US3935227A
Expired / Lapsed
US
⏱️ 0.0 years remaining
2-[(Substituted-piperidinyl or tetrahydropyridinyl)alkyl]-1H-benz[de]isoquinoline-1,3(2H)-diones
Assignee: ER Squibb and Sons LLC
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Filing: 1974-08-28
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Granted: 1976-01-27
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Expires: 1994-08-28
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 selected from ##SPC2## Wherein R 3 is selected from phenyl, phenyl-lower alkyl, and substituted phenyl and phenyl-lower alkyl are disclosed. These compounds exhibit antidepressant and anti-anxiety activity. In addition these compounds are useful as anti-inflammatory agents.
Inventors
- 👤 Peter C. Wade
- 👤 Berthold Richard Vogt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 07:57
CPC Classifications
C; C07; C07D; C07D221/00; C07D221/02; C07D221/04; C07D221/06; C07D221/14; C07D401/00; C07D401/02; C07D401/06
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
161 words
A compound of the formula ##SPC12## wherein R 1 and R 2 are each independently selected from the group consisting of hydrogen, chlorine, bromine, fluorine, straight or branched chain alkyl of 1 to 4 carbons, straight or branched chain alkoxy of 1 to 4 carbons, straight or branched chain alkylthio of 1 to 4 carbons, nitro, amino, cyano and trifluoromethyl; A is a straight or branched chain alkylene of 1 to 8 carbons; and Z is selected from the group consisting of ##SPC13## wherein R 3 is selected from the group consisting of phenyl, phenyl-alkyl, substituted phenyl and phenyl-alkyl wherein said alkyl is straight or branched chain of 1 to 4 carbons and said phenyl substituent is selected from the group consisting of chlorine, bromine, fluorine, di(chloro), di(bromo), straight or branched chain alkyl of 1 to 4 carbons, di(methyl), straight or branched chain alkoxy of 1 to 4 carbons, nitro, amino, and trifluoromethyl; and the pharmaceutically acceptable acid addition salts thereof.
Claim 2
Dependent Claim
161 words
A compound of the formula ##SPC12## wherein R 1 and R 2 are each independently selected from the group consisting of hydrogen, chlorine, bromine, fluorine, straight or branched chain alkyl of 1 to 4 carbons, straight or branched chain alkoxy of 1 to 4 carbons, straight or branched chain alkylthio of 1 to 4 carbons, nitro, amino, cyano and trifluoromethyl; A is a straight or branched chain alkylene of 1 to 8 carbons; and Z is selected from the group consisting of ##SPC13## wherein R 3 is selected from the group consisting of phenyl, phenyl-alkyl, substituted phenyl and phenyl-alkyl wherein said alkyl is straight or branched chain of 1 to 4 carbons and said phenyl substituent is selected from the group consisting of chlorine, bromine, fluorine, di(chloro), di(bromo), straight or branched chain alkyl of 1 to 4 carbons, di(methyl), straight or branched chain alkoxy of 1 to 4 carbons, nitro, amino, and trifluoromethyl; and 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
35 words
The compound of claim 2 wherein R 1 and R 2 are both hydrogen; A is a straight chain alkylene of 2 to 6 carbons; and Z is selected from the group consisting of ##SPC14##
Claim 5
Dependent Claim
9 words
The compound of claim 3 wherein Z is ##SPC15##
Claim 6
Dependent Claim
11 words
The compound of claim 4 having the name 2-[2-(4-phenyl-1-piperidinyl)ethyl]-1H-benz[de]isoquinoline-1,3(2H)-dione, hydrochloride (1:1).
Claim 7
Dependent Claim
11 words
The compound of claim 4 having the name 2-[2-[4-(phenylmethyl)-1-piperidinyl]ethyl]-1H-benz[de]isoquinoline-1,3(2H)-dione, hydrochoride (1:1).
Claim 8
Dependent Claim
11 words
The compound of claim 4 having the name 2-[2-[4-(3-phenylpropyl)-1-piperidinyl]ethyl]-1H-benz[de]isoquinoline-1,3(2H)-dione, hydrochloride (1:1).
Claim 9
Dependent Claim
11 words
The compound of claim 4 having the name 2-[3-(4-phenyl-1-piperidinyl)propyl]-1H-benz[de]isoquinoline-1,3(2H)-dione, hydrochloride (1:1).
Claim 10
Dependent Claim
11 words
The compound of claim 4 having the name 2-[4-(4-phenyl-1-piperidinyl)butyl]-1H-benz[de]isoquinoline-1,3(2H)-dione, hydrochloride (1:1).
Claim 11
Dependent Claim
11 words
The compound of claim 4 having the name 2-[5-(4-phenyl-1-piperidinyl)pentyl]-1H-benz[de]isoquinoline-1,3(2H)-dione, hydrochloride (1:1).
Claim 12
Dependent Claim
11 words
The compound of claim 4 having the name 2-[6-(4-phenyl-1-piperidinyl)hexyl]-1H-benz[de]isoquinoline-1,3(2H)-dione, hydrochloride (1:1).
Claim 13
Dependent Claim
9 words
The compound of claim 3 wherein Z is ##SPC16##
Claim 14
Dependent Claim
9 words
The compound of claim 12 having the name 2-[2-(4-hydroxy-4-phenyl-1-piperidinyl)ethyl]-1H-benz[de]isoquinoline-1,3(2H)-dione.
Claim 15
Dependent Claim
9 words
The compound of claim 12 having the name 2-[3-(4-hydroxy-4-phenyl-1-piperidinyl)propyl]-1H-benz[de]isoquinoline-1,3(2H)-dione.
Claim 16
Dependent Claim
9 words
The compound of claim 12 having the name 2-[4-(4-hydroxy-4-phenyl-1-piperidinyl)butyl]-1H-benz[de]isoquinoline-1,3(2H)-dione.
Claim 17
Dependent Claim
9 words
The compound of claim 3 where Z is ##SPC17##
Claim 18
Dependent Claim
11 words
The compound of claim 16 having the name 2-[2-(3,6-dihydro-4-phenyl-1(2H)-pyridinyl)ethyl]-1H-benz[de]isoquinoline-1,3(2H)-dione, hydrochloride (1:1).
Claim 19
Dependent Claim
11 words
The compound of claim 16 having the name 2-[2-[(4-chlorophenyl)-3,6-dihydro-1(2H)-pyridinyl]ethyl]-1H-benz[de]isoquinoline-1,3(2H)-dione, hydrochloride (1:1).
Claim 20
Dependent Claim
11 words
The compound of claim 16 having the name 2-[3-(3,6-dihydro-4-phenyl-1(2H)-pyridinyl)propyl]-1H-benz[de]isoquinoline-1,3(2H)-dione, hydrochloride (1:1).
Claim 21
Dependent Claim
11 words
The compound of claim 16 having the name 2-[4-(3,6-dihydro-4-phenyl-1(2H)-pyridinyl)butyl]-1H-benz[de]isoquinoline-1,3(2H)-dione, hydrochloride (1:1).
Claim 22
Dependent Claim
11 words
The compound of claim 16 having the name 2-[5-(3,6-dihydro-4-phenyl-1(2H)-pyridinyl)pentyl]-1H-benz[de]isoquinoline-1,3(2H)-dione, hydrochloride (1:1).
Claim 23
Dependent Claim
11 words
The compound of claim 16 having the name 2-[6-(3,6-dihydro-4-phenyl-1(2H)-pyridinyl)hexyl]-1H-benz[de]isoquinoline-1,3(2H)-dione, hydrochloride (1:1).
Claim 24
Dependent Claim
9 words
The compound of claim 2 having the name 2-[(4-phenyl-1-piperidinyl)methyl]-1H-benz[de]isoquinoline-1,3(2H)-dione.
Claim 25
Dependent Claim
9 words
The compound of claim 2 having the name 2-[(3,6-dihydro-4-phenyl-1(2H)-pyridinyl)methyl]-1H-benz[de]isoquinoline-1,3(2H)-dione.
Claim 26
Dependent Claim
11 words
The compound of claim 2 having the name 5-chloro-2-[2-(3,6-dihydro-4-phenyl-1(2H)-pyridinyl)ethyl]-1H-benz[de]isoquinoline-1,3(2H)-dione, hydrochloride (1:1).
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) | 1979-01-26 | 1979-07-28 | 1980-01-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-01-26 | 1983-07-28 | 1984-01-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-01-26 | 1987-07-28 | 1988-01-27 | $7700.00 | Window Closed / Lapsed |