US 4,879,284 AGranted

Naphthalene derivatives having retinoid type action, the process for preparation thereof and medicinal and cosmetic compositions containing them

AssigneeL'oreal

InventorsGerard Land, Jean Maignan, Serge Restle, Gerard Malle

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Abstract

The invention relates to a compound of formula: ##STR1## in which formula: R.sub.1 to R.sub.4 denote, independently, H, OH, C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 alkoxy; and A denotes --COR.sub.5, R.sub.5 being H when at least one of the substituents R.sub.1 to R.sub.4 is other than H; C.sub.1 -C.sub.6 alkyl; amino; (C.sub.1 -C.sub.6)alkylamino; di(C.sub.1 -C.sub.6) alkylamino; arylamino; benzylamino; amino drived from a cyclic or heterocyclic amine; (--COR.sub.5 being able, when it is an amide group, to be the amide group of an amino acid or of a glucosamine); or alternatively R.sub.5 denotes --OR.sub.6, R.sub.6 being H or (C.sub.1 -C.sub.6)alkyl; C.sub.1 -C.sub.6 mono- or polyhydroxyalkyl, or aryl or benzyl, both optionally substituted; --OR.sub.6 also being able to be derived from a sugar; and the salts and isomers of this compound. The invention also relates to a process for preparing this compound and medicinal and cosmetic compositions containing them.

Claims18

Dependent claims

A chemical compound having the formula ##STR25## wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are distributed on either of the rings or on both at once and are each, independently, selected from the group consisting of hydrogen, a linear or branched C.sub.1 -C.sub.6 alkyl, OH and C.sub.1 -C.sub.6 alkoxy;

and
A is selected from the group consisting of
(i) --COR.sub.5 wherein R.sub.5 is selected from the group consisting of hydrogen when at least one of R.sub.1 to R.sub.4 is other than hydrogen;
C.sub.1 -C.sub.6 alkyl;
amino;
amino mono-or-disubstituted by C.sub.1 -C.sub.6 alkyl or by C.sub.1 -C.sub.6 alkyl mono-or polysubstituted by OH or by C.sub.1 -C.sub.6 alkyl interrupted by one or more hetero atoms selected from the group consisting of O, S, and N, unsubstituted or substituted by one or more OH groups;
arylamino;
benzylamino;
alicyclic amino;
and N-heterocyclic amino radical,
(ii) an amide group of an amino acid or of a glucosamine;
and
(iii) --COOR.sub.6 wherein R.sub.6 is selected from the group consisting of hydrogen, C.sub.1 -C.sub.6 alkyl when one of R.sub.1 to R.sub.4 is other than hydrogen, C.sub.1 -C.sub.6 mono- or polyhydroxyalkyl, aryl and benzyl, or OR.sub.6 is (i') C.sub.6 H.sub.9 O.sub.6 --radical derived from glucose, (ii') C.sub.6 H.sub.11 O.sub.6 --radical derived from mannitol or (iii') C.sub.11 H.sub.9 O.sub.4 --radical derived from erythritol;
or an isomer or salt thereof.

11 more elements

A medicinal composition comprising in a pharmaceutically acceptable carrier at least one compound having the formula ##STR26## wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are distributed on either of the rings or on both at once and are each, independently, selected from the group consisting of hydrogen, a linear or branched C.sub.1 -C.sub.6 alkyl, OH and C.sub.1 -C.sub.6 alkoxy;

and
A is selected from the group consisting of
(i) --COR.sub.5 wherein R.sub.5 is selected from the group consisting of hydrogen when at least one of R.sub.1 to R.sub.4 is other than hydrogen;
C.sub.1 -C.sub.6 alkyl;
amino;
amino mono- or disubstituted by C.sub.1 -C.sub.6 alkyl or by C.sub.1 -C.sub.6 alkyl mono-or polysubstituted by OH or by C.sub.1 -C.sub.6 alkyl interrupted by one or more hetero atoms selected from the group consisting of O, S, and N, unsubstituted or substituted by one or more OH groups;
arylamino;
benzylamino;
alicyclic amino;
and N-heterocyclic amino radical,
(ii) an amide group of an amino acid or of a glucosamine;
and
(iii) --COOR.sub.6 wherein R.sub.6 is selected from the group consisting of hydrogen, C.sub.1 -C.sub.6 alkyl when one of R.sub.1 to R.sub.4 is other than hydrogen, C.sub.1 -C.sub.6 mono- or polyhydroxyalkyl, aryl and benzyl, or OR.sub.6 is (i') C.sub.6 H.sub.9 O.sub.6 --radical derived from glucose, (ii') C.sub.6 H.sub.11 O.sub.6 --radical derived from mannitol or (iii') C.sub.11 H.sub.9 O.sub.4 --radical derived from erythritol;
or an isomer or salt thereof.

11 more elements

A process for preparing a compound having the formula ##STR27## wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are distributed on either of the rings or on both at once and are each, independently, selected from the group consisting of hydrogen, a linear or branched C.sub.1 -C.sub.6 alkyl, OH and C.sub.1 -C.sub.6 alkoxy;

and
A is selected from the group consisting of
(i) --COR.sub.5 wherein R.sub.5 is selected from the group consisting of hydrogen when at least one of R.sub.1 to R.sub.4 is other than hydrogen;
C.sub.1 -C.sub.6 alkyl;
amino;
mono- or disubstituted by C.sub.1 -C.sub.6 alkyl or by C.sub.1 -C.sub.6 alkyl mono- or polysubstituted by OH or by C.sub.1 -C.sub.6 alkyl interrupted by one or more hetero atoms selected from the group consisting of O, S, and N, unsubstituted or substituted by one or more OH groups;
arylamino;
benzylamino;
alicyclic amino;
and N-heterocyclic amino radical,
(ii) an amide group of an amino acid or of a glucosamine;
and
(iii) --COOR.sub.6 wherein R.sub.6 is selected from the group consisting of hydrogen, C.sub.1 -C.sub.6 alkyl when one of R.sub.1 to R.sub.4 is other than hydrogen, C.sub.1 -C.sub.6 mono- or polyhydroxyalkyl, aryl and benzyl, or OR.sub.6 is (i') C.sub.6 H.sub.9 O.sub.6 --radical derived from glucose, (ii') C.sub.6 H.sub.11 O.sub.6 --radical derived from mannitol or (iii') C.sub.11 H.sub.9 O.sub.4 --radical derived from erythritol;
or an isomer or salt thereof, said process comprising reacting in a basic medium a substituted or unsubstituted 2-[1-(triphenylphosphonio)ethyl]naphthalene salt having the formula ##STR28## wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are distributed on either of the rings or on both at once and are each, independently selected from the group consisting of hydrogen, a linear or branched C.sub.1 -C.sub.6 alkyl, OH and C.sub.1 -C.sub.6 alkoxy and X represents halogen, with an aldehyde RCHO wherein R represents
wherein A is ##STR29## selected from the group consisting of (i') --COR.sub.5 wherein R.sub.5 is selected from the group consisting of hydrogen when at least one of R.sub.1 to R.sub.4 is other than hydrogen;
C.sub.1 -C.sub.6 alkyl;
amino mono- or disubstituted by C.sub.1 -C.sub.6 alkyl;
C.sub.1 -C.sub.6 alkyl mono- or polysubstituted by OH;
C.sub.1 -C.sub.6 alkyl interrupted by one or more heteroatoms selected from the group consisting of O, S and N, unsubstituted or substituted by one or more OH groups;
arylamino;
benzylamino;
alicyclic amino;
and N-heterocyclic amino radical;
(ii') an amide group or an amino acid or of a glusosamine;
and
(iii') --COOR.sub.6 wherein R.sub.6 is selected from the group consisting of hydrogen, C.sub.1 -C.sub.6 alkyl when on of R.sub.1 to R.sub.4 is other than hydrogen, C.sub.1 -C.sub.6 mono- or polyhydroxyalkyl, aryl and benzyl, or OR.sub.6 is (i") C.sub.6 H.sub.9 O.sub.6 --radical derived from glucose,
(ii") C.sub.6 H.sub.11 O.sub.6 --radical derived from mannitol or (iii") C.sub.11 H.sub.9 O.sub.4 --radical derived from erythritol.

24 more elements

Dependencies are inferred from the claim text.