CN101057831A - Docetaxel liposome novel preparations and its preparation method - Google Patents
Docetaxel liposome novel preparations and its preparation method Download PDFInfo
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Abstract
The invention discloses a new dosage form for polyene alcohols Paclitaxel liposome and the preparing method. The invention employs membrane dispersion method, organic solvent injection method to prepare polyene alcohols Paclitaxel liposome or employs PEG modified phosphatide or other liposome material to modify liposome and produce long circulating liposome, then produce polyene alcohols Paclitaxel injection and freeze drying agent through processes of super-sound, squeezing or high-pressure homogeneity. Compared with normal injection, the polyene alcohols Paclitaxel liposome is characterized in that it can reduce medicine toxic effect, the long circulating liposome greatly increases the circulating time of liposome in the body and the medicine can target tumor more effectively.
Description
Technical field:
The invention belongs to medical technical field, relate to targeting drug administration preparation docetaxel liposome formulation and preparation method thereof, more specifically be meant the common and long circulating liposomes that a kind of partially synthetic taxinane kind anti-cancer drugs-Docetaxel and suitable adjuvant are made, Docetaxel is by being prepared into the effect that common and long circulating liposomes reaches cancer target.
Background technology:
Liposome is a kind of novel form of targeting drug delivery system, and this system is up-to-date, the most promising drug-supplying system of present pharmaceutics.Liposome is the focus of pharmaceutics research as a member of this system always, it can with drug selectivity be transported to the target spot position, the performance therapeutical effect does not influence the function of normal cell, tissue or organ again simultaneously, thereby reaches the purpose that improves curative effect, reduces toxic and side effects.
Conventional liposome is very fast by reticuloendothelial system phagocytic in the body after entering in the body, and main targeting is in reticuloendothelial system organs such as liver, spleen, bone marrow, targeting to other positions is relatively poor, and it is subject to the effect of albumen, enzyme etc. in vivo and seepage takes place, and affects the treatment and toxicity is increased.In order to address this problem, the exploitation of anticarcinogen long circulating liposome preparation in recent years becomes the focus of the world, domestic research, because that said preparation has is efficient, long-acting, the characteristics of targeting, low toxicity, to the curative effect that improves anticarcinogen, alleviate toxicity and have great importance, greatly improved patient's quality of life.The relative conventional liposome of long circulating liposomes, with certain material its surface is modified, increased the hydrophilic of liposome and sterically hindered, can avoid by reticuloendothelial system phagocytic in the body, and easy to leak not in vivo, the longer body-internal-circulation time had, higher blood drug level, make medicine effectively be enriched in tumor locus, therefore can better bring into play curative effect, alleviate toxicity.
Docetaxel (commodity of import product are called taxotere) is the non-activity chemical compound that extracts in the needle by European yew, this product is by a semi-synthetic paclitaxel derivant of French Sanofi-Aventis exploitation, it is the microtubule depolymerization inhibitor, it acts on microtubule/tubulin system, by promoting the microtubule dimer to be assembled into microtubule, and by preventing that the multimerization process from making microtubule stable, the retardance cell is in G2 and M phase, thereby the mitosis of anticancer and propagation.Docetaxel is effective to advanced breast cancer, nonsmall-cell lung cancer, ovarian cancer, cancer of pancreas, hepatocarcinoma, tumor of head and neck etc.
Docetaxel is insoluble in water, even be mixed with injection, toxic and side effects in clinical practice is also bigger, cause more complication easily, as anaphylaxis, bone marrow depression, neurotoxicity, Cardiovascular Toxicity, alopecia or the like, bioavailability is lower in the body of medicine simultaneously, and needs life-time service.At present its structure of modification still there is not big progress with the trial that reduces untoward reaction.
Docetaxel mainly is with formulated injection such as polyoxyethylene hydrogenated Oleum Ricini and ethanol at present, the injection back is to the human body toxic side effect, particularly before using the Docetaxel injection, must take Claritin or injection Claritin earlier and help to alleviate the toxic and side effects such as serious allergy that the use owing to the Docetaxel injection produces, usually bring misery, directly influenced the use of this medicine to patient.
Patent CN 1660073A discloses a kind of docetaxel nano-particle and preparation method thereof.Though the more common Docetaxel injection of nanoparticle targeting with the biological degradable material preparation is good, is not long-acting targeting preparation.
Patent CN 1709236A discloses a kind of lipomul that contains docetaxel and preparation method thereof.The lipomul drug loading of this method preparation is less, maximum 1.0mg/ml, and do not have macrocyclic characteristic, the performance that affects the treatment in vivo.
More than two patents giving full play to the drug effect of Docetaxel, reducing and also have certain deficiency aspect the toxicity.
Summary of the invention
The object of the present invention is to provide the common of Docetaxel and long circulating liposomes novel form and preparation method, comprise injection and freeze-dried preparation.Characteristics of the present invention are that Docetaxel is prepared into liposome, can come modified liposome with phospholipid or other matrix materials that PEG modifies simultaneously,
Polyene taxol liposome among the present invention is to use phospholipid, and cholesterol also adds the long-circulation fat material and Docetaxel is written into liposome, the mean diameter≤500nm of decentralized photo in liposome.It can be soybean phospholipid that the present invention prepares the used phospholipid of liposome, Ovum Gallus domesticus Flavus lecithin, hydrogenated soya phosphatide, synthetic phospholipid or its any combining form.The DSPE (PEG-DSPE) that long recycled material can be modified with PEG, Polyethylene Glycol-distearyl acyl group PHOSPHATIDYL ETHANOLAMINE, Polyethylene Glycol-dipalmitoyl phosphatidyl choline, Polyethylene Glycol-two palmityl PHOSPHATIDYL ETHANOLAMINE, ganglioside, polyacrylamide, chitosan, polyvinylpyrrolidone or polyvinyl alcohol or other materials.The weight ratio of matrix material and medicine is 1: 1-100: 1, and the mol ratio of long circulation adjuvant and common phospholipid is 1: 10-1: 200, the ultimate density of Docetaxel is 0.1-20mg/ml in the preparation.Can add a certain amount of charge adjusting agent or surfactant in the film material to improve stability such as oleic acid, 18 carbonic acid, glucuronic acid, DCP, poloxamer or the Bian Ze of liposome.The present invention can also optionally contain one or more among vitamin E, vitamin C, fumaric acid, malic acid, propyl gallate, sodium sulfite and sodium metabisulfite, L-cysteine, L-isoleucine or pH buffer agent phosphate, the EDTA.
The polyene taxol liposome envelop rate of the present invention's preparation is greater than 80%.Preparation method is for to use film dispersion method, organic solvent injection method to prepare liposome, can carry out ultrasonicly thereafter, extrudes or high pressure homogenize.The Docetaxel long circulating liposomes of preparation can directly be preserved with liquid form or carry out making Docetaxel long circulating liposomes freeze-dried powder after the lyophilization.Freeze drying protectant can be sucrose, trehalose, and mannitol, sodium chloride, glucose, lactose, sorbitol, dextran, glycerol, glycine, lysine or its any combining form, the ratio of freeze drying protectant and phospholipid is 10-20: 0.5-6.0.
The polyene taxol liposome of gained can directly be preserved with liquid form or add freeze drying protectant and carry out making the polyene taxol liposome lyophilized injectable powder after the lyophilization.
The present invention prepares the common and long circulating liposomes of Docetaxel, and its disperse medium can be water, phosphate buffer, TriS buffer, carbonate buffer solution, 5% D/W, 0.9%Nacl etc.
Advantage of the present invention is: conventional liposome can be avoided some toxic and side effects of normal injection, and tumor is had certain targeting; Long circulating liposomes can significantly improve liposome circulation time in vivo, make medicine more long-term effectively targeting can bring into play drug effect better in tumor locus, reduce toxicity; It is ultrasonic that the present invention adopts film dispersion method or organic solvent injection method to prepare to adopt behind the liposome, and high pressure homogenize or the method for extruding can make the less and distribution uniform of liposome particle diameter of preparation.
Description of drawings:
Fig. 1 is the curve during rat plasma medicine among the embodiment 15
The specific embodiment:
The specific embodiment of the present invention, by following embodiment explanation, but protection scope of the present invention is not limited to this.
Embodiment 1
With the 100mg Docetaxel, 1500mg soybean phospholipid, 150mg cholesterol, 100mg Polyethylene Glycol-distearyl acyl group PHOSPHATIDYL ETHANOLAMINE (PEG-DSPE), 6.8mg vitamin E ultrasonic dissolution get solution A in the 10ml dehydrated alcohol.
With A rotary evaporation film forming in 50 ℃ of water-baths, get film B.
Phosphate buffer (pH7.4) 5ml was fully mixed aquation 30 minutes with film B, and 0.22 μ m microporous filter membrane is crossed in ultrasonic concussion 5 minutes, fills nitrogen, and embedding promptly.
With the 100mg Docetaxel, 1200mg soybean phospholipid, 300mg hydrogenation saturated phospholipid, 100mg cholesterol, 50mg ganglioside (GM), 6.5mg vitamin E ultrasonic dissolution get solution A in the 50ml dehydrated alcohol.
With A rotary evaporation film forming in 50 ℃ of water-baths, get film B.
Phosphate buffer (pH7.4) 50ml was fully mixed aquation 30 minutes with film B, and high pressure homogenizer circulation homogenizing 5～6 times is crossed 0.22 μ m microporous filter membrane then, and nitrogen is filled in packing, and embedding promptly.
Embodiment 3
With the 100mg Docetaxel, 1000mg soybean phospholipid, 250mg cholesterol, 100mg Polyethylene Glycol-distearyl acyl group PHOSPHATIDYL ETHANOLAMINE (PEG-DSPE), 6.5mg vitamin E, oleic acid 100mg ultrasonic dissolution get solution A in the 50ml dehydrated alcohol.
With A rotary evaporation film forming in 60 ℃ of water-baths, get film B.
Water for injection 50ml and film B were fully mixed aquation 30 minutes, and high pressure homogenizer circulation homogenizing 5～6 times is crossed 0.22 μ m microporous filter membrane then, and nitrogen is filled in packing, and embedding promptly.
Embodiment 4
With the 100mg Docetaxel, the 1000mg soybean phospholipid, 300mg hydrogenation saturated phospholipid, 100mg cholesterol, 100mg Polyethylene Glycol-dipalmitoyl phosphatidyl choline (PEG-DPPC), 6.5mg vitamin E, oleic acid 50mg ultrasonic dissolution get solution A in the 50ml dehydrated alcohol.
With A rotary evaporation film forming in 40 ℃ of water-baths, get film B.
Water for injection 50ml and film B were fully mixed aquation 30 minutes, and high pressure homogenizer circulation homogenizing 5～6 times is crossed 0.22 μ m microporous filter membrane then, and nitrogen is filled in packing, and embedding promptly.
Embodiment 5
With the 200mg Docetaxel; the 1500mg soybean phospholipid; 500mg hydrogenation saturated phospholipid, 150mg cholesterol, 100mg Polyethylene Glycol-distearyl acyl group PHOSPHATIDYL ETHANOLAMINE (PEG-DSPE), 7.2mg vitamin E, oleic acid 50mg ultrasonic dissolution get solution A in the 50ml dehydrated alcohol.
With A rotary evaporation film forming in 50 ℃ of water-baths, get film B.
9% aqueous sucrose solution 50ml and film B were fully mixed aquation 30 minutes, high pressure homogenizer circulation homogenizing 5～6 times, 121 ℃ of sterilizations then, packing, nitrogen is filled in lyophilization, and embedding is promptly.
Embodiment 6
With the 250mg Docetaxel, the 1500mg soybean phospholipid, 500mg hydrogenation saturated phospholipid, 150mg cholesterol, 150mg Polyethylene Glycol-two palmityl PHOSPHATIDYL ETHANOLAMINE (PEG-DPPE), 7.2mg vitamin E, oleic acid 50mg ultrasonic dissolution get solution A in the 10ml dehydrated alcohol.
With the phosphate buffer 50ml of 40 ℃ of heating in water bath of A injection, rotary evaporation in vacuo is removed ethanol, is settled to 50ml and gets solution B.
Solution B through high pressure homogenizer circulation homogenizing 5～6 times, is crossed 0.22 μ m microporous filter membrane then, and nitrogen is filled in packing, and embedding promptly.
Embodiment 7
With the 250mg Docetaxel; the 1500mg soybean phospholipid; 500mg hydrogenation saturated phospholipid, 150mg cholesterol, 150mg Polyethylene Glycol-distearyl acyl group PHOSPHATIDYL ETHANOLAMINE (PEG-DSPE), 7.2mg vitamin E, oleic acid 50mg ultrasonic dissolution get solution A in the 10ml dehydrated alcohol.
With the phosphate buffer 50ml of 50 ℃ of heating in water bath of A injection, rotary evaporation in vacuo is removed ethanol, is settled to 50ml and gets solution B.
Solution B through high pressure homogenizer circulation homogenizing 5～6 times, is added freeze drying protectant sucrose 4g, mannitol 1g dissolving, cross 0.22 μ m microporous filter membrane then, packing, lyophilization are promptly.
With the 200mg Docetaxel; the 800mg soybean phospholipid; 400mg hydrogenation saturated phospholipid, 100mg cholesterol, 100mg Polyethylene Glycol-distearyl acyl group PHOSPHATIDYL ETHANOLAMINE (PEG-DSPE), 7.2mg vitamin E, poloxamer 50mg ultrasonic dissolution get solution A in the 10ml dehydrated alcohol.
With the phosphate buffer 50ml of 60 ℃ of heating in water bath of A injection, rotary evaporation in vacuo is removed ethanol, is settled to 50ml and gets solution B.
Solution B through high pressure homogenizer circulation homogenizing 5～6 times, is added freeze drying protectant trehalose 3g, glucose 1.5g, the dissolving of L-cysteine, cross 0.22 μ m microporous filter membrane then, packing, lyophilization are promptly.
Embodiment 9
With the 200mg Docetaxel; the 800mg soybean phospholipid; 400mg hydrogenation saturated phospholipid, 100mg cholesterol; 100mg Polyethylene Glycol-distearyl acyl group PHOSPHATIDYL ETHANOLAMINE (PEG-DSPE), 5mg polyvinylpyrrolidone (PVP), 7.2mg vitamin E, poloxamer 50mg ultrasonic dissolution get solution A in the 10ml dehydrated alcohol.
With the phosphate buffer 50ml of 50 ℃ of heating in water bath of A injection, rotary evaporation in vacuo is removed ethanol, is settled to 50ml and gets solution B.
Solution B through high pressure homogenizer circulation homogenizing 5～6 times, is added freeze drying protectant sucrose 4g dissolving, cross 0.22 μ m microporous filter membrane then, packing, lyophilization are promptly.
With the 100mg Docetaxel, 3000mg soybean phospholipid, 700mg cholesterol, 6.8mg vitamin E ultrasonic dissolution get solution A in the 10ml dehydrated alcohol.
With A rotary evaporation film forming in 40 ℃ of water-baths, get film B.
Phosphate buffer (pH7.4) 5ml was fully mixed aquation 30 minutes with film B, and 0.22 μ m microporous filter membrane is crossed in ultrasonic concussion 5 minutes, fills nitrogen, and embedding promptly.
Embodiment 11
With the 250mg Docetaxel, 1500mg soybean phospholipid, 500mg hydrogenation saturated phospholipid, 150mg cholesterol, 7.2mg vitamin E, oleic acid 50mg ultrasonic dissolution get solution A in the 10ml dehydrated alcohol.
With A rotary evaporation film forming in 50 ℃ of water-baths, get film B.
9% aqueous sucrose solution 50ml and film B were fully mixed aquation 30 minutes, and high pressure homogenizer circulation homogenizing 5～10 times is crossed 0.22 μ m microporous filter membrane then, packing, and nitrogen is filled in lyophilization, and embedding is promptly.
With the 250mg Docetaxel, 1500mg soybean phospholipid, 500mg hydrogenation saturated phospholipid, 150mg cholesterol, 7.2mg vitamin E, oleic acid 50mg, poloxamer 50mg ultrasonic dissolution get solution A in the 10ml dehydrated alcohol.
With the phosphate buffer 50ml of 40 ℃ of heating in water bath of A injection, rotary evaporation in vacuo is removed ethanol, is settled to 50ml and gets solution B.
Solution B through high pressure homogenizer circulation homogenizing 5～6 times, is crossed 0.22 μ m microporous filter membrane then, and nitrogen is filled in packing, and embedding promptly.
Embodiment 13
With the 100mg Docetaxel, 1200mg soybean phospholipid, 300mgDPPC, 100mg cholesterol, 6.5mg vitamin E ultrasonic dissolution get solution A in the 50ml dehydrated alcohol.
With A rotary evaporation film forming in 60 ℃ of water-baths, get film B.
Phosphate buffer (pH7.4) 50ml was fully mixed aquation 30 minutes with film B, and high pressure homogenizer circulation homogenizing 5～6 times is crossed 0.22 μ m microporous filter membrane then, and nitrogen is filled in packing, and embedding promptly.
Embodiment 14
With the 100mg Docetaxel, 1200mg soybean phospholipid, 300mgDPPA, 100mg cholesterol, 6.5mg vitamin E ultrasonic dissolution get solution A in the 10ml dehydrated alcohol.
With the phosphate buffer 50ml of 60 ℃ of heating in water bath of A injection, rotary evaporation in vacuo is removed ethanol, is settled to 50ml and gets solution B.
With solution B through high pressure homogenizer circulation homogenizing 5～6 times, 121 ℃ of sterilizations then, nitrogen is filled in packing, embedding is promptly.
Embodiment 15 rat pharmacokinetic studies
Get 15 healthy Wistar rats, be divided into 3 groups at random, 5 every group.At one night of fasting before the experiment, femoral vein gives the normal injection of equivalent Docetaxel respectively, conventional liposome and long circulating liposomes, and dosage press coefficient by people's clinical use amount and is converted and be the dosage of rat.After the administration 0.25,0.5,1,2,4,8,12,14,16,24h gets blood 0.5mL in the dry centrifuge tube of 1.5mL anticoagulant heparin from the rat eye socket, the centrifugal 5min of 5000r/min, get plasma treatment by the drug level in the HPLC method mensuration blood plasma, curve when drawing medicine.
Embodiment 16 mouse tissues distribute and study
Get 18 of mices, be divided into two groups at random, the tail vein is converted the Docetaxel conventional liposome and the long circulating liposomes of dosage respectively, and in 3h, 8h, 12h put to death and get liver and spleen tissue, clean with normal saline after the administration, and filter paper blots.Precision takes by weighing handles the drug level in organizing with HPLC method mensuration after the back is smashed in tissue refiner to pieces with methanol.The result shows that long circulating liposomes is less by the liver spleen tissue of mice picked-up.
Embodiment 17 antitumor actions
Antitumor action test is a laboratory animal with colon 26 carcinoma lotus tumor BALB/C mice, connects behind the tumor cell begin treatment when diameter of tumor reaches 5mm, with 5mg/kg and the quiet notes of 15mg/kg, writes down tumor growth and survival rate.In the 15mg/kg group, the tumour inhibiting rate of Docetaxel long circulating liposomes improves 0.4 times and 1.3 times respectively than conventional liposome and normal injection.In the 15mg/kg group, the tumour inhibiting rate of Docetaxel long circulating liposomes improves 1.3 times and 2.5 times respectively than conventional liposome and normal injection, and survival rate has improved 2 times and 4 times respectively than conventional liposome and normal injection.
Claims (8)
1, docetaxel liposome formulation is characterized in that: with lipid and/or cholesterol is the film material, and available long circulation adjuvant carries out finishing, is prepared into the common or long circulating liposomes of Docetaxel, and the mol ratio of lipid and medicine is 1: 1-100: 1; The mol ratio of long circulation adjuvant and common phospholipid is 1: 10-1: 200; The ultimate density of Docetaxel is 0.1-20mg/ml in the preparation, the mean diameter≤500nm of decentralized photo, and its envelop rate is greater than 80%.
2, docetaxel liposome formulation according to claim 1 is characterized in that: preferred phospholipid of matrix material and cholesterol; Phospholipid can adopt natural phospholipid, synthetic phospholipid or its mixture; Can add a certain proportion of charge adjusting agent or surfactant in the film material, as oleic acid, 18 carbonic acid, glucuronic acid, DCP, poloxamer or Bian Ze.
3, docetaxel liposome formulation according to claim 1 is characterized in that: long circulation adjuvant can adopt Polyethylene Glycol-distearyl acyl group PHOSPHATIDYL ETHANOLAMINE, Polyethylene Glycol-dipalmitoyl phosphatidyl choline, Polyethylene Glycol-two palmityl PHOSPHATIDYL ETHANOLAMINE, ganglioside, polyacrylamide, chitosan, polyvinylpyrrolidone or polyvinyl alcohol.
4, docetaxel liposome formulation according to claim 1 is characterized in that: can optionally contain among vitamin E, vitamin C, fumaric acid, malic acid, propyl gallate, sodium sulfite and sodium metabisulfite, L-cysteine, L-isoleucine or pH buffer agent phosphate, the EDTA one or more.
5, the preparation method of docetaxel liposome formulation is characterized in that: with Docetaxel, and phospholipid, cholesterol, long circulation adjuvant, vitamin E ultrasonic dissolution get solution A in dehydrated alcohol, and wherein the mol ratio of lipid and medicine is 1: 1-100: 1; The mol ratio of long circulation adjuvant and common phospholipid is 1: 10-1: 200; The ultimate density of Docetaxel is 0.1-20mg/ml in the preparation, with A rotary evaporation film forming in 50 ℃ of water-baths, gets film B, the pH7.4 phosphate buffer was fully mixed aquation 30 minutes with film B, and 0.22 μ m microporous filter membrane is crossed in ultrasonic concussion 5 minutes, fill nitrogen, embedding promptly.
6, the preparation method of docetaxel liposome formulation, it is characterized in that: with Docetaxel, soybean phospholipid, hydrogenation saturated phospholipid, cholesterol, long circulation adjuvant, vitamin E ultrasonic dissolution are in dehydrated alcohol, get solution A, wherein the mol ratio of lipid and medicine is 1: 1-100: 1; The mol ratio of long circulation adjuvant and common phospholipid is 1: 10-1: 200; The ultimate density of Docetaxel is 0.1-20mg/ml in the preparation; A is injected the phosphate buffer of 60 ℃ of heating in water bath; rotary evaporation in vacuo is removed ethanol; be settled to 50ml and get solution B; solution B through high pressure homogenizer circulation homogenizing 5～6 times, is added freeze drying protectant trehalose, glucose, the dissolving of L-cysteine, cross 0.22 μ m microporous filter membrane then; packing, lyophilization are promptly.
7, the preparation method of docetaxel liposome formulation is characterized in that: the polyene taxol liposome of gained can directly be preserved with liquid form or add freeze drying protectant and carry out making the polyene taxol liposome lyophilized injectable powder after the lyophilization.
8, the common and long circulating liposomes of Docetaxel according to claim 8; it is characterized in that: the freeze drying protectant of freeze-dried powder can be sucrose; trehalose, mannitol, sodium chloride; glucose; lactose, sorbitol, dextran; in glycerol or the glycine one or more, the ratio of freeze drying protectant and phospholipid is 10-20: 0.5-6.0.
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| CN 200610082245 CN1846692A (en) | 2006-05-15 | 2006-05-15 | Long circulation liposome prepn of polyene taxol and its prepn process |
| CNA2007101015358A CN101057831A (en) | 2006-05-15 | 2007-04-26 | Docetaxel liposome novel preparations and its preparation method |
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| CN102579341A (en) * | 2011-01-11 | 2012-07-18 | 沈阳药科大学 | Docetaxel solid lipid nanoparticle and preparation method thereof |
| CN102920660A (en) * | 2012-10-18 | 2013-02-13 | 福建医科大学附属协和医院 | Novel liver cancer treatment preparation with physical and biological double-targeting effect |
| CN103768018A (en) * | 2012-10-17 | 2014-05-07 | 南京绿叶思科药业有限公司 | Cabazitaxel liposome injection and preparation method thereof |
| CN106310265A (en) * | 2015-06-30 | 2017-01-11 | 清华大学 | Pharmaceutical composition and preparation method and application thereof |
| CN107677528A (en) * | 2017-09-20 | 2018-02-09 | 上海贞元诊断用品科技有限公司 | Calibration object and quality-control product of a kind of anticoagulant heparin detection reagent and preparation method thereof |
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2007
- 2007-04-26 CN CNA2007101015358A patent/CN101057831A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102579341A (en) * | 2011-01-11 | 2012-07-18 | 沈阳药科大学 | Docetaxel solid lipid nanoparticle and preparation method thereof |
| CN103768018A (en) * | 2012-10-17 | 2014-05-07 | 南京绿叶思科药业有限公司 | Cabazitaxel liposome injection and preparation method thereof |
| CN102920660A (en) * | 2012-10-18 | 2013-02-13 | 福建医科大学附属协和医院 | Novel liver cancer treatment preparation with physical and biological double-targeting effect |
| CN102920660B (en) * | 2012-10-18 | 2013-12-11 | 福建医科大学附属协和医院 | Novel liver cancer treatment preparation with physical and biological double-targeting effect |
| CN106310265A (en) * | 2015-06-30 | 2017-01-11 | 清华大学 | Pharmaceutical composition and preparation method and application thereof |
| CN107677528A (en) * | 2017-09-20 | 2018-02-09 | 上海贞元诊断用品科技有限公司 | Calibration object and quality-control product of a kind of anticoagulant heparin detection reagent and preparation method thereof |
| WO2019218857A1 (en) * | 2018-05-18 | 2019-11-21 | 上海维洱生物医药科技有限公司 | Docetaxel palmitate liposome and preparation method therefor |
| CN110496103A (en) * | 2018-05-18 | 2019-11-26 | 上海维洱生物医药科技有限公司 | A kind of docetaxel palmitate lipid body and preparation method thereof |
| CN110496103B (en) * | 2018-05-18 | 2022-05-10 | 上海维洱生物医药科技有限公司 | Docetaxel palmitate liposome and preparation method thereof |
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