CN110003168A - A kind of preparation method of high-purity alpha-lipoic acid - Google Patents
A kind of preparation method of high-purity alpha-lipoic acid Download PDFInfo
- Publication number
- CN110003168A CN110003168A CN201910396382.7A CN201910396382A CN110003168A CN 110003168 A CN110003168 A CN 110003168A CN 201910396382 A CN201910396382 A CN 201910396382A CN 110003168 A CN110003168 A CN 110003168A
- Authority
- CN
- China
- Prior art keywords
- lipoic acid
- preparation
- added
- alpha
- crude product
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/02—Five-membered rings
- C07D339/04—Five-membered rings having the hetero atoms in positions 1 and 2, e.g. lipoic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Abstract
This application involves technical field of medicine preparation, and in particular to a kind of preparation method of high-purity alpha-lipoic acid includes the following steps: S1: the synthesis of lipoic acid ethyl ester;S2: lipoic acid second ester hydrolysis;S3: the acidification of sodium thioctate;S4: the purifying of lipoic acid crude product.The purity of cyclised products is controlled by felicity condition and carries out purifying crude at appropriate lower temperature, and limitation crude product generates less by-product when preparation, to improve yield, yield reaches 65% or more, and purity is 99% or more.
Description
Technical field
The present invention relates to technical field of medicine preparation, more specifically, it relates to a kind of preparation of high-purity alpha-lipoic acid
Method.
Background technique
Alpha-lipoic acid (alpha lipoic acid) is a kind of enzyme for being present in mitochondria, and similar vitamin can be eliminated and add
Fast aging and pathogenic free radical.Alpha-lipoic acid in vivo after intestinal absorption enter cell, have both it is fat-soluble with it is water-soluble
Characteristic, therefore can go everywhere without any hindrance here in whole body, any one cell area is reached, provides human body comprehensive efficiency, is that tool is fat-soluble
With water-soluble universal antioxidant.The Parker doctor (Dr.Lester Packer) in California, USA university Berkeley branch school is generation
The top alpha-lipoic acid in boundary and antioxidant authority.Alpha-lipoic acid is used to prevent even to treat certain diseases such as: AIDS, diabetes
And its symptoms such as complication, neural degenerative and hepatic insufficiency.But, at the beginning since alpha-lipoic acid is as diabetes
Medication, but in fact other than controlling diabetes, there are also many functions, main function includes: the stabilization of blood glucose value for it, is strengthened
Liver function recovers from fatigue, and improves dull-witted, protection body, and skin maintenance and cosmetic benefits is anti-aging.Its main mechanism are as follows: alpha-lipoic acid is participated in
Biochemical reaction, mainly in the center of energy of cell --- mitochondria, alpha-lipoic acid are also that human glucose energetic supersession follows
The necessary factor in ring.Alpha-lipoic acid can significantly improve patient of diabetes cell to the susceptibility of insulin, increase cellular energy and follow
The generation of ATP in ring has positive meaning for the improvement of diabetes complicated Myocardial damage.
Each synthetic route yield of lipoic acid is low at present, is usually no more than 60%, and most of route cost is high, synthesis
Step is loaded down with trivial details.Therefore, a kind of economical rationality is found, yield is higher, it is easy to accomplish the approach ten of industrialized synthesis alpha-lipoic acid
Divide important.
Summary of the invention
The purpose of the present invention is to provide a kind of preparation methods of high-purity alpha-lipoic acid, have the advantages that high income.
Above-mentioned technical purpose of the invention has the technical scheme that a kind of high-purity alpha-lipoic acid
Preparation method includes the following steps: S1: the synthesis of lipoic acid ethyl ester: 6,8-dichloro-octanoic acid ethyl ester, sulphur being added in aqueous solvent
Sulphur, tetrabutylammonium bromide are warming up to 82 DEG C~84 DEG C, are slowly added to sodium sulfide solution, react 5 hours;After reaction, cool down
To 65 DEG C, static about 60 minutes, it is layered to get lipoic acid ethyl ester is arrived;S2: lipoic acid second ester hydrolysis: be added sodium hydroxide and
Tetrabutylammonium bromide, stirring are warming up to 50 DEG C~80 DEG C, and heat preservation filters after reaction;S3: the acidification of sodium thioctate: will
The filtrate that S2 is obtained is cooled to 5 DEG C~10 DEG C, then adjusts the filtering of pH to 1~2 and obtains lipoic acid crude product;S4: lipoic acid is thick
The purifying of product: the lipoic acid crude product that S3 is obtained is added in the mixed solvent, under stirring, is completely dissolved lipoic acid crude product, so
After purified water is added, heat temperature raising keeps the temperature and is kept stirring 10 minutes, static 20 minutes branch vibration layers, by organic layer heat rise
Silica gel is added to after 40 DEG C~45 DEG C in temperature, after stirring 2h, filters, is subsequently cooled to 15 DEG C~19 DEG C of interior temperature, stirring and crystallizing 2~3
Hour, it filters and obtains the wet fine work of alpha-lipoic acid, it is then dry at a temperature of 10 DEG C~35 DEG C.
Further, the mixed solvent in S4 is hexamethylene: ethyl acetate=5:1 (w:w).
Further, it is hydrochloric acid that the pH in S3, which adjusts the acid being added,.
Further, the time dry in S4 is 8-12 hours.
Further, further include following steps: A1: weighing dehydrated alcohol, alpha-lipoic acid and syrup investment by weight and stir
It mixes in device, is passed through nitrogen, be stirred, investment sieving equipment sieving obtains lipoic acid slice;A2: by what is obtained by step A1
Lipoic acid slice is introduced into ball blast in shot-blasting machine and is granulated, and controls the time of ball blast granulation, then introduces drying device drying, obtains
To the non-uniform lipoic acid particle of partial size;A3: the non-uniform lipoic acid particle of the partial size obtained by step A2 is sieved, sieving sieve
The lipoic acid particle removed returns to step A1 reuse, obtains the lipoic acid particle of uniform particle diameter.
Further, the weight ratio of dehydrated alcohol, alpha-lipoic acid and syrup is 0.5:1:0.25 in A1.
Further, the mixing speed in A1 is 10-60rmp, and temperature control is 10-25 DEG C.
Further, the sieve crossed in A3 is the sieve of 30-100 mesh.
In conclusion the invention has the following advantages: controlling the purity of first step cyclised products by felicity condition
Purifying crude is carried out at appropriate lower temperature, less by-product is generated when limiting crude product preparation, to improve
Yield, yield reach 65% or more, and purity is 99% or more;And particle is made in the lipoic acid powder and is saved, it can reduce
The photodegradation of lipoic acid.Syrup is added, may make lipoic acid powder more easy to knot groups, convenient for granulation, is also conducive to subsequent coating and is made
The other processes such as pill.
Specific embodiment
Embodiment 1:
A kind of preparation method of high-purity alpha-lipoic acid, includes the following steps:
S1: the synthesis of lipoic acid ethyl ester: being added 6,8-dichloro-octanoic acid ethyl ester, sulphur, tetrabutylammonium bromide in aqueous solvent,
82 DEG C are warming up to, sodium sulfide solution is slowly added to, is reacted 5 hours;After reaction, 65 DEG C are cooled to, static about 60 minutes, is divided
Layer to get arrive lipoic acid ethyl ester;
S2: lipoic acid second ester hydrolysis: being added sodium hydroxide and tetrabutylammonium bromide, and stirring is warming up to 50 DEG C, keeps the temperature,
After reaction, it filters;
S3: the acidification of sodium thioctate: the filtrate that S2 is obtained is cooled to 5 DEG C, and salt acid for adjusting pH to 1 filtering is then added and is
Obtain lipoic acid crude product;
S4: the lipoic acid crude product that S3 is obtained the purifying of lipoic acid crude product: is added to mixed solvent (hexamethylene: acetic acid second
Ester=5~15:1 (w:w)) in, under stirring, it is completely dissolved lipoic acid crude product, purified water is then added, is heated to 40
DEG C, heat preservation is kept stirring 10 minutes for 30 minutes, static 20 minutes branch vibration layers, after organic layer is heated to 40 DEG C, is added
Silica gel after stirring 2h, filters, and is subsequently cooled to 15 DEG C of interior temperature, stirring and crystallizing 2 hours, filters and obtain the wet fine work of alpha-lipoic acid,
Then the dry 8h under 10 DEG C of degree, obtains lipoic acid powder, yield 65.1%, purity 99.3%.
Particle further is made in lipoic acid powder, further includes following steps:
A1: dehydrated alcohol, alpha-lipoic acid and syrup are weighed by weight and is thrown according to weight ratio 0.5:1:0.25 purity ratio
Enter in blender, be passed through nitrogen, be stirred with 10rmp, 10 DEG C, investment sieving equipment sieving obtains lipoic acid slice;
A2: the lipoic acid slice obtained by step A1 is introduced into ball blast in shot-blasting machine and is granulated, and controls ball blast granulation
Time then introduces drying device drying, obtains the non-uniform lipoic acid particle of partial size;
A3: the non-uniform lipoic acid particle of the partial size obtained by step A2 is crossed to the sieve of 30 mesh, be sieved the lipoic acid screened out
Particle returns to step A1 reuse, obtains the lipoic acid particle of uniform particle diameter.
Embodiment 2:
A kind of preparation method of high-purity alpha-lipoic acid, includes the following steps:
S1: the synthesis of lipoic acid ethyl ester: being added 6,8-dichloro-octanoic acid ethyl ester, sulphur, tetrabutylammonium bromide in aqueous solvent,
82 DEG C are warming up to, sodium sulfide solution is slowly added to, is reacted 5 hours;After reaction, 65 DEG C are cooled to, static about 60 minutes, is divided
Layer to get arrive lipoic acid ethyl ester;
S2: lipoic acid second ester hydrolysis: being added sodium hydroxide and tetrabutylammonium bromide, and stirring is warming up to 60 DEG C, keeps the temperature,
After reaction, it filters;
S3: the acidification of sodium thioctate: the filtrate that S2 is obtained is cooled to 6 DEG C, and salt acid for adjusting pH to 1 filtering is then added and is
Obtain lipoic acid crude product;
S4: the lipoic acid crude product that S3 is obtained the purifying of lipoic acid crude product: is added to mixed solvent (hexamethylene: acetic acid second
Ester=7:1 (w:w)) in, under stirring, it is completely dissolved lipoic acid crude product, purified water is then added, be heated to 41 DEG C, protected
Temperature is kept stirring 10 minutes for 32 minutes, static 20 minutes branch vibration layers, and after organic layer is heated to 41 DEG C, silica gel is added,
It after stirring 2h, filters, is subsequently cooled to 16 DEG C of interior temperature, stirring and crystallizing 2 hours, filters and obtain the wet fine work of alpha-lipoic acid, then
Dry 9h, obtains lipoic acid powder, yield 65.2%, purity 99.2% at a temperature of 10 DEG C.
Particle further is made in lipoic acid powder, further includes following steps:
A1: dehydrated alcohol, alpha-lipoic acid and syrup are weighed by weight and is thrown according to weight ratio 0.5:1:0.25 purity ratio
Enter in blender, be passed through nitrogen, be stirred, investment sieving equipment sieving obtains lipoic acid slice;
A2: the lipoic acid slice obtained by step A1 is introduced into ball blast in shot-blasting machine and is granulated, and controls ball blast granulation
Time then introduces drying device drying, obtains the non-uniform lipoic acid particle of partial size;
A3: the non-uniform lipoic acid particle of the partial size obtained by step A2 is crossed to the sieve of 50 mesh, be sieved the lipoic acid screened out
Particle returns to step A1 reuse, obtains the lipoic acid particle of uniform particle diameter.
Embodiment 3:
A kind of preparation method of high-purity alpha-lipoic acid, includes the following steps:
S1: the synthesis of lipoic acid ethyl ester: being added 6,8-dichloro-octanoic acid ethyl ester, sulphur, tetrabutylammonium bromide in aqueous solvent,
83 DEG C are warming up to, sodium sulfide solution is slowly added to, is reacted 5 hours;After reaction, 65 DEG C are cooled to, static about 60 minutes, is divided
Layer to get arrive lipoic acid ethyl ester;
S2: lipoic acid second ester hydrolysis: being added sodium hydroxide and tetrabutylammonium bromide, and stirring is warming up to 50 DEG C~80 DEG C,
Heat preservation filters after reaction;
S3: the acidification of sodium thioctate: the filtrate that S2 is obtained is cooled to 7.5 DEG C, and salt acid for adjusting pH is then added to 1.5 mistakes
Filter obtains lipoic acid crude product;
S4: the lipoic acid crude product that S3 is obtained the purifying of lipoic acid crude product: is added to mixed solvent (hexamethylene: acetic acid second
Ester=10:1 (w:w)) in, under stirring, it is completely dissolved lipoic acid crude product, purified water is then added, is heated to 42.5 DEG C,
Heat preservation is kept stirring 10 minutes for 35 minutes, static 20 minutes branch vibration layers, and after organic layer is heated to 42.5 DEG C, silicon is added
Glue after stirring 2h, filters, and is subsequently cooled to 17 DEG C of interior temperature, stirring and crystallizing 2.5 hours, filters and obtain the wet fine work of alpha-lipoic acid,
Then dry 10h at a temperature of 22.5 DEG C, obtains lipoic acid powder, yield 65.3%, purity 99.3%.
Particle further is made in lipoic acid powder, further includes following steps:
A1: dehydrated alcohol, alpha-lipoic acid and syrup are weighed by weight and is thrown according to weight ratio 0.5:1:0.25 purity ratio
Enter in blender, be passed through nitrogen, be stirred, investment sieving equipment sieving obtains lipoic acid slice;
A2: the lipoic acid slice obtained by step A1 is introduced into ball blast in shot-blasting machine and is granulated, and controls ball blast granulation
Time then introduces drying device drying, obtains the non-uniform lipoic acid particle of partial size;
A3: the non-uniform lipoic acid particle of the partial size obtained by step A2 is crossed to the sieve of 65 mesh, be sieved the lipoic acid screened out
Particle returns to step A1 reuse, obtains the lipoic acid particle of uniform particle diameter.
Embodiment 4:
A kind of preparation method of high-purity alpha-lipoic acid, includes the following steps:
S1: the synthesis of lipoic acid ethyl ester: being added 6,8-dichloro-octanoic acid ethyl ester, sulphur, tetrabutylammonium bromide in aqueous solvent,
84 DEG C are warming up to, sodium sulfide solution is slowly added to, is reacted 5 hours;After reaction, 65 DEG C are cooled to, static about 60 minutes, is divided
Layer to get arrive lipoic acid ethyl ester;
S2: lipoic acid second ester hydrolysis: being added sodium hydroxide and tetrabutylammonium bromide, and stirring is warming up to 70 DEG C, keeps the temperature,
After reaction, it filters;
S3: the acidification of sodium thioctate: the filtrate that S2 is obtained is cooled to 8 DEG C, and salt acid for adjusting pH is then added to 1~2 mistake
Filter obtains lipoic acid crude product;
S4: the lipoic acid crude product that S3 is obtained the purifying of lipoic acid crude product: is added to mixed solvent (hexamethylene: acetic acid second
Ester=12:1 (w:w)) in, under stirring, it is completely dissolved lipoic acid crude product, purified water is then added, be heated to 44 DEG C, protected
Temperature is kept stirring 10 minutes for 38 minutes, static 20 minutes branch vibration layers, and after organic layer is heated to 43 DEG C, silica gel is added,
It after stirring 2h, filters, is subsequently cooled to 18 DEG C of interior temperature, stirring and crystallizing 3 hours, filters and obtain the wet fine work of alpha-lipoic acid, then
Dry 11h, obtains lipoic acid powder, yield 65.4%, purity 99.4% at a temperature of 30 DEG C.
Particle further is made in lipoic acid powder, further includes following steps:
A1: dehydrated alcohol, alpha-lipoic acid and syrup are weighed by weight and is thrown according to weight ratio 0.5:1:0.25 purity ratio
Enter in blender, be passed through nitrogen, be stirred, investment sieving equipment sieving obtains lipoic acid slice;
A2: the lipoic acid slice obtained by step A1 is introduced into ball blast in shot-blasting machine and is granulated, and controls ball blast granulation
Time then introduces drying device drying, obtains the non-uniform lipoic acid particle of partial size;
A3: the non-uniform lipoic acid particle of the partial size obtained by step A2 is crossed to the sieve of 80 mesh, be sieved the lipoic acid screened out
Particle returns to step A1 reuse, obtains the lipoic acid particle of uniform particle diameter.
Embodiment 5:
A kind of preparation method of high-purity alpha-lipoic acid, includes the following steps:
S1: the synthesis of lipoic acid ethyl ester: being added 6,8-dichloro-octanoic acid ethyl ester, sulphur, tetrabutylammonium bromide in aqueous solvent,
84 DEG C are warming up to, sodium sulfide solution is slowly added to, is reacted 5 hours;After reaction, 65 DEG C are cooled to, static about 60 minutes, is divided
Layer to get arrive lipoic acid ethyl ester;
S2: lipoic acid second ester hydrolysis: being added sodium hydroxide and tetrabutylammonium bromide, and stirring is warming up to 80 DEG C, keeps the temperature,
After reaction, it filters;
S3: the acidification of sodium thioctate: the filtrate that S2 is obtained is cooled to 10 DEG C, and salt acid for adjusting pH is then added to 2 filterings
Obtain lipoic acid crude product;
S4: the lipoic acid crude product that S3 is obtained the purifying of lipoic acid crude product: is added to mixed solvent (hexamethylene: acetic acid second
Ester=15:1 (w:w)) in, under stirring, it is completely dissolved lipoic acid crude product, purified water is then added, be heated to 45 DEG C, protected
Temperature is kept stirring 10 minutes for 40 minutes, static 20 minutes branch vibration layers, and after organic layer is heated to 45 DEG C, silica gel is added,
It after stirring 2h, filters, is subsequently cooled to 19 DEG C of interior temperature, stirring and crystallizing 3 hours, filters and obtain the wet fine work of alpha-lipoic acid, then
Dry 12h, obtains lipoic acid powder, yield 65.2%, purity 99.1% at a temperature of 35 DEG C.
Particle further is made in lipoic acid powder, further includes following steps:
A1: dehydrated alcohol, alpha-lipoic acid and syrup are weighed by weight and is thrown according to weight ratio 0.5:1:0.25 purity ratio
Enter in blender, be passed through nitrogen, be stirred, investment sieving equipment sieving obtains lipoic acid slice;
A2: the lipoic acid slice obtained by step A1 is introduced into ball blast in shot-blasting machine and is granulated, and controls ball blast granulation
Time then introduces drying device drying, obtains the non-uniform lipoic acid particle of partial size;
A3: the non-uniform lipoic acid particle of the partial size obtained by step A2 is crossed to the sieve of 100 mesh, be sieved the lipoic acid screened out
Particle returns to step A1 reuse, obtains the lipoic acid particle of uniform particle diameter.
The above is only a preferred embodiment of the present invention, protection scope of the present invention is not limited merely to above-mentioned implementation
Example, all technical solutions belonged under thinking of the present invention all belong to the scope of protection of the present invention.It should be pointed out that for the art
Those of ordinary skill for, several improvements and modifications without departing from the principles of the present invention, these improvements and modifications
It should be regarded as protection scope of the present invention.
Claims (8)
1. a kind of preparation method of high-purity alpha-lipoic acid, characterized by the following steps:
S1: 6,8-dichloro-octanoic acid ethyl ester, sulphur, tetrabutylammonium bromide, heating the synthesis of lipoic acid ethyl ester: are added in aqueous solvent
To 82 DEG C~84 DEG C, it is slowly added to sodium sulfide solution, is reacted 5 hours;After reaction, 65 DEG C are cooled to, static about 60 minutes,
It is layered to get lipoic acid ethyl ester is arrived;
S2: lipoic acid second ester hydrolysis: being added sodium hydroxide and tetrabutylammonium bromide, and stirring is warming up to 50 DEG C~80 DEG C, protects
Temperature filters after reaction;
S3: the acidification of sodium thioctate: the filtrate that S2 is obtained is cooled to 5 DEG C~10 DEG C, then adjusts pH to 1~2 and filters to obtain the final product
To lipoic acid crude product;
S4: the purifying of lipoic acid crude product: the lipoic acid crude product that S3 is obtained is added in the mixed solvent, under stirring, makes lipoic acid
Crude product is completely dissolved, and purified water is then added, and heat temperature raising keeps the temperature and is kept stirring 10 minutes, static 20 minutes branch vibration layers,
After organic layer is heated to 40 DEG C~45 DEG C, silica gel is added, after stirring 2h, filters, is subsequently cooled to interior temperature 15 DEG C~19
DEG C, it stirring and crystallizing 2~3 hours, filters and obtains the wet fine work of alpha-lipoic acid, it is then dry at a temperature of 10 DEG C~35 DEG C.
2. preparation method according to claim 1, it is characterised in that: the mixed solvent in S4 is hexamethylene: ethyl acetate
=5~15:1 (w:w).
3. preparation method according to claim 1, it is characterised in that: it is hydrochloric acid that the pH in S3, which adjusts the acid being added,.
4. preparation method according to claim 1, it is characterised in that: the dry time is 8-12 hours in S4.
5. preparation method according to claim 1, it is characterised in that: further include following steps:
A1: it is weighed in dehydrated alcohol, alpha-lipoic acid and syrup investment blender by weight, is passed through nitrogen, is stirred, put into
Sieving equipment sieving, obtains lipoic acid slice;
A2: being introduced into ball blast in shot-blasting machine for the lipoic acid slice obtained by step A1 and be granulated, and control the time of ball blast granulation,
It is dry then to introduce drying device, obtains the non-uniform lipoic acid particle of partial size;
A3: the non-uniform lipoic acid particle of the partial size obtained by step A2 is sieved, the lipoic acid particle screened out that is sieved returns to
Step A1 reuse, obtains the lipoic acid particle of uniform particle diameter.
6. preparation method according to claim 5, it is characterised in that: the weight of dehydrated alcohol, alpha-lipoic acid and syrup in A1
Amount is than being 0.5:1:0.25.
7. preparation method according to claim 5, it is characterised in that: the mixing speed in A1 is 10-60rmp, temperature control
It is made as 10-25 DEG C.
8. preparation method according to claim 5, it is characterised in that: the sieve crossed in A3 is the sieve of 30-100 mesh.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910396382.7A CN110003168A (en) | 2019-05-14 | 2019-05-14 | A kind of preparation method of high-purity alpha-lipoic acid |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910396382.7A CN110003168A (en) | 2019-05-14 | 2019-05-14 | A kind of preparation method of high-purity alpha-lipoic acid |
Publications (1)
Publication Number | Publication Date |
---|---|
CN110003168A true CN110003168A (en) | 2019-07-12 |
Family
ID=67176798
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201910396382.7A Pending CN110003168A (en) | 2019-05-14 | 2019-05-14 | A kind of preparation method of high-purity alpha-lipoic acid |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN110003168A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112574171A (en) * | 2020-12-15 | 2021-03-30 | 南京新百药业有限公司 | Preparation method of lipoic acid |
CN113292533A (en) * | 2021-05-25 | 2021-08-24 | 四川智强医药科技开发有限公司 | Method for purifying polymer impurities in lipoic acid |
-
2019
- 2019-05-14 CN CN201910396382.7A patent/CN110003168A/en active Pending
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112574171A (en) * | 2020-12-15 | 2021-03-30 | 南京新百药业有限公司 | Preparation method of lipoic acid |
CN113292533A (en) * | 2021-05-25 | 2021-08-24 | 四川智强医药科技开发有限公司 | Method for purifying polymer impurities in lipoic acid |
CN113292533B (en) * | 2021-05-25 | 2024-04-16 | 四川智强医药科技开发有限公司 | Method for purifying polymer impurities in lipoic acid |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN110003168A (en) | A kind of preparation method of high-purity alpha-lipoic acid | |
CN103058989B (en) | Method for preparing alpha-lipoic acid | |
CN1247570C (en) | Novel pyridyl cyanoguandine compounds | |
CN104961715B (en) | A kind of preparation method of Dapagliflozin | |
CN106478762B (en) | A kind of preparation method of diammonium glycyrhetate | |
CN107001294A (en) | A kind of method for preparing Gadobutrol | |
CN112079742B (en) | Method for preparing lidocaine through continuous reaction | |
CN106854187A (en) | A kind of preparation method of AHU-377 and Valsartan trisodium salt eutectic hydrate crystal forms II | |
CN103102294A (en) | Production method carboxymethyl cysteine | |
EP1636185A1 (en) | Novel crystalline forms of perindopril erbumine | |
CN106478479B (en) | A kind of vitamin D3Production technology | |
CN105131037B (en) | Preparation method for high-purity tedizolid phosphate | |
CN114349768B (en) | Preparation method of cefotaxime acid | |
CN110028430A (en) | A kind of preparation method of sulindac | |
CN104710352B (en) | A kind of method for crystallising of vitamin B6 | |
CN110229075A (en) | A kind of preparation process of Indobufen intermediate | |
CN103910685A (en) | Method used for purifying sulfadimoxine | |
CN102241599B (en) | Method for preparing glycine | |
CN108079294B (en) | Ferrocene-lanthanide metal compound and preparation method and application thereof | |
CN108239052A (en) | Andrographolide and its extracting method | |
CN104557715A (en) | Preparation method of imidocarb dipropionate sterile APIs (active pharmaceutical ingredients) | |
CN102206185B (en) | Process for refining bendazac lysine and analogs thereof | |
CN104109133A (en) | Method for preparing N-acyl phenothiazine | |
CN108524518A (en) | A kind of antigout effect of tetrazole compound | |
CN111635304B (en) | Preparation method of ferrous gluconate |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
WD01 | Invention patent application deemed withdrawn after publication | ||
WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20190712 |