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US3975531A
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4-(5- And 7-)benzoylindolin-2-ones and pharmaceutical uses thereof
Assignee: AH Robins Co Inc
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Filing: 1975-01-29
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Granted: 1976-08-17
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Expires: 1995-01-29
Abstract
Abstract Novel 4-(5- and 7-)benzoylindolin-2-ones of the formula: ##SPC1## Wherein R is hydrogen, lower-alkyl, or methylthio, R 1 is hydrogen or lower-alkyl, R 2 is lower-alkyl, lower-alkoxy, halogen, nitro or trifluoromethyl, R 3 is hydrogen, halogen or lower-alkoxy, and n is 0, 1 or 2, are prepared by (a) acylation of indolin-2-one to give 5-benzoylindoline-2-one, (b) cyclization of 2-acetamido-3-benzoylphenylacetic acid or ethyl 2-acetamido-3-benzoylphenylacetate to give 7-benzoyindoline-2-one, or (c) by reacting aminobenzophenones with alkyl α(methylthio)acetates to give alkyl 2-amino-3-(5- or 6-)benzoyl-α-(methylthio)phenylacetates which are cyclized and demethylthiolated to 4-(5- and 7-)benzoylindolin-2-ones. The novel compounds possess anti-inflammatory activity and are intermediates for the preparation of 2-amino-3-(5- or 6-) benzoylphenylacetic acids which posess anti-inflammatory properties.
Inventors
- 👤 William John Welstead, Jr.
- 👤 Henry Wayne Moran
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 14:07
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/04; C07D209/08; C07D209/30; C07D209/32; C07D209/34
Claims Analysis
Total Claims: 35
Claim 1
Independent Claim
69 words
A 4-(5- and 7-)benzoylindolin-2-one of the formula: ##SPC6## wherein; R is selected from the group consisting of hydrogen, lower-alkyl or methylthio, R 1 is selected from the group consisting of hydrogen or lower-alkyl, R 2 is selected from the group consisting of lower-alkyl, lower-alkoxy, halogen, nitro or trifluoromethyl, R 3 is selected from the group consisting of hydrogen, halogen or lower alkoxy, and n is 0, 1 or 2.
Claim 2
Dependent Claim
69 words
A 4-(5- and 7-)benzoylindolin-2-one of the formula: ##SPC6## wherein; R is selected from the group consisting of hydrogen, lower-alkyl or methylthio, R 1 is selected from the group consisting of hydrogen or lower-alkyl, R 2 is selected from the group consisting of lower-alkyl, lower-alkoxy, halogen, nitro or trifluoromethyl, R 3 is selected from the group consisting of hydrogen, halogen or lower alkoxy, and n is 0, 1 or 2.
Claim 3
Dependent Claim
8 words
The compound of claim 1 which is 5-benzoylindolin-2-one.
Claim 4
Dependent Claim
8 words
The compound of claim 1 which is 7-benzoylindolin-2-one.
Claim 5
Dependent Claim
8 words
The compound of claim 1 which is 4-benzoylindolin-2-one.
Claim 6
Dependent Claim
8 words
The compound of claim 1 which is 3-methyl-7-benzoylindolin-2-one.
Claim 7
Dependent Claim
8 words
The compound of claim 1 which is 3-(n-butyl)-5-benzoylindolin-2-one.
Claim 8
Dependent Claim
8 words
The compound of claim 1 which is 7-benzoyl-5-chloroindolin-2-one.
Claim 9
Dependent Claim
8 words
The compound of claim 1 which is 7-benzoyl-5-methoxyindolin-2-one.
Claim 10
Dependent Claim
8 words
The compound of claim 1 which is 7-(4-chlorobenzoyl)indolin-2-one.
Claim 11
Dependent Claim
57 words
A 4-(5- and 7-)benzoyl-3-methylthioindolin-2-one of the formula: ##SPC7## wherein; R 1 is selected from the group consisting of hydrogen or lower-alkyl, R 2 is selected from the group consisting of lower-alkyl lower-alkoxy, halogen, nitro or trifluoromethyl, R 3 is selected from the group consisting of hydrogen, halogen, or lower alkoxy, and n is 0, 1 or 2.
Claim 12
Dependent Claim
57 words
A 4-(5- and 7-)benzoyl-3-methylthioindolin-2-one of the formula: ##SPC7## wherein; R 1 is selected from the group consisting of hydrogen or lower-alkyl, R 2 is selected from the group consisting of lower-alkyl lower-alkoxy, halogen, nitro or trifluoromethyl, R 3 is selected from the group consisting of hydrogen, halogen, or lower alkoxy, and n is 0, 1 or 2.
Claim 13
Dependent Claim
8 words
The compound of claim 10 which is 4-benzoyl-3-methylthioindolin-2-one.
Claim 14
Dependent Claim
8 words
The compound of claim 10 which is 7-(4-chlorobenzoyl)-3-methylthioindolin-2-one.
Claim 15
Dependent Claim
8 words
The compound of claim 10 which is 7-benzoyl-3-methyl-3-methylthioindolin-2-one.
Claim 16
Dependent Claim
8 words
The compound of claim 10 which is 7-benzoyl-3-methylthioindolin-2-one.
Claim 17
Independent Claim
95 words
A method of treating inflammation which comprises administering to an animal in need thereof an effective amount of a compound selected from the group consisting of 4-(5- and 7-)benzoylindolin-2-one of the formula: ##SPC8## wherein: R is selected from the group consisting of hydrogen, lower-alkyl or methylthio, R 1 is selected from the group consisting of hydrogen or lower alkyl, R 2 is selected from the group consisting of lower-alkyl, lower-alkoxy, halogen, nitro or trifluoromethyl, R 3 is selected from the group consisting of hydrogen, halogen or lower alkoxy, and n is 0, 1 or 2.
Claim 18
Independent Claim
95 words
A method of treating inflammation which comprises administering to an animal in need thereof an effective amount of a compound selected from the group consisting of 4-(5- and 7-)benzoylindolin-2-one of the formula: ##SPC8## wherein: R is selected from the group consisting of hydrogen, lower-alkyl or methylthio, R 1 is selected from the group consisting of hydrogen or lower alkyl, R 2 is selected from the group consisting of lower-alkyl, lower-alkoxy, halogen, nitro or trifluoromethyl, R 3 is selected from the group consisting of hydrogen, halogen or lower alkoxy, and n is 0, 1 or 2.
Claim 19
Dependent Claim
29 words
A method according to claim 15 wherein the active ingredient is administered together with a pharmaceutically acceptable carrier therefor and in an amount of about one to 100 milligrams.
Claim 20
Dependent Claim
11 words
The method of claim 16 wherein the active compound is 5-benzoylindolin-2-one.
Claim 21
Dependent Claim
11 words
The method of claim 16 wherein the active compound is 7-benzoylindolin-2-one.
Claim 22
Dependent Claim
11 words
The method of claim 16 wherein the active compound is 3-methyl-5-benzoylindolin-2-one.
Claim 23
Dependent Claim
11 words
The method of claim 16 wherein the active compound is 3-(n-butyl)-5-benzoylindolin-2-one.
Claim 24
Dependent Claim
11 words
The method of claim 16 wherein the active compound is 7-benzoyl-5-chloroindolin-2-one.
Claim 25
Dependent Claim
11 words
The method of claim 16 wherein the active compound is 7-benzoyl-5-methoxyindolin-2-one.
Claim 26
Dependent Claim
11 words
The method of claim 16 wherein the active compound is 7-(4-chlorobenzoyl)indolin-2-one.
Claim 27
Dependent Claim
95 words
A pharmaceutical composition, useful for its anti-inflammatory effect, comprising (a) an effective amount of about one to 100 milligrams of a 4-(5- and 7-)benzoylindolin-2-one of the formula: ##SPC9## wherein: R is selected from the group consisting of hydrogen, lower-alkyl or methylthio, R 1 is selected from the group consisting of hydrogen or lower-alkyl, R 2 is selected from the group consisting of lower-alkyl, lower-alkoxy, halogen, nitro or trifluoromethyl, R 3 is selected from the group consisting of hydrogen, halogen or lower alkoxy, n is 0, 1 or 2, and (b) a pharmaceutically acceptable carrier therefor.
Claim 28
Dependent Claim
95 words
A pharmaceutical composition, useful for its anti-inflammatory effect, comprising (a) an effective amount of about one to 100 milligrams of a 4-(5- and 7-)benzoylindolin-2-one of the formula: ##SPC9## wherein: R is selected from the group consisting of hydrogen, lower-alkyl or methylthio, R 1 is selected from the group consisting of hydrogen or lower-alkyl, R 2 is selected from the group consisting of lower-alkyl, lower-alkoxy, halogen, nitro or trifluoromethyl, R 3 is selected from the group consisting of hydrogen, halogen or lower alkoxy, n is 0, 1 or 2, and (b) a pharmaceutically acceptable carrier therefor.
Claim 29
Dependent Claim
12 words
A composition according to claim 24 wherein the active ingredient is 5-benzoylindolin-2-one.
Claim 30
Dependent Claim
12 words
A composition according to claim 24 wherein the active ingredient is 7-benzoylindolin-2-one.
Claim 31
Dependent Claim
12 words
A composition according to claim 24 wherein the active ingredient is 3-methyl-5-benzoylindolin-2-one.
Claim 32
Dependent Claim
12 words
A composition according to claim 24 wherein the active ingredient is 3-(n-butyl)-5-benzoylindolin-2-one.
Claim 33
Dependent Claim
12 words
A composition according to claim 24 wherein the active ingredient is 7-benzoyl-5-chloroindolin-2-one.
Claim 34
Dependent Claim
12 words
A composition according to claim 24 wherein the active ingredient is 7-benzoyl-5-methoxyindolin-2-one.
Claim 35
Dependent Claim
12 words
A composition according to claim 24 wherein the active ingredient is 7-(4-chlorobenzoyl)indolin-2-one.
References Cited (Backward Citations)
US3679701A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-08-17 | 1980-02-16 | 1980-08-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-08-17 | 1984-02-16 | 1984-08-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-08-17 | 1988-02-16 | 1988-08-17 | $7700.00 | Window Closed / Lapsed |