# US 11,306,067 B2 · Diphenyl substituted thiophene-2-amide derivatives and pharmaceutical compositions thereof useful as antimicrobial

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- Number: US 11,306,067 B2
- Document ID: US11306067B2
- Status: Granted
- Kind: B2
- Application number: 16/975,472
- Filed: 2019-03-01
- Published: 2021-01-21
- Granted: 2022-04-19
- Earliest claimed: 2018-03-05
- Assignees: Denovamed Inc.
- Applicants: Denovamed Inc.
- Inventors: Fan Wu; Erhu Lu; Shengguo Sun; Christopher J. Barden
- Web page: https://patentgrep.com/patent/US11306067B2

## CPC

- A61P 31/00: Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- C07D 333/38: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- A61K 31/381: having five-membered rings
- A61P 31/04: Antibacterial agents
- C07D 333/16: by oxygen atoms
- C07D 333/34: Sulfur atoms
- C07D 333/36: Nitrogen atoms
- A61K 31/43: Compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula [IMAGE cpc-sch-A61K-0952.gif], e.g. penicillins, penems
- A61K 31/7048: having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin {, digitoxin or digoxin}
- A61K 38/12: Cyclic peptides {, e.g. bacitracins; Polymyxins; Gramicidins S, C; Tyrocidins A, B or C (A61K38/043 - A61K38/046 take precedence)}
- Y02A 50/30: Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- Y02A: TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE

## Abstract

Compounds or pharmaceutical acceptable salts thereof of Formula (I), in which RM have the meaning described herein and pharmaceutical compositions thereof useful as antimicrobial and/or adjuvant:

## Claims

### Claim 1

A compound, or a pharmaceutically acceptable salt thereof, of Formula I:
in which R1 and R2 are each independently fluoro or chloro; R3 and R4 are each independently alkyl; R5 is hydrogen or alkyl; and R6 is amide, sulfonamide or —C(CF3)2OH.

### Claim 2 (depends on 1)

The compound of claim 1 in which R3 and R4 are each independently methyl, ethyl, or isopropyl.

### Claim 3 (depends on 1)

The compound of claim 1 in which R1 and R2 are each both chloro.

### Claim 4 (depends on 1)

The compound of claim 1 in which R3 and R4 are both methyl.

### Claim 5 (depends on 1)

The compound of claim 1 in which R3 and R4 are both isopropyl.

### Claim 6 (depends on 1)

The compound of claim 1 in which the compound is selected from compounds exemplified herein.

### Claim 7 (depends on 1)

A method of treatment of a microbial infection comprising administering an effective amount of an antimicrobial compound of claim 1 to a patient in need thereof.

### Claim 8 (depends on 7)

The method of treatment of claim 7 in which the microbial infection is substantially caused by Gram-positive bacteria.

### Claim 9 (depends on 8)

The method of treatment of claim 8 in which the microbial infection comprises Staphylococcal infection.

### Claim 10 (depends on 8)

The method of treatment of claim 8 in which the microbial infection comprises Enterococcal infection.

### Claim 11 (depends on 8)

The method of treatment of claim 8 in which the microbial infection comprises Bacillus infection.

### Claim 12 (depends on 8)

The method of treatment of claim 8 in which the microbial infection is substantially caused by a bacterial species selected from Staphylococcus aureus, Staphylococcus epidermidis, Enterococcus faecalis, Enterococcus faecium, Bacillus cereus, and Streptococcus sp.

### Claim 13 (depends on 1)

A method of treatment of a microbial infection comprising administering an effective amount of an antimicrobial adjuvant compound of claim 1 and an effective amount of an antimicrobial compound to a patient in need thereof.

### Claim 14 (depends on 13)

The method of treatment of claim 13 in which the microbial infection is substantially caused by Gram-negative bacteria.

### Claim 15 (depends on 13)

The method of treatment of claim 13 in which the microbial infection is substantially caused by Gram-positive bacteria.

### Claim 16 (depends on 13)

The method of treatment of claim 13 in which the microbial infection is polymicrobial.

### Claim 17 (depends on 13)

The method of treatment of claim 13 in which the microbial infection is substantially caused by a bacterial species selected from Pseudomonas aeruginosa, Klebsiella pneumoniae, Actinetobacter baumanii, and E. coli.

### Claim 18 (depends on 1, 13)

The method of treatment of claim 13 in which the antimicrobial adjuvant compound is a compound of claim 1.

### Claim 19 (depends on 13)

The method of treatment of claim 13 in which the antimicrobial compound is selected from the group consisting of colistin, ampicillin, erythromycin, and azithromycin.

### Claim 20 (depends on 1)

A pharmaceutical composition comprising a compound of claim 1 and a pharmaceutically acceptable excipient.

### Claim 21 (depends on 1)

The compound of claim 1 in which R1 and R2 are both chloro, R3 and R4 are both methyl, R5 is hydrogen, and R6 is —C(CF3)2OH.

### Claim 22 (depends on 1)

The compound of claim 1 in which R1 and R2 are both chloro, R3 and R4 are both methyl, R5 is hydrogen, and R6 is sulfonamide.