Water-soluble fluorinated sulfonamides as topical carbonic...

Details Water-soluble fluorinated sulfonamides as topical carbonic... Water-soluble fluorinated sulfonamides as topical carbonic...

C - Chemistry, Metallurgy

07

C

C07C 311/09 (2006.01) A61P 27/02 (2006.01)

Patent

CA 2361906

Improved water-soluble drugs which can inhibit carbonic anhydrase isozymes inside mammalian eyes are disclosed, for use in eyedrops by patients suffering from glaucoma or ocular hypertension. These compounds have a fluorinated (preferably perfluorinated) alkyl, aryl, or cycloalkyl group, coupled to an aromatic or heterocyclic ring with a pendant sulfonamide group. These new fluoro-sulfonamide compounds have several advantages over previously known CAI's used in eyedrops, such as dorzolamide and brinzolamide. These advantages include: (1) higher solubility in water, allowing fluoro-sulfonamides to be dissolved at desired concentrations in neutral aqueous solution without requiring potentially irritating acidifying or suspending agents; (2) ability to reduce intraocular pressure by more than twice as much as dorzolamide (e. g., 10.3 to 12.5 mm Hg in normal rabbits, compared to 4.1 for dorzolamide; 13.0 to 15.7 in glaucomatous rabbits, compared to 6.7 for dorzolamide); and, (3) substantially longer duration of action. Any of those results would be deemed important, in glaucoma treatments the fact that all three results were achieved simultaneously indicates that these new fluoro- sulfonamide drugs offer major improvements over the prior art.

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