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Ebastine salt as well as preparation method and application thereof

A technology of ebastine and hydrochloric acid, applied in the field of pharmacy, can solve the problems of limiting the therapeutic effect of ebastine, poor tablet dissolution, low bioavailability and the like, and achieves simple and convenient post-processing and mild reaction conditions. , the effect of high purity

Pending Publication Date: 2022-02-08
JIANGSU LIANHUAN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Most of the currently commercially available ebastine preparations are oral tablets. Because ebastine contains multiple hydrophobic groups in its molecular structure, it is insoluble in water, and the dissolution rate of the tablet is poor, and its bioavailability is low. Absorption, which limits the therapeutic effect of ebastine
The symptoms of allergic diseases are mostly in the skin, nasopharynx, eyes, etc., and are directly administered through pharmaceutical preparations such as solutions, sprays, lotions, liniments, ointments, eye drops, ointments, and ophthalmic gels. Applied to the symptom site, it has the advantages of rapid absorption, quick onset, low dose, and small side effects; however, this type of preparation also puts forward certain requirements for the water solubility of the raw material drug

Method used

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  • Ebastine salt as well as preparation method and application thereof
  • Ebastine salt as well as preparation method and application thereof
  • Ebastine salt as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Debas Tatin hydrochloride preparation:

[0035]

[0036] (1) Place the twistin (10.0 g, 21.3 mmol, 1.0 Equiv.) In a 100 ml round bottom flask, ethanol (15 ml). The hydrogen chlorinated hydrogen chlorinated solution (20% in etOh, 5.8 g, 32.0 mm, 1.5 equiv.) Was dripped into the twistin solution at room temperature at 25 ° C, and the solution gradually became clarified. After completion of the boss, stir it for 10 min, evaporate the solvent under reduced pressure, and gelatin hydrochloric acid was crude according to Bastine;

[0037] (2) The hydrochloric acid obtained in step (1) is added to hexane (15 ml), heating and reflow, gradually incorporating acetate (55 mL), continued to reflow for 1 h, then naturally cooled to room temperature and stir over night Filtration, filter cake was washed with EtOAc (EtOAc) The purity is 97.32%;

[0038] The identification data of the bisenine hydrochloride has been subjected to as follows:

[0039] 1 H NMR (500MHz, DMSO-D 6 : δ 10.82 (1H...

Embodiment 2

[0043] Debarst sulfate preparation:

[0044]

[0045](1) The ebastine (10.0g, 21.3mmol, 1.0equiv.) Was placed in a 100mL round bottomed flask was added acetone (15 mL), stirred at room temperature 25 ℃ Sulfuric acid (98%, 2.3g, 22.4mmol, 1.05 equiv.) was dissolved in acetone (5mL) was added dropwise, and the solution was heat gradually became clear. After the addition is complete stirring was continued for 10min, the solvent was evaporated under reduced pressure to give a crude gum sulfate ebastine;

[0046] (2) Sulfuric acid (1) obtained in hexane was added (15mL) to step ebastine crude product, heated to reflux, was added dropwise gradually ethyl acetate (20 mL), heating was continued at reflux IH, cooled to room temperature followed by stirring, the filter cake with hexane / ethyl acetate: washing under (1 1,5mL × 3) 60 ℃ dried 3h, to give 9.60 g of white solid sulfate ebastine, yield 79.6%, purity according to HPLC test results show to 97.67%;

[0047] Identification data ob...

Embodiment 3

[0052] Benzenesulfonate prepared by Bastin

[0053]

[0054] (1) The ebastine (10.0g, 21.3mmol, 1.0equiv.) Was placed in a 100mL round bottom flask was added ethanol (20 mL), a clear solution was heated to 50 deg.] C, stirring acid (3.5g, 22.4mmol, 1.05equiv.) was dissolved in ethanol (10 mL) was added dropwise. After the addition is complete stirring was continued for 10min, the solvent was evaporated under reduced pressure to give the crude acid ebastine;

[0055] (2) to step (1) obtained in the crude acid ebastine added acetone (15 mL), dissolved was heated to 80 deg.] C, cooled to 0 deg.] C with stirring, a white solid was precipitated, stirring was continued for 1h. Filtered, washed, the filter cake with acetone (5mL × 3) 60 ℃ dried 3h, ebastine acid as a white solid 11.62 g, yield 87.4%, according to HPLC results showed a purity of 98.89%;

[0056] Identification data obtained by ebastine benzenesulfonate follows:

[0057] 1 H NMR (500MHz, DMSO-d 6 ): Δ9.03 (1H, s), 7.91-7...

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Abstract

The invention discloses ebastine salts as well as a preparation method and application thereof, and belongs to the technical field of pharmacology. The preparation method of the ebastine salt comprises the following steps: dissolving ebastine in a solvent, adding an acid or an acid solution, uniformly performing mixing and stirring to react, and performing purifying to obtain the ebastine salt with the purity of more than 97%. The preparation method is simple and easy to implement, high in yield, good in purity and suitable for industrial production. The ebastine salt has better histamine H1 receptor antagonistic biological activity and water solubility, is convenient to prepare various liquid preparations, and shows very high clinical medication value.

Description

Technical field [0001] The present invention belongs to the technical field of pharmacology, and is specifically involved in a class of succin and its preparation methods and applications. Background technique [0002] Ebastine (Ebastine) 1- [4- (1,1-dimethyl) phenyl] -4- [4- (diphenoxy) -1-piperidyl) -1-butanone) is a long-acting, non-caloristic second-generation histamine H1 receptor antagonist, which has a high degree of selectivity to the H1 receptor, and no central suppression. In clinical treatment, including seasonal, allergic rhinitis and chronic idiophara, eczema, skin itching, etc. . [0003] At present, the commercially available Ibastine preparation is more oral tablets. Due to a plurality of hydrophobic groups in the moistine molecular structure, it causes it in water insoluble, the tablet is not good, the bioavailability is low, the body is difficult to Absorbed, limiting the therapeutic effect of Ettin. The symptoms of the allergic disease are mostly in the skin, n...

Claims

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Application Information

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IPC IPC(8): C07D211/46A61P11/00A61P11/06A61P37/08A61P17/00A61P27/02
CPCC07D211/46A61P11/00A61P11/06A61P37/08A61P17/00A61P27/02
Inventor 钟林睿牛犇李家慧黄坤
Owner JIANGSU LIANHUAN PHARMA
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