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US20030130297A1 - Oral administration of 6-hydroxy-oxymorphone for use as an analgesic - Google Patents

Oral administration of 6-hydroxy-oxymorphone for use as an analgesic Download PDF

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US20030130297A1
US20030130297A1 US10/189,897 US18989702A US2003130297A1 US 20030130297 A1 US20030130297 A1 US 20030130297A1 US 18989702 A US18989702 A US 18989702A US 2003130297 A1 US2003130297 A1 US 2003130297A1
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oxymorphone
hydroxy
hydroxy oxymorphone
pharmaceutical composition
blood plasma
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US10/189,897
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Huai-Hung Kao
Richard Smith-Carliss
Troy McCall
David Lee
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Endo Pharmaceuticals Inc
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Endo Pharmaceuticals Inc
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Priority to US10/189,897 priority Critical patent/US20030130297A1/en
Assigned to ENDO PHARMACEUTICALS, INC. reassignment ENDO PHARMACEUTICALS, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: LEE, DAVID, MCCALL, TROY, SMITH-CARLISS, RICHARD, KAO, HUAI-HUNG
Publication of US20030130297A1 publication Critical patent/US20030130297A1/en
Abandoned legal-status Critical Current

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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
    • 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
    • A61K47/02—Inorganic compounds
    • 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
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • 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
    • A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
    • 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
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • 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
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • A61K47/38—Cellulose; Derivatives thereof
    • 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
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
    • 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
    • A61K9/2009—Inorganic compounds
    • 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
    • A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
    • 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
    • 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
    • A61K9/2086—Layered tablets, e.g. bilayer tablets; Tablets of the type inert core-active coat
    • A61K9/209—Layered tablets, e.g. bilayer tablets; Tablets of the type inert core-active coat containing drug in at least two layers or in the core and in at least one outer layer
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]

Definitions

  • the invention relates to methods for alleviating pain. More particularly, the invention relates to methods for alleviating pain by administering 6-hydroxy oxymorphone. Most particularly, the invention relates to methods of inducing analgesia by increasing blood plasma levels of 6-hydroxy oxymorphone through oral administration of a pharmaceutical composition containing 6-hydroxy oxymorphone.
  • the present invention provides methods of treating pain by administering a pharmaceutical composition comprising 6-hydroxy oxymorphone in an amount sufficient to induce analgesia.
  • the pharmaceutical composition is administered orally. Any known or later developed method of oral delivery may be used.
  • blood plasma levels of 6-hydroxy oxymorphone are raised to at least about 0.2 ng/mL. Most preferably blood plasma levels of 6-hydroxy oxymorphone of at least about 0.3 ng/mL during treatment.
  • Methods for administering compositions comprising 6-hydroxy oxymorphone, and one or more carriers, diluents, and excipients in an amount sufficient to induce analgesia are also provided.
  • FIG. 1 is a pharmacokinetic profile for 6-hydroxy oxymorphone with PID scores.
  • FIG. 2 is a pharmacokinetic profile for oxymorphone with PID scores.
  • FIG. 3 is a pharmacokinetic profile for 6-hydroxy oxymorphone with categorical pain scores.
  • FIG. 4 is a pharmacokinetic profile for oxymorphone with categorical pain scores.
  • the methods described herein provide for the administration of a pharmaceutical composition containing 6-hydroxy oxymorphone as an active ingredient.
  • the preferred composition comprises 6-hydroxy oxymorphone alone (excepting, of course, carriers, diluents, and other excipients).
  • 6-hydroxy oxymorphone may be combined with other opioids or other pharmaceutical agents.
  • another preferred embodiment provides compositions comprising both 6-hydroxy oxymorphone and its parent, oxymorphone.
  • FIGS. 1 - 4 show graphical representation of the data combining the two studies such that the effect of blood plasma levels of oxymorphone and its metabolite, 6-hydroxy oxymorphone on pain can be evaluated.
  • Oxymorphone levels peak within 2 hours, fall slightly, and plateau. Interestingly, the level spikes again at 4-6 hours from administration. After this time, oxymorphone levels again drop and eventually fall to levels near the earlier plateau.
  • 6-hydroxy oxymorphone blood plasma levels peak within 2 hours after administration. After the initial peak, however, a more or less steady decline in the 6-hydroxy oxymorphones plasma levels is observed.
  • Formulation as a suspension, syrup, or other liquid, tablet, capsule, liquid-filled gel cap, or other solid or semi-solid means may be used.
  • the composition may alternately be in the form of a time release formulation, including timed, suspended and extended release formulations. Regardless of the formulation, an amount of 6-hydroxy oxymorphone sufficient to induce analgesia will be supplied to the patient. Blood plasma levels of 6-hydroxy oxymorphone must be raised to levels sufficient to induce the desired level of analgesia.
  • the amount administered will be dependent upon normal criteria such as patient weight, intensity of pain, and other factors. Based on the pharmacokinetic studies, blood plasma levels around at least 0.2 ng/mL will provide some analgesia. The upper plasma level limit will be ultimately established by safety concerns. Over-dosing of any opioid, including 6-hydroxy oxymorphone, may lead to respiratory failure and other undesirable side effects and can even result in death. Preferably, the blood plasma level of 6-hydroxy oxymorphone will be raised to at least 0.3 ng/mL. Subsequent doses may be required to maintain these blood levels.
  • the preferred administration is of 6-hydroxy oxymorphone with appropriate carriers and excipients as will be readily apparent to those skilled in the art.
  • the resulting blood plasma in these preferred administrations will therefore be substantially free of oxymorphone.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Inorganic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Molecular Biology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Emergency Medicine (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Biophysics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pain & Pain Management (AREA)
  • Organic Chemistry (AREA)
  • Biochemistry (AREA)
  • Physiology (AREA)
  • Nutrition Science (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Rheumatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Dental Preparations (AREA)

Abstract

In a method of treating pain, a patient is administered a pharmaceutical composition of 6-hydroxy oxymorphone in amount sufficient to induce analgesia. In one embodiment, the pharmaceutical composition is administered orally. Any known or later developed method of oral delivery may be used. To achieve the desired analgesic effect, blood plasma levels of 6-hydroxy oxymorphone are raised to at least approximately 0.2 ng/mL. Most preferably blood plasma levels of 6-hydroxy oxymorphone range at least 0.3 ng/mL during treatment. Administration of compositions containing 6-hydroxy oxymorphone, and one or more carriers, diluents, and excipients in an amount sufficient to induce analgesia is also contemplated.

Description

  • This application relates to provisional patent application serial Nos. 60/329,445 filed Oct. 15, 2001, .60/329,432 filed Oct. 15, 2001, 60/303,357 filed Jul. 6, 2001, and 60/329,444 filed Oct. 15, 2001.[0001]
    • BACKGROUND
  • 1. Field of Invention [0002]
  • The invention relates to methods for alleviating pain. More particularly, the invention relates to methods for alleviating pain by administering 6-hydroxy oxymorphone. Most particularly, the invention relates to methods of inducing analgesia by increasing blood plasma levels of 6-hydroxy oxymorphone through oral administration of a pharmaceutical composition containing 6-hydroxy oxymorphone. [0003]
  • 2. Summary of the Invention [0004]
  • The present invention provides methods of treating pain by administering a pharmaceutical composition comprising 6-hydroxy oxymorphone in an amount sufficient to induce analgesia. In one embodiment, the pharmaceutical composition is administered orally. Any known or later developed method of oral delivery may be used. To achieve the desired analgesic effect, blood plasma levels of 6-hydroxy oxymorphone are raised to at least about 0.2 ng/mL. Most preferably blood plasma levels of 6-hydroxy oxymorphone of at least about 0.3 ng/mL during treatment. Methods for administering compositions comprising 6-hydroxy oxymorphone, and one or more carriers, diluents, and excipients in an amount sufficient to induce analgesia are also provided. [0005]
    • BRIEF DESCRIPTION OF THE DRAWINGS
  • FIG. 1 is a pharmacokinetic profile for 6-hydroxy oxymorphone with PID scores. [0006]
  • FIG. 2 is a pharmacokinetic profile for oxymorphone with PID scores. [0007]
  • FIG. 3 is a pharmacokinetic profile for 6-hydroxy oxymorphone with categorical pain scores. [0008]
  • FIG. 4 is a pharmacokinetic profile for oxymorphone with categorical pain scores.[0009]
    • DETAILED DESCRIPTION
  • The methods described herein provide for the administration of a pharmaceutical composition containing 6-hydroxy oxymorphone as an active ingredient. In a preferred embodiment the preferred composition comprises 6-hydroxy oxymorphone alone (excepting, of course, carriers, diluents, and other excipients). In other preferred embodiments, 6-hydroxy oxymorphone may be combined with other opioids or other pharmaceutical agents. For example, another preferred embodiment provides compositions comprising both 6-hydroxy oxymorphone and its parent, oxymorphone. [0010]
  • In two separate studies, blood plasma levels and indications of pain relief were recorded over a 12 hour period after. FIGS. [0011] 1-4 show graphical representation of the data combining the two studies such that the effect of blood plasma levels of oxymorphone and its metabolite, 6-hydroxy oxymorphone on pain can be evaluated.
  • The administration of oxymorphone yields blood plasma levels of oxymorphone and all of its metabolites, 6-hydroxy oxymorphone. Oxymorphone levels peak within 2 hours, fall slightly, and plateau. Interestingly, the level spikes again at 4-6 hours from administration. After this time, oxymorphone levels again drop and eventually fall to levels near the earlier plateau. [0012]
  • Like oxymorphone, 6-hydroxy oxymorphone blood plasma levels peak within 2 hours after administration. After the initial peak, however, a more or less steady decline in the 6-hydroxy oxymorphones plasma levels is observed. [0013]
  • Comparing these levels to the pain profiles, a correlation between the 6-hydroxy oxymorphone blood plasma levels and pain relief can be seen. The pain levels nearly mirror the 6-hydroxy oxymorphone levels, with substantial rises in relief near the spikes associated with 6-hydroxy oxymorphone blood levels. Thus, pain relief can be achieved through administration of 6-hydroxy oxymorphone alone. [0014]
  • In addition to the pharmacokinetic studies, binding studies have been conducted to compare the binding affinity of 6-hydroxy oxymorphone to that of oxymorphone. The results are reported in TABLE 1. These results clearly indicate that 6-hydroxy oxymorphone has great binding affinity for the δ, κ, and μ receptor cites, comparable to the binding affinity of its parent. The inventors believe that by virtue of this binding affinity, 6-hydroxy oxymorphone has similar analgesic effects to its parent, oxymorphone. [0015]
    TABLE 1
    ASSAY REPORT
    6-HYDROXY
    OXYMORPHONE OXYMORPHONE
    10 nm 10 μm 10 nm 10 μm
    1.0 E−8 1.0 E−5 1.0 E−8 1.0 E−5
    Opiate, Delta 1 −4.12% 90.48% −18.26%  89.03%
    Opiate, Delta 2   7.19% 55.45%   7.76%  72.74%
    (Human
    Recombinant)
    Opiate, Kappa   2.45% 62.47%   10.35%  89.41%
    (Human
    Recombinant
    Opiate, Mu   63.16%  99.91%   85.42% 100.39%
    (Human
    Recombinant)
  • Accordingly, methods of administering the metabolite, 6-hydroxy oxymorphone, directly have been developed. It is believed that the β isomer has greater efficacy in the treatment of pain, but this disclosure is not limited to use of that isomer alone. Pharmaceutical compositions containing either 6-α-hydroxy oxymorphone, 6-β-hydroxy oxymorphone, or mixtures thereof can be used in the invention. [0016]
  • Formulation as a suspension, syrup, or other liquid, tablet, capsule, liquid-filled gel cap, or other solid or semi-solid means may be used. The composition may alternately be in the form of a time release formulation, including timed, suspended and extended release formulations. Regardless of the formulation, an amount of 6-hydroxy oxymorphone sufficient to induce analgesia will be supplied to the patient. Blood plasma levels of 6-hydroxy oxymorphone must be raised to levels sufficient to induce the desired level of analgesia. [0017]
  • The amount administered will be dependent upon normal criteria such as patient weight, intensity of pain, and other factors. Based on the pharmacokinetic studies, blood plasma levels around at least 0.2 ng/mL will provide some analgesia. The upper plasma level limit will be ultimately established by safety concerns. Over-dosing of any opioid, including 6-hydroxy oxymorphone, may lead to respiratory failure and other undesirable side effects and can even result in death. Preferably, the blood plasma level of 6-hydroxy oxymorphone will be raised to at least 0.3 ng/mL. Subsequent doses may be required to maintain these blood levels. [0018]
  • The preferred administration is of 6-hydroxy oxymorphone with appropriate carriers and excipients as will be readily apparent to those skilled in the art. The resulting blood plasma in these preferred administrations will therefore be substantially free of oxymorphone. [0019]
  • The above description encompasses some preferred embodiments of the invention. The disclosure is merely illustrative in nature and is not intended to limit the following claims. [0020]

Claims (8)

What is claimed is:
1. A method of treating pain comprising the step of:
administering to a patient a pharmaceutical composition comprising 6-hydroxy oxymorphone in an amount sufficient to induce analgesia.
2. The method of claim 1 wherein said pharmaceutical composition is administered orally.
3. The method of claim 2 wherein said pharmaceutical composition is administered in a form selected from a liquid formulation, syrup, suspension, solid formulation, tablet, capsule, liquid-filled gel cap, and a semi-solid formulation.
4. The method of claim 1 wherein said administration is sufficient to raise blood plasma levels of 6-hydroxy oxymorphone to at least about 0.2 ng/mL.
5. The method of claim 1 wherein said administration is sufficient to raise blood plasma levels of 6-hydroxy oxymorphone to at least about 0.3 ng/mL.
6. A method of treating pain comprising the step of:
orally administering to a patient a pharmaceutical composition comprising 6-hydroxy oxymorphone, and one or more carriers, diluents, and excipients in an amount sufficient to induce analgesia.
7. A method of treating pain comprising the step of:
orally administering to a patient a pharmaceutical composition comprising 6-hydroxy oxymorphone and oxymorphone in an amount sufficient to induce analgesia.
8. A pharmaceutical composition comprising 6-hydroxy oxymorphone in a formulation for oral delivery to animals including hormone.
US10/189,897 2001-07-06 2002-07-03 Oral administration of 6-hydroxy-oxymorphone for use as an analgesic Abandoned US20030130297A1 (en)

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US10/189,897 US20030130297A1 (en) 2001-07-06 2002-07-03 Oral administration of 6-hydroxy-oxymorphone for use as an analgesic

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US30335701P 2001-07-06 2001-07-06
US32944401P 2001-10-15 2001-10-15
US32944501P 2001-10-15 2001-10-15
US32943201P 2001-10-15 2001-10-15
US10/189,897 US20030130297A1 (en) 2001-07-06 2002-07-03 Oral administration of 6-hydroxy-oxymorphone for use as an analgesic

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US10/189,897 Abandoned US20030130297A1 (en) 2001-07-06 2002-07-03 Oral administration of 6-hydroxy-oxymorphone for use as an analgesic
US10/189,653 Abandoned US20040214849A1 (en) 2001-07-06 2002-07-03 Parenteral administration of 6-hydroxy-oxymorphone for use as an analgesic
US10/190,192 Expired - Lifetime US9820982B2 (en) 2001-07-06 2002-07-03 Oxymorphone controlled release formulations
US11/425,966 Abandoned US20070098792A1 (en) 2001-07-06 2006-06-22 Oxymorphone controlled release formulations
US11/426,170 Abandoned US20070098793A1 (en) 2001-07-06 2006-06-23 Oxymorphone controlled release formulations
US11/680,432 Active 2026-03-08 US8309122B2 (en) 2001-07-06 2007-02-28 Oxymorphone controlled release formulations
US12/167,859 Abandoned US20080262013A1 (en) 2001-07-06 2008-07-03 Oxymorphone controlled release formulations
US12/426,112 Abandoned US20090192183A1 (en) 2001-07-06 2009-04-17 Oxymorphone Controlled Release Formulations
US13/908,328 Abandoned US20140134250A1 (en) 2001-07-06 2013-06-03 Oxymorphone controlled release formulations
US14/492,701 Abandoned US20150011577A1 (en) 2001-07-06 2014-09-22 Oxymorphone controlled release formulations
US14/798,619 Abandoned US20160136152A1 (en) 2001-07-06 2015-07-14 Oxymorphone controlled release compositions
US16/049,390 Abandoned US20180338967A1 (en) 2001-07-06 2018-07-30 Oxymorphone controlled release compositions
US17/035,453 Abandoned US20210008063A1 (en) 2001-07-06 2020-09-28 Oxymorphone controlled release compositions

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US10/189,653 Abandoned US20040214849A1 (en) 2001-07-06 2002-07-03 Parenteral administration of 6-hydroxy-oxymorphone for use as an analgesic
US10/190,192 Expired - Lifetime US9820982B2 (en) 2001-07-06 2002-07-03 Oxymorphone controlled release formulations
US11/425,966 Abandoned US20070098792A1 (en) 2001-07-06 2006-06-22 Oxymorphone controlled release formulations
US11/426,170 Abandoned US20070098793A1 (en) 2001-07-06 2006-06-23 Oxymorphone controlled release formulations
US11/680,432 Active 2026-03-08 US8309122B2 (en) 2001-07-06 2007-02-28 Oxymorphone controlled release formulations
US12/167,859 Abandoned US20080262013A1 (en) 2001-07-06 2008-07-03 Oxymorphone controlled release formulations
US12/426,112 Abandoned US20090192183A1 (en) 2001-07-06 2009-04-17 Oxymorphone Controlled Release Formulations
US13/908,328 Abandoned US20140134250A1 (en) 2001-07-06 2013-06-03 Oxymorphone controlled release formulations
US14/492,701 Abandoned US20150011577A1 (en) 2001-07-06 2014-09-22 Oxymorphone controlled release formulations
US14/798,619 Abandoned US20160136152A1 (en) 2001-07-06 2015-07-14 Oxymorphone controlled release compositions
US16/049,390 Abandoned US20180338967A1 (en) 2001-07-06 2018-07-30 Oxymorphone controlled release compositions
US17/035,453 Abandoned US20210008063A1 (en) 2001-07-06 2020-09-28 Oxymorphone controlled release compositions

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EP (4) EP1406630A1 (en)
JP (4) JP2005520778A (en)
KR (1) KR20030034171A (en)
CN (3) CN1610551A (en)
AT (1) ATE359077T1 (en)
AU (3) AU2002318211B2 (en)
BR (1) BR0205721A (en)
CA (3) CA2452872A1 (en)
DE (1) DE60219478T2 (en)
ES (1) ES2284888T3 (en)
NO (1) NO20031018L (en)
WO (3) WO2003004030A1 (en)

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