CN103664756A - Perampanel new type crystal A and preparation method thereof - Google Patents
Perampanel new type crystal A and preparation method thereof Download PDFInfo
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- CN103664756A CN103664756A CN201310606707.2A CN201310606707A CN103664756A CN 103664756 A CN103664756 A CN 103664756A CN 201310606707 A CN201310606707 A CN 201310606707A CN 103664756 A CN103664756 A CN 103664756A
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- 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
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Abstract
The invention relates to a perampanel new type crystal A and a preparation method thereof. The new type crystal A is characterized in that an X-ray powder diffraction pattern has characteristic peaks when the 2 theta value is 7.4 plus or minus 0.2 degrees, 9.6 plus or minus 0.2 degrees, 19.2 plus or minus 0.2 degrees, 17.4 plus or minus 0.2 degrees, 15.2 plus or minus 0.2 degrees, 8.8 plus or minus 0.2 degrees, 12.0 plus or minus 0.2degrees, 22.9 plus or minus 0.2 degrees and 14.2 plus or minus 0.2 degrees.
Description
Affiliated technical field
The present invention relates to chemical field of medicaments, particularly relate to new crystal of pyrrole Lun Panai and preparation method thereof.
Background technology
Pyrrole Lun Panai (compound shown in formula I) is by Japanese Wei Cai company (Eisai) research and development, on December 22nd, 2012, obtains FDA approval for the assisting therapy of 12 years old age and above epileptic's partial seizures.Pyrrole Lun Panai is the different azoles propionic acid of alpha-amino group-3-hydroxyl-5 methyl-4-(AMPA) receptor antagonist, and it,, by suppressing postsynaptic ampa receptor glutamate activity, reduces neurone and be overexcited.This is the first antiepileptic drug with this mechanism of action of FDA approval.Its structure is as follows:
WO2013102897A1 discloses anhydrous crystal forms I, anhydrous crystal forms III, anhydrous crystal forms V and the anhydrous crystal forms VII of pyrrole Lun Panai.The X-ray powder diffraction figure of anhydrous crystal forms I is 7.840 °, 16.139 °, 9.537 °, 19.101 °, 10.301 °, 15.100 °, 20.460 °, 14.260 °, 24.238 ° in 2theta value and has characteristic peak.The X-ray powder diffraction figure of anhydrous crystal forms III is 4.7 ° ± 0.1 ° in 2theta value, 7.8 ° ± 0.1 °, 8.7 ° ± 0.1 °, 9.5 ° ± 0.1 °, 10.3 ° ± 0.1 °, 11.7 ° ± 0.1 °, 12.5 ° ± 0.1 °, 14.2 ° ± 0.1 °, 15.1 ° ± 0.1 °, 16.1 ° ± 0.1 °, 17.6 ° ± 0.1 °, 19.1 ° ± 0.1 °, 20.0 ° ± 0.1 °, 20.5 ° ± 0.1 °, 21.1 ° ± 0.1 °, 21.4 ° ± 0.1 °, 22.4 ° ± 0.1 °, 23.3 ° ± 0.1 °, 24.2 ° ± 0.1 °, 25.3 ° ± 0.1 °, 26.4 ° ± 0.1 °, 27.2 ° ± 0.1 °, locate to there is characteristic peak for 28.7 ° ± 0.1 °.The X-ray powder diffraction figure of anhydrous crystal forms V is 4.5 ° ± 0.1 °, 8.8 ° ± 0.1 °, 11.9 ° ± 0.1 °, 14.9 ° ± 0.1 °, 15.8 ° ± 0.1 °, 17.9 ° ± 0.1 °, 20.2 ° ± 0.1 °, 21.1 ° ± 0.1 °, 23.4 ° ± 0.1 °, 24.6 ° ± 0.1 °, 26.0 ° ± 0.1 °, 27.5 ° ± 0.1 °, 34.0 ° ± 0.1 ° in 2theta value and locates to have characteristic peak.The X-ray powder diffraction figure of anhydrous crystal forms VII is 4.5 ° ± 0.1 ° in 2theta value, 7.7 ° ± 0.1 °, 8.7 ° ± 0.1 °, 9.4 ° ± 0.1 °, 11.6 ° ± 0.1 °, 12.4 ° ± 0.1 °, 15.0 ° ± 0.1 °, 16.0 ° ± 0.1 °, 17.5 ° ± 0.1 °, 17.8 ° ± 0.1 °, 19.9 ° ± 0.1 °, 20.9 ° ± 0.1 °, 21.4 ° ± 0.1 °, 23.3 ° ± 0.1 °, 24.1 ° ± 0.1 °, 24.4 ° ± 0.1 °, 25.5 ° ± 0.1 °, 27.2 ° ± 0.1 °, 27.6 ° ± 0.1 °, locate to there is characteristic peak for 28.7 ° ± 0.1 °.
WO2007072868 discloses the anhydrous crystal forms IV of pyrrole Lun Panai, and its X-ray powder diffraction figure is 15.4 ° ± 0.2 °, 16.6 ° ± 0.2 °, 24.3 ° ± 0.2 ° in 2theta value and locates to have characteristic peak.
US2010/324297 discloses the hydrate crystal forms of pyrrole Lun Panai, and its X-ray powder diffraction figure is 8.7 ° ± 0.2 ° and 12.5 ° ± 0.2 ° in 2theta value and locates to have characteristic peak.
US7803818 discloses a kind of amorphous of pyrrole Lun Panai.
US7718807 discloses hydrochloride, hydrobromate, vitriol, mesylate, tosilate, benzene sulfonate, fumarate, tartrate, succinate, the benzoate of pyrrole Lun Panai.
Summary of the invention
Invention provides the new crystal of a kind of pyrrole Lun Panai, called after crystal form A in the present invention.
Further, the crystal form A of pyrrole Lun Panai provided by the invention, is characterized in that, its X-ray powder diffraction figure is 7.4 ° ± 0.2 °, 9.6 ° ± 0.2 °, 19.2 ° ± 0.2 ° in 2theta value and locates to have characteristic peak.
Further, the crystal form A of pyrrole Lun Panai provided by the invention, be further characterized in that, its X-ray powder diffraction figure is 17.4 ° ± 0.2 °, 15.2 ° ± 0.2 °, 8.8 ° ± 0.2 °, 12.0 ° ± 0.2 °, 22.9 ° ± 0.2 °, 14.2 ° ± 0.2 ° in 2theta value and locates to have characteristic peak, as shown in Figure 1.
Further, the crystal form A of pyrrole Lun Panai provided by the invention, is characterized in that, its dsc (DSC) is analyzed and to be heated to 30.1 ℃, occurs endotherm(ic)peak near 133.4 ℃ and 173.7 ℃, as shown in Figure 2.
Further, the crystal form A of pyrrole Lun Panai disclosed by the invention, when being heated to 135 ℃, has 8.3% weight loss gradient, and its thermogravimetric analysis figure (TGA) as shown in Figure 3.
Further, the preparation method of pyrrole Lun Panai crystal form A provided by the invention, it is characterized in that, its preparation method comprises the steps: the powder dissolution of pyrrole Lun Panai in the mixed solvent system of acetic acid and water, by slow volatilization, slow cooling or other crystallization method crystallizatioies, obtain crystal form A at ambient temperature.The volume ratio of described acetic acid and water is between 1:1 to 10:1, and more preferably volume ratio arrives 5:2 between 1:1.
Accompanying drawing explanation
Fig. 1 is the X-ray powder diffraction figure (X-ray powder diffraction (XRPD) figure of the crystal form A of Fig. 1 pyrrole Lun Panai) of pyrrole Lun Panai crystal form A
Fig. 2 is the means of differential scanning calorimetry figure (differential scanning calorimetric analysis (DSC) figure of the crystal form A of Fig. 2 pyrrole Lun Panai) of pyrrole Lun Panai crystal form A
Fig. 3 is the thermogravimetric analysis figure (thermogravimetric analysis (TGA) figure of the crystal form A of Fig. 3 pyrrole Lun Panai) of pyrrole Lun Panai crystal form A
Embodiment
Below will further set forth the present invention by specific embodiment, but be not limited to protection scope of the present invention.Those skilled in the art can make improvements preparation method and use instrument within the scope of claim, and these improvement also should be considered as protection scope of the present invention.Therefore, the protection domain of patent of the present invention should be as the criterion with claims.
In following embodiment, except as otherwise noted, described test method is implemented according to the condition of normal condition or manufacturer's suggestion conventionally; Shown raw material, reagent all can obtain by the mode of commercially available purchase.
X-ray powder diffraction figure of the present invention gathers on Panalytical Empyrean x-ray powder diffraction instrument.The method parameter of X-ray powder diffraction of the present invention is as follows:
X ray reflection parameter: CuKa
K α 2/K α 1 intensity: 0.50
Voltage: 45 KVs (kV)
Electric current: 40 milliampere(mA)s (mA)
Divergent slit: automatically
Scan pattern: continuously
Sweep limit: from 3.0 to 40.0 degree
Sampling step length: 0.013 degree
Every step Measuring Time: 16.32 seconds/step
Means of differential scanning calorimetry of the present invention (DSC) analysis chart gathers on TA Q2000.The method parameter that means of differential scanning calorimetry of the present invention (DSC) is analyzed is as follows:
Temperature range: room temperature-250 ℃
Scanning speed: 10 ℃/min
Shielding gas: nitrogen 50mL/min
Thermogravimetric analysis of the present invention (TGA) figure gathers on TA Q5000.The method parameter of thermogravimetric analysis of the present invention (TGA) is as follows:
Temperature range: room temperature-300 ℃
Scanning speed: 10 ℃/min
Shielding gas: nitrogen 25mL/min
Embodiment 1:
The preparation method of pyrrole Lun Panai crystal form A:
The powder of 50.1mg pyrrole Lun Panai is joined in the mixed solvent that 2.0mL acetic acid and water volume ratio are 1:1, obtain settled solution, at ambient temperature, suspend and stir this solution 1 day, centrifugation solid, vacuum-drying, after 24 hours, is collected solid and is obtained crystal form A.
Crystal form A described in above-described embodiment, is characterized in that, its X-ray powder diffraction figure is 7.4 °, 9.6 °, 19.2 °, 17.4 °, 15.2 °, 8.8 °, 12.0 °, 22.9 °, 14.2 ° in 2theta value and locates to have characteristic peak.
Embodiment 2:
The preparation method of pyrrole Lun Panai crystal form A:
The powder of 10.3mg pyrrole Lun Panai is dissolved in the mixed solvent that 0.7mL acetic acid and water volume ratio are 5:2, obtains settled solution, this solution is heated to 50 ℃, then slow cooling to 5 ℃, there is solid to separate out, vacuum-drying, after 24 hours, is collected solid and is obtained crystal form A.
Crystal form A described in above-described embodiment, is characterized in that, its X-ray powder diffraction figure is 7.4 °, 9.5 °, 19.2 °, 17.3 °, 15.2 °, 8.8 °, 12.0 °, 22.9 °, 14.2 ° in 2theta value and locates to have characteristic peak.
Embodiment 3:
The preparation method of pyrrole Lun Panai crystal form A:
The powder of 10.1mg pyrrole Lun Panai is dissolved in the mixed solvent that 0.7mL acetic acid and water volume ratio are 5:2, and the nylon film that passes through 0.22 μ m is by undissolved solid filtering, obtain saturated solution, the sample bottle that this solution is housed is sealed up to the sealed membrane of pricking hole, at ambient temperature, slowly evaporate into solid and separate out, vacuum-drying, after 24 hours, is collected solid and is obtained crystal form A.
Crystal form A described in above-described embodiment, is characterized in that, its X-ray powder diffraction figure is 7.4 °, 9.5 °, 19.2 °, 17.3 °, 15.2 °, 8.8 °, 12.0 °, 22.9 °, 14.2 ° in 2theta value and locates to have characteristic peak.
Claims (8)
1. a crystal form A of pyrrole Lun Panai, is characterized in that, is 7.4 ° ± 0.2 °, 9.6 ° ± 0.2 °, 19.2 ° ± 0.2 ° locates to have characteristic peak in its X-ray diffractogram in 2theta value.
2. crystal form A according to claim 1, be further characterized in that, its x-ray diffraction pattern is 17.4 ° ± 0.2 °, 15.2 ° ± 0.2 °, 8.8 ° ± 0.2 °, 12.0 ° ± 0.2 °, 22.9 ° ± 0.2 °, 14.2 ° ± 0.2 ° in 2theta value and locates to have characteristic peak.
3. according to the crystal form A described in claim 1 and 2, it is characterized in that, figure is substantially consistent with Fig. 1 for its X-ray powder diffraction (XRPD).
4. according to the crystal form A described in claim 1 and 2, it is characterized in that, crystal form A is acetic acid solvent compound.
5. according to the crystal form A described in claim 1 and 2, it is characterized in that the means of differential scanning calorimetry shown in accompanying drawing 2 (DSC) curve.
6. according to the crystal form A described in claim 1 and 2, it is characterized in that the thermogravimetric analysis shown in accompanying drawing 3 (TGA) curve.
7. a preparation method for pyrrole Lun Panai crystal form A, is characterized in that, by the dissolution of solid of pyrrole Lun Panai, in the mixed solvent system of acetic acid and water, logical slow volatilization, slow cooling or other crystallization method crystallizatioies, obtain crystal form A at ambient temperature.
8. mixed solvent according to claim 7, the volume ratio of described acetic acid and water between 1:1 to 10:1, more preferably volume ratio between 1:1 to 5:2.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310606707.2A CN103664756A (en) | 2013-11-26 | 2013-11-26 | Perampanel new type crystal A and preparation method thereof |
| CN201410468289.XA CN104292153B (en) | 2013-11-26 | 2014-09-15 | Pyrrole Lun Panai crystal formation A and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310606707.2A CN103664756A (en) | 2013-11-26 | 2013-11-26 | Perampanel new type crystal A and preparation method thereof |
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| CN103664756A true CN103664756A (en) | 2014-03-26 |
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| CN201310606707.2A Pending CN103664756A (en) | 2013-11-26 | 2013-11-26 | Perampanel new type crystal A and preparation method thereof |
| CN201410468289.XA Expired - Fee Related CN104292153B (en) | 2013-11-26 | 2014-09-15 | Pyrrole Lun Panai crystal formation A and preparation method thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016172333A1 (en) | 2015-04-21 | 2016-10-27 | Teva Pharmaceuticals International Gmbh | A solid state form of perampanel |
| CN107304183A (en) * | 2016-04-20 | 2017-10-31 | 扬子江药业集团上海海尼药业有限公司 | Pyrrole Lun Panai crystal formations and its production and use |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115745876A (en) * | 2022-11-01 | 2023-03-07 | 南京海纳医药科技股份有限公司 | Preparation method of Perampanel |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1300396B1 (en) * | 2000-06-12 | 2009-01-14 | Eisai R&D Management Co., Ltd. | 1,2-dihydropyridine compounds, process for preparation of the same and use thereof |
| MY148809A (en) * | 2004-07-06 | 2013-05-31 | Eisai R&D Man Co Ltd | Crystals of 1,2-dihydropyridine compound and their production process |
| CN101304970A (en) * | 2005-12-21 | 2008-11-12 | 卫材R&D管理有限公司 | Amorphous form of 1,2-dihydropyridine compound |
| JPWO2007072868A1 (en) * | 2005-12-21 | 2009-06-04 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | Crystals of 1,2-dihydropyridine compounds (type IV) |
| US7718807B2 (en) * | 2006-04-28 | 2010-05-18 | Eisai R&D Management Co., Ltd. | Salt of 1,2-dihydropyridine compound |
| US9096574B2 (en) * | 2012-01-03 | 2015-08-04 | Mapi Pharma Ltd. | Polymorphs of perampanel |
-
2013
- 2013-11-26 CN CN201310606707.2A patent/CN103664756A/en active Pending
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2014
- 2014-09-15 CN CN201410468289.XA patent/CN104292153B/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016172333A1 (en) | 2015-04-21 | 2016-10-27 | Teva Pharmaceuticals International Gmbh | A solid state form of perampanel |
| CN107304183A (en) * | 2016-04-20 | 2017-10-31 | 扬子江药业集团上海海尼药业有限公司 | Pyrrole Lun Panai crystal formations and its production and use |
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| Publication number | Publication date |
|---|---|
| CN104292153B (en) | 2017-03-01 |
| CN104292153A (en) | 2015-01-21 |
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Application publication date: 20140326 |