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A compound for treating diabetes

A compound and composition technology, applied in the field of treating diabetes compounds, can solve problems such as allergies, and achieve the effects of improving body weight, reducing toxic and side effects, improving blood lipid indexes and oral glucose tolerance

Active Publication Date: 2016-03-09
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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  • A compound for treating diabetes
  • A compound for treating diabetes
  • A compound for treating diabetes

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] The synthesis of embodiment 1 compound D1

[0032]

[0033] Synthesis of Compound 2

[0034] N 2 Under 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 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 HNMR (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 materia...

Embodiment 2

[0041] The synthesis of embodiment 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°C3 , 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 ad...

Embodiment 3

[0053] The synthesis of embodiment 3 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 in 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 o...

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PUM

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Abstract

The present invention provides a compound represented by formula I or a pharmaceutically acceptable salt, hydrate or solvate thereof. The present invention also provides new applications of the above compounds or pharmaceutically acceptable salts, hydrates or solvates thereof. The deuterated compound prepared by the present invention can obviously improve the body weight, fasting blood sugar, transaminase and fasting serum insulin of obese patients, improve insulin sensitivity, improve blood lipid index and oral glucose tolerance; this type of compound has good absorption in vivo, high bioavailability, and has It is conducive to the exertion of the drug effect, and the half-life is prolonged, which can reduce the number of administrations, reduce the toxic and side effects, and provide a safe and reliable new choice for clinical drug use. Formula I.

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 (YangW, et al. NEnglJMed, 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 wi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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