RU2014125430A - CONTROLLED RELEASE OF PARTICLES CONTAINING DIMETHYLFUMARATE - Google Patents
CONTROLLED RELEASE OF PARTICLES CONTAINING DIMETHYLFUMARATE Download PDFInfo
- Publication number
- RU2014125430A RU2014125430A RU2014125430/15A RU2014125430A RU2014125430A RU 2014125430 A RU2014125430 A RU 2014125430A RU 2014125430/15 A RU2014125430/15 A RU 2014125430/15A RU 2014125430 A RU2014125430 A RU 2014125430A RU 2014125430 A RU2014125430 A RU 2014125430A
- Authority
- RU
- Russia
- Prior art keywords
- particle
- dimethyl fumarate
- particles
- hours
- coating
- Prior art date
Links
- 239000002245 particle Substances 0.000 title claims abstract 37
- LDCRTTXIJACKKU-ONEGZZNKSA-N dimethyl fumarate Chemical compound COC(=O)\C=C\C(=O)OC LDCRTTXIJACKKU-ONEGZZNKSA-N 0.000 title claims abstract 18
- 229960004419 dimethyl fumarate Drugs 0.000 title claims abstract 18
- 238000013270 controlled release Methods 0.000 title 1
- 229920000642 polymer Polymers 0.000 claims abstract 10
- 239000011248 coating agent Substances 0.000 claims abstract 7
- 238000000576 coating method Methods 0.000 claims abstract 7
- 230000001419 dependent effect Effects 0.000 claims abstract 6
- 238000004090 dissolution Methods 0.000 claims abstract 4
- 229920003145 methacrylic acid copolymer Polymers 0.000 claims abstract 4
- 239000011247 coating layer Substances 0.000 claims abstract 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims abstract 3
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims abstract 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims abstract 2
- 229920001800 Shellac Polymers 0.000 claims abstract 2
- 238000007922 dissolution test Methods 0.000 claims abstract 2
- 235000011389 fruit/vegetable juice Nutrition 0.000 claims abstract 2
- 210000004051 gastric juice Anatomy 0.000 claims abstract 2
- 229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 claims abstract 2
- 229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 claims abstract 2
- 229920000639 hydroxypropylmethylcellulose acetate succinate Polymers 0.000 claims abstract 2
- 238000000338 in vitro Methods 0.000 claims abstract 2
- 230000000968 intestinal effect Effects 0.000 claims abstract 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims abstract 2
- 229920000193 polymethacrylate Polymers 0.000 claims abstract 2
- 229940100467 polyvinyl acetate phthalate Drugs 0.000 claims abstract 2
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 claims abstract 2
- 239000004208 shellac Substances 0.000 claims abstract 2
- 229940113147 shellac Drugs 0.000 claims abstract 2
- 235000013874 shellac Nutrition 0.000 claims abstract 2
- 239000002552 dosage form Substances 0.000 claims 5
- 238000000034 method Methods 0.000 claims 4
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- 229920000623 Cellulose acetate phthalate Polymers 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 229940081734 cellulose acetate phthalate Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000010410 layer Substances 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 229940081735 acetylcellulose Drugs 0.000 abstract 1
- 229920002301 cellulose acetate Polymers 0.000 abstract 1
- 239000010802 sludge Substances 0.000 abstract 1
Classifications
-
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5005—Wall or coating material
- A61K9/5021—Organic macromolecular compounds
- A61K9/5026—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
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
- A61K31/225—Polycarboxylic acids
-
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5005—Wall or coating material
- A61K9/5021—Organic macromolecular compounds
- A61K9/5036—Polysaccharides, e.g. gums, alginate; Cyclodextrin
- A61K9/5042—Cellulose; Cellulose derivatives, e.g. phthalate or acetate succinate esters of hydroxypropyl methylcellulose
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Emergency Medicine (AREA)
- Medicinal Preparation (AREA)
Abstract
1. Частица или множество частиц диметилфумарата, где каждая частица покрыта как минимум первым слоем покрытия, содержащим фармацевтически приемлемый, рН-зависимый, устойчивый в кишечнике полимер.2. Частица(ы) по п. 1, имеющие гранулометрический состав такой, что Dсоставляет от 50 до 1000 микрометров.3. Частица(ы) по п. 1 или 2, где рН-зависимый, устойчивый в кишечнике полимер представляет собой, отдельно или в комбинации, полиметакрилат, ацетат сукцинат гидроксипропилметилцеллюлозы, фталат гидроксипропилметилцеллюлозы, поливинил ацетат фталат, ацетат фталат целлюлозы или шеллак.4. Частица(ы) по п. 1, где полимер представляет собой сополимер метакриловой кислоты и метилметакрилата или сополимер метакриловой кислоты и этилакрилата.5. Частица(ы) по п. 1, где количество полимерного покрытия составляет от 10 до 100% масс. от массы частицы или частиц диметилфумарата.6. Частица(ы) по п. 1, способные к высвобождению диметилфумарата, что подтверждено в USP или Ph. Eur. тестах растворения in vitro в специальной корзине для оборудования при 100 об/мин с использованием искусственного желудочного сока для измерения показателей растворения в течение первых двух часов теста и искусственного кишечного сока для измерения показателей растворения в течение последующих часов, результаты которых следующие:- в течение первых двух часов после начала теста наблюдалось высвобождение max. 10% масс. от общего количества диметилфумарата;- в течение первых трех часов после начала теста наблюдалось высвобождение min. 50% масс., предпочтительно min. 60% масс. от общего количества диметилфумарата.7. Фармацевтический препарат для перорального введения, содержащий частицу ил1. A particle or a plurality of dimethyl fumarate particles, wherein each particle is coated with at least a first coating layer containing a pharmaceutically acceptable, pH dependent, intestinally stable polymer. Particle (s) according to claim 1, having a particle size distribution such that D is from 50 to 1000 micrometers. 3. Particle (s) according to claim 1 or 2, wherein the pH-dependent, intestinally stable polymer is, alone or in combination, polymethacrylate, hydroxypropyl methylcellulose acetate succinate, hydroxypropyl methylcellulose phthalate, polyvinyl acetate phthalate, cellulose acetate or shellac. 4. Particle (s) according to claim 1, wherein the polymer is a copolymer of methacrylic acid and methyl methacrylate or a copolymer of methacrylic acid and ethyl acrylate. Particle (s) according to claim 1, where the amount of polymer coating is from 10 to 100% of the mass. by weight of the particle or particles of dimethyl fumarate. 6. Particle (s) according to claim 1, capable of releasing dimethyl fumarate, as confirmed by USP or Ph. Eur. in vitro dissolution tests in a special equipment basket at 100 rpm using artificial gastric juice to measure dissolution during the first two hours of the test and artificial intestinal juice to measure dissolution during the next hours, the results of which are as follows: - during the first two hours after the start of the test, max. 10% of the mass. of the total amount of dimethyl fumarate; - during the first three hours after the start of the test, a release of min. 50 wt. -%, preferably min. 60% of the mass. of the total amount of dimethyl fumarate. 7. Pharmaceutical preparation for oral administration containing a particle of sludge
Claims (15)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EPPCT/EP2011/070955 | 2011-11-24 | ||
| EP2011070955 | 2011-11-24 | ||
| PCT/EP2012/073406 WO2013076216A1 (en) | 2011-11-24 | 2012-11-22 | Controlled release particles comprising dimethyl fumarate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2014125430A true RU2014125430A (en) | 2015-12-27 |
Family
ID=47226159
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2014125430/15A RU2014125430A (en) | 2011-11-24 | 2012-11-22 | CONTROLLED RELEASE OF PARTICLES CONTAINING DIMETHYLFUMARATE |
Country Status (2)
| Country | Link |
|---|---|
| RU (1) | RU2014125430A (en) |
| WO (1) | WO2013076216A1 (en) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2582942T3 (en) | 2004-10-08 | 2016-09-16 | Forward Pharma A/S | Pharmaceutical controlled release compositions comprising a fumaric acid ester |
| RU2554347C2 (en) | 2008-08-19 | 2015-06-27 | Ксенопорт, Инк. | Methylhydrofumarate prodrugs, pharmaceutical compositions containing them and methods for using |
| US10945984B2 (en) | 2012-08-22 | 2021-03-16 | Arbor Pharmaceuticals, Llc | Methods of administering monomethyl fumarate and prodrugs thereof having reduced side effects |
| EP2887933A1 (en) | 2012-08-22 | 2015-07-01 | XenoPort, Inc. | Oral dosage forms of methyl hydrogen fumarate and prodrugs thereof |
| JP6373353B2 (en) | 2013-03-14 | 2018-08-15 | アルカーメス ファーマ アイルランド リミテッド | Fumarate prodrugs and their use in the treatment of various diseases |
| US8669281B1 (en) | 2013-03-14 | 2014-03-11 | Alkermes Pharma Ireland Limited | Prodrugs of fumarates and their use in treating various diseases |
| US10179118B2 (en) | 2013-03-24 | 2019-01-15 | Arbor Pharmaceuticals, Llc | Pharmaceutical compositions of dimethyl fumarate |
| WO2014197860A1 (en) | 2013-06-07 | 2014-12-11 | Xenoport, Inc. | Method of making monomethyl fumarate |
| US9421182B2 (en) | 2013-06-21 | 2016-08-23 | Xenoport, Inc. | Cocrystals of dimethyl fumarate |
| WO2015035184A1 (en) | 2013-09-06 | 2015-03-12 | Xenoport, Inc. | Crystalline forms of (n,n-diethylcarbamoyl)methyl methyl (2e)but-2-ene-1,4-dioate, methods of synthesis and use |
| US20150079180A1 (en) * | 2013-09-18 | 2015-03-19 | Xenoport, Inc. | Nanoparticle compositions of dimethyl fumarate |
| NZ720287A (en) | 2013-12-12 | 2020-05-29 | Almirall Sa | Pharmaceutical compositions comprising dimethyl fumarate |
| US10172794B2 (en) * | 2013-12-13 | 2019-01-08 | Biogen Ma Inc. | Controlled release dosage form for once daily administration of dimethyl fumarate |
| WO2015127450A1 (en) | 2014-02-24 | 2015-08-27 | Alkermes Pharma Ireland Limited | Sulfonamide and sulfinamide prodrugs of fumarates and their use in treating various diseases |
| US10098863B2 (en) | 2014-02-28 | 2018-10-16 | Banner Life Sciences Llc | Fumarate esters |
| US9636318B2 (en) | 2015-08-31 | 2017-05-02 | Banner Life Sciences Llc | Fumarate ester dosage forms |
| AU2015222880B2 (en) | 2014-02-28 | 2016-11-24 | Banner Life Sciences Llc | Controlled release enteric soft capsules of fumarate esters |
| US9326947B1 (en) | 2014-02-28 | 2016-05-03 | Banner Life Sciences Llc | Controlled release fumarate esters |
| US9999672B2 (en) | 2014-03-24 | 2018-06-19 | Xenoport, Inc. | Pharmaceutical compositions of fumaric acid esters |
| MA40982A (en) * | 2014-11-19 | 2017-09-26 | Biogen Ma Inc | PHARMACEUTICAL BALL FORMULATION INCLUDING DIMETHYL FUMARATE |
| US10085961B2 (en) | 2015-06-01 | 2018-10-02 | Sun Pharmaceutical Industries Limited | Pharmaceutical compositions of dimethyl fumarate |
| HK1254054A1 (en) * | 2015-06-17 | 2019-07-12 | Biogen Ma Inc. | Dimethyl fumarate particles and pharmaceutical compositions thereof |
| EA201800403A1 (en) | 2015-12-31 | 2018-12-28 | Заклады Фармацеутицне Польфарма С.А. | METHOD OF OBTAINING COATED INTESTINAL SOLUTION OF GRANULATE CONTAINING CONTAINING DIMETHYLFUMARATE |
| PL3407873T3 (en) * | 2016-01-28 | 2025-01-13 | Zakłady Farmaceutyczne POLPHARMA S.A. | Process for preparation of a granulate comprising dimethyl fumarate |
| TR201616998A1 (en) * | 2016-11-23 | 2018-06-21 | Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi | DELAYED RELEASE DOSING FORMS WITH DIMETHYL FUMARATE |
| US11446055B1 (en) | 2018-10-18 | 2022-09-20 | Lumoptik, Inc. | Light assisted needle placement system and method |
| US11903918B2 (en) | 2020-01-10 | 2024-02-20 | Banner Life Sciences Llc | Fumarate ester dosage forms with enhanced gastrointestinal tolerability |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH664150A5 (en) | 1985-01-15 | 1988-02-15 | Peter Paul Prof Dr Speiser | FUMARIC ACID PRODUCT, METHOD FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL FORMS CONTAINING THIS. |
| US4959389A (en) | 1987-10-19 | 1990-09-25 | Speiser Peter P | Pharmaceutical preparation for the treatment of psoriatic arthritis |
| DE3834794A1 (en) | 1988-10-12 | 1990-04-19 | F Schielein | Composition for oral administration to treat psoriasis |
| DE19814358C2 (en) | 1998-03-31 | 2002-01-17 | Fumapharm Ag Muri | Use of alkyl hydrogen fumarates for the treatment of psoriasis, psoriatic arthritis, neurodermatitis and enteritis regionalis Crohn |
| DE19848260C2 (en) | 1998-10-20 | 2002-01-17 | Fumapharm Ag Muri | Fumaric microtablets |
| DE19853487A1 (en) | 1998-11-19 | 2000-05-25 | Fumapharm Ag Muri | Use of dialkyl fumarate for treating transplant rejection and autoimmune disease |
| JP2006502156A (en) | 2002-09-04 | 2006-01-19 | ランバクシー ラボラトリーズ リミテッド | Flavor-blocked dosage forms and methods for their formulation |
| ES2582942T3 (en) | 2004-10-08 | 2016-09-16 | Forward Pharma A/S | Pharmaceutical controlled release compositions comprising a fumaric acid ester |
| US20080299196A1 (en) * | 2005-10-07 | 2008-12-04 | Aditech Pharma Ab | Controlled Release Pharmaceutical Compositions Comprising a Fumaric Acid Ester |
| JP5167345B2 (en) | 2007-05-07 | 2013-03-21 | エボニック レーム ゲゼルシャフト ミット ベシュレンクテル ハフツング | Solid dosage form with enteric coating for accelerated drug release |
| CN102369000A (en) * | 2009-01-09 | 2012-03-07 | 前进制药公司 | Pharmaceutical composition comprising one or more fumarates |
-
2012
- 2012-11-22 RU RU2014125430/15A patent/RU2014125430A/en not_active Application Discontinuation
- 2012-11-22 WO PCT/EP2012/073406 patent/WO2013076216A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| WO2013076216A1 (en) | 2013-05-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA93 | Acknowledgement of application withdrawn (no request for examination) |
Effective date: 20151123 |