# US 10,766,888 B1 · HMOX1 inducers

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- Number: US 10,766,888 B1
- Document ID: US10766888B1
- Status: Granted
- Kind: B1
- Application number: 16/843,426
- Filed: 2020-04-08
- Granted: 2020-09-08
- Earliest claimed: 2019-04-12
- Assignees: Mitobridge, Inc.
- Applicants: Mitobridge Inc.
- Inventors: Margaret Biddle; Arthur Kluge; Sanjita Sasmal; Bharat Lagu; Xinyuan Wu; Takashi Ogiyama; Eric Bell
- Web page: https://patentgrep.com/patent/US10766888B1

## CPC

- C07D 413/14: containing three or more hetero rings
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 5/14: of the thyroid hormones, e.g. T3, T4
- A61P 7/00: Drugs for disorders of the blood or the extracellular fluid
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 9/08: Vasodilators for multiple indications
- A61P 17/00: Drugs for dermatological disorders
- A61P 21/00: Drugs for disorders of the muscular or neuromuscular 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 35/00: Antineoplastic agents
- C07D 235/30: Nitrogen atoms not forming part of a nitro radical
- C07D 403/12: linked by a chain containing hetero atoms as chain links
- C07D 413/12: linked by a chain containing hetero atoms as chain links
- C07D 417/12: linked by a chain containing hetero atoms as chain links
- C07D 417/14: containing three or more hetero rings
- C07D 513/04: Ortho-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention is related to compounds of structure (I) as heme oxygenase 1 (HMOX 1) inducers. The present invention is also related a method of controlling the activity or the amount, or both the activity and the amount, of heme-oxygenase 1 in a mammalian subject. The definitions of the variables are provided herein.

## Claims

### Claim 1

A compound represented by structural formula (III-B):
or a pharmaceutically acceptable salt thereof, wherein
R1 is —C(═O)NH(C1-C4)alkyl optionally substituted with —OH, —NH2, —(C1-C4)-alkoxy, or —(C1-C4)hydroxyalkoxy, and
R2 is H.

### Claim 2 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein
R1 is —C(═O)NH(C1-C4)alkyl substituted with —OH.

### Claim 3 (depends on 2)

The compound of claim 2, wherein the compound is:
2-(benzo[d]oxazol-2-ylamino)-N-(2-hydroxyethyl)-1-methyl-1H-benzo[d]imidazole-5-carboxamide or a pharmaceutically acceptable salt thereof.

### Claim 4 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein
R1 is —C(═O)NH(C1-C4)alkyl substituted with —NH2.

### Claim 5 (depends on 4)

The compound of claim 4, wherein the compound is:
N-(2-aminoethyl)-2-(benzo[d]oxazol-2-ylamino)-1-methyl-1H-benzo[d]imidazole-5-carboxamide or a pharmaceutically acceptable salt thereof.

### Claim 6 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein
R1 is —C(═O)NH(C1-C4)alkyl substituted with —(C1-C4)hydroxyalkoxy.

### Claim 7 (depends on 6)

The compound of claim 6, wherein the compound is:
2-(benzo[d]oxazol-2-ylamino)-N-(2-(2-hydroxyethoxy)ethyl)-1-methyl-1H-benzo[d]imidazole-5-carboxamide or a pharmaceutically acceptable salt thereof.

### Claim 8 (depends on 1)

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

### Claim 9 (depends on 1)

A method of increasing the activity of or the amount of HMOX-1 in a human subject comprising: administering to a human subject an effective amount of the compound of claim 1, or a pharmaceutically acceptable salt thereof.

### Claim 10 (depends on 1)

A method of activating transcription factor Nrf2 in a human subject comprising: administering to a human subject an effective amount of a compound of claim 1, or a pharmaceutically acceptable salt thereof.

### Claim 11 (depends on 1)

A method of reducing the amount of ROS in a human subject comprising: administering to a human subject an effective amount of the compound of claim 1, or a pharmaceutically acceptable salt thereof.