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1. WO2016139501 - GEM DIFLUOROCOMPOUNDS AS DEPIGMENTING OR LIGHTENING AGENTS

Note: Text based on automatic Optical Character Recognition processes. Please use the PDF version for legal matters

[ EN ]

CLAIMS

1. A compound having the following formula (I):


or a cosmetically or a pharmaceutically acceptable salt thereof, a stereoisomer or a mixture of stereoisomers in any proportion, particularly an enantiomer or a mixture of enantiomers, and more particularly a racemate mixture,

wherein:

- Ri and R2 represent, independently from each other, a hydrogen atom, OSiRsR jRs, OR6, OC(0)R7, OC02R8, OC(0)NR9Rio, OP(0)(ORn)2, or OSO3R12, or

Ri and R2 form together an oxo group (=0), or

Ri and R2 are linked together by a chain of formula -0(CH2)nO-, with n representing 2 or 3, and advantageously 2, and

- Xi, X2, X3, X4, X5 represent, independently from one another, a hydrogen atom, OSiR13Ri4Ri5, OR16, OC(0)R17, OC02R18, OC(O)NR19R20, OP(0)(OR21)2, or

OS03R22,

with:

R3i R4, R5, Ri3, Ri4 and R15 representing, independently from one another, a (Ci- C6)alkyl, aryl, aryl-(Ci-C6)alkyl or (Ci-C6)alkyl-aryl group,

R6 and Ri6 representing, independently from one another, a hydrogen atom; a O- protecting group; or a (Ci-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C3- C7)cycloalkyl, 5- to 7-membered heterocycloalkyl, aryl, heteroaryl, (C3- C7)cycloalkyl-(Ci-C6)alkyl, (5- to 7-membered heterocycloalkyl)-(Ci-C6)alkyl, aryl-(Ci-C6)alkyl or heteroaryl-(Ci-C6)alkyl group, said group being optionally substituted by one or several groups selected from a halogen atom, a (Ci-C6)alkyl group and a (Ci-C6)alkoxy group,

R7, R8, R17 and Ri8 representing, independently from one another, a (Ci-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C3-C7)cycloalkyl, 5- to 7-membered

heterocycloalkyl, aryl, heteroaryl, (C3-C7)cycloalkyl-(Ci-C6)alkyl, (5- to 7- membered heterocycloalkyl)-(Ci-C6)alkyl, aryl-(Ci-C6)alkyl or heteroaryl-(Ci- C6)alkyl group, said group being optionally substituted by one or several groups selected from a halogen atom, a (Ci-C6)alkyl group and a (Ci-C6)alkoxy group, R9, Rio, R19 and R2o, representing, independently from one another, a hydrogen atom; a N-protecting group; or a (Ci-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C3- C7)cycloalkyl, 5- to 7-membered heterocycloalkyl, aryl, heteroaryl, (C3- C7)cycloalkyl-(Ci-C6)alkyl, (5- to 7-membered heterocycloalkyl)-(Ci-C6)alkyl, aryl-(Ci-C6)alkyl or heteroaryl-(Ci-C6)alkyl group, said group being optionally substituted by one or several groups selected from a halogen atom, a (Ci-C6)alkyl group and a (Ci-C6)alkoxy group,

R11, R12, R21 and R22 representing, independently from one another, a hydrogen atom or a (Ci-C6)alkyl group.

2. The compound according to claim 1, wherein Ri represents a hydrogen atom and R2 represents a hydrogen atom, OSiR3R4R5, OR6, OC(0)R7, OC02R8, OC(O)NR9Ri0, OP(0)(ORn)2, or OS03Ri2; or Ri and R2 form together an oxo group (=0); or Ri and R2 are linked together by a chain of formula -0(CH2)nO-.

3. The compound according to claim 2, wherein Ri represents a hydrogen atom and R2 represents a hydrogen atom, OR6, OC(0)R7, OC02R8, or OC(O)NR9Ri0; or Ri and R2 form together an oxo group (=0); or Ri and R2 are linked together by a chain of formula -0(CH2)nO-.

4. The compound according to claim 3, wherein Ri represents a hydrogen atom and R2 represents a hydrogen atom or an OR6 group; or Ri and R2 form together an oxo group (=0); or Ri and R2 are linked together by a chain of formula -0(CH2)nO-.

5. The compound according to any one of claims 1 to 4, wherein Xi, X2, X3, X4, X5 represent, independently from one another, a hydrogen atom, ORi6, OC(0)Rn, OC02Ri8, OC(O)NRi9R20, OS03R22.

6. The compound according to any one of claims 1 to 5, wherein Xi, X2, X3, X4, X5 represent, independently from one another, a hydrogen atom, ORi6, OC(0)Rn, or OC02Ri8.

7. The compound according to any one of claims 1 to 6, wherein Xi, X2, X3, X4, X5 represent, independently from one another, hydrogen atom, ORi6 or OC(0)Rn.

8. The compound according to any one of claims 1 to 7, wherein Xi, X2, X4 and X5 each represent a hydrogen atom and X3 does not represent a hydrogen atom.

9. The compound according to any one of claims 1 to 8, wherein:

R6, R9, Rio, Ri6, R19 and R2o represent, independently from one another, a hydrogen atom; or a (Ci-C6)alkyl, aryl, or aryl-(Ci-C6)alkyl group, said group being optionally substituted by one or several groups selected from a halogen atom, a (Ci- C6)alkyl group and a (Ci-C6)alkoxy group, notably selected from a (Ci-C6)alkyl group and a (Ci-C6)alkoxy group, and

R7, R8, Ri7 and Rig represent, independently from one another, a (Ci-C6)alkyl, aryl, or aryl-(Ci-C6)alkyl group, said group being optionally substituted by one or several groups selected from a halogen atom, a (Ci-C6)alkyl group and a (Ci- C6)alkoxy group, notably selected from a (Ci-C6)alkyl group and a (Ci-C6)alkoxy group.

The compound according to claim 1, wherein it is chosen from the following

and the cosmetically and pharmaceutically salts thereof.

11. A cosmetic or pharmaceutical composition comprising at least one compound of formula (I) as defined in any one of claims 1 to 10 and at least one cosmetically or pharmaceutically acceptable excipient.

12. A cosmetic use of a compound of formula (I) as defined in any one of claims 1 to 10, as depigmenting, lightening, bleaching or whitening agent, more particularly for the skin.

13. A compound of formula (I) as defined in any one of claims 1 to 10 for use as a drug.

14. A compound of formula (I) as defined in any one of claims 1 to 10 for use in the treatment of pigmentation disorders.

15. The compound for use according to claim 14, wherein the pigmentation disorders are a hyperpigmentation such as lentigo, melasma, ephelides, postinflammatory hyperpigmentation, and hyperpigmentation causes by drugs, chemicals or sun.

16. A compound of formula (I) as defined in any one of claims 1 to 10 for use as an antioxidant, in particular to inhibit or to reduce oxidative stress, notably due to UV.

17. A method for the preparation of a compound of formula (I) as defined in claim 1 comprising:

(1) fluorinating the ketone function of a compound of the following formula (II):

in which Ri, R2, Xi, X2, X3, X4 and X5 are as defined in claim 1 and are optionally in a protected form,

(2) deprotecting the Ri, R2, Xi, X2, X3, X4 and/or X5 groups when they are in a protected form, and

(3) optionally salifying the compound of formula (I) obtained in previous step (1) or (2) to give a cosmetically or pharmaceutically acceptable salt of the compound of formula (I).