US5102907A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Novel squalene synthetase inhibitors
Assignee: Merck and Co Inc
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Filing: 1990-09-13
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Granted: 1992-04-07
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Expires: 2010-09-13
Abstract
Abstract This invention relates to compounds of structural formula (I): <IMAGE> (I) +TR <IMAGE> which are squalene synthetase inhibitors and thus useful as cholesterol lowering agents.
Inventors
- 👤 James D. Bergstrom
- 👤 Claude Dufresne
- 👤 Leeyuan Huang
- 👤 Mary Nallin
- 👤 Janet C. Onishi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 09:54
CPC Classifications
C; C07; C07D; C07D493/00; C07D493/02; C07D493/08
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
65 words
A compound of structural formula (I) ##STR6## wherein Z 1 Z 2 and Z 3 are each independently selected from a) H; b) C 1-5 alkyl; c) C 1-5 alkyl substituted with a member of the group consisting of i) phenyl, ii) phenyl substituted with methyl, methoxy, halogen (Cl, Br, I, F) or hydroxy; or a pharmaceutically acceptable salt of a compound of formula (I).
Claim 2
Dependent Claim
65 words
A compound of structural formula (I) ##STR6## wherein Z 1 Z 2 and Z 3 are each independently selected from a) H; b) C 1-5 alkyl; c) C 1-5 alkyl substituted with a member of the group consisting of i) phenyl, ii) phenyl substituted with methyl, methoxy, halogen (Cl, Br, I, F) or hydroxy; or a pharmaceutically acceptable salt of a compound of formula (I).
Claim 3
Dependent Claim
21 words
A compound of claim 1 wherein the stereochemical configuration of structural formula (I) is selected from the group consisting of: ##STR7##
Claim 4
Dependent Claim
21 words
A compound of claim 2 wherein the stereochemical configuration within structural formula (I) is selected from the group consisting of: ##STR8##
Claim 5
Dependent Claim
21 words
A compound of claim 3 wherein the stereochemical configuration of structural formula (I) is selected from the group consisting of: ##STR9##
Claim 6
Dependent Claim
24 words
A compound of claim 4 in which Z 1 , Z 2 and Z 3 are each hydrogen or a pharmaceutically acceptable salt thereof.
Claim 7
Dependent Claim
18 words
A compound of claim 4 in which Z 1 , Z 2 and Z 3 are each methyl.
Claim 8
Dependent Claim
8 words
A compound of claim 1 which is: ##STR10##
Claim 9
Dependent Claim
145 words
A compound of molecular formula C 40 H 50 O 14 and molecular weight 754 characterized by the (a) 13 C NMR chemical shifts, as measured in CD 3 OD at 22° C.: 173.06, 173.04, 172.43, 170.14, 168.46, 143.84, 141.88, 138.78, 130.15 (2×), 129.36 (2×), 129.24 (4×), 127.53, 126.89, 126.61, 107.17, 90.94, 82.15, 81.11, 78.10, 76.57, 75.56, 40.46, 39.62, 37.77, 37.56, 36.87, 36.21, 35.34, 32.43, 30.44, 28.75, 21.25, 21.13, 20.08, 14.32 ppm. (b) 1 H NMR chemical shifts, as measured in CD 3 OD at 22° C.: 7.22 (m, 4H), 7.13 (m, 6H), 6.23 (d, 1.8), 5.36 (m, 2H), 5.24 (s), 4.88 (q, 3.9), 4.03 (d, 1.8), 2.73 (dd, 13.3, 5.6 Hz), 2.54 (t, 7.6, 2H), 2.3 (m, 5H), 2.04 (s, 3H), 2.04 (m, 2H), 1.89 (br t, 7.0, 2H), 1.6 (m, 5H), 1.27 (m, 2H), 0.93 (d, 6.8, 3H), 0.86 (d, 6.8, 3H), ppm.
Claim 10
Dependent Claim
145 words
A compound of molecular formula C 40 H 50 O 14 and molecular weight 754 characterized by the (a) 13 C NMR chemical shifts, as measured in CD 3 OD at 22° C.: 173.06, 173.04, 172.43, 170.14, 168.46, 143.84, 141.88, 138.78, 130.15 (2×), 129.36 (2×), 129.24 (4×), 127.53, 126.89, 126.61, 107.17, 90.94, 82.15, 81.11, 78.10, 76.57, 75.56, 40.46, 39.62, 37.77, 37.56, 36.87, 36.21, 35.34, 32.43, 30.44, 28.75, 21.25, 21.13, 20.08, 14.32 ppm. (b) 1 H NMR chemical shifts, as measured in CD 3 OD at 22° C.: 7.22 (m, 4H), 7.13 (m, 6H), 6.23 (d, 1.8), 5.36 (m, 2H), 5.24 (s), 4.88 (q, 3.9), 4.03 (d, 1.8), 2.73 (dd, 13.3, 5.6 Hz), 2.54 (t, 7.6, 2H), 2.3 (m, 5H), 2.04 (s, 3H), 2.04 (m, 2H), 1.89 (br t, 7.0, 2H), 1.6 (m, 5H), 1.27 (m, 2H), 0.93 (d, 6.8, 3H), 0.86 (d, 6.8, 3H), ppm.
Claim 11
Dependent Claim
20 words
A pharmaceutical composition comprising a nontoxic anti-cholesterolemically effective amount of a compound of claim 1 and a pharmaceutically acceptable carrier.
Claim 12
Dependent Claim
18 words
A composition of claim 9 wherein the therapeutically effective compound is selected from the group consisting of: ##STR11##
Claim 13
Dependent Claim
27 words
A method of treating hypercholesterolemia comprising the administration to a subject in need of such treatment a nontoxic therapeutically effective amount of a compound of claim 1.
Claim 14
Dependent Claim
18 words
A method of claim 11 wherein the therapeutically effective compound is selected from the group consisting of: ##STR12##
References Cited (Backward Citations)
EP0045631A2
Cited
US4871721A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1995-04-07 | 1995-10-07 | 1996-04-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-04-07 | 1999-10-07 | 2000-04-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-04-07 | 2003-10-07 | 2004-04-07 | $7700.00 | Window Closed / Lapsed |