US 6,160,129 A · Cyclopentane heptan(ene)oic acid, 2-heteroarylalkenyl derivatives as therapeutic agents

Abstract

The invention relates to the use of derivatives of F-type prostaglandins as ocular hypotensives. The compounds used in accordance with the invention are represented by the following formula I: ##STR1## wherein wavy line attachments indicate either the alpha (.alpha.) or beta (.beta.) configuration; hatched segments indicate .alpha. configuration; the solid triangle is used to indicate .beta. configuration; dashed bonds represent a double bond, or a single bond; R is a substituted heteroaryl radical having at least two pendant substituents selected from the group consisting of C.sub.1 to C.sub.6 alkyl; halogen; trifluoromethyl; COR.sup.1 ; COCF.sub.3 ; SO.sub.2 NR.sup.1 ; NO.sub.2 and CN or at least one cyano group; R.sup.1 is hydrogen or a lower alkyl radical having up to six carbon atoms, X is selected from the group consisting of --OR.sup.1 and --N(R.sup.1).sub.2 ; Y is .dbd.O or represents 2 hydrogen radicals and the 9, 11 or 15 lower alkyl esters thereof; provided, however, when said heteroaryl radical is a dichlorothienyl radical, the compound is not a 1-carboxylic acid or amide thereof. Certain of the compounds represented by Formula I are novel and comprise another aspect of the present invention.

Claims10

Dependent claims

An ophthalmic solution comprising a therapeutically effective amount of a cyclopentane heptane(ene)oic acid, 2 heteroarylalkenyl compound of formula III, or a pharmaceutically acceptable salt thereof, in admixture with a non-toxic, ophthalmically acceptable liquid vehicle, packaged in a container suitable for metered application ##STR48## wherein the hatched segments represent .alpha. bonds, the solid triangle represents a .beta. bond;

the dashed bond represents a double bond or a single bond;
R.sup.5 represents hydrogen or a lower alkyl radical having up to six carbon atoms;
X is selected from the group consisting of --OR.sup.1 and --N(R.sup.1).sub.2 ;
Y is .dbd.O or represents 2 hydrogen radicals;
R.sup.1 is hydrogen or a lower alkyl radical having up to six carbon atoms;
Z is selected from the group consisting of O and S, A is C when A is bonded directly to said alkenyl of said 2-heteroalkenyl of the compound and CR.sup.2 when A is not bonded directly to said alkenyl of said 2-hetero alkenyl of the compound;
R.sup.2, R.sup.3 and R.sup.4 are selected from the group consisting of hydrogen, halogen, cyano and lower alkyl having from 1 to 6 carbon atoms;
wherein at least two of the radicals represented by R.sup.2, R.sup.3 and R.sup.4 are halogen, cyano, or a lower alkyl radical having from 1 to 6 carbon atoms;
and the 9, 11, or 15 alkyl esters thereof.

6 more elements

Dependencies are inferred from the claim text.

Cyclopentane heptan(ene)oic acid, 2-heteroarylalkenyl derivatives as therapeutic agents

Life of this patent

Cyclopentane heptan(ene)oic acid, 2-heteroarylalkenyl derivatives as therapeutic agents

Life of this patent

Abstract

Claims10