CN102652753A - Veterinary compound diminazene aceturate and artemisinin preparation and preparation technology thereof - Google Patents
Veterinary compound diminazene aceturate and artemisinin preparation and preparation technology thereof Download PDFInfo
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- CN102652753A CN102652753A CN2011100517762A CN201110051776A CN102652753A CN 102652753 A CN102652753 A CN 102652753A CN 2011100517762 A CN2011100517762 A CN 2011100517762A CN 201110051776 A CN201110051776 A CN 201110051776A CN 102652753 A CN102652753 A CN 102652753A
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Abstract
The invention relates to a veterinary compound diminazene aceturate and artemisinin preparation, which is a powder injection comprising the following medicinal components in percentage by mass: 10 to 85 percent of diminazene aceturate, 5 to 60 percent of artemisinin or artemisinin extract, and 2 to 30 percent of beta-cyclodextrin. The preparation is prepared by the following steps of: 1) refining the diminazene aceturate; 2) preparing a water-soluble inclusion complex of the artemisinin or the artemisinin extract; and 3) proportioning, mixing, sterilizing and filling the preparation. The veterinary compound diminazene aceturate and artemisinin preparation has the advantages that the preparation is quick in absorption and high in bioavailability in subcutaneous or intramuscular injection; by combined utilization of the artemisinin and the diminazene aceturate which serve as active Chinese medicinal ingredients, a synergistic effect of Chinese medicaments can be achieved, and the toxic or side effect of the diminazene aceturate is reduced; the artemisinin, particularly the artemisinin extract is cheaper than dihydroartemisinin, artemether and artesunate; and the preparation is suitable to be produced in injection workshops of animal pharmaceutical factories with good manufacturing practice (GMP) conditions, and does not require to update the investment.
Description
Technical field
The present invention relates to a kind of animal compound Diminazene Aceturate and arteannuin preparation, belong to field of pharmaceutical preparations.
Background technology
Diminazene Aceturate has another name called Benny's that, berenil, and realize industrial-scale production in China the seventies.Diminazene Aceturate and injection thereof have recorded People's Republic of China's veterinary drug allusion quotation.Be used for the dehab and the horse covering disease that cause by trypanosomicide.This product mechanism of action is that the DNA through selective exclusion trypanosomicide kinetoplast is synthetic and duplicate, and produces irreversibility with nuclear and combines, thereby makes the kinetoplast disappearance of trypanosomicide, can not schizogamy, reach therapeutic purposes.But its toxicity is big, safety range is less, and the application of treatment amount also the domestic animal muscular tremor can occur, plays unable to sleep soundly, urinates again and again, waits untoward reaction.Demand seeking to keep the Diminazene Aceturate curative effect urgently, reduce its toxic prescription again.
Medicinal arteannuin is from the Chinese medicine Herba Artemisiae Annuae is leaf and the alabastrum (Artemisia annua L.) of feverfew Herba Artemisiae annuae, to separate to obtain.The molecular formula of arteannuin is C
15H
22O
5, molecular weight 282.34 is a kind of sesquiterpene lactones, is white, needle-shaped crystals, fusing point is 156～157 ℃, [α] 17D=+66.3 ° (C=1.64 chloroform).Be soluble in the organic solvents such as chloroform, ethyl acetate, petroleum ether, ethanol, water-soluble hardly.
Herba Artemisiae Annuae is the herb of feverfew Herba Artemisiae annuae (Artemisia annua L.), and the history in China as the existing two thousand years of antimalarial also has a lot of other medical values, as can be used for relieving summer heat, antibacterial, brings down a fever, treat and catch a cold etc.Recent studies shows: arteannuin and derivant can significantly improve lymhocyte transformation rate, strengthen the immunologic function of antibody; Aspects such as parasite type disease, cardiovascular system diseases and tumor also there is certain curative effect.Particularly unique activity to a lot of protozoons.Artemisinin-based drug is safety low-poison, has the potentiation synergism, for this type medicine provides prospect as antiprotozoal drug compound recipe for animals.Present widely used artemisinin derivative Artemether, dihydroartemisinine and artesunate etc., their price is several times as much as arteannuin, and it is very more urgent to the application of artemisinin-based drug in domestic animal than the lower resource of arteannuin to seek price.Are we at Chinese patent? Disclose the low cost process of arteannuin extract preparation, and particularly pointed out: the Chinese medicine extract preparation rationally also can realize safety low-poison, and not necessarily purification is a monomer.In view of the arteannuin activity in vivo is higher than external activity, can use arteannuin or arteannuin extract, will reduce drug cost.
The Diminazene Aceturate crude drug has process route that commercial production is worth must be self-produced right-p-nitrile, the latter has severe toxicity to the people, serious environment pollution.Seek the source of the Diminazene Aceturate crude drug of reasonable price, receive user and pay attention to.The Diminazene Aceturate of abroad selling in China, the Diminazene Aceturate that price is produced far below China, but quality can not reach the requirement of veterinary drug level fully.Development is processed commercially available Diminazene Aceturate and is reached veterinary drug level quality index, has market value.
Summary of the invention
Problem to be solved by this invention is to propose a kind of absorption to above-mentioned prior art soon, and bioavailability is high, and the medication less expensive is difficult for producing chemical sproof animal compound Diminazene Aceturate and arteannuin injection.
The present invention is adopted solution to be by the problem of the above-mentioned proposition of solution: animal compound Diminazene Aceturate and arteannuin preparation include the injectable powder that following drug component is formed:
Press such scheme, described β one cyclodextrin is hydroxypropyl one β, one cyclodextrin or sulfobutyl ether one β one cyclodextrin.
Join usefulness when the present invention is clinical, with the injection water dissolving of injectable powder total amount 20～30 times (g/ml), the injection specification is that 0.5～4g/ props up, subcutaneous or intramuscular injection.
The preparation technology of animal compound Diminazene Aceturate of the present invention and arteannuin preparation includes following steps:
1) Diminazene Aceturate is refining
Diminazene Aceturate and combination solvent are mixed, and heating 0.6～2h filters, and crystallisation by cooling filters, and crystallization is drying to obtain purified Diminazene Aceturate, and described combination solvent is C
1～C
3Alcohol and the mixed solution of inorganic weak bases, described C
1～C
3Alcohol is methanol, ethanol, propanol or isopropyl alcohol, and the mass percent concentration of alcohol-water solution is 10～80%; 2) preparation of arteannuin or arteannuin extract water solublity inclusion coordination compound;
Arteannuin extract or arteannuin are dissolved in the ethanol for 40～50 ℃, splash in the solution of beta-schardinger dextrin-and distilled water under stirring, reacted 2～4 hours, filter, the filtrating vacuum concentration gets arteannuin-beta-schardinger dextrin-solid inclusion coordination compound to doing;
3) configuration of preparation, mixing and sterilization embedding
Take by weighing purified Diminazene Aceturate and arteannuin-beta-schardinger dextrin-solid inclusion coordination compound, compound recipe Diminazene Aceturate and arteannuin preparation are processed in configuration, mixing and embedding sterilization, and wherein component and mass percent are: Diminazene Aceturate 10%～85%; Arteannuin or arteannuin extract 5%～60%; β one cyclodextrin 2%～30% is mass percent.
Press such scheme, described Diminazene Aceturate and combination solvent proportioning are 1: 8～35 (g/ml).
Press such scheme; Described arteannuin preparation method of extract: adopting the content of arteannuin is raw material at leaf and the alabastrum of the Herba Artemisiae annuae more than 0.2%; Obtain paste arteannuin extract, its artemislnin content >=90%, quality meter through a plurality of extraction pot countercurrent extraction; Extraction pot adopts and extracts 50 ℃ of temperature; Extraction time 30～80min; 200～400 rev/mins of speeds of agitator; Extracting solvent is 30～60 ℃ of petroleum ether or industrial naptha; The solid-to-liquid ratio 1: 8～10 of leaf of Herba Artemisiae annuae and alabastrum and extraction solvent.
Diminazene Aceturate of the present invention adopts combination solvent refining, adopts carbon 1～carbon 3 pure and mild alkaline aqueous solutions, and yield can reach 70%～85%, and quality meets the veterinary drug allusion quotation.
Diminazene Aceturate of the present invention accounts for main share as anti-dehab, castellanella equiperdum disease and eperythrozoonosis, arteannuin, or the arteannuin extract through the potentiation synergism, improves drug effect to a lot of protozoacide unique activity, reduction toxicity, raising drug safety.Arteannuin, arteannuin extract water solublity are very low, can adopt to add solubilizing agent or cosolvent improves, but some cosolvent like polyoxyethylene castor oil and ethanol, are prone to cause allergic reaction and toxic and side effects.The present invention adopts beta-schardinger dextrin-solubilizing agent and arteannuin, arteannuin extract to process water solublity clathrate (solid); Be mixed and made into injectable powder with water miscible Diminazene Aceturate (solid) again; Mixing, dissolve formation compound recipe water injection with an amount of water for injection when clinical supplies to use; Adopting hydroxypropyl one β one cyclodextrin, sulfobutyl ether one β one cyclodextrin is that raw material is done solubilizing agent, and safe, cost is low.
Compound preparation of the present invention is mainly used to this giardiasis of treatment poultry domestic animal BABEI, Taylor's giardiasis, dehab, castellanella equiperdum disease and eperythrozoonosis.
Advantage of the present invention is: subcutaneous or administered intramuscular absorbs soon, bioavailability is high; Middle pharmaceutically active ingredient arteannuin and Diminazene Aceturate are united use, can bring into play the Synergistic of Chinese medicine, reduce the Diminazene Aceturate toxic and side effects; Arteannuin particularly arteannuin extract price than dihydroartemisinine, Artemether and artesunate considerably cheaper; Be fit to have between the animal pharmaceutical factory che injection of GMP condition and produce, need not to upgrade and drop into.
Description of drawings
Fig. 1 obtains FB(flow block) for arteannuin extract and arteannuin;
Fig. 2 connects sketch map for the multiple tank countercurrent extraction.
The specific embodiment
Animal compound Diminazene Aceturate of the present invention and arteannuin process for preparation of injection include following steps:
1) arteannuin extract or arteannuin obtains;
One. the arteannuin extract obtain (list of references: DANIEL L.KLAYMAN et.al; ISOLATION OFARTEMISININ (QINGHAOSU) FROM ARTEMISIA ANNUA GROWING IN THE UNITEDSTATES [J]; Journal of Natural Products; 1984,47 (4): 715-717; Zhao Bing etc., arteannuin extraction conditions research [J] Chinese herbal medicine, 2000,31 (6): 421; Wei Guofeng etc., the different Study on extraction process [J] of Herba Artemisiae Annuae, number reason medical magazine 2002,15 (2): 170)
The content that adopts area, Yunxi, Hubei to produce arteannuin is raw material at leaf and the alabastrum (Artemisia annua L.) of the feverfew Herba Artemisiae annuae more than 0.2%; Obtain arteannuin extract and arteannuin by Fig. 1 FB(flow block); The arteannuin extract is a paste, arteannuin >=90%, quality meter.
Wherein 1～4, extraction pot; 5～9, solvent or extracting solution shifting pump; 10～13, the backflow cooler
The extraction pot function: extract, heating is stirred, and filters.
Extraction pot operating parameter: 100 liters of jar appearances; The charge Herba Artemisiae Annuae is pulverized about material 10kg; Coefficient～0.7; 50 ℃ of temperature; Extraction time 30～80min; 200～400 rev/mins of speeds of agitator; Extract solvent: 30～60 ℃ of petroleum ether or industrial naptha; Solid-to-liquid ratio 1: 8～10; Herba Artemisiae Annuae is pulverized material 60 orders～0.25mm.
2) fine chemical products such as commercially available Diminazene Aceturate elaboration and bullion is refining to reach the veterinary drug specification;
Commercially available fine chemical product level Diminazene Aceturate and veterinary drug level compare, and impurity is more, and water solublity is relatively poor, and clarity is defective.Water-soluble according to Diminazene Aceturate, be insoluble to pure characteristic basically.The present invention adopts combination solvent refining, adopts carbon 1～carbon 3 pure and mild alkaline aqueous solutions.Combination solvent consists of: distilled water; Carbon 1～carbon 3 alcohol comprise methanol, ethanol, propanol and isopropyl alcohol; Basic species is an inorganic weak bases.The inorganic weak bases trace, the mass percent concentration 10～80% of alcohol-water solution.Fine chemical product level Diminazene Aceturate and combination solvent proportioning 1: 8～35 (g/ml).
Fine chemical product level Diminazene Aceturate is mixed with the combinations thereof stirring solvent, and heating 0.6～2hr. filters, and crystallisation by cooling filters drying.
3) preparation of arteannuin or arteannuin extract water solublity inclusion coordination compound;
Arteannuin extract or arteannuin that step 1) is made are dissolved in the ethanol for 50 ℃; Carefully splash in the solution of beta-schardinger dextrin-and distilled water under stirring, arteannuin (pure) reacted 2～4 hours than HP-1: 1～1.3 (mol ratio); Filter; The filtrating vacuum concentration gets arteannuin-beta-schardinger dextrin-solid inclusion coordination compound to doing, and pulverizes.
4) configuration of animal compound Diminazene Aceturate and arteannuin powder for injection, mixing and embedding sterilization etc.
Take by weighing purified Diminazene Aceturate and arteannuin-beta-schardinger dextrin-solid inclusion coordination compound powder, press following composition and quality percentage composition: Diminazene Aceturate 10%～85%; Arteannuin or arteannuin extract 5%～60%; β one cyclodextrin 2%～30% is mass percent, and it is compound recipe Diminazene Aceturate and the arteannuin preparation that 0.5～4g/ props up that specification is processed in configuration, mixing and embedding sterilization etc.
The specific embodiment
The present invention will describe with following embodiment, but the present invention is not limited to any one or the similar instance of embodiment.
Get the content that Yunxi, Hubei area produces arteannuin and put in the drying baker in 40 ℃ of oven dry, press document (Gao Tongwen, University Of Tianjin's Master's thesis, 2008,16～17) TLC method and distinguish between truth and false at the leaf of the feverfew Herba Artemisiae annuae more than 0.2%.Pulverize and cross 60 orders～0.25mm sieve.Press document (Li Chunli etc., [J], Medical University Of Chongqing's journal, 2007,32 (4), 413) again with the content of determined by ultraviolet spectrophotometry arteannuin, require above confession of artemislnin content >=0.2% to use.
Powder pure material in the title 10Kg left and right sides is inserted the extraction pot group, and is as shown in Figure 2, and (extraction pot adopts and extracts 50 ℃ of temperature to press Fig. 1 flow process and technological parameter countercurrent extraction; Extraction time 60min; 200～400 rev/mins of speeds of agitator; Extracting solvent is 50 ℃ of petroleum ether; The solid-to-liquid ratio of leaf of Herba Artemisiae annuae and alabastrum and extraction solvent 1: 9).The solvent that is rich in the arteannuin effective ingredient contacts with the fresh pure material of powder that is extracted before flowing out jar group, and the pure material of powder will contact with fresh solvent before flowing out jar group and will be extracted completely, make the extraction of effective ingredient more complete, extraction ratio～95%.Filter, press dry filter cake, merging filtrate, the vacuum concentration precipitation gets extractum, and the petroleum ether condensing and recycling is applied mechanically.Extractum adds 70% dissolve with ethanol, 50 ℃ of constant temperature refluxing and stirring, extraction dewaxing, extract filtrating added 50 ℃ of insulation decolourings of active carbon of 1～2% 1.5 hours, filter, vacuum concentration to do the arteannuin extract, the ethanol condensing and recycling is applied mechanically.
The arteannuin extract is refining with 70% ethanol, filtration, dry arteannuin.
Get commercially available fine chemical product level Diminazene Aceturate 100g add to band thermometer, reflux condenser, agitator and charging hopper the four-hole glass reaction and in; Add combination solvent; Consist of distilled water, methanol (or ethanol, propanol and isopropyl alcohol) and micro-inorganic weak bases, alcohol-water solution concentration 10～80%.Fine chemical product level Diminazene Aceturate and combination solvent proportioning 1: 8～35 (g/ml).Mix, heating in water bath 0.6～2hr., the heat filter, 105 ℃ of dryings of normal pressure are filtered in cooling (about 5 ℃) crystallization.Get veterinary drug level Diminazene Aceturate, by method check under People's Republic of China's veterinary drug allusion quotation Diminazene Aceturate item.
The arteannuin extract that makes (thick pure) is dissolved in the ethanol for 50 ℃; Stir down and carefully splash in the solution of 10 fens HP-s and 90 fens distilled water; Reacted 4 hours, and filtered, filtrating 5～10mm Hg is concentrated into dried; Get xanchromatic arteannuin-HP-solid inclusion coordination compound, pulverize.
Arteannuin-HP-solid inclusion coordination compound and purified Diminazene Aceturate pressed following composition and quality percentage composition: Diminazene Aceturate 60%; Arteannuin or arteannuin extract 30%; β one cyclodextrin 10% (being mass percent), it is compound recipe Diminazene Aceturate and the arteannuin powder for injection that 0.5～4g/ props up that specification is processed in configuration, mixing and embedding sterilization etc.
Claims (5)
1. animal compound Diminazene Aceturate and arteannuin preparation include the injectable powder that following drug component is formed:
Diminazene Aceturate 10%～85%; Arteannuin or arteannuin extract 5%～60%; β one cyclodextrin 2%～30% is mass percent.
2. by described animal compound Diminazene Aceturate of claim 1 and arteannuin preparation, it is characterized in that described β one cyclodextrin is hydroxypropyl one β, one cyclodextrin or sulfobutyl ether one β one cyclodextrin.
3. by the preparation technology of described animal compound Diminazene Aceturate of claim 1 and arteannuin preparation, it is characterized in that including following steps:
1) Diminazene Aceturate is refining
Diminazene Aceturate and combination solvent are mixed, and heating 0.6～2h filters, and crystallisation by cooling filters, and crystallization is drying to obtain purified Diminazene Aceturate, and described combination solvent is C
1～C
3Alcohol and the mixed solution of inorganic weak bases, described C
1～C
3Alcohol is methanol, ethanol, propanol or isopropyl alcohol, and the mass percent concentration of alcohol-water solution is 10～80%;
2) preparation of arteannuin or arteannuin extract water solublity inclusion coordination compound
Arteannuin extract or arteannuin are dissolved in the ethanol for 40～50 ℃, splash in the solution of beta-schardinger dextrin-and distilled water under stirring, reacted 2～4 hours, filter, the filtrating vacuum concentration gets arteannuin-beta-schardinger dextrin-solid inclusion coordination compound to doing;
3) configuration of preparation, mixing and sterilization embedding
Take by weighing purified Diminazene Aceturate and arteannuin-beta-schardinger dextrin-solid inclusion coordination compound, compound recipe Diminazene Aceturate and arteannuin preparation are processed in configuration, mixing and embedding sterilization, and wherein the mass percent of component and component is: Diminazene Aceturate 10%～85%; Arteannuin or arteannuin extract 5%～60%; β one cyclodextrin 2%～30% is mass percent.
4. by the preparation technology of described animal compound Diminazene Aceturate of claim 3 and arteannuin preparation, it is characterized in that described Diminazene Aceturate and combination solvent proportioning are 1: 8～35 (g/ml).
5. press the preparation technology of claim 3 or 4 described animal compound Diminazene Aceturate and arteannuin preparation; It is characterized in that described arteannuin preparation method of extract: adopting the content of arteannuin is raw material at leaf and the alabastrum of the Herba Artemisiae annuae more than 0.2%; Obtain paste arteannuin extract through a plurality of extraction pot countercurrent extraction; Its artemislnin content >=90%, the quality meter; Extraction pot adopts and extracts 50 ℃ of temperature; Extraction time 30～80min; 200～400 rev/mins of speeds of agitator; Extracting solvent is 30～60 ℃ of petroleum ether or industrial naptha; The solid-to-liquid ratio 1: 8～10 of leaf of Herba Artemisiae annuae and alabastrum and extraction solvent.
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| CN103550229A (en) * | 2013-11-08 | 2014-02-05 | 四川维尔康动物药业有限公司 | Compound artemisinin multiphase lipidosome injection as well as preparation method thereof |
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| CN1740176A (en) * | 2005-09-21 | 2006-03-01 | 天津大学 | Process of extracting and separating artemisinin from sweet wormwood plant |
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| CN103550229A (en) * | 2013-11-08 | 2014-02-05 | 四川维尔康动物药业有限公司 | Compound artemisinin multiphase lipidosome injection as well as preparation method thereof |
| CN103550229B (en) * | 2013-11-08 | 2015-05-20 | 四川维尔康动物药业有限公司 | Compound artemisinin multiphase lipidosome injection as well as preparation method thereof |
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