CN102503913A - 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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- CN102503913A CN102503913A CN2011103218669A CN201110321866A CN102503913A CN 102503913 A CN102503913 A CN 102503913A CN 2011103218669 A CN2011103218669 A CN 2011103218669A CN 201110321866 A CN201110321866 A CN 201110321866A CN 102503913 A CN102503913 A CN 102503913A
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- monocrystalline
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- 239000013078 crystal Substances 0.000 title claims abstract description 42
- 229940123237 Taxane Drugs 0.000 title claims abstract description 27
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 150000001875 compounds Chemical class 0.000 title abstract description 9
- 238000002050 diffraction method Methods 0.000 title abstract 4
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 238000004458 analytical method Methods 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 9
- 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
- 230000008034 disappearance Effects 0.000 claims description 7
- 238000001035 drying Methods 0.000 claims description 7
- 238000000967 suction filtration Methods 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 229960003328 benzoyl peroxide Drugs 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- 238000012512 characterization method Methods 0.000 abstract description 3
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- -1 3-t-butoxycarbonyl amino-2-hydroxyl-3-phenylpropionic acid ester Chemical class 0.000 description 3
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 2
- 238000002441 X-ray diffraction Methods 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
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000694 effects 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
- 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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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 dimethoxy bearing taxanes monocrystalline crystalline preparation method that the X ray single crystal diffraction is analyzed that directly is used for; Be 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)-the monocrystalline crystal preparation method of 3-t-butoxycarbonyl amino-2-hydroxyl-3-phenylpropionic acid 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-2-hydroxyl-3-phenylpropionic acid ester has significant anti-cancer activity, especially has significant curative effect for the malignant prostate cancer.
Therefore, its structural characterization is extremely important for the said compound of preparation following formula.
The structural characterization that is generally used for compound has nucleus magnetic resonance, mass spectrum, ultimate analysis, methods such as X ray single crystal diffraction.Wherein the characterizing method of X ray single crystal diffraction has characteristics such as simple and clear, accuracy height, and with nucleus magnetic resonance, mass spectrum, characterizing methods such as ultimate analysis have formed the most direct effective evidences and replenished.
Summary of the invention
The objective of the invention is to through at sherwood oil, normal hexane, normal heptane mixes heptane; Hexanaphthene, ETHYLE ACETATE, chloroform, methylene dichloride; Methyl alcohol, THF, 1, the 4-dioxane; Acetic acid, pyridine, the recrystallization system in the mixed solvent that the combination of different solvents such as toluene obtains can be used for the monocrystalline crystal that the X ray single crystal diffraction is analyzed.
Technical scheme of the present invention: said 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-2-hydroxyl-3-phenylpropionic acid ester cpds skeleton symbol is following:
Directly be used for the dimethoxy bearing taxanes monocrystalline crystalline preparation method that the X ray single crystal diffraction is analyzed; Step is following: 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-2-hydroxyl-3-phenylpropionic acid ester; Join in the optimum solvent, add-on is that every 500mg dimethoxy bearing taxanes adds 0.5-500mL, adds poor solvent subsequently while stirring; Until it muddy generation arranged; Be heated to 40-80 ℃ and make muddy the disappearance, left standstill crystallization under the room temperature 1 hour to 14 days, promptly get the monocrystalline crystal; With gained monocrystalline crystal suction filtration, clean with sherwood oil, clean after drying and promptly get the dimethoxy bearing taxanes monocrystalline crystal that directly is used for the analysis of X ray single crystal diffraction.
Said optimum solvent is an ETHYLE ACETATE, chloroform, and methylene dichloride, methyl alcohol, THF, 1, the 4-dioxane, acetic acid, one or more arbitrary proportions in pyridine and the toluene make up arbitrarily.
Said poor solvent is sherwood oil, normal hexane, normal heptane, mix heptane and hexanaphthene in one or more arbitrary proportions make up arbitrarily.
Beneficial effect of the present invention: the dimethoxy bearing taxanes monocrystalline crystal of the present invention's preparation can directly be used for the analysis of X ray single crystal diffraction, and is simple and clear, and accuracy is high.
Description of drawings
Fig. 1 dimethoxy bearing taxanes X-ray diffraction structure.
Embodiment
Dimethoxy bearing taxanes according to the invention is available 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-2-hydroxyl-3-phenylpropionic acid ester is dissolved in the ETHYLE ACETATE (0.5mL), drips sherwood oil (4.0mL) to muddy the generation arranged, be heated to 80 ℃ of muddy disappearances after; Left standstill 7 days, and had the monocrystalline crystal to separate out suction filtration; Sherwood oil is washed; Obtain monocrystalline crystal (300mg) after the drying, crystallographic dimension is 0.15 * 0.16 * 0.28mm, can directly be used for the analysis of X ray single crystal diffraction.
Embodiment 2
Get 500mg dimethoxy bearing taxanes and be dissolved in the methylene dichloride in (50mL), drip sherwood oil (4.0mL) to muddy the generation arranged, be heated to 40 ℃ of muddy disappearances after; Left standstill 7 days, and had the monocrystalline crystal to separate out suction filtration; Sherwood oil is washed; Obtain monocrystalline crystal (300mg) after the drying, crystallographic dimension is 0.11 * 0.14 * 0.22mm, can directly be used for the analysis of X ray single crystal diffraction.
Embodiment 3
Get 500mg dimethoxy bearing taxanes and be dissolved in chloroform (50mL), methyl alcohol (75mL) and acetate (75mL) mixed solvent, drip sherwood oil (4.0mL) to muddy the generation arranged, be heated to 80 ℃ of muddy disappearances after; Left standstill 7 days, and had the monocrystalline crystal to separate out suction filtration; Sherwood oil is washed; Obtain monocrystalline crystal (300mg) after the drying, crystallographic dimension is 0.10 * 0.18 * 0.21mm, can directly be used for the analysis of X ray single crystal diffraction.
Embodiment 4
Get two 500mg methoxyl group bearing taxanes and be dissolved in THF (100mL) and acetate (325mL) mixed solvent, drip sherwood oil (4.0mL) to muddy the generation arranged, be heated to 60 ℃ of muddy disappearances after; Left standstill 7 days, and had the monocrystalline crystal to separate out suction filtration; Sherwood oil is washed; Obtain monocrystalline crystal (300mg) after the drying, crystallographic dimension is 0.08 * 0.12 * 0.21mm, can directly be used for the analysis of X ray single crystal diffraction.
Embodiment 5
Get 500mg dimethoxy bearing taxanes and be dissolved in pyridine (0.5mL) and methyl alcohol (0.025mL) mixed solvent, add sherwood oil (4.0mL) to muddy the generation arranged, be heated to 80 ℃ of muddy disappearances after; Left standstill 7 days, and had the monocrystalline crystal to separate out suction filtration; Sherwood oil is washed; Obtain monocrystalline crystal (300mg) after the drying, crystallographic dimension is 0.10 * 0.16 * 0.24mm, can directly be used for the analysis of X ray single crystal diffraction.
X-ray diffraction:
Crystal is the water white transparency bulk, and it is 0.15 * 0.16 * 0.28mm that diffraction experiment uses crystallographic dimension, 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
Asymmetry unit is counted Z=2 in the structure cell.
Collect diffraction intensity data, CuK with Bruker SMART APEX-II diffractometer
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, can observe and count (| F|
2>=2 σ | F|
2) be 8081.Adopt direct method (Shelxs97) to resolve crystalline structure, final reliable factor R after the refine
1=0.0594, wR
2=0.1109 (w=1/ σ | F|
2), S=1.053.
Claims (3)
1. directly be used for the dimethoxy bearing taxanes monocrystalline crystalline preparation method that the X ray single crystal diffraction is analyzed; It is characterized in that step is following: 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-2-hydroxyl-3-phenylpropionic acid ester; Join in the optimum solvent, add-on is that every 500mg dimethoxy bearing taxanes adds 0.5-500mL, adds poor solvent subsequently while stirring; Until it muddy generation arranged; Be heated to 40-80 ℃ and make muddy the disappearance, left standstill crystallization under the room temperature 1 hour to 14 days, promptly get the monocrystalline crystal; With gained monocrystalline crystal suction filtration, clean with sherwood oil, clean after drying and promptly get the dimethoxy bearing taxanes monocrystalline crystal that directly is used for the analysis of X ray single crystal diffraction.
2. directly be used for the dimethoxy bearing taxanes monocrystalline crystalline preparation method that the X ray single crystal diffraction is analyzed according to claim 1 is said, it is characterized in that: said optimum solvent be ETHYLE ACETATE, chloroform, methylene dichloride, methyl alcohol, THF, 1,4-dioxane, acetic acid, pyridine and toluene in one or more arbitrary proportions make up arbitrarily.
3. directly be used for the dimethoxy bearing taxanes monocrystalline crystalline preparation method that the X ray single crystal diffraction is analyzed according to claim 1 is said, it is characterized in that: said poor solvent is sherwood oil, normal hexane, normal heptane, mix heptane and hexanaphthene in one or more arbitrary proportions make up arbitrarily.
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| CN102675257A (en) * | 2012-05-10 | 2012-09-19 | 上海金和生物技术有限公司 | Cabazitaxel crystal and preparation method thereof |
| CN102746258A (en) * | 2012-07-25 | 2012-10-24 | 重庆泰濠制药有限公司 | Crystal forms of cabazitaxel 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 |
| CN102898406A (en) * | 2012-11-02 | 2013-01-30 | 上海金和生物技术有限公司 | Cabazitaxel crystal and preparation method thereof |
| 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 |
| WO2013134534A3 (en) * | 2012-03-08 | 2013-12-05 | Plus Chemicals S.A. | Solid state forms of cabazitaxel and processes for preparation thereof |
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| US9394266B2 (en) | 2012-03-08 | 2016-07-19 | IVAX International GmbH | Solid state forms of cabazitaxel and processes for preparation thereof |
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| US9353076B2 (en) | 2012-07-25 | 2016-05-31 | Chongqing Taihao Pharmaceutical Co., Ltd. | Crystal form of cabazitaxel and preparation method thereof |
| CN102898406A (en) * | 2012-11-02 | 2013-01-30 | 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 |
| 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 |
| 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 |
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