- Synthesis method of teprenone and intermediate thereof
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The invention relates to synthesis methods of teprenone and an intermediate thereof. The synthesis of the intermediate all-trans (5E,9E)-farnesyl acetone comprises: 1) in the presence of a catalyst, carrying out a carroll rearrangement reaction on the mixture of 5E-nerolidol and 5Z-nerolidol and hydrocarbonyl acetoacetate to obtain the isomer mixture of (5Z,9Z)-farnesyl acetone, (5Z,9E)-farnesyl acetone, (5E,9Z)-farnesyl acetone, and (5E,9E)-farnesyl acetone, wherein the content of (5E,9E)-farnesyl acetone in the isomer mixture is controlled at more than 18%; and 2) carrying out low-temperature crystallization separation on the isomer mixture in a moderately polar solvent to obtain the all-trans (5E,9E)-farnesyl acetone. According to the present invention, the high-purity all-trans (5E,9E)-farnesyl acetone is obtained by using the mixture of 5E-nerolidol and 5Z-nerolidol as the raw material through the low-temperature crystallization separation, such that the teprenone with the qualified quality can be conveniently obtained.
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Paragraph 0080; 0081
(2021/08/19)
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- Novel intermediate for synthesizing teprenone and application of novel intermediate
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The invention discloses a novel intermediate for synthesizing teprenone. The novel intermediate is a compound shown as a formula 5. The novel intermediate has the advantages that process routes for synthesizing the teprenone by the compound shown as the formula 5 are simple, raw materials are easily available, reaction conditions are mild, side reaction rarely can be carried out, and accordingly the novel intermediate is favorable for industrial production; the high-purity teprenone can be obtained by the aid of the process routes without rectification, and the requirements on ratios of isomermono-cis-form (5Z, 9E and 13E) to all-trans-forms (5E, 9E and 13E) of the teprenone can be met.
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Paragraph 0045; 0066-0069
(2019/04/17)
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- Process for synthesizing teprenone
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The invention discloses a process for synthesizing teprenone.According to the process for synthesizing teprenone, nerolidol is adopted as an initial raw material and subjected to selenium dioxide and tert-butyl hydroperoxide oxidizing in sequence, nerolidol and dihydropyran are subjected to acid catalysis to form acetal, acetal reacts with a Grignard reagent on the presence of copper salt and reacts with methyl acetoacetate on the presence of aluminum salt, and the teprenone product consistent with the configuration of products sold on the market is obtained through four steps of reactions.According to a preparation method of teprenone, the raw material is cheap and easy to obtain, operation is easy and convenient, the reaction conditions are mild, and industrial production is expected to be achieved.
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- A process for the preparation of Teprenone
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The invention discloses a method for preparing teprenone. The method comprises the following steps: (a) mixing geranyl linalool, acetyl Meldrum's acid and aluminum isopropoxide according to a molar ratio of 1: (1.2-1.5): (0.02-0.1), dissolving the mixture in a paraxylene solvent, heating up to 50-160 DEG C, refluxing for 6-10 hours, cooling and removing the solvent to obtain a teprenone mixture; (b) washing and extracting the teprenone mixture, mixing organic layers, and drying to obtain a crude product of teprenone; (c) carrying out molecular distillation, impurity removal, decompression rectifying and impurity removal on the crude product of teprenone to obtain a teprenone product. The method is simple and easy to control, the conversion rate of the product is high, and the prepared product is high in purity, stable in quality and high in safety, thereby being convenient to promote and use in clinical and industrial production.
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Paragraph 0025-0026
(2016/10/07)
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- GGA DERIVATIVES
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This invention relates to geranylgeranyl acetone (GGA) derivatives, pharmaceutical compositions comprising GGA derivatives and the use of GGA derivatives.
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- METHODS FOR TREATING NEURON DAMAGE
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This invention relates to the use of geranylgeranyl acetone (GGA), its isomers, and GGA derivatives in a method for for treating a disease in a subject mediated in part by miRNA-378 or miRNA-711 increased activity comprising administering to the subject a therapeutically effective amount of 5-trans-GGA or a derivative thereof.
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- GGA AND GGA DERIVATIVES COMPOSITIONS THEREOF AND METHODS FOR TREATING NEURODEGENERATIVE DISEASES INCLUDING PARALYSIS INCLUDING THEM
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This invention relates to geranylgeranyl acetone (GGA) derivatives and the use of GGA, its isomers, and GGA derivatives in methods for inhibiting neural death, increasing neural activity, increasing axon growth and cell viability, and increasing the survival rate of subjects administered the GGA or GGA derivatives.
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- GGA AND GGA DERIVATIVES, COMPOSITIONS THEREOF AND METHODS FOR TREATING NEURODEGENERATIVE DISEASES INCLUDING PARALYSIS INCLUDING THEM
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This invention relates to geranylgeranyl acetone (GGA) derivatives and the use of GGA, its isomers, and GGA derivatives in methods for inhibiting neural death, increasing neural activity, increasing axon growth and cell viability, and increasing the survival rate of subjects administered the GGA or GGA derivatives.
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- GERANYLGERANYLACETONE DERIVATIVES
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Provided herein are geranylgeranylacetone derivatives and methods of using them.
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- METHODS FOR TREATING NEURODEGENERATIVE DISEASES
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This invention relates to the 5-cis and 5-trans isomers of geranylgeranyl acetone, preferably such synthetic isomers, and pharmaceutical compositions containing such isomers. Other aspects of this invention relate to the use of geranylgeranyl acetone and its isomers in methods for inhibiting neural death, increasing neural activity, and increasing axon growth and cell viability. Geranylgeranyl acetone is a known anti-ulcer drug used commercially and in clinical situations. GGA has also been shown to exert cytoprotective effects on a variety of organs, such as the eye, brain, and heart.
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- A strategy for position-selective epoxidation of polyprenols
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An effective strategy has been developed for the efficient site-selective epoxidation of poylolefinic isoprenoid alcohols, based on the use of an internal control element for intramolecular reaction. The approach is illustrated by application to a series of polyisoprenoid alcohols (polyprenols) at substrate concentration of 0.5 mM. With polyprenol substrates having the hydroxyl function at one terminus, the internal epoxidation can be directed at the double bond of the polyprenol, which is either four or five away from the terminal hydroxyprenyl subunit.
- Gnanadesikan, Vijay,Corey
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supporting information; experimental part
p. 8089 - 8093
(2009/02/01)
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- PROCESS FOR PREPARING GERANYLGERANYLACETONE
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The present invention provides a process for preparing geranylgeranylacetone comprises the steps of: reacting geranyl linalool with methyl acetoacetate in the presence of an aluminum catalyst; hydrolyzing aluminum catalyst in a reaction solution; washing the reaction solution with a wash solution containing a lower alcohol; and distilling the washed reaction solution.
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Page/Page column 7-9
(2008/12/05)
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- Superacidic low-temperature cyclization of terpenols and their acetates
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The superacidic low-temperature cyclization of terpenols and their acetates be fluorosulfonic acid represents a highly efficient chemo- and structurally selective and stereospecific process.Homoallylic alcohols (α-isomers of cycloterpenols) are the products of cyclization of terpenols; the configuration of the hydroxymethyl group in the products is predetermined by the configuration of the allylic double bond in aliphatic or partially cyclized precursors.The cyclization of terpenyl acetates yields monoacetates of fully cyclized diastereomeric primary-tertiary γ-diols.Their stereochemistry also depends on the configuration of the allylic double bond in the starting substrates. - Key words: terpenols; terpenyl acetates; cyclization, fluorosulfonic acid, drimanes, isoagathanes, scarlanes.
- Vlad, P. F.,Ungur, N. D.,Nguen Van Hung,Perutsky, V. B.
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p. 2391 - 2403
(2007/10/03)
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- β,γ-dihydropolyprenyl alcohol derivatives and pharmaceutical composition containing a polyprenyl compound
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A β,γ-dihydropolyprenyl alcohol derivative having the formula: STR1 wherein n is an integer of 5 to 7 and R is hydrogen, a lower alkyl group or an aliphatic or aromatic acyl group, is new and useful as a phylactic agent against human and animal infectious diseases. Other disclosed polyprenyl compounds are also useful as such agents.
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- Structure and Biosynthesis of Cleomeprenols from the Leaves of Cleome spinosa
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Cleomeprenols isolated from Cleome spinosa L. (Capparidaceae) have been identified as nonaprenol (1), decaprenol (2), and undecaprenol (3), which are composed of an ω-terminal isoprene, three internal E-isoprene, and the remaining Z-isoprene residues, respectively.Feeding experiments using stereospecifically double-labelled radioactive mevalonate showed that all the cleomeprenols are composed of four biogenetically E- and the remaining biogenetically Z-isoprene residues.Occurence of the succesive cis-condensation of isoprene residues with (2E,6E,10E)-geranylgeranyl pyrophosphate was demonstrated by comparing the incorporation of a homologue of all-E-prenyl pyrophosphates with that of the corresponding 2Z-isomer.
- Suga, Takayuki,Shishibori, Tsuyoshi
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p. 2098 - 2104
(2007/10/02)
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- Therapeutic preparations for peptic ulcers comprising aliphatic ketone derivative
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A therapeutic preparation having excellent effect for peptic ulcers with low toxicity which comprises aliphatic ketone derivative of the general formula: STR1 wherein represents a saturated or unsaturated bond, R1 is hydrogen or a lower alkyl group, R2 is hydrogen atom, a lower alkyl group or a lower alkylcarbonyl group, R3 is an aliphatic hydrocarbon group of the general formula: STR2 WHEREIN L, M AND N ARE 0 OR 1, PROVIDED THAT L+M+N≥2; AND A, B, C, D, E AND F ARE HYDROGEN ATOM, OR THEY MAY FORM A BOND OF A--B, C--D OR E--F, PROVIDED THAT IF THE BOND IS A SATURATED BOND, THE A, B, C, D, E AND F REPRESENT ALL HYDROGEN ATOM.
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