CN105906558A - Anti-fibrosis drug pirfenidone crystal forms and preparation method thereof - Google Patents
Anti-fibrosis drug pirfenidone crystal forms and preparation method thereof Download PDFInfo
- Publication number
- CN105906558A CN105906558A CN201610284441.8A CN201610284441A CN105906558A CN 105906558 A CN105906558 A CN 105906558A CN 201610284441 A CN201610284441 A CN 201610284441A CN 105906558 A CN105906558 A CN 105906558A
- Authority
- CN
- China
- Prior art keywords
- pirfenidone
- crystal formation
- preparation
- pyriphenanthrenone
- dissolved
- 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
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Abstract
The invention discloses anti-fibrosis drug pirfenidone crystal forms and a preparation method thereof, and belongs to the technical field of anti-fibrosis drug pirfenidone. The technical scheme includes that the anti-fibrosis drug pirfenidone crystal forms include a pirfenidone crystal form II and a pirfenidone crystal form III, and the preparation method for the pirfenidone crystal form II and the pirfenidone crystal form III is provided specifically. The prepared pirfenidone crystal form II and the prepared pirfenidone crystal form III have the advantages of stable chemical-physical property, uniform crystal grain, suitability for long-term storage, convenience in preparation manufacture and the like.
Description
Technical field
The invention belongs to pyriphenanthrenone as anti-fibrosis medicine technical field, be specifically related to pyriphenanthrenone as anti-fibrosis medicine brilliant
Type and preparation method thereof.
Background technology
Pirfenidone, English name: Pirfenidone, chemical name: 5-methyl isophthalic acid-phenyl-2 (1H) pyridone is
Planting white or off-white powder shape solid, chemical structural formula is:.Fibrotic disease such as renal fibrosis, liver is hard
Change, myocardial fibrosis etc. are the important diseases that a class is seriously healthy for endangering human life, along with global industry and people
Life, the change of diet style, the sickness rate of fibrotic disease is just gradually increased.For Fibrotic morbidity link, both at home and abroad
Scholar has carried out a large amount of anti-fibrosis medicine from different field such as natural drug, chemicals, biological preparation and gene therapies
Screening and research, find that pyridine compounds is a class effective fibrosis compound.Wherein, pirfenidone is pyridone
The representative compound of compounds, has carried out much research the most.In November, 2008, lnterMune company announces that Japan is thick
Deep work saves the pirfenidone (pirfenidone) of approval the said firm and is used for treating idiopathic pulmonary fibrosis (idiopathic
Pulmonary fibrosis, IPF).Pirfenidone is first medicine got the Green Light in the whole world for treating IPF, and
Obtain U.S.'s Orphan drug and tight tracking design and the design of European seldom used medicine has authorized.
Preparation method and the technique of pirfenidone all reported in the most a lot of patents and article, but are all not directed to pirfenidone
Crystal formation.Crystal formation situation when the patent report of Publication No. CN105315198A pirfenidone crystallizes in ethyl acetate,
And specifically disclose characteristic peaks and the preparation method of angle of reflection 2 θ of the X-ray powder diffraction of obtained crystal formation I.But,
This patent documentation only discloses a kind of crystal formation of pirfenidone, the most more relevant records about pirfenidone crystal formation.
Summary of the invention
Present invention solves the technical problem that and there is provided a kind of pyriphenanthrenone as anti-fibrosis medicine crystal formation and preparation method thereof.
The present invention solves that above-mentioned technical problem adopts the following technical scheme that, pyriphenanthrenone as anti-fibrosis medicine crystal formation, its
It is characterised by including pirfenidone crystal formation II, the eigenvalue of angle of reflection 2 θ of the X-ray powder diffraction of this pirfenidone crystal formation II
Be 8.95 ± 0.2,14.48 ± 0.2,15.23 ± 0.2,18.62 ± 0.2,18.98 ± 0.2,20.14 ± 0.2,
23.05 ± 0.2,24.57 ± 0.2,27.46 ± 0.2,28.72 ± 0.2,30.56 ± 0.2,32.64 ± 0.2 Hes
47.94 ± 0.2, corresponding I/I0Value is respectively 6,7,100,30,28,6,16,6,9,11,8,17 and 8.
The preparation method of pyriphenanthrenone as anti-fibrosis medicine crystal formation of the present invention, it is characterised in that concretely comprise the following steps:
Being dissolved in by pirfenidone in the ethanol solution that volume fraction is 10%, wherein the volume of 1g pirfenidone correspondence ethanol solution is 4-
10mL, oil bath heated and stirred is completely dissolved to raw material, is cooled to 0-5 DEG C and stands crystallize, is dried to obtain pyrrole in 30-70 DEG C after filtration
Non-Buddhist nun ketone crystal formation II.
Pyriphenanthrenone as anti-fibrosis medicine crystal formation of the present invention, it is characterised in that include pirfenidone crystal formation III, should
The eigenvalue of angle of reflection 2 θ of the X-ray powder diffraction of pirfenidone crystal formation III is 9.03 ± 0.2,14.51 ± 0.2,
15.21±0.2º、18.64±0.2º、19.00±0.2º、21.27±0.2º、22.25±0.2º、22.93±0.2º、23.16
± 0.2,24.60 ± 0.2,27.49 ± 0.2,28.48 ± 0.2,32.63 ± 0.2,37.29 ± 0.2 and 45.79 ±
0.2, corresponding I/I0Value is respectively 70,52,37,100,64,23,17,48,48,46,48,11,15,12 and 12.
Pyriphenanthrenone as anti-fibrosis medicine crystal formation preparation method of the present invention, it is characterised in that concretely comprise the following steps: will
Pirfenidone is dissolved in ethyl acetate, and wherein the volume of 1g pirfenidone correspondence ethyl acetate is 2-8mL, is stirred at room temperature to raw material
Being completely dissolved, dropwise drip normal heptane under stirring, wherein the volume of 1g pirfenidone correspondence normal heptane is 20-40mL, after dripping off
It is cooled to 0-5 DEG C and stands crystallize, after filtration, be dried to obtain pirfenidone crystal formation III in 30-70 DEG C.
Pyriphenanthrenone as anti-fibrosis medicine crystal formation preparation method of the present invention, it is characterised in that concretely comprise the following steps: will
Pirfenidone is dissolved in dehydrated alcohol, and wherein the volume of 1g pirfenidone correspondence dehydrated alcohol is 2-6mL, and oil bath heated and stirred is extremely
Raw material is completely dissolved, and is cooled to 0-5 DEG C and stands crystallize, is dried to obtain pirfenidone crystal formation III in 30-70 DEG C after filtration.
Pyriphenanthrenone as anti-fibrosis medicine crystal formation preparation method of the present invention, it is characterised in that concretely comprise the following steps: will
Pirfenidone is dissolved in acetone, and wherein the volume of 1g pirfenidone correspondence acetone is 2-8mL, and oil bath heated and stirred is complete to raw material
Dissolve, be cooled to 0-5 DEG C and stand crystallize, after filtration, be dried to obtain pirfenidone crystal formation III in 30-70 DEG C.
Pyriphenanthrenone as anti-fibrosis medicine crystal formation preparation method of the present invention, it is characterised in that concretely comprise the following steps: will
Pirfenidone is dissolved in isopropanol, and wherein the volume of 1g pirfenidone correspondence isopropanol is 4-10mL, and oil bath heated and stirred is to former
Material is completely dissolved, and is cooled to 0-5 DEG C and stands crystallize, is dried to obtain pirfenidone crystal formation III in 30-70 DEG C after filtration.
Pyriphenanthrenone as anti-fibrosis medicine crystal formation preparation method of the present invention, it is characterised in that concretely comprise the following steps: will
Pirfenidone is dissolved in pure water, and wherein the volume of 1g pirfenidone correspondence pure water is 2-8mL, and oil bath heated and stirred is complete to raw material
Dissolve, be cooled to 0-5 DEG C and stand crystallize, after filtration, be dried to obtain pirfenidone crystal formation III in 30-70 DEG C.
Pyriphenanthrenone as anti-fibrosis medicine crystal formation preparation method of the present invention, it is characterised in that concretely comprise the following steps: will
Pirfenidone is dissolved in the tetrahydrofuran aqueous solution that mass fraction is 10%, wherein 1g pirfenidone correspondence tetrahydrofuran aqueous solution
Volume be 2-6mL, oil bath heated and stirred is completely dissolved to raw material, be cooled to 0-5 DEG C stand crystallize, in 30-70 DEG C after filtration
It is dried to obtain pirfenidone crystal formation III.
Pyriphenanthrenone as anti-fibrosis medicine crystal formation preparation method of the present invention, it is characterised in that concretely comprise the following steps: will
Pirfenidone is dissolved in the aqueous acetone solution that mass fraction is 10%, and wherein the volume of 1g pirfenidone correspondence aqueous acetone solution is
4-10mL, oil bath heated and stirred is completely dissolved to raw material, is cooled to 0-5 DEG C and stands crystallize, is dried to obtain in 30-70 DEG C after filtration
Pirfenidone crystal formation III.
Pirfenidone crystal formation II and pirfenidone crystal formation III prepared by the present invention have chemical physical property and stablize, crystal
Granule is uniform, is suitable for long term storage, it is simple to the advantages such as the manufacture of preparation.
Accompanying drawing explanation
Fig. 1 is the XRD figure spectrum of the pirfenidone crystal formation II that the embodiment of the present invention 1 prepares;
Fig. 2 is the XRD figure spectrum of the pirfenidone crystal formation III that the embodiment of the present invention 2 prepares.
Detailed description of the invention
By the following examples the foregoing of the present invention is described in further details, but this should be interpreted as this
The scope inventing above-mentioned theme is only limitted to below example, and all technology realized based on foregoing of the present invention belong to this
Bright scope.
Embodiment 1
Being placed in by 10g pirfenidone in two mouthfuls of flasks of 100mL, add the ethanol solution 60mL that volume fraction is 10%, oil bath adds
Thermal agitation is completely dissolved to raw material, stops heating after raw material is completely dissolved, and is progressively cooled to 0-5 DEG C and stands two hours, filters,
In 50 DEG C of normal pressure forced air dryings 12 hours, obtain the powder of pirfenidone crystal formation II.
Embodiment 2
Being placed in by 10g pirfenidone in two mouthfuls of flasks of 100mL, add dehydrated alcohol 40mL, oil bath heated and stirred is molten to raw material
Solve, after raw material is completely dissolved, stops heating, be progressively cooled to 0-5 DEG C and stand two hours, filter, in 50 DEG C of normal pressure forced air dryings
12 hours, obtain the powder of pirfenidone crystal formation III.
Embodiment 3
10g pirfenidone is placed in two mouthfuls of flasks of 500mL, adds ethyl acetate 50mL, be stirred at room temperature to raw material the most molten
Solve, under stirring, gradually drip 300mL normal heptane, filter after being incubated 8 hours in 0-5 DEG C after dripping, do in 50 DEG C of normal pressure air blast
Dry 12 hours, obtain the powder of pirfenidone crystal formation III.
Embodiment 4
Being placed in by 10g pirfenidone in two mouthfuls of flasks of 100mL, add acetone 40mL, oil bath heated and stirred is the most molten to raw material
Solve, after raw material is completely dissolved, stops heating, be progressively cooled to 0-5 DEG C and stand two hours, filter, in 50 DEG C of normal pressure forced air dryings
The powder obtaining pirfenidone crystal formation III in 12 hours.
Embodiment 5
Being placed in by 10g pirfenidone in two mouthfuls of flasks of 100mL, add isopropanol 70mL, oil bath heated and stirred is complete to raw material
Dissolve, after raw material is completely dissolved, stops heating, be progressively cooled to 0-5 DEG C and stand two hours, filter, do in 50 DEG C of normal pressure air blast
Dry 12 hours, obtain the powder of pirfenidone crystal formation III.
Embodiment 6
Being placed in by 10g pirfenidone in two mouthfuls of flasks of 500mL, add pure water 400mL, oil bath heated and stirred is the most molten to raw material
Solve, after raw material is completely dissolved, stops heating, be progressively cooled to 0-5 DEG C and stand two hours, filter, in 50 DEG C of normal pressure forced air dryings
12 hours, obtain the powder of pirfenidone crystal formation III.
Embodiment 7
10g pirfenidone is placed in two mouthfuls of flasks of 100mL, adds the tetrahydrofuran aqueous solution 30mL that mass fraction is 10%,
Oil bath heated and stirred is completely dissolved to raw material, stops heating after raw material is completely dissolved, and is progressively cooled to 0-5 DEG C of standing two little
Time, filter, in 50 DEG C of normal pressure forced air dryings 12 hours, obtain the powder of pirfenidone crystal formation III.
Embodiment 8
Being placed in by 10g pirfenidone in two mouthfuls of flasks of 100mL, adding mass fraction is 10% aqueous acetone solution 60mL, and oil bath adds
Thermal agitation is completely dissolved to raw material, stops heating after raw material is completely dissolved, and is progressively cooled to 0-5 DEG C and stands two hours, filters,
In 50 DEG C of normal pressure forced air dryings 12 hours, obtain the powder of pirfenidone crystal formation III.
Embodiment above describes the ultimate principle of the present invention, principal character and advantage, the technical staff of the industry should
Understanding, the present invention is not restricted to the described embodiments, and the simply explanation present invention's described in above-described embodiment and description is former
Reason, under the scope without departing from the principle of the invention, the present invention also has various changes and modifications, and these changes and improvements each fall within
In the scope of protection of the invention.
Claims (10)
1. pyriphenanthrenone as anti-fibrosis medicine crystal formation, it is characterised in that include pirfenidone crystal formation II, this pirfenidone crystal formation II
The eigenvalue of angle of reflection 2 θ of X-ray powder diffraction be 8.95 ± 0.2,14.48 ± 0.2,15.23 ± 0.2,18.62 ±
0.2º、18.98±0.2º、20.14±0.2º、23.05±0.2º、24.57±0.2º、27.46±0.2º、28.72±0.2º、
30.56 ± 0.2,32.64 ± 0.2 and 47.94 ± 0.2, corresponding I/I0Value be respectively 6,7,100,30,28,6,16,6,
9,11,8,17 and 8.
2. the preparation method of the pyriphenanthrenone as anti-fibrosis medicine crystal formation described in a claim 1, it is characterised in that specifically walk
Suddenly it is: pirfenidone is dissolved in the ethanol solution that volume fraction is 10%, wherein the volume of 1g pirfenidone correspondence ethanol solution
For 4-10mL, oil bath heated and stirred is completely dissolved to raw material, is cooled to 0-5 DEG C and stands crystallize, is dried in 30-70 DEG C after filtration
To pirfenidone crystal formation II.
3. pyriphenanthrenone as anti-fibrosis medicine crystal formation, it is characterised in that include pirfenidone crystal formation III, this pirfenidone crystal formation
The eigenvalue of angle of reflection 2 θ of the X-ray powder diffraction of III is 9.03 ± 0.2,14.51 ± 0.2,15.21 ± 0.2,
18.64±0.2º、19.00±0.2º、21.27±0.2º、22.25±0.2º、22.93±0.2º、23.16±0.2º、24.60
± 0.2,27.49 ± 0.2,28.48 ± 0.2,32.63 ± 0.2,37.29 ± 0.2 and 45.79 ± 0.2, corresponding I/
I0Value is respectively 70,52,37,100,64,23,17,48,48,46,48,11,15,12 and 12.
4. the preparation method of the pyriphenanthrenone as anti-fibrosis medicine crystal formation described in a claim 3, it is characterised in that specifically walk
Suddenly it is: pirfenidone is dissolved in ethyl acetate that wherein the volume of 1g pirfenidone correspondence ethyl acetate is 2-8mL, and room temperature is stirred
Mixing and be completely dissolved to raw material, dropwise drip normal heptane under stirring, wherein the volume of 1g pirfenidone correspondence normal heptane is 20-
40mL, is cooled to 0-5 DEG C and stands crystallize, be dried to obtain pirfenidone crystal formation III in 30-70 DEG C after filtration after dripping off.
5. the preparation method of the pyriphenanthrenone as anti-fibrosis medicine crystal formation described in a claim 3, it is characterised in that specifically walk
Suddenly it is: pirfenidone is dissolved in dehydrated alcohol that wherein the volume of 1g pirfenidone correspondence dehydrated alcohol is 2-6mL, and oil bath adds
Thermal agitation is completely dissolved to raw material, is cooled to 0-5 DEG C and stands crystallize, is dried to obtain pirfenidone crystal formation in 30-70 DEG C after filtration
III。
6. the preparation method of the pyriphenanthrenone as anti-fibrosis medicine crystal formation described in a claim 3, it is characterised in that specifically walk
Suddenly it is: pirfenidone is dissolved in acetone that wherein the volume of 1g pirfenidone correspondence acetone is 2-8mL, and oil bath heated and stirred is extremely
Raw material is completely dissolved, and is cooled to 0-5 DEG C and stands crystallize, is dried to obtain pirfenidone crystal formation III in 30-70 DEG C after filtration.
7. the preparation method of the pyriphenanthrenone as anti-fibrosis medicine crystal formation described in a claim 3, it is characterised in that specifically walk
Suddenly being: be dissolved in isopropanol by pirfenidone that wherein the volume of 1g pirfenidone correspondence isopropanol is 4-10mL, oil bath heating is stirred
Mix and be completely dissolved to raw material, be cooled to 0-5 DEG C and stand crystallize, after filtration, be dried to obtain pirfenidone crystal formation III in 30-70 DEG C.
8. the preparation method of the pyriphenanthrenone as anti-fibrosis medicine crystal formation described in a claim 3, it is characterised in that specifically walk
Suddenly it is: pirfenidone is dissolved in pure water that wherein the volume of 1g pirfenidone correspondence pure water is 2-8mL, and oil bath heated and stirred is extremely
Raw material is completely dissolved, and is cooled to 0-5 DEG C and stands crystallize, is dried to obtain pirfenidone crystal formation III in 30-70 DEG C after filtration.
9. the preparation method of the pyriphenanthrenone as anti-fibrosis medicine crystal formation described in a claim 3, it is characterised in that specifically walk
Suddenly it is: pirfenidone is dissolved in the tetrahydrofuran aqueous solution that mass fraction is 10%, wherein 1g pirfenidone correspondence oxolane
The volume of aqueous solution is 2-6mL, and oil bath heated and stirred is completely dissolved to raw material, be cooled to 0-5 DEG C stand crystallize, after filtration in
30-70 DEG C is dried to obtain pirfenidone crystal formation III.
10. the preparation method of the pyriphenanthrenone as anti-fibrosis medicine crystal formation described in a claim 3, it is characterised in that specifically walk
Suddenly it is: pirfenidone is dissolved in the aqueous acetone solution that mass fraction is 10%, wherein 1g pirfenidone correspondence aqueous acetone solution
Volume is 4-10mL, and oil bath heated and stirred is completely dissolved to raw material, is cooled to 0-5 DEG C and stands crystallize, does in 30-70 DEG C after filtration
Dry obtain pirfenidone crystal formation III.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201610284441.8A CN105906558A (en) | 2016-05-04 | 2016-05-04 | Anti-fibrosis drug pirfenidone crystal forms and preparation method thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201610284441.8A CN105906558A (en) | 2016-05-04 | 2016-05-04 | Anti-fibrosis drug pirfenidone crystal forms and preparation method thereof |
Publications (1)
Publication Number | Publication Date |
---|---|
CN105906558A true CN105906558A (en) | 2016-08-31 |
Family
ID=56752224
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201610284441.8A Pending CN105906558A (en) | 2016-05-04 | 2016-05-04 | Anti-fibrosis drug pirfenidone crystal forms and preparation method thereof |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN105906558A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT201600071672A1 (en) * | 2016-07-08 | 2018-01-08 | Dipharma Francis Srl | METHOD FOR SYNTHESIZING AN IMMUNOSUPPRESSOR DRUG |
WO2018083709A1 (en) * | 2016-11-07 | 2018-05-11 | Msn Laboratories Private Limited, R&D Center | Improved process for the preparation of pure 5-methyl-1-phenyl-2-1 (h)-pyridone |
CN112409246A (en) * | 2019-08-21 | 2021-02-26 | 北京凯因科技股份有限公司 | Novel pirfenidone crystal form and preparation method thereof |
CN114195708A (en) * | 2021-11-30 | 2022-03-18 | 岳阳新华达制药有限公司 | Method for purifying pirfenidone |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013018685A1 (en) * | 2011-07-29 | 2013-02-07 | 東レ株式会社 | Lactam derivative and use thereof for medical purposes |
CN105315198A (en) * | 2015-11-02 | 2016-02-10 | 重庆康乐制药有限公司 | Crystal form of pirfenidone and preparation method of crystal form |
CN105330598A (en) * | 2015-12-02 | 2016-02-17 | 新发药业有限公司 | Preparing method for pirfenidone |
-
2016
- 2016-05-04 CN CN201610284441.8A patent/CN105906558A/en active Pending
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013018685A1 (en) * | 2011-07-29 | 2013-02-07 | 東レ株式会社 | Lactam derivative and use thereof for medical purposes |
CN105315198A (en) * | 2015-11-02 | 2016-02-10 | 重庆康乐制药有限公司 | Crystal form of pirfenidone and preparation method of crystal form |
CN105330598A (en) * | 2015-12-02 | 2016-02-17 | 新发药业有限公司 | Preparing method for pirfenidone |
Non-Patent Citations (1)
Title |
---|
郭成: "吡非尼酮的合成及结构确证", 《安徽医药》 * |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT201600071672A1 (en) * | 2016-07-08 | 2018-01-08 | Dipharma Francis Srl | METHOD FOR SYNTHESIZING AN IMMUNOSUPPRESSOR DRUG |
WO2018083709A1 (en) * | 2016-11-07 | 2018-05-11 | Msn Laboratories Private Limited, R&D Center | Improved process for the preparation of pure 5-methyl-1-phenyl-2-1 (h)-pyridone |
CN112409246A (en) * | 2019-08-21 | 2021-02-26 | 北京凯因科技股份有限公司 | Novel pirfenidone crystal form and preparation method thereof |
CN112409246B (en) * | 2019-08-21 | 2023-04-07 | 北京凯因科技股份有限公司 | Crystal form of pirfenidone and preparation method thereof |
CN114195708A (en) * | 2021-11-30 | 2022-03-18 | 岳阳新华达制药有限公司 | Method for purifying pirfenidone |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN105906558A (en) | Anti-fibrosis drug pirfenidone crystal forms and preparation method thereof | |
CN101412700B (en) | Crystal form and preparation of febuxostat | |
CN105237504B (en) | Nitrogenous analog derivative of myricetin and its preparation method and application | |
CN104603123B (en) | Solid-state form of bent Ge Lieting and its production and use | |
CN103348923A (en) | High water-absorbing straw cat litter | |
CN104788438A (en) | B crystal form of empagliflozin and preparation of B crystal form | |
CN104230923A (en) | Method for preparing 2,3-dihydro-1H-pyrrolo pyridine hydrochloride | |
CN101559074B (en) | Coccidiostat-decoquinate dry suspension for livestock and poultry and preparation method thereof | |
CN104945385A (en) | Novel crystal form of Tipracil hydrochloride and preparation method thereof | |
CN101891671B (en) | Crystals of carvidilol dihydric phosphate and preparation method thereof | |
CN104628723A (en) | Banisterine benzoyl urea compounds and preparation method and application thereof | |
CN104119282B (en) | The decolouring of a kind of Fluoxastrobin and method of purification | |
CN102265831A (en) | Botanical pesticide Chamaejasmine A suspension and preparation method thereof | |
CN101928260B (en) | Febuxostat new crystal form R and preparation method thereof | |
CN106478636B (en) | Ticagrelor crystal form and preparation method | |
CN102477041A (en) | Preparation method of cepharanthine hydrochloride | |
CN101602764B (en) | Method for preparing acyclovir 2/3 hydrate | |
CN104151242B (en) | Dihydro-isoquinoline compounds and the purposes in preparing neuroprotective or antidepressant drug thereof | |
CN102775405B (en) | High-solubility doxofylline compound | |
CN102718722B (en) | The novel fragrant phenoxy ramification of carboxylic esters preparations and applicatio research that a kind of water oil is double molten | |
CN102058585B (en) | Application of Rhodanine derivates as antineoplastic medicine | |
CN105218560A (en) | The synthesis technique of 7-bromo-4-diuril phenol also [3,2-D] pyrimidine | |
CN109336801A (en) | A kind of doxercalciferol derivative and preparation method thereof | |
CN105461716B (en) | Two NK007 optical pure isomers and synthesis and application thereof | |
CN104829497B (en) | A kind of biguanide compound and its preparation method and application |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
WD01 | Invention patent application deemed withdrawn after publication | ||
WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20160831 |