IP Library Granted Patent US 11,390,581
Granted Patent B2
US 11,390,581 · App. 17/506,822 · Granted Jul 19, 2022

Crystalline 5-(dimethylamino)-n-(4-(morpholinomethyl)phenyl)naphthalene-1-sulfonamide di-hydrochloride di-hydrate

Inventors: Adam Galan (Alameda, CA); Ritu Lal (Palo Alto, CA); Wendy Luo (Palo Alto, CA)
Assignee: GEN1E LIFESCIENCES INC.
C07C311/29C07B2200/13
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Quick Facts
Patent No.
US 11,390,581
App. No.
17/506,822
Granted
Jul 19, 2022
Kind
B2
Abstract

Crystalline 5-(dimethylamino)-N-(4-(morpholinomethyl)phenyl)naphthalene-1-sulfonamide dihydrochloride dihydrate, methods of preparing the crystalline salt, pharmaceutical compositions containing the crystalline salt, and methods of treatment using the crystalline salt are disclosed.

Claims (27)

1. A compound, crystalline 5-(dimethylamino)-N-(4-(morpholinomethyl)phenyl)naphthalene-1-sulfonamide dihydrochloride dihydrate:

2. The compound of claim 1 , wherein the compound is characterized by an XRPD pattern comprising characteristic diffraction peaks at least at 10.5°±0.2°, 13.9°±0.2°, 14.8°±0.2°, 17.2±0.2°, 20.4±0.2°, 22.6±0.2°, 25.7±0.2°, and 27.9±0.2° expressed as 2θ angles and determined using Cu-Kα radiation.

3. The compound of claim 1 , wherein the compound is characterized by an XRPD pattern comprising characteristic diffraction peaks at least at 10.5°±0.1°, 13.9°±0.1°, 14.8°±0.1°, 17.2±0.1°, 20.4±0.1°, 22.6±0.1°, 25.7±0.1°, and 27.9±0.2° expressed as 2θ angles and determined using Cu-Kα radiation.

4. The compound of claim 1 , wherein the compound is characterized by an XRPD pattern comprising characteristic diffraction peaks at least at 7.5±0.2°, 8.5±0.2°, 10.5°±0.2°, 12.8±0.2°, 13.9°±0.2°, 14.8°±0.2°, 15.5±0.2°, 17.2±0.2°, 18.2±0.2°, 20.1±0.2°, 20.4±0.2°, 21.1±0.2°, 22.6±0.2°, 22.9±0.2°, 23.5±0.2°, 23.8±0.2°, 24.6±0.2°, 25.7±0.2°, 26.1±0.2°, 26.4±0.2°, 27.1±0.2°, 27.5±0.2°, 27.9±0.2°, and 32.4±0.2° expressed as 2θ angles and determined using Cu-Kα radiation.

5. The compound of claim 1 , wherein the compound is characterized by an XRPD pattern comprising characteristic diffraction peaks at least at 7.5±0.1°, 8.5±0.1°, 10.5°±0.1°, 12.8±0.1°, 13.9°±0.1°, 14.8°±0.1°, 15.5±0.1°, 17.2±0.1°, 18.2±0.1°, 20.1±0.1°, 20.4±0.1°, 21.1±0.1°, 22.6±0.1°, 22.9±0.1°, 23.5±0.1°, 23.8±0.1°, 24.6±0.1°, 25.7±0.1°, 26.1±0.1°, 26.4±0.1°, 27.1±0.1°, 27.5±0.1°, 27.9±0.1°, and 32.4±0.1° expressed as 2θ angles and determined using Cu-Kα radiation.

6. The compound of claim 1 , wherein the compound is characterized by an XRPD pattern as shown in FIG. 1 .

7. The compound of claim 1 , wherein the compound has a melting onset temperature from 161° C. to 167° C., and wherein the melting onset temperature is determined by differential scanning calorimetry.

8. The compound of claim 1 , wherein the compound has a melting enthalpy from 89 J/g to 99 J/g, and wherein the melting enthalpy is determined by differential scanning calorimetry.

9. The compound of claim 1 , wherein the compound has a melting peak from 178.5 J/g to 184.5 J/g, and wherein the melting peak is determined by differential scanning calorimetry.

10. The compound of claim 1 , wherein the compound exhibits a differential scanning calorimetry curve as shown in FIG. 2 .

11. The compound of claim 1 , wherein the compound has a weight loss from 13% to 15% at a temperature from 25° C. to 210° C., and wherein the weight loss is determined by thermogravimetric analysis at a scan rate of 2° C./min.

12. The compound of claim 1 , wherein the compound exhibits a differential thermal calorimetry curve as shown in FIG. 3 .

13. The compound of claim 1 , wherein the compound has a weight loss from 2% to 6% at a temperature from 25° C. to 122° C., and wherein the weight loss is determined by thermogravimetric analysis at a scan rate of 4.25° C./min.

14. The compound of claim 1 , wherein the compound exhibits a differential thermal calorimetry curve as shown in FIG. 4 .

15. A pharmaceutical composition comprising the compound of claim 1 .

16. The pharmaceutical composition of claim 15 , wherein the pharmaceutical composition comprises a therapeutically effective amount of the compound for treating a disease in a patient, wherein the disease is selected from cancer, an inflammatory disease, and an autoimmune disease.

17. The pharmaceutical composition of claim 15 , wherein the pharmaceutical composition comprises a therapeutically effective amount of the compound for treating a disease in a patient, wherein the disease is selected from acute lung injury, acute respiratory distress syndrome (ARDS), and chronic obstructive pulmonary disease (COPD).

18. A method of treating a disease in a patient comprising administering to a patient in need of such treatment a therapeutically effective of amount of the compound of claim 1 , wherein the disease is selected from breast cancer and melanoma.

19. A method of treating a disease in a patient comprising administering to a patient in need of such treatment a therapeutically effective of amount of the compound of claim 1 , wherein the disease is an inflammatory disease, wherein the inflammatory disease is selected from acute respiratory distress syndrome, focal segmental glomerulonephritis, atherosclerosis/acute coronary syndrome, chronic obstructive pulmonary disease, asthma, inflammatory bowel disease, Crohn's disease, psoriasis, lupus, multiple sclerosis, inflammation in hypercholesteremia, pain, diabetes, and rheumatoid arthritis.

20. A method of treating a disease in a patient comprising administering to a patient in need of such treatment a therapeutically effective of amount of the compound of claim 1 , wherein the disease is an autoimmune disease, wherein the autoimmune disease is selected from segmental glomerulonephritis, asthma, inflammatory disease, Crohn's disease, psoriasis, lupus, multiple sclerosis, pain, diabetes and rheumatoid arthritis.

21. A method of treating a disease in a patient comprising administering to a patient in need of such treatment a therapeutically effective of amount of the compound of claim 1 , wherein the disease is an age-related disease, wherein the age-related disease is selected from hearing loss, muscle degeneration, Werner's syndrome, cellular aging, and Alzheimer's disease.

22. A method of treating a disease in a patient comprising administering to a patient in need of such treatment a therapeutically effective of amount of the compound of claim 1 , wherein the disease is selected from acute lung injury, acute respiratory distress syndrome (ARDS), and chronic obstructive pulmonary disease (COPD).

23. A method of treating a disease in a patient comprising administering to a patient in need of such treatment a therapeutically effective of amount of the pharmaceutical composition of claim 15 , wherein the disease is selected from breast cancer and melanoma.

24. A method of treating a disease in a patient comprising administering to a patient in need of such treatment a therapeutically effective of amount of the pharmaceutical composition of claim 15 , wherein the disease is an inflammatory disease, wherein the inflammatory disease is selected from acute respiratory distress syndrome, focal segmental glomerulonephritis, atherosclerosis/acute coronary syndrome, chronic obstructive pulmonary disease, asthma, inflammatory bowel disease, Crohn's disease, psoriasis, lupus, multiple sclerosis, inflammation in hypercholesteremia, pain, diabetes, and rheumatoid arthritis.

25. A method of treating a disease in a patient comprising administering to a patient in need of such treatment a therapeutically effective of amount of the pharmaceutical composition of claim 15 , wherein the disease is an autoimmune disease, wherein the autoimmune disease is selected from segmental glomerulonephritis, asthma, inflammatory disease, Crohn's disease, psoriasis, lupus, multiple sclerosis, pain, diabetes and rheumatoid arthritis.

26. A method of treating a disease in a patient comprising administering to a patient in need of such treatment a therapeutically effective of amount of the pharmaceutical composition of claim 15 , wherein the disease is an age-related disease, wherein the age-related disease is selected from hearing loss, muscle degeneration, Werner's syndrome, cellular aging, and Alzheimer's disease.

27. A method of treating a disease in a patient comprising administering to a patient in need of such treatment a therapeutically effective of amount of the pharmaceutical composition of claim 15 , wherein the disease is selected from acute lung injury, acute respiratory distress syndrome (ARDS), and chronic obstructive pulmonary disease (COPD).

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 21, 2021
From: GALAN, ADAM; LAL, RITU; LUO, WENDY
To: GEN1E LIFESCIENCES INC.
Reel/Frame 057861/0631 →
Continuity (2)
Provisional Application 63106991 · Oct 29, 2020
Related Publication 20220135520A1 · May 5, 2022
Cited By (1)
US 12,269,792