US5173490A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Benzisoxazole and benzisothiazole compounds
Assignee: Institut Servier de Medecine Translationnelle SARL
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Filing: 1992-01-07
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Granted: 1992-12-22
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Expires: 2012-01-07
Abstract
Abstract The compounds are N-substituted N'-(benzisoxazolyl or benzisothiazolyl) piperazines useful as sedative, anxiolytic, anti-aggressive and analgesic agents and for the treatment of schizophrenia and depression. A compound disclosed is (R,S)-3-{1-[(benzocyclobutan-1-yl)methyl]piperazin-4-yl}-6-fluoro-1,2- benzisoxazole.
Inventors
- 👤 Jean-Louis Peglion
- 👤 Joel Vian
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 08:24
CPC Classifications
C; C07; C07D; C07D275/00; C07D275/04; A; A61; A61P; A61P25/00; A61P25/04; A61P25/18; A61P25/20; A61P25/24; A61P25/26; C07D261/00; C07D261/20
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
161 words
A compound selected from the group consisting of: benzisoxazole and benzisothiazole compounds of formula I: ##STR10## in which: X 1 , X 2 , X 3 , X 4 and X 5 : which are the same or different, each represent: hydrogen, halogen, alkyl, alkoxy, or alkylthio in each of which the alkyl moiety is straight-chained or branched and contains 1 to 5 carbon atoms, inclusive, hydroxy, carboxylic acid, acyloxy, trifluoromethyl, nitro, amino, or acetamido, or two of them in adjacent positions together form methylenedioxy, ethylenedioxy, or vinylenedioxy; R 1 represents hydrogen or straight-chained or branched alkyl containing 1 to 5 carbon atoms, inclusive; m and n each represent 0, 1, 2, or 3, provided that m+n≧1; p represents 0 or an integer of 1 to 6 inclusive; q represents 2 or 3; and Y represents oxygen or S(O) z in which z is 0, 1, or 2; in racemic and optically active forms, and the physiologically-tolerable acid addition salts thereof.
Claim 2
Dependent Claim
161 words
A compound selected from the group consisting of: benzisoxazole and benzisothiazole compounds of formula I: ##STR10## in which: X 1 , X 2 , X 3 , X 4 and X 5 : which are the same or different, each represent: hydrogen, halogen, alkyl, alkoxy, or alkylthio in each of which the alkyl moiety is straight-chained or branched and contains 1 to 5 carbon atoms, inclusive, hydroxy, carboxylic acid, acyloxy, trifluoromethyl, nitro, amino, or acetamido, or two of them in adjacent positions together form methylenedioxy, ethylenedioxy, or vinylenedioxy; R 1 represents hydrogen or straight-chained or branched alkyl containing 1 to 5 carbon atoms, inclusive; m and n each represent 0, 1, 2, or 3, provided that m+n≧1; p represents 0 or an integer of 1 to 6 inclusive; q represents 2 or 3; and Y represents oxygen or S(O) z in which z is 0, 1, or 2; in racemic and optically active forms, and the physiologically-tolerable acid addition salts thereof.
Claim 3
Dependent Claim
17 words
A compound of claim 1 which is selected from: (R,S)-3-{1-[(benzocyclobutan-1-yl)methyl]piperazin-4-yl}-6-fluoro-1,2-benzisoxazole and the physiologically-tolerable acid addition salts thereof.
Claim 4
Dependent Claim
13 words
A compound of claim 1 which is selected from: (R,S)-3-{1-[(benzocyclobutan-1-yl)methyl]piperazin-4-yl}-6-fluoro-1,2-benzisoxazole and its hydrochloride.
Claim 5
Dependent Claim
13 words
A compound of claim 1 which is selected from: (R,S)-3-{1-[4-(benzocyclobutan-1-yl)butyl]piperazin-1-yl}-1,2-benzisothiazole and its hydrochloride.
Claim 6
Dependent Claim
13 words
A compound of claim 1 which is selected from: (R,S)-3-{1-[(benzocyclobutan-1-yl)methyl]piperazin-4-yl}-1,2-benzisoxazole and its hydrochloride.
Claim 7
Dependent Claim
13 words
A compound of claim 1 which is selected from: 3-[1-(indan-2-yl)piperazin-4-yl]-6-fluoro-1,2-benzisoxazole and its fumarate.
Claim 8
Dependent Claim
13 words
A compound of claim 1 which is selected from: (R,S)-3-{1-[3-(benzocyclobutan-1-yl)propyl]piperazin-4-yl}-1,2-benzisothiazole and its hydrochloride.
Claim 9
Dependent Claim
8 words
A compound of claim 1 which is: 3-{1-[(5,6-dimethoxyindan-2-yl)methyl]piperazin-4-yl}-1,2-benzisothiazole.
Claim 10
Dependent Claim
8 words
A compound of claim 1 which is: (R,S)-3-{1-[(4,5-dimethoxybenzocyclobutan-1-yl)-methyl]piperazin-4-yl}-6-fluoro-1,2-benzisoxazole.
Claim 11
Dependent Claim
8 words
A compound of claim 1 which is: (R,S)-3-{1-[(4,5-dimethoxybenzocyclobutan-1-yl)-methyl]piperazin-4-yl}-1,2-benzisoxazole.
Claim 12
Dependent Claim
29 words
A pharmaceutical composition useful to treat psychosis and anxiety containing as active ingredient an effective amount of a compound of claim 1 together, with one or more pharmaceutically-acceptable excipients.
Claim 13
Dependent Claim
41 words
A method for treating a living animal afflicted with anxiety and psychosis, or comprising the step of administering to the said living animal an amount of a compound of claim 1 which is effective for the alleviation of the said condition.
Claim 14
Dependent Claim
48 words
As a intermediate, an amide compound of formula V: ##STR11## in which: X 1 , X 2 , X 3 , X 4 , X 5 , R 1 , m, n, p', q and Y have the meanings defined in claim 1 and p' is 1-6 inclusive.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1995-12-22 | 1996-06-22 | 1996-12-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-12-22 | 2000-06-22 | 2000-12-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-12-22 | 2004-06-22 | 2004-12-22 | $7700.00 | Window Closed / Lapsed |