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WO2003101419A1 - Produit d'injection a liberation soutenue contenant des substances anti-parasites - Google Patents

Produit d'injection a liberation soutenue contenant des substances anti-parasites Download PDF

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Publication number
WO2003101419A1
WO2003101419A1 PCT/CN2003/000389 CN0300389W WO03101419A1 WO 2003101419 A1 WO2003101419 A1 WO 2003101419A1 CN 0300389 W CN0300389 W CN 0300389W WO 03101419 A1 WO03101419 A1 WO 03101419A1
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WO
WIPO (PCT)
Prior art keywords
hco
solid dispersion
preparation
water
add
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/CN2003/000389
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English (en)
Chinese (zh)
Inventor
Yuwan Wang
Zhende Pan
Xiaoxi Dai
Yan Xue
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eco Animal Health Ltd
Original Assignee
Eco Animal Health Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Eco Animal Health Ltd filed Critical Eco Animal Health Ltd
Priority to AU2003234894A priority Critical patent/AU2003234894A1/en
Publication of WO2003101419A1 publication Critical patent/WO2003101419A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents

Definitions

  • the invention relates to a veterinary preparation, specifically, a sustained-release injection containing an antiparasitic drug.
  • the preparation is a solid dispersion composed of an antiparasitic drug and a hydrogenated castor oil (HCO). This is a salient feature of the present invention.
  • Solid dispersions containing HCO and antiparasite drugs can be prepared by solvent evaporation or melt dispersion condensation or solvent-non-solvent methods.
  • glycerol triacetate has a certain ability to dissolve ivermectin (about 3%) and acetylated monoglyceride (non-ionic lipophilic surfactant) has a strong ability to disperse HCO. Therefore, the The active ingredient and HCO are uniformly dispersed in triglyceride and acetylated monoglyceride, and the appearance of the preparation is in a colloidal state.
  • composition and preparation of the preparation of the present invention are different from those described in patents WO99 / 27906 and EP0535734.
  • the present invention combines HCO with macrolide insect repellent or N-phenylpyrazole insect repellent or other insect repellent to form solid dispersion particles (hereinafter referred to as HCO drug-loaded particles), and
  • HCO drug-loaded microparticles are dispersed in a dispersion medium mainly composed of water or other hydrophilic liquid to prepare an injection.
  • the preparation is essentially a suspension injection containing drug-loaded microparticles.
  • the therapeutic drug is dispersed in HCO, and the two constitute drug-loaded microparticles.
  • the injection prepared with the HCO drug-loaded microparticles Due to the strong hydrophobicity and slow biodegradability of HCO, the injection prepared with the HCO drug-loaded microparticles has a good sustained-release effect and does not have Permanent residue, the drug-loaded microparticles have good biocompatibility and little irritation to the injection site.
  • the liquid dispersion medium used as a component of the formulation also affects the formulation.
  • the sustained-release effect, stability, and biocompatibility have a great impact. If the liquid dispersion medium is not selected properly, the drug in the drug-loaded microparticles may be dissolved or partially dissolved. This has a great impact on the sustained-release effect and may also It can lead to drug delamination and even disintegration of drug-loaded particles.
  • the selection of a suitable liquid dispersion medium is also important to ensure the stability, clinical effect, and biocompatibility of the formulation.
  • the present invention particularly preferably uses water or 1,2-propanediol as the main dispersion medium of the preparation.
  • the prepared preparation has good biocompatibility, stable physical and chemical properties, and good sustained-release effect.
  • the agent is injected subcutaneously, and is used once. Up to 50-90 days or longer.
  • the specific gravity of the preparation medium can be adjusted by adding an appropriate amount of organic substances, such as adding a smaller specific gravity of ethanol or dimethylacetamide, or adding a larger specific gravity of 1, 2-propanediol, glycerol, acetal glycerol, or triple pear Alcohol and so on.
  • the preparation composition of the present invention is as follows:
  • auxiliaries can be added to the preparation, including surfactants, suspending agents, antioxidants and local pain relief agents;
  • the preparation method of the preparation of the present invention is as follows:
  • Method 1 Mixing a low-boiling organic solvent or a micronized active compound (such as a macrolide insect repellent or N-phenylpyrazole insect repellent) with the melted HCO, and stir Then, quickly lower the temperature to below 45 ° C to solidify, and then naturally dry or dry under reduced pressure, remove the solvent, and pulverize the obtained active ingredient I HCO solid dispersion to less than 250 ⁇ m to obtain the active ingredient / solid dispersion particles ( Drug-loaded microparticles); quantitatively take the drug-loaded microparticles prepared above, add non-ionic surfactants, and add an appropriate amount of water to prepare a viscous After the thick liquid, colloid mill is used to further grind the fineness of the drug-loaded particles to less than 100 ⁇ m, and then add water-soluble antioxidants, preservatives and water for injection to the final volume.
  • a micronized active compound such as a macrolide insect repellent or N-phenylpyrazole insect repellent
  • Method (2) Supersaturated active ingredient solution (with or without suspending agent) or a solution containing a high concentration of anti-parasite drugs (with or without suspending agent) or micronized active ingredient with melted or Dissolved HCO or other hydrophobic carrier materials are mixed uniformly, with or without non-ionic surfactants, and then controlled at a certain temperature, mixed with water or other liquids with poor ability to dissolve active ingredients under stirring conditions, and the solids in the system will be dispersed. After the body is formed, grind, add the remaining medium, and if necessary, add other additives (such as non-ionic surfactants, suspending agents, antioxidants, etc.) to obtain the active dispersion / hydrophobic carrier material solid dispersion. Release injection. Or, the solid body in the system is separated, dried, and pulverized, and then a liquid medium is added to disperse and homogenize to obtain a suspension injection.
  • additives such as non-ionic surfactants, suspending agents, antioxidants, etc.
  • the antiparasitic drugs or active ingredients include antiprotozoal drugs, antihelmintic drugs and antiparasitic drugs; preferably macrolide insect repellents (Avermectin abamitin, Ivermectin ivermectin, Emma Emamectin, eprinomectin, doramectin, moxidectin), salicylanilide antiparasitic drugs (preferably chlorocyanamide and its sodium salt), organic monument antiparasitic Insecticides, tetraimidazoles (such as levamisole), N-phenylpyrazole insect repellents (such as fipronil), insect growth regulators (such as fenprobenil, cyclopromazine), and triazines (Such as Diclazuril, Baiqiuqing).
  • macrolide insect repellents Avermectin abamitin, Ivermectin ivermectin, Emma Emamectin,
  • the hydrophobic carrier material includes animal wax, vegetable wax, alkane compounds in a solid state below 45 ° C, fatty acids or fatty acid ester compounds in a solid state below 45 ° C, and Esters of mono- or polyhydric alcohols, hydrogen Chemical vegetable oil, rosin and its derivatives, ethyl cellulose, polyethylene, polyvinyl butyral; hydrogenated castor oil (HCO), Brazilian wax, ethyl cellulose, rosin pentaerythritol ester, etc. are preferred Rosin esters, which can be used in combination of two or more.
  • the liquid dispersion medium or the solvent for preparing a supersaturated solution of the active ingredient or the liquid having poor solubility to the active ingredient includes: water, a hydrophilic organic liquid, and an ester compound; preferably water, 1, 2-propanediol, and polyethylene Alcohol, glycerol, acetal glycerol, dimethylacetamide, N-methylpyrrolidone, benzyl benzoate, triacetin.
  • the low-boiling organic solvents are acetone, ethyl acetate, ethanol, and the like. During the preparation of the preparation, the above-mentioned hydrophilic organic liquid medium is used in combination with water to obtain better results.
  • the nonionic surfactant is a pharmaceutically usable nonionic surfactant; polyoxyethylene sorbitan fatty acid ester (Tween series), sorbitan fatty acid ester (Span series), and castor oil polymer are preferred. Oxyethylene ether (EL series); they can be used alone or in combination. Especially choose Span, Tween series emulsifiers.
  • the suspending agent is preferably carboxyfluorenyl cellulose (sodium), fluorenyl cellulose, xanthan gum, polyvinylpyrrolidone. Polyethylene glycol, sodium alginate, propylene glycol sodium alginate, etc. with a molecular weight greater than 1000. These suspending agents are well known in the art.
  • HCO has good "affinity" with hydrophobic antiparasitic drugs such as ivermectin (IVM for short). Therefore, the present invention specifically selects HCO as a solid dispersion medium to prepare solid dispersion particles containing antiparasitic drugs.
  • OK in HCO solid dispersion particles Add ethyl cellulose or rosin pentaerythritol ester;
  • the HCO solid dispersion particles are combined into a compound sustained-release preparation.
  • compositions and preparation method of the present invention are:
  • Formulation A Sustained-release injection containing ivermectin / HCO drug-loaded microparticles
  • Formulation B slow-release injection containing IVM / HCO drug-loaded microparticles
  • composition of preparation (1) Composition of preparation:
  • Formulation C Sustained-release injection of fipronil / HCO drug-loaded microparticles
  • Preparation method (1) take fipronil and dissolve it with acetone, add it to an aqueous solution with or without PVP under stirring conditions to rapidly crystallize, centrifuge or filter, remove water / acetone, and obtain the fipronil ⁇
  • the powder is dispersed in the melted HCO. When it is cooled to semi-solidified, it is ground with water, and then (or without) non-ionic surfactant, and the remaining medium is added to the final volume, so that the micronized powder containing fipronil is obtained. Release injection.
  • Preparation method (2) Dissolve fipronil with a small amount of an injectable solvent to make a supersaturated solution or a high-concentration solution, and then mix it with the melted HCO uniformly. Then, under the conditions of controlling temperature and stirring speed, Mix with water to solidify, grind, homogenize, add (or not) non-ionic surfactants, and add the remaining medium to the final volume.
  • Preparation method (3) Dissolve fipronil with a solvent having a boiling point of less than 100 ° C (such as acetone) to prepare a supersaturated solution, and then mix it with the melted HCO and mix, and cool under stirring. However, it is solidified to obtain a fipronil / HCO solid dispersion, which is naturally dried or pulverized after drying under reduced pressure to obtain fine particles of fipronil / HCO solid dispersion. The solid dispersion fine powder is taken and dispersed in a medium to obtain Sustained-release injection containing micronized fipronil / HCO solid dispersion.
  • a solvent having a boiling point of less than 100 ° C such as acetone
  • compositions and preparation method of the present invention are:
  • Formulation A Sustained-release injection containing 2-10% IVM 16-20% HCO drug-loaded microparticles (1)
  • Formulation B Sustained-release injection containing fipronil / HCO drug-loaded microparticles, the preparation method is to use fipronil 1-3 times the solvent (acetone, ethanol, 1, 2-propanediol, acetaldehyde glycerol, difluorene Acetacetamide or N-fluorenyl-pyrrolidone) is dissolved, mixed with the melted HCO uniformly, and then under the conditions of controlled temperature and stirring speed, mixed with water to solidify, grind, homogenize, add the remaining medium and Additive to final volume.
  • the slow-release preparation containing the antiparasitic drug according to the present invention is injectable or oral, and is used to prevent and treat animal parasitic diseases.
  • the subcutaneous injection is selected, and the dosage is 0.4-4 mg (macrolide deworming drug). ) / Per kilogram of body weight, the suitable dosage is: 0.7-1.5mg macrolide insect repellent per kilogram of body weight.
  • HCO / IVM solid dispersion prepared above is dried under reduced pressure and pulverized to 150 ⁇ m or less to obtain HCO / IVM (2: 1) solid dispersion particles.
  • Example 2 Preparation of a sustained-release injection containing 7% IVM / 14% HCO solid particles. Take 1 kg of IVM and 2 kg of HCO, and heat with dimethylacetamide or 1,2-propanediol to 95. C is dissolved. When the temperature of the solution drops to room temperature and solidifies, 6 L of water is poured into the mouth, ground, and then Tween-80 and Span-80 are added, ground and stirred for 2-4 hours, and then water is added to the final volume. You can also add emulsifier first, then add water, stir and homogenize, and then add the remaining medium to the final volume.
  • Example 3 Preparation of a sustained-release injection containing 5% IVM and 15% HCO solid particles. Take lkglVM, add 1,2-propanediol, and dissolve it at 90 ° C. Add 1 kg of HCO. After thawing, add water and glycerol at room temperature when it just solidifies. Triacetate, grind, then add Tween-80 and Span-80, stir for 2-4 hours and add water to the final volume.
  • Example 4 Preparation of a sustained-release injection containing 3% IVM / 6% HCO solid particles. Take 1 kg of IVM which has been ultra-pulverized (less than 2 ⁇ ), and add it to a 2 kg HCO solution that has been cooled to about 60 ° C. Add 1 L of 1,2-propanediol / water (1: 1) solution, grind, add OP-10, add water to the final volume.
  • IVM3g Take IVM3g, EC (RT10) 3g, add 10ml diamidoacetamide, heat to dissolve, add 3g HCO, melt and homogenize, add 20ml water, grind, homogenize, add a certain amount of glycerin or a certain amount of OP-10, add water to the final volume.
  • EC (RT10) 3g add 10ml diamidoacetamide, heat to dissolve, add 3g HCO, melt and homogenize, add 20ml water, grind, homogenize, add a certain amount of glycerin or a certain amount of OP-10, add water to the final volume.
  • Example 8 Preparation of a sustained-release injection containing 7% IVM 1 14% HCO solid particles. Take 3.5 kg of IVM, dissolve it with 6 L of aldol and heat it to 90 ° C, and mix with 7 kg of melted HCO. Mix in cold water, grind, and add 10 L of 1,2-propanediol solution containing 0.5 L of really methanol and 1.5 kg of PVP to obtain it.
  • HCO I IVM (0.5: 1) solid dispersion fine powder, add 3-6 times (weight / volume ratio) glycerol triacetate and 5-20% ethanol / water (2: 1)
  • the solution is prepared as a suspension injection. This preparation is used for the prevention and treatment of animal parasitic diseases, and the subcutaneous injection dose is 1-2 mg IVM / kg body weight. The duration of effect is more than 60 days.
  • Example 10 Sustained-release injection containing 10% IVM
  • Example 11 Sustained-release injection containing 2% avermectin (AVM)
  • Example 12 Preparation of a sustained-release injection containing 5% IVM 1 15% HCO Take 5g of IVM, add 10ml of dimethylacetamide and 1ml of phenethyl alcohol, stir to dissolve IVM, add 15g of melted HCO and mix well, mix with 30-40ml of water for injection under stirring, grind, homogenize, Add 10-20 ml of glycerol and an aqueous solution containing 0.3 g of sodium thiosulfate and 3 g of polyvinylpyrrolidone to the final volume.
  • Example 13 The preparation of Example 12 was used for the control of nematodes and pruritus in sheep. Select 200 sheep that are naturally infected with nematodes and itch mites, of which 20 are control sheep, and the remaining groups are 60 sheep. Group 1 was injected with the preparation of 1ml / 50kgb.w. Example 12; group 2 was injected with 2ml / 50kg bw The preparation of Example 12; the third group was injected with conventional 1% ivermectin injection 5ml / 50kg, and the above four groups of experimental sheep were mixed and fed.
  • Example 9 In the drug control group (Group 3), 8 sheep had bitten on the 31st day, and 37 sheep had bitten on the 50th day, and live mites were detected by microscopy; No biting occurred and no live mites were detected; in the first group, four sheep had bites and the live mites were detected on the 55th day; the second group had four sheep had bites and the live mites were detected on the 85th day; It can be seen that a) the preparation of Example 9 has a good sustained-release effect; b) with the increase of the dosage, the holding period is prolonged. (4) On the 95th day, 10 sheep were dissected from each group, and worms were detected in the control group and the third group. The average number of worms was 272 per sheep, and neither group 1 nor group 2 was detected. Nematode body.
  • Example 14 Blood samples were taken from the sheep in the medication group of Example 13 on the 1st, 2nd, 3rd, 4th, 5th, 6th, 20th, 40th, 60th, 80th, 95th, and 110th days after the administration, and the ivermectin content in the plasma was analyzed. Three sheep. The experimental results show that the peak blood drug time in the medication group is 2-6 days, and the peak blood drug concentrations are 19-23ng / ml in the first group, 24-30ng / ml in the second group, and 85-94ng in the third group.
  • the blood concentration of group 1 dropped to 2-4 ng / ml, and the blood concentration of group 3 fell below 1 ng / ml; on day 60, the blood concentration of group 1 decreased to 2 ng / ml.
  • the blood concentration of the third group dropped to below 0.3 ng / ml, while the blood concentration of the second group was about 5 ng / ml, and the blood concentration on the 95th day remained at 2-3 ng / ml.

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  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Molecular Biology (AREA)
  • Epidemiology (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne un produit d'injection à libération soutenue comprenant des substances anti-parasites. Le composant actif de la préparation se présente sous la forme d'une dispersion solide de particules. Le produit d'injection est, de préférence, constitué de particules de dispersion solides formées d'insectifuges macrolides et d'huile de ricin hydrogénée (HCO). Le procédé de préparation est de préférence un procédé sans solvant, consistant à : dissoudre de l'envimycine dans une quantité correspondant à une à deux fois celle de diméthyle acétamide; mélanger le tout de manière homogène avec de l'huile HCO fondue; mélanger le tout à de l'eau et à de la glycérine; le moudre pour l'obtention d'une dispersion solides possédant une taille de particules <100 μm, puis ajouter de l'eau injectable et un excipient de manière qu'un volume final soit obtenu. Un produit d'injection peut aussi être préparé par la dispersion de particules de dispersion solide pré-préparées de HCO et de l'envimycine dans le véhicule liquide. Le produit d'injection de l'invention est biocompatible et a un effet de libération soutenue excellent.
PCT/CN2003/000389 2002-05-31 2003-05-26 Produit d'injection a liberation soutenue contenant des substances anti-parasites Ceased WO2003101419A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003234894A AU2003234894A1 (en) 2002-05-31 2003-05-26 Anti-parasite containing sustained release injection

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
CN02120747 2002-05-31
CN02120747.X 2002-05-31
CN02131198.6 2002-10-17
CN02131198 2002-10-17
CNB02153425XA CN1275589C (zh) 2002-05-31 2002-11-27 含抗寄生虫药物的缓释注射剂
CN02153425.X 2002-11-27

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WO2003101419A1 true WO2003101419A1 (fr) 2003-12-11

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PCT/CN2003/000389 Ceased WO2003101419A1 (fr) 2002-05-31 2003-05-26 Produit d'injection a liberation soutenue contenant des substances anti-parasites

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AU (1) AU2003234894A1 (fr)
WO (1) WO2003101419A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013165264A1 (fr) * 2012-05-01 2013-11-07 Nexan Corporation Limited Compositions anthelminthiques
CN108392424A (zh) * 2018-05-14 2018-08-14 山西鑫煜制药有限公司 一种在制药过程中使微量成分混合均一的方法及应用
CN112190567A (zh) * 2020-11-09 2021-01-08 山东华辰制药有限公司 一种伊维菌素缓释微球的制备方法及应用

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005084688A1 (fr) * 2004-03-04 2005-09-15 Yuwan Wang Poudre injectable contenant un vermifuge
BRPI0611433A2 (pt) * 2005-05-05 2010-09-08 Sanofi Aventis Us Llc formulações estáveis de nanopartìcula
CN101152184B (zh) * 2007-09-06 2010-05-26 浙江大学 一种禽用地克珠利泡腾片
RU2361616C1 (ru) * 2008-04-28 2009-07-20 Государственное образовательное учреждение высшего профессионального образования "БАШКИРСКИЙ ГОСУДАРСТВЕННЫЙ МЕДИЦИНСКИЙ УНИВЕРСИТЕТ Федерального Агентства по здравоохранению и социальному развитию" (ГОУ ВПО БГМУ РОСЗДРАВА) Инъекционный растворитель пролонгированного действия
MA34052B1 (fr) * 2010-04-01 2013-03-05 Rotam Agrochem Int Co Ltd Composition insecticide et procédé de lutte contre des insectes l'utilisant
CN103705445A (zh) * 2014-01-06 2014-04-09 王玉万 含乙酰甲喹/氢化蓖麻油的原位胶凝注射剂
CN103721266A (zh) * 2014-01-06 2014-04-16 王玉万 含阿维菌素类药物/氢化蓖麻油的原位胶凝注射剂
CN104095812B (zh) * 2014-07-30 2017-09-19 北京中农华威制药有限公司 含阿维菌素类药物可乳化油质注射剂的制备方法
CN104666244B (zh) * 2015-03-18 2017-08-08 王玉万 含巴西蜡的兽用抗寄生虫制剂

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1215331A (zh) * 1996-04-09 1999-04-28 拜尔公司 以蓖麻油为基础的阿凡曼菌素和米尔倍霉素的注射制剂
CN1283990A (zh) * 1997-12-03 2001-02-14 麦克公司 含有氢化蓖麻油的长效注射制剂

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1215331A (zh) * 1996-04-09 1999-04-28 拜尔公司 以蓖麻油为基础的阿凡曼菌素和米尔倍霉素的注射制剂
CN1283990A (zh) * 1997-12-03 2001-02-14 麦克公司 含有氢化蓖麻油的长效注射制剂

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013165264A1 (fr) * 2012-05-01 2013-11-07 Nexan Corporation Limited Compositions anthelminthiques
AU2013257335B2 (en) * 2012-05-01 2017-03-02 Nexan Corporation Limited Anthelmintic compositions
CN108392424A (zh) * 2018-05-14 2018-08-14 山西鑫煜制药有限公司 一种在制药过程中使微量成分混合均一的方法及应用
CN112190567A (zh) * 2020-11-09 2021-01-08 山东华辰制药有限公司 一种伊维菌素缓释微球的制备方法及应用

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Publication number Publication date
CN1461640A (zh) 2003-12-17
CN1275589C (zh) 2006-09-20
AU2003234894A1 (en) 2003-12-19

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