CN104356121A - Crystal form B of 1-(beta-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl] benzene and preparation method of crystal form B - Google Patents

Crystal form B of 1-(beta-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl] benzene and preparation method of crystal form B Download PDF

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Publication number
CN104356121A
CN104356121A CN201410542984.6A CN201410542984A CN104356121A CN 104356121 A CN104356121 A CN 104356121A CN 201410542984 A CN201410542984 A CN 201410542984A CN 104356121 A CN104356121 A CN 104356121A
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China
Prior art keywords
crystal form
methyl
glucopyranosyl
fluorophenyl
benzene
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CN201410542984.6A
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Inventor
陈敏华
张炎锋
杨朝惠
陆飞
张晓宇
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Crystal Pharmatech Co Ltd
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Crystal Pharmatech Co Ltd
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Priority to CN201410542984.6A priority Critical patent/CN104356121A/en
Priority to EP14862830.8A priority patent/EP3068779A4/en
Priority to JP2016530967A priority patent/JP2016536321A/en
Priority to US15/035,751 priority patent/US20160280731A1/en
Priority to PCT/IB2014/003013 priority patent/WO2015071761A2/en
Publication of CN104356121A publication Critical patent/CN104356121A/en
Pending legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings

Abstract

The invention relates to a crystal form B of 1-(beta-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl] benzene and a preparation method of the crystal form B. The crystal form B is characterized in that an X-ray powder diffraction pattern has characteristic peaks when a 2 theta value is in ranges of 6.3 degrees plus or minus 0.2 degrees, 9.4 degrees plus or minus 0.2 degrees, 12.6 degrees plus or minus 0.2 degrees, 19.9 degrees plus or minus 0.2 degrees, 11.7 degrees plus or minus 0.2 degrees and 16.9 degrees plus or minus 0.2 degrees. Compared with the prior art, the solubility of the crystal form B is improved; further, the crystal form B has good stability, and long-term storage of medicine is facilitated; and the preparation method is simple to operate, cost control in technological production is facilitated, and the crystal form has very high economic values.

Description

Crystal form B of 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] benzene and preparation method thereof
Technical field
The present invention relates to chemical medicine, particularly relate to crystal formation of 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] benzene and preparation method thereof.
Background technology
1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] benzene (compound shown in formula I), have another name called Kan Gelie clean, researched and developed by the Janssen Pharmaceutica of Subsidiary Company of Johnson & Johnson's pharmacy (Johnson & Johnson), obtaining on March 29th, 2013 hypoglycemic drug that FDA ratifies to be used for the treatment of type II diabetes, is first sodium glucose co-transporter 2 white 2 (SGLT2) inhibitor of FDA approval.SGLT2 inhibitor can specificity suppress kidney to the heavily absorption of glucose, makes excessive glucose discharge from urine thus directly reduce glucose level.The structure of this drug molecule is as follows:
As everyone knows, the different crystal forms of same medicine often causes drug solubility there are differences, and can cause the difference of drug dissolution and bioavailability, thus affects medicine absorbing in vivo, then makes curative effect of medication produce difference.Therefore, can one of matter of utmost importance paid close attention to when the solubleness of different crystal forms is dosage form selection in drug development be also one of medicine key that effectively absorb.Many medicines are often insoluble in water, thus by screening different crystal formations improve solubleness, thus improve its bioavailability and curative effect significant.
Patent CN101573368B discloses the clean semihydrate crystal formation of Kan Gelie.This crystal formation is finally used to suitability for industrialized production.
Patent CN101801371B discloses the clean crystal formation of Kan Gelie and crystallization method thereof, and the crystallization method step described in the document is more, and needs to carry out under the condition of argon shield.
Patent CN103889429A discloses the clean eutectic with L-PROLINE, D-PROLINE, L-Phe of Kan Gelie and amorphous, and this patent mainly describes Kan Gelie only and the eutectic that formed of other various assistant agents and crystallization method thereof.
The present inventor, in process of experimental, finds that Kan Gelie also exists another crystal formation only, is different from existing disclosed crystal formation.Surprisingly, this crystal formation, compared with the crystal formation of semihydrate disclosed in patent CN101573368B, has higher dissolving and more spends, and is conducive to improving bioavailability and curative effect of medication.Further, crystal formation of the present invention has satisfactory stability, and the long storage periods being conducive to medicine is placed.Preparation method is simple to operate, is conducive to the cost control in suitability for industrialized production, has high economic worth.
Summary of the invention
An object of the present invention is to provide the crystal formation of a kind of 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] benzene, called after crystal form B in the present invention.
On the one hand, the crystal form B of 1-provided by the invention (β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] benzene, it is characterized in that, its X-ray powder diffraction figure is that 6.3 ° ± 0.2 °, 9.4 ° ± 0.2 °, 12.6 ° ± 0.2 °, 19.9 ° ± 0.2 °, 11.7 ° ± 0.2 °, 16.9 ° ± 0.2 ° place has characteristic peak in 2theta value.
Further, the crystal form B of 1-provided by the invention (β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] benzene, be further characterized in that, its X-ray powder diffraction figure is that 18.2 ° ± 0.2 °, 22.3 ° ± 0.2 °, 24.4 ° ± 0.2 °, 28.9 ° ± 0.2 ° place has characteristic peak in 2theta value.
Further, the crystal form B of 1-provided by the invention (β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] benzene, is further characterized in that, its X-ray powder diffraction figure is basic consistent with Fig. 1.
On the other hand, the crystal form B of 1-provided by the invention (β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] benzene, it is characterized in that, near being heated to 86.2 DEG C, occur endotherm(ic)peak, its differential scanning calorimetric thermogram is basic consistent with Fig. 2.
On the other hand, the crystal form B of 1-provided by the invention (β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] benzene, is characterized in that, be heated to the weightlessness that 100 DEG C have about 2.95%.Its thermogravimetric analysis figure is substantially consistent with Fig. 3.
Another object of the present invention is to provide the preparation method of the crystal form B of 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] benzene, it is characterized in that, its preparation method comprises the steps: the powder dissolution of 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] benzene in the mixed solvent system of water and organic solvent, filter to obtain settled solution, obtained by the crystallization method slowly volatilizing, lower the temperature.
Further, described mixed solvent, the volume ratio of water and organic solvent between 1:10 to 10:1, more preferably volume ratio 1:1.
Further, described organic solvent includes but not limited to methyl alcohol, ethanol, Virahol, acetonitrile, acetone, tetrahydrofuran (THF), is preferably ethanol, tetrahydrofuran (THF).
Another object of the present invention is to provide a kind of 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-the fluorophenyl)-2-thienyl methyl] crystal form B of benzene and the pharmaceutical composition of pharmaceutical excipient that comprise effective therapeutic dose.Be generally the crystal form B of 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-the fluorophenyl)-2-thienyl methyl] benzene for the treatment of significant quantity is mixed with one or more pharmaceutical excipients or contacted make pharmaceutical composition or preparation, this pharmaceutical composition or preparation are prepared in the mode known in pharmacy field.
Further, in pharmaceutical composition of the present invention, the crystal form B of 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] benzene can be used for the purposes prepared in the hypoglycemic pharmaceutical preparation for the treatment of type II diabetes.
Beneficial effect of the present invention is:
Crystal formation provided by the invention, compared with prior art, solubleness is higher, for raising drug effect, reduces medicine carrying capacity and is significant.
Crystal formation provided by the invention, has satisfactory stability, and the long storage periods being conducive to medicine is placed.Further, preparation method is simple to operate, reproducible, and yield is high, is conducive to the cost control in suitability for industrialized production, has high economic worth.
Accompanying drawing explanation
Fig. 1 is the XRPD figure of the crystal form B of 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] benzene
Fig. 2 is the DSC figure of the crystal form B of 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] benzene
Fig. 3 is the TGA figure of the crystal form B of 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] benzene
Fig. 4 be 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] benzene crystal form B stability test XRPD comparison diagram (upper figure be crystal form B place before XRPD figure, figure below be crystal form B at 25 DEG C, place the figure of the XRPD after 30 days under 60% relative humidities)
embodiment
Below will set forth the present invention further 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 in right, 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, the described test method condition that conveniently conditioned disjunction manufacturer advises usually is implemented; Shown raw material, reagent all obtain by the mode of commercially available purchase.
Being explained as follows of abbreviation used in the present invention:
XRPD:X ray powder diffraction
DSC: differential scanning calorimetric analysis
TGA: thermogravimetric analysis
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: Cu, K α
1.540598； 1.544426
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
Differential scanning calorimetric analysis of the present invention (DSC) figure gathers on TA Q2000.The present invention
The method parameter of described differential scanning calorimetric analysis (DSC) is as follows:
Temperature range/DEG C: room temperature-120 DEG C
Scanning speed/DEG C/min: 10 DEG C/min
Shielding gas: nitrogen 50 ml/min
Thermogravimetric analysis (TGA) figure in the present invention described in embodiment gathers on TA Q5000.
The method parameter of described thermogravimetric analysis (TGA) is as follows:
Temperature range: room temperature-300 DEG C
Scanning speed: 10 DEG C/min
Shielding gas: nitrogen 25 ml/min
Embodiment 1
The preparation of the crystal form B of 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] benzene:
The powder of 10.6mg1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] benzene is dissolved in ethanol: in the mixed system of water=1:1 (v:v), and by the nylon leaching film of 0.45 micron by undissolved solid filtering, slowly evaporate into solid at ambient temperature to separate out, collect solid and namely obtain crystal form B.The X-ray powder diffraction data of the crystal form B that the present embodiment obtains are as shown in table 1.
As shown in Figure 1, as shown in Figure 2, thermogravimetric analysis (TGA) figure as shown in Figure 3 for differential scanning calorimetric analysis (DSC) figure for its X-ray powder diffraction (XRPD) figure.
The X-ray powder diffraction data of table 1 crystal form B
2theta D interval Intensity %
3.79 23.34 4.05
6.26 14.11 100.00
6.66 13.26 4.82
7.33 12.06 4.32
9.43 9.38 47.40
10.55 8.39 4.36
11.80 7.50 12.13
12.60 7.02 34.31
13.78 6.42 8.24
14.68 6.04 6.80
15.05 5.89 6.09
15.33 5.78 6.80
15.79 5.61 17.32
16.88 5.25 8.28
17.49 5.07 10.62
17.74 5.00 11.46
18.20 4.88 9.95
18.36 4.83 7.09
18.85 4.71 14.89
19.01 4.67 14.09
19.66 4.52 33.63
19.90 4.46 53.58
20.69 4.29 6.49
21.19 4.19 6.82
21.43 4.15 10.20
21.91 4.06 6.09
22.24 3.99 12.76
22.33 3.99 13.13
22.60 3.93 6.63
23.39 3.80 6.03
23.90 3.72 6.23
24.17 3.68 15.01
24.43 3.64 11.25
24.88 3.58 6.69
25.40 3.50 8.39
26.58 3.35 4.50
26.81 3.32 7.40
27.07 3.29 10.62
27.44 3.25 5.49
28.24 3.16 2.92
28.82 3.10 5.74
29.11 3.07 4.51
29.57 3.02 3.68
30.03 2.97 4.73
31.27 2.86 2.93
31.99 2.80 3.83
32.71 2.74 2.86
33.62 2.66 3.06
34.34 2.61 1.53
34.97 2.56 1.92
Embodiment 2
The preparation of the crystal form B of 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] benzene:
The powder of 52.3mg1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] benzene is dissolved in tetrahydrofuran (THF): in the mixed system of water=1:1 (v:v), and by the nylon leaching film of 0.45 micron by undissolved solid filtering, slowly evaporate into solid at ambient temperature to separate out, the X-ray powder diffraction data that namely collection solid obtains the crystal form B that crystal formation the present embodiment obtains are as shown in table 2.
The X-ray powder diffraction data of table 2 crystal form B
2theta D interval Intensity %
3.15 28.03 0.87
6.28 14.07 100.00
6.67 13.25 2.06
7.35 12.03 1.26
8.98 9.85 2.45
9.28 9.53 9.78
9.41 9.39 98.37
11.51 7.69 3.75
11.70 7.57 7.40
12.35 7.17 4.89
12.55 7.05 58.47
13.66 6.48 2.90
14.57 6.08 1.78
14.92 5.94 2.24
15.20 5.83 2.99
15.52 5.71 3.08
15.70 5.64 17.35
16.71 5.31 2.87
17.54 5.06 6.12
17.97 4.94 3.81
18.23 4.87 6.04
18.86 4.70 26.22
18.91 4.70 19.63
19.63 4.52 7.34
19.74 4.49 7.94
19.88 4.46 6.97
20.03 4.43 5.43
20.63 4.30 2.44
21.26 4.18 5.20
21.81 4.07 2.18
22.02 4.03 6.43
22.36 3.97 3.47
23.36 3.81 2.21
23.71 3.75 3.25
23.93 3.72 3.48
24.14 3.68 4.90
24.54 3.62 2.35
24.76 3.59 5.06
25.12 3.54 3.14
25.24 3.53 3.41
26.38 3.38 1.51
26.81 3.32 11.73
27.08 3.29 3.34
28.12 3.17 1.06
28.36 3.14 1.22
28.70 3.11 1.93
29.05 3.07 0.80
29.85 2.99 1.49
31.18 2.87 1.59
31.83 2.81 6.71
Embodiment 3
The preparation of the crystal form B of 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] benzene:
The powder of 508.1mg1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] benzene is dissolved in 10ml tetrahydrofuran solvent, and then adds 30ml H 2o obtains settled solution, heats this solution to 60 DEG C, and under 60 DEG C of conditions constant temperature 2 hours, then slow cooling to 20 DEG C, more uncovered stirring is spent the night, the solid of gained is crystal form B.The X-ray powder diffraction data of the crystal form B that the present embodiment obtains are as shown in table 3.
The X-ray powder diffraction data of table 3 crystal form B
2theta D interval Intensity %
6.21 14.23 35.70
6.75 13.10 9.67
7.37 12.00 6.84
9.00 9.82 11.90
9.55 9.26 22.48
10.60 8.34 7.40
11.71 7.55 21.45
12.42 7.13 26.51
12.58 7.04 33.61
13.75 6.44 19.38
15.29 5.80 24.45
15.58 5.69 24.53
15.88 5.58 27.97
16.81 5.28 29.57
17.55 5.05 32.37
18.05 4.92 23.60
18.29 4.85 20.60
18.95 4.68 30.34
19.68 4.51 76.97
19.82 4.48 100.00
20.03 4.43 72.65
20.70 4.29 22.76
21.33 4.17 43.49
22.20 4.00 41.24
22.32 3.98 40.53
23.45 3.79 23.82
24.01 3.71 31.99
24.26 3.67 48.67
24.86 3.58 28.58
25.24 3.53 28.50
26.38 3.38 12.29
26.80 3.32 28.09
26.92 3.31 35.51
28.19 3.17 13.44
28.82 3.10 27.26
28.96 3.09 24.67
29.76 3.00 25.74
31.09 2.87 12.15
31.81 2.81 13.43
33.74 2.65 14.07
34.34 2.61 7.92
35.50 2.53 10.13
36.64 2.45 12.29
37.18 2.42 9.11
37.63 2.39 10.02
38.96 2.31 6.62
Embodiment 4
The stability study of the crystal form B of 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] benzene:
Get two parts of crystal form B samples be placed in respectively 25 DEG C, 60% relative humidity and 40 DEG C, 75% relative humidity the uncovered placement of climatic chamber 30 days, then X-ray powder diffraction (XRPD) is surveyed in sampling, 25 DEG C, under 60% relative humidity, X-ray powder diffraction (XRPD) comparison diagram is as Fig. 4, and result is as shown in table 4.
Table 4 crystal form B stability study
Crystal form B is at 25 DEG C, and 60% relative humidity and 40 DEG C, under 75% relative humidities, within 30 days, crystal formation is constant, and above-mentioned test-results shows, crystal form B has satisfactory stability.
Embodiment 5
Hemihydrate dissolves degree comparative study in the crystal form B of 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] benzene and patent CN101573368B:
At ambient temperature, PH5.0 FeSSIF (under fed conditions simulated intestinal fluid) and PH6.5 FaSSIF (under fasted conditions simulated intestinal fluid) semihydrate crystal form samples in crystal form B and patent CN101573368B is used to be mixed with saturated solution respectively, 1 as a child after, 4 as a child after and measure the concentration of sample in solution by high performance liquid chromatography (HPLC) after 24 hours.Experimental result is as shown in table 5.
Hemihydrate dissolves degree comparative study in table 5 crystal form B and patent CN101573368B
Can be found out by above-mentioned comparing result, place after 1 hour in FeSSIF and FaSSIF, after 4 hours with crystal form B of the present invention after 24 hours compared with semihydrate crystal formation in patent CN101573368B, solubleness is higher.

Claims (8)

1. the crystal form B of 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] benzene, it is characterized in that, its X-ray powder diffraction figure is that 6.3 ° ± 0.2 °, 9.4 ° ± 0.2 °, 12.6 ° ± 0.2 °, 19.9 ° ± 0.2 °, 11.7 ° ± 0.2 °, 16.9 ° ± 0.2 ° place has characteristic peak in 2theta value.
2. crystal form B according to claim 1, is further characterized in that, its X-ray powder diffraction figure is that 18.2 ° ± 0.2 °, 22.3 ° ± 0.2 °, 24.4 ° ± 0.2 °, 28.9 ° ± 0.2 ° place has characteristic peak in 2theta value.
3. crystal form B according to claim 1, is characterized in that, its X-ray powder diffraction figure is substantially consistent with Fig. 1.
4. crystal form B according to claim 1, is characterized in that, its differential scanning calorimetric thermogram is basic consistent with Fig. 2.
5. the preparation method of the crystal form B of 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] benzene, it is characterized in that, by the powder dissolution of 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] benzene in the mixed solvent system of water and organic solvent, at ambient temperature by the method for slowly volatilization, obtain crystal form B, described organic solvent is methyl alcohol, ethanol, Virahol, acetonitrile, acetone, tetrahydrofuran (THF).
6. preparation method according to claim 5, is characterized in that, described organic solvent is ethanol or tetrahydrofuran (THF).
7. preparation method according to claim 5, is characterized in that, the volume ratio of described water and organic solvent is between 1:10 to 10:1.
8. preparation method according to claim 5, is characterized in that, the volume ratio of described water and organic solvent is 1:1.
CN201410542984.6A 2013-11-11 2014-10-14 Crystal form B of 1-(beta-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl] benzene and preparation method of crystal form B Pending CN104356121A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
CN201410542984.6A CN104356121A (en) 2013-11-11 2014-10-14 Crystal form B of 1-(beta-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl] benzene and preparation method of crystal form B
EP14862830.8A EP3068779A4 (en) 2013-11-11 2014-11-11 Crystalline forms b, c, and d of canagliflozin
JP2016530967A JP2016536321A (en) 2013-11-11 2014-11-11 Canagliflozin B-form, C-form and D-form
US15/035,751 US20160280731A1 (en) 2013-11-11 2014-11-11 CRYSTALLINE FORMS B, C, and D OF CANAGLIFLOZIN
PCT/IB2014/003013 WO2015071761A2 (en) 2013-11-11 2014-11-11 Crystalline forms b, c, and d of canagliflozin

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CN201310556655.2 2013-11-11
CN201310556655.2A CN103554092A (en) 2013-11-11 2013-11-11 New crystal form B of 1-(beta-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl] benzene and preparation method of new crystal form B
CN201410542984.6A CN104356121A (en) 2013-11-11 2014-10-14 Crystal form B of 1-(beta-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl] benzene and preparation method of crystal form B

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CN201410542984.6A Pending CN104356121A (en) 2013-11-11 2014-10-14 Crystal form B of 1-(beta-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl] benzene and preparation method of crystal form B

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WO2015071761A3 (en) * 2013-11-11 2015-09-24 Crystal Pharmatech Co., Ltd. Crystalline forms b, c, and d of canagliflozin

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US10174010B2 (en) 2014-03-19 2019-01-08 Hangzhou Pushai Pharmaceutical Technology Co., Ltd. Canagliflozin monohydrate and its crystalline forms, preparation methods and uses thereof
CN103980261B (en) * 2014-04-01 2016-06-29 天津大学 The A crystal formation of canagliflozin and crystallization preparation method thereof
CN103980262B (en) * 2014-04-01 2016-06-22 天津大学 The B crystal form of canagliflozin and crystallization preparation method thereof
EP2933255A1 (en) 2014-04-17 2015-10-21 LEK Pharmaceuticals d.d. Novel crystalline form of 1-(beta-D-glucopyranosyl)-4- methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene
CN103936726B (en) * 2014-04-18 2016-06-15 王军 Crystal, preparation method and its usage
CN104130246A (en) * 2014-05-28 2014-11-05 华润赛科药业有限责任公司 New crystal form of 1-(beta-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene and preparation method thereof
CN104761546A (en) * 2014-06-21 2015-07-08 山东富创医药科技有限公司 Novel (1S)-1,5-dehydro-1-[3-[[5-(4-(4-fluorophenyl)-2-thiophene] methyl]-4-methyl phenyl)-D-glucitol crystal form and preparation method thereof
CN104230907B (en) * 2014-08-07 2017-05-10 王军 Method for preparing crystals and application of crystals
CN104530023A (en) * 2014-12-25 2015-04-22 重庆医药工业研究院有限责任公司 Crystal form I of Canagliflozin and preparation method thereof
CN104945392A (en) * 2015-01-27 2015-09-30 江苏嘉逸医药有限公司 Crystal-type canagliflozin-hydrate as well as preparation method and application of crystal-type canagliflozin hydrate
CN104530024B (en) 2015-02-04 2017-08-08 上海迪赛诺药业有限公司 Crystal formation of 1 (β D glycopyranosyls) 4 methyl 3 [5 (4 fluorophenyl) 2 thienyl methyls] benzene and preparation method thereof
CN108017626A (en) * 2016-11-04 2018-05-11 上海奥博生物医药技术有限公司 A kind of canagliflozin semihydrate novel crystal forms

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