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US4289784A
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Pyromellitic diimides and method of increasing feed efficiency in ruminant animals
Assignee: Merck and Co Inc
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Filing: 1980-04-22
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Granted: 1981-09-15
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Expires: 2000-04-22
Abstract
Abstract Novel substituted pyromellitic diimides are disclosed wherein the compounds are assymetrically substituted with a variety of substituent groups. Processes for the preparation of such compounds are also disclosed. The novel assymetrically substituted pyromellitic diimides are useful for administration to ruminant animals to increase feed efficiency, shift volatile fatty acid production in the ruminants from acetate with an increase in the more energetically efficient propionate and butyrate and to suppress methane formation in the rumen. Composition and methods of treatment utilizing said compounds as the active ingredient thereof are also disclosed.
Inventors
- 👤 Richard J. Bochis
- 👤 Michael H. Fisher
- 👤 Bruce O. Linn
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 10:16
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/44; C07D209/48; A; A23; A23K; A23K20/00; A23K20/10; A23K20/116; A23K20/137; C07D307/00; C07D307/77; C07D307/87; C07D307/89; C07D487/00; C07D487/02; C07D487/04; C07D491/00; C07D491/02; C07D491/04
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
94 words
A compound having the formula: ##STR15## wherein R 1 is hydrogen and R 2 is loweralkyl, loweralkenyl, loweralkynyl, cycloalkyl, loweralkanoyl, benzoyl, substituted phenyl wherein the substituent is sulfonamido, hydroxy, carboxy, nitro, methylthio, or hydroxy loweralkyl; substituted loweralkyl wherein the substituents are one or two of hydroxy, halogen nitro, loweralkoxy, carboxy, phenyl, hydroxyloweralkoxy, loweralkanoyloxy, phenoxy, amino, mono- or di-loweralkylamino, mercapto, loweralkylthio, loweralkylsulfinyl, loweralkylsulfonyl, loweralkoxycarbonyl, carbamyl, hydroxyloweralkylthio, hydroxyloweralkylsulfinyl, hydroxyloweralkylsulfonyl, hydroxyloweralkylamino, di-(hydroxyloweralkyl)amino, loweralkanoylamino or hydroxyphenyl; diloweralkylamino, or mono-substituted amino wherein the substituent is loweralkanoyl, benzoyl or loweralkoxycarbonyl; and X and Y are independently hydrogen, loweralkyl or halogen.
Claim 2
Dependent Claim
94 words
A compound having the formula: ##STR15## wherein R 1 is hydrogen and R 2 is loweralkyl, loweralkenyl, loweralkynyl, cycloalkyl, loweralkanoyl, benzoyl, substituted phenyl wherein the substituent is sulfonamido, hydroxy, carboxy, nitro, methylthio, or hydroxy loweralkyl; substituted loweralkyl wherein the substituents are one or two of hydroxy, halogen nitro, loweralkoxy, carboxy, phenyl, hydroxyloweralkoxy, loweralkanoyloxy, phenoxy, amino, mono- or di-loweralkylamino, mercapto, loweralkylthio, loweralkylsulfinyl, loweralkylsulfonyl, loweralkoxycarbonyl, carbamyl, hydroxyloweralkylthio, hydroxyloweralkylsulfinyl, hydroxyloweralkylsulfonyl, hydroxyloweralkylamino, di-(hydroxyloweralkyl)amino, loweralkanoylamino or hydroxyphenyl; diloweralkylamino, or mono-substituted amino wherein the substituent is loweralkanoyl, benzoyl or loweralkoxycarbonyl; and X and Y are independently hydrogen, loweralkyl or halogen.
Claim 3
Dependent Claim
47 words
The compound of claim 1 wherein R 2 is, loweralkyl, loweralkenyl, substituted loweralkyl wherein the substituent is one or two of hydroxy, amino, mono- or di-loweralkylamino, loweralkoxy, carboxy, carbamyl, phenyl, hydroxyloweralkoxy, hydroxyloweralkylthio, loweralkanoyloxy, mercapto, loweralkylthio, loweralkylsulfinyl, loweralkylsulfonyl, loweralkoxycarbonyl; loweralkanoyl, diloweralkylamino, benzoylamino; and X and y are hydrogen.
Claim 4
Dependent Claim
30 words
The compound of claim 2 wherein R 2 is, loweralkyl, loweralkenyl, substituted loweralkyl, wherein the substituent is one of hydroxy, or loweralkanoyloxy; loweralkylthio, loweralkylsulfinyl, loweralkylsulfonyl, hydroxyloweralkylthio, hydroxyloweralkoxy; loweralkanoyl or diloweralkylamino.
Claim 5
Dependent Claim
22 words
The compound of claim 3 wherein R 2 is, loweralkyl, substituted loweralkyl wherein the substituent is one of hydroxy, hydroxyloweralkoxy, or hydroxyloweralkylthio.
Claim 6
Dependent Claim
10 words
The compound of claim 1 which is N-methyl pyromellitic diimide.
Claim 7
Dependent Claim
9 words
The compound of claim 1 which is N-(2-hydroxyethyl)pyromellitic diimide.
Claim 8
Dependent Claim
9 words
The compound of claim 1 which is N-[2-(2-hydroxyethylthio)ethyl]pyromellitic diimide.
Claim 9
Dependent Claim
9 words
The compound of claim 1 which is N-[2-(2-hydroxyethoxy)ethyl]pyromellitic diimide.
Claim 10
Dependent Claim
9 words
The compound of claim 1 which is N-[2-(methylthio)ethyl]pyromellitic diimide.
Claim 11
Dependent Claim
9 words
The compound of claim 1 which is N-[2-(methylsulfinyl)ethyl]pyromellitic diimide.
Claim 12
Dependent Claim
9 words
The compound of claim 1 which is [2-(methylsulfonyl)ethyl]pyromellitic diimide.
Claim 13
Dependent Claim
28 words
A method for increasing the feed efficiency of a ruminant animal which comprises orally administering to said ruminant animal an effective amount of a compound of claim 1.
Claim 14
Dependent Claim
26 words
A composition useful for increasing the feed efficiency of ruminant animals which comprises an inert carrier and an effective amount of a compound of claim 1.
References Cited (Backward Citations)
US3078228A
Cited
GB1157503A
Cited
US3624212A
Cited
GB1173943A
Cited
GB1181020A
Cited
US3738840A
Cited
US3931224A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-09-14 | 1985-03-16 | 1985-09-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-09-14 | 1989-03-16 | 1989-09-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-09-14 | 1993-03-16 | 1993-09-15 | $7700.00 | Window Closed / Lapsed |