Medicine for treatment of cholecystitis and applications thereof

A technology of pharmacy, compounds, applied in the field of medicine

Inactive Publication Date: 2017-07-14
MUDANJIANG MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Modern medicine believes that the only reasonable cure for this disease is surgical removal of the gallbladder. However, patients ...

Method used

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  • Medicine for treatment of cholecystitis and applications thereof
  • Medicine for treatment of cholecystitis and applications thereof
  • Medicine for treatment of cholecystitis and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Example 1: 3-[2-(pyridin-2-ylimino)butyl]-3,4-dihydro-2H-pyran[2,3-b]pyridin-2-one (Compound A)

[0042]

[0043] Dissolve 1-bromobutan-2-one (1.6g, 11mmol) in 50mL of anhydrous ether, and drop it into a flask containing freshly planed magnesium chips (0.29g, 12mmol) and 1 grain of iodine under stirring, for about 20 minutes. Complete, then stir and reflux until the magnesium chips are basically completely dissolved, stop heating, wait for the Grignard reagent to cool to 30-40°C, add 2H-pyran[2,3-b]pyridin-2-one (1.5g, 10mmol), Then react at 30-40°C for 3 hours, after the reaction, cool the reaction solution to room temperature, and then add saturated NaCO 3 Aqueous solution (50mL), extracted with petroleum ether (50mL×3), anhydrous CaCl 2 After drying, the solvent was distilled off under reduced pressure, the crude product was recrystallized with ethanol, and dried under vacuum at 50°C to obtain a light yellow solid 3-(2-oxobutyl)-3,4-dihydro-2H-pyran[2, 3-b] Pyri...

Embodiment 2

[0050] Example 2: 3-[6-Hydroxy-4-(1-methylpiperidin-2-ylimino)hexyl]-7-methyl-3,4-dihydro-2H-pyran[2,3 -b] pyridin-2-one (Compound B)

[0051]

[0052] According to the method of Example 1, replace 1-bromobutan-2-one with 6-bromo-1-hydroxyhexan-3-one, and use 7-methyl-2H-pyrano[2,3-b]pyridine -2-one in place of 2H-pyrano[2,3-b]pyridin-2-one and 1-methylpiperidin-2-amine in place of pyridin-2-amine gave a white solid 3-[6-hydroxy- 4-(1-Methylpiperidin-2-ylimino)hexyl]-7-methyl-3,4-dihydro-2H-pyran[2,3-b]pyridin-2-one, two steps Overall yield 59%.

[0053] ESI-MS: 374.24[M+H] +

[0054] Elemental analysis: theoretical value / measured value, C(67.53 / 67.46), H(8.37 / 8.44), N(11.25 / 11.36), O(12.85 / 12.74)

[0055] 1 H NMR (400MHz, CDCl 3 )δ7.55(d,1H),6.03(d,1H),4.77(s,1H),3.95(t,2H),2.90(d,2H),2.70(m,1H),2.52-2.56(m ,7H), 2.26-2.30(m,7H), 1.68(m,3H), 1.49-1.55(m,6H).

Embodiment 3

[0056] Example 3: 3-[3-(1H-pyrazol-5-ylimino)-4-(pyrimidin-2-yl)butyl)-7-fluoro-3,4-dihydro-2H-pyran [2,3-b]pyridin-2-one (Compound C)

[0057]

[0058] According to the method of Example 1, 6-bromo-1-hydroxyhexan-3-one was used instead of 1-bromobutan-2-one, and 7-fluoro-2H-pyrano[2,3-b]pyridine- Substitution of 2H-pyrano[2,3-b]pyridin-2-one by 2-keto and pyridin-2-amine by 1H-pyrazol-5-amine afforded 3-[3-(1H-pyrazole -5-ylimino)-4-(pyrimidin-2-yl)butyl)-7-fluoro-3,4-dihydro-2H-pyran[2,3-b]pyridin-2-one, two The overall yield was 51%.

[0059] ESI-MS: 381.14[M+H] +

[0060] Elemental analysis: theoretical value / measured value, C(59.99 / 59.81), H(4.50 / 4.59), F(4.99 / 4.93), N(22.09 / 22.01), O(8.41 / 8.66)

[0061] 1 H NMR (400MHz, CDCl 3 )δ12.51(s,1H),8.75(d,2H),7.95(d,1H),7.53-7.56(m,2H),6.36(d,1H),6.13(d,1H),2.96(d ,2H), 2.74(m,1H), 2.56(s,2H), 1.61(m,2H), 1.33(t,2H).

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Abstract

The invention relates to a medicine for treatment of cholecystitis. A pharmacodynamic test proves that the compound has significant choleretic effect and after drug delivery, can significant bile secretion quantity. The medicine has long lasting time and is better in effect of promoting excretion effect of bilirubin in the bile, so that the compound is suitable for treatment of the cholecystitis.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a medicine for treating cholecystitis. Background technique [0002] Cholecystitis is an inflammatory lesion of the gallbladder caused by bacterial infection or chemical stimulation (change in bile composition). It is a common disease of the gallbladder and often coexists with cholelithiasis. It is divided into acute and chronic. Second only to appendicitis. Acute cholecystitis can cause right upper quadrant pain, which is very similar to biliary colic at first, but the duration of abdominal pain caused by acute cholecystitis is often longer, and breathing and changing body positions can often aggravate the pain. Chronic cholecystitis is the most common gallbladder disease. Chronic cholecystitis can sometimes be a sequela of acute cholecystitis, but most patients have not suffered from acute cholecystitis in the past. Due to long-term inflammation of the gallbladder, the gall...

Claims

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Application Information

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IPC IPC(8): C07D491/052A61K31/444A61K31/4545A61K31/506A61P1/16
CPCC07D491/052
Inventor 王维宋静孙治国韩光宇李海林
Owner MUDANJIANG MEDICAL UNIV
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