CN103655539B - A kind of oral solid formulation of canagliflozin and preparation method thereof - Google Patents
A kind of oral solid formulation of canagliflozin and preparation method thereof Download PDFInfo
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Abstract
The present invention relates to a kind of canagliflozin oral solid drug compositions and preparation method thereof, and the composition contains canagliflozin and pharmaceutic adjuvant, wherein canagliflozin is unformed form, and mean particle size is 2.5~30 μm.The composition efficiently solves technical problem of the canagliflozin in solid pharmaceutical preparation preparation process transfer crystalline substance and poor compressibility of unformed form.
Description
Technical field
The invention belongs to field of pharmaceutical preparations, and in particular to a kind of canagliflozin oral solid drug composition and its preparation
Method.
Technical background
Canagliflozin, general entitled canagliflozin, chemical name are as follows: 1- (β-D- glycopyranosyl) -4- methyl -3-
[5- (4- fluorophenyl) -2- thienyl methyl] benzene, structural formula are shown in formula I.
Canagliflozin belongs to 2 type sodium glucose cotransporter (SGLT2) inhibitor of selectivity, has obtained the U.S. at present
Ratify the treatment for being used for diabetes B with European Union.
Under normal circumstances, kidney plays an important role in the adjusting of blood glucose.Glucose is all inhaled again when passing through renal tubule
Blood is withdrawn, therefore is practically free of glucose in urine eventually, maintains the stabilization of blood glucose.Glucose is uncharged organic
Object, its reabsorption are the active reabsorption processes that inverse concentration difference carries out, and it is white to rely primarily on sodium glucose co-transporter 2
(SGLT).SGLT points are SGLT1 and SGLT2 two types.SGLT2 is the transport vehicle of a kind of low-affinity, high capacity, right
Glucose and sodium carry out the transhipment of 1:1, are distributed mainly on the segment kidney proximal tubule S1, to the grape for entering kidney convoluted tubule high concentration
Sugar carries out reabsorption, and SGLT2 reabsorption glucose accounts for the 90% of whole reabsorption glucose.SGLT1 be then a kind of high-affinity,
The glucose transporter of low-load, the glucose for transporting 1 molecule transport the Na+ of 2 molecules simultaneously, are distributed in the section of kidney proximal tubule S2 ~ 3
Section, remaining 10% glucose of SGLT1 reabsorption.
Canagliflozin selective depression SGLT2 can inhibit the reabsorption of most of glucose in vivo, promote glucose sugar big
Amount discharge from urine achievees the purpose that control blood glucose level.Since the mechanism of action of canagliflozin is unrelated with insulin, and
Other any treating diabetes schemes (including insulin), which are used in combination, can provide additional blood sugar reducing function.It both can be with it
Its oral hypoglycemic agents joint is used for poor blood glucose control or insulin resistance problem patient under existing therapeutic scheme, and can be with pancreas islet
The patient that element joint can not be acted on for the very low and existing oral drugs of β cell function.
Currently, the medicinal forms of the canagliflozin of USA and EU approval are canagliflozin semihydrate, structural formula is such as
Shown in Fig. 2.The semihydrate discloses in CN101573368.
Summary of the invention
The purpose of the present invention is to provide a kind of canagliflozin oral solid drug compositions, wherein canagliflozin is with nothing
Stereotypic morphological exists.The inventors discovered that though its dissolubility of the canagliflozin of unformed form is better than canagliflozin semihydrate,
But insoluble compound is still fallen within, and there are poor compressibility, is not easy to be prepared into solid pharmaceutical preparation, is held if using the granulation of a large amount of solvents
Easily it is converted to the technical problems such as canagliflozin semihydrate.The partial size by controlling bulk pharmaceutical chemicals is had been surprisingly found that by numerous studies,
The compressibility and dissolution rate and without using granulating solvent that canagliflozin can be effectively improved, efficiently solve the card of unformed form
Lattice arrange only in the important technology problem of formulation process transfer crystalline substance and poor compressibility.
It is flat to have collected different volumes by the way that the canagliflozin raw material of unformed form is carried out micronization processes by the present inventor
The sample of equal partial size prepares the tablet of different average grain diameter bulk pharmaceutical chemicals by dry granulation process using different auxiliary materials, investigates
Compressibility, tablet appearance character and Dissolution of Tablet when tabletting.As a result, it has been found that when the volume average particle size of canagliflozin raw material
When being 1 μm, dissolution rate early period of tablet is remarkably decreased, and is unable to satisfy product quality requirement, and work as canagliflozin bulk pharmaceutical chemicals
When the average grain diameter of grain is 1 μm and 50 μm, the tableting pressure and tablet hardness correlation of tablet are poor, and by canagliflozin raw material
The average grain diameter of medicine controls in 2.5~30 μ ms, can effectively ensure in the preparation process of preparation the compressibility of material and
The dissolution rate of finished tablet and do not turn brilliant, so as to complete the present invention.
Canagliflozin oral solid drug composition to realize the present invention, provides the scheme of being implemented as follows.
In one embodiment, a kind of canagliflozin oral solid drug composition of the invention, comprising canagliflozin and
Pharmaceutic adjuvant, wherein canagliflozin be unformed form, mean particle size be 2.5~30 μm, preferably 2.5~20 μm, more
Preferably 2.5~10 μm.
In the above-described embodiment, canagliflozin oral solid drug composition of the invention, the weight of canagliflozin are
The 10% ~ 60% of composition weight；The pharmaceutic adjuvant includes filler, disintegrating agent or lubricant, and the filler is that crystallite is fine
Dimension element, lactose, pregelatinized starch, mannitol, starch, sorbierite or their any mixture, preferably microcrystalline cellulose,
Lactose or their any mixture, weight are the 30% ~ 75% of composition weight；The disintegrating agent is cross-linked carboxymethyl fiber
Plain sodium, low-substituted hydroxypropyl cellulose, sodium carboxymethyl starch, crospovidone or their any mixture, are preferably handed over
Join sodium carboxymethylcellulose, weight is the 3% ~ 10% of composition weight；The lubricant is magnesium stearate, calcium stearate, hard
Resin acid, sodium stearyl fumarate or their any mixture, preferably magnesium stearate, lubricant weight are the 0.5% of composition weight
~5%。
In the above-described embodiment, canagliflozin oral solid drug composition of the invention, the content of canagliflozin are
50 ~ 300mg, preferably 100 ~ 300 mg.
In the above-described embodiment, canagliflozin oral solid drug composition of the invention, the pharmaceutic adjuvant also into
One
Step includes surfactant, and the surfactant is selected from lauryl sodium sulfate, polysorbate, fatty acid sorb
Smooth, poloxamer, Emulsifier EL-60 and their any mixture.
In the above-described embodiment, canagliflozin oral solid drug composition of the invention, the composition are tablet.
In one embodiment, canagliflozin oral solid drug composition of the invention, comprising canagliflozin and
Pharmaceutic adjuvant containing filler, disintegrating agent and lubricant, wherein canagliflozin is unformed form, mean particle size
Be 2.5~30 μm, preferably 2.5~20 μm, more preferably 2.5~10 μm, canagliflozin weight be composition weight 10% ~
60%, filler is 30% ~ 75% that weight is composition weight, and disintegrating agent weight is the 3% ~ 10% of composition weight, lubricant weight
Amount is the 0.5% ~ 5% of composition weight.
In above-mentioned specific embodiment, canagliflozin oral solid drug composition of the invention, the filler is
Microcrystalline cellulose, lactose, pregelatinized starch, mannitol, starch, sorbierite or their any mixture, preferably crystallite
Cellulose, lactose or their any mixture；The disintegrating agent is croscarmellose sodium, low substituted hydroxy-propyl fiber
Element, sodium carboxymethyl starch, crospovidone or their any mixture, preferably croscarmellose sodium；It is described
Lubricant is magnesium stearate, calcium stearate, stearic acid, sodium stearyl fumarate or their any mixture, preferably magnesium stearate.
In above-mentioned specific embodiment, canagliflozin oral solid drug composition of the invention, canagliflozin contains
Amount is 50 ~ 300mg, preferably 100 ~ 300mg.
In above-mentioned specific embodiment, canagliflozin oral solid drug composition of the invention is further comprised
Surfactant, the surfactant are selected from lauryl sodium sulfate, polysorbate, fatty acid sorbitan, poloxamer, gather
Any mixture of ethylene oxide castor oil and they.
In a preferred embodiment, canagliflozin oral solid drug composition of the invention includes canagliflozin 10%
~ 60%, filler 30% ~ 75%, disintegrating agent 3% ~ 10% and lubricant 0.5% ~ 5%, wherein the filler be microcrystalline cellulose,
Lactose or their any mixture, the disintegrating agent are croscarmellose sodium, and the lubricant is magnesium stearate, institute
Stating canagliflozin is unformed form, and the average grain diameter of particle is 2.5~30 μm, preferably 2.5~20 μm, more preferably 2.5
~10 μm.
In above-mentioned preferred embodiment, canagliflozin oral solid drug composition of the invention, canagliflozin contains
Amount is 50 ~ 300mg, preferably 100 ~ 300 mg.
In above-mentioned preferred embodiment, canagliflozin oral solid drug composition of the invention may be used also as needed
Further include surfactant, the surfactant be selected from lauryl sodium sulfate, polysorbate, fatty acid sorbitan,
Poloxamer, Emulsifier EL-60 and their any mixture, dosage of surfactant are conventional amount used.
In above-mentioned preferred embodiment, the dosage form of the composition is preferably tablet.
The object of the invention is also to provide a kind of method of canagliflozin oral solid drug composition processed, this method
It is not necessary that granulating solvent is added.
In one embodiment, a method of preparing canagliflozin oral solid drug composition of the invention, the party
Method the following steps are included:
A) unformed canagliflozin is micronized, obtains the particle that average grain diameter is 2.5~30 μm；
B) by the canagliflozin of micronization and filler, disintegrating agent and mix lubricant at uniform powder；
C) it pelletizes；
D) disintegrating agent, lubricant is added, is mixed rear tabletting, obtains canagliflozin piece finished product.
The method of aforementioned present invention, preferably 2.5~20 μm of the average grain diameter of described step a), more preferable 2.5-10 μm；Institute
The filler said is one of microcrystalline cellulose, lactose, pregelatinized starch, mannitol, starch, sorbierite or their times
Meaning mixture, being preferably filled with agent is or mixtures thereof lactose, microcrystalline cellulose；The disintegrating agent is cross-linked carboxymethyl cellulose
Sodium, low-substituted hydroxypropyl cellulose, sodium carboxymethyl starch, crospovidone or their any mixture, preferred disintegrating agent
For croscarmellose sodium；The lubricant be magnesium stearate, calcium stearate, stearic acid, sodium stearyl fumarate or
Their any mixture, preferred lubricant are magnesium stearate.The dosage of lubricant is 0.5% ~ 5%.
The method of aforementioned present invention in described step b), can also be added and also can further include surface-active as needed
Agent, the surfactant are selected from lauryl sodium sulfate, polysorbate, fatty acid sorbitan, poloxamer, polyoxyethylene castor
The dosage of any mixture of sesame oil and they, surfactant is conventional amount used, is chosen as the 1-4.5% of film weight.
Influence research of the raw material volume Average Particle Diameters to unformed form canagliflozin compressibility
The present invention by by unformed form canagliflozin carry out micronization processes, have collected volume average particle size be 1 μm,
The canagliflozin bulk pharmaceutical chemicals particle of 2.5 μm, 10 μm, 20 μm, 30 μm, 50 μm etc. 6 kinds different average grain diameters, passes through dry granulation work
Skill prepares the tablet of 6 kinds of canagliflozins containing different average grain diameters, investigates the relationship of tableting pressure and tablet hardness, and measures
The friability of tablet.The result shows that: when the average grain diameter of canagliflozin bulk pharmaceutical chemicals particle is 2.5 μm, 10 μm, 20 μm, 30 μm,
The tableting pressure of tablet and tablet hardness correlation are good, and the friability of tablet meets Chinese Pharmacopoeia version correlation rule in 2010
It is fixed；And the average grain diameter of canagliflozin bulk pharmaceutical chemicals particle be 1 μm and 50 μm when, the tableting pressure of tablet is related to tablet hardness
Property is poor, and the friability of tablet does not meet Chinese Pharmacopoeia version relevant regulations in 2010.
The studies above the result shows that, when the mean particle sizes of canagliflozin bulk pharmaceutical chemicals is controlled between 2.5~30 μm,
The tablet of preparation has compressibility well, and friability meets Chinese Pharmacopoeia version relevant regulations in 2010.Preferably, by card lattice
The average grain diameter for arranging net bulk pharmaceutical chemicals particle controls between 2.5~20 μm, and further preferably 2.5~10 μm.
The preparation of canagliflozin tablet of the present invention uses dry granulation tablet forming technique, i.e., mixed by supplementary material,
The technical process of granulation, particle mixing, tabletting.
Influence research of the raw material volume Average Particle Diameters to canagliflozin tablet appearance character
Canagliflozin tablet prepared by above-mentioned 6 kinds of variable grains partial size raw material carries out appearance character comparison and investigates.As a result
Show: when the average grain diameter of canagliflozin bulk pharmaceutical chemicals particle is 2.5 μm, 10 μm, 20 μm, 30 μm, unilateral bright and clean, the base of tablet
, without fine powder, appearance character is good for this；And the average grain diameter of canagliflozin bulk pharmaceutical chemicals particle be 1 μm and 50 μm when, the piece of tablet
There is concave-convex sense in face, and easily picking, appearance character are poor.
It is investigated by comparative study, the volume average particle size of canagliflozin raw material controls between 2.5~30 μm, can be effective
Ensure the appearance character of product.
Influence research of the raw material volume Average Particle Diameters to canagliflozin tablet In Vitro Dissolution
Canagliflozin tablet prepared by above-mentioned 6 kinds of variable grains partial size raw material, carries out and the comparison of dissolution curve is investigated.
Study the canagliflozin tablet of variable grain partial size and the relationship of dissolution rate.
Dissolution measuring method of the present invention is using in two annex XC dissolution methods of Chinese Pharmacopoeia version in 2010
The second method, using 0.75% lauryl sodium sulfate aqueous solution as dissolution medium, dissolution medium volume be 900ml, revolving speed
It is 37 ± 0.5 DEG C for 75r/min, temperature.
It is found by comparative study, the volume average particle size of canagliflozin raw material controls between 2.5~30 μm, can be effective
Ensure the dissolution of product.
Detailed description of the invention
Fig. 1: the hardness of the canagliflozin tablet of Examples 1 to 6 preparation and the curve of tableting pressure
Fig. 2: the hardness of canagliflozin tablet prepared by embodiment 7~13 and the curve of tableting pressure
Fig. 3: dissolution of the canagliflozin tablet of Examples 1 to 6 preparation in 0.75% lauryl sodium sulfate aqueous solution
Curve
Fig. 4: the dissolution of canagliflozin tablet prepared by embodiment 7~13 in 0.75% lauryl sodium sulfate aqueous solution
Curve
Specific embodiment mode:
Following embodiments are for being explained further the present invention, it is not intended that the scope of the present invention is only limitted to following implementation
Example.
Embodiment 1 ~ 6
The prescription of embodiment 1 ~ 6 is shown in Table 1:
Preparation process:
1. taking the unformed form canagliflozin raw material for standby of above-mentioned volume average particle size；
2. it is spare that lactose, microcrystalline cellulose, croscarmellose sodium and magnesium stearate are crossed 80 meshes respectively；
3. by the bulk pharmaceutical chemicals of each embodiment, lactose, microcrystalline cellulose, 70% recipe quantity croscarmellose sodium and
The magnesium stearate of 70% recipe quantity is uniformly mixed, and the material of mixing is added dry granulation in dry granulating machine, particle obtained with
The croscarmellose sodium of the magnesium stearate of 30% recipe quantity and 30% recipe quantity mixes, and obtains semi-finished product；
4. measuring semi-finished product content, slice weight is calculated.According to semi-finished product content adjustment sheet weight piece, measured in tableting processes
Tablet hardness under each tableting pressure, and measure the friability of 6 kinds of tablets.
The prescription and preparation process of above embodiments 1 ~ 6 are completely the same, are only that the volume of bulk pharmaceutical chemicals canagliflozin is averaged grain
Diameter is different.
Tablet hardness measurement result of the canagliflozin tablet of Examples 1 to 6 preparation under different tableting pressures is shown in Table 2,
Change curve of the tablet hardness under different tableting pressures is shown in Fig. 1.
Table 2 the result shows that, raw material volume average grain diameter is 2.5 μm, 10 μm, 20 μm, 30 μm of canagliflozin tablet
Hardness increases with tableting pressure and is increased, and correlation is good；And the canagliflozin tablet that raw material volume average grain diameter is 50 μm
Hardness does not have correlation, and the hardness very little of tablet with tableting pressure substantially, is unable to satisfy normal production requirement；Unexpected
It is that when raw material volume average grain diameter is 1 μm, hardness and the tableting pressure of tablet also do not have correlation, and the hardness of tablet becomes
It is small, and occur sticking phenomenon in tableting processes, it is unable to satisfy normal production requirement.
The tablet measurement friability for taking above embodiments 1~6 to prepare under 25 KN tableting pressures, measurement result are shown in Table 3.
Table 3 the result shows that, the canagliflozin tablet friability of embodiment 2 ~ 5 meets Chinese Pharmacopoeia two pieces of version in 2010
The relevant regulations of agent friability；The canagliflozin tablet of embodiment 1 and embodiment 6 does not meet Chinese Pharmacopoeia two pieces of version in 2010
The relevant regulations of agent friability.
To sum up, present invention determine that canagliflozin volume average particle size control can effectively ensure to produce in 2.5 ~ 30 μ ms
The compressibility and hardness of product.
Embodiment 7 ~ 13
The prescription of embodiment 7 ~ 13 is shown in Table 4:
Preparation process:
1, the canagliflozin raw material for standby of above-mentioned volume average particle size is taken；
2, respectively by lactose, mannitol, starch, pregelatinized starch, microcrystalline cellulose, croscarmellose sodium, friendship
It is spare that connection povidone, sodium carboxymethyl starch, lauryl sodium sulfate, silica and magnesium stearate cross 80 meshes；
3, all auxiliary materials in above each prescription in addition to silica and magnesium stearate are uniformly mixed respectively, the object of mixing
Dry granulation in dry granulating machine is added in material, and the silica of respective recipe quantity is added in particle obtained and magnesium stearate mixes,
Obtain semi-finished product；
4, semi-finished product content is measured, slice weight is calculated.According to semi-finished product content adjustment sheet weight piece to get embodiment 6 ~ 12
Canagliflozin tablet.
The tablet hardness measurement result of canagliflozin tablet prepared by embodiment 7~13 under different tableting pressures is shown in Table 5,
Change curve of the tablet hardness under different tableting pressures is shown in Fig. 2.
The above table 5 the result shows that, by the control of raw material volume average grain diameter in 2.5~30 selected μ ms, preparation
Canagliflozin tablet hardness with tableting pressure increase and increase, correlation is good, and tablet hardness can have by tableting pressure
Effect control.
The tablet measurement friability for taking above embodiments 7~13 to prepare under 25 KN tableting pressures, measurement result are shown in Table 6.
The above table 6 the result shows that, the canagliflozin tablet friability of embodiment 7 ~ 13 meets Chinese Pharmacopoeia version in 2010
The relevant regulations of two tablet friabilities.
The dissolution curve of the canagliflozin tablet of embodiment 1 ~ 6, which compares, to be investigated
The purpose that comparison is investigated is the optimal volume average grain diameter control range of determining tablet of the present invention.
It is canagliflozin tablet made from 1 ~ embodiment of embodiment 6 that the tablet selected is investigated in comparison.
Dissolution measuring method of the present invention is using in two annex XC dissolution methods of Chinese Pharmacopoeia version in 2010
The second method, dissolution medium uses 0.75% lauryl sodium sulfate aqueous solution, the dissolution medium volume to be for 900ml, revolving speed
75r/min, temperature are 37 ± 0.5 DEG C.
In 5,10,15,30,60min sampling, after 0.45 μm of the filtering with microporous membrane of dissolution fluid of taking-up, use is ultraviolet
Spectrophotometry canagliflozin content therein, and the dissolution rate at each time point is calculated, measurement result is shown in Table 7, and dissolution is bent
Line is shown in Fig. 3.
Table 7 the result shows that: the dissolution rate of canagliflozin tablet made from 2 ~ embodiment of embodiment 5 is preferable, and 30min's is molten
Out-degree reaches 90% or more；Canagliflozin Dissolution of Tablet made from embodiment 6 is poor, and the dissolution rate of 30min is also not up to
75%, it is unable to satisfy drug quality requirement.Surprisingly, canagliflozin tablet early period made from embodiment 1 dissolves out also very
Slowly, although the dissolution rate of 60min has reached 90% or more dissolution rate, but still it is unable to satisfy drug quality requirement.As it can be seen that will
The volume average particle size control of bulk pharmaceutical chemicals can effectively ensure that the dissolution rate of product in 2.5 ~ 30 μ ms.
The dissolution curve of the canagliflozin tablet of embodiment 7 ~ 13 is investigated
The measurement of canagliflozin tablet In Vitro Dissolution:
In Vitro Dissolution measuring method of the present invention is using in two annex XC dissolution methods of Chinese Pharmacopoeia version in 2010
Second method, dissolution medium use 0.75% lauryl sodium sulfate aqueous solution, dissolution medium volume for 900ml, revolving speed 75r/
Min, temperature are 37 ± 0.5 DEG C.
In 5,10,15,30,60min sampling, after 0.45 μm of the filtering with microporous membrane of dissolution fluid of taking-up, use is ultraviolet
Spectrophotometry canagliflozin content therein, and the dissolution rate at time point is calculated, measurement result is shown in Table 8, and dissolution is bent
Line is shown in Fig. 4.
The In Vitro Dissolution of 7 ~ embodiment of embodiment 13 of table 8 the result shows that: canagliflozin raw material is average in selected volume
In particle size range, using the tablet of identical (or different) prescription preparation, under identical leaching condition, In Vitro Dissolution behavior ten is tapped
Closely.
In summary the dissolution curve of embodiment 1-13 is investigated known to result: present invention determine that canagliflozin volume it is average
Size controlling can effectively ensure the dissolution of product in 2.5 ~ 30 μ ms.
Flexible modification is carried out on the basis of essence of the invention or simple modification also belongs to right of the invention and wants
The range asked.
Claims (7)
1. a kind of canagliflozin oral solid drug composition, contains canagliflozin and pharmaceutic adjuvant, wherein canagliflozin is nothing
Stereotypic morphological, mean particle size are 2.5~30 μm, and the pharmaceutic adjuvant includes filler and disintegrating agent, wherein described to fill out
Filling agent is microcrystalline cellulose, lactose, pregelatinized starch, mannitol, starch or their any mixture, and weight is combination
The 30% ~ 75% of object weight, the disintegrating agent be croscarmellose sodium, sodium carboxymethyl starch, crospovidone or it
Any mixture, weight is the 3% ~ 10% of composition weight, and the composition is tablet, and the composition passes through dry method
Granulation is made.
2. composition according to claim 1, the filler is microcrystalline cellulose, lactose or their any mixing
Object, the disintegrating agent are croscarmellose sodium.
3. composition according to claim 1, the weight of canagliflozin is the 12% ~ 60% of composition weight.
4. composition according to claim 1, the content of canagliflozin is 50 ~ 300mg.
5. composition according to claim 4, the content of canagliflozin is 100 ~ 300 mg.
6. composition according to claim 1, the pharmaceutic adjuvant is further comprised selected from one of the following or more
Kind surfactant: lauryl sodium sulfate, polysorbate, fatty acid sorbitan, poloxamer and Emulsifier EL-60.
7. a kind of method for preparing composition described in claim 1, comprising the following steps:
A) unformed canagliflozin is micronized, obtains the particle that average grain diameter is 2.5~30 μm；
B) canagliflozin is uniformly mixed with the pharmaceutic adjuvant containing filler and disintegrating agent；
C) it pelletizes；
D) addition mix lubricant is uniform, and tabletting obtains canagliflozin piece.
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| CN113648304A (en) * | 2021-09-06 | 2021-11-16 | 扬子江药业集团上海海尼药业有限公司 | Pharmaceutical composition containing dapagliflozin and preparation method and application thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102985075A (en) * | 2010-05-11 | 2013-03-20 | 田边三菱制药株式会社 | Canagliflozin containing tablets |
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| BR112013011404A2 (en) * | 2010-11-12 | 2016-08-02 | Procter & Gamble | elastomeric compositions that resist disintegration |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102985075A (en) * | 2010-05-11 | 2013-03-20 | 田边三菱制药株式会社 | Canagliflozin containing tablets |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11857559B2 (en) | 2018-09-10 | 2024-01-02 | Aurobindo Pharma Ltd. | Pharmaceutical composition comprising Canagliflozin, process of preparation and use thereof |
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| CN103655539A (en) | 2014-03-26 |
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