US4186199A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Indolo-,1,2-dihydroindolo-, and 1,2,6,7-tetrahydroindolo [1,7-ab][1,5] benzodiazepines
Assignee: CNA Holdings LLC
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Filing: 1978-11-02
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Granted: 1980-01-29
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Expires: 1998-11-02
Abstract
Abstract What is disclosed are ##STR1## wherein X is hydrogen, halogen or trifluoromethyl; Y is hydrogen, halogen or trifluoromethyl; R is hydrogen, loweralkyl, cycloalkyl, phenyl, halophenyl, furyl, pyridinyl, 4-methylpiperazin-1-ylethyl or phenylloweralkyl; R 1 is hydrogen; n and m are independently 0 or 1, but n is not 0 when m is 1, and the bonds between ring positions 1 and 2 and between positions 6 and 7 are respectively saturated when n and m are 1 and are unsaturated when n and m are 0; pharmaceutically acceptable acid addition salts thereof; methods of preparing said compounds; pharmaceutical compositions including said compounds; methods of treatment using the compounds; and intermediates therefor. These compounds are useful as analgesic and anti-inflammatory agents, as well as intermediates for the preparation of other pharmaceutically active compounds.
Inventors
- 👤 Edward J. Glamkowski
- 👤 James M. Fortunato
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 14:24
CPC Classifications
C; C07; C07D; C07D487/00; C07D487/02; C07D487/06; C07D209/00; C07D209/02; C07D209/04; C07D209/08
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
96 words
A compound of the formula ##STR7## or a pharmaceutically acceptable acid addition salt thereof, wherein X is hydrogen or halogen; Y is hydrogen, halogen or trifluoromethyl; R is hydrogen, lower alkyl, cycloalkyl of 3 to 6 carbon atoms, phenyl, halophenyl, furyl or phenylloweralkyl; R 1 is hydrogen; n and m are independently 0 or 1, but n is not 0 when m is 1, and the bonds between positions 1 and 2 and between positions 6 and 7 are respectively saturated when n and m are 1 and are unsaturated when n and ma are 0.
Claim 2
Dependent Claim
96 words
A compound of the formula ##STR7## or a pharmaceutically acceptable acid addition salt thereof, wherein X is hydrogen or halogen; Y is hydrogen, halogen or trifluoromethyl; R is hydrogen, lower alkyl, cycloalkyl of 3 to 6 carbon atoms, phenyl, halophenyl, furyl or phenylloweralkyl; R 1 is hydrogen; n and m are independently 0 or 1, but n is not 0 when m is 1, and the bonds between positions 1 and 2 and between positions 6 and 7 are respectively saturated when n and m are 1 and are unsaturated when n and ma are 0.
Claim 3
Dependent Claim
12 words
A compound or salt as in claim 1 having the formula ##STR8##
Claim 4
Dependent Claim
14 words
The compound as defined in claim 1 which is 1,2-dihydroindolo[1,7-ab][1,5]benzodiazepine or a salt thereof.
Claim 5
Dependent Claim
14 words
The compound as defined in claim 1 which is 4-chloro-1,2-dihydroindolo[1,7-ab][1,5]benzodiazepine or a salt thereof.
Claim 6
Dependent Claim
14 words
The compound as defined in claim 1 which is 1,2-dihydro-6-methylindolo[1,7-ab][1,5]benzodiazepine or a salt thereof.
Claim 7
Dependent Claim
14 words
The compound as defined in claim 1 which is 4-chloro-1,2-dihydro-6-methylindolo[1,7-ab][1,5]benzodiazepine or a salt thereof.
Claim 8
Dependent Claim
14 words
The compound as defined in claim 1 which is 1,2-dihydro-6-methyl-9-trifluoromethylindolo[1,7-ab][1,5]benzodiazepine or a salt thereof.
Claim 9
Dependent Claim
14 words
The compound as defined in claim 1 which is 6-benzyl-1,2-dihydroindolo[1,7-ab][1,5]benzodiazepine or a salt thereof.
Claim 10
Dependent Claim
14 words
The compound as defined in claim 1 which is 1,2-dihydro-6-(2-phenylethyl)-indolo[1,7-ab][1,5]benzodiazepine or a salt thereof.
Claim 11
Dependent Claim
14 words
The compound as defined in claim 1 which is 6-cyclohexyl-1,2-dihydroindolo[1,7-ab][1,5]benzodiazepine or a salt thereof.
Claim 12
Dependent Claim
14 words
The compound as defined in claim 1 which is 1,2-dihydro-6-phenylindolo[1,7-ab][1,5]benzodiazepine or a salt thereof.
Claim 13
Dependent Claim
14 words
The compound as defined in claim 1 which is 1,2-dihydro-6-(o-fluorophenyl)indolo[1,7-ab][1,5]benzodiazepine or a salt thereof.
Claim 14
Dependent Claim
14 words
The compound as defined in claim 1 which is 4-chloro-1,2-dihydro-6-phenylindolo[1,7][1,5]benzodiazepine or a salt thereof.
Claim 15
Dependent Claim
14 words
The compound as defined in claim 1 which is 1,2-dihydro-6-furylindolo[1,7-ab][1,5]benzodiazepine or a salt thereof.
Claim 16
Dependent Claim
14 words
The compound as defined in claim 1 which is 6-phenylindolo[1,7-ab][1,5]benzodiazepine or a salt thereof.
Claim 17
Dependent Claim
14 words
The compound as defined in claim 1 which is 1,2,6,7-tetrahydroindolo[1,7-ab][1,5]benzodiazepine or a salt thereof.
Claim 18
Dependent Claim
14 words
The compound as defined in claim 1 which is 4-chloro-1,2,6,7-tetrahydroindolo[1,7-ab][1,5]benzodiazepine or a salt thereof.
Claim 19
Dependent Claim
14 words
The compound as defined in claim 1 which is 6-methyl-1,2,6,7-tetrahydroindolo[1,7-ab][1,5]benzodiazepine or a salt thereof.
Claim 20
Dependent Claim
14 words
The compound as defined in claim 1 which is 4-chloro-6-methyl-1,2,6,7-tetrahydroindolo[1,7-ab][1,5]benzodiazepine or a salt thereof.
Claim 21
Dependent Claim
14 words
The compound as defined in claim 1 which is 6-(2-phenylethyl)-1,2,6,7-tetrahydroindolo[1,7-ab][1,5]benzodiazepine or a salt thereof.
Claim 22
Dependent Claim
14 words
The compound as defined in claim 1 which is 6-cyclohexyl-1,2,6,7-tetrahydroindolo[1,7-ab][1,5]benzodiazepine or a salt thereof.
Claim 23
Dependent Claim
14 words
The compound as defined in claim 1 which is 6-phenyl-1,2,6,7-tetrahydroindolo[1,7-ab][1,5]benzodiazepine or a salt thereof.
Claim 24
Dependent Claim
14 words
The compound as defined in claim 1 which is 4-chloro-6-phenyl-1,2,6,7-tetrahydroindolo[1,7-ab][1,5]benzodiazepine or a salt thereof.
Claim 25
Dependent Claim
14 words
The compound as defined in claim 1 which is 6-furyl-1,2,6,7-tetrahydroindolo[1,7-ab][1,5]benzodiazepine or a salt thereof.
Claim 26
Dependent Claim
25 words
A method of treating inflammation which comprises administering to a patient in need thereof a pharmaceutically effective amount of a compound defined in claim 1.
Claim 27
Dependent Claim
25 words
A method of treating pain which comprises administering to a patient in need thereof a pharmaceutically effective amount of a compound defined in claim 1.
Claim 28
Dependent Claim
27 words
A pharmaceutical composition which comprises between about 0.5 and about 70 percent by weight of a compound defined in claim 1 and a pharmaceutically acceptable carrier therefor.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-01-28 | 1983-07-30 | 1984-01-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-01-28 | 1987-07-30 | 1988-01-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-01-28 | 1991-07-30 | 1992-01-29 | $7700.00 | Window Closed / Lapsed |