CN108484543A - A kind of preparation method of potassium dehydroandrographolide succinate or andrographolide - Google Patents
A kind of preparation method of potassium dehydroandrographolide succinate or andrographolide Download PDFInfo
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- CN108484543A CN108484543A CN201810245914.2A CN201810245914A CN108484543A CN 108484543 A CN108484543 A CN 108484543A CN 201810245914 A CN201810245914 A CN 201810245914A CN 108484543 A CN108484543 A CN 108484543A
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- andrographolide
- dehydroandrographolide succinate
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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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- 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
Abstract
The invention discloses the preparation methods of a kind of potassium dehydroandrographolide succinate or andrographolide, including：The crude step of dehydroandrographolide succinate：Using andrographolide and succinic anhydride as raw material, catalyst is added, is passed through nitrogen or argon gas protection, dehydroandrographolide succinate crude product is obtained through back flow reaction；Pure step processed：Crude product is extracted, the detection of upper prop, thin-layer chromatography, collect dehydroandrographolide succinate chromatographic solution, concentration, vacuum drying obtain pure product；The preparation process of potassium dehydroandrographolide succinate or andrographolide：The pure product of dehydroandrographolide succinate is dissolved into solution with organic solvent；The alkaline compound solution that potassium is added dropwise in the solution is reacted, and potassium dehydroandrographolide succinate is generated, or, the alkaline compound solution for the alkaline compound solution and sodium that potassium is added dropwise in the solution is reacted, generates andrographolide；The improvement of binding reagents and technique, greatly improves the purity for generating potassium dehydroandrographolide succinate or andrographolide, and the safety of technique and product is promoted.
Description
Technical field
The present invention relates to the preparation methods of a kind of potassium dehydroandrographolide succinate or andrographolide, belong to chemosynthesis technical field.
Background technology
Potassium dehydroandrographolide succinate is bis- dehydrogenation andrographolide -3,19- disuccinic acid half ester monopotassium salt of 14- deshydroxies -11,12-；Extensively
Acute upper respiratory infection caused by for treating viral pneumonia, influenza virus, acute bronchitis, children's bronchial lung
Inflammation, it is especially largely effective to viral and bacterial upper respiratory tract infection and dysentery, it has better effect to infantile pneumonia, is current
Ideal important antibiotic.
Andrographolide is 14-Dehydroxy-11,12-didehydroandrographolide-3,19-disuccinic acid half ester potassium sodium salt.It is applicable in
In viral pneumonia and viral infection of upper respiratory tract, andrographolide has become at present since its is antiviral, heat clearing and inflammation relieving is significant in efficacy
For one of the principal item of heat-clearing injecting drug use in the market.
The existing potassium dehydroandrographolide succinate or the main technique of andrographolide of preparing mainly has：
Synthesis technology one：In CN102584752B " a kind of andrographolide bulk pharmaceutical preparation method ", under inert gas protection,
Under catalyst action, andrographolide reacts in pyridine with 50-100 DEG C of heating of succinic anhydride, it is post-treated obtain dehydration wear
Heart lotus lactone succinic acid half-ester, dehydroandrograpolide succinate is in the mixed solvent and KHCO3Or K2CO3And NaHCO3
Or Na2CO3Mixed aqueous solution reacted at a temperature of 40-60 DEG C, it is post-treated to obtain andrographolide.
Synthesis technology two：A kind of CN103360350B " the preparations of Andrographolide in Andrographolide for Injection suitable for industrialized production, high-purity
It is starting material with andrographolide and succinic anhydride under nitrogen protection, pyridine is solvent, with anhydrous sulfurous acid in method "
Sodium is antioxidant, temperature programming, and reaction finishes, and is cooled down, and pyridine is removed using nonpolar solvent-weak acid hydrate, concentration, de-
Color；Then using acetone-water as solvent, salt-forming reaction is carried out under nitrogen protection, is added in acetone-water and carries out crystallization, and nitrogen is protected
Shield is lower to be filtered.
Synthesis technology three：CN100465171C " in the preparation method of andrographolide, andrographolide preparation and preparation method thereof ", it is lazy
Under property gas shield, andrographolide is reacted with amber platinic acid acid anhydride at 50-90 DEG C in pyridine, then temperature rising reflux, after
Manage to obtain two amber platinic acid half ester of andrographolide, two amber platinic acid half ester of andrographolide in water with potassium hydroxide or saleratus or
Carbonic acid nak response forms two amber platinic acid half ester monopotassium salt of andrographolide, then uses sodium hydroxide or sodium bicarbonate or sodium carbonate tune
Save pH to 7-8, post-treated andrographolide.
Synthesis technology four：It is original with andrographolide in CN102617527A " preparation method of potassium dehydroandrographolide succinate or andrographolide "
Material, in specific non-pyridine solvent (ethyl acetate, acetonitrile, tetrahydrofuran, butanone, propionitrile), the effect of catalyst and anhydrous
Under the protection of sodium sulfite, andrographolide two amber platinic acid half ester is made with amber platinic acid acid anhydride heating reflux reaction, then methanol,
In ethyl alcohol or aqueous solvent, two amber platinic acid half ester of andrographolide after purification is reacted into preparation with alkaline potassium salt and alkaline sodium salt and is worn
Amber is peaceful or andrographolide.
Synthesis technology five：In CN102863408B " a kind of preparation method of andrographolide ", under the protection of inert gas, with
Andrographolide and amber platinic acid acid anhydride are raw material, in non-protonic solvent (halogenated hydrocarbon, esters, ethers, ketone, nitrile etc.),
Using aliphatic small molecule amine as catalyst, at 30-90 DEG C, react and andrographolide two amber platinic acid half ester be made, then with potassium
Alkali compounds and the alkali compounds of sodium react and at salt andrographolide be made.
All the use of toxic and stench pyridine is solvent, while pyridine is difficult to remove in synthesis technology one, two, three,
Make in product pyridine solvent residual higher, in addition, when removing pyridine using a large amount of sour waters, will produce a large amount of pyridine waste water or
Sour water causes larger pressure to environmental protection.In synthesis technology four, using specific non-pyridine solvent, in the temperature of the solvent boiling point
The lower back flow reaction of degree, but these solvent boiling points are relatively low (100 DEG C or less), even if the reaction time extends, often react and endless
Entirely (hydroxyl reaction that amber platinic acid acid anhydride can be first and on andrographolide forms Dehydro and drographolide amber platinic acid monoesters, with
Reaction time extends and temperature increases, and can generate two amber of title intermediate Dehydro and drographolide again with another hydroxyl reaction
Platinic acid half ester also has more Dehydro and drographolide amber platinic acid monoesters to be not converted to take off in 100 DEG C of reaction temperatures below
Two amber platinic acid half ester of water andrographolide), in addition, being refined using a large amount of water in technique four, both wasted water, obtained dehydration is worn
Two amber platinic acid half ester purity of heart lotus lactone is not high.In synthesis technology five, it is relatively low similarly to there is reaction temperature (30-90 DEG C)
The problem of, cause reaction incomplete.In addition, it is after completion of the reaction, solvent and catalyst are removed using the method for reduced pressure
Method is refined, actually similar to the higher solvent of the boiling points such as propyl acetate, butyl acetate be difficult except clean, furthermore extra raw material
Amber platinic acid acid anhydride is also that can not be removed by concentrating.Therefore the purity and content of its product andrographolide is not high.
Invention content
For overcome the deficiencies in the prior art, the purpose of the present invention is to provide the preparation sides of a kind of potassium dehydroandrographolide succinate or andrographolide
Method, whether this method with or not pyridine as solvent, the improvement of binding reagents and technique, greatly improves and generates potassium dehydroandrographolide succinate or andrographolide
The safety of purity, technique and product greatly promotes.
Achieving the object of the present invention can be reached by adopting the following technical scheme that：A kind of preparation of potassium dehydroandrographolide succinate or andrographolide
Method, including：
The crude step of dehydroandrographolide succinate：Using andrographolide and succinic anhydride as raw material, with
At least one of propyl acetate and butyl acetate are solvent, and catalyst is added, and are passed through nitrogen or argon gas protection, vacuumize and add
Heat, through back flow reaction, obtains dehydroandrographolide succinate crude product to 100 DEG C or more；
The pure step processed of dehydroandrographolide succinate：By dehydroandrographolide succinate crude product
It is extracted, the detection of upper prop, thin-layer chromatography, collects dehydroandrographolide succinate chromatographic solution, chromatographic solution is concentrated,
Vacuum drying, obtains the pure product of dehydroandrographolide succinate；
The preparation process of potassium dehydroandrographolide succinate：The pure product of dehydroandrographolide succinate is dissolved into organic solvent molten
Liquid；The alkaline compound solution that potassium is added dropwise in dehydroandrographolide succinate solution is reacted, and amber is worn in generation
Rather；
Or, the preparation process of andrographolide：The pure product of dehydroandrographolide succinate is dissolved with organic solvent
At solution；The alkaline chemical combination of the alkaline compound solution and sodium of potassium is added dropwise in dehydroandrographolide succinate solution
Object solution is reacted, and andrographolide is generated.
Further, in the crude step of dehydroandrographolide succinate, the andrographolide and amber
The mass ratio of acid anhydrides is 1:1-3；The quality of the solvent is 5-15 times of andrographolide quality；The andrographolide and
The mass ratio of catalyst is 1:1-2；The catalyst is diethylamine or triethylamine.
Further, in the crude step of dehydroandrographolide succinate, suction be -0.08~-
0.1MPa, heating temperature are 100-125 DEG C, reflux time 3-8h.
Further, in the pure step processed of dehydroandrographolide succinate, with dichloromethane to being dehydrated punching
Lotus lactone disuccinic acid half ester crude product is extracted, and the quality of dichloromethane is dehydroandrographolide succinate crude product
5-10 times of quality.
Further, in the pure step processed of dehydroandrographolide succinate, upper silicagel column, the silica gel of silicagel column
Mesh number is 100-600 mesh, the ratio between mobile phase volume dichloromethane:Methanol:Formic acid is 500:(10-20):(1-10).
Further, in the preparation process of potassium dehydroandrographolide succinate or andrographolide, organic solvent is methanol or ethyl alcohol, the matter of organic solvent
Amount is 3-8 times of dehydroandrographolide succinate.
Further, in the preparation process of potassium dehydroandrographolide succinate or andrographolide, the alkali compounds of potassium be potassium hydroxide, potassium carbonate or
Saleratus；The mass percent concentration of the alkaline compound solution of potassium is 15-25%.
Further, in the preparation process of potassium dehydroandrographolide succinate, the alkaline chemical combination of dehydroandrographolide succinate and potassium
The molar ratio of object is 1:The reaction temperature of the alkali compounds of 0.8-1.2, dehydroandrographolide succinate and potassium is
30-40 DEG C, reaction time 3-5h.
Further, in the preparation process of andrographolide, the alkali compounds of sodium is sodium hydroxide, sodium carbonate or bicarbonate
Sodium；The mass percent concentration of the alkaline compound solution of sodium is 10-20%.
Further, in the preparation process of andrographolide, dehydroandrographolide succinate, potassium alkaline chemical combination
Object, sodium alkali compounds molar ratio be 1:(0.8-1.2):(0.4-0.6), dehydroandrographolide succinate with
The alkali compounds of potassium, the alkali compounds of sodium reaction temperature be 20-40 DEG C, reaction time 3-4h.
Compared with prior art, the beneficial effects of the present invention are：
1, the present invention is using propyl acetate and butyl acetate as solvent, instead of stench and the big pyridine of toxicity as solvent,
The residual of pyridine in product is avoided simultaneously, and the safety of technique and product greatly promotes；
2, the crude of dehydroandrographolide succinate improves heating temperature to 100 DEG C or more, cooperation vacuum,
Heating, the method to flow back are reacted, and high performance liquid chromatography is shown, raw material andrographolide total overall reaction finishes, two kinds of dehydrations
The sum of andrographolide amber platinic acid monoester concentration is remaining to be no more than 4%；
3, the pure system of dehydroandrographolide succinate with upper prop, thin-layer chromatography remove excessive amber platinic acid acid anhydride and
The Dehydro and drographolide amber platinic acid monoesters that reaction not exclusively generates, promotes product purity, and the mobile phase of chromatography can recycle
It uses again, avoids generating a large amount of waste acid waters, reduce environmental protection pressure.
Specific implementation mode
In the following, in conjunction with specific implementation mode, the present invention is described further：
Embodiment 1：
The preparation of potassium dehydroandrographolide succinate：
Andrographolide quality 50g, succinic anhydride quality 110g, butyl acetate quality 353g, triethylamine 60g；
The crude step of dehydroandrographolide succinate：Using andrographolide and succinic anhydride as raw material, with
Butyl acetate is solvent, and triethylamine is added as catalyst, is passed through nitrogen or argon gas protection, vacuumizes -0.085MPa, and heat
To 105 DEG C, through back flow reaction 6h, dehydroandrographolide succinate crude product is obtained；
The pure step processed of dehydroandrographolide succinate：By dehydroandrographolide succinate crude product
It carries out being extracted (quality of addition dichloromethane is 397.5g every time), upper silicagel column (silica gel mesh number three times with dichloromethane
For 200-300 mesh, mobile phase：Dichloromethane:Methanol:The ratio between volume of formic acid is 500:15:3), thin-layer chromatography detects, and collects
Chromatographic solution concentration, vacuum drying are obtained two amber of Dehydro and drographolide by dehydroandrographolide succinate chromatographic solution
The pure product 52g of amber acid half ester；
The preparation process of potassium dehydroandrographolide succinate：It is with ethyl alcohol 197.25g that the pure product 52g of dehydroandrographolide succinate is molten
Solution is at solution；Under the conditions of 35 DEG C, potassium bicarbonate solution (10g is added dropwise in dehydroandrographolide succinate solution
Saleratus is dissolved in 50mL water) carry out reaction 4h after, filtering absolute ethyl alcohol rinse, drying, obtain potassium dehydroandrographolide succinate 44.8g, yield
88.4%, purity 99.3%.
Embodiment 2
The preparation of andrographolide：
Andrographolide quality 30g, succinic anhydride quality 75g, propyl acetate quality 399.51g, triethylamine 35g；
The crude step of dehydroandrographolide succinate：Using andrographolide and succinic anhydride as raw material, with
Propyl acetate is solvent, and triethylamine is added as catalyst, is passed through nitrogen or argon gas protection, vacuumizes -0.095MPa, and heat
To 115 DEG C, through back flow reaction 4h, dehydroandrographolide succinate crude product is obtained；
The pure step processed of dehydroandrographolide succinate：By dehydroandrographolide succinate crude product
It carries out being extracted (quality of addition dichloromethane is 463.75g every time), upper silicagel column (silica gel mesh number three times with dichloromethane
For 300-400 mesh, mobile phase：Dichloromethane:Methanol:The ratio between volume of formic acid is 500:12:2), thin-layer chromatography detects, and collects
Chromatographic solution concentration, vacuum drying are obtained two amber of Dehydro and drographolide by dehydroandrographolide succinate chromatographic solution
The pure product 30g of amber acid half ester；
The preparation process of andrographolide：It is with methanol 158.36g that the pure product 30g of dehydroandrographolide succinate is molten
Solution is at solution；Under the conditions of 38 DEG C, potassium bicarbonate solution (6g carbon is added dropwise in dehydroandrographolide succinate solution
Potassium hydrogen phthalate is dissolved in 30mL water) and after sodium carbonate liquor (3g sodium carbonate is dissolved in 25mL water) carries out reaction 3.5h, filtering is anhydrous
Ethyl alcohol rinses, and drying obtains andrographolide 26.3g, yield 87.6%, purity 99.4%.
Embodiment 3
The preparation of andrographolide：
Andrographolide quality 60g, succinic anhydride quality 150g, butyl acetate quality 529.5g, triethylamine 95g；
The crude step of dehydroandrographolide succinate：Using andrographolide and succinic anhydride as raw material, with
Butyl acetate is solvent, and triethylamine is added as catalyst, is passed through nitrogen or argon gas protection, vacuumizes -0.09MPa, and heat
To 110 DEG C, through back flow reaction 4h, dehydroandrographolide succinate crude product is obtained；
The pure step processed of dehydroandrographolide succinate：By dehydroandrographolide succinate crude product
It carries out being extracted (quality of addition dichloromethane is 662.5g every time), upper silicagel column (silica gel mesh number three times with dichloromethane
For 200-300 mesh, mobile phase：Dichloromethane:Methanol:The ratio between volume of formic acid is 500:16:2), thin-layer chromatography detects, and collects
Chromatographic solution concentration, vacuum drying are obtained two amber of Dehydro and drographolide by dehydroandrographolide succinate chromatographic solution
The pure product 63g of amber acid half ester；
The preparation process of andrographolide：It is with ethyl alcohol 331.38g that the pure product 63g of dehydroandrographolide succinate is molten
Solution is at solution；Under the conditions of 36 DEG C, solution of potassium carbonate (18g carbon is added dropwise in dehydroandrographolide succinate solution
Sour potassium is dissolved in 100mL water) and after sodium bicarbonate solution (19g sodium bicarbonates are dissolved in 125mL water) carries out reaction 4h, filter nothing
Water-ethanol rinses, and drying obtains andrographolide 52.2g, yield 87%, purity 99.3%.
For those skilled in the art, technical solution that can be as described above and design are made other each
Kind is corresponding to be changed and deforms, and all these change and deform the protection model that should all belong to the claims in the present invention
Within enclosing.
Claims (10)
1. the preparation method of a kind of potassium dehydroandrographolide succinate or andrographolide, it is characterised in that including：
The crude step of dehydroandrographolide succinate：Using andrographolide and succinic anhydride as raw material, with acetic acid
At least one of propyl ester and butyl acetate are solvent, and catalyst is added, and are passed through nitrogen or argon gas protection, vacuumize and be heated to
100 DEG C or more, through back flow reaction, obtain dehydroandrographolide succinate crude product；
The pure step processed of dehydroandrographolide succinate：Dehydroandrographolide succinate crude product is carried out
Extraction, upper prop, thin-layer chromatography detection, collect dehydroandrographolide succinate chromatographic solution, by chromatographic solution concentration, vacuum
It is dry, obtain the pure product of dehydroandrographolide succinate；
The preparation process of potassium dehydroandrographolide succinate：The pure product of dehydroandrographolide succinate is dissolved into solution with organic solvent；
The alkaline compound solution that potassium is added dropwise in dehydroandrographolide succinate solution is reacted, and potassium dehydroandrographolide succinate is generated；
Or, the preparation process of andrographolide：The pure product of dehydroandrographolide succinate is dissolved into organic solvent molten
Liquid；The alkali compounds of alkaline compound solution and sodium that potassium is added dropwise in dehydroandrographolide succinate solution is molten
Liquid is reacted, and andrographolide is generated.
2. the preparation method of potassium dehydroandrographolide succinate as described in claim 1 or andrographolide, which is characterized in that two amber of Dehydro and drographolide
In the crude step of amber acid half ester, the mass ratio of the andrographolide and succinic anhydride is 1:1-3；The quality of the solvent
It is 5-15 times of andrographolide quality；The mass ratio of the andrographolide and catalyst is 1:1-2；The catalyst is
Diethylamine or triethylamine.
3. the preparation method of potassium dehydroandrographolide succinate as described in claim 1 or andrographolide, which is characterized in that two amber of Dehydro and drographolide
In the crude step of amber acid half ester, suction is -0.08~-0.1MPa, and heating temperature is 100-125 DEG C, when back flow reaction
Between be 3-8h.
4. the preparation method of potassium dehydroandrographolide succinate as described in claim 1 or andrographolide, which is characterized in that two amber of Dehydro and drographolide
In the pure step processed of amber acid half ester, dehydroandrographolide succinate crude product is extracted with dichloromethane, dichloro
The quality of methane is 5-10 times of dehydroandrographolide succinate crude product quality.
5. the preparation method of potassium dehydroandrographolide succinate as described in claim 1 or andrographolide, which is characterized in that two amber of Dehydro and drographolide
In the pure step processed of amber acid half ester, the silica gel mesh number of upper silicagel column, silicagel column is 100-600 mesh, the ratio between mobile phase volume dichloro
Methane:Methanol:Formic acid is 500:(10-20):(1-10).
6. the preparation method of potassium dehydroandrographolide succinate as described in claim 1 or andrographolide, which is characterized in that the system of potassium dehydroandrographolide succinate or andrographolide
In standby step, organic solvent is methanol or ethyl alcohol, and the quality of organic solvent is the 3-8 of dehydroandrographolide succinate
Times.
7. the preparation method of potassium dehydroandrographolide succinate as described in claim 1 or andrographolide, which is characterized in that the system of potassium dehydroandrographolide succinate or andrographolide
In standby step, the alkali compounds of potassium is potassium hydroxide, potassium carbonate or saleratus；The quality hundred of the alkaline compound solution of potassium
It is 15-25% to divide specific concentration.
8. the preparation method of potassium dehydroandrographolide succinate as described in claim 1 or andrographolide, which is characterized in that the preparation process of potassium dehydroandrographolide succinate
In, the molar ratio of the alkali compounds of dehydroandrographolide succinate and potassium is 1:0.8-1.2 is dehydrated in Herba Andrographitis
The reaction temperature of the alkali compounds of ester disuccinic acid half ester and potassium is 30-40 DEG C, reaction time 3-5h.
9. the preparation method of potassium dehydroandrographolide succinate as described in claim 1 or andrographolide, which is characterized in that the preparation process of andrographolide
In, the alkali compounds of sodium is sodium hydroxide, sodium carbonate or sodium bicarbonate；The mass percent of the alkaline compound solution of sodium is dense
Degree is 10-20%.
10. the preparation method of potassium dehydroandrographolide succinate as described in claim 1 or andrographolide, which is characterized in that the preparation process of andrographolide
In, dehydroandrographolide succinate, the alkali compounds of potassium, sodium alkali compounds molar ratio be 1:(0.8-
1.2):The alkali compounds of (0.4-0.6), dehydroandrographolide succinate and potassium, the alkali compounds of sodium it is anti-
It is 20-40 DEG C to answer temperature, reaction time 3-4h.
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| CN107857747A (en) * | 2017-10-16 | 2018-03-30 | 广州普星药业有限公司 | A kind of preparation method of potassium dehydroandrographolide succinate |
| CN112552267A (en) * | 2020-12-25 | 2021-03-26 | 成都通德药业有限公司 | Purification process of potassium dehydroandrographolide succinate atomizing agent |
| CN113387913A (en) * | 2021-05-14 | 2021-09-14 | 宜宾职业技术学院 | Preparation method of high-purity dehydroandrographolide succinate |
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| CN107857747A (en) * | 2017-10-16 | 2018-03-30 | 广州普星药业有限公司 | A kind of preparation method of potassium dehydroandrographolide succinate |
| CN112552267A (en) * | 2020-12-25 | 2021-03-26 | 成都通德药业有限公司 | Purification process of potassium dehydroandrographolide succinate atomizing agent |
| CN113387913A (en) * | 2021-05-14 | 2021-09-14 | 宜宾职业技术学院 | Preparation method of high-purity dehydroandrographolide succinate |
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