CN102503913B - Preparation method for dimethoxy taxanes compound monocrystal directly used for X-ray single crystal diffraction analysis - Google Patents
Preparation method for dimethoxy taxanes compound monocrystal directly used for X-ray single crystal diffraction analysis Download PDFInfo
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- CN102503913B CN102503913B CN201110321866.9A CN201110321866A CN102503913B CN 102503913 B CN102503913 B CN 102503913B CN 201110321866 A CN201110321866 A CN 201110321866A CN 102503913 B CN102503913 B CN 102503913B
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- 239000013078 crystal Substances 0.000 title claims abstract description 44
- 229940123237 Taxane Drugs 0.000 title claims abstract description 25
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 238000002050 diffraction method Methods 0.000 title claims abstract description 8
- 150000001875 compounds Chemical class 0.000 title abstract description 9
- 239000002904 solvent Substances 0.000 claims abstract description 13
- 238000002425 crystallisation Methods 0.000 claims abstract description 3
- 230000008025 crystallization Effects 0.000 claims abstract description 3
- 238000003756 stirring Methods 0.000 claims abstract description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 7
- 230000008034 disappearance Effects 0.000 claims description 7
- 238000000967 suction filtration Methods 0.000 claims description 7
- 229960003328 benzoyl peroxide Drugs 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 3
- 238000004140 cleaning Methods 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 238000012512 characterization method Methods 0.000 abstract description 3
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000004458 analytical method Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- -1 methoxyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Analysing Materials By The Use Of Radiation (AREA)
Abstract
The invention relates to a preparation method for a dimethoxy taxanes compound monocrystal directly used for X-ray single crystal diffraction analysis, which belongs to the technical field of compound structural characterization sample preparation. The preparation method for the dimethoxy taxanes compound monocrystal directly used for the X-ray single crystal diffraction analysis comprises the following steps: adding a dimethoxy taxanes compound to a good solvent, wherein the addition is shown as follows: every 500mg of dimethoxy taxanes compound is added to 0.5-500mL of good solvent; subsequently, adding to a poor solvent while stirring is performed until cloudy matter is generated in the solvent; heating to enable the cloudy matter to disappear; and standing at room temperature for crystallization to obtain the monocrystal. The dimethoxy taxanes compound monocrystal prepared by the invention can be directly used for the X-ray single crystal diffraction analysis, is simple and clear and has high accuracy.
Description
Technical field
The present invention relates to a kind of preparation method who is directly used in the dimethoxy bearing taxanes monocrystalline crystal of X ray single crystal diffraction analysis, be 4-acetoxyl group-2 α-benzoyloxy-5 β, 20-epoxy group(ing)-1-hydroxyl-7 β, the monocrystalline crystal preparation method of 10 β-dimethoxy-9-oxo yew-11-alkene-13 α-Ji (2R, 3S)-3-t-butoxycarbonyl amino-PLA ester.
Background technology
Dimethoxy bearing taxanes 4-acetoxyl group-2 α-benzoyloxy-5 β, 20-epoxy group(ing)-1-hydroxyl-7 β, 10 β-dimethoxy-9-oxo yew-11-alkene-13 α-Ji (2R, 3S)-3-t-butoxycarbonyl amino-PLA ester has significant antitumour activity, especially for malignant prostate cancer, has significant curative effect.
Therefore, its structural characterization is extremely important for preparing compound described in above formula.
The structural characterization that is generally used for compound has nucleus magnetic resonance, mass spectrum, ultimate analysis, the methods such as X ray single crystal diffraction.Wherein the characterizing method of X ray single crystal diffraction have simple and clear, accuracy high, with nucleus magnetic resonance, mass spectrum, the characterizing methods such as ultimate analysis have formed the most effectively evidence and have supplemented.
Summary of the invention
The object of the invention is to by sherwood oil normal hexane, normal heptane, mixed heptane, hexanaphthene, ethyl acetate, chloroform, methylene dichloride, methyl alcohol, tetrahydrofuran (THF), 1,4-dioxane, acetic acid, pyridine, the recrystallization system in the mixed solvent that the combination of the different solvents such as toluene obtains can be used for the monocrystalline crystal that X ray single crystal diffraction is analyzed.
Technical scheme of the present invention: described 4-acetoxyl group-2 α-benzoyloxy-5 β, 20-epoxy group(ing)-1-hydroxyl-7 β, 10 β-dimethoxy-9-oxo yew-11-alkene-13 α-Ji (2R, 3S)-3-t-butoxycarbonyl amino-PLA ester cpds skeleton symbol is as follows:
Be directly used in the preparation method of the dimethoxy bearing taxanes monocrystalline crystal of X ray single crystal diffraction analysis, step is as follows: get dimethoxy bearing taxanes 4-acetoxyl group-2 α-benzoyloxy-5 β, 20-epoxy group(ing)-1-hydroxyl-7 β, 10 β-dimethoxy-9-oxo yew-11-alkene-13 α-Ji (2R, 3S)-3-t-butoxycarbonyl amino-PLA ester, join in optimum solvent, add-on is that every 500mg dimethoxy bearing taxanes adds 0.5-500mL, add while stirring subsequently poor solvent, until it has muddy generation, be heated to 40-80 ℃ and make muddy disappearance, under room temperature, standing crystallization is 1 hour to 14 days, obtain monocrystalline crystal, by gained monocrystalline crystal suction filtration, with sherwood oil, clean, after cleaning, be drying to obtain and be directly used in the dimethoxy bearing taxanes monocrystalline crystal that X ray single crystal diffraction is analyzed.
Described optimum solvent is ethyl acetate, chloroform, and methylene dichloride, methyl alcohol, tetrahydrofuran (THF), 1,4-dioxane, acetic acid, one or more arbitrary proportions in pyridine and toluene combine arbitrarily.
Described poor solvent be sherwood oil, normal hexane, normal heptane, mixed heptane and hexanaphthene in one or more arbitrary proportions combine arbitrarily.
Beneficial effect of the present invention: dimethoxy bearing taxanes monocrystalline crystal prepared by the present invention can be directly used in the analysis of X ray single crystal diffraction, and simple and clear, accuracy is high.
Accompanying drawing explanation
Fig. 1 dimethoxy bearing taxanes X-ray diffraction structure.
Embodiment
Dimethoxy bearing taxanes of the present invention is purchased from market.
Embodiment 1
Get 500mg dimethoxy bearing taxanes 4-acetoxyl group-2 α-benzoyloxy-5 β, 20-epoxy group(ing)-1-hydroxyl-7 β, 10 β-dimethoxy-9-oxo yew-11-alkene-13 α-Ji (2R, 3S)-3-t-butoxycarbonyl amino-PLA ester is dissolved in ethyl acetate (0.5mL), drip sherwood oil (4.0mL) to there being muddy generation, be heated to after 80 ℃ of muddy disappearances, standing 7 days, there is monocrystalline crystal to separate out, suction filtration, sherwood oil is washed, after dry, obtain monocrystalline crystal (300mg), crystallographic dimension is 0.15 * 0.16 * 0.28mm, can be directly used in the analysis of X ray single crystal diffraction.
Embodiment 2
Getting 500mg dimethoxy bearing taxanes is dissolved in methylene dichloride in (50mL), drip sherwood oil (4.0mL) to there being muddy generation, be heated to after 40 ℃ of muddy disappearances, standing 7 days, there is monocrystalline crystal to separate out, suction filtration, sherwood oil is washed, after dry, obtain monocrystalline crystal (300mg), crystallographic dimension is 0.11 * 0.14 * 0.22mm, can be directly used in the analysis of X ray single crystal diffraction.
Embodiment 3
Getting 500mg dimethoxy bearing taxanes is dissolved in chloroform (50mL), methyl alcohol (75mL) and acetic acid (75mL) mixed solvent, drip sherwood oil (4.0mL) to there being muddy generation, be heated to after 80 ℃ of muddy disappearances, standing 7 days, there is monocrystalline crystal to separate out, suction filtration, sherwood oil is washed, after dry, obtain monocrystalline crystal (300mg), crystallographic dimension is 0.10 * 0.18 * 0.21mm, can be directly used in the analysis of X ray single crystal diffraction.
Embodiment 4
Getting two 500mg methoxyl group bearing taxanes is dissolved in tetrahydrofuran (THF) (100mL) and acetic acid (325mL) mixed solvent, drip sherwood oil (4.0mL) to there being muddy generation, be heated to after 60 ℃ of muddy disappearances, standing 7 days, there is monocrystalline crystal to separate out, suction filtration, sherwood oil is washed, after dry, obtain monocrystalline crystal (300mg), crystallographic dimension is 0.08 * 0.12 * 0.21mm, can be directly used in the analysis of X ray single crystal diffraction.
Embodiment 5
Getting 500mg dimethoxy bearing taxanes is dissolved in pyridine (0.5mL) and methyl alcohol (0.025mL) mixed solvent, add sherwood oil (4.0mL) to there being muddy generation, be heated to after 80 ℃ of muddy disappearances, standing 7 days, there is monocrystalline crystal to separate out, suction filtration, sherwood oil is washed, after dry, obtain monocrystalline crystal (300mg), crystallographic dimension is 0.10 * 0.16 * 0.24mm, can be directly used in the analysis of X ray single crystal diffraction.
X-ray diffraction:
Crystal is water white transparency bulk, and diffraction experiment crystallographic dimension is 0.15 * 0.16 * 0.28mm, belongs to oblique system, and spacer is P2
1, unit cell parameters: a=12.01110, b=17.44220,
α=γ=90.00 °, β=108.46 °, unit cell volume
in structure cell, asymmetry unit is counted Z=2.
With Bruker SMART APEX-II diffractometer, collect diffracted intensity data, CuK
αradiation, graphite monochromator, single conduit diameter ф=0.50mm, crystal and ccd detector are apart from d=60.3mm, pipe is pressed 40kV, pipe stream 30mA, scan mode: ω scanning, collecting that total diffraction counts is 17129, and it is 8518 that independent diffraction is counted, observable count (| F|
2>=2 σ | F|
2) be 8081.Adopt direct method (Shelxs97) to resolve crystalline structure, final reliable factor R after refine
1=0.0594, wR
2=0.1109 (w=1/ σ | F|
2), S=1.053.
Claims (1)
1. be directly used in the preparation method of the dimethoxy bearing taxanes monocrystalline crystal of X ray single crystal diffraction analysis, it is characterized in that step is as follows: get dimethoxy bearing taxanes 4-acetoxyl group-2 α-benzoyloxy-5 β, 20-epoxy group(ing)-1-hydroxyl-7 β, 10 β-dimethoxy-9-oxo yew-11-alkene-13 α-Ji (2R, 3S)-3-t-butoxycarbonyl amino-PLA ester, join in optimum solvent, add-on is that every 500mg dimethoxy bearing taxanes adds 0.5-500mL, add while stirring subsequently poor solvent, until it has muddy generation, be heated to 40-80 ℃ and make muddy disappearance, under room temperature, standing crystallization is 1 hour to 14 days, obtain monocrystalline crystal, by gained monocrystalline crystal suction filtration, with sherwood oil, clean, after cleaning, be drying to obtain and be directly used in the dimethoxy bearing taxanes monocrystalline crystal that X ray single crystal diffraction is analyzed,
Described optimum solvent is that one or more arbitrary proportions in ethyl acetate, chloroform, methylene dichloride, methyl alcohol, tetrahydrofuran (THF), 1,4-dioxane, acetic acid, pyridine and toluene combine arbitrarily;
Described poor solvent be sherwood oil, normal hexane, normal heptane and hexanaphthene in one or more arbitrary proportions combine arbitrarily.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2014514306A (en) | 2011-04-12 | 2014-06-19 | プラス・ケミカルス・エスアー | Solid form of cabazitaxel and method for producing the same |
| US9394266B2 (en) | 2012-03-08 | 2016-07-19 | IVAX International GmbH | Solid state forms of cabazitaxel and processes for preparation thereof |
| CN102675257B (en) * | 2012-05-10 | 2014-07-02 | 上海金和生物技术有限公司 | Cabazitaxel crystal and preparation method thereof |
| CN102746258B (en) * | 2012-07-25 | 2015-02-04 | 重庆泰濠制药有限公司 | Crystal forms of cabazitaxel and preparation method thereof |
| CN102898406B (en) * | 2012-11-02 | 2014-12-03 | 上海金和生物技术有限公司 | Cabazitaxel crystal and preparation method thereof |
| CN102887877A (en) * | 2012-11-05 | 2013-01-23 | 江苏红豆杉生物科技股份有限公司 | Method for purifying cabazitaxel |
| CN103044364B (en) * | 2013-01-07 | 2016-01-20 | 重庆泰濠制药有限公司 | Amorphous crystalline substance of a kind of Cabazitaxel 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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| EP2330100A1 (en) * | 2009-11-04 | 2011-06-08 | Emcure Pharmaceuticals Limited | An improved process for preparation of taxane derivatives |
| WO2011081373A2 (en) * | 2009-12-31 | 2011-07-07 | Samyang Genex Corporation | Method for preparing highly pure anhydrous crystalline docetaxel |
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- 2011-10-20 CN CN201110321866.9A patent/CN102503913B/en active Active
Patent Citations (5)
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|---|---|---|---|---|
| CN101282955A (en) * | 2005-10-12 | 2008-10-08 | 西科尔公司 | Crystalline forms of docetaxel and processes for their preparation |
| CN101918385A (en) * | 2008-01-17 | 2010-12-15 | 安万特医药股份有限公司 | Crystalline forms of dimethoxy docetaxel and methods for preparing same |
| CA2779009A1 (en) * | 2009-10-29 | 2011-05-05 | Aventis Pharma S.A. | Novel antitumoral use of cabazitaxel |
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| WO2011081373A2 (en) * | 2009-12-31 | 2011-07-07 | Samyang Genex Corporation | Method for preparing highly pure anhydrous crystalline docetaxel |
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