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New DPP-IV inhibitor

A compound, pharmaceutical technology, applied in the field of new DPP-IV inhibitors

Active Publication Date: 2011-05-18
BEIJING AOHE DRUG RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are many highly active DPP-IV inhibitors, and the selectivity and specificity of DPP-IV are difficult to solve

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0105] Example 17-(2-Chloro-acetyl)-3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazol[4,3-a]pyridine Preparation of oxazine

[0106] In a dry reaction flask, add 9.6g (50mmol) 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a] Pyrazine (see J.Med.Chem.2005, 48, 141-151 for its preparation method), 100ml of DMF, heated and stirred to dissolve, lowered to -5 ~ 0 ° C, slowly added dropwise 6.8g (60mmol) of chloroacetyl chloride Dichloromethane solution 100ml, dropwise, keep warm for 5h. Then warmed to room temperature and stirred for 0.5h. 100ml of water was added to the reaction solution, and the pH was slowly adjusted to 9 with 5% sodium bicarbonate solution under an ice-water bath. The organic layer was separated, and the aqueous layer was extracted twice with 50 ml of dichloromethane. The organic layers were combined, washed with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to o...

Embodiment 27-

[0107] Example 27-[2-(2,4,5-trifluorobenzylamino)-acetyl]-3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2 , 4] triazol[4,3-a] Preparation of pyrazine

[0108] 10.7 g (40 mmol) of 7-(2-chloro-acetyl)-3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazol[4, 3-a] Add pyrazine into a dry reaction flask, add 100ml of dichloromethane, 8g (80mmol) of triethylamine, heat and stir until reflux. Under the protection of nitrogen, 6.8g (42mmol) of 2,4,5-trifluorobenzylamine was added dropwise, and the mixture was refluxed for 12 hours. After the reaction was completed, the reaction solution was washed with water and dried over anhydrous magnesium sulfate. It was concentrated under reduced pressure, and the residue was purified by silica gel column (eluent gradient from 10% ethyl acetate and 90% petroleum ether to 90% ethyl acetate and 10% petroleum ether). 10.8 g of light yellow solid was obtained, yield: 68.6%.

[0109] Molecular formula: C 15 h 13 f 6 N 5 o

[0110] Molecular we...

Embodiment 37-

[0117] Example 37-[2-(N-2,4,5-trifluorobenzylamino)-acetyl]-3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1, 2,4]triazol[4,3-a] Preparation of pyrazine

[0118] Add 7-[2-(2,4,5-trifluorobenzylamino)-acetyl]-3-(trifluoromethyl)-5,6,7,8 prepared in the previous step to the dry reaction bottle -Tetrahydro-[1,2,4]triazol[4,3-a]pyrazine 19.7g (50mmol), dissolved in 50ml of acetonitrile, slowly added tert-butyl nitrite 6.2g (60mmol) / 50ml of acetonitrile solution, stirred for 5h. Then add 100ml of 36% acetic acid, stir and heat up to reflux, add 9.8g (150mmol) of zinc powder in portions, and reflux until the reaction solution changes from reddish brown to off-white, then stop the reaction. After the reaction was completed, cool to room temperature, separate layers, pour the supernatant into a beaker, adjust the pH to 7 with dilute alkali under ice cooling, and precipitate a solid, filter, wash with water, and dry to obtain 10.8 g of the target product, yield: 53.1%.

[0119] Molecu...

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Abstract

The invention belongs to the medicine technology field, particularly relates to a new DPP-IV inhibitor, the pharmaceutically acceptable salt and the isomer thereof shown in the formula (I); wherein, the R<1>, R<2>, Ar and Q are defined in the specification. The invention also relates to preparing methods of the compounds and the drug combination containing the compounds and the applications of the compounds in preparing the medicine for treating or preventing diabetes, non-insulin-dependent diabetes, hyperglycemia and insulin resistance.

Description

1. Technical field [0001] The invention belongs to the field of medical technology, and in particular relates to new DPP-IV inhibitor compounds, pharmaceutically acceptable salts and isomers thereof, preparation methods of these compounds, pharmaceutical compositions containing these compounds, and the use of these compounds in Application in the preparation of medicines for treating and / or preventing diabetes, non-insulin dependent diabetes, hyperglycemia and insulin resistance. 2. Background technology [0002] Type II diabetes (ie, non-insulin-dependent diabetes mellitus) is a metabolic disease characterized by insulin resistance, hyperglycemia and hyperlipidemia. Insulin polypeptide (GIP) can treat type II diabetes. Dipeptidyl peptidase IV (DPP-IV) can partially or completely inactivate active polypeptides. GLP-1, GIP is one of its substrates. Therefore, inhibiting the enzymatic hydrolysis of DPP-IV to GLP-1 and GIP can control type II diabetes upstream. [0003] DPP...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04A61K31/4985A61P3/10
Inventor 黄振华赵红宇
Owner BEIJING AOHE DRUG RES INST
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