Indole analogs of mevalonolactone and derivatives thereof
DC CAFCFirst Claim
1. A compound of the formula ##STR223## wherein one of R and Ro is and the other is ##STR224## and the other is primary or secondary C1-6 alkyl not containing an asymmetric carbon atom, C1-3 cycloalkyl or phenyl-(CH2)m --,wherein R4 is hydrogen, C1-3 alkyl, n-butyl, i-butyl, t-butyl, C1-3 alkoxy, n-butoxy, i-butoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy,R5 is hydrogen, C1-3 alkyl, C1-3 alkoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy,R5a is hydrogen, C1-2 alkyl, C1-2 alkoxy, fluoro, or chloro, andm is 1, 2 or 3, with the provisos that both R5 and R5a must be hydrogen when R4 is hydrogen, R5a must be hydrogen when R5 is hydrogen, not more than one of R4 and R5 is trifluoromethyl, not more than one of R4 and R5 is phenoxy, and not more than one of R4 and R5 is benzyloxy,R2 is hydrogen, C1-3 alkyl, n-butyl, i-butyl, t-butyl, C3-6 cycloalkyl, C1-3 alkoxy, n-butoxy, i-butoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy,R3 is hydrogen, C1-3 alkyl, C1-3 alkoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, with the provisos that R3 must be hydrogen when R2 is hydrogen, not more than one of R2 and R3 is trifluoromethyl, not more than one of R2 and R3 is phenoxy, and not more than one of R2 and R3 is benzyloxy,X is --(CH2)n -- or --CH═
- CH--, wherein n is 0, 1, 2 or 3, andZ is ##STR225## wherein R6 is hydrogen or C1-3 alkyl, and R7 is hydrogen, C1-3 alkyl, n-butyl, i-butyl, t-butyl, benzyl, or M, wherein M is a cation.
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Abstract
Compounds of the formula ##STR1## wherein one of R and Ro is ##STR2## and the other is primary or secondary C1-6 alkyl not containing an asymmetric carbon atom, C3-6 cycloalkyl or phenyl-(CH2)m --,
wherein
R4 is hydrogen, C1-3 alkyl, n-butyl, i-butyl, t-butyl, C1-3 alkoxy, n-butoxy, i-butoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy,
R5 is hydrogen, C1-3 alkyl, C1-3 alkoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy,
R5a is hydrogen, C1-2 alkyl, C1-2 alkoxy, fluoro or chloro, and
m is 1, 2 or 3, with the provisos that both R5 and R5a must be hydrogen when R4 is hydrogen, R5a must be hydrogen when R5 is hydrogen, not more than one of R4 and R5 is trifluoromethyl, not more than one of R4 and R5 is phenoxy, and not more than one of R4 and R5 is benzyloxy,
R2 is hydrogen, C1-3 alkyl, n-butyl, i-butyl, t-butyl, C3-6 cycloalkyl, C1-3 alkoxy, n-butoxy, i-butoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy,
R3 is hydrogen, C1-3 alkyl, C1-3 alkoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, with the provisos that R3 must be hydrogen when R2 is hydrogen, not more than one of R2 and R3 is trifluoromethyl, not more than one of R2 and R3 is phenoxy, and not more than one of R2 and R3 is benzyloxy,
X is --(CH2)n -- or --CH═CH--, wherein n is 0, 1, 2 or 3, and
Z is ##STR3## wherein R6 is hydrogen or C1-3 alkyl, and
R7 is hydrogen, R7b or M,
wherein
R7b is a physiologically acceptable and hydrolyzable ester group, and
M is a pharmaceutically acceptable cation, the use thereof for inhibiting cholesterol biosynthesis and lowering the blood cholesterol level, and therefore, in the treatment of hyperliopoproteinemia and atherosclerosis, pharmaceutical compositions comprising such compounds and processes for and intermediates in the synthesis of such compounds.
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Citations
30 Claims
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1. A compound of the formula ##STR223## wherein one of R and Ro is and the other is ##STR224## and the other is primary or secondary C1-6 alkyl not containing an asymmetric carbon atom, C1-3 cycloalkyl or phenyl-(CH2)m --,
wherein R4 is hydrogen, C1-3 alkyl, n-butyl, i-butyl, t-butyl, C1-3 alkoxy, n-butoxy, i-butoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R5 is hydrogen, C1-3 alkyl, C1-3 alkoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R5a is hydrogen, C1-2 alkyl, C1-2 alkoxy, fluoro, or chloro, and m is 1, 2 or 3, with the provisos that both R5 and R5a must be hydrogen when R4 is hydrogen, R5a must be hydrogen when R5 is hydrogen, not more than one of R4 and R5 is trifluoromethyl, not more than one of R4 and R5 is phenoxy, and not more than one of R4 and R5 is benzyloxy, R2 is hydrogen, C1-3 alkyl, n-butyl, i-butyl, t-butyl, C3-6 cycloalkyl, C1-3 alkoxy, n-butoxy, i-butoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R3 is hydrogen, C1-3 alkyl, C1-3 alkoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, with the provisos that R3 must be hydrogen when R2 is hydrogen, not more than one of R2 and R3 is trifluoromethyl, not more than one of R2 and R3 is phenoxy, and not more than one of R2 and R3 is benzyloxy, X is --(CH2)n -- or --CH═ - CH--, wherein n is 0, 1, 2 or 3, and
Z is ##STR225## wherein R6 is hydrogen or C1-3 alkyl, and R7 is hydrogen, C1-3 alkyl, n-butyl, i-butyl, t-butyl, benzyl, or M, wherein M is a cation. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30)
- CH--, wherein n is 0, 1, 2 or 3, and
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11. The compound of the formula ##STR231## in racemic erythro form.
Specification