# US 2016/0256459 A1 · Solid forms of 2-(tert-butylamino)-4-((1r,3r,4r)-3-hydroxy-4-methylcyclohexylamino)-pyrimidine-5-carboxamide, compositions thereof and methods of their use

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 2016/0256459 A1
- Document ID: US20160256459A1
- Status: Published application
- Kind: A1
- Application number: 15/152,653
- Filed: 2016-05-12
- Published: 2016-09-08
- Earliest claimed: 2014-01-30
- Assignees: Signal Pharmaceuticals, LLC
- Applicants: Signal Pharmaceuticals, LLC
- Inventors: Hon-Wah Man; Jean Xu; Marie Georges Beauchamps; Mohit Atul Kothare; Nanfei Zou; Ying Li; Lianfeng Huang; Daozhong Zou
- Web page: https://patentgrep.com/patent/US20160256459A1

## CPC

- A61K 31/505: Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- C07D 239/42: One nitrogen atom (nitro radicals C07D239/30)
- C07D 239/48: Two nitrogen atoms
- 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)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Provided herein are formulations, processes, solid forms and methods of use relating to 2-(tert-butylamino)-4-((1R,3R,4R)-3-hydroxy-4-methylcyclohexylamino)-pyrimidine-5-carboxamide.

## Claims

### Claim at position 1

1-20. (canceled)

### Claim 21

A method for treating a condition treatable by inhibition of a kinase pathway, comprising administering to a subject having a condition treatable by inhibition of a kinase pathway an effective amount of a crystal form of Compound 1, or a tautomer thereof:

### Claim 22 (depends on 21)

The method of claim 21, wherein the crystal form has an X-ray powder diffraction pattern comprising peaks at 10.55, 13.61 and 19.84±0.2° 2θ.

### Claim 23 (depends on 21)

The method of claim 21, wherein the crystal form has an X-ray powder diffraction pattern comprising peaks at 9.80, 17.29, 20.66 and 21.74±0.2° 2θ.

### Claim 24 (depends on 21)

The method of claim 21, wherein the crystal form has an X-ray powder diffraction pattern comprising peaks at 9.83, 10.21, 17.26 and 21.86±0.2° 2θ.

### Claim 25 (depends on 21)

The method of claim 21, wherein the crystal form has an X-ray powder diffraction pattern comprising peaks at 10.37, 13.41, 19.52 and 22.47±0.2° 2θ.

### Claim 26 (depends on 21)

The method of claim 21, wherein the crystal form has an X-ray powder diffraction pattern comprising peaks at 9.92, 17.29, 20.10 and 21.81±0.2° 2θ.

### Claim 27 (depends on 21)

The method of claim 21, wherein the crystal form has an X-ray powder diffraction pattern comprising peaks at 18.53, 20.85 and 21.10±0.2° 2θ.

### Claim 28 (depends on 21)

The method of claim 21, wherein the crystal form has an X-ray powder diffraction pattern comprising peaks at 9.51, 10.34, 17.90 and 21.28±0.2° 2θ.

### Claim 29 (depends on 21)

The method of claim 21, wherein the crystal form has an X-ray powder diffraction pattern comprising peaks at 9.74, 17.22, 18.04 and 21.76±0.2° 2θ.

### Claim 30 (depends on 21)

The method of claim 21, wherein the crystal form has an X-ray powder diffraction pattern comprising peaks at 7.94, 16.00 and 18.27±0.2° 2θ.

### Claim 31

A method for treating interstitial pulmonary fibrosis, systemic sclerosis, scleroderma, chronic allograft nephropathy, antibody mediated rejection, or lupus, comprising administering to a subject having interstitial pulmonary fibrosis, systemic sclerosis, scleroderma, chronic allograft nephropathy, antibody mediated rejection, or lupus an effective amount of a crystal of comprising Compound 1, or a tautomer thereof:

### Claim 32 (depends on 31)

The method of claim 31, wherein the crystal form has an X-ray powder diffraction pattern comprising peaks at 10.55, 13.61, 17.20 and 19.84±0.2° 2θ.

### Claim 33 (depends on 31)

The method of claim 31, wherein the crystal form has an X-ray powder diffraction pattern comprising peaks at 9.80, 17.29, 20.66 and 21.74±0.2° 2θ.

### Claim 34 (depends on 31)

The method of claim 31, wherein the crystal form has an X-ray powder diffraction pattern comprising peaks at 9.83, 10.21, 17.26 and 21.86±0.2° 2θ.

### Claim 35 (depends on 31)

The method of claim 31, wherein the crystal form has an X-ray powder diffraction pattern comprising peaks at 10.37, 13.41, 19.52 and 22.47±0.2° 2θ.

### Claim 36 (depends on 31)

The method of claim 31, wherein the crystal form has an X-ray powder diffraction pattern comprising peaks at 9.92, 17.29, 20.10 and 21.81±0.2° 2θ.

### Claim 37 (depends on 31)

The method of claim 31, wherein the crystal form has an X-ray powder diffraction pattern comprising peaks at 18.53, 20.85 and 21.10±0.2° 2θ.

### Claim 38 (depends on 31)

The method of claim 31, wherein the crystal form has an X-ray powder diffraction pattern comprising peaks at 9.51, 10.34, 17.90 and 21.28±0.2° 2θ.

### Claim 39 (depends on 31)

The method of claim 31, wherein the crystal form has an X-ray powder diffraction pattern comprising peaks at 9.74, 17.22, 18.04 and 21.76±0.2° 2θ.

### Claim 40 (depends on 31)

The method of claim 31, wherein the crystal form has an X-ray powder diffraction pattern comprising peaks at 7.94, 16.00 and 18.27±0.2° 2θ.

### Claim 41 (depends on 31)

The method of claim 31, wherein the subject has interstitial pulmonary fibrosis.

### Claim 42

A method for treating a liver fibrotic disorder, diabetes, metabolic syndrome leading to a liver fibrotic disorder, or a condition treatable by inhibition of a kinase pathway, comprising administering to a subject having a liver fibrotic disorder, diabetes, metabolic syndrome leading to a liver fibrotic disorder, or a condition treatable by inhibition of a kinase pathway an effective amount a crystal form of Compound 1, or a tautomer thereof:

### Claim 43 (depends on 42)

The method of claim 42, wherein the crystal form has an X-ray powder diffraction pattern comprising peaks at 10.55, 13.61, 17.20 and 19.84±0.2° 2θ.

### Claim 44 (depends on 42)

The method of claim 42, wherein the crystal form has an X-ray powder diffraction pattern comprising peaks at 9.80, 17.29, 20.66 and 21.74±0.2° 2θ.

### Claim 45 (depends on 42)

The method of claim 42, wherein the crystal form has an X-ray powder diffraction pattern comprising peaks at 9.83, 10.21, 17.26 and 21.86±0.2° 2θ.

### Claim 46 (depends on 42)

The method of claim 42, wherein the crystal form has an X-ray powder diffraction pattern comprising peaks at 10.37, 13.41, 19.52 and 22.47±0.2° 2θ.

### Claim 47 (depends on 42)

The method of claim 42, wherein the crystal form has an X-ray powder diffraction pattern comprising peaks at 9.92, 17.29, 20.10 and 21.81±0.2° 2θ.

### Claim 48 (depends on 42)

The method of claim 42, wherein the crystal form has an X-ray powder diffraction pattern comprising peaks at 18.53, 20.85 and 21.10±0.2° 2θ.

### Claim 49 (depends on 42)

The method of claim 42, wherein the crystal form has an X-ray powder diffraction pattern comprising peaks at 9.51, 10.34, 17.90 and 21.28±0.2° 2θ.

### Claim 50 (depends on 42)

The method of claim 42, wherein the crystal form has an X-ray powder diffraction pattern comprising peaks at 9.74, 17.22, 18.04 and 21.76±0.2° 2θ.

### Claim 51 (depends on 42)

The method of claim 42, wherein the crystal form has an X-ray powder diffraction pattern comprising peaks at 7.94, 16.00 and 18.27±0.2° 2θ.