# US 10,946,004 B2 · Solid forms of an ASK1 inhibitor

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- Number: US 10,946,004 B2
- Document ID: US10946004B2
- Status: Granted
- Kind: B2
- Application number: 16/530,205
- Filed: 2019-08-02
- Published: 2020-02-27
- Granted: 2021-03-16
- Earliest claimed: 2014-12-23
- Assignees: Gilead Sciences, Inc.
- Applicants: Gilead Sciences, Inc.
- Inventors: Mark Andres; Brenda J. Burke Chan; Ernest A. Carra; Anna Chiu; Olga Viktorovna Lapina; Stephen P. Lathrop; Gregory Notte; Valeriya N. Smolenskaya; Lok Him Yu
- Web page: https://patentgrep.com/patent/US10946004B2

## CPC

- A61K 31/4439: containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole (nicotine A61K31/465)
- A61K 31/422: not condensed and containing further heterocyclic rings
- A61K 31/541: Non-condensed thiazines containing further heterocyclic rings
- A61P 1/00: Drugs for disorders of the alimentary tract or the digestive system
- A61P 1/04: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A61P 1/16: for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A61P 3/00: Drugs for disorders of the metabolism (of the blood or the extracellular fluid A61P7/00)
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 9/12: Antihypertensives
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 13/12: of the kidneys
- A61P 19/00: Drugs for skeletal disorders
- A61P 19/02: for joint disorders, e.g. arthritis, arthrosis
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/28: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 35/00: Antineoplastic agents
- A61P 37/00: Drugs for immunological or allergic disorders
- A61P 37/02: Immunomodulators
- A61P 37/06: Immunosuppressants, e.g. drugs for graft rejection
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07C 55/07: Salts thereof
- C07C 57/145: Maleic acid
- C07C 57/15: Fumaric acid
- C07C 59/06: Glycolic acid
- C07C 309/04: containing only one sulfo group
- C07D 401/14: containing three or more hetero rings
- C07D 413/12: linked by a chain containing hetero atoms as chain links
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Crystalline forms of 5-(4-cyclopropyl-1H-imidazol-1-yl)-N-(6-(4-isopropyl-4H-1,2,4-triazol-3-yl)pyridin-2-yl)-2-fluoro-4-methylbenzamide (Compound I) were prepared and characterized in the solid state: Also provided are processes of manufacture and methods of using the crystalline forms.

## Claims

### Claim 1

A method of treating chronic kidney disease in a patient in need thereof comprising administering a therapeutically effective amount of crystalline 5-4-cyclopropyl-1 H-imidazol-1-yl)-N-(6-(4-isopropyl-4H-1,2,4-triazol-3-yl)pyridin-2-yl)-2-fluoro-4-methylbenzamide (Compound I Form I) characterized by an X-ray powder diffractogram comprising the following peaks: 16.7, 21.3, and 22.8 °2θ±0.2 °2θ, as determined on a diffractometer using Cu-Kα radiation at a wavelength of 1.5406 Å.

### Claim 2 (depends on 1)

The method of claim 1, further comprising administering another therapeutic agent.

### Claim 3 (depends on 2)

The method of claim 2, wherein the additional therapeutic agent is filgotinib.

### Claim 4 (depends on 2)

The method of claim 2, wherein the additional therapeutic agent is a compound of formula:
or a salt thereof.

### Claim 5

A method of treating diabetic kidney disease in a patient in need thereof comprising administering a therapeutically effective amount of crystalline 5-4-cyclopropyl-1 H-imidazol-1-yl)-N-(6-(4-isopropyl-4H-1,2,4-triazol-3-yl)pyridin-2-yl)-2-fluoro-4-methylbenzamide (Compound I Form I) characterized by an X-ray powder diffractogram comprising the following peaks: 16.7, 21.3, and 22.8 °2θ±0.2 °2θ, as determined on a diffractometer using Cu-Kα radiation at a wavelength of 1.5406 Å.

### Claim 6 (depends on 5)

The method of claim 5, further comprising administering another therapeutic agent.

### Claim 7 (depends on 6)

The method of claim 6, wherein the additional therapeutic agent is filgotinib.

### Claim 8 (depends on 6)

The method of claim 6, wherein the additional therapeutic agent is a compound of formula:
or a salt thereof.