Antihypercholesterolemic compounds
DC
First Claim
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1. A compound of the formula:
- ##STR68## wherein R'"'"' is H or CH3 ;
R is(1) 1,1-dimethylpropyl,(2) C3-10 cycloalkyl,(3) C2-10 alkenyl,(4) C1-10 CF3 -substituted alkyl,(5) phenyl,(6) halophenyl,(7) phenyl-C1-3 alkyl,(8) substituted phenyl-C1-3 alkyl in which the substituent is halo, C1-3 alkyl or C1-3 alkoxy;
the dotted lines at X, Y and Z represent possible double bonds, said double bonds, when any are present, being either X and Z in combination or X, Y or Z alone;
or the corresponding dihydroxy acid of the formula;
##STR69## or a pharmaceutically acceptable salt of said acid, a C1-4 alkyl ester of said acid or a phenyl-, dimethylamino-, or acetylamino-substituted-C1-4 alkyl ester of said acid.
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Abstract
6(R)-[2-(8'"'"'-acyloxy-2'"'"'-methyl-6'"'"'-methyl (or hydrogen)-polyhydronaphthyl-1'"'"')-ethyl]-4 (R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-ones are prepared by acylation of the corresponding 8'"'"'-hydroxy compounds. The products are strong inhibitors of the biosynthesis of cholesterol.
507 Citations
18 Claims
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1. A compound of the formula:
- ##STR68## wherein R'"'"' is H or CH3 ;
R is(1) 1,1-dimethylpropyl, (2) C3-10 cycloalkyl, (3) C2-10 alkenyl, (4) C1-10 CF3 -substituted alkyl, (5) phenyl, (6) halophenyl, (7) phenyl-C1-3 alkyl, (8) substituted phenyl-C1-3 alkyl in which the substituent is halo, C1-3 alkyl or C1-3 alkoxy; the dotted lines at X, Y and Z represent possible double bonds, said double bonds, when any are present, being either X and Z in combination or X, Y or Z alone;
or the corresponding dihydroxy acid of the formula;
##STR69## or a pharmaceutically acceptable salt of said acid, a C1-4 alkyl ester of said acid or a phenyl-, dimethylamino-, or acetylamino-substituted-C1-4 alkyl ester of said acid. - View Dependent Claims (2, 3, 4, 5)
- ##STR68## wherein R'"'"' is H or CH3 ;
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6. A pharmaceutical antihypercholesterolemic composition comprising a pharmaceutical carrier and an antihypercholesterolemic effective amount of a compound of structural formula:
- ##STR70## in which R'"'"' is H or CH3 ;
R is(1) 1,1-dimethylpropyl, (2) C3-10 cycloalkyl, (3) C2-10 alkenyl, (4) C1-10 CF3 -substituted alkyl, (5) phenyl, (6) halophenyl, (7) phenyl-C1-3 alkyl, (8) substituted phenyl-C1-3 alkyl in which the substituent is halo, C1-3 alkyl or C1-3 alkoxy; the dotted lines at X, Y and Z represent possible double bonds, said double bonds, when any are present, being either X and Z in combination or X, Y or Z alone;
orthe corresponding dihydroxy acid of the formula;
##STR71## or a pharmaceutically acceptable salt of said acid, a C1-4 alkyl ester of said acid or a phenyl-, dimethylamino-, or acetylamino-substituted-C1-4 alkyl ester of said acid. - View Dependent Claims (7, 8, 9, 10)
- ##STR70## in which R'"'"' is H or CH3 ;
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11. A method of treating hypercholesterolemia in a patient in need of such treatment which comprises administration of an antihypercholesterolemic effective amount of a compound of structural formula:
- ##STR72## in which R'"'"' is H or CH3 ;
R is(1) 1,1-dimethylpropyl, (2) C3-10 cycloalkyl, (3) C2-10 alkenyl, (4) C1-10 CF3 -substituted alkyl, (5) phenyl, (6) halophenyl, (7) phenyl-C1-3 alkyl, (8) substituted phenyl-C1-3 alkyl in which the substituent is halo, C1-3 alkyl or C1-3 alkoxy; the dotted lines at X, Y and Z represent possible double bonds, said double bonds, when any are present, being either X and Z in combination or X, Y or Z alone;
orthe corresponding dihydroxy acid of the formula;
##STR73## or a pharmaceutically acceptable salt of said acid, a C1-4 alkyl ester of said acid or a phenyl-, dimethylamino-, or acetylamino-substituted-C1-4 alkyl ester of said acid. - View Dependent Claims (12, 13, 14, 15)
- ##STR72## in which R'"'"' is H or CH3 ;
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16. A compound of the formula:
- ##STR74## wherein R'"'"' is H or CH3 ;
R is(1) C3-10 cycloalkyl, (2) C2-10 alkenyl, (3) C1-10 CF3 -substituted alkyl, (4) phenyl, (5) halophenyl, (6) phenyl-C1-3 alkyl (7) substituted phenyl-C1-3 alkyl in which the substituent is halo, C1-3 alkyl or C1-3 alkoxy; the dotted lines at X, Y and Z represent possible double bonds, said double bonds, when any are present, being either X and Z in combination or X, Y or Z alone or the corresponding dihydroxy acid of the formula;
##STR75## or a pharmaceutically acceptable salt of said acid, a C1-4 alkyl ester of said acid or a phenyl-, dimethylamino-, or acetylamino-substituted-C1-4 alkyl ester of said acid.
- ##STR74## wherein R'"'"' is H or CH3 ;
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17. A pharmaceutical antihypercholesterolemic composition comprising a pharmaceutical carrier and an antihypercholesterolemic effective amount of a compound of structural formula:
- ##STR76## in which R'"'"' is H or CH3 ;
R is(1) C3-10 cycloalkyl, (2) C2-10 alkenyl, (3) C1-10 CF3 -substituted alkyl, (4) phenyl, (5) halophenyl, (6) phenyl-C1-3 alkyl, (7) substituted phenyl-C1-3 alkyl in which the substituent is halo, C1-3 alkyl or C1-3 alkoxy; the dotted lines at X, Y and Z represent possible double bonds, said double bonds, when any are present, being either X and Z in combination or X, Y or Z alone;
orthe corresponding dihydroxy acid of the formula;
##STR77## or a pharmaceutically acceptable salt of said acid, a C1-4 alkyl ester of said acid or a phenyl-, dimethylamino-, or acetylamino-substituted-C1-4 alkyl ester of said acid.
- ##STR76## in which R'"'"' is H or CH3 ;
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18. A method of treating hypercholesterolemia in a patient in need of such treatment which comprises administration of an antihypercholesterolemic effective amount of a compound of structural formula:
- ##STR78## in which R'"'"' is H or CH3 ;
R is(1) C3-10 cycloalkyl, (2) C2-10 alkenyl, (3) C1-10 CF3 -substituted alkyl, (4) phenyl, (5) halophenyl, (6) phenyl-C1-3 alkyl, (7) substituted phenyl-C1-3 alkyl in which the substituent is halo, C1-3 alkyl or C1-3 alkoxy; the dotted lines at X, Y and Z represent possible double bonds, said double bonds, when any are present, being either X and Z in combination or X, Y or Z alone;
orthe corresponding dihydroxy acid of the formula;
##STR79## or a pharmaceutically acceptable salt of said acid, a C1-4 alkyl ester of said acid or a phenyl-, dimethylamino-, or acetylamino-substituted C1-4 alkyl ester of said acid.
- ##STR78## in which R'"'"' is H or CH3 ;
Specification
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Litigation Data
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Current AssigneeMSD Techology L.P.
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Original AssigneeMerck & Co., Inc.
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InventorsSmith, Robert L., Hoffman, William F., Willard, Alvin K.
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Primary Examiner(s)Love, Ethel G.
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Application NumberUS06/217,640Time in Patent Office1,223 DaysField of Search260/343.5, 560/185, 560/119, 560/256, 560/107, 549/292, 562/501, 424/279US Class Current514/460CPC Class CodesC07D 309/30 Oxygen atoms, e.g. delta-la...
