Pigmented and fluorescent compounds derived from the addition of a primary or secondary amine to an aldehyde

A compound of formula (Ia):

• wherein:
• R1 is 3,5-dimethoxy-4-hydroxyphenyl;
• R2 is selected from the group consisting of H, residue of an amino acid, residue of saccharide, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C1-C6)alkoxy, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkanoyl, (C1-C6)alkoxycarbonyl, (C1-C6)alkylthio and (C2-C6)alkanoyloxy, wherein any (C1-C6)alkyl, (C3-C6)cycloalkyl, (C1-C6)alkoxy, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkanoyl, (C1-C6)alkoxycarbonyl, (C1-C6)alkylthio and (C2-C6)alkanoyloxy is optionally substituted with one or more groups independently selected from the group consisting of halo, carboxy, —OH and cyano;
• R3 is selected from the group consisting of H, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C1-C6)alkoxy, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkanoyl, (C1-C6)alkoxycarbonyl, (C1-C6)alkylthio and (C2-C6)alkanoyloxy, wherein any (C1-C6)alkyl, (C3-C6)cycloalkyl, (C1-C6)alkoxy, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkanoyl, (C1-C6)alkoxycarbonyl, (C1-C6)alkylthio and (C2-C6)alkanoyloxy is optionally substituted with one or more groups independently selected from the group consisting of halo, carboxy, —OH and cyano;
• or R2 and R3 together with the nitrogen to which they are attached form a 4-10 membered ring heterocycle, wherein heterocycle is optionally substituted with one or more groups independently selected from the group consisting of halo, nitro, carboxy, —OH, cyano, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C1-C6)alkoxy, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkanoyl, (C1-C6)alkoxycarbonyl, (C1-C6)alkylthio, (C2-C6)alkanoyloxy, —NRaR′, —C(═O)NH(C1-C6 alkyl)(S(O)2Ra), —C(═O)NH(C1-C6 alkyl)(C(═O) ORa), —C(═O) NRaRb, —OS(O)3Ra, —C(═O)NH(S(O)2Ra), and —C(═O) (C1-C6 alkyl), wherein any (C1-C6)alkyl, (C3-C6)cycloalkyl, (C1-C6)alkoxy, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkanoyl, (C1-C6)alkoxycarbonyl, (C1-C6)alkylthio and (C2-C6)alkanoyloxy is optionally substituted with one or more groups independently selected from the group consisting of halo, carboxy, —OH, —NRaRb and cyano;
• and
• each Ra and Rb is independently selected from the group consisting of H, (C1-C6)alkyl, and (C3-C6)cycloalkyl;
• or Ra and Rb together with the nitrogen to which they are attached form a 4-10 membered ring heterocycle;
• and
• X is a suitable counter anion.

A compound of formula I

• wherein:
• R1 is 3,5-dimethoxy-4-hydroxyphenyl;
• R2 is (C1-C6)alkyl which is optionally substituted with one or more groups independently selected from the group consisting of carboxy and —OH;
• R3 is absent;
• or R3 is selected from the group consisting of H, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C1-C6)alkoxy, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkanoyl, (C1-C6)alkoxycarbonyl, (C1-C6)alkylthio and (C2-C6)alkanoyloxy, wherein any (C1-C6)alkyl, (C3-C6)cycloalkyl, (C1-C6)alkoxy, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkanoyl, (C1-C6)alkoxycarbonyl, (C1-C6)alkylthio and (C2-C6)alkanoyloxy is optionally substituted with one or more groups independently selected from the group consisting of halo, carboxy, —OH and cyano;
• provided that when R3 is other than absent, the nitrogen to which R3 is attached is a quaternary nitrogen and is associated with a suitable counter anion X− to provide a salt;
• and
• X is a suitable counter anion.

A compound of formula I

• wherein:
• R1 is 3,5-dimethoxy-4-hydroxyphenyl;
• R2 is carboxymethyl or tris(hydroxymethyl)methyl;
• R3 is absent;
• or R3 is selected from the group consisting of H, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C1-C6)alkoxy, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkanoyl, (C1-C6)alkoxycarbonyl, (C1-C6)alkylthio and (C2-C6)alkanoyloxy, wherein any (C1-C6)alkyl, (C3-C6)cycloalkyl, (C1-C6)alkoxy, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkanoyl, (C1-C6)alkoxycarbonyl, (C1-C6)alkylthio and (C2-C6)alkanoyloxy is optionally substituted with one or more groups independently selected from the group consisting of halo, carboxy, —OH and cyano;
• provided that when R3 is other than absent, the nitrogen to which R3 is attached is a quaternary nitrogen and is associated with a suitable counter anion X− to provide a salt;
• and
• X is a suitable counter anion.

A compound of formula I

• wherein:
• R1 is 3,5-dimethoxy-4-hydroxyphenyl;
• R2 is selected from the group consisting of H, residue of an amino acid, residue of saccharide, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C1-C6)alkoxy, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkanoyl, (C1-C6)alkoxycarbonyl, (C1-C6)alkylthio and (C2-C6)alkanoyloxy, wherein any (C1-C6)alkyl, (C3-C6)cycloalkyl, (C1-C6)alkoxy, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkanoyl (C1-C6)alkoxycarbonyl, (C1-C6)alkylthio and (C2-C6)alkanoyloxy is optionally substituted with one or more groups independently selected from the group consisting of halo, carboxy, —OH and cyano;
• R3 is (C1-C6)alkyl which is optionally substituted with one or more groups independently selected from the group consisting of carboxy and —OH;
• provided that the nitrogen to which R3 is attached is a quaternary nitrogen and is associated with a suitable counter anion X to provide a salt;
• and
• X is a suitable counter anion.

A compound of formula I

• wherein:
• R1 is 3,5-dimethoxy-4-hydroxyphenyl;
• R2 and R3 together with the nitrogen to which they are attached form a 4-10 membered ring heterocycle, wherein heterocycle is optionally substituted with one or more groups independently selected from the group consisting of carboxy, —OH, (C1-C6)alkoxycarbonyl, (C2-C6)alkanoyloxy and —C(═O)(C1-C6 alkyl), wherein any (C1-C6)alkoxycarbonyl and (C2-C6)alkanoyloxy is optionally substituted with one or more groups independently selected from the group consisting of halo, carboxy, —OH, —NRaRb and cyano;
• provided that the nitrogen to which R3 is attached is a quaternary nitrogen and is associated with a suitable counter anion X to provide a salt;
• each Ra and Rb is independently selected from the group consisting of H, (C1-C6)alkyl, and (C3-C6)cycloalkyl;
• or Ra and Rb together with the nitrogen to which they are attached form a 4-10 membered ring heterocycle;
• and
• X is a suitable counter anion.