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US3969366A
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3[Substituted-2-(methylamino)phenyl]4-[2-oxo-2-(heterocyclic)ethyl]-5-substituted-1,2,4-triazoles
Assignee: ER Squibb and Sons LLC
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Filing: 1975-05-30
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Granted: 1976-07-13
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Expires: 1995-05-30
Abstract
Abstract Compounds of the following formula and their pharmaceutically acceptable salts ##SPC1## Wherein R 1 and R 4 are the same or different and are each a five or six membered N containing heterocycle attached at an available N atom; R 2 is hydrogen, alkyl, trifluoromethyl, phenyl, benzyl, --(CH 2 ) n --R 4 or --(CH 2 ) n --N(alkyl) 2 ; R 3 is hydrogen, halogen, nitro, trifluoromethyl, alkyl, alkoxy, or alkylthio; and n is an integer from 1 to 4; are disclosed. These compounds are useful as anti-inflammatory agents.
Inventors
- 👤 Peter C. Wade
- 👤 Berthold Richard Vogt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 02:04
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/02; C07D401/06; C07D403/00; C07D403/02; C07D403/06; C07D413/00; C07D413/02; C07D413/06; C07D487/00; C07D487/02; C07D487/04
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
111 words
A compound of the formula ##SPC7## wherein R 1 and R 4 are the same or different and each is a N containing heterocycle of the formula ##EQU9## wherein m is 0 or 1; A is CH-Q; Q is hydrogen or alkyl of 1 to 4 carbons; R 2 is hydrogen, alkyl of 1-4 carbons, trifluoromethyl, phenyl, benzyl, ##EQU10## wherein each alkyl is of 1 to 4 carbons or --(CH 2 ) n --R 4 ; n is an integer from 1 to 4; and R 3 is hydrogen, halogen, nitro, trifluoromethyl, alkyl of 1-4 carbons, alkoxy of 1-4 carbons, or alkylthio of 1-4 carbons; and a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
111 words
A compound of the formula ##SPC7## wherein R 1 and R 4 are the same or different and each is a N containing heterocycle of the formula ##EQU9## wherein m is 0 or 1; A is CH-Q; Q is hydrogen or alkyl of 1 to 4 carbons; R 2 is hydrogen, alkyl of 1-4 carbons, trifluoromethyl, phenyl, benzyl, ##EQU10## wherein each alkyl is of 1 to 4 carbons or --(CH 2 ) n --R 4 ; n is an integer from 1 to 4; and R 3 is hydrogen, halogen, nitro, trifluoromethyl, alkyl of 1-4 carbons, alkoxy of 1-4 carbons, or alkylthio of 1-4 carbons; and a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
35 words
The compound of claim 1 wherein R 1 is 1-pyrrolidinyl, 1-piperidinyl, 4-methyl-1-piperidinyl, or 3-methyl-1-pyrrolidinyl; R 2 is hydrogen, alkyl of 1-4 carbons, trifluoromethyl or phenyl; and R 3 is hydrogen, chloro, bromo, methyl, or methoxy.
Claim 4
Dependent Claim
10 words
The compound of claim 2 wherein R 3 is chloro.
Claim 5
Dependent Claim
10 words
The compound of claim 3 wherein R 1 is 1-pyrrolidinyl.
Claim 6
Dependent Claim
8 words
The compound of claim 4, 3-[5-chloro-2-(methylamino)-phenyl]-4-[2-oxo-2-(1-pyrrolidinyl)ethyl]-5-(trifluoromethyl)-1,2,4-triazole, hydrochloride (1:1).
Claim 7
Dependent Claim
52 words
The compound of claim 1 wherein R 2 is --(CH 2 ) n --R 4 and R 1 and R 4 are independently selected from the group consisting of 1-pyrrolidinyl, 1-piperidinyl, 4-methyl-1-piperidinyl, and 3-methyl-1-pyrrolidinyl; n is an integer from 1 to 4; and R 3 is hydrogen, chloro, bromo, methyl or methoxy.
Claim 8
Dependent Claim
10 words
The compound of claim 6 wherein R 3 is chloro.
Claim 9
Dependent Claim
15 words
The compound of claim 7 wherein R 1 is 1-pyrrolidinyl and R 2 is 1-pyrrolidinylmethyl.
Claim 10
Dependent Claim
8 words
The compound of claim 8, 3-[5-chloro-2-(methylamino)-phenyl]-4-[2-oxo-2-(1-pyrrolidinyl)ethyl]-5-(1-pyrrolidinylmethyl)-1,2,4-triazole, hydrochloride (1:1).
References Cited (Backward Citations)
US3308131A
Cited
US3376306A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-07-13 | 1980-01-12 | 1980-07-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-07-13 | 1984-01-12 | 1984-07-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-07-13 | 1988-01-12 | 1988-07-13 | $7700.00 | Window Closed / Lapsed |