# US 8,569,363 B2 · Antimicrobial and radioprotective compounds

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 8,569,363 B2
- Document ID: US8569363B2
- Status: Granted
- Kind: B2
- Application number: 13/425,054
- Filed: 2012-03-20
- Published: 2012-09-06
- Granted: 2013-10-29
- Earliest claimed: 2001-06-18
- Assignees: Biodiem Ltd.
- Applicants: Peter Prokofievich Denisenko; Nikolay Sergeevich Sapronov; Alexander Alexandrovich Tarasenko
- Inventors: Peter Prokofievich Denisenko; Nikolay Sergeevich Sapronov; Alexander Alexandrovich Tarasenko
- Web page: https://patentgrep.com/patent/US8569363B2

## CPC

- A61K 31/357: having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
- A61K 31/36: Compounds containing methylenedioxyphenyl groups, e.g. sesamin
- A61K 31/4184: condensed with carbocyclic rings, e.g. benzimidazoles
- A61P 1/00: Drugs for disorders of the alimentary tract or the digestive system
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 15/02: for disorders of the vagina
- A61P 27/02: Ophthalmic agents
- A61P 31/00: Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P 31/02: Local antiseptics
- A61P 31/04: Antibacterial agents
- A61P 31/06: for tuberculosis
- A61P 31/08: for leprosy
- A61P 31/10: Antimycotics
- A61P 31/12: Antivirals
- A61P 33/02: Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P 33/06: Antimalarials
- A61P 39/00: General protective or antinoxious agents
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 235/06: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D 235/08: Radicals containing only hydrogen and carbon atoms
- C07D 263/56: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D 317/46: condensed with one six-membered ring
- C07D 317/52: Radicals substituted by halogen atoms or nitro radicals
- 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- Y02A: TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE

## Abstract

Disclosed is a method of treatment and/or prophylaxis of a microbial infection, employing compounds of formula (I), in which X and Y are either the same of different and selected from a hereroatiom; is a double or single bond depending on the heteroatoms X and Y; R1 to R5 are either the same or different and selected from hydrogen or a non-deleterious substituent; and R6 to R7 are either the same or different and selected from hydrogen and a non-deleterious substituent or one of R6 to R7 are absent when there is a double bond present. Also disclosed are methods for protecting a subject from radiation damage, methods of cancer radiotherapy, and use of the disclosed compounds as an antimicrobial or radioprotective agent.

## Claims

### Claim 1

A method for the therapeutic treatment of a skin or soft tissue infection wherein the infection is caused by an organism selected from the group consisting of Enterococcus faecalis, Staphylococcus epidermidis, Clostridium perfringens, Proteus vulgaris, Proteus mirabilis, Streptococcus pyogenes, Candida albicans, Microsporum, and Epidermophyte; the method comprising administering to an animal in need thereof an effective amount of a compound of general formula I:
in which
X and V are O;
is a double or single bond depending on the heteroatoms X and Y;
R1 to R5 are either the same or different, and are each hydrogen, alkyl, alkenyl, alkynyl, aryl, halo, haloalkyl, haloalkenyl, haloalkynyl, haloaryl, hydroxy, alkoxy, alkenyloxy, aryloxy, benzyloxy, haloalkoxy, haloalkenyloxy, haloaryloxy, nitro, nitroalkyl, nitroalkenyl, nitroalkynyl, nitroaryl, nitroheterocyclyl, amino, alkylamino, dialkylamino, alkenylamino, alkynylamino, arylamino, diarylamino, benzylamino, dibenzylamino, acyl, alkenylacyl, alkynylacyl, arylacyl, acylamino, diacylamino, acyloxy, alkylsulphonyloxy, arylsulphenyloxy, heterocyclyl, heterocycloxy, heterocyclamino, haloheterocyclyl, alkylsulphenyl, arylsulphenyl, carboalkoxy, carboaryloxy, mercapto, alkylthio, arylthio, acylthio, or a phosphorus-containing group; and
R6 and R7 are either the same or different, and are each hydrogen, alkyl, alkenyl, alkynyl, aryl, halo, haloalkyl, haloalkenyl, haloalkynyl, haloaryl, hydroxy, alkoxy, alkenyloxy, aryloxy, benzyloxy, haloalkoxy, haloalkenyloxy, haloaryloxy, nitro, nitroalkyl, nitroalkenyl, nitroalkynyl, nitroaryl, nitroheterocyclyl, amino, alkylamino, dialkylamino, alkenylamino, alkynylamino, arylamino, diarylamino, benzylamino, dibenzylamino, acyl, alkenylacyl, alkynylacyl, arylacyl, acylamino, diacylamino, acyloxy, alkylsulphonyloxy, arylsulphenyloxy, heterocyclyl, heterocycloxy, heterocyclamino, haloheterocyclyl, alkylsulphenyl, arylsulphenyl, carboalkoxy, carboaryloxy, mercapto, alkylthio, arylthio, acylthio, or a phosphorus-containing compound; or one of R6 and R7 is absent when there is a double bond present, or a pharmaceutically-acceptable salt thereof.

### Claim 2 (depends on 1)

The method of claim 1, wherein R1 and R2 are either the same or different, and are each hydrogen, hydroxy, halogen, or optionally-substituted C1-6 alkyl.

### Claim 3 (depends on 1)

The method of claim 1, wherein R3 to R5 are either the same or different, and are each hydrogen, hydroxy, halogen, nitro, C1-6 alkoxy, or optionally-substituted C1-6 alkyl.

### Claim 4 (depends on 1)

The method as claimed in claim 1, in which X, Y, , R6 and R7 are each as defined in claim 1; R1 and R2 are either the same or different, and are each hydrogen, hydroxy, Cl, Br, or C1-4 alkyl; and R3 to R5 are either the same or different, and are each hydrogen, hydroxy, Cl, Br, nitro, C1-4 alkoxy or C1-4 alkyl.

### Claim 5 (depends on 1)

The method of claim 1, wherein the compound is 3,4-methylenedioxy-β-methyl-β-nitrostyrene.

### Claim 6 (depends on 1)

The method of claim 1, wherein the compound is 3,4-methylenedioxy-β-nitrostyrene.

### Claim 7 (depends on 1)

The method of claim 1, wherein the animal is a human.