Di (aromatic) compounds and their use in human and veterinary medicine and in cosmetics
AssigneeCentre International de Recherches Dermatologiques Galderma (Cird Galderma)
InventorsJean-Michel Bernardon, William Robert Pilgrim
Life of this patent
Estimating the term…
Abstract
Di(aromatic) compounds corresponding to the following formula: ##STR1## in which: Ar represents either ##STR2## n=1 or 2 or: ##STR3## X represents a divalent radical, Z represents O, S or a divalent radical, and R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 represent a hydrogen atom or various organic radicals, and the salts of the compounds of formula (I) when R.sub.1 is a carboxylic acid function. Use in human and veterinary medicine and in cosmetics.
Claims22
A di(aromatic) compound having the formula ##STR15## wherein Ar represents ##STR16## wherein n=1 or 2 or ##STR17## wherein R.sub.3 and R.sub.5 represent hydrogen, OH, alkoxy having 1-6 carbon atoms, .alpha.-branched alkyl having from 3-12 carbon atoms, .alpha.,.alpha.-branched alkyl having from 4-12 carbon atoms, cycloalkyl having 3-12 carbon atoms, or mono- or polycyclic cycloalkyl having 5-12 carbon atoms in which the carbon having the free valence is trisubstituted,
- R.sub.4 represents hydrogen, OH, alkoxy having 1-6 carbon atoms, .alpha.-branched alkyl having 3-12 carbon atoms, .alpha.,.alpha.-branched alkyl having 4-12 carbon atoms, cycloalkyl having 3-12 carbon atoms, mono-or polycyclic cycloalkyl having 5-12 carbon atoms in which the carbon having the free valence is trisubstituted, monohydroxyalkyl, polyhydroxyalkyl, fluorine, chlorine, SH, SR.sub.6, SOR.sub.6, SO.sub.2 R.sub.6, alkenyl having 2-6 carbon atoms or alkenyloxy having 2 to 6 carbon atoms,
- R.sub.6 represents lower alkyl,
- R.sub.1 represents hydrogen, OH, --CH.sub.3, --CH.sub.2 OH, --COR.sub.7, --CH(OH)CH.sub.3, --CH.sub.2 OCOR.sub.8, --SO.sub.2 R.sub.9, --SOR.sub.9 or --SR.sub.9,
- R.sub.7 represents hydrogen, OH, --OR.sub.10, --N(r'r"), lower alkyl, monohydroxyalkyl, polyhydroxyalkyl or a sugar residue,
- R.sub.10 represents alkyl having 1-12 carbon atoms or alkenyl having 2-12 carbon atoms,
- r' and r", each independently, represent hydrogen, lower alkyl, aryl, aralkyl, an amino acid residue, a sugar residue, an amino sugar residue or a heterocycle, or r' and r" taken together form a heterocycle,
- R.sub.8 represents a saturated or unsaturated, linear or branched alkyl having 1-20 carbon atoms or a sugar residue,
- R.sub.9 represents OH, alkyl or --N(r'r"),
- R.sub.2 represents OH,
- Z represents an oxygen atom, a sulphur atom, --CH.dbd.CR.sub.11 --, --N.dbd.CH-- or --N.dbd.CR.sub.6 --
- wherein
- R.sub.6 has the meaning given above,
- R.sub.11 represents hydrogen, OH, lower alkyl, alkoxy having 1-6 carbon atoms, fluorine, chlorine or CF.sub.3,
- X represents a divalent radical which can be read from left to right or vice versa and has the formula ##STR18## wherein R' represents hydrogen or --CH.sub.3 and
- W represents an oxygen atom, a sulfur atom or --NR' wherein R' has the meaning given above, and salts thereof of said compound, with the proviso that when X from left to right represents the formula:
- ##STR19## wherein:
- R' is hydrogen and W is an oxygen or a sulphur atom,
- R.sub.3 and R.sub.4 do not simultaneously represent OH.
A pharmaceutical composition comprising in a vehicle suitable for enteral, parenteral, topical or ocular administration at least one di(aromatic) compound having the formula ##STR20## wherein Ar represents ##STR21## wherein n=1 or 2 or ##STR22## wherein R.sub.3 and R.sub.5 represent hydrogen, OH, alkoxy having 1-6 carbon atoms, .alpha.-branched alkyl having from 3-12 carbon atoms, .alpha.,.alpha.-branched alkyl having from 4-12 carbon atoms, cycloalkyl having 3-12 carbon atoms, or mono- or polycyclic cycloalkyl having 5-12 carbon atoms in which the carbon having the free valence is trisubstituted,
- R.sub.4 represents hydrogen, OH, alkoxy having 1-6 carbon atoms, .alpha.-branched alkyl having 3-12 carbon atoms, .alpha.,.alpha.-branched alkyl having 4-12 carbon atoms, cycloalkyl having 3-12 carbon atoms, mono-or polycyclic cycloalkyl having 5-12 carbon atoms in which the carbon having the free valence is trisubstituted, monohydroxyalkyl, polyhydroxyalkyl, fluorine, chlorine, SH, SR.sub.6, SOR.sub.6, SO.sub.2 R.sub.6, alkenyl having 2-6 carbon atoms or alkenyloxy having 2 to 6 carbon atoms,
- R.sub.6 represents lower alkyl,
- R.sub.1 represents hydrogen, OH, --CH.sub.3, --CH.sub.2 OH, --COR.sub.7, --CH(OH)CH.sub.3, --CH.sub.2 OCOR.sub.8, --SO.sub.2 R.sub.9, --SOR.sub.9 or --SR.sub.9,
- R.sub.7 represents hydrogen, OH, --OR.sub.10, --N(r'r") , lower alkyl, monohydroxyalkyl, polyhydroxyalkyl or a sugar residue,
- R.sub.10 represents alkyl having 1-12 carbon atoms or alkenyl having 2-12 carbon atoms,
- r' and r", each independently, represent hydrogen, lower alkyl, aryl, aralkyl, an amino acid residue, a sugar residue, an amino sugar residue or a heterocycle, or r' and r" taken together form a heterocycle,
- R.sub.8 represents a saturated or unsaturated, linear or branched alkyl having 1-20 carbon atoms or a sugar residue,
- R.sub.9 represents OH, alkyl or --N(r'r"),
- R.sub.2 represents OH,
- Z represents an oxygen atom, a sulphur atom, --CH.dbd.CR.sub.11 --, --N.dbd.CH-- or --N.dbd.CR.sub.6 --
- wherein
- R.sub.6 has the meaning given above,
- R.sub.11 represents hydrogen, OH, lower alkyl, alkoxy having 1-6 carbon atoms, fluorine, chlorine or CF.sub.3,
- X represents a divalent radical which can be read from left to right or vice versa and has the formula ##STR23## wherein R' represents hydrogen or --CH.sub.3 and
- W represents an oxygen atom, a sulfur atom or --NR' wherein R' has the meaning given above, and salts thereof of said compound.
A cosmetic composition for body and hair hygiene comprising, in a cosmetically acceptable vehicle at least one di(aromatic) compound having the formula ##STR24## wherein Ar represents ##STR25## wherein n=1 or 2 or ##STR26## wherein R.sub.3 and R.sub.5 represent hydrogen, OH, alkoxy having 1-6 carbon atoms, .alpha.-branched alkyl having from 3-12 carbon atoms, .alpha.,.alpha.-branched alkyl having from 4-12 carbon atoms, cycloalkyl having 3-12 carbon atoms, or mono- or polycyclic cycloalkyl having 5-12 carbon atoms in which the carbon having the free valence is trisubstituted,
- R.sub.4 represents hydrogen, OH, alkoxy having 1-6 carbon atoms, .alpha.-branched alkyl having 3-12 carbon atoms, .alpha.,.alpha.-branched alkyl having 4-12 carbon atoms, cycloalkyl having 3-12 carbon atoms, mono-or polycyclic cycloalkyl having 5-12 carbon atoms in which the carbon having the free valence is trisubstituted, monohydroxyalkyl, polyhydroxyalkyl, fluorine, chlorine, SH, SR.sub.6, SOR.sub.6, SO.sub.2 R.sub.6, alkenyl having 2-6 carbon atoms or alkenyloxy having 2 to 6 carbon atoms,
- R.sub.6 represents lower alkyl,
- R.sub.1 represents hydrogen, OH, --CH.sub.3, --CH.sub.2 OH, --COR.sub.7, --CH(OH)CH.sub.3, --CH.sub.2 OCOR.sub.8, --SO.sub.2 R.sub.9, --SOR.sub.9 or --SR.sub.9,
- R.sub.7 represents hydrogen, OH, --OR.sub.10, --N(r'r"), lower alkyl, monohydroxyalkyl, polyhydroxyalkyl or a sugar residue,
- R.sub.10 represents alkyl having 1-12 carbon atoms or alkenyl having 2-12 carbon atoms,
- r' and r", each independently, represent hydrogen, lower alkyl, aryl, aralkyl, an amino acid residue, a sugar residue, an amino sugar residue or a heterocycle, or r' and r" taken together form a heterocycle,
- R.sub.8 represents a saturated or unsaturated, linear or branched alkyl having 1-20 carbon atoms or a sugar residue,
- R.sub.9 represents OH, alkyl or --N(r'r"),
- R.sub.2 represents OH,
- Z represents an oxygen atom, a sulphur atom, --CH.dbd.CR.sub.11 --, --N.dbd.CH-- or --N.dbd.CR.sub.6 --
- wherein
- R.sub.6 has the meaning given above,
- R.sub.11 represents hydrogen, OH, lower alkyl, alkoxy having 1-6 carbon atoms, fluorine, chlorine or CF.sub.3,
- X represents a divalent radical which can be read from left to right or vice versa and has the formula ##STR27## wherein R' represents hydrogen or --CH.sub.3 and
- W represents an oxygen atom, a sulfur atom or --NR' wherein R' has the meaning given above, and salts thereof of said compound.
Dependencies are inferred from the claim text.