CA2465077C - Administration amelioree de doses multiples de medicaments - Google Patents

Administration amelioree de doses multiples de medicaments Download PDF

Info

Publication number: CA2465077C
Authority: CA; Canada
Prior art keywords: methylphenidate; particles; drug; dose; group
Prior art date: 1997-07-14
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.): Expired - Lifetime

Application number

CA2465077A

Other languages

English (en)

Other versions

CA2465077A1 (fr

Inventor

Atul M. Mehta

Andrew L. Zeitlin

Maghsoud M. Dariani

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Celgene Corp

Original Assignee

Celgene Corp

Priority date (The priority date 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 date listed.)

1997-07-14

Filing date

1998-06-11

Publication date

2011-05-17

1997-07-14 Priority claimed from US08/892,190 external-priority patent/US5837284A/en

1998-06-11 Application filed by Celgene Corp filed Critical Celgene Corp

1999-01-14 Publication of CA2465077A1 publication Critical patent/CA2465077A1/fr

2011-05-17 Application granted granted Critical

2011-05-17 Publication of CA2465077C publication Critical patent/CA2465077C/fr

2018-06-11 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000003814 drug Substances 0.000 title claims abstract description 108
229940079593 drug Drugs 0.000 title claims abstract description 107
238000002483 medication Methods 0.000 title description 2
239000002552 dosage form Substances 0.000 claims abstract description 75
DUGOZIWVEXMGBE-UHFFFAOYSA-N Methylphenidate Chemical compound C=1C=CC=CC=1C(C(=O)OC)C1CCCCN1 DUGOZIWVEXMGBE-UHFFFAOYSA-N 0.000 claims abstract description 57
229960001344 methylphenidate Drugs 0.000 claims abstract description 53
150000003839 salts Chemical class 0.000 claims abstract description 12
239000002245 particle Substances 0.000 claims description 85
229920001577 copolymer Polymers 0.000 claims description 39
DUGOZIWVEXMGBE-CHWSQXEVSA-N dexmethylphenidate Chemical compound C([C@@H]1[C@H](C(=O)OC)C=2C=CC=CC=2)CCCN1 DUGOZIWVEXMGBE-CHWSQXEVSA-N 0.000 claims description 14
208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 11
208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 11
JUMYIBMBTDDLNG-OJERSXHUSA-N hydron;methyl (2r)-2-phenyl-2-[(2r)-piperidin-2-yl]acetate;chloride Chemical compound Cl.C([C@@H]1[C@H](C(=O)OC)C=2C=CC=CC=2)CCCN1 JUMYIBMBTDDLNG-OJERSXHUSA-N 0.000 claims description 10
239000011230 binding agent Substances 0.000 claims description 9
229960001042 dexmethylphenidate Drugs 0.000 claims description 8
239000000843 powder Substances 0.000 claims description 8
208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 7
230000036470 plasma concentration Effects 0.000 claims description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
206010065040 AIDS dementia complex Diseases 0.000 claims description 2
201000010099 disease Diseases 0.000 claims description 2
DUGOZIWVEXMGBE-STQMWFEESA-N methyl (S)-phenyl[(S)-piperidin-2-yl]acetate Chemical compound C([C@H]1[C@@H](C(=O)OC)C=2C=CC=CC=2)CCCN1 DUGOZIWVEXMGBE-STQMWFEESA-N 0.000 claims 1
230000037406 food intake Effects 0.000 abstract description 20
238000000034 method Methods 0.000 abstract description 16
238000000576 coating method Methods 0.000 description 38
239000011248 coating agent Substances 0.000 description 30
230000003111 delayed effect Effects 0.000 description 25
239000008188 pellet Substances 0.000 description 18
239000000945 filler Substances 0.000 description 17
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 14
125000001453 quaternary ammonium group Chemical group 0.000 description 14
229920000642 polymer Polymers 0.000 description 13
239000006185 dispersion Substances 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
239000000463 material Substances 0.000 description 11
239000000203 mixture Substances 0.000 description 11
239000000565 sealant Substances 0.000 description 11
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
208000015802 attention deficit-hyperactivity disease Diseases 0.000 description 9
239000000178 monomer Substances 0.000 description 9
239000007787 solid Substances 0.000 description 9
239000003826 tablet Substances 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
239000002775 capsule Substances 0.000 description 8
230000000694 effects Effects 0.000 description 8
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 7
239000000546 pharmaceutical excipient Substances 0.000 description 7
239000008367 deionised water Substances 0.000 description 6
229910021641 deionized water Inorganic materials 0.000 description 6
239000012729 immediate-release (IR) formulation Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
238000005507 spraying Methods 0.000 description 6
239000000454 talc Substances 0.000 description 6
229910052623 talc Inorganic materials 0.000 description 6
-1 2-(N,N-dibutylamino) ethyl Chemical group 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
241000124008 Mammalia Species 0.000 description 5
239000006057 Non-nutritive feed additive Substances 0.000 description 5
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 5
239000000654 additive Substances 0.000 description 5
125000000217 alkyl group Chemical group 0.000 description 5
238000009472 formulation Methods 0.000 description 5
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 5
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 5
238000000338 in vitro Methods 0.000 description 5
229960001033 methylphenidate hydrochloride Drugs 0.000 description 5
238000002156 mixing Methods 0.000 description 5
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 5
238000003756 stirring Methods 0.000 description 5
230000001225 therapeutic effect Effects 0.000 description 5
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 4
DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 4
238000000151 deposition Methods 0.000 description 4
238000004090 dissolution Methods 0.000 description 4
239000012530 fluid Substances 0.000 description 4
DUGOZIWVEXMGBE-OLZOCXBDSA-N methyl (S)-phenyl[(R)-piperidin-2-yl]acetate Chemical compound C([C@@H]1[C@@H](C(=O)OC)C=2C=CC=CC=2)CCCN1 DUGOZIWVEXMGBE-OLZOCXBDSA-N 0.000 description 4
239000004014 plasticizer Substances 0.000 description 4
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
208000030507 AIDS Diseases 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
230000002411 adverse Effects 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
239000007894 caplet Substances 0.000 description 3
235000019441 ethanol Nutrition 0.000 description 3
239000008187 granular material Substances 0.000 description 3
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 3
UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 3
238000005259 measurement Methods 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
230000000541 pulsatile effect Effects 0.000 description 3
239000007921 spray Substances 0.000 description 3
238000013268 sustained release Methods 0.000 description 3
239000012730 sustained-release form Substances 0.000 description 3
239000001069 triethyl citrate Substances 0.000 description 3
VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 3
235000013769 triethyl citrate Nutrition 0.000 description 3
JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical group CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 2
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
YQEMORVAKMFKLG-UHFFFAOYSA-N 2-stearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 2
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 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical class O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
229920003157 Eudragit® RL 30 D Polymers 0.000 description 2
229920003161 Eudragit® RS 30 D Polymers 0.000 description 2
229920003134 Eudragit® polymer Polymers 0.000 description 2
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
238000005054 agglomeration Methods 0.000 description 2
230000002776 aggregation Effects 0.000 description 2
125000005907 alkyl ester group Chemical group 0.000 description 2
239000003125 aqueous solvent Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
210000004027 cell Anatomy 0.000 description 2
229920002301 cellulose acetate Polymers 0.000 description 2
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical class OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
229940125368 controlled substance Drugs 0.000 description 2
239000000599 controlled substance Substances 0.000 description 2
230000008021 deposition Effects 0.000 description 2
FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
230000036267 drug metabolism Effects 0.000 description 2
SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 2
230000002209 hydrophobic effect Effects 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
VHCHHBPOHDOOPP-UHFFFAOYSA-N 1,1-dihydroxypropyl acetate Chemical compound CCC(O)(O)OC(C)=O VHCHHBPOHDOOPP-UHFFFAOYSA-N 0.000 description 1
KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 1
JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
PYGXAGIECVVIOZ-UHFFFAOYSA-N Dibutyl decanedioate Chemical compound CCCCOC(=O)CCCCCCCCC(=O)OCCCC PYGXAGIECVVIOZ-UHFFFAOYSA-N 0.000 description 1
206010013486 Distractibility Diseases 0.000 description 1
206010013954 Dysphoria Diseases 0.000 description 1
229920003163 Eudragit® NE 30 D Polymers 0.000 description 1
239000004606 Fillers/Extenders Substances 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
244000046052 Phaseolus vulgaris Species 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
MFOPEVCFSVUADB-UHFFFAOYSA-N acetic acid;methyl carbamate Chemical compound CC(O)=O.COC(N)=O MFOPEVCFSVUADB-UHFFFAOYSA-N 0.000 description 1
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
AJXBTRZGLDTSST-UHFFFAOYSA-N amino 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)ON AJXBTRZGLDTSST-UHFFFAOYSA-N 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
239000002269 analeptic agent Substances 0.000 description 1
208000022531 anorexia Diseases 0.000 description 1
125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
238000000498 ball milling Methods 0.000 description 1
230000004888 barrier function Effects 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
230000037058 blood plasma level Effects 0.000 description 1
238000012662 bulk polymerization Methods 0.000 description 1
238000003490 calendering Methods 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000000969 carrier Substances 0.000 description 1
208000015114 central nervous system disease Diseases 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
239000008199 coating composition Substances 0.000 description 1
230000006999 cognitive decline Effects 0.000 description 1
208000010877 cognitive disease Diseases 0.000 description 1
239000008119 colloidal silica Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000013270 controlled release Methods 0.000 description 1
229920006037 cross link polymer Polymers 0.000 description 1
206010061428 decreased appetite Diseases 0.000 description 1
SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
CRVGKGJPQYZRPT-UHFFFAOYSA-N diethylamino acetate Chemical compound CCN(CC)OC(C)=O CRVGKGJPQYZRPT-UHFFFAOYSA-N 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
239000012738 dissolution medium Substances 0.000 description 1
208000002173 dizziness Diseases 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
238000007720 emulsion polymerization reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
IFDFMWBBLAUYIW-UHFFFAOYSA-N ethane-1,2-diol;ethyl acetate Chemical compound OCCO.CCOC(C)=O IFDFMWBBLAUYIW-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
230000002743 euphoric effect Effects 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
238000001125 extrusion Methods 0.000 description 1
230000006870 function Effects 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
239000010440 gypsum Substances 0.000 description 1
229910052602 gypsum Inorganic materials 0.000 description 1
238000000265 homogenisation Methods 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
229910001867 inorganic solvent Inorganic materials 0.000 description 1
239000003049 inorganic solvent Substances 0.000 description 1
206010022437 insomnia Diseases 0.000 description 1
230000003993 interaction Effects 0.000 description 1
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
229940011051 isopropyl acetate Drugs 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000011068 loading method Methods 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000012528 membrane Substances 0.000 description 1
229940050176 methyl chloride Drugs 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000003801 milling Methods 0.000 description 1
CLEVPNBIFDJCTD-UHFFFAOYSA-N n-[5-(diethylamino)pentan-2-yl]-2-methylprop-2-enamide Chemical compound CCN(CC)CCCC(C)NC(=O)C(C)=C CLEVPNBIFDJCTD-UHFFFAOYSA-N 0.000 description 1
KUTYRKSEXLKSTE-UHFFFAOYSA-N n-[5-(diethylamino)pentan-2-yl]prop-2-enamide Chemical compound CCN(CC)CCCC(C)NC(=O)C=C KUTYRKSEXLKSTE-UHFFFAOYSA-N 0.000 description 1
210000000653 nervous system Anatomy 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000193 polymethacrylate Polymers 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
238000003825 pressing Methods 0.000 description 1
230000000506 psychotropic effect Effects 0.000 description 1
235000021251 pulses Nutrition 0.000 description 1
229940099204 ritalin Drugs 0.000 description 1
239000012812 sealant material Substances 0.000 description 1
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical class OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000010557 suspension polymerization reaction Methods 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
230000002123 temporal effect Effects 0.000 description 1
230000004580 weight loss Effects 0.000 description 1
208000016261 weight loss Diseases 0.000 description 1
XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1

Landscapes

Medicinal Preparation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA2465077A 1997-07-14 1998-06-11 Administration amelioree de doses multiples de medicaments Expired - Lifetime CA2465077C (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US08/892,190 US5837284A (en)	1995-12-04	1997-07-14	Delivery of multiple doses of medications
US08/892,190		1997-07-14
CA002240329A CA2240329C (fr)	1997-07-14	1998-06-11	Administration amelioree de doses multiples de medicaments

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002240329A Division CA2240329C (fr)	1997-07-14	1998-06-11	Administration amelioree de doses multiples de medicaments

Publications (2)

Publication Number	Publication Date
CA2465077A1 CA2465077A1 (fr)	1999-01-14
CA2465077C true CA2465077C (fr)	2011-05-17

Family

ID=32597859

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA2465077A Expired - Lifetime CA2465077C (fr)	1997-07-14	1998-06-11	Administration amelioree de doses multiples de medicaments

Country Status (1)

Country	Link
CA (1)	CA2465077C (fr)

1998
- 1998-06-11 CA CA2465077A patent/CA2465077C/fr not_active Expired - Lifetime

Also Published As

Publication number	Publication date
CA2465077A1 (fr)	1999-01-14

Legal Events

Date	Code	Title	Description
2004-05-12	EEER	Examination request
2018-08-13	MKEX	Expiry	Effective date: 20180611

Publication	Publication Date	Title
CA2240329C (fr)	2004-12-28	Administration amelioree de doses multiples de medicaments
US8557282B2 (en)	2013-10-15	Extended release compositions comprising as active compound venlafaxine hydrochloride
EP0067539B1 (fr)	1985-09-18	Composition pharmaceutique à libération prolongée
US9468633B2 (en)	2016-10-18	Oral controlled release dosage form
EP0711152B1 (fr)	2002-12-04	Formes galeniques pour une administration orale, ayant une couche de poudre
AU680891C (en)	2002-01-03	Controlled release preparation containing a salt of morphine
US6077533A (en)	2000-06-20	Powder-layered oral dosage forms
IE59200B1 (en)	1994-01-26	Therapeutic compositions for oral administration
HU226582B1 (en)	2009-04-28	New controlled release bead, a method of producing the same and multiple unit formulation comprising it
JPS6296420A (ja)	1987-05-02	医薬製剤
US6638533B2 (en)	2003-10-28	Pulse dosage formulations of methylphenidate and method to prepare same
CA2698347A1 (fr)	2000-11-30	Preparations d'inhibiteurs specifiques du recaptage de la serotonine a liberation multiparticulaire regulee
US7060293B1 (en)	2006-06-13	Powder-layered oral dosage forms
CA2465077C (fr)	2011-05-17	Administration amelioree de doses multiples de medicaments
HK1084889A (en)	2006-08-11	Improved delivery of multiple doses of medications
US20160158212A1 (en)	2016-06-09	Extended release aqueous suspension of methylphenidate or salts thereof
HK1033271B (en)	2002-08-16	Multiparticulate pharmaceutical form with programmed and timed release and preparation method
HK1033271A1 (en)	2001-08-24	Multiparticulate pharmaceutical form with programmed and timed release and preparation method