CN102786573A - Glycyrrhetinic acid crystal B substance, its preparation method, and its applications in medicines and healthcare products - Google Patents
Glycyrrhetinic acid crystal B substance, its preparation method, and its applications in medicines and healthcare products Download PDFInfo
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Abstract
The invention discloses a new glycyrrhetinic acid crystal B substance with the structure represented by formula (I), a preparation method of a glycyrrhetinic acid crystal B sample, products prepared through treating the glycyrrhetinic acid crystal B substance as an active component, and applications of the glycyrrhetinic acid crystal B in the disease control and the healthcare, wherein the products comprise medicines and healthcare products
Description
Technical field
The present invention relates to a kind of new crystal type A state of matter of glycyrrhetinic acid, the preparation method of glycyrrhetinic acid crystal type A sample adopts the product of glycyrrhetinic acid crystal type A material as activeconstituents, and the purposes of glycyrrhetinic acid crystal type A, belongs to medical technical field.
Background technology
Glycyrrhetinic acid, English Glycyrrhetinic acid by name, molecular structure is suc as formula shown in (I)
In Chinese patent CN101899081A (publication number), put down in writing " the glycyrrhetinic acid ester derivative compound method and the deoxidation glycyrrhetinic acid ester cpds " of inventions such as Zhang Aiming
[1], wherein related to the preparation method of the ester derivative of glycyrrhetinic acid.Do not relate to the glycyrrhetinic acid compound.
In Chinese patent CN1563073 (publication number), put down in writing " preparation method of glycyrrhetinic acid " of inventions such as Fan Yunge
[2], wherein relating to the glycyrrhizic acid inclusion compound is raw material, uses Potenlini to obtain the preparation method of glycyrrhetinic acid through acidolysis.It is different with the preparation method of present patent application that this patent belongs to the glycyrrhetinic acid compounds process for production thereof.
In Chinese patent CN1846705 (publication number), put down in writing " application in preparation treatment inflammatory bowel medicine of Potenlini or glycyrrhetinic acid " of Wuhan University's fourth rainbow invention
[3], wherein relate to the application in preparation inflammatory enteropathy medicine of Potenlini or glycyrrhetinic acid.Belong to the clinical application of glycyrrhetinic acid, do not relate to the glycyrrhetinic acid crystal formation and prepare problem.
In Chinese patent CN101254308 (publication number), put down in writing " glycyrrhetinic acid-polyoxyethylene glycol/chitosan liver target composite drug administration system and the preparation method " of inventions such as Yuan Zhi
[4], wherein relate to a kind of novel hepatic targeting drug carrier-glycyrrhetinic acid-polyoxyethylene glycol/chitosan or chitosan derivatives liver target composite drug administration system.Patent relates to the mixture preparation method with glycyrrhetinic acid, does not relate to the glycyrrhetinic acid crystal formation and prepares problem.
In Chinese patent CN101292952 (publication number), put down in writing " Potenlini, glycyrrhetinic acid or its salt or derivatives thereof thermo-sensitive gel and the method for making and the application " of inventions such as Ding Hong
[5], wherein related to Potenlini, glycyrrhetinic acid or its salt or derivatives thereof thermo-sensitive gel.Patent relates to glycyrrhetinic acid mixture preparation method, and the crystal formation that does not relate to glycyrrhetinic acid prepares problem.
In Chinese patent CN101919870A (publication number), put down in writing " glycyrrhetinic acid, the application of Potenlini in preparation prevention or treatment pulmonary fibrosis medicine " of inventions such as Zhang Lurong
[6], wherein relate to glycyrrhetinic acid, the application of Potenlini in preparation prevention or treatment pulmonary fibrosis medicine.Belong to the clinical application of glycyrrhetinic acid, do not relate to the glycyrrhetinic acid crystal formation and prepare problem.
In Chinese patent CN101920017A (publication number), put down in writing the inventions such as Wang Qing of Dalian University of Technology " being used to promote the compsn of glycyrrhetinic acid to realize percutaneous permeation "
[7], wherein related to a kind of compsn that is used to promote glycyrrhetinic acid to realize percutaneous permeation, belong to field of medicaments, patent relates to glycyrrhetinic acid mixture preparation method, and the crystal formation that does not relate to glycyrrhetinic acid prepares problem.
In Chinese patent CN101926815A (publication number), put down in writing inventions such as Zhou Haibin " a kind of peoniflorin and glycyrrhetinic acid composition and preparation method thereof and application "
[8], wherein related to peoniflorin and glycyrrhetinic acid composition.Patent relates to glycyrrhetinic acid mixture preparation method, and the crystal formation that does not relate to glycyrrhetinic acid prepares problem.
In Chinese patent CN101838303A (publication number), put down in writing " preparation method of glycyrrhetinic acid " of the inventions such as Pan Xuejun of Kunming University of Science and Technology
[9], wherein related to the process for purification of glycyrrhetinic acid.Wherein related to and utilized microwave technology to prepare the glycyrrhetinic acid method, the crystal formation that does not relate to glycyrrhetinic acid prepares problem.
In Chinese patent CN101817867A (publication number), put down in writing " a kind of preparation method of glycyrrhetinic acid " of inventions such as Gao Ying
[10], wherein related to the purification process of glycyrrhetinic acid, be about to Potenlini acid powder through extracting with organic solvent dissolution, concentrate and obtain extract, in acetic acid, obtain the acetyl glycyrrhetinic acid with ore deposit acid-catalyzed hydrolysis and acetylize; In the acetyl glycyrrhetinic acid, add entry or alcohol then, hydrolysis obtains thick glycyrrhetinic acid under base catalysis, adds the gac reflux decolour, and crystallization obtains glycyrrhetinic acid.The glycyrrhetinic acid inorganic salt that this method relates to are removed and decoloring method, and are different with the crystal formation preparation method of present patent application.
Through patent and literature search both at home and abroad, find progress relevant for glycyrrhetinic acid
[11,12], extraction process
[13], detection method
[14]And formulation
[15,16,17]Bibliographical information, but do not find the research of the relevant crystal formation of relevant glycyrrhetinic acid and crystal formation patent or bibliographical information.
It is different with above-mentioned patent or literature research report content that the present invention has found, is discovery, specimen preparation and the purposes of glycyrrhetinic acid new crystal material.Research purpose of the present invention is to start with from the research of glycyrrhetinic acid crystal formation solid matter; Through crystal formation triage techniques, crystal formation evaluated biological activity technology; The advantage crystal-form substances state that on identical active substance different crystal forms state aspect, seek, find, exploitation has the glycyrrhetinic acid of optimal clinical curative effect and healthcare products effect is for application country or international intellecture property invention patent protection provide science data from glycyrrhetinic acid crystal-form substances basis.
Summary of the invention
The technical problem that the present invention will solve provides a kind of new crystal formation of the glycyrrhetinic acid shown in the formula (I), i.e. crystal B-type
Another technical problem that the present invention will solve provides the preparation method of glycyrrhetinic acid crystal B-type material.
Another technical problem that the present invention will solve provides the product of glycyrrhetinic acid crystal B-type composition as activeconstituents.
Another technical problem that the present invention will solve provides the application of glycyrrhetinic acid crystal B-type.
Particularly, the technical problem for solving, adopt following technical scheme:
1. the crystal B-type sample morphological specificity of glycyrrhetinic acid:
1.1 the glycyrrhetinic acid crystal B-type solid matter, (CuK when using powder x-ray diffraction analysis
αRadiation), show as the diffraction peak position that has 1 Height%=100 2-Theta=14.9 ° ± 0.2 ° or
The position.Accompanying drawing 1 provides the x-ray diffractogram of powder spectrum of glycyrrhetinic acid crystal B-type sample.
1.2 glycyrrhetinic acid crystal B-type solid matter, its infrared absorption spectrum (Fig. 2) 3433,2928,2867,2089,1701,1652,1454,1386,1361,1326,1312,1280,1257,1209,1173,1136,1101,1085,1036,992,959,947,919,880,868,818,751,700,684,666cm
-1± 2cm
-1Absorption peak be the diffuse reflectance infrared spectroscopy peak position that the glycyrrhetinic acid crystal B-type solid matter is appeared.Accompanying drawing 2 provides the infrared absorpting light spectra of glycyrrhetinic acid crystal B-type sample.
1.3 the glycyrrhetinic acid crystal B-type solid matter contains three Peak endotherm(ic)peaks respectively 78 ℃ ± 3 ℃, 105 ℃ ± 3 ℃, 297 ℃ ± 3 ℃ positions in its DSC collection of illustrative plates (Fig. 3) when temperature rise rate is 10 ℃ of PMs.
1.4 glycyrrhetinic acid crystal B-type solid matter, its melting point values are 293 ℃ ± 2 ℃.
2. the preparation method characteristic of glycyrrhetinic acid crystal B-type sample:
2.1 the invention provides a kind of preparation method of glycyrrhetinic acid crystal B-type sample, the glycyrrhetinic acid crystal B-type solid sample that it is characterized in that using earlier the chloroform single solvent under normal temperature or high temperature, the glycyrrhetinic acid sample to be dissolved fully and directly or indirectly prepare through 4 ℃～80 ℃ of envrionment temperatures, ambient moisture 10%～75%, normal pressure or vacuum pressure condition.
2.2 the invention provides the preparation method of other a kind of glycyrrhetinic acid crystal B-type sample, it is characterized in that using earlier any two or more make up that the mixed solvent system processed dissolves the glycyrrhetinic acid sample fully and directly or indirectly prepare through 4 ℃～80 ℃ of envrionment temperatures, ambient moisture 10%～75%, normal pressure or vacuum pressure condition through different proportionings under normal temperature or high temperature the glycyrrhetinic acid crystal B-type solid sample in chloroform and normal hexane, hexanaphthene, the water different sorts solvent.
3. the crystal B-type of glycyrrhetinic acid is as the using dosage and the purposes characteristic of active substance:
3.1 of the present invention a kind of product is provided also, with glycyrrhetinic acid crystal B-type composition as activeconstituents and contain other auxiliary materials.Product of the present invention comprises medicine, healthcare products.
The crystal formation purity of glycyrrhetinic acid crystal B-type is 1%～100% in the described product.
The formulation of said product is selected from tablet, capsule, pill, injection, slowly-releasing or control-released agent, pulvis.
Used the various products of glycyrrhetinic acid crystal B-type material 3.2 the invention provides, comprised medicine, healthcare products, it is characterized in that the glycyrrhetinic acid crystal B-type absorbs dosage in 1mg～40g scope its every day as the activeconstituents exploitation.
The various products of glycyrrhetinic acid crystal B-type material have been used 3.3 the invention provides as the activeconstituents exploitation; Comprise medicine, healthcare products; It is characterized in that, used glycyrrhetinic acid crystal B-type composition to guarantee its in vivo absorption characteristic, effectively bioavailability, effective blood drug concentration, stable time that continues and reach prevention, treatment, health-care effect and the application of making the most of the advantage as active substance.
4. the new crystal B-type oral administration of glycyrrhetinic acid absorbs characteristic:
The invention provides and use the various products of glycyrrhetinic acid crystal B-type material as the activeconstituents exploitation; Comprise medicine, healthcare products; And the bio-absorbable effect after the oral administration, it is characterized in that glycyrrhetinic acid crystal B-type material can reach peak concentration value, the active function characteristic in 12 hours maintenance platform cycles at 15 minutes quick actings, 1 hour blood through gi tract as activeconstituents.Fig. 4 provides the rat plasma concentration curve after the administration of glycyrrhetinic acid crystal B-type sample oral administration.
5. the application of glycyrrhetinic acid crystal B-type in pharmacy.
The invention provides the application of glycyrrhetinic acid crystal B-type in the medicine of preparation treatment bronzed disease, inflammatory enteropathy and prevention or treatment pulmonary fibrosis.
Description of drawings
The x-ray diffractogram of powder spectrum of Fig. 1 glycyrrhetinic acid crystal B-type sample
The infrared absorpting light spectra of Fig. 2 glycyrrhetinic acid crystal B-type sample
The DSC collection of illustrative plates of Fig. 3 glycyrrhetinic acid crystal B-type sample
Rat plasma concentration curve after the administration of Fig. 4 glycyrrhetinic acid crystal B-type sample oral administration
Embodiment
Be better explanation technical scheme of the present invention, the spy provides following examples, but the present invention is not limited to this.
The direct preparation method of glycyrrhetinic acid crystal B-type sample:
The crystal B-type sample preparation methods of glycyrrhetinic acid is characterized in that using the 20ml chloroform solvent under normal temperature condition, the glycyrrhetinic acid sample to be dissolved fully that to be placed on temperature be under 45 ℃ the vacuum condition solvent to be drained, and prepares the glycyrrhetinic acid crystal form samples.
The x-ray diffractogram of powder spectrum of gained glycyrrhetinic acid crystal form samples is shown in accompanying drawing 1
The infrared absorpting light spectra of gained glycyrrhetinic acid crystal form samples is shown in accompanying drawing 2
The DSC collection of illustrative plates of gained glycyrrhetinic acid crystal form samples is shown in accompanying drawing 3
Above spectrum data result shows that present embodiment gained crystalline crystal formation is the glycyrrhetinic acid crystal B-type.
The direct preparation method of glycyrrhetinic acid crystal B-type sample:
The crystal B-type sample preparation methods of glycyrrhetinic acid; It is characterized in that using the 20ml chloroform to be placed on that to separate out solid under 10 ℃ of constant temperatures dry through vacuum filtration again processing oversaturated chloroformic glycyrrhetinic acid solution under 45 ℃ of water bath condition, prepare the glycyrrhetinic acid crystal form samples.
The x-ray diffractogram of powder spectrum of gained glycyrrhetinic acid crystal form samples is shown in accompanying drawing 1
The infrared absorpting light spectra of gained glycyrrhetinic acid crystal form samples is shown in accompanying drawing 2
The DSC collection of illustrative plates of gained glycyrrhetinic acid crystal form samples is shown in accompanying drawing 3
Above spectrum data result shows that present embodiment gained crystalline crystal formation is the glycyrrhetinic acid crystal B-type.
Embodiment 3
The direct preparation method of glycyrrhetinic acid crystal B-type sample:
The crystal B-type sample preparation methods of glycyrrhetinic acid; It is characterized in that using the 20ml chloroform to add 20ml～40ml normal hexane mixed solvent and under 40 ℃ of temperature condition, the glycyrrhetinic acid sample is dissolved back room temperature or stand at low temperature fully to separate out solid dry through vacuum filtration again, prepare the glycyrrhetinic acid crystal form samples.
The x-ray diffractogram of powder spectrum of gained glycyrrhetinic acid crystal form samples is shown in accompanying drawing 1
The infrared absorpting light spectra of gained glycyrrhetinic acid crystal form samples is shown in accompanying drawing 2
The DSC collection of illustrative plates of gained glycyrrhetinic acid crystal form samples is shown in accompanying drawing 3
Above spectrum data result shows that present embodiment gained crystalline crystal formation is the glycyrrhetinic acid crystal B-type.
The glycyrrhetinic acid crystal B-type absorbs characteristic and Plasma Concentration characteristic in the rat body:
Adopt the conventional raising condition of SD rat of body weight 230 ± 5g to raise, freely drink water, behind the fasting 12h, give medicine, before administration, reach after the administration 0.083,0.25,0.5,1,1.5,2,3,4,6,8,12,24 (h) by 200mg/kg filling stomach.Eye socket is got the about 0.4ml of blood, and 4, the centrifugal 15min of 000rpm, preparation blood plasma.Get 150 μ l blood plasma, add methyl alcohol 200 μ l, vortex oscillation 1min, 13, the centrifugal 15min of 400rpm draws supernatant through 0.45 μ m filtering with microporous membrane, gets 20 μ l and carries out HPLC detection, Aligent XDB-C
18(150 * 4.6mm, 5 μ m), moving phase: methyl alcohol: 0.4% aqueous acetic acid=90: 10, flow velocity: 1ml/min detects wavelength: 254nm.The result shows behind the oral glycyrrhetinic acid crystal B-type solid material can detect the glycyrrhetinic acid activeconstituents in the blood, reaches peak concentration value, the active function characteristic in 12 hours maintenance platform cycles through gi tract at 15 minutes quick actings, 1 hour blood.
Glycyrrhetinic acid crystal B-type Plasma Concentration data
Embodiment 5
Glycyrrhetinic acid crystal B-type sample is as the dosage of active constituents of medicine:
The medicinal tablet or other preparations that use crystal B-type glycyrrhetinic acid material to manufacture as active constituents of medicine; It is characterized in that containing the activeconstituents of glycyrrhetinic acid crystal B-type as medicine; Every day, dosage was 300mg; Can be prepared into 3 times/each 1 100mg conventional tablet every day respectively, every day 2 times/each 1 150mg conventional tablet or every day 1 time/each 1 300mg the tablet type.
The problem that needs explanation: the glycyrrhetinic acid crystal formation pharmaceutical composition that the present invention relates to has many factor affecting on the dosage of effective constituent, for example: be used to prevent different with the purposes of treating and cause the difference of dosage every day; Ill character is different with ill severity and cause the different of dosage every day; The difference of patient's sex, age, body surface area, route of administration, administration number of times, therapeutic purpose are different and cause the difference of dosage every day; In addition, absorption that exists between crystal form samples and Plasma Concentration are not equal, also cause the present invention to be the 0.01-150mg/kg body weight in appropriate dose scope every day of using glycyrrhetinic acid crystal B-type composition, are preferably the 1-100mg/kg body weight.Should formulate different glycyrrhetinic acid crystal B-type effective constituent total dose schemes with treatment different situations demand according to the prevention of reality during use, and can be divided into the single or multiple administering mode.
Glycyrrhetinic acid crystal B-type sample is as the healthcare products dosage of active constituents of medicine:
Use crystal B-type glycyrrhetinic acid material as the functional health product that activeconstituents manufactures, it is characterized in that containing in the healthcare products glycyrrhetinic acid crystal B-type as the health active component substances, its consumption is from 1mg 40g.
Reference
1. Chinese patent, publication number CN101899081C.
2. Chinese patent, publication number CN1563073.
3. Chinese patent, publication number CN1846705.
4. Chinese patent, publication number CN101254308.
5. Chinese patent, publication number CN101292952.
6. Chinese patent, publication number CN101919870C.
7. Chinese patent, publication number CN101920017C.
8. Chinese patent, publication number CN101926815C.
9. Chinese patent, publication number CN101838303C.
10. Chinese patent, publication number CN101817867C.
The honor 11. pass away, Zhao Jie etc.The research of glycyrrhetinic acid and prospect.University Of Dalian's journal, 2005,26 (4): 85-88
12. surplus side, Gao Jianpei etc.From Radix Glycyrrhizae, extract the progress that Potenlini prepares glycyrrhetinic acid.Jiangxi agricultural journal, 2008,20 (8): 91-94.
13. once opened China.From Radix Glycyrrhizae, extract the technical study of Potenlini and glycyrrhetinic acid.2006，8(1)：62-64
14. the refined duckweed of king, Cao Bo etc.Glycyrrhetinic acid method for measurement of concentration research in the rat plasma.People's Armed Police medical college journal, 2008,17 (3): 201-203.
15. Zhu Ling, square petrel etc.The preparation of glycyrrhetinic acid emulsifiable paste and lipolysis research.Modern food science and technology, 2009,25 (11): 1335-1337.
16. Wang Jun, Zhang Jian etc.The preparation of glycyrrhetinic acid polylactic acid microsphere and property research thereof.The time precious traditional Chinese medical science traditional Chinese medicines, 2009,20 (4): 1002-1003.
17. Guo Bo is red, Cheng Yi etc.The preparation of glycyrrhetinic acid liposome and pharmaceutics Study on Properties thereof.Herbal medicine, 2010,41 (3): 380-383.
Claims (10)
1. the new crystal B-type solid matter of the glycyrrhetinic acid shown in the formula (I),
It is characterized in that (CuK when using powder x-ray diffraction analysis
αRadiation) show as the diffraction peak position that has 1 Height%=100 2-Theta=14.9 ° ± 0.2 ° or
The position.
2. the preparation method of the said glycyrrhetinic acid crystal B-type of claim 1 sample; It is characterized in that the glycyrrhetinic acid crystal B-type solid sample that uses earlier the chloroform single solvent under normal temperature or high temperature, the glycyrrhetinic acid sample to be dissolved fully and directly or indirectly prepare through 4 ℃～80 ℃ of envrionment temperatures, ambient moisture 10%～75%, normal pressure or vacuum pressure condition.
3. the preparation method of the said glycyrrhetinic acid crystal B-type of claim 1 sample; It is characterized in that, use earlier any two or more make up that the mixed solvent system processed dissolves the glycyrrhetinic acid sample fully and directly or indirectly prepare through 4 ℃～80 ℃ of envrionment temperatures, ambient moisture 10%～75%, normal pressure or vacuum pressure condition through different proportionings under normal temperature or high temperature the glycyrrhetinic acid crystal B-type solid sample in chloroform and normal hexane, hexanaphthene, the water different sorts solvent.
4. a product is characterized in that, as activeconstituents, and contains other auxiliary materials with the described glycyrrhetinic acid crystal B-type of claim 1 composition.
5. according to the product of claim 4, it is characterized in that the crystal formation purity of described glycyrrhetinic acid crystal B-type is 1%～100%.
6. according to the product of claim 4, it is characterized in that said product is selected from medicine, healthcare products.
7. according to each product among the claim 4-6, the formulation of said product is selected from tablet, capsule, pill, injection, slowly-releasing or control-released agent, pulvis.
8. the application of the glycyrrhetinic acid crystal B-type of claim 1 in the medicine of preparation treatment bronzed disease.
9. the application of the glycyrrhetinic acid crystal B-type of claim 1 in the medicine of preparation inflammatory enteropathy.
10. the application of the glycyrrhetinic acid crystal B-type of claim 1 in the medicine of preparation prevention or treatment pulmonary fibrosis.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104045679A (en) * | 2014-06-06 | 2014-09-17 | 北京健坤和医药科技有限公司 | Glycyrrhetinic acid crystal type C, preparation method and use thereof in pharmaceutical compositions or health-care products |
| CN106543261A (en) * | 2016-10-27 | 2017-03-29 | 深圳市新阳唯康科技有限公司 | A kind of enoxolone crystal-form substances and preparation method thereof |
| CN106632575A (en) * | 2016-12-20 | 2017-05-10 | 深圳市新阳唯康科技有限公司 | Novel glycyrrhetinic acid crystal form and preparation method thereof |
| CN106749485A (en) * | 2016-11-25 | 2017-05-31 | 深圳市新阳唯康科技有限公司 | A kind of enoxolone novel crystal forms and preparation method thereof |
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| US3262851A (en) * | 1958-06-26 | 1966-07-26 | Biorex Laboratories Ltd | Pharmacological compositions containing glycyrrhetinic acid derivative |
| CN1563073A (en) * | 2004-04-06 | 2005-01-12 | 南开大学 | Method for preparing enoxolone |
| CN101607980A (en) * | 2009-06-15 | 2009-12-23 | 北京九草堂药物研究院有限公司 | A kind of preparation of licorice extract of bulk drug for livestock |
| CN101838303A (en) * | 2010-06-07 | 2010-09-22 | 昆明理工大学 | Preparation method of glycyrrhetinic acid |
-
2011
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3262851A (en) * | 1958-06-26 | 1966-07-26 | Biorex Laboratories Ltd | Pharmacological compositions containing glycyrrhetinic acid derivative |
| CN1563073A (en) * | 2004-04-06 | 2005-01-12 | 南开大学 | Method for preparing enoxolone |
| CN101607980A (en) * | 2009-06-15 | 2009-12-23 | 北京九草堂药物研究院有限公司 | A kind of preparation of licorice extract of bulk drug for livestock |
| CN101838303A (en) * | 2010-06-07 | 2010-09-22 | 昆明理工大学 | Preparation method of glycyrrhetinic acid |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104045679A (en) * | 2014-06-06 | 2014-09-17 | 北京健坤和医药科技有限公司 | Glycyrrhetinic acid crystal type C, preparation method and use thereof in pharmaceutical compositions or health-care products |
| CN104045679B (en) * | 2014-06-06 | 2016-04-27 | 北京健坤和医药科技有限公司 | Glycyrrhetinic acid crystal C type, its preparation method and the purposes in pharmaceutical composition or healthcare products thereof |
| CN106543261A (en) * | 2016-10-27 | 2017-03-29 | 深圳市新阳唯康科技有限公司 | A kind of enoxolone crystal-form substances and preparation method thereof |
| CN106749485A (en) * | 2016-11-25 | 2017-05-31 | 深圳市新阳唯康科技有限公司 | A kind of enoxolone novel crystal forms and preparation method thereof |
| CN106632575A (en) * | 2016-12-20 | 2017-05-10 | 深圳市新阳唯康科技有限公司 | Novel glycyrrhetinic acid crystal form and preparation method thereof |
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| Publication number | Publication date |
|---|---|
| CN102786573B (en) | 2016-01-13 |
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