# US 10,865,201 B2 · Bicyclic compounds useful as GPR120 modulators

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- Number: US 10,865,201 B2
- Document ID: US10865201B2
- Status: Granted
- Kind: B2
- Application number: 16/331,928
- Filed: 2017-09-11
- Published: 2019-07-18
- Granted: 2020-12-15
- Earliest claimed: 2016-09-12
- Assignees: Valo Health, Inc.
- Applicants: Valo Health, Inc.
- Inventors: Brian Raimundo; Elena S. Koltun; John Griffin; Eric Stangeland
- Web page: https://patentgrep.com/patent/US10865201B2

## CPC

- C07D 417/12: linked by a chain containing hetero atoms as chain links
- A61P 1/16: for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A61P 3/08: for glucose homeostasis (pancreatic hormones A61P5/48)
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- 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]
- C07D 275/06: with hetero atoms directly attached to the ring sulfur atom
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- C07D 417/14: containing three or more hetero rings
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Provided herein are compounds, compositions including them, and methods of modulating GPR120 activity and treating diseases mediated by GPR120 by administering such compounds and compositions.

## Claims

### Claim 1

A compound of formula:
wherein
each X independently is CH, CR3, or N;
Y is SO2;
Z is —CH2—, —CH(CH3)—, —C(CH2CH2)—(cyclopropano), —(CO)CH2—, or —CHCH—;
U is CH2, —CH(CH3)—, —C(CH3)2—, or —CH2CH2—;
R1 is an optionally substituted alkyl group, an optionally substituted 3-7 membered cycloalkyl or heterocyclyl group, an optionally substituted 6-membered aryl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 5,6- or 6,6-membered bicyclic heteroaryl group, or an optionally substituted bicyclic aryl group;
R2 is an optionally substituted 3-7 membered cycloalkyl or heterocyclyl group, an optionally substituted 6-membered aryl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 5,6- or 6,6-membered bicyclic aryl or heteroaryl group, or an optionally substituted bicyclic aryl group; and
R3 is a halogen, or an optionally substituted alkyl or alkoxy group.

### Claim 2 (depends on 1)

The compound of claim 1 of formula
wherein
U is CH2, —CH(CH3)—, —C(CH3)2—, or —CH2CH2—;
R1 is an optionally substituted alkyl group, an optionally substituted 3-7 membered cycloalkyl or heterocyclyl group, an optionally substituted 6-membered aryl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 5,6- or 6,6-membered bicyclic heteroaryl group, or an optionally substituted bicyclic aryl group; and
R2 is an optionally substituted 3-7 membered cycloalkyl or heterocyclyl group, an optionally substituted 6-membered aryl group, an optionally substituted 5- or 6-membered heteroaryl group, an optionally substituted 5,6- or 6,6-membered bicyclic heteroaryl group, or an optionally substituted bicyclic aryl group.

### Claim 3

A compound of the structure
or a tautomer thereof, or an isotopomer thereof, or a stereoisomer thereof, or a pharmaceutically acceptable salt of each thereof, or a prodrug thereof, or a pharmaceutically acceptable solvate of each of the foregoing.

### Claim 4 (depends on 1)

A pharmaceutical composition comprising a compound of claim 1 and a pharmaceutically acceptable excipient.

### Claim 5 (depends on 1)

A method for agonizing GPR120, comprising contacting the GPR120 with a compound of claim 1.

### Claim 6 (depends on 1)

A method for modulating metabolism in a mammal in need thereof, comprising contacting GPR120 in the mammal with an amount of the compound of claim 1 effective to modulate metabolism in the mammal.

### Claim 7 (depends on 4)

A method for modulating metabolism in a mammal in need thereof, comprising administering to the mammal an amount of the composition of claim 4 effective to modulate metabolism in the mammal.

### Claim 8 (depends on 1)

A method for reducing inflammation in a mammal, comprising contacting GPR120 in the mammal with an amount of the compound of claim 1 effective to reduce the inflammation.

### Claim 9 (depends on 4)

A method for reducing inflammation in a mammal, comprising administering to the mammal an amount of the composition of claim 4 effective to reduce the inflammation.

### Claim 10 (depends on 1)

A method for reducing neuroinflammation in a mammal, comprising contacting GPR120 in the mammal with an amount of the compound of claim 1 effective to reduce the neuroinflammation.

### Claim 11 (depends on 4)

A method for reducing neuroinflammation in a mammal, comprising administering to the mammal an amount of the composition of claim 4 effective to reduce neuroinflammation.

### Claim 12 (depends on 1)

A method for treating diabetes, pre-diabetes or metabolic syndrome, or one or more symptoms of each thereof in a mammal, comprising contacting GPR120 in the mammal with a therapeutically effective amount of the compound of claim 1.

### Claim 13 (depends on 4)

A method for treating diabetes, pre-diabetes or metabolic syndrome, or one or more symptoms of each thereof in a mammal, comprising administering to the mammal a therapeutically effective amount of the composition of claim 4.

### Claim 14 (depends on 1)

A method for treating steatohepatitis in a mammal, comprising contacting GPR120 in the mammal with a therapeutically effective amount of the compound of claim 1.

### Claim 15 (depends on 4)

A method for treating steatohepatitis in a mammal, comprising administering to the mammal a therapeutically effective amount of the composition of claim 4.

### Claim 16 (depends on 1)

A method for treating non-alcoholic steatohepatitis in a mammal, comprising contacting GPR120 in the mammal with a therapeutically effective amount of the compound of claim 1.

### Claim 17 (depends on 4)

A method for treating non-alcoholic steatohepatitis in a mammal, comprising administering to the mammal a therapeutically effective amount of the composition of claim 4.

### Claim 18 (depends on 1)

A method for treating a disorder associated with, leading to, or resulting from neuroinflammation in a mammal, comprising contacting GPR120 in the mammal with a therapeutically effective amount of the compound of claim 1.

### Claim 19 (depends on 4)

A method for treating a disorder associated with, leading to, or resulting from neuroinflammation in a mammal, comprising administering to the mammal a therapeutically effective amount of the composition of claim 4.

### Claim 20 (depends on 1)

A method for treating Alzheimer's disease, Parkinson's disease, frontotemporal dementia, amyotrophic lateral sclerosis or multi-system atrophy, or one or more symptoms of each thereof, in a patient, comprising contacting GPR120 in the patient with a therapeutically effective amount of the compound of claim 1.