Cyclopentane heptanoic acid, 2-cycloalkyl or arylalkyl derivatives as therapeutic agents
DC CAFCFirst Claim
1. A method of treating ocular hypertension or glaucoma which comprises applying to the eye an amount sufficient to treat ocular hypertension or glaucoma of a compound represented by the formula V ##STR14## wherein X is a radical selected from the group consisting --OR4 and --N(R4)2 wherein R4 is selected from the group consisting of hydrogen, a lower alkyl radical having from one to six carbon atoms, ##STR15## wherein R5 is a lower alkyl radical having from one to six carbon atoms;
- Z is ═
O or represents 2 hydrogen radicals;
Y'"'"' is Cl or trifluoromethyl and the 9- and/or 11- and/or 15 esters, thereof.
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Abstract
The present invention provides cyclopentane heptanoic acid, 2-cycloalkyl or arylalkyl compounds, which may be substituted in the 1-position with amino, amido, ether or ester groups, e.g., a 1-OH cyclopentane heptanoic acid, 2-(cycloalkyl or arylalkyl) compound. The cyclopentane heptanoic acid, 2-(cycloalkyl or arylalkyl) compounds of the present invention are potent ocular hypotensives, and are particularly suitable for the management of glaucoma. Moreover, the cyclopentane heptanoic, 2-(cycloalkyl or arylalkyl) compounds of this invention are smooth muscle relaxants with broad application in systemic hypertensive and pulmonary diseases; smooth muscle relaxants with application in gastrointestinal disease, reproduction, fertility, incontinence, shock, etc.
279 Citations
20 Claims
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1. A method of treating ocular hypertension or glaucoma which comprises applying to the eye an amount sufficient to treat ocular hypertension or glaucoma of a compound represented by the formula V ##STR14## wherein X is a radical selected from the group consisting --OR4 and --N(R4)2 wherein R4 is selected from the group consisting of hydrogen, a lower alkyl radical having from one to six carbon atoms, ##STR15## wherein R5 is a lower alkyl radical having from one to six carbon atoms;
- Z is ═
O or represents 2 hydrogen radicals;
Y'"'"' is Cl or trifluoromethyl and the 9- and/or 11- and/or 15 esters, thereof. - View Dependent Claims (2, 3, 4)
- Z is ═
-
5. A method of treating ocular hypertension or glaucoma which comprises applying to the eye an amount sufficient to treat ocular hypertension or glaucoma of the formula ##STR16## wherein the dashed bonds represent a single or double bond which can be in the cis or trans configuration, X is a radical selected from the group consisting of --OR4 and --N(R4)2 wherein R4 is selected from the group consisting or hydrogen, a lower alkyl radical having from one to six carbon atoms, ##STR17## wherein R5 is a lower alkyl radical having from one to six carbon atoms;
- Z is ═
O or represents 2 hydrogen radicals;
R3 is ═
O, --OH or --O(CO)R6 ;
one of R1 and R2 is ═
O, --OH or a --O(CO)R6 group, and the other one is --OH or --O(CO)R6, or R1 is ═
O and R2 is H, wherein R6 is a saturated or unsaturated acyclic hydrocarbon group having from 1 to about 20 carbon atoms, or --(CH2)m R7 wherein m is 0-10, and R7 is cycloalkyl radical, having from three to seven carbon atoms, or a hydrocarbyl aryl or heteroaryl radical having from four to ten carbon atoms wherein the heteroatom is selected from the group consisting of nitrogen, oxygen and sulfur atoms;
or a pharmaceutically-acceptable salt thereof, provided however that when Z is ═
O, then X is not --OR4. - View Dependent Claims (6, 7, 8, 9, 10)
- Z is ═
-
11. A method of treating cardiovascular pulmonary-respiratory, gastrointestinal, reproductive and allergic diseases and shock in a human which comprises administering to said human an effective amount of a compound of formula I ##STR21## wherein the dashed bonds represent a single or double bond which can be in the cis or trans configuration, A is alkylene or alkenylene radical having from two to six carbon atoms, which radical may be interrupted by one or more oxide radicals and substituted with one or more hydroxy, oxo, alkyloxy or alkylcarboxy groups wherein said alkyl radical comprises from one to six carbon atoms, or an aryl radical selected from the group consisting of hydrocarbyl aryl and heteroaryl radicals having from four to ten carbon atoms wherein the heteroatom is selected from the group consisting of nitrogen, oxygen and sulfur atoms;
- B is a cycloalkyl radical having from three to seven carbon atoms, or an aryl radical, selected from the group consisting of hydrocarbyl aryl and heteroaryl radicals having from four to ten carbon atoms wherein the heteroatom is selected from the group consisting of nitrogen, oxygen and sulfur atoms;
X is a radical selected from the group consisting of --OR4 and --N(R4)2 wherein R4 is selected from the group consisting or hydrogen, a lower alkyl radical having from one to six carbon atoms, ##STR22## wherein R5 is a lower alkyl radical having from one to six carbon atoms;
Z is ═
O or represents 2 hydrogen radicals;
one of R1 and R2 is ═
O, --OH or a --O(CO)R6 group, and the other one is --OH or --O(CO)R6, or R1 is ═
O and R2 is H, wherein R6 is a saturated or unsaturated acyclic hydrocarbon group having from 1 to about 20 carbon atoms, or --(CH2)m R7 wherein m is 0-10, and R7 is cycloalkyl radical, having from three to seven carbon atoms, or a hydrocarbyl aryl or heteroaryl radical, as defined above, or a pharmaceutically-acceptable salt thereof, provided however that when B is not substituted with a pendant heteroatom-containing radical and Z is ═
O, then X is not --OR4. - View Dependent Claims (12, 13, 14, 15, 16, 17, 18, 19, 20)
- B is a cycloalkyl radical having from three to seven carbon atoms, or an aryl radical, selected from the group consisting of hydrocarbyl aryl and heteroaryl radicals having from four to ten carbon atoms wherein the heteroatom is selected from the group consisting of nitrogen, oxygen and sulfur atoms;
Specification