CN107955021A - A kind of production method of the Ceftriaxone Sodium of low impurity - Google Patents
A kind of production method of the Ceftriaxone Sodium of low impurity Download PDFInfo
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- CN107955021A CN107955021A CN201711026274.8A CN201711026274A CN107955021A CN 107955021 A CN107955021 A CN 107955021A CN 201711026274 A CN201711026274 A CN 201711026274A CN 107955021 A CN107955021 A CN 107955021A
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- ceftriaxone sodium
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/36—Methylene radicals, substituted by sulfur atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/02—Preparation
- C07D501/04—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents
- C07D501/06—Acylation of 7-aminocephalosporanic acid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/02—Preparation
- C07D501/12—Separation; Purification
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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
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- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Abstract
The present invention provides a kind of production method of the Ceftriaxone Sodium of low impurity, and specific preparation method is：By 7 ACA and triazine ring in acetonitrile solution, with boron trifluoride acetonitrile solution catalyzing, react at normal temperatures, triithylamine is added dropwise and adjusts pH value to faintly acid, is separated out to solid, washs drying, obtain 7 ACT；Using 7 ACT as raw material, triethylamine and cefotaxime is added dropwise, is reacted in low temperature environment, obtains coarse salt of ceftriaxone sodium；By the ground screening of coarse salt of ceftriaxone sodium, Ceftriaxone Sodium fine grain is obtained, Ceftriaxone Sodium fine grain is added in aqueous acetone solution, after constant temperature stirring and dissolving, activated carbon is added, is stirred at room temperature, is filtered, stream solubilization analysis agent, crystal is separated out, growing the grain, filtering and washing drying, obtains Ceftriaxone Sodium.Ceftriaxone Sodium reaction temperature prepared by the present invention is low, and high income, effect is good, and impurity is low, is easy to industrialized production.
Description
Technical field
The invention belongs to medicinal chemistry art, and in particular to a kind of production method of the Ceftriaxone Sodium of low impurity.
Background technology
Ceftriaxone Sodium is a kind of water miscible beta-lactam cynnematin, be a kind of parenteral route, it is semi-synthetic,
The Third generation Cephalosporins antibiotic of broad-spectrum long-acting, antibacterial very sensitive for most of gram-positive bacteria and negative bacterium
Spectrum width, antibacterial action is strong, and resistance to enzyme degraded, toxicity is low, tissue penetration is strong, long half time.The beta-lactam structure of ceftriaxone
The carboxypeptidase, endopeptidase, transpeptidase of bacterial cell plasma membrane are acted on, these enzymes both participate in cell synthesis and cell division,
Cause Cell Wall Deficient and cell death by these, it is suppressed that the glutinous peptide symthesis of bacteria cell wall, reaches therapeutic effect, controlling
Treat the infection such as lower respiratory tract infection, skin histology, urinary tract infection, Bones and joints and bacterial septicemia illness has been achieved for well
Therapeutic effect.But the price of Ceftriaxone Sodium and yield are influenced very big by 7-ACA, current foreign countries major part 7-ACA is adopted
It is made with enzyme process, and it is prepared by the domestic method that cephalosporin chemical cracking is generally adopted, enzyme law catalysis reaction prepares 7-ACA institutes
Accounting example is small.
A kind of synthetic method of Ceftriaxone Sodium disclosed in Chinese patent CN 104130273B, by dimethyl carbonate, trifluoro
After change boron, dimethyl carbonate and organic acid quickly stir cooling, addition triazine ring and 7-ACA, low-temp reaction, addition cold water,
EDTA-2Na, sodium dithionite, separate out filtration drying and obtain 7-ACT, then 7-ACT is added to dichloromethane and ethanol mixing
In solvent, to be stirred at -10 DEG C, tetramethylguanidine and AE active ester is added dropwise, reaction is stood, and water intaking is added to sodium salt, and crystal separates out,
Growing the grain, is dried in vacuo after filtering, obtains Ceftriaxone Sodium.The reaction temperature reduces, and the reaction time shortens, the yield of product and pure
Degree is all significantly improved.The side of phase transfer catalysis process synthesizing coarse salt of ceftriaxone sodium disclosed in Chinese patent CN 101747346B
Method, is raw material by 7-amino-cephalosporanic acid and triazine ring, in the presence of boron trifluoride-acetonitrile catalyst, carries out electrophilic substitution reaction,
Then adding Carboxypeptidase A and reaction is hydrolyzed, crystallization filtering, obtains 7-ACT, then by 7-ACT and 2-(2-Amino-4-thiazolyl)-2-methoxyiminoacetic,thiobenzothiazole ester in organic phase
Add phase transfer catalyst and carry out N- acylation reactions and obtain ceftriaxone acid, re-forming salt-forming reaction, to obtain Ceftriaxone Sodium thick
Salt.This method reduces the production of macromolecule impurity using phase transfer catalysis process synthesis ceftriaxone sodium salt, therefore product
Purity is high, high income.
The content of the invention
The technical problem to be solved in the present invention is to provide a kind of production method of the Ceftriaxone Sodium of low impurity, by 7-ACA
With triazine ring in acetonitrile solution, with boron trifluoride acetonitrile solution catalyzing, react at normal temperatures, be added dropwise triithylamine adjust pH value to
Faintly acid, separates out to solid, washs drying, obtains 7-ACT；Using 7-ACT as raw material, triethylamine and cefotaxime is added dropwise, in low temperature
Environment reaction, obtains coarse salt of ceftriaxone sodium；By the ground screening of coarse salt of ceftriaxone sodium, Ceftriaxone Sodium fine grain is obtained, will
Ceftriaxone Sodium fine grain is added in aqueous acetone solution, after constant temperature stirring and dissolving, is added activated carbon, is stirred at room temperature, filter, stream adds
Dissolved agent, separates out crystal, growing the grain, filtering and washing drying, obtains Ceftriaxone Sodium.Ceftriaxone Sodium reaction temperature prepared by the present invention
Low, high income is spent, effect is good, and impurity is low, is easy to industrialized production.
In order to solve the above technical problems, the technical scheme is that：
A kind of production method of the Ceftriaxone Sodium of low impurity, comprises the following steps：
(1) 7-ACA and triazine ring, with boron trifluoride acetonitrile solution catalyzing, are reacted at normal temperatures in acetonitrile solution, dripped
Add triithylamine to adjust pH value to faintly acid, separated out to solid, wash drying, obtain 7-ACT；
(2) 7-ACT prepared using step (1) is added dropwise triethylamine and cefotaxime, reacts, obtain at low ambient temperatures as raw material
To coarse salt of ceftriaxone sodium；
(3) the ground screening of coarse salt of ceftriaxone sodium for preparing step (2), obtains Ceftriaxone Sodium fine grain, by cephalo
Qusong sodium fine grain is added in aqueous acetone solution, after constant temperature stirring and dissolving, is added activated carbon, is stirred at room temperature, filters, stream solubilization analysis
Agent, separates out crystal, growing the grain, filtering and washing drying, obtains the Ceftriaxone Sodium of low impurity.
As the preferred of above-mentioned technical proposal, in the step (1), weakly acidic pH value is 3.5-5.
As the preferred of above-mentioned technical proposal, in the step (1), the temperature reacted under room temperature is 25-30 DEG C, and the time is
3-4h。
As the preferred of above-mentioned technical proposal, in the step (2), the temperature of low-temp reaction is -10~0 DEG C, during reaction
Between be 4-6h.
As the preferred of above-mentioned technical proposal, in the step (3), the particle diameter of Ceftriaxone Sodium fine grain is 19-20 μm.
As the preferred of above-mentioned technical proposal, in the step (3), the mass fraction of acetone is 30- in aqueous acetone solution
60%.
As the preferred of above-mentioned technical proposal, in the step (3), the temperature of constant temperature stirring is 0-15 DEG C.
As the preferred of above-mentioned technical proposal, in the step (3), the mass ratio of activated carbon and Ceftriaxone Sodium is 1:
10。
As the preferred of above-mentioned technical proposal, in the step (3), dissolved agent is ethanol and neopelex
The mass fraction 0.5-1% of mixture, wherein neopelex.
As the preferred of above-mentioned technical proposal, in the step (3), the temperature of growing the grain is 5-15 DEG C.
Compared with prior art, the invention has the advantages that：
The Ceftriaxone Sodium of low impurity prepared by the present invention is using 7-ACA as parent nucleus, first through triazine heterocyclic substituted, is being carried out
The N- acylation reactions of cefotaxime heterocycle, it is simple and convenient, by low-temp reaction, the quality and yield of product are improved, will be prepared in addition
Coarse salt of ceftriaxone sodium through aqueous acetone solution dissolving recrystallization processing, coarse salt of ceftriaxone sodium solubility in aqueous acetone solution
It is good, there is the degree of supersaturation of adequate operation, dielectric constant is small, is more conducive to the precipitation of solute, then through containing dodecyl benzene sulfonic acid
The ethanol solution dissolved of sodium, growing the grain make that the granularity of the Ceftriaxone Sodium of the recrystallization of preparation is big, and particle diameter distribution is homogeneous, and impurity is few,
Purity is high, is easy to industrialized production.
Embodiment
Below in conjunction with specific embodiment, the present invention will be described in detail, herein illustrative examples and explanation of the invention
For explaining the present invention, but it is not as a limitation of the invention.
Embodiment 1：
(1) it is anti-under 25 DEG C of room temperature with boron trifluoride acetonitrile solution catalyzing by 7-ACA and triazine ring in acetonitrile solution
3h is answered, triithylamine is added dropwise and adjusts pH value to 3.5 faintly acids, is separated out to solid, washs drying, obtain 7-ACT.
(2) using 7-ACT as raw material, triethylamine and cefotaxime is added dropwise, 4h is reacted under -10 DEG C of low temperature environments, obtains cephalo
Qusong sodium crude salt.
(3) by the ground screening of coarse salt of ceftriaxone sodium, the Ceftriaxone Sodium fine grain that particle diameter is 19-20 μm is obtained, by head
Spore Qusong sodium fine grain is added in the aqueous acetone solution that mass fraction is 30%, after 0 DEG C of constant temperature stirring and dissolving, according to activated carbon
Mass ratio with Ceftriaxone Sodium is 1:10, activated carbon is added, is stirred at room temperature, is filtered, stream plus ethanol and dodecyl benzene sulfonic acid
The mass fraction 0.5% of the mixture dissolved agent, wherein neopelex of sodium, separates out crystal, at 5 DEG C growing the grain, takes out
Filter washing is dried, and obtains the Ceftriaxone Sodium of low impurity.
Embodiment 2：
(1) it is anti-under 30 DEG C of room temperature with boron trifluoride acetonitrile solution catalyzing by 7-ACA and triazine ring in acetonitrile solution
4h is answered, triithylamine is added dropwise and adjusts pH value to 5 faintly acids, is separated out to solid, washs drying, obtain 7-ACT.
(2) using 7-ACT as raw material, triethylamine and cefotaxime is added dropwise, reacts 6h under 0 DEG C of low temperature environment, obtain cephalo song
Loose sodium crude salt.
(3) by the ground screening of coarse salt of ceftriaxone sodium, the Ceftriaxone Sodium fine grain that particle diameter is 19-20 μm is obtained, by head
Spore Qusong sodium fine grain is added in the aqueous acetone solution that mass fraction is 60%, after 15 DEG C of constant temperature stirring and dissolvings, according to activity
The mass ratio of charcoal and Ceftriaxone Sodium is 1:10, activated carbon is added, is stirred at room temperature, is filtered, stream plus ethanol and detergent alkylate sulphur
The mass fraction 1% of the mixture dissolved agent, wherein neopelex of sour sodium, separates out crystal, the growing the grain at 15 DEG C, takes out
Filter washing is dried, and obtains the Ceftriaxone Sodium of low impurity.
Embodiment 3：
(1) it is anti-under 26 DEG C of room temperature with boron trifluoride acetonitrile solution catalyzing by 7-ACA and triazine ring in acetonitrile solution
3.5h is answered, triithylamine is added dropwise and adjusts pH value to 4 faintly acids, is separated out to solid, washs drying, obtain 7-ACT.
(2) using 7-ACT as raw material, triethylamine and cefotaxime is added dropwise, 5h is reacted under -5 DEG C of low temperature environments, obtain cephalo song
Loose sodium crude salt.
(3) by the ground screening of coarse salt of ceftriaxone sodium, the Ceftriaxone Sodium fine grain that particle diameter is 19-20 μm is obtained, by head
Spore Qusong sodium fine grain is added in the aqueous acetone solution that mass fraction is 40%, after 5 DEG C of constant temperature stirring and dissolvings, according to activated carbon
Mass ratio with Ceftriaxone Sodium is 1:10, activated carbon is added, is stirred at room temperature, is filtered, stream plus ethanol and dodecyl benzene sulfonic acid
The mass fraction 0.6% of the mixture dissolved agent, wherein neopelex of sodium, separates out crystal, the growing the grain at 10 DEG C, takes out
Filter washing is dried, and obtains the Ceftriaxone Sodium of low impurity.
Embodiment 4：
(1) it is anti-under 28 DEG C of room temperature with boron trifluoride acetonitrile solution catalyzing by 7-ACA and triazine ring in acetonitrile solution
3.5h is answered, triithylamine is added dropwise and adjusts pH value to 4.5 faintly acids, is separated out to solid, washs drying, obtain 7-ACT.
(2) using 7-ACT as raw material, triethylamine and cefotaxime is added dropwise, 4.5h is reacted under -8 DEG C of low temperature environments, obtains cephalo
Qusong sodium crude salt.
(3) by the ground screening of coarse salt of ceftriaxone sodium, the Ceftriaxone Sodium fine grain that particle diameter is 19-20 μm is obtained, by head
Spore Qusong sodium fine grain is added in the aqueous acetone solution that mass fraction is 45%, after 3 DEG C of constant temperature stirring and dissolvings, according to activated carbon
Mass ratio with Ceftriaxone Sodium is 1:10, activated carbon is added, is stirred at room temperature, is filtered, stream plus ethanol and dodecyl benzene sulfonic acid
The mass fraction 0.7% of the mixture dissolved agent, wherein neopelex of sodium, separates out crystal, the growing the grain at 8 DEG C, takes out
Filter washing is dried, and obtains the Ceftriaxone Sodium of low impurity.
Embodiment 5：
(1) it is anti-under 30 DEG C of room temperature with boron trifluoride acetonitrile solution catalyzing by 7-ACA and triazine ring in acetonitrile solution
3h is answered, triithylamine is added dropwise and adjusts pH value to 5 faintly acids, is separated out to solid, washs drying, obtain 7-ACT.
(2) using 7-ACT as raw material, triethylamine and cefotaxime is added dropwise, 6h is reacted under -10 DEG C of low temperature environments, obtains cephalo
Qusong sodium crude salt.
(3) by the ground screening of coarse salt of ceftriaxone sodium, the Ceftriaxone Sodium fine grain that particle diameter is 19-20 μm is obtained, by head
Spore Qusong sodium fine grain is added in the aqueous acetone solution that mass fraction is 30%, after 15 DEG C of constant temperature stirring and dissolvings, according to activity
The mass ratio of charcoal and Ceftriaxone Sodium is 1:10, activated carbon is added, is stirred at room temperature, is filtered, stream plus ethanol and detergent alkylate sulphur
The mass fraction 0.5% of the mixture dissolved agent, wherein neopelex of sour sodium, precipitation crystal, the growing the grain at 15 DEG C,
Filtering and washing is dried, and obtains the Ceftriaxone Sodium of low impurity.
Embodiment 6：
(1) it is anti-under 25 DEG C of room temperature with boron trifluoride acetonitrile solution catalyzing by 7-ACA and triazine ring in acetonitrile solution
4h is answered, triithylamine is added dropwise and adjusts pH value to 3.5 faintly acids, is separated out to solid, washs drying, obtain 7-ACT.
(2) using 7-ACT as raw material, triethylamine and cefotaxime is added dropwise, reacts 6h under -10~0 DEG C of low temperature environment, obtains to the end
Spore Qusong sodium crude salt.
(3) by the ground screening of coarse salt of ceftriaxone sodium, the Ceftriaxone Sodium fine grain that particle diameter is 19-20 μm is obtained, by head
Spore Qusong sodium fine grain is added in the aqueous acetone solution that mass fraction is 30%, after 15 DEG C of constant temperature stirring and dissolvings, according to activity
The mass ratio of charcoal and Ceftriaxone Sodium is 1:10, activated carbon is added, is stirred at room temperature, is filtered, stream plus ethanol and detergent alkylate sulphur
The mass fraction 0.5% of the mixture dissolved agent, wherein neopelex of sour sodium, precipitation crystal, the growing the grain at 15 DEG C,
Filtering and washing is dried, and obtains the Ceftriaxone Sodium of low impurity.
After testing, the particle diameter of the Ceftriaxone Sodium of low impurity prepared by embodiment 1-6, the result of purity are as follows：
As seen from the above table, the uniform particle sizes of the Ceftriaxone Sodium of low impurity prepared by the present invention, purity are high.
The above-described embodiments merely illustrate the principles and effects of the present invention, not for the limitation present invention.It is any ripe
Know the personage of this technology all can carry out modifications and changes under the spirit and scope without prejudice to the present invention to above-described embodiment.Cause
This, those of ordinary skill in the art is complete without departing from disclosed spirit and institute under technological thought such as
Into all equivalent modifications or change, should by the present invention claim be covered.
Claims (10)
1. a kind of production method of the Ceftriaxone Sodium of low impurity, it is characterised in that comprise the following steps：
(1) 7-ACA and triazine ring, with boron trifluoride acetonitrile solution catalyzing, are reacted at normal temperatures in acetonitrile solution, is added dropwise three
Second ammonia adjusts pH value to faintly acid, is separated out to solid, washs drying, obtain 7-ACT；
(2) 7-ACT prepared using step (1) is added dropwise triethylamine and cefotaxime, reacts, obtained to the end at low ambient temperatures as raw material
Spore Qusong sodium crude salt；
(3) the ground screening of coarse salt of ceftriaxone sodium for preparing step (2), obtains Ceftriaxone Sodium fine grain, by ceftriaxone
Sodium fine grain is added in aqueous acetone solution, after constant temperature stirring and dissolving, is added activated carbon, is stirred at room temperature, filters, stream solubilization analysis agent,
Crystal is separated out, growing the grain, filtering and washing drying, obtains the Ceftriaxone Sodium of low impurity.
A kind of 2. production method of the Ceftriaxone Sodium of low impurity according to claim 1, it is characterised in that：The step
(1) in, weakly acidic pH value is 3.5-5.
A kind of 3. production method of the Ceftriaxone Sodium of low impurity according to claim 1, it is characterised in that：The step
(1) in, the temperature reacted under room temperature is 25-30 DEG C, time 3-4h.
A kind of 4. production method of the Ceftriaxone Sodium of low impurity according to claim 1, it is characterised in that：The step
(2) in, the temperature of low-temp reaction is -10~0 DEG C, reaction time 4-6h.
A kind of 5. production method of the Ceftriaxone Sodium of low impurity according to claim 1, it is characterised in that：The step
(3) in, the particle diameter of Ceftriaxone Sodium fine grain is 19-20 μm.
A kind of 6. production method of the Ceftriaxone Sodium of low impurity according to claim 1, it is characterised in that：The step
(3) in, the mass fraction of acetone is 30-60% in aqueous acetone solution.
A kind of 7. production method of the Ceftriaxone Sodium of low impurity according to claim 1, it is characterised in that：The step
(3) in, the temperature of constant temperature stirring is 0-15 DEG C.
A kind of 8. production method of the Ceftriaxone Sodium of low impurity according to claim 1, it is characterised in that：The step
(3) in, the mass ratio of activated carbon and Ceftriaxone Sodium is 1:10.
A kind of 9. production method of the Ceftriaxone Sodium of low impurity according to claim 1, it is characterised in that：The step
(3) in, dissolved agent is ethanol and the mass fraction of the mixture, wherein neopelex of neopelex
0.5-1%.
A kind of 10. production method of the Ceftriaxone Sodium of low impurity according to claim 1, it is characterised in that：The step
Suddenly in (3), the temperature of growing the grain is 5-15 DEG C.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110396101A (en) * | 2018-12-03 | 2019-11-01 | 广东金城金素制药有限公司 | Qu Suofen Ceftriaxone Sodium pharmaceutical preparation treats the new indication of bacillary intimitis |
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| CN102702233A (en) * | 2012-05-18 | 2012-10-03 | 苏州中联化学制药有限公司 | Preparation method of ceftriaxone sodium |
| CN105418641A (en) * | 2015-12-30 | 2016-03-23 | 中山市金城道勃法制药有限公司 | Original-quality ceftriaxone sodium and pharmaceutical preparation thereof |
| CN105585581A (en) * | 2016-03-09 | 2016-05-18 | 上海宁瑞生化技术有限公司 | Method for synthesizing ceftriaxone sodium |
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2017
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| CN110396101A (en) * | 2018-12-03 | 2019-11-01 | 广东金城金素制药有限公司 | Qu Suofen Ceftriaxone Sodium pharmaceutical preparation treats the new indication of bacillary intimitis |
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Application publication date: 20180424 |