CN106749322A - The method for separating Ofloxacin enantiomter - Google Patents
The method for separating Ofloxacin enantiomter Download PDFInfo
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- CN106749322A CN106749322A CN201510819239.6A CN201510819239A CN106749322A CN 106749322 A CN106749322 A CN 106749322A CN 201510819239 A CN201510819239 A CN 201510819239A CN 106749322 A CN106749322 A CN 106749322A
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- ofloxacin
- chromatographic column
- lefofloxacin
- dextrorotation
- moving bed
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/06—Peri-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B57/00—Separation of optically-active compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
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- Treatment Of Liquids With Adsorbents In General (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Abstract
The invention discloses a kind of method for separating Ofloxacin enantiomter.The method includes：(1) Ofloxacin sample is dissolved, to obtain Ofloxacin solution；(2) the Ofloxacin enantiomter in the Ofloxacin solution is separated using simulated moving bed chromatography system, chromatographic condition is as follows：Chromatographic column：Chiralcel OD-H chiral columns；Fixing phase：Surface is coated with the silica gel of cellulose-three [3,5- xylyls carbamate]；Mobile phase：Mixed liquor containing ethanol, n-hexane and phosphoric acid.Present invention process is simple, and product is reliable and stable, can be used for industrialized production.
Description
Technical field
The present invention relates to pharmaceutical field, in particular it relates to chiral drug resolution, separates oxygen fluorine husky more particularly, to one kind
The method of star enantiomter.
Background technology
Ofloxacin (compound shown in formula 1) is a class quinolones extensive pedigree antibiotic, mainly passes through Selective depression bacterium
The activity of DNA gyrases, hinders the synthesis of DNA of bacteria, so as to reach the effect of sterilization.Medicine Ofloxacin is that it is left
Rotation and the raceme compound of dextroisomer, wherein left-handed antibacterial activity is stronger.Lavo-ofloxacin most earlier than 1993
Japan's listing, medicine treatment respiratory tract infection, urogenital infections and skin soft-tissue infection etc..
Have not yet to see the technical method that relevant simulated moving bed chromatography separation point prepares Ofloxacin.
The content of the invention
It is contemplated that at least solving one of technical problem in correlation technique to a certain extent.Therefore, one of the invention
Purpose is to propose a kind of method for separating Ofloxacin enantiomter, and the method can be by the levo form of Ofloxacin and the right side
Rotation body is separated, and purity can reach more than 90%.Present invention process is simple, and the composition and content of product medicine are more accurate, medicine
The more stable reliability of effect, can be used for industrialized production.
In one aspect of the invention, the invention provides a kind of method for separating Ofloxacin enantiomter.According to this hair
Bright embodiment, the method includes：(1) Ofloxacin sample is dissolved, to obtain Ofloxacin solution；(2) profit
The Ofloxacin enantiomter in the Ofloxacin solution is separated with simulated moving bed chromatography system, chromatographic condition is as follows：
Chromatographic column：Chiralcel OD-H chiral columns；Fixing phase：Surface is coated with cellulose-three [3,5- xylyls carbamate]
Silica gel；Mobile phase：Mixed liquor containing ethanol, n-hexane and phosphoric acid.
The method of separation Ofloxacin enantiomter according to embodiments of the present invention, can make lefofloxacin and dextrorotation oxygen
Flucloxacillin is able to efficient separating, and the purity of lefofloxacin and dextrorotation Ofloxacin is high.Also, the technique of the method is very
Simplicity, is capable of achieving continuous production, and product quality is stablized.Additionally, using the mixture conduct of ethanol, n-hexane and phosphoric acid
Mobile phase, nontoxic, mobile phase can be recycled fully, and environmental protection is cost-effective.
In addition, the method that SMBC separation according to embodiments of the present invention prepares Ofloxacin, can also have with
Lower additional technical feature：
In some embodiments of the invention, in the mixed liquor containing ethanol, n-hexane and phosphoric acid, the ethanol, institute
The volume ratio for stating n-hexane and the phosphoric acid is (0-100)：(0-100)：(0-100), preferably (80-100)：(0-20)：
(0.5-1), more preferably 95；5：0.5.Thus be conducive to separating.
In some embodiments of the invention, the simulated moving bed chromatography system includes：Chromatographic column area：The chromatographic column area
It is made up of 4~12 root chromatogram columns, and the chromatographic column divides into I, II, III, IV area, wherein, include per area：1~
3 root chromatogram columns；Sampling pump；Wash-out pump；Extraction pump；And magnetic valve.The number of chromatographic column is more, and separating effect is better,
But disengaging time is also longer, inventor's numerous studies find, chromatographic column area is made up of 4~12 root chromatogram columns, reach separation effect
Fruit and the best of breed of disengaging time.
With reference to Fig. 1, in some embodiments of the invention, the simulated moving bed chromatography system is by 4~12 root chromatogram column groups
Into, it is divided into I, II, III, IV area, there is 1~3 root chromatogram column per area.Wherein, Ith area is located at eluent entrance and extract
Between outlet, the desorption of dextrorotation Ofloxacin is mainly realized in Ith area；IIth area is located at extract and exports and injection port between,
IIth area makes dextrorotation Ofloxacin adsorb repeatedly, parse, concentrate；IIIth area is located between injection port and raffinate outlet, in IIIth area
Obtain lefofloxacin；IVth area obtains between eluent entrance positioned at raffinate outlet, and on the one hand the eluent in IIIth area enters IV
Area's reusable edible, on the other hand, IVth area separates out IIIth area and I, so as to prevent the lefofloxacin in raffinate from entering
Enter Ith area.
In some embodiments of the invention, the method includes：(1) the Ofloxacin sample is dissolved in mobile phase, so as to
The Ofloxacin solution is obtained, wherein, the concentration of Ofloxacin is 0.1~200mg/ml in the Ofloxacin solution；(2)
The adjustment of the switching time according to the magnetic valve, so as to isolated lefofloxacin and dextrorotation Ofloxacin product.
In some embodiments of the invention, according to the switching time adjustment of magnetic valve in simulated moving bed chromatography system, separate
Obtain lefofloxacin and dextrorotation Ofloxacin product.
In some embodiments of the invention, the particle diameter of filler is 10~60 μm, preferably 20~30 μm in the chromatographic column.
Thus, it is possible to further improve the separating degree of each chiral component in Ofloxacin.Particle diameter is smaller, and separating effect is better.But grain
Footpath is too small, can increase post pressure.When the particle diameter of filler is 10~60 μm, especially 20~30 μm, good separating effect, post
Pressure is appropriate.
In some embodiments of the invention, step (3) can respectively to lefofloxacin solution and dextrorotation Ofloxacin solution
Further concentrated, recrystallized, being filtered, being dried, to obtain lefofloxacin and dextrorotation of the purity more than 95%
Ofloxacin.
In some embodiments of the invention, in the simulated moving bed chromatography system elute pump discharge be 0ml/min~
100ml/min, 0~10MPa of pressure；Sample introduction pump discharge is 0ml/min~50ml/min, 0~10MPa of pressure；Extraction pump
Flow is 0ml/min~100ml/min, 0~10MPa of pressure.Thus, it is possible to further improve each chiral group in Ofloxacin
The separating degree divided.
In some embodiments of the invention, the switching time of the magnetic valve is 5min~20min.Thus, it is easy to obtain
The lefofloxacin of high-purity and dextrorotation Ofloxacin.
In some embodiments of the invention, the operation temperature of the simulated moving bed chromatography system is 20~40 DEG C, preferably
25~30 DEG C.Thus, it is possible to further improve the separating degree of each chiral component in Ofloxacin.
In some embodiments of the invention, the simulated moving bed chromatography system by the continuous feed of PLC program control realization,
Continuous discharge.
One of the method for the separation Ofloxacin enantiomter of the embodiment of the present invention, at least have the advantages that：
(1) levo form of Ofloxacin and d-isomer are separated using SMBC technology, the levo form of Ofloxacin
More than 90% is can reach with d-isomer purity.
(2) technological process is very easy, is capable of achieving continuous production, the content of the levo form of Ofloxacin and d-isomer in product
Accurately, the quality of medicine is more stable.
(3) whole technique is not related to poisonous and harmful substance, using the mixture of ethanol, n-hexane and phosphoric acid as mobile phase,
Can fully recycle, it is environmental protection, cost-effective.
Additional aspect of the invention and advantage will be set forth in part in the description, and partly will from the following description become bright
It is aobvious, or recognized by practice of the invention.
Brief description of the drawings
Fig. 1 shows the structural representation of simulated moving bed chromatography system according to an embodiment of the invention.
Specific embodiment
Embodiments of the invention are described below in detail.The embodiments described below is exemplary, is only used for explaining the present invention,
And be not considered as limiting the invention.Unreceipted particular technique or condition in embodiment, according to document in the art
Described technology or condition are carried out according to product description.Agents useful for same or the unreceipted production firm person of instrument, are
Can by city available from conventional products.
Ofloxacin raw material used in the embodiment of the present invention is made by oneself for applicant.
Conventional method：
1st, equipment and condition are selected
Using simulated moving bed chromatography system, the system is by wash-out pump, sampling pump, extraction pump, chromatographic column, magnetic valve, unidirectional
Valve, thermostat and PLC system controller and computer are constituted.Sample solution and eluent are respectively from sample liquid entrance and wash-out
Liquid entrance injected system, two enantiomer monomers of Ofloxacin flow out from two outlets of raffinate and extract respectively, often
At regular intervals, sample liquid and eluent entrance, extract and raffinate outlet are switched to down along the direction that mobile phase flows
One chromatographic column.
2nd, chromatographic column filler and mobile phase (solvent) are selected
With the silica gel of cellulose-three [3,5- xylyl carbamate] for chiral stationary phase, filler particle size is 10~60 μm, stream
Dynamic is mutually the mixture of ethanol, n-hexane and phosphoric acid.
3rd, separating step
(1) after sample is with flowing phased soln, system is entered by sampling pump, system is divided into 4 areas, and chromatographic column number is more
Separation purity is higher, but the complexity and system pressure of system are higher, and what is be best suitable for is 4~16, by Simulation moving bed color
The controller of spectra system, the periodically opening and closing of control magnetic valve, makes wash-out mouth, injection port, extract and raffinate outlet along stream
Dynamic phase direction exchange-column shift, makes two enantiomer monomers of Ofloxacin from extract and raffinate outlet outflow system；
(2) product solution for obtaining, by concentrating, being recrystallized to give qualified products of the purity more than 90%；
(3) check analysis
Mobile phase：Ethanol：N-hexane：Phosphoric acid=95：5：0.5
Flow velocity：0.5mL/min
Pump：10ml analyzes pump
Chromatographic column：Chiralcel OD-H (4.6*250mm, 20 μm)
Detector：UV-detector
Column temperature：25℃
Detection wavelength：294nm.
Embodiment 1
Mobile phase：Ethanol：N-hexane：Phosphoric acid=95：5：0.5
Flow velocity：1ml/min
Sample introduction concentration：Ofloxacin raceme：0.2mg/ml
Sample introduction flow velocity：V1=0.1ml/min
Flow rate of mobile phase：V2=1.0ml/min
Rinse flow velocity：V3=2.0ml/min
F pump pressures：6.8MPa
P pump pressures：7.5MPa
D pump pressures：6.8MPa
Switching time：8.5min
Column temperature：25℃
Check analysis
Constituted using chiral column Chiralcel OD-H analytical extractions liquid and raffinate, wherein, lefofloxacin or dextrorotation oxygen fluorine
The content of Sha Xing is respectively 100%, 98%.
Embodiment 2
Mobile phase：Ethanol：N-hexane：Phosphoric acid=85：15：1
Flow velocity：1ml/min
Sample introduction concentration：Ofloxacin raceme：0.2mg/ml
Sample introduction flow velocity：V1=0.1ml/min
Flow rate of mobile phase：V2=1.0ml/min
Rinse flow velocity：V3=0.5ml/min
F pump pressures：6.5MPa
P pump pressures：4.5MPa
D pump pressures：6.5MPa
Switching time：8.5min
Column temperature：25℃
Check analysis
Constituted using chiral column Chiralcel OD-H analytical extractions liquid and raffinate, wherein, lefofloxacin or dextrorotation oxygen fluorine
The content of Sha Xing is respectively 90%, 100%.
Embodiment 3
Mobile phase：Ethanol：N-hexane：Phosphoric acid=90：10：0.5
Flow velocity：1ml/min
Sample introduction concentration：Ofloxacin raceme：0.2mg/ml
Sample introduction flow velocity：V1=0.1ml/min
Flow rate of mobile phase：V2=1.0ml/min
Rinse flow velocity：V3=2.0ml/min
F pump pressures：6.8MPa
P pump pressures：7.5MPa
D pump pressures：7.0MPa
Switching time：8.5min
Column temperature：25℃
Check analysis
Constituted using chiral column Chiralcel OD-H analytical extractions liquid and raffinate, wherein, lefofloxacin or dextrorotation oxygen fluorine
The content of Sha Xing is respectively 100%, 90%.
Comparative example 1
Mobile phase：Ethanol：N-hexane：Phosphoric acid=75：5：0.5
Flow velocity：1ml/min
Sample introduction concentration：Ofloxacin raceme：0.2mg/ml
Sample introduction flow velocity：V1=0.1ml/min
Flow rate of mobile phase：V2=1.0ml/min
Rinse flow velocity：V3=2.0ml/min
F pump pressures：6.1MPa
P pump pressures：8.2MPa
D pump pressures：6.6MPa
Switching time：9min
Column temperature：25℃
Check analysis
Constituted using chiral column Chiralcel OD-H analytical extractions liquid and raffinate, wherein, lefofloxacin or dextrorotation oxygen fluorine
The content of Sha Xing is respectively 75%, 85%, and the purity of lefofloxacin or dextrorotation Ofloxacin is low, and separating effect is significantly low
In the separating effect of embodiment 1-3.
In the description of the invention, it is to be understood that term " first ", " second " are only used for describing purpose, without being understood that
To indicate or implying relative importance or the implicit quantity for indicating indicated technical characteristic.Thus, " first ", " are defined
Two " one or more this feature can be expressed or be implicitly included to feature.In the description of the invention, " multiple "
Two or more are meant that, unless otherwise expressly limited specifically.
In the description of this specification, reference term " one embodiment ", " some embodiments ", " example ", " specific example ",
Or the description of " some examples " etc. means to combine specific features, structure, material or feature bag that the embodiment or example are described
It is contained at least one embodiment of the invention or example.In this manual, to the schematic representation of above-mentioned term necessarily
It is directed to identical embodiment or example.And, the specific features of description, structure, material or feature can be any
Combined in an appropriate manner in individual or multiple embodiments or example.Additionally, in the case of not conflicting, the skill of this area
Can be combined for the feature of the different embodiments or example described in this specification and different embodiments or example by art personnel
And combination.
Although embodiments of the invention have been shown and described above, it is to be understood that above-described embodiment be it is exemplary,
It is not considered as limiting the invention, one of ordinary skill in the art within the scope of the invention can be to above-described embodiment
It is changed, changes, replacing and modification.
Claims (10)
1. it is a kind of separate Ofloxacin enantiomter method, it is characterised in that including：
(1) Ofloxacin sample is dissolved, to obtain Ofloxacin solution；
(2) the Ofloxacin enantiomter in the Ofloxacin solution, chromatostrip are separated using simulated moving bed chromatography system
Part is as follows：
Chromatographic column：Chiralcel OD-H chiral columns；
Fixing phase：Surface is coated with the silica gel of cellulose-three [3,5- xylyls carbamate]；
Mobile phase：Mixed liquor containing ethanol, n-hexane and phosphoric acid.
2. method according to claim 1, it is characterised in that the mixed liquor containing ethanol, n-hexane and phosphoric acid
In, the volume ratio of the ethanol, the n-hexane and the phosphoric acid is (0-100)：(0-100)：(0-100), preferably
(80-100)：(0-20)：(0.5-1), more preferably 95；5：0.5.
3. method according to claim 1, it is characterised in that the simulated moving bed chromatography system includes：
Chromatographic column area：The chromatographic column area is made up of 4~12 root chromatogram columns, and the chromatographic column divide into I, II, III,
IVth area, wherein, include per area：
1~3 root chromatogram column；
Sampling pump；
Wash-out pump；
Extraction pump；And
Magnetic valve.
4. method according to claim 3, it is characterised in that including：
(1) the Ofloxacin sample is dissolved in mobile phase, to obtain the Ofloxacin solution, wherein, the oxygen fluorine
The concentration of Ofloxacin is 0.1~200mg/ml in husky star solution；
(2) adjustment of the switching time according to the magnetic valve, so as to isolated lefofloxacin and dextrorotation Ofloxacin.
5. method according to claim 1, it is characterised in that the particle diameter of filler is 10~60 μm in the chromatographic column,
Preferably 20~30 μm.
6. method according to claim 4, it is characterised in that further include：
The lefofloxacin and the dextrorotation Ofloxacin are concentrated, are recrystallized, filtered and dried, to obtain
Lefofloxacin sterling and dextrorotation Ofloxacin sterling, wherein, the lefofloxacin sterling is husky with the dextrorotation oxygen fluorine
The purity of star sterling is not less than 90%.
7. the method that separation according to claim 3 prepares Ofloxacin, it is characterised in that
The wash-out pump discharge is 0ml/min~100ml/min, 0~10MPa of pressure；
The sample introduction pump discharge is 0ml/min~50ml/min, 0~10MPa of pressure；
The extraction pump discharge is 0ml/min~100ml/min, 0~10MPa of pressure.
8. the method that separation according to claim 3 prepares Ofloxacin, it is characterised in that the switching of the magnetic valve
Time is 5min~20min.
9. the method that separation according to claim 1 prepares Ofloxacin, it is characterised in that the Simulation moving bed color
The operation temperature of spectra system is 20~40 DEG C, preferably 25~30 DEG C.
10. the method that separation according to claim 3 prepares Ofloxacin, it is characterised in that the Simulation moving bed
Chromatographic system by PLC program control, to realize continuous feed and continuous discharge.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109580837A (en) * | 2018-12-31 | 2019-04-05 | 辰欣药业股份有限公司 | A kind of detection method of Levofloxacin Hydrochloride Injection |
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