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Blood sugar reducing compound, preparation method of blood sugar reducing compound, medicine composition including blood sugar reducing compound and application of medicine composition

A technology of compounds and mixtures, applied in the field of preparation of hypoglycemic drugs

Inactive Publication Date: 2014-07-02
BEIJING LABSOLUTIONS PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Moreover, when saxagliptin is used in combination with thiazolidinediones (TZDs), common adverse reactions include hypoglycemia

Method used

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  • Blood sugar reducing compound, preparation method of blood sugar reducing compound, medicine composition including blood sugar reducing compound and application of medicine composition
  • Blood sugar reducing compound, preparation method of blood sugar reducing compound, medicine composition including blood sugar reducing compound and application of medicine composition
  • Blood sugar reducing compound, preparation method of blood sugar reducing compound, medicine composition including blood sugar reducing compound and application of medicine composition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0510] Example 1: Compound 91

[0511]

[0512] ((1S,5S)-1-((1S)-1-amino-2-((3S)-3-nitrile-2-azabicyclo[3,1,0]hexan-2-yl)- 2-oxoethyl)adamantan-3-yl) 2-aminoacetate

[0513] At room temperature, dissolve saxagliptin (4g, 12mmol) in 50ml DMF, add K 2 CO 3 (5g, 36mmol), (Boc) 2 O (5.2g, 24mmol), reacted for 18 hours, added 100ml of dichloromethane, washed four times with water, Na 2 SO 4 Drying and concentration gave 5.4g of the product N-tert-butoxycarbonyl-(1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxyl-1-adamantyl)-acetyl Base]-2-azabicyclo[3.1.0]hexane-3-carbonitrile, the compound is C 23 h 33 N 3 o 4 , the calculated value of MS-ESI (m / z) is 415.25; the found value is 438.24 (100, MNa+).

[0514] At room temperature, N-tert-butoxycarbonyl-(1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxy-1-adamantyl)-acetyl]-2 -Azabicyclo[3.1.0]hexane-3-carbonitrile (500mg, 1.2mmol) was dissolved in 20ml of dichloromethane, N-Boc-glycine (1053mg, 6.1mmol) was added, DIC (922mg, 7.2mmol) , DMA...

Embodiment 2

[0516] Example 2: Compound 92

[0517]

[0518] (2S)-((1S,5S)-1-((1S)-1-amino-2-((3S)-3-nitrile-2-azabicyclo[3,1,0]hexane-2 -yl)-2-oxoethyl)adamantan-3-yl) 2-aminopropionate

[0519] Prepared as described in Example 1 except that N-tert-butoxycarbonyl-L-alanine was used instead of N-tert-butoxycarbonyl-L-glycine. The resulting compound is C 21 h 30 N 4 o 3 , the calculated value of MS-ESI (m / z) is 386.23; the measured value is 387.13 (100, MH + ).

Embodiment 3

[0520] Example 3: Compound 93

[0521]

[0522] (2R)-((1S,5S)-1-((1S)-1-amino-2-((3S)-3-nitrile-2-azabicyclo[3,1,0]hexane-2 -yl)-2-oxoethyl)adamantan-3-yl) 2-aminopropionate

[0523] Prepared as described in Example 1 except that N-tert-butoxycarbonyl-D-alanine was used instead of N-tert-butoxycarbonyl-L-glycine. The resulting compound is C 21 h 30 N 4 o 3 , the calculated value of MS-ESI (m / z) is 386.23; the measured value is 387.11 (100, MH + ).

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Abstract

The invention provides a blood sugar reducing compound, a preparation method of the blood sugar reducing compound, a medicine composition including the blood sugar reducing compound and an application of the medicine composition. The compound is a compound shown in a general formula (I) or a pharmaceutically acceptable salt, a solvate, a polymorphism body, an enantiomer or a racemic mixture thereof, the general formula is described in the specification, wherein R1, R2, R3 and R4 are independently H, optionally substituted alkyl, optionally substituted naphthenic base, optionally substituted alkoxy, optionally substituted aryl, optionally substituted aralkyl, or optionally substituted naphthenic base formed by R1 and R2, or optionally substituted heterocyclic radical formed by R2 and R3, or optionally substituted heterocyclic radical formed by R3 and R4. The compound is actively transported by a PepT1 transporter to be absorbed by the gastrointestinal tract, and decomposed in the intestinal tract and the liver to slowly generate saxagliptin, thus the blood concentration of the saxagliptin is increased, and the retention time of the saxagliptin in blood is prolonged. The blood sugar reducing treatment effect is favorably increased and the side reaction is favorably reduced due to stable blood concentration.

Description

technical field [0001] The present invention relates to a kind of hypoglycemic compound and a preparation method thereof, as well as a pharmaceutical composition containing the hypoglycemic compound and the use of the hypoglycemic compound in preparing hypoglycemic drugs. Background technique [0002] Diabetes mellitus is a metabolic disease characterized by elevated blood sugar caused by defects in insulin secretion and (or) action. Diabetic patients with long-term poor blood sugar control may be accompanied by various organs, especially eye, heart, blood vessel, kidney, nerve damage or organ insufficiency or failure, resulting in disability or premature death. In recent years, with the development of social economy and the improvement of residents' living standards in various countries in the world, the incidence and prevalence of diabetes have increased year by year, becoming a major social problem that threatens people's health, causing governments, health departments an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/12C07D401/12C07D209/52A61K31/403A61K31/454A61K31/55A61K31/4178A61K31/405A61P3/10A61P13/12A61P9/10A61P25/00A61P9/00
CPCC07D209/52C07D401/12C07D403/12
Inventor 王建民卢华君尹磊张小光李志强
Owner BEIJING LABSOLUTIONS PHARMA
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