874899-97-5

Upstream product

• 16444-13-6 N-(4-formyl-1,3-thiazol-2-yl)acetamide 

Downstream Products

• 1197294-33-9 methyl {4-[2-(2-amino-1,3-thiazol-4-yl)ethyl]phenyl}acetate 
• 1442469-22-8 tert-butyl (4-{4-[2-(2-acetamido-1,3-thiazol-4-yl)ethyl]benzyl}-1H-imidazol-2-yl)carbamate 
• 1030892-01-3 N-{4-[2-(4-hydrazinocarbonylmethylphenyl)ethyl]-1,3-thiazol-2-yl}acetamide 

Relevant academic research and scientific papers

Novel 1H-imidazol-2-amine derivatives as potent and orally active vascular adhesion protein-1 (VAP-1) inhibitors for diabetic macular edema treatment

Novel thiazole derivatives were synthesized and evaluated as vascular adhesion protein-1 (VAP-1) inhibitors. Although we previously identified a compound (2) with potent VAP-1 inhibitory activity in rats, the human activity was relatively weak. Here, to improve the human VAP-1 inhibitory activity of compound 2, we first evaluated the structure-activity relationships of guanidine bioisosteres as simple small molecules and identified a 1H-benzimidazol-2-amine (5) with potent activity compared to phenylguanidine (1). Based on the structure of compound 5, we synthesized a highly potent VAP-1 inhibitor (37b; human IC50 = 0.019 μM, rat IC50 = 0.0051 μM). Orally administered compound 37b also markedly inhibited ocular permeability in streptozotocin-induced diabetic rats after oral administration, suggesting it is a promising compound for the treatment of diabetic macular edema.

BENZENE OR THIOPHENE DERIVATIVE AND USE THEREOF AS VAP-1 INHIBITOR

The present invention provides a novel benzene derivative or thiophene derivative useful as a VAP-1 inhibitor, or a medicament for the prophylaxis or treatment of a VAP-1 associated disease and the like, namely, a compound represented by the formula (I): wherein each symbol is as defined in the present specification, or a pharmaceutically acceptable salt thereof.

THIAZOLE DERIVATIVES HAVING VAP-1 INHIBITORY ACTIVITY

A compound of the formula (I), (II), (III) or (IV): wherein each symbol is as defined in the specification,or a pharmaceutically acceptable salt thereof useful as a vascular adhesion protein-1 (VAP-1) inhibitor, a pharmaceutical composition, a method for preventing or treating a VAP-1 associated disease, especially macular edema, which method includes administering an effective amount of the compound or a pharmaceutically acceptable salt thereof to a subject, and the like.

THIAZOLE DERIVATIVES HAVING VAP-1 INHIBITORY ACTIVITY

A compound of the formula (I): U-V-W-X-Y-Z (I) wherein U is lower alkyl; V is -CONH- or -NR1CO- wherein R1 is a hydrogen or lower alkyl; W is a bond or lower alkylene; X is a bivalent residue derived from optionally substituted thiazole; Y is a bond or lower alkylene; and Z is a group of the formula: or wherein R2 is a group of the formula: -A-B-D-E-F-G wherein A is a bond or lower alkylene; B is a bond, -NH- or ; D is a bond, -CS- or -CO-; E is a bond or -NH-; F is a bond, -CO-, -O- or -SO2-; and G is lower alkyl, optionally protected amino, -OH, phenyl, or ; and R3 is lower alkyl, provided that when Z is a group of the formula: , then G should not be amino, when Z is a group of the formula: , then G should not be , when Z is a group of the formula: and G is optionally protected amino, then D should be -CS-, or then A should be lower alkylene, B or E should be -NH- and F should be -CO-; or a pharmaceutically acceptable salt thereof useful as a vascular adhesion protein-1 (VAP-1) inhibitor as well as a pharmaceutical composition and a method for preventing or treating a VAP-1 associated disease, especially macular edema, which method includes administering an effective amount of the compound or a pharmaceutically acceptable salt thereof to a subject, and the like.