Patent US4426387A successfully refreshed from Google Patents.
US4426387A
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Piperid-4-yl ureas and thio ureas used as anti-depressant agents
Assignee: John Wyeth and Brother Ltd
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Filing: 1982-04-07
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Granted: 1984-01-17
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Expires: 2002-04-07
Abstract
Abstract The invention concerns compounds of formula ##STR1## and acid addition and quaternary ammonium salts thereof, wherein the dotted line represents an optional bond, Ar represents a ring system of formula ##STR2## in which Q is O,S,--CR 7 ═CR 8 --, --N═CR 8 -- and --N═N--; R 4 , R 5 and R 6 , and R 7 and R 8 when present, each represent hydrogen or defined substituents and additionally either R 4 and R 5 when adjacent or R 6 and R 8 when adjacent, together with the carbon atoms to which they are attached also represent a fused five or six membered carbocyclic or heterocyclic ring optionally carrying one or more defined substituents; R is an optionally substituted aryl or heteroaryl radical or a cycloalkyl radical containing 5 to 7 carbon atoms; R 1 , R 2 , R 3 and R 9 are each hydrogen or a lower alkyl group; n is 0 or 1; X is ═O, ═S or ═NH; Y is --O-- or a direct bond and Z is --CO-- or --CH 2 -- with the proviso that when Ar is unsubstituted phenyl and R 9 is hydrogen then Y is --O--. The compounds of formula I exhibit psychotropic activity and are useful as antidepressants. Processes for preparing the compounds and pharmaceutical compositions containing them are disclosed.
Inventors
- 👤 John L. Archibald
- 👤 Terrence J. Ward
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 19:30
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/72; C07D213/75; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/56; C07D211/58; C07D211/68; C07D211/72
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
188 words
A compound of the formula ##STR20## wherein n is 0 or 1; R 2 , R 3 , and R 9 are, independently, hydrogen or a lower alkyl group; X is ═O, or ═S; Y is --O-- or a direct bond; R is phenyl or phenyl substituted by one or two of the same substituents selected from loweralkyl, lower alkenyl, lower alkoxy, hydroxy, hydroxyloweralkyl, fluoro, bromo, chloro, chloroloweralkyl, fluoroloweralkyl, amino, aminoloweralkyl, substituted amino, loweralkoxycarboxyl, nitro, cyano, or amido; Ar is ##STR21## in which R 4 ,R 5 , and R 6 , when present, independently, are hydrogen, lower alkyl, lower alkenyl, lower alkoxy, hydroxy, hydroxyloweralkyl, fluoro, bromo, chloro, chloroloweralkyl, fluoroloweralkyl, amino, aminoloweralkyl, substituted amino, loweralkoxycarbonyl, nitro, cyano, or amide, or R 4 and R 5 , when adjacent, together with the carbon atoms to which they are attached also are fused five or six member carbocyclic ring with 0-2 double bonds and optionally carrying one or two substituents as defined above for said R 4 and R 5 , or an acid addition or quaternary ammonium salt thereof, in which the dotted line represents an optional double bond.
Claim 2
Dependent Claim
188 words
A compound of the formula ##STR20## wherein n is 0 or 1; R 2 , R 3 , and R 9 are, independently, hydrogen or a lower alkyl group; X is ═O, or ═S; Y is --O-- or a direct bond; R is phenyl or phenyl substituted by one or two of the same substituents selected from loweralkyl, lower alkenyl, lower alkoxy, hydroxy, hydroxyloweralkyl, fluoro, bromo, chloro, chloroloweralkyl, fluoroloweralkyl, amino, aminoloweralkyl, substituted amino, loweralkoxycarboxyl, nitro, cyano, or amido; Ar is ##STR21## in which R 4 ,R 5 , and R 6 , when present, independently, are hydrogen, lower alkyl, lower alkenyl, lower alkoxy, hydroxy, hydroxyloweralkyl, fluoro, bromo, chloro, chloroloweralkyl, fluoroloweralkyl, amino, aminoloweralkyl, substituted amino, loweralkoxycarbonyl, nitro, cyano, or amide, or R 4 and R 5 , when adjacent, together with the carbon atoms to which they are attached also are fused five or six member carbocyclic ring with 0-2 double bonds and optionally carrying one or two substituents as defined above for said R 4 and R 5 , or an acid addition or quaternary ammonium salt thereof, in which the dotted line represents an optional double bond.
Claim 3
Dependent Claim
12 words
A compound of claim 1 in which Y represents a direct bond.
Claim 4
Dependent Claim
30 words
A compound of claim 1 in which R is phenyl or phenyl subtituted with one or two substituents selected from fluoro, bromo, chloro, lower alkyl, lower alkoxy, hydroxy, or nitro.
Claim 5
Dependent Claim
51 words
A compound of claim 1 in which Ar is phenyl substituted by one or two lower alkyl or alkoxy groups of 2-6 carbon atoms or is naphth-1-yl or naphthy-2-yl, unsubstituted or substituted by one or two lower alkyl, lower alkoxy, fluoro, bromo, chloro, nitro, trifluoromethyl, amino, loweralkylamino, diloweralkylamino, or cyano groups.
Claim 6
Dependent Claim
10 words
A compound as claimed in claim 1 which is 1-benzoyl-3-[1-naphth-2-ylmethyl)piperid-4-yl]urea.
Claim 7
Dependent Claim
10 words
A compound as claimed in claim 1 which is 1-benzoyl-3-[1-(naphth-1-ylmethyl)piperid-4-yl]urea.
Claim 8
Dependent Claim
10 words
A compound as claimed in claim 1 which is 1-benzoyl-3-[1-(4-isopropylbenzyl)piperid-4-yl]urea.
Claim 9
Dependent Claim
10 words
A compound as claimed in claim 1 which is 1-benzoyl-3-[1-(5,6,7,8-tetrahydronaphth-2-ylmethyl)-piperid-4-yl]-urea.
Claim 10
Dependent Claim
10 words
A compound as claimed in claim 1 which is 1-benzoyl-3-[1-(3,4-dimethylbenzyl)piperid-4-yl]urea.
Claim 11
Dependent Claim
10 words
A compound as claimed in claim 1 which is 1-benzoyl-3-[1-(indan-5-ylmethyl)piperid-4-yl]urea.
Claim 12
Dependent Claim
10 words
A compound as claimed in claim 1 which is 1-benzoyl-3-{1-[1-(naphth-2-yl)ethyl]-piperid-4-yl}urea.
Claim 13
Dependent Claim
10 words
A compound as claimed in claim 1 which is 1-benzoyl-3-[1-(4-ethylbenzyl)piperid-4-yl]urea.
Claim 14
Dependent Claim
10 words
A compound as claimed in claim 1 which is 1-benzoyl-3-[1-(6-methoxynaphth-2-ylmethyl)piperid-4-yl]urea.
Claim 15
Dependent Claim
10 words
A compound as claimed in claim 1 which is 1-benzoyl-3-[1-(2-[naphth-1-yloxy]ethyl)piperid-4-yl]urea.
Claim 16
Dependent Claim
10 words
A compound as claimed in claim 1 which is 1-benzoyl-3-[1-(3,4-dibromobenzyl)piperid-4-yl]urea.
Claim 17
Dependent Claim
10 words
A compound as claimed in claim 1 which is 1-benzoyl-3-[1-(4-n-propoxybenzyl)piperid-4-yl]urea.
Claim 18
Dependent Claim
37 words
A pharmaceutical composition comprising an amount effective for alleviating depression of a compound of formula I as defined in claim 1 or a pharmaceutically acceptable acid addition or quaternary ammonium salt thereof and a pharmaceutically acceptable carrier.
Claim 19
Dependent Claim
43 words
A method for alleviating depression in a warm blooded animal afflicted with depression which comprises administering to said animal an effective amount of a compound of formula I as defined in claim 1 or pharmaceutically acceptable acid addition or quaternary ammonium salt thereof.
Claim 20
Dependent Claim
10 words
A compound as claimed in claim 1 which is 1-(3,4-dimethylbenzoyl)-3-[1-naphth-2-ylmethyl)piperid-4-yl]urea.
Claim 21
Dependent Claim
10 words
A compound as claimed in claim 1 which is 1-[1-(naphth-2-ylmethyl)piperid-4-yl]-3-(4-nitrobenzoyl)urea.
Claim 22
Dependent Claim
10 words
A compound as claimed in claim 1 which is 1-(p-fluorobenzoyl)-3-[1-(naphth-2-ylmethyl)piperid-4-yl]urea.
Claim 23
Dependent Claim
9 words
A compound as claimed in claim 1 which 1-benzoyl-3-[1-(6-cyanonaphth-2-ylmethyl)piperid-4-yl]urea.
Claim 24
Dependent Claim
10 words
A compound as claimed in claim 1 which is 1-benzoyl-3-[1-(6-fluoronaphth-2-ylmethyl)piperid-4-yl]urea.
Claim 25
Dependent Claim
10 words
A compound as claimed in claim 1 which is 1-benzoyl-3-[1-(1-naphth-2-yl)propyl]piperid-4-yl]urea.
Claim 26
Dependent Claim
10 words
A compound as claimed in claim 1 which is 1-benzolyl-3-[1-(3-amino-4-methylbenzyl)piperid-4-yl]-urea.
References Cited (Backward Citations)
DE2545501A1
Cited
FR2387955B1
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-01-16 | 1987-07-18 | 1988-01-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-01-16 | 1991-07-18 | 1992-01-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-01-16 | 1995-07-18 | 1996-01-17 | $7700.00 | Window Closed / Lapsed |