# US 10,441,588 B2 · Methods and compositions for treating bacterial infection

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- Number: US 10,441,588 B2
- Document ID: US10441588B2
- Status: Granted
- Kind: B2
- Application number: 15/711,648
- Filed: 2017-09-21
- Published: 2018-02-15
- Granted: 2019-10-15
- Earliest claimed: 2012-05-02
- Assignees: The Curators of the University of Missouri; Nanova, Inc.
- Applicants: Curators of the University of Missouri; Nanova, Inc.
- Inventors: Hongmin Sun; David W. Anderson; Feng Qi
- Web page: https://patentgrep.com/patent/US10441588B2

## CPC

- A61K 31/517: ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
- A61K 9/0014: {Skin, i.e. galenical aspects of topical compositions (non-active ingredients are additionally classified in A61K47/00; A61K9/0009, A61K9/0021, A61K9/7015, A61K9/7023 take precedence; cosmetic preparations A61K8/00, A61Q; preparations for wound dressings or bandages A61L26/00)}
- A61K 31/505: Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K 31/519: ortho- or peri-condensed with heterocyclic rings
- A61K 31/527: spiro-condensed
- A61K 31/5377: not condensed and containing further heterocyclic rings, e.g. timolol
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61K 47/06: Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K 47/44: Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin (synthetic glycerides, e.g. medium-chain triglycerides, A61K47/14)
- A61L 27/54: Biologically active materials, e.g. therapeutic substances {(A61L27/227 takes precedence)}
- A61L 29/16: Biologically active materials, e.g. therapeutic substances {(A61L29/048 takes precedence)}
- A61L 31/16: Biologically active materials, e.g. therapeutic substances {(A61L31/047 takes precedence)}
- A61L 2300/404: Biocides, antimicrobial agents, antiseptic agents
- 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
- 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)
- A61L: METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K)
- Y02A: TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE

## Abstract

The present disclosure relates to chemical compounds, methods for their discovery, and their therapeutic and research use. In particular, the present disclosure provides compounds as therapeutic agents against bacterial infections (e.g., biofilms). The present disclosure also provides topical formulations for use in methods for treating bacterial infections.

## Claims

### Claim 1

A topical formulation for treating a bacterial infection comprising:
a compound having the structure of Formula V
wherein X is SR1, NH2, NHR1, NR1R, OH, OR1, or Cl; wherein R and R1 are, independently, H, a C1-C8 alkyl or alkenyl or cycloalkyl, optionally substituted with F, CN, OR6, NR62, COR6, CO2R6, CONHR6, aryl or heteroaryl, wherein one or more alkyl carbons may be replaced by O; R2 is H or a Cl alkyl; R3 and R4 are, independently, a C1-C8 alkyl; R5 is C1-C6 alkyl, CN, OR6, NR62, COR6, CO2R6, CONHR6, aryl, heteroaryl, SO2R6, NHCOR6, SO2NHR6, or OCOR6; R6 is H, C1-C6 alkyl, C0-C3 alkyl-aryl, or C0-C3 alkyl-heteroaryl, all optionally substituted; and R11 is H or a C1 alkyl; and
a base comprising a hydrocarbon base, an oil, and combinations thereof.

### Claim 2 (depends on 1)

The topical formulation of claim 1, wherein the compound is selected from the group consisting of:
and combinations thereof.

### Claim 3 (depends on 1)

The topical formulation of claim 1 comprising about 0.05 wt. % to about 5.0 wt. % of the compound having the structure of Formula V.

### Claim 4 (depends on 1)

The topical formulation of claim 1, wherein the hydrocarbon base comprises liquid paraffin, white petrolatum, a wax, esters of fatty alcohols, saturated fatty acids, oleic acid, olive oil, starch glycerin, purified lanolin, cetyl alcohol, glyceryl monostearate, methylparaben, propylparaben, glycol ethers, gelation hydrocarbon, polyethylene glycol, polyoxyl 40 stearate, polysorbates, hydrophilic ointment base, ceresine, white ointment base, absorptive ointment base, Macrogol ointment base, simple ointment base, beeswax, wool fat, mineral oil, and combinations thereof.

### Claim 5 (depends on 1)

The topical formulation of claim 1, wherein the oil comprises a vegetable oil.

### Claim 6

A topical formulation for treating a bacterial infection comprising:
a compound having the structure of Formula V
wherein X is SR1, NH2, NHR1, NR1R, OH, OR1, or Cl; wherein R, R1 and R2 are, independently, H, a C1-C8 alkyl or alkenyl or cycloalkyl, optionally substituted with F, CN, OR6, NR62, COR6, CO2R6, CONHR6, aryl or heteroaryl, wherein one or more alkyl carbons may be replaced by O; R3 and R4 are, independently, a C1-C8 alkyl; R5 is H, C1-C6 alkyl, CN, OR6, NR62, COR6, CO2R6, CONHR6, aryl, heteroaryl, SO2R6, NHCOR6, SO2NHR6, or OCOR6; R6 is H, C1-C6 alkyl, C0-C3 alkyl-aryl, or C0-C3 alkyl-heteroaryl, all optionally substituted; and R11 is H or a Cl alkyl; and
a base comprising a vegetable oil,
wherein the formulation is a topical formulation.

### Claim 7 (depends on 6)

The topical formulation of claim 6, wherein the compound is selected from the group consisting of:
and combinations thereof.

### Claim 8 (depends on 6)

The topical formulation of claim 6 comprising about 0.05 wt. % to about 5.0 wt. % of the compound having the structure of Formula V.