Use of N-arylmethylene, ethylenediaminetriacetates, N-arymethylene iminodiacetates or N,N'-diarylmethylene ethylenediamineacetates against oxidative stress
AssigneeL'oreal
InventorsJean Baptiste Galey, Jacqueline Dumats
Life of this patent
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Abstract
N-arylmethylene ethylenediaminetriacetate, N-arylmethylene iminodiacetate or N,N'-diarylmethylene ethylenediaminediacetate type compounds and their use in combatting oxidative stress, and pharmaceutical and cosmetic compositions comprising said compounds. The invention also concerns a process for the preparation of said compounds.
Claims12
Process for protecting the human body against oxidative stress which comprises administering to it an effective amount of a compound of formula (I):
- ##STR18## in which:
- Z.sub.1, Z.sub.2 and Z.sub.3, independently of one another, represent NO.sub.2, COOH, CF.sub.3, a halogen atom or an R.sub.1, OR.sub.1, SR.sub.1 or NR.sub.1 R.sub.2 group,
- Z.sub.4 represents an R.sub.1 group;
- where R, R.sub.1 and R.sub.2, independently of one another, represent H or a linear or branched C.sub.1 to C.sub.8 alkyl group,
- X.sub.1, X.sub.2 and X.sub.3 represent:
- ##STR19## or --N.dbd., provided that if X.sub.1 =N, then X.sub.2 --X.sub.3 =C and there is no Z.sub.1 substituent at X.sub.1,
- if X.sub.1 =N, then X.sub.1 .dbd.X.sub.3 =C and there is no Z.sub.2 substituent at X.sub.2,
- if X.sub.3 =N, then X.sub.2 .dbd.X.sub.1 =C and there is no Z.sub.3 substituent at X.sub.3, that is to say that it is a pyridine ring;
- if X.sub.1, X.sub.2 and X.sub.3 all represent C, it is then a benzene ring;
- Z.sub.5 represents:
- the group:
- --COOR (a)
- or the group:
- ##STR20## or the group:
- ##STR21## in which Z.sub.1, Z.sub.2, Z.sub.3, Z.sub.4, X.sub.1, X.sub.2, X.sub.3, R, R.sub.1 and R.sub.2 have the same meanings as above;
- or of its salts and metal complexes.
Cosmetic composition comprising at least one compound of formula (I):
- ##STR22## in which:
- Z.sub.1, Z.sub.2 and Z.sub.3, independently of one another, represent NO.sub.2, COOH, CF.sub.3, a halogen atom or an R.sub.1, OR.sub.1, SR.sub.1 or NR.sub.1 R.sub.2 group,
- Z.sub.4 represents an R.sub.1 group;
- where R, R.sub.1 and R.sub.2, independently of one another, represent H or a linear or branched C.sub.1 to C.sub.8 alkyl group,
- X.sub.1, X.sub.2 and X.sub.3 represent:
- ##STR23## or --N.dbd., provided that if X.sub.1 =N, then X.sub.2 .dbd.X.sub.3 =C and there is no Z.sub.1 substituent at X.sub.1,
- if X.sub.2 =N, then X.sub.1 .dbd.X.sub.3 =C and there is no Z.sub.2 substituent at X.sub.2,
- if X.sub.3 =N, then X.sub.2 .dbd.X.sub.1 =C and there is no Z.sub.3 substituent at X.sub.3, that is to say that it is a pyridine ring;
- if X.sub.1, X.sub.2 and X.sub.3 all represent C, it is then a benzene ring;
- Z.sub.5 represents:
- the group:
- --COOR (a)
- or the group:
- ##STR24## or the group:
- ##STR25## in which Z.sub.1, Z.sub.2, Z.sub.3, Z.sub.4, X.sub.1, X.sub.2, X.sub.3, R, R.sub.1 and R.sub.2 have the same meanings as above;
- or its salts or metal complexes, in a cosmetically acceptable medium.
Pharmaceutical composition comprising, in a pharmaceutically acceptable medium, at least one compound of formula (I):
- ##STR26## in which:
- Z.sub.1, Z.sub.2 and Z.sub.3, independently of one another, represent NO.sub.2, COOH, CF.sub.3, a halogen atom or an R.sub.1, OR.sub.1, SR.sub.1 or NR.sub.1 R.sub.2 group,
- Z.sub.4 represents an R.sub.1 group;
- where R, R.sub.1 and R.sub.2, independently of one another, represent H or a linear or branched C.sub.1 to C.sub.8 alkyl group,
- X.sub.1, X.sub.2 and X.sub.3 represent:
- ##STR27## or --N.dbd., provided that if X.sub.1 =N, then X.sub.2 .dbd.X.sub.3 =C and there is no Z.sub.1 substituent at X.sub.1,
- if X.sub.2 =N, then X.sub.1 .dbd.X.sub.3 =C and there is no Z.sub.2 substituent at X.sub.2,
- if X.sub.3 =N, then X.sub.2 .dbd.X.sub.1 =C and there is no Z.sub.3 substituent at X.sub.3, that is to say that it is a pyridine ring;
- if X.sub.1, X.sub.2 and X.sub.3 all represent C, it is then a benzene ring;
- Z.sub.5 represents:
- the group:
- --COOR (a)
- or the group:
- ##STR28## or the group:
- ##STR29## in which Z.sub.1, Z.sub.2, Z.sub.3, Z.sub.4, X.sub.1, X.sub.2, X.sub.3, R, R.sub.1 and R.sub.2 have the same meanings as above;
- or its salts or metal complexes.
Compound of formula (I):
- ##STR30## in which:
- Z.sub.1, Z.sub.2 and Z.sub.3, independently of one another, represent NO.sub.2, COOH, CF.sub.3, a halogen atom or an R.sub.1, OR.sub.1, SR.sub.1 or NR.sub.1 R.sub.2 group, Z.sub.4 represents an R.sub.1 group;
- where R, R.sub.1 and R.sub.2, independently of one another, represent H or a linear or branched C.sub.1 to C.sub.8 alkyl group,
- X.sub.1, X.sub.2 and X.sub.3 represent:
- ##STR31## or --N.dbd., provided that if X.sub.1 =N, then X.sub.2 .dbd.X.sub.3 =C and there is no Z.sub.1 substituent at X.sub.1,
- if X.sub.2 =N, then X.sub.1 .dbd.X.sub.3 =C and there is no Z.sub.2 substituent at X.sub.2,
- if X.sub.3 =N, then X.sub.2 .dbd.X.sub.1 =C and there is no Z.sub.3 substituent at X.sub.3, that is to say that it is a pyridine ring;
- if X.sub.1, X.sub.2 and X.sub.3 all represent C, it is then a benzene ring;
- Z.sub.5 represents:
- the group:
- --COOR (a)
- or the group ##STR32## or the group:
- ##STR33## in which Z.sub.1, Z.sub.2, Z.sub.3, Z.sub.4, X.sub.1, X.sub.2, X.sub.3, R, R.sub.1 and R.sub.2 have the same meanings as above provided that when X.sub.1, X.sub.2 and X.sub.3 all represent C, Z.sub.5 does not represent the group (c);
- with the exception of the following compounds:
- benzyliminodiacetic acid and its dimethyl ester, diethyl ester, monoethyl ester and ethyl-tert.-butyl ester, (3-aminobenzyl)iminodiacetic acid, (3-nitrobenzyl)iminodiacetic acid, (4-nitrobenzyl)iminodiacetic acid, (4-aminobenzyl)iminodiacetic acid, (4-hydroxybenzyl)iminodiacetic acid, (4-dimethylaminobenzyl)iminodiacetic acid, (4-methylbenzyl)-iminodiacetic acid, (4-fluorobenzyl)iminodiacetic acid, (3-nitro-4-chlorobenzyl)iminodiacetic acid, benzylethylenediaminetriacetic acid and (3-pyridylmethylene)iminodiacetic acid, N,N'-bis(3-hydroxy-2,5-dimethyl-4-pyridylmethylene)ethylenediamine diacetic acid;
- or its salts or metal complexes.
A compound of the formula:
- ##STR35## wherein Z.sub.2 and Z.sub.4 represent H and Z.sub.1 and Z.sub.3 are independently of each other CH.sub.3, OCH.sub.3, CF.sub.3, NO.sub.2 or a halogen atom.
Dependencies are inferred from the claim text.