Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Patent
1986-04-09
1988-12-13
Killos, Paul J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
C07C 6976
Patent
active
047912170
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to sulphur derivatives of para-methoxycinnamic acid not penetrating into the circulatory stream. They relate also to the production of said sulphur derivatives. The invention also relates to the cosmetological use, and the protection of the human skin against solar radiation; it relates also to the dermo-pharmaceutical and cosmetic compositions containing them.
The derivatives of para-methoxycinnamic acid correspond to the following formula I: ##STR1## in which R represents non-sulfurized alkyl groups. These compounds are widely used as solar filters and contained in cosmetological compositions as active ingredient.
2-ethyl hexyl para-methoxycinnamate is the molecule which possesses to present one of the most selective filtering powers; it is very widely used in antisolar preparations in France and in the world. It is recognised by the FDA as corresponding to the necessary criteria for a selective sun screen. However D. Claus (These de doctorat d'Universite mention Pharmacie, 1982, Strasbourg) has been able to show that this sun filter penetrated into the blood after application to rabbit skin.
The present invention relates to sulphur derivatives of para-methoxycinnamic acid. The compounds of the invention correspond to the following general formula III: ##STR2## in which: the cinnamic double bond can exist either in the cis or in the trans form or 2 group, R can also be an amino-alkyl or amino-aryl, or have an amino-acid structure giving a peptide linkage formula R'--CO--, R' being an alkyl or aryl group or again R'--CO-- having an amino-acid structure giving a peptide linkage.
In the present description, the term "alkyl" denotes aliphatic hydrocarbon groups containing 1 to 12 carbon atoms, with a straight or branched chain. Lower alkyl groups are preferred, that is to say alkyl groups containing 1 to 4 carbon atoms.
The term "aryl"denotes non heterocyclic-aromatic groups of the phenyl type, benzyl and higher homologues, substituted or not, as well as heterocyclic aromatic groups having 4 to 7 carbon atoms in the aromatic ring and 1 to 4 heteroatoms which can be oxygen, nitrogen, sulphur, furan type, pyridine, oxazole, as well as their saturated derivatives, respectively cyclohexane and tetrahydrofuran, piperidine, oxazolidine.
The present invention also relates to a process of synthesis of sulphur derivatives of para-methoxycinnamic acid with a disulfide bridge and with an amino-acid group, of the above formula III, which is characterized in that it consists of reacting a compound taken from the group which comprises sulphurized amino-acids and peptides having a free SH group, as well as their derivatives, with thio-2-ethanol para-methoxycinnamate of the following formula II:
According to an advantageous method of practising the process according to the invention, thio-2-ethanol para-methoxycinnamate, of formula II, used to prepare the compounds of formula III according to the present invention is itself obtained by reacting, in the course of a first step, thionyl chloride on para-methoxycinnamic acid, to obtain the chloride of para-methoxycinnamic acid which is reacted, in the course of a second step, with dithio-2,2'-diethanol to obtain dithio-2,2'-diethanol bis-(para-methoxycinnamate) which corresponds to the following formula IV: --S--S--CH.sub.2 --CH.sub.2 --OCO--CH.dbd.CH--C.sub.6 H.sub.4 --OCH.sub.3 (IV) para-methoxycinnamate of formula II.
It is also an object of the present invention to provide thio-2-ethanol para-methoxycinnamate of formula II, as an intermediate for the preparation of the compounds of formula III.
According to one method of practising the process of preparing the compound of formula III according to the present invention, the sulphurized amino acid used is cysteine or one of its higher homologues such as homocysteine, or a derivative of these amino acids.
According to another method of practising the process of preparing the compounds of formula III according to the present invention, the reaction of the amino acid or of the sulphurized protein wi
Jung Louis L.
Robert Dominique D.
Killos Paul J.
Universite Louis Pasteur
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