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Benzo[5,6]cycloheptyl[1,2-b]pyridine derivative, preparation method, pharmaceutical composition and use thereof for anti-allergic diseases

A technology of compounds and alkyl groups, applied in allergic diseases, drug combinations, antipyretics, etc.

Inactive Publication Date: 2011-11-30
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Classical H1 receptor antagonists easily pass through the blood-brain barrier and have affinity with related receptors, causing major side effects such as drowsiness and sedation
In addition, this type of drug has a short action time, and if the dose is increased, it will produce more toxic and side effects.

Method used

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  • Benzo[5,6]cycloheptyl[1,2-b]pyridine derivative, preparation method, pharmaceutical composition and use thereof for anti-allergic diseases
  • Benzo[5,6]cycloheptyl[1,2-b]pyridine derivative, preparation method, pharmaceutical composition and use thereof for anti-allergic diseases
  • Benzo[5,6]cycloheptyl[1,2-b]pyridine derivative, preparation method, pharmaceutical composition and use thereof for anti-allergic diseases

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] 8-Chloro-11-{1-[(5-phenyl-2-[1,3,4]oxadiazolyl)methyl]4-piperidinylidene}-6,11-dihydro-5H- Benzo[5,6]cycloheptane[1,2-b]pyridine (I 1 )

[0049] 1. Preparation of methyl benzoate

[0050] Weigh 3 g of benzoic acid dissolved in 15 ml of methanol, then add 15 ml of cyclohexane, then slowly add concentrated H 2 SO 4 1ml, reflux for 7h, and use a water separator to separate the water generated by the reaction during the reflux. After the reaction is over, the reaction solution is concentrated under reduced pressure to about 1 / 3 volume, poured into water, and diluted with 1% NaHCO 3 The solution adjusted the mixture to neutral, and extracted with ethyl acetate, 10 ml each time, until the ethyl acetate layer had no fluorescence under the ultraviolet lamp. The ethyl acetate layers were combined and backwashed once with saturated NaCl solution, and then washed with anhydrous NaCl 2 SO 4 After drying, the ethyl acetate was evaporated to dryness to obtain 3.33 g of a color...

Embodiment 2

[0063] 8-Chloro-11-{1-[(5-(2-n-butoxyphenyl)-2-[1,3,4]oxadiazolyl)methyl]4-piperidinylidene}-6 , 11-dihydro-5H-benzo[5,6]cycloheptane[1,2-b]pyridine (I 2 )

[0064] 1. Preparation of Methylparaben

[0065] Using p-hydroxybenzoic acid as raw material, the preparation method is the same as that of methyl benzoate, white crystal, mp: 165-167°C, yield 98.7%.

[0066] 2. Preparation of methyl 4-n-butoxybenzoate

[0067] Dissolve 3g of methyl p-hydroxybenzoate in 30ml of ethyl acetate, add K 2 CO 3 2.6g, then add 4ml of n-bromobutane dropwise, heat to reflux for 8h, end the reaction, filter out the remaining solid and wash the solid with ethyl acetate until the lotion does not show fluorescence under the ultraviolet lamp. Combine the filtrate and washing liquid, mix the sample with crude silica gel, make sand, and separate the product by column chromatography (petroleum ether: ethyl acetate = 10:1) to obtain a colorless transparent oily liquid.

[0068] 3.I 2 preparation of ...

Embodiment 3

[0074] 8-chloro-11-{1-[(5-(2-methoxyphenyl)-2-[1,3,4]oxadiazolyl)methyl]4-piperidinylidene}-6, 11-Dihydro-5H-benzo[5,6]cycloheptane[1,2-b]pyridine (I 3 )

[0075] Preparation method is the same as I 1 . Pale red solid, mp: 154-155°C, yield 78%.

[0076] MS (ESI, 70ev, m / z): 499.2 [M+H] + ;521.2[M+Na] +

[0077] 1 H NMR (300MHz, CDCl 3 ) δ: 2.35-2.58 (m, 6H, = C (CH 2 ) 2 , N(CH 2 ) 2 ); 2.75-2.83(m, 2H, N(CH 2 ) 2 ); 2.88-2.91 (m, 2H, PhCH 2 ); 3.32-3.37(m, 2H, ); 3.92(m, 5H, -OCH 3 ); 7.02-7.13 (m, 6H, Ar); 7.39-7.42 (dd, 1H, ); 7.45-7.51 (m, 1H, Ar); 7.88-7.91 (dd, 1H, Ar); 8.37-8.39 (dd, 1H, )

[0078]IR (cm -1 ): 3357, 2939, 2901, 2823, 1708, 1588, 1477, 1436, 1258, 1243, 1116, 1018, 983, 829, 750

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Abstract

The invention relates to compounds disclosed as a general formula (I) and pharmaceutically acceptable salts thereof. The compounds have favorable anti-anaphylactic and anti-inflammatory actions. The invention also relates to a preparation method of the compounds and pharmaceutical preparations containing the compounds. In the invention, a series of compounds disclosed as the general formula (I) and pharmaceutically acceptable salts thereof are synthesized.

Description

technical field [0001] The invention relates to a benzo[5,6]cycloheptyl[1,2-b]pyridine derivative, a preparation method, a pharmaceutical composition and an anti-allergic application thereof. Background technique [0002] Allergic disease is a common disease. With the development of industrial society and increasingly serious environmental pollution, its incidence is on the rise in the world. According to the World Health Organization (WHO), there are currently 250 million people suffering from allergic diseases worldwide, and the incidence of the disease is rising rapidly. By 2010, 40% to 50% of people worldwide will suffer from allergies. WHO has listed allergic diseases as one of the three major diseases that need to be researched and prevented in the 21st century. [0003] Allergic diseases are related to autoactive substances (Autacoids) in the body. Histamine is one of the main chemical mediators of allergic reactions, and its physiological effects are the direct ca...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/14A61K31/4545A61P37/08A61P29/00
Inventor 周金培张惠斌黄文龙吴斐华刘武昆钱海程艳华
Owner CHINA PHARM UNIV