# US 2013/0158090 A1 · Metronidazole esters for treating rosacea

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- Number: US 2013/0158090 A1
- Document ID: US20130158090A1
- Status: Published application
- Kind: A1
- Application number: 13/806,732
- Filed: 2011-06-29
- Published: 2013-06-20
- Earliest claimed: 2010-06-29
- Assignees: Galderma Research & Development
- Inventors: Jean-Guy Boiteau; Jean-Michel Linget
- Web page: https://patentgrep.com/patent/US20130158090A1

## CPC

- C07D 233/94: with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to other ring members
- 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 31/4164: 1,3-Diazoles
- A61P 17/00: Drugs for dermatological disorders
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

A compound of formula (I): is described, as well as enantiomers, pharmaceutically acceptable salts thereof, for its use as a medicament.

## Claims

### Claim 1

A method for treating an inflammatory pathology, said method comprising administrating to a subject in need of such treatment, a compound of formula (I) below:
or an enantiomer or pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

The method as defined in claim 1, for treating rosacea.

### Claim 3

(canceled)

### Claim 4 (depends on 1)

The method as defined in claim 1, wherein the salt of the compound of formula (I) or of an enantiomer thereof is a salt of the compound or an enantiomer thereof with a pharmaceutically acceptable acid.

### Claim 5 (depends on 4)

The method as defined in claim 4, wherein the pharmaceutically acceptable acid is selected from the group consisting of:
a) a pharmaceutically acceptable inorganic acid; and
b) a pharmaceutically acceptable organic acid.

### Claim 6 (depends on 1)

The method as defined in claim 1, wherein the compound is selected from the group consisting of a compound of formula (I), a hydrochloride of the compound of formula (I), a citrate of the compound of formula (I), a salicylate of the compound of formula (I), a benzoate of the compound of formula (I), and an S enantiomer of any one of these compounds.

### Claim 7 (depends on 1)

The method as defined in claim 1, wherein the compound is 2-(2-methyl-5-nitroimidazol-1-yl)ethyl (S)-2-(4-isobutylphenyl)propionate.

### Claim 8 (depends on 1)

The method as defined in claim 1, wherein the compound is in the form of a pharmaceutical composition for topical application.

### Claim 9 (depends on 8)

The method as defined in claim 8, wherein the pharmaceutical composition is in the form of a solution, a gel or an emulsion.

### Claim 10 (depends on 8)

The method as defined in claim 8, wherein the compound is present in an amount of 0.001% to 10% by weight relative to the total weight of the composition.

### Claim 11

The compound 2-(2-Methyl-5-nitroimidazol-1-yl)ethyl (S)-2-(4-isobutylphenyl)propionate of structure corresponding to formula (Ia):
or a pharmaceutically acceptable salt thereof.

### Claim 12 (depends on 5)

The method as defined in claim 5, wherein the pharmaceutically acceptable inorganic acid is selected from the group consisting of hydrochloric acid, sulfuric acid, phosphoric acid, nitric acid, and hydrobromic acid.

### Claim 13 (depends on 5)

The method as defined in claim 5, wherein the pharmaceutically acceptable organic acid is selected from the group consisting of acetic acid, tartaric acid, maleic acid, hydroxymaleic acid, fumaric acid, citric acid, lactic acid, mucic acid, gluconic acid, benzoic acid, succinic acid, oxalic acid, phenylacetic acid, methanesulfonic acid, toluenesulfonic acid, benzenesulfonic acid, salicylic acid, sulfanilic acid, aspartic acid, glutamic acid and ascorbic acid.