US4177274A
Expired / Lapsed
US
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Substituted imidazo [1,2-a] pyridines
Assignee: Merck and Co Inc
•
Filing: 1978-06-05
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Granted: 1979-12-04
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Expires: 1998-06-05
Abstract
Abstract Certain novel substituted imidazo [1,2-a] pyridines with a substituted amino group at the 2- or 3-position are active anthelmintic agents. The novel compounds are prepared from the appropriate substituted 2-aminopyridine precursor. Compositions which utilize said novel imidazo [1,2-a] pyridines as the active ingredient thereof for the treatment of helminthiasis are also disclosed.
Inventors
- 👤 Richard J. Bochis
- 👤 Peter Kulsa
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 23:13
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/36; C07D213/42; C07D213/38; C07D213/44; C07D213/53; C07D213/60; C07D213/78; C07D213/86; C07D471/00; C07D471/02; C07D471/04
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
94 words
A compound having the formula: ##STR40## wherein: X is oxygen; R 1 is halogen, trifluoromethyl, loweralkyl, loweralkoxy, loweralkoxycarbonyl, loweralkylthio, loweralkylsulfinyl, loweralklysulfonyl, loweralkanoyl, hydroxy, sulfonamido, mono- or di-loweralkylsulfonamido, amino, mono- or di-loweralklyamino, carboxy, carboxamido, mono- and di-loweralkylcarboxamido, loweralkanolyloxy, loweralkoxycarbonylamino, loweralkanoylamino, cyano or nitro; n is 1 or 2, such that when n is 2, the two R 1 groups need not be identical; R 2 is loweralkyl or loweralkoxy; and R 3 is hydrogen, loweralkyl, loweralkenyl, or loweralkyl substituted with loweralkoxy, loweralkoxycarbonyl, carboxy, loweralkylthio, loweralkylsulfinyl, loweralkylsulfonyl, amino and mono- or di-loweralklylamino, phenyl, halophenyl, or loweralkoxyphenyl.
Claim 2
Dependent Claim
94 words
A compound having the formula: ##STR40## wherein: X is oxygen; R 1 is halogen, trifluoromethyl, loweralkyl, loweralkoxy, loweralkoxycarbonyl, loweralkylthio, loweralkylsulfinyl, loweralklysulfonyl, loweralkanoyl, hydroxy, sulfonamido, mono- or di-loweralkylsulfonamido, amino, mono- or di-loweralklyamino, carboxy, carboxamido, mono- and di-loweralkylcarboxamido, loweralkanolyloxy, loweralkoxycarbonylamino, loweralkanoylamino, cyano or nitro; n is 1 or 2, such that when n is 2, the two R 1 groups need not be identical; R 2 is loweralkyl or loweralkoxy; and R 3 is hydrogen, loweralkyl, loweralkenyl, or loweralkyl substituted with loweralkoxy, loweralkoxycarbonyl, carboxy, loweralkylthio, loweralkylsulfinyl, loweralkylsulfonyl, amino and mono- or di-loweralklylamino, phenyl, halophenyl, or loweralkoxyphenyl.
Claim 3
Dependent Claim
28 words
The compound of claim 1 in which the ##STR41## is at the 2-positions and the phenyl containing substituent is at the 6-position of the imidazo [1,2-a] pyridine molecule.
Claim 4
Dependent Claim
18 words
The compound of claim 2 in which R 2 is loweralkoxy, and R 3 is hydrogen or loweralkyl.
Claim 5
Dependent Claim
21 words
The compound of claim 3 in which R 2 is methoxy or ethoxy, and R 3 is hydrogen, methyl or ethyl.
Claim 6
Dependent Claim
9 words
The compound of claim 2 wherein n is 1.
Claim 7
Dependent Claim
48 words
The compound of claim 5 in which n is 1, R 2 is loweralkoxy, R 3 is hydrogen or loweralkyl and R 1 is amino, loweralkanoylamino, loweralkoxy, loweralkylsulfinyl, mono- or di-loweralkylamino, or loweralkyl, and that such groups are in the 3- or 4- position of the phenyl ring.
Claim 8
Dependent Claim
21 words
The compound of claim 6 in which P 1 is amino, loweralkanoylamino, or loweralkoxy in the 4-position of the phenyl ring.
Claim 9
Dependent Claim
23 words
The compound of claim 7 in which R 2 is methoxy,, R 3 is hydrogen and R 1 is amino, acetamido or methoxy.
Claim 10
Dependent Claim
66 words
A compound having the formula: ##STR42## wherein X is oxygen; R 1 is halogen, trifluoromethyl, loweralkyl, loweralkoxy, loweralkoxycarbonyl, loweralkylthio, loweralkylsulfinyl, loweralkylsulfonyl, loweralkanoyl, hydroxy sulfonamido, amino, mono- or di-loweralkylamino, carboxy, carboxamido, mono- or di-loweralkylcarboxamido, loweralkanoyloxy, loweralkoxycarbonylamino, loweralkanoylamino, cyano or nitro; R 4 is loweralkyl of trifluoromethyl; and n is 1 to 2 such that when n is 2 the two R 1 groups need not be identical.
Claim 11
Dependent Claim
66 words
A compound having the formula: ##STR42## wherein X is oxygen; R 1 is halogen, trifluoromethyl, loweralkyl, loweralkoxy, loweralkoxycarbonyl, loweralkylthio, loweralkylsulfinyl, loweralkylsulfonyl, loweralkanoyl, hydroxy sulfonamido, amino, mono- or di-loweralkylamino, carboxy, carboxamido, mono- or di-loweralkylcarboxamido, loweralkanoyloxy, loweralkoxycarbonylamino, loweralkanoylamino, cyano or nitro; R 4 is loweralkyl of trifluoromethyl; and n is 1 to 2 such that when n is 2 the two R 1 groups need not be identical.
Claim 12
Dependent Claim
110 words
An anthelmintic composition which comprises a pharmaceutically acceptable inert carrier and an effective amount of a compound having the formula: ##STR43## wherein X is oxygen, R 1 is halogen, trifluoromethyl, loweralkyl, loweralkoxy, loweralkoxycarbonyl, loweralkylthio, loweralkylsulfinyl, loweralkylsulfonyl, loweralkanoyl, hydroxy, sulfonamido, mono- or di-loweralkylsulfonamido, amino, mono- or di-loweralkylamino, carboxy, carboxamido, mono- and di-loweralkylcarboxamido, loweralkanoyloxy, loweralkoxycarbonylamino, loweralkanoylamino, cyano or nitro; n is 1 or 2, such that when n is 2, the two R 1 groups need not be identical; R 2 is loweralkyl or loweralkoxy; and R 3 is hydrogen, loweralkyl, loweralkenyl, or loweralkyl substituted with loweralkoxy, loweralkoxy carbonyl, carboxy, loweralkylthio, loweralkylsulfinyl, loweralkylsulfonyl, amino and mono- or di-loweralkylamino, phenyl, halophenyl, or loweralkoxyphenyl.
Claim 13
Dependent Claim
110 words
An anthelmintic composition which comprises a pharmaceutically acceptable inert carrier and an effective amount of a compound having the formula: ##STR43## wherein X is oxygen, R 1 is halogen, trifluoromethyl, loweralkyl, loweralkoxy, loweralkoxycarbonyl, loweralkylthio, loweralkylsulfinyl, loweralkylsulfonyl, loweralkanoyl, hydroxy, sulfonamido, mono- or di-loweralkylsulfonamido, amino, mono- or di-loweralkylamino, carboxy, carboxamido, mono- and di-loweralkylcarboxamido, loweralkanoyloxy, loweralkoxycarbonylamino, loweralkanoylamino, cyano or nitro; n is 1 or 2, such that when n is 2, the two R 1 groups need not be identical; R 2 is loweralkyl or loweralkoxy; and R 3 is hydrogen, loweralkyl, loweralkenyl, or loweralkyl substituted with loweralkoxy, loweralkoxy carbonyl, carboxy, loweralkylthio, loweralkylsulfinyl, loweralkylsulfonyl, amino and mono- or di-loweralkylamino, phenyl, halophenyl, or loweralkoxyphenyl.
Claim 14
Independent Claim
119 words
A method for the prevention and treatment of helminthiasis which comprises administration to an animal suspected of or infected with helminths an effective amount of a compound having the formula: ##STR44## wherein X is oxygen; R 1 is halogen, trifluoromethyl, loweralkyl, loweralkoxy, loweralkoxycarbonyl, loweralkylthio, loweralkylsulfinyl, loweralkylsulfonyl, loweralkanoyl, hydroxy, sulfonamido, mono- or di-loweralkylsulfonamido, amino mono- or di-loweralkylamino, carboxy, carboxamido, mono- and di-loweralkylcarboxamido, loweralkanoyloxy, loweralkoxycarbonylamino, loweralkanoylamino, cyano or nitro; n is 1 or 2, such that when n is 2, the two R 1 groups need not be identical; R 2 is loweralkyl or loweralkoxy; and R 3 is hydrogen, loweralkyl, loweralkenyl, or loweralkyl substituted with loweralkoxy, loweralkoxycarbonyl, carboxy, loweralkylthio, loweralkylsulfinyl, loweralkylsulfonyl, amino and mono- or di-loweralkylamino, phenyl, halophenyl, or loweralkoxyphenyl.
Claim 15
Independent Claim
119 words
A method for the prevention and treatment of helminthiasis which comprises administration to an animal suspected of or infected with helminths an effective amount of a compound having the formula: ##STR44## wherein X is oxygen; R 1 is halogen, trifluoromethyl, loweralkyl, loweralkoxy, loweralkoxycarbonyl, loweralkylthio, loweralkylsulfinyl, loweralkylsulfonyl, loweralkanoyl, hydroxy, sulfonamido, mono- or di-loweralkylsulfonamido, amino mono- or di-loweralkylamino, carboxy, carboxamido, mono- and di-loweralkylcarboxamido, loweralkanoyloxy, loweralkoxycarbonylamino, loweralkanoylamino, cyano or nitro; n is 1 or 2, such that when n is 2, the two R 1 groups need not be identical; R 2 is loweralkyl or loweralkoxy; and R 3 is hydrogen, loweralkyl, loweralkenyl, or loweralkyl substituted with loweralkoxy, loweralkoxycarbonyl, carboxy, loweralkylthio, loweralkylsulfinyl, loweralkylsulfonyl, amino and mono- or di-loweralkylamino, phenyl, halophenyl, or loweralkoxyphenyl.
References Cited (Backward Citations)
US3701780A
Cited
US4092321A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-12-03 | 1983-06-04 | 1983-12-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-12-03 | 1987-06-04 | 1987-12-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-12-03 | 1991-06-04 | 1991-12-04 | $7700.00 | Window Closed / Lapsed |