Hydantoin derivative compounds, methods of use and methods of treatment

• US 10,457,646 B1
• Filed: 11/28/2017
• Issued: 10/29/2019
• Est. Priority Date: 11/28/2016
• Status: Active Grant

• Current Assignee: University of South Florida (State University System of Florida)
• Original Assignee: University of South Florida (State University System of Florida)
• Inventors: Cai, Jianfeng, Su, Ma, Nimmagadda, Alekhya, Teng, Peng
• Primary Examiner(s): Anderson, Rebecca L
• Application Number:
  US15/823,667
• Time in Patent Office: 700 Days
• CPC Class Codes: A61K 31/4166 having oxo groups directly attached to the heterocyclic ring, e.g. phenytoin
• CPC Class Codes: C07D 233/72 Two oxygen atoms, e.g. hydantoin
• CPC Class Codes: C07D 233/76 with substituted hydrocarbon radicals attached to the third ring carbon atom

Abstract

The present disclosure provides compositions including a hydantoin derivative compound, pharmaceutical compositions including a hydantoin derivative compound, methods of treatment of a condition (e.g., bacterial infection) or disease, methods of treatment using compositions or pharmaceutical compositions, and the like.

Claims

1. A hydantoin derivative compound having the following structure:

2. The hydantoin derivative compound of claim 1, wherein the lipid tail X is a 5 to 15 carbon alkyl group.

3. The hydantoin derivative compound of claim 2, wherein the lipid tail X is selected from a 10 to 12 carbon linear alkyl group.

4. The hydantoin derivative compound of claim 2, wherein R₁ is an alkyl group, aryl group, or a cycloalkyl group, each of which is substituted or unsubstituted.

5. The hydantoin derivative compound of claim 4, wherein R₁ is an ethyl group, a phenyl group, meta-chlorobenzyl, indole, biphenyl, terphenyl, or 6-chloro indole.

6. The hydantoin derivative compound of claim 2, wherein the hydantoin derivative compound has the following structure:

7. A pharmaceutical composition comprising:

a hydantoin derivative compound, or a pharmaceutically acceptable salt of the hydantoin derivative compound, having the following structure;

8. The pharmaceutical composition of claim 7, wherein the lipid tail X is a 5 to 15 carbon alkyl group.

9. The pharmaceutical composition of claim 7, wherein the lipid tail X is selected from a 10 to 12 carbon linear alkyl group.

10. The pharmaceutical composition of claim 7, wherein R₁ is an alkyl group, aryl group, or a cycloalkyl group, each of which is substituted or unsubstituted.

11. The pharmaceutical composition of claim 10, wherein R₁ is an ethyl group, a phenyl group, meta-chlorobenzyl, indole, biphenyl, terphenyl, or 6-chloro indole.

12. The pharmaceutical composition of claim 7, wherein the hydantoin derivative compound has the following structure: