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Benzimidazole derivatives and pharmaceutical compositions and uses thereof

A technology of imidazoles and compounds, applied in the field of benzimidazole derivatives, can solve the problems of long strongest time and large individual differences in pharmacokinetics

Active Publication Date: 2014-07-09
XUANZHU BEIJING BIOPHARMACEUTICAL LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] 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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  • Benzimidazole derivatives and pharmaceutical compositions and uses thereof
  • Benzimidazole derivatives and pharmaceutical compositions and uses thereof
  • Benzimidazole derivatives and pharmaceutical compositions and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0176] Example 1: 2-[[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl]- Preparation of 6,7-dihydro-3H-benzofuro[5,6-d]imidazole (compound 1)

[0177] Step 1: Preparation of 5-nitro-2,3-dihydrobenzofuran

[0178]

[0179] 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%).

[0180] Step 2: Preparation of 5-amino-2,3-dihydrobenzofuran

[0181]

[0182] 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 2

[0210] Example 2: 2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]- Preparation of 6,7-dihydro-3H-benzofuro[5,6-d]imidazole (compound 2)

[0211] Steps 1-7 are carried out with reference to Steps 1-7 of Example 1.

[0212] Step 8: 2-[(4-Methoxy-3,5-dimethylpyridin-2-yl)methylthio]-6,7-dihydro-3H-benzofuro[5,6-d ] The preparation of imidazole

[0213]

[0214] 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 ( 10mL), water (10mL), 2-(chloromethyl)-4-methoxy-3,5-lutidine (1.45g, 7.8mmol), and the product (1.51g, 56.7%) was obtained.

[0215] Step 9: Preparation of Compound 2

[0216]

[0217] Referring to step 9 of Example 1, cast 2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylthio]-6,7-dihydro-3H-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%).

[0218] 1 H-NMR (DMSO, 600MHz): δ2.21 (6H...

Embodiment 3

[0223] Example 3: 2-[[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl]- Preparation of 6,7-dihydro-3H-benzofuro[5,6-d]imidazole (compound 3)

[0224] Steps 1-7 are carried out with reference to Steps 1-7 of Example 1.

[0225] Step 8: 2-[[3-Methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylthio]-6,7-dihydro-3H-benzo Preparation of furo[5,6-d]imidazole

[0226]

[0227] 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 ( 10mL), water (10mL), 2-(chloromethyl)-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine (1.87g, 7.8mmol), the product (1.63g , 52.8%).

[0228] Step 9: Preparation of compound 3

[0229]

[0230] Referring to step 9 of Example 1, cast 2-[[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylthio]-6,7-dihydro -3H-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%).

[0231] ...

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Abstract

The present invention relates to benzimidazole derivatives and their pharmaceutical compositions and uses, specifically to benzimidazole derivatives of Formula (I), or their stereoisomer, pharmaceutically acceptable salt or solvates thereof, in which R 1 , R 2 , R 3 , R 4 , R 5 and n have the definitions in the description; the present invention further relates to a pharmaceutical composition containing the compounds, methods for preparing the compounds, and use of the compounds for manufacturing of a medicament for prophylaxis and / or treatment of peptic ulcer, ulcer hemorrhage and diseases associated with gastric acid.

Description

technical field [0001] The invention belongs to the technical field of medicine, and specifically relates to benzimidazole derivatives, or stereoisomers, solvates or pharmaceutically acceptable salts thereof. The present invention also relates to the pharmaceutical composition containing these compounds, the method for preparing 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. Background technique [0002] Digestive system diseases are one of the common frequently-occurring diseases, among which 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 se...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04C07D491/04C07D513/04C07D515/04A61K31/4439A61P1/04
CPCC07D491/056C07D491/048C07D487/04C07D491/052A61P1/00A61P1/04A61P43/00
Inventor 黄振华周广连
Owner XUANZHU BEIJING BIOPHARMACEUTICAL LTD
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