# US 11,999,720 B2 · Pyrazolylacylpyrazoline compounds and method for treating pain

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- Number: US 11,999,720 B2
- Document ID: US11999720B2
- Status: Granted
- Kind: B2
- Application number: 17/251,473
- Filed: 2019-09-19
- Published: 2021-05-27
- Granted: 2024-06-04
- Earliest claimed: 2018-09-19
- Assignees: The Trustees of Indiana University; The United States Government as represented by the Department of Veterans Affairs
- Applicants: The Trustees of Indiana University; The United States Government AS Represented By the Department of Veterans Affairs
- Inventors: Samy Meroueh; Fletcher A. White; Alexander G. Obukhov
- Web page: https://patentgrep.com/patent/US11999720B2

## CPC

- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- C07D 403/04: directly linked by a ring-member-to-ring-member bond
- C07D 231/12: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D 401/14: containing three or more hetero rings
- C07D 403/14: containing three or more hetero rings
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

This invention relates to pyrazolylacylpyrazoline compounds or pharmaceutically acceptable salts thereof, and for the use of the compounds to treat neurological disorders.

## Claims

### Claim 1

A compound of Formula (1)
wherein
R1 is selected from the group consisting of (C1-C4 alkyl)-CO2H, —CO2H substituted phenyl, and tetrazole substituted phenyl;
R2 is selected from the group consisting of phenyl, methoxy substituted phenyl, and pyridinyl;
R3 is selected from the group consisting of (C1-C3 alkyl) substituted phenyl and halo substituted phenyl; and
R4 is selected from the group consisting of alkoxy substituted phenyl and pyridyl substituted phenyl;
with the proviso that the compound of Formula (1) is not
or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

The compound or pharmaceutically acceptable salt thereof of claim 1, wherein R1 is tetrazole substituted phenyl.

### Claim 3 (depends on 2)

The compound or pharmaceutically acceptable salt thereof of claim 2, wherein R2 is phenyl, or methoxy substituted phenyl.

### Claim 4 (depends on 2)

The compound or pharmaceutically acceptable salt thereof of claim 2, wherein R2 is phenyl.

### Claim 5 (depends on 1)

The compound or pharmaceutically acceptable salt thereof of claim 1, wherein R3 is methyl-phenyl or chloro-phenyl.

### Claim 6 (depends on 4)

The compound or pharmaceutically acceptable salt thereof of claim 4, wherein R3 is (C1-C3 alkyl) substituted phenyl.

### Claim 7 (depends on 1)

The compound or pharmaceutically acceptable salt thereof of claim 1, wherein R4 is methoxy-phenyl.

### Claim 8

A compound selected from the group consisting of
or a pharmaceutically acceptable salt thereof.

### Claim 9 (depends on 8)

The compound of claim 8, selected from the group consisting of
or a pharmaceutically acceptable salt thereof.

### Claim 10

A compound of Formula (1)
wherein:
R1 is selected from the group consisting of —CO2H substituted phenyl, and tetrazole substituted phenyl;
R2 is selected from the group consisting of phenyl, methoxy substituted phenyl and pyridinyl;
R3 is (C1-C3 alkyl) substituted phenyl and halo substituted phenyl; and
R4 is alkoxy substituted phenyl;
or a pharmaceutically acceptable salt thereof.

### Claim 11 (depends on 10)

The compound of claim 10, wherein:
R1 is tetrazole substituted phenyl;
R2 is phenyl;
R3 is methyl-phenyl; and
R4 is methoxy-phenyl.

### Claim 12 (depends on 10)

The compound of claim 10, wherein:
R1 is tetrazole substituted phenyl;
R2 is selected from the group consisting of phenyl, and methoxy substituted phenyl;
R3 is (C1-C3 alkyl) substituted phenyl; and
R4 is alkoxy substituted phenyl;
or a pharmaceutically acceptable salt thereof.