2-Oxothiazolidine 4-Carboxylic acid compounds for promoting desquamation of the skin

• US 20070232574A1
• Filed: 05/30/2007
• Published: 10/04/2007
• Est. Priority Date: 11/17/2000
• Status: Abandoned Application

• Current Assignee: L'Oreal SA
• Original Assignee: L'Oreal SA
• Inventors: Bernard, Dominique, Simonetti, Lucie, Galey, Jean-Baptiste
• Application Number:
  US11/806,218
• Publication Number:
  US 20070232574A1
• Time in Patent Office: Days
• US Class Current: 514/154
• CPC Class Codes: A61K 2800/28 Rubbing or scrubbing compositions; Peeling or abrasive compositions; Containing exfoliants
• CPC Class Codes: A61K 8/49 containing heterocyclic compounds
• CPC Class Codes: A61P 17/00 Drugs for dermatological disorders
• CPC Class Codes: A61P 17/06 Antipsoriatics
• CPC Class Codes: A61P 17/12 Keratolytics, e.g. wart or anti-corn preparations
• CPC Class Codes: A61P 17/16 Emollients or protectives, e.g. against radiation
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: A61Q 19/00 Preparations for care of the skin
• CPC Class Codes: A61Q 19/08 Anti-ageing preparations

Abstract

2-oxothiazolidine-4-carboxylic acid compounds having the structural formula (I): are suited for promoting desquamation of the skin and/or stimulating epidermal renewal and/or combating aging of the skin.

Claims

1. A method for promoting desquamation of the skin in an individual afflicted with xerosis or dryness of the skin, comprising administering to said individual, a thus effective amount of at least one 2-oxothiazolidine-4-carboxylic acid compound having the structural formula (I):

in which X is —

OH or —

NHR₂; and

R₁ and R₂, which may be identical or different, are each a hydrogen atom, a linear or branched C₁-C₈ alkyl radical, optionally substituted with at least one radical —

OR and/or one radical —

COOR and/or one radical —

NHR and/or one radical —

SR and/or one radical —

R in which R is a hydrogen atom or a linear or branched C₁-C₄ alkyl, a radical COR₃ in which R₃ is a linear or branched C₁-C₈ alkyl radical, optionally substituted with at least one radical —

OR and/or one radical —

COOR and/or one radical —

NHR and/or one radical —

SR and/or one radical —

R in which R is a hydrogen atom or a linear or branched C₁-C₄ alkyl radical, a benzenic or heterocyclic aralkyl or aryl radical optionally substituted with at least one radical —

OR and/or one radical —

COOR and/or one radical —

NHR and/or one radical —

SR and/or one radical —

R in which R is a hydrogen atom or a linear or branched C₁-C₄ alkyl radical, formulated into a physiologically acceptable medium therefor.

2. The method as defined by claim 1, wherein in formula (I), X is —

OH or —

NHR₂; and

R₁ and R₂, which may be identical or different, are each a hydrogen atom, an unsubstituted linear C₁-C₄ alkyl radical, a linear C₁-C₄ alkyl radical substituted with at least one radical —

COOR and/or one radical —

NHR in which R is a hydrogen atom or a linear or branched C₁-C₄ alkyl, a radical COR₃ in which R₃ is a linear C₁-C₄ alkyl radical substituted with at least one radical —

COOR and/or one radical —

NHR in which R is a hydrogen atom or a linear or branched C₁-C₄ alkyl radical, or an unsubstituted benzenic or heterocyclic aralkyl or aryl radical.

3. The method as defined by claim 1, said at least one 2-oxothiazolidine-2-carboxylic acid compound of formula (I) comprising procysteine or L-2-oxo-4-thiazolidinecarboxylic acid;

N-(2-oxothiazolidin-4-ylcarbonyl)glycine;

2-oxo-3-(L-glutamyl)thiazolidine-4-carboxylic acid;

or N-[2-oxo-3-(L--glutamyl)thiazolidin-4-ylcarbonyl]glycine.

4. The method as defined by claim 1, further comprising coadministering to said individual, an effective amount of at least one other active agent selected from the group consisting of retinoic acid;

retinol and its esters;

vitamin D;

extradiol, kojic acid, hydroquinone, clindamycin phosphate, erythromycin, a tetracycline antibiotic, metronidazole, crotamiton, a pyrethroid;

econazole, ketoconazole and miconazole and their salts;

amphotericin B, terbinafine, octopirox, acyclovir, hydrocortisone, betamethasone valerate, clobetasol propionate;

ibuprofen and its salts;

diclofenac and its salts;

acetylsalicylic acid, acetaminophen, glycerrhizic acid, lidocaine hydrochloride, thenaldine, trimeprazine, cyproheptadine;

α

-hydroxycarboxylic acids, β

-hydroxycarboxylic acids and β

-keto carboxylic acids and their salts, amides and esters;

α

-tocopherol and its esters;

superoxide dismutases;

ascorbic acid and its esters;

progesterone, zinc pyrithione, benzoyl peroxide, diazoxide, spiroxazone, lecithin, linoleic acid, linolenic acid, anthralin, a carotenoid;

eicosatetraenoic acid and eicosatuinoic acid and their esters and amides; and

mixtures thereof.

5. The method as defined by claim 1, further comprising coadministering to said individual with said at least one compound of formula (I), an effective amount of at least one other pro-desquamating agent selected from the group consisting of:

hydroxy acids and their salts, amides and esters;

glycerol;

urea;

pyrrolidonecarboxylic acid; and

ammonium salts of lactic acid.

6. The method as defined by claim 5, said at least one other pro-desquamating agent being selected from the group consisting of glycerol, urea, pyrrolidonecarboxylic acid, and the ammonium salts of lactic acid.

7. The method as defined by claim 5, said at least one other pro-desquamating agent comprising a hydroxy acid, or salt, amide or ester thereof.

8. The method as defined by claim 7, said hydroxy acid, or salt, amide or ester thereof comprising an α

- or β

-hydroxycarboxylic acid, a β

-keto carboxylic acid, or salt, amide or ester thereof.

9. The method as defined by claim 8, said hydroxy acid comprising glycolic acid, lactic acid, salicylic acid, citric acid, a fruit acid or 5-n-octanoylsalicylic acid.

10. The method as defined by claim 1, comprising topically applying said at least one 2-oxothiazolidine-4-carboxylic acid compound of formula (I) onto the skin of said individual.

11. The method as defined by claim 1, comprising administering 0.01% to 50% by weight of said at least one 2-oxothiazolidine-4-carboxylic acid compound formulated into said physiologically acceptable medium therefor.

12. The method as defined by claim 1, comprising administering 0.1% to 10% by weight of said at least one 2-oxothiazolidine-4-carboxylic acid compound formulated into said physiologically acceptable medium therefor.

13. The method as defined by claim 10, wherein said at least one of 2-oxothiazolidine-4-carboxylic acid compound of formula (I) is formulated as an aqueous or oily solution, lotion, serum, emulsion, milk, suspension, cream, gel, microcapsules, microparticles, mousse, solid, aerosol, permanent wave, or shampoo.

14. The method as defined in claim 1, wherein X is —

OH.

15. The method as defined in claim 1, wherein R₁ is hydrogen.

16. The method as defined in claim 1, wherein X is —

OH and R₁ is hydrogen.