Patent US4003909A successfully refreshed from Google Patents.
US4003909A
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[(1,2,4-Oxadiazol-3-yl)phenyl]carbamic or thiocarbamic acid esters
Assignee: ER Squibb and Sons LLC
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Filing: 1975-04-09
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Granted: 1977-01-18
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Expires: 1995-04-09
Abstract
Abstract Compounds of the formula ##STR1## and their acid-addition salts wherein X is O or S; R is hydrogen, lower alkyl, phenyl, chloro, bromo, trifluoromethyl, lower alkoxy, phenoxy, or di(lower alkyl)amino; R 1 is hydrogen, lower alkyl, phenyl, substituted-phenyl, cycloalkyl, or heterocyclic; and R 3 is lower alkyl, substituted-lower alkyl, cycloalkyl, lower alkenyl, lower alkynyl, phenyl, or substituted phenyl; are disclosed. These compounds exhibit anthelmintic and antibacterial and antifungal activity.
Inventors
- 👤 Venkatachala L. Narayanan
- 👤 Rudiger D. Haugwitz
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 08:48
CPC Classifications
C; C07; C07D; C07D271/00; C07D271/02; C07D271/06
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
136 words
A compound of the formula ##STR8##wherein X is oxygen or sulfur; R is selected from the group consisting of hydrogen, lower alkyl, phenyl, chloro, bromo, lower alkoxy, trifluoromethyl, phenoxy, and di(lower alkyl)-amino; R 1 is selected from the group consisting of hydrogen, lower alkyl, cycloalkyl of 3 to 6 carbons, phenyl, and substituted-phenyl; and R 3 is selected from the group consisting of lower alkyl, substituted-lower alkyl, lower alkenyl, lower alkynyl; cycloalkyl of 3 to 6 carbons, phenyl and substituted phenyl; said phenyl substituent being one or two members selected from the group consisting of fluoro, chloro, bromo, iodo, nitro, amino, trifluoromethyl, lower alkyl, and lower alkoxy or trimethoxy and said lower alkyl substituent being one or more members selected from the group consisting of chloro, bromo, fluoro and iodo; and the pharmaceutically acceptable salts thereof.
Claim 2
Dependent Claim
136 words
A compound of the formula ##STR8##wherein X is oxygen or sulfur; R is selected from the group consisting of hydrogen, lower alkyl, phenyl, chloro, bromo, lower alkoxy, trifluoromethyl, phenoxy, and di(lower alkyl)-amino; R 1 is selected from the group consisting of hydrogen, lower alkyl, cycloalkyl of 3 to 6 carbons, phenyl, and substituted-phenyl; and R 3 is selected from the group consisting of lower alkyl, substituted-lower alkyl, lower alkenyl, lower alkynyl; cycloalkyl of 3 to 6 carbons, phenyl and substituted phenyl; said phenyl substituent being one or two members selected from the group consisting of fluoro, chloro, bromo, iodo, nitro, amino, trifluoromethyl, lower alkyl, and lower alkoxy or trimethoxy and said lower alkyl substituent being one or more members selected from the group consisting of chloro, bromo, fluoro and iodo; and the pharmaceutically acceptable salts thereof.
Claim 3
Dependent Claim
33 words
The compound of claim 1 wherein R is hydrogen or chlorine; and R 1 is selected from the group consisting of hydrogen, lower alkyl, cycloaklyl of 3 to 6 carbons, phenyl and substituted-phenyl.
Claim 4
Dependent Claim
77 words
The compound of claim 2 wherein R is hydrogen; R 1 is selected from the group consisting of hydrogen, cyclopropyl, cyclohexyl, phenyl, 4-chlorophenyl, and 3,4,5-trimethoxyphenyl; and R 3 is selected from the group consisting of alkyl of 1 to 4 carbons, phenyl, substituted-phenyl, and substituted-alkyl of 1 to 4 carbons wherein said alkyl substituent is one, two, or three chloro, bromo, or fluoro groups, alkenyl of 2 to 4 carbons, and alkynyl of 2 to 4 carbons.
Claim 5
Dependent Claim
116 words
A compound of the formula ##STR9##wherein X is oxygen or sulfur; R 1 is selected from the group consisting of hydrogen, lower alkyl, cycloalkyl of 3 to 6 carbons, phenyl, and substituted phenyl; and R 3 is selected from the group consisting of lower alkyl, lower alkenyl, lower alkynyl, substituted-lower alkyl, cycloalkyl of 3 to 6 carbons, phenyl, and substituted phenyl; said phenyl substituent being one or two members selected from the group consisting of fluoro, chloro, bromo, iodo, nitro, amino, trifluoromethyl, lower alkyl and lower alkoxy or trimethoxy and said lower alkyl substituent being one or more members selected from the group consisting of chloro, bromo, fluoro, and iodo; and the pharmaceutically acceptable salts thereof.
Claim 6
Dependent Claim
116 words
A compound of the formula ##STR9##wherein X is oxygen or sulfur; R 1 is selected from the group consisting of hydrogen, lower alkyl, cycloalkyl of 3 to 6 carbons, phenyl, and substituted phenyl; and R 3 is selected from the group consisting of lower alkyl, lower alkenyl, lower alkynyl, substituted-lower alkyl, cycloalkyl of 3 to 6 carbons, phenyl, and substituted phenyl; said phenyl substituent being one or two members selected from the group consisting of fluoro, chloro, bromo, iodo, nitro, amino, trifluoromethyl, lower alkyl and lower alkoxy or trimethoxy and said lower alkyl substituent being one or more members selected from the group consisting of chloro, bromo, fluoro, and iodo; and the pharmaceutically acceptable salts thereof.
Claim 7
Dependent Claim
80 words
The compound of claim 4 wherein R 1 is selected from the group consisting of hydrogen, cyclopropyl, cyclohexyl, phenyl, 4-chlorophenyl, and 3,4,5-trimethoxyphenyl; and R 3 is selected from the group consisting of alkyl of 1 to 4 carbons, alkenyl of 2 to 4 carbons, alkynyl of 2 to 4 carbons, cycloalkyl of 3 to 6 carbons, phenyl, substituted-phenyl, and substituted alkyl of 1 to 4 carbons wherein said alkyl substituent is one, two, or three chloro, bromo, or fluoro groups.
Claim 8
Dependent Claim
33 words
The compound of claim 5 wherein R 1 is hydrogen and R 3 is selected from the group consisting of alkyl of 1 to 4 carbons, allyl, 2-propynyl, cyclopropyl, phenyl, 2,2,2-trichloroethyl, and 4-fluorophenyl.
Claim 9
Dependent Claim
17 words
The compound of claim 6 wherein X is oxygen and R 3 is methyl, phenyl, or 2,2,2-trichloroethyl.
Claim 10
Dependent Claim
10 words
The compound of claim 7 wherein R 3 is methyl.
Claim 11
Dependent Claim
10 words
The compound of claim 7 wherein R 3 is phenyl.
Claim 12
Dependent Claim
10 words
The compound of claim 7 wherein R 3 is 2,2,2-trichloroethyl.
References Cited (Backward Citations)
US3270028A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-01-18 | 1980-07-19 | 1981-01-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-01-18 | 1984-07-19 | 1985-01-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-01-18 | 1988-07-19 | 1989-01-18 | $7700.00 | Window Closed / Lapsed |