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Claims for Patent: 4,681,893

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Claims for Patent: 4,681,893

Title: Trans-6-[2-(3- or 4-carboxamido-substituted pyrrol-1-yl)alkyl]-4-hydroxypyran-2-one inhibitors of cholesterol synthesis
Abstract:Certain trans-6-[2-(3- or 4-carboxamido-substituted pyrrol-1-yl)alkyl]-4-hydroxypyran-2-ones and the corresponding ring-opened acids derived therefrom which are potent inhibitors of the enzyme 3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMG CoA reductase and are thus useful hypolipidemic or hypocholesterolemic agents. Pharmaceutical compositions containing such compounds, and a method of inhibiting the biosynthesis of cholesterol employing such pharmaceutical compositions are also disclosed.
Inventor(s): Roth; Bruce D. (Ann Arbor, MI)
Assignee: Warner-Lambert Company (Morris Plains, NJ)
Application Number:06/868,867
Patent Claims: 1. A compound of structural formula I ##STR17## wherein X is --CH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 --, or --CH.sub.2 CH(CH.sub.3)--;

R.sub.1 is

1-naphthyl;

2-naphthyl;

cyclohexyl;

norbornenyl;

phenyl;

phenyl substituted with

fluorine,

chlorine,

bromine,

hydroxyl,

trifluoromethyl,

alkyl of from one to four carbon atoms,

alkoxy of from one to four carbon atoms, or

alkanoyloxy of from two to eight carbon atoms;

either of R.sub.2 or R.sub.3 is --CONR.sub.5 R.sub.6 where R.sub.5 and R.sub.6 are independently

hydrogen;

alkyl of from one to six carbon atoms;

phenyl;

phenyl substituted with

fluorine,

chlorine,

bromine,

cyano,

trifluoromethyl, or

carboalkoxy of from three to eight carbon atoms;

and the other of R.sub.2 or R.sub.3 is

hydrogen;

alkyl of from one to six carbon atoms;

cyclopropyl;

cyclobutyl;

cyclopentyl;

cyclohexyl;

phenyl; or

phenyl substituted with

fluorine,

chlorine,

bromine,

hydroxyl,

trifluoromethyl,

alkyl of from one to four carbon atoms,

alkoxy of from one to four carbon atoms, or

alkanoyloxy of from two to eight carbon atoms;

R.sub.4 is

alkyl of from one to six carbon atoms;

cyclopropyl;

cyclobutyl;

cyclopentyl;

cyclohexyl; or

trifluoromethyl;

or a hydroxy acid or pharmaceutically acceptable salts thereof, corresponding to the opened lactone ring of the compounds of structural formula I above.

2. A compound as defined by claim 1 wherein X is --CH.sub.2 CH.sub.2 --.

3. A compound as defined by claim 2 wherein R.sub.1 is phenyl; or phenyl substituted with fluorine, chlorine, bromine, hydroxyl; trifluoromethyl; alkyl of from one to four carbon atoms, alkoxy of from one to four carbon atoms, or alkanoyloxy of from two to eight carbon atoms.

4. A compound as defined by claim 2 wherein R.sub.4 is alkyl of from one to six carbon atoms.

5. A compound as defined by claim 1 having the name trans-(.+-.)-5-(4-fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl-1-[2-(tetra hydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1H-pyrrole-3-carboxamide.

6. A compound as defined by claim 1 having the name trans-2-(4-fluorophenyl)-N,4-diphenyl-1-[2-(tetrahydro-4-hydroxy-6-oxo-2H- pyran-2-yl)ethyl]-5-trifluoromethyl-1H-pyrrole-3-carboxamide.

7. A compound as defined by claim 1 having the name trans-5-(4-fluorophenyl)-N,4-diphenyl-1-[2-(tetrahydro-4-hydroxy-6-oxo-2H- pyran-2-yl)ethyl]-2-trifluoromethyl-1H-pyrrole-3-carboxamide.

8. A pharmaceutical composition, useful as a hypocholesterolemic agent, comprising a hypocholesterolemic effective amount of a compound in accordance with claim 1 in combination with a pharmaceutically acceptable carrier.

9. A method of inhibiting cholesterol biosynthesis in a patient in need of such treatment by administering a pharmaceutical composition as defined by claim 8.
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