Benzimidazole-derived compounds, method for preparing the same,

Details Benzimidazole-derived compounds, method for preparing the same, Benzimidazole-derived compounds, method for preparing the same,

1994-01-10

1995-08-29

Gerstl, Robert

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

5483101, C07D23518, A61K 31415

Patent

active

054460590

DESCRIPTION:

BRIEF SUMMARY
The subject of the present invention is new benzimidazole derivatives, method for preparing the same and therapeutical and cosmetic uses thereof.
These new benzimidazole derivatives have proved to have, in human or veterinary medicine, good activity with respect to inflammatory and/or immunoallergic conditions.
In cosmetics, these new benzimidazole derivatives constitute particularly advantageous substances in body and hair hygiene.
The state of the art relating to benzimidazole derivatives is essentially represented by French Patent Application No. 85 13747 (2,570,377) which describes certain benzimidazole derivatives having a biological profile assigning them to the compounds known under the name of "retinoid" and having a reinforced activity in the treatment of dermatological ailments linked to a keratinization disorder (differentiation/proliferation).
The benzimidazole derivatives according to the invention can be represented by the following general formula: ##STR1## in which:
R.sub.1 and R.sub.2 represent a hydrogen atom, a lower alkyl radical, an OR.sub.4 radical, a lower fluoroalkyl radical or a halogen atom,
R.sub.3 represents a hydrogen atom, a lower alkyl radical, a halogen, a hydroxyl or a lower alkoxyradical having from 1 to 6 carbon atoms,
R.sub.4 represents a hydrogen atom, a lower alkyl radical, a benzyl radical, or a ##STR2## PO.sub.3 H or SO.sub.3 H radical or an amino acid residue,
R.sub.7 represents a lower alkyl radical, a lower alkoxy radical having from 1 to 6 carbon atoms, the --(CH.sub.2).sub.n --COOH radical, n=1 to 6, or the ##STR3## radical,
r' and r" representing a hydrogen atom or a lower alkyl radical or r' and r", taken together, form, with the nitrogen atom, a 5- or 6-membered heterocycle optionally interrupted by a heteroatom,
R.sub.5 and R.sub.6, which are different, represent the OR.sub.8 radical or a mono- or polycyclic cycloalkyl radical having from 5 to 12 carbon atoms, linked to the phenyl ring via a tertiary carbon;
R.sub.8 represents a hydrogen atom, a lower alkyl radical, an acyl radical having from 2 to 7 carbon atoms, a benzyl radical optionally substituted by one or a number of halogen atoms or the benzoyl radical, and the salts of the said compounds obtained by addition of a pharmaceutically acceptable acid or base.
According to the invention, the salts are obtained by addition of a base when R.sub.4 represents SO.sub.3 H, PO.sub.3 H or --CO(CH.sub.2).sub.n --COOH. These salts can also be obtained by addition of an acid when R.sub.5 represents the ##STR4## radical,
r' and r", taken together forming a basic heterocycle.
It is also possible to form salts by addition of an acid to the nitrogen atoms of the benzimidazole system.
Lower alkyl radical must be understood to mean a linear or branched radical having from 1 to 6 carbon atoms, especially a methyl, ethyl, isopropyl, butyl, 1-methylpropyl, 1-ethylpropyl, tert-butyl, 1,1-dimethylpropyl and 1-methyl-1-ethylpropyl radical.
Lower fluoroalkyl radical must be understood to mean a radical having from 1 to 6 carbon atoms and from 1 to 5 fluorine atoms, such as the trifluoromethyl radical.
The halogen atom is according to the invention preferably a chlorine, bromine or fluorine atom.
Lower alkoxy radical having from 1 to 6 carbon atoms must be understood to mean especially a methoxy, ethoxy, isopropoxy or butoxy radical.
Mono- or polycyclic cycloalkyl radical, having from 5 to 12 carbon atoms, linked to the phenyl ring via a tertiary carbon, must be understood to mean especially 1-adamantyl or 1-methylcyclohexyl radicals.
Acyl radical, having from 2 to 7 carbon atoms, must be understood to mean especially acetyl, propionyl, butyryl, isobutyryl, valeryl or pivalyl radicals.
When r' and r", taken together, form, with the nitrogen atom, a 5- or 6-membered heterocycle, the latter is preferably a piperidino, morpholino, pyrrolidino or piperazino radical, optionally substituted in position 4 by a lower alkyl radical.
Amino acid residue must be understood to mean more particularly residues deriving from lysine, glycine or

REFERENCES:
patent: 4717720 (1988-01-01), Shroot et al.
patent: 4920140 (1990-04-01), Shroot
patent: 4940696 (1990-07-01), Shroot et al.
patent: 5098895 (1992-03-01), Shroot et al.
Katritzky, Comprehensive Heterocyclic Chemistry p. 472 (1984).

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