US4060609A
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Biphenylyl ethers and method of use
Assignee: Merck Patent GmbH
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Filing: 1974-10-29
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Granted: 1977-11-29
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Expires: 1994-10-29
Abstract
Abstract Biphenylyl ethers of the formula R--O--CH 2 --CR 1 (OH)--CH 2 Z wherein R 1 is H or CH 3 ; Z is dialkylamino of 2-8 carbon atoms, morpholino, pyrrolidino, piperidino, homopiperidino, hydroxypyrrolidino, hydroxypiperidino or hydroxyhomopiperidino; R is either biphenylyl substituted by at least one of F, Cl, Br, I, CF 3 , NO 2 and piperidino or, when R 1 is CH 3 or when Z is homopiperidino, hydroxypyrrolidino, hydroxypiperidino or hydroxyhomopiperidino, unsubstituted biphenyl, and the physiologically acceptable acid addition salts thereof, possess cholesterol blood-level-lowering activity and can be produced by reacting a compound of the formula R--O--CH 2 --Y wherein Y is ##STR1## or --CR 1 (OH)--CH 2 X, X being Cl, Br, I or a free or functionally modified OH-group, with an amine of the formula H-Z.
Inventors
- 👤 Erich Schacht
- 👤 Werner Mehrhof
- 👤 Rochus Jonas
- 👤 Herbert Nowak
- 👤 Zdenek Simane
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 10:28
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/04; C07D295/08; C07D295/084; C07D295/088
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
43 words
A biphenylyl ether of the formula R--O--CH 2 --CH(OH)--CH 2 Z wherein Z is piperidino and R is biphenylyl-4 substituted in the 4'-position by F, Cl, Br, I, CF 3 , NO 2 or piperidino; or a physiologically acceptable acid addition salt thereof.
Claim 2
Dependent Claim
43 words
A biphenylyl ether of the formula R--O--CH 2 --CH(OH)--CH 2 Z wherein Z is piperidino and R is biphenylyl-4 substituted in the 4'-position by F, Cl, Br, I, CF 3 , NO 2 or piperidino; or a physiologically acceptable acid addition salt thereof.
Claim 3
Dependent Claim
14 words
A compound of claim 1, 1-[4-(4-trifluoromethylphenyl)-phenoxy]-3-piperidino-2-propanol or a physiologically acceptable acid addition salt thereof.
Claim 4
Dependent Claim
14 words
A compound of claim 1, 1-[4-(4-fluorophenyl)-phenoxy]-3-piperidino-2-propanol or a physiologically acceptable acid addition salt thereof.
Claim 5
Dependent Claim
13 words
A compound of claim, 1-[4-(4-chlorophenyl)-phenoxy]-3-piperidino-2-propanol or a physiologically acceptable acid addition salt thereof.
Claim 6
Dependent Claim
14 words
A compound of claim 1, 1-[4-(4-bromophenyl)-phenoxy]-3-piperidino-2-propanol or a physiologically acceptable acid addition salt thereof.
Claim 7
Dependent Claim
14 words
A compound of claim 1, 1-[4-(4-iodophenyl)-phenoxy]-3-piperidino-2-propanol or a physiologically acceptable acid addition salt thereof.
Claim 8
Dependent Claim
14 words
A compound of claim 1, 1-[4-(4-nitrophenyl)-phenoxy]-3-piperidino-2-propanol or a physiologically acceptable acid addition salt thereof.
Claim 9
Dependent Claim
14 words
A compound of claim 1, 1-[4-(4-piperidinophenyl)-phenoxy]-3-piperidino-2-propanol or a physiologically acceptable acid addition salt thereof.
Claim 10
Dependent Claim
52 words
A biphenylyl ether of the formula R--O--CH 2 --CCH 3 (OH)--CH 2 Z wherein Z is morpholino, pyrrolidino, piperidino or homopiperidino, hydroxypiperidino or hydroxyhomopiperidino, and R is biphenylyl-4 substituted in the 4'-position by F, Cl, Br, I, CF 3 , NO 2 or piperidino; or a physiologically acceptable acid addition salt thereof.
Claim 11
Dependent Claim
52 words
A biphenylyl ether of the formula R--O--CH 2 --CCH 3 (OH)--CH 2 Z wherein Z is morpholino, pyrrolidino, piperidino or homopiperidino, hydroxypiperidino or hydroxyhomopiperidino, and R is biphenylyl-4 substituted in the 4'-position by F, Cl, Br, I, CF 3 , NO 2 or piperidino; or a physiologically acceptable acid addition salt thereof.
Claim 12
Dependent Claim
9 words
A compound of claim 9 wherein Z is pyrrolidino.
Claim 13
Dependent Claim
9 words
A compound of claim 9 wherein Z is piperidino.
Claim 14
Dependent Claim
9 words
A compound of claim 9 wherein Z is morpholino.
Claim 15
Dependent Claim
14 words
A compound of claim 9, 1-[4-(4-chlorophenyl)-phenoxy]-2-methyl-3-piperidino-2-propanol or a physiologically acceptable acid addition salt thereof.
Claim 16
Dependent Claim
14 words
A compound of claim 9, 1-[4-(4-piperidinophenyl)-phenoxy]-2-methyl-3-pyrrolidino-2-propanol or a physiologically acceptable acid addition salt thereof.
Claim 17
Dependent Claim
14 words
A compound of claim 9, 1-[4-(4-piperidinophenyl)-phenoxy]-2-methyl-3-piperidino-2-propanol or a physiologically acceptable acid addition salt thereof.
Claim 18
Dependent Claim
14 words
A compound of claim 9, 1-[4-(4-piperidinophenyl)-phenoxy]-2-methyl-3-homopiperidino-2-propanol or a physiologically acceptable acid addition salt thereof.
Claim 19
Dependent Claim
14 words
A compound of claim 9, 1-[4-(4-piperidinophenyl)-phenoxy]-2-methyl-3-(3-hydroxypiperidino)-2-propanol or a physiologically acceptable acid addition salt thereof.
Claim 20
Dependent Claim
9 words
1-(2-phenyl-4-nitrophenoxy)-3-piperidino-2-propanol or a physiologically acceptable acid addition salt thereof.
Claim 21
Dependent Claim
9 words
1-(2-phenyl-4-nitrophenoxy)-3-piperidino-2-propanol or a physiologically acceptable acid addition salt thereof.
Claim 22
Dependent Claim
9 words
1-[4-(4-piperidinophenyl)-phenoxy]-3-pyrrolidino-2-propanol or a physiologically acceptable acid addition salt thereof.
Claim 23
Dependent Claim
9 words
1-[4-(4-piperidinophenyl)-phenoxy]-3-pyrrolidino-2-propanol or a physiologically acceptable acid addition salt thereof.
Claim 24
Dependent Claim
36 words
A pharmaceutical composition comprising at least a cholesterol blood serum lowering amount per unit dosage of one compound of claim 1 or a physiologically acceptable acid addition salt thereof in admixture with a pharmaceutically acceptable carrier.
Claim 25
Dependent Claim
34 words
A method of lowering abnormally high blood serum cholesterol levels which comprises administering systemically to the affected patient an amount of a compound of claim 1 effective to lower the abnormally high cholesterol level.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-11-28 | 1981-05-30 | 1981-11-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-11-28 | 1985-05-30 | 1985-11-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-11-28 | 1989-05-30 | 1989-11-29 | $7700.00 | Window Closed / Lapsed |