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US4902686A
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Tricyclic heterocyclic compounds and their use in treating benzodiazepin receptor-related ailments
Assignee: Novo Nordisk AS
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Filing: 1989-04-20
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Granted: 1990-02-20
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Expires: 2009-04-20
Abstract
Abstract New heterocyclic compounds having the general formula ##STR1## wherein R 3 is ##STR2## CO 2 R' or CONR'R", wherein R' and R" independently are C 1-6 -alkyl, C 3-7 -cycloalkyl or C 1-6 -alkoxymethyl; --A-- is --C(═O)--NR'"--, --NR'"--C(═O)--, or ##STR3## wherein R'" is C 1-6 -alkyl; X is C or N; and R 4 is hydrogen, halogen, CN, C 1-6 -alkyl, C 1-6 -alkynyl, trimethylsilyl-C 1-6 -alkynyl, aryloxy which may be substituted with halogen, aralkoxy, C 3-7 -cycloalkoxy which may be substituted with one or more C 1-6 -alkyl groups, or NR""R'"", wherein R"" and R""' independently are C 1-6 -alkyl or together with the nitrogen atom form a 3-7 membered heterocyclic ring. The compounds are useful in psychopharmaceutical preparations as anticonvulsants, anxiolytics, hypnotics, and nootropics.
Inventors
- 👤 Frank Watjen
- 👤 Holger C. Hansen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 17:10
CPC Classifications
C; C07; C07D; C07D471/00; C07D471/02; C07D471/04; A; A61; A61P; A61P25/00; A61P25/20; C07D471/12; C07D471/14; C07D487/00; C07D487/02; C07D487/04; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/0803; C07F7/081; C07F7/0812
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
154 words
A heterocyclic compound having the formula I ##STR23## wherein R 3 is ##STR24## wherein R' is C 1-6 -alkyl, C 3-7 -cycloalkyl, or C 1-6 -alkoxymethyl; --A-- is --C(═O)--NR'"--or --NR'"--C(═O)-- wherein R'" is C 1-6 -alkyl; X is C or N; and R 4 is hydrogen, halogen, CN, C 1-6 -alkyl, C 2-6 -alkynyl, trimethylsilyl-C 2-6 -alkynyl, aryloxy which may be substituted with halogen, aralkoxy, C 3-7 -cycloalkoxy which may be substituted with one or more C 1-6 -alkyl groups, or NR""R'"", wherein R"" and R'"" independently are C 1-6 -alkyl or together with the nitrogen atom form a piperidine ring, provided that R 4 is not hydrogen, methyl or halogen when A is --C(C═O)--NR'"-- and R 3 is oxadiazole, R' is C 1-6 -alkyl or C 3-7 -cycloalkyl, and X is C, and that R 4 is not hydrogen, methyl or halogen when A is --NR'"--C(═O)--R 3 is oxadiazole, and X is C.
Claim 2
Dependent Claim
154 words
A heterocyclic compound having the formula I ##STR23## wherein R 3 is ##STR24## wherein R' is C 1-6 -alkyl, C 3-7 -cycloalkyl, or C 1-6 -alkoxymethyl; --A-- is --C(═O)--NR'"--or --NR'"--C(═O)-- wherein R'" is C 1-6 -alkyl; X is C or N; and R 4 is hydrogen, halogen, CN, C 1-6 -alkyl, C 2-6 -alkynyl, trimethylsilyl-C 2-6 -alkynyl, aryloxy which may be substituted with halogen, aralkoxy, C 3-7 -cycloalkoxy which may be substituted with one or more C 1-6 -alkyl groups, or NR""R'"", wherein R"" and R'"" independently are C 1-6 -alkyl or together with the nitrogen atom form a piperidine ring, provided that R 4 is not hydrogen, methyl or halogen when A is --C(C═O)--NR'"-- and R 3 is oxadiazole, R' is C 1-6 -alkyl or C 3-7 -cycloalkyl, and X is C, and that R 4 is not hydrogen, methyl or halogen when A is --NR'"--C(═O)--R 3 is oxadiazole, and X is C.
Claim 3
Dependent Claim
8 words
A compound of claim 1 which is 3-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)-4-methyl-5-oxo-6-(4-fluorophenoxy)-4,5-dihydro-imidazo(1,5-a)quinazoline.
Claim 4
Dependent Claim
8 words
A compound of claim 1 which is 3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-5-ethyl-4,5-dihydro-4-oxo-imidazo(1,5-a)pyrido(2,3-e)pyrazine.
Claim 5
Dependent Claim
8 words
A compound of claim 1 which is 4,5-dihydro-4-methyl-3-(5-methyl-1,2,4-oxadiazol-3-yl)-5-oxo-6-trimethylsilylethynyl-imidazo(1,5-a)quinazoline.
Claim 6
Dependent Claim
9 words
A compound of claim 1 which is 3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-4,5-dihydro-5-methyl-4-oxo-imidazo (1,5-a)pyrido(2,3-e)pyrazine.
Claim 7
Dependent Claim
9 words
A compound of claim 1 which is 5-ethyl-4,5-dihydro-3-(3-methyl-1,2,4-oxadiazol-5-yl)-4-oxo-imidazo(1,5-a)pyrido (2,3-e)pyrazine.
Claim 8
Dependent Claim
8 words
A compound of claim 1 which is 6-(3-chlorophenoxy)-3-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5-a)quinazoline.
Claim 9
Dependent Claim
45 words
A pharmaceutical composition suitable for use in the treatment of a central nervous system ailment related to the benzodiazepin receptors comprising an amount of a compound of claim 1 which is effective for the alleviation of such disorder together with a pharmaceutically-acceptable carrier or diluent.
Claim 10
Dependent Claim
22 words
A pharmaceutical composition according to claim 8 in the form of an oral dosage unit containing 1-100 mg of the active compound.
Claim 11
Dependent Claim
47 words
A method of treating a central nervous system ailment related to the benzodiazepin receptors in a subject in need of such treatment comprising the step of administering to said subject an amount of a compound of claim 1 which is effective for the alleviation of such ailment.
Claim 12
Dependent Claim
67 words
A method of treating a central nervous system ailment related to the benzodiazepin receptors in a subject in need of such treatment comprising the step of administering to said subject an amount of a compound of claim 1 which is effective for the alleviation of such ailment in the form of a pharmaceutical composition thereof, in which it is present together with a pharmaceutically-acceptable carrier or diluent.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1993-02-19 | 1993-08-21 | 1994-02-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-02-19 | 1997-08-21 | 1998-02-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-02-19 | 2001-08-21 | 2002-02-20 | $7700.00 | Window Closed / Lapsed |