CA2491572A1 - Abuse-deterrent pharmaceutical compositions of opiods and other drugs - Google Patents
Abuse-deterrent pharmaceutical compositions of opiods and other drugs Download PDFInfo
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- CA2491572A1 CA2491572A1 CA002491572A CA2491572A CA2491572A1 CA 2491572 A1 CA2491572 A1 CA 2491572A1 CA 002491572 A CA002491572 A CA 002491572A CA 2491572 A CA2491572 A CA 2491572A CA 2491572 A1 CA2491572 A1 CA 2491572A1
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- 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
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- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof
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- 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
- A61K9/145—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 compounds
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- 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
- A61K9/16—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
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- 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
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1682—Processes
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- 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
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1682—Processes
- A61K9/1694—Processes resulting in granules or microspheres of the matrix type containing more than 5% of excipient
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- 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
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4858—Organic compounds
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- 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
-
- 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
- A61K9/5021—Organic macromolecular compounds
- A61K9/5052—Proteins, e.g. albumin
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- 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
- A61K9/5084—Mixtures of one or more drugs in different galenical forms, at least one of which being granules, microcapsules or (coated) microparticles according to A61K9/16 or A61K9/50, e.g. for obtaining a specific release pattern or for combining different drugs
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
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- 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
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- 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
- A61P25/20—Hypnotics; Sedatives
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- 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
- A61P25/24—Antidepressants
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- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
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- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
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- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
Abstract
An abuse-deterrent pharmaceutical composition has been developed to reduce t he likelihood of improper administration of drugs, especially drugs such as opiods. In the preferred embodiment, a drug is modified to increase its lipophilicity. In preferred embodiments the modified drug is homogeneously dispersed within microparticles composed of a material that is either slowly soluble or not soluble in water. In some embodiments the drug containing microparticles or drug particles are coated with one or more coating layers, where at least one coating is water insoluble and preferably organic solvent insoluble, but enzymatically degradable by enzymes present in the human gastrointestinal tract. The abuse-deterrent composition retards the release of drug, even if the physical integrity of the formulation is compromised (for example, by chopping with a blade or crushing) and the resulting material is placed in water, snorted, or swallowed. However, when administered as directed, the drug is slowly released from the composition as the compositio n is broken down or dissolved gradually within the GI tract by a combination o f enzymatic degradation, surfactant action of bile acids, and mechanical erosi on.
Claims (32)
1. An orally administerable abuse-deterrent pharmaceutical composition comprising a therapeutically effective amount of a drug prone to abuse selected from the group of compositions consisting of (a) a composition comprising a therapeutically effective amount of a lipophilic derivative of a drug prone to abuse, and (b) a water-insoluble, preferably lipophilic, formulation comprising a therapeutically effective amount of a drug prone to abuse.
2. The composition of claim 1 comprising a therapeutically effective amount of a lipophilic derivative of a drug prone to abuse in one or more pharmaceutically acceptable excipients.
3. The composition of Claim 1, wherein the composition is a controlled-release pharmaceutical composition.
4. The composition of Claim 1, wherein the composition prevents the immediate release of a substantial portion of incorporated drug when the physical integrity of the composition is compromised and the resulting material is exposed to an aqueous medium.
5. The composition of Claim 4, wherein the portion of the drug released immediately is less than 80% of the total amount of drug incorporated into formulation.
6. The composition of Claim 1, wherein the composition prevents the immediate release of a substantial portion of incorporated drug when the physical integrity of the composition is compromised and the resulting material is exposed to a non-aqueous medium.
7. The composition of Claim 6, wherein the portion of the drug released immediately is less than 80% of the total amount of the drug incorporated into the composition.
8. The composition of Claim 1 wherein the drug prone to abuse is selected from the group consisting of 1-phenylcyclohexylamine, 1-piperidinocyclohexanecarbonitrile, alfentanil, alphacetylmethadol, alphaprodine, alprazolam, amobarbital, amphetamine, anileridine, apomorphine, aprobarbital, barbital, barbituric acid derivative, bemidone, benzoylecgonine, benzphetamine, betacetylmethadol, betaprodine, bezitramide, bromazepam, buprenorphine, butabarbital, butalbital, butorphanol, camazepam, cathine, chloral, chlordiazepoxide, clobazam, clonazepam, clorazepate, clotiazepam, cloxazolam, cocaine, codeine, chlorphentermine, delorazepam, dexfenfluramine, dextromoramide, dextropropoxyphen, dezocine, diazepam, diethylpropion, difenoxin, dihydrocodeine, dihydromorphine, dioxaphentyl butyrate, dipanone, diphenoxylate, diprenorphine, ecgonine, enadoline, eptazocine, estazolam, ethoheptazine, ethyl loflazepate, ethylmorphine, etorphine, femproponex, fencamfamin, fenfluramine, fentanyl, fludiazepam, flunitrazepam, flurazepam, glutethimide, halazepam, haloxazolam, hexalgon, hydrocodone, hydromorphone, isomethadone, hydrocodone, ketamine, ketazolam, ketobemidone, levanone, levoalphacetylmethadol, levomethadone, levomethadyl acetate, levomethorphan, levorphanol, lofentanil, loperamide, loprazolam, lorazepam, lormetazepam, lysergic acid, lysergic acid amide, mazindol, medazepam, mefenorex, meperidine, meptazinol, metazocine, methadone, methamphetamine, methohexital, methotrimeprazine, methyldihydromorphinone, methylphenidate, methylphenobarbital, metopon, morphine, nabilone, nalbuphine, nalbupine, nalorphine, narceine, nefopam, nicomorphine, nimetazepam, nitrazepam, nordiazepam, normethadone, normorphine, oxazepam, oxazolam, oxycodone, oxymorphone, pentazocine, pentobarbital, phenadoxone, phenazocine, phencyclidine, phendimetrazine, phenmetrazine, pheneridine, piminodine, prodilidine, properidine, propoxyphene, racemethorphan, racemorphan, racemoramide, remifentanil, secobarbital, sufentanil, talbutal, thebaine, thiamylal, thiopental, tramadol, trimeperidine, vinbarbital, allobarbitone, alprazolam, amylobarbitone, aprobarbital, barbital, barbitone, benzphetamine, brallobarbital, bromazepam, brotizolam, buspirone, butalbital, butobarbitone, butorphanol, camazepam, captodiame, carbromal, carfentanil, carpipramine, cathine, chloral, chloral betaine, chloral hydrate, chloralose, chlordiazepoxide, chlorhexadol, chlormethiazole edisylate, chlormezanone, cinolazepam, clobazam, potassium clorazepate, clotiazepam, cloxazolam, cyclobarbitone, delorazepam, dexfenfluramine, diazepam, diethylpropion, difebarbamate, difenoxin, enciprazine, estazolam, ethyl loflazepate, etizolam, febarbamate, fencamfamin, fenfluramine, fenproporex, fluanisone, fludiazepam, flunitraam, flunitrazepam, flurazepam, flutoprazepam, gepirone, glutethimide, halazepam, haloxazolam, hexobarbitone, ibomal, ipsapirone, ketazolam, loprazolam mesylate, lorazepam, lormetazepam, mazindol, mebutamate, medazepam, mefenorex, mephobarbital, meprobamate, metaclazepam, methaqualone, methohexital, methylpentynol, methylphenobarbital, midazolam, milazolam, morphine, nimetazepam, nitrazepam, nordiazepam, oxazepam, oxazolam, paraldehyde, pemoline, pentabarbitone, pentazocine, pentobarbital, phencyclidine, Phenobarbital, phendimetrazine, phenmetrazine, phenprobamate, phentermine, phenyacetone, pinazepam, pipradol, prazepam, proxibarbal, quazepam, quinalbaritone, secobarbital, secbutobarbitone, sibutramine, temazepam, tetrazepam, triazolam, triclofos, zalepan, zaleplon, zolazepam, zolpidem, and zopiclone.
9. The composition of Claim 2, wherein the lipophilic derivative of a drug is a free base or a free acid of the drug.
10. The composition of Claim 2, wherein the lipophilic derivative of a drug is a salt comprising the ionized drug and a lipophilic counter-ion.
11. The composition of Claim 2, wherein the lipophilic derivative of a drug is a complex comprising one or more components selected from the group consisting of drug molecules, metal cations, and lipophilic counter-ions.
12. The composition of Claim 2, wherein the lipophilic derivative of a drug is a complex comprising one or more components selected from the group consisting of drug molecules, metal cations, and cyclodextrin molecules.
13. The composition of Claim 2 wherein the drug is complexed with a metal cation selected from the group consisting of zinc, calcium, magnesium, bismuth and combinations thereof.
14. The composition of Claim 11 wherein the drug is oxycodone, and wherein the metal cation is selected from the group consisting of zinc, calcium, magnesium, and bismuth and the lipophilic counter-ion is selected from the group consisting of stearate, oleate, palmitate, laurate and linoleate.
15. The composition of Claim 2, wherein the lipophilic derivative of a drug is a complex comprising the drug and a cyclodextrin.
16. The composition of Claim 2, wherein the lipophilic derivative of a drug is an ester or amide formed between the drug and a fatty acid.
17. The composition of Claim 1, wherein the drug is incorporated into a plurality of individual microparticles comprising a material that is either slowly soluble in water or water insoluble.
18. The composition of Claim 17 wherein the microparticles comprise a wax or wax-like material.
19. The composition of Claim 17 wherein the microparticles comprise a fat or a fatty substance.
20. The composition of Claim 17 wherein the microparticles comprise a material selected from the group consisting of naturally water insoluble proteins, naturally water insoluble polysaccharides, naturally water insoluble lipids and phospholipids, cross-linked water soluble proteins, cross-linked water soluble polysaccharides, cross-linked water soluble cyclodextrins and combinations thereof.
21. The composition of Claim 17 wherein the individual microparticles are coated with one or more independent layers, where at least one of the layers is water insoluble and is degraded by enzymes of the human gastrointestinal tract.
22. The composition of Claim 1 wherein the drug is in the form of individual drug particles coated with one or more independent layers where at least one of the layers is water insoluble and is degraded by enzymes of the human gastrointestinal tract.
23. The composition of Claim 21 wherein at least one of the layers is water-insoluble, organic solvent-insoluble, and degradable by enzymes present in the human gastrointestinal tract.
24. The composition of Claim 21 comprising materials wherein a combination of these materials is not soluble in water, organic solvent, or any combination thereof.
25. The composition of Claim 21 wherein the composition is not completely soluble, and wherein the drug is not fully released in a single solvent or enzyme solution.
26. The composition of Claim 21 wherein the enzymatically degradable layer(s) comprise a material selected from the group consisting of naturally water insoluble proteins, naturally water insoluble polysaccharides, naturally water insoluble lipids and phospholipids, cross-linked proteins, cross-linked polysaccharides, and combinations thereof.
27. The composition of Claim 1 wherein the drug prone to abuse is co-administered with a drug that has no appreciable abuse potential.
28. The composition of claim 1 formulated for the drug to be immediately released upon oral administration.
29. The composition of claim 1 wherein the drug prone to abuse is oxycodone.
30. A method of manufacturing an abuse-resistant pharmaceutical composition comprising homogeneously dispersing a therapeutically effective amount of a drug prone to abuse, in one or more pharmaceutically acceptable carrier(s), diluent(s), and/or additives, to form an orally administerable abuse-deterrent pharmaceutical composition comprising a therapeutically effective amount of a drug prone to abuse selected from the group of compositions consisting of (a) a composition comprising a therapeutically effective amount of a lipophilic derivative of a drug prone to abuse, and (b) a water-insoluble, preferably lipophilic, formulation comprising a therapeutically effective amount of a drug prone to abuse, as defined by any of claims 1-29.
31. The method of claim 30 further comprising formulating the composition into a capsule or tablet.
32. A method of administering an abuse-resistant pharmaceutical composition comprising orally administering to a patient in need thereof an abuse-deterrent pharmaceutical composition comprising a therapeutically effective amount of a drug prone to abuse selected from the group of compositions consisting of (a) a composition comprising a therapeutically effective amount of a lipophilic derivative of a drug prone to abuse, and (b) a water-insoluble, preferably lipophilic, formulation comprising a therapeutically effective amount of a drug prone to abuse, as defined by any of claims 1-29.
Applications Claiming Priority (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US39387602P | 2002-07-05 | 2002-07-05 | |
US60/393,876 | 2002-07-05 | ||
US43652302P | 2002-12-23 | 2002-12-23 | |
US60/436,523 | 2002-12-23 | ||
US44322603P | 2003-01-28 | 2003-01-28 | |
US60/443,226 | 2003-01-28 | ||
US46351403P | 2003-04-15 | 2003-04-15 | |
US46351803P | 2003-04-15 | 2003-04-15 | |
US60/463,514 | 2003-04-15 | ||
US60/463,518 | 2003-04-15 | ||
PCT/US2003/021095 WO2004004693A1 (en) | 2002-07-05 | 2003-07-07 | Abuse-deterrent pharmaceutical compositions of opiods and other drugs |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2491572A1 true CA2491572A1 (en) | 2004-01-15 |
CA2491572C CA2491572C (en) | 2010-03-23 |
Family
ID=30119451
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA2491572A Expired - Fee Related CA2491572C (en) | 2002-07-05 | 2003-07-07 | Abuse-deterrent pharmaceutical compositions of opiods and other drugs |
Country Status (6)
Country | Link |
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US (6) | US7399488B2 (en) |
EP (1) | EP1594467A4 (en) |
JP (5) | JP4694207B2 (en) |
AU (1) | AU2003247876B2 (en) |
CA (1) | CA2491572C (en) |
WO (1) | WO2004004693A1 (en) |
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DE102004020220A1 (en) * | 2004-04-22 | 2005-11-10 | Grünenthal GmbH | Process for the preparation of a secured against misuse, solid dosage form |
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EP1604666A1 (en) * | 2004-06-08 | 2005-12-14 | Euro-Celtique S.A. | Opioids for the treatment of the Chronic Obstructive Pulmonary Disease (COPD) |
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-
2003
- 2003-07-07 JP JP2004562624A patent/JP4694207B2/en not_active Expired - Fee Related
- 2003-07-07 WO PCT/US2003/021095 patent/WO2004004693A1/en active Application Filing
- 2003-07-07 EP EP03763229A patent/EP1594467A4/en not_active Withdrawn
- 2003-07-07 CA CA2491572A patent/CA2491572C/en not_active Expired - Fee Related
- 2003-07-07 US US10/614,866 patent/US7399488B2/en active Active
- 2003-07-07 AU AU2003247876A patent/AU2003247876B2/en not_active Ceased
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2008
- 2008-04-30 US US12/112,993 patent/US20080199530A1/en not_active Abandoned
- 2008-04-30 US US12/112,937 patent/US20080260819A1/en not_active Abandoned
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2009
- 2009-10-01 JP JP2009230021A patent/JP2009298822A/en not_active Withdrawn
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2012
- 2012-07-17 US US13/551,455 patent/US9044398B2/en not_active Expired - Lifetime
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2013
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2015
- 2015-05-20 US US14/717,232 patent/US20150265596A1/en not_active Abandoned
- 2015-07-03 JP JP2015134210A patent/JP2015166402A/en not_active Withdrawn
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2017
- 2017-03-03 JP JP2017040407A patent/JP2017101075A/en active Pending
- 2017-10-05 US US15/725,818 patent/US20180028528A1/en not_active Abandoned
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JP2017101075A (en) | 2017-06-08 |
JP2009298822A (en) | 2009-12-24 |
US20040052731A1 (en) | 2004-03-18 |
JP2013216707A (en) | 2013-10-24 |
JP4694207B2 (en) | 2011-06-08 |
US20080199530A1 (en) | 2008-08-21 |
US20080260819A1 (en) | 2008-10-23 |
EP1594467A1 (en) | 2005-11-16 |
JP2006500426A (en) | 2006-01-05 |
WO2004004693A1 (en) | 2004-01-15 |
US7399488B2 (en) | 2008-07-15 |
US9044398B2 (en) | 2015-06-02 |
EP1594467A4 (en) | 2008-10-22 |
US20150265596A1 (en) | 2015-09-24 |
US20180028528A1 (en) | 2018-02-01 |
JP2015166402A (en) | 2015-09-24 |
AU2003247876B2 (en) | 2006-10-05 |
US20130045960A1 (en) | 2013-02-21 |
AU2003247876A1 (en) | 2004-01-23 |
CA2491572C (en) | 2010-03-23 |
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