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Beta-hydroxyl butyryl-amino acid compound, preparing method and application

A technology of hydroxybutyryl and amino acid, which is applied in the field of compounds, can solve the problems of different doses, different effects, low bioavailability, ketoacidosis in blood vessels, etc.

Active Publication Date: 2018-05-11
郑州海斯威生物技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, BHB is very unstable in the human body. Whether BHB or BHB salt is introduced, it will not only cause great damage to the gastrointestinal digestive system, resulting in low bioavailability, but also cause differences in dosage due to differences in each person's physique. The effects are different; at the same time, BHB cannot be injected routinely, and it is easy to cause intravascular ketoacidosis poisoning, which limits the application of BHB

Method used

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  • Beta-hydroxyl butyryl-amino acid compound, preparing method and application
  • Beta-hydroxyl butyryl-amino acid compound, preparing method and application
  • Beta-hydroxyl butyryl-amino acid compound, preparing method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment A1

[0122] β-Hydroxybutyryl-leucine pseudo-dipeptide

[0123] (1) Preparation of intermediate tert-butyldimethylsilyl ether β-hydroxybutyric acid

[0124] synthetic route:

[0125]

[0126]Ethyl β-hydroxybutyrate (132g, 1mol) and imidazole (136g, 2mol) were dissolved in 200mL of dichloromethane, cooled to 0-5°C, tert-butyldimethylsilyl chloride (195.8g, 1.3mol) was dissolved in 200 mL of dichloromethane was added dropwise into the reaction solution. After the dropwise addition, the ice bath was removed, and the reaction was carried out overnight at room temperature. After the gas chromatography monitors that the reaction is complete, add water to quench the reaction. After liquid separation, the organic phase is washed once with 50mL of 0.1M dilute hydrochloric acid and 50mL of saturated sodium chloride aqueous solution, and dried and concentrated to obtain tert-butyldimethylsilyl ether β-hydroxyl Crude ethyl butyrate. Add 2 times the volume of ethanol to the protected crude...

Embodiment A2

[0135] β-Hydroxybutyryl-phenylalanine pseudo-dipeptide

[0136]

[0137] The synthetic route can refer to the synthetic route of Example A1, which is prepared from the intermediate tert-butyldimethylsiloxane β-hydroxybutyric acid and ethyl phenylalanine hydrochloride, with a yield of 67.8%.

[0138] 1H NMR (400MHz, D2O) δ7.16(m,5H),4.40(m,1H),3.94(m,1H),3.12(m,1H),2.82(m,1H),2.19(m,2H) ,0.98(d,3H).

Embodiment A3

[0140] β-Hydroxybutyryl-isoleucine pseudo-dipeptide

[0141]

[0142] The synthetic route can refer to the synthetic route of Example A1, which is prepared from the intermediate tert-butyldimethylsilyl ether β-hydroxybutyric acid and isoleucine ethyl ester hydrochloride, with a yield of 62.8%.

[0143] 1H NMR (400MHz, D2O) δ4.11(m,1H),4.02(m,1H),2.34(m,2H),1.75(m,1H),1.32(m,1H),1.12(d,3H) ,1.05(m,1H),0.80(m,6H).

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Abstract

The invention relates to the technical field of compounds, in particular to a beta-hydroxyl butyryl-amino acid compound, a preparing method and application. The compound comprises compounds with the structural formulas shown in the formulas I, II, III, IV, V, VI, VII, VIII, IX and X, pharmaceutically-accepted salts or solvates of the compounds and pharmaceutically-accepted esterification products.Through rat experiments, cell experiments and safety evaluation, it is proved that the compound can be metabolized into BHB, amino acids and pseudopeptide metabolites in a human body, has an in-vivometabolism time half-life period of 4-6 hours, is safe and free of toxin and side effects, has high stability and certain anti-cancer activity (commonly 30-80 for esophageal cancer cell lines IC50), has good functions for reducing weight, resisting ageing, treating Alzheimer's disease and epilepsy and reducing blood fat and blood pressure, and is expected to become a novel food material for supplementing energy and being developed into different healthcare foods or pharmaceutically-accepted OTC medicines.

Description

technical field [0001] The invention relates to the technical field of compounds, in particular to a β-hydroxybutyryl-amino acid compound and its preparation method and application. Background technique [0002] In recent years, the development of pharmaceutical science has shown a rapid development in the direction of improving the body's own immunity and using the body's own immunity to treat various diseases. The research on endogenous substances, such as amino acids, small molecule active peptides, polypeptides etc. have become one of the mainstream and hot spots in the development of pharmaceutical science. The research on the medicinalization of endogenous substances is in the ascendant and developing in depth. The progress and breakthroughs in this area not only directly promote the industry of new drugs and new health care products, but also have important significance for the study of the material basis of human life and the code of life activities. [0003] β-hyd...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C235/12C07C231/12C07D207/16C07D233/64C07D209/20C07C323/59C07C319/20C07C237/22C07C279/14C07C277/08C07K5/097C07K5/065C07K5/107C07K5/103C07K5/062C07K5/068C07K7/06C07K5/072C07K5/078C07K5/093C07K5/09C07K5/087C07K5/083A61K38/05A61K38/06A61K31/198A61K31/401A61K31/4172A61K31/405A61P3/04A61P3/06A61P25/00A61P25/08A61P25/16A61P25/28A61P35/00A61P39/00A61P29/00A61P3/02A61P3/00A61P3/12A61P37/04A61K8/44A61K8/64A61Q19/08A23L33/175A23L33/18
CPCA23V2002/00A61K8/44A61K8/64A61K38/00A61Q19/08A23L33/175A23L33/18C07C235/12C07C237/22C07C279/14C07C323/59C07D207/16C07D209/20C07D233/64C07K5/06026C07K5/06034C07K5/06043C07K5/06052C07K5/0606C07K5/06069C07K5/06078C07K5/06086C07K5/06104C07K5/06113C07K5/06165C07K5/0806C07K5/0808C07K5/081C07K5/0812C07K5/0815C07K5/0819C07K5/0823C07K5/1008C07K5/1016C07K7/06A23V2200/308A23V2200/322A23V2200/3262A23V2200/332A23V2250/06A23V2250/55Y02P20/55
Inventor 刘成张红雨孙光辉
Owner 郑州海斯威生物技术有限公司
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