CA2491572A1 - Abuse-deterrent pharmaceutical compositions of opiods and other drugs - Google Patents

Abuse-deterrent pharmaceutical compositions of opiods and other drugs Download PDF

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Publication number
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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Prior art keywords
drug
composition
abuse
prone
lipophilic
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CA002491572A
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French (fr)
Other versions
CA2491572C (en
Inventor
Jane Hirsh
Alexander M. Klibanov
Timothy M. Swager
Stephen L. Buchwald
Whe Yong Lo
Alison B. Fleming
Roman V. Rariy
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Collegium Pharmaceutical Inc
Original Assignee
Collegium Pharmaceutical, Inc.
Jane Hirsh
Alexander M. Klibanov
Timothy M. Swager
Stephen L. Buchwald
Whe Yong Lo
Alison B. Fleming
Roman V. Rariy
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Application filed by Collegium Pharmaceutical, Inc., Jane Hirsh, Alexander M. Klibanov, Timothy M. Swager, Stephen L. Buchwald, Whe Yong Lo, Alison B. Fleming, Roman V. Rariy filed Critical Collegium Pharmaceutical, Inc.
Publication of CA2491572A1 publication Critical patent/CA2491572A1/en
Application granted granted Critical
Publication of CA2491572C publication Critical patent/CA2491572C/en
Anticipated expiration legal-status Critical
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic 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
    • A61K31/47Quinolines; Isoquinolines
    • A61K31/485Morphinan derivatives, e.g. morphine, codeine
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/185Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19Carboxylic acids, e.g. valproic acid
    • A61K31/20Carboxylic 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/12Carboxylic acids; Salts or anhydrides thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/14Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/141Intimate 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
    • A61K9/145Intimate 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/14Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605Excipients; Inactive ingredients
    • A61K9/1617Organic compounds, e.g. phospholipids, fats
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/14Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1682Processes
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/14Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1682Processes
    • A61K9/1694Processes resulting in granules or microspheres of the matrix type containing more than 5% of excipient
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/48Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/4841Filling excipients; Inactive ingredients
    • A61K9/4858Organic compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/48Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50Microcapsules 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/48Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50Microcapsules 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
    • A61K9/5005Wall or coating material
    • A61K9/5021Organic macromolecular compounds
    • A61K9/5052Proteins, e.g. albumin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/48Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50Microcapsules 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
    • A61K9/5084Mixtures 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P23/00Anaesthetics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/04Centrally acting analgesics, e.g. opioids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/20Hypnotics; Sedatives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/24Antidepressants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/26Psychostimulants, e.g. nicotine, cocaine
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/30Drugs for disorders of the nervous system for treating abuse or dependence
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/30Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/36Opioid-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.
CA2491572A 2002-07-05 2003-07-07 Abuse-deterrent pharmaceutical compositions of opiods and other drugs Expired - Fee Related CA2491572C (en)

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

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CA2491572A Expired - Fee Related CA2491572C (en) 2002-07-05 2003-07-07 Abuse-deterrent pharmaceutical compositions of opiods and other drugs

Country Status (6)

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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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