US4045576A
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US
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Anti-inflammatory methods using 2-amino-3-(5- and 6-)benzoylphenylacetic acids, esters and metal salts thereof and the compounds
Assignee: AH Robins Co Inc
•
Filing: 1975-08-13
•
Granted: 1977-08-30
•
Expires: 1995-08-13
Abstract
Abstract Novel 2-amino-3-(5- and 6-)benzoylphenylacetic acids, esters and metal salts of the formula: ##STR1## wherein R is hydrogen or lower alkyl, R 1 is hydrogen, lower-alkyl, sodium or potassium, R 2 is hydrogen, halogen or lower alkoxy, X is hydrogen, lower alkyl, halogen, nitro or trifluoromethyl, Y is hydrogen, lower alkyl, halogen, nitro or trifluoromethyl, and Am is primary amino (--NH 2 ) methylamino or dimethylamino. The compounds are prepared by hydrolysis of 4-(5- and 7-)benzoylindolin-2-ones to give the 2-amino-3-(5- and 6-)benzoylphenylacetic acids wherein amino is primary amino. The free acids are converted to the esters and metal salts. The calcium and magnesium salts are disclosed and are within the scope of the present invention. The compounds have anti-inflammatory activity, are effective in lowering the cholesterol levels in hyperlipemic rats and inhibit blood platelet aggregation.
Inventors
- 👤 William J. Welstead, Jr.
- 👤 Henry W. Moran
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 16:36
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/04; C07D209/30; C07D209/32; C07D209/34; A; A61; A61P; A61P29/00; A61P9/00; A61P9/10; C07D209/08; C07D317/00; C07D317/08; C07D317/44; C07D317/46; C07D317/48; C07D317/50; C07D317/54
Claims Analysis
Total Claims: 76
Claim 1
Independent Claim
145 words
The method for alleviating inflammation in a living animal body with a minimum of undesirable side effects comprising internally administering to said living animal body an effective amount of a compound selected from the group having the formula: ##STR8## wherein: R is selected from the group consisting of hydrogen and lower alkyl, R 1 is selected from the group consisting of hydrogen, lower alkyl, sodium and potassium R 2 is selected from the group consisting of hydrogen, halogen having an atomic weight less than 80 and lower alkoxy, X is selected from the group consisting of hydrogen, lower alkyl, halogen having an atomic weight less than 80, nitro and trifluoromethyl, Y is selected from the group consisting of hydrogen, lower alkyl, halogen having an atomic weight less than 80, nitro and trifluoromethyl, and Am is selected from the group consisting of primary amino and dimethylamino.
Claim 2
Independent Claim
145 words
The method for alleviating inflammation in a living animal body with a minimum of undesirable side effects comprising internally administering to said living animal body an effective amount of a compound selected from the group having the formula: ##STR8## wherein: R is selected from the group consisting of hydrogen and lower alkyl, R 1 is selected from the group consisting of hydrogen, lower alkyl, sodium and potassium R 2 is selected from the group consisting of hydrogen, halogen having an atomic weight less than 80 and lower alkoxy, X is selected from the group consisting of hydrogen, lower alkyl, halogen having an atomic weight less than 80, nitro and trifluoromethyl, Y is selected from the group consisting of hydrogen, lower alkyl, halogen having an atomic weight less than 80, nitro and trifluoromethyl, and Am is selected from the group consisting of primary amino and dimethylamino.
Claim 3
Dependent Claim
11 words
The method of claim 1 wherein the compound is 2-amino-5-benzoylphenylacetic acid.
Claim 4
Dependent Claim
11 words
The method of claim 1 wherein the compound is 2-amino-3-benzoyl-5-chlorophenylacetic acid.
Claim 5
Dependent Claim
10 words
The method of claim 1 wherein the compound is ethyl-2-amino-3-benzoylphenylacetate.
Claim 6
Dependent Claim
10 words
The method of claim 1 wherein the compound is methyl-2-amino-3-benzoylphenylacetate.
Claim 7
Dependent Claim
10 words
The method of claim 1 wherein the compound is methyl-2-dimethylamino-3-benzoylphenylacetate.
Claim 8
Dependent Claim
11 words
The method of claim 1 wherein the compound is 2-dimethylamino-3-benzoylphenylacetic acid.
Claim 9
Independent Claim
31 words
The method for alleviating inflammation in a living animal body with a minimum of undesirable side effects comprising internally administering to said living animal body an effective amount of 2-amino-3-benzoylphenylacetic acid.
Claim 10
Independent Claim
31 words
The method for alleviating inflammation in a living animal body with a minimum of undesirable side effects comprising internally administering to said living animal body an effective amount of 2-amino-3-benzoylphenylacetic acid.
Claim 11
Independent Claim
32 words
The method for alleviating inflammation in a living animal body with a minimum of undesirable side effects comprising internally administering to said living animal body an effective amount of sodium 2-amino-3-benzoyl-5-methoxyphenylacetate sesquihydrate.
Claim 12
Independent Claim
32 words
The method for alleviating inflammation in a living animal body with a minimum of undesirable side effects comprising internally administering to said living animal body an effective amount of sodium 2-amino-3-benzoyl-5-methoxyphenylacetate sesquihydrate.
Claim 13
Independent Claim
32 words
The method for alleviating inflammation in a living animal body with a minimum of undesirable side effects comprising internally administering to said living animal body an effective amount of sodium 2-amino-3-benzoylphenylacetate dihydrate.
Claim 14
Independent Claim
32 words
The method for alleviating inflammation in a living animal body with a minimum of undesirable side effects comprising internally administering to said living animal body an effective amount of sodium 2-amino-3-benzoylphenylacetate dihydrate.
Claim 15
Independent Claim
32 words
The method for alleviating inflammation in a living animal body with a minimum of undesirable side effects comprising internally administering to said living animal body an effective amount of potassium 2-amino-3-benzoylphenylacetate hydrate.
Claim 16
Independent Claim
32 words
The method for alleviating inflammation in a living animal body with a minimum of undesirable side effects comprising internally administering to said living animal body an effective amount of potassium 2-amino-3-benzoylphenylacetate hydrate.
Claim 17
Dependent Claim
143 words
A therapeutic composition suitable for alleviating inflammation comprising (a) an effective amount of between about 0.1 and 150 milligrams of a compound selected from the group having the formula: ##STR9## wherein: R is selected from the group consisting of hydrogen and lower alkyl, R 1 is selected from the group consisting of hydrogen, lower alkyl, sodium and potassium, R 2 is selected from the group consisting of hydrogen, halogen having an atomic weight less than 80, and lower alkoxy, X is selected from the group consisting of hydrogen, lower alkyl, halogen having an atomic weight less than 80, nitro and trifluoromethyl, Y is selected from the group consisting of hydrogen, lower alkyl, halogen having an atomic weight less than 80, nitro and trifluoromethyl, and Am is selected from the group consisting of primary amino, and dimethylamino, and (b) a pharmaceutically acceptable carrier therefor.
Claim 18
Dependent Claim
143 words
A therapeutic composition suitable for alleviating inflammation comprising (a) an effective amount of between about 0.1 and 150 milligrams of a compound selected from the group having the formula: ##STR9## wherein: R is selected from the group consisting of hydrogen and lower alkyl, R 1 is selected from the group consisting of hydrogen, lower alkyl, sodium and potassium, R 2 is selected from the group consisting of hydrogen, halogen having an atomic weight less than 80, and lower alkoxy, X is selected from the group consisting of hydrogen, lower alkyl, halogen having an atomic weight less than 80, nitro and trifluoromethyl, Y is selected from the group consisting of hydrogen, lower alkyl, halogen having an atomic weight less than 80, nitro and trifluoromethyl, and Am is selected from the group consisting of primary amino, and dimethylamino, and (b) a pharmaceutically acceptable carrier therefor.
Claim 19
Dependent Claim
11 words
The composition of claim 12 wherein the compound is 2-amino-5-benzoylphenylacetic acid.
Claim 20
Dependent Claim
11 words
The composition of claim 12 wherein the compound is 2-amino-3-benzoyl-5-chlorophenylacetic acid.
Claim 21
Dependent Claim
11 words
The composition of claim 12 wherein the compound is ethyl 2-amino-3-benzoylphenylacetate.
Claim 22
Dependent Claim
11 words
The composition of claim 12 wherein the compound is methyl 2-amino-3-benzoylphenylacetate.
Claim 23
Dependent Claim
11 words
The composition of claim 12 wherein the compound is methyl 2-dimethylamino-3-benzoylphenylacetate.
Claim 24
Dependent Claim
11 words
The composition of claim 12 wherein the compound is 2-dimethylamino-3-benzoylphenylacetic acid.
Claim 25
Dependent Claim
30 words
A therapeutic composition suitable for alleviating inflammation comprising (a) an effective amount of between about 0.1 and 150 milligrams of sodium 2-amino-3-benzoylphenylacetic acid and (b) a pharmaceutically acceptable carrier thereof.
Claim 26
Dependent Claim
30 words
A therapeutic composition suitable for alleviating inflammation comprising (a) an effective amount of between about 0.1 and 150 milligrams of sodium 2-amino-3-benzoylphenylacetic acid and (b) a pharmaceutically acceptable carrier thereof.
Claim 27
Dependent Claim
30 words
A therapeutic composition suitable for alleviating inflammation comprising (a) an effective amount of between about 0.1 and 150 milligrams of sodium 2-amino-3-benzoyl-5-methoxyphenylacetate sesquihydrate and (b) a pharmaceutically acceptable carrier thereof.
Claim 28
Dependent Claim
30 words
A therapeutic composition suitable for alleviating inflammation comprising (a) an effective amount of between about 0.1 and 150 milligrams of sodium 2-amino-3-benzoyl-5-methoxyphenylacetate sesquihydrate and (b) a pharmaceutically acceptable carrier thereof.
Claim 29
Dependent Claim
30 words
A therapeutic composition suitable for alleviating inflammation comprising (a) an effective amount of between about 0.1 and 150 milligrams of sodium 2-amino-3-benzoyl-phenylacetate dihydrate and (b) a pharmaceutically acceptable carrier thereof.
Claim 30
Dependent Claim
30 words
A therapeutic composition suitable for alleviating inflammation comprising (a) an effective amount of between about 0.1 and 150 milligrams of sodium 2-amino-3-benzoyl-phenylacetate dihydrate and (b) a pharmaceutically acceptable carrier thereof.
Claim 31
Dependent Claim
30 words
A therapeutic composition suitable for alleviating inflammation comprising (a) an effective amount of between about 0.1 and 150 milligrams of potassium 2-amino-3-benzoylphenylacetate hydrate and (b) a pharmaceutically acceptable carrier thereof.
Claim 32
Dependent Claim
30 words
A therapeutic composition suitable for alleviating inflammation comprising (a) an effective amount of between about 0.1 and 150 milligrams of potassium 2-amino-3-benzoylphenylacetate hydrate and (b) a pharmaceutically acceptable carrier thereof.
Claim 33
Dependent Claim
119 words
A compound selected from the group having the formula: ##STR10## wherein; R is selected from the group consisting of hydrogen and lower alkyl, R 1 is selected from the group consisting of hydrogen, lower alkyl, sodium and potassium, R 2 is selected from the group consisting of hydrogen, halogen having an atomic weight less than 80, and lower alkoxy, X is selected from the group consisting of hydrogen, lower alkyl, halogen having an atomic weight less than 80, nitro and trifluoromethyl, Y is selected from the group consisting of hydrogen, lower alkyl, halogen having an atomic weight less than 80, nitro and trifluoromethyl, and Am is selected from the group consisting of primary amino (-NH 2 ) and dimethylamino.
Claim 34
Dependent Claim
119 words
A compound selected from the group having the formula: ##STR10## wherein; R is selected from the group consisting of hydrogen and lower alkyl, R 1 is selected from the group consisting of hydrogen, lower alkyl, sodium and potassium, R 2 is selected from the group consisting of hydrogen, halogen having an atomic weight less than 80, and lower alkoxy, X is selected from the group consisting of hydrogen, lower alkyl, halogen having an atomic weight less than 80, nitro and trifluoromethyl, Y is selected from the group consisting of hydrogen, lower alkyl, halogen having an atomic weight less than 80, nitro and trifluoromethyl, and Am is selected from the group consisting of primary amino (-NH 2 ) and dimethylamino.
Claim 35
Dependent Claim
9 words
The compound of claim 23 which is 2-amino-5-benzoylphenylacetic acid.
Claim 36
Dependent Claim
9 words
The compound of claim 23 which is 2-amino-3-benzoyl-5-chlorophenylacetic acid.
Claim 37
Dependent Claim
9 words
The compound of claim 23 which is ethyl 2-amino-3-benzoylphenylacetate.
Claim 38
Dependent Claim
9 words
The compound of claim 23 whcih is methyl 2-amino-3-benzoylphenylacetate.
Claim 39
Dependent Claim
9 words
The compound of claim 23 which is methyl 2-dimethylamino-3-benzoylphenylacetate.
Claim 40
Dependent Claim
9 words
The compound of claim 23 which is 2-dimethylamino-3-benzoylphenylacetic acid.
Claim 41
Dependent Claim
116 words
A compound selected from the group having the formula: ##STR11## wherein; R is selected from the group consisting of hydrogen and lower alkyl, R 2 is selected from the group consisting of hydrogen, halogen having an atomic weight less than 80 and lower alkoxy, R 3 is selected from the group consisting of calcium and magnesium, X is selected from the group consisting of hydrogen, lower alkyl, halogen having an atomic weight less than 80, nitro and trifluoromethyl, Y is selected from the group consisting of hydrogen, lower alkyl, halogen having an atomic weight less than 80, nitro and trifluoromethyl, and Am is selected from the group consisting of primary amino (--NH 2 ) and dimethylamino.
Claim 42
Dependent Claim
116 words
A compound selected from the group having the formula: ##STR11## wherein; R is selected from the group consisting of hydrogen and lower alkyl, R 2 is selected from the group consisting of hydrogen, halogen having an atomic weight less than 80 and lower alkoxy, R 3 is selected from the group consisting of calcium and magnesium, X is selected from the group consisting of hydrogen, lower alkyl, halogen having an atomic weight less than 80, nitro and trifluoromethyl, Y is selected from the group consisting of hydrogen, lower alkyl, halogen having an atomic weight less than 80, nitro and trifluoromethyl, and Am is selected from the group consisting of primary amino (--NH 2 ) and dimethylamino.
Claim 43
Dependent Claim
3 words
Calcium 2-amino-3-benzoylphenylacetate dihydrate.
Claim 44
Dependent Claim
3 words
Calcium 2-amino-3-benzoylphenylacetate dihydrate.
Claim 45
Dependent Claim
3 words
Magnesium 2-amino-3-benzoylphenylacetate trihydrate.
Claim 46
Dependent Claim
3 words
Magnesium 2-amino-3-benzoylphenylacetate trihydrate.
Claim 47
Dependent Claim
2 words
2-Amino-3-benzoylphenylacetic acid.
Claim 48
Dependent Claim
2 words
2-Amino-3-benzoylphenylacetic acid.
Claim 49
Dependent Claim
2 words
Sodium 2-amino-3-benzoyl-5-methoxyphenylacetate.
Claim 50
Dependent Claim
2 words
Sodium 2-amino-3-benzoyl-5-methoxyphenylacetate.
Claim 51
Dependent Claim
3 words
Sodium 2-amino-3-benzoyl-5-methoxyphenylacetate sesquihydrate.
Claim 52
Dependent Claim
3 words
Sodium 2-amino-3-benzoyl-5-methoxyphenylacetate sesquihydrate.
Claim 53
Dependent Claim
2 words
Sodium 2-amino-3-benzoylphenylacetate.
Claim 54
Dependent Claim
2 words
Sodium 2-amino-3-benzoylphenylacetate.
Claim 55
Dependent Claim
3 words
Sodium 2-amino-3-benzoylphenylacetate dihydrate.
Claim 56
Dependent Claim
3 words
Sodium 2-amino-3-benzoylphenylacetate dihydrate.
Claim 57
Dependent Claim
2 words
Potassium 2-amino-3-benzoylphenylacetate.
Claim 58
Dependent Claim
2 words
Potassium 2-amino-3-benzoylphenylacetate.
Claim 59
Dependent Claim
3 words
Potassium 2-amino-3-benzoylphenylacetate hydrate.
Claim 60
Dependent Claim
3 words
Potassium 2-amino-3-benzoylphenylacetate hydrate.
Claim 61
Dependent Claim
3 words
Sodium 2-amino-3-(p-chlorobenzoyl)phenylacetate hydrate.
Claim 62
Dependent Claim
3 words
Sodium 2-amino-3-(p-chlorobenzoyl)phenylacetate hydrate.
Claim 63
Dependent Claim
2 words
Ethyl 2-amino-3-(p-chlorobenzoyl)phenylacetate.
Claim 64
Dependent Claim
2 words
Ethyl 2-amino-3-(p-chlorobenzoyl)phenylacetate.
Claim 65
Dependent Claim
4 words
Sodium 2-amino-3-benzoyl-α-methylphenylacetate hydrate 2.5.
Claim 66
Dependent Claim
4 words
Sodium 2-amino-3-benzoyl-α-methylphenylacetate hydrate 2.5.
Claim 67
Dependent Claim
2 words
2-Amino-3-(p-fluorobenzoyl)phenylacetic acid.
Claim 68
Dependent Claim
2 words
2-Amino-3-(p-fluorobenzoyl)phenylacetic acid.
Claim 69
Dependent Claim
3 words
Sodium 2-amino-3-(p-fluorobenzoyl)phenylacetate hydrate.
Claim 70
Dependent Claim
3 words
Sodium 2-amino-3-(p-fluorobenzoyl)phenylacetate hydrate.
Claim 71
Dependent Claim
2 words
Calcium 2-amino-3-benzoylphenylacetate.
Claim 72
Dependent Claim
2 words
Calcium 2-amino-3-benzoylphenylacetate.
Claim 73
Dependent Claim
2 words
Magnesium 2-amino-3-benzoylphenylacetate.
Claim 74
Dependent Claim
2 words
Magnesium 2-amino-3-benzoylphenylacetate.
Claim 75
Dependent Claim
2 words
2-Amino-3-(p-methoxybenzoyl)phenylacetic acid.
Claim 76
Dependent Claim
2 words
2-Amino-3-(p-methoxybenzoyl)phenylacetic acid.
References Cited (Backward Citations)
US3828093A
Cited
DE2324768A1
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-08-29 | 1981-02-28 | 1981-08-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-08-29 | 1985-02-28 | 1985-08-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-08-29 | 1989-02-28 | 1989-08-30 | $7700.00 | Window Closed / Lapsed |