DE9219234U1 - Oxycodon-Zusammensetzung mit kontrollierter Freisetzung - Google Patents
Oxycodon-Zusammensetzung mit kontrollierter FreisetzungInfo
- Publication number
- DE9219234U1 DE9219234U1 DE9219234U DE9219234U DE9219234U1 DE 9219234 U1 DE9219234 U1 DE 9219234U1 DE 9219234 U DE9219234 U DE 9219234U DE 9219234 U DE9219234 U DE 9219234U DE 9219234 U1 DE9219234 U1 DE 9219234U1
- Authority
- DE
- Germany
- Prior art keywords
- oxycodone
- formulation
- controlled release
- salt
- hours
- 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.)
- Expired - Lifetime
Links
- BRUQQQPBMZOVGD-XFKAJCMBSA-N Oxycodone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(OC)C2=C5[C@@]13CCN4C BRUQQQPBMZOVGD-XFKAJCMBSA-N 0.000 title claims abstract 45
- 229960002085 oxycodone Drugs 0.000 title claims abstract 33
- 239000000203 mixture Substances 0.000 title claims abstract 26
- 238000013270 controlled release Methods 0.000 title claims abstract 18
- 238000009472 formulation Methods 0.000 claims abstract 24
- 150000003839 salts Chemical class 0.000 claims abstract 6
- 239000011159 matrix material Substances 0.000 claims abstract 4
- 239000003795 chemical substances by application Substances 0.000 claims abstract 3
- 238000004090 dissolution Methods 0.000 claims abstract 3
- 239000002552 dosage form Substances 0.000 claims abstract 3
- 239000007888 film coating Substances 0.000 claims abstract 3
- 238000009501 film coating Methods 0.000 claims abstract 3
- 238000000338 in vitro Methods 0.000 claims abstract 3
- 229930195733 hydrocarbon Natural products 0.000 claims abstract 2
- 229920001600 hydrophobic polymer Polymers 0.000 claims abstract 2
- 229920001515 polyalkylene glycol Polymers 0.000 claims abstract 2
- 230000036470 plasma concentration Effects 0.000 claims 9
- 239000003814 drug Substances 0.000 claims 5
- 208000002193 Pain Diseases 0.000 claims 3
- 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 class 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 claims 2
- 229920000178 Acrylic resin Polymers 0.000 claims 2
- 239000004925 Acrylic resin Substances 0.000 claims 2
- 230000000202 analgesic effect Effects 0.000 claims 2
- BQNSLJQRJAJITR-UHFFFAOYSA-N 1,1,2-trichloro-1,2-difluoroethane Chemical group FC(Cl)C(F)(Cl)Cl BQNSLJQRJAJITR-UHFFFAOYSA-N 0.000 claims 1
- 208000000094 Chronic Pain Diseases 0.000 claims 1
- 229920002319 Poly(methyl acrylate) Polymers 0.000 claims 1
- 208000004550 Postoperative Pain Diseases 0.000 claims 1
- 229920001800 Shellac Polymers 0.000 claims 1
- 229920002494 Zein Polymers 0.000 claims 1
- 239000012062 aqueous buffer Substances 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 229920002678 cellulose Polymers 0.000 claims 1
- 239000001913 cellulose Substances 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 229920001477 hydrophilic polymer Polymers 0.000 claims 1
- 239000002198 insoluble material Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- MUZQPDBAOYKNLO-RKXJKUSZSA-N oxycodone hydrochloride Chemical compound [H+].[Cl-].O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(OC)C2=C5[C@@]13CCN4C MUZQPDBAOYKNLO-RKXJKUSZSA-N 0.000 claims 1
- 229960003617 oxycodone hydrochloride Drugs 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- 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 1
- 229940113147 shellac Drugs 0.000 claims 1
- 235000013874 shellac Nutrition 0.000 claims 1
- 239000004208 shellac Substances 0.000 claims 1
- 229940093612 zein Drugs 0.000 claims 1
- 239000005019 zein Substances 0.000 claims 1
- 229920006243 acrylic copolymer Polymers 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 239000006186 oral dosage form Substances 0.000 abstract 1
- 229920000058 polyacrylate Polymers 0.000 abstract 1
- 239000007787 solid 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/485—Morphinan derivatives, e.g. morphine, codeine
-
- 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
-
- 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
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
-
- 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
- A61K9/2072—Pills, tablets, discs, rods characterised by shape, structure or size; Tablets with holes, special break lines or identification marks; Partially coated tablets; Disintegrating flat shaped forms
- A61K9/2077—Tablets comprising drug-containing microparticles in a substantial amount of supporting matrix; Multiparticulate tablets
- A61K9/2081—Tablets comprising drug-containing microparticles in a substantial amount of supporting matrix; Multiparticulate tablets with microcapsules or coated microparticles according to A61K9/50
-
- 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
- A61K9/5015—Organic compounds, e.g. fats, sugars
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
Description
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Claims (16)
1. Oxycodon-Formulierung mit kontrollierter Freisetzung zur oralen Verabrei
chung an menschliche Patienten, umfassend:
- a) ein Oxycodonsalz in einer zu 10 mg bis 160 mg des Oxycodonhydrochlorid salzes äquivalenten Menge, und
- b) eine Dosierformulierung mit kontrollierter Freisetzung, mit Ausnahme einer Acrylharzmatrix, die so ausgewählt ist, daß die Formulierung pH-unabhängige Auflösungs eigenschaften aufweist,
- c) wobei die Formulierung bei stationären Bedingungen nach wiederholter Verab reichung in 12 Stundenintervallen eine mittlere maximale Plasmakonzentration von Oxyco don von 6 bis 240 ng/ml 2 bis 4,5 Stunden nach Verabreichung und eine mittlere minimale Plasmakonzentration von Oxycodon von 3 bis 120 ng/ml 10 bis 14 Stunden nach Verabrei chung gewährleistet.
2. Oxycodon-Formulierung mit kontrollierter Freisetzung nach Anspruch 1,
umfassend eine wirksame Menge eines Materials mit kontrollierter Freisetzung ausgewählt
aus der Gruppe bestehend aus hydrophilen Polymeren, hydrophoben Polymeren, verdaubaren
substituierten oder unsubstituierten Kohlenwasserstoffen mit 8 bis 50 Kohlenstoffatomen,
Polyalkylenglykolen, Acrylharzen und Mischungen jeder der vorgenannten.
3. Die Oxycodon-Formulierung mit kontrollierter Freisetzung nach Anspruch 1
oder 2, umfassend 10 mg bis 50 mg Oxycodonsalz, wobei die Formulierung im stationären
Zustand nach wiederholter Verabreichung in 12 Stundenintervallen 2 bis 4,5 Stunden nach
Verabreichung eine mittlere maximale Plasmakonzentration von Oxycodon von 6 bis
60 ng/ml und nach 10 bis 14 Stunden nach Verabreichung eine mittlere minimale Plasma
konzentration von 3 bis 30 ng/ml gewährleistet.
4. Oxycodon-Formulierung mit kontrollierter Freisetzung nach einem der
Ansprüche 1 bis 3, ferner umfassend ein pharmazeutisches Streckmittel.
5. Formulierung mit kontrollierter Freisetzung nach einem der Ansprüche 1, 2
oder 4, in Form einer Tablette umfassend 10 bis 160 mg Oxycodonsalz, dispergiert in einer
Matrix mit kontrollierter Freisetzung.
6. Oxycodon-Formulierung mit kontrollierter Freisetzung zur Verabreichung an
menschliche Patienten, umfassend:
- a) eine analgetisch wirksame Menge von Sphäroiden umfassend Oxycodon oder ein Salz davon und ein Sphäronisiermittel;
- b) wobei jedes Sphäroid mit einem Filmüberzug beschichtet ist, welches die Frei setzung des Oxycodons oder Oxycodonsalzes mit einer kontrollierten Geschwindigkeit in einem wäßrigen Medium kontrolliert.
7. Oxycodon-Formulierung mit kontrollierter Freisetzung nach Anspruch 6,
umfassend: eine analgetisch wirksame Menge von Sphäroiden umfassend ein Oxycodonsalz
und ein Sphäronisiermittel, so daß die Gesamtdosis des Oxycodonsalzes in der Arzneiform 10
bis 160 mg beträgt.
8. Oxycodon-Formulierung mit kontrollierter Freisetzung nach den Ansprüchen 6
oder 7, wobei der Filmüberzug ein wasserunlösliches Material umfaßt, das aus der Gruppe
bestehend aus Schellack, Zein, einer wasserunlöslichen Zellulose oder ein Polymethylacrylat
umfaßt.
9. Dosierformulierung mit kontrollierter Freisetzung nach einem der vorge
nannten Ansprüche, wobei die Dosierformulierung eine In-vitru-Auflösung der Arzneiform
gewährleistet, die, gemessen nach der USP Paddle-Methode bei 100 UPM in 900 ml
wäßrigem Puffer (pH zwischen 1,6 und 7,2) bei 37°C zwischen 12,5 Gew.-% und 42,5 Gew.-
% freigesetztes Oxycodon nach einer Stunde, zwischen 25 Gew.-% und 55 Gew.-% freige
setztes Oxycodon nach 2 Stunden, zwischen 45 Gew.-% und 75 Gew.-% freigesetztes
Oxycodon nach 4 Stunden und zwischen 55 Gew.-% und 85 Gew.-% freigesetztes Oxycodon
nach 6 Stunden aufweist, und die In-vitro-Freisetzungsgeschwindigkeit unabhängig vom pH
ist, wobei im stationären Zustand nach wiederholter Verabreichung in 12 Stundenintervallen
bei 2 bis 4,5 Stunden nach Verabreichung eine mittlere maximale Plasmakonzentration von
Oxycodon von 6 bis 20 ng/ml erhalten wird, und nach 10 bis 14 Stunden nach Verabreichung
eine mittlere minimale Plasmakonzentration von 3 bis 120 ng/ml erhalten wird.
10. Die Oxycodon-Formulierung mit kontrollierter Freisetzung nach den
Ansprüchen 1 bis 9, wobei das Oxycodon in Form eines Hydrochloridsalzes vorliegt.
11. Verwendung einer Oxycodon-Formulierung mit kontrollierter Freisetzung
enthaltend Oxycodonsalz in einer zu 10 mg bis 160 mg des Hydrochloridsalz äquivalenten
Menge, zur Herstellung eines Medikamentes, wobei das Medikament bei Anwendung in viel
fachen 12-Stunden-Intervallen bei menschlichen Patienten im stationären Zustand gewähr
leistet:
- a) eine mittlere maximale Plasmakonzentration von Oxycodon von 6 bis 240 ng/ml nach 2 bis 4,5 Stunden nach Verabreichung;
- b) eine mittlere minimale Plasmakonzentration von Oxycodon von 3 bis 120 ng/ml nach 10 bis 14 Stunden nach Verabreichung; und
- c) Schmerzerleichterung bei im wesentlichen allen menschlichen Patienten für mindestens 12 Stunden.
12. Verwendung nach Anspruch 11, wobei die Formulierung 10 bis 40 mg
Oxycodonsalz enthält, und das Medikament im stationären Zustand gewährleistet:
- a) eine mittlere maximale Plasmakonzentration von Oxycodon von 6 bis 60 ng/ml nach 2 bis 4,5 Stunden nach Verabreichung;
- b) eine mittlere minimale Plasmakonzentration von Oxycodon von 3 bis 30 ng/ml nach 10 bis 14 Stunden nach Verabreichung; und
- c) Schmerzerleichterung bei mindestens 90% aller menschlichen Patienten für mindestens 12 Stunden.
13. Verwendung einer Formulierung nach den Ansprüchen 11 oder 12, wobei das
Oxycodonsalz Oxycodonhydrochlorid ist.
14. Verwendung einer Formulierung nach den Ansprüchen 11 bis 13, wobei das
Oxycodonsalz sich in einer Matrix befindet.
15. Verwendung einer Formulierung nach den Ansprüchen 11 bis 14, wobei das
Medikament für die Anwendung an einem Patienten, der unter moderaten oder schweren
chronischen Schmerzen leidet, vorgesehen ist.
16. Verwendung einer Formulierung nach den Ansprüchen 11 bis 14, wobei das
Medikament für die Anwendung bei einem Patienten, der unter postoperativen Schmerzen
leidet, vorgesehen ist.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/800,549 US5266331A (en) | 1991-11-27 | 1991-11-27 | Controlled release oxycodone compositions |
EP96102992.3A EP0722730B2 (de) | 1991-11-27 | 1992-11-25 | Oxycodonhaltiges Arzneimittel mit verzögerter Wirkstoffabgabe |
Publications (1)
Publication Number | Publication Date |
---|---|
DE9219234U1 true DE9219234U1 (de) | 2001-03-29 |
Family
ID=25178688
Family Applications (10)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE69233326T Expired - Lifetime DE69233326T2 (de) | 1991-11-27 | 1992-11-25 | Oxycodonhaltige Zubereitungen mit gesteuerter Wirkstoffabgabe |
DE69233778T Expired - Lifetime DE69233778D1 (de) | 1991-11-27 | 1992-11-25 | Oxycodonzusammensetzungen mit kontrollierter Freisetzung |
DE69232837.8T Expired - Lifetime DE69232837T3 (de) | 1991-11-27 | 1992-11-25 | Oxycodonhaltiges Arzneimittel mit verzögerter Wirkstoffabgabe |
DE9219234U Expired - Lifetime DE9219234U1 (de) | 1991-11-27 | 1992-11-25 | Oxycodon-Zusammensetzung mit kontrollierter Freisetzung |
DE69233328T Expired - Lifetime DE69233328T3 (de) | 1991-11-27 | 1992-11-25 | Oxycodonhaltige Arzneizusammensetzungen mit verzögerter Wirkstoffabgabe |
DE69233640T Expired - Lifetime DE69233640T2 (de) | 1991-11-27 | 1992-11-25 | Oxycodonsalzzusammensetzungen mit kontrollierter Freisetzung |
DE69233699T Expired - Lifetime DE69233699T2 (de) | 1991-11-27 | 1992-11-25 | Oxycodonzusammensetzungen mit kontrollierter Freisetzung |
DE69233691T Expired - Lifetime DE69233691T2 (de) | 1991-11-27 | 1992-11-25 | Oxycodonzusammensetzungen mit kontrollierter Freisetzung |
DE69233327T Expired - Lifetime DE69233327T2 (de) | 1991-11-27 | 1992-11-25 | Oxycodonhaltige Arzneizusammensetzungen mit verzögerter Wirkstoffabgabe |
DE69214802T Expired - Lifetime DE69214802T2 (de) | 1991-11-27 | 1992-11-25 | Oxycodon-zusammensetzungen mit kontrollierter freisetzung |
Family Applications Before (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE69233326T Expired - Lifetime DE69233326T2 (de) | 1991-11-27 | 1992-11-25 | Oxycodonhaltige Zubereitungen mit gesteuerter Wirkstoffabgabe |
DE69233778T Expired - Lifetime DE69233778D1 (de) | 1991-11-27 | 1992-11-25 | Oxycodonzusammensetzungen mit kontrollierter Freisetzung |
DE69232837.8T Expired - Lifetime DE69232837T3 (de) | 1991-11-27 | 1992-11-25 | Oxycodonhaltiges Arzneimittel mit verzögerter Wirkstoffabgabe |
Family Applications After (6)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE69233328T Expired - Lifetime DE69233328T3 (de) | 1991-11-27 | 1992-11-25 | Oxycodonhaltige Arzneizusammensetzungen mit verzögerter Wirkstoffabgabe |
DE69233640T Expired - Lifetime DE69233640T2 (de) | 1991-11-27 | 1992-11-25 | Oxycodonsalzzusammensetzungen mit kontrollierter Freisetzung |
DE69233699T Expired - Lifetime DE69233699T2 (de) | 1991-11-27 | 1992-11-25 | Oxycodonzusammensetzungen mit kontrollierter Freisetzung |
DE69233691T Expired - Lifetime DE69233691T2 (de) | 1991-11-27 | 1992-11-25 | Oxycodonzusammensetzungen mit kontrollierter Freisetzung |
DE69233327T Expired - Lifetime DE69233327T2 (de) | 1991-11-27 | 1992-11-25 | Oxycodonhaltige Arzneizusammensetzungen mit verzögerter Wirkstoffabgabe |
DE69214802T Expired - Lifetime DE69214802T2 (de) | 1991-11-27 | 1992-11-25 | Oxycodon-zusammensetzungen mit kontrollierter freisetzung |
Country Status (31)
Country | Link |
---|---|
US (13) | US5266331A (de) |
EP (15) | EP1327445B1 (de) |
JP (2) | JP3375960B2 (de) |
KR (1) | KR100280973B1 (de) |
CN (2) | CN1165307C (de) |
AT (9) | ATE365041T1 (de) |
AU (1) | AU657027B2 (de) |
BG (1) | BG61753B1 (de) |
BR (1) | BR9205498A (de) |
CA (1) | CA2098738C (de) |
CZ (4) | CZ298499B6 (de) |
DE (10) | DE69233326T2 (de) |
DK (10) | DK1502592T3 (de) |
ES (9) | ES2268189T3 (de) |
FI (5) | FI113152B (de) |
GR (1) | GR3022273T3 (de) |
HK (6) | HK1073255A1 (de) |
HU (10) | HU227815B1 (de) |
IL (1) | IL103909A (de) |
MX (1) | MX9302968A (de) |
NO (6) | NO307028B3 (de) |
PH (1) | PH31679A (de) |
PL (2) | PL173574B1 (de) |
PT (8) | PT1502592E (de) |
RO (1) | RO115112B1 (de) |
RS (3) | RS50055B (de) |
RU (1) | RU2122411C1 (de) |
SK (1) | SK280295B6 (de) |
WO (1) | WO1993010765A1 (de) |
YU (1) | YU49495B (de) |
ZA (1) | ZA929227B (de) |
Families Citing this family (296)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5656295A (en) * | 1991-11-27 | 1997-08-12 | Euro-Celtique, S.A. | Controlled release oxycodone compositions |
US5266331A (en) † | 1991-11-27 | 1993-11-30 | Euroceltique, S.A. | Controlled release oxycodone compositions |
US5478577A (en) * | 1993-11-23 | 1995-12-26 | Euroceltique, S.A. | Method of treating pain by administering 24 hour oral opioid formulations exhibiting rapid rate of initial rise of plasma drug level |
US5958459A (en) * | 1991-12-24 | 1999-09-28 | Purdue Pharma L.P. | Opioid formulations having extended controlled released |
US5968551A (en) * | 1991-12-24 | 1999-10-19 | Purdue Pharma L.P. | Orally administrable opioid formulations having extended duration of effect |
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1991
- 1991-11-27 US US07/800,549 patent/US5266331A/en not_active Expired - Lifetime
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1992
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2000
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2001
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2002
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2003
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2004
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2005
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2006
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