CN106632396B - The preparation method and purposes of γ crystal form rifaximin - Google Patents
The preparation method and purposes of γ crystal form rifaximin Download PDFInfo
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- CN106632396B CN106632396B CN201710010821.7A CN201710010821A CN106632396B CN 106632396 B CN106632396 B CN 106632396B CN 201710010821 A CN201710010821 A CN 201710010821A CN 106632396 B CN106632396 B CN 106632396B
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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
- C07D498/22—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 four or more hetero rings
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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
- C07B2200/13—Crystalline forms, e.g. polymorphs
Abstract
The invention belongs to chemical medicines, and in particular to the preparation method and purposes of γ crystal form rifaximin.The technical problem to be solved by the present invention is to recrystallisation solvents to contain large quantity of moisture, so that solvent recovery dehydration is difficult, and yield is not high, so that product cost is excessively high.The scheme that invention solves above-mentioned technical problem is to provide a kind of preparation method of γ crystal form rifaximin, comprising the following steps: a, rifaximin is dissolved in rudimentary ether solvent, obtains mixed solution；B, above-mentioned mixed solution is dry, then filter；C, filtered mixed solution is cooled to -50 DEG C~-80 DEG C, and keeps mutually synthermal and is dried under reduced pressure to solvent volatilization completely, obtain γ crystal form rifaximin.The method provided by the invention for preparing γ crystal form rifaximin is convenient for recycling design, and the crystallization yield of γ crystal form rifaximin is high, and no product loss, yield reaches 100%.
Description
Technical field
The invention belongs to chemical medicines, and in particular to the preparation method and purposes of γ crystal form rifaximin.
Background technique
Rifaximin is the semi-synthetic derivative of Rifamycin Sodium, is a kind of wide spectrum enteron aisle antibiotic, to most grams
Positive and gramnegative bacterium, the infection including aerobic bacteria and anaerobic bacteria have a bactericidal effect, chemistry it is entitled [2S- (2R*,
16Z, 18E, 20R*, 21R*, 22S*, 23S*, 24S*, 25R*, 26S*, 27R*, 28E)] -25- acetoxyl group -5,6,21,23-
Tetrahydroxy -27- methoxyl group -2,4, (epoxy pentadecane [1,11,13] triolefin is sub- for 11,16,20,22,24,26- prestoxs -2,7-
Amine) benzofuran [4,5-e] pyrido [1,2-a] benzimidazole -1,15 (2H)-diketone, structure is as shown in Equation 1:
At present, it has been found that rifaximin crystal form type reach more than ten kinds, comprising: α, β, γ, η, ξ etc., but be used for medicine
Main still α, β, γ these types crystal form of the crystal form of object treatment, wherein again most commonly seen with γ crystal form.United States Patent (USP)
US70456202B2 discloses a kind of preparation method of γ crystal form rifaximin: using ethanol/water mixed solvent to rifaximin
Crude product is crystallized, and crystalline solid is dried under reduced pressure constant weight under ambient temperature and obtains γ crystal form rifaximin, and crystallization yield is
84.7%.United States Patent (USP) US9403844B2 discloses the preparation method of another γ crystal form rifaximin: mixed using acetic acid/water
Bonding solvent crystallizes rifaximin crude product, and crystalline solid is dried to obtain γ crystal form rifaximin at a temperature of 100-110 DEG C, knot
Brilliant yield is 62~65%.The above obtains γ crystal form rifaximin and all there are some drawbacks: as recrystallisation solvent contains largely
Moisture, so that solvent recovery, especially solvent dehydration become difficult；And the yield of method crystallized above is not high, so that producing
Product cost is excessively high.
Summary of the invention
The technical problem to be solved by the present invention is to recrystallisation solvents to contain large quantity of moisture, so that solvent recovery dehydration is difficult, and
And yield is not high, so that product cost is excessively high.
The scheme that invention solves above-mentioned technical problem is to provide a kind of preparation method of γ crystal form rifaximin, including following
Step:
A, rifaximin is dissolved in rudimentary ether solvent, obtains mixed solution；
B, above-mentioned mixed solution is dry, then filter；
C, filtered mixed solution is cooled to -50 DEG C~-80 DEG C, and mutually synthermal be dried under reduced pressure to solvent is kept to wave
It distributes entirely, obtains γ crystal form rifaximin.
Wherein, in the preparation method of above-mentioned γ crystal form rifaximin, rudimentary ether solvent described in step a is ether, two
Any one in isopropyl ether, methyl tertiary butyl ether(MTBE), tetrahydrofuran or glycol dimethyl ether.
Wherein, in above-mentioned preparation method, the mass volume ratio of rifaximin described in step a and rudimentary ether solvent is 1 ︰ 4
~10.
Wherein, in above-mentioned preparation method, the desiccant used when dry described in step b be anhydrous sodium sulfate, molecular sieve or
Any one in active carbon.
Wherein, in above-mentioned preparation method, drying described in step b is to dry to mixed solution water content below 0.5%.
The present invention also provides the pharmaceutical compositions for the γ crystal form rifaximin being prepared containing the above method, and its system
At tablet.The pharmaceutical composition is to be added other drugs with γ crystal form rifaximin active constituent and often prepared with auxiliary material
It forms.The constituent of aforementioned pharmaceutical compositions are as follows: 550 milligrams of γ crystal form rifaximin, 340 milligrams of microcrystalline cellulose, carboxylic first
42 milligrams of base sodium cellulosate, 50 milligrams of tristerin, 5 milligrams of silica gel and 4 milligrams of titanium dioxide.After the composition tabletting
As tablet.
The beneficial effects of the present invention are: the present invention provides a kind of new methods for preparing γ crystal form rifaximin.With
Hygroscopicity is below 1% to the γ crystal form rifaximin of this method preparation in air, therefore can be reserved for and use the longer time,
Extend shelf life of products.In addition, the preparation method provided by the present invention for preparing γ crystal form rifaximin, due to aqueous in solvent
It measures low, is convenient for recycling design, the rate of recovery is high, can reuse after solvent recovery without dehydration.Finally, provided by the present invention
The method crystallization yield for preparing γ crystal form rifaximin is high, and no product loss, yield reaches 100%.
Detailed description of the invention
The X-ray diffracting spectrum of γ crystal form rifaximin prepared by Fig. 1 present invention.Using X ' Pert Pro MRD X-
X ray diffractometer x, (PANalytical, Netherland), Cu K α 1 radiate (0.154056nm), graphite monochromator, tube voltage
40kV, tube current 40mA, 20 ° of θ scanning ranges~60 °, 0.01 °/s of sweep speed, 0.01 ° of step-length.As seen from Figure 1, γ crystal form
Rifaximin on the X-ray powder diffraction spectrogram indicated with 2 θ, 5.04 ± 0.20 °, 7.11 ± 0.20 °, 8.41 ±
0.20 ° has characteristic diffraction peak.
Specific embodiment
The preparation method of γ crystal form rifaximin, comprising the following steps:
A, rifaximin is dissolved in rudimentary ether solvent, obtains mixed solution；
B, above-mentioned mixed solution is dry, then filter；
C, filtered mixed solution is cooled to -50 DEG C~-80 DEG C, and mutually synthermal be dried under reduced pressure to solvent is kept to wave
It distributes entirely, obtains γ crystal form rifaximin.
Wherein, in the preparation method of above-mentioned γ crystal form rifaximin, rudimentary ether solvent described in step a is ether, two
Any one in isopropyl ether, methyl tertiary butyl ether(MTBE), tetrahydrofuran or glycol dimethyl ether.
Wherein, in above-mentioned preparation method, the mass volume ratio of rifaximin described in step a and rudimentary ether solvent is 1 ︰ 4
~10.
Wherein, in above-mentioned preparation method, the desiccant used when dry described in step b be anhydrous sodium sulfate, molecular sieve or
Any one in active carbon.
Wherein, in above-mentioned preparation method, drying described in step b is to dry to mixed solution water content below 0.5%.
The preparation of 1 γ crystal form rifaximin of embodiment
1 gram of unformed rifaximin solid is added under stiring in 4 milliliters of ether, is all dissolved to solid, by 0.5
Gram anhydrous sodium sulfate is added in solution, and closed stirring 2 hours, solution filters under dry nitrogen atmosphere, and filtrate passes through K.F
It is 0.42% that method, which measures moisture content, and filtrate is cooled to -50 DEG C under dry nitrogen atmosphere, keeps solution temperature in -50 DEG C
It is dried under reduced pressure, after solvent volatilizees completely, residue is restored to room temperature under a dry nitrogen atmosphere, it is powdered to obtain cerise
1 gram of solid.
The solid has the feature that on the X-ray powder diffraction spectrogram indicated with 2 θ, 5.04 ± 0.20 °,
7.11 ± 0.20 °, 8.41 ± 0.20 °, have characteristic diffraction peak, it was demonstrated that be γ crystal form rifaximin.
The preparation of 2 γ crystal form rifaximin of embodiment
1 gram of unformed rifaximin solid is added under stiring in 7 milliliters of ether, is all dissolved to solid, by 1 gram
Anhydrous sodium sulfate is added in solution, and closed stirring 2 hours, solution filters under dry nitrogen atmosphere, and filtrate passes through K.F method
Measuring moisture content is 0.44%, and filtrate is cooled to -50 DEG C under dry nitrogen atmosphere, and solution temperature is kept to subtract in -50 DEG C
It press dry dry, after solvent volatilizees completely, residue is restored to room temperature under a dry nitrogen atmosphere, it is powdered solid to obtain cerise
1 gram of body.
The solid has the feature that on the X-ray powder diffraction spectrogram indicated with 2 θ, 5.04 ± 0.20 °,
7.11 ± 0.20 °, 8.41 ± 0.20 °, have characteristic diffraction peak, it was demonstrated that be γ crystal form rifaximin.
The preparation of 3 γ crystal form rifaximin of embodiment
1 gram of unformed rifaximin solid is added under stiring in 10 milliliters of ether, is all dissolved to solid, by 1
Gram anhydrous sodium sulfate is added in solution, and closed stirring 2 hours, solution filters under dry nitrogen atmosphere, and filtrate passes through K.F
It is 0.38% that method, which measures moisture content, and filtrate is cooled to -50 DEG C under dry nitrogen atmosphere, keeps solution temperature in -50 DEG C
It is dried under reduced pressure, after solvent volatilizees completely, residue is restored to room temperature under a dry nitrogen atmosphere, it is powdered to obtain cerise
1 gram of solid.
The solid has the feature that on the X-ray powder diffraction spectrogram indicated with 2 θ, 5.04 ± 0.20 °,
7.11 ± 0.20 °, 8.41 ± 0.20 °, have characteristic diffraction peak, it was demonstrated that be γ crystal form rifaximin.
The preparation of 4 γ crystal form rifaximin of embodiment
1 gram of unformed rifaximin solid is added under stiring in 4 milliliters of diisopropyl ethers, is all dissolved to solid,
0.5 gram of anhydrous sodium sulfate is added in solution, closed stirring 2 hours, solution filters under dry nitrogen atmosphere, filtrate warp
Crossing K.F method measurement moisture content is 0.47%, and filtrate is cooled to -50 DEG C under dry nitrogen atmosphere, keep solution temperature in -
50 DEG C are dried under reduced pressure, and after solvent volatilizees completely, residue are restored to room temperature under a dry nitrogen atmosphere, obtain scarlet toner
1 gram of last shape solid.
The solid has the feature that on the X-ray powder diffraction spectrogram indicated with 2 θ, 5.04 ± 0.20 °,
7.11 ± 0.20 °, 8.41 ± 0.20 °, have characteristic diffraction peak, it was demonstrated that be γ crystal form rifaximin.
The preparation of 5 γ crystal form rifaximin of embodiment
1 gram of unformed rifaximin solid is added under stiring in 4 milliliters of methyl tertiary butyl ether(MTBE)s, it is all molten to solid
Solution, 0.5 gram of anhydrous sodium sulfate is added in solution, and closed stirring 2 hours, solution filters under dry nitrogen atmosphere, filter
Liquid is 0.33% by K.F method measurement moisture content, and filtrate is cooled to -50 DEG C under dry nitrogen atmosphere, keeps solution temperature
It spends and is dried under reduced pressure in -50 DEG C, after solvent volatilizees completely, residue is restored to room temperature under a dry nitrogen atmosphere, obtained fresh
1 gram of red powder solid.
The solid has the feature that on the X-ray powder diffraction spectrogram indicated with 2 θ, 5.04 ± 0.20 °,
7.11 ± 0.20 °, 8.41 ± 0.20 °, have characteristic diffraction peak, it was demonstrated that be γ crystal form rifaximin.
The preparation of 6 γ crystal form rifaximin of embodiment
1 gram of unformed rifaximin solid is added under stiring in 4 milliliters of tetrahydrofurans, is all dissolved to solid,
0.5 gram of anhydrous sodium sulfate is added in solution, closed stirring 2 hours, solution filters under dry nitrogen atmosphere, filtrate warp
Crossing K.F method measurement moisture content is 0.43%, and filtrate is cooled to -50 DEG C under dry nitrogen atmosphere, keep solution temperature in -
50 DEG C are dried under reduced pressure, and after solvent volatilizees completely, residue are restored to room temperature under a dry nitrogen atmosphere, obtain scarlet toner
1 gram of last shape solid.
The solid has the feature that on the X-ray powder diffraction spectrogram indicated with 2 θ, 5.04 ± 0.20 °,
7.11 ± 0.20 °, 8.41 ± 0.20 °, have characteristic diffraction peak, it was demonstrated that be γ crystal form rifaximin.
The preparation of 7 γ crystal form rifaximin of embodiment
1 gram of unformed rifaximin solid is added under stiring in 4 milliliters of glycol dimethyl ethers, it is all molten to solid
Solution, 0.5 gram of anhydrous sodium sulfate is added in solution, and closed stirring 2 hours, solution filters under dry nitrogen atmosphere, filter
Liquid is 0.27% by K.F method measurement moisture content, and filtrate is cooled to -50 DEG C under dry nitrogen atmosphere, keeps solution temperature
It spends and is dried under reduced pressure in -50 DEG C, after solvent volatilizees completely, residue is restored to room temperature under a dry nitrogen atmosphere, obtained fresh
1 gram of red powder solid.
The solid has following characteristics on the X-ray powder diffraction spectrogram indicated with 2 θ, in 5.04 ± 0.20 °, 7.11
± 0.20 °, 8.41 ± 0.20 °, have characteristic diffraction peak, it was demonstrated that be γ crystal form rifaximin.
The preparation of 8 γ crystal form rifaximin of embodiment
1 gram of unformed rifaximin solid is added under stiring in 4 milliliters of ether, is all dissolved to solid, by 1 gram
Activated 3A molecular sieve is added in solution, and closed stirring 2 hours, solution filters under dry nitrogen atmosphere, filtrate warp
Crossing K.F method measurement moisture content is 0.19%, and filtrate is cooled to -50 DEG C under dry nitrogen atmosphere, keep solution temperature in -
50 DEG C are dried under reduced pressure, and after solvent volatilizees completely, residue are restored to room temperature under a dry nitrogen atmosphere, obtain scarlet toner
1 gram of last shape solid.
The solid has the feature that on the X-ray powder diffraction spectrogram indicated with 2 θ, 5.04 ± 0.20 °,
7.11 ± 0.20 °, 8.41 ± 0.20 °, have characteristic diffraction peak, it was demonstrated that be γ crystal form rifaximin.
The preparation of 9 γ crystal form rifaximin of embodiment
1 gram of unformed rifaximin solid is added under stiring in 4 milliliters of ether, is all dissolved to solid, by 1 gram
Active carbon is added in solution, and closed stirring 2 hours, solution filters under dry nitrogen atmosphere, and filtrate measures by K.F method
Moisture content is 0.45%, and filtrate is cooled to -50 DEG C under dry nitrogen atmosphere, keeps solution temperature dry in -50 DEG C of decompressions
It is dry, after solvent volatilizees completely, residue is restored to room temperature under a dry nitrogen atmosphere, obtains cerise pulverulent solids 1
Gram.
The solid has the feature that on the X-ray powder diffraction spectrogram indicated with 2 θ, 5.04 ± 0.20 °,
7.11 ± 0.20 °, 8.41 ± 0.20 °, have characteristic diffraction peak, it was demonstrated that be γ crystal form rifaximin.
The preparation of 10 γ crystal form rifaximin of embodiment
1 gram of unformed rifaximin solid is added under stiring in 4 milliliters of ether, is all dissolved to solid, by 0.5
Gram anhydrous sodium sulfate is added in solution, and closed stirring 2 hours, solution filters under dry nitrogen atmosphere, and filtrate passes through K.F
It is 0.42% that method, which measures moisture content, and filtrate is cooled to -65 DEG C under dry nitrogen atmosphere, keeps solution temperature in -65 DEG C
It is dried under reduced pressure, after solvent volatilizees completely, residue is restored to room temperature under a dry nitrogen atmosphere, it is powdered to obtain cerise
1 gram of solid.
The solid has the feature that on the X-ray powder diffraction spectrogram indicated with 2 θ, 5.04 ± 0.20 °,
7.11 ± 0.20 °, 8.41 ± 0.20 °, have characteristic diffraction peak, it was demonstrated that be γ crystal form rifaximin.
The preparation of 11 γ crystal form rifaximin of embodiment
1 gram of unformed rifaximin solid is added under stiring in 4 milliliters of ether, is all dissolved to solid, by 0.5
Gram anhydrous sodium sulfate is added in solution, and closed stirring 2 hours, solution filters under dry nitrogen atmosphere, and filtrate passes through K.F
It is 0.44% that method, which measures moisture content, and filtrate is cooled to -80 DEG C under dry nitrogen atmosphere, keeps solution temperature in -80 DEG C
It is dried under reduced pressure, after solvent volatilizees completely, residue is restored to room temperature under a dry nitrogen atmosphere, it is powdered to obtain cerise
1 gram of solid.
The solid has the feature that on the X-ray powder diffraction spectrogram indicated with 2 θ, 5.04 ± 0.20 °,
7.11 ± 0.20 °, 8.41 ± 0.20 °, have characteristic diffraction peak, it was demonstrated that be γ crystal form rifaximin.
The preparation of 12 γ crystal form rifaximin of embodiment
1 gram of alpha-crystal form rifaximin solid is added under stiring in 4 milliliters of ether, is all dissolved to solid, by 1 gram
Anhydrous sodium sulfate is added in solution, and closed stirring 2 hours, solution filters under dry nitrogen atmosphere, and filtrate passes through K.F method
Measuring moisture content is 0.37%, and filtrate is cooled to -80 DEG C under dry nitrogen atmosphere, and solution temperature is kept to subtract in -80 DEG C
It press dry dry, after solvent volatilizees completely, residue is restored to room temperature under a dry nitrogen atmosphere, it is powdered solid to obtain cerise
1 gram of body.
The solid has the feature that on the X-ray powder diffraction spectrogram indicated with 2 θ, 5.04 ± 0.20 °,
7.11 ± 0.20 °, 8.41 ± 0.20 °, have characteristic diffraction peak, it was demonstrated that be γ crystal form rifaximin.
The preparation of 13 γ crystal form rifaximin of embodiment
1 gram of beta crystal rifaximin solid is added under stiring in 4 milliliters of ether, is all dissolved to solid, by 1 gram
Anhydrous sodium sulfate is added in solution, and closed stirring 2 hours, solution filters under dry nitrogen atmosphere, and filtrate passes through K.F method
Measuring moisture content is 0.48%, and filtrate is cooled to -80 DEG C under dry nitrogen atmosphere, and solution temperature is kept to subtract in -80 DEG C
It press dry dry, after solvent volatilizees completely, residue is restored to room temperature under a dry nitrogen atmosphere, it is powdered solid to obtain cerise
1 gram of body.
The solid has the feature that on the X-ray powder diffraction spectrogram indicated with 2 θ, 5.04 ± 0.20 °,
7.11 ± 0.20 °, 8.41 ± 0.20 °, have characteristic diffraction peak, it was demonstrated that be γ crystal form rifaximin.
The preparation of 14 γ crystal form rifaximin of embodiment
1 gram of solid of ξ crystal form rifaximin is added under stiring in 4 milliliters of ether, is all dissolved to solid, by 0.5
Gram anhydrous sodium sulfate is added in solution, and closed stirring 2 hours, solution filters under dry nitrogen atmosphere, and filtrate passes through K.F
It is 0.41% that method, which measures moisture content, and filtrate is cooled to -80 DEG C under dry nitrogen atmosphere, keeps solution temperature in -80 DEG C
It is dried under reduced pressure, after solvent volatilizees completely, residue is restored to room temperature under a dry nitrogen atmosphere, it is powdered to obtain cerise
1 gram of solid.
The solid has the feature that on the X-ray powder diffraction spectrogram indicated with 2 θ, 5.04 ± 0.20 °,
7.11 ± 0.20 °, 8.41 ± 0.20 °, have characteristic diffraction peak, it was demonstrated that be γ crystal form rifaximin.
The experiment of 15 γ crystal form rifaximin X-ray diffraction of embodiment
Using X ' Pert Pro MRD x-ray diffractometer, (PANalytical, Netherland), Cu K α 1 is radiated
(0.154056nm), graphite monochromator, tube voltage 40kV, tube current 40mA, 20 ° of θ scanning ranges~60 °, sweep speed
0.01 °/s, 0.01 ° of step-length.The X-ray diffracting spectrum (attached drawing: Fig. 1) of γ crystal form rifaximin is obtained, the γ crystal form benefit good fortune
Former times is bright on the X-ray powder diffraction spectrogram indicated with 2 θ, in 5.04 ± 0.20 °, 7.11 ± 0.20 °, 8.41 ± 0.20 °, tool
There is characteristic diffraction peak.
16 γ crystal form rifaximin hygroscopicity of embodiment is investigated
γ crystal form rifaximin prepared by above example is weighed about 0.5 gram as in weighing bottle respectively, is done in 105 DEG C
It dry 6 hours, then as room temperature is cooled in drier, after precise weighing, is placed in the humidistat that humidity is 90% and balances 10
It, weighing, according to formula: (weight before weight-balance after balance)/preceding weight Х 100%=hydroscopicity calculating hydroscopicity is balanced,
Measurement result is shown in Table 1.
1 γ crystal form rifaximin hygroscopicity data of table
From above-mentioned experimental result it can be seen that the hygroscopicity of γ crystal form rifaximin provided by the invention is significantly lower than 1%.
Pharmaceutical composition of the embodiment 17 containing γ crystal form rifaximin
The present invention provides γ crystal form rifaximins to prepare the purposes in rifaximin tablet, the pharmaceutical composition be with
γ crystal form rifaximin active constituent, addition other drugs are often prepared with auxiliary material.The constituent of aforementioned pharmaceutical compositions
Are as follows: 550 milligrams of γ crystal form rifaximin, 340 milligrams of microcrystalline cellulose, 42 milligrams of sodium carboxymethylcellulose, tristerin
50 milligrams, 5 milligrams of silica gel and 4 milligrams of titanium dioxide, combination of the above object become every and contain γ crystal form benefit good fortune former times by tabletting
Bright 550 milligrams of tablet.
Claims (4)
1. the preparation method of γ crystal form rifaximin, comprising the following steps:
A, rifaximin is dissolved in rudimentary ether solvent, obtains mixed solution；
B, above-mentioned mixed solution is dry, then filter；
C, filtered mixed solution is cooled to -50 DEG C~-80 DEG C, and mutually synthermal be dried under reduced pressure to solvent is kept to be evaporated completely
Entirely, γ crystal form rifaximin is obtained；
Rudimentary ether solvent described in step a is ether, any one in methyl tertiary butyl ether(MTBE).
2. the preparation method of γ crystal form rifaximin according to claim 1, it is characterised in that: benefit good fortune former times described in step a
The bright mass volume ratio with rudimentary ether solvent is 1:4~10.
3. the preparation method of γ crystal form rifaximin according to claim 1, it is characterised in that: when dry described in step b
The desiccant used is any one in anhydrous sodium sulfate, molecular sieve or active carbon.
4. the preparation method of γ crystal form rifaximin according to claim 1, it is characterised in that: drying described in step b
To dry to mixed solution water content below 0.5%.
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