US4066776A
Expired / Lapsed
US
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Anti-bacterial compositions containing certain 3-nitropyrazoles
Assignee: Eli Lilly and Co
•
Filing: 1976-06-18
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Granted: 1978-01-03
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Expires: 1996-06-18
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-pyrazole-carbonitrile 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
2026-11-04 02:37
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: 44
Claim 1
Independent Claim
82 words
An antibacterial composition which comprises a physiologically-acceptable inert carrier and an antibacterially-effective amount of a compound of the formula ##STR18## 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
Claim 2
Dependent Claim
82 words
An antibacterial composition which comprises a physiologically-acceptable inert carrier and an antibacterially-effective amount of a compound of the formula ##STR18## 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
Claim 3
Dependent Claim
91 words
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, ##STR19## wherein R 1 represents a. C 1 -C 3 alkyl, b. C 1 -C 3 alkoxy, c. C 1 -C 3 haloalkyl, d. amino, e. C 3 -C 6 cycloalkyl, f. phenoxy, g. phenyl, or h. phenyl monosubstituted with
Claim 4
Dependent Claim
91 words
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, ##STR19## wherein R 1 represents a. C 1 -C 3 alkyl, b. C 1 -C 3 alkoxy, c. C 1 -C 3 haloalkyl, d. amino, e. C 3 -C 6 cycloalkyl, f. phenoxy, g. phenyl, or h. phenyl monosubstituted with
Claim 5
Dependent Claim
33 words
C 1 -C 3 alkyl, 2. C 1 -C 3 haloalkyl, 3. halo, or 4. hydroxy, or 12. cyano, or D. 4-nitrophenyl, 5-nitro-2-thiazolyl, or 3-nitro-2-pyridyl; and X represents A. 5-methylamino-1,3,4-thiadiazol-2-yl, B. cyano, ##STR20##
Claim 6
Dependent Claim
33 words
C 1 -C 3 alkyl, 2. C 1 -C 3 haloalkyl, 3. halo, or 4. hydroxy, or 12. cyano, or D. 4-nitrophenyl, 5-nitro-2-thiazolyl, or 3-nitro-2-pyridyl; and X represents A. 5-methylamino-1,3,4-thiadiazol-2-yl, B. cyano, ##STR20##
Claim 7
Dependent Claim
40 words
wherein R 2 represents 1. hydrogen, or 2. C 1 -C 6 alkyl; or ##STR21## 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 8
Dependent Claim
40 words
wherein R 2 represents 1. hydrogen, or 2. C 1 -C 6 alkyl; or ##STR21## 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 9
Dependent Claim
43 words
A composition of claim 1 wherein the compound is of the formula ##STR22## wherein R 4 represents A. C 2 -C 4 alkenyl, B. cyclopropylmethyl, C. oxopropyl, D. c 1 -c 3 alkyl, E. benzyl, F. c 2 -c 3 alkyl substituted with
Claim 10
Dependent Claim
51 words
hydroxy, 2. chloro, or 3. bromo, or G. ethyl substituted with 1. C 1 -C 2 alkoxy, 2. C 1 -C 2 alkylsulfonyl, or ##STR23## wherein R 5 represents a. C 1 -C 2 alkyl, b. C 1 -C 2 alkoxy, c. phenoxy, d. phenyl, or e. phenyl monosubstituted with 3.
Claim 11
Dependent Claim
51 words
hydroxy, 2. chloro, or 3. bromo, or G. ethyl substituted with 1. C 1 -C 2 alkoxy, 2. C 1 -C 2 alkylsulfonyl, or ##STR23## wherein R 5 represents a. C 1 -C 2 alkyl, b. C 1 -C 2 alkoxy, c. phenoxy, d. phenyl, or e. phenyl monosubstituted with 3.
Claim 12
Dependent Claim
12 words
methyl, or 2. halo; and X 1 represents A. cyano, or ##STR24##
Claim 13
Dependent Claim
12 words
methyl, or 2. halo; and X 1 represents A. cyano, or ##STR24##
Claim 14
Dependent Claim
7 words
wherein R 6 represents 1. hydrogen, or
Claim 15
Dependent Claim
7 words
wherein R 6 represents 1. hydrogen, or
Claim 16
Dependent Claim
45 words
methyl. 3. A composition of claim 1 wherein the compound is of the formula ##STR25## wherein R 7 represents A. nonyl, B. hydroxyethyl, C. 4-nitrophenyl, D. nitrothiazolyl, or ##STR26## R 8 represents A. hydrogen, or B. methyl; R 9 represents A. amino, or B. methyl.
Claim 17
Dependent Claim
42 words
A composition of claim 1 wherein R represents hydrogen, alkyl, alkenyl, alkynyl, cyclopropylmethyl, cycloalkyl, cycloalkenyl, alkyl mono- or disubstituted with halo or alkoxy, or alkyl monosubstituted with mercapto, carboxamido, keto oxygen, hydroxy, phthalimido, alkylthio, alkylsulfonyl, alkanoyl, phenyl, substituted phenyl, cyano or ##STR27##
Claim 18
Dependent Claim
40 words
A composition of claim 4 wherein R represents hydrogen, alkyl, alkenyl, alkynyl, cyclopropylmethyl, cycloalkyl, cycloalkenyl, alkyl mono- or disubstituted with halo or alkoxy, or alkyl monosubstituted with mercapto, carboxamido, keto oxygen, hydroxy, alkylthio, alkylsulfonyl, alkanoyl, phenyl, substituted phenyl or cyano.
Claim 19
Dependent Claim
28 words
A composition of claim 5 wherein R represents hydrogen, alkyl, alkenyl , cyclopropylmethyl, alkyl mono- or disubstituted with halo or alkoxy, or alkyl monosubstituted with hydroxy or alkylsulfonyl.
Claim 20
Dependent Claim
43 words
A composition of claim 6 wherein R represents hydrogen, C 1 -C 4 alkyl, C 2 -C 3 alkenyl, cyclopropylmethyl, C 2 -C 4 alkyl mono- or disubstituted with halo or alkoxy, or C 2 -C 4 alkyl monosubstituted with hydroxy or alkylsulfonyl.
Claim 21
Dependent Claim
10 words
A composition of claim 4 wherein X represents cyano, ##STR28##
Claim 22
Dependent Claim
10 words
A composition of claim 5 wherein X represents cyano, ##STR29##
Claim 23
Dependent Claim
10 words
A composition of claim 6 wherein X represents cyano, ##STR30##
Claim 24
Dependent Claim
10 words
A composition of claim 7 wherein X represents cyano, ##STR31##
Claim 25
Dependent Claim
11 words
A composition of claim 11 wherein X represents cyano or ##STR32##
Claim 26
Dependent Claim
10 words
The composition of claim 12 wherein the compound is 1-(2-hydroxyethyl)-3-nitro-4-pyrazolecarboxamide.
Claim 27
Dependent Claim
10 words
The composition of claim 12 wherein the compound is 1-(2-hydroxyethyl)-N-methyl-3-nitro-4-pyrazolecarboxamide.
Claim 28
Dependent Claim
10 words
The composition of claim 12 wherein the compound is 1-(2-ethoxyethyl)-3-nitro-4-pyrazolecarboxamide.
Claim 29
Dependent Claim
10 words
The composition of claim 12 wherein the compound is 1-allyl-3-nitro-4-pyrazolecarboxamide.
Claim 30
Dependent Claim
10 words
The composition of claim 12 wherein the compound is 3-nitro-1-vinyl-4-pyrazolecarboxamide.
Claim 31
Dependent Claim
10 words
The composition of claim 12 wherein the compound is 1-(2-hydroxypropyl)-3-nitro-4-pyrazolecarboxamide.
Claim 32
Dependent Claim
10 words
The composition of claim 12 wherein the compound is 1-(3-chloropropyl)-3-nitro-4-pyrazolecarbonitrile.
Claim 33
Dependent Claim
10 words
The composition of claim 12 wherein the compound is 1-(2-ethylsulfonylethyl)-3-nitro-4-pyrazolecarboxamide.
Claim 34
Dependent Claim
10 words
The composition of claim 12 wherein the compound is 1-cyclopropylmethyl-3-nitro-4-pyrazolecarboxamide.
Claim 35
Dependent Claim
10 words
The composition of claim 12 wherein the compound is 1-(2-chloroethyl)-3-nitro-4-pyrazolecarbonitrile.
Claim 36
Dependent Claim
12 words
A composition of claim 4 wherein R represents alkyl monosubstituted with ##STR33##
Claim 37
Dependent Claim
10 words
A composition of claim 23 wherein X represents cyano, ##STR34##
Claim 38
Dependent Claim
11 words
A composition of claim 24 wherein X represents cyano or ##STR35##
Claim 39
Dependent Claim
11 words
The composition of claim 25 wherein the compound is 2-(4-carbamoyl-3-nitropyrazol-1-yl)ethyl acetate.
Claim 40
Dependent Claim
12 words
The composition of claim 25 wherein the compound is [2-(4-carbamoyl-3-nitropyrazol-1-yl)ethyl] phenyl carbonate.
Claim 41
Dependent Claim
12 words
A composition of claim 7 wherein X represents thiadiazolyl or substituted thiadiazolyl.
Claim 42
Dependent Claim
10 words
The composition of claim 28 wherein the compound is 2-amino-5-(1-methyl-3-nitro-4-pyrazolyl)-1,3,4-thiadiazole.
Claim 43
Dependent Claim
15 words
An antibacterial composition which comprises a physiologically-acceptable inert carrier and an antibacterially-effective amount of 1,1'-(2,5-cyclohexadien-1,4-ylene)-bis-(3-nitro-4-pyrazolecarboxamide).
Claim 44
Dependent Claim
15 words
An antibacterial composition which comprises a physiologically-acceptable inert carrier and an antibacterially-effective amount of 1,1'-(2,5-cyclohexadien-1,4-ylene)-bis-(3-nitro-4-pyrazolecarboxamide).
References Cited (Backward Citations)
US3121092A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-01-02 | 1981-07-04 | 1982-01-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-01-02 | 1985-07-04 | 1986-01-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-01-02 | 1989-07-04 | 1990-01-03 | $7700.00 | Window Closed / Lapsed |