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Tricyclic compound with antihistamine activity, preparation method and application

A compound, antihistamine technology, applied in the fields of organic chemistry, drug combination, allergic diseases, etc., can solve problems such as cardiovascular system impact, and achieve the effect of low toxic side effects and strong antihistamine activity

Active Publication Date: 2014-04-02
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, desloratadine has a certain inhibitory effect on potassium channels at high concentrations, which may also affect the cardiovascular system

Method used

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  • Tricyclic compound with antihistamine activity, preparation method and application
  • Tricyclic compound with antihistamine activity, preparation method and application
  • Tricyclic compound with antihistamine activity, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] (1) Add 20mL of methanol and methyl acrylate (2.58g, 0.03mol) into a dry 50mL four-neck flask, and slowly add (S)-4-aminocyclohexanol (1.15g, 0.01mol) dropwise under stirring at room temperature, After dripping, the oil bath was heated to 40°C, reacted for 14 hours, and the excess methyl acrylate was evaporated under reduced pressure to obtain a light yellow oil. The crude product was separated and purified by silica gel column chromatography to obtain 2.62 g of the addition product, and the molar yield was 91.4%. .

[0035] Its structural formula is

[0036]

[0037] 1 H NMR (CDCl 3 ,500MHz)δ:3.64(s,6H),3.52(d,J=4.0Hz,1H),2.73(t,J=6.0Hz,4H),2.39(t,J=6.0Hz,5H),1.98( d,J=10.5Hz,2H),1.69(d,J=12.5Hz,2H),1.31~1.23(m,4H); 13 CNMR (CDCl 3 ,125MHz) δ:173.34,70.66,59.24,51.68,46.50,35.00,34.76,26.65.

[0038] Experiments have proved that the addition product can also be obtained by substituting ethanol, dichloromethane or ethyl acetate for methanol in this step.

[00...

Embodiment 2

[0064] Example 2: Antiasthmatic effect of compound (I) on guinea pigs with histamine-induced asthma

[0065] Take guinea pigs, place them in a plexiglass bell jar, spray them with saline histamine solution (0.8mg / mL) for 40s by ultrasonic atomization, record the time when guinea pigs develop asthma, take the time of convulsions and falls as the incubation period, and guinea pigs that exceed 180s will not be treated. Selected, 30 selected guinea pigs were randomly grouped, 10 in each group, divided into 3 groups: normal control group, desloratadine group (1mg / kg), compound (I) group (0.01mg / kg). Oral administration with 2mL / kg bw, 60 minutes after administration, put them into glass bell jars respectively, spray histamine hydrochloride solution according to the same conditions as pre-selection, record the incubation period of asthma, if no asthma occurs after 6 minutes, In terms of 6 minutes, the results were statistically processed.

[0066] The results are shown in Table 1 ...

Embodiment 3

[0070] Example 3: Effects on Muscle Tension of Guinea Pig Isolated Ileum Smooth Muscle

[0071] Guinea pigs (48 guinea pigs) were stunned with a wooden stick, and the abdomen was immediately opened, and the ileum about 15 cm long was separated, and the contents of the intestinal segment were washed with Tyrode's solution, and placed in Tyrode's solution at a constant temperature of 37°C for later use. oxygen. Cut the experimental intestinal tube (length 1cm) into 20mL Tyrode's solution at a constant temperature of 37°C, continue oxygenation, fix one end on the ventilation hook, and connect the other end to the muscle tension transducer and lead it to the computer interface, use BL The muscle tension value of the ileal smooth muscle was recorded systematically, and the experiment was carried out after the contraction of the intestinal segment was stable.

[0072] After the ileal contraction curve stabilized, record the tension value before adding the drug, then add the drug or...

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Abstract

The invention discloses a tricyclic compound with antihistamine activity, a preparation method and an application. The tricyclic compound with the antihistamine activity is named as N-(4-chlorocyclohexyl) desloratadine (I) and the structural formula is shown in the specification. An experiment verifies that the tricyclic compound with the antihistamine activity can be contestably combined with an organism H1 acceptor to block the effect between antihistamine and the organism H1, so that the antihistamine is prevented from expressing a biological effect and the antiallergic effect is realized. The experiment shows that the compound has stronger antihistamine activity and lower sedation side effects and anti-cholinergie side effects as compared with a positive control desloratadine.

Description

technical field [0001] The invention relates to a tricyclic compound with antihistamine activity, a preparation method and an application. Background technique [0002] Tricyclines are the second generation H 1 An important branch of receptor antagonists, which is composed of ethylenediamines, aminoalkyl ethers and propylamines H 1 The two aromatic rings of receptor antagonists are connected by different groups in the ortho position to form a tricyclic structure, and then modified by bioelectronic isosteres to form a class of antiallergic drugs. [0003] h 1 Receptor antagonists can compete with H 1 Receptor binding to block histamine and H 1 The role of receptors, thereby inhibiting the biological effects of histamine and playing an anti-allergic effect. h 1 Receptor antagonists can be roughly divided into two generations. The first generation is called traditional antihistamine drugs. They easily pass through the blood-brain barrier and have affinity reactions with r...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/04A61K31/4545A61P37/08
Inventor 陈立功王东华闫喜龙李阳林艳
Owner TIANJIN UNIV
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