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Compound for treating diabetes mellitus

A technology of compounds and hydrates, which is applied in the field of compounds for treating diabetes, can solve problems such as allergies, and achieve the effects of improving body weight, high bioavailability, and reducing toxic and side effects

Active Publication Date: 2013-12-11
SICHUAN GOODDOCTOR PHARMA GRP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

After hard work, a number of antidiabetic drugs with new mechanisms of action have been approved for marketing, such as dipeptidyl peptidase-4 (DPP-4) inhibitors and glucagon-like polypeptide-1 (GLP-1) inhibitors The disadvantages of such drugs are that they can cause side effects such as pancreatitis, nasopharyngitis, respiratory tract infection, headache, and allergies

Method used

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  • Compound for treating diabetes mellitus
  • Compound for treating diabetes mellitus
  • Compound for treating diabetes mellitus

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1 Synthesis of Compound D1

[0032]

[0033] Synthesis of Compound 2

[0034] N 2 Under protection, DMF was added to a three-neck flask containing 5 g of compound 1 and 1.25 g of NaH, stirred at 0°C for 10 min, and then slowly added CD 3 I, stirred overnight at room temperature. TLC monitoring, after the reaction was completed, slowly added water dropwise to the reaction flask, then extracted with EA, washed the organic phase with saturated brine, dried over anhydrous sodium sulfate, concentrated and then column chromatographed to obtain 3.95 g of a light yellow solid with a yield of 78.9%. . 1 H NMR (400MHz, CDCl 3 ) 8.36 (t, 1H), 7.92 (q, 1H), 7.57–7.42 (m, 5H), 7.11–7.07 (m, 1H), 6.52 (s, 1H).

[0035] Synthesis of compound 3

[0036] N 2 Under protection, after dissolving 3.94g of compound 2 in DMF, slowly add 2.4mL of POCl dropwise at 0°C 3 , After stirring for 3 h, the reaction was monitored by TLC. After the reaction of the raw materials was c...

Embodiment 2

[0041] Synthesis of Example 2 Compound D2

[0042]

[0043] Synthesis of compound 7

[0044] Under nitrogen protection, DMF was added to a three-necked flask containing 5 g of compound 1 and 1.25 g of NaH, stirred at 0°C for 10 min, and then CH was slowly added dropwise. 3 I, stirred overnight at room temperature. After the reaction was completed, water was slowly added dropwise to the reaction flask, and then extracted with EA. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, concentrated and then column chromatographed to obtain about 4.05 g of a light yellow product with a yield of 79.5%.

[0045] Synthesis of Compound 8

[0046]Under nitrogen protection, after dissolving 4.05g of compound 7 in DMF, slowly add 2.4mL of POCl dropwise at 0°C 3 , After stirring for 3 h, the reaction was monitored by TLC. After the reaction of the raw materials was complete, 50 mL of ice water was added to the reaction flask, and the pH was adjusted...

Embodiment 3

[0053] Example 3 Synthesis of Compound D3

[0054]

[0055] Synthesis of Compound 13

[0056] Take 28.1mg (0.1mmol) compound 4, 27mg (0.2mmol) HOBT, 57.5mg (0.3mmol) EDCI, dissolve with 2mL DMF, add 0.05mL triethylamine, stir at room temperature for 30 minutes; then add 29.5mg (0.12mmol) ) 1,2,3,4-tetrahydro-6,7-isoquinoline diol hydrobromide (10), stirred overnight at room temperature. TLC monitoring, after the completion of the reaction, add water, extract with EA three times (15 mL each time), wash the organic phase with saturated brine, dry over anhydrous sodium sulfate, concentrate and directly use in the next reaction.

[0057] Synthesis of Compound 14 (D3)

[0058] in N 2 Under protection, dissolve the above crude product and appropriate amount of NaH in DMF, stir at 0°C for 30 minutes, then slowly add CD 3 I, reaction at room temperature. After the reaction was complete, water was slowly added dropwise to the reaction flask, and then extracted with EA. The orga...

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PUM

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Abstract

The invention provides a compound shown in the formula I or pharmaceutically acceptable salts, hydrates or solvates thereof, and also provides new application of the compound or the pharmaceutically acceptable salts, hydrates or solvents thereof. A deuterated compound can be used for remarkably improving the conditions of the weight, fasting blood-glucose, transaminase and fasting serum insulin of an obese patient, increasing the insulin sensitivity can be improve, and enhancing the serum lipid parameter and oral glucose tolerance; the compound has the advantages that internal absorption effect is excellent;, the bioavailability is high, which is favorable for the taking of drug effect; the half-life period is prolonged, so that the administration frequency can be reduced and toxic and side effects can be reduced; therefore a new safe and reliable choice is provided to clinical administration. The formula I can be found in the specification.

Description

technical field [0001] The present invention relates to a compound for treating diabetes. Background technique [0002] According to statistics, the number of people with diabetes in my country has reached 92.4 million, ranking first in the world (Yang W, et al. N Engl J Med, 2010, 362(12): 1090-1101). The cost of diabetes treatment in China is as high as 173.4 billion yuan per year, and the direct medical expenditure caused by diabetes has accounted for 13% of China's total medical expenditure (Alcorn T, et al. Lancet, 2012, 379(9833): 2227-2228). It can be seen that diabetes not only seriously endangers the health of the people, but also brings a heavy economic burden to the country. Therefore, it is urgent to prevent and treat diabetes. [0003] According to different etiology and clinical manifestations, diabetes is mainly divided into 4 types: insulin-dependent (type 1), non-insulin-dependent (type 2), malnutrition-related and secondary diabetes. Among them, patients...

Claims

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Application Information

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IPC IPC(8): C07D471/04A61K31/4725A61K31/496A61K31/4545A61K31/5377A61K31/551A61K31/437A61P5/50A61P3/10A61P3/04A61P3/06A61P1/16
CPCA61P1/16A61P3/04A61P3/06A61P3/10A61P5/50C07D471/04
Inventor 谢永美魏于全耿福能
Owner SICHUAN GOODDOCTOR PHARMA GRP
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