Calixpyrrole compounds and creatinine-selective electrodes comprising them

A compound of formula (Ia), or alternatively (Ib) or alternatively (Ic), or any of the stereoisomers of (Ia), (Ib) or (Ic)

• wherein
• R1 is a monoradical selected from the group consisting of hydrogen;
• (C1-C20)alkyl;
• (C3-C20)alkenyl;
• (C3-C20)alkynyl;
• (C 1-C6)alkyl-O—;
• (C 1-C20)haloalkyl;
• (C6-C20)aryl;
• (C6-C20)aryl substituted with one or more radicals independently selected from (C1-C20)alkyl, (C1-C6)alkyl-O—, (C1-C6)haloalkyl, halogen, cyano, and nitro;
• (C6-C20)heteroaryl;
• and (C6-C20)heteroaryl substituted with one or more radicals independently selected from (C1-C20)alkyl, (C1-C6)alkyl-O—, (C1-C6)haloalkyl, halogen, cyano, and nitro;
• R2, and R2′ are monoradicals each one being independently selected from the group consisting of hydrogen, (C1-C20)alkyl, (C1-C6)alkyl-O—, (C1-C6)haloalkyl, halogen, cyano, and nitro;
• and
• Z1 to Z4 are diradicals of formula (III)
• wherein Al and A2 are independently selected from the group consisting of —O—and —NR3—, wherein R3 is selected from the group consisting of hydrogen and (C1-C20)alkyl;
• and
• G is a diradical selected from the group consisting of —NH2, —P(═S)(R5), —S(═O)2—, (C1-C6)alkyl, —S(═O)—, —C(═O)—, —P(═O)(R4)—, —P(═O)(NR6R7)— and —P(═O)(OR4);
• R4 and R5 are monoradicals independently selected from the group consisting of (C1-C20)alkyl;
• (C3-C8)cycloalkyl;
• (C2-C20)alkenyl;
• (C3-C20)cycloalkyl;
• (C 1-C20)haloalkyl;
• (C1-C20)alkyl-O—;
• (C6-C20)aryl;
• (C6-C20)heteroaryl;
• (C6-C20)aryl substituted with one or more radicals independently selected from (C1-C20)alkyl, (C1-C6)haloalkyl, (C1-C6)alkyl-O —, halogen, cyano, nitro;
• and (C6-C20)heteroaryl substituted with one or more radicals independently selected from (C1-C20)alkyl, (C1-C6)alkyl-O—, (C1-C6)haloalkyl, halogen, cyano, and nitro;
• Y1 to Y4 are triradicals each one independently selected from the group consisting of (C1-C8)alkyl;
• (C3-C7)cycloalkyl;
• (C6-C20)aryl;
• (C6-C20)aryl substituted with one or more radicals independently selected from the group consisting of:
• (C1-C20)alkyl, (C1-C6)alkyl-O—, (C1-C6)haloalkyl, halogen, cyano, and nitro;
• (C6-C20)heteroaryl;
• and (C6-C20)heteroaryl substituted with one or more radicals independently selected from the group consisting of:
• (C1-C20)alkyl, (C1-C6)alkyl-O—, (C1-C6)haloalkyl, halogen, cyano, and nitro;
• R6 and R7 are monoradicals independently selected from the group consisting of—H and (C1-C20)alkyl;
• FG1 and FG2 are monoradicals independently selected from the group consisting of H, OH, and NHR8 wherein R8 is a radical selected from the group consisting of hydrogen and (C1-C20)alkyl;
• wherein:
• (C6-C20)aryl represents a ring system from 6 to 20 carbon atoms, the system comprising from 1 to 3 rings, where each one of the rings forming the ring system:
• is saturated, partially unsaturated, or aromatic;
• and is isolated, partially fused or totally fused;
• (C6-C20)heteroaryl represents a C—radical of a ring system from 6 to 20 members, the system comprising from 1 to 3 rings, wherein at least one of the rings contains from one to four heteroatoms independently selected from O, S and N, and wherein each one of the rings forming the ring system:
• is saturated, partially unsaturated or aromatic;
• and is isolated, partially fused or totally fused;
• and
• (C3-C20)cycloalkyl refers to a saturated carbocyclic ring containing from 3 to 7 carbon atoms;
• provided that the compound of formula (Ib) is other than a compound of formula (IV) or (V) or stereoisomers thereof, and provided that the compound of formula (Ic) is other than a compound of formula (VI):
• wherein R9 is C12H23.