Compounds and Their Use in Filtering Ultraviolet and/or High-Energy Visible Light

A compound of formula (II)

• or a tautomer, a stereoisomer, a hydrate, a solvate, a salt, or a polymorph thereof, wherein R1a, R2a, R3a, and R4a are each independently Rza;
• each Rza is independently selected from the group comprising hydrogen, halo, alkyl, haloalkyl, alkylcarbonyl, alkenyl, alkynyl, aryl, heterocyclyl, heteroaryl, cycloalkyl, aryl-alkylene, aryl-alkenylene, aryl-alkynylene, heteroaryl-alkylene, heteroaryl-alkenylene, heteroaryl-alkynylene, heterocyclyl-alkylene, heterocyclyl-alkenylene, heterocyclyl-alkynylene, cycloalkyl-alkylene, cycloalkyl-alkenylene, cycloalkyl-alkynylene, —ORa, non-acylated or acylated glycosyl, non-acylated or acylated —O-glycosyl, non-acylated or acylated —NRb-glycosyl, non-acylated or acylated —C-glycosyl, non-acylated or acylated —S-glycosyl, —SRa, —S(O)Ra, —NRaRb, and —NRbC(O)Ra;
• each Ra is independently selected from the group comprising hydrogen, halo, alkyl, haloalkyl, alkylcarbonyl, alkenyl, alkynyl, aryl, heterocyclyl, heteroaryl, cycloalkyl, aryl-alkylene, aryl-alkenylene, aryl-alkynylene, heteroaryl-alkylene, heteroaryl-alkenylene, heteroaryl-alkynylene, heterocyclyl-alkylene, heterocyclyl-alkenylene, heterocyclyl-alkynylene, cycloalkyl-alkylene, cycloalkyl-alkenylene, cycloalkyl-alkynylene, and —Rf1-Rg1;
• wherein each of said alkyl, haloalkyl, alkylcarbonyl, alkenyl, alkynyl, aryl, heterocyclyl, heteroaryl, cycloalkyl, aryl-alkylene, aryl-alkenylene, aryl-alkynylene, heteroaryl-alkylene, heteroaryl-alkenylene, heteroaryl-alkynylene, heterocyclyl-alkylene, heterocyclyl-alkenylene, heterocyclyl-alkynylene, cycloalkyl-alkylene, cycloalkyl-alkenylene, and cycloalkyl-alkynylene, can be unsubstituted or substituted with one or more Rza1;
• wherein each Rza1 is independently selected from the group comprising —COO—Rh,
• NRa1Rb, —Rf1-Rg1, halo, alkyl, haloalkyl, alkylcarbonyl, alkenyl, and alkynyl;
• wherein Rh is selected from the group comprising hydrogen, alkyl, alkenyl, and alkynyl;
• Ra1 is selected from the group comprising hydrogen, alkyl, alkenyl, and alkynyl;
• Rb1 is selected from the group comprising hydrogen, alkyl, alkenyl, and alkynyl;
• Rc1 is selected from the group comprising hydrogen, alkyl, alkenyl, and alkynyl;
• Rf1 is alkylene, wherein said alkylene can be interrupted by one or more O or S;
• Rg1 is hydrogen, or alkyl;
• each Rb is independently selected from the group comprising hydrogen, halo, alkyl, haloalkyl, alkylcarbonyl, aryl, heterocyclyl, heteroaryl, cycloalkyl, aryl-alkylene, heteroaryl-alkylene, heterocyclyl-alkylene, and cycloalkyl-alkylene;
• X1a is —NRb—;
• Z1a is selected from the group comprising hydrogen, —CO—Ra, —CO—Re—CO—O—Rb, —CO—Rf—Rg, —Rf-Rg, halo, alkyl, haloalkyl, alkylcarbonyl, alkenyl, alkynyl, aryl, heterocyclyl, heteroaryl, cycloalkyl, aryl-alkylene, aryl-alkenylene, aryl-alkynylene, heteroaryl-alkylene, heteroaryl-alkenylene, heteroaryl-alkynylene, heterocyclyl-alkylene, heterocyclyl-alkenylene, heterocyclyl-alkynylene, cycloalkyl-alkylene, cycloalkyl-alkenylene, and cycloalkyl-alkynylene;
• X2a is —(CRcRd)n—;
• wherein n is an integer selected from 1, 2 or 3;
• each Rc and Rd is independently selected from the group comprising hydrogen, halo, alkyl, haloalkyl, alkenyl, alkynyl, aryl, heterocyclyl, heteroaryl, cycloalkyl, aryl-alkylene, aryl-alkenylene, aryl-alkynylene, heteroaryl-alkylene, heteroaryl-alkenylene, heteroaryl-alkynylene, heterocyclyl-alkylene, heterocyclyl-alkenylene, heterocyclyl-alkynylene, cycloalkyl-alkylene, cycloalkyl-alkenylene, and cycloalkyl-alkynylene;
• Re is selected from the group comprising alkylene, alkenylene, alkynylene, arylene, heterocyclylene, heteroarylene, and cycloalkylene;
• Rf is alkylene, wherein said alkylene can be interrupted by one or more O or S;
• Rg is selected from hydrogen, alkyl, N-maleimidyl, N-maleimidyloxy, or N-maleimidyloxycarbonyl;
• W1a is selected from —NRbZ2a, —Ra, or —ORa;
• Z2a is selected from the group comprising hydrogen, —CO—Ra, halo, alkyl, haloalkyl, alkylcarbonyl, alkenyl, alkynyl, aryl, heterocyclyl, heteroaryl, cycloalkyl, aryl-alkylene, aryl-alkenylene, aryl-alkynylene, heteroaryl-alkylene, heteroaryl-alkenylene, heteroaryl-alkynylene, heterocyclyl-alkylene, heterocyclyl-alkenylene, heterocyclyl-alkynylene, cycloalkyl-alkylene, cycloalkyl-alkenylene, and cycloalkyl-alkynylene;
• Y1a is selected from —ORa, —Ra, or —NRaRb, or Y1a is a moiety of formula (A);
• wherein
• Ar2 is aryl or heteroaryl;
• wherein each of said aryl or heteroaryl can be unsubstituted or substituted with one or more Rzb;
• each Rzb is independently selected from the group comprising hydrogen, halo, alkyl, haloalkyl, —ORa, alkenyl, alkynyl, aryl, heterocyclyl, heteroaryl, cycloalkyl, aryl-alkylene, aryl-alkenylene, aryl-alkynylene, heteroaryl-alkylene, heteroaryl-alkenylene, heteroaryl-alkynylene, heterocyclyl-alkylene, heterocyclyl-alkenylene, heterocyclyl-alkynylene, cycloalkyl-alkylene, cycloalkyl-alkenylene, cycloalkyl-alkynylene, —SRa, non-acylated or acylated glycosyl, non-acylated or acylated —O-glycosyl, non-acylated or acylated —NRb-glycosyl, non-acylated or acylated —C-glycosyl, non-acylated or acylated —S-glycosyl, —C(O)—Ra, —S(O)Ra, —NRaRb, and —NRbC(O)Ra;
• X1b is selected from —NRb—, —O—, —S—, SO2—O—, or —SO—O—;
• Z1b is selected from the group comprising hydrogen, —CO—Ra, —CO—Re—CO—O—Rb, —CO—Rf-Rg, —Rf-Rg, halo, alkyl, haloalkyl, alkylcarbonyl, alkenyl, alkynyl, aryl, heterocyclyl, heteroaryl, cycloalkyl, aryl-alkylene, aryl-alkenylene, aryl-alkynylene, heteroaryl-alkylene, heteroaryl-alkenylene, heteroaryl-alkynylene, heterocyclyl-alkylene, heterocyclyl-alkenylene, heterocyclyl-alkynylene, cycloalkyl-alkylene, cycloalkyl-alkenylene, and cycloalkyl-alkynylene;
• X2b is —(CRcRd)m—;
• wherein m is an integer selected from 1, 2 or 3;
• and
• Y1b is selected from —ORa, —NRbRa, or —Ra;
• with the proviso that said compound is not:
• 2-amino-4-(2-aminophenyl)-4-oxobutanoic acid;
• (R)-2-amino-4-(2-aminophenyl)-4-oxobutanoic acid;
• (S)-2-amino-4-(2-aminophenyl)-4-oxobutanoic acid;
• 4-(2-acetamidophenyl)-2-amino-4-oxobutanoic acid;
• 2-acetamido-4-(2-aminophenyl)-4-oxobutanoic acid;
• (S)-2-amino-4-(2-amino-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)-4-oxobutanoic acid;
• 2-amino-4-oxo-4-(2-(((3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)amino)phenyl)butanoic acid;
• (2S)-2-amino-4-oxo-4-(2-(((3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)amino)phenyl)butanoic acid;
• (S)-2-amino-4-(2-amino-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)-4-oxobutanoic acid;
• methyl 2-amino-4-(2-aminophenyl)-4-oxobutanoate;
• 4-(2-amino-3-(((3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)-4-oxobutanoic acid;
• 2-acetamido-4-(2-amino-3-(((3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)-4-oxobutanoic acid;
• (S)-2-acetamido-4-(2-amino-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)-4-oxobutanoic acid;
• (R)-2-acetamido-4-(2-amino-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)-4-oxobutanoic acid;
• (2R,3R,4S,5R)-2-(acetoxymethyl)-6-(2-amino-3-(4-methoxy-4-oxobutanoyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate;
• 2-amino-4-(2-amino-5-hydroxyphenyl)-4-oxobutanoic acid;
• (S)-2-amino-4-(2-amino-5-hydroxyphenyl)-4-oxobutanoic acid;
• (R)-2-amino-4-(2-amino-5-hydroxyphenyl)-4-oxobutanoic acid;
• 5-(2-aminophenyl)-5-oxopentanoic acid;
• 4-(2-aminophenyl)-4-oxobutanoic acid;
• methyl 6-(2-aminophenyl)-6-oxohexanoate;
• methyl 4-(2-aminophenyl)-2-((tert-butoxycarbonyl)amino)-4-oxobutanoate;
• butyl 2-amino-4-(2-aminophenyl)-4-oxobutanoate;
• ethyl (S)-2-amino-4-(2-aminophenyl)-4-oxobutanoate;
• (S)-2-amino-4-(2-aminophenyl)-4-oxobutanoic acid diacetate;
• (R)-2-amino-4-(2-formamidophenyl)-4-oxobutanoic acid;
• (S)-2-amino-4-(2-formamidophenyl)-4-oxobutanoic acid;
• 2-amino-4-(2-formamidophenyl)-4-oxobutanoic acid;
• methyl 2-acetamido-4-(2-acetamidophenyl)-4-oxobutanoate;
• 4-(2-amino-3-(((2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-((((2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)-4-oxobutanoic acid;
• 4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid O-beta-D-diglucoside);
• 4-(2-amino-3-(((2R,3S,4R,5R,6S)-3,4-5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)-4-oxobutanoic acid;
• 4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid O-beta-d-glucoside;
• 2-amino-4-(2-formamido-5-hydroxyphenyl)-4-oxobutanoic acid;
• 2-amino-4-(2-amino-3-chlorophenyl)-4-oxobutanoic acid;
• (R)-2-amino-4-(2-amino-3-chlorophenyl)-4-oxobutanoic acid;
• (S)-2-amino-4-(2-amino-3-chlorophenyl)-4-oxobutanoic acid;
• 2-amino-4-(2-amino-4-chlorophenyl)-4-oxobutanoic acid;
• (R)-2-amino-4-(2-amino-4-chlorophenyl)-4-oxobutanoic acid;
• (S)-2-amino-4-(2-amino-4-chlorophenyl)-4-oxobutanoic acid;
• 2-amino-4-(2-amino-5-fluorophenyl)-4-oxobutanoic acid;
• (R)-2-amino-4-(2-amino-5-fluorophenyl)-4-oxobutanoic acid;
• (S)-2-amino-4-(2-amino-5-fluorophenyl)-4-oxobutanoic acid;
• 2-amino-4-(2-amino-5-bromophenyl)-4-oxobutanoic acid;
• (R)-2-amino-4-(2-amino-5-bromophenyl)-4-oxobutanoic acid;
• (S)-2-amino-4-(2-amino-5-bromophenyl)-4-oxobutanoic acid;
• 2-amino-4-(2-amino-5-methylphenyl)-4-oxobutanoic acid;
• (R)-2-amino-4-(2-amino-5-methylphenyl)-4-oxobutanoic acid;
• (S)-2-amino-4-(2-amino-5-methylphenyl)-4-oxobutanoic acid;
• 2-amino-4-(2-amino-5-ethylphenyl)-4-oxobutanoic acid;
• (R)-2-amino-4-(2-amino-5-ethylphenyl)-4-oxobutanoic acid;
• (S)-2-amino-4-(2-amino-5-ethylphenyl)-4-oxobutanoic acid;
• 2-amino-4-(2-amino-5-propylphenyl)-4-oxobutanoic acid;
• (R)-2-amino-4-(2-amino-5-propylphenyl)-4-oxobutanoic acid;
• (S)-2-amino-4-(2-amino-5-propylphenyl)-4-oxobutanoic acid;
• 2-amino-4-(2-amino-5-isopropylphenyl)-4-oxobutanoic acid;
• (R)-2-amino-4-(2-amino-5-isopropylphenyl)-4-oxobutanoic acid;
• (S)-2-amino-4-(2-amino-5-isopropylphenyl)-4-oxobutanoic acid;
• 2-amino-4-(2-amino-5-cyclohexylphenyl)-4-oxobutanoic acid;
• (R)-2-amino-4-(2-amino-5-cyclohexylphenyl)-4-oxobutanoic acid;
• (S)-2-amino-4-(2-amino-5-cyclohexylphenyl)-4-oxobutanoic acid;
• 2-amino-4-(2-(methylamino)phenyl)-4-oxobutanoic acid;
• (S)-2-amino-4-(2-(methylamino)phenyl)-4-oxobutanoic acid;
• (R)-2-amino-4-(2-(methylamino)phenyl)-4-oxobutanoic acid;
• 2-amino-4-(2-(dimethylamino)phenyl)-4-oxobutanoic acid;
• (S)-2-amino-4-(2-(dimethylamino)phenyl)-4-oxobutanoic acid;
• (R)-2-amino-4-(2-(dimethylamino)phenyl)-4-oxobutanoic acid;
• 2-amino-4-(2-amino-5-chlorophenyl)-4-oxobutanoic acid;
• (R)-2-amino-4-(2-amino-5-chlorophenyl)-4-oxobutanoic acid;
• (S)-2-amino-4-(2-amino-5-chlorophenyl)-4-oxobutanoic acid;
• 2-amino-4-(2-amino-6-chlorophenyl)-4-oxobutanoic acid;
• (R)-2-amino-4-(2-amino-6-chlorophenyl)-4-oxobutanoic acid;
• (S)-2-amino-4-(2-amino-6-chlorophenyl)-4-oxobutanoic acid;
• 2-acetamido-4-(2-amino-5-chlorophenyl)-4-oxobutanoic acid;
• (R)-2-acetamido-4-(2-amino-5-chlorophenyl)-4-oxobutanoic acid;
• (S)-2-acetamido-4-(2-amino-5-chlorophenyl)-4-oxobutanoic acid;
• 2-amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid;
• (S-)2-amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid;
• (R-)2-amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid;
• methyl (S-)2-amino-4-(2-aminophenyl)-4-oxobutanoate;
• 2-amino-4-(2-aminophenyl)-4-oxobutanamide;
• (R)-2-amino-4-(2-aminophenyl)-4-oxobutanamide;
• (S)-2-amino-4-(2-aminophenyl)-4-oxobutanamide;
• (S)-2-acetamido-4-(2-acetamidophenyl)-4-oxobutanoic acid;
• (S)-2-formamido-4-(2-formamidophenyl)-4-oxobutanoic acid;
• 4-(2-aminophenyl)-4-oxo-2-phenylbutanamide.