IP Library › Granted Patent US 12,091,431

Granted Patent B2

US 12,091,431 · App. 18/351,472 · Granted Sep 17, 2024

Crystals

Inventors: Paul Robert Mcguirk (Spring Hill, FL); Robert Zamboni (Beaconsfield, CA); Melanie Bevill (West Lafayette, IN); Stephan Parent (West Lafayette, IN)

Assignee: Aeromics, Inc.

C07F9/12 A61K31/167 C07B2200/13

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Quick Facts

Patent No.: US 12,091,431
App. No.: 18/351,472
Granted: Sep 17, 2024
Kind: B2

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Abstract

Provided are crystals of 2-{[3,5-bis(trifluoromethyl)phenyl]carbamoyl}-4-chlorophenyl dihydrogen phosphate, compositions comprising the same, and methods of making and using such crystals.

Claims (39)

1. An ethyl acetate solvate of 2-{[3,5-bis(trifluoromethyl)phenyl]carbamoyl}-4-chlorophenyl dihydrogen phosphate

wherein the ethyl acetate solvate exhibits at least one of:

an XRPD pattern comprising at least five 2-theta (°) values selected from the group consisting of 5.1, 6.6, 8.0, 8.7, 10.2, 11.3, 11.5, 12.6, 13.3, 13.8, 14.2, 14.5, 14.6, 15.4, 16.1, 16.5, 17.2, 17.4, 17.7, 18.3, 19.3, 20.0, 20.2, 20.7, 20.9, 21.2, 21.7, 22.0, 23.2, 23.8, 24.3, 24.7, 25.0, 25.2, 25.9, 26.2, 26.8, 27.0, 27.5, 27.9, 28.2, 28.6, and 29.4, wherein the XRPD is measured using an incident beam of Cu Kα radiation;

an XRPD pattern comprising at least five d-spacing (Å) values selected from the group consisting of 17.4, 13.4, 11.1, 10.2, 8.7, 7.9, 7.7, 7.0, 6.7, 6.4, 6.2, 6.1, 5.8, 5.5, 5.4, 5.2, 5.1, 5.0, 4.9, 4.6, 4.4, 4.3, 4.2, 4.1, 4.0, 3.8, 3.7, 3.6, 3.5, 3.4, 3.3, 3.2, 3.1, and 3.0;

an XRPD pattern comprising at least five 2-theta (°) values selected from the group consisting of 5.1, 6.7, 8.1, 8.7, 10.2, 10.4, 11.3, 11.5, 12.6, 14.0, 14.3, 14.6, 16.3, 16.6, 16.9, 17.2, 17.4, 17.7, 18.3, 18.5, 19.3, 19.7, 20.1, 20.5, 20.7, 21.0, 21.2, 21.7, 22.1, 22.2, 23.2, 23.9, 24.3, 24.8, 25.2, 25.4, 25.7, 26.0, 26.2, 26.5, 27.1, 27.6, 28.4, 28.8, and 29.5, wherein the XRPD is measured using an incident beam of Cu Kα radiation; and

an XRPD pattern comprising at least five d-spacing (Å) values selected from the group consisting of 17.3, 13.3, 10.9, 10.2, 8.6, 8.5, 7.8, 7.7, 7.0, 6.3, 6.2, 6.1, 5.4, 5.3, 5.2, 5.1, 5.0, 4.8, 4.6, 4.5, 4.4, 4.3, 4.2, 4.1, 4.0, 3.8, 3.7, 3.6, 3.5, 3.4, 3.3, 3.2, 3.1, and 3.0.

2. The ethyl acetate solvate of claim 1 , wherein the ethyl acetate solvate exhibits at least one of:

an XRPD pattern comprising at least ten 2-theta (°) values selected from the group consisting of 5.1, 6.6, 8.0, 8.7, 10.2, 11.3, 11.5, 12.6, 13.3, 13.8, 14.2, 14.5, 14.6, 15.4, 16.1, 16.5, 17.2, 17.4, 17.7, 18.3, 19.3, 20.0, 20.2, 20.7, 20.9, 21.2, 21.7, 22.0, 23.2, 23.8, 24.3, 24.7, 25.0, 25.2, 25.9, 26.2, 26.8, 27.0, 27.5, 27.9, 28.2, 28.6, and 29.4, wherein the XRPD is measured using an incident beam of Cu Kα radiation; and

an XRPD pattern comprising at least ten d-spacing (Å) values selected from the group consisting of 17.4, 13.4, 11.1, 10.2, 8.7, 7.9, 7.7, 7.0, 6.7, 6.4, 6.2, 6.1, 5.8, 5.5, 5.4, 5.2, 5.1, 5.0, 4.9, 4.6, 4.4, 4.3, 4.2, 4.1, 4.0, 3.8, 3.7, 3.6, 3.5, 3.4, 3.3, 3.2, 3.1, and 3.0.

3. The ethyl acetate solvate of claim 1 , wherein the ethyl acetate solvate exhibits at least one of:

an XRPD pattern comprising at least ten 2-theta (°) values selected from the group consisting of 5.1, 6.7, 8.1, 8.7, 10.2, 10.4, 11.3, 11.5, 12.6, 14.0, 14.3, 14.6, 16.3, 16.6, 16.9, 17.2, 17.4, 17.7, 18.3, 18.5, 19.3, 19.7, 20.1, 20.5, 20.7, 21.0, 21.2, 21.7, 22.1, 22.2, 23.2, 23.9, 24.3, 24.8, 25.2, 25.4, 25.7, 26.0, 26.2, 26.5, 27.1, 27.6, 28.4, 28.8, and 29.5, wherein the XRPD is measured using an incident beam of Cu Kα radiation; and

an XRPD pattern comprising at least ten d-spacing (Å) values selected from the group consisting of 17.3, 13.3, 10.9, 10.2, 8.6, 8.5, 7.8, 7.7, 7.0, 6.3, 6.2, 6.1, 5.4, 5.3, 5.2, 5.1, 5.0, 4.8, 4.6, 4.5, 4.4, 4.3, 4.2, 4.1, 4.0, 3.8, 3.7, 3.6, 3.5, 3.4, 3.3, 3.2, 3.1, and 3.0.

4. The ethyl acetate solvate of claim 2 , wherein the ethyl acetate solvate exhibits at least one of:

an XRPD pattern comprising 2-theta (°) values of 5.1, 6.6, 8.0, 8.7, 10.2, 11.3, 11.5, 12.6, 13.3, 13.8, 14.2, 14.5, 14.6, 15.4, 16.1, 16.5, 17.2, 17.4, 17.7, 18.3, 19.3, 20.0, 20.2, 20.7, 20.9, 21.2, 21.7, 22.0, 23.2, 23.8, 24.3, 24.7, 25.0, 25.2, 25.9, 26.2, 26.8, 27.0, 27.5, 27.9, 28.2, 28.6, and 29.4, wherein the XRPD is measured using an incident beam of Cu Kα radiation; and

an XRPD pattern comprising d-spacing (Å) values of 17.4, 13.4, 11.1, 10.2, 8.7, 7.9, 7.7, 7.0, 6.7, 6.4, 6.2, 6.1, 5.8, 5.5, 5.4, 5.2, 5.1, 5.0, 4.9, 4.6, 4.4, 4.3, 4.2, 4.1, 4.0, 3.8, 3.7, 3.6, 3.5, 3.4, 3.3, 3.2, 3.1, and 3.0.

5. The ethyl acetate solvate of claim 1 wherein the ethyl acetate solvate exhibits at least one of:

an XRPD pattern comprising 2-theta (°) values of 5.1, 6.7, 8.1, 8.7, 10.2, 10.4, 11.3, 11.5, 12.6, 14.0, 14.3, 14.6, 16.3, 16.6, 16.9, 17.2, 17.4, 17.7, 18.3, 18.5, 19.3, 19.7, 20.1, 20.5, 20.7, 21.0, 21.2, 21.7, 22.1, 22.2, 23.2, 23.9, 24.3, 24.8, 25.2, 25.4, 25.7, 26.0, 26.2, 26.5, 27.1, 27.6, 28.4, 28.8, and 29.5, wherein the XRPD is measured using an incident beam of Cu Kα radiation; and

an XRPD pattern comprising d-spacing (Å) values of 17.3, 13.3, 10.9, 10.2, 8.6, 8.5, 7.8, 7.7, 7.0, 6.3, 6.2, 6.1, 5.4, 5.3, 5.2, 5.1, 5.0, 4.8, 4.6, 4.5, 4.4, 4.3, 4.2, 4.1, 4.0, 3.8, 3.7, 3.6, 3.5, 3.4, 3.3, 3.2, 3.1, and 3.0.

6. The ethyl acetate solvate of claim 1 , wherein the ethyl acetate solvate exhibits at least one of:

an XRPD pattern comprising at least five 2-theta (°) values selected from the group consisting of 5.1, 6.6, 8.0, 13.8, 14.5, 16.1, 16.5, 17.4, 19.3, 20.9, 21.2, 22.0, 23.2, and 23.8, wherein the XRPD is measured using an incident beam of Cu Kα radiation; and

an XRPD pattern comprising at least five d-spacing (Å) values selected from the group consisting of 17.4, 13.4, 11.1, 6.4, 6.1, 5.5, 5.4, 5.1, 4.6, 4.2, 4.0, 3.8, and 3.7.

7. The ethyl acetate solvate of claim 1 , wherein the ethyl acetate solvate exhibits at least one of:

an XRPD pattern comprising 2-theta (°) values of 5.1, 6.6, 8.0, 13.8, 14.5, 16.1, 16.5, 17.4, 19.3, 20.9, 21.2, 22.0, 23.2, and 23.8, wherein the XRPD is measured using an incident beam of Cu Kα radiation of wavelength 1.54059 Å; and

an XRPD pattern comprising d-spacing (Å) values of 17.4, 13.4, 11.1, 6.4, 6.1, 5.5, 5.4, 5.1, 4.6, 4.2, 4.0, 3.8, and 3.7.

8. The ethyl acetate solvate of claim 1 , wherein the ethyl acetate solvate exhibits at least one of:

an XRPD pattern comprising at least five 2-theta (°) values selected from the group consisting of 5.1, 6.7, 14.6, 16.6, 19.3, 21.2, 22.1, 23.2, and 23.9, wherein the XRPD is measured using an incident beam of Cu Kα radiation; and

an XRPD pattern comprising at least five d-spacing (Å) values selected from the group consisting of 17.3, 13.3, 6.1, 5.3, 4.6, 4.2, 4.0, 3.8, and 3.7.

9. The ethyl acetate solvate of claim 1 , wherein the ethyl acetate solvate exhibits at least one of:

an XRPD pattern comprising 2-theta (°) values of 5.1, 6.7, 14.6, 16.6, 19.3, 21.2, 22.1, 23.2, and 23.9, wherein the XRPD is measured using an incident beam of Cu Kα radiation of wavelength 1.54059 Å; and

an XRPD pattern comprising d-spacing (Å) values of 17.3, 13.3, 6.1, 5.3, 4.6, 4.2, 4.0, 3.8, and 3.7.

10. The ethyl acetate solvate of claim 1 , wherein the ethyl acetate solvate exhibits an XRPD pattern substantially as shown in FIG. 10 or 11 , wherein the XRPD is measured using radiation of wavelength 1.54059 Å.

11. The ethyl acetate solvate of claim 2 , wherein the ethyl acetate solvate exhibits an XRPD pattern substantially as shown in FIG. 31 , wherein the XRPD is measured using radiation of wavelength 1.54059 Å.

12. The ethyl acetate solvate of claim 3 , wherein the ethyl acetate solvate exhibits an XRPD pattern substantially as shown in FIG. 32 , wherein the XRPD is measured using radiation of wavelength 1.54059 Å.

13. A pharmaceutical composition comprising the ethyl acetate solvate of claim 1 .

14. A pharmaceutical composition comprising the ethyl acetate solvate of claim 6 .

15. A pharmaceutical composition comprising the ethyl acetate solvate of claim 7 .

16. A process for preparing a pharmaceutical composition comprising a mono- or di-anion of 2-{[3,5-bis(trifluoromethyl)phenyl]carbamoyl}-4-chlorophenyl dihydrogen phosphate, wherein the process comprises admixing the ethyl acetate solvate of claim 1 and a pharmaceutically acceptable liquid.

17. A process for preparing a pharmaceutical composition comprising a mono- or di-anion of 2-{[3,5-bis(trifluoromethyl)phenyl]carbamoyl}-4-chlorophenyl dihydrogen phosphate, wherein the process comprises admixing the ethyl acetate solvate of claim 6 and a pharmaceutically acceptable liquid.

18. A process for preparing a pharmaceutical composition comprising a mono- or di-anion of 2-{[3,5-bis(trifluoromethyl)phenyl]carbamoyl}-4-chlorophenyl dihydrogen phosphate, wherein the process comprises admixing the ethyl acetate solvate of claim 7 and a pharmaceutically acceptable liquid.

Assignments (4)

ASSIGNEE CHANGE OF ADDRESS Recorded Oct 5, 2023

From: AEROMICS, INC.

To: AEROMICS, INC.

Reel/Frame 065155/0526 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 22, 2023

From: MCGUIRK, PAUL ROBERT; ZAMBONI, ROBERT

To: AEROMICS, INC.

Reel/Frame 064660/0337 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 22, 2023

From: BEVILL, MELANIE; PARENT, STEPHAN

To: AMRI SSCI, LLC