Topically active carbonic anhydrase inhibitors. 2. Benzo[b]thiophenesulfonamide derivatives with ocular hypotensive activity

S L Graham; K L Shepard; P S Anderson; J J Baldwin; D B Best; M E Christy; M B Freedman; P Gautheron; C N Habecker; J M Hoffman

doi:10.1021/jm00132a009

Topically active carbonic anhydrase inhibitors. 2. Benzo[b]thiophenesulfonamide derivatives with ocular hypotensive activity

J Med Chem. 1989 Dec;32(12):2548-54. doi: 10.1021/jm00132a009.

Authors

S L Graham¹, K L Shepard, P S Anderson, J J Baldwin, D B Best, M E Christy, M B Freedman, P Gautheron, C N Habecker, J M Hoffman, et al.

Affiliation

¹ Merck Sharp & Dohme Research Laboratories, West Point, Pennsylvania 19486.

PMID: 2585443
DOI: 10.1021/jm00132a009

Abstract

Derivatives of benzo[b]thiophene-2-sulfonamide were prepared to investigate their potential utility as topically active inhibitors of ocular carbonic anhydrase. Such an agent would be useful in the treatment of glaucoma. Among the compounds described are 6-hydroxybenzo[b]thiophene-2-sulfonamide (16) and its acetate ester (23), which are among the most potent ocular hypotensive agents in this class, as assessed in the alpha-chymotrypsinized rabbit. These compounds were selected for clinical evaluation.

MeSH terms

Animals
Carbonic Anhydrase Inhibitors / chemical synthesis
Carbonic Anhydrase Inhibitors / therapeutic use*
Chemical Phenomena
Chemistry
Glaucoma / drug therapy*
Guinea Pigs
Intraocular Pressure / drug effects
Ocular Hypertension / drug therapy*
Rabbits
Skin / drug effects
Sulfonamides / chemical synthesis
Sulfonamides / therapeutic use*
Thiophenes / chemical synthesis
Thiophenes / therapeutic use*

Substances

Carbonic Anhydrase Inhibitors
Sulfonamides
Thiophenes
L 650719
6-hydroxybenzo(b)thiophene-2-sulfonamide acetate ester