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Generated: July 28, 2017

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Title: Non-acidic cyclopentane heptanoic acid, 2-cycloalkyl or arylalkyl derivatives as therapeutic agents
Abstract:The present invention provides cyclopentane heptanoic acid, 2-cycloalkyl or arylalkyl derivatives, substituted in the 1-position with halo, methyl, hydroxyl, nitro, amino, amido, azido, oxime, cyano, thiol, either or thioether groups, e.g., a 1-OH cyclopentane heptanoic acid, 2-(cycloalkyl or arylalkyl) derivatives. The cyclopentane heptanoic acid, 2-(cycloalkyl or arylalkyl) derivatives 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) derivatives 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.
Inventor(s): Woodward; David F. (El Toro, CA), Andrews; Steven W. (Irvine, CA), Burk; Robert M. (Irvine, CA), Garst; Michael E. (Newport Beach, CA)
Assignee: Allergan (Waco, TX)
Filing Date:Jan 11, 1995
Application Number:08/371,339
Claims:1. 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 ##STR11## wherein the dashed bonds represent a single or double bond which can be in the cis or trans configuration, A is an alkylene or alkenylene radical having from two to six carbon atoms, which radical may substituted with one or more hydroxy, oxo, alkyloxy or akylcarboxy groups, B is a cycloalkyl radical having from three to seven carbon atoms, or an aryl radical, selected from the group consisting of phenyl, thienyl, furanyl and pyridyl;

X is a radical selected from the group consisting of amino, radicals; one of R.sub.1 and R.sub.2 is .dbd.O,--OH or a --O(CO)R.sub.6 group, and the other one is --OH or --O(CO)R.sub.6, or R.sub.1 is .dbd.O and R.sub.2 is H, wherein R.sub.6 is a saturated or unsaturated acyclic hydrocarbon group having from 1 to about 20 carbon atoms, or --(CH.sub.2)m R.sub.7 wherein m is 0-10, and R.sub.7 is cycloalkyl radical, having from three to seven carbon atoms, or an aryl radical, as defined above, or a pharmaceutically-acceptable salt thereof.

2. A method of treating ocular hypertension which comprises applying to the eye an amount sufficient to treat ocular hypertension of a compound is a compound of formula II ##STR12## wherein y is 0 or 1 and either the .alpha. or .omega. chain may be unsaturated, Y is a radical selected from the group consisting of halo, nitro, amino, thiol, hydroxy, alkyloxy and alkylcarboxy, n is 0 or an integer of from 1 to 3 R.sub.3 and is .dbd.O,--OH or --O(CO)R.sub.6.

3. The method of claim 2 wherein said compound is a compound of formula III ##STR13## wherein hatched lines indicate .alpha. configuration and solid triangles indicate .beta. configuration.

4. The method of claim 3 wherein said compound is a compound of formula IV. ##STR14##

5. The method of claim 4 wherein said compound is a compound of formula V ##STR15## and the 9- and/or 11- and/or 15 esters, thereof.

6. The method of claim 2 wherein X is selected from the group consisting of

--N(R.sub.4)(R.sub.4), wherein R.sub.4 is hydrogen or C.sub.1 to C.sub.3 alkyl.

7. The method of claim 6 wherein R.sub.4 is hydrogen.

8. The method of claim 7 wherein said compound is:

cyclopentane hepteneamine-5-cis-2-(3-.alpha.hydroxy-5-phenyl-1-trans-pentyl)-3, 5 dihydroxy, [1.sub..alpha., 2.sub..beta., 3.sub..alpha., 5.sub..alpha. ].
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