US5354772A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Indole analogs of mevalonolactone and derivatives thereof
Assignee: Novartis Pharmaceuticals Corp
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Filing: 1993-11-24
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Granted: 1994-10-11
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Expires: 2013-11-24
Abstract
Abstract Compounds of the formula ##STR1## wherein one of R and R o is ##STR2## and the other is primary or secondary C 1-6 alkyl not containing an asymmetric carbon atom, C 3-6 cycloalkyl or phenyl-(CH 2 ) m --, wherein R 4 is hydrogen, C 1-3 alkyl, n-butyl, i-butyl, t-butyl, C 1-3 alkoxy, n-butoxy, i-butoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R 5 is hydrogen, C 1-3 alkyl, C 1-3 alkoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R 5a is hydrogen, C 1-2 alkyl, C 1-2 alkoxy, fluoro or chloro, and m is 1, 2 or 3, with the provisos that both R 5 and R 5a must be hydrogen when R 4 is hydrogen, R 5a must be hydrogen when R 5 is hydrogen, not more than one of R 4 and R 5 is trifluoromethyl, not more than one of R 4 and R 5 is phenoxy, and not more than one of R 4 and R 5 is benzyloxy, R 2 is hydrogen, C 1-3 alkyl, n-butyl, i-butyl, t-butyl, C 3-6 cycloalkyl, C 1-3 alkoxy, n-butoxy, i-butoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R 3 is hydrogen, C 1-3 alkyl, C 1-3 alkoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, with the provisos that R 3 must be hydrogen when R 2 is hydrogen, not more than one of R 2 and R 3 is trifluoromethyl, not more than one of R 2 and R 3 is phenoxy, and not more than one of R 2 and R 3 is benzyloxy, X is --(CH 2 ) n -- or --CH═CH--, wherein n is 0, 1, 2 or 3, and Z is ##STR3## wherein R 6 is hydrogen or C 1-3 alkyl, and R 7 is hydrogen, R 7b or M, wherein R 7b 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.
Inventors
- 👤 Faizulla G. Kathawala
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 00:21
CPC Classifications
C; C07; C07D; C07D405/00; C07D405/02; C07D405/06; C07D209/00; C07D209/02; C07D209/04; C07D209/10; C07D209/12; C07D209/18; C07D209/30; C07D209/42; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/553; C07F9/572; C07F9/5728
Claims Analysis
Total Claims: 32
Claim 1
Independent Claim
307 words
A compound of the formula ##STR223## wherein one of R and R o is and the other is ##STR224## and the other is primary or secondary C 1-6 alkyl not containing an asymmetric carbon atom, C 1-3 cycloalkyl or phenyl-(CH 2 ) m --, wherein R 4 is hydrogen, C 1-3 alkyl, n-butyl, i-butyl, t-butyl, C 1-3 alkoxy, n-butoxy, i-butoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R 5 is hydrogen, C 1-3 alkyl, C 1-3 alkoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R 5a is hydrogen, C 1-2 alkyl, C 1-2 alkoxy, fluoro, or chloro, and m is 1, 2 or 3, with the provisos that both R 5 and R 5a must be hydrogen when R 4 is hydrogen, R 5a must be hydrogen when R 5 is hydrogen, not more than one of R 4 and R 5 is trifluoromethyl, not more than one of R 4 and R 5 is phenoxy, and not more than one of R 4 and R 5 is benzyloxy, R 2 is hydrogen, C 1-3 alkyl, n-butyl, i-butyl, t-butyl, C 3-6 cycloalkyl, C 1-3 alkoxy, n-butoxy, i-butoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R 3 is hydrogen, C 1-3 alkyl, C 1-3 alkoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, with the provisos that R 3 must be hydrogen when R 2 is hydrogen, not more than one of R 2 and R 3 is trifluoromethyl, not more than one of R 2 and R 3 is phenoxy, and not more than one of R 2 and R 3 is benzyloxy, X is --(CH 2 ) n -- or --CH═CH--, wherein n is 0, 1, 2 or 3, and Z is ##STR225## wherein R 6 is hydrogen or C 1-3 alkyl, and R 7 is hydrogen, C 1-3 alkyl, n-butyl, i-butyl, t-butyl, benzyl, or M, wherein M is a cation.
Claim 2
Dependent Claim
307 words
A compound of the formula ##STR223## wherein one of R and R o is and the other is ##STR224## and the other is primary or secondary C 1-6 alkyl not containing an asymmetric carbon atom, C 1-3 cycloalkyl or phenyl-(CH 2 ) m --, wherein R 4 is hydrogen, C 1-3 alkyl, n-butyl, i-butyl, t-butyl, C 1-3 alkoxy, n-butoxy, i-butoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R 5 is hydrogen, C 1-3 alkyl, C 1-3 alkoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R 5a is hydrogen, C 1-2 alkyl, C 1-2 alkoxy, fluoro, or chloro, and m is 1, 2 or 3, with the provisos that both R 5 and R 5a must be hydrogen when R 4 is hydrogen, R 5a must be hydrogen when R 5 is hydrogen, not more than one of R 4 and R 5 is trifluoromethyl, not more than one of R 4 and R 5 is phenoxy, and not more than one of R 4 and R 5 is benzyloxy, R 2 is hydrogen, C 1-3 alkyl, n-butyl, i-butyl, t-butyl, C 3-6 cycloalkyl, C 1-3 alkoxy, n-butoxy, i-butoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R 3 is hydrogen, C 1-3 alkyl, C 1-3 alkoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, with the provisos that R 3 must be hydrogen when R 2 is hydrogen, not more than one of R 2 and R 3 is trifluoromethyl, not more than one of R 2 and R 3 is phenoxy, and not more than one of R 2 and R 3 is benzyloxy, X is --(CH 2 ) n -- or --CH═CH--, wherein n is 0, 1, 2 or 3, and Z is ##STR225## wherein R 6 is hydrogen or C 1-3 alkyl, and R 7 is hydrogen, C 1-3 alkyl, n-butyl, i-butyl, t-butyl, benzyl, or M, wherein M is a cation.
Claim 3
Dependent Claim
13 words
A compound according to claim 1 wherein M is a pharmaceutically acceptable cation.
Claim 4
Dependent Claim
294 words
A compound according to claim 2 having the formula ##STR226## wherein R 1 is primary or secondary C 1-3 alkyl not containing an asymmetric carbon atom, C 3-6 cycloalkyl or phenyl-(CH 2 ) m --, wherein m is 1, 2 or 3, R 2 is hydrogen, C 1-3 alkyl, n-butyl, i-butyl, t-butyl, C 3-6 cycloalkyl, C 1-3 alkoxy, n-butoxy, i-butoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R 3 is hydrogen, C 1-3 alkyl, C 1-3 alkoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, with the provisos that R 3 must be hydrogen when R 2 is hydrogen, not more than one of R 2 and R 3 is trifluoromethyl, not more than one of R 2 and R 3 is phenoxy, and not more than one of R 2 and R 3 is benzyloxy, R 4 is hydrogen, C 1-3 alkyl, n-butyl, i-butyl, t-butyl, C 1-3 alkoxy, n-butoxy, i-butoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R 5 is hydrogen, C 1-3 alkyl, C 1-3 alkoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R 5a is hydrogen, C 1-2 alkyl, C 1-2 alkoxy, fluoro or chloro, with the provisos that both R 5 and R 5a must be hydrogen when R 4 is hydrogen, R 5a must be hydrogen when R 5 is hydrogen, not more than one of R 4 and R 5 is trifluoromethyl, not more than one of R 4 and R 5 is phenoxy, and not more than one of R 4 and R 5 is benzyloxy, R 6 is hydrogen or Cl 1-3 alkyl, R 7 is hydrogen, C 1-3 alkyl, n-butyl, i-butyl, t-butyl, benzyl or M, wherein M is a pharmaceutically acceptable cation, and X is --(CH 2 ) n -- or --CH═CH--, wherein n is 0, 1, 2 or 3.
Claim 5
Dependent Claim
135 words
A compound according to claim 3 wherein R 1 is primary or secondary C 1-5 alkyl not containing an asymmetric carbon atom, R 2 is hydrogen or C 1-3 alkyl, R 3 is hydrogen or Cl 1-3 alkyl, with the proviso that R 3 must be hydrogen when R 2 is hydrogen, R 4 is hydrogen, C 1-2 alkyl, trifluoromethyl or fluoro, R 5 is hydrogen or methyl, R 5a is hydrogen or methyl with the proviso that both R 5 and R 5a must be hydrogen when R 4 is hydrogen and R 5 must be hydrogen when R 5 is hydrogen, R 6 is hydrogen or methyl, R 7 is hydrogen, C 1-2 alkyl or M, wherein M is a pharmaceutically acceptable cation, and X is --CH 2 CH 2 -- or --CH═CH--.
Claim 6
Dependent Claim
170 words
A compound according to claim 3 wherein R 1 is primary or secondary C 1-6 alkyl not containing an asymmetric carbon atom, R 2 is hydrogen, C 1-3 alkyl, C 1-3 alkoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R 3 is hydrogen, C 1-3 alkyl, C 1-2 alkoxy, fluoro or chloro, with the proviso that R 3 must be hydrogen when R 2 is hydrogen, R 4 is hydrogen, C 1-3 alkyl, C 1-3 alkoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R 5 is hydrogen, C 1-2 alkyl, C 1-2 alkoxy, fluoro or chloro, R 5a is hydrogen or methyl, with the provisos that both R 5 and R 5a must be hydrogen when R 4 is hydrogen and R 5a must be hydrogen when R 5 is hydrogen, R 6 is hydrogen or C 1-2 alkyl, R 7 is hydrogen, C 1-3 alkyl or M, wherein M is a pharmaceutically acceptable cation, and X is --(CH 2 ) m -- or ##STR227## wherein m is 1, 2 or 3.
Claim 7
Dependent Claim
133 words
A compound according to claim 5 wherein R 1 is C 1-3 alkyl, R 2 is hydrogen, C 1-3 alkyl, methoxy, fluoro, chloro or 4-, 5- or 6-benzyloxy, R 3 is hydrogen or C 1-3 alkyl, with the proviso that R 3 must be hydrogen when R 2 is hydrogen, R 4 is hydrogen, methyl, methoxy, fluoro or chloro, R 5 is hydrogen, methyl, methoxy, fluoro or chloro, R 5a is hydrogen or methyl, with the proviso that both R 5 and R 5a must be hydrogen when R 4 is hydrogen and R 5a must be hydrogen when R 5 is hydrogen, R 6 is hydrogen, R 7 is hydrogen, C 1-2 alkyl or M, wherein M is a pharmaceutically acceptable cation, and X is --CH 2 CH 2 -- or ##STR228##
Claim 8
Dependent Claim
17 words
A compound according to claim 6 having the formula ##STR229## wherein M.sup.⊕ is a pharmaceutically acceptable cation.
Claim 9
Dependent Claim
9 words
A compound to claim 7 in racemic erythro form.
Claim 10
Dependent Claim
10 words
The compound according to claim 7 having the formula ##STR230##
Claim 11
Dependent Claim
10 words
The compound according to claim 9 having the 3R,5S configuration.
Claim 12
Dependent Claim
10 words
The compound of the formula ##STR231## in racemic erythro form.
Claim 13
Dependent Claim
10 words
The compound of the formula ##STR231## in racemic erythro form.
Claim 14
Dependent Claim
274 words
A compound according to claim 2 having the formula ##STR232## wherein R 1 is primary or secondary C 1-6 alkyl not containing an asymmetric carbon atom, C 3-6 cycloalkyl or phenyl-(CH 2 ) m --, wherein m is 1, 2 or 3, R 2 is hydrogen, C 1-3 alkyl, n-butyl, i-butyl, t-butyl, C 3-6 cycloalkyl, C 1-3 alkoxy, n-butoxy, i-butoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R 3 is hydrogen, C 1-3 alkyl, C 1-3 alkoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, with the provisos that R 3 must be hydrogen when R 2 is hydrogen, not more than one of R 2 and R 3 is trifluoromethyl, not more than one of R 2 and R 3 is phenoxy, and not more than one of R 2 and R 3 is benzyloxy, R 4 is hydrogen, C 1-3 alkyl, n-butyl, i-butyl, t-butyl, C 1-3 alkoxy, n-butoxy, i-butoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R 5 is hydrogen, C 1-3 alkyl, C 1-3 alkoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R 5a is hydrogen, C 1-2 alkyl, C 1-2 alkoxy, fluoro or chloro, with the provisos that both R 5 and R 5a must be hydrogen when R 4 is hydrogen, R 5a must be hydrogen when R 5 is hydrogen, not more than one of R 4 and R 5 is trifluoromethyl, not more than one of R 4 and R 5 is phenoxy, and not more than one of R 4 and R 5 is benzyloxy, R 6 is hydrogen or C 1-3 alkyl, and X is --(CH 2 ) n -- or --CH═CH--, wherein n is 0, 1, 2 or 3.
Claim 15
Dependent Claim
148 words
A compound according to claim 12 wherein R 1 is primary or secondary C 1-6 alkyl not containing an asymmetric carbon atom, R 2 is hydrogen, C 1-3 alkyl, C 1-3 alkoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R 3 is hydrogen, C 1-3 alkyl, C 1-2 alkoxy, fluoro or chloro, with the proviso that R 3 must be hydrogen when R 2 is hydrogen, R 4 is hydrogen, C 1-3 alkyl, C 1-3 alkoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R 5 is hydrogen, C 1-2 alkyl, C 1-2 alkoxy, fluoro or chloro, R 5a is hydrogen or methyl, with the provisos that both R 5 and R 5a must be hydrogen when R 4 is hydrogen and R 5a must be hydrogen when R 5 is hydrogen, R 6 is hydrogen or C 1-2 alkyl, and X is ##STR233## wherein m is 1, 2 or 3.
Claim 16
Dependent Claim
294 words
A compound according to claim 2 having the formula ##STR234## wherein R 1 is primary or secondary C 1-6 alkyl not containing an asymmetric carbon atom, C 3-6 cycloalkyl or phenyl-(CH 2 ) m --, wherein m is 1, 2 or 3, R 2 is hydrogen, C 1-3 alkyl, n-butyl, i-butyl, t-butyl, C 3-6 cycloalkyl, C 1-3 alkoxy, n-butoxy, i-butoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R 3 is hydrogen, C 1-3 alkyl, C 1-3 alkoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, with the provisos that R 3 must be hydrogen when R 2 is hydrogen, not more than one of R 2 and R 3 is trifluoromethyl, not more than one of R 2 and R 3 is phenoxy, and not more than one of R 2 and R 3 is benzyloxy, R 4 is hydrogen, C 1-3 alkyl, n-butyl, i-butyl, t-butyl, C 1-3 alkoxy, n-butoxy, i-butoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R 5 is hydrogen, C 1-3 alkyl, C 1-3 alkoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R 5a is hydrogen, C 1-2 alkyl, C 1-2 alkoxy, fluoro or chloro, with the provisos that both R 5 and R 5a must be hydrogen when R 4 is hydrogen, R 5a must be hydrogen when R 5 is hydrogen, not more than one of R 4 and R 5 is trifluoromethyl, not more than one of R 4 and R 5 is phenoxy, and not more than one of R 4 and R 5 is benzyloxy, R 6 is hydrogen or C 1-3 alkyl, R 7 is hydrogen, C 1-3 alkyl, n-butyl, i-butyl, t-butyl, benzyl or M, wherein M is a pharmaceutically acceptable cation, and X is --(CH 2 ) n -- or --CH═CH--, wherein n is 0, 1, 2 or 3.
Claim 17
Dependent Claim
164 words
A compound according to claim 14 wherein R 1 is primary or secondary C 1-6 alkyl not containing an asymmetric carbon atom, R 2 is hydrogen, C 1-3 alkyl, C 1-3 alkoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R 3 is hydrogen, C 1-3 alkyl, C 1-2 alkoxy, fluoro or chloro, with the proviso that R 3 must be hydrogen when R 2 is hydrogen, R 4 is hydrogen, C 1-3 alkyl, C 1-3 alkoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R 5 is hydrogen, C 1-2 alkyl, C 1-2 alkoxy, fluoro or chloro, R 5a is hydrogen or methyl, with the provisos that both R 5 and R 5a must be hydrogen when R 4 is hydrogen and R 5a must be hydrogen when R 5 is hydrogen, R 6 is hydrogen or C 1-2 alkyl, R 7 is hydrogen, C 1-3 alkyl or M, wherein M is a pharmaceutically acceptable cation, and X is ##STR235## wherein m is 1, 2 or 3.
Claim 18
Dependent Claim
274 words
A compound according to claim 2 having the formula ##STR236## wherein R 1 is primary or secondary C 1-6 alkyl not containing an asymmetric carbon atom, C 3-6 cycloalkyl or phenyl-(CH 2 ) m --, wherein m is 1, 2 or 3, R 2 is hydrogen, C 1-3 alkyl, n-butyl, i-butyl, t-butyl, C 3-6 cycloalkyl, C 1-3 alkoxy, n-butoxy, i-butoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R 3 is hydrogen, C 1-3 alkyl C 1-3 alkoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, with the provisos that R 3 must be hydrogen when R 2 is hydrogen, not more than one of R 2 and R 3 is trifluoromethyl, not more than one of R 2 and R 3 is phenoxy, and not more than one of R 2 and R 3 is benzyloxy, R 4 is hydrogen, C 1-3 alkyl, n-butyl, i-butyl, t-butyl, C 1-3 alkoxy, n-butoxy, i-butoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R 5 is hydrogen, C 1-3 alkyl, C 1-3 alkoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R 5a is hydrogen, C 1-2 alkyl, C 1-2 alkoxy, fluoro or chloro, with the provisos that both R 5 and R 5a must be hydrogen when R 4 is hydrogen, R 5a must be hydrogen when R 5 is hydrogen, not more than one of R 4 and R 5 is trifluoromethyl, not more than one of R 4 and R 5 is phenoxy, and not more than one of R 4 and R 5 is benzyloxy, R 6 is hydrogen or C 1-3 alkyl, and X is --(CH 2 ) n -- or --CH═CH--, wherein n is 0, 1, 2 or 3.
Claim 19
Dependent Claim
149 words
A compound according to claim 16 wherein R 1 is primary or secondary C 1-6 alkyl not containing an asymmetric carbon atom, R 2 is hydrogen, C 1-3 alkyl, C 1-3 alkoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R 3 is hydrogen, C 1-3 alkyl, C 1-2 alkoxy, fluoro or chloro, with the proviso that R 3 must be hydrogen when R 2 is hydrogen, R 4 is hydrogen, C 1-3 alkyl, C 1-3 alkoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R 5 is hydrogen, C 1-2 alkyl, C 1-2 alkoxy, fluoro or chloro, R 5a is hydrogen or methyl, with the provisos that both R 5 and R 5a a must be hydrogen when R 4 is hydrogen and R 5a must be hydrogen when R 5 is hydrogen, R 6 is hydrogen or C 1-2 alkyl, and X is ##STR237## wherein m is 1, 2 or 3.
Claim 20
Dependent Claim
33 words
A pharmaceutical composition comprising an effective amount of a compound according to claim 2 and a pharmaceutically acceptable carrier, said effective amount being an amount sufficient to inhibit cholesterol biosynthesis in a mammal.
Claim 21
Dependent Claim
24 words
A pharmaceutical composition according to claim 18 wherein the compound is a compound of the formula ##STR238## wherein M.sup.⊕ is a pharmaceutically acceptable cation.
Claim 22
Dependent Claim
28 words
A pharmaceutical composition according to claim 19 wherein the compound is a compound of the formula ##STR239## wherein M.sup.⊕ is a pharmaceutically acceptable cation, in racemic erythro form.
Claim 23
Dependent Claim
21 words
A pharmaceutical composition according to claim 20 wherein the compound is the compound of the formula ##STR240## in racemic erythro form.
Claim 24
Dependent Claim
37 words
A method of inhibiting cholesterol biosynthesis comprising administering to a mammal in need of such treatment an effective amount of a compound according to claim 2, said effective amount being an amount effective for inhibiting cholesterol biosynthesis.
Claim 25
Dependent Claim
27 words
A method of inhibiting cholesterol biosynthesis according to claim 22 wherein the compound is a compound of the formula ##STR241## wherein M.sup.⊕ is a pharmaceutically acceptable cation.
Claim 26
Dependent Claim
31 words
A method of inhibiting cholesterol biosynthesis according to claim 23 wherein the compound is a compound of the formula ##STR242## wherein M.sup.⊕ is a pharmaceutically acceptable cation, in racemic erythro form.
Claim 27
Dependent Claim
24 words
A method of inhibiting cholesterol biosynthesis according to claim 24 wherein the compound is the compound of the formula ##STR243## in racemic erythro form.
Claim 28
Dependent Claim
37 words
A method of treating atherosclerosis comprising administering to a mammal in need of such treatment an effective amount of a compound according to claim 2, said effective amount being an amount effective for the treatment of atherosclerosis.
Claim 29
Dependent Claim
303 words
A method of treating atherosclerosis according to claim 26 wherein the compound is a compound of the formula ##STR244## wherein R 1 is primary or secondary C 1-6 alkyl not containing an asymmetric carbon atom, C 3-6 cycloalkyl or phenyl-(CH 2 ) m --, wherein m is 1, 2 or 3, R 2 is hydrogen, C 1-3 alkyl, n-butyl, i-butyl, t-butyl, C 3-6 cycloalkyl, C 1-3 alkoxy, n-butoxy, i-butoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R 3 is hydrogen, C 1-3 alkyl, C 1-3 alkoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, with the provisos that R 3 must be hydrogen when R 2 is hydrogen, not more than one of R 2 and R 3 is trifluoromethyl, not more than one of R 2 and R 3 is phenoxy, and not more than one of R 2 and R 3 is benzyloxy, R 4 is hydrogen, C 1-3 alkyl, n-butyl, i-butyl, t-butyl, C 1-3 alkoxy, n-butoxy, i-butoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R 5 is hydrogen, C 1-3 alkyl, C 1-3 alkoxy, trifluoromethyl, fluoro, chloro, phenoxy or benzyloxy, R 5a is hydrogen, C 1-2 alkyl, C 1-2 alkoxy, fluoro or chloro, with the provisos that both R 5 and R 5a must be hydrogen when R 4 is hydrogen, R 5a must be hydrogen when R 5 is hydrogen, not more than one of R 4 and R 5 is trifluoromethyl, not more than one of R 4 and R 5 is phenoxy, and not more than one of R 4 and R 5 is benzyloxy, R 6 is hydrogen or C 1-3 alkyl, R 7 is hydrogen, C 1-3 alkyl, n-butyl, i-butyl, t-butyl, benzyl or M, wherein M is a pharmaceutically acceptable cation, and X is --(CH 2 ) n -- or --CH═CH-- wherein n is 0, 1, 2 or 3.
Claim 30
Dependent Claim
26 words
A method of treating atherosclerosis according to claim 27 wherein the compound is a compound of the formula ##STR245## wherein M.sup.⊕ is a pharmaceutically acceptable cation.
Claim 31
Dependent Claim
30 words
A method of treating atherosclerosis according to claim 28 wherein the compound is a compound of the formula ##STR246## wherein M.sup.⊕ is a pharmaceutically acceptable cation, in racemic erythro form.
Claim 32
Dependent Claim
23 words
A method of treating atherosclerosis according to claim 29 wherein the compound is the compound of the formula ##STR247## in racemic erythro form.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1997-10-10 | 1998-04-11 | 1998-10-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2001-10-10 | 2002-04-11 | 2002-10-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2005-10-10 | 2006-04-11 | 2006-10-11 | $7700.00 | Window Closed / Lapsed |