US2012095099A1PendingUtilityA1
Trans carotenoids, their synthesis, formulation and uses
Est. expiryFeb 24, 2025(expired)· nominal 20-yr term from priority
A61P 9/06A61P 43/00A61P 9/12A61P 3/06A61P 9/00A61P 35/00A61P 25/02A61P 25/00A61P 25/28A61P 29/00A61K 9/19A61N 5/10C07C 69/602A61K 31/202C07C 57/13A61K 31/11C07C 57/03A61K 41/0038A61K 45/06C07C 59/185C07F 1/04C07C 69/52
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Claims
Abstract
The invention relates to trans carotenoid compounds and salts thereof as well as compositions thereof, methods for making them, and uses thereof. These compounds are useful in improving diffusivity of oxygen between red blood cells and body tissues in mammals including humans.
Claims
exact text as granted — not AI-modified1 . A compound having the structure:
2 . A compound having the structure:
3 . A compound having the structure:
4 . A compound having the structure:
5 . A compound having the structure:
6 . A compound having the structure:
7 . A compound having the structure:
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24 . A lyophilized composition of a bipolar trans carotenoid.
25 . A composition as in claim 24 wherein the bipolar trans carotenoid is TSC.
26 . A method of synthesizing a BTCS compound having the formula
YZ-TCRO-ZY where:
Y=a cation
Z=a polar group which is associated with the cation, and
TCRO=trans carotenoid skeleton,
comprising the steps of: coupling a symmetrical dialdehyde containing conjugated carbon-carbon double bonds with a Wittig agent, and saponifying the product of the coupling step.
27 . A method as in claim 26 wherein the product of the coupling step is reacted with a second Wittig agent.
28 . A method as in claim 26 wherein the symmetrical dialdehyde containing conjugated carbon-carbon double bonds is a C10 or C20 dial.
29 . A method as in claim 26 wherein the coupling reaction is made in a pH neutral solvent system.
30 . A method as in claim 29 wherein said pH neutral system is a butylene oxide solvent system.
31 . A method as in claim 29 wherein said pH neutral system includes toluene, or methylene chloride/sodium hydroxide and sodium ethylate or sodium methylate.
32 . A method as in claim 26 wherein the Wittig agent is a triphenylphosphorane.
33 . A method as in claim 32 wherein the Wittig agent is [3-carbomethoxy-2-buten-1-ylidene]triphenylphosphorane.
34 . A method as in claim 26 wherein the Wittig agent is a triphenyl phosphonium bromide or triphenyl phosphonium chloride or a mixture of the two.
35 . A method as in claim 34 wherein the Wittig agent is D (2-(Ethoxycarbonyl)-2-buten-4-yl-triphenyl-phosphoniumbromide).
36 . A method as in claim 26 wherein the Wittig agent is a C2, C3, C5, C10 or C15 Wittig ester halogenide.
37 . A method as in claim 26 wherein the Wittig agent is a C2, C3, or C5 phosphonoester.
38 . A method as in claim 37 wherein the phosphonoester is triphenyl phosphono acetate.
39 . A method as in claim 26 wherein the coupling of step is made using butylene oxide as the solvent system.
40 . A method as in claim 26 wherein after the coupling step is the step of isolating the desired product of the coupling reaction.
41 . A method as in claim 26 wherein the product is saponified using a solution of NaOH, LiOH, KOH and methanol, ethanol or isopropanol as the solvent.
42 . A method as in claim 26 wherein the product of the coupling step is saponified using NaOH and ethanol.
43 . A method as in claim 26 wherein the product of the coupling step is saponified using a solution of NaOH and methanol.
44 . A method as in claim 26 wherein the step of saponifying the product of the coupling step comprises the steps of:
a) solubilizing the coupling product in ethanol, and
b) mixing the solution of step a) with a base.
45 . A method as in claim 44 wherein the base is selected from the group consisting of NaOH, KOH, and LiOH.
46 . A method as in claim 44 wherein the coupling product is saponified using ethanol and NaOH.
47 . A method as in claim 26 wherein after the saponifying step, the desired product is washed with ethanol.
48 . A method as in claim 26 wherein after the saponifying step, the desired product is washed with water.
49 . A method as in claim 26 wherein the desired product is TSC.
50 . A method of synthesizing a BTC compound having the formula
YZ-TCRO-ZY where:
Y=H
Z=a polar group which is associated with the H, and
TCRO=trans carotenoid skeleton,
comprising the steps of: coupling a symmetrical dialdehyde containing conjugated carbon-carbon double bonds with a Wittig agent.
51 . A method as in claim 50 wherein the coupling reaction is made in a pH neutral solvent system.
52 . A method as in claim 51 wherein said pH neutral system is a butylene oxide solvent system.
53 . A method as in claim 51 wherein said pH neutral system includes toluene, or methylene chloride/sodium hydroxide and sodium ethylate or sodium methylate.
54 . A method as in claim 50 wherein the Wittig agent is a triphenylphosphorane.
55 . A method as in claim 54 wherein the Wittig agent is [3-carbomethoxy-2-buten-1-ylidene]triphenylphosphorane.
56 . A method as in claim 50 wherein the Wittig agent is a triphenyl phosphonium bromide or triphenyl phosphonium chloride or a mixture thereof.
57 . A method as in claim 50 wherein the Wittig agent is a C5 Wittig ester halogenide.
58 . A method as in claim 50 wherein the Wittig agent is D (2-(Ethoxycarbonyl)-2-buten-4-yl-triphenyl-phosphoniumbromide).
59 . A method as in claim 50 wherein the coupling of step is made using butylene oxide as the solvent system.
60 . A method as in claim 50 wherein after the coupling step is the step of isolating the desired product of the coupling reaction.
61 . A method as in claim 60 wherein the desired product is washed with ethanol.
62 . A method as in claim 60 wherein the desired product is washed with water.
63 . A method as in claim 50 wherein the desired product is crocetin.
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71 . A method of treating hypertension in a mammal comprising administering to the mammal in need of treatment an amount of a trans carotenoid sufficient to reduce the hypertension.
72 . A method of treating ventricular fibrillations or tachycardia in a mammal comprising administering to a mammal in need of treatment an amount of a trans carotenoid sufficient to stop the ventricular fibrillations or tachycardia.
73 . A compound having the structure:
74 . A compound selected from the group consisting of TPC and TLC.
75 . A compound selected from the group consisting of Compounds AA and CC.Cited by (0)
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