Polyaromatic heterocyclic compounds and pharmaceutical/cosmetic compositions comprised thereof
AssigneeCentre International de Recherches Dermatologiques Galderma
InventorsBruno Charpentier, Philippe Diaz, Philippe Nedoncelle
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Abstract
Novel pharmaceutically/cosmetically-active polyaromatic heterocyclic compounds have the structural formula (I): ##STR1## in which Z is a divalent radical selected from among --O--, --S-- or --Nr'-- and Ar is either a radical having the following structural formula (II): ##STR2## or a radical having the following structural formula (III): ##STR3## and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.
Claims37
A polyaromatic heterocyclic compound having the structural formula (I):
- ##STR12## in which Z is --O--;
- Ar is either a radical having the following structural formula (II):
- ##STR13## or a radical having the following structural formula (III):
- ##STR14## wherein m is equal to 0 or 1;
- R.sub.1 is (i) a hydrogen atom, (ii) the --CH.sub.3 radical, (iii) a radical --(CH.sub.2).sub.p --O--R.sub.12, (iv) a radical OR.sub.12, (v) a radical:
- ##STR15## or (vi) a radical --S(O).sub.t R.sub.14, wherein R.sub.12, R.sub.13, R.sub.14, p and t are as defined below;
- R.sub.2 is a hydrogen atom, a halogen atom, a lower alkyl radical or a radical --OR.sub.12 I wherein R.sub.12 is as defined below;
- R.sub.3 and R.sub.4, which may be identical or different, are each a halogen atom, a hydrogen atom, a lower alkyl radical or a radical OR.sub.12, wherein R.sub.12 is as defined below;
- R.sub.5 is a halogen atom, a hydrogen atom, a lower alkyl radical or a radical --OR.sub.15, wherein R.sub.15 is as defined below;
- R.sub.6, R.sub.7, R.sub.8 and R.sub.9, which may be identical or different, are each a hydrogen atom, a halogen atom, an alkyl radical, a cycloalkyl radical, a radical --(Z.sub.2).sub.n --(CH.sub.2).sub.q --CO--R.sub.13 or a radical --Z.sub.2 --R.sub.12, with the proviso that at least two of the radicals R.sub.6, R.sub.7, R.sub.8 and R.sub.9 are other than a hydrogen atom and further wherein Z.sub.1, Z.sub.2, R.sub.12, R.sub.13, n and q are as defined below;
- R.sub.10 and R.sub.11 are lower alkyl radicals;
- Y is a divalent radical selected from among --C(R.sub.11).sub.2 --, --O--, --S--, --CH(OH)--, --CO--, --SO-- and --SO.sub.2 --, wherein R.sub.11 is as defined above, with the proviso that R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 cannot simultaneously each be a hydrogen atom;
- R.sub.12 is a hydrogen atom, a lower alkyl radical, an aryl radical, an aralkyl radical, a polyhydroxyalkyl radical, a polyether radical or a lower acyl radical;
- R.sub.13 is (a) a hydrogen atom, (b) a radical:
- ##STR16## wherein r and r' are as defined below, or (c) a radical --OR.sub.14, wherein R.sub.14 is as defined below;
- R.sub.14 is a hydrogen atom, an alkyl radical, a mono- or polyhydroxyalkyl radical, an optionally substituted aryl or aralkyl radical, or a sugar or amino acid residue;
- R.sub.1 is a hydrogen atom, a lower alkyl radical, an aryl radical, an aralkyl radical or a polyether radical;
- r and r', which may be identical or different, are each a hydrogen atom, a lower alkyl radical, an optionally substituted aryl radical, or an amino acid or sugar residue, or r and r' may together form, with the nitrogen atom from which they depend, a heterocycle;
- Z.sub.1 is O, S or Nr';
- Z.sub.2 is O, n is equal to 0 or 1;
- p is equal to 0, 1, 2 or 3;
- q is an integer ranging from 0 to 10;
- t is equal to 0, 1, 2 or 3;
- and the further provisos that at least one of R.sub.6, R.sub.7, R.sub.8 and R.sub.9 is a cycloalkyl radical or an alkyl radical selected from the group consisting of isopropyl and tert-butyl radicals;
- and R.sub.1 and R.sub.2 cannot be --O--R.sub.12 or (CH.sub.2).sub.p OR.sub.12, when p equals 0. Ar is of formula (II), and one of the substituents R.sub.6, R.sub.7, R.sub.8 or R.sub.9 is an alkyl radical;
- and the pharmaceutically/cosmetically acceptable optical and geometric isomers and salts thereof.
Dependencies are inferred from the claim text.