Patent DE-10013318-A1 (DE)
Title: Quinoxaline derivatives are used as photo-stable UV filters in cosmetic or pharmaceutical sunscreens for the hair or skin
Inventor: PFLUECKER FRANK
IPC: C09K3/00
Filed: 2000-03-17
Abstract: Photo-stable UV filters in cosmetic or pharmaceutical sunscreens for the hair or skin of quinoxaline derivatives, are new. Optionally also present are known UV-absorbers.  Photo-stable UV filters in cosmetic or pharmaceutical sunscreens for the hair or skin of quinoxaline derivatives of formula (I) - (III), are new. Optionally also present are known UV-absorbers.  R<1> and R<2>  = H, up to 20C alkyl, alkoxy, alkenyl or alkynyl, up to 10C cycloalkyl, cycloalkoxy, cycloalkenyl or bicyclic systems (with each of these groups having one or more H atom substituted by Sub<1> and/or having 1 or 2 CH2 groups replaced by C:O and with the cyclic systems optionally containing 1-3 O, S and/or N as heteroatoms), Hal, OH, NO2, -(CR<5>R<6>)n-NR<5>R<6>, -(CR<5>R<6>)n-N=CR<5>R<6>, -(CR<5>R<6>)n-CR<5>=NR<5>, -(CR<5>R<6>)n-NHCOR<5>, -(CR<5>R<6>)n-NHCOOR<5>, water-solubilizing groups comprising carboxylate, sulfonate or ammonium residues, COR<5>, COOR<5>, CONR<5>R<6>, CN, O=S(R<5>)=O, O=S(OR<5>)=O, O=S(NR<5>R<6>)=O, R<7>-OP(OR<8>)=O, OAr, -(CR<5>R<6>)nAr, OHet or -(CR<5>R<6>)-Het; or R<1> and R<2> together with bonded C atoms form unsaturated or partly or completely saturated 4-7-membered rings which optionally contain S, N and/or O heteroatoms and which are optionally annelated and/or substituted;  Sub<1>  = hal, OH, CN, amino, NO2, 1-4C (di)alkylamino, alkyl or alkoxy, COOH or COOalkyl; hal  = F, Cl, Br or I;  n  = 0-4;  R<5> - R<8>  = H, up to 20C alkyl, alkoxy, alkenyl or alkynyl, up to 10C cycloalkyl, cycloalkoxy, cycloalkenyl or bicyclic systems (with each of these groups having 1-3 Sub<1> groups and/or having 1 or 2 CH2 groups replaced by C:O and with the cyclic systems optionally containing 1-3 O, S and/or N as heteroatoms), -(CR'R'')n-Ar or -(CR'R'')n-Het or R<5> - R<8> together with bonded C atoms form unsaturated or partly or completely saturated 4-7-membered rings which optionally contain S, N and/or O heteroatoms and which are optionally annelated and/or substituted; R' and R''  = H or 1-4C alkyl optionally with 1 or 2 CH2 groups replaced by C:O;  Ar  = optionally substituted, optionally condensed 6-18C ring system optionally with 1 or 2 CH2 groups replaced by C:O; Het  = optionally substituted, optionally condensed 5-7-membered heteroatom system containing 1 or more N, S and/or O atom and optionally with 1 or 2 CH2 groups replaced by C:O;  R<3>, R<4>  = H, up to 20C alkyl, alkoxy, alkenyl or alkynyl, up to 10C cycloalkyl, cycloalkoxy, cycloalkenyl or bicyclic systems (with each of these groups having 1-3 Sub<2> groups and/or having 1 or 2 CH2 groups replaced by C:O and with the cyclic systems optionally containing 1-3 O, S and/or N as heteroatoms), Hal, OH, NO2, -(CR<5>R<6>)n-NR<5>R<6>, -(CR<5>R<6>)n-N=CR<5>R<6>, -(CR<5>R<6>)n-CR<5>=NR<5>, -(CR<5>R<6>)n-NHCOR<5>, -(CR<5>R<6>)n-NHCOOR<5>, water-solubilizing groups comprising carboxylate, sulfonate or ammonium residues, COR<5>, COOR<5>, CONR<5>R<6>, CN,O=S(R<5>)=O, O=S(OR<5>)=O, O=S(NR<5>R<6>)=O, R<7>-OP(OR<8>)=O, OAr, -(CR<5>R<6>)nAr, OHet or -(CR<5>R<6>)-Het; or R<3> and R<4> together with bonded C atoms (or with the adjacent N atom) form unsaturated or partly or completely saturated 4-7-membered rings which optionally contain S, N and/or O heteroatoms and which are optionally annelated and/or substituted; and  Sub<2>  = hal, OH, CN, amino, NO2, 1-4C alkyl or alkoxy, COR<5>, COOR<5>, OAr, OHet, -(CR<5>R<6>)n-Ar, -(CR<5>R<6>)n-Het, -(CR<5>R<6>)n-NR<5>R<6>, CONR<5>R<6>, CN,O=S(R<5>)=O, O=S(OR<5>)=O, O=S(NR<5>R<6>)=O or R<7>-OP(OR<8>)=O An Independent claim is also for 12 new quinoxaline derivatives including, viz. 5-nitro-2,3,6-trimethoxy-quinoxaline; 2,3,7-trimethoxy-6,8-dinitro-quinoxaline; N-(2-quinoxalinyl)-4-aminobenzoic acid isopropyl ester; N,N-benzoyl-(2-quinoxalinyl)-4-aminobenzoic acid; N-(2-quinoxalinyl)-4-aminomethylbenzoic acid; N-(2-quinoxalinyl)-2-amino-4,5-dimethoxybenzoic acid; N-(2-quinoxalinyl)-2-amino-pyrimidine; N-(2-quinoxalinyl)-2-amino-benzophenone; N-(2-quinoxalinyl)-4-amino-anisole; N-(2-quinoxalinyl)-3,4,5-trimethoxy-aniline; N-(bis-(2-quinoxalinyl))-2,4,6-trifluoro-aniline; and N-(2-(3-phenyl)-quinoxalinyl)-4-amino-benzoic acid.