- Synthesis method of voglibose
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The invention provides a synthesis method of voglibose, and solves the technical problems that in an existing synthesis method of voglibose, raw materials are difficult to obtain, high in price, large in investment, low in yield and not suitable for industrial production. The synthesis method comprises the steps: synthesizing a compound V by taking glucose monohydrate and sodium acetate as raw materials through eleven reaction steps; and preparing a compound VIII from the compound V through an addition reaction, a ring-opening reaction and an aldol condensation reaction, and thus obtaining voglibose through amination reduction of the compound VIII. The synthesis method of voglibose can be widely applied to the technical field of voglibose synthesis methods.
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- Preparation method of voglibose
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The invention discloses a preparation method of voglibose. The preparation method comprises the steps of adopting tetrabenzyl voltolose as a raw material for a reaction in an aprotic solvent in the presence of boron halide, and adding a basic substance for crystallization, suction filtration and recrystallization to obtain the high-purity and high-yield voglibose after the reaction is completed. The whole synthesis process has the advantages that the raw material cost is extremely low, the reaction time is short, and the product yield and the quality are high; the method is suitable for industrial production.
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Paragraph 0007; 0019-0022
(2019/10/22)
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- Method for preparing voglibose and corresponding intermediate
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The invention relates to a novel intermediate for preparing voglibose and a preparation method of the voglibose. In particular, the intermediate is shown as a formula II as shown in the specification.The intermediate is prepared by a reaction of a compound shown as a formula I with peroxide; in addition, the intermediate can be hydrolyzed to form valiolamine; and voglibose is further synthesized.The method is simple, environmentally-friendly and high in yield.
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Paragraph 0152-0154
(2019/01/23)
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- Preparation method for voglibose
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The invention discloses a preparation method for a drug namely voglibose (AO128) I for treatment of diabetes. With the preparation method provided by the invention, a target product with a yield of atleast 15% is obtained through seven steps by using an intermediate II derived from shikimic acid as a raw material. The method comprises the following steps: with a ring-opening product II as a starting raw material, allowing the ring-opening product II to undergo nucleophilic substitution with sodium azide so as to obtain a configuration-inverted intermediate III; allowing the intermediate III to react with benzoyl chloride so as to obtain a product IV; then allowing double bonds of the product IV to undergo high-selectivity catalytic oxidation through rhodium so as to obtain a diol productV; reducing an ester group of the diol product V through sodium borohydride so as to obtain a compound VI containing three hydroxyl groups; protecting the primary hydroxyl group and the secondary hydroxyl group of the compound VI so as to obtain an intermediate VII; allowing the intermediate VII to connect with dibenzoyl oxyacetone for further reduction so as to obtain a compound VIII; and removing all protecting groups from the compound VIII by one step so as to obtain a target product I, i.e., the voglibose (AO128). The preparation method provided by the invention has the advantages of cheapand easily-available raw materials and used reagents, high stereoselectivity, high yield and possibility of industrial production.
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Paragraph 0032; 0033
(2018/11/27)
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- Amino sugar compound and preparation method and application thereof
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The invention discloses an amino sugar compound as shown in formula I, a preparation method of the amino sugar compound and application of the amino sugar compound to the preparation of a compound as shown in formula A.
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Paragraph 0060; 0068; 0069
(2017/09/13)
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- Structural identification of 4-benzyl-voglibose hydrochloride monohydrate using NMR and single-crystal X-ray diffraction methods
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The chemical structure studies on an important related substance of voglibose have been carried out using NMR spectroscopy and single crystal X-ray crystallography. For the structure identification study, hydrochloride monohydrate of this compound was iso
- Zhang, Fen-Fen,Zhao, Yu-Qin,Fan, Jian-Ping,Liu, Li-Gang,Li, Rui-Wen,Shen, Wen-Bin,Ding, Ya
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- Diastereospecific epoxidation and highly regioselective ring-opening of (+)-valienamine: Practical synthesis of (+)-valiolamine
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An efficient and practical synthesis of (+)-valiolamine starting from readily available aminocyclitol (+)-valienamine in five steps and up to 80% total yield in gram-scale quantities is reported. Diastereospecific epoxidation by means of substrate directable reaction and regioselective ring-opening of corresponding epoxide are the key reactions in the synthesis, which circumvent laborious purification of products using chromatographical separation. The detailed mechanisms of epoxidation and ring-opening attacked by halide, including the directing and steric hindrance effect, are also discussed.
- Ji, Li,Zhang, Ding-Feng,Zhao, Qian,Hu, San-Ming,Qian, Chao,Chen, Xin-Zhi
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p. 7031 - 7037
(2013/07/26)
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- HYPOGLYCEMIC EFFECT ENHANCER
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A hypoglycemic effect enhancer for enhancing the activity of an α-glucosidase inhibitor, the enhancer comprising at least one kind of bacteria selected from the group consisting of bifidobacteria, lactic acid bacteria, saccharifying bacteria, and butyric acid bacteria.
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- PROCESSES FOR THE PURIFICATION OF VOGLIBOSE AND INTERMEDIATES THEREOF
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Processes for the purification of voglibose are provided. Also provided are processes for the purification of substituted or unsubstituted 5-oxo-1,2,3,4-cyclohexanetetrol and substituted 5-amino-1,2,3,4-cyclohexanetetrol, which compounds are useful intermediates in the preparation of voglibose.
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Page/Page column 8
(2008/06/13)
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- USE OF SUBSTITUTED 2 PHENYLBENZIMIDAZOLES AS MEDICAMENTS
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The present invention relates to the use of a substituted 2-phenylbenzimidazole of formula I wherein R1, R2, R3, R 4, R5 and m have the meanings given in the claims, for the preparation of a medicament for the treatment or prevention of diseases involving glucagon receptors, as well as new compounds of formula I wherein R1 is a group of formula
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- Process for preparation of voglibose
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A process capable of conveniently preparing voglibose at a low cost in a safe process, and an intermediate which can be suitably used in the process and a process for preparing the intermediate are provided. An inositol derivative represented by the formula (VI): wherein Prt is a protecting group of hydroxyl group; a process for preparing the inositol derivative, wherein a cyclohexanone compound represented by the formula (IV): wherein Prt is as defined above, is dihydroxyaminated using a dihydroxyaminating agent and a reducing agent; and a process for preparing voglibose represented by the formula (VIII): wherein the inositol derivative is oxidized to give an inositol compound, and the protecting group, Prt of the inositol compound is deprotected.
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Page/Page column 6
(2008/06/13)
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- PROCESS FOR THE PREPARATION OF VOGLIBOSE
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The invention relates to processes for the preparation of pure voglibose. The invention also relates to the preparation of acid addition salts of voglibose. More particularly, it relates to the preparation of crystalline hydrochloride salt of voglibose. The invention also relates to pharmaceutical compositions that include the pure voglibose or voglibose hydrochloride and use of said compositions for treatment or prevention of hyperglycemic symptoms and various disorders caused by hyperglycemia such as diabetes, obesity, and hyperlipemia.
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Page/Page column 9-10
(2008/06/13)
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- PROCESS FOR THE PREPARATION OF 1,2,3,4-CYCLOHEXANETETROL DERIVATIVES
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Provided herein are processes for the preparation of 1,2,3,4-cyclohexanetetrol derivatives, which are useful intermediates for the synthesis of voglibose; processes for the preparation of substituted 2,3,4,5-tetrahydroxycyclohexanone; and processes for preparing voglibose. Also provided are compounds formed by such processes.
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Page/Page column 20
(2008/06/13)
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- Valiolone, a method of preparing it, and its use to prepare acarbose and voglibose
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Disclosed is the compound valiolone, which has the formula (I): a method of preparing valiolone, and a method of using valiolone to prepare acarbose and voglibose.
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- Inosose derivatives, production and use thereof
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Disclosed is a novel inosose compound represented by the general formula: STR1 wherein X1 and X2 are both halogen; X1 is hydrogen and X2 is halogen; or X1 is --SQ1 and X2 is --SQ2 (each of Q1 and Q2 is lower alkyl or Q1 and Q2 may form lower alkylene), R1 is a protective group for hydroxyl and Y is =O, =N--Z (Z is hydroxyl which may be protected) or STR2 (A is hydrogen or an amine residue), particularly to the compound wherein the symbol Y is oxygen. The inosose compound is useful as intermediates for production of valiolamine and the N-substituted derivatives thereof, which have potent α-glucosidase inhibiting activities and are useful as preventives or therapeutics for symptoms of hyperglycemia and various diseases derived therefrom in human and animals, such as diabetes, obesity and hyperlipemia.
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- Inosose derivatives and production thereof
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The novel inosose derivatives STR1 wherein Y1 stands for hydroxyl group and Y2 stands for hydrogen atom, or Y1 and Y2 are joined to form a bond between carbon and carbon atoms, and R1 and is a protective group for hydroxyl group, are useful as a starting material for producing valienamine, valiolamine and their N-substituted derivatives.
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- N-SUBSTITUTED PSEUDO-AMINOSUGARS, THEIR PRODUCTION AND USE
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A compound of the formula: wherein A is a chain hydrocarbon group having 1 to 10 carbon atoms optionally substituted by hydroxyl, phenoxy, thienyl, furyl, pyridyl, cyclohexyl or an optionally substituted phenyl group, or a cyclic hydrocarbon group having 3 to 7 carbon atoms optionally substituted by hydroxyl, B is hydrogen or hydroxyl, and their production and use. These compounds exhibit excellent inhibitory activity against alpha-glucoside hydrolase, thus are useful for hyperglycemic symptoms and various disorders caused by hyperglycemia.
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