US3932416A
Expired / Lapsed
US
⏱️ 0.0 years remaining
N-tetrazolyl quinaldamides
Assignee: Allen and Hanburys Ltd
•
Filing: 1973-06-21
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Granted: 1976-01-13
•
Expires: 1993-06-21
Abstract
Abstract Compounds of the general formula (I): ##SPC1## in which R 1 , R 2 and R 3 may be the same or different and each represents a hdyrogen atom, an alkyl group, a nitro group, a halogen atom or a group of the formula --NR 4 R 5 or --OR 4 ; in which the groups R 4 and R 5 may be the same or different and each represent a hydrogen atom, or an alkyl, alkenyl or cycloalkyl group (which alkyl group may optionally be substituted by alkoxy, hydroxy, amino, alkylamino, dialkylamino or aryl groups) or R 4 and R 5 together with the nitrogen atom form a heterocyclic ring which may optionally contain additional hetero atoms, e.g. morpholino or piperazinyl; and R 6 represents a hydrogen atom or an alkyl group. These compounds have biological activity, particularly in inhibiting the release of spasmogenic substances arising as a consequence of antigen-antibody reactions.
Inventors
- 👤 David Edmund Bays
- 👤 Mervyn Evan Peel
- 👤 David Martin Waters
- 👤 Gwynn Pennant Ellis
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 08:44
CPC Classifications
C; C07; C07D; C07D215/00; C07D215/02; C07D215/16; C07D215/48; C07D401/00; C07D401/02; C07D401/12; C07D401/14
Claims Analysis
Total Claims: 36
Claim 1
Independent Claim
143 words
A compound of the formula: ##SPC6## in which R 1 , R 2 and R 3 independently represent a hydrogen atom, alkyl, nitro, a halogen atom or --NR 4 R 5 or --OR 4 ; in which R 4 and R 5 independently represent a hydrogen atom, alkenyl, cycloalkyl, alkyl, or alkyl substituted by alkoxy, hydroxy, amino, alkylamino, dialkylamino or phenyl and R 6 represents a hydrogen atom or a pharmaceutically acceptable ester thereof with a simple aliphatic acid; or a pharmaceutically acceptable salt thereof, any alkyl moiety being of 1 to 6 carbon atoms, any alkenyl moiety being of 2 to 6 carbon atoms, any cycloalkyl moiety being of 5 or 6 carbon atoms, R 2 and R 3 , when both are vicinal and other than hydrogen, said substituents are methyl and there being present no more than one nitro substituent.
Claim 2
Dependent Claim
143 words
A compound of the formula: ##SPC6## in which R 1 , R 2 and R 3 independently represent a hydrogen atom, alkyl, nitro, a halogen atom or --NR 4 R 5 or --OR 4 ; in which R 4 and R 5 independently represent a hydrogen atom, alkenyl, cycloalkyl, alkyl, or alkyl substituted by alkoxy, hydroxy, amino, alkylamino, dialkylamino or phenyl and R 6 represents a hydrogen atom or a pharmaceutically acceptable ester thereof with a simple aliphatic acid; or a pharmaceutically acceptable salt thereof, any alkyl moiety being of 1 to 6 carbon atoms, any alkenyl moiety being of 2 to 6 carbon atoms, any cycloalkyl moiety being of 5 or 6 carbon atoms, R 2 and R 3 , when both are vicinal and other than hydrogen, said substituents are methyl and there being present no more than one nitro substituent.
Claim 3
Dependent Claim
32 words
A compound as claimed in claim 1 in which the group R 1 is hydrogen, halogen, hydroxy, alkylamiho, hydroxyalkylamino, hydroxyalkyl-alkylamino, dihydroxyalkylamino, alkoxyalkylamino, aminoalkylamino, dialkylaminoalkylalkylamino, cycloalkylamino, alkoxy, alkenyloxy, aralkyloxy, hydroxyalkoxy,- 2-formyloxyethoxy, or alkoxyalkoxy.
Claim 4
Dependent Claim
32 words
A compound as claimed in claim 1 in which at least one of the groups R 2 and R 3 is hydrogen, 6-alkoxy, 6-nitro, 6-amino, 6-alkyl, 7-alkyl 8-alkyl, 7-alkoxy, 8-nitro or 8-amino.
Claim 5
Dependent Claim
13 words
A compound as claimed in claim 1 in which R 6 is hydrogen.
Claim 6
Dependent Claim
8 words
The compound of claim 1 which is N-(1H-Tetrazol-5-yl)quinaldamide.
Claim 7
Dependent Claim
8 words
The compound of claim 1 which is 4-Chloro-(1H-tetrazol-5-yl)quinaldamide.
Claim 8
Dependent Claim
8 words
The compound of claim 1 which is 6-Butyl-4-chloro-N(1H-tetrazol-5-yl)quinaldamide.
Claim 9
Dependent Claim
8 words
The compound of claim 1 which is 4(2-Hydroxy-ethylamino)-N(1H-tetrazol-5-yl)quinaldamide.
Claim 10
Dependent Claim
16 words
The compound of claim 1 which is the sodium salt of the compound of claim 7.
Claim 11
Dependent Claim
8 words
The compound of claim 1 which is 4(3-Hydroxy-propylamino)-N(1H-tetrazol-5-yl)quinaldamide.
Claim 12
Dependent Claim
10 words
The compound of claim 1 which is 4[(2-Hydroxy ethyl)methylamino]-N(1H-tetrazol-5-yl)quinaldamide, hydrochloride.
Claim 13
Dependent Claim
9 words
The compound of claim 1 which is 4(2,3-Dihydroxypropylamino)-N(1H-tetrazol-5-yl)quinaldamide, hydrochloride.
Claim 14
Dependent Claim
8 words
The compound of claim 1 which is 4(2-Methoxyethylamino)-N(1H-tetrazol-5-yl)quinaldamide.
Claim 15
Dependent Claim
9 words
The compound of claim 1 which is 4(2-Aminoethylamino)-N(1H-tetrazol-5-yl)quinaldamide, hydrochloride.
Claim 16
Dependent Claim
9 words
The compound of claim 1 which is 4[(2-Dimethylaminoethyl)methylamino]-N(1H-tetrazol-5-yl)quinaldamide, dihydrochloride.
Claim 17
Dependent Claim
9 words
The compound of claim 1 which is 4(2-Dimethylaminoethylamino)-N(1H-tetrazol-5-yl)quinaldamide, dihydrochloride.
Claim 18
Dependent Claim
9 words
The compound of claim 1 which is 4-Cyclohexylamino-N(1H-tetrazol-5-yl)quinaldamide, hydrochloride.
Claim 19
Dependent Claim
8 words
The compound of claim 1 which is 4-Chloro-6-methoxy-N(1H-tetrazol-5-yl)quinaldamide.
Claim 20
Dependent Claim
8 words
The compound of claim 1 which is 4-Chloro-7,8-dimethyl-N(1H-tetrazol-5-yl)quinaldamide.
Claim 21
Dependent Claim
8 words
The compound of claim 1 which is 4,7-Dimethoxy-N(1H-tetrazol-5-yl)quinaldamide.
Claim 22
Dependent Claim
8 words
The compound of claim 1 which is 4-Methoxy-N(1H-tetrazol-5yl)quinaldamide.
Claim 23
Dependent Claim
10 words
The compound of claim 1 which is 4-Methoxy-N(1H-tetrazol-5-yl)quinaldamide, sodium salt.
Claim 24
Dependent Claim
8 words
The compound of claim 1 which is 4-Methoxy-6-nitro-N(1H-tetrazol-5-yl)quinaldamide.
Claim 25
Dependent Claim
8 words
The compound of claim 1 which is 4-Methoxy-8-nitro-N(1H-tetrazol-5-yl)quinaldamide.
Claim 26
Dependent Claim
8 words
The compound of claim 1 which is 6-Amino-4-methoxy-N(1H-tetrazol-5-yl)quinaldamide.
Claim 27
Dependent Claim
8 words
The compound of claim 1 which is 8-Amino-4-methoxy-N(1H-tetrazol-5-yl)quinaldamide.
Claim 28
Dependent Claim
8 words
The compound of claim 1 which is 4-Allyloxy-N(1H-tetrazol-5-yl)quinaldamide.
Claim 29
Dependent Claim
8 words
The compound of claim 1 which is 4(2-Formyloxyethoxy)-N(1H-tetrazol-5-yl)quinaldamide.
Claim 30
Dependent Claim
8 words
The compound of claim 1 which is 4(2-Hydroxyethoxy)-N(1H-tetrazol-5-yl)quinaldamide.
Claim 31
Dependent Claim
8 words
The compound of claim 1 which is 4-Benzyloxy-N(1H-tetrazol-5-yl)quinaldamide.
Claim 32
Dependent Claim
8 words
The compound of claim 1 which is 4-Hydroxy-N(1H-tetrazol-5-yl)quinaldamide.
Claim 33
Dependent Claim
8 words
The compound of claim 1 which is 4-Butyloxy-N(1H-tetrazol-5-yl)quinaldamide.
Claim 34
Dependent Claim
8 words
The compound of claim 1 which is 4,6-dimethoxy-N(1H-tetrazol-5-yl)quinaldamide.
Claim 35
Dependent Claim
8 words
The compound of claim 1 which is 4-(2-Methoxyethoxy)-N(1H-tetrazol-5-yl)quinaldamide.
Claim 36
Dependent Claim
8 words
The compound of claim 1 which is 4-Ethylamino-N(1H-tetrazol-5-yl)quinaldamide.
References Cited (Backward Citations)
US3391146A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-01-12 | 1979-07-14 | 1980-01-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-01-12 | 1983-07-14 | 1984-01-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-01-12 | 1987-07-14 | 1988-01-13 | $7700.00 | Window Closed / Lapsed |