Solid forms

Patent metadata

Field	Value
Publication number	US-12134599-B2
Application number	US-202318484722-A
Country	US
Kind code	B2
Filing date	Oct 11, 2023
Priority date	Sep 8, 2021
Publication date	Nov 5, 2024
Grant date	Nov 5, 2024

Abstract

The disclosure is in part directed to crystalline forms of 5-(3,4-dichlorophenyl)-N-((1R,2R)-2-hydroxycyclohexyl)-6-(2,2,2-trifluoroethoxy)nicotinamide and pharmaceutical compositions thereof.

First claim

What is claimed is:

1. A crystalline form of 5-(3,4-dichlorophenyl)-N-((1R,2R)-2-hydroxycyclohexyl)-6-(2,2,2-trifluoroethoxy)nicotinamide, monohydrate (Form B), characterized by a powder X-ray diffraction pattern having a characteristic peak in degrees 2θ at about 6.5, 11.2, 13.0, 17.2, 19.4, 22.5, 23.4, 26.0, 28.2, 29.8, 32.7, and 34.0, wherein the powder X-ray diffraction pattern was obtained using Cu Kα radiation.

2. The crystalline form of claim 1 , characterized by a differential scanning calorimetry (DSC) profile having a characteristic endotherm with an onset of about 74° C. and a peak of about 87° C.; a characteristic endotherm with an onset of about 163° C. and a peak of about 164° C.; a characteristic exotherm with an onset and a peak of about 165° C.; and a characteristic endotherm with an onset of about 168° C. and a peak of about 169° C.

3. A crystalline form of 5-(3,4-dichlorophenyl)-N-((1R,2R)-2-hydroxycyclohexyl)-6-(2,2,2-trifluoroethoxy)nicotinamide, anhydrate (Form C), characterized by a powder X-ray diffraction pattern having a characteristic peak in degrees 2θ at about 5.1, 5.3, 6.9, 9.0, 18.0, 18.8, 19.7, 20.3, 20.9, 22.2, 23.5, and 24.4, wherein the powder X-ray diffraction pattern was obtained using Cu Kα radiation.

4. The crystalline form of claim 3 , characterized by a differential scanning calorimetry (DSC) profile having a characteristic endotherm with an onset of about 144° C.; a characteristic endotherm with an onset of about 164° C.; and a characteristic endotherm with an onset of about 168° C.

5. A crystalline form of 5-(3,4-dichlorophenyl)-N-((1R,2R)-2-hydroxycyclohexyl)-6-(2,2,2-trifluoroethoxy)nicotinamide, anhydrate (Form D), characterized by a powder X-ray diffraction pattern having a characteristic peak in degrees 2θ at about 7.1, 11.8, 19.1, 19.4, 21.0, 22.1, 22.8, 23.1, 24.9, 26.4, 26.6, and 27.6, wherein the powder X-ray diffraction pattern was obtained using Cu Kα radiation.

6. The crystalline form of claim 5 , characterized by a differential scanning calorimetry (DSC) profile having a characteristic endotherm with an onset of about 152° C.; a characteristic endotherm with an onset of about 165° C.; and a characteristic endotherm with an onset of about 168° C.

7. A crystalline form of 5-(3,4-dichlorophenyl)-N-((1R,2R)-2-hydroxycyclohexyl)-6-(2,2,2-trifluoroethoxy)nicotinamide, anhydrate (Form H), characterized by a powder X-ray diffraction pattern having a characteristic peak in degrees 2θ at about 9.2, 12.1, 18.8, 19.1, 19.9, 20.5, 21.9, 22.5, 22.8, 24.5, 26.0, and 31.7, wherein the powder X-ray diffraction pattern was obtained using Cu Kα radiation.

8. The crystalline form of claim 7 , characterized by a differential scanning calorimetry (DSC) profile having a characteristic exotherm with an onset of about 120° C.; a characteristic endotherm with an onset of about 136° C.; a characteristic endotherm with an onset of about 164° C.; and a characteristic endotherm with an onset of about 169° C.

9. A pharmaceutical composition comprising the crystalline form of claim 1 , and a pharmaceutically acceptable excipient.

10. A pharmaceutical composition comprising the crystalline form of claim 3 , and a pharmaceutically acceptable excipient.

11. A pharmaceutical composition comprising the crystalline form of claim 5 , and a pharmaceutically acceptable excipient.

12. A pharmaceutical composition comprising the crystalline form of claim 7 , and a pharmaceutically acceptable excipient.

13. A method of treating a kidney disease in a patient in need thereof, comprising administering to the patient an effective amount of a crystalline form of claim 1 .

14. A method of treating a cancer in a patient in need thereof, comprising administering to the patient an effective amount of a crystalline form of claim 1 .

15. A method of treating a kidney disease in a patient in need thereof, comprising administering to the patient an effective amount of a crystalline form of claim 5 .

16. A method of treating a cancer in a patient in need thereof, comprising administering to the patient an effective amount of a crystalline form of claim 5 .

17. A method of treating a kidney disease in a patient in need thereof, comprising administering to the patient an effective amount of a crystalline form of claim 3 .

18. A method of treating a cancer in a patient in need thereof, comprising administering to the patient an effective amount of a crystalline form of claim 3 .

19. A method of treating a kidney disease in a patient in need thereof, comprising administering to the patient an effective amount of a crystalline form of claim 7 .

20. A method of treating a cancer in a patient in need thereof, comprising administering to the patient an effective amount of a crystalline form of claim 7 .

Assignees

• River 3 Renal Corp
• Hoffmann La Roche

Inventors

• Hongyan He
• Siyi Jiang
• Schwitter Urs
• Dott Pascal Jean Claude
• Diodone Ralph
• Wyttenbach Nicole
• Grassmann Olaf

Classifications

• C07B2200/13

  Crystalline forms, e.g. polymorphs · CPC title

• A61P13/12

  of the kidneys · CPC title

• C07D213/64 Primary

  attached in position 2 or 6 · CPC title

• C07D213/82 Primary

  in position 3 · CPC title