Diphenolic compound, and preparation method therefor and use thereof

Abstract

The present invention provides a class of compounds derived from resorcinol as represented by formula A. The compound can be used for preparing a drug for inhibiting hyperpigmentation, and can be used cosmetically and non-therapeutically for treating hyperpigmentation. The compounds of the present invention have significant effects on inhibiting pigmentation caused by ultraviolet and / or visible light radiation, and anti-skin aging, etc., wherein W is [formula], T is H, [formula] or [formula], and the definitions of R1 to R8 are as defined in the description.

Description

group is preferably one of OH, H2O, OTs, OMs, Cl, Br and I. 10. A preparation method for preparing the compound of formula (la), wherein the compound of formula (II) reacts with the compound of formula (Illa) and a synthetic route is , wherein R1, R2 and R3 are defined as claim 1, and Z1 and Z2 are defined as claim 3. 11. A preparation method for preparing the compound of formula (V), wherein the compound of formula (II) reacts with the compound of formula (IVa) and a synthetic route is rvr2 r3V wherein R1, R2, R3 and R4 are defined as claim 1, wherein R5 is selected from a leaving group, and the leaving group is preferably one of OH, H2O, OTs, OMs, Cl, Br and I. 12. A preparation method for preparing the compound of formula (Va), wherein the compound of formula (II) reacts with the compound of formula (Illa) and a synthetic route is as follows: Z1 and Z2 are defined as claim 5. 13. A preparation method for preparing the compound of formula (VI), wherein the compound of formula (I) reacts with the compound of formula (IVb) and a synthetic route is as follows: (IVb) , wherein R1, R2, R3, R4, R6, R7 andR8 are defined as claim 1, wherein R5 is selected from a leaving group, and the leaving group is selected from one of OH, H2O, OTs, OMs, Cl, Br and I. 14. A preparation method for preparing the compound of formula (Via), wherein the compound of formula (I) reacts with the compound of formula (Illb) and a synthetic route is as follows: R1, R2, R3, R4, R6 andR7 are defined as claim 1, and Z1 and Z2 are defined as claim 7. 15. A pharmaceutical composition, comprising the compound according to any one of claims 1-8 or a pharmaceutically acceptable salt thereof 16. A use of the compound according to any one of claims 1-8 in preparation of a drug for treating, preventing and / or alleviating hyperpigmentation. 17. A non-therapeutic and cosmetic use of the compound according to any one of claims 1-8 or a salt thereof in treating, preventing and / or alleviating hyperpigmentation. 18. A cosmetic composition, comprising the compound according to any one of claims 18 or a salt thereof. ABSTRACT The present invention provides a kind of resorcinol-derived compounds shown in formula A, which can be used for preparing drugs for inhibiting hyperpigmentation and a cosmetic and non-therapeutic use for treating hyperpigmentation. The compounds of the present invention have significant effects on inhibiting pigmentation caused by ultraviolet and / or visible light radiation and anti-aging of skin. , wherein W is          , and T is H,          or R1 to R8 are defined in the description.

Claims

1. A kind of compounds of formula A,OHTA, wherein W isand T is H,orwherein R1 is selected from H, optionally substituted alkyl and optionally substituted arylalkyl;R2 and R6 can be identical or different, and are independently selected from optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, optionally substituted amide and optionally substituted ester respectively; R3, R4, R7 and R8 can be identical or different, and are independently selected from hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl and optionally substituted amide respectively; R3 and R4 can be connected to carbon atoms jointly connected to form a ring; R7 and R8 can be connected to carbon atoms jointly connected to form a ring, wherein the amide group is preferably -NHCOCH3, -NHCOH, -NHCOCH2CH3, -NHCOCH2CH2CH3, -NHCOCH(CH3)2,-NHCOCH(CH2)2, -N(COCH3)2, -CONH2, -CON(CH3)2, -CONHCH3, -CONHCH2CH3, -CON(CH2CH3)2, -CONHCH(CH3)2, -CONHCH2CH2CH3, -CONHCH2CH2CH2CH3,phthaloyl, succinimido, glutarimido, maleimido,           n and R , wherein R9is selected from optionally substituted alkyl or optionally substituted aryl, carboxyl or a saltthereof, cyano, optionally substituted amide and optionally substituted ester; n is selected from a natural number from 1 to 6; and the ester is preferably one of -COOCH3, -COOCH2CH3, -COOCH(CH3)2, -COOCH2CH2CH3 and -COOCH2CH2CH2CH3;or cosmetically or pharmaceutically acceptable salt, stereoisomers or a mixture ofstereoisomers of any proportion, particularly enantiomers or a mixture of enantiomers, and more particularly a racemic mixture.

2. The compound according to claim 1, wherein the compound A is a compound of formula(I),                         (I), wherein R1 to R4 are defined as claim 1.

3. The compound according to claim 1 or 2, wherein the compound A is a compound ofOH R2(la)formula (la),                        , wherein R1 to R3 are defined as claim 1 or 2; Z1 and Z2can be identical or different, and are independently selected from hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl and optionally substituted amide respectively; Z1 and Z2 can be connected with carbon atoms jointly connected to form a ring; and the ring can be substituted.

4. The compound according to claim 1, wherein the compound A is a compound of formula (V),OH R2r2^R3R4(V), wherein R1 to R4 are defined as claim 1.

5. The compound according to claim 4, wherein the compound A is a compound of formulaOH R2R2—R3 z2^1(Va),, wherein R1 to R3 are defined as claim 4; Z1 and Z2 can beidentical or different, and are independently selected from hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl and optionally substituted amide respectively; Z1 and Z2 can be connected with carbon atoms jointly connected to form a ring; and the ring can be substituted.

6. The compound according to claim 1, wherein the compound A is a compound of formula(VI),(VI), wherein R1 to R4 and R6 to R8 are defined as claim 1.

7. The compound according to claim 6, wherein the compound A is (Via),(Via), wherein R1 to R4 and R6 to R7 are defined as claim 1; Z1 and Z2can be identical or different, and are independently selected from hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, and optionally substituted amide respectively; Z1 and Z2 can be connected with carbon atoms jointly connected to form a ring; and the ring can be substituted.

8. The compound according to any one of claims 1-7, selected from the followingcompounds:N-(l-(2,4-dihydroxyphenyl) ethyl)-2-pyrrolidone;N-(l-(2,4-dihydroxyphenyl) propyl)-2-pyrrolidone;N-(l-(2,4-dihydroxyphenyl) ethyl)-2-piperidone;N-(l-(2,4-dihydroxyphenyl) propyl)-2-piperidone;N-(l-(2,4-dihydroxyphenyl) ethyl)-2- azepanone;N-(l-(2,4-dihydroxyphenyl) propyl)-2- azepanone;l,l’-((4,6-dihydroxy-l,3- phenylene) bis (ethane-1,1-diyl)) bis (pyrrolidin-2-one);l,l’-((4,6-dihydroxy-l,3- phenylene) bis (propane-1,1-diyl)) bis (pyrrolidin-2-one);l,l’-((4,6-dihydroxy-l,3- phenylene) bis (ethane-1,1-diyl)) bis (piperidin-2-one);l,l’-((4,6-dihydroxy-l,3- phenylene) bis (propane-1,1-diyl)) bis (piperidin-2-one);l,l’-((4,6-dihydroxy-l,3- phenylene) bis (ethane-1,1-diyl)) bis (azepan-2-one);l,l’-((4,6-dihydroxy-l,3- phenylene) bis (propane-1,1-diyl)) bis (azepan-2-one);4,6-bis (1 -phenylethyl)-1,3-resorcinol.

9. A preparation method for preparing the compound of formula (I), wherein the compound of formula (II) reacts with the compound of formula (IVa) and a synthetic route is as follows:(IVa), wherein R1, R2, R3and R4 are defined as claim 1, wherein R5 is selected from a leaving group, and the leavinggroup is preferably one of OH, H2O, OTs, OMs, Cl, Br and I.

10. A preparation method for preparing the compound of formula (la), wherein thecompound of formula (II) reacts with the compound of formula (Illa) and a synthetic route is(la), whereinR1, R2 and R3 are defined as claim 1, and Z1 and Z2 are defined as claim 3.

11. A preparation method for preparing the compound of formula (V), wherein the compound of formula (II) reacts with the compound of formula (IVa) and a synthetic route isrvr2 r3Vwherein R1,R2, R3 and R4 are defined as claim 1, wherein R5 is selected from a leaving group, and theleaving group is preferably one of OH, H2O, OTs, OMs, Cl, Br and I.

12. A preparation method for preparing the compound of formula (Va), wherein the compound of formula (II) reacts with the compound of formula (Illa) and a synthetic route is as follows:Z1 and Z2 are defined as claim 5.

13. A preparation method for preparing the compound of formula (VI), wherein the compound of formula (I) reacts with the compound of formula (IVb) and a synthetic route is as follows:(IVb), wherein R1, R2, R3,R4, R6, R7 andR8 are defined as claim 1, wherein R5 is selected from a leaving group, and theleaving group is selected from one of OH, H2O, OTs, OMs, Cl, Br and I.

14. A preparation method for preparing the compound of formula (Via), wherein the compound of formula (I) reacts with the compound of formula (Illb) and a synthetic route is as follows:R1, R2, R3, R4, R6 andR7 are defined as claim 1, and Z1 and Z2 are defined as claim 7.

15. A pharmaceutical composition, comprising the compound according to any one of claims 1-8 or a pharmaceutically acceptable salt thereof16. A use of the compound according to any one of claims 1-8 in preparation of a drug for treating, preventing and / or alleviating hyperpigmentation.

17. A non-therapeutic and cosmetic use of the compound according to any one of claims 1-8 or a salt thereof in treating, preventing and / or alleviating hyperpigmentation.

18. A cosmetic composition, comprising the compound according to any one of claims 18 or a salt thereof.

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