# US 11,999,677 B2 · Benzylamino-oxoethyl benzamide analogs and methods of use

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- Number: US 11,999,677 B2
- Document ID: US11999677B2
- Status: Granted
- Kind: B2
- Application number: 17/666,692
- Filed: 2022-02-08
- Published: 2022-05-26
- Granted: 2024-06-04
- Earliest claimed: 2018-09-04
- Assignees: The Board of Regents of the University of Oklahoma
- Applicants: The Board of Regents of the University of Oklahoma
- Inventors: Weidong Wang; Venkateswararao Eeda
- Web page: https://patentgrep.com/patent/US11999677B2

## CPC

- C07C 233/73: of a carbon skeleton containing six-membered aromatic rings
- C07D 213/40: Acylated substituent nitrogen atom
- C07C 237/22: having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated (peptides C07K)
- C07C 311/46: Y being a hydrogen or a carbon atom
- C07D 231/56: Benzopyrazoles; Hydrogenated benzopyrazoles
- C07D 317/54: Radicals substituted by oxygen atoms
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Benzylamino-oxoethyl benzamide compounds for use in treating diseases and conditions associated with abnormal cell function related to endoplasmic reticulum (ER) stress. For example, the compounds can be used as suppressors of ER stress-induced pancreatic β-cell dysfunction and death, for example in the treatment of Type 1 and Type 2 diabetes. The compounds can also be used in treatments for chronic heart disease, neurodegenerative diseases, retinal degeneration, and other metabolic disorders associated with ER stress.

## Claims

### Claim 1

A compound having a formula as represented by chemical structure I:
wherein:
R=H, Alkyl, or Phenyl;
R1=H, Me, Cl, F, OMe, OH, or Phenyl;
R2=H or OH;
R3=H, NH2, Me, Cl, F, OMe, OH, or Phenyl;
R4=H or OH;
R5=H, Me, Cl, F, OMe, or OH;
R6=H, Me, Cl, F, OMe, OH, CCl3, or CF3;
R7=H, Me, Cl, F, OMe, OH, or Piperonyl;
R8=CCl3, CF3, or Piperonyl;
R9=H, Me, Cl, F, or OMe;
R10=H, Me, Cl, F, OMe, OH, CCl3, or CF3; and
n=1, and
wherein one of R2 and R4=H, and one of R2 and R4=OH.

### Claim 2 (depends on 1)

The compound of claim 1, wherein R, R1, R3, R4, R5, R6, R7, R9, and R10=H, R2=OH, and R8=CF3.

### Claim 3 (depends on 1)

The compound of claim 1, wherein R, R1, R2, R3, R5, R6, R7, R9, and R10=H, R4=OH, and R8=CF3.

### Claim 4 (depends on 1)

A composition comprising the compound of claim 1 disposed in a pharmaceutically-acceptable carrier, diluent or vehicle.