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4H-thieno[2,3-b]thiapyran-4-ketone compound and application thereof

A compound, 3-b technology, applied in the field of medicine, can solve problems such as diarrhea, rash, itching, and reduced bioavailability

Active Publication Date: 2018-09-04
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Existing epidermal growth factor receptor tyrosine kinase inhibitors, such as gefitinib, erlotinib, lapatinib, etc., all have skin reactions such as diarrhea, rash, itching, and possible headache, heart attack, etc. Prolonged QT interval and decreased bioavailability, etc. (Li Ying, Tian Chi, Wang Lei, Xie Mengmeng, Cheng Zeneng. Research progress of small molecule epidermal growth factor receptor tyrosine kinase inhibitors. Oncology Pharmaceutics, 2016, 6(2) :81-88.)

Method used

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  • 4H-thieno[2,3-b]thiapyran-4-ketone compound and application thereof
  • 4H-thieno[2,3-b]thiapyran-4-ketone compound and application thereof
  • 4H-thieno[2,3-b]thiapyran-4-ketone compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Example 1: 6,6-Dimethyl-2-[2-(4-phenyl-1-piperazinyl)acetyl]-5,6-dihydro-4H-thieno[2,3-b ] Preparation of thiopyran-4-one

[0042] Step A: Preparation of 3-methyl-3-(thiophen-2-thio)butanoic acid

[0043] Add 0.04mol 2-mercaptothiophene, 0.04mol 3-methyl-2-butenoic acid, and 80mL tetrahydrofuran into a 250mL round bottom flask, add 11mL triethylamine dropwise with stirring, and heat and reflux for 20h under the protection of nitrogen. complete. The tetrahydrofuran was evaporated, 40 mL of ethyl acetate and water were added after cooling, the pH of the solution was adjusted to 2 with 18% hydrochloric acid, the organic layer was collected, the aqueous layer was extracted with ethyl acetate, the organic layers were combined, and dried over anhydrous magnesium sulfate. After suction filtration, the filtrate was evaporated to remove the solvent. After cooling, a brown solid was precipitated, which was recrystallized with petroleum ether to obtain a white powdery solid with a yi...

Embodiment 2

[0050] Example 2: 6,6-Dimethyl-2-{2-[4-(4-fluorophenyl)-1-piperazinyl]acetyl}-5,6-dihydro-4H-thieno[ 2,3-b] Preparation of thiopyran-4-one

[0051] With reference to the preparation method of Example 1, a yellow solid was obtained with a yield of 24.0%. m.p.: 193-196°C. IR(KBr,cm -1 ): 3428,2977,2938,2676,2603,1650,1477,1444,1397, 1384,1171,1118,1036,850,806; 1 H-NMR (600MHz, CDCl 3 ): δ1.54(s, 6H), 2.75~2.76(t,4H), 2.79(s,2H), 3.18~3.19(t,4H), 3.64(s,2H), 6.87~6.90(m,2H) ), 6.95~6.99(m,2H),8.26(s,1H); MS(m / z): 419.1([M+H] + ).

Embodiment 3

[0052] Example 3: 6,6-Dimethyl-2-{2-[4-(4-chlorophenyl)-1-piperazinyl]acetyl}-5,6-dihydro-4H-thieno[ 2,3-b] Preparation of thiopyran-4-one

[0053] With reference to the preparation method of Example 1, a yellow solid was obtained with a yield of 11.51%. m.p.: 145-148°C. IR(KBr,cm -1 ): 3443,2923,2851,2826,1667,1595,1521,1494,1452, 1388,1384,1228,1201,1153,1038,948,814; 1 H-NMR (600MHz, CDCl 3 ): δ1.54(s,6H), 2.74~2.75(t,4H), 2.79(s,2H), 3.23~3.24(t,4H), 3.64(s,2H), 6.85~6.86(d,2H) ,J=9.0Hz), 7.07~7.09(d,2H,J=9.0Hz), 8.25(s,1H); MS(m / z): 435.1([M+H] + ).

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Abstract

The invention belongs to the technical field of medicines, and relates to a 4H-thieno[2,3-b]thiapyran-4-ketone compound, a preparation method thereof and application thereof as an epidermal growth factor receptor tyrosine kinase inhibitor. The compound, a prodrug thereof, a pharmaceutically active metabolite thereof and a pharmaceutically acceptable salt thereof have structural formula as shown inthe specification, wherein R is independently selected from hydrogen, halogen, hydroxy, nitro, cyan, C1-C4 alkyl, C1-C4 alkoxy, halogen atoms substituted C1-C4 alkyl, and halogen atoms substituted C1-C4 alkoxy. The formula is shown in the description.

Description

Technical field [0001] The invention belongs to the technical field of medicine, and relates to 4H-thieno[2,3-b]thiopyran-4-one compounds, a preparation method thereof, and application as an epidermal growth factor receptor tyrosine kinase inhibitor. Background technique [0002] In recent years, the incidence and death of various types of tumors in our country have shown a significant upward trend. At present, the tumors with the highest morbidity and mortality in men are lung cancer, and breast cancer and lung cancer in women. Smoking, excessive drinking, insufficient physical activity and other unhealthy lifestyle habits, haze, and the work and life pressures caused by rapid economic and social development and social transformation on people’s health cannot be ignored. Lung cancer related to the environment and lifestyle The increasing trend of mortality from cancer, liver cancer, colorectal cancer, and breast cancer is even more pronounced. Among them, lung cancer and breast ...

Claims

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Application Information

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IPC IPC(8): C07D495/04A61K31/496A61P35/00
CPCA61P35/00C07D495/04
Inventor 胡春袁紫薇闫燚思柯佳黄二芳吴盛杰潘漫钰高嘉
Owner SHENYANG PHARMA UNIVERSITY
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