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Ambroxol cysteine analogs and their preparation process and use thereof

A technology of cysteine ​​and acetylcysteine, which is applied in the field of ambroxol cysteine ​​analogue salt and its preparation and application, to achieve good curative effect and tolerance, improve therapeutic curative effect and reduce dosage

Inactive Publication Date: 2005-11-23
JIANGSU HANSOH PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The object of the present invention is to prepare better curative effect ambroxol cysteine ​​analogue salt, overcome the deficiency of existing preparation clinical curative effect and therapeutic range

Method used

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  • Ambroxol cysteine analogs and their preparation process and use thereof
  • Ambroxol cysteine analogs and their preparation process and use thereof

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Experimental program
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Effect test

Embodiment 1

[0027] Embodiment 1: the preparation of ambroxol N-acetyl cysteine ​​salt

[0028] In a 2000ml reaction flask, put 37.8g (0.1mol) of ambroxol, 28.2g (0.1mol) of N-acetylcysteine, add 200ml of ethanol, stir to dissolve, concentrate under reduced pressure to dryness to obtain an oily substance, add dichloro Heat 1000ml of methane in a water bath to dissolve, concentrate under reduced pressure until cloudy and precipitate oily precipitate, add 400ml of diethyl ether, stir until the precipitate turns into white crystals, then concentrate and evaporate most of the solvent, then add 200ml of diethyl ether dropwise, then stir at 40°C for 2 hours , placed at room temperature for 2 hours, filtered, washed with ether, and dried under vacuum at 50°C to obtain 46.3 g of white crystals with a yield of 85.6%. Melting point: 75-78°C. ( 1 HNMR (D 2O)δ: 1.18(m, 4H), 1.95(m, 4H), 2.08(s, 3H), 2.72(m, 1H), 2.95(d, 2H), 3.35(m, 1H), 3.95(s, 2H), 4.60(m, 1H), 7.25(d, 1H), 7.50(d, 1H))

Embodiment 2

[0029] Embodiment 2: Ambroxol erdosteine ​​salt

[0030] In a 500ml reaction flask, Ambroxol (37.8g, 0.1mol) and Erdosteine ​​(24.9g, 0.1mol) were dissolved in 150ml absolute ethanol respectively, filtered, the two filtrates were combined, heated to reflux, Allow to cool, filter, wash with ethanol, and dry to obtain 58 g of white solid, with a yield of 92.5% and a melting point of 170-172°C. ( 1 HNMR (D 2 O), 1.20(m, 4H), δ: 1.20(m, 4H), 1.90(m, 4H), 2.13(m, 1H), 2.40(m, 1H), 2.70(m, 1H), 3.20(s , 2H), 3.25(s, 2H), 3.30(m, 1H), 3.40(m, 2H), 3.90(s, 2H), 4.50(m, 1H), 7.31(d, 1H), 7.54(d, 1H))

Embodiment 3

[0031] Embodiment 3: the preparation of ambroxol double N-acetyl cysteine ​​salt lyophilized powder

[0032] In the 250ml reaction bottle, drop into Ambroxol 4.00g (10.6mmol), N-acetyl cysteine ​​3.454g (21.2mmol), add deionized water 60ml, stir and dissolve, filter with microporous membrane, freeze-dry, 7.34 g of freeze-dried powder was obtained, with a yield of 98.5%.

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Abstract

The invention relates to an ambroxol cysteine analogs and their preparation , the medicinal composition containing the compound, and the use in preparing apophlegmatic medicaments. The method for preparation comprises reacting ambroxol and sulfo-aminolactic acid analogue in solvent, the crystallizing, wherein n=1, 2, A is defined in the specification.

Description

technical field [0001] The present invention relates to ambroxol cysteine ​​analogue salt and its preparation method, as well as a pharmaceutical composition containing the compound in an effective dose of medicine, and its application in the preparation of expectorant pharmaceutical preparations. Background technique [0002] Ambroxol (Ambroxol) is the active metabolite of bromhexine, and its chemical name is trans-4-[(2-amino-3,5-dibromobenzyl)amino]cyclohexanol. The sputum medicine has low toxicity, definite curative effect, and stronger expectorant effect than bromhexine. Its preparation method and pharmacological effects have been published in US Patent No. 3,536,713. The drug was used clinically in the form of hydrochloride in 1984. Its clinical application has been published in Respiration 51 Suppl.1, 37 (1987). At present, ambroxol hydrochloride has been widely used in the treatment of respiratory diseases in many countries such as the United States, Britain, German...

Claims

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Application Information

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IPC IPC(8): C07C215/44C07C321/04C07C323/58C07C323/59C07D333/38
CPCC07C323/59C07D333/36C07C2101/14C07C215/44A61P11/10C07C2601/14
Inventor 岑均达钟慧娟
Owner JIANGSU HANSOH PHARMA CO LTD
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