- Preparation method 8 -hydroxy -2, 2, 14 and 14 -tetramethyl-pentadecanedioic acid
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The invention relates to a preparation method of 8 - hydroxyl -2, 2, 14 and 14 -tetramethyldodecanedioic acid. The method utilizes isobutyronitrile (II) and 1, 4 - dihalogenated butane as raw materials to obtain 2, 2 -dimethyl -6 -halogenated n-hexanenitrile, then with 1, 3 -di P-substituted acetone (substituent P) COOR. CN Or CONH2 Through substitution reaction, hydrolysis, acidification and decarboxylation, 8 - oxo -2, 2, 14, 14 - tetramethyldodecanedioic acid, and a boric acid reducing agent are subjected to reduction reaction, and then hydrolyzed and acidified to obtain a target product. To the invention, isobutyronitrile is adopted as an initial raw material, and raw materials are cheap and easily available. Easy operation, reaction conditions easily realize. The system is safe, environment-friendly and small in wastewater generation amount. The method has the advantages of low cost, high reaction selectivity, less byproducts, high target product yield and purity and suitability for green industrial production.
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- Preparation method of bempedoic acid
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The invention discloses a preparation method of bempedoic acid. The method comprises the following steps: carrying out a condensation reaction on ethyl isobutyrate and 1,11-dibromo-undecane-6-alcohol under the action of an alkali accelerator to generate 8-hydroxy-2, 2, 14, 14-tetramethyl pentadecanedioic acid diethyl ester, and carrying out hydrolysis reaction on the intermediate to obtain the bempedoic acid. The preparation method is simple in process, mild in condition, safe and environment-friendly, and provides a new way for industrial production.
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- Preparation method of Bempedoic acid
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The invention discloses a preparatino method ofBempedoic acid. The preparation method comprises the following steps: carrying out condensation reaction on ethyl isobutyrate and 2-(5-bromo-n-amyl)-1, 3-dioxocyclopentane under the effect of an alkali accelerator, carrying out hydrolysis reaction to obtain an intermediate 8-oxa-2, 2-dimethyl octanoic acid, and carrying out Grignard reaction on the intermediate and 7-bromo-2, 2-dimethyl heptanoic acid to obtain the Bempedoic acid. The preparation method is simple in process, mild in condition, safe and environment-friendly, and provides a new way for industrial production.
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Paragraph 0032-0033
(2021/07/24)
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- Synthetic method of bepidic acid
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The invention belongs to the field of medicine synthesis, and relates to a novel synthesis method of a compound bepidic acid. The preparation method comprises the following steps: (1) carrying out primary alkylation on ethyl isobutyrate and 1, 5-dibromopentane under the action of lithium diisopropylamide to generate a compound 1; (2) carrying out alkylation twice on dibenzyl malonate and the compound 1 under the action of sodium hydride to generate a compound 2; (3) removing benzyl from the compound 2 under the action of Pd/C and hydrogen to obtain a compound 3; (4) carrying out electrochemical reaction on the compound 3 in a methanol solution of methanol and ammonia to obtain a compound 4; (5) finally carrying out sodium borohydride hydrolysis and potassium hydroxide hydrolysis on the compound 4, and acidifying to obtain the final bepidic acid. The method is carried out under electrochemical conditions, is mild in conditions and high in efficiency, and is suitable for industrial production.
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- Synthesis of bempedoic acid through electrochemical decarboxylation of dialkylated malonic acid
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Bempedoic acid is a small-molecule inhibitor of adenosine triphosphate-citrate lyase (ACL) that is effective in the treatment of hypercholesterolemia and hypertension. In this paper, a new, six-step synthesis of bempedoic acid with 42% overall yield is reported. Ketone formation by electrochemical decarboxylation of dialkylated malonic acid is introduced as the key step of this process. This method uses mild conditions and its high efficiency makes it potentially suitable for industrial production.
- Xu, Zhimin,Zheng, Yue,Tian, Lifang,Wang, Yahui
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p. 3608 - 3612
(2021/05/21)
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- Preparation method of bepiridic acid
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The invention relates to a preparation method of bepiridic acid, and the method comprises the following process steps: (1) synthesis of an intermediate BP-B: dissolving a compound A in nitromethane, and carrying out nucleophilic reaction under alkaline conditions to obtain the intermediate BP-B; (2) synthesis of an intermediate BP-C: carrying out a Nef Reaction reaction on the intermediate BP-B obtained in the step (1) under an alkaline condition to obtain the intermediate BP-C; (3) synthesis of beparidic: carrying out a reduction reaction on the intermediate BP-C obtained in the step (2) and a reducing agent to obtain the beparidic. In the second-step reaction of the process, use of an expensive p-toluenesulfonyl methyl isocyanide reagent is avoided. The third-step reaction of the process avoids the use of column chromatography separation, and is more suitable for industrial production.
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- Synthesis method of 8-hydroxy-2, 2, 14, 14-tetramethyl pentadecanedioic acid
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The invention provides a synthesis method for preparing 8-hydroxy-2, 2, 14, 14-tetramethyl pentadecanedioic acid, which comprises the step of carrying out addition reaction on a compound III and a compound IV to obtain a compound II. The method has the advantages of cheap and easily available raw materials and short steps, and can greatly reduce the production cost; the operation is simple, and industrial production is facilitated; and the quality of reaction products in each step is controllable, and the obtained product is high in purity and small in single impurity.
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Paragraph 0067-0070
(2021/09/11)
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- METHODS OF MAKING BEMPEDOIC ACID AND COMPOSITIONS OF THE SAME
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The invention provides methods of preparing 8-hy droxy-2,2, 14,14- tetramethylpentadecanedioic acid and methods of making a pharmaceutical material comprising a purified amount of 8-hy droxy-2,2, 14, 14-tetramethylpentadecanedioic acid. Also provided are compositions and pharmaceutical materials including a purified amount of 8- hydroxy-2,2, 14, 14-tetramethylpentadecanedioic acid as well as methods of treating various diseases and conditions using the compositions and pharmaceutical materials.
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- Synthetic method of bempedoic acid and intermediate thereof
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The invention discloses new intermediate compounds 6 and 7 of bempedoic acid, and also discloses a synthetic method of bempedoic acid. The method shortens the route steps, improves the yield, lowers the process cost, improves the structure of the bempedoic acid intermediate, enhances the crystallinity of the intermediate compounds, and is beneficial to enhancing the purity of the final product, and suitable for enlarged production. The structural formulas of the compound 6 and the compound 7 are shown in the specification, wherein -N(R2)2 represents N,N-dimethylamino, cyclohexylamino, morpholinyl or amino; and M is an inorganic base or organic alkali, and comprises sodium, potassium, calcium, cyclohexanediamine or morpholine.
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Paragraph 0166-0168
(2020/12/31)
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- Synthetic method of bempedoic acid
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The invention discloses a synthetic method of bempedoic acid. The method comprises the following steps of: taking isobutyronitrile (ester) as a starting raw material, carrying out reaction with 2, 5-dibromopentane under the catalysis of alkali to generate 7-bromo-2, 2-dimethylheptonitrile (ester), then forming a Grignard reagent with magnesium, carrying out reaction with formate to generate 8-hydroxy-2, 2, 14, 14-tetramethylpentadecane dinitrile (ester), and finally carrying out alkaline hydrolysis and acidification to obtain bempedoic acid. The synthetic route is short, all the used raw materials are easy to obtain, the cost is low, the yield of each step of reaction is high, and the purity is high, therefore the method is suitable for industrial production.
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Paragraph 0047; 0053-0056; 0057; 0063-0066; 0067-0068
(2020/11/05)
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- NOVEL SALTS AND POLYMORPHIC FORM OF BEMPEDOIC ACID
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The present invention relates to novel pharmaceutically acceptable salts of Bempedoic acid, novel intermediates of Bempedoic acid, novel crystalline form of Bempedoic acid and novel processes for the preparation of Bempedoic acid or its intermediates thereof.
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- PROCESS FOR PREPARATION OF BEMPEDOIC ACID
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Aspect of the present application provides cost effective and commercially viable process for preparation of Bempedoic acid. The process involves the reduction of compound formula I to obtain compound formula II which is hydrolyzed to get Bempedoic acid. The present application also provides the process for preparation of Bempedoic acid using compound of formula II without purification.
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- Compound and method for synthesizing 8-hydroxy-2,2,14,14-tetramethyl pentadecanedioic acid by adopting compound
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The invention belongs to the field of chemical synthesis, and relates to a compound with a structural formula as described in the specification. In the structural formula, R1, R2 and R3 are independently selected from C1-C6 alkyl groups, alkenyl groups and cycloalkyl groups respectively. The invention also provides a method for synthesizing 8-hydroxy-2,2,14,14-tetramethyl pentadecanedioic acid byusing the compound. The method has the advantages of short reaction steps, simplified operation and greatly reduced production cost; and the use of raw materials with high toxicity and danger is avoided, so the method is safer.
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- Synthetic method of bempedoic acid and intermediate
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The invention discloses a synthesis method of bempedoic acid, which comprises the following steps: reacting methyl 3-bromo-2,2-dimethyl propionate serving as a raw material with bis(pinacolato)diboronto generate an intermediate compound I, reacting with 5-keto-1,9-dibromononane to generate an intermediate compound II, and hydrolyzing and reducing to generate the bempedoic acid.
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- Synthetic method for 8-hydroxyl-2,2,14,14-tetramethyl-pentadecanedioic acid
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The invention belongs to the technical field of medicines, and specifically provides a synthetic method for 8-hydroxyl-2,2,14,14-tetramethyl-pentadecanedioic acid. The synthetic method comprises the following steps: (1) pouring 8-keto-2,2,14,14-tetramethyl-pentadecanedioic acid into purified water, and adding a proper amount of alkali until the 8-keto-2,2,14,14-tetramethyl-pentadecanedioic acid iscompletely dissolved so as to obtain 8-keto-2,2,14,14-tetramethyl-pentadecanediate; (2) adding sodium borohydride into an above-mentioned reaction solution, and carrying out a carbonyl reduction reaction under the condition of 20 to 25 DEG C so as to obtain 8-hydroxyl-2,2,14,14-tetramethyl-pentadecanediate; and (3) adding concentrated hydrochloric acid into an above-mentioned reaction solution until the pH value of the reaction solution is adjusted to 1 to 3 so as to generate the 8-hydroxyl-2,2,14,14-tetramethyl-pentadecanedioic acid. The synthetic method provided by the invention reduces theusage amount of the sodium borohydride, decreases the dangerousness of a reaction, simplifies operation, reduces the cost input amounts of a solvent and raw materials, and is applicable to industrialproduction.
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Paragraph 0025-0047
(2019/05/16)
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- HYDROXYL COMPOUNDS AND COMPOSITIONS FOR CHOLESTEROL MANAGEMENT AND RELATED USES
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The present invention relates to novel hydroxyl compounds, compositions comprising hydroxyl compounds, and methods useful for treating and preventing a variety of diseases and conditions such as, but not limited to aging, Alzheimer's Disease, cancer, cardiovascular disease, diabetic nephropathy, diabetic retinopathy, a disorder of glucose metabolism, dyslipidemia, dyslipoproteinemia, hypertension, impotence, inflammation, insulin resistance, lipid elimination in bile, obesity, oxysterol elimination in bile, pancreatitis, pancreatitius, Parkinson's disease, a peroxisome proliferator activated receptor-associated disorder, phospholipid elimination in bile, renal disease, septicemia, metabolic syndrome disorders (e.g., Syndrome X), thrombotic disorder. Compounds and methods of the invention can also be used to modulate C reactive protein or enhance bile production in a patient. In certain embodiments, the compounds, compositions, and methods of the invention are useful in combination therapy with other therapeutics, such as hypocholesterolemic and hypoglycemic agents.
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Page 263-264
(2008/06/13)
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