CN101396354B - Stable taxabe compound liquid combination and preparation method and use thereof - Google Patents
Stable taxabe compound liquid combination and preparation method and use thereof Download PDFInfo
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- 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
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- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
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- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
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- A61K9/0012—Galenical forms characterised by the site of application
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Abstract
The invention provides a liquid combination. The combination is surfactant solution solved with taxane derivative which is characterized in that the pH value of the solution is less than 5, and the preferential pH value is 3 to 5. The liquid combination is particularly fit for being used as injection, is not degraded easily during the storage and is safer and more effective. The invention also provides the preparation method and the application of the liquid combination.
Description
Technical field
The present invention relates to a kind of fluid composition, particularly relate to a kind of stable taxanes compounds fluid composition and preparation method thereof and its application.
Background technology
The taxanes analog derivative is the double terpene compound that can be used for drug world, as tumor treatment agent such as ovarian cancer, breast carcinoma, pulmonary carcinoma.With the docetaxel is example (docetaxel/Taxotere), docetaxel is a present clinical application effect medicine preferably, it also is semi-synthetic antitumor drug by the exploitation of French Rhone-Poulenc Rorer company, in the nineteen ninety-five Initial Public Offering, can impel the microtubule assembling, stop the microtubule partition, suppress the tumor cell differentiation, finally cause death of neoplastic cells, show, become the most wide antitumor drug of clinical practice at present the reliable curative effect of multiple kinds of tumor.Taxanes analog derivatives such as docetaxel generally are used for clinical to concentrate infusion with liquid dosage form.For example, the conventional recommended dose scheme of docetaxel was 1 time/3 weeks, 1 hour venoclysis 75mg/m
2
Existing a lot of at the intravenously administrable dosage form research of taxanes analog derivative (for example docetaxel).The water solublity of this type of medicine is relatively poor, generally is made into the concentrated solution that is dissolved in surfactant and ethanol water, it is dissolved in the transfusion during clinical use again and uses.Rowinsky, Lorraine, Cazenave and Donehower etc. are in August 1 nineteen ninety (" National Cancer Institute magazine ", 82 volumes, 15 phases: 1247-1259) disclose following compound method, people prepare a kind of solution of called after " mother solution " earlier, described " mother solution " is the mixed solution that the polyoxyethylene castor oil of 50% volume of ethanol and 50% volume is formed, the paclitaxel that contains the 6mg/ml that has an appointment in the mixed solution, during injection, this solution mixes with the infusion liquid of sodium chloride-containing or glucose.
A kind of Injectable composition that contains the taxanes analog derivative has been described in the Chinese patent application 93119653.1 and 02147245.9, described compositions is dissolved in taxanes compounds docetaxel in the surfactants such as Tween 80, add diluent solutions such as ethanol again, described diluent solution can separate with surfactant solution to be placed or mixing, the drug solution when the two mixed liquid uses as the clinical infusion of preparation.
The embodiment 1 of U.S. Pat 5403858A specifically discloses the method for preparing the docetaxel mother solution, docetaxel is dissolved in the dehydrated alcohol, add Tween 80 subsequently, again ethanol is removed, obtain mother solution, it is 0.1,0.3 and during 0.5mg/ml that mother solution is diluted to concentration with 5% glucose infusion liquid, and observation post gets the stability of dilute solution.Applicant of the present invention studies it on this basis, is surprised to find, and by adjusting the production technology of mother solution, has improved the stability of mother solution greatly, and the degraded or the related substance of effective ingredient significantly reduce, and obviously improve the safety of medicine.
Summary of the invention
The technical problem to be solved in the present invention is that a kind of taxanes analog derivative fluid composition with higher stability is provided.Fluid composition of the present invention is particularly useful for making the injection of taxanes analog derivative, as the fluid composition or the ejection preparation (claiming injection again) of docetaxel, and is difficult for degraded in depositing process, and is safer and more effective.
At present, during the injection of taxanes class such as preparation docetaxel etc., all with medicine dissolution in surfactant, to make its surfactant solution (claiming " mother solution " again), and must not regulate the pH value of mother solution with acid or alkali, after treating diluted dose of mother solution (as glucose solution or sodium chloride solution) dilution, the pH value of gained injection is fit to physiological need.Because this product itself meets physiological need, therefore, according to the preparation method of general preparation, the technical staff does not need can not adjust its Acidity of Aikalinity yet.
Applicant of the present invention is by after investigating each factor of preparation, and unexpected the discovery added a certain amount of acid reagent (claiming acid regulator again) in the surface activity solution at mother solution, make it become faintly acid after, the stability of mother solution improves greatly.According to embodiment 1 (the calling former prescription technology in the following text) method of US5403858A, this inventor makes the mother solution that contains surfactant, does not add acid regulator when adjusting its Acidity of Aikalinity, and its pH value is 6.0～8.0.And the inventor finds through experimental study, if add acid regulator at this product solution, when its adjustment was faintly acid, medicinal liquid was more stable.Adopt former its mother solution of prescription prepared, under 40 ℃ of conditions, placed 10 days, the content that records its related substance is 11.7%.Prepare its mother solution according to formulation and technology of the present invention, under 40 ℃ of conditions, placed 10 days, the content that records its related substance is 0.84%.This shows that it is more harsh that former prescription technology makes transportation, the storage requirement of product, and product of the present invention can be placed for a long time under normal temperature condition, helps the transportation and the storage of product.The above results exceeds those skilled in the art's expectation.Particularly the mother solution pH value is 3.0～5.0 o'clock, has mother liquid obtainedly not only improved stability, and after diluted dose (as glucose solution or sodium chloride solution) dilution, the pH value of gained injection still is fit to physiological need.In other words, whether add acid regulator in the mother solution, gained injection after the diluent dilution is acceptable clinically physiological pH, as about pH4-4.5.
Therefore, the object of the present invention is to provide a kind of fluid composition, said composition is the surfactant solution that is dissolved with the taxanes analog derivative, it is characterized in that, the pH value of surfactant solution is below 5, and preferred pH value is 3-5, more preferably 3.5-4.5.
Taxanes analog derivative as herein described is preferably following formula: compound or its pharmaceutically acceptable ester:
Wherein R represents hydrogen atom or acetyl group, R
1Expression uncle-butoxy carbonyl ammonia or benzamido is preferably docetaxel or its ester.
In order to make fluid composition have required faintly acid, can in compositions, add acid regulator, being applied to clinical the most suitable compositions can only be made up of derivative of taxane, surfactant and acid regulator, and not containing other materials, preferred taxanes analog derivative is docetaxel or its ester.
Acid regulator can be any or its combination of organic acid, the mineral acid of the adjustment of acidity of this area routine.Operation for convenience, the acid regulator of use is solution state preferably, it can be prepared into the appropriate solution use for solid organic acid or mineral acid, preferably uses the ethanol preparation acid regulator.Employed organic acid, mineral acid can be this area acid commonly used, and for example citric acid, fumaric acid, maleic acid, malic acid, hydrochloric acid, sulphuric acid, tartaric acid etc. are preferably citric acid, more preferably the alcoholic solution of citric acid.The content of acid regulator in compositions is generally 0.01-20mg/ml, is preferably 0.05-10mg/ml, and more preferably 0.1-5mg/ml most preferably is 0.1-2.8mg/ml.
The surfactant that the present invention is used for dissolved substance is the conventional surfactant that uses in this area, the surfactant that particularly is used for taxanes class medicine in the prior art, any or its combination as polyoxy ethylether, ethylene oxide ester, glyceride, castor oil hydrogenated, polyoxyethylene castor oil, Oleum Ricini, be preferably polyoxy ethylether, particularly Tween 80.
Existing discovering, the injection liquid of taxanes compounds, the ethanol content in its surfactant solution should reduce as best one can, is beneficial to the stability of taxanes compounds solution.Therefore, alcoholic acid content preferably is no more than 10% in the fluid composition, preferably is no more than 5%, more preferably no more than 3%, especially preferably is no more than 1.5%.
Can select its concentration in surfactant according to the needs and the dissolubility of taxanes analog derivative in surfactant that use.At present, the concentration that is used for clinical ejection preparation is generally every 100ml surfactant solution and contains the 1-10g medicine, and the typical concentrations of injection docetaxel is 4g/100ml.
The present invention specifically provides a kind of fluid composition, and especially for the fluid composition of injection, said composition is made up of docetaxel, citric acid and Tween 80, ethanol content≤1.5% wherein, and the content of docetaxel can be 4g/100ml.
On the other hand, the invention provides the purposes of aforesaid liquid compositions in preparation medicine for treating tumor thing.
The present invention provides a kind of method for preparing taxanes compounds ejection preparation on the other hand, particularly prepares the method for docetaxel ejection preparation.When preparing ejection preparation of the present invention, prepare the surfactant solution of taxanes compounds according to conventional methods, add acid regulator in surfactant solution, regulate its pH to 3-5, preferred taxanes analog derivative is docetaxel or its ester.
The present invention specifically provides a kind of method for preparing docetaxel injection, and docetaxel adds anhydrous alcohol solution, adds Tween 80 again, stirs, and to 3-5, removes ethanol, to ethanol content≤1.5% with citric acid anhydrous alcoholic solution adjust pH.
The method of the surfactant solution of preparation taxanes compounds can adopt disclosed method in the prior art.For example:
1) the lower solution of preparation ethanol content, earlier derivative of taxane is dissolved in the ethanol, add surfactant then, can form the micelle of surfactant parcel derivative of taxane in aqueous medium dilution back, removing ethanol in the solution by boulton process or other proper methods, is that part is removed at least;
2) derivative of taxane directly is dissolved in the surfactant, preferable methods is that preparation contains the alcoholic acid surfactant solution of 1-2% earlier, constantly adds derivative of taxane then, and uses screw mixer or cintrifugal disintegrator constantly to stir.
This paper alleged " mother solution " is meant the surfactant solution that is dissolved with the taxanes compounds.The method of measuring the mother solution pH value is: taking liquid is an amount of, adds 13% (V/V) alcoholic solution, it is diluted to the taxanes compounds solution of about 10mg/ml after, measure its pH value, preferably the taxanes analog derivative is docetaxel or its ester.
Except as otherwise noted, percentage composition of the present invention is weight percentage.
The specific embodiment
Specify the present invention below with reference to embodiment, embodiments of the invention only are used to this art scheme is described, and non-limiting essence of the present invention.
Embodiment 1The preparation of docetaxel mother solution
Docetaxel 20g
Tween 80 500ml
Preparation method: embodiment 1 disclosed method according to US5403858A prepares the docetaxel mother solution.
Embodiment 2The preparation of docetaxel mother solution
Docetaxel 20g
The citric acid alcoholic solution is an amount of
Tween 80 500ml
Preparation method: take by weighing docetaxel 20g, add dehydrated alcohol 1000ml, stirring and dissolving, add recipe quantity tween 80 (Tween-80) again, stir, an amount of with citric acid (preparing) with dehydrated alcohol, adjust pH, through 0.22 μ m filtering with microporous membrane, be sub-packed in the cillin bottle, vacuum decompression is removed ethanol, measures ethanol content≤1.5% o'clock, jump a queue and roll enclosing cover, promptly.
Embodiment 3-10PH value influences the docetaxel injecta Study on Stability
According to the preparation method of embodiment 1 and 2, make the mother solution that contains acid regulator (embodiment 3-9) and do not contain acid regulator (embodiment 10) respectively, placed 30 days respectively at 30 ℃ and 2～8 ℃, measure relevant examination project.Embodiment 10 does not add citric acid soln and adjusts the mother solution pH value, and its pH value is 6.0～8.0, the results are shown in Table 1:
Table 1 pH value influences the docetaxel injecta Study on Stability
| Embodiment | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | |
| Citric acid consumption (mg/ml) | 14 | 8 | 4.8 | 3.6 | 3 | 2 | 1 | 0 | |
| Measure pH value | Initial | 3.01 | 3.50 | 3.96 | 4.26 | 4.56 | 4.88 | 5.67 | 6.26 |
| 30 ℃ 30 days | 3.05 | 3.52 | 4.00 | 4.21 | 4.60 | 4.90 | 5.66 | 6.20 | |
| 2～8 ℃ 30 days | 3.00 | 3.48 | 3.95 | 4.22 | 4.62 | 4.86 | 5.67 | 6.26 | |
| Related substance % | Initial | 0.51 | 0.53 | 0.56 | 0.52 | 0.52 | 0.54 | 0.53 | 0.52 |
| 30 ℃ 30 days | 0.53 | 0.56 | 0.55 | 0.58 | 0.61 | 0.76 | 0.83 | 1.22 | |
| 2～8 ℃ 30 days | 0.52 | 0.53 | 0.52 | 0.55 | 0.53 | 0.53 | 0.53 | 0.64 | |
| Content % | Initial | 100.5 | 99.8 | 101.0 | 100.1 | 99.4 | 99.8 | 100.2 | 100.7 |
| 30 ℃ 30 days | 99.5 | 99.2 | 100.4 | 100.5 | 100.4 | 100.2 | 99.7 | 99.4 | |
| 2～8 ℃ 30 days | 100.1 | 100.3 | 99.9 | 99.7 | 100.0 | 100.7 | 99.5 | 99.7 | |
| Appearance character | Initial | Yellowish | Yellowish | Yellowish | Yellowish | Yellowish | Yellowish | Yellowish | Yellowish |
| Color is sticking | Color is sticking | Color is sticking | Color is sticking | Color is sticking | Color is sticking | Color is sticking | Color is sticking | ||
| Magma | Magma | Magma | Magma | Magma | Magma | Magma | Magma | ||
| 30 ℃ 30 days | Yellowish | Yellowish | Yellowish | Yellowish | Yellowish | Yellowish | Yellowish | Yellowish | |
| Color is sticking | Color is sticking | Color is sticking | Color is sticking | Color is sticking | Color is sticking | Color is sticking | Color is sticking | ||
| Magma | Magma | Magma | Magma | Magma | Magma | Magma | Magma | ||
| 2～8 ℃ 30 days | Yellowish | Yellowish | Yellowish | Yellowish | Yellowish | Yellowish | Yellowish | Yellowish | |
| Color is sticking | Color is sticking | Color is sticking | Color is sticking | Color is sticking | Color is sticking | Color is sticking | Color is sticking | ||
| Magma | Magma | Magma | Magma | Magma | Magma | Magma | Magma |
The result shows: when the pH value of mother solution less than 5.0 the time, under 30 ℃ of conditions, placed one month, the content of its related substance is significantly less than pH value greater than 5.0 mother solution; PH value is 3.5～4.5 o'clock, places one month the content basically identical of related substance under 30 ℃ of conditions.Do not add the citron acid for adjusting pH value among the embodiment 10, measuring pH value is 6.26, under 30 ℃ of conditions, placed one month, its related substance apparently higher than pH value less than 5.0 mother solution.Draw thus, the mother solution pH value is on the weak side when acid, and medicinal liquid is more stable, especially when pH value is 3.0～5.0.
Embodiment 11Fluid composition Study on Stability of the present invention
Under hot conditions (40 ℃, 60 ℃, illumination 4500lux), placed 10 days, and carried out fluid composition of the present invention and embodiment 1 stability test, respectively at sampling in 0,5,10 day, adopt high effective liquid chromatography for measuring related substance and content, the results are shown in Table 2,3.
The stability test result of table 2 fluid composition of the present invention
The stability test result of table 3 embodiment 1
Draw thus, fluid composition of the present invention contains acid regulator, and is more stable than the known taxanes analog derivative of prior art mother solution, can place for a long time at normal temperatures, is beneficial to transportation and storage.
Claims (21)
1. fluid composition, described compositions is the surfactant solution that is dissolved with the taxanes analog derivative, it is characterized in that, the pH value of surfactant solution is more than 3 and less than 3.5, compositions contains acid regulator, described acid regulator is a mineral acid, and described taxanes analog derivative is following formula: compound or its pharmaceutically acceptable salt:
Wherein R represents hydrogen atom or acetyl group, R
1Expression uncle-butoxy carbonyl ammonia or benzamido.
2. fluid composition according to claim 1, described taxanes analog derivative are docetaxel or its salt.
3. fluid composition according to claim 2, the assay method of described pH value are to add 13% ethanol water, the measured value when it is diluted to 10mg/ml taxanes analog derivative solution in surfactant solution.
4. fluid composition according to claim 1, described compositions is made up of derivative of taxane, surfactant and acid regulator.
5. fluid composition according to claim 1, the solution of described acid regulator are alcoholic solution.
6. according to each described fluid composition of claim 1-5, described surfactant is selected from any or its combination of polyoxy ethylether, ethylene oxide ester, glyceride, castor oil hydrogenated, Oleum Ricini.
7. fluid composition according to claim 6, described surfactant are the polyoxy ethylether.
8. fluid composition according to claim 7, described surfactant are Tween 80.
9. fluid composition according to claim 1, the content of mineral acid is 0.01-10mg/ml in the described compositions.
10. fluid composition according to claim 9, the content of described mineral acid are 0.05-5mg/ml.
11. fluid composition according to claim 10, the content of described mineral acid are 0.1-5mg/ml.
12. fluid composition according to claim 11, the content of described mineral acid are 0.1-2.8mg/ml.
13. according to each described fluid composition of claim 1-5, wherein alcoholic acid content is no more than 10%.
14. fluid composition according to claim 13, wherein alcoholic acid content is no more than 5%.
15. fluid composition according to claim 14, wherein alcoholic acid content is no more than 3%.
16. fluid composition according to claim 15, wherein alcoholic acid content is no more than 1.5%.
17. fluid composition according to claim 1, wherein the concentration of taxanes analog derivative is 1-10g/100ml.
18. fluid composition according to claim 17, wherein the concentration of taxanes analog derivative is 4g/100ml.
19. fluid composition according to claim 1, this fluid composition are injection.
20. the purposes of claim 1 one 19 each described fluid compositions in preparation medicine for treating tumor thing.
21. the preparation method of each described fluid composition of claim 1-19 is characterized in that, adds the mineral acid acid regulator in the surfactant solution of the derivative of taxane that makes, and regulates its pH value more than 3 and less than 3.5.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2007101623048A CN101396354B (en) | 2007-09-30 | 2007-09-30 | Stable taxabe compound liquid combination and preparation method and use thereof |
| TW097128746A TW201004656A (en) | 2007-09-30 | 2008-07-30 | A stable fluid composition of taxane derivatives, preparing method and use thereof |
| PCT/CN2008/001426 WO2009043226A1 (en) | 2007-09-30 | 2008-08-05 | A stable liquid composition comprising taxan derivatives and its preparation method. |
| HK09105112.3A HK1126405A1 (en) | 2007-09-30 | 2009-06-08 | A stable fluid composition of taxan derivatives, preparing method and use thereof |
Applications Claiming Priority (1)
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|---|---|---|---|
| CN2007101623048A CN101396354B (en) | 2007-09-30 | 2007-09-30 | Stable taxabe compound liquid combination and preparation method and use thereof |
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| CN101396354B true CN101396354B (en) | 2010-12-01 |
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| CN (1) | CN101396354B (en) |
| HK (1) | HK1126405A1 (en) |
| TW (1) | TW201004656A (en) |
| WO (1) | WO2009043226A1 (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| SG185389A1 (en) | 2010-05-03 | 2012-12-28 | Teikoku Pharma Usa Inc | Non-aqueous taxane pro-emulsion formulations and methods of making and using the same |
| JO3685B1 (en) | 2012-10-01 | 2020-08-27 | Teikoku Pharma Usa Inc | Non-aqueous taxane nanodispersion formulations and methods of using the same |
| EP3679925A4 (en) | 2017-09-07 | 2021-04-21 | Shenzhen Salubris Pharmaceuticals Co. Ltd | Pharmaceutical composition of docetaxel conjugate and preparation method |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997023208A1 (en) * | 1995-12-21 | 1997-07-03 | Genelabs Technologies, Inc. | Taxane composition and method |
| CN1636560A (en) * | 1992-12-02 | 2005-07-13 | 阿文蒂斯药物股份有限公司 | Injectable taxane derivative based compositions |
| WO2007085067A1 (en) * | 2006-01-30 | 2007-08-02 | Quiral Química Do Brasil S.A. | Pharmaceutical compositions containing docetaxel and a degradation inhibitor and a process for obtaining the same. |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ258044A (en) * | 1992-11-27 | 1995-12-21 | Faulding F H & Co Ltd | Pharmaceutical composition comprising taxol, solubilising agent, an acid and an organic solvent |
| US6136846A (en) * | 1999-10-25 | 2000-10-24 | Supergen, Inc. | Formulation for paclitaxel |
| CN1676125A (en) * | 2004-03-31 | 2005-10-05 | 张昊 | Nano-level emulsion containing taxine or hard-soluble medicine |
| KR20050099311A (en) * | 2004-04-09 | 2005-10-13 | 에이엔에이치 케어연구소(주) | Composition for injection comprising anticancer drug |
| US8557861B2 (en) * | 2004-09-28 | 2013-10-15 | Mast Therapeutics, Inc. | Low oil emulsion compositions for delivering taxoids and other insoluble drugs |
| US7361683B2 (en) * | 2004-11-24 | 2008-04-22 | Yung Shin Pharm. Ind., Co., Ltd | Paclitaxel aqueous injection solution and methods for preparing the same |
-
2007
- 2007-09-30 CN CN2007101623048A patent/CN101396354B/en active Active
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- 2008-07-30 TW TW097128746A patent/TW201004656A/en unknown
- 2008-08-05 WO PCT/CN2008/001426 patent/WO2009043226A1/en active Application Filing
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1636560A (en) * | 1992-12-02 | 2005-07-13 | 阿文蒂斯药物股份有限公司 | Injectable taxane derivative based compositions |
| WO1997023208A1 (en) * | 1995-12-21 | 1997-07-03 | Genelabs Technologies, Inc. | Taxane composition and method |
| WO2007085067A1 (en) * | 2006-01-30 | 2007-08-02 | Quiral Química Do Brasil S.A. | Pharmaceutical compositions containing docetaxel and a degradation inhibitor and a process for obtaining the same. |
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| Publication number | Publication date |
|---|---|
| WO2009043226A1 (en) | 2009-04-09 |
| CN101396354A (en) | 2009-04-01 |
| TW201004656A (en) | 2010-02-01 |
| HK1126405A1 (en) | 2009-09-04 |
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