Use of amidation product of glycine and metformin in preparation of drug for treating diabetes

The technology of a diabetes drug, metformin, is applied in the field of preparation of drugs for the treatment of diabetes, which can solve the problems of stably controlling blood sugar and achieve strong hypoglycemic effect and long-term effect

Inactive Publication Date: 2015-11-11
NANJING MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Due to the rapid metabolism of metformin hydrochloride and glycine, even with combined administration, blood sugar cannot be stably controlled for a long period of time, and multiple administrations are required

Method used

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  • Use of amidation product of glycine and metformin in preparation of drug for treating diabetes
  • Use of amidation product of glycine and metformin in preparation of drug for treating diabetes
  • Use of amidation product of glycine and metformin in preparation of drug for treating diabetes

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Synthesis of Phthalylglycine (Pht-Gly-OH):

[0024] Put 15.5g (0.105mol) of phthalic anhydride, 7.5g (0.1mol) of glycine, 50mL toluene and 0.8mL triethylamine in a 250mL eggplant-shaped flask, and heat to reflux at 140°C for 8h. After the reaction was completed, cool to room temperature, add 0.6 mL of concentrated hydrochloric acid to the reaction liquid in an ice-water bath, and stir for 30 min. After filtering, the filter cake was washed with water and dried to obtain 20.3 g of white solid with a yield of 99.0%.

[0025] 1HNMR(DMSO-d6,300MHz)δ(ppm):13.21(s,1H,-COOH),7.88-7.90(m,2H,ArH),7.92-7.94(m,2H,ArH),4.32(s,2H ,-CH2-).

[0026] Synthesis of phthaloylglycyl metformin (Pht-Gly-Met):

[0027] Put 4 g (0.024 mol) of metformin hydrochloride (0.024 mol) and 40 mL of sodium hydroxide solution with a concentration of 1 mol / L in a 250 mL eggplant-shaped bottle, and stir at room temperature for 30 min. The reaction solution was spin-dried, and 120 mL of methanol was ad...

Embodiment 2

[0035]Embodiment 2 Synthesis of phthaloylglycylglycyl metformin (Pht-Gly-Gly-Met)

[0036] Take a 250 mL eggplant-shaped bottle, add 2.22 g (0.01 mol) of glycyl metformin hydrochloride (Gly-Met HCl), 150 mL THF, 2.08 mL (0.015 mol) of triethylamine, and stir at room temperature for 3 -4h standby.

[0037] Put 2.04g (0.01mol) of phthalylglycine and 8mL of thionyl chloride in a 50mL eggplant-shaped bottle, stir and reflux at 80°C for 5h, and spin off the excess thionyl chloride to obtain Pale yellow acid chloride for use.

[0038] Add 5.3 g (0.025 mol) of tripotassium phosphate to the above-mentioned THF solution of glycyl metformin, and stir under an ice-water bath. The acid chloride prepared above was dissolved in 20 mL THF, and added dropwise to the metformin solution through a constant pressure dropping funnel. After the dropwise addition, the ice-water bath was removed, and the reaction solution was stirred at room temperature for 2-3 h.

[0039] After the reaction, 60 ...

Embodiment 3

[0044] The preparation of embodiment 3 diabetes mouse model

[0045] Streptozotocin (STZ) can damage islet cells, resulting in insufficient insulin secretion and hyperglycemia, leading to type Ⅰ diabetes. We used the method of intraperitoneal injection of STZ (50mg / kg) to establish a type Ⅰ diabetes model, selected 8-week-old male C57 mice, injected STZ intraperitoneally for five consecutive days, and tested blood glucose one week later. The mice with blood glucose greater than 11.1mmol / L were returned to For the diabetes group (Wld(S)protectsagainstperipheralneuropathyandretinopathyanexperimentalmodelofdiabetesinmice. Diabetologia. 2011,54(9):2440-50.)

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Abstract

The invention discloses a use of an amidation product of glycine and metformin in preparation of a drug for treating diabetes. Compared with the metformin hydrochloride-glycine combined drug, the amide derivative of glycine and metformin has better hypoglycemic effects and longer action time.

Description

technical field [0001] The invention belongs to the technical field of medicines for treating diabetes, and in particular relates to the application of an amidation product of glycine and metformin in the preparation of medicines for treating diabetes. Background technique [0002] Diabetes is a common chronic disease, mainly due to the absolute or relative lack of insulin in the blood, which leads to high blood sugar and diabetes, and then causes fat and protein metabolism disorders. Clinically, polyuria, polydipsia, polydipsia, and polyphagia may occur. Emaciation and other manifestations, severe cases are prone to acute complications such as ketoacidosis or chronic complications such as blood vessels and nerves. CN103263405B (Chinese Patent Application No. 201310168000.8, Nanjing Medical University) discloses a pharmaceutical composition comprising glycine and metformin hydrochloride and its application for treating diabetes. When glycine and metformin hydrochloride are ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/16A61P3/10
Inventor 陈琪李飞李科学
Owner NANJING MEDICAL UNIV
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