US4212880A
Expired / Lapsed
US
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Symmetrically substituted pyromellitic diimides as ruminant feed additives
Assignee: Merck and Co Inc
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Filing: 1978-10-23
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Granted: 1980-07-15
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Expires: 1998-10-23
Abstract
Abstract Symmetrically substituted pyromellic diimides are disclosed wherein the compounds are substituted with a variety of substituent groups. The symmetrically substituted compounds are useful for administration to ruminant animals to increase feed efficiency, shift volatile fatty acid production in the ruminant from acetate with an increase in the more energetically efficient propionate and butyrate and to suppress methane formation in the rumen. Compositions and methods of treatment utilizing said compounds as the active ingredient thereof are also disclosed.
Inventors
- 👤 Michael H. Fisher
- 👤 Peter Kulsa
- 👤 Bruce O. Linn
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 09:53
CPC Classifications
C; C07; C07D; C07D487/00; C07D487/02; C07D487/04; A; A23; A23K; A23K20/00; A23K20/10; A23K20/116; A23K20/137
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
94 words
A method for improving the feed efficiency of ruminant animals which comprises orally administering to a ruminant animal an effective amount of a compound having the formula: ##STR3## wherein each R is the same and represents hydrogen, loweralkyl, loweralkenyl, loweralkynyl, cyclopropyl, nitrophenyl; substituted loweralkyl wherein the substituent is one or two of hydroxy, hydroxyloweralkoxy, hydroxyloweralkylthio, amino, mono- or di-loweralkylamino, mono- or di-(hydroxy substituted loweralkyl)amino, loweralkanoyloxy, loweralkoxy, mercapto, loweralkylthio, loweralkylsulfinyl, loweralkylsulfonyl or loweralkoxycarbonyl; loweralkanoyl, benzoyl, diloweralkylamino, mono-substituted amino wherein the substituent is loweralkanoyl, benzoyl or loweralkanoyloxy; X and Y are independently hydrogen, halogen or loweralkyl.
Claim 2
Independent Claim
94 words
A method for improving the feed efficiency of ruminant animals which comprises orally administering to a ruminant animal an effective amount of a compound having the formula: ##STR3## wherein each R is the same and represents hydrogen, loweralkyl, loweralkenyl, loweralkynyl, cyclopropyl, nitrophenyl; substituted loweralkyl wherein the substituent is one or two of hydroxy, hydroxyloweralkoxy, hydroxyloweralkylthio, amino, mono- or di-loweralkylamino, mono- or di-(hydroxy substituted loweralkyl)amino, loweralkanoyloxy, loweralkoxy, mercapto, loweralkylthio, loweralkylsulfinyl, loweralkylsulfonyl or loweralkoxycarbonyl; loweralkanoyl, benzoyl, diloweralkylamino, mono-substituted amino wherein the substituent is loweralkanoyl, benzoyl or loweralkanoyloxy; X and Y are independently hydrogen, halogen or loweralkyl.
Claim 3
Dependent Claim
64 words
The method of claim 1 wherein the compound being administered to the ruminant has the structural formula of claim 1 and wherein R is hydrogen, loweralkyl, loweralkenyl, substituted loweralkyl wherein the substituents are one or two of hydroxy, amino, mono- or di-loweralkylamino, hydroxyloweralkoxy, hydroxyloweralkylthio, loweralkanoyloxy, loweralkoxy or loweralkoxycarbonyl; loweralkanoyl, diloweralkylamino or mono-substituted amino wherein the substituent is loweralkanoyl; and X and Y are hydrogen.
Claim 4
Dependent Claim
36 words
The method of claim 2 wherein the compound being administered to the ruminant has the formula wherein R is hydrogen loweralkyl, loweralkenyl, substituted loweralkyl wherein the substituent is one of hydroxy or loweralkanoyloxy; loweralkanoyl, or diloweralkylamino.
Claim 5
Dependent Claim
22 words
The method of claim 2 wherein the compound being administered to the ruminant has the formula wherein R is hydrogen or hydroxyloweralkyl.
Claim 6
Dependent Claim
13 words
The method of claim 4 wherein the compound being administered is pyromellitic diimide.
Claim 7
Dependent Claim
13 words
The method of claim 4 wherein the compound being administered is N,N'-bis(2-hydroxyethyl)pyromellitic diimide.
Claim 8
Dependent Claim
19 words
The method of claim 1 wherein the compound is administered at the rate of from 0.1 to 10 mg./kg/day.
Claim 9
Dependent Claim
19 words
The method of claim 7 wherein the compound is administered at the rate of from 0.5 to 5 mg./kg/day.
Claim 10
Dependent Claim
93 words
A composition useful for the improvement of feed efficiency in ruminants when orally administered to ruminants which comprises an inert carrier and a compound having the formula: ##STR4## wherein each R is the same and represents hydrogen, loweralkenyl, loweralkynyl, cyclopropyl, nitrophenyl; substituted loweralkyl wherein the substituent is one or two of hydroxy, hydroxyloweralkoxy, hydroxyloweralkylthio, amino, mono- or di-loweralkylamino, mono- or di-(hydroxy substituted loweralkyl)amino, loweralkanoyloxy, loweralkoxy, mercapto, loweralkylthio, loweralkylsulfinyl, loweralkylsulfonyl or loweralkoxycarbonyl; benzoyl, diloweralkylamino, or mono-substituted amino wherein the substituent is loweralkanoyl, benzoyl or loweralkanoyloxy; X and Y are independently hydrogen, halogen or loweralkyl.
Claim 11
Dependent Claim
93 words
A composition useful for the improvement of feed efficiency in ruminants when orally administered to ruminants which comprises an inert carrier and a compound having the formula: ##STR4## wherein each R is the same and represents hydrogen, loweralkenyl, loweralkynyl, cyclopropyl, nitrophenyl; substituted loweralkyl wherein the substituent is one or two of hydroxy, hydroxyloweralkoxy, hydroxyloweralkylthio, amino, mono- or di-loweralkylamino, mono- or di-(hydroxy substituted loweralkyl)amino, loweralkanoyloxy, loweralkoxy, mercapto, loweralkylthio, loweralkylsulfinyl, loweralkylsulfonyl or loweralkoxycarbonyl; benzoyl, diloweralkylamino, or mono-substituted amino wherein the substituent is loweralkanoyl, benzoyl or loweralkanoyloxy; X and Y are independently hydrogen, halogen or loweralkyl.
Claim 12
Dependent Claim
61 words
The composition of claim 9 wherein the active compound of said composition has the structural formula of claim 7 wherein R is hydrogen, loweralkyl, loweralkenyl, substituted loweralkyl wherein the substituents are one or two of hydroxy, amino, mono- or di-loweralkylamino, hydroxyloweralkoxy, hydroxyloweralkylthio, loweralkanoyloxy, loweralkoxy or loweralkoxycarbonyl; diloweralkylamino or mono-substituted amino wherein the substituent is loweralkanoyl; and X and Y are hydrogen.
Claim 13
Dependent Claim
34 words
The composition of claim 10 wherein the active compound of the composition has the formula wherein R is hydrogen, loweralkyl, loweralkenyl, substituted loweralkyl wherein the substituent is one of hydroxy or loweralkanoyloxy; or diloweralkylamino.
Claim 14
Dependent Claim
23 words
The composition of claim 11 wherein the compound being administered to the ruminant has the formula wherein R is hydrogen or hydroxy loweralkyl.
Claim 15
Dependent Claim
12 words
The composition of claim 12 wherein the active compound is pyromellitic diimide.
Claim 16
Dependent Claim
12 words
The composition of claim 12 wherein the active compound is N,N'-bis-(2-hydroxyethyl)pyromellitic diimide.
Claim 17
Dependent Claim
24 words
The composition of claim 9 which is a feed premix containing from about 1 to 400 g. of active compound per pound of premix.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-07-15 | 1984-01-14 | 1984-07-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-07-15 | 1988-01-14 | 1988-07-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-07-15 | 1992-01-14 | 1992-07-15 | $7700.00 | Window Closed / Lapsed |