IP Library Granted Patent US 11,834,443
Granted Patent B2
US 11,834,443 · App. 17/810,545 · Granted Dec 5, 2023

Crystalline form of the compound (s)-3-{4-[5-(2-cyclopentyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-propane-1,2-diol

Inventors: Cyrille Lescop (Allschwil, CH); Jasper Dingemanse (Allschwil, CH); Andreas Krause (Allschwil, CH)
Assignee: Idorsia Pharmaceuticals Ltd
C07D413/04A61K31/047A61K31/4245A61K31/44A61P37/00G01N23/20075
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 11,834,443
App. No.
17/810,545
Granted
Dec 5, 2023
Kind
B2
Abstract

The present invention relates to a crystalline form of the compound (S)-3-{4-[5-(2-cyclopentyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-propane-1,2-diol.

Claims (26)

1. A pharmaceutical composition comprising a crystalline form of the compound (S)-3-{4-[5-(2-cyclopentyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-propane-1,2-diol and a pharmaceutically acceptable carrier, wherein the crystalline form is characterized by the presence of peaks in the X-ray powder diffraction diagram at the following angles of refraction 2θ: 5.4°, 8.5°, and 10.8°; and wherein the pharmaceutical composition comprises about 2 mg or about 4 mg of the compound.

2. The pharmaceutical composition according to claim 1 , wherein the pharmaceutical composition comprises about 2 mg of the compound (S)-3-{4-[5-(2-cyclopentyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-propane-1,2-diol.

3. The pharmaceutical composition according to claim 1 , wherein the pharmaceutical composition comprises about 4 mg of the compound (S)-3-{4-[5-(2-cyclopentyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-propane-1,2-diol.

4. The pharmaceutical composition according to claim 2 , wherein the crystalline form of the compound is characterized by the presence of peaks in the X-ray powder diffraction diagram at the following angles of refraction 2θ: 4.2°, 5.4°, 8.0°, 8.5°, and 10.8°.

5. The pharmaceutical composition according to claim 3 , wherein the crystalline form of the compound is characterized by the presence of peaks in the X-ray powder diffraction diagram at the following angles of refraction 2θ: 4.2°, 5.4°, 8.0°, 8.5°, and 10.8°.

6. The pharmaceutical composition according to claim 2 , wherein the crystalline form of the compound is characterized by the presence of peaks in the X-ray powder diffraction diagram at the following angles of refraction 2θ: 4.2°, 5.4°, 8.0°, 8.5°, 10.8°, 12.7°, 14.4°, 17.7°, 20.4°, and 21.3°.

7. The pharmaceutical composition according to claim 3 , wherein the crystalline form of the compound is characterized by the presence of peaks in the X-ray powder diffraction diagram at the following angles of refraction 2θ: 4.2°, 5.4°, 8.0°, 8.5°, 10.8°, 12.7°, 14.4°, 17.7°, 20.4°, and 21.3°.

8. The pharmaceutical composition according to claim 6 , wherein the crystalline form of the compound has a melting point of about 79° C. as determined by differential scanning calorimetry.

9. The pharmaceutical composition according to claim 7 , wherein the crystalline form of the compound has a melting point of about 79° C. as determined by differential scanning calorimetry.

10. The pharmaceutical composition according to claim 1 , wherein the pharmaceutical composition comprises 2 mg of the compound (S)-3-{4-[5-(2-cyclopentyl-6-methoxy-pyridin-4-yl)[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-propane-1,2-diol.

11. The pharmaceutical composition according to claim 1 , wherein the pharmaceutical composition comprises 4 mg of the compound (S)-3-{4-[5-(2-cyclopentyl-6-methoxy-pyridin-4-yl)[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-propane-1,2-diol.

12. The pharmaceutical composition according to claim 6 , wherein the pharmaceutical composition comprises 2 mg of the compound (S)-3-{4-[5-(2-cyclopentyl-6-methoxy-pyridin-4-yl)[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-propane-1,2-diol.

13. The pharmaceutical composition according to claim 7 , wherein the pharmaceutical composition comprises 4 mg of the compound (S)-3-{4-[5-(2-cyclopentyl-6-methoxy-pyridin-4-yl)[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-propane-1,2-diol.

14. A method for manufacturing a pharmaceutical composition comprising the compound (S)-3-{4-[5-(2-cyclopentyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-propane-1,2-diol and a pharmaceutically acceptable carrier, wherein the manufacturing of the pharmaceutical composition comprises the step of admixing a crystalline form of the compound (S)-3-{4-[5-(2-cyclopentyl-6-methoxy-pyridin-4-yl)[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-propane-1,2-diol with the pharmaceutically acceptable carrier; and wherein the crystalline form of the compound (S)-3-{4-[5-(2-cyclopentyl-6-methoxy-pyridin-4-yl)[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-propane-1,2-diol is characterized by the presence of peaks in the X-ray powder diffraction diagram at the following angles of refraction 2θ: 5.4°, 8.5°, and 10.8°.

15. The method according to claim 14 , wherein the pharmaceutical composition comprises about 2 mg or about 4 mg of the compound (S)-3-{4-[5-(2-cyclopentyl-6-methoxy-pyridin-4-yl)[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-propane-1,2-diol.

16. The method according to claim 14 , wherein the pharmaceutical composition comprises about 4 mg of the compound (S)-3-{4-[5-(2-cyclopentyl-6-methoxy-pyridin-4-yl)[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-propane-1,2-diol.

17. The method according to claim 14 , wherein the crystalline form of the compound is characterized by the presence of peaks in the X-ray powder diffraction diagram at the following angles of refraction 2θ: 4.2°, 5.4°, 8.0°, 8.5°, and 10.8°.

18. The method according to claim 16 , wherein the crystalline form of the compound is characterized by the presence of peaks in the X-ray powder diffraction diagram at the following angles of refraction 2θ: 4.2°, 5.4°, 8.0°, 8.5°, and 10.8°.

19. The method according to claim 14 , wherein the crystalline form of the compound is characterized by the presence of peaks in the X-ray powder diffraction diagram at the following angles of refraction 2θ: 4.2°, 5.4°, 8.0°, 8.5°, 10.8°, 12.7°, 14.4°, 17.7°, 20.4°, and 21.3°.

20. The method according to claim 16 , wherein the crystalline form of the compound is characterized by the presence of peaks in the X-ray powder diffraction diagram at the following angles of refraction 2θ: 4.2°, 5.4°, 8.0°, 8.5°, 10.8°, 12.7°, 14.4°, 17.7°, 20.4°, and 21.3°.

21. The method according to claim 19 , wherein the crystalline form of the compound has a melting point of about 79° C. as determined by differential scanning calorimetry.

22. The method according to claim 20 , wherein the crystalline form of the compound has a melting point of about 79° C. as determined by differential scanning calorimetry.

23. The method according to claim 14 , wherein the pharmaceutical composition comprises 2 mg of the compound (S)-3-{4-[5-(2-cyclopentyl-6-methoxy-pyridin-4-yl)[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-propane-1,2-diol.

24. The method according to claim 14 , wherein the pharmaceutical composition comprises 4 mg of the compound (S)-3-{4-[5-(2-cyclopentyl-6-methoxy-pyridin-4-yl)[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-propane-1,2-diol.

25. The method according to claim 19 , wherein the pharmaceutical composition comprises 2 mg of the compound (S)-3-{4-[5-(2-cyclopentyl-6-methoxy-pyridin-4-yl)[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-propane-1,2-diol.

26. The method according to claim 19 , wherein the pharmaceutical composition comprises 4 mg of the compound (S)-3-{4-[5-(2-cyclopentyl-6-methoxy-pyridin-4-yl)[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-propane-1,2-diol.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 6, 2024
From: IDORSIA PHARMACEUTICALS LTD.
To: VIATRIS ASIA PACIFIC PTE. LTD.
Reel/Frame 067647/0303 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 5, 2022
From: DINGEMANSE, JASPER; KRAUSE, ANDREAS; LESCOP, CYRILLE
To: ACTELION PHARMACEUTICALS LTD
Reel/Frame 060398/0616 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 5, 2022
From: ACTELION PHARMACEUTICALS LTD
To: IDORSIA PHARMACEUTICALS LTD
Reel/Frame 060398/0700 →
Priority Claims (1)
WO PCT/EP2015/061153 · May 20, 2015 · international
Continuity (4)
Continuation 17070876 · Oct 14, 2020
Continuation 16503245 · Jul 3, 2019
Continuation 15575332
Related Publication 20230002365A1 · Jan 5, 2023