CN1687044A - Method for producing pure product of paclitaxel - Google Patents
Method for producing pure product of paclitaxel Download PDFInfo
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- CN1687044A CN1687044A CN 200510063054 CN200510063054A CN1687044A CN 1687044 A CN1687044 A CN 1687044A CN 200510063054 CN200510063054 CN 200510063054 CN 200510063054 A CN200510063054 A CN 200510063054A CN 1687044 A CN1687044 A CN 1687044A
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Abstract
The present invention adopts branch, leaf and bark or Taxus Chinese as raw material, and utilizes the processes of extraction, defatting and degumming to obtain extract, using solvent to dissolve the extract, adding adsorbent and mixing them to make concentration and adsorption, adopting industrial solid-liquid phase column chromatographic separation technique and using polar and low-polar solvent or mixed solvent to make elution to remove impurities, and making the section richly containing taxol undergo the processes of concentration, crystallization and vacuum drying so as to obtain the toxol pure product whose purity is greater than 99%.
Description
The technical field taxol, English Paclitaxel by name, systematic naming method is 5 β, 20-epoxy-1,2 α, 4,7 β, 10 β, 13 α-hexahydroxy-Taxan-11-alkene-9-ketone-4,10-diacetate esters-2-benzoic ether-13-[(2 ' R, 3 ' S)-N-benzoyl-3 ' phenylisoserine ester].Its molecular formula is C
47H
51NO
14, molecular weight is 853.9, is the important source material of making the paclitaxel kind anti-cancer drugs thing.The present invention is a raw material with natural or artificial Ramulus et folium taxi cuspidatae and bark, obtains purity greater than 99% elaboration through lixiviate, roughing out, technological process such as refining, belongs to biological chemical field.
The background technology taxol can combine with tubulin, promote that tubulin polymerization is assembled into the microtubule dimer, thereby the physiology depolymerization of microtubule in the inhibition cell, make cell mitogen stop at G2 phase and M phase, stoped the quick breeding of cancer cells, the mechanism of action of this mechanism and the toxic cancer therapy drug of other spindle body is just the opposite, is still unique so far.Clinical study shows, paclitaxel treatment advanced ovarian cancer overall response rate is 56%, the treatment metastatic breast cancer, and the overall response rate is 30%, treatment nonsmall-cell lung cancer overall response rate is 24%, and prostate cancer, upper gastrointestinal cancer, head and neck cancer, leukemia etc. are also had better curative effect.Just from berry Ramulus et folium taxi cuspidatae (Taxus baccataL.), separate to have obtained alkaline matter Taxine as far back as Lucas in 1856, but up to 1960's, on the basis of modern optical spectral technology development, the research of relevant this respect is in full swing.1967, Americanized scholar M.E.Wall at first separated from yewtree with M.C.Wani and obtains taxol, was identified structure and was illustrated that it has antitumour activity by M.C.Wani and colleague thereof in 1971.1979, the Susan B.Horwitz of U.S. einstein medical college etc. found the anticancer mechanism of taxol uniqueness.Carried out the research of administration rules in 1980, nineteen eighty-two, the U.S. began the I clinical trial phase, beginning II clinical trial phase in 1986.On December 29th, 1992, U.S. food and drug administration (FDA) at first ratify the new anti-cancer drug listing of taxol as the treatment advanced ovarian cancer, ratify to be used for the treatment of mammary cancer after 1 year again.Since the nineties, the research of taxol develops on an unprecedented scale, and mainly concentrates on the research or the like of industrialization, low toxicity and the water-soluble novel form of the industrialization of improvement, the cell tissue culture method of raising, the separation method of raw material leaching yield, semi-synthetic and complete synthesizing process.
Existing taxol leach extraction method generally all is with after raw material drying, the pulverizing, leaches with methyl alcohol, ethanol earlier, and thin up with hexane or petroleum ether extraction degreasing, methylene dichloride or chloroform extraction, obtains medicinal extract after concentrating.Its shortcoming is that the extraction consumption of organic solvent is big, and emulsification is serious, leaches yield and is difficult to surpass 85%, and medicinal extract purity is low.
Both at home and abroad at present the method for isolation of taxol generally is to use medicinal extract through multistage silica gel column chromatography, silica gel bonded C-18 column chromatography or polymeric adsorbent column chromatography, obtains product again behind crystallization, recrystallization.The aforesaid method isolation of taxol is the comparison difficulty with contiguous derivative Cephalomannine, and output is very little, thereby needs sometimes through recycle silicon plastic column chromatography after bromination or the oxidation the two to be separated.Aforesaid method products obtained therefrom purity＞98%, but have following defective: (1) yield is low.There is irreversible adsorption in silica gel to taxol, causes product loss, and production purity is greater than 98% taxol, and total recovery is less than 60%.(2) complex operation, output are little.(3) solvent-oil ratio is big, the cost height.(4) a little less than the polymeric adsorbent anti-pressure ability, post is imitated low.(5) be difficult to utilize reproducible Ramulus et folium taxi cuspidatae to carry out suitability for industrialized production for raw material.
Summary of the invention the purpose of this invention is to provide a kind of stable, industrialization, purifies and obtain the method for high-purity taxol at low cost.The present invention adopt content of taxol greater than ten thousand/ Ramulus et folium taxi cuspidatae or bark be raw material, obtain content through lixiviate, degreasing, after coming unstuck greater than 1 percent five medicinal extract.With the medicinal extract dissolution with solvents, add sorbent material and mix concentrated absorption, adopt industrial solid-liquid phase column chromatography separation technology, with polarity, weak polar solvent or mixed solvent wash-out, the impurity different with taxol polarity is removed in segmentation, to be rich in the taxol section through concentrating, obtaining highly purified taxol elaboration after the crystallization, vacuum-drying, purity is greater than 99%.Press the taxol amount and calculate, the direct yield of product is greater than 70%, and total recovery is greater than 85%.Details are as follows for its processing step:
A. extract Ramulus et folium taxi cuspidatae or bark are dried in the shade, pulverized 5mm diameter sieve, divide three adding vat liquors to carry out three grades of intermittently lixiviates, pulverize raw material: vat liquor=1: 7 (W/V), vat liquor are Jia Chun ethanol, particular methanol.One-level vat liquor when wherein third stage vat liquor feeds intake as following batch.First and second grade vat liquor merges concentrated, obtains concentrated solution, and organic solvent is recycled.
B. take off concentrated solution that ester produces steps A and add degreasing fluid at twice and carry out intermittently degreasing of secondary, concentrated solution: degreasing fluid=1: 1 (V/V), degreasing fluid are No. 6 solvent wet goods of Shi Youmi Zheng Jiwan Huan Jiwan, preferred sherwood oil.Stirred 20 minutes, left standstill 60 minutes, discard lower floor's glue or flocculent precipitate, collect subnatant, upper strata liquid merges the recovery solvent.
C. come unstuck with the subnatant adding methylene dichloride of step B subnatant: methylene dichloride=1: 1 (V/V), stirred 15 minutes, left standstill 30 minutes, discard lower floor's glue or flocculent precipitate, get mixed solution.
D. stripping contains the mixed solution adding of step C in the water of 1%NaCl, stirs 20 minutes, leaves standstill 60 minutes, discards upper strata liquid, mixed solution: salt solution=1: 1 (V/V); Add methyl alcohol and salt solution in the subnatant at twice again, stirred 20 minutes at every turn, left standstill 60 minutes, discard upper strata liquid, subnatant: methyl alcohol: salt solution=1: 1: 1 (V/V/V) gets lower floor's organic phase.
E. the lower floor's organic phase that concentrates step C reclaims organic solvent in 60 ℃ of concentrating under reduced pressure, obtains containing the medicinal extract of taxol more than 1.5%.
F. the system material adds acetone solution with step e gained medicinal extract, adds sorbent material, and the taxol net content: sorbent material=1: 200 (W/W) is evaporated to dried at 60 ℃.Sorbent material be gac diatomite atlapulgite silica gel aluminum oxide ion exchange resin polymeric adsorbent etc., preferred silica gel.
G. solid-liquid chromatographic separation material that step F is made pre-column of packing into, the free setting compacting.Pre-column is connected with separator column, carry out gradient elution with the mixed solution of polar solvent and weak polar solvent, wash-out is collected liquid and is detected by TLC and HPLC and carry out staging treating.Gradient is a polar solvent: the stagewise gradient of weak polar solvent=10: 90～100: 0.Above-mentioned polar solvent be methyl alcohol ethanol Virahol acetonitrile the trimethyl carbinol acetone ethyl acetate, ethyl acetate.Above-mentioned weak polar solvent is Lv Fang Si Lvhuatan Er Lvjiawan 1, No. 6 solvent wet goods of 2-Er Lvyiwan Shi Youmi Zheng Jiwan Huan Jiwan, preferred normal hexane.Above-mentioned pre-column is the stainless steel or the glass column of 300mm diameter * 1000mm length; Above-mentioned separator column is the stainless steel or the glass column of 200mm diameter * 2000mm length, is silica gel or aluminum oxide in the post, preferred silica gel.
H. make the collection liquid of expecting step G gained is rich in the taxol section again, add sorbent material, the taxol net content: sorbent material=1: 200 (W/V), at 60 ℃ of concentrating under reduced pressure.Sorbent material be gac atlapulgite silica gel aluminum oxide ion exchange resin polymeric adsorbent etc., preferred polymeric adsorbent.
I. secondary solid-liquid chromatographic separation material that step H the is made pre-column of packing into, the free setting compacting.Pre-column is connected with separator column, carry out gradient elution with the mixed solution of polar solvent and water, wash-out is collected liquid and is detected by TLC and HPLC and carry out staging treating.Gradient is a polar solvent: the stagewise gradient of water=40: 60～100: 0.Above-mentioned polar solvent be methyl alcohol ethanol Virahol acetonitrile the trimethyl carbinol acetone, preferred acetone.Above-mentioned pre-column is the stainless steel or the glass column of 300mm diameter * 1000mm length; Above-mentioned separator column is the stainless steel or the glass column of 200mm diameter * 2000mm length, in the post for bonding octadecyl filler or with silica gel zirconium white be matrix coat polystyrene polystyrene-divinylbenzene polyhutadiene polyacrylic ester polyacrylonitrile polyethylene oxide polyethers the filler of polyacrylamide etc., preferred silica gel zirconium white be that matrix coats polyacrylic ester.
J. crystallization step I gained is rich in the taxol section collection liquid in 60 ℃ of concentrating under reduced pressure, left standstill 12 hours, filter, primary crystallization.
K. recrystallization adds acetone solution with step J gained primary crystallization, and lysate concentration is 8g/L, stirs to add methylene dichloride, stirs ageing 4 hours, filtration, and stirring adds normal hexane in the filtrate, stirs ageing 8 hours, filters, and gets the recrystallization filter cake.Acetone: methylene dichloride: normal hexane=1: 1: 7 (V/V/V).
L. drying obtains highly purified taxol elaboration with step K gained recrystallization filter cake at 60 ℃ of temperature drying under reduced pressure, and purity is greater than 99%, and directly yield is greater than 70%.
M. the low collection liquid that contains the taxol section of step I gained and step J, K gained are reclaimed the mother liquor concentrating under reduced pressure, repeating step F～L continues to obtain highly purified taxol elaboration, and purity is greater than 99%, and total recovery is greater than 85%.
Appended drawings 1 is leaching process process flow sheet of the present invention; Accompanying drawing 2 is treating process process flow sheet of the present invention; Accompanying drawing 3 is the connection diagram of pre-column of the present invention and separator column.
Embodiment
Taxusyunnanensis bark 400kg is got in embodiment 1:1. pre-treatment, and contain taxol and be 0.016% and use methyl alcohol 2800L, three grades of lixiviates, extracting solution is concentrated into 480L, carries out the secondary degreasing with the normal hexane of 480L; Use the 480L methylene dichloride, in methyl alcohol: methylene dichloride: the ratio of 1% salt solution=1: 1: 1 (V/V/V), strip for continuous three times, with lower floor's organic phase concentrate paste 2.6kg, detecting content of taxol through HPLC is 2.2%.
2. the system material adds acetone solution with step 1 gained taxol medicinal extract 2.6Kg, adds silica gel 11Kg, is evaporated to dried at 60 ℃.
3. wash-out material that step 2 the is made pre-column of packing into, the free setting compacting.Pre-column is connected with separator column, and gradient is an ethyl acetate: the stagewise gradient of normal hexane=10: 90～100: 0.Above-mentioned pre-column is the stainless steel column of 300mm diameter * 1000mm length; Above-mentioned separator column is the stainless steel column of 200mm diameter * 2000mm length, is silica gel in the post.
4. make the collection liquid of expecting step 3 gained is rich in the taxol section again, add diatomite 11Kg, be evaporated to dried at 60 ℃.
5. secondary solid-liquid chromatographic separation material that step 4 the is made pre-column of packing into, the free setting compacting.Pre-column is connected with separator column, and gradient is an acetone: the stagewise gradient of water=40: 60～100: 0.Above-mentioned pre-column is the stainless steel column of 300mm diameter * 1000mm length; Above-mentioned separator column is the stainless steel column of 200mm diameter * 2000mm length, coats polyacrylic ester filler for silica matrix in the post.
Crystallization step 5 gained is rich in the taxol section collection liquid in 60 ℃ of concentrating under reduced pressure, left standstill 12 hours, filter, primary crystallization.Primary crystallization is added acetone solution, and lysate concentration is 8g/L, stirs to add methylene dichloride, stirs ageing 4 hours, filtration, and stirring adds normal hexane in the filtrate, stirs ageing 8 hours, filters, and gets the recrystallization filter cake.Acetone: methylene dichloride: normal hexane=1: 1: 7 (V/V/V).
7. drying obtains highly purified taxol elaboration 49.9g with step 6 gained recrystallization filter cake at 60 ℃ of temperature drying under reduced pressure, purity 99.6%, directly yield 77.9%.
Embodiment 2 is with artificial growth Media Ramulus et folium taxi cuspidatae 400kg, and containing taxol is 0.025%, and its technological process is fully identical with embodiment 1, gained taxol elaboration 99.70%, directly yield 75%.
Claims (12)
- The present invention adopt content of taxol greater than ten thousand/ Ramulus et folium taxi cuspidatae or bark be raw material, obtain content through lixiviate, degreasing, after coming unstuck greater than 1 percent five medicinal extract.With the medicinal extract dissolution with solvents, add sorbent material and mix concentrated absorption, adopt industrial solid-liquid phase column chromatography separation technology, with polarity, weak polar solvent or mixed solvent wash-out, the impurity different with taxol polarity is removed in segmentation, will be rich in the taxol section through concentrating, obtaining highly purified taxol elaboration after the crystallization, vacuum-drying.Details are as follows for its processing step:A. extract Ramulus et folium taxi cuspidatae or bark are dried in the shade, pulverized 5mm diameter sieve, divide three adding vat liquors to carry out three grades of intermittently lixiviates, pulverize raw material: vat liquor=1: 7 (W/V).One-level vat liquor when wherein third stage vat liquor feeds intake as following batch.First and second grade vat liquor merges concentrated, obtains concentrated solution, and organic solvent is recycled.B. taking off concentrated solution that ester produces steps A adds degreasing fluid at twice and carries out intermittently degreasing of secondary, concentrated solution: degreasing fluid=1: 1 (V/V).Stirred 20 minutes, left standstill 60 minutes, discard lower floor's glue or flocculent precipitate, collect subnatant, upper strata liquid merges the recovery solvent.C. come unstuck with the subnatant adding methylene dichloride of step B subnatant: methylene dichloride=1: 1 (V/V), stirred 15 minutes, left standstill 30 minutes, discard lower floor's glue or flocculent precipitate, get mixed solution.D. stripping contains the mixed solution adding of step C in the water of 1%NaCl, stirs 20 minutes, leaves standstill 60 minutes, discards upper strata liquid, mixed solution: salt solution=1: 1 (V/V); Add methyl alcohol and salt solution in the subnatant at twice again, subnatant: methyl alcohol: salt solution=1: 1: 1 (V/V/V), stirred 20 minutes at every turn, left standstill 60 minutes, discard upper strata liquid, get lower floor's organic phase.E. the lower floor's organic phase that concentrates step C reclaims organic solvent in 60 ℃ of concentrating under reduced pressure, obtains containing the medicinal extract of taxol more than 1.5%.F. the system material adds acetone solution with step e gained medicinal extract, adds sorbent material, and the taxol net content: sorbent material=1: 200 (W/W) is evaporated to dried at 60 ℃.G. solid-liquid chromatographic separation material that step F is made pre-column of packing into, the free setting compacting.Pre-column is connected with separator column, carry out gradient elution with the mixed solution of polar solvent and weak polar solvent, wash-out is collected liquid and is detected by TLC and HPLC and carry out staging treating.H. make the collection liquid of expecting step G gained is rich in the taxol section again, add sorbent material, the taxol net content: sorbent material=1: 200 (W/V), at 60 ℃ of concentrating under reduced pressure.I. secondary solid-liquid chromatographic separation material that step H the is made pre-column of packing into, the free setting compacting.Pre-column is connected with separator column, carry out gradient elution with the mixed solution of polar solvent and water, wash-out is collected liquid and is detected by TLC and HPLC and carry out staging treating.Gradient is a polar solvent: the stagewise gradient of water=40: 60～100: 0.Above-mentioned pre-column is the stainless steel or the glass column of 300mm diameter * 1000mm length; Above-mentioned separator column is the stainless steel or the glass column of 200mm diameter * 2000mm length.J. crystallization step I gained is rich in the taxol section collection liquid in 60 ℃ of concentrating under reduced pressure, left standstill 12 hours, filter, primary crystallization.K. recrystallization adds acetone solution with step J gained primary crystallization, and lysate concentration is 8g/L, stirs to add methylene dichloride, stirs ageing 4 hours, filtration, and stirring adds normal hexane in the filtrate, stirs ageing 8 hours, filters, and gets the recrystallization filter cake.Acetone: methylene dichloride: normal hexane=1: 1: 7 (V/V/V).L. drying obtains highly purified taxol elaboration with step K gained recrystallization filter cake at 60 ℃ of temperature drying under reduced pressure, and purity is greater than 99%, and directly yield is greater than 70%.M. the low collection liquid that contains the taxol section of step I gained and step J, K gained are reclaimed the mother liquor concentrating under reduced pressure, repeating step F～L continues to obtain highly purified taxol elaboration, and purity is greater than 99%, and total recovery is greater than 85%.
- 2. claim 1 indication Ramulus et folium taxi cuspidatae is meant the Ramulus et folium taxi cuspidatae of various natural Ramulus et folium taxi cuspidatae and artificial growth.
- The described vat liquor of the steps A of claim 1 be methyl alcohol ethanol, particular methanol.
- 4. the step B of claim 1 adopts methyl alcohol and degreasing fluid two-phase to distribute degreasing, does not add water.Described degreasing fluid is No. 6 solvent wet goods of Shi Youmi Zheng Jiwan Huan Jiwan, preferred sherwood oil.
- 5. the step C of claim 1 adopts methyl alcohol to mix with methylene dichloride to come unstuck, do not add water.
- 6. the step D of claim 1 adopts the salt solution of 1% concentration to strip.
- The described sorbent material of the step F of claim 1 be gac diatomite atlapulgite silica gel aluminum oxide ion exchange resin polymeric adsorbent etc., preferred silica gel.
- The described sorbent material of the step H of claim 1 be gac diatomite atlapulgite silica gel aluminum oxide ion exchange resin polymeric adsorbent etc., preferred polymeric adsorbent.
- The described polar solvent of the step I of claim 1 be methyl alcohol ethanol Virahol acetonitrile the trimethyl carbinol acetone, preferred acetone.
- In the described separator column of the step I of claim 1 filler be bonding octadecyl filler or with silica gel zirconium white be matrix coat polystyrene polystyrene-divinylbenzene polyhutadiene polyacrylic ester polyacrylonitrile polyethylene oxide polyethers the filler of polyacrylamide etc., preferred silica gel zirconium white be that matrix coats polyacrylic ester.
- Add methylene dichloride 11. the described re-crystallization step of the step J of claim 1 for primary crystallization is added acetone solution, stirs, stir ageing 4 hours, filtration, stirring adds normal hexane in the filtrate, stirs ageing 8 hours, filters, and gets the recrystallization filter cake.
- 12. the described recrystallization solvent ratio of the step J of claim 1 is an acetone: methylene dichloride: normal hexane=1: 1: 7 (V/V/V).
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102250047A (en) * | 2011-08-26 | 2011-11-23 | 贺金凤 | More-stable taxol compound and medicament composition thereof |
| CN103288785A (en) * | 2013-06-27 | 2013-09-11 | 江苏红豆杉药业有限公司 | Treatment method of paclitaxel waste residues |
| CN104031008A (en) * | 2014-06-30 | 2014-09-10 | 牛兆颖 | Method for preparing taxol crude extract |
| CN105315242A (en) * | 2015-11-17 | 2016-02-10 | 重庆臻源红豆杉发展有限公司 | Removal method of colloid and pigment in crude paclitaxel product |
| CN105503781A (en) * | 2016-01-07 | 2016-04-20 | 吉林省德盛农牧科技发展有限公司 | Method for extracting taxol from filbert shells |
| CN106243066A (en) * | 2016-08-05 | 2016-12-21 | 上海贝美医药科技有限公司 | The crystallization purifications of paclitaxel |
| CN110003143A (en) * | 2019-04-15 | 2019-07-12 | 云南汉德生物技术有限公司 | A method of extracting natural Japanese yew alcohol |
-
2005
- 2005-04-05 CN CN 200510063054 patent/CN1687044A/en active Pending
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102250047A (en) * | 2011-08-26 | 2011-11-23 | 贺金凤 | More-stable taxol compound and medicament composition thereof |
| CN102250047B (en) * | 2011-08-26 | 2013-06-05 | 贺金凤 | Preparation method of taxol compound |
| CN103288785A (en) * | 2013-06-27 | 2013-09-11 | 江苏红豆杉药业有限公司 | Treatment method of paclitaxel waste residues |
| CN103288785B (en) * | 2013-06-27 | 2016-02-03 | 江苏红豆杉药业有限公司 | A kind for the treatment of process of taxol waste residue |
| CN104031008A (en) * | 2014-06-30 | 2014-09-10 | 牛兆颖 | Method for preparing taxol crude extract |
| CN104031008B (en) * | 2014-06-30 | 2015-12-09 | 牛兆颖 | A kind of preparation method of taxol crude extract |
| CN105315242A (en) * | 2015-11-17 | 2016-02-10 | 重庆臻源红豆杉发展有限公司 | Removal method of colloid and pigment in crude paclitaxel product |
| CN105503781A (en) * | 2016-01-07 | 2016-04-20 | 吉林省德盛农牧科技发展有限公司 | Method for extracting taxol from filbert shells |
| CN105503781B (en) * | 2016-01-07 | 2016-12-14 | 吉林省德盛农牧科技发展有限公司 | A kind of hazelnut shell extracts the method for paclitaxel |
| CN106243066A (en) * | 2016-08-05 | 2016-12-21 | 上海贝美医药科技有限公司 | The crystallization purifications of paclitaxel |
| CN110003143A (en) * | 2019-04-15 | 2019-07-12 | 云南汉德生物技术有限公司 | A method of extracting natural Japanese yew alcohol |
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Open date: 20051026 |