Azido derivatives of cyclopentane heptanoic or heptenoic acid
AssigneeAllergan, Inc.
InventorMing F. Chan
Life of this patent
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Abstract
The present invention provides novel 2-aliphatic or arylaliphatic cyclopentane heptanoic and heptenoic acid derivatives including at least one azido substituent. In particular 2-aliphatic or arylaliphatic cyclopentane heptenyloic and cyclopentane heptanoic acids and esters thereof, substituted at the 3 and/or 5 position of the cyclopentane ring with radicals selected from the group consisting of hydroxy, azido and mixtures thereof, are disclosed. These azido compounds are useful as ocular hypotensives and are intermediates for the preparation of other compounds useful as ocular hypotensives.
Claims30
A method of treating ocular hypertension which comprises administering an effective amount of a derivative of cyclopentane heptanoic or heptenoic acid, 2-aliphatic or arylaliphatic represented by the formula I ##STR10## wherein A is an alkylene or alkenylene radical having from two to seven carbon atoms, which radical may be substituted with one or more hydroxy, oxo, alkyloxy or alkylcarboxy groups wherein the alkyl moiety has from 1 to 10 atoms, the dashed bonds represent a single bond or a double bond which can be in the cis or trans configuration, B is a methyl radical or a cycloalkyl radical having from three to seven carbon atoms, or an aryl radical selected from the group consisting of carbon aryl and monoheteroaryl radicals having from 4 to 10 carbon atoms wherein the heteroatom is selected from the group consisting of nitrogen, oxygen and sulfur atoms, any of the groups defining B may be substituted by radicals from the group consisting of halo, nitro, amino, thiol, hydroxy, alkyloxy and alkylcarboxy having from 1 to 10 atoms in the alkyl moiety , R.sub.1 and R.sub.2 are independently selected from the group consisting of hydroxy, 1-10 carbon ester derivatives thereof and azido radicals, provided that at least one of R.sub.1 and R.sub. 2 is an azido group and X is hydroxyl or 1 to 10 carbon alkyloxy and pharmaceutically-acceptable salts thereof.
A pharmaceutical composition for treating ocular hypertension which comprises an effective amount of a derivative of cyclopentane heptanoic or heptenoic acid, 2-aliphatic or arylaliphatic represented by the formula I ##STR15## wherein A is an alkylene or alkenylene radical having from two to seven carbon atoms, which radical may be substituted with one or more hydroxy, oxo, alkyloxy or alkylcarboxy groups wherein the alkyl moiety has from 1 to 10 atoms, the dashed bonds represent a single bond or a double bond which can be in the cis or trans configuration, B is a methyl radical or a cycloalkyl radical having from three to seven carbon atoms, or an aryl radical selected from the group consisting of aryl and monoheteroaryl radicals having from 4 to 10 carbon atoms wherein the heteroatom is selected from the group consisting of nitrogen, oxygen and sulfur atoms, any of the groups defining B may be substituted by radicals from the group consisting of halo, nitro, amino, thiol, hydroxy, alkyloxy and alkylcarboxy having from 1 to 10 atoms in the alkyl moiety , R.sub.1 and R.sub.2 are independently selected from the group consisting of hydroxy, 1-10 carbon ester derivatives thereof and azido radicals, provided that at least one of R.sub.1 and R.sub.2 is an azido group and X is hydroxyl or 1 to 10 carbon alkyloxy and pharmaceutically-acceptable salts thereof in combination with a non-toxic, pharmaceutically-acceptable vehicle.
A compound, useful for treating ocular hypertension, which comprises administering an effective amount of a derivative of cyclopentane heptanoic or heptenoic acid, 2-aliphatic or arylaliphatic represented by the formula I ##STR20## wherein A is an alkylene or alkenylene radical having from two to seven carbon atoms, which radical may be with one or more hydroxy, oxo, alkyloxy or alkylcarboxy groups, B is a methyl radical or a cycloalkyl radical having from three to seven carbon atoms, or an aryl radical selected from the group consisting of hydrocarbyl aryl and mono heteroaryl radicals having from 4 to 10 carbon atoms wherein the heteroatom is selected from the group consisting of nitrogen, oxygen and sulfur atoms and any of the groups defining B may be substituted by radicals from the group consisting of halo, nitro, amino, thiol, hydroxy, alkyloxy and alkylcarboxy having from 1 to 10 atoms in the alkyl moiety, R.sub.1 and R.sub.2 are independently selected from the group consisting of hydroxy, ester derivatives thereof and azido radicals, provided that at least one of R.sub.1 and R.sub.2 is an azido group and X is hydroxyl or 1 to 10 carbon alkyloxy.
Dependencies are inferred from the claim text.