1-(6,7-dihydro-5H-furan-[3,2-g]chromene-3-acetyl)-4-phenylpiperazine and applications thereof

A technology of phenylpiperazine and 2-g, which is applied in the medical field

Inactive Publication Date: 2012-10-31
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

, the above drugs all have different degrees of shortcomings and deficiencies. Therefore, finding a gastrointestinal antispasmodic drug with relatively strong selectivity and less adverse reactions should have broad application prospects.

Method used

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  • 1-(6,7-dihydro-5H-furan-[3,2-g]chromene-3-acetyl)-4-phenylpiperazine and applications thereof
  • 1-(6,7-dihydro-5H-furan-[3,2-g]chromene-3-acetyl)-4-phenylpiperazine and applications thereof
  • 1-(6,7-dihydro-5H-furan-[3,2-g]chromene-3-acetyl)-4-phenylpiperazine and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Example 1: Preparation of 1-(6,7-dihydro-5H-furan[3,2-g]chromene-3-acetyl)-4-phenylpiperazine (WY-42)

[0017] Add 0.26 mol of 2',4'-dihydroxyacetophenone into a round bottom flask, mix it with 232 mL of triethyl orthoformate, and then slowly drop 26.4 mL of perchloric acid into it. After reacting for 30 minutes, 300 mL of ether was added to precipitate a solid. Suction filtration, transfer the dried solid into a 1000mL round bottom flask, add 250mL hot water, reflux for two hours, suction filtration, recrystallize with ethanol to obtain 22.69g of 7-hydroxychromone, yield 53.2%, MS: m / z 162 (M + ).

[0018] Put 0.15 mol of 7-hydroxychromone into a 1000 mL round bottom flask, add 2.50 g of 5% palladium on carbon and 300 mL of ethanol, pass in hydrogen, and react at 50°C for 48 hours, remove the palladium on carbon by suction, and remove the ethanol by rotary evaporation. Obtained 7-hydroxy color over 21.39 g, yield 92.4%, MS: m / z 150 (M + ).

[0019] Put the 7-hydroxy color...

Embodiment 2

[0022] Example 2: Relaxation effect of WY-42 on isolated rabbit small intestine smooth muscle

[0023] 1. Experimental materials: (1) Animals: New Zealand rabbits, both male and female, weighing 2.0 ~ 2.5 kg, provided by the Experimental Animal Center of Shenyang Pharmaceutical University, certificate number: scxk (Liao) 2009-2002. (2) Instruments: HSS-1(B) constant temperature bath, RM6240B multi-channel physiological signal acquisition and processing system, JZJ01 muscle tension transducer, TG-328A electro-optical analytical balance, T-500 electronic balance, medical oxygen supply (95%O2+5%CO2), micropipette Ⅲ WKY type 50-250μl. (3) Medicines and reagents: sodium chloride (NaCl): potassium chloride (KCl), magnesium sulfate (MgSO) 4 ·7H2O), sodium dihydrogen phosphate (NaH 2 PO4), anhydrous calcium chloride (CaCl 2 ), sodium bicarbonate (NaHCO 3 ), glucose (Glucose), barium chloride (BaCl 2 ), potassium dihydrogen phosphate (KH 2 PO 4 ), acetylcholine chloride (ACh), dimethyl ...

Embodiment 3

[0036] Example 3: The relationship between the relaxation mechanism of WY-42 on the smooth muscle of the small intestine and the calcium channel

[0037] 1. Experimental materials: the same as in Example 2.

[0038] 2. experimental method:

[0039] (1) Specimen preparation: The same as in Example 2.

[0040] ( 2) Verapamil vs. WY-42 Diastolic BaCl 2 The effect of contraction of isolated rabbit small intestine smooth muscle

[0041] After the tension of the rabbit small intestine specimen is stable, adjust the baseline to zero, record a section of waveform, and add BaCl to the bath tube 2 (2mg / ml), after obtaining a stable contraction, add WY-42 (10 -9 mol / L~10 -4 mol / L), get WY-42 diastolic BaCl 2 Dose-response curve of contraction; after fully flushing the tissues, after the specimens are reactivated, add Glivirapamil (10 -7 mol / L), incubate for 10 minutes to block Ca + Channel, add BaCl to the bath tube again 2 (2mg / ml), after obtaining a stable contraction, add WY-42(10 -9 mo...

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Abstract

The invention relates to the technical field of medicines, and relates to applications of 1-(6,7-dihydro-5H-furan-[3,2-g]chromene-3-acetyl)-4-phenylpiperazine (piperazine compound WY-42), pharmaceutically acceptable salts thereof, stereo-isomers thereof, pro-drugs thereof, and carries and diluents thereof acceptable in pharmaceutical formulation, in preparing medicines used for treating intestinal smooth muscle spasm diseases, and in gastrointestinal diseases as calcium ion channel antagonists. In animal in-vitro experiments, WY-42 can relax small intestine smooth muscle contraction caused by acetylcholine chloride, barium chloride, and potassium chloride. In a preliminary study of the relaxation mechanism of the compounds, it is found that, after an intestinal smooth muscle is incubated by using a calcium channel antagonist verapamil, the relaxation effect of WY-42 is inhibited. Therefore, the WY-42 can be used for preparing medicines used for treating intestinal smooth muscle spasm diseases, and can be used as a calcium ion channel antagonist.

Description

technical field [0001] The present invention belongs to the field of medical technology and relates to 1-(6,7-dihydro-5H-fur[3,2-g]chromene-3-acetyl)-4-phenylpiperazine (piperazine compound WY -42) and its preparation method, including its pharmaceutical composition, and the use of piperazine compound WY-42 for the preparation of intestinal smooth muscle spasmolytic agent and antidiarrheal agent. Background technique [0002] There are many reasons for gastrointestinal cramping pain, but most of them are caused by gastrointestinal dysfunction, and some are caused by organic lesions of the gastrointestinal tract. Generally, anticholinergic drugs are the first choice for gastrointestinal spasm, which work by selectively blocking the M-choline receptors of gastrointestinal smooth muscle. Rubensin, Weifukang, etc. However, common doses of anticholinergic drugs are accompanied by common side effects, including dry nose, dry mouth, photophobia, anuria, blurred near-distance vi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/04A61K31/496A61P1/06A61P1/12A61P1/00
Inventor 胡春付守廷宋媛王岩付娟黄二芳
Owner SHENYANG PHARMA UNIVERSITY
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