US3940397A
Expired / Lapsed
US
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2-[(Substituted-piperazinyl)alkyl]-1H-benz[de]isoquinoline-1,3(2H)-diones
Assignee: ER Squibb and Sons LLC
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Filing: 1974-11-13
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Granted: 1976-02-24
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Expires: 1994-11-13
Abstract
Abstract Compounds of the following formula and their acid addition salts ##SPC1## Wherein R 1 and R 2 are independently selected from hydrogen, halogen, lower alkyl, lower alkoxy, lower alkylthio, nitro, cyano, amino and trifluoromethyl; A is a straight or branched chain alkylene of 1 to 8 carbons; and Z is ##SPC2## Wherein R 3 is selected from phenyl, phenyl-lower alkyl, and substituted phenyl and phenyl-lower alkyl are disclosed. These compounds exhibit antidepressant activity. In addition these compounds are useful as antiinflammatory agents.
Inventors
- 👤 Peter C. Wade
- 👤 Berthold Richard Vogt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 07:53
CPC Classifications
C; C07; C07D; C07D221/00; C07D221/02; C07D221/04; C07D221/06; C07D221/14
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
103 words
A compound of the formula ##SPC12## wherein R 1 and R 2 are each independently selected from the group consisting of hydrogen, halogen, lower alkyl, lower alkoxy, lower alkylthio, nitro, cyano, amino, and trifluoromethyl; A is a straight or branched chain alkylene of 1 to 8 carbons; and Z is ##SPC13## wherein R 3 is selected from the group consisting of phenyl, phenyl-lower alkyl and substituted phenyl and phenyl-lower alkyl and said phenyl substituents are one or more selected from the group consisting of halogen, lower alkyl, lower alkoxy, lower alkylthio, nitro, amino, and trifluoromethyl; or the pharmaceutically acceptable acid addition salts thereof.
Claim 2
Dependent Claim
103 words
A compound of the formula ##SPC12## wherein R 1 and R 2 are each independently selected from the group consisting of hydrogen, halogen, lower alkyl, lower alkoxy, lower alkylthio, nitro, cyano, amino, and trifluoromethyl; A is a straight or branched chain alkylene of 1 to 8 carbons; and Z is ##SPC13## wherein R 3 is selected from the group consisting of phenyl, phenyl-lower alkyl and substituted phenyl and phenyl-lower alkyl and said phenyl substituents are one or more selected from the group consisting of halogen, lower alkyl, lower alkoxy, lower alkylthio, nitro, amino, and trifluoromethyl; or the pharmaceutically acceptable acid addition salts thereof.
Claim 3
Dependent Claim
48 words
The compound of claim 1 wherein at least one of R 1 and R 2 is hydrogen and the other is selected from the group consisting of hydrogen, Cl, Br, F, methyl and methoxy; and A is a straight or branched chain alkylene of 1 to 6 carbons.
Claim 4
Dependent Claim
9 words
The compound of claim 2 having the name 2-[(4-phenyl-1-piperazinyl)methyl]-1H-benz[de]isoquinoline-1,3(2H)-dione.
Claim 5
Dependent Claim
11 words
The compound of claim 2 having the name 5-chloro-2-[2-(4-phenyl-1-piperazinyl)ethyl]-1H-benz[de]isoquinoline-1,3-(2H)-dione, hydrochloride (1:1).
Claim 6
Dependent Claim
11 words
The compound of claim 2 having the name 6-chloro-2-[2-(4-phenyl-1-piperazinyl)ethyl]-1H-benz[de]isoquinoline-1,3-(2H)-dione, hydrochloride (1:1).
Claim 7
Dependent Claim
26 words
The compound of claim 2 wherein R 1 and R 2 are both hydrogen and A is a straight chain alkylene of 2 to 6 carbons.
Claim 8
Dependent Claim
13 words
The compound of claim 6 wherein A is --(CH 2 ) 3 --.
Claim 9
Dependent Claim
13 words
The compound of claim 6 wherein A is --(CH 2 ) 5 --.
Claim 10
Dependent Claim
13 words
The compound of claim 6 wherein A is --(CH 2 ) 6 --.
Claim 11
Dependent Claim
13 words
The compound of claim 6 wherein A is --(CH 2 ) 2 --.
Claim 12
Dependent Claim
11 words
The compound of claim 10 having the name 2-[2-(4-phenyl-1-piperazinyl)ethyl]-1H-benz[de]isoquinoline-1,3(2H)-dione, hydrochloride (1:2).
Claim 13
Dependent Claim
11 words
The compound of claim 10 having the name 2-[2-[4-(4-methoxyphenyl)-1-piperazinyl]ethyl]-1H-benz[de]isoquinoline-1,3-(2H)-dione, hydrochloride (1:2).
Claim 14
Dependent Claim
11 words
The compound of claim 10 having the name 2-[2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl]-1H-benz[de]isoquinoline-1,3(2H)-dione, hydrochloride (1:2).
Claim 15
Dependent Claim
11 words
The compound of claim 10 having the name 2-[2-[4-(4-chlorophenyl)-1-piperazinyl]ethyl]-1H-benz[de]isoquinoline-1,3-(2H)-dione, hydrochloride (1:1).
Claim 16
Dependent Claim
11 words
The compound of claim 10 having the name 2-[2-[4-(2-chlorophenyl)-1-piperazinyl]ethyl]-1H-benz[de]isoquinoline-1,3(2H)-dione, hydrochloride (1:1).
Claim 17
Dependent Claim
11 words
The compound of claim 10 having the same 2-[2-[4-[3-(trifluoromethyl)phenyl]-1-piperazinyl]ethyl]-1H-benz[de]isoquinoline-1,3(2H)-dione, hydrochloride (1:1).
Claim 18
Dependent Claim
11 words
The compound of claim 10 having the name 2-[2-[4-(4-fluorophenyl)-1-piperazinyl]ethyl]-1H-benz[de]isoquinoline-1,3(2H)-dione, hydrochloride (1:1).
Claim 19
Dependent Claim
11 words
The compound of claim 10 having the name 2-[2-[4-(phenylmethyl)-1-piperazinyl]ethyl]-1H-benz[de]isoquinoline-1,3(2H)-dione, hydrochloride (1:1).
Claim 20
Dependent Claim
14 words
The compound of claim 6 wherein A is -- (CH 2 ) 4 --.
Claim 21
Dependent Claim
12 words
A compound of claim 19 having the name of 2-[4-(4-phenyl-1-piperazinyl)butyl]-1H-benz[de]isoquinoline-1,3(2H)-dione, hydrochloride (1:1).
Claim 22
Dependent Claim
19 words
A composition consisting essentially of a compound or mixture of compounds of claim 1 and a pharmaceutically acceptable carrier.
Claim 23
Dependent Claim
16 words
The method of treating depression comprising administering an effective amount of the composition of claim 21.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-02-23 | 1979-08-25 | 1980-02-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-02-23 | 1983-08-25 | 1984-02-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-02-23 | 1987-08-25 | 1988-02-24 | $7700.00 | Window Closed / Lapsed |