Patent US5482950A successfully refreshed from Google Patents.
US5482950A
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Methods for lowering serum cholesterol
Assignee: Eli Lilly and Co
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Filing: 1993-10-15
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Granted: 1996-01-09
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Expires: 2013-10-15
Abstract
Abstract A method of lowering serum cholesterol levels comprising administering to a human in need of treatment an effective amount of a compound having the formula <IMAGE> (I) wherein R is hydrogen; hydroxy; C1-C6 alkoxy; a group of the formula -O-C(O)-Ra, wherein Ra is hydrogen, optionally substituted C1-C6 alkyl, C1-C6 alkenyl optionally substituted with aryl, C3-C7 cycloalkyl, optionally substituted aryl or Ra is optionally substituted -O-aryl, or R is a group of the formula -O-SO2-Rb wherein Rb may be C1-C6 alkyl or optionally substituted aryl; or R is carbamoyloxy wherein the nitrogen may be substituted once or twice with C1-C6 alkyl; or R is a group of the formula -O-C(O)Rc-O-(C1-C6 alkyl) wherein Rc is a bond or C1-C6 alkanediyl; R1 is halo, C1-C6 alkyl, C1-C7 alkyl substituted with C1-C6 alkyl, substituted or unsubstituted C3-C7 cycloalkyl, or substituted or unsubstituted C3-C7 cycloalkenyl; R2 is O or CH2; R3 is CH2 or (CH2)2; R4 is <IMAGE> CH2, or a bond; and R5 is pyrrolidinyl or piperidinyl.
Inventors
- 👤 Henry U. Bryant
- 👤 Timothy A. Grese
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 17:47
CPC Classifications
A; A61; A61K; A61K31/00; A61K31/33; A61K31/38; A61K31/381; A61K31/395; A61K31/40; A61K31/4025; A61K31/435; A61K31/44; A61K31/445; A61K31/4523; A61K31/4535; A61K31/47; A61P; A61P3/00; A61P3/06; A61P9/00; A61P9/10; C; C07; C07D; C07D333/00; C07D333/50; C07D333/52; C07D333/54; C07D333/56; C07D409/00; C07D409/02; C07D409/10
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
300 words
A method of lowering serum cholesterol levels comprising administering to a human in need of treatment a serum cholesterol lowering amount of a compound having the formula ##STR13## wherein R is hydrogen; hydroxy; C 1 -C 6 alkoxy; a group of the formula --O--C(O)--R a , wherein R a is hydrogen, C 1 -C 6 alkyl optionally substituted with amino, halo, carbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 7 alkanoyloxy, carbamoyl and/or aryl; or R a is C 1 -C 6 alkenyl optionally substituted with aryl; or R a is a C 3 -C 7 cycloalkyl; or R a is aryl optionally substituted with hydroxy, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, and/or halo; or R a is --O--aryl, said aryl optionally substituted with hydroxy C 1 -C 6 alkyl, C 1 -C 6 alkoxy, and/or halo, or R is a group of the formula --O--SO 2 --R b wherein R b may be C 1 -C 6 alkyl or aryl optionally substituted with C 1 -C 6 alkyl; or R is carbamoyloxy wherein the nitrogen may be substituted once or twice with C 1 -C 6 alkyl; or R is a group of the formula --O--C(O)R c --O--(C 1 -C 6 alkyl) wherein R c is a bond or C 1 -C 6 alkanediyl; R 1 is halo, C 1 -C 6 alkyl, C 1 -C 7 alkyl substituted with C 1 -C 6 alkyl, substituted or unsubstituted C 3 -C 7 cycloalkyl, or substituted or unsubstituted C 3 -C 7 cycloalkenyl; R 2 is O or CH 2 ; R 3 is CH 2 or (CH 2 ) 2 ; R 4 is ##STR14## or a bond; and R 5 is a pyrrolidinyl or piperidinyl; or a pharmaceutically acceptable salt or solvate thereof.
Claim 2
Independent Claim
300 words
A method of lowering serum cholesterol levels comprising administering to a human in need of treatment a serum cholesterol lowering amount of a compound having the formula ##STR13## wherein R is hydrogen; hydroxy; C 1 -C 6 alkoxy; a group of the formula --O--C(O)--R a , wherein R a is hydrogen, C 1 -C 6 alkyl optionally substituted with amino, halo, carbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 7 alkanoyloxy, carbamoyl and/or aryl; or R a is C 1 -C 6 alkenyl optionally substituted with aryl; or R a is a C 3 -C 7 cycloalkyl; or R a is aryl optionally substituted with hydroxy, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, and/or halo; or R a is --O--aryl, said aryl optionally substituted with hydroxy C 1 -C 6 alkyl, C 1 -C 6 alkoxy, and/or halo, or R is a group of the formula --O--SO 2 --R b wherein R b may be C 1 -C 6 alkyl or aryl optionally substituted with C 1 -C 6 alkyl; or R is carbamoyloxy wherein the nitrogen may be substituted once or twice with C 1 -C 6 alkyl; or R is a group of the formula --O--C(O)R c --O--(C 1 -C 6 alkyl) wherein R c is a bond or C 1 -C 6 alkanediyl; R 1 is halo, C 1 -C 6 alkyl, C 1 -C 7 alkyl substituted with C 1 -C 6 alkyl, substituted or unsubstituted C 3 -C 7 cycloalkyl, or substituted or unsubstituted C 3 -C 7 cycloalkenyl; R 2 is O or CH 2 ; R 3 is CH 2 or (CH 2 ) 2 ; R 4 is ##STR14## or a bond; and R 5 is a pyrrolidinyl or piperidinyl; or a pharmaceutically acceptable salt or solvate thereof.
Claim 3
Dependent Claim
11 words
A method of claim 1 wherein the human is a female.
Claim 4
Dependent Claim
11 words
A method of claim 2 wherein the female is estrogen deficient.
Claim 5
Dependent Claim
10 words
A method of claim 3 wherein the female is post-menopausal.
Claim 6
Dependent Claim
40 words
A method according to claim 1 wherein R 1 is a group having the formula ##STR15## or a cycloalkyl group with a carbon number of three to seven that may be substituted with C 1 -C 6 alkyl or hydroxy.
Claim 7
Dependent Claim
9 words
A method of claim 5 wherein R is hydroxy.
Claim 8
Dependent Claim
18 words
A method according to claim 6 wherein R 2 is O and R 4 is CH 2 .
Claim 9
Dependent Claim
17 words
The method according to claim 1 wherein said compound is (6-hydroxy-2-cyclohexylbenzo[b]thien-3-yl)[4-[2(1-pyrrolidinyl)ethoxy]phenyl]methanone, (6-hydroxy-2-cyclohexylbenzo[b]thien-3-yl)[4-[2-(1-piperidinyl)ethoxy]phenyl]methanone, (6-hydroxy-2-cycloheptylbenzo[b]thien-3-yl)[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]methanone, (6-hydroxy-2-cycloheptylbenzo[b]thien-3-yl)[4-[2-(1-piperidinyl)ethoxy]phenyl]methanone, (6-hydroxy-2-isopropylbenzo[b]thien-3-yl)[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]methanone, or (6-hydroxy-2-isopropylbenzo[b]thien-3-yl)[4-[2-(1-piperidinyl)ethoxy]phenyl]methanone.
Claim 10
Dependent Claim
13 words
The method according to claim 6 wherein R 2 is CH 2 .
Claim 11
Dependent Claim
14 words
The method according to claim 9 wherein said compound is (6-hydroxy-2-cyclohexylbenzo[b]thien-3-yl)[4-[3-(1-pyrrolidinyl)propyl]phenyl]methanone, (6-hydroxy-2-cyclohexylbenzo[[b]thien-3-yl)[4-[3-(1-piperidinyl)propyl]phenyl]methanone, or (6-hydroxy-2-cyclohexylbenzo[b]thien-3-yl)[4-[2-(1-pyrrolidinylcarbonyl)ethyl]phenyl]methanone.
Claim 12
Dependent Claim
13 words
The method according to claim 5 wherein R is C 1-C 6 alkoxy.
Claim 13
Dependent Claim
13 words
The method according to claim 11, wherein said compound is (6-methoxy-2-cyclohexylbenzo[b]thien-3-yl)[4-[2-(1-piperidinyl)ethoxy]phenyl]methanone or (6-acetoxy-2-cyclohexylbenzo[b]thien-3-yl)[4-[2-(1-piperidinyl)ethoxy]phenyl]methanone.
Claim 14
Independent Claim
22 words
A method of lowering serum cholesterol comprising administering to a human in need of treatment a serum cholesterol lowering amount of (6-methoxy-2-cyclohexylbenzo[b]thien-3-yl)[4-[2-(1-piperidinyl)ethoxy]phenyl]methanone.
Claim 15
Independent Claim
22 words
A method of lowering serum cholesterol comprising administering to a human in need of treatment a serum cholesterol lowering amount of (6-methoxy-2-cyclohexylbenzo[b]thien-3-yl)[4-[2-(1-piperidinyl)ethoxy]phenyl]methanone.
References Cited (Backward Citations)
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