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Loratadine compound and preparation method thereof

A technology of loratadine and compounds, applied in the field of loratadine compounds and its purification process, can solve the problems of reduced yield of purified products or intermediates, low purity of target products, less purity can be obtained, etc. Achieve the effects of easy control and industrialized production, low cost, and reduced toxic and side effects

Inactive Publication Date: 2012-09-26
HAINAN LINGKANG PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The syntheses described so far thus involve various disadvantages, including a high number of steps, use of reagents which are difficult to handle on an industrial level, generation of unwanted side reaction products, and consequently reactions to purify products or intermediates with reduced yields
[0011] These methods can effectively prepare loratadine, but the unavoidable problem is that the purity of the target product is not high, and the product post-treatment or purification method provided is a conventional method in organic chemical synthesis, and these methods are rarely able to obtain 95% or Purity above

Method used

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  • Loratadine compound and preparation method thereof
  • Loratadine compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] 10g of 94.8% loratadine crude product was dissolved in 100ml of isopropanol, then 0.1g of gac was added, stirred at 30°C for 10 minutes, and filtered to obtain primary purified loratadine; After the solution is concentrated, add 10g of pretreated DA-201 macroporous adsorption tree, stir well, add to the top of DA-201 macroporous adsorption resin column, wash with 1 to 2 column volumes of purified water until clarified , and then elute with 50% isopropanol containing 0.01mol / L hydrochloric acid, collect the eluate, concentrate under reduced pressure to about two-fifths of the volume, and obtain secondary purified loratadine; stir at 50~60°C Add ammonia water to the concentrated solution until the pH value is 8.0, cool to 0-4°C overnight, precipitate crystals, centrifuge, wash, and dry to obtain 9.07 g of three-stage purified loratadine with a purity of 99.63% and a yield of 95.70 %. MP: 135~136℃

Embodiment 2

[0043] 10g of 94.8% loratadine crude product was dissolved in 100ml of isopropanol, then 0.3g of gac was added, stirred at 40°C for 15 minutes, filtered to obtain primary purified loratadine; After the solution is concentrated, add 10g of pretreated Diaion HP2MG macroporous adsorption resin, stir well, add to the top of Diaion HP2MG macroporous adsorption resin column, wash with 1 to 2 column volumes of purified water until clarification, and then Elute with 50% isopropanol containing 0.01mol / L hydrochloric acid, collect the eluate, concentrate under reduced pressure to about two-fifths of the volume, and obtain secondary purified loratadine; Ammonia water was added to the concentrated solution until the pH value was 8.2, cooled to 0-4°C overnight, crystals were precipitated, centrifuged, washed and dried to obtain 9.03 g of tertiary purified loratadine with a purity of 99.75% and a yield of 95.28%. MP: 135-136°C.

Embodiment 3

[0045] 10g of 94.8% loratadine crude product was dissolved in 100ml of isopropanol, then 0.4g of gac was added, stirred at 50°C for 20 minutes, and filtered to obtain primary purified loratadine; After the solution is concentrated, add 10g of the pretreated AB-8 macroporous adsorption resin, stir well, add to the top of the AB-8 macroporous adsorption resin column, and wash with 1 to 2 column volumes of purified water until clarification , and then elute with 50% isopropanol containing 0.01mol / L hydrochloric acid, collect the eluate, concentrate under reduced pressure to about two-fifths of the volume, and obtain secondary purified loratadine; stir at 50~60°C Add ammonia water to the concentrated solution until the pH value is 8.5, cool to 0-4°C overnight, precipitate crystals, centrifuge, wash, and dry to obtain 8.99 g of tertiary purified loratadine with a purity of 99.87% and a yield of 94.8 %. MP: 135-136°C.

[0046] The following enumerates some comparative examples of ...

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Abstract

The invention relates to a method for preparing a loratadine compound. The method comprises the following steps of: (1) dissolving crude loratadine into an appropriate organic solvent, adding active carbon for adsorbing, heating, stirring, and filtering to obtain primarily-purified loratadine; (2) concentrating the solution, loading onto a macroporous absorption resin column, washing to clear state with purified water, eluting with 50 percent isopropyl alcohol containing 0.01 mol / L HCl, and collecting an eluent to obtain secondarily-purified loratadine; and (3) adjusting the pH of the eluent with an alkaline solution, cooling for crystalizing, centrifuging the separated crystal, washing and drying to obtain trebly-purified loratadine. The purity of fine loratadine obtained with the methodis not less than 99.5 percent, the quantity of ignition residues is extremely small, and the heavy metal content is extremely low. The method has the characteristics of easiness, convenience and easiness for controlling and industrial production; and simultaneously, the toxic and side effects of the loratadine compound which is taken as an antihistamine medicament are reduced, and the preparationproduct quality is improved.

Description

technical field [0001] The invention relates to a loratadine compound and a purification process thereof, belonging to the technical field of medicine. Background technique [0002] Loratadine (Loratadine), chemical name: 4-(8-chloro-5,6-dihydro-11H-benzo 5,6 cyclohepta 1,2-b pyridin-11-ylidene)-1 -Ethyl piperidinecarboxylate, molecular formula: C 22 h 23 ClN 2 o 2 , molecular weight: 382.89, structural formula: [0003] [0004] Loratadine is a non-sedating long-acting tricyclic antihistamine developed by Schering-Plough Company, which has selective anti-peripheral H1 receptor effect. It was first introduced by Schering-Plough Company in 1988. Listed in Belgium, it is a third-generation antihistamine with the characteristics of fast onset and strong effect. Studies with guinea pigs have shown that the action time of this product is 18-24 hours, and studies on central effects have shown that this product has little or no inhibitory or anticholinergic effects on mice...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/04A61P37/08
Inventor 陶灵刚
Owner HAINAN LINGKANG PHARMA CO LTD