# US 10,370,352 B2 · Cyclobutyl-imidazolidinone compounds

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- Number: US 10,370,352 B2
- Document ID: US10370352B2
- Status: Granted
- Kind: B2
- Application number: 16/123,916
- Filed: 2018-09-06
- Published: 2019-03-07
- Granted: 2019-08-06
- Earliest claimed: 2017-09-07
- Assignees: Eli Lilly and Company
- Applicants: Eli Lilly and Company
- Inventors: Lian Zhu Liu; Haizhen Zhang; Xiaoqing Wang; Gang Liu
- Web page: https://patentgrep.com/patent/US10370352B2

## CPC

- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- A61P 1/16: for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention provides a compound of Formula I wherein Q is selected from the group consisting of —CH(CH3)2 and R is selected from the group consisting of or a pharmaceutically acceptable salt thereof; compositions, methods to treat liver disease and NASH.

## Claims

### Claim 1

A compound of the formula
wherein:
Q is selected from the group consisting of —CH(CH3)2 and
and
R is selected from the group consisting of
or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein: Q is —CH(CH3)2.

### Claim 3 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein: R is selected from the group consisting of

### Claim 4 (depends on 3)

The compound of claim 3, or a pharmaceutically acceptable salt thereof, wherein: R is selected from the group consisting of

### Claim 5 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein: R is selected from the group consisting of

### Claim 6 (depends on 5)

The compound of claim 5, or a pharmaceutically acceptable salt thereof, wherein: R is selected from the group consisting of

### Claim 7 (depends on 1)

The compound of claim 1, which is: 1-[6-(4-isopropyl-1,2,4-triazol-3-yl)-2-pyridyl]-3-[3-(6-methyl-3-pyridyl)cyclobutyl]imidazolidin-2-one, or a pharmaceutically acceptable salt thereof.

### Claim 8 (depends on 1)

The compound of claim 1, which is: 1-[3-(4-cyclopropylimidazol-1-yl)cyclobutyl]-3-[6-(4-isopropyl-1,2,4-triazol-3-yl)-2-pyridyl]imidazolidin-2-one, or a pharmaceutically acceptable salt thereof.

### Claim 9 (depends on 1)

The compound of claim 1, which is: 1-(3-(4-(tert-butyl)-1H-imidazol-1-yl)cyclobutyl)-3-(6-(4-isopropyl-4H-1,2,4-triazol-3-yl)pyridin-2-yl)imidazolidin-2-one, or a pharmaceutically acceptable salt thereof.

### Claim 10 (depends on 1)

The compound of claim 1, which is: 1-(6-(4-isopropyl-4H-1,2,4-triazol-3-yl)pyridin-2-yl)-3-(3-(2-methylpyrimidin-5-yl)cyclobutyl)imidazolidin-2-one, or a pharmaceutically acceptable salt thereof.

### Claim 11 (depends on 1)

A pharmaceutical composition comprising the compound of claim 1, or a pharmaceutically acceptable salt thereof, and at least one pharmaceutically acceptable carrier, diluent, or excipient.

### Claim 12 (depends on 1)

A method for treating nonalcoholic steatohepatitis (NASH) in a mammal in need thereof, comprising administering to an effective amount of the compound of claim 1, or a pharmaceutically acceptable salt thereof, to the mammal.

### Claim 13 (depends on 2)

The compound of claim 2, or a pharmaceutically acceptable salt thereof, wherein: R is selected from the group consisting of

### Claim 14 (depends on 13)

The compound of claim 13, or a pharmaceutically acceptable salt thereof, wherein: R is selected from the group consisting of

### Claim 15 (depends on 2)

The compound of claim 2, or a pharmaceutically acceptable salt thereof, wherein: R is selected from the group consisting of:

### Claim 16 (depends on 15)

The compound of claim 15, or a pharmaceutically acceptable salt thereof, wherein: R is selected from the group consisting of

### Claim 17 (depends on 12)

The method of claim 12, wherein the mammal is a human.

### Claim 18 (depends on 12)

The method of claim 12, wherein the compound is:
1-[6-(4-isopropyl-1,2,4-triazol-3-yl)-2-pyridyl]-3-[3-(6-methyl-3-pyridyl)cyclobutyl]imidazolidin-2-one,
or a pharmaceutically acceptable salt thereof.

### Claim 19 (depends on 12)

The method of claim 12, wherein the compound is:
1-[3-(4-cyclopropylimidazol-1-yl)cyclobutyl]-3-[6-(4-isopropyl-1,2,4-triazol-3-yl)-2-pyridyflimidazolidin-2-one,
or a pharmaceutically acceptable salt thereof.

### Claim 20 (depends on 12)

The method of claim 12, wherein the compound is:
1-(3-(4-(tert-butyl)-1H-imidazol-1-yl)cyclobutyl)-3-(6-(4-isopropyl-4H-1,2,4-triazol-3-yl)pyridin-2-yl)imidazolidin-2-one,
or a pharmaceutically acceptable salt thereof.

### Claim 21 (depends on 12)

The method of claim 12, wherein the compound is:
1-(6-(4-isopropyl-4H-1,2,4-triazol-3-yl)pyridin-2-yl)-3-(3-(2-methylpyrimidin-5-yl)cyclobutyl)imidazolidin-2-one,
or a pharmaceutically acceptable salt thereof.

### Claim 22 (depends on 11)

The pharmaceutical composition of claim 11, wherein the compound is:
1-[6-(4-isopropyl-1,2,4-triazol-3-yl)-2-pyridyl]-3-[3-(6-methyl-3-pyridyl)cyclobutyl]imidazolidin-2-one,
or a pharmaceutically acceptable salt thereof.

### Claim 23 (depends on 11)

The pharmaceutical composition of claim 11, wherein the compound is:
1-[3-(4-cyclopropylimidazol-1-yl)cyclobutyl]-3-[6-(4-isopropyl-1,2,4-triazol-3-yl)-2-pyridyflimidazolidin-2-one,
or a pharmaceutically acceptable salt thereof.

### Claim 24 (depends on 11)

The pharmaceutical composition of claim 11, wherein the compound is:
1-(3-(4-(tert-butyl)-1H-imidazol-1-yl)cyclobutyl)-3-(6-(4-isopropyl-4H-1,2,4-triazol-3-yl)pyridin-2-yl)imidazolidin-2-one,
or a pharmaceutically acceptable salt thereof.

### Claim 25 (depends on 11)

The pharmaceutical composition of claim 11, wherein the compound is:
1-(6-(4-isopropyl-4H-1,2,4-triazol-3-yl)pyridin-2-yl)-3-(3-(2-methylpyrimidin-5-yl)cyclobutyl)imidazolidin-2-one,
or a pharmaceutically acceptable salt thereof.