US4622330A
Expired / Lapsed
US
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Antiprotozoal 3-amino or substituted amino pyrazoles
Assignee: Merck and Co Inc
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Filing: 1984-06-19
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Granted: 1986-11-11
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Expires: 2004-06-19
Abstract
Abstract Novel 3-amino or substituted amino pyrazoles are disclosed as having antiprotozoal and antiparasitic activity in particular anticoccidial activity and are useful for controlling cecal and or intestinal coccidiosis when administered in minor quantities to animals, in particular to poultry usually in admixture with animal sustenance.
Inventors
- 👤 Richard J. Bochis
- 👤 Richard A. Dybas
- 👤 Edward F. Rogers
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 06:59
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/02; C07D231/10; C07D231/14; C07D231/38; A; A23; A23K; A23K20/00; A23K20/10; A23K20/116; A23K20/137
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
153 words
A compound having the formula: ##STR67## wherein: R 1 is substituted phenyl alkyl (1-3 carbon chain) wherein the substituents are one or more of halogen, cyano, trifluoromethyl, loweralkanol, nitro, loweralkyl, loweralkoxy, carboxy, carbalkoxy (1-3 carbon chain), acetamido, benzoyl, halobenzoyl, trifluoromethylbenzoyl, phenoxy, halophenoxy, trifluoromethylphenoxy, phenyl, halophenyl, trifluoromethylphenyl, phenylthio, phenylsulfinyl, phenylsulfonyl, halo or trifluoromethyl substituted phenylthio, halo or trifluoromethyl substituted phenylsulfinyl, halo or trifluoromethyl substituted phenylsulfonyl, loweralkylthio, loweralkylsulfinyl, or loweralkylsulfonyl, provided that R 1 is unsubstituted phenylalkyl only when R 3 is other than cyano; R 1 may also be phenacyl, 3-phenyl-2-propenyl, phenoxyethyl, pyridyl, pyridylmethyl, thiazolyl, naphthyl, naphthylmethyl, quinolyl, or quinolylmethyl; R 2 is amino, mono or diloweralkylamino, acetamido, acetimido, ureido, formamido, formimido or guanidino; R 3 is carbamoyl, carbazoyl, amidino or N-hydroxycarbamoyl; and R 4 is hydrogen, loweralkyl, hydroxy, amino, mono or diloweralkylamino, phenyl, cyano, loweralkoxy, loweralkanoyloxy, loweralkylthio, loweralkylsulfinyl, or loweralkylsulfonyl; provided that when R 3 is carbamoyl, R 2 is other than pyridyl.
Claim 2
Dependent Claim
153 words
A compound having the formula: ##STR67## wherein: R 1 is substituted phenyl alkyl (1-3 carbon chain) wherein the substituents are one or more of halogen, cyano, trifluoromethyl, loweralkanol, nitro, loweralkyl, loweralkoxy, carboxy, carbalkoxy (1-3 carbon chain), acetamido, benzoyl, halobenzoyl, trifluoromethylbenzoyl, phenoxy, halophenoxy, trifluoromethylphenoxy, phenyl, halophenyl, trifluoromethylphenyl, phenylthio, phenylsulfinyl, phenylsulfonyl, halo or trifluoromethyl substituted phenylthio, halo or trifluoromethyl substituted phenylsulfinyl, halo or trifluoromethyl substituted phenylsulfonyl, loweralkylthio, loweralkylsulfinyl, or loweralkylsulfonyl, provided that R 1 is unsubstituted phenylalkyl only when R 3 is other than cyano; R 1 may also be phenacyl, 3-phenyl-2-propenyl, phenoxyethyl, pyridyl, pyridylmethyl, thiazolyl, naphthyl, naphthylmethyl, quinolyl, or quinolylmethyl; R 2 is amino, mono or diloweralkylamino, acetamido, acetimido, ureido, formamido, formimido or guanidino; R 3 is carbamoyl, carbazoyl, amidino or N-hydroxycarbamoyl; and R 4 is hydrogen, loweralkyl, hydroxy, amino, mono or diloweralkylamino, phenyl, cyano, loweralkoxy, loweralkanoyloxy, loweralkylthio, loweralkylsulfinyl, or loweralkylsulfonyl; provided that when R 3 is carbamoyl, R 2 is other than pyridyl.
Claim 3
Dependent Claim
87 words
The compound of claim 1 wherein R 1 is substituted benzyl wherein the substituents are 1 to 3 of halo, cyano, trifluoromethyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, benzoyl, halo or trifluoromethyl substituted phenoxy, halo or trifluoromethyl substituted phenylthio, halo or trifluoromethyl substituted phenyl sulfinyl, halo or trifluoromethyl substituted phenyl sulfonyl, or halo or trifluoromethyl substituted benzoyl, provided that when R 1 is benzyl R 3 is other than cyano; R 2 is amino or mono or diloweralkylamino; R 3 is carbamoyl; and R 4 is hydrogen or loweralkyl.
Claim 4
Dependent Claim
56 words
The compound of claim 2 wherein R 1 is substituted benzyl wherein the substituents are 2 or 3 of halo, cyano, trifluoromethyl, halo or trifluoromethylphenoxy, halo or trifluoromethyl phenylthio, halo or trifluoromethyl phenylsulfinyl, halo or trifluoromethyl phenyl sulfonyl, or halo or trifluoromethyl benzoyl; R 2 is amino; R 3 is carbamoyl; and R 4 is hydrogen.
Claim 5
Dependent Claim
177 words
A composition useful for the prevention and treatment of protozoal diseases which comprises an inert carrier and an effective amount of a compound having the formula: ##STR68## wherein: R 1 is phenylalkyl (1-3 carbon chain) or substituted phenyl alkyl wherein the substituents are one or more of halogen, cyano, trifluoromethyl, loweralkanoyl, nitro, loweralkyl, loweralkoxy, carboxy, carbalkoxy (1-3 carbon chain), acetamido, benzoyl, halobenzoyl, trifluoromethylbenzoyl, phenoxy, halophenoxy, trifluoromethylphenoxy, phenyl, halphenyl, trifluoromethylphenyl, phenylthio, phenylsulfinyl, phenylsulfonyl, halo or trifluoromethyl substituted phenylthio, halo or trifluoromethyl substituted phenylsulfinyl, halo or trifluoromethyl substituted phenylsulfonyl, loweralkylthio, loweralkylsulfinyl, or loweralkylsulfonyl, provided that R 1 is unsubstituted phenylalkyl only when R 3 is other than cyano; R 1 may also be phenacyl, 3-phenyl-2-propenyl, phenoxyethyl, pyridyl, pyridylmethyl, thiazolyl, naphthyl, naphthylmethyl, quinolyl, or quinolylmethyl; R 2 is amino, mono or diloweralkylamino, acetamido, acetimido, ureido, formamido, formimido or quanidino; R 3 is carbamoyl, cyano, carbazoyl, amidino or N-hydroxycarbamoyl; and R 4 is hydrogen, loweralkyl, hydroxy, amino, mono or diloweralkylamino, phenyl, cyano, loweralkoxy, loweralkanoyloxy, loweralkylthio, loweralkylsulfinyl, or loweralkylsulfonyl; provided that when R 3 is carbamoyl, R 2 is other than pyridyl.
Claim 6
Dependent Claim
177 words
A composition useful for the prevention and treatment of protozoal diseases which comprises an inert carrier and an effective amount of a compound having the formula: ##STR68## wherein: R 1 is phenylalkyl (1-3 carbon chain) or substituted phenyl alkyl wherein the substituents are one or more of halogen, cyano, trifluoromethyl, loweralkanoyl, nitro, loweralkyl, loweralkoxy, carboxy, carbalkoxy (1-3 carbon chain), acetamido, benzoyl, halobenzoyl, trifluoromethylbenzoyl, phenoxy, halophenoxy, trifluoromethylphenoxy, phenyl, halphenyl, trifluoromethylphenyl, phenylthio, phenylsulfinyl, phenylsulfonyl, halo or trifluoromethyl substituted phenylthio, halo or trifluoromethyl substituted phenylsulfinyl, halo or trifluoromethyl substituted phenylsulfonyl, loweralkylthio, loweralkylsulfinyl, or loweralkylsulfonyl, provided that R 1 is unsubstituted phenylalkyl only when R 3 is other than cyano; R 1 may also be phenacyl, 3-phenyl-2-propenyl, phenoxyethyl, pyridyl, pyridylmethyl, thiazolyl, naphthyl, naphthylmethyl, quinolyl, or quinolylmethyl; R 2 is amino, mono or diloweralkylamino, acetamido, acetimido, ureido, formamido, formimido or quanidino; R 3 is carbamoyl, cyano, carbazoyl, amidino or N-hydroxycarbamoyl; and R 4 is hydrogen, loweralkyl, hydroxy, amino, mono or diloweralkylamino, phenyl, cyano, loweralkoxy, loweralkanoyloxy, loweralkylthio, loweralkylsulfinyl, or loweralkylsulfonyl; provided that when R 3 is carbamoyl, R 2 is other than pyridyl.
Claim 7
Dependent Claim
11 words
The composition of claim 4 wherein the protozoal disease is coccidiosis.
Claim 8
Independent Claim
179 words
A method for preventing or treating protozoal diseases which comprises administering to an animal in need of such treatment an effective amount of a compound having the formula: ##STR69## wherein: R 1 is phenylalkyl (1-3 carbon chain) or substituted phenyl alkyl wherein the substituents are one or more of halogen, cyano, trifluoromethyl, loweralkanoyl, nitro, loweralkyl, loweralkoxy, carboxy, carbalkoxy (1-3 carbon chain), acetamido, benzoyl, halobenzoyl, trifluoromethyl-benzoyl, phenoxy, halophenoxy, trifluoromethyl-phenoxy, phenyl, halophenyl, trifluoromethylphenyl, phenylthio, phenylsulfinyl, phenylsulfonyl, halo or trifluoromethyl substituted phenylthio, halo or trifluoromethyl substituted phenylsulfinyl, halo or trifluoromethyl substituted phenylsulfonyl, loweralkylthio, loweralkylsulfinyl, or loweralkylsulfonyl, provided that R 1 is unsubstituted phenylalkyl only when R 3 is other than cyano; R 1 may also be phenacyl, 3-phenyl-2-propenyl, phenoxyethyl, pyridyl, pyridylmethyl, thiazolyl, naphthyl, naphthylmethyl, quinolyl, or quinolylmethyl; R 2 is amino, mono or diloweralkylamino, acetamido, acetimido, ureido, formamido, formimido or quanidino; R 3 is carbamoyl, cyano, carbazoyl, amidino or N-hydroxycarbamoyl; and R 4 is hydrogen, loweralkyl, hydroxy, amino, mono or diloweralkylamino, phenyl, cyano, loweralkoxy, loweralkanoyloxy, loweralkylthio, loweralkylsulfinyl, or loweralkylsulfonyl; provided that when R 3 is carbamoyl, R 2 is other than pyridyl.
Claim 9
Independent Claim
179 words
A method for preventing or treating protozoal diseases which comprises administering to an animal in need of such treatment an effective amount of a compound having the formula: ##STR69## wherein: R 1 is phenylalkyl (1-3 carbon chain) or substituted phenyl alkyl wherein the substituents are one or more of halogen, cyano, trifluoromethyl, loweralkanoyl, nitro, loweralkyl, loweralkoxy, carboxy, carbalkoxy (1-3 carbon chain), acetamido, benzoyl, halobenzoyl, trifluoromethyl-benzoyl, phenoxy, halophenoxy, trifluoromethyl-phenoxy, phenyl, halophenyl, trifluoromethylphenyl, phenylthio, phenylsulfinyl, phenylsulfonyl, halo or trifluoromethyl substituted phenylthio, halo or trifluoromethyl substituted phenylsulfinyl, halo or trifluoromethyl substituted phenylsulfonyl, loweralkylthio, loweralkylsulfinyl, or loweralkylsulfonyl, provided that R 1 is unsubstituted phenylalkyl only when R 3 is other than cyano; R 1 may also be phenacyl, 3-phenyl-2-propenyl, phenoxyethyl, pyridyl, pyridylmethyl, thiazolyl, naphthyl, naphthylmethyl, quinolyl, or quinolylmethyl; R 2 is amino, mono or diloweralkylamino, acetamido, acetimido, ureido, formamido, formimido or quanidino; R 3 is carbamoyl, cyano, carbazoyl, amidino or N-hydroxycarbamoyl; and R 4 is hydrogen, loweralkyl, hydroxy, amino, mono or diloweralkylamino, phenyl, cyano, loweralkoxy, loweralkanoyloxy, loweralkylthio, loweralkylsulfinyl, or loweralkylsulfonyl; provided that when R 3 is carbamoyl, R 2 is other than pyridyl.
Claim 10
Dependent Claim
11 words
The method of claim 6 wherein the protozoal disease is coccidiosis.
References Cited (Backward Citations)
US3864359A
Cited
JPS4910508A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1989-11-10 | 1990-05-12 | 1990-11-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-11-10 | 1994-05-12 | 1994-11-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-11-10 | 1998-05-12 | 1998-11-11 | $7700.00 | Window Closed / Lapsed |