Bis-cyclic guanidine compound compositions, methods of use and treatment thereof

Patent metadata

Field	Value
Publication number	US-10052309-B2
Application number	US-201715691955-A
Country	US
Kind code	B2
Filing date	Aug 31, 2017
Priority date	Feb 25, 2014
Publication date	Aug 21, 2018
Grant date	Aug 21, 2018

Abstract

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

First claim

We claim:

1. A bis-cyclic guanidine compound of the following structure:

R 1 is selected from the group consisting of: 2-(3-trifluoromethyl-phenyl)-ethyl, cyclohexyl-butyl, and adamantan-1-yl-ethyl;
R 2 is selected from the group consisting of: (S or R)-butyl, (S or R)-2-naphthylmethyl, and (S or R)-cyclohexylmethyl; and
R 3 is selected from the group consisting of: heptyl, cyclohexyl-butyl, and 2-biphenyl-4-yl-ethyl.

2. The bis-cyclic guanidine compound of claim 1 , wherein the bis-cyclic guanidine compound has the following structure:

3. The bis-cyclic guanidine compound of claim 1 , wherein the bis-cyclic guanidine compound has the following structure:

4. The bis-cyclic guanidine compound of claim 1 , wherein the bis-cyclic guanidine compound has the following structure:

5. The bis-cyclic guanidine compound of claim 1 , wherein the bis-cyclic guanidine compound has the following structure:

6. The bis-cyclic guanidine compound of claim 1 , wherein the bis-cyclic guanidine compound has the following structure:

7. A method of treating an infection comprising:
delivering, to a subject in need thereof, a composition comprising a therapeutically effective amount of a bis-cyclic guanidine compound, or a pharmaceutically acceptable salt of the bis-cyclic guanidine compound, to treat the infection, wherein the bis-cyclic guanidine compound has the following structure:

R 1 is selected from the group consisting of: 2-(3-trifluoromethyl-phenyl)-ethyl, cyclohexyl-butyl, and adamantan-1-yl-ethyl;
R 2 is selected from the group consisting of: (S or R)-butyl, (S or R)-2-naphthylmethyl, and (S or R)-cyclohexylmethyl; and
R 3 is selected from the group consisting of: heptyl, cyclohexyl-butyl, and 2-biphenyl-4-yl-ethyl; and
wherein the infection is caused by one or more bacteria selected from the group consisting of: Enterococcus faecium, Staphylococcus aureus, Klebsiella pneumoniae, Acinetobacter baumannii, Pseudomonas aeruginosa , and Enterobacter cloacae.

8. The method of claim 7 , wherein the composition is a broad spectrum antibiotic.

9. The method of claim 7 , wherein the bis-cyclic guanidine compound has the following structure:

10. The method of claim 7 , wherein the bis-cyclic guanidine compound has the following structure:

11. The method of claim 7 , wherein the bis-cyclic guanidine compound has the following structure:

12. The method of claim 7 , wherein the bis-cyclic guanidine compound has the following structure:

13. The method of claim 7 , wherein the bis-cyclic guanidine compound has the following structure:

Assignees

• Univ South Florida
• Torey Pines Inst For Molecular Studies
• Torrey Pines Inst For Molecular Studies

Inventors

• Shaw Lindsey Neil
• Fleeman Renee Marie
• Houghten Richard Allen
• Giulianotti Marcello Angelo
• Santos Radleigh G
• Nefzi Adel

Classifications

• C07D233/46

  with only hydrogen atoms attached to said nitrogen atoms · CPC title

• A01N43/50

  1,3-Diazoles; Hydrogenated 1,3-diazoles · CPC title

• A61K31/4178 Primary

  not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin · CPC title