CN108239051A - Dehydroandrograpolide succinate and purifying technique and potassium dehydroandrographolide succinate - Google Patents
Dehydroandrograpolide succinate and purifying technique and potassium dehydroandrographolide succinate Download PDFInfo
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- CN108239051A CN108239051A CN201611206563.1A CN201611206563A CN108239051A CN 108239051 A CN108239051 A CN 108239051A CN 201611206563 A CN201611206563 A CN 201611206563A CN 108239051 A CN108239051 A CN 108239051A
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- succinate
- dehydroandrograpolide
- dehydroandrograpolide succinate
- purifying technique
- potassium dehydroandrographolide
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/58—One oxygen atom, e.g. butenolide
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/60—Two oxygen atoms, e.g. succinic anhydride
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- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention provides a kind of purifying technique of dehydroandrograpolide succinate, it is characterised in that：Ethyl alcohol, heating nitrogen charging dissolving are added in dehydroandrograpolide succinate, dehydroandrograpolide succinate is completely dissolved rear low temperature crystallization, separating, washing, drying.The dehydroandrograpolide succinate purified using above-mentioned purifying technique is used to prepare potassium dehydroandrographolide succinate, improves the purity of its potassium dehydroandrographolide succinate, reduces undesirable generation.
Description
Technical field
Purifying technique and obtained dehydration the present invention relates to potassium dehydroandrographolide succinate intermediate-dehydroandrograpolide succinate
Andrographolide succinic acid half-ester and its thus obtained potassium dehydroandrographolide succinate.
Background technology
Potassium dehydroandrographolide succinate is carried using acanthaceous plant Herba Andrographitis [Andrographis paniculata (Burm.f.) Nee s]
Take object andrographolide through being esterified, being dehydrated, into salt and manufactured POTASSIUM DEHYDRO-OGRAPHOLIDE SUCCINATE, wherein being dehydrated
Andrographolide succinic acid half-ester is potassium dehydroandrographolide succinate intermediate.Clinically it is widely used in treatment high fever, respiratory tract infection, children's autumn
The viral diseases such as diarrhea, mumps are one of indispensable pure Chinese medicinal preparation of Emergency department in hospital of TCM (room), at present potassium dehydroandrographolide succinate
Oneself is recorded in Pharmacopoeia of People's Republic of China (two).Chuanhuning preparation product includes potasium dehydroandrographolisuccinate succinate injection and injection wears amber
Rather, while oral preparation is further included.In recent years, with the extensive use of the medicine, the adverse reaction of injection happens occasionally.According to
National drug adverse reaction monitoring center was notified in recent years, and the main adverse reaction in relation to Induced by Chuanhuning Injection is allergic reaction
And decrease of platelet.Main reason that adverse reaction generates is made a concrete analysis of in addition to individual difference (allergic constitution), mainly due to wearing
The impurity contained in the peaceful product of amber excessively causes.Wherein it is pure to include (1) andrographolide original material for its reason of the generation of impurity
Degree is not high；(2) stability itself is poor, easily in generation caused by ester hydrolysis, open loop, isomerization and the oxidation of unsaturated bond
Unstable product quality；(3) andrographolide production technology in esterification, dehydration is unstable, among obtained potassium dehydroandrographolide succinate
Body, that is, andrographolide succinic acid half-ester impurity excessively causes the potassium dehydroandrographolide succinate product impurity subsequently obtained into salt excessive, and then influences
The quality of potassium dehydroandrographolide succinate product.Therefore, how to reduce the impurity in potassium dehydroandrographolide succinate, for clinic provide the potassium dehydroandrographolide succinate product of superperformance into
For technical staff's problem to be solved.
Invention content
First purpose of the present invention is to provide a kind of purifying technique of dehydroandrograpolide succinate, it is therefore an objective to
Prior art problem is solved, the purification that dehydroandrograpolide succinate purity is improved by low temperature crystallization method is provided
Technique reduces the impurity in dehydroandrograpolide succinate.
Second object of the present invention is to provide a kind of dehydroandrograpolide succinate of high-purity, can effectively carry
The purity of potassium dehydroandrographolide succinate that height is subsequently obtained into salt.
Third object of the present invention is to provide a kind of potassium dehydroandrographolide succinate of high-purity.
It is of the present invention solve the problems, such as the technical solution adopted is that：
The purifying technique of dehydroandrograpolide succinate, adds in second in dehydroandrograpolide succinate
Alcohol, heating nitrogen charging dissolving, dehydroandrograpolide succinate are completely dissolved rear low temperature crystallization, separating, washing, drying；It is above-mentioned
Purification process carries out at least once.
Ethyl alcohol can take away the hydrotrope in the relative substance being dehydrated in succinic acid half-ester and alcohol soluble substance.It is molten in low temperature simultaneously
The succinic acid half-ester of the dehydration Herba Andrographitis before not refining can also be taken away in solution preocess because of the dimerization object (oxygen generated during pyroreaction
Compound) so that the quality of product can be higher than 2015 2-3 times of Chinese Pharmacopoeia standards.It is dehydrated in Herba Andrographitis using ethyl alcohol for dissolving
Ester succinic acid half-ester is since the toxicity of ethyl alcohol is very low, and obtained Product Safety is high.
The heating nitrogen charging dissolving, i.e., during heating for dissolving, entire reaction is in nitrogen environment, to reduce oxidation
The generation of object impurity.
Further, dehydroandrograpolide succinate is purified three times.The number of purification can be according to reality
Border situation determines, to reach aimed purity.
Further, the concentration of alcohol is 40%-80%.
Further, the concentration of alcohol is 50%-60%.
Further, the ethyl alcohol is medicinal alcohol.Solvent for dissolving dehydroandrograpolide succinate is adopted
It is since the impurity in common ethyl alcohol is more than medicinal alcohol with the purpose of medicinal alcohol, can allows impurity in the case where dissolving is heated
Oxidation increase.Impurity in medicinal alcohol is less, can it is significantly more efficient reduce Impurities In Solvents introducing, so medicinal alcohol
Impurity content can more be reduced.But meanwhile in the case where solvent purity meets the requirements, non-medicinal alcohol can also be used.
Further, the weight ratio of medicinal alcohol and dehydroandrograpolide succinate is 5-10:1.
Further, the weight ratio of medicinal alcohol and dehydroandrograpolide succinate is 6-8:1.
Further, the solution temperature of dehydroandrograpolide succinate is controlled at 20 DEG C -60 DEG C.
Further, the solution temperature of dehydroandrograpolide succinate is controlled at 40 DEG C -50 DEG C.
Further, dehydroandrograpolide succinate is in subzero 10 DEG C-subzero 20 DEG C of low temperature crystallizations.
Further, dehydroandrograpolide succinate is in subzero 13 DEG C-subzero 17 DEG C of low temperature crystallizations.
Using the Methods For Purification of low temperature crystallization, water-solubility impurity is made to be separated and is dissolved in ethyl alcohol, improved dehydration and wear
The purity of heart lotus lactone succinic acid half-ester crystallization, and then the potassium dehydroandrographolide succinate purity for going out subsequent production is also improved, and reduces
The adverse reaction of drug.
Dehydroandrograpolide succinate is purified using purifying technique described above.
Potassium dehydroandrographolide succinate is prepared by the dehydroandrograpolide succinate after the purification of above-mentioned purifying technique.
Specifically, potassium dehydroandrographolide succinate, is made by following steps,
S1, andrographolide obtain dehydroandrograpolide succinate through being esterified, being dehydrated；
S2, dehydroandrograpolide succinate purification, purifying technique are as described above；
S3, the dehydroandrograpolide succinate after purification obtain potassium dehydroandrographolide succinate through salt-forming reaction.
Beneficial effects of the present invention：
(1) it is used in the present invention and dehydroandrograpolide succinate is dissolved in ethyl alcohol, and low temperature crystallization
Methods For Purification makes water-solubility impurity be separated and is dissolved in ethyl alcohol, improves dehydroandrograpolide succinate crystallization
Purity, and then the potassium dehydroandrographolide succinate purity for going out subsequent production is also improved, and reduces the adverse reaction of drug.
(2) in the present invention when dehydroandrograpolide succinate is dissolved in ethyl alcohol, using the side of nitrogen charging dissolving
Method and heating for dissolving process are in nitrogen environment, reduce the oxidation of dehydroandrograpolide succinate, and then reduce
The generation of oxide impurity further improves the purity of the crystallization of dehydroandrograpolide succinate, similary to reduce
The content of impurity in the potassium dehydroandrographolide succinate that subsequent production goes out, reduces the adverse reaction of drug.
Description of the drawings
Fig. 1 is the chromatogram of unpurified dehydroandrograpolide succinate；
Fig. 2 is the chromatogram of the dehydroandrograpolide succinate after being purified in embodiment 2；
Fig. 3 is the chromatogram of the potassium dehydroandrographolide succinate of purification；
Fig. 4 be it is unpurified after potassium dehydroandrographolide succinate chromatogram.
Specific embodiment
Below in conjunction with specific embodiment, the present invention will be further described in detail.
In the present invention, high-efficient liquid phase color is used to the purity detecting of dehydroandrograpolide succinate and potassium dehydroandrographolide succinate
Spectrometry, condition are as follows：
Instrument model：Efficient liquid phase LC-10AT Gradient methods：Constant current
Detector：Ultraviolet wavelength (nm)：251
Column type number：VP-ODS 4.6*250 column temperatures (DEG C)：25
Embodiment 1
It is prepared by dehydroandrograpolide succinate.
Andrographolide obtains dehydroandrograpolide succinate through being esterified, being dehydrated.Details are provided below.
Andrographolide adds in succinic anhydride, pyridine, anhydrous sodium sulfite, be heated to 110 degree, nitrogen charging reaction stirring it is 3 small
Shi Jinhang is synthesized, and purified water uniform speed slow is added in after synthesis and is stirred 12 hours makes its curing；Separating, washing (adverse current is carried out after curing
It rinses 1 hour)；It is dried after separating, washing (8 hours time of 65 DEG C of temperature)；Dehydro and drographolide amber is obtained after drying
Sour half fat.
Purity testing is carried out to half fat of Dehydro and drographolide succinic acid.
Detect obtained chromatogram as shown in fig. 1, the result is shown in table 1, tables 2.
Table 1
Analysis result table
Table 2
System evaluation
Half fat purity of Dehydro and drographolide succinic acid is 41.7%.
Embodiment 2
The dehydroandrograpolide succinate obtained in embodiment 1 is purified, and details are provided below.
50% medicinal alcohol of 5 times of weight is added in dehydroandrograpolide succinate, heating nitrogen charging dissolves,
Temperature control at 50 DEG C, dehydroandrograpolide succinate be completely dissolved after subzero 15 DEG C of low temperature crystallizations, separating, washing,
It is dry；Purification process carries out 3 times.
Purity testing is carried out to half fat of Dehydro and drographolide succinic acid.
Obtained chromatogram is shown in Fig. 2, and the result is shown in table 3, tables 4.
Table 3
Analysis result table
Table 4
System evaluation
Half fat purity of Dehydro and drographolide succinic acid is 84.2%.
Embodiment 3
Be separately added into the dehydroandrograpolide succinate obtained in embodiment 13 times, 4 times, 4.5 times, 5 times, 6
Again, 50% medicinal alcohol of 7 times, 8 times, 9 times, 10 times, 10.5 times, 11 times weight, heating nitrogen charging dissolving, temperature is controlled 50
DEG C, dehydroandrograpolide succinate be completely dissolved after in subzero 15 DEG C of low temperature crystallizations, separating, washing, dryings；It is purified
Cheng Jinhang 3 times, obtains the dehydroandrograpolide succinate product of 11 parts of purifications, and respective purity is as shown in table 2.
Table 5
Embodiment 4
50% medicinal alcohol of 5 times of weight, heating are added in embodiment 1 obtains dehydroandrograpolide succinate
Nitrogen charging dissolves, temperature is controlled respectively at 10 DEG C, 15 DEG C, 20 DEG C, 30 DEG C, 40 DEG C, 50 DEG C, 60 DEG C, 65 DEG C, 70 DEG C, is dehydrated punching
Lotus lactone succinic acid half-ester be completely dissolved after in subzero 15 DEG C of low temperature crystallizations, separating, washing, dryings；Purification process carries out 3 times, obtains
The dehydroandrograpolide succinate product purified to 9 parts, the purity of 9 parts of products are as shown in table 6.
Table 6
Embodiment 5
50% medicinal alcohol of 5 times of weight is added in the dehydroandrograpolide succinate obtained in embodiment 1, is added
The dissolving of hot nitrogen charging, temperature is controlled at 15 DEG C, be dehydrated after succinic acid half-ester is completely dissolved in Herba Andrographitis respectively subzero 25 DEG C, zero
Lower 20 DEG C, 15 DEG C subzero, 10 DEG C subzero, subzero 5 DEG C of low temperature crystallizations, separating, washing, dryings；Purification process carries out 3 times, obtains 5
The dehydroandrograpolide succinate product of part purification, the purity of 5 parts of products are as shown in table 7.
Table 7
| Subzero 25 DEG C | Subzero 20 DEG C | Subzero 15 DEG C | Subzero 10 DEG C | Subzero 5 DEG C | |
| Purity (%) | 80.1 | 83.9 | 85.3 | 84.1 | 80.9 |
Embodiment 6
The dehydroandrograpolide succinate obtained in embodiment 1 is purified.
40% medicinal alcohol of 10 times of weight is added in dehydroandrograpolide succinate, heating nitrogen charging dissolves,
Temperature control at 20 DEG C, dehydroandrograpolide succinate be completely dissolved after subzero 17 DEG C of low temperature crystallizations, separating, washing,
It is dry；Purification process carries out 3 times.
Obtained dehydroandrograpolide succinate purity is 83.8%.
Embodiment 7
The dehydroandrograpolide succinate obtained in embodiment 1 is purified.
60% medicinal alcohol of 7 times of weight, heating nitrogen charging dissolving, temperature are added in dehydroandrograpolide succinate
Degree control at 60 DEG C, dehydroandrograpolide succinate be completely dissolved after in subzero 13 DEG C of low temperature crystallizations, separating, washing, dry
It is dry；Purification process carries out 3 times.
Obtained dehydroandrograpolide succinate purity is 84.2%.
Embodiment 8
The dehydroandrograpolide succinate obtained in embodiment 1 is purified.
80% medicinal alcohol of 6 times of weight, heating nitrogen charging dissolving, temperature are added in dehydroandrograpolide succinate
Degree control at 40 DEG C, dehydroandrograpolide succinate be completely dissolved after in subzero 20 DEG C of low temperature crystallizations, separating, washing, dry
It is dry；Purification process carries out 2 times.
Obtained dehydroandrograpolide succinate purity is 84.5%.
Embodiment 9
The dehydroandrograpolide succinate obtained in embodiment 1 is purified.
70% medicinal alcohol of 8 times of weight, heating nitrogen charging dissolving, temperature are added in dehydroandrograpolide succinate
Degree control at 30 DEG C, dehydroandrograpolide succinate be completely dissolved after in subzero 10 DEG C of low temperature crystallizations, separating, washing, dry
It is dry；Purification process carries out 3 times.
Obtained dehydroandrograpolide succinate purity is 84.1%.
Embodiment 10
Potassium dehydroandrographolide succinate is prepared using the dehydroandrograpolide succinate after the purification obtained in embodiment 2.After purification
Dehydroandrograpolide succinate obtain potassium dehydroandrographolide succinate through salt-forming reaction, details are provided below.
Added in into dehydroandrograpolide succinate in heating stirring with liquid (wherein with liquid by saleratus and
Purified water is formulated), salt-forming reaction is carried out after dissolving until milky to clarification, adds 12 times of 95% ethyl alcohol；Into
It is crystallized after reactant salt；It is filtered after crystallization.Using stainless-steel sheet press filtration in the present embodiment, 95% medicine is added in after press filtration
It is rinsed with ethyl alcohol, actually filter method and rinse solvent can be adjusted as needed.Half obtained after filtering into
Product are dried, and using drying 8 hours at a temperature of 55 DEG C in the present embodiment, drying time and temperature equally can be according to practical feelings
Condition is adjusted.It is crushed after drying, can be crushed to 80-200 mesh according to different requirements for pharmaceuticals；Mixing-inner packing-outsourcing
Dress-potassium dehydroandrographolide succinate finished product.
Purity testing is carried out to obtained potassium dehydroandrographolide succinate, obtained chromatogram is shown in Fig. 3, and the result is shown in tables 8.
8 analysis result table of table
Potassium dehydroandrographolide succinate purity is 99.351%.
In Chinese Pharmacopoeia, 2015 editions are that efficient liquid phase is detected with 4 times of times to the control parameter of potassium dehydroandrographolide succinate related substances
When, always miscellaneous to be not greater than 2%, maximum list is miscellaneous to be not greater than 1%.In the present embodiment, the Dehydro and drographolide after refined
Potassium dehydroandrographolide succinate made of half acid of succinic acid is detected with 6 times of times, as can be seen from Table 8, total miscellaneous less than 0.8-1%, maximum single miscellaneous
Less than 0.2-0.5%, quality is more than doubled than Chinese Pharmacopoeia standard.
Comparative example
Potassium dehydroandrographolide succinate is prepared using the dehydroandrograpolide succinate obtained in embodiment 1, process is as described below.
Added in into dehydroandrograpolide succinate in heating stirring with liquid (wherein with liquid by saleratus and
Purified water is formulated), salt-forming reaction is carried out after dissolving until milky to clarification, adds 12 times of 95% ethyl alcohol；Into
It is crystallized after reactant salt；It is filtered after crystallization.Using stainless-steel sheet press filtration in the present embodiment, 95% medicine is added in after press filtration
It is rinsed with ethyl alcohol, actually filter method and rinse solvent can be adjusted as needed.Half obtained after filtering into
Product are dried, and using drying 8 hours at a temperature of 55 DEG C in the present embodiment, drying time and temperature equally can be according to practical feelings
Condition is adjusted.It is crushed after drying, can be crushed to 80-200 mesh according to different requirements for pharmaceuticals；Mixing-inner packing-outsourcing
Dress-potassium dehydroandrographolide succinate finished product.
Purity testing is carried out to obtained potassium dehydroandrographolide succinate, obtained chromatogram is shown in Fig. 4, and the result is shown in tables 9.
9 analysis result table of table
Potassium dehydroandrographolide succinate purity is 98.487%.
Claims (10)
1. the purifying technique of dehydroandrograpolide succinate, it is characterised in that：In Dehydro and drographolide succinic acid half
Ethyl alcohol is added in ester, heating nitrogen charging dissolving, dehydroandrograpolide succinate is completely dissolved rear low temperature crystallization, separation is washed
It washs, dry；Above-mentioned purification process carries out at least once.
2. the purifying technique of dehydroandrograpolide succinate as described in claim 1, it is characterised in that：The second
Determining alcohol is 40%-80%；A concentration of 50%-60% of preferred alcohol.
3. the purifying technique of dehydroandrograpolide succinate as described in claim 1, it is characterised in that：The second
Alcohol is medicinal alcohol.
4. the purifying technique of dehydroandrograpolide succinate as described in claim 1, it is characterised in that：Ethyl alcohol with
The weight ratio of dehydroandrograpolide succinate is 5-10:1；Preferably, ethyl alcohol and Dehydro and drographolide succinic acid half
The weight ratio of ester is 6-8:1.
5. the purifying technique of dehydroandrograpolide succinate as described in claim 1, it is characterised in that：Dehydration is worn
The solution temperature of heart lotus lactone succinic acid half-ester is controlled at 20 DEG C -60 DEG C；Preferably, dehydroandrograpolide succinate
Solution temperature is controlled at 40 DEG C -50 DEG C.
6. the purifying technique of dehydroandrograpolide succinate as described in claim 1, it is characterised in that：Dehydration is worn
Heart lotus lactone succinic acid half-ester is in subzero 10 DEG C-subzero 20 DEG C of low temperature crystallizations.
7. the purifying technique of dehydroandrograpolide succinate as described in claim 5, it is characterised in that：Dehydration is worn
Heart lotus lactone succinic acid half-ester is in subzero 13 DEG C-subzero 17 DEG C of low temperature crystallizations.
8. dehydroandrograpolide succinate, it is characterised in that：It is carried using the technique as described in any in claim 1-7
It is pure.
9. potassium dehydroandrographolide succinate, it is characterised in that：It is prepared by the dehydroandrograpolide succinate of claim 8.
10. potassium dehydroandrographolide succinate, it is characterised in that：It adopts and is prepared by the following steps,
S1, andrographolide obtain dehydroandrograpolide succinate through being esterified, being dehydrated；
S2, dehydroandrograpolide succinate are used such as the technique purification as described in any in claim 1-7；
S3, the dehydroandrograpolide succinate after purification obtain potassium dehydroandrographolide succinate through salt-forming reaction.
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| JP2007254293A (en) * | 2006-03-20 | 2007-10-04 | Mitsubishi Rayon Co Ltd | METHOD FOR PRODUCING alpha-METHYLENE-beta-ALKYL-gamma-BUTYROLACTONE |
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| CN103113331A (en) * | 2013-02-28 | 2013-05-22 | 成都倍特药业有限公司 | Andrographolide synthetic method |
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Application publication date: 20180703 |