Patent US3952104A successfully refreshed from Google Patents.
US3952104A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Benzopyran-2-carboxylic acids in the prevention of asthmatic symptoms
Assignee: Fisons Ltd
•
Filing: 1973-07-26
•
Granted: 1976-04-20
•
Expires: 1993-07-26
Abstract
Abstract There are described certain mono-chromone-2-carboxylic acids of formula, ##SPC1## Having one substituent in the 5 or 6 position or having 2 or more substituents in the 5,6,7 or 8 positions. There are also described processes for making the compounds and pharmacetuical compositions, for the treatment of asthma, containing the compounds.
Inventors
- 👤 Hugh Cairns
- 👤 Albert Chambers
- 👤 Thomas Brian Lee
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 17:53
CPC Classifications
C; C07; C07C; C07C45/00; C07C45/45; C07C45/46; C07C45/61; C07C45/67; C07C45/68; C07C45/70; C07C45/71; C07C59/00; C07C59/40; C07C59/58; C07C59/64; C07C59/66; C07C59/68; C07D; C07D311/00; C07D311/02; C07D311/04; C07D311/22; C07D311/24
Claims Analysis
Total Claims: 42
Claim 1
Independent Claim
84 words
A composition useful for the prevention of asthmatic symptoms comprising an effective amount of a. 8-allyl-5-(2-hydroxypropoxy)-4-oxo-4H-1-benzo-pyran-2-carboxylic acid b. 5-(3-methyl-n-butoxy)-8-n-propyl-4-oxo-4H-1-benzopyran-2-carboxylic acid c. 8-allyl-5-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid d. 6,8-diallyl-5-hydroxy-4-oxo-4H-1-benzopyran-2-carboxylic acid e. 7-(2-ethoxyethoxy)-6-hexyl-4-oxo-4H-1-benzopyran-2-carboxylic acid f. 8-ethyl-5-tetrahydrofurfuryloxy-4-oxo-4H-1-benzopyran-2-carboxylic acid g. 8-allyl-5-tetrahydrofurfuryloxy-4-oxo-4H-1-benzopyran-2-carboxylic acid h. 8-ethyl-5-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid i. 6,8-diallyl-4-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid j. 6,8-diallyl-4-oxo-4H-1-benzopyran-2-carboxylic acid k. 5-(3-ethyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid l. 5-(3-ethyl-n-hexyloxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid m. 5-n-hexyloxy-4-oxo-4H-1-benzopyran-2-carboxylic acid n. 5-n-pentyloxy-4-oxo-4H-1-benzopyran-2-carboxylic acid o. 6,8-diethyl-5-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid p. 6,8-dialllyl-5-tetrahydrofurfuryloxy-4-oxo-4H-1-benzopyuran-2-carboxylic acid q. 6,8-diethyl-5-tetrahydrofurfuryloxy-4-oxo-4H-1-benzopyran-2-carboxylic acid r. 6,8-dimethyl-5-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid or a pharmaceutically acceptable salt thereof as active ingredient, in combination with a pharmaceutically acceptable carrier.
Claim 2
Dependent Claim
84 words
A composition useful for the prevention of asthmatic symptoms comprising an effective amount of a. 8-allyl-5-(2-hydroxypropoxy)-4-oxo-4H-1-benzo-pyran-2-carboxylic acid b. 5-(3-methyl-n-butoxy)-8-n-propyl-4-oxo-4H-1-benzopyran-2-carboxylic acid c. 8-allyl-5-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid d. 6,8-diallyl-5-hydroxy-4-oxo-4H-1-benzopyran-2-carboxylic acid e. 7-(2-ethoxyethoxy)-6-hexyl-4-oxo-4H-1-benzopyran-2-carboxylic acid f. 8-ethyl-5-tetrahydrofurfuryloxy-4-oxo-4H-1-benzopyran-2-carboxylic acid g. 8-allyl-5-tetrahydrofurfuryloxy-4-oxo-4H-1-benzopyran-2-carboxylic acid h. 8-ethyl-5-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid i. 6,8-diallyl-4-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid j. 6,8-diallyl-4-oxo-4H-1-benzopyran-2-carboxylic acid k. 5-(3-ethyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid l. 5-(3-ethyl-n-hexyloxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid m. 5-n-hexyloxy-4-oxo-4H-1-benzopyran-2-carboxylic acid n. 5-n-pentyloxy-4-oxo-4H-1-benzopyran-2-carboxylic acid o. 6,8-diethyl-5-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid p. 6,8-dialllyl-5-tetrahydrofurfuryloxy-4-oxo-4H-1-benzopyuran-2-carboxylic acid q. 6,8-diethyl-5-tetrahydrofurfuryloxy-4-oxo-4H-1-benzopyran-2-carboxylic acid r. 6,8-dimethyl-5-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid or a pharmaceutically acceptable salt thereof as active ingredient, in combination with a pharmaceutically acceptable carrier.
Claim 3
Dependent Claim
18 words
The composition of claim 1 wherein the active ingredient is 8-allyl-5(2-hydroxypropoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid or a pharmaceutically acceptable salt thereof.
Claim 4
Dependent Claim
18 words
The composition of claim 1 wherein the active ingredient is 5-(3-methyl-n-butoxy)-8-n-propyl-4-oxo-4H-1-benzopyran-2-carboxylic acid or a pharmaceutically acceptable salt thereof.
Claim 5
Dependent Claim
18 words
The composition of claim 1 wherein the active ingredient is 8-allyl-5-(3-methyl-n-butoxy(-4-oxo-4H-1-benzopyran-2-carboxylic acid or a pharmaceutically acceptable salt thereof.
Claim 6
Dependent Claim
18 words
The composition of claim 1 wherein the active ingredient is 6,8-diallyl-5-hydroxy-4-oxo-4H-1-benzopyran-2-carboxylic acid or a pharmaceutically acceptable salt therof.
Claim 7
Dependent Claim
18 words
The composition of claim 1 wherein the active ingredient is 7-(2-ethoxyethoxy)-6-hexyl-4-oxo-4H-1-benzopyran-2-carboxylic acid or a pharmaceutically acceptable salt thereof.
Claim 8
Dependent Claim
18 words
The composition of claim 1 wherein the active ingredient is 8-ethyl-5-tetrahydrofurfuryloxy-4-oxo-4H-1-benzopyran-2-carboxylic acid or a pharmaceutically acceptable salt thereof.
Claim 9
Dependent Claim
18 words
The composition of claim 1 wherein the active ingredient is 8-allyl-5-tetrahydrofurfuryloxy-4-oxo-4H-1-benzopyran-2-carboxylic acid or a pharmaceutically acceptable salt thereof.
Claim 10
Dependent Claim
18 words
The composition of claim 1 wherein the active ingredient is 8-ethyl-5-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid or a pharmaceutically acceptable salt thereof.
Claim 11
Dependent Claim
18 words
The composition of claim 1 wherein the active ingredient is 6,8-diallyl-4-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid or a pharmaceutically acceptable salt thereof.
Claim 12
Dependent Claim
18 words
The composition of claim 1 wherein the active ingredient is 6,8-diallyl-4-oxo-4H-1-benzopyran-2-carboxylic acid of a pharmaceutically acceptable salt thereof.
Claim 13
Dependent Claim
18 words
The composition of claim 1 wherein the active ingredient is 5-(3-ethyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid or a pharmaceutically acceptable salt thereof.
Claim 14
Dependent Claim
18 words
The composition of claim 1 wherein the active ingredient is 5-(3-ethyl-n-hexyloxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid or a pharmaceutically acceptable salt thereof.
Claim 15
Dependent Claim
18 words
The composition of claim 1 wherein the active ingredient is 5-n-hexyloxy-4-oxo-4H-1-benzopyran-2-carboxylic acid or a pharmaceutically acceptable salt thereof.
Claim 16
Dependent Claim
18 words
The composition of claim 1 wherein the active ingredient is 5-n-pentyloxy-4-oxo-4H-1-benzopyran-2-carboxylic acid or a pharmaceutically acceptable salt thereof.
Claim 17
Dependent Claim
18 words
The composition of claim 1 wherein the active ingredient is 6,8-diethyl-5-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid or a pharmaceutically acceptable salt thereof.
Claim 18
Dependent Claim
18 words
The composition of claim 1 wherein the active ingredient is 6,8-diallyl-5-tetrahydrofurfuryloxy-4-oxo-4H-1-benzopyran-2-carboxylic acid or a pharmaceutically acceptable salt thereof.
Claim 19
Dependent Claim
18 words
The composition of claim 1 wherein the active ingredient is 6,8-diethyl-5-tetrahydrofurfuryloxy-4-oxo-4H-1-benzopyran-2-carboxylic acid or a pharmaceutically acceptable salt thereof.
Claim 20
Dependent Claim
18 words
The composition of claim 1 wherein the active ingredient is 6,8-dimethyl-5-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid or a pharmaceutically acceptable salt thereof.
Claim 21
Independent Claim
85 words
A method of inhibiting the symptoms of asthma in a patient having asthma, which comprises administering to said patient an effective amount of a compound selected from the group consisting of a. 8-allyl-5-(2-hydroxypropoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid b. 5-(3-methyl-n-butoxy)-8-n-propyl-4-oxo-4H-1-benzopyran-2-carboxylic acid d. 8-allyl-5-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid d. 6,8-diallyl-5-hydroxy-4-oxo-4H-1-benzopyran-2-carboxylic acid e. 7-(2ethyoxyethoxy)-6-hexyl-4-oxo-4H-1-benzopyran-2-carboxylic acid f. 8-ethyl-5-tetrahydrofurfuryloxy-4-oxo-4H-1-benzopyran-2-carboxylic acid g. 8-allyl-5-tetrahydrofurfuryloxy-4-oxo-4H-1-benzopyran-2-carboxylic acid h. 8-ethyl-5-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopryan-2-carboxylic acid i. 6,8-diallyl-4-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid j. 6,8-diallyl-4-oxo-4H-1-benzopyran-2-carboxylic acid k. 5-(3-ethyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid l. 5-(3-ethyl-n-hexyloxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid m. 5-n-hexyloxy-4-oxo-4H-1-benzopyran-2-carboxylic acid n. 5-n-pentyloxy-4-oxo-4H-1-benzopyran-2carboxylic acid o. 6,8-diethyl-5-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid p. 6,8-diallyl-5-tetrahydrofurfuryloxy-4-oxo-4H-1-benzopyran-2-carboxylic acid q. 6,8-diethyl-5-tetrahydrofurfuryloxy-4-oxo-4H-1-benzopyran-2-carboxylic acid r. 6,8-dimethyl-5-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopyran-2carboxylic acid
Claim 22
Independent Claim
85 words
A method of inhibiting the symptoms of asthma in a patient having asthma, which comprises administering to said patient an effective amount of a compound selected from the group consisting of a. 8-allyl-5-(2-hydroxypropoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid b. 5-(3-methyl-n-butoxy)-8-n-propyl-4-oxo-4H-1-benzopyran-2-carboxylic acid d. 8-allyl-5-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid d. 6,8-diallyl-5-hydroxy-4-oxo-4H-1-benzopyran-2-carboxylic acid e. 7-(2ethyoxyethoxy)-6-hexyl-4-oxo-4H-1-benzopyran-2-carboxylic acid f. 8-ethyl-5-tetrahydrofurfuryloxy-4-oxo-4H-1-benzopyran-2-carboxylic acid g. 8-allyl-5-tetrahydrofurfuryloxy-4-oxo-4H-1-benzopyran-2-carboxylic acid h. 8-ethyl-5-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopryan-2-carboxylic acid i. 6,8-diallyl-4-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid j. 6,8-diallyl-4-oxo-4H-1-benzopyran-2-carboxylic acid k. 5-(3-ethyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid l. 5-(3-ethyl-n-hexyloxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid m. 5-n-hexyloxy-4-oxo-4H-1-benzopyran-2-carboxylic acid n. 5-n-pentyloxy-4-oxo-4H-1-benzopyran-2carboxylic acid o. 6,8-diethyl-5-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid p. 6,8-diallyl-5-tetrahydrofurfuryloxy-4-oxo-4H-1-benzopyran-2-carboxylic acid q. 6,8-diethyl-5-tetrahydrofurfuryloxy-4-oxo-4H-1-benzopyran-2-carboxylic acid r. 6,8-dimethyl-5-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopyran-2carboxylic acid
Claim 23
Dependent Claim
6 words
or a pharmaceutically acceptable salt thereof.
Claim 24
Dependent Claim
6 words
or a pharmaceutically acceptable salt thereof.
Claim 25
Dependent Claim
17 words
The method of claim 1 wherein said compound is 8-allyl-5-(2-hydroxypropoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid or a pharmaceutically acceptable salt thereof.
Claim 26
Dependent Claim
17 words
The method of claim 21 wherein said compound is 5-(3-methyl-n-butoxy)-8-n-propyl-4-oxo-4H-1-benzopyran-2-carboxylic acid or a pharmaceutically acceptable salt thereof.
Claim 27
Dependent Claim
17 words
The method of claim 21 wherein said compound is 8-allyl-5-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid or a pharmaceutically acceptable salt thereof.
Claim 28
Dependent Claim
17 words
The method of claim 21 wherein said compound is 6,8-diallyl-5-hydroxy-4-oxo-4H-1-benzopyran-2-carboxylic acid or a pharmaceutically acceptable salt thereof.
Claim 29
Dependent Claim
17 words
The method of claim 21 wherein said compound is 7-(2-ethoxyethoxy)-6-hexyl-4-oxo-4H-1-benzopyran-2-carboxylic acid or a pharmaceutically acceptable salt thereof.
Claim 30
Dependent Claim
17 words
The method of claim 21 wherein said compound is 8-ethyl-5-tetrahydrofurfuryloxy-4-oxo-4H-1-benzopyran-2-carboxylic acid or a pharmaceutically acceptable salt thereof.
Claim 31
Dependent Claim
17 words
The method of claim 21 wherein said compound is 8-allyl-5-tetrahydrofurfuryloxy-4-oxo-4H-1-benzopyran-2-carboxylic acid or a pharmaceutically acceptable salt thereof.
Claim 32
Dependent Claim
17 words
The method of claim 21 wherein said compound is 8-ethyl-5-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid or a pharmaceutically acceptable salt thereof.
Claim 33
Dependent Claim
17 words
The method of claim 21 wherein said compound is 6,8-diallyl-4-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid or a pharmaceutically acceptable salt thereof.
Claim 34
Dependent Claim
17 words
The method of claim 21 wherein said compound is 6,8-diallyl-4-oxo-4H-1-benzopyran-2-carboxylic acid or a pharmaceutically acceptable salt thereof.
Claim 35
Dependent Claim
17 words
The method of claim 21 wherein said compound is 5-(3-ethyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid or a pharmaceutically acceptable salt thereof.
Claim 36
Dependent Claim
17 words
The method of claim 21 wherein said compound is 5-(3-ethyl-n-hexyloxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid or a pharmaceutically acceptable salt thereof.
Claim 37
Dependent Claim
17 words
The method of claim 21 wherein said compound is 5-n-hexyloxy-4-oxo-4H-1-benzopyran-2-carboxylic acid or a pharmaceutically acceptable salt thereof.
Claim 38
Dependent Claim
17 words
The method of claim 21 wherein said compound is 5-n-pentyloxy-4-oxo-4H-1-benzopyran-2-carboxylic acid or a pharmaceutically acceptable salt thereof.
Claim 39
Dependent Claim
17 words
The method of claim 21 wherein said compound is 6,8-diethyl-5-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid or a pharmaceutically acceptable salt thereof.
Claim 40
Dependent Claim
17 words
The method of claim 21 wherein said compound is 6,8-diallyl-5-tetrahydrofurfuryloxy-4-oxo-4H-1-benzopyran-2-carboxylic acid or a pharmaceutically acceptable salt thereof.
Claim 41
Dependent Claim
17 words
The method of claim 21 wherein said compound is 6,8-diethyl-5-tetrahydrofurfuryloxy-4-oxo-4H-1-benzopyran-2-carboxylic acid or a pharmaceutically acceptable salt thereof.
Claim 42
Dependent Claim
17 words
The method of claim 21 wherein said compound is 6,8-dimethyl-5-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid or a pharmaceutically acceptable salt thereof.
References Cited (Backward Citations)
US3652765A
Cited
US3427324A
Cited
US3484445A
Cited
US3864493A
Cited
US3629290A
Cited
US3816470A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-04-20 | 1979-10-20 | 1980-04-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-04-20 | 1983-10-20 | 1984-04-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-04-20 | 1987-10-20 | 1988-04-20 | $7700.00 | Window Closed / Lapsed |