US4145554A
Expired / Lapsed
US
⏱️ 0.0 years remaining
3-Nitropyrazole derivatives
Assignee: Eli Lilly and Co
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Filing: 1977-10-13
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Granted: 1979-03-20
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Expires: 1997-10-13
Abstract
Abstract Novel 1,4-disubstituted-3-nitropyrazoles having antimicrobial, parasiticidal, and herbicidal activity are prepared by a reaction sequence of which the individual steps are conventional. The new 3-nitropyrazoles are characterized by a 1-substituent and a usually carbonyl-containing 4-substituent. The novel 3(5)-nitro-4-pyrazolecarbonitrile is obtained as an intermediate in the preparation of the biologically-active compounds. Preferred compounds are 1-alkyl or -alkenyl-4-pyrazolecarboxamides and carbonitriles. The new compounds are particularly useful for the control of bacterial animal diseases.
Inventors
- 👤 Reuben G. Jones
- 👤 Norman H. Terando
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 19:28
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/02; C07D231/10; C07D231/14; C07D231/38; A; A01; A01N; A01N43/00; A01N43/48; A01N43/56; A01N43/72; A01N43/74; A01N43/78; A01N43/82; A01N47/00; A01N47/02; A01N47/06; A01N47/08; A01N47/10; A01N47/12; A01N47/28; A01N47/38; C07D231/16; C07D231/40
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
216 words
A compound of the formula ##STR19## wherein R represents (A) C 3 -C 4 epoxyalkyl, (B) hydrogen (C) C 1 -C 10 alkyl, C 2 -C 10 alkenyl, C 3 -C 10 alkynyl, C 3 -C 10 cycloalkyl, cyclopropylmethyl, C 3 -C 10 cycloalkenyl, C 2 -C 10 alkyl mono- or disubstituted with halo or C 1 -C 3 alkoxy, or C 1 -C 10 alkyl monosubstituted with (1) mercapto, (2) carboxamido, (3) keto oxygen, (4) hydroxy, (5) phthalimido, (6) C 1 -C 3 alkylthio, (7) C 1 -C 3 alkylsulfonyl, (8) C 1 -C 3 alkanoyl, (9) phenyl, (10) phenyl monosubstituted with (a) C 1 -C 3 alkyl, (b) C 1 -C 3 haloalkyl, (c) hydroxy, or (d) halo, (11) ##STR20## wherein R 1 represents (a) C 1 -C 3 alkyl, (b) C 1 -C 3 haloalkyl, (c) C 3 -C 6 cycloalkyl, (d) phenyl, or (e) phenyl monosubstituted with (1) C 1 -C 3 alkyl, (2) C 1 -C 3 haloalkyl, (3) halo, or (4) hydroxy; and X represents (A) cyano, (B) ##STR21## wherein R 2 represents (1) hydrogen, or (2) C 1 -C 6 alkyl; or (C) ##STR22## wherein R 3 represents C 1 -C 6 alkyl; provided that a C 1 alkyl R group is substituted only with phenyl or substituted phenyl.
Claim 2
Dependent Claim
216 words
A compound of the formula ##STR19## wherein R represents (A) C 3 -C 4 epoxyalkyl, (B) hydrogen (C) C 1 -C 10 alkyl, C 2 -C 10 alkenyl, C 3 -C 10 alkynyl, C 3 -C 10 cycloalkyl, cyclopropylmethyl, C 3 -C 10 cycloalkenyl, C 2 -C 10 alkyl mono- or disubstituted with halo or C 1 -C 3 alkoxy, or C 1 -C 10 alkyl monosubstituted with (1) mercapto, (2) carboxamido, (3) keto oxygen, (4) hydroxy, (5) phthalimido, (6) C 1 -C 3 alkylthio, (7) C 1 -C 3 alkylsulfonyl, (8) C 1 -C 3 alkanoyl, (9) phenyl, (10) phenyl monosubstituted with (a) C 1 -C 3 alkyl, (b) C 1 -C 3 haloalkyl, (c) hydroxy, or (d) halo, (11) ##STR20## wherein R 1 represents (a) C 1 -C 3 alkyl, (b) C 1 -C 3 haloalkyl, (c) C 3 -C 6 cycloalkyl, (d) phenyl, or (e) phenyl monosubstituted with (1) C 1 -C 3 alkyl, (2) C 1 -C 3 haloalkyl, (3) halo, or (4) hydroxy; and X represents (A) cyano, (B) ##STR21## wherein R 2 represents (1) hydrogen, or (2) C 1 -C 6 alkyl; or (C) ##STR22## wherein R 3 represents C 1 -C 6 alkyl; provided that a C 1 alkyl R group is substituted only with phenyl or substituted phenyl.
Claim 3
Dependent Claim
11 words
A compound of claim 1 wherein X represents cyano or ##STR23##
Claim 4
Dependent Claim
8 words
The compound of claim 2 which is 1-(2-hydroxyethyl)-3-nitro-4-pyrazolecarboxamide.
Claim 5
Dependent Claim
8 words
The compound of claim 2 which is 1-(2-hydroxyethyl)-N-methyl-3-nitro-4-pyrazolecarboxamide.
Claim 6
Dependent Claim
8 words
The compound of claim 2 which is 1-(2-ethoxyethyl)-3-nitro-4-pyrazolecarboxamide.
Claim 7
Dependent Claim
8 words
The compound of claim 2 which is 1-allyl-3-nitro-4-pyrazolecarboxamide.
Claim 8
Dependent Claim
8 words
The compound of claim 2 which is 3-nitro-1-vinyl-4-pyrazolecarboxamide.
Claim 9
Dependent Claim
8 words
The compound of claim 2 which is 1-(2-ethylsulfonylethyl)-3-nitro-4-pyrazolecarboxamide.
Claim 10
Dependent Claim
8 words
The compound of claim 2 which is 1-(2-chloroethyl)-3-nitro-4-pyrazolecarbonitrile.
Claim 11
Dependent Claim
9 words
The compound of claim 2 which is 2-(4-carbamoyl-3-nitropyrazol-1-yl)ethyl acetate.
Claim 12
Dependent Claim
1 words
1,1'-(2,5-cyclohexadien-1,4-ylene)-bis(3-nitro-4-pyrazolecarboxamide).
Claim 13
Dependent Claim
1 words
1,1'-(2,5-cyclohexadien-1,4-ylene)-bis(3-nitro-4-pyrazolecarboxamide).
Claim 14
Dependent Claim
8 words
The compound of claim 2 which is 3(5)-nitro-4-pyrazolecarbonitrile.
Claim 15
Dependent Claim
8 words
The compound of claim 2 which is 3(5)-nitro-4-pyrazolecarboxamide.
Claim 16
Dependent Claim
9 words
The compound of claim 1 which is 3(5)-nitro-4-pyrazolecarboxylic acid.
Claim 17
Dependent Claim
9 words
The compound of claim 1 which is ethyl 3(5)-nitro-4-pyrazolecarboxylate.
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) | 1982-03-19 | 1982-09-18 | 1983-03-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-03-19 | 1986-09-18 | 1987-03-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-03-19 | 1990-09-18 | 1991-03-20 | $7700.00 | Window Closed / Lapsed |