Cyclopentane heptan(ene)oic acid, 2-thiocarbamoyloxy and 2-carbamoyloxy compounds as therapeutic agents

An ophthalmic solution comprising a therapeutically effective amount of a compound of formula I:

• 10
• wherein a wavy segments indicate either the alpha (α) or beta (β) configuration;
• the dashed bond represents a double bond or a single bond;
• Ar is selected from the group consisting of aryl or heteroaryl radicals having from 4 to 10 carbon atoms and substituted derivatives of said aryl and heteroaryl radicals;
• n is 0 or an integer of from 1 to 4;
• x and y are 1 or 0, provided that when x is 1, y is 0 and when x is 0, y is 1;
• R1 is hydrogen or a lower alkyl radical or a substituted lower alkyl radical having up to six carbon atoms;
• X is selected from the group consisting of —OR1 and —N(R1)2;
• Y is ═O or represents 2 hydrogen radicals, and the 9 and/or 11 esters thereof and/or the pharmaceutically acceptable salts of said compounds and/or esters, or a pharmaceutically acceptable salt thereof, in admixture with a non-toxic, ophthalmically acceptable liquid vehicle, packaged in a container suitable for metered application.

A pharmaceutical product, comprising a container adapted to dispense the contents of said container in metered form;

• and an ophthalmic solution in said container comprising a compound of formula I:
• 12
• wherein a wavy segments indicate either the alpha (α) or beta (β) configuration;
• the dashed bond represents a double bond or a single bond;
• Ar is selected from the group consisting of aryl or heteroaryl radicals having from 4 to 10 carbon atoms and substituted derivatives of said aryl and heteroaryl radicals;
• n is 0 or an integer of from 1 to 4;
• x and y are 1 or 0, provided that when x is 1, y is 0 and when x is 0, y is 1;
• R1 is hydrogen or a lower alkyl radical or a substituted lower alkyl radical having up to six carbon atoms;
• X is selected from the group consisting of —OR1 and —N(R1)2;
• Y is ═O or represents 2 hydrogen radicals, and the 9 and/or 11 esters thereof and/or the pharmaceutically acceptable salts of said compounds and/or esters, or a pharmaceutically acceptable salt thereof, in admixture with a non-toxic, ophthalmically acceptable liquid vehicle.

The product of claim 13 wherein said compound is a compound of Formula III:

• 13
• wherein n is 0 or 1, 2 or 4;
• hatched lines at position C-8, C-9 and C-11 indicate the α orientation;
• and the triangle at position C-12 represents the β orientation.

The compound represented by Formula I:

• 14
• wherein a wavy segments indicate either the alpha (α) or beta (β) configuration;
• the dashed bond represents a double bond or a single bond;
• Ar is a heteroaryl radical selected from the group consisting of thienyl and furyl radicals and substituted derivatives thereof;
• n is 0 or an integer of from 1 to 4;
• x is 1 and y is 0;
• R1 is hydrogen or a lower alkyl radical or a substituted lower alkyl radical having up to six carbon atoms wherein the substituent on the lower alkyl or heteroaryl radical is selected from the group consisting of lower alkyl, hydroxy, lower alkyloxy, halogen, trifluoromethyl (CF3), COR1, COCF3, SO2NR1, SO2NH2, NO2 and CN.;
• X is selected from the group consisting of —OR1 and —N(R1)2;
• Y is ═O or represents 2 hydrogen radicals, and the 9 and/or 11 esters thereof and/or the pharmaceutically acceptable salts of said compounds and/or esters.