US 7,022,317 B2 · Heterocyclic derivatives of 2-oxothiazolidine-4-carboxylic acid, and use as active photoprotective agents

Abstract

The present invention relates to novel heterocyclic derivatives of 2-oxothiazolidine-4-carboxylic acid, to a process for synthesizing them and to compositions containing them. The invention also relates to the use of at least one heterocyclic derivative of 2-oxathiazolidine-4-carboxylic acid in a composition or for the manufacture of a composition, the said derivative or the said composition being intended to induce active photoprotection of the skin, advantageously to prepare the skin to receive sunlight and/or to protect the skin and other epidermal growths during or after exposure to UV. Another subject of the invention also relates to a cosmetic process for treating the skin by oral administration or topical administration to the skin of a cosmetic composition as defined above.

Claims31

Dependent claims

A 2-oxothiazolidine-4-carboxylic acid derivative of formula (I):

in which:
X represents an oxygen atom or a radical NR″;
R″ represents a linear, cyclic or branched alkyl radical containing from 1 to 12 carbon atoms, which is optionally substituted;
Y represents a group (CH2)n;
Z represents a group (CRR′)
n is an integer chosen from 0, 1, 2 and 3;
R and R′, which may be identical or different, represent:
a hydrogen atom;
an —Si—(CH3)3, —Si(CH3)2—OH, Si—(CH3)2—OEt, —Si—(CH3)2—O—CH2—Ph or —Si—(iPr)2—OEt radical;
a halogen;
an alkyl radical as defined above;
an optionally substituted aryl radical;
an optionally substituted arylalkyl radical;
wherein when X represents a radical NR″, R″ and R′ taken together can form, with the 2 atoms bearing them, a heterocycle containing 4, 5 or 6 carbon atoms;
or wherein
Y and Z each represent a carbon atom and together form an aromatic heterocycle or ring containing 5, 6 or 7 carbon atoms, the said ring or heterocycle being optionally substituted;
and
the optical or geometrical isomers thereof, alone or as a mixture in all proportions, and the physiologically acceptable salts thereof.

15 more elements

A 2-oxothiazolidine-4-carboxylic acid derivative selected from:

tetrahydrothiazolo[3,4-a]pyrazine-3,5,8-trione;
6-methyltetrahydro[1,3]thiazolo[3,4-a]pyrazine-3,5,8-trione;
6-ethyltetrahydro[1,3]thiazolo[3,4-a]pyrazine-3,5,8-trione;
6-propyltetrahydro[1,3]thiazolo[3,4-a]pyrazine-3,5,8-trione;
6-iso-propyltetrahydro[1,3]thiazolo[3,4-a]pyrazine-3,5,8-trione;
6-propyltetrahydro[1,3]thiazolo[3,4-a]pyrazine-3,5,8-trione;
6-[1-methylpropyl]tetrahydro[1,3]thiazolo[3,4-a]pyrazine-3,5,8-trione;
6-isobutyltetrahydro[1,3]thiazolo[3,4-a]pyrazine-3,5,8-trione;
6-phenyltetrahydro[1,3]thiazolo[3,4-a]pyrazine-3,5,8-trione;
6-benzyltetrahydro[1,3]thiazolo[3,4-a]pyrazine-3,5,8-trione;
6-(methylsulphanyl)ethyltetrahydro[1,3]thiazolo[3,4-a]pyrazine-3,5,8-trione;
6-(ethylsulphanyl)methyltetrahydro[1,3]thiazolo[3,4-a]pyrazine-3,5,8-trione;
7-methyltetrahydrotetra[1,3]thiazolo[3,4-a]pyrazine-3,5,8-trione;
7-ethyltetrahydrotetra[1,3]thiazolo[3,4-a]pyrazine-3,5,8-trione;
tetrahydro-1 H,5H-pyrrolo[1,2a][1,3]thiazolo[3,4d]pyrazine-3,5,10(10aH)trione;
3-(3,5,8-trioxohexahydrothiazolo[3,4-a]pyrazin-6-yl)propionic acid;
6-mercaptomethyltetrahydrothiazolo[3,4-a]pyrazine-3,5,8-trione;
7-methyltetrahydrothiazolo[3,4-a]pyrazine-3,5,8-trione;
6,7-dimethyltetrahydro[1,3]thiazolo[3,4-a]pyrazine-3,5,8-trione;
6-ethyl-7-methyltetrahydro[1,3]thiazolo[3,4-a]pyrazine-3,5,8-trione;
6-propyl-7-methyltetrahydro[1,3]thiazolo[3,4-a]pyrazine-3,5,8-trione;
6-iso-propyl-7-methyltetrahydro[1,3]thiazolo[3,4-a]pyrazine-3,5,8-trione;
6-propyl-7-methyltetrahydro[1,3]thiazolo[3,4-a]pyrazine-3,5,8-trione;
6-[1-methylpropyl]-7-methyltetrahydro[1,3]thiazolo[3,4-a]pyrazine-3,5,8-trione;
6-iso-butyl-7-methyltetrahydro[1,3]thiazolo[3,4-a]pyrazine-3,5,8-trione;
6-phenyl-7-methyltetrahydro[1,3]thiazolo[3,4-a]pyrazine-3,5,8-trione,
6-benzyl-7-methyltetrahydro[1,3]thiazolo[3,4-a]pyrazine-3,5,8-trione;
6-(methylsulphanyl)ethyl-7-methyltetrahydro[1,3]thiazolo[3,4-a]pyrazine-3,5,8-trione;
6-(ethylsulphanyl)methyl-7-methyltetrahydro[1,3]thiazolo[3,4-a]pyrazine-3,5,8-trione;
3-(3,5,8-trioxohexahydro-7-methylthiazolo[3,4-a]pyrazin-6-yl)propionic acid;
6-mercaptomethyl-7-methyltetrahydrothiazolo[3,4-a]pyrazine-3,5,8-trione;
1H-[1,3]thiazolo[4,3-c]oxazine-3,5,8-[6H,8aH]trione;
1,10a-dihydro-9-oxa-2-thia-3a-azabenzo[f]azulene-3,4,10-trione;
6-octanoyl-1,10a-dihydro-9-oxa-2-thia-3a-azabenzo[f]azulene-3,4,10-trione;
and
(6-carboxymethyl-3,5,8-trioxotetrahydrothiazolo[4,3-c][1,4]oxazin-6-yl)acetic acid.

33 more elements

Dependencies are inferred from the claim text.

Heterocyclic derivatives of 2-oxothiazolidine-4-carboxylic acid, and use as active photoprotective agents

Life of this patent

Heterocyclic derivatives of 2-oxothiazolidine-4-carboxylic acid, and use as active photoprotective agents

Life of this patent

Abstract

Claims31