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US5026704A Expired / Lapsed US ⏱️ 0.0 years remaining

Benzo[f]quinoxaline-2,3(1H,4H)-diones

Assignee: Novo Nordisk AS
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Filing: 1989-12-26
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Granted: 1991-06-25
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Expires: 2009-12-26
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Abstract

Abstract Heterocyclic dihydroxyquinoxaline compounds having the formula ##STR1## wherein R 1 is C 1-12 -alkyl, which may optionally be substututed by hydroxy, formyl, carboxy, carboxylic esters, amides or amines, C 3-8 -cycloalkyl, aryl, aralkyl; and wherein R 6 is, hydrogen, halogen, CN, CF 3 , NO 2 , or OR', wherein R' is C 1-4 -alkyl and R 5 , R 7 and R 8 is hydrogen, provided R 6 is not CF 3 , OCH 3 , NO 2 , Cl or Br when R 1 is CH 3 ; or R 6 and R 7 independently are NO 2 , halogen, CN, CF 3 , or OR', wherein R' is C 1-4 -alkyl, and R 5 and R 8 are each hydrogen; or R 5 and R 6 together form a further fused aromatic ring, which may be substituted with halogen, NO 2 , CN, CF 3 or OR', wherein R' is C 1-4 -alkyl, and R 7 and R 8 independently are hydrogen, halogen, CN, CF 3 , NO 2 or OR', wherein R' is C 1-4 - alkyl; or R 7 and R 8 together form a further fused aromatic ring, which may be substituted with halogen, NO 2 , CN, CF 3 or OR', wherein R' is C 1-4 -alkyl, and R 5 and R 6 independently are hydrogen, halogen, CN, CF 3 , NO 2 or OR', wherein R' is C 1-4 -alkyl. The invention also relates to a method of preparing the compounds, pharmaceutical compositions thereof, and their use. The compounds are useful in the treatment of indications caused by hyperactivity of the excitatory neurotransmitters, particularly the quisqualate receptors, and especially as neuroleptics.

Inventors

  • 👤 Tage Honore
  • 👤 Poul Jacobsen
  • 👤 Flemming E. Nielsen
  • 👤 Lars Naerum

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-02 13:32
CPC Classifications
C; C07; C07D; C07D241/00; C07D241/36; C07D241/38; A; A61; A61K; A61K31/00; A61K31/33; A61K31/395; A61K31/495; A61P; A61P25/00; A61P25/08; A61P25/28; C07D241/40; C07D241/44; C07D241/50; C07D241/52; C07D403/00; C07D403/02; C07D403/06

Claims Analysis

Total Claims: 13
Claim 1
Independent Claim 155 words
A quinoxaline compound having the formula I ##STR7## wherein R 1 is C 1-12 -alkyl, which may optionally be substituted by hydroxy, formyl, carboxy, carlomoyl, piperedino, amino, C 3-8 -cycloalkyl, or phenyl; or R is C 3-6 cycloalkyl and in any case R 5 and R 6 together form a further fused benzene ring, which may be substituted with halogen, NO 2 , CN, CF 3 or OR', wherein R' is C 1-4 -alkyl, and R 7 and R 8 independently are hydrogen, halogen, CN, CF 3 , NO 2 or OR', wherein R' is C 1-4 -alkyl; or R 7 and R 8 together form a further fused benzene ring, which may be substituted with halogen, NO 2 , CN, CF 3 or OR', wherein R' is C 1-4 -alkyl, and R 5 and R 6 independently are hydrogen, halogen, CN, CF 3 , NO 2 or OR', wherein R' is C 1-4 -alkyl.
Claim 2
Dependent Claim 155 words
A quinoxaline compound having the formula I ##STR7## wherein R 1 is C 1-12 -alkyl, which may optionally be substituted by hydroxy, formyl, carboxy, carlomoyl, piperedino, amino, C 3-8 -cycloalkyl, or phenyl; or R is C 3-6 cycloalkyl and in any case R 5 and R 6 together form a further fused benzene ring, which may be substituted with halogen, NO 2 , CN, CF 3 or OR', wherein R' is C 1-4 -alkyl, and R 7 and R 8 independently are hydrogen, halogen, CN, CF 3 , NO 2 or OR', wherein R' is C 1-4 -alkyl; or R 7 and R 8 together form a further fused benzene ring, which may be substituted with halogen, NO 2 , CN, CF 3 or OR', wherein R' is C 1-4 -alkyl, and R 5 and R 6 independently are hydrogen, halogen, CN, CF 3 , NO 2 or OR', wherein R' is C 1-4 -alkyl.
Claim 3
Dependent Claim 8 words
A compound of claim 1, which is 4-methylbenzo[f]quinoxaline-2,3(1H,4H)-dione.
Claim 4
Dependent Claim 8 words
A compound of claim 1, which is 4-butylbenzo[f]quinoxaline-2,3(1H,4H)-dione.
Claim 5
Dependent Claim 9 words
A compound of claim 1, which is 4-(2-piperidinoethyl) benzo[f]quinoxaline-2,3(1H,4H)-dione.
Claim 6
Dependent Claim 8 words
A compound of claim 1, which is 4-cyclohexylbenzo[f]-quinoxaline-2,3(1H,4H)-dione.
Claim 7
Dependent Claim 8 words
A compound of claim 1, which is 1-methyl-6,7-dinitrobenzo[f]-quinoxaline-2,3(1H,4H-dione.
Claim 8
Dependent Claim 34 words
A pharmaceutical composition useful as a neuroleptic comprising as active component a neuroleptically effective amount of a quinoxaline compound according to claim 1 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.
Claim 9
Dependent Claim 23 words
A pharmaceutical composition according to claim 7 in the form of an oral dosage unit containing about 50-200 mg of the active compound.
Claim 10
Dependent Claim 39 words
A method of treating hyperactivity of the excitatory neurotransmitters in a subject in need thereof, which comprises the step of administering to the said subject a neuroleptically-effective amount of a compound of claim 1 or a pharmaceutically-acceptable salt thereof.
Claim 11
Dependent Claim 28 words
A method according to claim 9 wherein the compound is administered in the form of an oral dosage unit containing about 50 to 200 mg of the compound.
Claim 12
Dependent Claim 25 words
A method of claim 9, wherein the compound is administered in the form of a pharmaceutical composition containing the same together with a pharmaceutically-acceptable carrier.
Claim 13
Dependent Claim 27 words
A method of claim 9, wherein the neurotransmitters treated are the quisqualate receptors and the amount of the compound administered is a quisqualate-antagonistic amount of the compound.

References Cited (Backward Citations)

US3431111A Cited
EP0283959A1 Cited
US4889855A Cited
US4912108A Cited
US4948794A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1994-06-24 1994-12-24 1995-06-25 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1998-06-24 1998-12-24 1999-06-25 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2002-06-24 2002-12-24 2003-06-25 $7700.00 Window Closed / Lapsed

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