Cyclopentane heptan(ene)oic acid, 2-heteroarylalk(en)yl derivatives as therapeutic agents

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

• wherein the hatched segments represent α bonds, the solid triangle represents a β bond, wavy line attachments indicate either the alpha (α) or bela (β) configuration;
• dashed bonds represent a double bond or a single bond, R is a substituted hetero aryl radical having at least two pendant substituents selected from the group consisting of C1 to C6 alkyl;
• halogen;
• trifluoromethyl;
• COR1;
• COCF3;
• SO2NR1;
• NO2 and CN or at least one cyano group;
• R1 is hydrogen or a 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, 11, or 15 alkyl esters thereof;
• provided, however, when said heteroaryl radical is a dichlorothienyl radical, said compound is not a 1-carboxylic acid or amide thereof 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
• wherein the hatched segments represent α bonds, the solid triangle represents β bond, wavy line attachments indicate either the alpha (α) or beta (β) configuration;
• dashed bonds represent a double bond or a single bond, R is a substituted hetero aryl radical having at least two pendant substituents selected from the group consisting of C1 C6 alkyl;
• halogen;
• trifluoromethyl;
• COR1, COCF3;
• SO2NR1;
• NO2 and CN or at least one cyano group;
• R1 is hydrogen or a 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, 11, or 15 alkyl esters thereof;
• provided, however, when said heteroaryl radical is a dichlorothienyl radical, said compound is not a 1-carboxylic acid or amide thereof.

The cyclopentane heptan(ene)oic acid, 2-heteroarylalk(en)yl compound represented by Formula II:

• wherein Z is selected from the group consisting of O and S, A is C when A is bonded directly to said alkenyl or alkyl of said heteroarylalk(en)yl compound and CR2 when A is not bonded directly to said alkenyl or alkyl of said heteroarylalk(en)yl compound;
• wherein at least two of the radicals represented by R2, R3 and R4 are selected from the group consisting of trifluoromethyl, COR1;
• COCF3;
• SO2NR1;
• NO2 and CN and R1 is hydrogen or a lower alkyl radical having up to six carbon atoms;
• and the 9, 11 or 15 alkyl esters thereof.