US4255444A
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4-Hydroxy-2-pyrone derivatives having antihyperlipaemic activity
Assignee: Sankyo Co Ltd
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Filing: 1979-10-26
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Granted: 1981-03-10
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Expires: 1999-10-26
Abstract
Abstract 4-Hydroxy-2-pyrone derivatives of formula (I): <IMAGE> (I) (wherein A represents an alkylene group which is optionally alkyl-substituted or an alkenylene group, and Z represents a substituted or unsubstituted aryl or aryloxy group) may be prepared by cyclizing an ester of formula (II): <IMAGE> (II) (wherein A and Z are as defined above and R represents an organic group) and have valuable antilipaemic activities.
Inventors
- 👤 Hidehiko Oka
- 👤 Akira Terahara
- 👤 Akira Endo
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 12:38
CPC Classifications
C; C07; C07D; C07D309/00; C07D309/16; C07D309/28; C07D309/30
Claims Analysis
Total Claims: 29
Claim 1
Independent Claim
120 words
A compound of formula (I): ##STR6## wherein A represents a C 1 -C 2 alkylene group, a C 1 -C 4 alkylene group having one or more C 1 -C 3 alkyl substituents, or a C 2 -C 3 alkenylene group; and Z represents an aromatic ring group selected from the group consisting of (i) a phenyl, naphthyl or tetrahydronaphthyl group, (ii) a substituted phenyl, naphthyl or tetrahydronaphthyl group wherein the aromatic ring is substituted with at least one substituent selected from the group consisting of halogen atoms and C 1 -C 3 alkyl groups, (iii) phenoxy or naphthoxy group, and (iv) a substituted phenoxy or naphthoxy group wherein the aromatic ring is substituted with one or more halogen atoms.
Claim 2
Dependent Claim
120 words
A compound of formula (I): ##STR6## wherein A represents a C 1 -C 2 alkylene group, a C 1 -C 4 alkylene group having one or more C 1 -C 3 alkyl substituents, or a C 2 -C 3 alkenylene group; and Z represents an aromatic ring group selected from the group consisting of (i) a phenyl, naphthyl or tetrahydronaphthyl group, (ii) a substituted phenyl, naphthyl or tetrahydronaphthyl group wherein the aromatic ring is substituted with at least one substituent selected from the group consisting of halogen atoms and C 1 -C 3 alkyl groups, (iii) phenoxy or naphthoxy group, and (iv) a substituted phenoxy or naphthoxy group wherein the aromatic ring is substituted with one or more halogen atoms.
Claim 3
Dependent Claim
34 words
The compound of claim 1, wherein A represents a C 1 or C 2 alkylene group or a C 1 or C 2 alkylene group substituted with a C 1 -C 3 alkyl group.
Claim 4
Dependent Claim
15 words
The compound of claim 2, wherein A represents a methylene, ethylene, methylethylene or dimethylmethylene group.
Claim 5
Dependent Claim
16 words
The compound of claim 1, wherein A represents a C 2 or C 3 alkenylene group.
Claim 6
Dependent Claim
13 words
The compound of claim 4, wherein A represents a vinylene or propenylene group.
Claim 7
Dependent Claim
32 words
The compound of claim 1 or 2 or 4, wherein Z represents a phenyl group, a naphthyl group or a tetrahydronaphthyl group or one of said groups substituted by a halogen atom.
Claim 8
Dependent Claim
24 words
The compound of claim 6, wherein Z represents a phenyl, naphthyl or tetrahydronaphthyl group or one of said groups, substituted with a chlorine atom.
Claim 9
Dependent Claim
23 words
The compound of claim 1, or 3 or 5, wherein Z represents an o-chlorophenyl, m-chlorophenyl, p-chlorophenyl, 2,4-dichlorophenyl, 3,5-dichlorophenyl, 2,6-dichlorophenyl, 2-methyl-1-naphthyl, or 2-methyl-5,6,7,8-tetrahydro-1-naphthyl group.
Claim 10
Dependent Claim
31 words
The compound of claim 1, or 2 or 4, wherein Z represents a phenoxy group or a naphthoxy group or one of said groups substituted with one or more halogen atoms.
Claim 11
Dependent Claim
21 words
The compound of claim 1, or 3 or 5, wherein Z represents a o-chlorophenoxy, m-chlorophenoxy, p-chlorophenoxy, 2,4-dichlorophenoxy, 3,5-dichlorophenoxy or 2,6-dichlorophenoxy group.
Claim 12
Dependent Claim
7 words
4-Hydroxy-6-[2-(2-methyl-1-naphthyl)ethyl]-3,4,5,6-tetrahydro-2H-pyran-2-one of the formula of claim 1.
Claim 13
Dependent Claim
7 words
4-Hydroxy-6-(1-phenoxyethyl)-3,4,5,6-tetrahydro-2H-pyran-2-one of the formula of claim 1.
Claim 14
Dependent Claim
7 words
4-Hydroxy-6-[2-(1-naphthyl)ethyl]-3,4,5,6-tetrahydro-2H-pyran-2-one of the formula of claim 1.
Claim 15
Dependent Claim
7 words
6-[1-(4-Chlorophenoxy)-1-methylethyl]-4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one of the formula of claim 1.
Claim 16
Dependent Claim
7 words
6-[2-(2,6-Dimethyl-1-naphthyl)ethyl]-4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one of the formula of claim 1.
Claim 17
Dependent Claim
7 words
4-Hydroxy-6-[2-(2-methyl-5,6,7,8-tetrahydro-1-naphthyl)ethyl]-3,4,5,6-tetrahydro-2H-pyran-2-one of the formula of claim 1.
Claim 18
Dependent Claim
7 words
4-Hydroxy-6-[1-(2-methylphenyl)ethyl]-3,4,5,6-tetrahydro-2H-pyran-2-one of the formula of claim 1.
Claim 19
Dependent Claim
7 words
6-[1-(2,6-Dimethylphenyl)ethyl]-4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one of the formula of claim 1.
Claim 20
Dependent Claim
7 words
6-[1-(2-Chlorophenyl)ethyl]-4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one of the formula of claim 1.
Claim 21
Dependent Claim
7 words
6-[1-(2,6-Dichlorophenyl)ethyl]-4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one of the formula of claim 1.
Claim 22
Dependent Claim
7 words
4-Hydroxy-6-[3-(2-methyl-1-naphthyl)propyl]-3,4,5,6-tetrahydro-2H-pyran-2-one of the formula of claim 1.
Claim 23
Dependent Claim
7 words
4-Hydroxy-6-[3-(1-naphthyl)propyl]-3,4,5,6-tetrahydro-2H-pyran-2-one of the formula of claim 1.
Claim 24
Dependent Claim
7 words
4-Hydroxy-6-(1-phenylethyl)-3,4,5,6-tetrahydro-2H-pyran-2-one of the formula of claim 1.
Claim 25
Dependent Claim
7 words
6-[1-(4-Chlorophenyl)ethyl]-4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one of the formula of claim 1.
Claim 26
Dependent Claim
140 words
An antihyperlipaemic composition comprising as active ingredient an effective amount of a compound of formula (I): ##STR7## wherein A represents a C 1 -C 2 alkylene group, a C 1 -C 2 alkylene group having one or more C 1 -C 3 alkyl substituents, or a C 2 -C 3 alkenylene group; and Z represents an aromatic ring group selected from the group consisting of (i) a phenyl, naphthyl or tetrahydronaphthyl group, (ii) a substituted phenyl, naphthyl or tetrahydronaphthyl group wherein the aromatic ring is substituted with at least one substituent selected from the group consisting of halogen atoms and C 1 -C 3 alkyl groups, (iii) phenoxy or naphthoxy group, and (iv) a substituted phenoxy or naphthoxy group wherein the aromatic ring is substituted with one or more halogen atoms in admixture with a pharmaceutically acceptable carrier or excipient.
Claim 27
Dependent Claim
140 words
An antihyperlipaemic composition comprising as active ingredient an effective amount of a compound of formula (I): ##STR7## wherein A represents a C 1 -C 2 alkylene group, a C 1 -C 2 alkylene group having one or more C 1 -C 3 alkyl substituents, or a C 2 -C 3 alkenylene group; and Z represents an aromatic ring group selected from the group consisting of (i) a phenyl, naphthyl or tetrahydronaphthyl group, (ii) a substituted phenyl, naphthyl or tetrahydronaphthyl group wherein the aromatic ring is substituted with at least one substituent selected from the group consisting of halogen atoms and C 1 -C 3 alkyl groups, (iii) phenoxy or naphthoxy group, and (iv) a substituted phenoxy or naphthoxy group wherein the aromatic ring is substituted with one or more halogen atoms in admixture with a pharmaceutically acceptable carrier or excipient.
Claim 28
Dependent Claim
16 words
The composition as claimed in claim 25, in a form suitable for oral or parenteral administration.
Claim 29
Dependent Claim
25 words
The composition as claimed in claim 25, wherein said compound of formula (I) is selected from the group consisting of: 4-hydroxy-6-[2-(2-methyl-1-naphthyl)ethyl]-3,4,5,6-tetrahydro-2H-pyran-2-one; 4-hydroxy-6-(1-phenoxyethyl)-3,4,5,6-tetrahydro-2H-pyran-2-one; 4-hydroxy-6-[2-(1-naphthyl)ethyl]-3,4,5,6-tetrahydro-2H-pyran-2-one; and 6-[1-(4-chlorophenoxy)-1-methylethyl]-4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one.
References Cited (Backward Citations)
US3983140A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-03-09 | 1984-09-08 | 1985-03-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-03-09 | 1988-09-08 | 1989-03-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-03-09 | 1992-09-08 | 1993-03-10 | $7700.00 | Window Closed / Lapsed |