WO2006037342A2 - Controlled release pharmaceutical compositions comprising a fumaric acid ester - Google Patents
Controlled release pharmaceutical compositions comprising a fumaric acid ester Download PDFInfo
- Publication number
- WO2006037342A2 WO2006037342A2 PCT/DK2005/000648 DK2005000648W WO2006037342A2 WO 2006037342 A2 WO2006037342 A2 WO 2006037342A2 DK 2005000648 W DK2005000648 W DK 2005000648W WO 2006037342 A2 WO2006037342 A2 WO 2006037342A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- fumaric acid
- controlled release
- composition according
- pharmaceutical composition
- acid ester
- Prior art date
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- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Natural products OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 title claims abstract description 364
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 title claims abstract description 244
- 239000001530 fumaric acid Substances 0.000 title claims abstract description 242
- -1 fumaric acid ester Chemical class 0.000 title claims abstract description 211
- 238000013270 controlled release Methods 0.000 title claims abstract description 103
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 72
- 239000000203 mixture Substances 0.000 claims abstract description 271
- 239000013543 active substance Substances 0.000 claims abstract description 89
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- 238000012360 testing method Methods 0.000 claims description 121
- 238000000034 method Methods 0.000 claims description 59
- 150000003839 salts Chemical class 0.000 claims description 58
- LDCRTTXIJACKKU-ONEGZZNKSA-N dimethyl fumarate Chemical compound COC(=O)\C=C\C(=O)OC LDCRTTXIJACKKU-ONEGZZNKSA-N 0.000 claims description 57
- 125000005907 alkyl ester group Chemical group 0.000 claims description 40
- 239000002775 capsule Substances 0.000 claims description 37
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical group CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 claims description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 30
- 238000002360 preparation method Methods 0.000 claims description 30
- 238000004090 dissolution Methods 0.000 claims description 28
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 28
- 238000000338 in vitro Methods 0.000 claims description 25
- 229960004419 dimethyl fumarate Drugs 0.000 claims description 24
- 239000012738 dissolution medium Substances 0.000 claims description 24
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- NKHAVTQWNUWKEO-UHFFFAOYSA-N fumaric acid monomethyl ester Natural products COC(=O)C=CC(O)=O NKHAVTQWNUWKEO-UHFFFAOYSA-N 0.000 claims description 16
- NKHAVTQWNUWKEO-NSCUHMNNSA-N monomethyl fumarate Chemical compound COC(=O)\C=C\C(O)=O NKHAVTQWNUWKEO-NSCUHMNNSA-N 0.000 claims description 16
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- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 10
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 9
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- XLYMOEINVGRTEX-ONEGZZNKSA-N (e)-4-ethoxy-4-oxobut-2-enoic acid Chemical compound CCOC(=O)\C=C\C(O)=O XLYMOEINVGRTEX-ONEGZZNKSA-N 0.000 claims description 7
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- XLYMOEINVGRTEX-UHFFFAOYSA-N fumaric acid monoethyl ester Natural products CCOC(=O)C=CC(O)=O XLYMOEINVGRTEX-UHFFFAOYSA-N 0.000 claims description 6
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- IEPRKVQEAMIZSS-AATRIKPKSA-N diethyl fumarate Chemical compound CCOC(=O)\C=C\C(=O)OCC IEPRKVQEAMIZSS-AATRIKPKSA-N 0.000 claims description 4
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- VPSJAYGPROOVSR-BQYQJAHWSA-N (E)-2-methyl-3-pentylbut-2-enedioic acid Chemical compound CCCCC\C(C(O)=O)=C(\C)C(O)=O VPSJAYGPROOVSR-BQYQJAHWSA-N 0.000 claims description 2
- CGEMPWFQTSQCKJ-VOTSOKGWSA-N (e)-2-butyl-3-methylbut-2-enedioic acid Chemical compound CCCC\C(C(O)=O)=C(\C)C(O)=O CGEMPWFQTSQCKJ-VOTSOKGWSA-N 0.000 claims description 2
- HVZKWAQLXHTHSG-SNAWJCMRSA-N (e)-2-ethyl-3-methylbut-2-enedioic acid Chemical compound CC\C(C(O)=O)=C(\C)C(O)=O HVZKWAQLXHTHSG-SNAWJCMRSA-N 0.000 claims description 2
- BDJSZICOAPUZNY-AATRIKPKSA-N (e)-2-methyl-3-propylbut-2-enedioic acid Chemical compound CCC\C(C(O)=O)=C(\C)C(O)=O BDJSZICOAPUZNY-AATRIKPKSA-N 0.000 claims description 2
- UTOVMEACOLCUCK-SNAWJCMRSA-N (e)-4-butoxy-4-oxobut-2-enoic acid Chemical compound CCCCOC(=O)\C=C\C(O)=O UTOVMEACOLCUCK-SNAWJCMRSA-N 0.000 claims description 2
- BOFGUJVLYGISIU-AATRIKPKSA-N (e)-4-oxo-4-pentoxybut-2-enoic acid Chemical compound CCCCCOC(=O)\C=C\C(O)=O BOFGUJVLYGISIU-AATRIKPKSA-N 0.000 claims description 2
- AYAUWVRAUCDBFR-ONEGZZNKSA-N (e)-4-oxo-4-propoxybut-2-enoic acid Chemical compound CCCOC(=O)\C=C\C(O)=O AYAUWVRAUCDBFR-ONEGZZNKSA-N 0.000 claims description 2
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Definitions
- Fumaraat 120® Another marketed composition is Fumaraat 120® containing 120 mg of dimethylfumarate and 95 mg of calcium monoethylfumarate (TioFarma, Oud-Beijerland, Netherlands).
- Fumaraat 120® containing 120 mg of dimethylfumarate and 95 mg of calcium monoethylfumarate (TioFarma, Oud-Beijerland, Netherlands).
- the pharmacokinetic profile of Fumaraat 120® is described in healthy subjects. The results show that a single oral dose of Fumaraat 120® is followed by a rise in serum monomethylfumarate concentration and only negligible concentrations of dimethylfumarate and fumaric acid is observed.
- the active substance in a composition of the invention is any fumaric acid ester.
- the fumaric acid ester is preferably selected from the group consisting of dimethylfumarate, diethylfumarate, dipropylfumarate, dibutylfumarate, dipentylfumarate, methyl-ethylfumarate, methyl-propylfumarate, methyl-butylfumarate, methyl-pentylfumarate, monomethylfumarate, monoethylfumarate, monopropylfumarate, monobutylfumarate and monopentylfumarate, including pharmaceutically acceptable salts thereof.
- composition of the invention comprises the active substance in the form of micro-crystals with hydroph ilic surfaces.
- the micro-crystals are filmcoated directly, in order to achieve a sustained release formulation.
- a controlled release pharmaceutical composition comprising as an active substance one or more fumaric acid esters selected from CJi-(C 1 - C 5 )alkylesters of fumaric acid and mono-(C 1 -C 5 )alkylesters of fumaric acid, or a pharmaceutically acceptable salt thereof, characterized in that it consists of a controlled- release dosage form adapted to release di-(Ci-C 5 )alkylester and/or a mono-(Ci-C 5 )alkylester of fumaric acid or a pharmaceutically acceptable salt thereof over a predetermined time period, according to a in vitro profile of dissolution when measured according to USP in 0.1 N hydrochloric acid during the first 2 hours and then 0.05 M phosphate buffer at a pH 6.5 or 6.8,
- the most about 85% w/w such as, e.g., from about 50% to about 85% w/w, from about 60% to about 80% w/w, or about 75% w/w of the total amount of the fumaric acid ester contained in the composition is released, and/or within the first 8 hours after start of the test at the most about 92% w/w such as, e.g., from about 30% to about 92% w/w, from about 35% to about 90% w/w, from about 40% to about 85% w/w, from about 45% to about 80% w/w, from about 50% to about 75% w/w, from about 55% to about 75% w/w, from about 60% to about 75% w/w, or about 65% w/w, or about 70% w/w of the total amount of the fumaric acid ester contained in the composition is released, and/or
- the composition within the first 10 hours after start of the test at the most about 85% w/w such as, e.g., from about 50% to about 85% w/w such as, e.g., from about 60% to about 80% w/w, or about 75% w/w of the total amount of the fumaric acid ester contained in the composition is released, and/or within the first 12 hours after start of the test at least about 80% w/w such as, e.g., about 80% w/w or more such as, e.g., about 85% w/w or more, about 90% w/w or more or about 95% w/w or more of the total amount of the fumaric acid ester contained in the composition is released.
- 80% w/w such as, e.g., about 80% w/w or more such as, e.g., about 85% w/w or more, about 90% w/w or more or about 95% w/w or more of the total amount of
- the most about 95% w/w such as, e.g., from about 35% to about 95% w/w, from about 40% to about 90% w/w, from about 45% to about 85% w/w, from about 50% to about 85% w/w, from about 55% to about 85% w/w, from about 60% to about 85% w/w, from about 65% to about 85% w/w, from about 70% to about 85% w/w, from about 75% to about 85% w/w, or about 65% w/w, or about 70% w/w, or about 75% w/w, or about 80% w/w of the total amount of the fumaric acid ester contained in the composition is released, and/or
- the invention relates to a controlled release pharmaceutical composition for oral use comprising as an active substance one or more fumaric acid esters selected from di-(C 1 -C 5 )alkylesters of fumaric acid and mono-(C 1 -C 5 )alkylesters of fumaric acid, or a pharmaceutically acceptable salt thereof, wherein the release of the fumaric acid ester - when subjected to an in vitro dissolution test according to the "half-change" method - is as follows:
- One aspect of the invention relates to a zero-order dissolution release profile. Another aspect relates to a first-order dissolution release profile. A further aspect relates to a square-root (Higuchi 's equation) dissolution release profile.
- an oral anti-psoriatic drug such as 1) an oral retinoid (such as acitretin or etretinate) combined or not combined with PUVA, 2) cyclosporine and other calcineurin inhibitors, such as ISA247, tacrolimus and pimecrolimus, 3) methotrexate, 4) hydroxyurea, 5) azathioprine, 6) sulphasalazine, 7) a fumarate derivative (such as e.g.
- nutritional therapies such as elemental or polymeric formulas or pre- and probiotics
- Eudragit ® L30D-55 is sprayed at drying temperatures of 6O°C to 80 0 C onto the tablets in an amount of 6 mg polymeric material per mm 2 . Pigments and talc are added in an appropriate amount.
- a saturated solution of 50 g DMF in 300 ml 2-propanol is prepared at 60 0 C and slowly cooled under permanent stirring.
- the precipitated crystals are filtered off and dried at 50 0 C.
- the crystals are sieved and the 315 - 710 ⁇ m fraction is used for a coating process in either a pan coater or a fluid-bed coater (Mini-Glatt).
- a coating solution of 12 g ethyl cellulose (e.g. Ethocel ® NF premium) and 3 g polyethylene glycole 400 in 500 g ethanol is sprayed at 60 0 C onto the powder surface. After drying, the coated crystals are sieved through a 1.00 mm sieve.
- Ethylcellulose e.g. Ethocel ® NF premium
- Polyethylenglycole 400 which is dissolved in 150 ml Ethanol 96%, passed through a 1,0 mm sieve, dried at 50° to 6O 0 C over 30 min and again passed through a sieve 1,0 mm.
- a placebo granulate is prepared as follows: Tablettose ® and Avicel ® 102 are mixed in equal shares and granulated with 2% povidone (e.g.
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- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Emergency Medicine (AREA)
- Immunology (AREA)
- Diabetes (AREA)
- Molecular Biology (AREA)
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- Transplantation (AREA)
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- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Priority Applications (56)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
LTEP05789026.1T LT1799196T (lt) | 2004-10-08 | 2005-10-07 | Kontroliuojamo atpalaidavimo farmacinė kompozicija, apimanti fumaro rūgšties esterį |
PT10182198T PT2316430E (pt) | 2004-10-08 | 2005-10-07 | Composições farmacêuticas de libertação controlada compreendendo um éster de ácido fumárico |
DK05789026.1T DK1799196T3 (en) | 2004-10-08 | 2005-10-07 | Controlled release pharmaceutical compositions comprising a fumaric acid ester |
EP10182198A EP2316430B8 (en) | 2004-10-08 | 2005-10-07 | Controlled release pharmaceutical compositions comprising a fumaric acid ester |
PCT/DK2005/000648 WO2006037342A2 (en) | 2004-10-08 | 2005-10-07 | Controlled release pharmaceutical compositions comprising a fumaric acid ester |
US11/576,871 US20140099364A2 (en) | 2004-10-08 | 2005-10-07 | Controlled release pharmaceutical compositions comprising a fumaric acid ester |
EP05789026.1A EP1799196B1 (en) | 2004-10-08 | 2005-10-07 | Controlled release pharmaceutical compositions comprising a fumaric acid ester |
PL10182198T PL2316430T3 (pl) | 2004-10-08 | 2005-10-07 | Kompozycje farmaceutyczne o kontrolowanym uwalnianiu, zawierające ester kwasu fumarowego |
ES10182198T ES2387192T3 (es) | 2004-10-08 | 2005-10-07 | Composiciones farmacéuticas de liberación controlada que comprenden un éster de ácido fumárico |
HK07114067.2A HK1108836B (en) | 2004-10-08 | 2005-10-07 | Controlled release pharmaceutical compositions comprising a fumaric acid ester |
JP2007535023A JP2008515822A (ja) | 2004-10-08 | 2005-10-07 | フマル酸エステルを含む制御放出医薬組成物 |
SI200531565T SI2316430T1 (sl) | 2004-10-08 | 2005-10-07 | Farmacevtski sestavki z nadziranim sproščanjem, ki obsegajo ester fumarne kisline |
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US14/209,584 Continuation US20140200272A1 (en) | 2004-10-08 | 2014-03-13 | Controlled release pharmaceutical compositions comprising a fumaric acid ester |
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US14/209,480 Continuation US20170112793A2 (en) | 2004-10-08 | 2014-03-13 | Controlled release pharmaceutical compositions comprising a fumaric acid ester |
US14/209,823 Continuation US20150024049A1 (en) | 2004-10-08 | 2014-03-13 | Controlled release pharmaceutical compositions comprising a fumaric acid ester |
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US14/212,685 Continuation US20140199392A1 (en) | 2004-10-08 | 2014-03-14 | Controlled release pharmaceutical compositions comprising a fumaric acid ester |
US14/213,321 Continuation US20140199387A1 (en) | 2004-10-08 | 2014-03-14 | Controlled release pharmaceutical compositions comprising a fumaric acid ester |
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US14/213,399 Continuation US20140205659A1 (en) | 2004-10-08 | 2014-03-14 | Controlled release pharmaceutical compositions comprising a fumaric acid ester |
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2013
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2017
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