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Medicine for preventing and treating diabetes and preparation method thereof

A prodrug and compound technology, applied in the field of medicine, can solve problems such as affecting insulin action, and achieve the effect of reducing blood sugar level in rats and improving hypoglycemic effect.

Inactive Publication Date: 2018-06-29
HEILONGJIANG UNIV OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although a variety of PTPases are expressed in insulin-sensitive tissues, such as transmembrane CD45 and LAR-PTPase; Receptor or post-receptor links affect normal insulin action

Method used

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  • Medicine for preventing and treating diabetes and preparation method thereof
  • Medicine for preventing and treating diabetes and preparation method thereof
  • Medicine for preventing and treating diabetes and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0052] The preparation method of the compound of formula I of the present invention or its pharmaceutically acceptable salt comprises the following steps:

[0053] step one:

[0054]

[0055] This step involves reacting a compound of formula II with a compound of formula III and a base in an inert solvent to prepare a compound of formula IV.

[0056]Solvents used in this step can be alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, tert-butanol, isoamyl alcohol, octanol, cyclohexanol; aromatic hydrocarbons such as benzene , toluene or xylene; halogenated hydrocarbons such as chloroform, dichloromethane. The solvent is preferably an aromatic hydrocarbon, more preferably toluene.

[0057] The base used in this step can be a hydroxide such as sodium hydroxide, potassium hydroxide; a carbonate such as sodium carbonate, potassium carbonate; a bicarbonate such as sodium bicarbonate, potassium bicarbonate; an acetate such as Sodium acetate or p...

Embodiment 1

[0074] Example 1: 2-(2-methyl-2H-1,2,3-triazol-4-yl)-3-(pyridine-2-formyl)pyridin[3,4-d]pyrimidine-4( 3H)-Kone (Compound 1)

[0075]

[0076] Step 1: Add 3.08g (25.0mmol) of 2-pyridinecarboxylic acid, 100ml of toluene and DMF2ml in a 500ml there-necked flask with a stirring and reflux device, heat up and reflux, add dropwise a mixed solution of 10ml of thionyl chloride and 50ml of toluene, half Hours added, and then reflux constant temperature reaction for 4 hours. After the reaction is complete, stand still for half an hour to separate the liquid and remove the reaction impurities, then distill off excess thionyl chloride and toluene under reduced pressure to obtain 2-pyridinecarbonyl chloride, then add 50ml of toluene to dissolve it, and set aside. In a 500ml three-necked flask with a stirring and reflux device, add 4.48g (20.0mmol) of 2-bromopyridin[3,4-d]pyrimidin-4(3H)-one, 5.0g (50.0mmol) of potassium bicarbonate, A small amount of water and 100ml of toluene were st...

Embodiment 2

[0081] Example 2: 2-(2-methyl-2H-1,2,3-triazol-4-yl)-3-(piperidine-3-formyl)-8-(trifluoromethyl)pyridine[ 3,4-d]pyrimidin-4(3H)-one (Compound 2)

[0082]

[0083] According to the method of Example 1, replace 2-pyridinecarboxylic acid with piperidine-3-carboxylic acid, and use 2-bromo-8-(trifluoromethyl)-pyridin[3,4-d]pyrimidin-4(3H)-one Substitution of 2-bromopyridin[3,4-d]pyrimidin-4(3H)-one afforded the title compound as a white solid in 54% overall yield over two steps.

[0084] ESI-MS: 408.13[M+H] +

[0085] Elemental analysis: theoretical value / measured value, C(50.12 / 50.02), H(3.96 / 3.87), F(13.99 / 14.07), N(24.07 / 24.12), O(7.86 / 9.92)

[0086] 1 H NMR (400MHz, CDCl 3 )δ8.89(d,1H),8.14(s,1H),7.69(d,1H),3.63(s,3H),3.12(q,1H),2.86(q,1H),2.74(m,2H ), 2.47(s,1H), 2.06(s,1H), 1.86(m,1H), 1.64(m,1H), 1.56(m,1H), 1.42(m,1H).

[0087] Following a similar method, the following compounds were synthesized:

[0088]

[0089]

[0090]

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Abstract

The invention relates to medicine with protein tyrosine phosphatase 1B(PTP1B) inhibition activity and application thereof. The compound is prepared from compound shown in a formula I or pharmaceuticalsalt and precursor of the compound. The compound disclosed by the invention shows an obvious inhibition effect on the PTP1B and can obviously reduce a rat blood sugar value in animal experiments; compared with positive control rosiglitazone, a sugar reducing effect of the compound is further improved; thus, the compound has an effect of remarkably controlling a blood sugar value of a diabetes ratand can be applied to preventing and treating diabetes, especially II type diabetes.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a medicine for preventing and treating diabetes, and also relates to a preparation method and application of the medicine. Background technique [0002] Diabetes is a series of clinical syndromes caused by absolute or relative insufficiency of insulin in the body. Studies have shown that it is not only closely related to genetics, but also closely related to daily life habits. The main clinical symptoms of diabetes are polydipsia, polyuria, polyphagia but weight loss ("three more and one less"), high blood sugar level, and glucose in urine (normal urine should not contain glucose), etc. , a variety of clinical conditions. [0003] Diabetes can cause a variety of complications. If diabetics are not treated effectively, it will cause some acute complications, such as non-ketone hyperosmolar coma, hypoglycemia, ketoacidosis, etc. If the condition is serious, it will lead to long-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04A61K31/519A61P3/10
CPCC07D471/04
Inventor 韩洁茹
Owner HEILONGJIANG UNIV OF CHINESE MEDICINE
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