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Novel gvs series compound and its application
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A technology of compounds and uses, applied in the field of pharmaceutical applications, can solve the problems of patient intolerance, retention, weight gain, etc.
Active Publication Date: 2022-06-28
ZHEJIANG XUCHEN PHARMA TECH CO LTD
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At present, there are many types of drugs and health foods for the prevention and treatment of non-alcoholic fatty liver, but there are also many problems, such as patients' intolerance, and various adverse reactions such as weight gain, fluid retention, and cardiovascular diseases after taking drugs.
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Embodiment 1
[0147] Example 1: Synthesis of GVS-1:
[0148]
[0149] Step 1: p-hydroxybenzoic acid (1.38g, 10mmol) and benzylamine (1.08g, 10mmol) were placed in a 25mL round bottom flask, BOP condensing agent (5.3g, 12mmol) and DMAP (1.46g, 12mmol) were added, Then add dry DMF 20mL, stir at room temperature, follow the reaction by TLC, after 3h the reaction is complete, EA extraction, washing and concentration to obtain intermediate 1, MS(EI): m / z 227.1 [M+H] + .
[0150] Step 2: Intermediate 1 (230 mg, 1 mmol) and 3,4-difluorobenzyl bromide (206 mg, 1 mmol) were placed in a 25 mL round bottom flask, Cs was added 2 CO 3 (490 mg, 1.5 mmol) in a flask, then add 8 mL of dry DMF, stir at room temperature, follow the reaction by TLC, the reaction is complete after 3 h, extract with water / ethyl acetate, until the aqueous phase has no compound, the combined organic phases are washed twice with water , washed with saturated NaCl solution, dried over anhydroussodiumsulfate, and finally sep...
Embodiment 2
[0151] Example 2: Synthesis of GVS-2:
[0152]
[0153] GVS-2 (85% yield) was prepared as GVS-1 using 3-fluoro-4-chlorobenzyl bromide instead of 3,4-difluorobenzyl bromide. 1 H NMR (400MHz, chloroform-d) δ 7.80–7.73 (m, 2H), 7.36 (d, J=4.4Hz, 4H), 7.33–7.25 (m, 2H), 7.25–7.10 (m, 2H), 7.01–6.93(m, 2H), 6.32(t, J=5.4Hz, 1H), 5.05(s, 2H), 4.64(d, J=5.6Hz, 2H). LCMS(ESI): m / z 354.1[ M+H] + .
Embodiment 3
[0154] Example 3: Synthesis of GVS-3:
[0155]
[0156] GVS-3 (81% yield) was prepared as GVS-1 using 4-trifluoromethylbenzyl bromide instead of 3,4-difluorobenzyl bromide. 1 H NMR (400MHz, chloroform-d) δ 7.80–7.74 (m, 2H), 7.69–7.61 (m, 2H), 7.54 (m, 2H), 7.35 (d, J=4.6Hz, 4H), 7.33– 7.27(m, 1H), 7.02–6.95(m, 2H), 6.34(s, 1H), 5.17(s, 2H), 4.63(d, J=5.6Hz, 2H). LCMS(ESI): m / z 386.1[M+H] + .
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technical field [0001] The invention belongs to the field of pharmaceutical application, and specifically, the invention relates to GVS series compounds and uses thereof. The compounds of the invention can obviously improve non-alcoholic fatty liverdisease and fat accumulation. Background technique [0002] Non-alcoholic fatty liverdisease (NAFLD) refers to a clinicopathological syndrome characterized by excessive deposition of fat in hepatocytes except for alcohol and other definite liver-damaging factors. It is an acquired disease closely related to insulin resistance and genetic susceptibility. Metabolic stress-induced liver injury, including simple fatty liver (SFL), nonalcoholic steatohepatitis (NASH) and its associated cirrhosis. With the global trend of obesity and its related metabolic syndrome, non-alcoholic fatty liver disease has now become an important cause of chronic liver disease in developed countries such as Europe and the United States and in wealthy area...
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