Crystalline forms of (S)-5-benzyl-N-(5-methyl-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-yl)-4H-1,2,4-triazole-3-carboxamide

Patent metadata

Field	Value
Publication number	US-10287280-B2
Application number	US-201615548500-A
Country	US
Kind code	B2
Filing date	Feb 12, 2016
Priority date	Feb 13, 2015
Publication date	May 14, 2019
Grant date	May 14, 2019

Abstract

Disclosed are novel crystalline forms of (S)-5-benzyl-N-(5-methyl-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-yl)-4H-1,2,4-triazole-3-carboxamide, and solvates thereof and pharmaceutical compositions containing the same. Also disclosed are processes for the preparation thereof and methods for use thereof.

First claim

What is claimed is:

1. A crystalline form of a compound represented by:

wherein the crystalline form is a crystalline solvate of the compound and the crystalline solvate is selected from the group consisting of a methyl acetate, n-propyl acetate, isopropyl acetate, water, iso-propyl alcohol, methyl-isobutylketone, 2-methyl-tetrahydrofuran, dimethyl carbonate, and methoxy-cyclopentane solvate of the compound, wherein the water solvate is a monohydrate.

2. The crystalline form according to claim 1 , wherein the crystalline solvate is a methyl acetate solvate, and wherein the crystalline form is characterized by an X-ray powder diffraction pattern substantially in accordance with FIG. 2 .

3. The crystalline form according to claim 1 , wherein the crystalline solvate is a methyl acetate solvate, and wherein the crystalline form is characterized by diffraction data substantially in accordance with the following:

Diffraction Angle (°2θ)
d-spacing [Å]

10.4238
8.4868

10.6954
8.2719

11.0553
8.00343

11.4849
7.70496

13.2805
6.667

15.1819
5.83602

15.4879
5.7214

16.6418
5.3272

18.2579
4.85916

19.6627
4.51503

20.0874
4.42053

20.9768
4.23506

22.2546
3.99471

22.9385
3.87714

23.1494
3.84228

23.4462
3.79432

24.3277
3.6588

24.6278
3.61488

27.0968
3.29086

28.6495
3.11594

30.4083
2.93961.

4. The crystalline form according to claim 1 , wherein the crystalline solvate is an n-propyl acetate solvate, and wherein the crystalline form is characterized by an X-ray powder diffraction pattern substantially in accordance with FIG. 4 .

5. The crystalline form according to claim 1 , wherein the crystalline solvate is an n-propyl acetate solvate, and wherein the crystalline form is characterized by diffraction angle data substantially in accordance with the following: 4.77, 7.44, 8.38, 10.14, 11.80, 12.18, 13.33, 14.10, 14.96, 16.20, 16.41, 16.84 (°2θ).

6. The crystalline form according to claim 1 , wherein the crystalline solvate is an isopropyl acetate solvate, and wherein the crystalline form is characterized by an X-ray powder diffraction pattern substantially in accordance with FIG. 5 .

7. The crystalline form according to claim 1 , wherein the crystalline solvate is an isopropyl acetate solvate, and wherein the crystalline form is characterized by diffraction angle data substantially in accordance with the following: 4.74, 7.45, 8.31, 10.07, 11.75, 13.28, 14.97, 16.30, 16.71, 16.97, 18.03, 19.05 (°2θ).

8. The crystalline form according to claim 1 , wherein the crystalline solvate is a monohydrate, and wherein the crystalline form is characterized by an X-ray powder diffraction pattern substantially in accordance with FIG. 7 .

9. The crystalline form according to claim 1 , wherein the crystalline solvate is a monohydrate, and wherein the crystalline form is characterized by diffraction angle data substantially in accordance with the following: 9.03, 9.66, 10.29, 12.29, 13.02, 14.68, 15.11, 17.54, 17.98. 19.45, 20.60, 21.51 (°2θ).

10. The crystalline form according to claim 1 , wherein the crystalline solvate is an isopropyl alcohol solvate, and wherein the crystalline form is characterized by an X-ray powder diffraction pattern substantially in accordance with FIG. 8 .

11. The crystalline form according to claim 1 , wherein the crystalline solvate is an isopropyl alcohol solvate, and wherein the crystalline form is characterized by diffraction angle data substantially in accordance with the following: 8.22, 10.35, 12.03, 16.39, 18.69, 19.97, 23.24, 24.64, 26.18, 28.07 (°2θ).

12. The crystalline form according to claim 1 , wherein the crystalline solvate is a methyl-isobutyl ketone solvate, and wherein the crystalline form is characterized by an X-ray powder diffraction pattern substantially in accordance with FIG. 9 .

13. The crystalline form according to claim 1 , wherein the crystalline solvate is a methyl-isobutyl ketone solvate, and wherein the crystalline form is characterized by diffraction angle data substantially in accordance with the following:4.74, 7.51, 8.21, 11.76, 13.30, 13.87, 15.16, 16.22, 17.03, 18.26, 18.95, 19.69 (°2θ).

14. The crystalline form according to claim 1 , wherein the crystalline solvate is a 2-methyl-tetrahydrofuran solvate, and wherein the crystalline form is characterized by an X-ray powder diffraction pattern substantially in accordance with FIG. 10 .

15. The crystalline form according to claim 1 , wherein the crystalline solvate is a 2-methyl-tetrahydrofuran solvate, and wherein the crystalline form is characterized by diffraction angle data substantially in accordance with the following: 4.73, 7.50, 8.25, 11.72, 12.34, 13.14, 13.53, 15.02, 15.92, 16.16, 16.55, 16.89 (°2θ).

16. The crystalline form according to claim 1 , wherein the crystalline solvate is a dimethyl carbonate solvate, and wherein the crystal

Assignees

• Glaxosmithkline Ip Dev Ltd

Inventors

• Diederich Ann Marie
• Herrmann Robert

Classifications

• A61P43/00

  Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title

• A61P29/00

  Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] · CPC title

• A61P17/02

  for treating wounds, ulcers, burns, scars, keloids, or the like · CPC title

• A61P17/06

  Antipsoriatics · CPC title

• A61P19/02

  for joint disorders, e.g. arthritis, arthrosis · CPC title