US5591772A
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Tocotrienols and tocotrienol-like compounds and methods for their use
Assignee: ACH Food Companies Inc
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Filing: 1992-11-20
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Granted: 1997-01-07
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Expires: 2012-11-20
Abstract
Abstract PCT No. PCT/US92/10277 Sec. 371 Date Aug. 15, 1994 Sec. 102(e) Date Aug. 15, 1994 PCT Filed Nov. 20, 1992 PCT Pub. No. WO93/09777 PCT Pub. Date May 27, 1993The present invention relates to novel tocotrienols and tocotrienol-like compounds displaying biological activity. The tocotrienols and tocotrienol-like compounds of this invention may be conveniently obtained from biological sources or by chemical synthesis and may be used in pharmaceutical compositions, foodstuffs and dietary supplements. This invention also relates to the use of tocotrienols, tocotrienol-like compounds, and mixtures thereof, as hypocholesterolemic, antithrombotic, antioxidizing, antiatherogenic, antiinflammatory and immunoregulatory agents, or as agents useful to decrease lipoprotein (a) concentration in the blood or to increase feed conversion efficiency.
Inventors
- 👤 Ronald H. Lane
- 👤 Asaf A. Qureshi
- 👤 Winston A. Salser
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 13:17
CPC Classifications
C; C11; C11B; C11B3/00; C11B3/001; A; A23; A23K; A23K10/00; A23K10/30; A23K20/00; A23K20/10; A23K20/158; A23K20/174; A23L; A23L33/00; A23L33/10; A23L33/105; A23L33/15; A61; A61K; A61K31/00; A61K31/21; A61K31/215; A61K31/22; A61K31/33; A61K31/335; A61K31/35; A61K31/352; A61K31/353; A61K31/355; A61K31/365; A61K31/395; A61K31/435; A61K31/44; A61K31/455; A61P; A61P29/00; A61P3/00; A61P3/06; A61P3/08; A61P3/10; A61P35/00; A61P37/00; A61P43/00; A61P7/00; A61P7/02; C07; C07D; C07D311/00; C07D311/02; C07D311/04; C07D311/58; C07D311/70; C07D311/72; C11B1/00; C11B1/02; C11B1/10; A23V; A23V2002/00
Claims Analysis
Total Claims: 42
Claim 1
Independent Claim
11 words
A tocotrienol comprising 3,4-dihydro-2-(4,8,12-trimethyltrideca-3'(E), 7'(E), 11'-trienyl)-2H-1-benzopyran-6-ol), and having the structure: ##STR10##
Claim 2
Dependent Claim
11 words
A tocotrienol comprising 3,4-dihydro-2-(4,8,12-trimethyltrideca-3'(E), 7'(E), 11'-trienyl)-2H-1-benzopyran-6-ol), and having the structure: ##STR10##
Claim 3
Dependent Claim
4 words
A tocotrienol comprising: ##STR11##
Claim 4
Dependent Claim
4 words
A tocotrienol comprising: ##STR11##
Claim 5
Dependent Claim
125 words
A composition comprising a tocotrienol compound resulting from a process comprising the steps of: stabilizing a biological material by heating; extracting the biological material with a solvent to obtain an oil; eluting the oil from an HPLC colunto under the following conditions: 20 μl sample, μ-Porasil column (Waters column, 10μ, 4 mm×30 cm) using an isocratic system of hexane and isopropanol (99.75% :0.25%, v/v) at a flow rate of 1.3 ml/min.; and collecting compounds having an HPLC elution time of greater than 22 minutes, said compounds being detectable at an excitation wave length of about 295 nm, and having an emission wave length of about 330 nm, UV absorption at about 295 nm, and an ability to inhibit the synthesis β-hydroxy-β-methyl glutaryl coenzyme A reductase.
Claim 6
Dependent Claim
125 words
A composition comprising a tocotrienol compound resulting from a process comprising the steps of: stabilizing a biological material by heating; extracting the biological material with a solvent to obtain an oil; eluting the oil from an HPLC colunto under the following conditions: 20 μl sample, μ-Porasil column (Waters column, 10μ, 4 mm×30 cm) using an isocratic system of hexane and isopropanol (99.75% :0.25%, v/v) at a flow rate of 1.3 ml/min.; and collecting compounds having an HPLC elution time of greater than 22 minutes, said compounds being detectable at an excitation wave length of about 295 nm, and having an emission wave length of about 330 nm, UV absorption at about 295 nm, and an ability to inhibit the synthesis β-hydroxy-β-methyl glutaryl coenzyme A reductase.
Claim 7
Dependent Claim
32 words
The tocotrienol compound according to claim 3, wherein said HPLC elution time is selected from the group consisting of about 32 minutes, about 36 minutes, about 45 minutes and about 54 minute.
Claim 8
Dependent Claim
17 words
The tocotrienol compound according to claim 3 or 4, wherein the biological material is a plant source.
Claim 9
Dependent Claim
37 words
The tocotrienol compound according to claim 5, wherein the plant source is selected from the group consisting of oats, oat bran, oat bran oil, barley, barley bran, barley bran oil, rice, rice bran and rice bran oil.
Claim 10
Dependent Claim
18 words
The tocotrienol compound according to claim 6, wherein the plant source is rice bran or rice bran oil.
Claim 11
Dependent Claim
18 words
A foodstuff comprising the tocotrienol compound according to any one of claim 1 and 2, or mixtures thereof.
Claim 12
Dependent Claim
24 words
A foodstuff comprising a tocotrienol compound, or mixtures thereof, said tocotrienol compound being selected from the tocotrienol compound according to claim 3 or 4.
Claim 13
Dependent Claim
24 words
The foodstuff according to claim 8, further comprising a compound selected from the group consisting of α-tocotrienol, β-tocotrienol, γ-tocotrienol, δ-tocotrienol, and 3.4-dihydro-2-methyl-2-(4,8,12-trimethyltrideca-3'(E), 7'(E), 11'-trienyl)-2H-1-benzopyran-6-ol.
Claim 14
Dependent Claim
24 words
The foodstuff according to claim 9, further comprising a compound selected from the group consisting of α-tocotrienol, β-tocotrienol, γ-tocotrienol, δ-tocotrienol, and 3,4-dihydro-2-methyl-2-(4,8,12-trimethyltrideca-3'(E), 7'(E), 11'-trienyl)-2H-1-benzopyran-6-ol.
Claim 15
Dependent Claim
19 words
A dietary supplement comprising the tocotrienol compound according to any one of claims 1 and 2, or mixtures thereof.
Claim 16
Dependent Claim
25 words
A dietary supplement comprising a tocotrienol compound, or mixtures thereof, said tocotrienol compound being selected from the tocotrienol compound according to claim 3 or 4.
Claim 17
Dependent Claim
25 words
The dietary supplement according to claim 13, further comprising a compound selected from the group consisting of α-tocotrienol, β-tocotrienol, γ-tocotrienol, δ-tocotrienol, and 3,4-dihydro-2-methyl-2-(4,8,12-trimethyltrideca-3'(E), 7'(E), 11'-trienyl)-2H-1-benzopyran-6-ol.
Claim 18
Dependent Claim
26 words
The dietary supplement according to claim 13, further comprising a compound selected from the group consisting of α-tocotrienol, β-tocotrienol, γ-tocotrienol, δ-tocotrienol, and 3,4-dihydro-2-methyl-2-(4,8,12-trimethyltrideca-3'(E), 7'(E), 11'-trienyl)-2H- 1-benzopyran-6-ol.
Claim 19
Dependent Claim
23 words
A pharmaceutical composition comprising the tocotrienol compound according to any one of claims 1 and 2, or mixtures thereof, and a pharmaceutical carrier.
Claim 20
Dependent Claim
36 words
A pharmaceutical composition comprising a tocotrienol compound, or mixtures thereof, and a pharmaceutical carrier, said tocotrienol compound being selected from the group consisting of the tocotrienol compounds according to any one of claims 3 and 4.
Claim 21
Dependent Claim
25 words
The pharmaceutical composition according to claim 16, further comprising a compound selected from the group consisting of α-tocotrienol, β-tocotrienol, γ-tocotrienol, δ-tocotrienol, and 3,4-dihydro-2-methyl-2-(4,8,12-trimethyltrideca-3'(E), 7'(E), 11'-trienyl)-2H-1-benzopyran-6ol.
Claim 22
Dependent Claim
25 words
The pharmaceutical composition according to claim 17, further comprising a compound selected from the group consisting of α-tocotrienol, β-tocotrienol, γ-tocotrienol, δ-tocotrienol, and 3,4-dihydro-2-methyl-2-(4,8,12-trimethyltrideca-3'(E), 7'(E), 11'-trienyl)-2H-1-benzopyran-6ol.
Claim 23
Dependent Claim
64 words
A method for treating or preventing hypocholesterolemic-related diseases, thrombotic diseases, atherogenic diseases, inflammation, immunodeficiencies, fever, edema, diabetes mellitus, pain, septic shock, chronic fatigue syndrome or funclio laesa, to decrease lipoprotein (a) concentration in the blood or to increase feed conversion efficiency in a patient, comprising the step of administering to said patient a pharmaceutically effective amount of the pharmaceutical composition according to claim 16.
Claim 24
Dependent Claim
62 words
A method for treating hypocholesterolemic-related diseases, thrombotic diseases, atherogenic diseases, inflammation, immunodeficiencies, fever, edema, diabetes mellitus, pain, septic shock, chronic fatigue syndrome or functio laesa, to decrease lipoprotein (a) concentration in the blood or to increase feed conversion efficiency in a patient, comprising the step of administering to said patient a pharmaceutically effective amount of the pharmaceutical composition according to claim 17.
Claim 25
Dependent Claim
36 words
A method for decreasing the total serum cholesterol and LDL-cholesterol in a human or animal, comprising the step of administering to said human or animal a cholesterol-lowering effective amount of the foodstuff according to claim 8.
Claim 26
Dependent Claim
36 words
A method for decreasing the total serum cholesterol and LDL-cholesterol in a human or animal, comprising the step of administering to said human or animal a cholesterol-lowering effective amount of the foodstuff according to claim 9.
Claim 27
Dependent Claim
37 words
A method for deceasing the total serum cholesterol and LDL-cholesterol in a human or animal, comprising the step of administering to said human or animal a cholesterol-lowering effective amount of the dietary supplement according to claim 12.
Claim 28
Dependent Claim
37 words
A method for decreasing the total serum cholesterol and LDL-cholesterol in a human or animal, comprising the step of administering to said human or animal a cholesterol-lowering effective amount of the dietary supplement according to claim 13.
Claim 29
Dependent Claim
34 words
A method for increasing the HDL/LDL cholesterol ratio in a human or animal, comprising the step of administering to said human or animal a cholesterol-lowering effective amount of the foodstuff according to claim 8.
Claim 30
Dependent Claim
34 words
A method for increasing the HDL/LDL cholesterol ratio in a human or animal, comprising the step of administering to said human or animal a cholesterol-lowering effective amount of the foodstuff according to claim 9.
Claim 31
Dependent Claim
35 words
A method for decreasing the HDL/LDL cholesterol ratio in a human or animal, comprising the step of administering to said human or animal a cholesterol-lowering effective amount of the dietary supplement according to claim 12.
Claim 32
Dependent Claim
35 words
A method for decreasing the HDL/LDL cholesterol ratio in a human or animal, comprising the step of administering to said human or animal a cholesterol-lowering effective amount of the dietary supplement according to claim 13.
Claim 33
Independent Claim
76 words
A method for enhancing the yield of tocotrienol compounds as defined in any one of claims 1 and 2, wherein said tocotrienols are obtained from a tocotrienol-rich fraction of a biological source, said method comprising the steps of: (a) dissolving the tocotrienol rich fraction from a biological source in a solvent; (b) contacting the dissolved tocotrienol rich fraction with an amine column; and (c) eluting the tocotrienols with a solvent that does not substantially elute impurities.
Claim 34
Independent Claim
55 words
A method for enhancing the yield of tocotrienol compounds as defined in any one of claims 1 and 2 wherein said tocotrienols are obtained from a biological source, said method comprising the steps of: (a) extracting the biological source with an organic solvent, (b) heating the extracted source, and (c) extracting the heated biological source.
Claim 35
Dependent Claim
17 words
The method according to claim 31, wherein the heating of step (b) is accomplished with microwave heat.
Claim 36
Dependent Claim
14 words
The method according to claim 30, wherein the biological source is a plant source.
Claim 37
Dependent Claim
39 words
The method according to claim 31, wherein the plant source is selected from the group consisting of oats, peanuts, pine nuts, oat bran, oat bran oil, barley, barley bran, barley bran oil, rice, rice bran and rice bran oil.
Claim 38
Dependent Claim
17 words
The method according to claim 34, wherein the plant source is rice bran or rice bran oil.
Claim 39
Dependent Claim
14 words
The method according to claim 30, wherein the solvent of step (a) is hexane.
Claim 40
Dependent Claim
21 words
The method according to claim 30, wherein the amine column of step (b) is a Bond Elute amine or cyano column.
Claim 41
Dependent Claim
21 words
The method according to claim 30, wherein the solvent of step (c) is a gradient system of 0.5%-3% isopropanol in hexane.
Claim 42
Dependent Claim
14 words
The method according to claim 31, wherein the biological source is a plant source.
References Cited (Backward Citations)
GB870638A
Cited
US3064012A
Cited
US3122565A
Cited
GB1011319A
Cited
GB1506076A
Cited
DE3221506A1
Cited
US4603143A
Cited
US5034420A
Cited
US5138075A
Cited
EP0304842A2
Cited
US4788304A
Cited
JPH02264712A
Cited
EP0421419A2
Cited
US5217992A
Cited
US5348974A
Cited
US5393776A
Cited
US5204373A
Cited
US5296508A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 2000-01-07 | 2000-07-08 | 2001-01-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2004-01-07 | 2004-07-08 | 2005-01-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2008-01-07 | 2008-07-08 | 2009-01-07 | $7700.00 | Window Closed / Lapsed |