DIFLUORINATED COMPOUNDS AS DEPIGMENTING OR LIGHTENING AGENTS

• US 20190322608A1
• Filed: 08/24/2017
• Published: 10/24/2019
• Est. Priority Date: 08/24/2016
• Status: Active Grant

• Current Assignee: TFChem
• Original Assignee: TFChem
• Inventors: DELIENCOURT-GODEFROY, Geraldine, LOPES, Lenaig
• Granted Patent: US 10,640,441 B2
• Time in Patent Office: Days
• CPC Class Codes: A61K 8/69 containing fluorine
• CPC Class Codes: A61P 17/00 Drugs for dermatological disorders
• CPC Class Codes: A61Q 19/02 for chemically bleaching or whitening the skin
• CPC Class Codes: C07C 213/06 from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
• CPC Class Codes: C07C 217/52 having etherified hydroxy groups or amino groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
• CPC Class Codes: C07C 217/74 with rings other than six-membered aromatic rings being part of the carbon skeleton
• CPC Class Codes: C07C 2601/14 The ring being saturated
• CPC Class Codes: C07C 41/22 by introduction of halogens; by substitution of halogen atoms by other halogen atoms
• CPC Class Codes: C07C 43/247 containing halogen
• CPC Class Codes: C07C 43/253 containing hydroxy or O-metal groups

Abstract

The present invention relates to a compound having the following formula (I) as well as a method for preparing such a compound, a cosmetic or pharmaceutical composition containing such a compound, and the use thereof as a depigmenting, lightening, bleaching or whitening agent and for treating pigmentation disorders, notably by topical application on the skin.

Claims

1. A compound having the following formula I:

2. The compound according to claim 1, wherein it is a compound having the following formula Ia:

3. The compound according to claim 1, wherein it is a compound having the following formula Ib:

4. The compound according to claim 1, wherein R₁ represents a hydrogen atom, OH, OR6, OC(O)R7, OCO2R8 or OC(O)NR9R10.

5. The compound according to claim 1, wherein R₂ represents NH₂, NHR₃₃, NR₃₃R₃₄, OH, OR₁₆, OC(O)R₁₇, OCO₂R₁₈ or OC(O)NR₁₉R₂₀.

6. The compound according to claim 1, wherein X₁, X₂, X₃, X₄ and X₅ represent, independently from one another, a hydrogen atom, OH, OR₂₆, OC(O)R₂₇, OCO₂R₂₈, Or OC(O)NR₂₉R₃₀.

7. The compound according to claim 1, wherein at least one of X₁, X₂, X₃, X₄ and X₅ represents a group other than a hydrogen atom.

8. The compound according to claim 7, wherein X₃ represents a group other than a hydrogen atom.

9. The compound according to claim 8, wherein X₁, X₂, X₄ and X₅ each represent a hydrogen atom and X₃ represents a group other than a hydrogen atom.

10. The compound according to claim 9, wherein:

X₁, X₂, X₄ and X₅ each represent a hydrogen atom,

X₃ represents OH or OR₂₆,

R₁ represents H, OH or OR₆, and

R₂ represents NH₂, NHR₃₃, NR₃₃R₃₄, OH or OR₁₆.

11. The compound according to claim 1, wherein:

R₆, R₇, R₈, R₁₆, R₁₇, R₁₈, R₂₆, R₂₇, R₂₈, R₃₃ and R₃₄ represent, independently from one another, a (C₁-C₆)alkyl, aryl or aryl-(C₁-C₆)alkyl group, and

R₉, R₁₀, R₁₉, R₂₀, R₂₉ and R₃₀ represent, independently from one another, a hydrogen atom, or a (C₁-C₆)alkyl, aryl or aryl-(C₁-C₆)alkyl group.

12. The compound according to claim 1, wherein it is chosen among:

13. The compound according to claim 12, wherein it is chosen among:

14. A cosmetic or pharmaceutical composition comprising at least one compound according to claim 1 and at least one cosmetically or pharmaceutically acceptable excipient.

19. A method for the preparation of a compound according to claim 1 comprising:

reacting a compound of following formula II;

20. A method for the preparation of a compound according to claim 1 comprising:

fluorinating the ketone function of a compound of following formula XI;

21. A method for the preparation of a compound according to claim 1 with X₃═

OH comprising;

oxidizing the aldehyde function of a compound of following formula XV;

22. The method according to claim 21, wherein the compound of formula XV is prepared by reacting a compound of following formula XVI:

23. A method for depigmenting, lightening, bleaching or whitening a skin by applying on said skin an efficient amount of a compound according to claim 1 to a person in need thereof.

24. A method for treating a pigmentation disorder of a skin by applying on said skin an efficient amount of a compound according to claim 1 to a person in need thereof.

25. The method according to claim 24, wherein the pigmentation disorder is a hyperpigmentation.

26. The method according to claim 25, wherein the hyperpigmentation results from overexposure to the sun, inflammation, injuries, burns, medicines or hormonal alteration.

15-18. -18. (canceled)