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Novel pyridine derivative

A technology of compounds and solvates, applied in the field of new pyridine derivatives, which can solve the problems of large individual differences in pharmacokinetics and long peak time.

Inactive Publication Date: 2011-08-03
SHANDONG XUANZHU PHARMA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, proton pump inhibitors take a long time to achieve the strongest effect, and it takes 3-5 days to achieve the maximum acid-suppressing effect at a therapeutic dose, and this type of drug can have obvious interactions with other drugs, and the pharmacokinetics of individual big difference

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0135] Example 1 6-[[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl]-2,3-dihydro-7H-benzofur Preparation of fur[5,6-d]imidazole (compound 1)

[0136] Step 1 Preparation of 5-nitro-2,3-dihydrobenzofuran

[0137]

[0138] 2,3-Dihydrobenzofuran (5 g, 41.6 mmol) was dissolved in 35 mL of acetic acid, and 1 / 4 HNO was added dropwise 3 (0.9 mL, 45.4 mmol). It was heated to 70°C at the beginning of the reaction, and then the remaining HNO 3 join in. After half an hour the reaction was cooled, added to ice water, then washed with Na 2 CO 3 neutralize. The aqueous layer was extracted with ethyl acetate. The combined organic layers were dried, concentrated in vacuo, and purified by column chromatography to give the product (1 g, 14.6%).

[0139] Step 2 Preparation of 5-amino-2,3-dihydrobenzofuran

[0140]

[0141] The product obtained in Step 1 (1 g, 6.1 mmol), Raney Ni (0.1 g) and MeOH (10 mL) were hydrogenated at room temperature under a hydrogen pressure of...

Embodiment 26

[0171] Example 26-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-2,3-dihydro-7H-benzofuran[5,6-d ] imidazole (Compound 2) Preparation

[0172] For steps 1-7, refer to steps 1-7 of Example 1.

[0173] Step 86-[(4-Methoxy-3,5-dimethylpyridin-2-yl)methylthio]-2,3-dihydro-7H-benzofuro[5,6-d]imidazole preparation of

[0174]

[0175] Referring to Step 8 of Example 1, throw 6-mercapto-7H-2,3-dihydrobenzofuro[5,6-d]imidazole (1.5g, 7.8mmol), NaOH (0.78g, 19.5mmol), acetone ( 10 mL), water (10 mL), 2-(chloromethyl)-4-methoxy-3,5-lutidine (1.45 g, 7.8 mmol), and the product (1.51 g, 56.7%) was obtained.

[0176] Step 9 Preparation of compound 2

[0177]

[0178] Referring to step 9 of Example 1, cast 6-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylthio]-2,3-dihydro-7H-benzofuran[ 5,6-d] imidazole (1.42g, 4.16mmol), dichloromethane (20mL), m-CPBA (0.72g, 4.16mmol) to give the product (1.38g, 92.9%).

[0179] 1 H-NMR (DMSO, 600MHz): δ2.21 (6H, s), 3.18 (2H, t), 3.69 (...

Embodiment 36-

[0186] Example 36-[[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl]-2,3-dihydro-7H-benzo Furan Preparation of [5,6-d]imidazole (Compound 3)

[0187] For steps 1-7, refer to steps 1-7 of Example 1.

[0188] Step 86 - [[3-Methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylthio]-2,3-dihydro-7H-benzofuran[ 5,6-d] Preparation of imidazole

[0189]

[0190] Referring to Step 8 of Example 1, 6-mercapto-7-2,3-dihydrobenzofuro[5,6-d]imidazole (1.5g, 7.8mmol), NaOH (0.78g, 19.5mmol), acetone ( 10mL), water (10mL), 2-(chloromethyl)-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine (1.87g, 7.8mmol), the product (1.63g , 52.8%).

[0191] Step 9 Preparation of compound 3

[0192]

[0193] Referring to step 9 of Example 1, cast 6-[[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylthio]-2,3-dihydro -7H-benzofuro[5,6-d]imidazole (1.64g, 4.16mmol), dichloromethane (20mL), m-CPBA (0.72g, 4.16mmol) to give the product (1.55g, 90.7%).

[0194] Preparation of step 10 co...

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Abstract

The invention belongs to the technical field of medicines and particularly relates to a novel pyridine derivative shown, stereoisomers of the pyridine derivative, pharmaceutically acceptable salts of the pyridine derivative, solvates of the pyridine derivate in the general formula (I) and intermediates shown in the general formulas (I') and (II), wherein R1, R2, R3, R4, R5 and n are as defined in a specification; the invention also relates to preparation methods for the compounds, a medicine combination containing the medicine compounds, and the application of the compounds in medicines for preventing and / or treating peptic ulcers, ulcer bleeding and diseases related to gastric acids.

Description

1. Technical field [0001] The present invention belongs to the technical field of medicine, and specifically relates to new pyridine derivatives, their stereoisomers, solvates, pharmaceutically acceptable salts or intermediates thereof, methods for preparing these compounds, and pharmaceutical compositions containing these compounds , and the application of these compounds in the preparation of medicines for preventing and / or treating peptic ulcer, ulcer bleeding and diseases related to gastric acid. 2. Background technology [0002] Digestive system disease is one of the common frequently-occurring diseases, wherein the incidence of peptic ulcer accounts for about 10% to 12% of the total population, and gastric acid is the main cause of peptic ulcer. The initial treatment is mainly to use antacids (such as sodium bicarbonate, aluminum hydroxide, etc.) to neutralize gastric acid to relieve symptoms. After the 1970s, with the H 2 The discovery of gastric acid secretion inhi...

Claims

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Application Information

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IPC IPC(8): C07D491/048C07D487/04C07D491/056C07D491/052A61K31/4439A61P1/04
CPCC07D491/048C07D491/052C07D487/04C07D491/056A61P1/00A61P1/04A61P43/00
Inventor 黄振华宋运涛
Owner SHANDONG XUANZHU PHARMA TECH CO LTD
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