A NEW SALT OF THE COMPOUND IMIDAZO[1,2-a]PYRIDINE, ITS CRYSTALLINE FORM AND METHOD OF PRODUCTION
Patent Information
- Application Number
- RU2025104541
- Authority / Receiving Office
- RU · RU
- Patent Type
- Applications
- Current Assignee / Owner
- Filing Date
- 2023-07-28
- Publication Date
- 2026-09-04
Claims
1. Azetidin-1-yl{8-[(2,6-dimethylbenzyl)amino]-2,3-dimethylimidzo[1,2-a]pyridin-6-yl}methanone citrate.
2. The citrate of azetidin-1-yl{8-[(2,6-dimethylbenzyl)amino]-2,3-dimethylimidazo[1,2-a]pyridin-6-yl}methanone according to claim 1, wherein the molar ratio of azetidin-1-yl{8-[(2,6-dimethylbenzyl)amino]-2,3-dimethylimidazo[1,2-a]pyridin-6-yl}methanone and citric acid is from 1:0.3 to 1:1.
3.
3. The citrate of azetidin-1-yl{8-[(2,6-dimethylbenzyl)amino]-2,3-dimethylimidazo[1,2-a]pyridin-6-yl}methanone according to claim 1, wherein the citrate is anhydrous.
4. The citrate of azetidin-1-yl{8-[(2,6-dimethylbenzyl)amino]-2,3-dimethylimidazo[1,2-a]pyridin-6-yl}methanone according to claim 1, wherein the citrate is crystalline.
5. The citrate of azetidin-1-yl{8-[(2,6-dimethylbenzyl)amino]-2,3-dimethylimidazo[1,2-a]pyridin-6-yl}methanone according to claim 1, wherein the citrate is anhydrous crystalline.
6. The azetidin-1-yl{8-[(2,6-dimethylbenzyl)amino]-2,3-dimethylimidazo[1,2-a]pyridin-6-yl}methanone citrate of claim 1, wherein the azetidin-1-yl{8-[(2,6-dimethylbenzyl)amino]-2,3-dimethylimidazo[1,2-a]pyridin-6-yl}methanone citrate is Crystalline Form A comprising at least three diffraction peaks, wherein the 2θ (±0.2°) value of the powder X-ray diffraction pattern is selected from the group consisting of 5.46°, 7.14°, 10.61°, 11.82°, 18.27° and 25.77°.
7. The azetidin-1-yl{8-[(2,6-dimethylbenzyl)amino]-2,3-dimethylimidazo[1,2-a]pyridin-6-yl}methanone citrate of claim 6, wherein the azetidin-1-yl{8-[(2,6-dimethylbenzyl)amino]-2,3-dimethylimidazo[1,2-a]pyridin-6-yl}methanone citrate is Crystalline Form A, further comprising at least one diffraction peak, wherein the 2θ value (±0.2°) of the powder X-ray diffraction pattern is selected from the group consisting of 10.93°, 13.11°, 14.15°, 15.84°, 16.35°, 19.79° and 24.21°.
8. The azetidin-1-yl{8-[(2,6-dimethylbenzyl)amino]-2,3-dimethylimidazo[1,2-a]pyridin-6-yl}methanone citrate of claim 6, wherein the azetidin-1-yl{8-[(2,6-dimethylbenzyl)amino]-2,3-dimethylimidazo[1,2-a]pyridin-6-yl}methanone citrate has an endothermic differential scanning calorimetry (DSC) peak at 88.69°C, 135.61°C, and 154.84°C (±0.5°C) at a heating rate of 10°C / min.
9. The azetidin-1-yl{8-[(2,6-dimethylbenzyl)amino]-2,3-dimethylimidazo[1,2-a]pyridin-6-yl}methanone citrate of claim 1, wherein the azetidin-1-yl{8-[(2,6-dimethylbenzyl)amino]-2,3-dimethylimidazo[1,2-a]gyridin-6-yl}methanone citrate is Crystalline Form B comprising at least three diffraction peaks, wherein the 2θ (±0.2°) value of the powder X-ray diffraction pattern is selected from the group consisting of 7.03°, 7.69°, 9.47°, 13.21°, 14.86° and 21.13°.
10. The azetidin-1-yl{8-[(2,6-dimethylbenzyl)amino]-2,3-dimethylimidazo[1,2-a]pyridin-6-yl}methanone citrate of claim 9, wherein the azetidin-1-yl{8-[(2,6-dimethylbenzyl)amino]-dimethylimidazo[1,2-a]pyridin-6-yl}methanone citrate has an endothermic differential scanning calorimetry (DSC) peak at 144.57°C (±0.5°C) at a heating rate of 10°C / min.
11. The azetidin-1-yl{8-[(2,6-dimethylbenzyl)amino]-2,3-dimethylimidazo[1,2-a]pyridin-6-yl}methanone citrate of claim 1, wherein the azetidin-1-yl{8-[(2,6-dimethylbenzyl)amino]-dimethylimidazo[1,2-a]pyridin-6-yl}methanone citrate is Crystalline Form C1 comprising at least three diffraction peaks, wherein the 2θ value (±0.2°) of the powder X-ray diffraction pattern is selected from the group consisting of 7.35°, 15.31°, 17.42° and 22.26°.
12. The azetidin-1-yl{8-[(2,6-dimethylbenzyl)amino]-2,3-dimethylimidazo[1,2-a]pyridin-6-yl}methanone citrate of claim 11, wherein the azetidin-1-yl{8-[(2,6-dimethylbenzyl)amino]-dimethylimidazo[1,2-a]pyridin-6-yl}methanone citrate is Crystalline Form C1, further comprising at least one diffraction peak, wherein the 2θ value (±0.2°) of the powder X-ray diffraction pattern is selected from the group consisting of 10.23°, 12.90°, 14.68°, 15.97°, 18.21°, 21.22° and 26.00°.
13. The azetidin-1-yl{8-[(2,6-dimethylbenzyl)amino]-2,3-dimethylimidazo[1,2-a]pyridin-6-yl}methanone citrate of claim 11, wherein the azetidin-1-yl{8-[(2,6-dimethylbenzyl)amino]-dimethylimidazo[1,2-a]pyridin-6-yl}methanone citrate has an endothermic differential scanning calorimetry (DSC) peak at 168.93°C (±0.5°C) at a heating rate of 10°C / min.
14. The azetidin-1-yl{8-[(2,6-dimethylbenzyl)amino]-2,3-dimethylimidazo[1,2-a]pyridin-6-yl}methanone citrate of claim 1, wherein the azetidin-1-yl{8-[(2,6-dimethylbenzyl)amino]-dimethylimidazo[1,2-a]pyridin-6-yl}methanone citrate is Crystalline Form C2 comprising at least three diffraction peaks, wherein the 2θ value (±0.2°) of the powder X-ray diffraction pattern is selected from the group consisting of 5.63°, 8.90°, 9.51° and 13.01°.
15. The azetidin-1-yl{8-[(2,6-dimethylbenzyl)amino]-2,3-dimethylimidazo[1,2-a]pyridin-6-yl}methanone citrate of claim 14, wherein the azetidin-1-yl{8-[(2,6-dimethylbenzyl)amino]-dimethylimidazo[1,2-a]pyridin-6-yl}methanone citrate is Crystalline Form C2, further comprising at least one diffraction peak, wherein the 2θ value (±0.2°) of the powder X-ray diffraction pattern is selected from the group consisting of 12.31°, 14.34°, 14.80°, 18.38°, 18.75° and 19.62°.
16. The azetidin-1-yl{8-[(2,6-dimethylbenzyl)amino]-2,3-dimethylimidazo[1,2-a]pyridin-6-yl}methanone citrate of claim 14, wherein the azetidin-1-yl{8-[(2,6-dimethylbenzyl)amino]-dimethylimidazo[1,2-a]pyridin-6-yl}methanone citrate has an endothermic differential scanning calorimetry (DSC) peak at 161.48°C (±0.5°C) at a heating rate of 10°C / min.
17. The citrate of azetidin-1-yl{8-[(2,6-dimethylbenzyl)amino]-2,3-dimethylimidazo[1,2-a]pyridin-6-yl}methanone according to claim 1, wherein the citrate is amorphous.
18. A method for producing azetidin-1-yl{8-[(2,6-dimethylbenzyl)amino]-2,3-dimethylimidazo[1,2-a]pyridin-6-yl}methanone citrate, wherein the method comprises: reaction of azetidin-1-yl{8-[(2,6-dimethylbenzyl)amino]-2,3-dimethylimidazo[1,2-a]pyridin-6-yl}methanone and citric acid in the presence of at least one solvent selected from an alcohol containing from one to three carbon atoms, acetone, acetonitrile, tetrahydrofuran (THF), dichloromethane, dimethylformamide (DMF), N-methylpyrrolidone (NMP) and purified water.
19. The method according to claim 18, wherein azetidin-1-yl{8-[(2,6-dimethylbenzyl)amino]-2,3-dimethylimidazo[1,2-a]pyridin-6-yl}methanone at the stage of interaction with citric acid is a solvate.
20. The method according to claim 18, wherein at the reaction stage a citrate is obtained in which the molar ratio of azetidin-1-yl{8-[(2,6-dimethylbenzyl)amino]-2,3-dimethylimidazo[1,2-a]pyridin-6-yl}methanone and citric acid is from 1:0.3 to 1:1.
3.
21. The method of claim 18, wherein the reacting step comprises mixing a first solution containing avetidin-1-yl{8-[(2,6-dimethylbenzyl)amino]-2,3-dimethylimidazo[1,2-a]pyridin-6-yl}methanone and a first solvent, and a second solution containing citric acid and a second solvent, wherein the first solvent is a single solvent of acetone or a mixed solvent comprising acetone and at least one selected from an alcohol containing from one to three carbon atoms, acetonitrile, tetrahydrofuran (THF), dichloromethane, dimethylformamide (DMF) and N-methylpyrrolidone (NMP) and The second solvent is acetone.