US4119720A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Unsaturated esters of 4-hydroxy-2-quinolinone-3-carboxylic acids and salts thereof
Assignee: Sandoz Inc
•
Filing: 1977-07-06
•
Granted: 1978-10-10
•
Expires: 1997-07-06
Abstract
Abstract Disclosed are compounds which are unsaturated esters of 4-hydroxy-2-quinolinone-3-carboxylic acids, e.g., 1-allyl-6,7-dimethoxy-4-hydroxy-2-quinolinone-3-carboxylic acid allyl ester, useful as anti-allergic agents, and prepared by reacting an isatoic anhydride with an alkali metal salt of a malonic acid unsaturated ester.
Inventors
- 👤 Goetz E. Hardtmann
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 18:56
CPC Classifications
C; C07; C07D; C07D215/00; C07D215/02; C07D215/16; C07D215/48; C07D215/54; C07D215/56
Claims Analysis
Total Claims: 79
Claim 1
Independent Claim
224 words
A compound of the formula: ##STR6## wherein R p o is hydrogen, alkyl of 1 to 6 carbon atoms, alkenyl of 3 to 6 carbon atoms, alkynyl of 3 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, cycloalkylalkyl in which the cycloalkyl is of 3 to 6 carbon atoms and the alkyl portion is of 1 or 2 carbon atoms, or ##STR7## n is 0 or 1, M is hydrogen or a pharmaceutically acceptable cation, R is alkenyl of 3 to 6 carbon atoms or alkynyl of 3 to 6 carbon atoms, Y and Y' are independently hydrogen, fluoro, chloro, bromo, alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, trifluoromethyl or nitro, with the proviso that only one of Y and Y' can be from the group consisting of nitro and trifluoromethyl, and R p and R p ' are independently hydrogen, fluoro, chloro, bromo, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, nitro or trifluoromethyl, or R p and R p ' together form 6,7-methylenedioxy, with the proviso that only one of R p and R p ' can be from the group consisting of nitro and trifluoromethyl, with the further proviso that the unsaturation in any alkenyl or alkynyl is on other than the alpha carbon atom.
Claim 2
Dependent Claim
224 words
A compound of the formula: ##STR6## wherein R p o is hydrogen, alkyl of 1 to 6 carbon atoms, alkenyl of 3 to 6 carbon atoms, alkynyl of 3 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, cycloalkylalkyl in which the cycloalkyl is of 3 to 6 carbon atoms and the alkyl portion is of 1 or 2 carbon atoms, or ##STR7## n is 0 or 1, M is hydrogen or a pharmaceutically acceptable cation, R is alkenyl of 3 to 6 carbon atoms or alkynyl of 3 to 6 carbon atoms, Y and Y' are independently hydrogen, fluoro, chloro, bromo, alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, trifluoromethyl or nitro, with the proviso that only one of Y and Y' can be from the group consisting of nitro and trifluoromethyl, and R p and R p ' are independently hydrogen, fluoro, chloro, bromo, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, nitro or trifluoromethyl, or R p and R p ' together form 6,7-methylenedioxy, with the proviso that only one of R p and R p ' can be from the group consisting of nitro and trifluoromethyl, with the further proviso that the unsaturation in any alkenyl or alkynyl is on other than the alpha carbon atom.
Claim 3
Dependent Claim
10 words
A compound of claim 1 in which R is alkenyl.
Claim 4
Dependent Claim
10 words
A compound of claim 2 in which R is allyl.
Claim 5
Dependent Claim
12 words
A compound of claim 1 in which R p o is hydrogen.
Claim 6
Dependent Claim
12 words
A compound of claim 1 in which R p o is alkyl.
Claim 7
Dependent Claim
12 words
A compound of claim 1 in which R p o is alkynyl.
Claim 8
Dependent Claim
12 words
A compound of claim 1 in which R p o is cycloalkyl.
Claim 9
Dependent Claim
12 words
A compound of claim 1 in which R p o is cycloalkylalkyl.
Claim 10
Dependent Claim
12 words
A compound of claim 1 in which R p o is ##STR8##
Claim 11
Dependent Claim
10 words
A compound of claim 9 in which n is 0.
Claim 12
Dependent Claim
10 words
A compound of claim 9 in which n is 1.
Claim 13
Dependent Claim
22 words
A compound of claim 1 in which R p and R p ' are each alkoxy of 1 to 4 carbon atoms.
Claim 14
Dependent Claim
15 words
A compound of claim 12 in which R p and R p ' represent 6,7-dialkoxy.
Claim 15
Dependent Claim
15 words
A compound of claim 13 in which R p and R p ' represent 6,7-dimethoxy.
Claim 16
Dependent Claim
12 words
A compound of claim 14 in which R p o is allyl.
Claim 17
Dependent Claim
11 words
The compound of claim 3 which is 1-allyl-4-hydroxy-2-quinolinone-3-carboxylic acid allyl ester.
Claim 18
Dependent Claim
11 words
The compound of claim 15 which is 1-allyl-6,7-dimethoxy-4-hydroxy-2-quinolinone-3-carboxylic acid allyl ester.
Claim 19
Dependent Claim
11 words
The compound of claim 8 which is 1-cyclopropylmethyl-6,7-dimethoxy-4-hydroxy-2-quinolinone-3-carboxylic acid allyl ester.
Claim 20
Dependent Claim
11 words
The compound of claim 6 which is 1-propargyl-4-hydroxy-2-quinolinone-3-carboxylic acid allyl ester.
Claim 21
Dependent Claim
12 words
A compound of claim 14 in which R p o is alkyl.
Claim 22
Dependent Claim
11 words
The compound of claim 20 which is 1-methyl-6,7-dimethoxy-4-hydroxy-2-quinolinone-3-carboxylic acid allyl ester.
Claim 23
Dependent Claim
16 words
A compound of claim 1 in which R p and R p ' together form 6,7-methylenedioxy.
Claim 24
Dependent Claim
12 words
A compound of claim 22 in which R p o is alkyl.
Claim 25
Dependent Claim
12 words
A compound of claim 22 in which R p o is alkenyl.
Claim 26
Dependent Claim
12 words
A compound of claim 24 in which R p o is allyl.
Claim 27
Dependent Claim
11 words
The compound of claim 25 which is 1-allyl-6,7-methylenedioxy-4-hydroxy-2-quinolinone-3-carboxylic acid allyl ester.
Claim 28
Dependent Claim
12 words
A compound of claim 14 in which R p o is hydrogen.
Claim 29
Dependent Claim
11 words
The compound of claim 27 which is 6,7-dimethoxy-4-hydroxy-2-quinolinone-3-carboxylic acid allyl ester.
Claim 30
Dependent Claim
11 words
The compound of claim 15 which is 1-allyl-6,7-dimethoxy-4-hydroxy-2-quinolinone-3-carboxylic acid propargyl ester.
Claim 31
Dependent Claim
31 words
The method of treating allergic conditions due to histamine release comprising administering to a mammal in need of such treatment an allergy treating effective amount of a compound of claim 1.
Claim 32
Dependent Claim
36 words
The method of claim 30 in which R p and R p ' are independently hydrogen, fluoro, chloro, bromo, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, nitro or trifluoromethyl.
Claim 33
Dependent Claim
12 words
The method of claim 31 in which R p o is alkyl.
Claim 34
Dependent Claim
12 words
The method of claim 31 in which R p o is alkenyl.
Claim 35
Dependent Claim
12 words
The method of claim 31 in which R p o is hydrogen.
Claim 36
Dependent Claim
12 words
The method of claim 31 in which R p o is cycloalkyl.
Claim 37
Dependent Claim
12 words
The method of claim 31 in which R p o is alkynyl.
Claim 38
Dependent Claim
12 words
The method of claim 31 in which R p o is cycloalkylalkyl.
Claim 39
Dependent Claim
12 words
The method of claim 31 in which R p o is ##STR9##
Claim 40
Dependent Claim
10 words
The method of claim 38 in which n is 0.
Claim 41
Dependent Claim
10 words
The method of claim 38 in which n is 1.
Claim 42
Dependent Claim
10 words
The method of claim 30 in which M is hydrogen.
Claim 43
Dependent Claim
16 words
The method of claim 31 in which R p and R p ' are each alkoxy.
Claim 44
Dependent Claim
15 words
The method of claim 42 in which R p and R p ' represent 6,7-dialkoxy.
Claim 45
Dependent Claim
15 words
The method of claim 43 in which R p and R p ' represent 6,7-dimethoxy.
Claim 46
Dependent Claim
12 words
The method of claim 33 in which R p o is allyl.
Claim 47
Dependent Claim
15 words
The method of claim 45 in which R p and R p ' represent 6,7-dimethoxy.
Claim 48
Dependent Claim
15 words
The method of claim 32 in which R p and R p ' represent 6,7-dimethoxy.
Claim 49
Dependent Claim
52 words
The method of claim 34 in which R p is hydrogen, fluoro, chloro, bromo, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms and R p ' is fluoro, chloro, bromo, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms.
Claim 50
Dependent Claim
34 words
The method of claim 32 in which R p and R p ' are independently hydrogen, fluoro, chloro, bromo, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms.
Claim 51
Dependent Claim
14 words
The method of claim 48 in which the compound is 6,7-dimethoxy-4-hydroxy-2-quinolinone-3-carboxylic acid allyl ester.
Claim 52
Dependent Claim
14 words
The method of claim 49 in which the compound is 1-methyl-4-hydroxy-2-quinolinone-3-carboxylic acid allyl ester.
Claim 53
Dependent Claim
14 words
The method of claim 45 in which the compound is 1-allyl-4-hydroxy-2-quinolinone-3-carboxylic acid allyl ester.
Claim 54
Dependent Claim
14 words
The method of claim 46 in which the compound is 1-allyl-6,7-dimethoxy-4-hydroxy-2-quinolinone-3-carboxylic acid allyl ester.
Claim 55
Dependent Claim
14 words
The method of claim 47 in which the compound is 1-methyl-6,7-dimethoxy-4-hydroxy-2-quinolinone-3-carboxylic acid allyl ester.
Claim 56
Dependent Claim
18 words
The method of claim 30 in which R p and R p ' together form 6,7-methylenedioxy allyl ester.
Claim 57
Dependent Claim
12 words
The method of claim 55 in which R p o is allyl.
Claim 58
Dependent Claim
14 words
The method of claim 56 in which the compound is 1-allyl-6,7-methylenedioxy-4-hydroxy-2-quinolinone-3-carboxylic acid allyl ester.
Claim 59
Dependent Claim
14 words
The method of claim 46 in which the compound is 1-allyl-6,7-dimethoxy-4-hydroxy-2-quinolinone-3-carboxylic acid propargyl ester.
Claim 60
Dependent Claim
21 words
The method of claim 30 in which the compound is administered at a daily dosage of from 20 to 800 milligrams.
Claim 61
Dependent Claim
30 words
The pharmaceutical composition comprising in unit dosage form a pharmaceutically acceptable carrier and an amount effective to relieve allergic conditions due to histamine release of a compound of claim 1.
Claim 62
Dependent Claim
36 words
A composition of claim 60 in which R p and R p ' are independently hydrogen, fluoro, chloro, bromo, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, nitro or trifluoromethyl.
Claim 63
Dependent Claim
12 words
A composition of claim 61 in which R p o is alkyl.
Claim 64
Dependent Claim
12 words
A composition of claim 61 in which R p o is alkenyl.
Claim 65
Dependent Claim
10 words
A composition of claim 60 in which M is hydrogen.
Claim 66
Dependent Claim
16 words
A composition of claim 60 in which R p and R p ' are each alkoxy.
Claim 67
Dependent Claim
15 words
A composition of claim 65 in which R p and R p ' represent 6,7-dialkoxy.
Claim 68
Dependent Claim
15 words
A composition of claim 66 in which R p and R p ' represent 6,7-dimethoxy.
Claim 69
Dependent Claim
12 words
A composition of claim 63 in which R p o is allyl.
Claim 70
Dependent Claim
15 words
A composition of claim 68 in which R p and R p ' represent 6,7-dimethoxy.
Claim 71
Dependent Claim
15 words
A composition of claim 62 in which R p and R p ' represent 6,7-dimethoxy.
Claim 72
Dependent Claim
14 words
A composition of claim 68 in which the compound is 1-allyl-4-hydroxy-2-quinolinone-3-carboxylic acid allyl ester.
Claim 73
Dependent Claim
14 words
A composition of claim 69 in which the compound is 1-allyl-6,7-dimethoxy-4-hydroxy-2-quinolinone-3-carboxylic acid allyl ester.
Claim 74
Dependent Claim
14 words
A composition of claim 70 in which the compound is 1-methyl-6,7-dimethoxy-4-hydroxy-2-quinolinone-3-carboxylic acid allyl ester.
Claim 75
Dependent Claim
16 words
A composition of claim 60 in which R p and R p ' together form 6,7-methylenedioxy.
Claim 76
Dependent Claim
14 words
A composition of claim 74 in which the compound is 1-allyl-6,7-methylenedioxy-4-hydroxy-2-quinolinone-3-carboxylic acid allyl ester.
Claim 77
Dependent Claim
21 words
A composition of claim 60 containing the compound in an amount of from 5 to 400 milligrams and a solid carrier.
Claim 78
Dependent Claim
10 words
A composition of claim 60 in which R is alkenyl.
Claim 79
Dependent Claim
10 words
A composition of claim 77 in which R is allyl.
References Cited (Backward Citations)
BE806848A
Cited
US3960868A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-10-09 | 1982-04-10 | 1982-10-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-10-09 | 1986-04-10 | 1986-10-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-10-09 | 1990-04-10 | 1990-10-10 | $7700.00 | Window Closed / Lapsed |