2-(3,4-Dihydroxyphenyl)ethyl-substituted carbonic acid derivatives and their use
OwnerJakob Peter Leyinventor
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Abstract
The invention relates to the use of 2-(3,4-dihydroxyphenyl)ethyl-substituted carbonic acid derivatives as antioxidants or free-radical scavengers, in particular to the use for protecting human cells and tissues from the harmful, aging-accelerating effects of free-radicals and reactive oxygen compounds.
Claims9
An antioxidant or free-radical scavenger of 2-(3,4-dihydroxyphenyl)ethyl-substituted carbonic acid derivatives of the general formula I
- 4
- wherein
- R1 is a hydrogen atom, a lower alkyl, lower alkenyl, 1-oxo lower alkyl or 1-oxo lower alkenyl group or a group —O—R3, where R3 is a hydrogen atom, a lower alkyl, lower alkenyl, 1-oxo lower alkyl or 1-oxo lower alkenyl group, and
- X1, X2 and X3 independently of one another are oxygen, sulfur or NH, and
- R2 is a branched or unbranched cyclic or extended alkyl group having 1 to 22 carbon atoms or a branched or unbranched cyclic or extended alkenyl group having 2 to 22 carbon atoms, in which one or more of the carbon atoms can be replaced by oxygen atoms, or a nuclear-substituted arylalkyl group having 7 to 15 carbon atoms.
Cosmetic preparations, dermatological preparations and preparations serving for nutrition or pleasure comprising 2-(3,4-dihydroxy-phenyl)ethyl-substituted carbonic acid derivatives of the general formula I
- 5
- wherein
- R1 is a hydrogen atom, a lower alkyl, lower alkenyl, 1-oxo lower alkyl or 1-oxo lower alkenyl group or a group —O—R3, where R3 is a hydrogen atom, a lower alkyl, lower alkenyl, 1-oxo lower alkyl or 1-oxo lower alkenyl group, and
- X1, X2 and X3 independently of one another are oxygen, sulfur or NH, and
- R2 is a branched or unbranched cyclic or extended alkyl group having 1 to 22 carbon atoms or a branched or unbranched cyclic or extended alkenyl group having 2 to 22 carbon atoms, in which one or more of the carbon atoms can be replaced by oxygen atoms, or a nuclear-substituted arylalkyl group having 7 to 15 carbon atoms.
2-(3,4-Dihydroxyphenyl)ethyl-substituted carbonic acid derivatives of the general formula (II)
- 6
- wherein
- R1 is a hydrogen atom, a lower alkyl, lower alkenyl, 1-oxo lower alkyl or 1-oxo lower alkenyl group or a group —O—R3, where R3 is a hydrogen atom, a lower alkyl, lower alkenyl, 1-oxo lower alkyl or 1-oxo lower alkenyl group, and
- X3 is oxygen, sulfur or NH, and
- R2 is a branched or unbranched cyclic or extended alkyl group having 1 to 22 carbon atoms or a branched or unbranched cyclic or extended alkenyl group having 2 to 22 carbon atoms.
A process for preparing 2-(3,4-dihydroxyphenyl)ethyl substituted carbonic acid derivatives, comprising the step of reacting 2-(3,4-dihydroxyphenyl)ethylamines of the general formula (III)
- 7
- wherein R1is a hydrogen atom, a lower alkyl, lower alkenyl, 1-oxo lower alkyl or 1-oxo lower alkenyl group or a group —O—R3, where R3 is a hydrogen atom, a lower alkyl, lower alkenyl, 1-oxo lower alkyl or 1-oxo lower alkenyl group,
- or cationic salts thereof,
- with a heterocumulene of the general formula (IV),
- X4═C═N—R2 (IV)
- wherein
- X4 is an oxygen atom or a sulfur atom and
- R2 is a branched or unbranched cyclic or extended alkyl group having 1 to 22 carbon atoms or a branched or unbranched cyclic or extended alkenyl group having 2 to 22 carbon atoms, or
- with phosgene, thiophosgene or triphosgene with optionally, solvent and with optionally, addition of an auxiliary base and then either directly after purification or without purification with a compound of the general formula (V),
- Z-R2 (V)
- wherein
- Z is a group —O—H, —S—H, —NH2 or —(NH3)+ and
- R2 has the meaning specified above
- with optionally, solvent and with optionally, the addition of an auxiliary base.
Dependencies are inferred from the claim text.