Compounds for inhibiting the activity of SARS-COV-2 spike glycoprotein

A compound of formula (II):

• in which:
• X is selected from a group consisting of biguanidine, biguanidinium ion, biguanidinium dication, guanidine, guanidnium, amine, ammonium ion, aminoalkyl, alkylammonium ion, amide, urea, amino, and hydroxyl;
• Y is selected from a group consisting of methylene, methine, oxygen and amine;
• Z1-Z4 at each occurrence are independently selected from a group consisting of nitrogen and carbon atoms;
• R2 and R3 are independently selected from a group consisting of carboxylic acid, carboxylate ion, sulfonic acid, sulfonate ion, amide and sulfonamide;
• R4, R5, R6, and R7 at each occurrence are independently selected from the group consisting of hydrogen, halogen, amino, C1-12 alkylamino, C1-12 alkylammonium salts, alkoxy, hydroxyl, C6-24 aryl, C3-12 cycloalkyl, C1-12 alkyl, cyano and C3-18 heteroaryl;
• the alkyl, aryl, heteroaryl, amino, and alkylamino groups with respect to R4, R5, R6, and R7 may be unsubstituted;
• the alkylamino and alkylammonium salts with respect to R4, R5, R6, and R7 may be primary, secondary, or tertiary;
• R8 is selected from the group consisting of buta-1,3-diyne-1-sulfonamide, penta-2,4-diynamide, hydrogen, halogen, amino, C1-12 alkylamino, C1-12 alkylammonium salts, alkoxy, hydroxyl, C6-24 aryl, C3-12 cycloalkyl, C1-12 alkyl, cyano and C3-18 heteroaryl;
• the alkyl, aryl, heteroaryl, amino, and alkylamino groups with respect to R8 may be unsubstituted;
• the alkylamino and alkylammonium salts with respect to R8 may be primary, secondary, or tertiary;
• and
• R9-R11 at each occurrence are independently selected from a group consisting of is selected from the group consisting of hydrogen, halogen, amino, C1-12 alkylamino, C1-12 alkylammonium salts, alkoxy, hydroxyl, C6-24 aryl, C3-12 cycloalkyl, C1-12 alkyl, cyano, C3-18 heteroaryl, and hydroxyalkyl;
• the alkyl, aryl, heteroaryl, amino, and alkylamino groups may be unsubstituted;
• the alkylamino and alkylammonium salts with respect to R9-R11 may be primary, secondary, or tertiary.

A compound of formula (III):

• in which:
• X is selected from a group consisting of biguanidine, biguanidinium ion, biguanidinium dication, guanidine, guanidnium, amine, ammonium ion, aminoalkyl, alkylammonium ion, amide, urea, amino, and hydroxyl;
• Y is selected from a group consisting of methylene, methine, oxygen and amine;
• Z1-Z4 at each occurrence are independently selected from a group consisting of nitrogen and carbon atoms;
• R2 and R3 are independently selected from a group consisting of carboxylic acid, carboxylate ion, sulfonic acid, sulfonate ion, amide and sulfonamide;
• R4, R5, R6, and R7 at each occurrence are independently selected from the group consisting of hydrogen, halogen, amino, C1-12 alkylamino, C1-12 alkylammonium salts, alkoxy, hydroxyl, C6-24 aryl, C3-12 cycloalkyl, C1-12 alkyl, cyano and C3-18 heteroaryl;
• the alkyl, aryl, heteroaryl, amino, and alkylamino groups with respect to R4, R5, R6, and R7 may be unsubstituted;
• the alkylamino and alkylammonium salts with respect to R4, R5, R6, and R7 may be primary, secondary, or tertiary;
• R9-R11 at each occurrence are independently selected from a group consisting of is selected from the group consisting of hydrogen, halogen, amino, C1-12 alkylamino, C1-22 alkylammonium salts, alkoxy, hydroxyl, C6-24 aryl, C3-12 cycloalkyl, C1-12 alkyl, cyano, C3-18 heteroaryl, and hydroxyalkyl;
• the alkyl, aryl, heteroaryl, amino, and alkylamino groups may be unsubstituted;
• the alkylamino and alkylammonium salts with respect to R9-R11 may be primary, secondary, or tertiary;
• and
• R14 is selected from group consisting of amide and sulfonamide.