Centre International De Recherches Dermatologiques C.i.r.d.

Centre International De Recherches Dermatologiques Galderma (cird

Centre International De Recherches Dermatologiques Galderma

Centre International De Recherches Dermatologioues (cird)

Centre Internationale De Recherches Dermatologiques (c.i.r.d.)

Groupement Economique Dite: Centre National De Recherches

Groupement Economique Dit: Centre International De Recherces

Centre International De Recherches Dermatogologiques (c.i.r.d.)

Jacques Eustache

Braham Shroot

Jean-Michel Bernardon

Philippe Nedoncelle

Oliver Watts

Martine Bouclier

A polycyclic aromatic compound having the formula ##STR1## and its salts have useful therapeutic and cosmetic action particularly in psoriasis. In the formula, X represents --CH.dbd.CH--, O or S,

Polycyclic aromatic derivatives, process for preparing the same and

A polycyclic aromatic compound having the formula ##STR1## and its salts have useful therapeutic and cosmetic action particularly in psoriasis. In the formula,

The present invention relates to new polycyclic aromatic derivatives, to processes for their preparation and to their use in therapeutic and cosmetic formulations.

Aromatic heterocyclic derivatives have the formula ##STR1## wherein R.sub.1 represents (i)--CH.sub.3, (ii)--CH.sub.2 OH or (iii) ##STR2## wherein R.sub.3 represents hydrogen, --OR.sub.4 wherein R.sub.4 represents hydrogen, alkyl having 1-20 carbon atoms or mono- or polyhydroxyalkyl or R.sub.3 represents ##STR3## wherein r' and r' represent hydrogen, lower alkyl or together form a heterocycle, R.sub.2 represents hydrogen or --CH.sub.3 and Ar represents ##STR4## wherein R.sub.6 is hydrogen or alkyl having 1-10 carbon atoms and R.sub.7 represents alkyl having 4-12 carbon atoms or cycoalkyl, Y is CH or a nitrogen atom and X represents oxygen, sulfur or --N--R.sub.8 when R.sub.8 represents hydrogen, lower alkyl or lower alkoxycarbonyl, with the proviso that (i) when Y is CH and X is oxygen or sulfur Ar is other than C and (ii) when Y is nitrogen and X is oxygen, Ar is other than (C) or (D) in which R.sub.6 is alkyl having 1-4 carbon atoms and R.sub.7 is branched alkyl having 4-12 atoms.

Aromatic heterocyclic derivatives and their therapeutic and cosmetic use

Aromatic heterocyclic derivatives have the formula ##STR1## wherein R.sub.1 represents (i)--CH.sub.3, (ii)--CH.sub.2 OH or (iii) ##STR2## wherein R.sub.3 represents hydrogen, --OR.sub.4 wherein R.sub.4 represents hydrogen, alkyl having 1-20 carbon atoms or mono- or polyhydroxyalkyl or R.sub.3 represents ##STR3## wherein r' and r' represent hydrogen, lower alkyl or together form a heterocycle, R.sub.2 represents hydrogen or --CH.sub.3 and Ar represents ##STR4## wherein Z is O or S, ##STR5## wherein R.sub.5 is lower alkyl or ##STR6## wherein R.sub.6 is hydrogen or alkyl having 1-10 carbon atoms and R.sub.7 represents alkyl having 4-12 carbon atoms or cycloalkyl, Y is CH or a nitrogen atom and X represents oxygen, sulfur or --N--R.sub.8 when R.sub.8 represents hydrogen, lower alkyl or lower alkoxycarbonyl, with the proviso that (i) when Y is CH and X is oxygen or sulfur Ar is other than C and (ii) when Y is nitrogen and X is oxygen, Ar is other than (C) or (D) in which R.sub.6 is alkyl having 1-4 carbon atoms and R.sub.7 is branched alkyl having 4-12 atoms.

Aromatic heterocyclic derivatives have the formula ##STR1## wherein R.sub.1 represents (i)--CH.sub.3, (ii)--CH.sub.2 OH or (iii) ##STR2## wherein R.sub.3 represents hydrogen, --OR.sub.4 wherein R.sub.4 represents hydrogen, alkyl having 1-20 carbon atoms or mono- or polyhydroxyalkyl or R.sub.3 represents ##STR3## wherein r' and r' represent hydrogen, lower alkyl or together form a heterocycle, R.sub.2 represents hydrogen or --CH.sub.3 and Ar represents ##STR4## wherein R.sub.6 is hydrogen or alkyl having 1-10 carbon atoms and R.sub.7 represents alkyl having 4-12 carbon atoms or cycloalkyl, Y is CH or a nitrogen atom and X represents oxygen, sulfur or --N--R.sub.8 when R.sub.8 represents hydrogen, lower alkyl or lower alkoxycarbonyl, with the proviso that (i) when Y is CH and X is oxygen or sulfur Ar is other than C and (ii) when Y is nitrogen and X is oxygen, Ar is other than (C) or (D) in which R.sub.6 is alkyl having 1-4 carbon atoms and R.sub.7 is branched alkyl having 4-12 atoms.

An aromatic benzamido compound having the formula ##STR1## wherein R.sub.1 represents --CH.sub.2 OH, --CHOHCH.sub.3 or --COR.sub.5,

Aromatic benzamido compounds; their preparation and their use in human

A benzonaphthalene compound has the formula ##STR1## wherein R.sub.1 represents (i) ##STR2## or (ii) --CH.sub.2 OH; R.sub.6 represents ##STR3## or OR.sub.7 wherein R.sub.7 represents hydrogen, alkyl having 1-20 carbon atoms, monohydroxyalkyl or polyhydroxyalkyl, r' or r' represent hydrogen, lower alkyl, mono or polyhydroxyalkyl, aryl or a residue of an amino acid or a sugar, or together form a heterocycle; R.sub.2 represents hydrogen, alkyl having 1-15 carbon atoms, alkoxy having 1-4 carbon atoms or a cycloaliphatic radical; R.sub.3 represents hydrogen, hydroxy, alkyl having 1-4 carbon atoms, alkoxy having 1-10 carbon atoms, a cycloaliphatic radical, a thiocycloaliphatic radical or --0--Si(CH.sub.3).sub.2 --R.sub.8 wherein R.sub.8 represents lower alkyl; and R.sub.4 and R.sub.5 represent hydrogen, lower alkyl, hydroxy or lower acyloxy. This compound is useful in the topical and systemic treatment of dermatologic diseases and in the treatment of the degeneration of conjuctive tissues. The compound also possesses anti-tumor acitivity.

Benzonaphthalene derivatives, a process for their preparation and their

A benzonphthalene compound has the formula ##STR1## wherein R.sub.1 represents ##STR2## or (ii) --CH.sub.2 OH; R.sub.6 represents ##STR3## or OR.sub.7 wherein R.sub.7 represents hydrogen, alkyl having 1-20 carbon atoms, monohydroxyalkyl or polyhydroxyalkyl, r' or r' represent hydrogen, lower alkyl, mono or polyhydroxyalkyl, aryl or a residue of an amino acid or a sugar, or together form a heterocycle; R.sub.2 represents hydrogen, alkyl having 1-15 carbon atoms, alkoxy having 1-4 carbon atoms or a cycloaliphatic radical; R.sub.3 represents hydrogen, hydroxy, alkyl having 1-4 carbon atoms, alkoxy having 1-10 carbon atoms, a cycloaliphatic radical, a thiocycloaliphatic radical or --O--Si(CH.sub.3).sub.2 --R.sub.8 wherein R.sub.8 represents lower alkyl; and R.sub.4 and R.sub.5 represent hydrogen, lower alkyl, hydroxy or lower acyloxy. This compound is useful in the topical and systemic treatment of dermatologic diseases and in the treatment of the degeneration of conjuctive tissues. The compound also possesses anti-tumor activity.

Benzonaphtahalene derivatives, a process for their preparation and their

Aromatic esters and thioesters of the formula ##STR1## are useful in human and veterinary medicine and in cosmetic formulations. In the formula, X represents oxygen or sulfur, r' and 4' represent hydrogen, lower alkyl, monohydroxyalkyl, polyhydroxyalkyl, aryl or benzyl optionally substituted, the residue of an amino acid or aminated sugar, or taken together form a heterocycle, R.sub.2 represents .alpha., .alpha.'- dissubstituted alkyl having 4-12 carbon atoms or mono- or polycyclic cycloalkyl having 5-12 carbon atoms whose carbon linking carbon is trisubstituted and R.sub.3 and R.sub.4 represent hydrogen or lower alkyl.

Aromatic esters and thioesters, a process for their preparation and

A polycyclic aromatic compound having the formula ##STR1## and its salts have useful therapeutic and cosmetic action particularly in psoriasis.

A benzonaphthalene compound has the formula ##STR1## wherein R.sub.1 represents ##STR2## or (ii) --CH.sub.2 OH; R.sub.6 represents ##STR3## or OR.sub.7 wherein R.sub.7 represents hydrogen, alkyl having 1-20 carbon atoms, monohydroxyalkyl or polyhydroxyalkyl, r' or r' represent hydrogen, lower alkyl, mono or polyhydroxyalkyl, aryl or a residue of an amino acid or a sugar, or together form a heterocycle; R.sub.2 represents hydrogen, alkyl having 1-15 carbon atoms, alkoxy having 1-4 carbon atoms or a cycloaliphatic radial; R.sub.3 represents hydrogen, hydroxy, alkyl having 1-4 carbon atoms, alkoxy having 1-10 carbon atoms, a cycloaliphatic radical, a thiocycloaliphatic radical or --O--Si(CH.sub.3).sub.2 --R.sub.8 wherein R.sub.8 represents lower alkyl; and R.sub.4 and R.sub.5 represent hydrogen, lower alkyl, hydroxy or lower acyloxy. This compound is useful in the topical and systemic treatment of dermatologic diseases and in the treatment of the degeneration of conjunctive tissues. The compound also possesses anti-tumor activity.

An aromatic heterocyclic compound has the formula ##STR1## wherein R.sub.1 represents (i) --CH.sub.3, (ii) --CH.sub.2 OH or (iii) ##STR2## wherein R.sub.3 represents hydrogen, --OR.sub.4 wherein R.sub.4 represents hydrogen, alkyl having 1-20 carbon atoms, mono- or polyhydroxyalkyl or R.sub.3 represents ##STR3## wherein r'and r' represent hydrogen or lower alkyl, R.sub.2 represents hydrogen or --CH.sub.3 and Ar represents ##STR4## wherein Z is O or S, ##STR5## wherein R.sub.5 is lower alkyl or ##STR6## wherein R.sub.6 is hydrogen or alkyl having 1-10 carbon atoms and R.sub.7 represents alkyl having 4-12 carbon atoms or cycloalkyl, Y is CH and X represents oxygen or sulfur, with the proviso that (i) when Y is CH and X is oxygen or sulfur Ar is other than C wherein R.sub.5 is CH.sub.3 and (ii) when Y is CH and X represents sulfur Ar is other than A. The compound is useful in the treatment of dermatologic ailments linked to a keratinization disorder.

Aromatic heterocyclic derivatives and their thereapeutic and cosmetic use

New polysubstituted derivatives of naphthalene. These derivatives correspond to the following formula: ##STR1## in which: R.sub.1 to R.sub.4 is H or CH.sub.3

Polysubstituted derivatives of naphtalene, their process of preparation

A benzonaphthalene compound has the formula ##STR1## wherein R.sub.1 represents ##STR2## or (ii) --CH.sub.2 OH; R.sub.6 represents ##STR3## or OR.sub.7 wherein R.sub.7 represents hydrogen, alkyl having 1-20 carbon atoms, monohydroxyalkyl or polyhydroxyalkyl, r' or r' represent hydrogen, lower alkyl, mono or polyhydroxyalkyl, aryl or a residue of an amino acid or a sugar, or together form a heterocycle; R.sub.2 represents hydrogen, alkyl having 1-15 carbon atoms, alkoxy having 1-4 carbon atoms or a cycloaliphatic radical; R.sub.3 represents hydrogen, hydroxy, alkyl having 1-4 carbon atoms, alkoxy having 1-10 carbon atoms, a cycloaliphatic radical, a thiocycloaliphatic radical or --O--Si(CH.sub.3).sub.2 --R.sub.8 wherein R.sub.8 represents lower alkyl; and R.sub.4 and R.sub.5 represent hydrogen, lower alkyl, hydroxy or lower acyloxy. This compound is useful in the topical and systemic treatment of dermatologic diseases and in the treatment of the degeneration of conjunctive tissues. The compound also possesses anti-tumor acitivity.

Growing community of inventors

Grasse, France

Jacques Eustache