Sulfamates as antiglaucoma agents
AssigneeA. H. Robins Company, Incorporated
InventorsYoung S. Lo, Joseph C. Nolan, Dwight A. Shamblee
Life of this patent
Estimating the term…
Abstract
Sulfamate esters of the formula (HO).sub.p --A--[OSO.sub.2 NR.sup.1 R.sup.2 ].sub.z where A is aryloxyalkyl, p is the number of unreacted hydroxy groups present on the alkyl moiety and may be zero, z is the number of --OS(O).sub.2 NR.sup.1 R.sup.2 groups attached to carbons of the alkyl moiety and is always at least one; R.sup.1 and R.sup.2 are selected from hydrogen, loweralkyl, carboxy, and the like are useful in treating glaucoma.
Claims20
A method for reducing intraocular pressure in a mammal, comprising administering to said mammal an effective amount of a compound having the formula:
- (HO).sub.p --A--[--OS(O).sub.2 NR.sup.1 R.sup.2 ].sub.z
- wherein
- A is aryloxy-alkyl, in which the aryl moiety is a substituted phenyl group of the formula:
- ##STR10## where X is hydrogen, halo, CF.sub.3, nitro-, --SO.sub.2 NR.sub.1 R.sub.2, loweralkoxy, hydroxy, amino, loweralkylamino, diloweralkylamino, methylcarbonylamino, loweralkyl, methyloxycarbonyl, 1H-imidazol-1-yl, 3-thiazole, 1-pyrrole, phenyl, 1H-triazol-1-yl, cyano, 2-loweralkyl-1H-imidazol-1-yl, 4-loweralkyl-1H-imidazol-1-yl, 4-phenyl-1H-imidazol-1-yl, --COOH, --COOM wherein M is a pharmaceutically acceptable metal cation, aryloxy or aroyl;
- Y is hydrogen, halo, loweralkoxy, hydroxy or loweralkyl;
- and
- W is hydrogen, loweralkoxy or loweralkyl;
- and said alkyl portion of A being substituted on one or more carbon atoms by the depicted sulfamyloxy group, where Z is the number of --OS(O).sub.2 NR.sup.1 R.sup.2 groups present on the alkyl moiety of A and is always at least one;
- p is the number of hydroxyl groups present on the alkyl moiety of A which have not been converted to --OS(O).sub.2 NR.sup.1 R.sup.2 groups, including zero;
- R.sup.1 is hydrogen or loweralkyl;
- R.sup.2 is hydrogen, loweralkyl, --CO.sub.2 R.sup.1, or --CO.sub.2 --M+ wherein M is defined above;
- and the pharmaceutically acceptable salts thereof when they can be formed and the optical isomers thereof, when they can be formed.
A pharmaceutical composition for lowering intraocular pressure in a mammal comprising an effective amount of a compound of the formula:
- (HO).sub.p --A--[--OS(O).sub.2 NR.sup.1 R.sup.2 ].sub.z
- wherein
- A is aryloxy-alkyl, in which the aryl moiety is a substituted phenyl group of the formula:
- ##STR11## where X is hydrogen, halo, CF.sub.3, nitro-, --SO.sub.2 NR.sub.1 R.sub.2, loweralkoxy, hydroxy, amino, loweralkylamino, diloweralkylamino, methylcarbonylamino, loweralkyl, methyloxycarbonyl, 1H-imidazol-1-yl, 3-thiazole, 1-pyrrole, phenyl, 1H-triazol-1-yl, cyano, 2-loweralkyl-1H-imidazol-1-yl, 4-loweralkyl-1H-imidazol-1-yl, 4-phenyl-1H-imidazol-1-yl, --COOH, --COOM wherein M is a pharmaceutically acceptable metal cation, aryloxy or aroyl;
- Y is hydrogen, halo, loweralkoxy, hydroxy or loweralkyl;
- and
- W is hydrogen, loweralkoxy or loweralkyl;
- and said alkyl portion of A being substituted on one or more carbon atoms by the
- depicted sulfamyloxy group, where Z is the number of --OS(O).sub.2 NR.sup.1 R.sup.2 groups present on the alkyl moiety of A and is always at least one;
- p is the number of hydroxyl groups present of the alkyl moiety of A which have not been converted to --OS(O).sub.2 NR.sup.1 R.sup.2 groups, including zero;
- R.sup.1 is hydrogen or loweralkyl;
- R.sup.2 is hydrogen, loweralkyl, --CO.sub.2 R.sup.1, or --CO.sub.2 M+wherein M is defined above;
- and the pharmaceutically acceptable salts thereof when they can be formed and the optical isomers thereof, when they can be formed, and a pharmaceutically acceptable carrier.
A pharmaceutical composition for topical administration to the eye of a mammal in need thereof comprising an effective amount of a water soluble compound having the formula:
- (HO).sub.p --[OSO.sub.2 NH.sub.2 ].sub.2
- wherein:
- A is aryloxy-alkyl in which the aryl moiety is a substituted phenyl group of the formula:
- ##STR12## wherein X is amino, loweralkylamino, diloweralkylamino, 1H-imidazol-1-yl, 4-loweralkyl-1H-imidazol-1-yl, 1H-triazol-1-yl, --COOH or --COOM wherein M is a pharmaceutically acceptable cation;
- Y is hydrogen, halo, loweralkoxy, hydroxy or loweralkyl;
- W is hydrogen, loweralkoxy or loweralkyl;
- and said alkyl portion of A being substituted on one or more carbon atoms by the depicted sulfamoyloxy group, where Z is the number of --OS(O).sub.2 NH.sub.2 groups present and is always at least one;
- p is the number of hydroxygroups present on the alkyl moiety of A which have not been converted to --OS(O).sub.2 NH.sub.2 groups, including zero;
- or a pharmaceutically acceptable salt thereof when they can be formed;
- the optical isomers thereof when they can be formed;
- and a pharmaceutically acceptable carrier.
A pharmaceutical composition comprised of a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound which is a pharmaceutically acceptable salt of sulfamic acid 2-[4(1H-imidazol-1-yl)phenoxy]ethyl ester.
A pharmaceutical composition comprised of a pharmaceutically acceptable carrier and a therapeutically effective amount of methylsulfamic acid 1-[(2-methoxyphenoxy)-methyl]-1,2-ethanediyl ester.
Dependencies are inferred from the claim text.