WO2014067501A1 - Dispersible tablets containing deferasirox - Google Patents
Dispersible tablets containing deferasirox Download PDFInfo
- Publication number
- WO2014067501A1 WO2014067501A1 PCT/CZ2013/000138 CZ2013000138W WO2014067501A1 WO 2014067501 A1 WO2014067501 A1 WO 2014067501A1 CZ 2013000138 W CZ2013000138 W CZ 2013000138W WO 2014067501 A1 WO2014067501 A1 WO 2014067501A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- disintegrant
- pharmaceutically acceptable
- dispersible tablet
- tablet according
- deferasirox
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
Classifications
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4196—1,2,4-Triazoles
-
- 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
-
- 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/2027—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
-
- 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
Definitions
- the present invention relates to dispersible tablets containing 4-[3,5-bis(2-hydroxyphenyl)- lH-[l,2,4]triazol-l-yl]benzoic acid or its pharmaceutically acceptable salts or crystalline forms and a combination of at least two disintegrants that have the same or different chemical composition and a different average size of particles while the total amount of the disintegrant in a tablet is more than 35% by weight.
- Deferasirox is an orally active iron chelator that is indicated for treatment of iron overload in patients with anemia treated by blood transfusions, in specific cases for beta thalassemia, thalassemia intermedia and for sickle cell anemia to reduce morbidity and mortality caused by iron, and is also used to treat haemochromatosis.
- the patent application WO2004/035026A describes dispersible tablets containing 5 to 40% by weight of deferasirox or its pharmaceutically acceptable salts and at least one disintegrant in the amount of 10% to 35% by weight.
- the dispersible tablets are preferably prepared by wet granulation, which improves the physical characteristics of the drug, or the active substance, respectively, especially its poor flowability and sticking tendency.
- the description emphasizes that even with the use of wet granulation the active component keeps sticking and is difficult to handle during tabletting.
- This problem was solved by adding a lubricant to the tabletting mixtures.
- a lubricant in amounts exceeding 0.2% by weight made the disintegration of dispersible tablets longer than 3 minutes. For this reason the lubricant is not added to the mixture, but is directly sprayed onto the punches of the tabletting machine in amounts lower than 0.2% by weight in order to meet the requirement of the European Pharmacopoeia for disintegration, which should be shorter than 3 minutes.
- dispersible tablets containing deferasirox a combination of at least two disintegrants that have the same or different chemical composition and a different average size of particles, while the total amount of the disintegrant in a tablet is more than 35% by weight, and one or more pharmaceutically acceptable excipients have reduced the disintegration time of tablets and exhibited acceptable hardness and abrasion.
- a lubricant added in an amount of up to 2% by weight has no significant impact on the disintegration time of the tablet and improves processability of the active substance and excipients.
- the present invention provides a dispersible tablet containing deferasirox, its pharmaceutically acceptable salts or crystalline forms, a combination of at least two disintegrants that have the same or different chemical composition and a different average size of particles, the total amount of the disintegrant in the a tablet being more than 35% by weight, and one or more pharmaceutically acceptable excipients.
- the dispersible tablet contains a combination of at least two disintegrants that have the same or different chemical composition where the average particle size of the first disintegrant is less than 75 ⁇ and the average particle size of the other disintegrant is more than 75 ⁇ and less than 400 ⁇ , preferably, the particle size of the first disintegrant is smaller than 50 ⁇ , preferably smaller than 15 ⁇ and the average particle size of the other disintegrant is from 100 ⁇ to 400 ⁇ , preferably from 110 ⁇ to 140 ⁇ .
- the dispersible tablet contains deferasirox, its pharmaceutically acceptable salts or crystalline forms in an amount of from 15% by weight to 40% by weight.
- the tablet preferably contains 25 - 35% by weight of deferasirox, its pharmaceutically acceptable salt or crystalline form.
- the dispersible table contains the first and second disintegrant in a total amount of from 40% by weight to 58% by weight.
- the first disintegrant with the particle size of less than 75 um is crospovidone, sodium starch glycolate, corn starch, sodium crosscarmellose or low-substituted hydroxypropyl cellulose.
- the average particle size of examples of suitable disintegrants is presented in the table below.
- the other disintegrant exhibiting an average particle size of more than 75 ⁇ and less than 400 ⁇ is crospovidone.
- suitable variants of crospovidone with average particle sizes are presented in the table below.
- the dispersible tablet further contains one or more pharmaceutically acceptable excipients comprising fillers, wetting agents, glidants and lubricants.
- Suitable wetting agents are sodium lauryl sulphate, polysorbates, poloxamer, quaternary ammonium salts or any combinations thereof.
- the average particle size of the first disintegrant is 75 ⁇ , preferably less than 50 ⁇ , most preferably less than 15 ⁇ , and the average particle size of the other disintegrant is from 75 ⁇ to 400 ⁇ , preferably from 100 ⁇ to 400 ⁇ , most preferably from 110 ⁇ to 140 ⁇ .
- the dispersible tablets have a two-phase structure consisting of:
- the disintegration time of the dispersible tablets in aqueous solutions is shorter than 3 minutes.
- Crospovidone Polyplasdone XL 8.89
- Crospovidone (Kollidon CL-M) 2.95
- Example 3c Dispersible tablet formulation containing 1.99% by weight of magnesium stearate:
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Medicinal Preparation (AREA)
Abstract
The present invention relates to dispersible tablets containing 4-[3,5-bis(2-hydroxyphenyl)- 1H-[1,2,4]triazol-1-yl] benzoic acid (deferasirox), or its pharmaceutically acceptable salts or crystalline forms, and a combination of at least two disintegrants that have the same or different chemical composition and different average sizes of particles, the total amount of the disintegrant in the tablet being more than 35% by weight.
Description
Dispersible tablets containing deferasirox
Technical Field
The present invention relates to dispersible tablets containing 4-[3,5-bis(2-hydroxyphenyl)- lH-[l,2,4]triazol-l-yl]benzoic acid or its pharmaceutically acceptable salts or crystalline forms and a combination of at least two disintegrants that have the same or different chemical composition and a different average size of particles while the total amount of the disintegrant in a tablet is more than 35% by weight.
Background Art -[3,5-bis(2-hydroxyphenyl)-lH-[l,2,4] triazol-l-yl]benzoic acid (also known as deferasirox)
It has been unexpectedly found out that dispersible tablets containing deferasirox, a combination of at least two disintegrants that have the same or different chemical composition and a different average size of particles, while the total amount of the disintegrant in a tablet is more than 35% by weight, and one or more pharmaceutically acceptable excipients have reduced the disintegration time of tablets and exhibited acceptable hardness and abrasion. In addition, a lubricant added in an amount of up to 2% by weight has no significant impact on the disintegration time of the tablet and improves processability of the active substance and excipients.
Disclosure of Invention The present invention provides a dispersible tablet containing deferasirox, its pharmaceutically acceptable salts or crystalline forms, a combination of at least two disintegrants that have the same or different chemical composition and a different average size of particles, the total amount of the disintegrant in the a tablet being more than 35% by weight, and one or more pharmaceutically acceptable excipients.
In accordance with this invention the dispersible tablet contains a combination of at least two disintegrants that have the same or different chemical composition where the average particle size of the first disintegrant is less than 75 μπι and the average particle size of the other disintegrant is more than 75 μιη and less than 400 μπι, preferably, the particle size of the first disintegrant is smaller than 50 μιη, preferably smaller than 15 μιη and the average particle size of the other disintegrant is from 100 μπι to 400 μηι, preferably from 110 μπι to 140 μπι.
The dispersible tablet contains deferasirox, its pharmaceutically acceptable salts or crystalline forms in an amount of from 15% by weight to 40% by weight. The tablet preferably contains 25 - 35% by weight of deferasirox, its pharmaceutically acceptable salt or crystalline form. The dispersible table contains the first and second disintegrant in a total amount of from 40% by weight to 58% by weight.
The ratio of the first and second disintegrant in the dispersible tablet is in the range from 1 :2 to 1:15, preferably in the range from 1:3 to 1:13.
The first disintegrant with the particle size of less than 75 um is crospovidone, sodium starch glycolate, corn starch, sodium crosscarmellose or low-substituted hydroxypropyl cellulose. The average particle size of examples of suitable disintegrants is presented in the table below.
The other disintegrant exhibiting an average particle size of more than 75 μηι and less than 400 μιη is crospovidone. Examples of suitable variants of crospovidone with average particle sizes are presented in the table below.
Disintegrant Average particle size [μηι]
Kollidon CL (BASF) 110-130
Polyplasdone XL (ISP) 110-140
Crospopharm type A 100
The dispersible tablet further contains one or more pharmaceutically acceptable excipients comprising fillers, wetting agents, glidants and lubricants.
Suitable fillers are microcrystalline cellulose, powdered cellulose, microcrystalline cellulose with added silicon dioxide, lactose, calcium carbonate, calcium hydrogen phosphate, calcium lactate, sugar alcohols and any mixtures thereof.
Suitable wetting agents are sodium lauryl sulphate, polysorbates, poloxamer, quaternary ammonium salts or any combinations thereof.
Suitable glidants and lubricants are silicon dioxide, colloidal silicon dioxide, stearic acid, talc, magnesium trisilicate, stearates (e.g. magnesium stearate), behenates, fumarates, hydrogenated vegetable oil, hydrogenated castor oil or any combinations thereof. The dispersible tablets preferably have a two-phase structure consisting of:
a) an inner phase containing deferasirox, its pharmaceutically acceptable salts or crystalline forms, the first disintegrant, one or more pharmaceutically acceptable excipients and b) an outer phase containing the other disintegrant and one or more pharmaceutically acceptable excipients.
The average particle size of the first disintegrant is 75 μπι, preferably less than 50 μιη, most preferably less than 15 μτη, and the average particle size of the other disintegrant is from 75 μπι to 400 μπι, preferably from 100 μπι to 400 μπι, most preferably from 110 μπι to 140 μπι. In another variant the dispersible tablets have a two-phase structure consisting of:
a) an inner phase containing deferasirox, its pharmaceutically acceptable salts or crystalline forms, the first disintegrant and a portion of the other disintegrant, one or more pharmaceutically acceptable excipients, and
b) an outer phase containing the remaining portion of the other disintegrant and one or more pharmaceutically acceptable excipients.
The average particle size of the first disintegrant is 75 urn, preferably less than 50 μηι, most preferably less than 15 μηι and the average particle size of the other disintegrant is from 75 μπι to 400 μπι, preferably from 100 μπι to 400 μπι, most preferably from 110 μιη to 140 μπι. According to the invention the dispersible tablets are prepared by dry granulation followed by compression of the granules into tablets.
The preparation method of the dispersible tablets consists of the following steps: a) mixing deferasirox, its pharmaceutically acceptable salts or crystalline forms, with the first disintegrant and/or a portion of the other disintegrant and at least one pharmaceutically acceptable excipient,
b) mixing the mixture produced in step a) with a portion of the lubricant,
c) dry granulation of the mixture produced in step b),
d) mixing the granules obtained in step c) with the other disintegrant, the remaining lubricant and at least one pharmaceutically acceptable excipient,
e) compressing the mixture obtained in step d) into tablets,
f) compressing the mixture obtained in step e) to form a tablet.
In accordance with the invention the disintegration time of the dispersible tablets in aqueous solutions (e.g. in water) is shorter than 3 minutes.
Examples
Dispersible tablets were prepared in the following way:
The constituents of the inner phase, deferasirox, crospovidone, microcrystalline cellulose, sodium lauryl sulphate and colloidal silicon dioxide were screened through a sieve with the mesh size of 1 mm and homogenized for 10 minutes. Then, magnesium stearate was added, the mixture was homogenized for 5 minutes and then it was compacted using a Gerteis roller compactor with a force of 1 - 10 k /cm2, preferably 2 - 7 kN/cm2. The produced material strips were ground and the obtained granules were mixed with the constituents of the outer phase, lactose and crosspovidone, and homogenized for 10 minutes. Then, the remaining magnesium stearate was added and this mixture was homogenized for 5 minutes. The resulting granulate was compressed into tablets.
Example 1: Dispersible tablets with the disintegration time of 02:50 min.
Dispersible tablets containing different amounts of magnesium stearate were prepared using the above mentioned preparation procedure.
Example 3a: Dispersible tablets containing 1% by weight of magnesium stearate:
Constituents % by weight
Inner phase Deferasirox 29.63
Crospovidone (Kollidon CL-M) 2.96
Crospovidone (Polyplasdone XL) 8.89
Microcrystalline cellulose 5.93
Sodium lauryl sulphate 0.44
Colloidal silicon dioxide 0.18
Magnesium stearate 0.41
Outer phase Lactose 21.33
Crospovidone (Polyplasdone XL) 29.63
Magnesium stearate 0.60
Example 3b: Dispersible tablet formulation containing 1.5^
stearate:
Constituents % by weight
Inner phase Deferasirox 29.49
Crospovidone (Kollidon CL-M) 2.95
Crospovidone (Polyplasdone XL) 8.85
Microcrystalline cellulose 5.90
Sodium lauryl sulphate 0.44
Colloidal silicon dioxide 0.18
Magnesium stearate 0.41
Outer phase Lactose 21.23
Crospovidone (Polyplasdone XL) 29.49
Magnesium stearate 1.06
Example 3c: Dispersible tablet formulation containing 1.99% by weight of magnesium stearate:
The results show that the amount of the lubricant does not have any critical impact on the disintegration time of the tablets if the tablets are produced in accordance with the invention, even tablets containing up to 2% by weight of the lubricant comply with the requirement for the disintegration time in accordance with the European Pharmacopoeia.
Claims
1. A dispersible tablet containing deferasirox, its pharmaceutically acceptable salts or crystalline forms, characterized in that it contains a combination of at least two disintegrants that have the same or different chemical composition and a different average size of particles and one or more pharmaceutically acceptable excipients , the first disintegrant having an average particle size smaller than 75 μηι and the other disintegrant having an average particle size of from 75 μιη to 400 um and the total amount of the disintegrant in the tablet being more than 35% by weight.
2. The dispersible tablet according to claim 1, characterized in that it contains deferasirox, its pharmaceutically acceptable salts or crystalline forms in an amount of from 15% by weight to 40% by weight.
3. The dispersible tablet according to claim 2, characterized in that it contains the first and second disintegrants in a total amount of from 40% to 58% by weight.
4. The dispersible tablet according to claims 1-3, characterized in that the ratio between the first and second disintegrants is in the range of from 1:2 to 1:15.
5. The dispersible tablet according to claim 4, characterized in that the ratio between the first and second disintegrants is in the range of from 1:3 to 1:13.
6. The dispersible tablet according to claims 1-5, characterized in that the average particle size of the first disintegrant is less than 50 μιη, preferably less than 15 μηι.
7. The dispersible tablet according to claims 1-6, characterized in that the average particle size of the other disintegrant is in the range of from 100 μπι to 400 μπι, preferably from 110 μιη ΐο 140 μηι.
8. The dispersible tablet according to claim 6, characterized in the first disintegrant is crospovidone, sodium starch glycolate, corn starch, sodium crosscarmellose or low-substituted hydroxypropyl cellulose.
9. The dispersible tablet according to claim 7, characterized in that the other disintegrant is crospovidone.
10. The dispersible tablet according to any one of the preceding claims, characterized in that the first disintegrant is crospovidone with an average particle size of less than 15 μιη, and the other disintegrant is crospovidone with an average particle size of from 110 μπι to 140 μιη.
11. The dispersible tablet according to any one of the preceding claims, characterized in that it has a two-phase structure consisting of:
a) an inner phase containing deferasirox, its pharmaceutically acceptable salt or crystalline form, the first disintegrant, one or more pharmaceutically acceptable excipients, and b) an outer phase containing the other disintegrant and one or more pharmaceutically acceptable excipients.
12. The dispersible tablet according to claims 1-10, characterized in that it has a two-phase structure consisting of:
a) an inner phase containing deferasirox, its pharmaceutically acceptable salt or crystalline form, the first disintegrant and a portion of the other disintegrant, one or more pharmaceutically acceptable excipients, and
b) an outer phase containing the remaining portion of the other disintegrant and one or more pharmaceutically acceptable excipients.
13. A method for the preparation of the dispersible tablet according to any one of the preceding claims, characterized in that it consists of:
a) mixing deferasirox, its pharmaceutically acceptable salts or crystalline forms with the first disintegrant, or the first disintegrant and a portion of the other disintegrant, and at least one pharmaceutically acceptable excipient,
b) mixing the mixture produced in step a) with a lubricant,
c) dry granulation of the mixture produced in step b),
d) mixing the granules obtained in step c) with the other disintegrant and at least pharmaceutically acceptable excipient,
e) mixing the mixture obtained in step d) with a lubricant,
f) compressing the mixture obtained in step e) to form a tablet.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CZ2012-743A CZ2012743A3 (en) | 2012-10-31 | 2012-10-31 | Dispersible tablets containing deferasirox |
| CZPV2012-743 | 2012-10-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2014067501A1 true WO2014067501A1 (en) | 2014-05-08 |
Family
ID=49641429
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/CZ2013/000138 Ceased WO2014067501A1 (en) | 2012-10-31 | 2013-10-25 | Dispersible tablets containing deferasirox |
Country Status (2)
| Country | Link |
|---|---|
| CZ (1) | CZ2012743A3 (en) |
| WO (1) | WO2014067501A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016114624A3 (en) * | 2015-01-16 | 2016-09-09 | 대원제약주식회사 | Suspension containing deferasirox |
| WO2019151967A3 (en) * | 2017-12-29 | 2019-10-17 | Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi | Water-dispersible tablet formulations comprising deferasirox |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090142395A1 (en) * | 2007-11-19 | 2009-06-04 | Uri Zadok | Deferasirox pharmaceutical compositions |
| WO2012003987A1 (en) * | 2010-07-08 | 2012-01-12 | Ratiopharm Gmbh | Oral dosage form of deferasirox |
-
2012
- 2012-10-31 CZ CZ2012-743A patent/CZ2012743A3/en unknown
-
2013
- 2013-10-25 WO PCT/CZ2013/000138 patent/WO2014067501A1/en not_active Ceased
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090142395A1 (en) * | 2007-11-19 | 2009-06-04 | Uri Zadok | Deferasirox pharmaceutical compositions |
| WO2012003987A1 (en) * | 2010-07-08 | 2012-01-12 | Ratiopharm Gmbh | Oral dosage form of deferasirox |
Non-Patent Citations (2)
| Title |
|---|
| ROWE ET AL.: "Handbook of Pharmaceutical Excipients Fourth Edition", 26 November 2002, PUBLISHER - SCIENCE AND PRACTICE, ROYAL PHARMACEUTICAL SOCIETY OF GREAT BRITAIN, London, UK, article "Cellulose, Microcrystalline", pages: 108 - 111, XP002719369 * |
| ROWE ET AL.: "Handbook of Pharmaceutical Excipients Fourth Edition", 26 November 2002, PUBLISHER - SCIENCE AND PRACTICE, ROYAL PHARMACEUTICAL SOCIETY OF GREAT BRITAIN, London, Uk, article "Crospovidone", pages: 184 - 184, XP002719370 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016114624A3 (en) * | 2015-01-16 | 2016-09-09 | 대원제약주식회사 | Suspension containing deferasirox |
| WO2019151967A3 (en) * | 2017-12-29 | 2019-10-17 | Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi | Water-dispersible tablet formulations comprising deferasirox |
Also Published As
| Publication number | Publication date |
|---|---|
| CZ2012743A3 (en) | 2014-05-07 |
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