# US 9,751,826 B2 · 4-vinyl-2-cyclopenten-1-one derivatives, the production thereof, and the use of same as an antibiotic agent

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- Number: US 9,751,826 B2
- Document ID: US9751826B2
- Status: Granted
- Kind: B2
- Application number: 15/308,936
- Filed: 2015-05-06
- Published: 2017-05-04
- Granted: 2017-09-05
- Earliest claimed: 2014-05-06
- Assignees: Centre National de la Recherche Scientifique (CNRS)
- Applicants: Centre National de la Recherche Scientifique (CNRS)
- Inventors: Jamal Ouazzani; Emilie Adelin; Geraldine Le Goff
- Web page: https://patentgrep.com/patent/US9751826B2

## CPC

- C07C 69/738: Esters of keto-carboxylic acids {or aldehydo-carboxylic acids}
- A61P 31/04: Antibacterial agents
- C07C 45/59: in five-membered rings (from ozonides C07C45/40)
- C07C 67/475: by splitting of carbon-to-carbon bonds and redistribution, e.g. disproportionation or migration of [IMAGE cpc-sch-C07C-0963.gif] groups between different molecules
- C12N 1/14: Fungi (culture of mushrooms A01G18/00; as new plants A01H15/00); Culture media therefor
- C12P 5/007: {containing one or more isoprene units, i.e. terpenes (carotenes C12P23/00)}
- C12P 7/26: Ketones
- C12P 7/62: Carboxylic acid esters
- C07C 2601/10: the ring being unsaturated
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C12N: MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA (microbiological testing media C12Q1/00)
- C12P: FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE {(brewing of beer C12C; producing vinegar C12J; producing specific peptides or proteins C07K; producing enzymes C12N9/00; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; measuring or testing processes involving enzymes or microorganisms C12Q; measuring or testing processes involving nucleic acid amplification reactions C12Q1/6844; fermentation processes to form a food composition, A21 or A23; compounds in general, see the relevant compound class, e.g. C01, C07)}

## Abstract

The invention relates to a compound of general formula (I) wherein: R1 is a hydrogen atom or a C1 to C4 alkyl radical; R2 is a C1 to C4 hydroxyl or alkoxyl radical; and R3 and R4 are independently a hydrogen atom or a C1 à C4 alkyl radical; and the enantiomers and mixtures of enantiomers thereof, especially in a racemic form.

## Claims

### Claim 1

A method of treating a bacterial infection in a subject comprising administering to a subject in need thereof, an effective amount of a compound of the following general formula (I):
wherein:
R1 is a hydrogen atom or a C1 to C4 alkyl radical;
R2 is a C1 to C4 hydroxyl or alkoxyl radical, and
R3 and R4 are independently a hydrogen atom or a C1 to C4 alkyl radical;
the enantiomers and mixtures of enantiomers thereof;
and wherein the infection is a bacterial infection selected from among the group consisting of an Escherichia, Klebsiella, Enterobacter, Micrococcus, Bacillus, Streptococcus, Acinetobacter, and Stapylococcus infection.

### Claim 2 (depends on 1)

The method according to claim 1, wherein the compound is a compound of the following formula (Ia):

### Claim 3 (depends on 1, 2)

The method according to claim 1 or claim 2, wherein the compound is an antibiotic agent.

### Claim 4 (depends on 3)

The method according to claim 3, wherein the compound is a broad-spectrum antibiotic agent.

### Claim 5 (depends on 3)

The method according to claim 3, wherein the compound is an antibiotic agent against multiresistant Gram-positive and Gram-negative pathogenic bacteria.

### Claim 6 (depends on 1, 2)

The method of claim 1 or claim 2, wherein the compound is comprised in a pharmaceutical composition characterized in that it contains as an active ingredient at least a compound of formula (I) or (Ia) associated with a pharmaceutically acceptable excipient.

### Claim 7 (depends on 1, 2)

The method of claim 1 or claim 2, wherein the compound is administered as a racemic form.