ES2756711T3 - Formulaciones estabilizadas de compuestos del SNC - Google Patents
Formulaciones estabilizadas de compuestos del SNC Download PDFInfo
- Publication number
- ES2756711T3 ES2756711T3 ES17180576T ES17180576T ES2756711T3 ES 2756711 T3 ES2756711 T3 ES 2756711T3 ES 17180576 T ES17180576 T ES 17180576T ES 17180576 T ES17180576 T ES 17180576T ES 2756711 T3 ES2756711 T3 ES 2756711T3
- Authority
- ES
- Spain
- Prior art keywords
- release
- formulation
- molindone
- cellulose
- tablet
- 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.)
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- 239000000203 mixture Substances 0.000 title claims abstract description 108
- 238000009472 formulation Methods 0.000 title claims abstract description 91
- 150000001875 compounds Chemical class 0.000 title description 10
- KLPWJLBORRMFGK-UHFFFAOYSA-N Molindone Chemical compound O=C1C=2C(CC)=C(C)NC=2CCC1CN1CCOCC1 KLPWJLBORRMFGK-UHFFFAOYSA-N 0.000 claims abstract description 71
- 229960004938 molindone Drugs 0.000 claims abstract description 65
- 239000003814 drug Substances 0.000 claims abstract description 51
- 229920000642 polymer Polymers 0.000 claims abstract description 48
- 229940079593 drug Drugs 0.000 claims abstract description 45
- 239000012729 immediate-release (IR) formulation Substances 0.000 claims abstract description 43
- 230000001419 dependent effect Effects 0.000 claims abstract description 27
- 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 27
- 239000011248 coating agent Substances 0.000 claims abstract description 25
- 238000000576 coating method Methods 0.000 claims abstract description 25
- 230000002035 prolonged effect Effects 0.000 claims abstract description 16
- 239000004480 active ingredient Substances 0.000 claims abstract description 11
- 230000003111 delayed effect Effects 0.000 claims abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000003826 tablet Substances 0.000 claims description 90
- 239000002775 capsule Substances 0.000 claims description 19
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 18
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 18
- 230000003204 osmotic effect Effects 0.000 claims description 17
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 16
- 239000011159 matrix material Substances 0.000 claims description 16
- 239000002552 dosage form Substances 0.000 claims description 12
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 11
- 229920001577 copolymer Polymers 0.000 claims description 11
- 239000008187 granular material Substances 0.000 claims description 11
- 239000012528 membrane Substances 0.000 claims description 11
- 239000000843 powder Substances 0.000 claims description 11
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- 239000003381 stabilizer Substances 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 9
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 claims description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 6
- 235000019325 ethyl cellulose Nutrition 0.000 claims description 6
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 6
- 229920003145 methacrylic acid copolymer Polymers 0.000 claims description 6
- 229920002125 Sokalan® Polymers 0.000 claims description 5
- 239000008185 minitablet Substances 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- 206010001488 Aggression Diseases 0.000 claims description 4
- 208000027691 Conduct disease Diseases 0.000 claims description 4
- 239000001856 Ethyl cellulose Substances 0.000 claims description 4
- 229920003143 Eudragit® FS 30 D Polymers 0.000 claims description 4
- 229920003135 Eudragit® L 100-55 Polymers 0.000 claims description 4
- 229920003138 Eudragit® L 30 D-55 Polymers 0.000 claims description 4
- 229920003136 Eudragit® L polymer Polymers 0.000 claims description 4
- 229920003137 Eudragit® S polymer Polymers 0.000 claims description 4
- 229920002845 Poly(methacrylic acid) Polymers 0.000 claims description 4
- 229920001800 Shellac Polymers 0.000 claims description 4
- 229920002494 Zein Polymers 0.000 claims description 4
- 229960001631 carbomer Drugs 0.000 claims description 4
- 239000006185 dispersion Substances 0.000 claims description 4
- 229920001249 ethyl cellulose Polymers 0.000 claims description 4
- 229920001519 homopolymer Polymers 0.000 claims description 4
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- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 4
- 229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 claims description 4
- 229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 claims description 4
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000004208 shellac Substances 0.000 claims description 4
- 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 description 4
- 229940113147 shellac Drugs 0.000 claims description 4
- 235000013874 shellac Nutrition 0.000 claims description 4
- -1 trimethylammonioethyl Chemical group 0.000 claims description 4
- 239000005019 zein Substances 0.000 claims description 4
- 229940093612 zein Drugs 0.000 claims description 4
- 229920000623 Cellulose acetate phthalate Polymers 0.000 claims description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 3
- UGZICOVULPINFH-UHFFFAOYSA-N acetic acid;butanoic acid Chemical compound CC(O)=O.CCCC(O)=O UGZICOVULPINFH-UHFFFAOYSA-N 0.000 claims description 3
- 229940081734 cellulose acetate phthalate Drugs 0.000 claims description 3
- 229920001727 cellulose butyrate Polymers 0.000 claims description 3
- 239000011118 polyvinyl acetate Substances 0.000 claims description 3
- 229920002689 polyvinyl acetate Polymers 0.000 claims description 3
- 241000416162 Astragalus gummifer Species 0.000 claims description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 2
- 229920000084 Gum arabic Polymers 0.000 claims description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims description 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 2
- 229920001615 Tragacanth Polymers 0.000 claims description 2
- 235000010489 acacia gum Nutrition 0.000 claims description 2
- 239000000205 acacia gum Substances 0.000 claims description 2
- 235000010443 alginic acid Nutrition 0.000 claims description 2
- 239000000783 alginic acid Substances 0.000 claims description 2
- 229920000615 alginic acid Polymers 0.000 claims description 2
- 229960001126 alginic acid Drugs 0.000 claims description 2
- 150000004781 alginic acids Chemical class 0.000 claims description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims description 2
- 235000010418 carrageenan Nutrition 0.000 claims description 2
- 239000000679 carrageenan Substances 0.000 claims description 2
- 229920001525 carrageenan Polymers 0.000 claims description 2
- 229940113118 carrageenan Drugs 0.000 claims description 2
- 239000008298 dragée Substances 0.000 claims description 2
- 229940071826 hydroxyethyl cellulose Drugs 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
- 229920000639 hydroxypropylmethylcellulose acetate succinate Polymers 0.000 claims description 2
- 229960003943 hypromellose Drugs 0.000 claims description 2
- 229920000609 methyl cellulose Polymers 0.000 claims description 2
- 239000001923 methylcellulose Substances 0.000 claims description 2
- 235000010981 methylcellulose Nutrition 0.000 claims description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 2
- 229940069328 povidone Drugs 0.000 claims description 2
- 235000010487 tragacanth Nutrition 0.000 claims description 2
- 239000000196 tragacanth Substances 0.000 claims description 2
- 229940116362 tragacanth Drugs 0.000 claims description 2
- 235000012431 wafers Nutrition 0.000 claims description 2
- 235000010493 xanthan gum Nutrition 0.000 claims description 2
- 239000000230 xanthan gum Substances 0.000 claims description 2
- 229920001285 xanthan gum Polymers 0.000 claims description 2
- 229940082509 xanthan gum Drugs 0.000 claims description 2
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 claims description 2
- SSONCJTVDRSLNK-UHFFFAOYSA-N 2-methylprop-2-enoic acid;hydrochloride Chemical compound Cl.CC(=C)C(O)=O SSONCJTVDRSLNK-UHFFFAOYSA-N 0.000 claims 1
- DQEFEBPAPFSJLV-UHFFFAOYSA-N Cellulose propionate Chemical compound CCC(=O)OCC1OC(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C1OC1C(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C(COC(=O)CC)O1 DQEFEBPAPFSJLV-UHFFFAOYSA-N 0.000 claims 1
- 241000978776 Senegalia senegal Species 0.000 claims 1
- 239000002535 acidifier Substances 0.000 claims 1
- 229920006218 cellulose propionate Polymers 0.000 claims 1
- 239000004569 hydrophobicizing agent Substances 0.000 claims 1
- 229940117841 methacrylic acid copolymer Drugs 0.000 claims 1
- 239000011049 pearl Substances 0.000 claims 1
- 238000013265 extended release Methods 0.000 abstract description 8
- 239000010410 layer Substances 0.000 description 28
- 238000000034 method Methods 0.000 description 23
- 229960004684 molindone hydrochloride Drugs 0.000 description 22
- 239000002245 particle Substances 0.000 description 20
- GQWNECFJGBQMBO-UHFFFAOYSA-N Molindone hydrochloride Chemical compound Cl.O=C1C=2C(CC)=C(C)NC=2CCC1CN1CCOCC1 GQWNECFJGBQMBO-UHFFFAOYSA-N 0.000 description 15
- 230000002378 acidificating effect Effects 0.000 description 15
- 238000007906 compression Methods 0.000 description 15
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- 229920002678 cellulose Polymers 0.000 description 13
- 239000008186 active pharmaceutical agent Substances 0.000 description 10
- 229940088679 drug related substance Drugs 0.000 description 10
- 239000007916 tablet composition Substances 0.000 description 8
- 235000010980 cellulose Nutrition 0.000 description 7
- 239000001913 cellulose Substances 0.000 description 7
- 239000002609 medium Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 229920003139 Eudragit® L 100 Polymers 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 238000005469 granulation Methods 0.000 description 6
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- 239000012943 hotmelt Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000013563 matrix tablet Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 5
- 239000002357 osmotic agent Substances 0.000 description 5
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- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound 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 GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 4
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- 229920003163 Eudragit® NE 30 D Polymers 0.000 description 3
- 229920003165 Eudragit® NM 30 D Polymers 0.000 description 3
- 229920003152 Eudragit® RS polymer Polymers 0.000 description 3
- TYVWBCMQECJNSK-UHFFFAOYSA-N [2-methyl-3-(2-methylprop-2-enoyloxy)butan-2-yl]azanium;chloride Chemical compound [Cl-].CC([NH3+])(C)C(C)OC(=O)C(C)=C TYVWBCMQECJNSK-UHFFFAOYSA-N 0.000 description 3
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- 208000015114 central nervous system disease Diseases 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 3
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- YWPHCCPCQOJSGZ-LLVKDONJSA-N (2r)-2-[(2-ethoxyphenoxy)methyl]morpholine Chemical compound CCOC1=CC=CC=C1OC[C@@H]1OCCNC1 YWPHCCPCQOJSGZ-LLVKDONJSA-N 0.000 description 2
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 2
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- 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 description 2
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Classifications
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- 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
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1617—Organic compounds, e.g. phospholipids, fats
- A61K9/1623—Sugars or sugar alcohols, e.g. lactose; Derivatives thereof; Homeopathic globules
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- A—HUMAN NECESSITIES
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- 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
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1635—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)
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- Chemical & Material Sciences (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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| MX2011006463A (es) | 2008-12-19 | 2011-07-20 | Supernus Pharmaceuticals Inc | Metodo de tratamiento de agresion. |
| WO2011123497A1 (en) * | 2010-03-31 | 2011-10-06 | Supernus Pharmaceuticals Inc. | Stabilized formulations of cns compounds |
| EP2919787A1 (en) * | 2012-11-13 | 2015-09-23 | Supernus Pharmaceuticals, Inc. | Method of treatment of aggression |
| US20170312289A1 (en) | 2016-04-29 | 2017-11-02 | Supernus Pharmaceuticals, Inc. | Methods, system, and kit for monitoring, diagnosing, and treating impulsive aggression |
| US20180078516A1 (en) * | 2016-09-19 | 2018-03-22 | Innovazone Labs LLC | Pharmaceutical Composition of Ibuprofen Sodium for Oral Administration |
| WO2019014201A1 (en) * | 2017-07-10 | 2019-01-17 | Apicore Us Llc | MOLINDONE COMPOSITIONS WITH EXTENDED RELEASE |
| EP4212149A1 (en) * | 2022-01-18 | 2023-07-19 | Rijksuniversiteit Groningen | Oral dosage forms of acid-labile salt and methods and uses related thereto |
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| CN1228043C (zh) * | 1999-09-30 | 2005-11-23 | 爱德华·孟岱尔股份有限公司 | 用于高溶解度药物的缓释基质 |
| FR2814463B1 (fr) | 2000-09-22 | 2002-11-15 | Sanofi Synthelabo | Nouveaux polysaccharides a activite antithrombotique comprenant au moins une liaison covalente avec la biotine ou un derive de la biotine |
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| FR2891459B1 (fr) * | 2005-09-30 | 2007-12-28 | Flamel Technologies Sa | Microparticules a liberation modifiee d'au moins un principe actif et forme galenique orale en comprenant |
| CL2007002214A1 (es) * | 2006-08-14 | 2008-03-07 | Boehringer Ingelheim Int | Composicion farmaceutica en la forma de comprimido, donde al menos la longitud del comprimido en el estado anterior de la aplicacion es al menos 7/12 del diametro pilorico del paciente y despues de ingerirlo en estado alimentado, la longitud del comp |
| US20080069878A1 (en) | 2006-08-31 | 2008-03-20 | Gopi Venkatesh | Drug Delivery Systems Comprising Solid Solutions of Weakly Basic Drugs |
| JP2008189616A (ja) | 2007-02-07 | 2008-08-21 | Mitsubishi Tanabe Pharma Corp | 注意欠陥多動性障害の治療薬 |
| GB2447949B (en) | 2007-03-29 | 2010-03-31 | Renasci Consultancy Ltd | A method for identifying a compound for treating a disorder or condition associated with dysfunction of monoamine neurotransmission |
| US8637080B2 (en) * | 2007-06-28 | 2014-01-28 | Osmotica Kereskedelmi és Szolgáltató, KFT | Rupturing controlled release device comprising a subcoat |
| MX2011006463A (es) | 2008-12-19 | 2011-07-20 | Supernus Pharmaceuticals Inc | Metodo de tratamiento de agresion. |
| WO2011123497A1 (en) | 2010-03-31 | 2011-10-06 | Supernus Pharmaceuticals Inc. | Stabilized formulations of cns compounds |
| SE536078C2 (sv) | 2010-10-09 | 2013-04-30 | Core Link Ab | Anordning för bearbetning av hylsor |
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| JP2019189645A (ja) | 2019-10-31 |
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