Cyclopentane(ene) heptenoic or heptanoic acids and derivatives thereof useful as therapeutic agents
AssigneeAllergan, Inc.
InventorRobert M. Burk
Life of this patent
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Abstract
The invention relates to 7-[5-hydroxy-2-(hydroxyhydrocarbyl or heteroatom-substituted hydroxy hydrocarbyl)-3-hydroxycyclopentyl(enyl)] heptanoic or heptenoic acids and derivatives of said acids, wherein one or more of said hydroxy groups are replaced by an ether group. The compounds of the present invention are potent ocular hypotensives, and are particularly suitable for the management of glaucoma.
Claims29
A method of treating ocular hypertension which comprises applying to the eye an amount sufficient to treat ocular hypertension of a compound of formula (I) ##STR4## wherein either the cyclopentane(ene) radical or the .alpha. or .omega. chain may be unsaturated;
- R is a hydrocarbyl radical comprising up to ten carbon atoms, said hydrocarbyl radical may be substituted with nitro, amino, thiol, hydroxy, alkoxy or halogen;
- R.sub.1, R.sub.2 and R.sub.3 are selected from the group consisting of hydroxy and hydrocarbyloxy wherein said hydrocarbyl radical comprises up to 20 carbon atoms;
- Y represents 2 hydrogen radicals or an oxo radical and X represents a hydroxyl a hydrocarbyloxy wherein the hydrocarbyl radical has up to 20 carbon atoms, an amino or a mono or dialkyl amino radical wherein the alkyl radical has from one to ten carbon atoms;
- provided, however, at least one of R.sub.1, R.sub.2 and R.sub.3 is a hydrocarbyloxy.
A pharmaceutical composition comprising a therapeutically effective amount of a compound of formula (I) ##STR8## wherein either the cyclopentane(ene) radical or the .alpha. or .omega. chain may be unsaturated;
- R is a hydrocarbyl radical comprising up to ten carbon atoms, said hydrocarbyl radical may be substituted with nitro, amino, thiol, hydroxy, alkoxy or halogen;
- R.sub.1, R.sub.2 and R.sub.3 are selected from the group consisting of hydroxy and hydrocarbyloxy, wherein said hydrocarbyl radical comprises up to 20 carbon atoms;
- Y represents 2 hydrogen radicals or an oxo radical and X represents a hydroxyl, a hydrocarbyloxy wherein the hydrocarbyl radical has up to 20 carbon atoms, an amino or a mono or dialkyl amino radical wherein the alkyl radical has from one to ten carbon atoms;
- provided, however, R.sub.2 is a hydrocarbyloxy.
An ophthalmic solution comprising a therapeutically effective amount of a compound of formula (I) ##STR9## wherein either the cyclopentane(ene) radical or the .alpha. or .omega. chain may be unsaturated;
- R is a hydrocarbyl radical comprising up to ten carbon atoms, said hydrocarbyl radical may be substituted with nitro, amino, thiol, hydroxy, alkoxy or halogen;
- R.sub.1, R.sub.2 and R.sub.3 are selected from the group consisting of hydroxy and hydrocarbyloxy wherein said hydrocarbyl radical comprises up to 20 carbon atoms, Y represents 2 hydrogen radicals or an oxo radical and X represents a hydroxyl, a hydrocarbyloxy wherein the hydrocarbyl radical has up to 20 carbon atoms, an amino or a mono or dialkyl amino radical wherein the alkyl radical has from one to ten carbon atoms;
- provided, however, at least one of R.sub.1, R.sub.2 and R.sub.3 is a hydrocarbyloxy.
A compound of the formula (I) ##STR13## wherein either cyclopentane(ene) radical or the .alpha. or .omega. chain may be unsaturated;
- R is a hydrocarbyl radical comprising up to ten carbon atoms, said hydrocarbyl radical may be substituted with nitro, amino, thiol, hydroxy, alkoxy or halogen;
- R.sub.1, R.sub.2 and R.sub.3 are selected from the group consisting of hydroxy and hydrocarbyloxy wherein said hydrocarbyl radical comprises up to 20 carbon atoms, Y represents 2 hydrogen radicals or an oxo radical and X represents a hydroxyl, a hydrocarbyloxy wherein the hydrocarbyl radical has up to 20 carbon atoms, an amino or a mono or dialkyl amino radical wherein the alkyl radical has from one to ten carbon atoms;
- provided, however, R.sub.2 is a hydrocarbyloxy.
A compound of the formula (I) ##STR14## wherein either cyclopentane(ene) radical or the .alpha. or .omega. chain may be unsaturated;
- R is a hydrocarbyl radical comprising up to ten carbon atoms, said hydrocarbyl radical may be substituted with oxygen, sulfur, nitrogen, phosphorus or halogen;
- R.sub.1, R.sub.2 and R.sub.3 are selected from the group consisting of hydroxy and hydrocarbyloxy wherein said hydrocarbyl radical comprises up to 20 carbon atoms;
- Y represents 2 hydrogen radicals or an oxo radical and X represents a hydroxyl, a hydrocarbyloxy wherein the hydrocarbyl radical has up to 20 carbon atoms, an amino or a mono or dialkyl amino radical wherein said alkyl radical has from one to ten carbon atoms;
- provided, however, at least one of R.sub.1, R.sub.2 and R.sub.3 is a hydrocarbyloxy and when Y represents an oxo radical X represents an amino or a mono or dialky amino radical.
Dependencies are inferred from the claim text.