CN101883563A - Injection comprising docetaxel and its preparation - Google Patents
Injection comprising docetaxel and its preparation Download PDFInfo
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- CN101883563A CN101883563A CN2007801017629A CN200780101762A CN101883563A CN 101883563 A CN101883563 A CN 101883563A CN 2007801017629 A CN2007801017629 A CN 2007801017629A CN 200780101762 A CN200780101762 A CN 200780101762A CN 101883563 A CN101883563 A CN 101883563A
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- 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
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/337—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having four-membered rings, e.g. taxol
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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Abstract
The invention provides an injection comprising docetaxel, which contains a mother liquid, ethanol for preventing gel formation of injection, water for keeping the mother liquid in a uniformly flowing state. The mother liquid is a solution containing docetaxel and one or more pharmaceutically acceptable surfactants. The invention also provides a process for preparing the injection consisting of mixing the mother liquid with ethanol, then adding water and mixing uniformly. The injection has high uniformity and high stability, and can extend the time needed to form a crystal precipitation of docetaxel in the injectable solution.
Description
Injection and its compound method technical field containing docetaxel
The present invention provides a kind of injection containing docetaxel, in particular a kind of injection containing docetaxel for extending stability and facilitating healthcare givers to use, the injection is the injection containing docetaxel comprising three components.Background technology
Belong to taxanes（Taxane Paclitaxel)（Paclitaxel) in the approval by United States drug control food office (FDA) in 1992, and as PTS, it is considered as to pass by one of most important cancer therapy drug for over ten years, but the initial stage of medicine listing is not smooth, in addition to raw material such as Pacific yew and Chinese yew limited source, in the first stage（First phase) human trial when, it was found that there is serious allergic reaction in the patient for receiving Paclitaxel treatment, and anaphylactogen not Paclitaxel, but for dissolving the solvent C remophor EL of Paclitaxel, in order to solve the allergic reaction that Cremophor EL allow patient to produce, the solvent for looking for replacement Cremophor EL is the direction studied at present.
Due to the repellency of taxanes（Hydrophobicity）It is high, solubility to water is less than l (^g/mL, so it is not smooth with the solvent for dissolving Paclitaxel to look for replacement Cremophor EL, the intravenous injection that the Paclitaxel Department of Pharmacy of currently the only approval is researched and developed by Shi Guibao companies of the U.S.（), Taxof but the intravenous injection to be used for dissolving the solvent of Paclitaxel be still with 1 using ethanol and Cremophor EL：1 ratio is mixed, even if Cremophor EL content reduction, but still can cause the allergic reaction of patient.
Although also there is researcher to propose that substitute Cremophor EL with organic solvent enjoys (Andersson, B, " Parenteral Paclitaxel in a Stable Non-toxic Formulation " to dissolve the Pacific yew tenth of the twelve Earthly Branches, USP5,877,205, March 2,1999;Hausheer, F.H., Murali, D., and, Seetharamulu, P.,
USP6,040,330, " Pharmaceutical Formulations ofTaxanes ", March 21,2000), the preparation technology disclosed by it is simple, there is the market advantage very much, but these organic solvents have toxicity, therefore do not adopted widely.
Current many researchers are just carried out to look for the solvent of replacement towards two aspects：
1. improve the formula of injection：
It is mainly with micro- fat body formulation and emulsion dissolving Paclitaxel, but, micro- fat body formulation can produce precipitation during storing, so that the stability of drug products is not enough, so being stored during storage with the state for freezing crystalline flour end, but micro- fat body formulation is dried into gelation crystalline flour end and has to pass through the freeze-drying preparation technology of high cost, therefore does not meet economic benefit, product is lost commercialized meaning.
And the research of emulsion is in Panagyiotis, P. et al., Kaufinan are existing disclosed in the periodical that RJ. et al. and Chu, LM. et al. are delivered（Panayiotis, P. et al, WO02/26208, " Emulsion Vehicle for Poorly Soluble Drugs ", April 4,2002;Kaufinan, R.J., and Richard, T.J " USP5,616,330; " Stable Oil-In- Water Emulsions Incorporating a Taxine (Taxol) and Method of Making Same ", April 1,1997;Chu, I.M., and Wang, T.R., USP6,348,491, " Oil-In- Water Emulsion for Encapsulation Paclitaxel ", Feb.19,2002), and the existing fairly good effect of Paclitaxel emulsion being made with emulsion, but its process made is complicated, with high costs, and as micro- fat body formulation, crystalline deposit can be produced during storing, therefore the stability of the medicine is not enough.
2. synthesize the Docetaxel that solubility is higher than Paclitaxel（docetaxd):
Because taxanes are extremely low to the solubility of water, and it is extremely difficult search out good solvent, therefore the solubility Docetaxel high compared with Paclitaxel, the Docetaxel intravenous formulations made by the Docetaxel are synthesized with chemical synthesis（Taxotere) listed by the approval of U.S. FDA, said preparation is dissolved with surfactant, it breaks through to be sizable in this research field at present.
However, being replaced with surfactant in researchs of the Cremophor EL to dissolve Docetaxel or some shortcomings, although the surfactant uses tween（Tween), it can be reduced in the past with toxicity of the organic solvent as solvent, but when to inject with the medicament of Tween dissolving Docetaxels, the medicament must be mixed with the G/W of perfusion liquid such as 5%, but now the mixed liquor can form gel because of excessively sticky, just violent stirring is had to pass through to can dissolve, so that improve said circumstances, the grand Borland Luo Er companies of method business（R one-Poulenc) propose to add two component combine things of intermediate solution, thereby avoid the generation of gel（Precious Mike Bobi, handkerchief Cui Ke, moral, Lan Di, Ji Lisi chief are auspicious, John Cameron Mitchell Villard, " two component injection compositions of additive when being diluted containing the Japanese yew protective embankment derivative in surfactant and prevention ", TaiWan, China patent of invention notification number the 00271395th）The intermediate solution includes additive and the water such as organic compound of the molecular weight less than 200 or sodium chloride, i.e. the intermediate solution is the aqueous solution of the additive, big 6 wt% of its concentration ratio surfactant, in claims of the Patent Case, the concentration of the intermediate solution is the ethanol for being diluted with water into 13 ^%, however, adding the problem of producing following after the intermediate solution：
(a) problem is used：According to the 27th edition General Chapters of American Pharmacopeia<1151>Pharmaceutical dosage forms-injections suggestion, needs in injection in filling excess volume in injection tube for general viscous fluid（Excess volume), such as 0.5ml injection consumption, 0.12ml (24 wt%) excess volume need to additionally be filled, because the viscosity containing Docetaxel and the injection of surfactant is higher, the excess volume of required addition can also be improved, therefore the increase of cost is caused, and healthcare givers needs to spend long time to draw the sticky injection, and the dose of actual absorption can not be grasped, and then influence the precision and curative effect of patient medication, although the intermediate solution added helps to reduce the viscosity of injection, but reduce limitation, so above mentioned problem still occurs.
(b) risk is prepared：Due to the ethanol that intermediate solution is 13^%, but commercially available ethanol is usually 95%, therefore 95% ethanol has to pass through weighing, then goes out 13wt °/^ ethanol with water mixing preparation, however, often
Personal redeployed ethanol every time all might have a little difference, and for the sake of security, the step of sterilizing must being passed through again, so the complexity and risk on manufacturing are even more to greatly improve, comparatively using commercially available 95% ethanol, then more simplified production is with reducing sterile manufacture risk, and progressive is even more apparent.
Stability problem：The medicament allocated can not be in stable state for a long time, and method business dragon Borland Luo Er companies go out the specification of product and just have highlighted that the product has to use in 4 hours, and prove that the product about will produce crystalline deposit within 12 hours according to experiment, the crystallization can block blood vessel, therefore patient can be allowed to be absorbed in fatal danger.The content of the invention
The present inventor is in view of above-mentioned dissolving Docetaxel intravenous formulations（Taxotere solvent) is still that said preparation can not be made to have good stability, therefore invents this three component injection agent containing docetaxel.
It is an object of the invention to provide a kind of three component injection agent containing docetaxel for extending stability and facilitating healthcare givers to use.
For up to above-mentioned purpose, the three component injection agent of the invention containing docetaxel include：Mother liquor, it is the solution containing Docetaxel and medical acceptable surfactant；
Ethanol, it is to prevent injection from forming the anti-gelation agent of gel after mixing；
Water, it is to coordinate the flowable for making foregoing mother liquor be in uniform shape with foregoing ethanol.
Wherein the weight of anti-gelation agent is not less than 1 percent compared with surfactant weight ratio；The weight of flowable is not less than 10 compared with surfactant weight ratio.
The present invention can avoid gel of the mother liquor with perfusion liquid as produced by being mixed 5% G/W when using by addition anti-gelation agent, and flowable can coordinate anti-gelation agent to adjust the viscosity of mother liquor, therefore by
Reduced by the viscosity of the redeployed three component injections agent of compound method institute of the present invention, and reach uniform state（Homogeneous), without producing gel, healthcare givers is facilitated to draw the injection with syringe, and confirm extraction amount, furthermore it is also possible to extend the time that Docetaxel produces crystalline deposit from the solution of injection, therefore the stability of increase injection, to reduce fatal risk produced during patient's medication, thereby improve quality of medical care.
Injection of the present invention containing docetaxel, wherein, the medical acceptable surfactant is preferably tween.Wherein, the concentration of the ethanol used is preferably not less than 90%, more preferably no less than 95%;The concentration of Docetaxel is preferably 20mg/ml to 60mg/ml in the mother liquor;The weight of the anti-gelation agent ethanol is more preferably at least the 1% of tween weight;The weight of the water is more preferably at least the 10% of tween weight.
The present invention also provides a kind of method of the injection containing docetaxel prepared described in claim 1, and its step is included：A) mother liquor and ethanol are mixed into mixed liquor；B) add water in above-mentioned mixed liquor, and be well mixed.Brief description of the drawings
Fig. 1:The schematic top plan view of circular injection bottle during uniformity test of the present invention.Specific embodiment
The present invention is described in detail below in conjunction with accompanying drawing, but does not limit the practical range of the present invention.
Injection of the invention containing docetaxel, it includes：
Mother liquor, it contains Docetaxel and one or more pharmaceutically acceptable surfactant solutions, and the surfactant is tween（Tween, i.e. polysorbate）, and the concentration that the Docetaxel is dissolved in tween is 20 mg/mls（Mg/ml) to 60 mg/mls（mg/ml);
Anti-gelation agent, its G/W for acting as to avoid mother liquor when in use with perfusion liquid such as 5% is mixed
Produced gel, the anti-gelation agent is preferably 95% ethanol, and its weight is not less than 1 the percent of tween weight（The wt% of ethanol 1 tween)；Flowable, it is to coordinate with anti-gelation agent so that mother liquor is in the water of uniform shape, and it is the viscosity that can adjust mother liquor that it, which is acted on, and the flowable is pure water or water for injection, and its weight is not less than the 10 of tween weight（The wt/c^ tween of water 10).The three component injection agent that the anti-gelation agent, flowable and mother liquor are constituted, more can flexibly be allocated with intermediate solution of the prior art compared with the combination of mother liquor, and flexibly adjust the viscosity of mother liquor.
The compound method of the three component injection agent containing docetaxel of the present invention, it is after mother liquor is well mixed with anti-gelation agent, to add flowable, and be well mixed.
Above-mentioned compound method is to need in use, directly at room temperature in hand mode or such as desktop nest stream machine（) etc. Vortex the mode of machine auxiliary, allows each component to be reached in mixing uniform.The advantage of the injection containing docetaxel of the present invention is illustrated with several embodiments below：Embodiment one observes the phenomenon that gel is produced with different mixing modes
The present invention can be mixed with convenient use using different methods, and observes the situation of gel generation.Control group：
This group is tested as the intermediate solution of prior art, first it is about to the anti-gelation agent to mix with flowable, carry out different blend steps again, used mother liquor, anti-gelation agent and flowable such as table 1, and different mixed methods and its observation result such as table 2 and table 3.
Table 1.
The intermediate solution Docetaxel that mother liquor anti-gelation agent is mixed with flowable is lived with surface to be mixed 0.24ml ethanol and 1.26ml water to form the 1.5ml 13 common 0.5ml wt% ethanol of property agent tween
Table 2.
Compare two methods, the composition of its final mixed solution is identical, but the local composition of tween surrounding molecules is different, wherein the anti-gelation agent of mixed method 1 can be adsorbed first on tween molecules with flowable, tween surrounding molecules are made to contain the local concentration of more anti-freezing xanthan molecule, the i.e. anti-gelation agent of surfactant molecule（Local concentration) it is higher, therefore the generation of gel can be avoided；And in mixed method 2, when the mother liquor containing tween injects primer solution, the anti-gelation agent has first been poured solution dilution with flowable, causes the anti-gel molecular concentration of tween surrounding molecules too low, thus makes the gelatin phenomenon of generation varying degree in overall solution.
It can thus be appreciated that the consumption of anti-gelation agent not avoids the main cause that gel is produced, its main cause is that whether can fill part during mixing depending on anti-gelation agent to be well mixed with the surfactant molecule in mother liquor, thereby can just avoid and other surfactant molecules produce aggegation.
Experimental group：
Mother liquor, anti-gelation agent and flowable such as table 4, but blend step is different from control group used in this group, it is mixes anti-gelation agent with flowable with mother liquor respectively, its blend step and observation result such as table 5, and being made comparisons with control group.
Table 4.
Anti-gelation agent and flowable are sequentially put into mother liquor by the present embodiment（It is that mother liquor is put into liquid mixed by flowable with anti-gelation agent different from mixed method 2）, it is observed that anti-gelation agent molecule has higher concentration around surfactant molecule, this mixed method can make the ratio of anti-gelation agent molecule and surfactant molecule for 5wt% (<6 wt%), and produced without gel.The mobility of embodiment two is tested
There is the injection such as table 6 of no added flowable, and observe the mixed scenario with being compared each injection.
Table 6.
Mother liquor anti-gelation agent flowable observes result
0.5ml 0.24ml ethanol is without gel
0.5ml 0.24ml ethanol 1.26ml water is without gel and mobility is better than inspection product project 1.
1.0ml 0.24ml ethanol is without gel
1.0ml 0.24ml ethanol 1.26ml water is without gel and mobility is better than inspection product project 1.
Learn there is addition flowable to reduce solution viscosity in injection by the present embodiment, thus the filling of excess volume can be reduced to reduce production cost, and make the absorption injection more convenient, and the injection dosage of absorption can be precisely controlled.The uniformity of embodiment three is tested
After each component mixing, by different stirrings so that injection, its uniformity of re-test is made.
It refer to shown in Fig. 1, the test of the uniformity is on the basis of the top view of circular injection bottle, the central point that its circular radial cross-section is accumulated and the sample point that 0 degree of circumference, 90 degree, 180 degree and 270 degree are the uniformity are taken, is analyzed with high-performance liquid chromatograph (High Performance Liquid Chromatography).Control group：
This group is tested as the intermediate solution of prior art, first it is about to the anti-gelation agent and is mixed into intermediate solution with flowable, extract after intermediate solution and be slowly injected into mother liquor again, and stirred with different agitating modes, analyzed again, used mother liquor, anti-gelation agent and flowable such as table 7, and observation result such as table 8 and table 9 after stirring.The composition of the component injection agent composition of table 7. 2
After the intermediate solution for extracting above-mentioned inspection product project 1 and 2, slowly it is injected into mother liquor, carried out again in the way of gentle Stirring at least 40 seconds, the gentle Stirring is to allow intermediate solution not produce bubble when stirring with mother liquor, and resulting analysis result is as follows：
Gentle agitation uniformity testing pilot project central point 0 degree of 90 degree of 180 degree, 270 degree of relative standard deviations of the component of table 8. 2 note cun agent combination 4
1 5.5 4.4 1.7 8.2 4.3 49%
2 7.5 8.9 7.3 6.6 9.0 13%
(concentration unit is mg/ml）After the intermediate solution for extracting above-mentioned inspection product project 1 and 2, slowly it is injected into mother liquor, then with desktop turbine（Vortex) high degree of agitation at least 40 seconds, make intermediate solution and the mixing liquid of mother liquor produce bubble, resulting analysis result is as follows:The high degree of agitation uniformity testing of the component injection agent composition of table 9. 2
(concentration unit is mg/ml）From above-mentioned analysis result, the mixability of the injection after high degree of agitation is uniform compared with the injection after gentle agitation.Experimental group：
The experiment of this group respectively injects the anti-gelation agent and flowable in mother liquor, and stirred with different agitating modes, then analyzed, used mother liquor, anti-gelation agent and flowable such as table 10, and analysis result such as table 11 and table 12 after stirring, then made comparisons with control group.
The composition of the component injection agent composition of table 10. 3
The anti-gelation agent for extracting three component injection agent compositions of above-mentioned inspection product project 3,4,5,6 respectively is added in mother liquor, then with desktop turbine（Vortex) high degree of agitation at least 20 seconds, are then separately added into flowable and are stirred in the way of gentle Stirring at least 20 seconds again, and the gentle Stirring refers to allow final solution not produce bubble when stirring, and resulting analysis result is as follows：
The gentle agitation uniformity testing of the component injection agent composition of table 11. 3
The anti-gelation agent that (concentration unit is mg/ml) extracts three component injection agent compositions of above-mentioned inspection product project 3,4,5,6 respectively is added in mother liquor, then with desktop turbine（Vortex) high degree of agitation at least 20 seconds, are then separately added into flowable with desktop turbine again（Vortex) high degree of agitation at least 20 seconds, make anti-gelation agent and the mixing liquid of mother liquor produce bubble, resulting analysis result is as follows：
The high degree of agitation uniformity testing of the component injection agent composition of table 12. 3
(concentration unit is mg/ml）The local concentration of anti-gelation agent around the surfactant molecule known to embodiment 1（Local concentration) it is higher, therefore except the ratio of gel in the solution and gel can be reduced in itself in addition to produced uniformity resistance；Relative, for experimental group of the two component injection agent compared to the present invention of control group, because the surfactant of two components is diluted in advance, so that the anti-gelation agent local concentration around surfactant molecule（Local concentration) it is relatively low, so gel proportions and gel produced resistance in itself can not be reduced, after high degree of agitation, still three component injection agent more of the invention are poor for the uniformity of its solution.After example IV stability test mixes injection composition, place at room temperature, observe different standing times and the situation of crystallization.Control group：Extract after the intermediate solution that product project 1 and 2 is examined in table 7, be slowly injected into mother liquor, then with desktop turbine（Vortex) high degree of agitation at least 40 seconds, carry out the test of stability, as a result such as table 13:
Crystallization trial of the component injection agent composition of table 13. 2 after high degree of agitation
Experimental group：
The anti-gelation agent for extracting three component injection agent compositions of the inspection product project 3,4,5,6 in table 10 respectively is added in mother liquor, then with desktop turbine（Vortex) high degree of agitation at least 20 seconds, are then separately added into flowable with desktop turbine again（Vortex) high degree of agitation at least 20 seconds, carry out the test of stability again afterwards, its result such as table 14, and being made comparisons with control group：Crystallization trial inspection product project of the component injection agent composition of table 14. 3 after high degree of agitation 48 hours 24 hours 12 hours 8 hours 4 hours 0 hour
3 nodeless mesh nodeless mesh nodeless mesh nodeless mesh nodeless mesh nodeless mesh
4 nodeless mesh nodeless mesh nodeless mesh nodeless mesh nodeless mesh nodeless mesh
5 nodeless mesh nodeless mesh nodeless mesh nodeless mesh nodeless mesh nodeless mesh
6 nodeless mesh nodeless mesh nodeless mesh nodeless mesh nodeless mesh nodeless mesh
The local concentration of anti-gelation agent known to embodiment 1 and embodiment 3 around the surfactant molecule（Local concentration) it is higher, therefore except the ratio of gel in the solution and gel can be reduced in itself in addition to produced uniformity resistance, but also the energy barrier between the surfactant molecule can be improved, it is to avoid Docetaxel molecule produces crystalline deposit because of intermolecular aggregation；Relative, the anti-gelation agent local concentration around the surfactant molecule of two component injection agent of control group（Local concentration) it is relatively low, therefore the energy barrier between surfactant molecule is relatively low, therefore two component injection agent will produce crystalline deposit after 12 hours are placed, and three component injection agent of the experimental group of the present invention are being placed in 48 hours all without generation crystalline deposit.
Addition anti-gelation agent can avoid mother liquor from mixing produced gel with perfusion liquid when using, and flowable can coordinate anti-gelation agent to adjust the viscosity of mother liquor, therefore pass through the viscosity reduction of the redeployed three component injections agent of compound method institute of the present invention, and reach uniform state（Homogeneous), without producing gel, healthcare givers is facilitated to draw the injection with syringe, and confirm extraction amount, furthermore it is also possible to extend the time that Docetaxel produces crystalline deposit from the solution of injection, therefore the stability of increase injection, to reduce fatal risk produced during patient's medication, thereby improve quality of medical care.
Claims (1)
- Claims1. a kind of injection containing docetaxel, it includes：Mother liquor, it is the solution containing Docetaxel and medical acceptable surfactant；Ethanol, it is to prevent injection from forming the anti-gelation agent of gel after mixing；Water, it is to coordinate the flowable for making foregoing mother liquor be in uniform shape with foregoing ethanol.2. the injection as claimed in claim 1 containing docetaxel, wherein, the medical acceptable surfactant is tween.3. the injection as claimed in claim 1 containing docetaxel, wherein, the concentration of the ethanol is not less than 90%.4. the injection as claimed in claim 1 containing docetaxel, wherein, the concentration of the ethanol is not less than 95%.5. the injection as claimed in claim 2 containing docetaxel, wherein, the concentration of Docetaxel is 20mg/ml to 60mg/ml in the mother liquor.6. the injection as claimed in claim 2 containing docetaxel, wherein, the weight of the ethanol is at least the 1% of tween weight.7. the injection as claimed in claim 2 containing docetaxel, wherein, the weight of the water is at least the 10% of tween weight.8. a kind of method of the injection containing docetaxel prepared described in claim 1, its step is included：A) mother liquor and ethanol are mixed into mixed liquor；AndB) add water in above-mentioned mixed liquor, and be well mixed.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/CN2007/071274 WO2009079878A1 (en) | 2007-12-19 | 2007-12-19 | Injection comprising docetaxel and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101883563A true CN101883563A (en) | 2010-11-10 |
| CN101883563B CN101883563B (en) | 2014-07-09 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN200780101762.9A Active CN101883563B (en) | 2007-12-19 | 2007-12-19 | Injection comprising docetaxel and its preparation |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JP2011506495A (en) |
| KR (1) | KR20100113527A (en) |
| CN (1) | CN101883563B (en) |
| WO (1) | WO2009079878A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101862319B (en) * | 2010-06-28 | 2012-01-11 | 江苏奥赛康药业股份有限公司 | Docetaxel combination for injection and preparation method thereof |
| JP6124633B2 (en) * | 2013-03-18 | 2017-05-10 | ダイト株式会社 | Stable docetaxel injection |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5750561A (en) * | 1991-07-08 | 1998-05-12 | Rhone-Poulenc Rorer, S.A. | Compositions containing taxane derivatives |
| JP2005225818A (en) * | 2004-02-13 | 2005-08-25 | Otsuka Pharmaceut Factory Inc | Medicinal composition of paclitaxel or docetaxel |
| AU2007246077A1 (en) * | 2006-05-03 | 2007-11-08 | I.Q.A., A.S. | Pharmaceutical composition containing taxane derivative destined for the preparation of an infusion solution, method of preparation thereof and use thereof |
-
2007
- 2007-12-19 KR KR1020107016036A patent/KR20100113527A/en not_active Application Discontinuation
- 2007-12-19 WO PCT/CN2007/071274 patent/WO2009079878A1/en active Application Filing
- 2007-12-19 JP JP2010538312A patent/JP2011506495A/en active Pending
- 2007-12-19 CN CN200780101762.9A patent/CN101883563B/en active Active
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| Publication number | Publication date |
|---|---|
| WO2009079878A1 (en) | 2009-07-02 |
| CN101883563B (en) | 2014-07-09 |
| JP2011506495A (en) | 2011-03-03 |
| KR20100113527A (en) | 2010-10-21 |
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