Patent US3872050A successfully refreshed from Google Patents.
Patent US5482949A successfully refreshed from Google Patents.
US5482949A
Expired / Lapsed
US
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Sulfonate derivatives of 3-aroylbenzo[b]thiophenes
Assignee: Eli Lilly and Co
•
Filing: 1993-03-19
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Granted: 1996-01-09
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Expires: 2013-03-19
Abstract
Abstract The present invention relates to sulfonate derivatives of 3-aroylbenzo[b]thiophenes, pharmaceutical formulations containing these compounds and methods of using such compounds for inhibiting the loss of bone, lowering serum cholesterol levels and therapeutically treating hormone dependent mammalian breast and uterine carcinoma.
Inventors
- 👤 Larry J. Black
- 👤 Henry U. Bryant
- 👤 George J. Cullinan
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 12:36
CPC Classifications
C; C07; C07D; C07D333/00; C07D333/50; C07D333/52; C07D333/54; C07D333/56; A; A61; A61P; A61P19/00; A61P19/08; A61P19/10; A61P3/00; A61P3/06; A61P35/00; A61P37/00; A61P37/08; A61P43/00; A61P9/00; A61P9/10
Claims Analysis
Total Claims: 40
Claim 1
Independent Claim
93 words
A compound selected from the formula ##STR5## where X is a bond or --CH 2 --; R 2 is a heterocyclic ring selected froth pyrrolidino, piperidino or hexamethyleneimino; R is OH or --OSO 2 --(CH 2 ) n --CH 3 ; R 1 is hydrogen, OH, fluoro, chloro, or --OSO 2 --(CH 2 ) n --CH 3 ; each n is independently 3, 4 or 5; or its pharmaceutically acceptable salt or solvate; provided that at least one of R and R 1 is --OSO 2 --(CH 2 ) n --CH 3 .
Claim 2
Dependent Claim
93 words
A compound selected from the formula ##STR5## where X is a bond or --CH 2 --; R 2 is a heterocyclic ring selected froth pyrrolidino, piperidino or hexamethyleneimino; R is OH or --OSO 2 --(CH 2 ) n --CH 3 ; R 1 is hydrogen, OH, fluoro, chloro, or --OSO 2 --(CH 2 ) n --CH 3 ; each n is independently 3, 4 or 5; or its pharmaceutically acceptable salt or solvate; provided that at least one of R and R 1 is --OSO 2 --(CH 2 ) n --CH 3 .
Claim 3
Dependent Claim
14 words
A compound of claim 1 where R 2 is a pyrrolidino or piperidino ring.
Claim 4
Dependent Claim
23 words
A compound of claim 1 where R is --OSO 2 --(CH 2 ) n --CH 3 and n is 3, 4 or 5.
Claim 5
Dependent Claim
29 words
A compound of claim 3 where R 1 is hydrogen, OH, chloro, fluoro or --OSO 2 --(CH 2 ) n --CH 3 and n is 3, 4 or 5.
Claim 6
Dependent Claim
34 words
A compound of claim 1 where R 2 is a piperidino ring; R and R 1 are --OSO 2 --(CH 2 ) n --CH 3 ; and each n is independently 3 or 4.
Claim 7
Dependent Claim
18 words
A compound of claim 5 which is [6-(n-butylsulfonoyl)-2-[4-(n-butylsulfonoyl)phenyl-]benzo[b]thien 3-yl][4-[2-(1-piperidinyl)ethoxy]-phenyl] methanone or a pharmaceutically acceptable salt or solvate thereof.
Claim 8
Dependent Claim
16 words
A compound of claim 5 which is [6-(n-pentylsulfonoyl)-2-[4-(n-pentylsulfonoyl)phenyl]benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]-phenyl]methanone or a pharmaceutically acceptable salt or solvate thereof.
Claim 9
Dependent Claim
105 words
A pharmaceutical composition comprising a pharmaceutically acceptable carrier, diluent or excipient and a compound selected from the formula ##STR6## where X is a bond or --CH 2 --; R 2 is a heterocyclic ring selected from pyrrolidino, piperidino or hexamethyleneimino; R is OH or --OSO 2 --(CH 2 ) n --CH 3 ; R 1 is hydrogen, OH, fluoro, chloro, or --OSO 2 --(CH 2 ) n --CH 3 ; each n is independently 3, 4 or 5; or its pharmaceutically acceptable salt or solvate; provided that at east one of R and R 1 is --OSO 2 --(CH 2 ) n --CH 3 .
Claim 10
Dependent Claim
105 words
A pharmaceutical composition comprising a pharmaceutically acceptable carrier, diluent or excipient and a compound selected from the formula ##STR6## where X is a bond or --CH 2 --; R 2 is a heterocyclic ring selected from pyrrolidino, piperidino or hexamethyleneimino; R is OH or --OSO 2 --(CH 2 ) n --CH 3 ; R 1 is hydrogen, OH, fluoro, chloro, or --OSO 2 --(CH 2 ) n --CH 3 ; each n is independently 3, 4 or 5; or its pharmaceutically acceptable salt or solvate; provided that at east one of R and R 1 is --OSO 2 --(CH 2 ) n --CH 3 .
Claim 11
Dependent Claim
15 words
A pharmaceutical composition of claim 8 where R 2 is a pyrrolidino or piperidino ring.
Claim 12
Dependent Claim
24 words
A pharmaceutical composition of claim 8 where R is --OSO 2 --(CH 2 ) n --CH 3 and n is 3, 4 or 5.
Claim 13
Dependent Claim
30 words
A pharmaceutical composition of claim 10 where R 1 is hydrogen, OH, chloro, fluoro or --OSO 2 --(CH 2 ) n --CH 3 and n is 3, 4 or 5.
Claim 14
Dependent Claim
35 words
A pharmaceutical composition of claim 8 where R 2 is a piperidino ring; R and R 1 are --OSO 2 --(CH 2 ) n --CH 3 ; and each n is independently 3 or 4.
Claim 15
Dependent Claim
19 words
A pharmaceutical composition of claim 12 where said compound is [6-(n-butylsulfonoyl)-2-[4-(n-butylsulfonoyl)phenyl]benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]-phenyl]methanone or a pharmaceutically acceptable salt or solvate thereof.
Claim 16
Dependent Claim
19 words
A pharmaceutical composition of claim 12 where said compound is [6-(n-pentylsulfonoyl)-2-[4-(n-pentylsulfonoyl)phenyl]benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]-phenyl]methanone or a pharmaceutically acceptable salt or solvate thereof.
Claim 17
Independent Claim
112 words
A method of inhibiting bone loss comprising administering to a human in need of treatment an effective amount of a compound selected from the formula ##STR7## where X is a bond or --CH 2 --; R 2 is a heterocyclic ring selected from pyrrolidino, piperidino or hexamethyleneimino; R is OH or --OSO 2 --(CH 2 ) n --CH 3 ; R 1 is hydrogen, OH, fluoro, chloro, or --OSO 2 --(CH 2 ) n --CH 3 ; each n is independently 3, 4 or 5; or its pharmaceutically acceptable salt or solvate; provided that at least one of R and R 1 is --OSO 2 --(CH 2 ) n --CH 3 .
Claim 18
Independent Claim
112 words
A method of inhibiting bone loss comprising administering to a human in need of treatment an effective amount of a compound selected from the formula ##STR7## where X is a bond or --CH 2 --; R 2 is a heterocyclic ring selected from pyrrolidino, piperidino or hexamethyleneimino; R is OH or --OSO 2 --(CH 2 ) n --CH 3 ; R 1 is hydrogen, OH, fluoro, chloro, or --OSO 2 --(CH 2 ) n --CH 3 ; each n is independently 3, 4 or 5; or its pharmaceutically acceptable salt or solvate; provided that at least one of R and R 1 is --OSO 2 --(CH 2 ) n --CH 3 .
Claim 19
Dependent Claim
14 words
A method of claim 15 where R 2 is a pyrrolidino or piperidino ring.
Claim 20
Dependent Claim
23 words
A method of claim 15 where R is --OSO 2 --(CH 2 ) n --CH 3 and n is 3, 4 or 5.
Claim 21
Dependent Claim
29 words
A method of claim 17 where R 1 is hydrogen, OH, chloro, fluoro or --OSO 2 --(CH 2 ) n --CH 3 and n is 3, 4 or 5.
Claim 22
Dependent Claim
34 words
A method of claim 15 where R 2 is a piperidino ring; R and R 1 are --OSO 2 --(CH 2 ) n CH 3 ; and each n is independently 3 or 4.
Claim 23
Dependent Claim
18 words
A method of claim 19 where the compound is [6-(n-butylsulfonoyl)-2-[4-(n-butylsulfonoyl)phenyl]benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]-phenyl]methanone or a pharmaceutically acceptable salt or solvate thereof.
Claim 24
Dependent Claim
18 words
A method of claim 19 where the compound is [6-(n-Pentylsulfonoyl)-2-[4-(n-pentylsulfonoyl)phenyl]benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]-phenyl]methanone or a pharmaceutically acceptable salt or solvate thereof.
Claim 25
Independent Claim
114 words
A method of lower serum cholesterol levels comprising administering to a human in need of treatment a serum cholesterol lowering amount of a compound selected from formula ##STR8## where X is a bond or --CH 2 --; R 2 is a heterocyclic ring selected from pyrrolidino, piperidino or hexamethyleneimino: R is OH or --OSO 2 --(CH 2 ) n --CH 3 ; R 1 is hydrogen, OH, fluoro, chloro, or OSO 2 --(CH 2 ) n CH 3 ; each n is independently 3, 4 or 5; or its pharmaceutically acceptable salt or solvate; provided that at least one of R and R 1 is --OSO 2 --(CH 2 ) n --CH 3 .
Claim 26
Independent Claim
114 words
A method of lower serum cholesterol levels comprising administering to a human in need of treatment a serum cholesterol lowering amount of a compound selected from formula ##STR8## where X is a bond or --CH 2 --; R 2 is a heterocyclic ring selected from pyrrolidino, piperidino or hexamethyleneimino: R is OH or --OSO 2 --(CH 2 ) n --CH 3 ; R 1 is hydrogen, OH, fluoro, chloro, or OSO 2 --(CH 2 ) n CH 3 ; each n is independently 3, 4 or 5; or its pharmaceutically acceptable salt or solvate; provided that at least one of R and R 1 is --OSO 2 --(CH 2 ) n --CH 3 .
Claim 27
Dependent Claim
14 words
A method of claim 22 where R 2 is a pyrrolidino or piperidino ring.
Claim 28
Dependent Claim
23 words
A method of claim 22 where R is --OSO 2 (CH 2 ) n --CH 3 and n is 3, 4 or 5.
Claim 29
Dependent Claim
29 words
A method of claim 24 where R 1 is hydrogen, OH, chloro, fluoro or --OSO 2 --(CH 2 ) n --CH 3 and n is 3, 4 or 5.
Claim 30
Dependent Claim
33 words
A method of claim 22 where R 2 is a piperidino ring; R and R 1 are --OSO 2 --(CH 2 ) n --CH 3 ; each n is independently 3 or 4.
Claim 31
Dependent Claim
19 words
A method of claim 26 where the compound is [6-(n-butylsulfonoyl)-2-[4-(n-butylsulfonoyl)phenyl]benzo[b]thien-3 -yl][4-[2-(1-piperidinyl)ethoxy]-phenyl]methanone or a pharmaceutically acceptable salt or solvate thereof.
Claim 32
Dependent Claim
18 words
A method of claim 26 where the compound is [6-(n-pentylsulfonoyl)-2-[4-(n-pentylsulfonoyl)phenyl]benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]-phenyl]methanone or a pharmaceutically acceptable salt or solvate thereof.
Claim 33
Independent Claim
117 words
A method of treating estrogen dependent mammary or uterine carcinoma comprising administering to a human in need of treatment an effective amount of a compound selected from the formula ##STR9## where X is a bond or --CH 2 --; R 2 is a heterocyclic ring selected from pyrrolidino, piperidino or hexamethyleneimino; R is OH or --OSO 2 --(CH 2 ) n --CH 3 ; R 1 is hydrogen, OH, fluoro, chloro, or --OSO 2 --(CH 2 ) n --CH 3 ; each n is independently 3, 4 or 5; or its pharmaceutically acceptable salt or solvate thereof; provided that at least one of R and R 1 is --OSO 2 --(CH 2 ) n --CH 3 .
Claim 34
Independent Claim
117 words
A method of treating estrogen dependent mammary or uterine carcinoma comprising administering to a human in need of treatment an effective amount of a compound selected from the formula ##STR9## where X is a bond or --CH 2 --; R 2 is a heterocyclic ring selected from pyrrolidino, piperidino or hexamethyleneimino; R is OH or --OSO 2 --(CH 2 ) n --CH 3 ; R 1 is hydrogen, OH, fluoro, chloro, or --OSO 2 --(CH 2 ) n --CH 3 ; each n is independently 3, 4 or 5; or its pharmaceutically acceptable salt or solvate thereof; provided that at least one of R and R 1 is --OSO 2 --(CH 2 ) n --CH 3 .
Claim 35
Dependent Claim
14 words
A method of claim 29 where R 2 is a pyrrolidino or piperidino ring.
Claim 36
Dependent Claim
23 words
A method of claim 29 where R is --OSO 2 --(CH 2 ) n --CH 3 and n is 3, 4 or 5.
Claim 37
Dependent Claim
29 words
A method of claim 31 where R 1 is hydrogen, OH, chloro, fluoro or --OSO 2 --(CH 2 ) n --CH 3 and n is 3, 4 or 5.
Claim 38
Dependent Claim
34 words
A method of claim 29 where R 2 is a piperidino ring; R and R 1 are --OSO 2 --(CH 2 ) n --CH 3 ; and each n is independently 3 or 4.
Claim 39
Dependent Claim
18 words
A method of claim 33 where the compound is [6-(n-butylsulfonoyl)-2-[4-(n-butylsulfonoyl)phenyl]benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]-phenyl]methanone or a pharmaceutically acceptable salt or solvate thereof.
Claim 40
Dependent Claim
18 words
A method of claim 33 where the compound is [6-(n-pentylsulfonoyl)-2-[4-(n-pentylsulfonoyl)phenyl]benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]-phenyl]methanone or a pharmaceutically acceptable salt or solvate thereof.
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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) | 1999-01-08 | 1999-07-10 | 2000-01-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2003-01-08 | 2003-07-10 | 2004-01-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2007-01-08 | 2007-07-10 | 2008-01-09 | $7700.00 | Window Closed / Lapsed |