US4954502A
Expired / Lapsed
US
⏱️ 0.0 years remaining
1-indolyalkyl-4-(substituted-pyridinyl)piperazines
Assignee: Bristol Myers Co
•
Filing: 1989-04-14
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Granted: 1990-09-04
•
Expires: 2009-04-14
Abstract
Abstract A series of 1,4-disubstituted piperazine derivatives comprised of indol-3-ylalkyl and substituted pyridin-2-yl substituent groups. These compounds are useful as antidepressant agents.
Inventors
- 👤 David W. Smith
- 👤 Frank D. Yocca
- 👤 Joseph P. Yevich
- 👤 Ronald J. Mattson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 09:01
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/14; H; H01; H01M; H01M6/00; H01M6/04; H01M6/06; C07D401/02; C07D401/12; A; A61; A61K; A61K31/00; A61K31/33; A61K31/395; A61K31/495; A61P; A61P25/00; A61P25/24; A61P25/26; C07D487/00; C07D487/02; C07D487/08; H01M4/00; H01M4/02; H01M4/62; H01M4/621
Claims Analysis
Total Claims: 59
Claim 1
Independent Claim
135 words
A compound of Formula I aor the pharmaceutically acceptable acid addition salts thereof, ##STR58## wherein R 1 and R 2 are independently selected from hydrogen and lower alkyl, wherein lower means C 1-4 ; R 3 , R 4 , R 8 and R 9 are independently selected from hydrogen, lower alkyl, lower alkoxy, carboxamide, halogen, trifluoromethyl and thio-lower alkyl, with the proviso that R 8 and R 9 cannot both be hydrogen at the same time; A is a C 5-7 cycloalkanyl or cycloalkenyl ring, or A is ##STR59## wherein n is an integer from 1 to 3 and R 5 is the same as R 1 ; and R 6 and R 7 are independently selected from hydrogen, methyl or R 6 and R 7 can be taken together as a methylene bridge.
Claim 2
Dependent Claim
135 words
A compound of Formula I aor the pharmaceutically acceptable acid addition salts thereof, ##STR58## wherein R 1 and R 2 are independently selected from hydrogen and lower alkyl, wherein lower means C 1-4 ; R 3 , R 4 , R 8 and R 9 are independently selected from hydrogen, lower alkyl, lower alkoxy, carboxamide, halogen, trifluoromethyl and thio-lower alkyl, with the proviso that R 8 and R 9 cannot both be hydrogen at the same time; A is a C 5-7 cycloalkanyl or cycloalkenyl ring, or A is ##STR59## wherein n is an integer from 1 to 3 and R 5 is the same as R 1 ; and R 6 and R 7 are independently selected from hydrogen, methyl or R 6 and R 7 can be taken together as a methylene bridge.
Claim 3
Dependent Claim
15 words
The compound of claim 1 wherein A is a C 5-7 cycloalkanyl or cycloalkenyl ring.
Claim 4
Dependent Claim
9 words
The compound cf claim 1 wherein A is ##STR60##
Claim 5
Dependent Claim
17 words
The compound cf claim 1 wherein R 6 and R 7 are selected from hydrogen or methyl.
Claim 6
Dependent Claim
18 words
The compound cf claim 1 wherein R 6 and R 7 are taken together as a methylene bridge.
Claim 7
Dependent Claim
6 words
The compound of claim 1; 1-[2-(1H-indol-3-yl)ethyl]-4(3-methoxy-2-pyridinyl)piperazine.
Claim 8
Dependent Claim
7 words
The compound of claim 1; 1-[2-(1H-indol-3-yl)ethyl]-4(3-trifluoromethyl-2-pyridinyl) -piperazine.
Claim 9
Dependent Claim
6 words
The compound of claim 1; 1-[2-(1H-indol-3-yl)ethyl]-4(3-methoxy-2-pyridinyl)-2-methypiperazine.
Claim 10
Dependent Claim
7 words
The compound of claim 1; 1-[2-(1H-indol-3-yl)ethyl]-5(3-methoxy-2-pyridinyl)-(1R,4R)-2,5-diazabicyclo[2.2.1] heptane.
Claim 11
Dependent Claim
6 words
The compound of claim 1; 1-[2-(1H-indol-3-yl)ethyl]-4(6-chloro-2-pyridinyl)piperazine.
Claim 12
Dependent Claim
6 words
The compound of claim 1; 1-[2-(1H-indol-3-yl)ethyl]-4(6-methoxy-2-pyridinyl)piperazine.
Claim 13
Dependent Claim
8 words
The compound of claim 1; 1-[2-(1H-indol-3-yl)ethyl]-5(3-methoxy-2-pyridinyl)-(1S,4S)-b 2,5-diazabicyclo[2.2.1] heptane.
Claim 14
Dependent Claim
6 words
The compound of claim 1; 1-[3-(1H-indol-3-yl)propyl]-4(3-methoxy-2-pyridinyl)piperazine.
Claim 15
Dependent Claim
6 words
The compound of claim 1; 1-[3-(1H-indol-3-yl)propyl]-4(6-chloro-2-pyridinyl)piperazine.
Claim 16
Dependent Claim
6 words
The compound of claim 1; 1-[4-(1H-indol-3-yl)butyl]-4(3-methoxy-2-pyridinyl)piperazine.
Claim 17
Dependent Claim
6 words
The compound of claim 1; 1-[2-(1H-indol-3-yl)ethyl]-4(6-trifluoromethyl-2-pyridinyl)-piperazine.
Claim 18
Dependent Claim
6 words
The compound of claim 1; 2-[2-(1H-indol-3-yl)ethyl]-5(6-chloro-2-pyridinyl)-(1S,4S)-2,5diazabicyclo[2.2.1]heptane.
Claim 19
Dependent Claim
7 words
The compound of claim 1; 2-[2-(1H-indol-3-yl)ethyl]-5(6-chloro-2-pyridinyl)-(1R,4R)-2,5-diazabicyclo[2.2.1] heptane.
Claim 20
Dependent Claim
6 words
The compound of claim 1; 1-[3-(1H-indol-3-yl)propyl]-4(6-trifluoromethyl-2-pyridinyl)-piperazine.
Claim 21
Dependent Claim
6 words
The compound of claim 1; 1-[4-(1H-indol-3-yl)butyl]-4(6-chloro-2-pyridinyl)piperazine.
Claim 22
Dependent Claim
6 words
The compound of claim 1; 1-[4-(1H-indol-3-yl)butyl]-4(6-trifluoromethyl-2-pyridinyl)-piperazine.
Claim 23
Dependent Claim
6 words
The compound of claim 1; 1-[3-(1H-indol-3-yl)propyl]-4(4-trifluoromethyl-2-pyridinyl)-piperazine.
Claim 24
Dependent Claim
7 words
The compound of claim 1; 2-[3-(1H-indol-3-yl)propyl]-5(3-methoxy-2-pyridinyl)-(1S,4)-2,5-diazabicyclo[2.2.1] heptane.
Claim 25
Dependent Claim
8 words
The compound of claim 1; 2-[3-(1H-indol-3-yl)propyl]-5(3-methoxy-2-pyridinyl)-(1R,4R)- 2,5-diazabicyclo[2.2.1] heptane.
Claim 26
Dependent Claim
6 words
The compound of claim 1; 1-[2-(1H-indol-3-yl)ethyl]-4(6-chloro-2-pyridinyl)-2-methylpiperazine.
Claim 27
Dependent Claim
6 words
The compound of claim 1; 1-[2-(1H-indol-3-yl)ethyl]-4(4-trifluoromethyl-2-pyridinyl)-piperazine.
Claim 28
Dependent Claim
6 words
The compound of claim 1; 1-[2-(5-methoxy-1H-indol-3-yl)ethyl]-4-(3-methoxy-2-pyridinyl)piperazine.
Claim 29
Dependent Claim
6 words
The compound of claim 1; 1-[2-(5-fluoro-1H-indol-3-yl)ethyl]-4-(3-methoxy-2-pyridinyl)piperazine.
Claim 30
Dependent Claim
6 words
The compound of claim 1; 1-[2-(5-methoxy-1H-indol-3-yl)ethyl]-4-(6-chIoro-2-pyridinyl)piperazine.
Claim 31
Dependent Claim
6 words
The compound of claim 1; 1-[2-(5-fluoro-1H-indol-3-yl)ethyl]-4-(6-chloro-2-pyridinyl)piperazine.
Claim 32
Dependent Claim
6 words
The compound of claim 1; 1-[2-(1H-indol-3-yl)-ethyl]-4(3-chloro-2-pyridinyl)piperazine.
Claim 33
Dependent Claim
6 words
The compound of claim 1; 1-[2-(5-fluoro-1H-indol-3-yl)ethyl]-4-(6-trifluoromethyl-2-pyridinyl)piperazine.
Claim 34
Dependent Claim
6 words
The compound of claim 1; 1-[2-(5-methoxy-1H-indol-3-yl)ethyl]-4-(6-trifluoromethyl-2-pyridinyl)piperazine.
Claim 35
Dependent Claim
6 words
The compound of claim 1; 3-[4-[4-(6-chloro-2-pyridinyl)1-piperazinyl]-1-cyclohexen-1-yl]-5-methoxyindole.
Claim 36
Dependent Claim
6 words
The compound of claim 1; 3-[4-[4-(6-chloro-2-pyridinyl)-1-piperazinyl]-1-cyclohexen-1-yl]-1H-indole
Claim 37
Dependent Claim
6 words
The compound of claim 1; 3-[4-[4-(6-chloro-2-pyridinyl)1-piperazinyl]-1-cyclohexen-1-yl]-1H-indole-5-carboxamide.
Claim 38
Dependent Claim
6 words
The compound of claim 1; 1-[2-(N-methyl-1H-indol-3-yl)ethyl]-4-(3-methoxy-2-pyridinyl)-piperazine.
Claim 39
Dependent Claim
6 words
The compound of claim 1; 1-[2-(5,6-dimethoxy-1H-indol-3yl)ethyl]-4-(3-methoxy-2-pyridinyl)piperazine.
Claim 40
Dependent Claim
6 words
The compound of claim 1; 1-[3-(N-methyl-1H-indol-3-yl)propyl]-4-(3-methoxy-2-pyridinyl)-piperazine.
Claim 41
Dependent Claim
6 words
The compound of claim 1; 1-[3-(N-methyl-1H-indol-3-yl)propyl]-4-(6-chloro-2-pyridinyl)-piperazine.
Claim 42
Dependent Claim
6 words
The compound of claim 1; 1-[3-(5-fluoro-1H-indol-3-yl)propyl]-4-(6-chloro-2-pyridinyl)piperazine.
Claim 43
Dependent Claim
6 words
The compound of claim 1; 1-[3-(5-fluoro-1H-indol-3-yl)propyl]-4-(3-methoxy-2-pyridinyl)piperazine.
Claim 44
Dependent Claim
6 words
The compound of claim 1; 1-[2-(1H-indol-3-yl)ethyl]-4(5-chloro-2-pyridinyl)piperazine.
Claim 45
Dependent Claim
6 words
The compound of claim 1; 1-[2-[N-methyl-1H-indol-3-yl)ethyl]-4-(6-chloro-2-pyridinyl)-piperazine.
Claim 46
Dependent Claim
6 words
The compound of claim 1; 1-[2-(5-chloro-1H-indol-3-yl)ethyl]-4-(3-methoxy-2-pyridinyl)piperazine.
Claim 47
Dependent Claim
6 words
The compound of claim 1; 1-[2-(5-chloro-1H-indol-3-yl)ethyl]-4-(6-chloro-2-pyridinyl)piperazine.
Claim 48
Dependent Claim
6 words
The compound of claim 1; 1-[2-(5-chloro-1H-indol-3-yl)ethyl]-4-(6-trifluoromethyl-2-methyl-piperazine.
Claim 49
Dependent Claim
6 words
The compound of claim 1; 1-[2-(1H-indol-3-yl)ethyl]-4-(3-methoxy-2-pyridinyl)-2-methyl-piperazine.
Claim 50
Dependent Claim
6 words
The compound of claim 1; 4-(6-chloro-2-pyridinyl)-1-[2-(6-methoxy-1H-indol-3-yl)ethyl]-piperazine.
Claim 51
Dependent Claim
7 words
The compound of claim 1; 1- methoxy-1H-indol-3-yl)ethyl]-4-(3-methoxy-2-pyridinyl)-piperazine.
Claim 52
Dependent Claim
6 words
The compound of claim 1; 1-[3-(1H-indol-3-yl)-3-methylpropyl]-4-(6-chloro-2-pyridinyl)piperazine.
Claim 53
Dependent Claim
6 words
The compound of claim 1; 1-[3-(1H-indol-3-yl)-3-methylpropyl]-4-(3-methoxy-2-pyridiyl)piperazine.
Claim 54
Dependent Claim
6 words
The compound of claim 1; 1-[2-(5,6-dimethoxy-1H-indol3-yl)ethyl]-4-(6-trifluoromethyl-2-pyridinyl)piperazine.
Claim 55
Dependent Claim
6 words
The compound of claim 1; 3-[4-[4-(6-chloro-2-pyridinyl)-1piperazinyl]-1-cyclohexen-1-yl]-5-fluoro-1H-indole.
Claim 56
Dependent Claim
7 words
The compound of claim 1; 4-(5-chloro-3-methoxy-2-pyridinyl)-1-[3-(1H-indol-3-yl)-propypyl]-piperazine hydrochloride.
Claim 57
Dependent Claim
6 words
The compound of claim 1; 4-(6-chloro-2-pyridinyl)-1-[3-(1H-indol-3-yl)propyl]-2-methyl-piperazine.
Claim 58
Dependent Claim
26 words
A method for ameliorating of depression in a mammal comprising administration to said mammal of an effective antidepressant amount of a compound claimed in claim 1.
Claim 59
Dependent Claim
39 words
A antidepressant pharmaceutical composition in dosage unit form suitable for systemic administration to a mammalian host comprising a pharmaceutical carrier and from about 1 to 500 mg of an active compound selected from the compounds claimed in claim 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) | 1993-09-03 | 1994-03-05 | 1994-09-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-09-03 | 1998-03-05 | 1998-09-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-09-03 | 2002-03-05 | 2002-09-04 | $7700.00 | Window Closed / Lapsed |