US4309407A
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Alkenyl-substituted thienylalkanecarboxylic acids and derivatives thereof
Assignee: A NATTERMANN & CIE A GERMAN CORP GmbH
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Filing: 1980-11-12
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Granted: 1982-01-05
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Expires: 2000-11-12
Abstract
Abstract The invention provides novel ω-(5-alkenylthien-2-yl)alkanecarboxylic acids and their functional derivatives having the formula ##STR1## wherein n is an integer from 1 to 9, inclusive; R 1 is H and R 2 is --OH, or R 1 and R 2 together with the wavy lines represent a keto group; and R 3 is H, C 1 -C 6 straight or branched-chain saturated hydrocarbon, or a pharmaceutically acceptable alkali cation. The 3-oxoalkenyl-substituted compounds of formula (I) are prepared by a Wittig-Horner reaction using a 2-oxoheptylphosphonic acid dialkyl ester and an aldehyde of the formula ##STR2## as starting materials, while the 3-hydroxyalkenyl-substituted compounds are obtained by reduction of the corresponding 3-oxoalkenyl compounds. The esters of formula (I) can also be readily converted to the corresponding acids and salts of formula (I). The compounds of the invention have valuable anti-inflammatory, antipyretic and anti-arteriosclerotic properties, yet have low toxicity and do not irritate the gastric mucosa.
Inventors
- 👤 Hans-Heiner Lautenschlager
- 👤 Hans Betzing
- 👤 Johannes Winkelmann
- 👤 Manfred Probst
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 10:19
CPC Classifications
C; C07; C07D; C07D333/00; C07D333/02; C07D333/04; C07D333/06; C07D333/24; A; A61; A61P; A61P29/00; A61P9/00; A61P9/10
Claims Analysis
Total Claims: 39
Claim 1
Independent Claim
72 words
A compound of the formula ##STR6## wherein n is an integer from 1 to 9, inclusive; R 1 is a hydrogen atom and R 2 is a hydroxy group, or R 1 and R 2 together with the wavy lines represent a doubly bonded oxygen atom; and R 3 is a hydrogen atom, a straight or branched-chain saturated hydrocarbon group containing 1 to 6 carbon atoms, or a pharmaceutically acceptable alkali cation.
Claim 2
Dependent Claim
72 words
A compound of the formula ##STR6## wherein n is an integer from 1 to 9, inclusive; R 1 is a hydrogen atom and R 2 is a hydroxy group, or R 1 and R 2 together with the wavy lines represent a doubly bonded oxygen atom; and R 3 is a hydrogen atom, a straight or branched-chain saturated hydrocarbon group containing 1 to 6 carbon atoms, or a pharmaceutically acceptable alkali cation.
Claim 3
Dependent Claim
13 words
A compound according to claim 1 wherein n is 7, 8 or 9.
Claim 4
Dependent Claim
23 words
A compound according to claim 1 wherein R 1 and R 2 together with the wavy lines represent a doubly bonded oxygen atom.
Claim 5
Dependent Claim
16 words
A compound according to claim 1, 2 or 3 wherein R 3 is a hydrogen atom.
Claim 6
Dependent Claim
18 words
A compound according to claim 1, 2 or 3 wherein R 3 is a pharmaceutically acceptable alkali cation.
Claim 7
Dependent Claim
14 words
A compound according to claim 5 wherein R 3 is an alkali metal cation.
Claim 8
Dependent Claim
26 words
A compound according to claim 1, 2 or 3 wherein R 3 is a straight or branched-chain saturated hydrocarbon group containing 1 to 6 carbon atoms.
Claim 9
Dependent Claim
13 words
A compound according to claim 7 wherein R 3 is a methyl radical.
Claim 10
Dependent Claim
17 words
A compound according to claim 7 wherein R 3 is a C 2 -C 6 alkyl radical.
Claim 11
Dependent Claim
18 words
A compound according to claim 1 which is 2-[5-(3-oxooct-1-enyl)thien-2-yl]acetic acid or a pharmaceutically acceptable salt or ester thereof.
Claim 12
Dependent Claim
18 words
A compound according to claim 1 which is 3-[5-(3-oxooct-1-enyl)thien-2-yl]propionic acid or a pharmaceutically acceptable salt or ester thereof.
Claim 13
Dependent Claim
18 words
A compound according to claim 1 which is 4-[5-(3-oxooct-1-enyl)thien-2-yl]butyric acid or a pharmaceutically acceptable salt or ester thereof.
Claim 14
Dependent Claim
18 words
A compound according to claim 1 which is 5-[5-(3-oxooct-1-enyl)thien-2-yl]valeric acid or a pharmaceutically acceptable salt or ester thereof.
Claim 15
Dependent Claim
18 words
A compound according to claim 1 which is 6-[5-(3-oxooct-1-enyl)thien-2-yl]hexanoic acid or a pharmaceutically acceptable salt or ester thereof.
Claim 16
Dependent Claim
18 words
A compound according to claim 1 which is 7-[5-(3-oxooct-1-enyl)thien-2-yl]heptanoic acid or a pharmaceutically acceptable salt or ester thereof.
Claim 17
Dependent Claim
18 words
A compound according to claim 1 which is 8-[5-(3-oxooct-1-enyl)thien-2-yl]octanoic acid or a pharmaceutically acceptable salt or ester thereof.
Claim 18
Dependent Claim
18 words
A compound according to claim 1 which is 9-[5-(3-oxooct-1-yl)thien-2-yl]nonionic acid or a pharmaceutically acceptable salt or ester thereof.
Claim 19
Dependent Claim
18 words
A compound according to claim 1 which is 10-[5-(3-oxooct-1-enyl)thien-2-yl]decanoic acid or a pharmaceutically acceptable salt or ester thereof.
Claim 20
Dependent Claim
12 words
The compound according to claim 1 which is 7-[5-(3-hydroxyoct-1-enyl)thien-2-yl]heptanoic acid methyl ester.
Claim 21
Dependent Claim
12 words
The compound according to claim 1 which is 8-[5-(3-hydroxyoct-1-enyl)thien-2-yl]octanoic acid methyl ester.
Claim 22
Dependent Claim
12 words
The compound according to claim 1 which is 9-[5-(3-hydroxyoct-1-enyl)thien-2-yl]nonanoic acid methyl ester.
Claim 23
Dependent Claim
12 words
The compound according to claim 1 which is 10-[5-(3-hydroxyoct-1-enyl)thien-2-yl]decanoic acid methyl ester.
Claim 24
Dependent Claim
12 words
The compound according to claim 1 which is 5-[5-(3-oxooct-1-enyl)thien-2-yl]valeric acid methyl ester.
Claim 25
Dependent Claim
12 words
The compound according to claim 1 which is 6-[5-(3-oxooct-1-enyl)thien-2-yl]hexanoic acid methyl ester.
Claim 26
Dependent Claim
12 words
The compound according to claim 1 which is 7-[5-(3-oxooct-1-enyl)thien-2-yl]heptanoic acid methyl ester.
Claim 27
Dependent Claim
12 words
The compound according to claim 1 which is 8-[5-(3-oxooct-1-enyl)thien-2-yl]octanoic acid methyl ester.
Claim 28
Dependent Claim
12 words
The compound according to claim 1 which is 9-[5-(3-oxooct-1-enyl)thien-2-yl]nonanoic acid methyl ester.
Claim 29
Dependent Claim
12 words
The compound according to claim 1 which is 10-[5-(3-oxooct-1-enyl)thien-2-yl]decanoic acid methyl ester.
Claim 30
Dependent Claim
31 words
A pharmaceutical composition for the treatment of inflammation comprising an effective anti-inflammatory amount of a compound of formula (I) as defined by claim 1, and a non-toxic, pharmaceutically acceptable carrier therefor.
Claim 31
Dependent Claim
31 words
A pharmaceutical composition for the reduction of fever comprising an effective antipyretic amount of a compound of formula (I) as defined by claim 1, and a non-toxic pharmaceutically acceptable carrier therefor.
Claim 32
Dependent Claim
32 words
A pharmaceutical composition for the treatment of arteriosclerotic disorders comprising an effective anti-arteriosclerotic amount of a compound of formula (I) as defined by claim 1, and a non-toxic pharmaceutically acceptable carrier therefor.
Claim 33
Dependent Claim
50 words
A pharmaceutical composition according to claim 29, 30, or 31 wherein the compound of formula (I) is selected from the group consisting of: 2-[5-(3-oxooct-1-enyl)thien-2-yl]acetic acid, 3[5-(3-oxooct-1-enyl)thien-2-yl]propionic acid, 4-[5-(3-oxooct-1-enyl)thien-2-yl]butyric acid, 5-[5-(3-oxooct-1-enyl)thien-2-yl]valeric acid, 6-[5-(3-oxooct-1-enyl)thien-2-yl]hexanoic acid, 7-[5-(3-oxooct-1-enyl)thien-2-yl]heptanoic acid, 8-[5-(3-oxooct-1-enyl)thien-2-yl]octanoic acid, 9-[5-(3-oxooct-1-enyl)thien-2-yl]nonanoic acid, and 10-[5-(3-oxooct-1-enyl)thien-2-yl]decanoic acid, and the pharmaceutically acceptable salts and esters thereof.
Claim 34
Dependent Claim
39 words
A pharmaceutical composition of claim 29, 30 or 31 wherein the compound of formula (I) is selected from the group consisting of: 7-[5-(3-hydroxyoct-1-enyl)thien-2-yl]heptanoic acid methyl ester, 8-[5-(3-hydroxyoct-1-enyl)thien-2-yl]octanoic acid methyl ester, 9-[5-(3-hydroxyoct-1-enyl)thien-2-yl]nonanoic acid methyl ester, and 10-[5-(3-hydroxyoct-1-enyl)thien-2-yl]decanoic acid methyl ester.
Claim 35
Dependent Claim
48 words
A pharmaceutical composition according to claim 29, 30 or 31 wherein the compound of formula (I) is selected from the group consisting of: 5-[5-(3-oxooct-1-enyl)thien-2-yl]valeric acid methyl ester, 6-[5-(3-oxooct-1-enyl)thien-2-yl]hexanoic acid methyl ester, 7-[5-(3-oxooct-1-enyl)thien-2-yl]heptanoic acid methyl ester, 8-[5-(3-oxooct-1-enyl)thien-2-yl]octanoic acid methyl ester, 9-[5-(3-oxooct-1-enyl)thien-2-yl]nonanoic acid methyl ester, and 10-[5-(3-oxooct-1-enyl)thien-2-yl]decanoic acid methyl ester.
Claim 36
Dependent Claim
18 words
A pharmaceutical composition according to claim 34 wherein the compound of formula (I) is 9-[5-(3-oxooct-1-enyl)thien-2-yl]nonanoic acid methyl ester.
Claim 37
Dependent Claim
38 words
A method of treating inflammation in or on a mammal which comprises administering thereto an effective anti-inflammatory amount of a compound of formula (I) as defined by claim 1, in combination with a non-toxic pharmaceutically acceptable carrier therefor.
Claim 38
Dependent Claim
36 words
A method of reducing fever in a mammal which comprises administering thereto an effective antipyretic amount of a compound of formula (I) as defined by claim 1, in combination with a non-toxic pharmaceutically acceptable carrier therefor.
Claim 39
Dependent Claim
38 words
A method of treating an arteriosclerotic disorder in a mammal which comprises administering thereto an effective anti-arteriosclerotic amount of a compound of formula (I) as defined by claim 1, in combination with a non-toxic pharmaceutically acceptable carrier therefor.
References Cited (Backward Citations)
US3691202A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-01-04 | 1985-07-06 | 1986-01-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-01-04 | 1989-07-06 | 1990-01-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-01-04 | 1993-07-06 | 1994-01-05 | $7700.00 | Window Closed / Lapsed |