Triazine derivatives

Details Triazine derivatives Triazine derivatives

2000-04-06

2001-02-27

Dodson, Shelley A. (Department: 1616)

Drug, bio-affecting and body treating compositions

Topical sun or radiation screening, or tanning preparations

C424S060000, C424S400000, C424S401000, C514S241000

Reexamination Certificate

active

06193960

ABSTRACT:

The present invention relates to novel s-triazine compounds, processes for their preparation and the use of these novel compounds as UV filters in cosmetic compositions, in particular sunscreen compositions.
The novel s-triazine compounds are those of the formula
in which
R is halogen; straight-chain or branched C
1
-C
22
-Alkyl; straight-chain or branched C
1
-C
22
-Alkoxy; straight-chain or branched C
1
-C
22
-Hydroxyalkoxy; straight-chain or branched C
1
-C
22
-Alkoxyalkyl; —NHR
1
;
or a radical of the formula
X
1
, X
2
and X
3
independently of one another are —CONHR
1
;
 —SO
2
R
4
; —CN;
R
1
is hydrogen; straight-chain or branched C
1
-C
22
alkyl; C
6
-C
12
aryl which is unsubstituted, monosubstituted or polysubstituted by C
1
-C
4
alkyl; C
7
-C
10
aralkyl which is unsubstituted, monosubstituted or polysubstituted by C
1
-C
4
alkyl; C
5
-C
8
cycloalkyl; or a radical of the formula
 in which
A
1
is straight-chain or branched C
1
-C
8
alkyl; C
5
-C
8
-cycloalkyl; C
6
-C
12
aryl which is unsubstituted, monosubstituted or polysubstituted by C
1
-C
4
alkyl; C
7
-C
10
aralkyl which is unsubstituted, monosubstituted or polysubstituted by C
1
-C
4
alkyl; and
m
1
is 1 to 10;
R
2
and R
3
independently of one another are hydrogen; straight-chain or branched C
1
-C
22
alkyl; C
5
-C
8
cycloalkyl; C
6
-C
12
aryl which is unsubstituted, monosubstituted or polysubstituted by C
1
-C
4
alkyl; C
7
-C
10
aralkyl which is unsubstituted, monosubstituted or polysubstituted by C
1
-C
4
alkyl; a radical of the formula (1b); or a radical of the formula
R
4
is branched or straight-chain C
1
-C
22
alkyl; C
5
-C
8
cycloalkyl; C
6
-C
12
aryl which is unsubstituted, monosubstituted or polysubstituted by C
1
-C
4
alkyl; C
7
-C
10
aralkyl which is unsubstituted, monosubstituted or polysubstituted by C
1
-C
4
alkyl; a radical of the formula (1b); or
R
5
and R
6
independently of one another are hydrogen; straight-chain or branched C
1
-C
22
alkyl; C
5
-C
8
cycloalkyl; C
6
-C
12
aryl which is unsubstituted, monosubstituted or polysubstituted by C
1
-C
4
alkyl; C
7
-C
10
aralkyl which is unsubstituted, monosubstituted or polysubstituted by C
1
-C
4
alkyl; or a radical of the formula (1b);
X
4
, X
5
and X
6
are hydrogen; or hydroxy;
where compounds of the formula (1) are not additionally included in which X
1
and X
2
are —CONHR
1
; and X
3
is then
 or compounds in which X
1
and X
2
are
 and X
3
is —CONHR
1
; or compounds in which X
1
, X
2
and X
3
are
Straight-chain and branched C
1
-C
22
alkyl are, for example, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, 2-ethylbutyl, n-pentyl, isopentyl, 1-methylpentyl, 1,3-di-methylbutyl, n-hexyl, 1-methylhexyl, n-heptyl, isoheptyl, 1,1,3,3-tetramethylbutyl, 1-methylheptyl, 3-methylheptyl, n-octyl, 2-ethylhexyl, 1,1,3-trimethylhexyl, 1,1,3,3-tetramethylpentyl, nonyl, decyl, undecyl, 1-methylundecyl, dodecyl, 1,1,3,3,5,5-hexamethylhexyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl or eicosyl.
Examples of straight-chain and branched C
1
-C
22
alkoxy are methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentoxy, isopentoxy, n-heptyloxy, n-octyloxy, isooctyloxy, n-nonyloxy, isononyloxy, decyloxy, n-dodecyloxy, pentadecyloxy; heptadecyloxy, octadecyloxy or eicosyloxy.
C
5
-C
8
-Cycloalkyl is, for example, cyclopentyl, cycloheptyl, cyclooctyl and in particular cyclohexyl.
Examples of C
6
-C
12
aryl which may be mentioned in particular are phenyl, naphthyl and biphenylyl.
Examples of C
7
-C
10
aralkyl are benzyl, phenethyl, &agr;-methylphenethyl or &agr;,&agr;-dimethylbenzyl.
“Alkylene” in the formula (1b) is a bivalent alkylene group having 2 to 5, preferably 2 to 4, carbon atoms. It is in this case preferably the —CH
2
—CH
2
—; —CH
2
CH
2
CH
2
—; —CH
2
—CH
2
—CH
2
—;
group. Among these alkylene groups, the —CH
2
—CH
2
— and the
groups are very particularly preferred.
Halogen is fluorine, bromine or preferably chlorine.
Preferred triazine compounds are those of the formula
X
1
, X
2
and X
3
are as defined for formula (1).
Predominant triazine compounds are those of the formula (1), in which X
1
, X
2
and X
3
are in the ortho-position to the phenylamino radical of the triazine, i.e. compounds of the formula
or very particularly triazine compounds of the formula (1), in which X
1
, X
2
and X
3
are in the para-position to the phenylamino radical of the triazine, i.e. compounds of the formula
or compounds of formula
X
1
, X
2
, X
3
, X
5
and X
6
are defined as in formula (1).
Triazine compounds of the formula (1) are preferably used, in which
X
1
, X
2
and X
3
independently of one another are a radical of the formula
 and
R
2
and R
3
here are as defined in formula (1).
Among these compounds, in turn those are preferred in which
R
2
is hydrogen and
R
3
is a radical of the formula
 in which
R
7
is straight-chain or branched C
1
-C
22
alkyl or a radical of the formula (1b).
Further interesting triazine compounds of the formula (1) are those in which
X
1
and X
2
are a radical of the formula
 and
X
3
is a radical of the formula
 in which
R
5
and R
6
independently of one another are straight-chain or branched C
1
-C
8
alkyl.
Triazine compounds of the formula (1) are furthermore preferred in which X
1
and X
2
independently of one another are a radical of the formula
and
X
3
is a radical of the formula
 in which
R
2
is hydrogen;
R
3
is a radical of the formula
 and
R
1
and R
6
independently of one another are straight-chain or branched C
1
-C
8
alkyl.
Triazines of the formula (1) are particularly preferred in which X
1
, X
2
and X
3
have the same meaning.
Of predominant interest here are triazine compounds of the formula
in which
X
4
is —CONHR
8
;
 —SO
2
R
10
; —CN; or
R
8
is hydrogen; or straight-chain or branched C
1
-C
22
alkyl; or a radical of the formula (1b);
R
9
is a radical of the formula (6a)
R
10
is straight-chain or branched C
1
-C
22
alkyl; or —NH
2
;
R
11
is straight-chain or branched C
1
-C
22
alkyl; or a radical of the formula
&Parenopenst;alkylene-O&Parenclosest;A
2
  (6b)
R
12
is hydrogen; or straight-chain or branched C
1
-C
22
alkyl; and
A
2
is straight-chain or branched C
1
-C
8
alkyl.
Very particularly of interest here are compounds of the formula (6), in which
X
4
is CONHR
8
;
 in which
R
8
is hydrogen; or straight-chain or branched C
1
-C
8
alkyl; or a radical of the formula (1b); and R
9
and R
11
are as defined above.
Triazine compounds of the formula (1) are furthermore preferred in which
R
4
is branched or straight-chain C
1
-C
22
alkyl; or
and
R
2
and R
3
are as defined in formula (1).
Among these triazine compounds, those compounds are very particularly preferred in which
R
2
is hydrogen and
R
3
is C
1
-C
5
alkyl;
or triazine compounds in which
R
2
and R
3
are hydrogen.
The triazine compounds of the formula (1) according to the invention are prepared in a manner known per se, for example by reaction of 1 mol of cyanuric chloride with 1 mol in each case of the corresponding aniline compounds of the formula
or R—H.
R, X
2
, X
3
, X
5
and X
6
here are as defined in formula (1).
The reaction is usually carried out in a suitable solvent at a temperature from 50 to 200° C.
Suitable solvents here are, for example, acetonitrile, ketones, for example acetone or methyl ethyl ketone; ethers, for example diethyl ether, diisopropyl ether, tetrahydrofuran (THF), dimethylformamide (DMF) or dioxane; aliphatic or aromatic hydrocarbons, for example pentane, heptane, cyclohexane, benzene, toluene, xylene or mixtures thereof; or aliphatic carboxylic acid esters, for example ethyl acetate. The solvent used for the preparation process according to the invention is preferably dimethylformamide (DMF).
The general reaction of trihalotriazine compounds, for example cyanuric fluoride or cyanuric chloride, in which the three halogen atoms are replaced by amino radicals, is known and described in detail in the technical literature, in particu

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