# US 12,758,530 B2 · Antioxidant and use thereof

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- Number: US 12,758,530 B2
- Document ID: US12758530B2
- Status: Granted
- Kind: B2
- Application number: 17/424,334
- Filed: 2019-12-18
- Published: 2022-04-14
- Granted: 2026-10-13
- Earliest claimed: 2019-01-28
- Assignees: Bioradical Research Institute Corp.
- Applicants: Bioradical Research Institute Corp.
- Inventors: Keisuke Makino; Toshiyuki Arai; Yoko Arai; Masaichi Lee
- Web page: https://patentgrep.com/patent/US12758530B2

## CPC

- A61K 31/4155: non condensed and containing further heterocyclic rings
- A61P 39/06: Free radical scavengers or antioxidants
- 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention provides a new antioxidant. An antioxidant of the present invention includes: a compound represented by the following formula (1) or a salt thereof: where in the formula (1), an A ring and a B ring may be the same or different and are a pyrazole ring having a substituent or a pyrazoline ring having a substituent, and L is a saturated or unsaturated hydrocarbon group.

## Claims

### Claim 1

A compound represented by the following formula (1) or a salt thereof:
where in the formula (1),
an A ring and a B ring may be the same or different and represented by the following formula (2) or (3):
where in the formula (2),
R1 is a halogen atom, an alkyl group, an amino group, a cyano group, a hydroxy group, a sulfo group, a carboxyl group, an alkoxy group, a hydroxyalkyl group, an acyl group, an alkenyl group, an alkynyl group, or an aryl group that may have a substituent,
R2 is a halogen atom, an alkyl group, an amino group, a cyano group, a hydroxy group, a sulfo group, a carboxyl group, an alkoxy group, a hydroxyalkyl group, an acyl group, or an alkynyl group that may have a substituent, and
R3 is a halogen atom, an amino group, a cyano group, a hydroxy group, a sulfo group, a carboxyl group, an alkoxy group, a hydroxyalkyl group, an acyl group, an alkynyl group, or an aryl group that may have a substituent, and
where in the formula (3),
R4 is a halogen atom, an alkyl group, an amino group, a cyano group, a hydroxy group, a sulfo group, a carboxyl group, an alkoxy group, a hydroxyalkyl group, an acyl group, an alkenyl group, an alkynyl group, or an aryl group that may have a substituent,
R5 is a halogen atom, an alkyl group, an amino group, a cyano group, a hydroxy group, a sulfo group, a carboxyl group, an alkoxy group, a hydroxyalkyl group, an acyl group, an alkenyl group, an alkynyl group, or an aryl group that may have a substituent, and
R6 is an oxygen atom, a halogen atom, an alkyl group, an amino group, a cyano group, a hydroxy group, a sulfo group, a carboxyl group, an alkoxy group, a hydroxyalkyl group, an acyl group, an alkenyl group, an alkynyl group, or an aryl group that may have a substituent, and
L is a saturated hydrocarbon group having 2 to 6 carbon atoms.

### Claim 2 (depends on 1)

The compound antioxidant according to claim 1, wherein
the compound represented by the formula (1) is a compound represented by the following formula (4):
where in the formula (4),
R1 is a halogen atom, or an alkyl group,
R2 is an alkyl group or an aryl group that may have a substituent,
R3 is a halogen atom, or a hydroxy group,
R4 is a halogen atom, or an alkyl group,
R5 is an alkyl group or an aryl group that may have a substituent,
R6 is an oxygen atom, a halogen atom, or a hydroxy group, and
L is a saturated hydrocarbon group having 2 to 6 carbon atoms.

### Claim 3 (depends on 1)

The compound according to claim 1, wherein
the compound represented by the formula (1) is a compound represented by the following formula (12):
where in the formula (12),
R1 is a halogen atom or an alkyl group,
R2 is an alkyl group that may have a substituent,
R3 is a halogen atom or a hydroxy group,
R1′ is a halogen atom or an alkyl group,
R2′ is an alkyl group that may have a substituent,
R3′ is a halogen atom, an alkyl group, or a hydroxy group, and
L is a saturated hydrocarbon group having 2 to 6 carbon atoms.

### Claim 4 (depends on 1)

A cell protection or antioxidation method comprising contacting a cell with the compound according to claim 1.

### Claim 5 (depends on 1)

An antioxidation method comprising:
administering the compound of claim 1 to a subject having oxidative stress caused by reactive oxygen species.

### Claim 6 (depends on 4)

The antioxidation method according to claim 4, wherein the contacting is in vitro.

### Claim 7 (depends on 1)

A method for treating a disease caused by oxidative stress caused by reactive oxygen species, comprising the step of:
administering to a patient the compound according to claim 1.

### Claim 8 (depends on 7)

The method according to claim 7, wherein
the disease caused by oxidative stress is cerebral infarction, amyotrophic lateral sclerosis, Alzheimer's disease, or Parkinson's disease.

### Claim 9

A compound represented by the following formula (13) or a salt thereof:

### Claim 10 (depends on 4)

The antioxidation method according to claim 4, wherein the contacting is in vivo.

### Claim 11 (depends on 9)

A cell protection or antioxidation method comprising contacting a cell with the compound according to claim 9.

### Claim 12 (depends on 9)

An antioxidation method comprising:
administering the compound of claim 9 to a subject having oxidative stress caused by reactive oxygen species.

### Claim 13 (depends on 11)

The antioxidation method according to claim 11, wherein the contacting is in vitro.

### Claim 14 (depends on 11)

The antioxidation method according to claim 11, wherein the contacting is in vivo.

### Claim 15 (depends on 9)

A method for treating a disease caused by oxidative stress caused by reactive oxygen species in a subject in need thereof, comprising administering to the subject the compound according to claim 9.

### Claim 16 (depends on 15)

The method according to claim 15, wherein the subject is human.

### Claim 17 (depends on 15)

The method according to claim 15, wherein
the disease caused by oxidative stress is cerebral infarction, amyotrophic lateral sclerosis, Alzheimer's disease, or Parkinson's disease.