CN108191759A - A kind of gliquidone crystal, preparation method and the drug containing this crystal - Google Patents
A kind of gliquidone crystal, preparation method and the drug containing this crystal Download PDFInfo
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- CN108191759A CN108191759A CN201711478166.4A CN201711478166A CN108191759A CN 108191759 A CN108191759 A CN 108191759A CN 201711478166 A CN201711478166 A CN 201711478166A CN 108191759 A CN108191759 A CN 108191759A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
- C07D217/24—Oxygen atoms
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- 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
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Abstract
The present invention provides a kind of gliquidone crystal,Preparation method and the drug containing this crystal,Gliquidone crystal is A crystal forms,B crystal form or C crystal form,It is measured using powder x-ray diffraction measuring method,The X-ray powder diffraction pattern represented with the 2 θ ± 0.20 ° angles of diffraction,The collection of illustrative plates of A crystal forms is at 10.60 °,14.00°,16.10°,18.98°,Diffraction maximum is shown at 20.24 ° and 21.46 °,The collection of illustrative plates of B crystal form is at 10.60 °,14.00°,15.30°,16.10°,16.54°,17.54°,18.53°,18.98°,19.33°,20.24°,21.46°,Diffraction maximum is shown at 23.24 ° and 25.35 °,The collection of illustrative plates of C crystal form is at 10.70 °,15.24°,18.48°,Diffraction maximum is shown at 23.24 ° and 24.74 °.Preparation method includes：Gliquidone crude product is dissolved in solvent, then crystallization obtains gliquidone crystal.The invention discloses the crystal structures of gliquidone, the gliquidone of crystal state is than the gliquidone compound dissolubility higher of unformed state, storage stability is stronger, gliquidone crystal purity that the preparation method obtains is high, yield is high, preparation process is simple, it is reproducible, suitable for industrialized production.
Description
Technical field
The invention belongs to medicinal chemistry arts, more particularly, to a kind of gliquidone crystal, preparation method and contain this
The drug of crystal.
Background technology
Gliquidone, chemical name：[[[(3,4 pairs of hydrogen -7- methoxyl group -4,4- dimethyl -1,3- are bis- by 2- by 9- by 1- cyclohexyl -3-
Oxygroup -2- (1H)-isoquinolyl)-ethyl] phenyl] sulfonyl] urea.Its structural formula such as following formula：
The gliquidone system second generation takes orally sulfonylureas drugs for diabetes, is high activity parent's beta Cell of islet agent, with beta Cell of islet film
On specific receptor combine, can induce and generate appropriate insulin, to reduce blood sugar concentration.Oral this product reaches after 2~2.5 hours
Highest blood concentration is completely absorbed quickly.Plasma half-life is 1.5 hours, and metabolism is complete, and metabolite does not have drop
Blood glucose acts on, and the metabolite overwhelming majority is drained through biliary tract digestive system.
The only pertinent literature of unformed state gliquidone on the books and unformed state gliquidone in the prior art
The preparation method of compound, the not research about gliquidone crystal form.The method for preparing gliquidone in the prior art obtains
Gliquidone purity it is not high, and stability is poor during the gliquidone powder storage of unformed state, and safety is not high.
Invention content
The problem to be solved in the present invention is to provide a kind of gliquidone crystal, preparation method and the medicine containing this crystal
Object, reproducible, easy to operate, product yield and purity are high, are suitble to industrialized production.
In order to solve the above technical problems, the technical solution adopted by the present invention is：A kind of gliquidone crystal, gliquidone are brilliant
Body is A crystal forms, B crystal form or C crystal form, is measured using powder x-ray diffraction measuring method, is penetrated with the X that the 2 θ ± 0.20 ° angles of diffraction represent
Line powder diffraction spectrum, the collection of illustrative plates of A crystal forms are shown at 10.60 °, 14.00 °, 16.10 °, 18.98 °, 20.24 ° and 21.46 °
Diffraction maximum, the collection of illustrative plates of B crystal form 10.60 °, 14.00 °, 15.30 °, 16.10 °, 16.54 °, 17.54 °, 18.53 °, 18.98 °,
Show diffraction maximum at 19.33 °, 20.24 °, 21.46 °, 23.24 ° and 25.35 °, the collection of illustrative plates of C crystal form 10.70 °, 15.24 °,
Diffraction maximum is shown at 18.48 °, 23.24 ° and 24.74 °.
In technical solution, it is preferred that the collection of illustrative plates of B crystal form also shows diffraction maximum at 14.48 °, 24.17 ° and 24.62 °.
It is a further object of the present invention to provide the method for preparing above-mentioned gliquidone crystal, including：By gliquidone crude product
It dissolves in solvent, then crystallization obtains gliquidone crystal.
In technical solution, it is preferred that gliquidone crystal is A crystal forms, and the solvent of dissolving gliquidone crude product is acetonitrile.
In technical solution, it is preferred that gliquidone crystal is B crystal form, and the solvent of dissolving gliquidone crude product is acetic acid second
One or more mixing in ester, isopropyl ether, dichloromethane and tetrahydrofuran.
In technical solution, it is preferred that gliquidone crystal is C crystal form, and the solvent of dissolving gliquidone crude product is ethyl alcohol.
In technical solution, it is preferred that the temperature in Crystallization Process is -10-25 DEG C, it is preferred that the temperature in Crystallization Process
It it is -5-15 DEG C, it is furthermore preferred that the temperature in Crystallization Process is 0-5 DEG C.
In technical solution, it is preferred that be heated to reflux lower dissolving gliquidone crude product.
In technical solution, it is preferred that the crystallization time is 3-8 hours, it is preferred that the crystallization time is 3~5 hours, more preferably
, the crystallization time is 4 hours.
It is yet another object of the invention to provide the drug containing above-mentioned gliquidone crystal, above-mentioned lattice row quinoline is contained in drug
Ketone crystal and pharmaceutically acceptable pharmaceutic adjuvant.
The invention makes public for the first time the crystal structure of gliquidone, gliquidone crystal and existing unformed state
Gliquidone compound is compared, and dissolubility is more preferable, and the stability higher during storing can be prepared pure using the above method
The very high gliquidone crystal of degree, isoquinolin object are no more than 0.6%, and reproducible, easy to operate, product yield high, are suitble to
Industrialized production.
Description of the drawings
Fig. 1 is the XRPD collection of illustrative plates for the gliquidone crystal being prepared in the embodiment of the present invention one, two, three, four.
Fig. 2 is the XRPD data for the gliquidone crystal being prepared in the embodiment of the present invention one, two, three, four.
Fig. 3 is the XRPD collection of illustrative plates for the gliquidone crystal being prepared in the embodiment of the present invention five.
Fig. 4 is the XRPD data for the gliquidone crystal being prepared in the embodiment of the present invention five.
Fig. 5 is the XRPD collection of illustrative plates for the gliquidone crystal being prepared in the embodiment of the present invention six.
Fig. 6 is the XRPD data for the gliquidone crystal being prepared in the embodiment of the present invention six.
Fig. 7 is the XRPD collection of illustrative plates for the gliquidone crystal being prepared in the embodiment of the present invention seven.
Fig. 8 is the XRPD data for the gliquidone crystal being prepared in the embodiment of the present invention seven.
Fig. 9 is the XRPD collection of illustrative plates for the gliquidone crystal being prepared in the embodiment of the present invention eight.
Figure 10 is the XRPD data for the gliquidone crystal being prepared in the embodiment of the present invention eight.
Figure 11 is the XRPD collection of illustrative plates for the gliquidone crystal being prepared in the embodiment of the present invention nine.
Figure 12 is the XRPD data for the gliquidone crystal being prepared in the embodiment of the present invention nine.
Specific embodiment
The specific embodiment of the present invention is described further with reference to embodiment：
The gliquidone crude product used in following preparation process is commercially available gliquidone compound, and XRPD collection of illustrative plates makes
It tests to obtain with powder x-ray diffraction, the purity data of gliquidone compound is analyzed to obtain by HPLC, in existing literature has
The method that HPLC disclosed in many kinds analyzes gliquidone purity.
Embodiment one
The method that gliquidone crystal is prepared used by the present embodiment is as follows：
10g gliquidones crude product is taken to add in there-necked flask, adds in 20g acetonitriles, opens stirring and heating.Heating makes its time
Stream, maintains the reflux under state, and acetonitrile is slowly added dropwise to being completely dissolved (about adding 23g can be completely dissolved), after dissolving completely,
Continue reflux 2 hours, then filter while hot, brine ice reduces temperature to 0-5 DEG C, then keeps the temperature crystallization 4 hours, and filtering obtains
Forced air drying 6-8 hours of 50-60 DEG C of solid convection oven, obtain off-white powder 9.1g, yield 91%, gliquidone crystal form is pure
It is 98.5% to spend, and isoquinolin object is no more than 0.6%, Fig. 1 schemes for its XRPD, and Fig. 2 is its XRPD data, by XRPD collection of illustrative plates and its number
According to result as can be seen that obtained gliquidone crystal form be A crystal forms, collection of illustrative plates 2 θ for 10.58 °, 13.88 °, 16.20 °,
Diffraction maximum is shown at 18.94 °, 20.20 ° and 21.32 °.
Embodiment two
The method that gliquidone crystal is prepared used by the present embodiment is as follows：
10g gliquidones is taken to add in there-necked flask, add in 20g acetonitriles, open stirring and heating.Heating makes its reflux, protects
It holds under reflux state, acetonitrile is slowly added dropwise to being completely dissolved (about adding 23g can be completely dissolved), after dissolving completely, continues
Reflux 2 hours, is then filtered while hot, and brine ice reduces temperature to 0~5 DEG C, then keeps the temperature crystallization 6 hours, filtering, what is obtained consolidates
The forced air drying 6~8 hours of 50~60 DEG C of body convection oven.Obtain off-white powder 9.0g, yield 90%, gliquidone crystal form purity
It is 98.3%, isoquinolin object is no more than 0.6%, Fig. 1 schemes for its XRPD, and Fig. 2 is its XRPD data, by XRPD collection of illustrative plates and its data
As a result as can be seen that obtained gliquidone crystal form be A crystal forms, collection of illustrative plates 2 θ for 10.58 °, 13.88 °, 16.20 °,
Diffraction maximum is shown at 18.94 °, 20.20 ° and 21.32 °.
Embodiment three
The method that gliquidone crystal is prepared used by the present embodiment is as follows：
10g gliquidones is taken to add in there-necked flask, add in 20g acetonitriles, open stirring and heating.Heating makes its reflux, protects
It holds under reflux state, acetonitrile is slowly added dropwise to being completely dissolved (about adding 23g can be completely dissolved), after dissolving completely, continues
Reflux 2 hours, is then filtered while hot, and brine ice reduces temperature to 0~5 DEG C, then keeps the temperature crystallization 4 hours, filtering, what is obtained consolidates
The forced air drying 6~8 hours of 60~70 DEG C of body convection oven.Obtain off-white powder 9.1g, yield 91%, gliquidone crystal form purity
It is 98.2%, isoquinolin object is no more than 0.6%, Fig. 1 schemes for its XRPD, and Fig. 2 is its XRPD data, by XRPD collection of illustrative plates and its data
As a result as can be seen that obtained gliquidone crystal form be A crystal forms, collection of illustrative plates 2 θ for 10.58 °, 13.88 °, 16.20 °,
Diffraction maximum is shown at 18.94 °, 20.20 ° and 21.32 °.
Example IV
The method that gliquidone crystal is prepared used by the present embodiment is as follows：
10g gliquidones is taken to add in there-necked flask, add in 20g acetonitriles, open stirring and heating.Heating makes its reflux, protects
It holds under reflux state, acetonitrile is slowly added dropwise to being completely dissolved (about adding 23g can be completely dissolved), after dissolving completely, continues
Reflux 2 hours, is then filtered while hot, and brine ice reduces temperature to 20~25 DEG C, then keeps the temperature crystallization 4 hours, and filtering obtains
The forced air drying 6~8 hours of 50~70 DEG C of solid convection oven.Off-white powder 8.9g, yield 89%, gliquidone crystal form is pure
It is 98.4% to spend, and isoquinolin object is no more than 0.61%, Fig. 1 schemes for its XRPD, and Fig. 2 is its XRPD data, by XRPD collection of illustrative plates and its
The gliquidone crystal form that data result can be seen that be A crystal forms, collection of illustrative plates 2 θ for 10.58 °, 13.88 °, 16.20 °,
Diffraction maximum is shown at 18.94 °, 20.20 ° and 21.32 °.
Embodiment five
The method that gliquidone crystal is prepared used by the present embodiment is as follows：
10g gliquidones is taken to add in there-necked flask, add in 20g ethyl acetate, open stirring and heating.Heating makes its time
Stream, maintains the reflux under state, ethyl acetate is slowly added dropwise to (about adding 38g can be completely dissolved) is completely dissolved, has dissolved
Quan Hou continues reflux 2 hours, then filters while hot, and brine ice reduces temperature to 0~5 DEG C, then keeps the temperature crystallization 4 hours, mistake
Filter, the forced air drying 6~8 hours of 50~60 DEG C of obtained solid convection oven.Obtain off-white powder 7.2g, yield 72%, lattice row
Quinoline ketone crystal form purity is 98.7%, and isoquinolin object is no more than 0.6%, Fig. 3 schemes for its XRPD, and Fig. 4 is its XRPD data, by XRPD
The gliquidone crystal form that collection of illustrative plates and its data result can be seen that be B crystal form, collection of illustrative plates 2 θ for 10.52 °, 13.98 °,
15.30°、16.24°、16.55°、17.54°、18.48°、18.98°、19.32°、20.24°、21.46°、23.24°、25.38°
Place shows strong diffraction maximum, and stronger diffraction maximum is shown at 14.44 °, 24.16 °, 24.64 °.
Embodiment six
The method that gliquidone crystal is prepared used by the present embodiment is as follows：
10g gliquidones is taken to add in there-necked flask, add in 20g isopropyl ethers, open stirring and heating.Heating makes its reflux,
It maintains the reflux under state, isopropyl ether is slowly added dropwise to being completely dissolved (about adding 15g can be completely dissolved), after dissolving completely,
Continue reflux 2 hours, then filter while hot, brine ice reduces temperature to 0~5 DEG C, then keeps the temperature crystallization 4 hours, and filtering obtains
The forced air drying 6~8 hours of 50~60 DEG C of solid convection oven.Obtain off-white powder 7.5g, yield 75%, gliquidone crystal form
Purity is 98.6%, and isoquinolin object is no more than 0.6%, Fig. 5 schemes for its XRPD, and Fig. 6 is its XRPD data, by XRPD collection of illustrative plates and its
The gliquidone crystal form that data result can be seen that be B crystal form, collection of illustrative plates 10.70 °, 14.06 °, 15.40 °,
It is shown at 15.90 °, 16.54 °, 17.62 °, 18.56 °, 19.08 °, 19.4 °, 20.32 °, 21.54 °, 23.32 °, 25.46 ° strong
Diffraction maximum, and stronger diffraction maximum is shown at 14.62 °, 24.22 °, 24.70 °.
Embodiment seven
The method that gliquidone crystal is prepared used by the present embodiment is as follows：
10g gliquidones is taken to add in there-necked flask, add in 20g dichloromethane, open stirring and heating.Heating makes its time
Stream, maintains the reflux under state, dichloromethane is slowly added dropwise to (about adding 60g can be completely dissolved) is completely dissolved, has dissolved
Quan Hou continues reflux 2 hours, then filters while hot, and brine ice reduces temperature to 0~5 DEG C, then keeps the temperature crystallization 4 hours, mistake
Filter, the forced air drying 6~8 hours of 50~60 DEG C of obtained solid convection oven.Obtain off-white powder 8.1g, yield 81%, lattice row
Quinoline ketone crystal form purity is 98.5%, and isoquinolin object is no more than 0.6%, Fig. 7 schemes for its XRPD, and Fig. 8 is its XRPD data, by XRPD
The gliquidone crystal form that collection of illustrative plates and its data result can be seen that be B crystal form, collection of illustrative plates 10.52 °, 13.88 °,
15.20°、15.88°、16.48°、17.42°、18.58°、18.85°、19.24°、20.12°、21.34°、23.12°、25.26°
Place shows strong diffraction maximum, and stronger diffraction maximum is shown at 14.36 °, 24.10 °, 24.52 °.
Embodiment eight
The method that gliquidone crystal is prepared used by the present embodiment is as follows：
10g gliquidones is taken to add in there-necked flask, add in 20g tetrahydrofurans, open stirring and heating.Heating makes its time
Stream, maintains the reflux under state, tetrahydrofuran is slowly added dropwise to (about adding 30g can be completely dissolved) is completely dissolved, has dissolved
Quan Hou continues reflux 2 hours, then filters while hot, and brine ice reduces temperature to 0~5 DEG C, then keeps the temperature crystallization 4 hours, mistake
Filter, the forced air drying 6~8 hours of 50~60 DEG C of obtained solid convection oven.Obtain off-white powder 6.7g, yield 67%, lattice row
Quinoline ketone crystal form purity is 98.8%, and isoquinolin object is no more than 0.5%, Fig. 9 schemes for its XRPD, and Figure 10 is its XRPD data, by
The gliquidone crystal form that XRPD collection of illustrative plates and its data result can be seen that is B crystal form, collection of illustrative plates is 10.64,14.00,
15.32nd, display is strong at 16.26,16.58,17.59,18.50,19.02,19.34,20.26,21.48,23.26,25.30 spreads out
Peak is penetrated, and stronger diffraction maximum is shown at 14.48,24.18,24.66.
Embodiment nine
The method that gliquidone crystal is prepared used by the present embodiment is as follows：
10g gliquidones is taken to add in there-necked flask, add in 20g ethyl alcohol, open stirring and heating.Heating makes its reflux, protects
It holds under reflux state, ethyl alcohol is slowly added dropwise to being completely dissolved (about adding 15g can be completely dissolved), after dissolving completely, continues
Reflux 2 hours, is then filtered while hot, and brine ice reduces temperature to 0~5 DEG C, then keeps the temperature crystallization 4 hours, filtering, what is obtained consolidates
The forced air drying 6~8 hours of 50~60 DEG C of body convection oven.Obtain off-white powder 4.5g, yield 45%, gliquidone crystal form purity
It is 98.5%, isoquinolin object is no more than 0.6%, Figure 11 schemes for its XRPD, and Figure 12 is its XRPD data, by XRPD collection of illustrative plates and its number
According to result as can be seen that obtained gliquidone crystal form is C crystal form, collection of illustrative plates 10.70,15.24,18.48,23.24,
Strong diffraction maximum is shown at 24.74.
Several embodiments of the present invention are described in detail above, but the content is only the preferable implementation of the present invention
Example, it is impossible to be construed as limiting the practical range of the present invention.All all the changes and improvements made according to the present patent application range
Deng, should all still belong to the present invention patent covering scope within.
Claims (10)
1. a kind of gliquidone crystal, it is characterised in that：The gliquidone crystal is A crystal forms, B crystal form or C crystal form, uses powder
Last X-ray diffraction measure method measures, with the X-ray powder diffraction pattern that the 2 θ ± 0.20 ° angles of diffraction represent, the figure of the A crystal forms
Spectrum shows diffraction maximum at 10.60 °, 14.00 °, 16.10 °, 18.98 °, 20.24 ° and 21.46 °, and the collection of illustrative plates of the B crystal form exists
10.60°、14.00°、15.30°、16.10°、16.54°、17.54°、18.53°、18.98°、19.33°、20.24°、21.46°、
Show diffraction maximum at 23.24 ° and 25.35 °, the collection of illustrative plates of the C crystal form at 10.70 °, 15.24 °, 18.48 °, 23.24 ° and
Diffraction maximum is shown at 24.74 °.
2. gliquidone crystal according to claim 1, it is characterised in that：The collection of illustrative plates of the B crystal form also 14.48 °,
Diffraction maximum is shown at 24.17 ° and 24.62 °.
3. prepare the method for gliquidone crystal as claimed in claim 1 or 2, it is characterised in that：Including：Gliquidone is thick
Product are dissolved in solvent, and then crystallization obtains the gliquidone crystal.
4. the method according to claim 3 for preparing gliquidone crystal, it is characterised in that：The gliquidone crystal is
A crystal forms, the solvent for dissolving the gliquidone crude product are acetonitrile.
5. the method according to claim 3 for preparing gliquidone crystal, it is characterised in that：The gliquidone crystal is
B crystal form, the solvent for dissolving the gliquidone crude product are one kind in ethyl acetate, isopropyl ether, dichloromethane and tetrahydrofuran
Or a variety of mixing.
6. the method according to claim 3 for preparing gliquidone crystal, it is characterised in that：The gliquidone crystal is
C crystal form, the solvent for dissolving the gliquidone crude product are ethyl alcohol.
7. according to any methods for preparing gliquidone crystal of claim 3-6, it is characterised in that：In Crystallization Process
Temperature is -10-25 DEG C, it is preferred that the temperature in Crystallization Process is -5-15 DEG C, it is furthermore preferred that the temperature in Crystallization Process is 0-
5℃。
8. according to any methods for preparing gliquidone crystal of claim 3-7, it is characterised in that：In the case where being heated to reflux
Dissolve the gliquidone crude product.
9. according to any methods for preparing gliquidone crystal of claim 3-8, it is characterised in that：The crystallization time is 3-
8 hours, it is preferred that the crystallization time is 3~5 hours, it is furthermore preferred that the crystallization time is 4 hours.
10. the drug containing gliquidone crystal as claimed in claim 1 or 2.
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| CN201711478166.4A CN108191759A (en) | 2017-12-29 | 2017-12-29 | A kind of gliquidone crystal, preparation method and the drug containing this crystal |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109293570A (en) * | 2018-11-09 | 2019-02-01 | 威海迪素制药有限公司 | A kind of preparation method of the gliquidone crystallization of small grain size |
| CN115466213A (en) * | 2022-10-10 | 2022-12-13 | 山东药品食品职业学院 | Medicinal crystal form of gliquidone and preparation method thereof |
| WO2024061387A3 (en) * | 2023-12-19 | 2024-08-08 | 杭州国瑞生物科技有限公司 | Crystal form b of sodium zirconium cyclosilicate, and preparation method therefor and use thereof |
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| CN106316950A (en) * | 2015-06-29 | 2017-01-11 | 天津市亨必达化学合成物有限公司 | Gliquidone preparation method |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106316950A (en) * | 2015-06-29 | 2017-01-11 | 天津市亨必达化学合成物有限公司 | Gliquidone preparation method |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109293570A (en) * | 2018-11-09 | 2019-02-01 | 威海迪素制药有限公司 | A kind of preparation method of the gliquidone crystallization of small grain size |
| CN115466213A (en) * | 2022-10-10 | 2022-12-13 | 山东药品食品职业学院 | Medicinal crystal form of gliquidone and preparation method thereof |
| WO2024061387A3 (en) * | 2023-12-19 | 2024-08-08 | 杭州国瑞生物科技有限公司 | Crystal form b of sodium zirconium cyclosilicate, and preparation method therefor and use thereof |
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Application publication date: 20180622 |