IP Library Granted Patent US 11,390,615
Granted Patent B2
US 11,390,615 · App. 17/070,876 · Granted Jul 19, 2022

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-phenox

Inventors: Cyrille Lescop (Allswchill, CH); Jasper Dingemanse (Allswchill, CH); Andreas Krause (Allswchill, CH)
Assignee: IDORSIA PHARMACEUTICALS LTD
C07D413/04A61K31/047A61K31/4245A61K31/44A61P37/00G01N23/20075
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Quick Facts
Patent No.
US 11,390,615
App. No.
17/070,876
Granted
Jul 19, 2022
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 (19)

1. A method of treating multiple sclerosis comprising administering a pharmaceutically active amount of 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 to a subject in need thereof, 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°.

2. The method according to claim 1 , 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°.

3. The method according to claim 1 , 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°.

4. The method according to claim 1 , wherein the crystalline form of the compound has a melting point of about 79° C. as determined by differential scanning calorimetry.

5. The method according to claim 2 , wherein the crystalline form of the compound has a melting point of about 79° C. as determined by differential scanning calorimetry.

6. The method according to claim 3 , wherein the crystalline form of the compound has a melting point of about 79° C. as determined by differential scanning calorimetry.

7. A method of treating multiple sclerosis comprising administering a pharmaceutical composition to a subject in need thereof; wherein the pharmaceutical composition comprises 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, 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.

8. The method according to claim 7 , 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.

9. The method according to claim 7 , 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.

10. The method according to claim 7 , 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°.

11. The method according to claim 8 , 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°.

12. The method according to claim 9 , 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°.

13. The method according to claim 7 , 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°.

14. The method according to claim 8 , 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°.

15. The method according to claim 9 , 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°.

16. The method according to claim 11 , wherein the crystalline form of the compound has a melting point of about 79° C. as determined by differential scanning calorimetry.

17. The method according to claim 12 , wherein the crystalline form of the compound has a melting point of about 79° C. as determined by differential scanning calorimetry.

18. The method according to claim 14 , wherein the crystalline form of the compound has a melting point of about 79° C. as determined by differential scanning calorimetry.

19. The method according to claim 15 , wherein the crystalline form of the compound has a melting point of about 79° C. as determined by differential scanning calorimetry.

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 Dec 23, 2020
From: DINGEMANSE, JASPER; KRAUSE, ANDREAS; LESCOP, CYRILLE
To: ACTELION PHARMACEUTICALS LTD
Reel/Frame 054736/0422 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 23, 2020
From: ACTELION PHARMACEUTICALS LTD
To: IDORSIA PHARMACEUTICALS LTD
Reel/Frame 054736/0424 →
Priority Claims (1)
WO PCT/EP2015/061153 · May 20, 2015 · international
Continuity (3)
Continuation 16503245 · Jul 3, 2019
Continuation 15575332
Related Publication 20210024513A1 · Jan 28, 2021