US4234586A
Expired / Lapsed
US
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Nitrogen bridgehead compounds having anti-allergic effect
Assignee: Chinoin Private Co Ltd
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Filing: 1978-12-11
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Granted: 1980-11-18
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Expires: 1998-12-11
Abstract
Abstract Antiallergic and particularly antiasthmatic compounds of the formula: ##STR1## of which 9-phenylhydrazono-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido(1,2-a)pyrimidine-3-carboxylic acid is an especially significant example.
Inventors
- 👤 Istvan Hermecz
- 👤 Zoltan Meszaros
- 👤 Tibor Breining
- 👤 Sandor Virag
- 👤 Lelle V. Vasvari nee Debreczy
- 👤 Agnes Horvath
- 👤 Gabor Nagy
- 👤 Attila Mandi
- 👤 Tamas Szucs
- 👤 Istvan Bitter
- 👤 Gyula Sebestyen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 14:46
CPC Classifications
C; C07; C07D; C07D471/00; C07D471/02; C07D471/04; A; A61; A61P; A61P1/00; A61P1/04; A61P11/00; A61P11/06; A61P25/00; A61P25/04; A61P25/20; A61P29/00; A61P31/00; A61P31/04; A61P37/00; A61P37/08; A61P43/00; A61P7/00; A61P7/02; A61P9/00; A61P9/10
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
222 words
A compound of the formula: ##STR21## or a pharmaceutically acceptable salt, hydrate, stereoisomer, optically active isomer, geometric isomer or tautomeric form thereof, wherein: R is hydrogen or lower alkyl; R 1 is hydrogen, lower alkyl, styryl or carboxy; R 2 is hydrogen, lower alkyl or hydroxy; R 3 is hydrogen, lower alkyl, phenyl, naphthyl, formyl, lower alkanoyl, carboxyl, lower alkoxycarbonyl, carbamoyl, --CO--NH--NH 2 , cyano, --CH--NH--OH, or a group of the formulae --(CH 2 )m--COOH, --(CH 2 )m--COO--loweralkyl, --(CH 2 )m--CONH 2 , --(CH 2 )m--NH--NH 2 , --(CH 2 )m--CN or --(CH 2 )m--CO--NH--OH, wherein m=1, 2 or 3; R 4 is hydrogen, lower alkyl, lower alkyl substituted by hydroxy or carboxy, trifluoromethyl, phenyl, naphthyl, phenyl or naphthyl substituted by at least one halogen, lower alkyl, lower alkoxy, lower alkylenedioxy, trifluoromethyl, nitro, aminosulfonyl, carboxyl, sulfo, hydroxy, or amino, phenyl-loweralkyl, 2-, 3-, or 4-pyridyl, benzothiazol-2-yl, methoxycarbonyl or ethoxycarbonyl; and R 5 is hydrogen, lower alkanoyl, benzoyl or nicotinoyl; or R 4 and R 5 together with the adjacent nitrogen atom form a piperidino, pyrrolidino, or morpholino ring; or R 4 and R 5 together with the adjacent nitrogen atom form a group of the formula: ##STR22## wherein R 6 is hydrogen and R 7 is phenyl or phenyl substituted by N,N-dimethylamino; or R 4 and R 5 together form a 2-azepinylidene group.
Claim 2
Dependent Claim
222 words
A compound of the formula: ##STR21## or a pharmaceutically acceptable salt, hydrate, stereoisomer, optically active isomer, geometric isomer or tautomeric form thereof, wherein: R is hydrogen or lower alkyl; R 1 is hydrogen, lower alkyl, styryl or carboxy; R 2 is hydrogen, lower alkyl or hydroxy; R 3 is hydrogen, lower alkyl, phenyl, naphthyl, formyl, lower alkanoyl, carboxyl, lower alkoxycarbonyl, carbamoyl, --CO--NH--NH 2 , cyano, --CH--NH--OH, or a group of the formulae --(CH 2 )m--COOH, --(CH 2 )m--COO--loweralkyl, --(CH 2 )m--CONH 2 , --(CH 2 )m--NH--NH 2 , --(CH 2 )m--CN or --(CH 2 )m--CO--NH--OH, wherein m=1, 2 or 3; R 4 is hydrogen, lower alkyl, lower alkyl substituted by hydroxy or carboxy, trifluoromethyl, phenyl, naphthyl, phenyl or naphthyl substituted by at least one halogen, lower alkyl, lower alkoxy, lower alkylenedioxy, trifluoromethyl, nitro, aminosulfonyl, carboxyl, sulfo, hydroxy, or amino, phenyl-loweralkyl, 2-, 3-, or 4-pyridyl, benzothiazol-2-yl, methoxycarbonyl or ethoxycarbonyl; and R 5 is hydrogen, lower alkanoyl, benzoyl or nicotinoyl; or R 4 and R 5 together with the adjacent nitrogen atom form a piperidino, pyrrolidino, or morpholino ring; or R 4 and R 5 together with the adjacent nitrogen atom form a group of the formula: ##STR22## wherein R 6 is hydrogen and R 7 is phenyl or phenyl substituted by N,N-dimethylamino; or R 4 and R 5 together form a 2-azepinylidene group.
Claim 3
Dependent Claim
18 words
A compound according to claim 1 wherein R is hydrogen and R 1 is hydrogen or lower alkyl.
Claim 4
Dependent Claim
11 words
A compound according to claim 1 wherein R 3 is carboxyl.
Claim 5
Dependent Claim
19 words
A compound according to claim 1 wherein R 3 is lower alkoxycarbonyl, carbamoyl, cyano, phenyl, lower alkyl or formyl.
Claim 6
Dependent Claim
62 words
A compound according to claim 1 wherein R 4 is phenyl which can be substituted with one, two or three identical or different substituents selected from the group which consists of hydroxy, lower alkoxy, nitro, carboxylic group, lower alkyl, trifluoromethyl, methylenedioxy, amino and halogen; or a naphthyl group or a pyridyl group and R 5 is hydrogen, formyl, acetyl, benzoyl or nicotinoyl.
Claim 7
Dependent Claim
38 words
A compound according to claim 1 wherein R is hydrogen, R 1 is methyl attached to position 6, R 2 is hydrogen, R 3 is carboxyl, R 4 is substituted or unsubstituted phenyl and R 5 is hydrogen.
Claim 8
Dependent Claim
11 words
Racemic or optically active 9-phenylhydrazono-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido(1,2-a)pyrimidine-3-carboxylic acid as defined in claim 1.
Claim 9
Dependent Claim
11 words
Racemic or optically active 9-(p-bromo-phenyl-hydrazono)-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido(1,2-a)pyrimidine-3-carboxylic acid as defined in claim 1.
Claim 10
Dependent Claim
11 words
Racemic or optically active 9-(p-chloro-phenyl-hydrazono)-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido(1,2-a)pyrimidine-3-carboxylic acid as defined in claim 1.
Claim 11
Dependent Claim
11 words
Racemic or optically active 6-methyl-9-(3-pyridyl-hydrazono)-4-oxo-6,7,8,9-tetrahydro-4H-pyrido(1,2-a)pyrimidine-3-carboxylic acid as defined in claim 1.
Claim 12
Dependent Claim
11 words
Racemic or optically active 9-hydrazono-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido(1,2-a)pyrimidine-3-carboxylic acid as defined in claim 1.
Claim 13
Dependent Claim
11 words
Racemic or optically active 9-(p-ethoxy-phenyl-hydrazono)-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido(1,2-a)pyrimidine-3-carboxylic acid as defined in claim 1.
Claim 14
Dependent Claim
11 words
Racemic or optically active 9-(3,4-dichlorophenyl-hydrazono)-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido(1,2-a)pyrimidine-3-carboxylic acid as defined in claim 1.
Claim 15
Dependent Claim
11 words
Racemic or optically active 9-(3-nitro-phenyl)-hydrazono-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido(1,2-a)pyrimidine-3-carboxylic acid as defined in claim 1.
Claim 16
Dependent Claim
11 words
Racemic or optically active 9-(3-chloro-phenyl-hydrazano)-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido(1,2-a)pyrimidine-3-carboxylic acid as defined in claim 1.
Claim 17
Dependent Claim
11 words
Racemic or optically active 9-(4-carboxy-phenyl-hydrazano)-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido(1,2-a)pyrimidine-3-carboxylic acid as defined in claim 1.
Claim 18
Dependent Claim
11 words
Racemic or optically active 9-(3-methyl-phenyl-hydrazano)-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido(1,2-a)pyrimidine-3-carboxylic acid as defined in claim 1.
Claim 19
Dependent Claim
35 words
An anti-asthma composition comprising as active ingredient a pharmaceutically effective amount of the compound defined in claim 1 or a pharmaceutically acceptable salt thereof in admixture with an inert solid or liquid pharmaceutically acceptable carrier.
Claim 20
Dependent Claim
30 words
The anti-asthma composition defined in claim 18 wherein the active ingredient is a pharmaceutically effective amount of 9-phenyl-hydrazono-6-methyl-4-oxo-4H-pyrido(1,2-a)pyrimidine-3-carboxylic acid or an optically active andipode or a pharmaceutically acceptable salt thereof.
Claim 21
Dependent Claim
31 words
A method of treating asthma in an animal subject comprising administering to said subject an effective amount of a compound as defined in claim 1 or a pharmaceutically acceptable salt thereof.
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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) | 1983-11-18 | 1984-05-19 | 1984-11-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-11-18 | 1988-05-19 | 1988-11-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-11-18 | 1992-05-19 | 1992-11-18 | $7700.00 | Window Closed / Lapsed |