Antimicrobial analogues of gramicidin S

Patent metadata

Field	Value
Publication number	US-10351602-B1
Application number	US-201816234880-A
Country	US
Kind code	B1
Filing date	Dec 28, 2018
Priority date	May 31, 2018
Publication date	Jul 16, 2019
Grant date	Jul 16, 2019

Abstract

Disclosed herein are N-aminated variants of Gramicidin S and methods of using the same for treating infections in a subject.

First claim

What is claimed is:

1. A compound of formula (I),

or a pharmaceutically acceptable salt thereof, wherein
R 1 , R 2 , R 3 , and R 4 are each independently selected from hydrogen or —NH 2 ; and
at least one of R 1 , R 2 , R 3 , and R 4 is —NH 2 .

2. The compound of claim 1 , wherein R 3 is —NH 2 .

3. The compound of claim 1 , wherein R 4 is —NH 2 .

4. The compound of claim 1 , wherein two of R 1 , R 2 , R 3 , and R 4 are —NH 2 .

5. The compound of claim 4 , wherein R 1 and R 3 are —NH 2 .

6. The compound of claim 4 , wherein R 3 and R 4 are —NH 2 .

7. The compound of claim 4 , wherein R 2 and R 3 are —NH 2 .

8. The compound of claim 4 , wherein R 2 and R 4 are —NH 2 .

9. The compound of claim 1 , wherein three of R 1 , R 2 , R 3 , and R 4 are —NH 2 .

10. The compound of claim 9 , wherein R 1 , R 3 and R 4 are —NH 2 .

11. The compound of claim 9 , wherein R 2 , R 3 and R 4 are —NH 2 .

12. The compound of claim 1 , wherein each of R 1 , R 2 , R 3 , and R 4 are —NH 2 .

13. A pharmaceutical composition comprising an effective amount of the compound of claim 1 or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.

14. A method of treating an infection in a subject, comprising administering to the subject an effective amount of the pharmaceutical composition of claim 13 .

15. The method of claim 14 , wherein the infection is a fungal infection or a bacterial infection.

16. The method of claim 15 , wherein the infection is a gram-positive bacterial infection.

17. The method of claim 15 , wherein the infection is a gram-negative bacterial infection.

18. The method of claim 15 , wherein the infection is a multi-drug resistant infection.

19. The method of claim 14 , wherein the subject is a human.

Assignees

• Del Valle Juan R
• Shaw Lindsey
• Univ South Florida

Inventors

• Del Valle Juan R
• Shaw Lindsey

Classifications

• A61P31/10

  Antimycotics · CPC title

• A61K38/00

  Medicinal preparations containing peptides (peptides containing beta-lactam rings A61K31/00; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, A61K31/00; ergot alkaloids of the cyclic peptide type A61K31/48; containing macromolecular compounds having statistically distributed amino acid units A61K31/74; medicinal preparations containing antigens or antibodies A61K39/00; medicinal preparations characterised by the non-active ingredients, e.g. peptides as drug carriers, A61K47/00) · CPC title

• C07K7/66 Primary

  Gramicidins S, C; Tyrocidins A, B, C; Related peptides · CPC title

• A61P31/04

  Antibacterial agents · CPC title

• Y02A50/30

  Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change · CPC title