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US4560689A Expired / Lapsed US ⏱️ 0.0 years remaining

Heterocyclic-fused pyrazolo-[3,4-d]pyridin-3-ones as benzodiazepine receptor modulators

Assignee: Novartis Corp
•
Filing: 1984-08-06
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Granted: 1985-12-24
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Expires: 2004-08-06
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Abstract

Abstract Disclosed are heterocyclic-fused pyrazolo[3,4-d]pyridin-3-ones useful as benzodiazepine receptor modulators.

Inventors

  • 👤 Naokata Yokoyama

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-30 16:38
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/72; C07D213/74; C07D213/75; C07D213/78; C07D213/79; C07D213/80; C07D231/00; C07D231/02; C07D231/10; C07D231/14; C07D231/28; C07D231/30; C07D231/32; C07D231/34; C07D401/00; C07D401/02; C07D401/04; C07D401/12; C07D471/00; C07D471/02; C07D471/04; C07D471/12; C07D471/14; C07D495/00; C07D495/12; C07D495/14

Claims Analysis

Total Claims: 12
Claim 1
Independent Claim 211 words
A compound of the formula ##STR11## or ##STR12## wherein A together with the two carbon atoms to which it is attached represents a fused heterocyclic ring selected from (a) thieno, furo, and N-unsubstituted or N-lower alkyl substituted pyrrolo, wherein the carbon atoms in any of said rings are unsubstituted or one of them is substituted by lower alkyl, carbo-(lower)-alkoxy, halogen or trifluoromethyl; (b) N-unsubstituted or lower alkyl substituted-imidazo, wherein the carbon atom in said ring is unsubstituted or substituted by lower alkyl, lower alkoxy, halogen or trifluoromethyl; (c) thiazolo, oxazolo, isoxazolo, and pyridazino, wherein the carbon atoms forming any of said rings are unsubstituted or one or two are substituted by lower alkyl, lower alkoxy or halogen; (d) pyrimido and pyrazino wherein the carbon atoms in any of said rings are unsubstituted or one is substituted by lower alkyl or lower alkoxy; R 1 represents phenyl, or phenyl mono- or disubstituted by lower alkyl, lower alkoxy, halogen or trifluoromethyl; or R 1 represents an aromatic heterocyclic radical selected from pyridyl, quinolyl, isoquinolyl, pyrimidyl and thiazolyl, or any said heterocyclic radical mono- or di-substituted by lower alkyl, lower alkoxy or halogen; R 2 , R 3 and R 3 ' independently represent hydrogen or lower alkyl; or a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim 211 words
A compound of the formula ##STR11## or ##STR12## wherein A together with the two carbon atoms to which it is attached represents a fused heterocyclic ring selected from (a) thieno, furo, and N-unsubstituted or N-lower alkyl substituted pyrrolo, wherein the carbon atoms in any of said rings are unsubstituted or one of them is substituted by lower alkyl, carbo-(lower)-alkoxy, halogen or trifluoromethyl; (b) N-unsubstituted or lower alkyl substituted-imidazo, wherein the carbon atom in said ring is unsubstituted or substituted by lower alkyl, lower alkoxy, halogen or trifluoromethyl; (c) thiazolo, oxazolo, isoxazolo, and pyridazino, wherein the carbon atoms forming any of said rings are unsubstituted or one or two are substituted by lower alkyl, lower alkoxy or halogen; (d) pyrimido and pyrazino wherein the carbon atoms in any of said rings are unsubstituted or one is substituted by lower alkyl or lower alkoxy; R 1 represents phenyl, or phenyl mono- or disubstituted by lower alkyl, lower alkoxy, halogen or trifluoromethyl; or R 1 represents an aromatic heterocyclic radical selected from pyridyl, quinolyl, isoquinolyl, pyrimidyl and thiazolyl, or any said heterocyclic radical mono- or di-substituted by lower alkyl, lower alkoxy or halogen; R 2 , R 3 and R 3 ' independently represent hydrogen or lower alkyl; or a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim 73 words
A compound according to claim 1 of formula IA or IB wherein A together with the two carbon atoms to which it is attached represent fused 2,3- or 3,2-thieno, and the carbon atoms in said thieno ring are unsubstituted or monosubstituted by lower alkyl, carbo-(lower)-alkoxy, halogen or trifluoromethyl; R 1 , R 2 , R 3 and R 3 ' have meaning as given in claim 1; or a pharmaceutically acceptable salt thereof.
Claim 4
Dependent Claim 76 words
A compound according to claim 2 of formula IV ##STR13## wherein R 1 represents phenyl or phenyl mono- or di-substituted by lower alkyl, lower alkoxy, halogen or trifluoromethyl; or an aromatic heterocyclic radical selected from pyridyl, quinolyl, isoquinolyl, pyrimidyl and thiazolyl, or any said heterocyclic radical mono- or disubstituted by lower alkyl, lower alkoxy or halogen; R 8 represents hydrogen, lower alkyl, carbo-(lower)-alkoxy, halogen or trifluoromethyl; or a tautomer thereof; or a pharmaceutically acceptable salt thereof.
Claim 5
Dependent Claim 76 words
A compound according to claim 2 of formula V ##STR14## wherein R 1 represents phenyl or phenyl mono- or di-substituted by lower alkyl, lower alkoxy, halogen or trifluoromethyl; or an aromatic heterocyclic radical selected from pyridyl, quinolyl, isoquinolyl, pyrimidyl and thiazolyl, or any said heterocyclic radical mono- or disubstituted by lower alkyl, lower alkoxy or halogen; R 9 represents hydrogen, lower alkyl, carbo-(lower)-alkoxy, halogen or trifluoromethyl; or a tautomer thereof; or a pharmaceutically acceptable salt thereof.
Claim 6
Dependent Claim 83 words
A compound according to claim 1 of formula IA or IB wherein A together with the two carbon atoms to which it is attached represents fused N-unsubstituted or N-lower alkyl substituted 5,4-imidazo, and the carbon atom in said 5,4-imidazo ring is unsubstituted or substituted by lower alkyl, phenyl or phenyl mono-substituted by lower alkyl, lower alkoxy, halogen, or trifluoromethyl; R 1 , R 2 , R 3 and R 3 ' have meaning as given claim 1; or a pharmaceutically acceptable salt thereof.
Claim 7
Dependent Claim 96 words
A compound according to claim 5 of formula VI ##STR15## wherein R 1 represents phenyl or phenyl mono- or di-substituted by lower alkyl, lower alkoxy, halogen or trifluoromethyl; or an aromatic heterocyclic radical selected from pyridyl, quinolyl, isoquinolyl, pyrimidyl and thiazolyl, or any said heterocyclic radical substituted by lower alkyl, lower alkoxy or halogen; R 2 represents hydrogen or lower alkyl; R 10 represents hydrogen, lower alkyl, phenyl or phenyl monosubstituted by lower alkyl, lower alkoxy, halogen or trifluoromethyl; R 11 represents hydrogen or lower alkyl; or a tautomer thereof; or a pharmaceutically acceptable salt thereof.
Claim 8
Dependent Claim 13 words
A compound of claim 3 being 2-p-chlorophenylthieno[2,3-b]pyrazolo[4,3-d]pyridin-3(5H)-one or a pharmaceutically acceptable salt thereof.
Claim 9
Dependent Claim 13 words
A compound of claim 4 being 2-(3-pyridyl)-thieno[3,2-b]pyrazolo-[4,3-d]pyridin-3(5H)-one or a pharmaceutically acceptable salt thereof.
Claim 10
Dependent Claim 35 words
An anxiolytic pharmaceutical composition suitable for oral or parenteral administration to mammals comprising an effective anxiolytically amount of a compound of claim 1 having anxiolytic activity in combination with one or more pharmaceutically acceptable carriers.
Claim 11
Dependent Claim 25 words
A method for treating anxiety in mammals which comprises administering to a mammal in need thereof an effective amount of a composition of claim 9.
Claim 12
Dependent Claim 222 words
A process for preparing a compound of claim 1 comprising (a) reacting a compound of formula VII ##STR16## wherein A, R 2 and R 3 have meaning as defined in claim 1, and Y is lower alkoxy; with a compound of the formula VIII R.sub.3 '--NH--NH--R.sub.1 (VIII) wherein R 1 has meaning as defined in claim 1, and R 3 ' is hydrogen; (b) reacting a compound of the formula IX ##STR17## wherein A and R 2 have meaning as defined in claim 1; X represents reactive etherified or esterified hydroxy; and Y represents lower alkoxy; with a compound of formula VIII wherein R 1 has meaning as defined in claim 1; and R 3 ' represents hydrogen or lower alkyl; (c) ring closing a compound of formula IX wherein X is --NR 3 '--NHR 1 and Y is lower alkoxy or hydroxy; or X is hydroxy, reactive esterified or etherified hydroxy and Y is --NR 1 NHR 3 '; and wherein A, R 1 , R 2 and R 3 ' have meaning as defined in claim 1; and if desired, converting a resulting compound of formula IA or IB into another compound of the invention; and, if desired, converting a resulting compound of formula IA or IB into a salt thereof or liberating a free compound from such a salt.

References Cited (Backward Citations)

US4312870A Cited
US4479955A Cited
EP0126970A2 Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1988-12-23 1989-06-24 1989-12-24 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1992-12-23 1993-06-24 1993-12-24 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1996-12-23 1997-06-24 1997-12-24 $7700.00 Window Closed / Lapsed

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