Oleic acid derivatives as treatments for Friedreich ataxia and inhibitors of ferroptosis

Patent metadata

Field	Value
Publication number	US-12378178-B2
Application number	US-202017776222-A
Country	US
Kind code	B2
Filing date	Nov 12, 2020
Priority date	Nov 12, 2019
Publication date	Aug 5, 2025
Grant date	Aug 5, 2025

Abstract

The invention relates to compounds of Formula I or Formula II: to compositions comprising such compounds, and to methods of use thereof for treating neurodegenerative disorders, such as Friedreich ataxia.

First claim

What is claimed is:

1. A compound represented by Formula I

wherein
R is H or C 1 -C 6 alkyl;
m is an integer from 3 to 8;
n is an integer from 3 to 8; and
Y is CF 3 or CCl 3 ,

or an optical isomer thereof.

2. The compound of claim 1 , wherein Y is CF 3 .

3. The compound of claim 1 , wherein R is H.

4. The compound of claim 1 , wherein R is CH 3 or CH 3 CH 2 .

5. The compound of claim 1 , wherein said compound is represented by Formula IA or by Formula IB

6. The compound of claim 5 , wherein said compound has an S configuration.

7. The compound of claim 5 , wherein said compound has an R configuration.

8. The compound of claim 5 , wherein the weight ratio of the R isomer to the S isomer is from 70:30 to 99.99:0.01.

9. The compound of claim 5 , wherein the weight ratio of the S isomer to the R isomer is from 70:30 to 99.99:0.01.

10. The compound of claim 5 , wherein the compound is a racemic mixture.

11. The compound of claim 1 , wherein said compound is

12. The compound of claim 1 , wherein said compound is

13. The compound of claim 1 , wherein said compound is

14. A pharmaceutical composition comprising a compound according to claim 1 , and
a pharmaceutically acceptable carrier.

15. The pharmaceutical composition of claim 14 , wherein said compound is

16. A method of treating Friedreich ataxia in a subject, comprising administering to the subject an effective amount of a compound having the following formula:

or a pharmaceutical composition thereof.

Assignees

• Univ Pennsylvania
• Childrens Hospital Philadelphia

Inventors

• Smith Amos
• Wilson Robert B
• Huryn Donna M
• Cotticelli Maria Grazia
• Xia Shujuan
• Lee Taehee
• Forestieri Roberto

Classifications

• C07C49/227

  containing halogen · CPC title

• A61P25/14

  for treating abnormal movements, e.g. chorea, dyskinesia · CPC title

• A61P25/00

  Drugs for disorders of the nervous system · CPC title

• A61P43/00

  Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title

• C07C33/423 Primary

  containing only double bonds as unsaturation · CPC title