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US 2006/0222607 A1Published application
Tricyclic quinoxaline and quinoline derivatives as UV filters
OwnerFrank Pflucker, Michael Schwarz +2inventors
InventorsFrank Pflucker, Michael Schwarz, Volker Scholz, Hans Neunhoeffer
Life of this patent
Estimating the term…
Abstract
The invention relates to the use of quinoxaline derivatives of formula I, represented by formulas Ia and Ib, as photostable UV filters, in particular in cosmetic and pharmaceutical preparations for protecting the human epidermis or human hair against UV radiation, above all in the 280-400 nm range.
Claims21
1-14. (canceled)
A quinoxaline compound of formula VIII
- wherein
- R, R1 and R2 are each, independently of one another, H, alkyl, alkoxy, alkenyl or alkynyl, each having up to 20 carbon atoms, cycloalkyl, cycloalkoxy, cycloalkenyl or bicyclic systems, each having up to 10 carbon atoms, where, in all of these groups, one or more hydrogen atoms may also be substituted by Sub1 and/or one or two CH2 groups may be replaced by C═O, and the cyclic systems may contain 1 to 3 heteroatoms, Hal, OH, NO2, —(CR5R6)n—NR5R6—(CR5R6)n—N═CR5R6, —(CR5R6)n—CR5═NR5, —(CR5R6)n—NHCOR5, —(CR5R6)n—NHCOOR5, —SR5, —SO2—R5, NR5—SO—R6, —SO—R5, water-solubilising substituents, carboxylate, sulfonate or ammonium radicals, COR5, COOR5, CON5R6, CN, O═S(—R5)═O, O═S(—OR5)═O, O═S(—NR5R6)═O, R5OP(—OR6)═O, OAr, —(CR5R6)n—Ar, —Si(alkyl)3, —Si(alkyl)2H, -Het, —NHHet, —OHet or —(CR5R6)n-Het,
- R1 and R2 together, with carbon atoms to which they are bonded, may jointly form an unsaturated, partially or fully saturated 4-, 5-, 6- or 7-membered ring, which optionally contains one or more heteroatoms, may be further fused and/or may also be monosubstituted or polysubstituted,
- R4 is H or a branched or unbranched C1-20-alkyl radical, in which optionally one or more H atoms may be replaced by Sub,
- Sub is Hal, hydroxyl, cyano, amino, nitro, C1-C4-alkyl or C1-C4-alkoxy, COR5, COOR5, OAr, OHet, —(CR5R6)n—Ar or —(CR5R6)n—Het, —(CR5R6)n—NR5R6, CONR5R6, CN, O═S(—R5)═O, O═S(—OR5)═O, O═S(—NR5R6)═O or R5OP(—OR6)═O,
- Sub1 is Hal, hydroxyl, cyano, amino, nitro, C1-C4-alkylamino, C1-C4-dialkylamino, C1-C4-alkyl or C1-C4-alkoxy, COOH or COO-alkyl,
- Hal is fluorine, chlorine, bromine or iodine,
- n is 0, 1, 2, 3 or 4,
- m is 1, 2 or 3,
- R5 and R6 are each, independently of one another, H, alkyl, alkenyl, alkynyl, each having up to 20 carbon atoms, cycloalkyl, cycloalkenyl, bicyclic systems, each having up to 10 carbon atoms, where these radicals may be up to trisubstituted by Sub1 and/or one or two CH2 groups may be replaced by C═O, and the cyclic systems may also contain 1 to 3 heteroatoms, —(CR′R″)n—Ar or —(CR′R″)n—Het, or the radicals R5 and R6 may also, with one another, in each case together with carbon atoms to which they are bonded, jointly form an unsaturated, partially or fully saturated 4-, 5-, 6- or 7-membered ring, which optionally contains one or more heteroatoms, may also be monosubstituted or polysubstituted and/or may be further fused,
- R′ and R″ are each, independently of one another, H or C1-C4-alkyl, in which one or two CH2 groups may also be replaced by C═O,
- Ar is an unsubstituted or monosubstituted or polysubstituted aromatic ring or fused ring systems having 6 to 18 carbon atoms, in which one or two CH groups may also be replaced by C═O, and
- Het is an unsubstituted or monosubstituted or polysubstituted heteroaromatic ring having 5 to 7 ring members or a fused ring system, where the heteroatoms present are one or more N, S and/or O atoms, and in which one or two CH groups in the α- or β-position to the heteroatoms may also be replaced by C═O.
10 more elements
Dependencies are inferred from the claim text.