US4020094A
Expired / Lapsed
US
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2-Substituted-5-oxo-5H-dibenzo[a,d]cycloheptenes, the salts and esters thereof, having pharmaceutical activity
Assignee: Syntex USA LLC
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Filing: 1975-03-24
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Granted: 1977-04-26
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Expires: 1995-03-24
Abstract
Abstract 2-Substituted-5-oxo-5H-dibenzo[a,d]cycloheptenes represented by the following formula: <IMAGE> where R' is hydrogen, alkyl having 1 to 12 carbon atoms, or <IMAGE> where n is an integer from 2 to 4, inclusive, and R4 and R5 are independently lower alkyl having 1 to 6 carbon atoms or together R4 and R5 and the nitrogen atom to which they are attached form a heterocyclic ring having 5 or 6 total ring atoms; one of R2 and R3 is hydrogen and the other is hydrogen, methyl, or ethyl, or together R2 and R3 are methylene; and the pharmaceutically acceptable salts thereof. The compounds have anti-inflammatory, analgesic, and antipyretic activities and, accordingly, are useful in the treatment of inflammation, pain and/or pyrexia.
Inventors
- 👤 Peter H. Nelson
- 👤 Karl G. Untch
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 04:07
CPC Classifications
C; C07; C07C; C07C65/00; C07C65/32; C07C65/38; C07C51/00; C07C51/41; C07C51/412; C07C59/00; C07C59/40; C07C59/76; C07C59/86; C07C63/00; C07C63/33; C07C63/331; C07C63/66; C07C65/34; C07C65/36
Claims Analysis
Total Claims: 31
Claim 1
Independent Claim
82 words
A compound selected from the group of compounds represented by the formula: ##STR6## where R' is hydrogen, alkyl having 1 to 12 carbon atoms, or ##STR7## n is an integer from 2 through 4, inclusive; R 4 and R 5 are independently lower alkyl having 1 to 6 carbon atoms; one of R 2 and R 3 is hydrogen and the other is hydrogen, methyl, or ethyl, or together R 2 and R 3 are methylene; and the pharmaceutically acceptable salts thereof.
Claim 2
Dependent Claim
82 words
A compound selected from the group of compounds represented by the formula: ##STR6## where R' is hydrogen, alkyl having 1 to 12 carbon atoms, or ##STR7## n is an integer from 2 through 4, inclusive; R 4 and R 5 are independently lower alkyl having 1 to 6 carbon atoms; one of R 2 and R 3 is hydrogen and the other is hydrogen, methyl, or ethyl, or together R 2 and R 3 are methylene; and the pharmaceutically acceptable salts thereof.
Claim 3
Dependent Claim
9 words
The compound of claim 1 where R' is hydrogen.
Claim 4
Dependent Claim
15 words
The compound of claim 1 where R' is alkyl having 1 to 12 carbon atoms.
Claim 5
Dependent Claim
19 words
The compound of claim 1 where R' is ##STR8## and R 4 and R 5 are independently lower alkyl.
Claim 6
Dependent Claim
14 words
The compound of claim 1 where both R 2 and R 3 are hydrogen.
Claim 7
Dependent Claim
14 words
The compound of claim 1 where said compound of Formula I is (5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)acetic acid.
Claim 8
Dependent Claim
18 words
The compound of claim 1 wherein said compound is the sodium, potassium or calcium salt of 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)acetic acid.
Claim 9
Dependent Claim
14 words
The compound of claim 1 where said compound of Formula I is 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)butyric acid.
Claim 10
Dependent Claim
14 words
The compound of claim 1 where said compound of Formula I is 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)acrylic acid.
Claim 11
Dependent Claim
70 words
A compound selected from the group of compounds represented by the formula: ##STR9## where R' is hydrogen, alkyl having 1 to 12 carbon atoms, or ##STR10## n is an integer from 2 through 4, inclusive; R 4 and R 5 are independently lower alkyl having 1 to 6 carbon atoms; one of R 2 and R 3 is hydrogen and the other is methyl; and the pharmaceutically acceptable salts thereof.
Claim 12
Dependent Claim
70 words
A compound selected from the group of compounds represented by the formula: ##STR9## where R' is hydrogen, alkyl having 1 to 12 carbon atoms, or ##STR10## n is an integer from 2 through 4, inclusive; R 4 and R 5 are independently lower alkyl having 1 to 6 carbon atoms; one of R 2 and R 3 is hydrogen and the other is methyl; and the pharmaceutically acceptable salts thereof.
Claim 13
Dependent Claim
15 words
The compound of claim 10 wherein R' is alkyl having 1 to 12 carbon atoms.
Claim 14
Dependent Claim
19 words
The compound of claim 10 wherein R' is ##STR11## where R 4 and R 5 are independently lower alkyl.
Claim 15
Dependent Claim
2 words
2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propionic acid.
Claim 16
Dependent Claim
2 words
2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propionic acid.
Claim 17
Dependent Claim
18 words
The compound of claim 10 wherein said compound is the sodium, potassium, or calcium salt of 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propionic acid.
Claim 18
Dependent Claim
15 words
The compound of claim 10 wherein said compound is the sodium salt of 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propionic acid.
Claim 19
Dependent Claim
11 words
The compound of claim 10 wherein said compound is isopentyl 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propionate.
Claim 20
Dependent Claim
11 words
The compound of claim 10 wherein said compound is dodecyl 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propionate.
Claim 21
Dependent Claim
11 words
The compound of claim 10 wherein said compound is β-N,N-dimethylaminoethyl 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propionate.
Claim 22
Dependent Claim
11 words
The compound of claim 10 wherein said compound is β-N,N-diethylaminoethyl 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propionate.
Claim 23
Dependent Claim
11 words
The compound of claim 10 wherein said compound is β-N,N-methylethylaminoethyl 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propionate.
Claim 24
Dependent Claim
3 words
d 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propionic acid.
Claim 25
Dependent Claim
3 words
d 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propionic acid.
Claim 26
Dependent Claim
19 words
The compound of claim 10 wherein said compound is the sodium, potassium or calcium salt of d 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propionic acid.
Claim 27
Dependent Claim
16 words
The compound of claim 10 wherein said compound is the sodium salt of d 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propionic acid.
Claim 28
Dependent Claim
15 words
The compound of claim 10 wherein said compound of Formula I is 1 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-1-yl)propionic acid.
Claim 29
Dependent Claim
16 words
The compound of claim 10 wherein said compound is the sodium salt of 1 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propionic acid.
Claim 30
Dependent Claim
15 words
A compound selected from the group consisting of 2'-carboxyphenyl 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propionate, 2'-carbomethoxyphenyl 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propionate, and phenyl 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propionate.
Claim 31
Dependent Claim
15 words
A compound selected from the group consisting of 2'-carboxyphenyl 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propionate, 2'-carbomethoxyphenyl 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propionate, and phenyl 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)propionate.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-04-25 | 1980-10-25 | 1981-04-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-04-25 | 1984-10-25 | 1985-04-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-04-25 | 1988-10-25 | 1989-04-26 | $7700.00 | Window Closed / Lapsed |