WO2013115743A1 - Effervescent tablet formulations comprising the combination of voglibose and metformin - Google Patents
Effervescent tablet formulations comprising the combination of voglibose and metformin Download PDFInfo
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- WO2013115743A1 WO2013115743A1 PCT/TR2013/000052 TR2013000052W WO2013115743A1 WO 2013115743 A1 WO2013115743 A1 WO 2013115743A1 TR 2013000052 W TR2013000052 W TR 2013000052W WO 2013115743 A1 WO2013115743 A1 WO 2013115743A1
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- effervescent
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0002—Galenical forms characterised by the drug release technique; Application systems commanded by energy
- A61K9/0007—Effervescent
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/133—Amines having hydroxy groups, e.g. sphingosine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
Definitions
- the present invention relates to pharmaceutical formulations comprising voglibose and metformin that shall be used in the treatment of diabetes.
- Voglibose was first disclosed in the application numbered EP0056194 (Bl).
- the a-glucosidase inhibitor voglibose is effective in slowing carbohydrate metabolism, in removing hyperglycaemic symptoms and in the treatment of patients with metabolic disorders and it has a role in prevention of high blood sugar level and it is used in the treatment of diabetes.
- Metformin on the other hand, was first disclosed in the application numbered US3174901 (A). In said document, it was disclosed that metformin is effective in the treatment of diabetes.
- Metformin is available in 500, 850, 1000 mg film coated tablet forms on the market.
- an alpha glucosidase inhibitor voglibose prevents digestion of polysaccharides and due to undigested polysaccharides in the intestine, flatulence, diarrhea and similar digestive system complaints are frequently observed in the patients.
- the present invention relates to effervescent tablet formulations comprising voglibose and metformin hydrochloride as the active agent.
- the present invention relates to effervescent formulations comprising voglibose-metformin hydrochloride combination, effervescent couple comprising at least one effervescent acid and at least one effervescent base and at least one pharmaceutically acceptable excipient.
- the present invention relates to selection of effervescent acid and base constituting the effervescent couple from a specific group of substances for the effervescent tablet formulations comprising voglibose-metformin hydrochloride combination.
- At least one pharmaceutically acceptable effervescent acid that can be used in said voglibose- metformin hydrochloride formulations is selected from a group comprising organic acids such as malic acid, citric acid, tartaric acid, fumaric acid.
- physico-chemical parameters such as tablet dispersion time and tablet hardness vary according to the excipients and their amounts used in the effervescent tablet formulations.
- the dosage forms obtained may crumble quickly and be broken during packaging, storing and carrying.
- Hard tablets on the other hand, take long to dissolve. Long dissolution time is an important problem especially for formulations in effervescent form.
- the effervescent couple comprising citric acid as the effervescent acid and an effervescent base selected from a specific group of effervescent bases provides said physico-chemical characteristics.
- the present invention relates to effervescent tablet formulations comprising voglibose-metformin hydrochloride combination and effervescent couple that is composed of citric acid as the effervescent acid and an effervescent base selected from a specific group of effervescent bases.
- At least one pharmaceutically acceptable effervescent base that can be used in said voglibose- metformin hydrochloride formulations is selected from a group comprising sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate.
- the effervescent base is preferably selected from bicarbonates; preferably it is potassium hydrogen carbonate.
- the inventors have obtained ideal tablet dispersion time and hardness by using citric acid in the range of 30 to 55%, preferably in the range of 35 to 50% in proportion to weight of unit formulation in the effervescent tablet formulations comprising voglibose-metformin hydrochloride combination.
- a characteristic feature of the present invention relates to effervescent tablet formulations comprising voglibose-metformin hydrochloride combination wherein citric acid is used in the range of 30 to 55%, preferably in the range of 35 to 50% in proportion to weight of unit formulation.
- the moisture ratio of citric acid that shall be used in the formulations of the present invention varies in the range of 0.01% to 0.3%, preferably in the range of 0.05 to 01%.
- the hardness of the tablets obtained from said formulations varies in the range of 3 to 15 kP, preferably in the range of 5 to 10 kP. It was observed that effervescent tablets comprising voglibose and metformin hydrochloride having said hardness value are durable under abrasive conditions such as carrying, production, etc. as well as they can disperse in a short time.
- the inventors have obtained a pharmaceutical mixture that can remain homogeneous during production and also disperse in a short time, for instance in less than 5 minutes by using effervescent acid having a specific particle size in said effervescent tablet formulations.
- citric acid having a dso value in the range of 100 to 250 ⁇ , preferably in the range of 150 to 200 ⁇ and a d9 0 value in the range of 280 to 380 ⁇ , preferably in the range of 300 to 350 ⁇ has a positive effect on dispersion of the formulation.
- d 5 o signifies that half of the said substance by volume has a particle size over the value stated with d 50 and other half of the substance has a particle size below the value stated with d5o.
- d ⁇ signifies that 90% of the said substance by volume has a particle size below the value stated with dgo and 10% of the substance has a particle size over the value stated with d 0.
- D50 and dgs values can be measured with one of the known measuring devices, for instance with a device which measures particle distribution by laser diffraction (for instance, Malvern Mastersizer etc.).
- the present invention relates to effervescent tablet formulations comprising voglibose-metformin hydrochloride combination, wherein citric acid having a d 5 o value in the range of 100 to 250 ⁇ , preferably in the range of 150 to 200 ⁇ and a dcio value in the range of 280 to 380 ⁇ , preferably in the range of 300 to 350 ⁇ and a moisture ratio in the range of 0.01% to 0.3%, preferably in the range of 0.05% to 0.1%, is used in the range of 30 to 55%, preferably in the range of 35 to 50% in proportion to total weight of unit formulation.
- the ratio of the effervescent base to citric acid constituting the effervescent couple is in the range of 1:1 to 1 :3, preferably in the range of 1:1.5 to 1 :2.
- At least one pharmaceutically acceptable excipient that can be used in addition to effervescent couple in voglibose-metformin formulations of the present invention can be selected from a group comprising diluent, binder, lubricant, flavouring agent and glidant.
- the diluent that can be used in said formulations is selected from a group comprising calcium carbonate, dibasic calcium phosphate, tribasic calcium phosphate, calcium sulphate, microcrystalline cellulose, dextrose, fructose, lactitol, lactose, magnesium carbonate, magnesium oxide, maltitol, maltodextrin, maltose, mannitol, simethicone, sorbitol, starch, sodium chloride, sucrose, talc, xylitol.
- the binder that can be used in said formulations can be selected from a group comprising carboxymethyl cellulose sodium, ethyl cellulose, gelatine, hydroxyethyl cellulose, hydroxymethyl cellulose, hydroxypropyl cellulose, hypromellose, magnesium aluminium silicate, maltodextrin, methylcellulose, povidone, starch.
- the lubricant that can be used in said formulations can be selected from a group comprising calcium stearate, magnesium stearate, polyethylene glycol, sodium benzoate, potassium benzoate, sodium lauryl sulphate, talc, stearic acid, zinc stearate.
- the flavouring agent that can be used in said formulations can be selected from blackberry, menthol, lemon, orange, vanilla, strawberry, raspberry, caramel and similar flavours.
- the glidant that can be used in said formulations is selected from a group comprising tribasic calcium phosphate, colloidal silicone dioxide, magnesium silicate, magnesium trisilicate, talc.
- the formulations of the present invention are preferably prepared by wet granulation method.
- wet granulation method two active agents are mixed with the excipients for a length of time.
- the mixture obtained is granulated with the granulation solution and the granules are dried. After this phase, the diluent and the lubricant are added and mixed again.
- the mixture obtained is compressed in tablet form and packaged.
- Example 1 Formulation for Preparation of Effervescent Tablets Comprising Voglibose and Metformin.
- excipients 3.490 The formulation given above is prepared by wet granulation method. Firstly, the effervescent couple and the active agents are mixed. The granulation solution comprising at least one excipient and water is added into this solution. The mixture obtained is dried. The granules obtained are sieved and mixed with the other excipients. In the last step, tablet compression and packaging processes are realized.
- Example 2 Formulation for Preparation of Effervescent Sachets Comprising Voglibose and Metformin.
- the formulation given above is prepared by wet granulation method. Firstly, the effervescent couple and active agents are mixed. The granulation solution comprising at least one excipient and water is added into this mixture. The mixture obtained is dried. The granules obtained are sieved and mixed with the other excipients. The formulation obtained is filled into sachets.
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Abstract
The present invention relates to effervescent formulations comprising voglibose-metformin hydrochloride combination, an effervescent couple comprising at least one effervescent acid and at least one effervescent base and at least one pharmaceutically acceptable excipient.
Description
EFFERVESCENT TABLET FORMULATIONS COMPRISING THE
COMBINATION OF VOGLIBOSE AND METFORMIN
The present invention relates to pharmaceutical formulations comprising voglibose and metformin that shall be used in the treatment of diabetes. Voglibose was first disclosed in the application numbered EP0056194 (Bl).
In said document, it was disclosed that the a-glucosidase inhibitor voglibose is effective in slowing carbohydrate metabolism, in removing hyperglycaemic symptoms and in the treatment of patients with metabolic disorders and it has a role in prevention of high blood sugar level and it is used in the treatment of diabetes.
Metformin, on the other hand, was first disclosed in the application numbered US3174901 (A). In said document, it was disclosed that metformin is effective in the treatment of diabetes.
Metformin is available in 500, 850, 1000 mg film coated tablet forms on the market.
It is usually preferred to use combined drug treatments in treatment of type 2 diabetes. However, use of these drugs in different dosage forms makes treatment compliance difficult especially for elderly patients. This problem was tried to be solved by combining the active agents in a single dosage form.
During formulating the two active agents with different excipients, they interact with each other and this affects pharmacological characteristics of the active agents negatively and prevents the desired pharmaceutical effect.
In addition, when the formulations comprising high amounts of different active agents are mixed with the excipients in order to provide the required physical characteristics, they become quite large in volume and it complicates use of the drug and therefore compliance of the patient to the treatment. In other aspect, an alpha glucosidase inhibitor voglibose prevents digestion of polysaccharides and due to undigested polysaccharides in the intestine, flatulence, diarrhea and similar digestive system complaints are frequently observed in the patients.
As a result of the studies they conducted, the inventors have surprisingly observed that said problems can be overcome in the case that the formulations comprising voglibose and metformin hydrochloride combination are in effervescent tablet form.
According to this, the present invention relates to effervescent tablet formulations comprising voglibose and metformin hydrochloride as the active agent.
In another aspect, the present invention relates to effervescent formulations comprising voglibose-metformin hydrochloride combination, effervescent couple comprising at least one effervescent acid and at least one effervescent base and at least one pharmaceutically acceptable excipient.
In another aspect, the present invention relates to selection of effervescent acid and base constituting the effervescent couple from a specific group of substances for the effervescent tablet formulations comprising voglibose-metformin hydrochloride combination. At least one pharmaceutically acceptable effervescent acid that can be used in said voglibose- metformin hydrochloride formulations is selected from a group comprising organic acids such as malic acid, citric acid, tartaric acid, fumaric acid. In other aspect, physico-chemical parameters such as tablet dispersion time and tablet hardness vary according to the excipients and their amounts used in the effervescent tablet formulations. Due to the tablets that do not have sufficient hardness, the dosage forms obtained may crumble quickly and be broken during packaging, storing and carrying. Hard tablets, on the other hand, take long to dissolve. Long dissolution time is an important problem especially for formulations in effervescent form. As a result of the studies conducted during preparation of the effervescent tablet formulation, the inventor has found that the selection of the effervescent acid and base has an effect on dispersion time and hardness of the tablet made with these formulations. Consequently, it has been seen that the effervescent couple comprising citric acid as the
effervescent acid and an effervescent base selected from a specific group of effervescent bases provides said physico-chemical characteristics.
According to this, in another aspect, the present invention relates to effervescent tablet formulations comprising voglibose-metformin hydrochloride combination and effervescent couple that is composed of citric acid as the effervescent acid and an effervescent base selected from a specific group of effervescent bases.
At least one pharmaceutically acceptable effervescent base that can be used in said voglibose- metformin hydrochloride formulations is selected from a group comprising sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate. The effervescent base is preferably selected from bicarbonates; preferably it is potassium hydrogen carbonate.
The inventors have obtained ideal tablet dispersion time and hardness by using citric acid in the range of 30 to 55%, preferably in the range of 35 to 50% in proportion to weight of unit formulation in the effervescent tablet formulations comprising voglibose-metformin hydrochloride combination.
According to this, a characteristic feature of the present invention relates to effervescent tablet formulations comprising voglibose-metformin hydrochloride combination wherein citric acid is used in the range of 30 to 55%, preferably in the range of 35 to 50% in proportion to weight of unit formulation. The moisture ratio of citric acid that shall be used in the formulations of the present invention varies in the range of 0.01% to 0.3%, preferably in the range of 0.05 to 01%.
The hardness of the tablets obtained from said formulations varies in the range of 3 to 15 kP, preferably in the range of 5 to 10 kP. It was observed that effervescent tablets comprising voglibose and metformin hydrochloride having said hardness value are durable under abrasive conditions such as carrying, production, etc. as well as they can disperse in a short time.
The inventors have obtained a pharmaceutical mixture that can remain homogeneous during production and also disperse in a short time, for instance in less than 5 minutes by using effervescent acid having a specific particle size in said effervescent tablet formulations.
According to this, the inventors have found that use of citric acid having a dso value in the range of 100 to 250 μπι, preferably in the range of 150 to 200 μπι and a d90 value in the range
of 280 to 380 μηι, preferably in the range of 300 to 350 μιη has a positive effect on dispersion of the formulation.
The term d5o signifies that half of the said substance by volume has a particle size over the value stated with d50 and other half of the substance has a particle size below the value stated with d5o.
The term d^ signifies that 90% of the said substance by volume has a particle size below the value stated with dgo and 10% of the substance has a particle size over the value stated with d 0.
D50 and dgs values can be measured with one of the known measuring devices, for instance with a device which measures particle distribution by laser diffraction (for instance, Malvern Mastersizer etc.).
According to this, the present invention relates to effervescent tablet formulations comprising voglibose-metformin hydrochloride combination, wherein citric acid having a d5o value in the range of 100 to 250 μπι, preferably in the range of 150 to 200 μπι and a dcio value in the range of 280 to 380 μιη, preferably in the range of 300 to 350 μιη and a moisture ratio in the range of 0.01% to 0.3%, preferably in the range of 0.05% to 0.1%, is used in the range of 30 to 55%, preferably in the range of 35 to 50% in proportion to total weight of unit formulation.
Another characteristic feature of said invention is that the ratio of the effervescent base to citric acid constituting the effervescent couple is in the range of 1:1 to 1 :3, preferably in the range of 1:1.5 to 1 :2. At least one pharmaceutically acceptable excipient that can be used in addition to effervescent couple in voglibose-metformin formulations of the present invention can be selected from a group comprising diluent, binder, lubricant, flavouring agent and glidant.
The diluent that can be used in said formulations is selected from a group comprising calcium carbonate, dibasic calcium phosphate, tribasic calcium phosphate, calcium sulphate, microcrystalline cellulose, dextrose, fructose, lactitol, lactose, magnesium carbonate, magnesium oxide, maltitol, maltodextrin, maltose, mannitol, simethicone, sorbitol, starch, sodium chloride, sucrose, talc, xylitol.
The binder that can be used in said formulations can be selected from a group comprising carboxymethyl cellulose sodium, ethyl cellulose, gelatine, hydroxyethyl cellulose,
hydroxymethyl cellulose, hydroxypropyl cellulose, hypromellose, magnesium aluminium silicate, maltodextrin, methylcellulose, povidone, starch.
The lubricant that can be used in said formulations can be selected from a group comprising calcium stearate, magnesium stearate, polyethylene glycol, sodium benzoate, potassium benzoate, sodium lauryl sulphate, talc, stearic acid, zinc stearate.
The flavouring agent that can be used in said formulations can be selected from blackberry, menthol, lemon, orange, vanilla, strawberry, raspberry, caramel and similar flavours.
The glidant that can be used in said formulations is selected from a group comprising tribasic calcium phosphate, colloidal silicone dioxide, magnesium silicate, magnesium trisilicate, talc.
The formulations of the present invention are preferably prepared by wet granulation method. In wet granulation method, two active agents are mixed with the excipients for a length of time. The mixture obtained is granulated with the granulation solution and the granules are dried. After this phase, the diluent and the lubricant are added and mixed again. The mixture obtained is compressed in tablet form and packaged. The examples for the formulations of the present invention are given below.
Example 1 : Formulation for Preparation of Effervescent Tablets Comprising Voglibose and Metformin.
Component name Amount fbv weight %)
Active agent
Voglibose 0.007
Metformin Hydrochloride 35.700
ExciDients
Citric Acid 36.303
Effervescent base 21.700
Binder 2.800
Other excipients 3.490
The formulation given above is prepared by wet granulation method. Firstly, the effervescent couple and the active agents are mixed. The granulation solution comprising at least one excipient and water is added into this solution. The mixture obtained is dried. The granules obtained are sieved and mixed with the other excipients. In the last step, tablet compression and packaging processes are realized.
Example 2: Formulation for Preparation of Effervescent Sachets Comprising Voglibose and Metformin.
The formulation given above is prepared by wet granulation method. Firstly, the effervescent couple and active agents are mixed. The granulation solution comprising at least one excipient and water is added into this mixture. The mixture obtained is dried. The granules obtained are sieved and mixed with the other excipients. The formulation obtained is filled into sachets.
Claims
1. A formulation comprising voglibose and metformin hydrochloride combination, characterized in that said formulation
- comprises an effervescent couple which is composed of at least one effervescent acid and at least one effervescent base and
- at least one pharmaceutically acceptable excipient and
- is in effervescent form.
2. The formulation according to claim 1, wherein the effervescent acid is selected from a group comprising organic acids such as malic acid, citric acid, tartaric acid, furnaric acid.
3. The formulation according to claims 1-2, wherein the effervescent acid is citric acid.
4. The formulation according to claims 1-3, wherein the effervescent base is selected from a group comprising the agents such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate.
5. The formulation according to claims 1-4, wherein the effervescent base is potassium hydrogen carbonate.
6. The formulation according to claims 3-5, wherein said formulation comprises citric acid in the range of 30 to 55% in proportion to weight of unit formulation.
7. The formulation according to claims 3-6, wherein said formulation comprises citric acid in the range of 35 to 50% in proportion to weight of unit formulation.
8. The formulation according to claims 3-7, wherein said formulation comprises citric acid having a d50 value in the range of 100 to 250 μηι and a d90 value in the range of 280 to 380 μπι.
9. The formulation according to claims 3-8, wherein said formulation comprises citric acid having a d50 value in the range of 150 to 200 μηι and a d90 value in the range of 300 to 350 μιη.
10. The formulation according to claims 3-9, wherein the moisture ratio of citric acid comprised in said formulation is in the range of 0.01% to 0.3%.
11. The formulation according to claims 3-10, wherein the moisture ratio of citric acid comprised in said formulation is in the range of 0.05% to 0.1%.
12. The effervescent tablet formulation comprising the voglibose-metformin hydrochloride combination, characterized in that said formulation comprises citric acid having a d50 value in the range of 100 to 250 μηι, a d90 value in the range of in the range of 280 to 380 μιη and a moisture ratio in the range of 0.01% to 0.3%, in the range of 30 to 55% in proportion to weight of unit formulation, and at least one effervescent base and at least one pharmaceutically acceptable excipient.
13. The formulation according to claims 3-12, wherein the ratio of effervescent base to citric acid constituting the effervescent couple is in the range of 1 : 1 tol :3 by weight.
14. The formulation according to claims 1-13, wherein the ratio of effervescent base to citric acid constituting the effervescent couple is in the range of 1 : 1.5 to 1 :2 by weight.
15. The formulation according to claims 1-14, wherein at least one pharmaceutically acceptable excipient that can be used in addition to effervescent couple is selected from a group comprising diluent, binder, lubricant, flavouring agent and glidant.
16. The formulation according to claims 1-15, wherein the diluent is selected from a group comprising calcium carbonate, dibasic calcium phosphate, tribasic calcium phosphate, calcium sulphate, microcrystalline cellulose, dextrose, fructose, lactitol, lactose, magnesium carbonate, magnesium oxide, maltitol, maltodextrin, maltose, mannitol, simethicone, sorbitol, starch, sodium chloride, sucrose, talc, xylitol.
17. The formulation according to claims 1-16, wherein the binder can be selected from a group comprising carboxymethyl cellulose sodium, ethyl cellulose, gelatine, hydroxyethyl cellulose, hydroxymethyl cellulose, hydroxypropyl cellulose, hypromellose, magnesium aluminium silicate, maltodextrin, methyl cellulose, povidone, starch.
18. The formulation according to claims 1-17, wherein the lubricant can be selected from a group comprising calcium stearate, magnesium stearate, polyethylene glycol, sodium benzoate, potassium benzoate, sodium lauryl sulphate, talc, stearic acid, zinc stearate.
19. The formulation according to claims 1-18, wherein the flavouring agent can be selected from blackberry, menthol, lemon, orange, vanilla, strawberry, raspberry, caramel and similar flavours.
20. The formulation according to claims 1-19, wherein glidant is selected from a group comprising tribasic calcium phosphate, colloidal silicone dioxide, magnesium silicate, magnesium trisilicate, talc.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13714364.0A EP2809311A1 (en) | 2012-01-31 | 2013-01-31 | Effervescent tablet formulations comprising the combination of voglibose and metformin |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| TR201201094 | 2012-01-31 | ||
| TR2012/01094 | 2012-01-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2013115743A1 true WO2013115743A1 (en) | 2013-08-08 |
Family
ID=48048164
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/TR2013/000052 WO2013115743A1 (en) | 2012-01-31 | 2013-01-31 | Effervescent tablet formulations comprising the combination of voglibose and metformin |
Country Status (2)
| Country | Link |
|---|---|
| EP (1) | EP2809311A1 (en) |
| WO (1) | WO2013115743A1 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015040460A1 (en) * | 2013-09-21 | 2015-03-26 | Effrx Pharmaceuticals Sa | Low-sodium effervescent pharmaceutical formulations |
| US20180325823A1 (en) * | 2015-11-12 | 2018-11-15 | Sensidose Ab | Compacted powder |
| WO2021054912A1 (en) * | 2019-09-16 | 2021-03-25 | Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi | Effervescent tablet formulations comprising dapagliflozin and metformin |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3174901A (en) | 1963-01-31 | 1965-03-23 | Jan Marcel Didier Aron Samuel | Process for the oral treatment of diabetes |
| EP0056194B1 (en) | 1981-01-05 | 1984-09-12 | Takeda Chemical Industries, Ltd. | N-substituted pseudo-aminosugars, their production and use |
| EP0203768A2 (en) * | 1985-05-31 | 1986-12-03 | Warner-Lambert Company | A therapeutic effervescent composition and a method of preparing the same |
| EP0396972A2 (en) * | 1989-05-09 | 1990-11-14 | Bayer Ag | An aqueous granulation solution and a method of tablet granulation |
| CN101590007A (en) * | 2008-05-27 | 2009-12-02 | 北京瑞伊人科技发展有限公司 | A kind of metformin hydrochloride/voigelibo sugar-lowering oral preparation compositions and preparation thereof |
| WO2011093823A2 (en) * | 2010-01-29 | 2011-08-04 | Mahmut Bilgic | Effervescent formulations comprising cefaclor and clavulanic acid |
-
2013
- 2013-01-31 EP EP13714364.0A patent/EP2809311A1/en not_active Withdrawn
- 2013-01-31 WO PCT/TR2013/000052 patent/WO2013115743A1/en active Application Filing
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3174901A (en) | 1963-01-31 | 1965-03-23 | Jan Marcel Didier Aron Samuel | Process for the oral treatment of diabetes |
| EP0056194B1 (en) | 1981-01-05 | 1984-09-12 | Takeda Chemical Industries, Ltd. | N-substituted pseudo-aminosugars, their production and use |
| EP0203768A2 (en) * | 1985-05-31 | 1986-12-03 | Warner-Lambert Company | A therapeutic effervescent composition and a method of preparing the same |
| EP0396972A2 (en) * | 1989-05-09 | 1990-11-14 | Bayer Ag | An aqueous granulation solution and a method of tablet granulation |
| CN101590007A (en) * | 2008-05-27 | 2009-12-02 | 北京瑞伊人科技发展有限公司 | A kind of metformin hydrochloride/voigelibo sugar-lowering oral preparation compositions and preparation thereof |
| WO2011093823A2 (en) * | 2010-01-29 | 2011-08-04 | Mahmut Bilgic | Effervescent formulations comprising cefaclor and clavulanic acid |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015040460A1 (en) * | 2013-09-21 | 2015-03-26 | Effrx Pharmaceuticals Sa | Low-sodium effervescent pharmaceutical formulations |
| US20180325823A1 (en) * | 2015-11-12 | 2018-11-15 | Sensidose Ab | Compacted powder |
| US11040013B2 (en) * | 2015-11-12 | 2021-06-22 | Sensidose Ab | Compacted powder |
| WO2021054912A1 (en) * | 2019-09-16 | 2021-03-25 | Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi | Effervescent tablet formulations comprising dapagliflozin and metformin |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2809311A1 (en) | 2014-12-10 |
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