CN103058960A - Cabazitaxel polymorphic form and preparation method thereof - Google Patents
Cabazitaxel polymorphic form and preparation method thereof Download PDFInfo
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Abstract
The invention belongs to the technical field of medicines, relating to a cabazitaxel polymorphic form and a preparation method thereof, and particularly provides a novel crystalline form of anhydride, monohydrate and dehydrate of cabazitaxel and a preparation method thereof. The novel crystalline form provided by the invention is good in product stability, simple in preparation technology, good in quality reproducibility and easy to control for product purity, and is suitable for industrial production.
Description
Technical field
The invention belongs to medical technical field, relate to particularly new Cabazitaxel polymorphic forms and preparation method thereof.
Background technology
The antitumour drug Cabazitaxel; namely 7,10-bi-methoxy docetaxel, chemistry (2 α by name; 5 β; 7 β, 10 β, 13 α)-4-acetoxyl group-13-({ (2R; 3S)-and the 3-[(tert-butoxycarbonyl) amino]-2-hydroxyl-3-hydrocinnamoyl } oxygen)-1-hydroxyl-7; 10-dimethoxy-9-oxo Japanese yew-5,20-epoxy group(ing)-11-alkene-2-benzoic ether, its chemical structural formula is as follows:
Cabazitaxel belongs to the taxanes antitumour drug, and it is by using from the semi-synthetic preparation of precursor of Ramulus et folium taxi cuspidatae extraction, being mainly used in treating the hormone refractory metastatic prostate cancer.Cabazitaxel is a kind of microtubule inhibitors, by with tubulin binding, promote the microtubule dimer to be assembled to microtubule, by preventing that the multimerization process from suppressing microtubule and decomposing and make microtubule stable, the retardance cell is in G simultaneously
2With the M phase, thus the mitotic division of anticancer and propagation.It has anti-tumor activity to people's knurl in late period of transplanting in the mouse, and the responsive tumor line of docetaxel also has activity, in addition, still has activity in chemotherapy being comprised the insensitive tumor model of docetaxel.This medicine was gone on the market through preferential examination and approval procedures approval by U.S. FDA on June 17th, 2010, was that it gets the Green Light in the world first specifically, had wide market outlook.
In the pharmaceutical production, the specific polymorphic of bulk drug takes advantage in stability, thus in the production process, find stability strong, be beneficial to long storage and under certain environment, keep in other words the crystal formation of its specific physics, stable chemical nature significant.At present patent and the patent application about the Cabazitaxel crystal formation mainly contains ZL200480026128.X, CN101918385A, CN102659722A, CN102675257A etc., acetone solvate crystal formation of the disclosed Cabazitaxel of ZL200480026128.X and preparation method thereof wherein, but not to stablize very much according to the experimental result acetone solvate, all easily slough part acetone under long-term placement or the hot conditions, and the quality of bulk drug can descend to some extent also; Although CN101918385A discloses a variety of crystal formations, its preparation method is very unique, is not suitable for industrialized production; CN102659722A discloses the Cabazitaxel amorphous form; CN102675257A discloses a kind of Cabazitaxel anhydrous form crystal.
Summary of the invention
The object of the present invention is to provide three kinds of new Cabazitaxel polymorphic forms, its stable crystal form is good, is difficult for transformation and preparation method repeatability and circulation ratio better, preparation is simple, easy to operate, be fit to industrialized production, have wide industrial prospect and huge industrial value.
One of purpose of the present invention is to provide a kind of Cabazitaxel anhydrate form, the Cabazitaxel anhydrate form that provides among the present invention is carried out x-ray powder diffraction test, 2 θ of the X-ray powder diffraction figure that obtains have located diffraction peak at 7.28,8.12,9.84,12.68,13.00,17.64 and 18.56 ± 0.2 °.
Further, 2 θ of the X-ray powder diffraction figure of described Cabazitaxel anhydrate form have located diffraction peak at 7.28,8.12,9.84,10.36,11.10,12.68,13.00,15.86,17.20,17.64,18.56 and 21.98 ± 0.2 °.
Cabazitaxel anhydrate form provided by the invention, its dsc analysis collection of illustrative plates has obvious crystalline exotherm peak at 161.78 ℃; TG analyzes collection of illustrative plates and shows that this crystal formation does not have weightlessness.
The invention provides the method for the described Cabazitaxel anhydrate form of a kind of preferred preparation, comprising: the Cabazitaxel acetone solvate is dissolved in the acetone, drips water under the room temperature, stirs, and filters, and filter cake washes with water, and vacuum-drying gets described Cabazitaxel anhydrous form.
Preferably, with respect to every gram Cabazitaxel acetone solvate, the consumption of described acetone is 10～20ml, and the consumption of water is 100～200ml in the described reaction.
Another object of the present invention is to provide a kind of new Cabazitaxel monohydrate form, the Cabazitaxel monohydrate form that provides among the present invention is carried out x-ray powder diffraction test, 2 θ of the X-ray powder diffraction figure that obtains have located diffraction peak at 8.82,11.02,13.94,17.74 and 19.34 ± 0.2 °.
Further, 2 θ of the X-ray powder diffraction figure of described Cabazitaxel monohydrate form have located diffraction peak at 8.82,10.32,11.02,12.42,13.94,15.36,17.74,18.42,19.34,19.78 and 23.28 ± 0.2 °.
Further, 2 θ of the X-ray powder diffraction figure of described Cabazitaxel monohydrate form have located diffraction peak at 4.42,724,824,882,1032,1102,1242,1300,1342,1394,1536,1652,17.18,17.74,18.42,19.34,19.78,20.38 and 21.38 ± 0.2 °.
Cabazitaxel monohydrate form provided by the invention, its dsc analysis collection of illustrative plates has obvious crystalline exotherm peak at 150.20 ℃; TG analyzes collection of illustrative plates and shows that this crystal formation weightlessness is 1.9 ± 0.1%.
The invention provides the method for the described Cabazitaxel monohydrate of a kind of preferred preparation form, comprising: the Cabazitaxel acetone solvate is dissolved in the ethanol, drips water under the room temperature, stir, filter, filter cake washes with water, and vacuum-drying gets described Cabazitaxel monohydrate form.
Preferably, with respect to every gram Cabazitaxel acetone solvate, the consumption of described ethanol is 10～20ml, and the consumption of water is 100～200ml in the described reaction.
Another object of the present invention is to provide a kind of new Cabazitaxel dihydrate form, 2 θ of the X-ray powder diffraction figure of described Cabazitaxel dihydrate form have located diffraction peak at 7.46,7.80,10.16,17.68 and 19.68 ± 0.2 °.
Further, 2 θ of the X-ray powder diffraction figure of described Cabazitaxel dihydrate form have located diffraction peak at 7.46,7.80,10.16,12.60,12.82,14.42,17.00,17.68,18.14,19.68 and 21.94 ± 0.2 °.
Further, 2 θ of the X-ray powder diffraction figure of described Cabazitaxel dihydrate form have located diffraction peak at 7.46,7.80,10.16,12.60,12.80,13.40,14.42,17.00,17.68,18.14,19.68,21.08,21.62 and 21.94 ± 0.2 °.
Cabazitaxel dihydrate form provided by the invention, its dsc analysis collection of illustrative plates has obvious crystalline exotherm peak at 156.17 ℃; TG analyzes collection of illustrative plates and shows that this crystal formation weightlessness is 4.4 ± 0.1%.
The invention provides the method for the described Cabazitaxel monohydrate of a kind of preferred preparation form, comprising: the Cabazitaxel acetone solvate is dissolved in the tetrahydrofuran (THF), drips water under the room temperature, stir, filter, filter cake washes with water, and vacuum-drying gets described Cabazitaxel dihydrate form.
Preferably, with respect to every gram Cabazitaxel acetone solvate, the consumption of described tetrahydrofuran (THF) is 10～20ml, and the consumption of water is 100～200ml in the described reaction.
The preparation of above-mentioned Cabazitaxel acetone solvate can referenced patent ZL200480026128.X embodiment 1.Above-mentioned " consumption of water in the reaction " refers to the consumption of water in " dripping water under the room temperature " operation; Above-mentioned institute water is preferably purified water.
The invention provides the crystalline forms of three kinds of Cabazitaxels, three kinds of crystalline forms are all more stable, and under hot and humid environment, crystal formation does not change, and purity and stable content are all better, and are single assorted very little; And preparation method's repeatability and circulation ratio are better, simple to operation, and be very little to environment and personnel's harm, is fit to industrialized production.
Description of drawings:
Fig. 1 is the XRPD figure of Cabazitaxel anhydrate form of the present invention
Fig. 2 is the DSC figure of Cabazitaxel anhydrate form of the present invention
Fig. 3 is the TG figure of Cabazitaxel anhydrate form of the present invention
Fig. 4 is the XRPD figure of Cabazitaxel monohydrate form of the present invention
Fig. 5 is the DSC figure of Cabazitaxel monohydrate form of the present invention
Fig. 6 is the TG figure of Cabazitaxel monohydrate form of the present invention
Fig. 7 is the XRPD figure of Cabazitaxel dihydrate form of the present invention
Fig. 8 is the DSC figure of Cabazitaxel dihydrate form of the present invention
Fig. 9 is the TG figure of Cabazitaxel dihydrate form of the present invention
Embodiment
The more detailed description that following embodiment just carries out invention not should be understood to be to scope of the present invention or ask for protection the restriction of scope.
Related XPRD all adopts Swiss X'TRA type X-ray diffractometer among the present invention, and condition determination is the copper target, tube voltage 40kV, tube current 100mA, 10.00 °/min of sweep velocity, 3.00～45.00 ° of sweep limits.
DSC and TG related among the present invention all adopt U.S. Perkin Elmer company to produce PYRTS-1-DSC type thermal analyzer, and the TGA test condition is heat-up rate: 20 ° of C/min; Temperature range: 25 ° of C～700 ° C; The DSC test condition is heat-up rate: 10 ° of C/min; Temperature range: 50 ° of C～300 ° C.
The analysis liquid-phase condition of the purity testing of related product is among the present invention: all adopt Japanese Shimadzu LC/20AT high performance liquid phase detector, add the alkyl linked silicagel column of Rec C18, specification 250*4.6mm, post footpath 5 μ m, the detection wavelength is 230nm, and moving phase is acetonitrile/methanol=45:55.
Embodiment 1
Take by weighing Cabazitaxel acetone solvate 500mg stirring and be dissolved in the 5ml acetone, in above-mentioned solution, drip the 50ml purified water under the room temperature, a large amount of white solids are arranged.Filter after at room temperature stirring 30min, the white filter cake that obtains gets white solid powder 458mg, yield 98.0% with purified water washing 3 times after the vacuum-drying; The XPRD spectrogram of this product is seen Fig. 1, and the DSC spectrogram is seen Fig. 2, and the TGA spectrogram is seen Fig. 3, judges according to spectrogram and data, and this compound is the Cabazitaxel anhydrate form.
Take by weighing Cabazitaxel acetone solvate 500mg stirring and be dissolved in the 10ml acetone, in above-mentioned solution, drip the 100ml purified water under the room temperature, a large amount of white solids are arranged.Filter after at room temperature stirring 45min, the white filter cake that obtains gets white solid powder 452mg, yield 96.6% with purified water washing 3 times after the vacuum-drying; The XPRD of this product, DSC spectrogram, TGA spectrogram are substantially the same manner as Example 1, and product is the Cabazitaxel anhydrate form.
Embodiment 3
Take by weighing Cabazitaxel acetone solvate 500mg stirring and be dissolved in the 5ml ethanol, in above-mentioned solution, drip the 50ml purified water under the room temperature, a large amount of white solids are arranged.Filter after at room temperature stirring 30min, the white filter cake that obtains gets white solid powder 459mg, yield 96.2% with purified water washing 3 times after the vacuum-drying; The XPRD spectrogram of this product is seen Fig. 4, and the DSC spectrogram is seen Fig. 5, and the TGA spectrogram is seen Fig. 6, and residual by organic solvent-free in this crystal formation of vapor detection, judges according to spectrogram and data, and this product is Cabazitaxel monohydrate form.
Embodiment 4
Take by weighing Cabazitaxel acetone solvate 500mg stirring and be dissolved in the 10ml ethanol, in above-mentioned solution, drip the 100ml purified water under the room temperature, a large amount of white solids are arranged.Filter after at room temperature stirring 60min, the white filter cake that obtains gets white solid powder 465mg, yield 97.4% with purified water washing 3 times after the vacuum-drying; The XPRD of this product, DSC spectrogram, TGA spectrogram and embodiment 3 products are basic identical, and product is Cabazitaxel monohydrate form.
Embodiment 5
Take by weighing Cabazitaxel acetone solvate 500mg stirring and be dissolved in the 5ml tetrahydrofuran (THF), in above-mentioned solution, drip the 50ml purified water under the room temperature, a large amount of white solids are arranged.Filter after at room temperature stirring 30min, the white filter cake that obtains gets white solid powder 471mg, yield 96.5% with purified water washing 3 times after the vacuum-drying; The XPRD spectrogram of this product is seen Fig. 7, and the DSC spectrogram is seen Fig. 8, and the TGA spectrogram is seen Fig. 9, and residual by organic solvent-free in this crystal formation of vapor detection, judges according to spectrogram and data, and this product is the Cabazitaxel dihydrate form.
Embodiment 6
Take by weighing Cabazitaxel acetone solvate 500mg stirring and be dissolved in the 10ml tetrahydrofuran (THF), in above-mentioned solution, drip the 100ml purified water under the room temperature, a large amount of white solids are arranged.Filter after at room temperature stirring 45min, the white filter cake that obtains gets white solid powder 465mg, yield 95.3% with purified water washing 3 times after the vacuum-drying; The XPRD of this product, DSC spectrogram, TGA spectrogram are substantially the same manner as Example 5, and product is the Cabazitaxel dihydrate form.
Embodiment 7 Cabazitaxel polymorphic forms Detection of Stability
1, high temperature experiment
The Cabazitaxel crystalline forms that the present invention is made is positioned in the vial of sealing clean, places 60 ℃ of thermostatic drying chambers, and respectively sampling in 5,10 days detects, and contrasts with 0 day result, the results are shown in Table 1, table 2 and table 3:
The experiment of table 1 Cabazitaxel anhydrate form high temperature
The experiment of table 2 Cabazitaxel monohydrate form high temperature
The experiment of table 3 Cabazitaxel dihydrate form high temperature
2, high humidity experiment
The Cabazitaxel crystalline forms that the present invention makes is evenly shared to uncovered culture dish, and thickness≤5mm places room temperature (about 25 ℃), relative humidity is in 75 ± 5% the constant incubator, respectively sampling in 5,10 days detects, and contrasts with 0 day result, the results are shown in Table 4, table 5 and table 6:
The experiment of table 4 Cabazitaxel anhydrate form high humidity
The experiment of table 5 Cabazitaxel monohydrate form high humidity
Stability experiment is the result show, Cabazitaxel anhydrate form of the present invention, and under hot and humid environment, crystal formation does not change, and purity and stable content are all better, and be single assorted very little; Cabazitaxel monohydrate form and Cabazitaxel dihydrate form, under hot and humid environment, crystal formation does not change, and related substance does not have considerable change, and single assorted less, content only has slightly reduction; Experimental result shows that three kinds of crystalline forms of the resulting Cabazitaxel of the present invention are all more stable.
Claims (9)
1. a Cabazitaxel anhydrate form is characterized in that, 2 θ of its X-ray powder diffraction figure have located diffraction peak at 7.28,8.12,9.84,12.68,13.00,17.64 and 18.56 ± 0.2 °.
2. Cabazitaxel anhydrous form according to claim 1, it is characterized in that, 2 θ of X-ray powder diffraction figure have located diffraction peak at 7.28,8.12,9.84,10.36,11.10,12.68,13.00,15.86,17.20,17.64,18.56 and 21.98 ± 0.2 °.
3. Cabazitaxel anhydrate form according to claim 1 is characterized in that, its dsc analysis collection of illustrative plates has obvious crystalline exotherm peak at 161.78 ℃.
4. according to claim 1 to the preparation method of 3 arbitrary described Cabazitaxel anhydrate form, comprising: the Cabazitaxel acetone solvate is dissolved in the acetone, drips water under the room temperature, stirs, and filters, and filter cake washes with water, and vacuum-drying gets described Cabazitaxel anhydrous form.
5. preparation method according to claim 4 is characterized in that, with respect to every gram Cabazitaxel acetone solvate, the consumption of described acetone is 10～20ml, the consumption 100～200ml of water in the described reaction.
6. a Cabazitaxel monohydrate form is characterized in that, 2 θ of its X-ray powder diffraction figure have located diffraction peak at 8.82,11.02,13.94,17.74 and 19.34 ± 0.2 °; Preferably, 2 θ of its X-ray powder diffraction figure have located diffraction peak at 8.82,10.32,11.02,12.42,13.94,15.36,17.74,18.42,19.34,19.78 and 23.28 ± 0.2 °; Further preferably, 2 θ of its X-ray powder diffraction figure have located diffraction peak at 4.42,7.24,8.24,8.82,10.32,11.02,12.42,13.00,13.42,13.94,15.36,16.52,17.18,17.74,18.42,19.34,19.78,20.38 and 21.38 ± 0.2 °.
7. Cabazitaxel monohydrate form according to claim 6 is characterized in that, its dsc analysis collection of illustrative plates has obvious crystalline exotherm peak at 150.20 ℃.
8. a Cabazitaxel dihydrate form is characterized in that, 2 θ of its X-ray powder diffraction figure have located diffraction peak at 7.46,7.80,10.16,17.68 and 19.68 ± 0.2 °; Preferably, 2 θ of its X-ray powder diffraction figure have located diffraction peak at 7.46,7.80,10.16,12.60,12.82,14.42,17.00,17.68,18.14,19.68 and 21.94 ± 0.2 °; Further preferably, 2 θ of X-ray powder diffraction figure have located diffraction peak at 7.46,7.80,10.16,12.60,12.80,13.40,14.42,17.00,17.68,18.14,19.68,21.08,21.62 and 21.94 ± 0.2 °.
9. Cabazitaxel dihydrate form according to claim 8 is characterized in that, its dsc analysis collection of illustrative plates has obvious crystalline exotherm peak at 156.17 ℃.
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| CN103044364A (en) * | 2013-01-07 | 2013-04-17 | 重庆泰濠制药有限公司 | Cabazitaxel amorphous crystal and preparation method thereof |
| CN103333138A (en) * | 2013-07-22 | 2013-10-02 | 北京科莱博医药开发有限责任公司 | Novel Cabazitaxel crystal form, preparation method, application and pharmaceutical compositions thereof |
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| CN103450119A (en) * | 2013-09-24 | 2013-12-18 | 天津炜捷制药有限公司 | Cabazitaxel with crystal form W and method for preparing same |
| WO2015000165A1 (en) * | 2013-07-04 | 2015-01-08 | 北京新天宇科技开发有限公司 | Stable transformation product of dimethoxy docetaxel mono-acetonate and crystalline forms thereof, and methods for preparation of same |
| JP2015518012A (en) * | 2012-07-25 | 2015-06-25 | チョンチン・タイハオ・ファーマシューティカル・カンパニー・リミテッド | Crystal form of cabazitaxel and process for its preparation |
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| CN103450119A (en) * | 2013-09-24 | 2013-12-18 | 天津炜捷制药有限公司 | Cabazitaxel with crystal form W and method for preparing same |
| CN103450119B (en) * | 2013-09-24 | 2015-06-17 | 天津炜捷制药有限公司 | Cabazitaxel with crystal form W and method for preparing same |
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