A substituted fused imidazole ring compound and its pharmaceutical composition

A compound and composition technology, applied in the field of medicine, can solve problems such as inability to alleviate eye allergy symptoms

Active Publication Date: 2021-03-02
SHENZHEN TARGETRX INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The second-generation antihistamines developed after the 1980s, including terfenadine and loratadine, have high selectivity for H1 receptors and no central sedative side effects. However, in the clinical application process, terfenadine The withdrawal of diazepam and astemizole from the market due to the

Method used

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  • A substituted fused imidazole ring compound and its pharmaceutical composition
  • A substituted fused imidazole ring compound and its pharmaceutical composition
  • A substituted fused imidazole ring compound and its pharmaceutical composition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Example 1 Preparation of 6,11-dihydro-11-(1-(d3-methyl)piperidin-4-ylidene)-5H-imidazo[2,1-b][3] Benzazepine -3-Formaldehyde (Compound 8)

[0050]

[0051] Concrete synthetic steps are as follows:

[0052]

[0053] Step 1. Synthesis of compound 3.

[0054] Dissolve N-benzyloxycarbonylpiperidine-4-carboxylic acid (2.63 g, 10 mmol) in 20 mL of dichloromethane, add 6 mL of oxalyl chloride and 1 drop of DMF, and react at room temperature for 2 hours under nitrogen protection. Concentrate the reaction solution to dryness under reduced pressure, add 20 mL of acetonitrile to dissolve, add triethylamine (4.1 mL, 30 mmol) under ice-cooling, and stir for 3 minutes. A solution of 1-phenethyl-1H-imidazole (2.06 g, 12 mmol) in 5 mL of acetonitrile was slowly added dropwise, and after the addition was completed, the reaction was allowed to rise to room temperature overnight. After completion of the reaction, concentrate to dryness, add 30mL ethyl acetate and 20mL water...

Embodiment 2

[0065] Example 2 Preparation of 6,6-d2-6,11-dihydro-11-(1-methylpiperidin-4-ylidene)-5H-imidazo[2,1-b] [3] Benzazepines -3-Formaldehyde (compound 19)

[0066]

[0067] Concrete synthetic steps are as follows:

[0068]

[0069] Step 1. Synthesis of compound 10.

[0070] Phenylacetic acid (3.15g, 23mmol) was added to 10mL of 3.5M heavy aqueous solution of deuterated sodium oxide, reacted at 100°C for 24 hours under nitrogen protection, cooled to room temperature, the reaction solution was acidified with 4N hydrochloric acid, extracted with dichloromethane, and the organic phase was After drying with anhydrous sodium sulfate and concentrating, the above operation was repeated once more for the obtained crude product, and finally about 2.88 g of compound 10 was obtained by silica gel column separation, with a yield of 90%. 1 H NMR (400MHz, DMSO-d 6 )δ12.30(s, 1H), 7.34-7.21(m, 5H); ESI-MS: 139[M + +1].

[0071] Step 2. Synthesis of Compound 11.

[0072] Lithium ...

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PUM

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Abstract

The invention relates to a substituted condensed imidazole ring compound, a composition containing the compound and applications thereof. Specifically, the invention discloses a fused imidazole ring compound represented by formula (), or a pharmaceutical composition of its crystal form, pharmaceutically acceptable salt, prodrug, stereoisomer, hydrate or solvate. The compound of the present invention can be used as a histamine H1-receptor antagonist and a mast cell stabilizer, which can inhibit the release of histamine from mast cells and prevent the action of histamine, thereby alleviating allergic reactions. Formula (I).

Description

technical field [0001] The invention belongs to the field of medicine. Specifically, the present invention relates to a substituted fused imidazole ring compound and its use, more specifically, the fused imidazole ring compound and its pharmaceutical composition can be used as a histamine H1-receptor antagonist and a mast cell stabilizer , for the treatment and prevention of symptoms associated with allergies. Background technique [0002] Allergic disease, also known as allergic disease, is due to the high sensitivity of the patient, which produces a specific immunoglobulin E antibody (IgE) in the blood that is allergic to a particular allergen. This patient has a genetic tendency . IgE sensitivity can lead to the following typical allergic diseases: asthma, rhinitis, atopic eczema, conjunctivitis, food allergy, drug allergy, and anaphylactic shock. The most common of these are allergic rhinitis and allergic asthma caused by allergens such as pollen, dust mites, fungi an...

Claims

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Application Information

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IPC IPC(8): C07D487/04A61K31/55A61P37/08A61P27/14A61P27/02A61P11/02
CPCC07D487/04A61K31/55A61P11/02A61P27/02A61P27/14A61P37/08
Inventor 王义汉邢青峰
Owner SHENZHEN TARGETRX INC
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