CN104130246A - New crystal form of 1-(beta-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene and preparation method thereof - Google Patents
New crystal form of 1-(beta-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene and preparation method thereof Download PDFInfo
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- CN104130246A CN104130246A CN201410230836.0A CN201410230836A CN104130246A CN 104130246 A CN104130246 A CN 104130246A CN 201410230836 A CN201410230836 A CN 201410230836A CN 104130246 A CN104130246 A CN 104130246A
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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
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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
Abstract
Belonging to the field of pharmacy, the invention in particular relates to a new crystal form of 1-(beta-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene and a preparation method thereof. The X-ray powder diffraction diagram of the crystal form has characteristic peaks at sites that the 2theta value is 6.5+/-0.2 degrees, 9.7+/-0.2 degrees, 19.5+/-0.2 degrees, 22.9+/-0.2 degrees and 28.0+/-0.2 degrees.
Description
Technical field
The invention belongs to pharmaceutical field, be specifically related to a kind of 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] new crystal of benzene and preparation method thereof.
Background technology
The clean semihydrate of Ka Gelie, chemistry 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl by name] benzene semihydrate, its structural formula is suc as formula shown in I, be the novel sodium dependent glucose of one translocator (SGLT) inhibitor of Janssen Pharmaceutica of Johnson & Johnson of the U.S. and the joint development development of Mitsubishi Pharmaceutical Co., Ltd, commodity are called Invokana.Medicine, for suppressing the filtration heavy absorption process of blood sugar at renal glomerulus, can stop the heavily absorption of glucose at kidney by alpha-glucosidase inhibitor to the restraining effect of this process, plays thereby increase the excretion of glucose in urine the hypoglycemic effect of falling.Obtain FDA (Food and Drug Adminstration) (FDA) approval listing on March 29th, 2013, and be first alpha-glucosidase inhibitor that obtains FDA approval.Compared with traditional type II diabetes medicine, the clean sheet of Ka Gelie has good effect, feature that untoward reaction is few, and security is higher.Drug market analyst prediction, the annual sales amount of the clean sheet of Ka Gelie will be up to 10,000,000,000 dollars, and market outlook are wide.
The clean crystal formation of current existing Ka Gelie, mainly comprise following several: Chinese patent CN101573368B discloses a kind of crystal type 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl of novelty] benzene semihydrate, its X-ray powder diffraction figure is 4.36 ° ± 0.2 °, 13.54 ° ± 0.2 °, 16.00 ° ± 0.2 °, 19.32 ° ± 0.2 ° and 20.80 ° ± 0.2 ° in 2theta value and has characteristic peak.In Chinese patent CN103554092A, disclose crystal form B and preparation method thereof, its X-ray powder diffraction pattern is 6.3 ° ± 0.2 °, 9.4 ° ± 0.2 °, 12.6 ° ± 0.2 °, 11.7 ° ± 0.2 °, 16.9 ° ± 0.2 °, 18.2 ° ± 0.2 °, 19.9 ° ± 0.2 °, 22.3 ° ± 0.2 °, 24.4 ° ± 0.2 ° and 28.9 ° ± 0.2 ° in 2theta value and has characteristic peak.Crystal C and D and preparation method thereof are disclosed in Chinese patent CN103588762A, the X-ray powder diffraction pattern of its crystal C is 6.5 ° ± 0.2 ° in 2theta value, 9.8 ° ± 0.2 °, 16.4 ° ± 0.2 °, 13.1 ° ± 0.2 °, 19.8 ° ± 0.2 °, 23.7 ° ± 0.2 °, 25.2 ° ± 0.2 °, 19.5 ° ± 0.2 °, locate to there is characteristic peak for 26.5 ° ± 0.2 ° and 17.1 ° ± 0.2 °, the X-ray powder diffraction pattern of its crystal formation D is 6.8 ° ± 0.2 ° in 2theta value, 13.6 ° ± 0.2 °, 20.5 ° ± 0.2 °, 17.1 ° ± 0.2 °, 19.2 ° ± 0.2 °, 22.9 ° ± 0.2 °, 16.5 ° ± 0.2 °, 10.2 ° ± 0.2 °, 18.5 ° ± 0.2 ° and 24.4 ° ± 0.2 ° has characteristic peak.US Patent No. 2009233874A1 discloses the clean a kind of crystal formation of Ka Gelie, it is characterized in that, its x-ray diffraction pattern is 14.60 ° ± 0.2 °, 16.38 ° ± 0.2 °, 18.62 ° ± 0.2 °, 19.20 ° ± 0.2 °, 19.86 ° ± 0.2 ° and 20.76 ° ± 0.2 ° in 2theta value and locates to have characteristic peak.In patent WO2013064909A2 specification sheets, disclose Ka Gelie only amorphous, Ka Gelie only with other acid mix crystal formation and preparation method thereof, in specification sheets, mention amorphously under super-humid conditions, easily turning brilliant phenomenon, but not under super-humid conditions, turn brilliant after crystal formation study.
Applicant is by constantly research, by naturally turning brilliant method, find a kind of new 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] crystal formation of benzene (clean referred to as Ka Gelie).
Summary of the invention
The object of the present invention is to provide a kind of 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] new crystal of benzene (clean referred to as Ka Gelie).
The present invention is by above-mentioned new crystal called after crystal formation E.
1-of the present invention (β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] the crystal formation E of benzene, in its X-ray powder diffraction pattern, 2theta value is 6.5 ° ± 0.2 °, 9.7 ° ± 0.2 °, 19.5 ° ± 0.2 °, 22.9 ° ± 0.2 ° and 28.0 ° ± 0.2 ° and locates to have characteristic peak.
1-of the present invention (β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] the crystal formation E of benzene, on DSC collection of illustrative plates, there is the feature endotherm(ic)peak of 80 ± 1 DEG C.
1-of the present invention (β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] the crystal formation E of benzene, 3385.01cm in infrared spectra
-1, 2919.48cm
-1, 2360.26cm
-1, 1599.94cm
-1, 1509.11cm
-1, 1401.82cm
-1, 1232.64cm
-1, 1160.51cm
-1, 1086.71cm
-1, 831.14cm
-1, 798.32cm
-1, 613.41cm
-1there is characteristic peak at place.
1-of the present invention (β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] the crystal formation E of benzene, its X-ray powder diffraction pattern is the diffractogram shown in accompanying drawing 1.
1-of the present invention (β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] the crystal formation E of benzene, its DSC collection of illustrative plates is the collection of illustrative plates shown in accompanying drawing 2.
1-of the present invention (β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] the crystal formation E of benzene, its infrared spectra is the collection of illustrative plates described in accompanying drawing 3.
Another object of the present invention is to provide 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] preparation method of the crystal formation E of benzene.
Preparation method of the present invention, comprising the following steps: by amorphous 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] benzene powder is positioned in the room temperature environment of high humidity and naturally turns brilliant, obtains crystal formation E.
Amorphous 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] benzene powder can buy, also can prepare by prior art on market.
Wherein, described high humidity refers to that humidity is within the scope of 75%-92.5%.
Wherein, described in, turning the brilliant time is generally 5-10 days.
Wherein, described room temperature refers generally to 20-40 DEG C.
Another object of the present invention is to provide 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] the crystal formation E of the benzene application in the medicine of preparation treatment diabetes.
Another object of the present invention is to provide one to contain 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] pharmaceutical composition of the crystal formation E of benzene.
Pharmaceutical composition of the present invention, also contains pharmaceutically acceptable carrier.
Pharmaceutical composition of the present invention, 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] the shared weight percent of crystal formation E of benzene can be 0.1-99.9%, all the other are medicine acceptable carrier.
Pharmaceutical composition of the present invention can be prepared into any pharmaceutically useful formulation, and these formulations comprise: tablet, sugar coated tablet, film coated tablet, enteric coated tablet, capsule, hard capsule, soft capsule, oral liquid, suck agent, granule, electuary, pill, powder, paste, sublimed preparation, suspensoid, pulvis, solution, injection, suppository, ointment, plaster, creme, sprays, drops, patch.Preparation of the present invention, preferably oral dosage form, as: capsule, tablet, oral liquid, granule, pill, powder, sublimed preparation, paste etc.Most preferably capsule.
Pharmaceutical composition of the present invention, the preparation of its oral administration can contain conventional vehicle, such as tackiness agent, weighting agent, thinner, tablet agent, lubricant, disintegrating agent, tinting material, seasonings and wetting agent, can carry out dressing to tablet if desired.
Applicable weighting agent comprises Mierocrystalline cellulose, mannitol, lactose and other similar weighting agent.Suitable disintegrating agent comprises starch, polyvinylpyrrolidone and starch derivative, for example sodium starch glycollate.Suitable lubricant comprises, for example Magnesium Stearate.The acceptable wetting agent of suitable medicine comprises sodium lauryl sulphate.
Can, by mixing, fill, the method that compressing tablet etc. are conventional is prepared solid oral composition.Repeatedly mix in those compositions that can make active substance be distributed in a large amount of weighting agents of whole use.
The form of oral liquid can be for example water-based or oily suspensions, solution, emulsion, syrup or elixir, or can be a kind of used water before use or the composite drying products of other suitable carrier.This liquid preparation can contain conventional additive, such as suspension agent, for example sorbyl alcohol, syrup, methylcellulose gum, gelatin, Natvosol, carboxymethyl cellulose, aluminium stearate gel or hydrogenation edible-fat, emulsifying agent, for example Yelkin TTS, anhydro sorbitol monooleate or gum arabic; Non-aqueous carrier (they can comprise edible oil), for example Prunus amygdalus oil, fractionated coconut oil, such as oily ester, propylene glycol or the ethanol of the ester of glycerine; Sanitas, for example para hydroxybenzene methyl esters or propylparaben or Sorbic Acid, and if need, can contain conventional flavouring agent or tinting material.
For injection, the liquid unit dosage of preparation contains active substance of the present invention and sterile carrier.According to carrier and concentration, this compound can be suspended or dissolve.The preparation of solution, normally by active substance being dissolved in a kind of carrier, being packed into filter-sterilized before a kind of suitable bottle or ampoule, then seals.Auxiliary material for example a kind of local anesthetic, sanitas and buffer reagent also can be dissolved in this carrier.In order to improve its stability, can be by freezing this composition after packing bottle into, and under vacuum, water is removed.
Pharmaceutical composition of the present invention, in the time being prepared into medicament, optionally add applicable medicine acceptable carrier, described medicine acceptable carrier is selected from: N.F,USP MANNITOL, sorbyl alcohol, Sodium Pyrosulfite, sodium bisulfite, Sulfothiorine, cysteine hydrochloride, Thiovanic acid, methionine(Met), vitamins C, EDETATE SODIUM, Ethylenediaminetetraacetic Acid Calcium Salt, the alkali-metal carbonate of monovalence, acetate, phosphoric acid salt or its aqueous solution, hydrochloric acid, acetic acid, sulfuric acid, phosphoric acid, amino acid, sodium-chlor, Repone K, Sodium.alpha.-hydroxypropionate, Xylitol, maltose, glucose, fructose, dextran, glycine, starch, sucrose, lactose, mannitol, silicon derivative, Mierocrystalline cellulose and derivative thereof, alginate, gelatin, polyvinylpyrrolidone, glycerine, POLYSORBATE 80, agar, calcium carbonate, Calcium hydrogen carbonate, tensio-active agent, polyoxyethylene glycol, cyclodextrin, beta-cyclodextrin, phospholipid material, kaolin, talcum powder, calcium stearate, Magnesium Stearate etc.
Another object of the present invention is to provide the application of pharmaceutical composition of the present invention in the medicine of preparation treatment diabetes.
Crystal formation E of the present invention characterizes by X-ray powder diffraction, heat analysis and infrared spectra etc.
Wherein X-ray powder diffraction is to measure with CuK α 1 radiation with x-ray diffractometer (XD2/3 series diffractometer, Beijing Puxi General Instrument Co., Ltd).
The method of X-ray powder diffraction is as follows:
Sweep velocity: 2 degrees/min
Target: Cu K α 1,1.5406 dust
Voltage: 36 kilovolts (kV)
Electric current: 20 milliampere(mA)s (mA)
Scan pattern: automatically
Sweep limit: 3 to 50 degree
Sampling step is wide: 0.0100 degree
TGA-DSC heat analysis method is to gather by SDT Q600 simultaneous thermal analysis instrument, and concrete grammar parameter is as follows:
Temperature range: 25 degrees Celsius-150 degrees Celsius
Sweep velocity: 5 degrees celsius/minute
Shielding gas: nitrogen, 100 ml/min
Infrared spectrometry method is to gather by ALPHA-Bruker twin-beam infrared spectrophotometer: adopt pellet technique at 4000～400cm
-1in scope, measure, take the about 1.5mg of sample, add the about 300mg grinding of anhydrous Potassium Bromide powder and be evenly pressed into suitable thin slice, measure infrared spectrogram.
Crystal formation E of the present invention compares with existing crystal formation, has good stability, yield height and purity high, and particularly preparation technology of the present invention is simple, greatly reduces costs and operating process.
Brief description of the drawings
The X-ray diffracting spectrum of the clean crystal formation E of accompanying drawing 1: embodiment 1 Ka Gelie
The DSC-TGA collection of illustrative plates of the clean crystal formation E of accompanying drawing 2: embodiment 1 Ka Gelie
The IR collection of illustrative plates of the clean crystal formation E of accompanying drawing 3: embodiment 1 Ka Gelie
The X-diffracting spectrum of the clean crystal formation E of accompanying drawing 4: embodiment 2 Ka Gelie
The X-diffracting spectrum of the clean crystal formation E of accompanying drawing 5: embodiment 3 Ka Gelie
The X-diffracting spectrum of the clean crystal formation E of accompanying drawing 6: embodiment 4 Ka Gelie
Embodiment
By following specific embodiment, the present invention is further illustrated, but not as restriction of the present invention.
Embodiment 1:75% humidity and prepare the clean crystal formation E of Ka Gelie for 5 days under condition
Get the clean powder tiling of the amorphous Ka Gelie of 1g and be placed in watch-glass, room temperature lucifuge is placed in the sealed vessel under 75% humidity condition, places 5 days, obtains the clean crystal formation E of white solid Ka Gelie.
DSC endotherm(ic)peak is 75.95 DEG C at 79.87 DEG C, initial melting temperature, and on TGA collection of illustrative plates, 25 DEG C of-105 DEG C of weight loss are that 4.247%, HPLC purity is 99.65%.
Embodiment 2:92.5% humidity and prepare the clean crystal formation E of Ka Gelie for 5 days under condition
Get the clean powder tiling of the amorphous Ka Gelie of 1g and be placed in watch-glass, room temperature lucifuge is placed in the sealed vessel under 92.5% humidity condition, places 5 days, obtains the clean crystal formation E of light yellow solid Ka Gelie.
DSC endotherm(ic)peak is 75.95 DEG C at 79.06 DEG C, initial melting temperature, and on TGA collection of illustrative plates, 25 DEG C of-105 DEG C of weight loss are that 5.085%, HPLC purity is 99.62%.
Embodiment 3:75% humidity and prepare the clean crystal formation E of Ka Gelie for 10 days under condition
Get the clean powder tiling of the amorphous Ka Gelie of 1g and be placed in watch-glass, room temperature lucifuge is placed in the sealed vessel under 75% humidity condition, places 10 days, obtains the clean crystal formation E of light yellow solid Ka Gelie.
DSC endotherm(ic)peak is 76.20 DEG C at 80.10 DEG C, initial melting temperature, and on TGA collection of illustrative plates, 25 DEG C of-105 DEG C of weight loss are that 3.672%, HPLC purity is 99.55%.
Embodiment 4:92.5% humidity and prepare the clean crystal formation E of Ka Gelie for 10 days under condition
Get the clean powder tiling of the amorphous Ka Gelie of 1g and be placed in watch-glass, room temperature lucifuge is placed in the sealed vessel under 92.5% humidity condition, places 10 days, obtains the clean crystal formation E of light yellow solid Ka Gelie.
DSC endotherm(ic)peak is 76.14 DEG C at 79.47 DEG C, initial melting temperature, and on TGA collection of illustrative plates, 25 DEG C of-105 DEG C of weight loss are that 3.859%, HPLC purity is 99.51%.
Experimental example 5: stability test
Following table is that the clean new crystal E of Ka Gelie of the present invention turns before and after crystalline substance by amorphous, and it is as follows that HPLC detects related substance situation:
| Numbering | Main peak | Newly-increased impurity | Color outward appearance | Crystal formation |
| Amorphous samples | 99.70％ | - | White powder | Amorphous |
| Embodiment 175% humidity 5 days | 99.65％ | Nothing | White solid | E crystal formation |
| Embodiment 292.5% humidity 5 days | 99.62％ | Nothing | Light yellow solid | E crystal formation |
| 25 DEG C of placements of amorphous 40% humidity 5 days | 99.66％ | 0.02％ | White powder | Amorphous |
| Embodiment 375% humidity 10 days | 99.55％ | 0.06％ | Light yellow solid | E crystal formation |
| Embodiment 492.5% humidity 10 days | 99.51％ | 0.05％ | Light yellow solid | E crystal formation |
| 25 DEG C of placements of amorphous 40% humidity 10 days | 99.52％ | 0.04％ | White powder | Amorphous |
Experimental result demonstration, the clean crystal formation E of Ka Gelie of the present invention turns before and after crystalline substance by amorphous: in HPLC, main peak content all slightly reduces for 5 days and 10 days; Turning newly-increased impurity in brilliant process is not significantly increased; Crystal formation E stability is higher than amorphous stability.Therefore the preparation method of the clean crystal formation E of this Ka Gelie does not have a significant effect to quality product.
Claims (10)
1. 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] the crystal formation E of benzene, it is characterized in that, in its X-ray powder diffraction pattern, 2theta value is 6.5 ° ± 0.2 °, 9.7 ° ± 0.2 °, 19.5 ° ± 0.2 °, 22.9 ° ± 0.2 ° and 28.0 ° ± 0.2 ° and has characteristic peak.
2. crystal formation E according to claim 1, is characterized in that, has the feature endotherm(ic)peak of 80 ± 1 DEG C on DSC collection of illustrative plates.
3. crystal formation E according to claim 1, is characterized in that, has 3385.01cm on infrared spectra
-1, 2919.48cm
-1, 2360.26cm
-1, 1599.94cm
-1, 1509.11cm
-1, 1401.82cm
-1, 1232.64cm
-1, 1160.51cm
-1, 1086.71cm
-1, 831.14cm-
1, 798.32cm
-1, 613.41cm
-1characteristic peak.
4. the preparation method of crystal formation E claimed in claim 1, it is characterized in that, by amorphous 1-(β-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] benzene powder is positioned in the room temperature environment of high humidity and naturally turns brilliant, obtains crystal formation E.
5. preparation method according to claim 4, is characterized in that, super-humid conditions specifically refers within the scope of 75%-92.5%.
6. preparation method according to claim 4, is characterized in that, turning the brilliant time is 5-10 days.
7. the application of crystal formation E claimed in claim 1 in the medicine of preparation treatment diabetes.
8. a pharmaceutical composition, contains crystal formation E claimed in claim 1.
9. pharmaceutical composition claimed in claim 1, contains pharmaceutically acceptable carrier.
10. the application of pharmaceutical composition claimed in claim 1 in the medicine of preparation treatment diabetes.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104530024A (en) * | 2015-02-04 | 2015-04-22 | 上海迪赛诺药业有限公司 | Crystal form of 1-(beta-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] benzene and preparation method thereof |
| WO2016016774A1 (en) * | 2014-07-31 | 2016-02-04 | Sun Pharmaceutical Industries Limited | Crystalline forms of canagliflozin |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013064909A2 (en) * | 2011-10-31 | 2013-05-10 | Scinopharm Taiwan, Ltd. | Crystalline and non-crystalline forms of sglt2 inhibitors |
| CN103554092A (en) * | 2013-11-11 | 2014-02-05 | 苏州晶云药物科技有限公司 | 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 |
| CN103588762A (en) * | 2013-11-27 | 2014-02-19 | 苏州晶云药物科技有限公司 | Novel crystal form of canagliflozin and its preparation method |
-
2014
- 2014-05-28 CN CN201410230836.0A patent/CN104130246A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013064909A2 (en) * | 2011-10-31 | 2013-05-10 | Scinopharm Taiwan, Ltd. | Crystalline and non-crystalline forms of sglt2 inhibitors |
| CN103554092A (en) * | 2013-11-11 | 2014-02-05 | 苏州晶云药物科技有限公司 | 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 |
| CN103588762A (en) * | 2013-11-27 | 2014-02-19 | 苏州晶云药物科技有限公司 | Novel crystal form of canagliflozin and its preparation method |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016016774A1 (en) * | 2014-07-31 | 2016-02-04 | Sun Pharmaceutical Industries Limited | Crystalline forms of canagliflozin |
| CN104530024A (en) * | 2015-02-04 | 2015-04-22 | 上海迪赛诺药业有限公司 | Crystal form of 1-(beta-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienyl methyl] benzene and preparation method thereof |
| EP3053919A1 (en) | 2015-02-04 | 2016-08-10 | Shanghai Desano Pharmaceuticals Investment Co., Ltd | Crystalline form of 1-(beta-d-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene and preparation method thereof |
| US10167306B2 (en) | 2015-02-04 | 2019-01-01 | Shanghai Desano Pharmaceuticals Investment Co., Ltd. | Crystalline form of 1-(beta-D-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene and preparation method thereof |
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Application publication date: 20141105 |