US2001006697A1PendingUtilityA1
Composition and method for producing low cholesterol eggs
Priority: Sep 29, 1997Filed: Dec 4, 2000Published: Jul 5, 2001
Est. expirySep 29, 2017(expired)· nominal 20-yr term from priority
A23K 50/75A23K 20/121A23K 20/105A23L 15/00
37
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Claims
Abstract
An animal food composition effective in reducing the amount of cholesterol in an egg including an animal food and an HMG-CoA reductase inhibitor, preferably a, statin, is described. A method of reducing the amount of cholesterol in an egg by administering to an egg-laying animal an amount of a cholesterol-reducing component effective in reducing the amount of cholesterol in said egg and the eggs produced are also described.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . An animal food composition effective in reducing the amount of cholesterol in an egg, comprising an oviparous vertebrate animal food and a cholesterol-reducing component selected from the group consisting of:
a. a compound of the formula:
wherein
R 1 is C 3-10 cycloalkyl; C 1-10 alkyl provided that the C 1-10 alkyl is not 1-methylpropyl if R 2 and R 3 are both methyl groups; C 1-10 CF 3 -substituted alkyl; phenyl; halophenyl; phenyl-C 1-3 alkyl; substituted phenyl-C 1-3 alkyl in which the substituent is halo, C 1-3 alkyl or C 1-3 alkoxy;
R 2 is H, C 1-10 alkyl, or hydroxyl;
R 3 is H, C 1-10 alkyl; and
the dotted lines at X, Y and Z represent possible double bonds, said double bonds when present being either X and Z in combination or X, Y or Z alone;
b. the corresponding dihydroxy acid of the formula:
c. a pharmaceutically acceptable salt of said dihydroxy acid; d. a C 1-4 alkyl ester of said dihydroxy acid; e. a phenyldimethylamino-substituted-C 1-4 alkyl ester of said dihydroxy acid; and f. an acetylamino-substituted-C 1-4 alkyl ester of said dihydroxy acid.
2 . The animal food composition of claim 1 , wherein R 2 is an alkyl group.
3 . The animal food composition of claim 2 , wherein the alkyl group is methyl.
4 . The animal food composition of claim 1 , wherein R 1 is an alkyl group.
5 . The animal food composition of claim 4 , wherein the alkyl group is 1,1-dimethylpropyl.
6 . The animal food composition of claim 1 , wherein R 2 is a hydroxyl group.
7 . The animal food composition of claim 1 , wherein R 3 is an alkyl group.
8 . The animal feed composition of claim 7 , wherein the alkyl group is methyl.
9 . The animal food composition of claim 1 , wherein said cholesterol-reducing component is selected from the group consisting of:
a. a compound having the following configuration:
wherein R 1 , R 2 and R 3 are as defined in claim 1 ; b. the corresponding dihydroxy acid having the following configuration:
c. a pharmaceutically acceptable salt of said dihydroxy acid; d. a C 1-4 alkyl ester of said dihydroxy acid; e. a phenyldimethylamino-substituted-C 1-4 alkyl ester of said dihydroxy acid; and f. an acetylamino-substituted-C 1-4 alkyl ester of said dihydroxy acid.
10 . The animal food composition of claim 1 , wherein said animal is a bird.
11 . The animal food composition of claim 10 , wherein said bird is a chicken.
12 . The animal food composition of claim 9 , wherein said cholesterol-reducing component is simvastatin.
13 . The animal food composition of claim 1 , wherein said cholesterol-reducing component is included in an amount effective to reduce the amount of cholesterol in said egg by at least about 20% per gram of yolk.
14 . An animal food composition effective in reducing the amount of cholesterol in an egg, comprising an oviparous vertebrate animal food and a cholesterol-reducing component selected from the group consisting of:
a. a compound of the formula:
wherein
X is —CH 2 —, —CH 2 CH 2 ', —CH 2 CH 2 CH 2 — or —CH 2 CH(CH 3 )—;
R 1 is 1-naphthyl; 2-naphthyl; cyclohexyl; norbomenyl; 2-, 3-, or 4-pyridinyl; 2-, 3- or 4-pyridinyl-N-oxide; 2-, 3- or 4-(N-C 1-4 alkyl) pyridinium halide; phenyl; phenyl substituted with halogen, hydroxyl, trifluoromethyl, C 1-4 alkyl, C 1-4 alkoxy, C 2-8 alkanoyloxy; C 1-8 alkyl;
R 2 and R 3 are independently hydrogen; cyano; trifluoromethyl; phenyl; C 1-4 alkyl; C 2-8 carboalkoxy; —CH 2 OR 7 where R 7 is hydrogen, C 1-6 alkanoyl, —CONHR 8 where R 8 is a C 1-6 alkyl, phenyl or phenyl substituted with halogen or C 1-4 alkyl; halogen provided that if R 1 is 1-methylethyl, R 4 is 4-fluorophenyl and either of R 2 or R 3 is bromine, the other of R 2 or R 3 is not bromine; or
either of R 2 or R 3 is —CONR 5 R 6 where R 5 and R 6 are independently hydrogen; C 1-6 alkyl; 2-, 3- or 4-pyridinyl; phenyl; phenyl substituted with halogen, cyano, trifluoromethyl or C 3-8 carboalkoxy; and the other of R 2 or R 3 is hydrogen; C 1-6 alkyl; cyclopropyl; cyclobutyl; cyclopentyl; cyclohexyl; phenyl; phenyl substituted with halogen, hydroxyl, trifluoromethyl, C 1-4 alkyl, C 1-4 alkoxy, or C 2-8 alkanoyloxy; and
R 4 is C 1-6 alkyl, cyclopropyl; cyclobutyl; cyclopentyl; cyclohexyl; trifluoromethyl; phenyl; or phenyl substituted with halogen;
b. the corresponding dihydroxy acid of the formula:
and c. a pharmaceutically acceptable salt thereof.
15 . The animal food composition of claim 14 , wherein R 1 is an alkyl group.
16 . The animal food composition of claim 14 , wherein said alkyl group is 1-methylethyl.
17 . The animal food composition of claim 14 , wherein R 5 is hydrogen and R 6 is phenyl.
18 . The animal food composition of claim 14 , wherein X is —CH 2 CH 2 —.
19 . The animal food composition of claim 14 , wherein R 2 and R 3 are both methylene groups and are joined together in a ring through 3 or 4 methylene groups.
20 . The animal food composition of claim 14 , wherein R 2 and R 3 are both methylene groups and are joined together in a ring through an oxygen atom.
21 . The animal food composition of claim 14 , wherein R 2 and R 3 are carbonyl groups and are joined together in a ring through a nitrogen atom, said nitrogen atom attached to a hydrogen, a C 1-4 alkyl, or a benzyl group.
22 . The animal food composition of claim 14 , wherein R 2 is —COR 9 , R 3 is —COR 10 , said R 9 and R 10 attached to each other to form a ring, said R 9 and R 10 each being a nitrogen atom, said nitrogen atom independently attached to hydrogen, C 1-4 alkyl, or a benzyl group.
23 . The animal food composition of claim 14 , wherein said cholesterol-reducing component is atorvastatin.
24 . The animal food composition of claim 14 , wherein said animal is a bird.
25 . The animal food composition of claim 14 , wherein said bird is a chicken.
26 . The animal food composition of claim 14 , wherein said cholesterol-reducing component is included in an amount effective to reduce the amount of cholesterol in said egg by at least about 20% by weight.
27 . The animal food composition of claim 14 , wherein said cholesterol-reducing component being is selected from the group consisting of:
a. a compound having the following configuration:
wherein R 1 , R 2 , R 3 and R 4 are as defined in claim 14 ; b. the corresponding dihydroxy acid having the following configuration:
and c. a pharmaceutically acceptable salt thereof.
28 . A method of reducing the amount of cholesterol in an egg, comprising administering to an egg-laying animal an amount of a cholesterol-reducing component effective in reducing the amount of cholesterol in said egg, said component being selected from the group consisting of:
a. a compound of the formula:
wherein
R 1 is C 3-10 cycloalkyl; C 1-10 alkyl provided that the C 1-10 alkyl is not 1-methylpropyl if R 2 and R 3 are both methyl groups; C 1-10 CF 3 -substituted alkyl; phenyl; halophenyl; phenyl-C 1-3 alkyl; substituted phenyl-C 1-3 alkyl in which the substituent is halo, C 1-3 alkyl or C 1-3 alkoxy;
R 2 is H, C 1-10 alkyl, or hydroxyl;
R 3 is H, C 1-10 alkyl; and
the dotted lines at X, Y and Z represent possible double bonds, said double bonds when present being either X and Z in combination or X, Y or Z alone;
b. the corresponding dihydroxy acid of the formula:
c. a pharmaceutically acceptable salt of said dihydroxy acid; d. a C 1-4 alkyl ester of said dihydroxy acid; e. a phenyldimethylamino-substituted-C 1-4 alkyl ester of said dihydroxy acid; and f. an acetylamino-substituted-C 1-4 alkyl ester of said dihydroxy acid.
29 . The method of claim 28 , wherein R 2 is an alkyl group.
30 . The method of claim 29 , wherein the alkyl group is methyl.
31 . The method of claim 28 , wherein R 1 is an alkyl group.
32 . The method of claim 31 , wherein the alkyl group is 1,1-dimethylpropyl.
33 . The method of claim 28 , wherein R 2 is hydroxyl.
34 . The method of claim 28 , wherein said cholesterol-reducing component selected from the group consisting of:
a. a compound having the following configuration:
wherein R 1 , R 2 and R 3 are as defined in claim 28 ; b. the corresponding dihydroxy acid having the following configuration:
c. a pharmaceutically acceptable salt of said dihydroxy acid; d. a C 1-4 alkyl ester of said dihydroxy acid; e. a phenyldimethylamino-substituted-C 1-4 alkyl ester of said dihydroxy acid; and f. an acetylamino-substituted-C 1-4 alkyl ester of said dihydroxy acid.
35 . The method of claim 28 , wherein said egg-laying animal is a bird.
36 . The method of claim 35 , wherein said bird is a chicken.
37 . The method of claim 28 , wherein said cholesterol-reducing component is simvastatin.
38 . The method of claim 28 , wherein said cholesterol-reducing component is included in an amount effective in reducing the amount of cholesterol in said egg by at least about 20% per gram of yolk.
39 . The method of claim 28 , wherein said component is administered orally to said egg-laying animal.
40 . The method of claim 28 , wherein said effective amount of said cholesterol-reducing component ranges from about 5 mg/animal/day to about 265 mg/animal/day.
41 . The method of claim 28 , wherein said effective amount of said cholesterol-reducing component ranges from about 30 mg/animal/day to about 60 mg/animal/day.
42 . The method of claim 28 , wherein said method includes adding said component to the feed of the egg-laying animal and administering said feed to said egg-laying animal.
43 . A method of reducing the amount of cholesterol in an egg, comprising administering to an egg-laying animal an amount of a cholesterol-reducing component effective in reducing the amount of cholesterol in said egg, said component being selected from the group consisting of:
a. a compound of the formula:
wherein
X is —CH 2 —, —CH 2 CH 2 —, —CH 2 CH 2 CH 2 — or —CH 2 CH(CH 3 )—;
R 1 is 1-naphthyl; 2-naphthyl; cyclohexyl; norbomenyl; 2-, 3-, or 4-pyridinyl; 2-, 3- or 4-pyridinyl-N-oxide; 2-, 3- or 4-(N-C 1-4 alkyl) pyridinium halide; phenyl; phenyl substituted with halogen, hydroxyl, trifluoromethyl, C 1-4 alkyl, C 1-4 alkoxy, C 2-8 alkanoyloxy; C 1-8 alkyl;
R 2 and R 3 are independently hydrogen; cyano; trifluoromethyl; phenyl; C 1-4 alkyl; C 2-8 carboalkoxy; —CH 2 OR 7 where R 7 is hydrogen, C 1-6 alkanoyl, —CONHR 8 where R 8 is a C 1-4 alkyl, phenyl or phenyl substituted with halogen or C 1-4 alkyl; halogen provided that if R 1 is 1-methylethyl, R 4 is 4-fluorophenyl and either of R 2 or R 3 is bromine, the other of R 2 or R 3 is not bromine; or
either of R 2 or R 3 is —CONR 5 R 6 where R 5 and R 6 are independently hydrogen; C 1-6 alkyl; 2-, 3- or 4-pyridinyl; phenyl; phenyl substituted with halogen, cyano, trifluoromethyl or C 3-8 carboalkoxy; and the other of R 2 or R 3 is hydrogen; C 1-6 alkyl; cyclopropyl; cyclobutyl; cyclopentyl; cyclohexyl; phenyl; phenyl substituted with halogen, hydroxyl, trifluoromethyl, C 1-4 alkyl, C 1-4 alkoxy, or C 2-8 alkanoyloxy; and
R 4 is C 1-6 alkyl, cyclopropyl; cyclobutyl; cyclopentyl; cyclohexyl; trifluoromethyl; phenyl; or phenyl substituted with halogen;
b. the corresponding dihydroxy acid of the formula:
and c. a pharmaceutically acceptable salt thereof.
44 . The method of claim 43 , wherein R 1 is an alkyl group.
45 . The method of claim 44 , wherein the alkyl group is 1-methylethyl.
46 . The method of claim 43 , wherein R 2 is —CONR 5 R 6 , R 5 is hydrogen and R 6 is phenyl.
47 . The animal food composition of claim 43 , wherein X is —CH 2 CH 2 —.
48 . The animal food composition of claim 43 , wherein R 2 and R 3 are both methylene groups and are joined together in a ring through 3 or 4 methylene groups.
49 . The animal food composition of claim 43 , wherein R 2 and R 3 are both methylene groups and are joined together in a ring through an oxygen atom.
50 . The animal food composition of claim 43 , wherein R 2 and R 3 are carbonyl groups and are joined together in a ring through a nitrogen atom, said nitrogen atom attached to a hydrogen, a C 1-4 alkyl, or a benzyl group.
51 . The animal food composition of claim 43 , wherein R 2 is —COR 9 , R 3 is —COR 10 , said R 9 and R 10 attached to each other to form a ring, said R 9 and R 10 each being a nitrogen atom, said nitrogen atom independently attached to hydrogen, C 1-4 alkyl, or a benzyl group.
52 . The method of claim 43 , wherein said cholesterol-reducing component is atorvastatin.
53 . The method of claim 43 , wherein said egg-laying animal is a bird.
54 . The method of claim 53 , wherein said bird is a chicken.
55 . The method of claim 43 , wherein said cholesterol-reducing component is included in an amount effective in reducing the amount of cholesterol in said egg by at least about 20% per gram of yolk.
56 . The method of claim 43 , wherein said component is administered orally to said egg-laying animal.
57 . The method of claim 43 , wherein said effective amount of said cholesterol-reducing component ranges from about 5 mg/animal/day to about 265 mg/animal/day.
58 . The method of claim 43 , wherein said effective amount of said cholesterol-reducing component ranges from about 30 mg/animal/day to about 60 mg/animal/day.
59 . The method of claim 43 , wherein said method comprises adding said cholesterol-reducing component to the feed of the egg-laying animal and administering said feed to said egg-laying animal.
60 . The method of claim 43 , wherein said cholesterol-reducing component is selected from the group consisting of:
a. a compound having the following configuration:
wherein R 1 , R 2 , R 3 and R 4 are as defined in claim 43 ; b. the corresponding dihydroxy acid having the following configuration:
and c. a pharmaceutically acceptable salt thereof.
61 . An egg produced by the method of claim 28 .
62 . An egg produced by the method of claim 43 .Join the waitlist — get patent alerts
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