IP Library › Granted Patent US 12,187,689
Granted Patent B2
US 12,187,689 · App. 18/197,414 · Granted Jan 7, 2025

Crystalline forms of 3-substituted 1,2,4-oxadiazole

Inventors: Pottayil Govindan N. Sasikumar (Bangalore, IN); Seetharamaiah Setty S. Naremaddepalli (Bangalore, IN)
Assignee: Aurigene Oncology Limited
C07D271/06C07B2200/13
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Quick Facts
Patent No.
US 12,187,689
App. No.
18/197,414
Granted
Jan 7, 2025
Kind
B2
Abstract

The invention relates to crystalline forms of a 3-substituted 1,2,4-oxadiazole compound, methods of their preparation, and related pharmaceutical preparations thereof. The invention also relates to preparations suitable for pharmaceutical, veterinary, and agriculturally-relevant uses.

Claims (37)

1. A method for preparing a crystalline compound, comprising the steps of:

a) providing a mixture comprising the crystalline compound and a first solvent;

b) crystallizing the compound from the mixture by:

i) contacting the mixture with an anti-solvent; or

ii) heating the mixture for a period of time; and

wherein the crystalline compound and the compound have the structure of formula (I):

2. The method of claim 1 , wherein the crystalline compound is solvated.

3. The method of claim 1 , wherein the crystalline compound is a hydrate.

4. The method of claim 1 , wherein the crystalline compound is a monohydrate.

5. The method of claim 4 , wherein the crystalline compound has 2θ values 8.4±0.2, 13.6±0.2, 16.5±0.2, 16.8±0.2, 21.4±0.2, and 28.4±0.2.

6. The method of claim 4 , wherein the crystalline compound has 2θ values 8.4±0.2, 13.6±0.2, 16.5±0.2, 16.8±0.2, 19.3±0.2, 20.4±0.2, 21.4±0.2, and 28.4±0.2.

7. The method of claim 4 , wherein the crystalline compound has 2θ values 8.4±0.2, 13.6±0.2, 16.5±0.2, 16.8±0.2, 19.3±0.2, 19.9±0.2, 20.4±0.2, 21.4±0.2, 24.5±0.2, 26.5±0.2, and 28.4±0.2.

8. The method of claim 4 , wherein the crystalline compound has 2θ values 8.4±0.2, 11.5±0.2, 13.6±0.2, 16.5±0.2, 16.8±0.2, 19.3±0.2, 19.9±0.2, 20.4±0.2, 21.4±0.2, 21.8±0.2, 24.5±0.2, 26.5±0.2, 27.5±0.2, 28.0±0.2, 28.4±0.2, 30.0±0.2, and 32.4±0.2.

9. The method of claim 4 , wherein the crystalline compound has 2θ values of 6.8±0.2, 8.4±0.2, 10.0±0.2, 10.6±0.2, 11.5±0.2, 13.6±0.2, 16.5±0.2, 16.8±0.2, 17.6±0.2, 18.8±0.2, 19.3±0.2, 19.9±0.2, 20.4±0.2, 20.6±0.2, 21.00±0.2, 21.4±0.2, 21.8±0.2, 22.6±0.2, 23.6±0.2, 24.5±0.2, 24.8±0.2, 25.3±0.2, 26.5±0.2, 27.1±0.2, 27.5±0.2, 28.0±0.2, 28.4±0.2, 29.3±0.2, 30.1±0.2, 30.8±0.2, 31.5±0.2, 32.4±0.2, 33.0±0.2, 33.5±0.2, 34.3±0.2, 35.3±0.2, 36.5±0.2, 37.6±0.2, 38.1±0.2, and 38.7±0.2.

10. The method of claim 4 , wherein the crystalline compound has an XRD pattern substantially as shown in FIG. 1 .

11. The method of claim 1 , wherein the compound is a dihydrate.

12. The method of claim 11 , wherein the crystalline compound has 2θ values 12.9±0.2, 13.5±0.2, 15.7±0.2, 17.0±0.2, 29.7±0.2, and 33.7±0.2.

13. The method of claim 11 , wherein the crystalline compound has 2θ values 12.9±0.2, 13.5±0.2, 15.7±0.2, 17.0±0.2, 20.3±0.2, 28.9±0.2, 29.7±0.2, and 33.7±0.2.

14. The crystalline compound of claim 11 , wherein the crystalline compound has 2θ values 12.9±0.2, 13.5±0.2, 15.7±0.2, 17.0±0.2, 19.6±0.2, 20.3±0.2, 26.2±0.2, 28.9±0.2, 29.7±0.2, and 33.7±0.2.

15. The method of claim 11 , wherein the crystalline compound has 2θ values 12.9±0.2, 13.5±0.2, 15.7±0.2, 17.0±0.2, 19.1±0.2, 19.6±0.2, 20.3±0.2, 21.1±0.2, 21.4±0.2, 26.2±0.2, 27.2±0.2, 28.9±0.2, 29.7±0.2, 32.2±0.2, and 33.7±0.2.

16. The method of claim 11 , wherein the crystalline compound has 2θ values of 10.9±0.2,11.6±0.2,12.9±0.2,13.5±0.2,15.7±0.2,16.1±0.2,17.0±0.2, 19.1±0.2, 19.6±0.2, 20.3±0.2, 21.1±0.2, 21.4±0.2, 22.2±0.2, 22.9±0.2, 24.2±0.2, 24.5±0.2, 24.8±0.2, 25.1±0.2, 25.8±0.2, 26.2±0.2, 26.4±0.2, 27.2±0.2, 28.2±0.2, 28.9±0.2, 29.7±0.2, 30.2±0.2, 31.0±0.2, 32.2±0.2, 33.7±0.2, 34.2±0.2, 36.0±0.2, 37.0±0.2, 38.4±0.2, and 39.0±0.2.

17. The method of claim 11 , wherein the crystalline compound has an XRD pattern substantially as shown in FIG. 2 .

18. The method of claim 1 , wherein step b) comprises contacting the mixture with an anti-solvent.

19. The method of claim 18 , wherein the first solvent is selected from acetonitrile, anisole, dichloromethane, ethanol, isopropyl acetate, methyl tert-butyl ether (MTBE), n-heptane, tetrahydrofuran, water, and mixtures thereof.

20. The method of claim 18 , wherein the first solvent is selected from acetonitrile, ethanol, methyl tert-butyl ether (MTBE), water, and mixtures thereof.

21. The method of claim 18 , wherein the first solvent is a mixture comprising water.

22. The method of claim 18 , wherein the antisolvent is selected from THF, methanol, isopropyl alcohol, ethanol, 1,4-dioxane, acetonitrile or acetone.

23. The method of claim 18 , wherein the antisolvent is acetonitrile.

24. The method of claim 1 , wherein step b) comprises heating the mixture for a period of time.

25. The method of claim 24 , wherein the first solvent is selected from acetonitrile, anisole, dichloromethane, ethanol, isopropyl acetate, methyl tert-butyl ether (MTBE), n-heptane, tetrahydrofuran, water, and mixtures thereof.

26. The method of claim 24 , wherein the first solvent is selected from acetonitrile, ethanol, methyl tert-butyl ether (MTBE), water, and mixtures thereof.

27. The method of claim 24 , wherein the first solvent is a mixture comprising water.

28. The method of claim 1 , wherein the mixture is heated to room temperature.

29. The method of claim 1 , wherein the mixture is heated to 50° C.

30. The method of claim 1 , wherein the period of time is about 3 days.

31. The method of claim 28 , wherein the period of time is about 3 days.

32. The method of claim 29 , wherein the period of time is about 3 days.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 9, 2023
From: SASIKUMAR, POTTAYIL GOVINDAN N.; NAREMADDEPALLI, SEETHARAMAIAH SETTY S.
To: AURIGENE DISCOVERY TECHONOLOGIES LIMITED
Reel/Frame 063911/0683 →
CHANGE OF NAME Recorded Jun 9, 2023
From: AURIGENE DISCOVERY TECHNOLOGIES LIMITED
To: AURIGENE ONCOLOGY LIMITED
Reel/Frame 064412/0358 →
Priority Claims (1)
IN 201741036169 · Oct 11, 2017 · national
Continuity (3)
Continuation 17461512 · Aug 30, 2021
Continuation 16755439
Related Publication 20230278970A1 · Sep 7, 2023
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Cited By (1)
US 12,643,870