Naphthalene derivatives having retinoid type action, the process

Details Naphthalene derivatives having retinoid type action, the process Naphthalene derivatives having retinoid type action, the process

1986-12-05

1989-11-07

Griffin, Ronald W.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Carbohydrate doai

549398, 549404, 549408, 546187, 546189, 546196, 546205, 546206, C07C 5742, C07C10358, A61K 700, A61K 3119

Patent

active

048792845

DESCRIPTION:

BRIEF SUMMARY
The invention relates to new chemical compounds consisting of 2-substituted naphthalene derivatives and also to a preparation process by means of which these new compounds may be obtained. The invention also relates to the use of these new compounds, either in cosmetics or as pharmaceutical preparations in the treatment of dermatological conditions linked to a disorder of keratinization (differentiation/proliferation), in the treatment of dermatological or other conditions having an inflammatory and/or immuno-allergic component and in the treatment of atopy, whether cutaneous or respiratory, and also as pharmaceutical preparations for the ophthalmological field, in particular in the treatment of corneopathies.
The therapeutic action of vitamin A in its acid, aldhyde or alcohol form is well known in dermatology [in this connection, see the publication EXPERIENTIA, volume 34, pages 1105-1119 (1978)]; this action in the treatment of cutaneous proliferations, acne, psoriasis and similar conditions will be designated hereinafter by the generic term "retinoid type action". It was found that products having a structure analogous to vitamin A also showed a retinoid type action, but that the side effect of toxic hypervitaminosis could, for certain compounds, be boosted by a smaller factor than the boosting factor of the retinoid type effect sought (in this connection, see EUR. J. MED. CHEM.-CHIMICA THERAPEUTICA, Jan.-Feb. 1980, 15, No. 1, pages 9-15); in this latter publication, P. LOELIGER et al. described a derivative of formula (I): ##STR2##
The unsaturated side chain of this compound of formula (I) is identical to that of natural retinoic acid of formula (II): ##STR3##
From German patent application Ser. No. 2,437,607, there is also known a family of compounds having retinoid type action corresponding to the general formula (III): ##STR4## in which formula the substituents R.sup.3 and R.sup.4, inter alia, together form a benzene ring fused to the first ring, the compound of formula (III) then corresponding to a naphthalene derivative substituted at the 2-position with a 3,7-dimethyltetraene chain, which is the same as that in the abovementioned compounds (I) and (II).
From German Patent No. 3,121,091, a compound having anti-seborrhoeic action is also known, corresponding to the general formula (IV): ##STR5## in which formula n equals 0 or 1, which means that the side chain contains at most two double bonds, and in which R'.sub.1 and R'.sub.2 can form together a benzene ring fused to the first ring, so that the resulting compound is a naphthalene derivative substituted in the 2-position.
From U.S. Pat. No. 3,755,604, a method is known for decreasing sebum production by means of a 2-trans-4-trans-pentanedienoic acid of formula: ##STR6## where R can represent hydrogen.
Finally, M. AKHTAR et al., in the publication J. CHEM. SOC., CHEM. COMMUN., 1982, page 44, have described the aldehyde of formula (V): ##STR7##
This publication gives no indication of the fact that the aldehyde of formula (V) might show any medicinal or cosmetic action.
It has been found, according to the invention, that the aldehyde of formula (V) shows a retinoic action and that it was possible to synthesise compounds of formula (V) modified by the presence of substituents on the naphthalene ring, and/or by the replacement of the aldehyde group by other groups, these compounds still enjoying the retinoid action.
The subject of the invention is hence the new industrial product represented by a new chemical compound corresponding to the general formula (VI): ##STR8## in which formula:
R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which can be distributed on either of the rings or on both at once, denote, independently, a hydrogen atom, a linear or branched C.sub.1 -C.sub.6 alkyl radical, a hydroxyl group or a C.sub.1 -C.sub.6 alkoxy radical; and
A denotes a group --COR.sub.5 in which R.sub.5 is:
(a) a hydrogen atom when at least one of the substituents R.sub.1 to R.sub.4 is other than hydrogen; a C.sub.1 -C.sub.6 alkyl radical; an amino radical; an alkylam

REFERENCES:
patent: 3984444 (1976-10-01), Bollag et al.
patent: 4193931 (1980-03-01), Loeliger
Journal of the Chemical Society-Chemical Communications, No. 1, 1982, M. Akhtar et al.: "Interaction of a Conformationally Rigid Analogue of Retinal with Bacterio-Opsin", pp. 44-46, p. 44, alinea 1; Formule 2.
FR, A, 2239996 (F. Hoffmann-La Roche) 7 Mars 1975, voir revendications 1,6,22-26.
Helvetica Chimica Acta, vol. 63, Fasc. 6, No. 168, (1980), P. Loeliger et al.: "Synthese Bicyclischer Retinoide aus Retinsaule", pp. 1604-1608, p. 1604, "Summary"; p. 1605, Formule 2.
Biochemistry, vol. 23, No. 5, 28 Fevrier 1984, American Chemical Society, (U.S) Tatsuo Iwasa et al.: "Properties of an Analogue Pigment of Bacteriorhodopsin Synthesized with Naphthylretinal", pp. 838-843, voir, p. 838.

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