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US5100902A Expired / Lapsed US ⏱️ 0.0 years remaining

1,2-benzisoxazole compounds

Assignee: Institut Servier de Medecine Translationnelle SARL
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Filing: 1990-10-26
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Granted: 1992-03-31
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Expires: 2010-10-26
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Abstract

Abstract Compounds of formula I <IMAGE> (I) in which m represents an integer from 0 to 5, n represents an integer from 1 to 2, p is equal to 0, 1 or 2, X, Y and Z, which may be identical or different, each represent a hydrogen atom, a halogen atom, a linear or branched alkyl radical, a trifluoromethyl radical, an alkoxy radical, an alkylthio radical or a hydroxyl radical, and R represents a 2-benzofuranyl or 2,3-dihydro-2-benzofuranyl radical (it being possible for each to be substituted on the benzene ring), a 2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran-2-yl radical, a 4-oxo-4H-chromen-2-yl radical (optionally substituted on the benzene ring), a benzocyclobutenyl radical of formula A or an indanyl radical of formula B: <IMAGE> (A) <IMAGE> (B) (in which: R1 and R2, which may be identical or different, each represent a hydrogen atom, a halogen atom, a trifluoromethyl radical, an alkyl radical, an alkoxy radical, a hydroxyl radical, a hydroxyalkyl radical or an alkylthio radical, or together form a methylenedioxy radical or an ethylenedioxy radical, and R3 represents a hydrogen atom or a linear or branched alkyl radical having 1 to 6 carbon atoms), or a radical of formula C: <IMAGE> (C) (in which R4, R5 and R6, which may be identical or different, each represent a hydrogen atom, a halogen atom, a trifluoromethyl radical, a hydroxyl radical, an alkyl radical, an alkoxy radical or an alkylthio radical, their optical isomers and their addition salts with a pharmaceutically acceptable organic or inorganic acid.

Inventors

  • 👤 Jean L. Peglion
  • 👤 Francis Colpaert

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-05 20:07
CPC Classifications
C; C07; C07D; C07D413/00; C07D413/02; C07D413/04; A; A61; A61P; A61P25/00; A61P25/04; A61P25/18; A61P25/20; A61P25/24; A61P25/26; C07D413/14; C07D471/00; C07D471/02; C07D471/04; C07D493/00; C07D493/02; C07D493/04

Claims Analysis

Total Claims: 11
Claim 1
Independent Claim 239 words
A compound selected from the group consisting of: a 1,2-benzisoxazole compound of the formula I: ##STR80## in which m is selected from the group consisting of: zero and the integers 1 to 5, n is 2, p is selected from the group consisting of: 0, 1 and 2, X, Y and Z, which may be identical or different, are each selected from the group consisting of a hydrogen atom, halogen atoms, linear and branched alkyl radicals having 1 to 6 carbon atoms, a trifluoromethyl radical, alkoxy radicals having 1 to 6 carbon atoms, alkylthio radicals having 1 to 6 carbon atoms and a hydroxyl radical, and a benzocyclobutenyl radical of formula A and an indanyl radical of formula B: ##STR81## in which R 1 and R 2 , which may be identical or different, are each selected from the group consisting of a hydrogen atom, halogen atoms, a trifluoromethyl radical, linear and branched alkyl radicals having 1 to 6 carbon atoms, alkoxy radicals having 1 to 6 carbon atoms, a hydroxyl radical, hydroxyalkyl radicals having 1 to 6 carbon atoms, and alkylthio radicals having 1 to 6 carbon atoms, and which together may form a methylenedioxy radical or an ethylenedioxy radical, and R 3 is selected from the group consisting of a hydrogen atom, linear and branched alkyl radicals having 1 to 6 carbon atoms, their optical isomers and their addition salts with a pharmaceutically-acceptable organic or inorganic acid.
Claim 2
Dependent Claim 239 words
A compound selected from the group consisting of: a 1,2-benzisoxazole compound of the formula I: ##STR80## in which m is selected from the group consisting of: zero and the integers 1 to 5, n is 2, p is selected from the group consisting of: 0, 1 and 2, X, Y and Z, which may be identical or different, are each selected from the group consisting of a hydrogen atom, halogen atoms, linear and branched alkyl radicals having 1 to 6 carbon atoms, a trifluoromethyl radical, alkoxy radicals having 1 to 6 carbon atoms, alkylthio radicals having 1 to 6 carbon atoms and a hydroxyl radical, and a benzocyclobutenyl radical of formula A and an indanyl radical of formula B: ##STR81## in which R 1 and R 2 , which may be identical or different, are each selected from the group consisting of a hydrogen atom, halogen atoms, a trifluoromethyl radical, linear and branched alkyl radicals having 1 to 6 carbon atoms, alkoxy radicals having 1 to 6 carbon atoms, a hydroxyl radical, hydroxyalkyl radicals having 1 to 6 carbon atoms, and alkylthio radicals having 1 to 6 carbon atoms, and which together may form a methylenedioxy radical or an ethylenedioxy radical, and R 3 is selected from the group consisting of a hydrogen atom, linear and branched alkyl radicals having 1 to 6 carbon atoms, their optical isomers and their addition salts with a pharmaceutically-acceptable organic or inorganic acid.
Claim 3
Dependent Claim 17 words
(RS)-3-[1-(Benzocyclobuten-1-ylmethyl)-4-piperidyl]-6-fluoro-1,2-benzisoxazole, as claimed in claim 1, and its addition salts with a pharmaceutically-acceptable inorganic or organic acid.
Claim 4
Dependent Claim 17 words
(+)-3-[1-(Benzocyclobuten-1-ylmethyl)-4-piperidyl]-6-fluoro-1,2-benzisoxazole, as claimed in claim 1, and its addition salts with a pharmaceutically-acceptable inorganic or organic acid.
Claim 5
Dependent Claim 17 words
(-)-3-[1-(Benzocyclobuten-1-ylmethyl)-4-piperidyl]-6-fluoro-1,2-benzisoxazole, as claimed in claim 1, and its addition salts with a pharmaceutically-acceptable inorganic or organic acid.
Claim 6
Dependent Claim 20 words
(RS)-3-[1-(2-Benzocyclobuten-1-ylethyl)-4-piperidyl]-6-fluoro-1,2-benzisoxazole, as claimed in claim 1, its optical isomers and its addition salts with a pharmaceutically-acceptable inorganic or organic acid.
Claim 7
Dependent Claim 20 words
(RS)-6-Fluoro-3-{1-[(1-methylbenzocyclobuten-1-yl)methyl]-4-piperidyl}-1,2-benzisoxazole, as claimed in claim 1, its optical isomers and its addition salts with a pharmaceutically-acceptable inorganic or organic acid.
Claim 8
Dependent Claim 20 words
(RS)-3-[1-(4,5-Dimethoxybenzocyclobuten-1-ylmethyl)-4-piperidyl]-6-fluoro-1,2-benzisoxazole, as claimed in claim 1, its optical isomers and its addition salts with a pharmaceutically-acceptable inorganic or organic acid.
Claim 9
Dependent Claim 20 words
(RS)-6-Fluoro-3-[1-(1-indanylmethyl)-4-piperidyl]-1,2-benzisoxazole, as claimed in claim 1, its optical isomers and its addition salts with a pharmaceutically-acceptable inorganic or organic acid.
Claim 10
Dependent Claim 33 words
A pharmaceutical composition useful in dopamine and serctonin antagonist containing as active principle an effective amount of a compound of claim 1, in combination or mixed with a pharmaceutically acceptable, vehicle or excipient.
Claim 11
Dependent Claim 46 words
A method for treating a living animal body afflicted with a disease requiring a dopamine and serctonin antagonist, 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.

References Cited (Backward Citations)

US4528376A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1995-03-31 1995-09-30 1996-03-31 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1999-03-31 1999-09-30 2000-03-31 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2003-03-31 2003-09-30 2004-03-31 $7700.00 Window Closed / Lapsed

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