CZ2013621A3 - Termodynamicky stabilní tuhý roztok agomelatinu pro použití ve farmaceutické formulaci - Google Patents
Termodynamicky stabilní tuhý roztok agomelatinu pro použití ve farmaceutické formulaci Download PDFInfo
- Publication number
- CZ2013621A3 CZ2013621A3 CZ2013-621A CZ2013621A CZ2013621A3 CZ 2013621 A3 CZ2013621 A3 CZ 2013621A3 CZ 2013621 A CZ2013621 A CZ 2013621A CZ 2013621 A3 CZ2013621 A3 CZ 2013621A3
- Authority
- CZ
- Czechia
- Prior art keywords
- agomelatine
- solid solution
- weight
- pharmaceutical composition
- extrudate
- Prior art date
Links
- 229960002629 agomelatine Drugs 0.000 title claims abstract description 141
- YJYPHIXNFHFHND-UHFFFAOYSA-N agomelatine Chemical compound C1=CC=C(CCNC(C)=O)C2=CC(OC)=CC=C21 YJYPHIXNFHFHND-UHFFFAOYSA-N 0.000 title claims abstract description 139
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 38
- 239000006104 solid solution Substances 0.000 claims abstract description 76
- 238000000034 method Methods 0.000 claims abstract description 30
- 238000002360 preparation method Methods 0.000 claims abstract description 28
- 230000008569 process Effects 0.000 claims abstract description 14
- 229920002689 polyvinyl acetate Polymers 0.000 claims abstract description 10
- 239000011118 polyvinyl acetate Substances 0.000 claims abstract description 10
- 239000002245 particle Substances 0.000 claims description 51
- 229920000642 polymer Polymers 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 32
- 238000000227 grinding Methods 0.000 claims description 24
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 24
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 16
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 15
- 238000002844 melting Methods 0.000 claims description 13
- 230000008018 melting Effects 0.000 claims description 13
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims description 12
- 235000019359 magnesium stearate Nutrition 0.000 claims description 12
- 229940016286 microcrystalline cellulose Drugs 0.000 claims description 12
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims description 12
- 239000008108 microcrystalline cellulose Substances 0.000 claims description 12
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 11
- 235000021355 Stearic acid Nutrition 0.000 claims description 11
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 11
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 11
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 11
- 239000008117 stearic acid Substances 0.000 claims description 11
- 229960000913 crospovidone Drugs 0.000 claims description 10
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 claims description 10
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 claims description 10
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 10
- 229940075614 colloidal silicon dioxide Drugs 0.000 claims description 9
- 229920001577 copolymer Polymers 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 238000005516 engineering process Methods 0.000 claims description 7
- 239000000945 filler Substances 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 5
- 229920001531 copovidone Polymers 0.000 claims description 5
- 239000007884 disintegrant Substances 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 4
- 235000019700 dicalcium phosphate Nutrition 0.000 claims description 4
- 238000001125 extrusion Methods 0.000 claims description 4
- 238000009474 hot melt extrusion Methods 0.000 claims description 4
- 239000000314 lubricant Substances 0.000 claims description 4
- 238000009826 distribution Methods 0.000 claims description 3
- 238000007908 dry granulation Methods 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- WSVLPVUVIUVCRA-KPKNDVKVSA-N Alpha-lactose monohydrate Chemical compound O.O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O WSVLPVUVIUVCRA-KPKNDVKVSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 2
- 229930195725 Mannitol Natural products 0.000 claims description 2
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 claims description 2
- XAAHAAMILDNBPS-UHFFFAOYSA-L calcium hydrogenphosphate dihydrate Chemical compound O.O.[Ca+2].OP([O-])([O-])=O XAAHAAMILDNBPS-UHFFFAOYSA-L 0.000 claims description 2
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 claims description 2
- 235000013539 calcium stearate Nutrition 0.000 claims description 2
- 239000008116 calcium stearate Substances 0.000 claims description 2
- MVPICKVDHDWCJQ-UHFFFAOYSA-N ethyl 3-pyrrolidin-1-ylpropanoate Chemical compound CCOC(=O)CCN1CCCC1 MVPICKVDHDWCJQ-UHFFFAOYSA-N 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims description 2
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 2
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 2
- 229960001021 lactose monohydrate Drugs 0.000 claims description 2
- 229940031703 low substituted hydroxypropyl cellulose Drugs 0.000 claims description 2
- 239000000594 mannitol Substances 0.000 claims description 2
- 235000010355 mannitol Nutrition 0.000 claims description 2
- 229940045902 sodium stearyl fumarate Drugs 0.000 claims description 2
- 239000000600 sorbitol Substances 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 16
- 229920003083 Kollidon® VA64 Polymers 0.000 description 27
- 239000000126 substance Substances 0.000 description 19
- 238000004090 dissolution Methods 0.000 description 17
- 230000000052 comparative effect Effects 0.000 description 15
- 238000004458 analytical method Methods 0.000 description 11
- 238000000634 powder X-ray diffraction Methods 0.000 description 11
- 239000007962 solid dispersion Substances 0.000 description 11
- 238000012790 confirmation Methods 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 238000005029 sieve analysis Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 229920003081 Povidone K 30 Polymers 0.000 description 6
- 239000013543 active substance Substances 0.000 description 6
- 238000012545 processing Methods 0.000 description 6
- 238000007711 solidification Methods 0.000 description 6
- 230000008023 solidification Effects 0.000 description 6
- 238000012430 stability testing Methods 0.000 description 5
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- 239000011888 foil Substances 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000008240 homogeneous mixture Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 238000012795 verification Methods 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000000305 Fourier transform infrared microscopy Methods 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 238000005056 compaction Methods 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 239000012943 hotmelt Substances 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000005033 polyvinylidene chloride Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 101100370100 Mus musculus Tor3a gene Proteins 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000002144 chemical decomposition reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000007922 dissolution test Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000012729 immediate-release (IR) formulation Substances 0.000 description 1
- 230000001193 melatoninergic effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229940069328 povidone Drugs 0.000 description 1
- 230000002295 serotoninergic effect Effects 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
- A61K9/146—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic macromolecular compounds
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CZ2013-621A CZ2013621A3 (cs) | 2013-08-13 | 2013-08-13 | Termodynamicky stabilní tuhý roztok agomelatinu pro použití ve farmaceutické formulaci |
| PCT/CZ2014/000088 WO2015021949A1 (fr) | 2013-08-13 | 2014-08-13 | Solution d'agomélatine solide et thermodynamiquement stable destinée à être utilisée dans une préparation pharmaceutique |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CZ2013-621A CZ2013621A3 (cs) | 2013-08-13 | 2013-08-13 | Termodynamicky stabilní tuhý roztok agomelatinu pro použití ve farmaceutické formulaci |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CZ2013621A3 true CZ2013621A3 (cs) | 2015-02-25 |
Family
ID=51589032
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ2013-621A CZ2013621A3 (cs) | 2013-08-13 | 2013-08-13 | Termodynamicky stabilní tuhý roztok agomelatinu pro použití ve farmaceutické formulaci |
Country Status (2)
| Country | Link |
|---|---|
| CZ (1) | CZ2013621A3 (fr) |
| WO (1) | WO2015021949A1 (fr) |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2658818B1 (fr) | 1990-02-27 | 1993-12-31 | Adir Cie | Nouveaux derives a structure naphtalenique, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| FR2866335B1 (fr) | 2004-02-13 | 2006-05-26 | Servier Lab | Nouveau procede de synthese de l'agomelatine |
| FR2889523B1 (fr) | 2005-08-03 | 2007-12-28 | Servier Lab | Nouvelle forme cristalline v de l'agomelatine, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
| FR2889521B1 (fr) | 2005-08-03 | 2007-12-28 | Servier Lab | Nouvelle forme cristalline iii de l'agomelatine, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
| FR2889522B1 (fr) | 2005-08-03 | 2007-12-28 | Servier Lab | Nouvelle forme cristalline iv de l'agomelatine, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
| FR2923482B1 (fr) | 2007-11-09 | 2010-01-29 | Servier Lab | Nouvelle forme cristalline vi de l'agomelatine, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
| WO2011006387A1 (fr) | 2009-07-11 | 2011-01-20 | 浙江华海药业股份有限公司 | Procédé pour la préparation d'agomélatine, cristaux d'agomélatine et leur procédé de préparation |
| CN102106807B (zh) * | 2009-12-29 | 2013-03-27 | 上海中西制药有限公司 | 一种固体制剂的制备方法及所得固体制剂 |
| EP2705023A4 (fr) * | 2011-01-04 | 2014-11-19 | Symed Labs Ltd | Procédés pour la préparation de n-[2-(7-méthoxy-1-naphtyléthyl]acétamide |
| WO2012130837A1 (fr) * | 2011-03-28 | 2012-10-04 | Ratiopharm Gmbh | Agomélatine solide sous une forme non cristalline |
| CN102670514B (zh) * | 2012-04-29 | 2017-05-10 | 浙江华海药业股份有限公司 | 阿戈美拉汀固体制剂 |
-
2013
- 2013-08-13 CZ CZ2013-621A patent/CZ2013621A3/cs unknown
-
2014
- 2014-08-13 WO PCT/CZ2014/000088 patent/WO2015021949A1/fr not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| WO2015021949A1 (fr) | 2015-02-19 |
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