Patent DE-102006006115-A1 (DE)
Title: New quinoxaline derivatives useful e.g. in cosmetic and pharmaceutical preparation as photo stable UV-filter with reduced skin penetration potential to protect human skin or hair against sun radiation
Inventor: PFLUECKER FRANK
IPC: C08G77/388
Filed: 2006-02-10
Abstract: Quinoxaline derivatives (I) are new. Quinoxaline derivatives (I) of formula (R-(Si(-CH3)2-O)n-(Si(CH3)(X-Y1>)-O)m-Si((CH3)2)-R) are new. m, n, o : 0-6 (where n is less than m); R : 1-20C alkyl, phenyl or quinoxaline; X : a spacer of 1-20C alkylene, alkoxyalkylene, oxyalkylene, amino-benzoic acid ester compound of formula (IIa) or amino-N-propyl-benzamide compound of formula (IIb) (where in X, silicon is bound to Si via oxygen of (IIa) and Q of (IIb)); Y1>quinoxaline compound of formula (IIIa or IIIb) (where the bond between X and Y1> can be attached to any C atom on (IIIa) or (IIIb)); either R1>, R2>H, alkyl, tert-butyl, isopropyl, alkoxy, ethylenehexyl, alkenyl or alkynyl with up to 20C atom, cycloalkyl, cycloalkoxy, cycloalkenyl or bicyclic system substituted with up to 10C atom, Hal, OH, NO2, -(CR5>R6>)p-NR5>R6>, -(CR5>R6>)p-N=CR5>R6>, -(CR5>R6>)p-CR5>=NR5>, -(CR5>R6>)p-NHCOR5>, -(CR5>R6>)p-NHCOOR5>, -SR5>, -SO2-R5>, NR5>-SO-R6>, -SO-R5> (where water-soluble making substituents such as carboxylate-, sulfonate- or ammonium), COR5>, COOR5>, CONR5>R6>, CN, O=S(-R5>)=O, O=S(-OR5>)=O, O=S(-NR5>R6>)=O, R5>OP(-OR6>)=O, OAr, -(CR5>R6>)p-Ar, -Het, -NHHet, -OHet or -(CR5>R6>)p-Het (where one or more H are optionally replaced by Sub1>, one or more CH2 groups are optionally replaced by (CO), and the cyclic system optionally contains 1-3 heteroatoms such as S, N or O); or R1>+R2>4-7 membered ring optionally containing heteroatoms of S, N and/or O; Sub1>Hal, OH, CN, NH2, NO2, 1-4C-alkylamino, 1-4C-dialkylamino, 1-4C alkyl, 1-4C alkoxy, COOH or COOalkyl; Hal : F, Cl, Br or I; p : 0-4; either R5>, R6>H, alkyl, alkenyl, alkynyl substituted with upto 20C atoms, cycloalkyl, cycloalkenyl, bicyclic system with up to 10C atoms (where one or more H atoms are optionally replaced by Sub1> and CH2 groups are optionally replaced by (CO), and the cyclic system contains 1-3 of heteroatoms such as S, N or O), -(CR-aR-b)p-Ar or -(CR-aR-b)p-Het; or CR5>R6>4-7 membered ring containing heteroatoms of S, N and/or O; R-a, R-b : H or 1-4C alkyl (where CH2 groups are substituted by CO); Ar : optionally substituted aromatic ring or condensed ring with 6-18C atom (where the CH2 group in alpha or beta position is substituted by heteroatom or CO); Het : optionally substituted 5-7 heteroaromatic ring or condensed ring (where the heteroatoms are N-, S- and/or O and the CH3 group in alpha and beta position is substituted by CO or heteroatom); either R3>, R4>H, alkyl, alkoxy, alkenyl or alkynyl with up to 20C atoms, cycloalkyl, cycloalkoxy, cycloalkenyl or bicyclic system with up to 10C atoms, Hal, OH, NO2, -(CR5>R6>)p-NR5>R6>, -(CR5>R6>)p-N=CR5>R6>, -(CR5>R6>)p-CR5>=NR5>, -(CR5>R6>)p-NHCOR5>, -(CR5>R6>)p-NHCOOR5>, -SR5>, -SO2-R5>, NR5>-SO-R6>, -SO-R5> (where water-soluble making substituents are carboxylate-, sulfonate- or ammonium), COR5>, COOR5>, COR5>R6>, CN, O=S(-R5>)=O, O=S(-OR5>)=O, O=S(-NR5>R6>)=O, R5>OP(-OR6>)=O, OAr, -(CR5>R6>)p-Ar, -Het, -NHHet, -OHet or -(CR5>R6>)p-Het (where one or more H atoms are substituted by Sub2>, CH2 group is replaced by (CO), or and the cyclic system contains 1-3 of heteroatoms such as S, N or O); or CR3>R4>4-7 membered ring containing heteroatoms of S, N and/or O; R7>H, alkyl, alkoxy, alkynyl with up to 20C atoms, cycloalkyl, cycloalkoxy, cycloalkenyl, bicyclic system with up to 10C (where one or more H atoms are optinally replaced by Sub1> and CH2 groups are optionally replaced by (CO), or the cyclic system contains 1-3 of heteroatoms such as S, N or O); Sub2>Hal, OH, CN, NH2, NO2, 1-4C-alkyl or 1-4C-alkoxy, COR5>, COOR5>, OAr, OHet, -(CR5>R6>)p-Ar or -(CR5>R6>)n-Het, -(CR5>R6>)p-NR5>R6>, CONR5>R6>, CN, O=S(-R5>)=O, O=S(-OR5>)=O, O=S(-NR5>R6>)=O or R7>OP(-OR8>)=O; and Q : carbon. Independent claims are included for: (1) a light protection agent comprising cosmetic and pharmaceutical preparation to protect human epidermis or hair against UV light of 280-400 nm with suitable carrier or in combination with cosmetic and pharmaceutical preparation with UV absorbent compound, as photo-stable UV filter containing (I); (2) a cosmetic or pharmaceutical preparation (A) comprising UV filter such as 3-(4'-methylbenzylidine)-di-camphor, 1-(4-tert-butylphenyl)-3-(4-methoxyphenyl)propan-1,3-dione, 4-isopropyldibenzoyl methane, 2-hydroxy-4-methoxybenzophenone, methoxyacidoctyl ester, 3,3,5-trimethyl cyclohexyl salicylate, 4-(dimethylamino)benzoic acid-2-ethylhexylester, 2-cyano-3,3-diphenylacrylic acid-2-ethylhexylester, 2-phenylbenzimidazol-5-sulfonic acid, potassium, sodium or triethanolamine salt; and (3) use of (I) in combination with antioxidant in (A). [Image] [Image] ACTIVITY : Dermatological. MECHANISM OF ACTION : None given.