# US 7,745,456 B2 · Synthesis and antimicrobial activity of novel dicationic “reversed amidines”

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- Number: US 7,745,456 B2
- Document ID: US7745456B2
- Status: Granted
- Kind: B2
- Application number: 11/825,786
- Filed: 2007-07-09
- Published: 2008-03-06
- Granted: 2010-06-29
- Earliest claimed: 2000-11-06
- Assignees: The University of North Carolina at Chapel Hill; Duke University; Georgia State University Research Foundation, Inc.
- Inventors: David W. Boykin; Richard R. Tidwell; W. David Wilson; John R. Perfect; Chad F. Stephens
- Web page: https://patentgrep.com/patent/US7745456B2

## CPC

- C07D 307/10: with substituted hydrocarbon radicals attached to ring carbon atoms
- A61P 31/04: Antibacterial agents
- C07D 307/14: Radicals substituted by nitrogen atoms not forming part of a nitro radical
- C07D 307/52: Radicals substituted by nitrogen atoms not forming part of a nitro radical
- C07D 333/20: by nitrogen atoms (nitro, nitroso radicals C07D333/12)
- C07D 405/12: linked by a chain containing hetero atoms as chain links
- C07D 405/14: containing three or more hetero rings
- C07D 409/12: linked by a chain containing hetero atoms as chain links
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention relates to novel 2,5-bis{[alkyl (or aryl) imino] aminophenyl}furans and thiophenes of the general formula in which R1, R2, R3 and R4 are each independently selected from the group consisting of H, alkyl, alkoxy, halide, and alkylhalide groups; R5 is H, alkyl or aryl; R6 is H, alkyl, aryl, or NR7R8, in which R7 and R8 are each independently selected from the group consisting of H, alkyl and aryl; and X is O, S or NR9, in which R9 is H or alkyl, and to the use of such compounds.

## Claims

### Claim 1

A compound according to Formula I:
wherein:
R1, R2, R3 and R4 are each independently selected from the group consisting of H, alkyl, alkoxy, halide, and alkylhalide groups;
R5 is H, alkyl or aryl;
R6 is aryl; and
X is O.

### Claim 2 (depends on 1)

The compound according to claim 1, wherein R1 and R2 are each an H.

### Claim 3 (depends on 1)

The compound according to claim 1, wherein R1 and R2 are each an H and R3 and R4 are each lower alkyls.

### Claim 4 (depends on 1)

The compound according to claim 1, wherein R3 and R4 are each a halide.

### Claim 5 (depends on 1)

The compound according to claim 1, wherein R3 and R4 are each alkoxy.

### Claim 6 (depends on 1)

The compound according to claim 1, wherein R3 and R4 are each alkyl halides.

### Claim 7 (depends on 1)

The compound according to claim 1, wherein R6 is a pyridyl.

### Claim 8 (depends on 1)

The compound according to claim 1, wherein R6 is a substituted pyridyl.

### Claim 9 (depends on 1)

The compound according to claim 1, wherein R6 is a quinolinyl.

### Claim 10

A pharmaceutical composition comprising a compound according to Formula I:
wherein:
R1, R2, R3 and R4 are each independently selected from the group consisting of H, alkyl, alkoxy, halide, and alkylhalide groups;
R5 is H alkyl or aryl;
R6 is aryl; and
X is O;
in a pharmaceutically acceptable carrier.

### Claim 11 (depends on 10)

The pharmaceutical composition of claim 10, wherein the composition is formulated for parenteral administration.

### Claim 12 (depends on 10)

The pharmaceutical composition of claim 10, wherein the composition is formulated for oral administration.

### Claim 13 (depends on 10)

The pharmaceutical composition of claim 10, wherein the composition is formulated for topical administration.

### Claim 14

A method of treating an microbial infection in a subject in need of such treatment, wherein the microbial infection is caused by a microorganism selected from the group consisting of Mycobacterium tuberculosis, Trypanosoma spp., Candida albicans, Aspergillus spp., Cryptosporidium parvum, Giardia lamblia, Plasmodium spp., Pneumocystis carinii, Toxoplasma gondii, Fusarium solani, and Cryptococcus neoformans, said method comprising administering to the subject a compound according to Formula I or a pharmaceutically acceptable salt thereof:
wherein:
R1, R2, R3 and R4 are each independently selected from the group consisting of H, alkyl, alkoxy, halide, and alkylhalide groups;
R5 is H, alkyl or aryl;
R6 is aryl; and
X is O.

### Claim 15 (depends on 14)

The method according to claim 14, wherein the compound is administered parenterally.

### Claim 16 (depends on 14)

The method according to claim 14, wherein the compound is administered orally.

### Claim 17 (depends on 14)

The method according to claim 14, wherein the compound is administered topically.

### Claim 18 (depends on 1)

A process for preparing a pharmaceutical composition comprising admixing the compound of Formula (I) according to claim 1 and optionally a pharmaceutically utilizable carrier.