic vaginitis; ventricular dysfunction; and wasting.

14. The process of claim 13 , wherein the disease or disorder is selected from the group consisting of: loss of muscle strength and/or function; muscular dystrophies; muscle loss following surgery; and muscular atrophy.

15. A composition comprising a crystalline form of claim 4 , wherein the total weight of the compound of Formula (I) in the composition comprises greater than 80% by weight of the crystalline form.

16. The composition of claim 15 , wherein the crystalline form is crystalline Form E.

17. A method of treating a disease or disorder comprising administering to a subject a therapeutically effective amount of a composition comprising the crystalline form of claim 4 , wherein the disease or disorder is selected from the group consisting of: aging skin; Alzheimer's disease; anemias; anorexia; arthritis; arteriosclerosis; atherosclerosis; bone disease; distraction osteogenesis; reduced bone mass, density or growth; bone weakening; musculoskeletal impairment; cachexia; cancer; cardiac dysfunction; catabolic side effects of glucocorticoids; Crohn's disease; growth retardation in connection with Crohn's disease; short bowel syndrome; irritable bowel syndrome; inflammatory bowel disease; ulcerative colitis; cognitive decline and impairment; dementia; short term memory loss; contraception (male and female); chronic obstructive pulmonary disease (COPD); chronic bronchitis; decreased pulmonary function; emphysema; decreased libido in both men and women; depression; nervousness, irritability and/or stress; reduced mental energy and low self-esteem; dyslipidemia; erectile dysfunction; frailty; age-related functional decline (“ARFD”) in the elderly; growth hormone deficiency; hematopoietic disorders; hormone replacement (male and female); hyper-cholesterolemia; hyperinsulinemia; hyperlipidemia; hypertension; hyperandrogenemia; hypogonadism; hypothermia; impotence; insulin resistance; type 2 diabetes; lipodystrophy; male menopause; metabolic syndrome (syndrome X); loss of muscle strength and/or function; muscular dystrophies; muscle loss following surgery; muscular atrophy; neurodegenerative diseases; neuromuscular disease; decreased platelet count; platelet aggregation disorders; obesity; osteoporosis; osteopenia; glucocorticoid-induced osteoporosis; osteochondro-dysplasias; periodontal disease; premenstrual syndrome; postmenopausal symptoms in women; Reaven's syndrome; rheumatological disease; sarcopenia; male and female sexual dysfunction; physiological short stature; tooth damage; thrombocytopenia; vaginal dryness; atrophic vaginitis; ventricular dysfunction; and wasting.

18. The process of claim 17 , wherein the disease or disorder is selected from the group consisting of: loss of muscle strength and/or function; muscular dystrophies; muscle loss following surgery; and muscular atrophy.

19. A composition comprising a crystalline form of claim 7 , wherein the total weight of the compound of Formula (I) in the composition comprises greater than 80% by weight of the crystalline form.

20. The composition of claim 19 , wherein the crystalline form is crystalline Form B.

21. A method of treating a disease or disorder comprising administering to a subject a therapeutically effective amount of a composition comprising the crystalline form of claim 7 , wherein the disease or disorder is selected from the group consisting of: aging skin; Alzheimer's disease; anemias; anorexia; arthritis; arteriosclerosis; atherosclerosis; bone disease; distraction osteogenesis; reduced bone mass, density or growth; bone weakening; musculoskeletal impairment; cachexia; cancer; cardiac dysfunction; catabolic side effects of glucocorticoids; Crohn's disease; growth retardation in connection with Crohn's disease; short bowel syndrome; irritable bowel syndrome; inflammatory bowel disease; ulcerative colitis; cognitive decline and impairment; dementia; short term memory loss; contraception (male and female); chronic obstructive pulmonary disease (COPD); chronic bronchitis; decreased pulmonary function; emphysema; decreased libido in both men and women; depression; nervousness, irritability and/or stress; reduced mental energy and low self-esteem; dyslipidemia; erectile dysfunction; frailty; age-related functional decline (“ARFD”) in the elderly; growth hormone deficiency; hematopoietic disorders; hormone replacement (male and female); hyper-cholesterolemia; hyperinsulinemia; hyperlipidemia; hypertension; hyperandrogenemia; hypogonadism; hypothermia; impotence; insulin resistance; type 2 diabetes; lipodystrophy; male menopause; metabolic syndrome (syndrome X); loss of muscle strength and/or function; muscular dystrophies; muscle loss following surgery; muscular atrophy; neurodegenerative diseases; neuromuscular disease; decreased platelet count; platelet aggregation disorders; obesity; osteoporosis; osteopenia; glucocorticoid-induced osteoporosis; osteochondro-dysplasias; periodontal disease; premenstrual syndrome; postmenopausal symptoms in women; Reaven's syndrome; rheumatological disease; sarcopenia; male and female sexual dysfunction; physiological short stature; tooth damage; thrombocytopenia; vaginal dryness; atrophic vaginitis; ventricular dysfunction; and wasting.

22. The method of claim 21 , wherein the disease or disorder is selected from the group consisting of: loss of muscle strength and/or function; muscular dystrophies; muscle loss following surgery; and muscular atrophy.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 14, 2025
From: ZHI, LIN; SASMOR, HENRI
To: LIGAND PHARMACEUTICALS INC.
Reel/Frame 072023/0979 →
SECURITY INTEREST Recorded Oct 18, 2023
From: CYDEX PHARMACEUTICALS, INC.; LIGAND PHARMACEUTICALS INCORPORATED; METABASIS THERAPEUTICS, INC.; PFENEX INC.
To: CITIBANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 065271/0025 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 30, 2022
From: ZHI, LIN; SASMOR, HENRI
To: LIGAND PHARMACEUTICALS INC.
Reel/Frame 061277/0280 →
Continuity (2)
Provisional Application 62836517 · Apr 19, 2019
Related Publication 20220204448A1 · Jun 30, 2022
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