# US 2017/0283404 A1 · Crystalline forms of 2-(4-(4-ethoxy-6-oxo-1,6-dihydropyridin-3-yl)-2-fluorophenyl)-n-(5-(1,1,1-trifluoro-2-methylpropan-2-yl)isoxazol-3-yl)acetamide

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- Number: US 2017/0283404 A1
- Document ID: US20170283404A1
- Status: Published application
- Kind: A1
- Application number: 15/509,255
- Filed: 2015-09-04
- Published: 2017-10-05
- Earliest claimed: 2014-09-08
- Assignees: GlaxoSmithKline Intellectual Property Development Limited
- Applicants: Glaxosmithkline Intellectual Property Development Limited
- Inventors: Mui CHEUNG; William M. CLARK; Hilary Schenck EIDAM; Kimberly Anne LAMEY; James V. THOMAS
- Web page: https://patentgrep.com/patent/US20170283404A1

## CPC

- C07D 413/12: linked by a chain containing hetero atoms as chain links
- A61P 1/00: Drugs for disorders of the alimentary tract or the digestive system
- A61P 1/12: Antidiarrhoeals
- A61P 35/00: Antineoplastic agents
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07B 2200/13: Crystalline forms, e.g. polymorphs
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

Disclosed are novel crystalline forms of 2-(4-(4-ethoxy-6-oxo-1,6-dihydropyridin-3-yl)-2-fluorophenyl)-N-(5-(1,1,1-trifluoro-2-methylpropan-2-yl)isoxazol-3-yl)acetamide and pharmaceutical compositions containing the same. Also disclosed are processes for the preparation thereof and methods for use thereof.

## Claims

### Claim 1

A crystalline form of 2-(4-(4-ethoxy-6-oxo-1,6-dihydropyridin-3-yl)-2-fluorophenyl)-N-(5-(1,1,1-trifluoro-2-methylpropan-2-yl)i soxazol-3 -yl)acetamide.

### Claim 2 (depends on 1)

The crystalline form according to claim 1, wherein the crystalline form is characterized by an X-ray powder diffraction (XRPD) pattern comprising at least three diffraction angles, when measured using Cu Kα radiation, selected from a group consisting of about 10.1, 10.7, 11.5, 13.2, 13.9, 14.3, 16.7, 17.1, 17.6, 18.3, 18.4, 18.9, 20.3, 20.7, 21.4, 21.6, 22.0, 23.2, 23.9, 24.9, 25.2, 26.3, 26.6, 27.4, 28.6, 29.3, 30.0, 30.7, 31.2, 32.6, 34.3, 35.9, 38.5, and 39.4 degrees 2θ.

### Claim 3 (depends on 1)

The crystalline form according to claim 1, wherein the crystalline form is characterized by an X-ray powder diffraction (XRPD) pattern comprising at least three diffraction angles, when measured using Cu Kα radiation, selected from a group consisting of about 10.1, 10.7, 11.5, 13.9, 17.1, 18.3, 18.4, 20.3, 20.7, 21.4, 21.6, 22.0, 23.2, 23.9, 24.9, 25.2, 26.3, 26.6, 28.6, 30.0, and 32.6 degrees 2θ.

### Claim 4 (depends on 1)

The crystalline form according to claim 1, wherein the crystalline form is characterized by an X-ray powder diffraction (XRPD) pattern comprising at least three diffraction angles, when measured using Cu Kα radiation, selected from a group consisting of about 10.1, 10.7, 11.5, 13.9, 17.1, 18.3, 18.4, 20.3, 20.7, 21.4, 21.6, 22.0, 23.2, 23.9, 24.9, and 26.6 degrees 2θ.

### Claim 5 (depends on 1)

The crystalline form according to claim 1, wherein the crystalline form is characterized by an X-ray powder diffraction (XRPD) pattern comprising diffraction angles, when measured using Cu Kα radiation, of about 13.9, 17.1, 18.3, 18.4, 21.4, 21.6, and 23.9 degrees 2θ.

### Claim 6 (depends on 2)

The crystalline form according to claim 2, wherein the crystalline form is characterized by an X-ray powder diffraction (XRPD) pattern substantially in accordance with FIG. 1.

### Claim 7 (depends on 1)

The crystalline form according to claim 1, wherein the crystalline form is characterized by an X-ray powder diffraction (XRPD) pattern comprising at least three diffraction angles, when measured using Cu Kα radiation, selected from a group consisting of about 4.5, 5.0, 6.0, 7.9, 9.3, 10.0, 11.2, 13.1, 13.3, 13.8, 15.0, 15.5, 16.6, 17.1, 18.2, 18.7, 19.0, 19.7, 20.2, 20.7, 21.6, 22.6, 23.3, 23.8, 24.3, 26.0, 26.6, 27.2, 28.1, 28.7, 29.1, 30.3, 31.3, and 35.6 degrees 2θ.

### Claim at position 8

8-9. (canceled)

### Claim 10 (depends on 1)

The crystalline form according to claim 1, wherein the crystalline form is characterized by an X-ray powder diffraction (XRPD) pattern comprising diffraction angles, when measured using Cu Kα radiation, of about 13.1, 13.3, 17.1, 18.2, 21.6, 23.3, and 23.8 degrees 2θ.

### Claim 11 (depends on 7)

The crystalline form according to claim 7, wherein the crystalline form is characterized by an X-ray powder diffraction (XRPD) pattern substantially in accordance with FIG. 5.

### Claim 12 (depends on 1)

The crystalline form according to claim 1, wherein the crystalline form is characterized by an X-ray powder diffraction (XRPD) pattern comprising at least three diffraction angles, when measured using Cu Kα radiation, selected from a group consisting of about 6.4, 12.7, 14.2, 15.4, 16.1, 17.2, 17.9, 18.9, 19.6, 20.1, 21.2, 21.9, 22.8, 23.7, 24.7, 25.6, 26.6, 28.7, 29.5, 32.3, and 34.9 degrees 2θ.

### Claim at position 12

13-14. (canceled)

### Claim 15 (depends on 1)

The crystalline form according to claim 1, wherein the crystalline form is characterized by an X-ray powder diffraction (XRPD) pattern comprising diffraction angles, when measured using Cu Kα radiation, of about 6.4, 12.7, 14.2, 17.2, 18.9, 20.1, and 21.2 degrees 2θ.

### Claim 16 (depends on 12)

The crystalline form according to claim 12, wherein the crystalline form is characterized by an X-ray powder diffraction (XRPD) pattern substantially in accordance with FIG. 9.

### Claim 17 (depends on 1)

The crystalline form according to claim 1, wherein the crystalline form is characterized by an X-ray powder diffraction (XRPD) pattern comprising at least three diffraction angles, when measured using Cu Kα radiation, selected from a group consisting of about 9.6, 11.0, 11.7, 13.8, 14.3, 15.3, 16.6, 17.2, 17.5, 18.8, 19.3, 20.3, 21.1, 21.4, 22.0, 23.0, 23.6, 24.5, 25.8, 26.2, 27.4, 27.7, 28.6, 29.6, 30.8, 31.0, 31.4, 32.3, 33.3, 35.9, and 39.2 degrees 2θ.

### Claim at position 16

18-19. (canceled)

### Claim 20 (depends on 1)

The crystalline form according to claim 1, wherein the crystalline form is characterized by an X-ray powder diffraction (XRPD) pattern comprising diffraction angles, when measured using Cu Kα radiation, of about 9.6, 13.8, 20.3, 21.4, 22.0, 24.5, and 26.2 degrees 2θ.

### Claim 21 (depends on 17)

The crystalline form according to claim 17, wherein the crystalline form is characterized by an X-ray powder diffraction (XRPD) pattern substantially in accordance with FIG. 12.

### Claim 22 (depends on 1)

A pharmaceutical composition comprising the crystalline form according to claim 1 and a pharmaceutically acceptable carrier.

### Claim 23 (depends on 22)

The composition according to claim 22 wherein the composition is adapted for oral administration.

### Claim 24 (depends on 23)

The composition according to claim 23 wherein the composition is in the form of a tablet or capsule.

### Claim 25 (depends on 1)

A method of treating irritable bowel syndrome in a human in need thereof comprising administering to said human an effective amount of the crystalline form according to claim 1.

### Claim 26 (depends on 22)

A method of treating irritable bowel syndrome in a human in need thereof comprising administering to said human an effective amount of the composition according to claim 22.

### Claim at position 24

27-30. (canceled)