FIELD: chemistry.
SUBSTANCE: present invention relates to novel aromatic sulphonamide derivatives, general formula 1 and pharmaceutically acceptable salts thereof, which are selective inhibitors of carbonic anhydrase II (CA II). Substituted sulphonamides correspond to general formula 1
,
where A is phenyl or thiophene; R1 is C1-C5alkyl, C-3C6cycloalkyl, -C(O)R3; provided that R1 is not methyl, when A is phenyl, R2 represents hydrogen; R3 is a 5-6 member heterocyclyl with one or two heteroatoms, selected from nitrogen or oxygen atoms; R2 is C1-C3alkyl, C1-C3alkoxy. Invention also relates to a method of producing compounds of general formula 1. Method involves two stages: a) sulphochlorination of corresponding oxazole derivative of general formula 5 (a-o) or 6 (a-j) with a mixture chlorosulphonic acid and thionyl chloride to produce intermediate sulphochlorides of formula 7 (a-o) or 8 (a-j), respectively, and b) with subsequent conversion of obtained sulphochlorides into primary sulphamides of formula 9 (b-o) or 10 (a-j) by reacting with ammonia according to following scheme
,
where
,
where R1 is C1-C5alkyl, C3-C6cycloalkyl; NR'Rʺ is a morpholine or pyrrolidine.
EFFECT: compounds can be used for treating glaucoma, in particular, open-angle glaucoma, and other diseases caused by high intraocular pressure, age-related macular degeneration, diabetic macular edema, diabetic retinopathy, hypertensive retinopathy and retinal vasculopathy mediated by activity of carbonic anhydrase II.
11 cl, 2 dwg, 2 tbl, 57 ex
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