# US 2019/0315697 A1 · Isotopologues of 2-(tert-butylamino)-4-((1r,3r,4r)-3-hydroxy-4-methylcyclohexylamino)-pyrimidine-5-carboxamide

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- Number: US 2019/0315697 A1
- Document ID: US20190315697A1
- Status: Published application
- Kind: A1
- Application number: 16/452,691
- Filed: 2019-06-26
- Published: 2019-10-17
- Earliest claimed: 2015-01-29
- Assignees: Signal Pharmaceuticals, LLC
- Applicants: Signal Pharmaceuticals, LLC
- Inventors: Hon-Wah MAN; Mohit Atul KOTHARE
- Web page: https://patentgrep.com/patent/US20190315697A1

## CPC

- C07D 239/48: Two nitrogen atoms
- C07B 59/002: {Heterocyclic compounds}
- C07B 2200/05: Isotopically modified compounds, e.g. labelled
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

Provided herein are isotopologues of Compound A, which are enriched with isotopes such as, for example, deuterium. Pharmaceutical compositions comprising the isotope-enriched compounds, and methods of using such compounds are also provided.

## Claims

### Claim 1

A compound, wherein the compound is a compound having the following structure:
or a pharmaceutically acceptable salt, stereoisomer or solvate thereof,
wherein one or more of Y1, Y2, Y3, Y4, Y5, Y6, Y7, Y8, Y9, Y10, Y11, Y12, Y13, Y14, Y15, Y16, Y17, Y18, Y19, Y20, Y21, and Y22 is a hydrogen that is isotopically enriched with deuterium, and the others of Y1, Y2, Y3, Y4, Y5, Y6, Y7, Y8, Y9, Y10, Y11, Y12, Y13, Y14, Y15, Y16, Y17, Y18, Y19, Y20, Y21, and Y22 are non-enriched hydrogen atoms.

### Claim 2 (depends on 1)

The compound of claim 1, wherein the compound has the following structure:

### Claim 3 (depends on 1)

The compound of claim 1, wherein one of Y1, Y2, Y3, Y4, Y5, Y6, Y7, Y8, Y9, Y10, Y11, Y12, Y13, Y14, Y15, Y16, Y17, Y18, Y19, Y20, Y21, and Y22 is isotopically enriched with deuterium, and the others are non-enriched hydrogens.

### Claim 4 (depends on 1)

The compound of claim 1, wherein two of Y1, Y2, Y3, Y4, Y5, Y6, Y7, Y8, Y9, Y10, Y11, Y12, Y13, Y14, Y15, Y16, Y17, Y18, Y19, Y20, Y21, and Y22 are isotopically enriched with deuterium, and the others are non-enriched hydrogens.

### Claim 5 (depends on 1)

The compound of claim 1, wherein the compound is:

### Claim 6 (depends on 1)

A pharmaceutical composition comprising a compound of claim 1, or a pharmaceutically acceptable salt or solvate thereof.

### Claim 7 (depends on 1)

A method of treating a liver fibrotic disorder, diabetes or a metabolic syndrome leading to a liver fibrotic disorder comprising administering to a patient having a liver fibrotic disorder, diabetes or a metabolic syndrome leading to a liver fibrotic disorder a compound of claim 1, or a pharmaceutically acceptable salt or solvate thereof.