CA2630703C - Processes for reducing contaminating michael acceptor levels in oxycodone and other compositions - Google Patents
Processes for reducing contaminating michael acceptor levels in oxycodone and other compositions Download PDFInfo
- Publication number
- CA2630703C CA2630703C CA2630703A CA2630703A CA2630703C CA 2630703 C CA2630703 C CA 2630703C CA 2630703 A CA2630703 A CA 2630703A CA 2630703 A CA2630703 A CA 2630703A CA 2630703 C CA2630703 C CA 2630703C
- Authority
- CA
- Canada
- Prior art keywords
- thiol
- oxycodone
- michael
- michael acceptor
- salt
- 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 - Fee Related
Links
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- 229960002085 oxycodone Drugs 0.000 title claims description 207
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- LLPOLZWFYMWNKH-CMKMFDCUSA-N hydrocodone Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)CC(=O)[C@@H]1OC1=C2C3=CC=C1OC LLPOLZWFYMWNKH-CMKMFDCUSA-N 0.000 claims description 3
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- 229940006193 2-mercaptoethanesulfonic acid Drugs 0.000 claims description 2
- FFFHZYDWPBMWHY-VKHMYHEASA-N L-homocysteine Chemical compound OC(=O)[C@@H](N)CCS FFFHZYDWPBMWHY-VKHMYHEASA-N 0.000 claims description 2
- VLSOAXRVHARBEQ-UHFFFAOYSA-N [4-fluoro-2-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=C(F)C=C1CO VLSOAXRVHARBEQ-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
- C07D489/02—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: with oxygen atoms attached in positions 3 and 6, e.g. morphine, morphinone
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
- A23L5/20—Removal of unwanted matter, e.g. deodorisation or detoxification
- A23L5/27—Removal of unwanted matter, e.g. deodorisation or detoxification by chemical treatment, by adsorption or by absorption
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
- C07D489/06—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: with a hetero atom directly attached in position 14
- C07D489/08—Oxygen atom
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/62—Detectors specially adapted therefor
- G01N30/74—Optical detectors
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/02—Food
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/15—Medicinal preparations ; Physical properties thereof, e.g. dissolubility
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N2030/022—Column chromatography characterised by the kind of separation mechanism
- G01N2030/027—Liquid chromatography
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Food Science & Technology (AREA)
- Physics & Mathematics (AREA)
- Medicinal Chemistry (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Nutrition Science (AREA)
- Polymers & Plastics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cleaning Or Drying Semiconductors (AREA)
- Processing Of Solid Wastes (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73908705P | 2005-11-22 | 2005-11-22 | |
| US60/739,087 | 2005-11-22 | ||
| PCT/US2006/045316 WO2007062184A2 (en) | 2005-11-22 | 2006-11-22 | Processes for reducing contaminating michael acceptor levels in oxycodone and other compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2630703A1 CA2630703A1 (en) | 2007-05-31 |
| CA2630703C true CA2630703C (en) | 2014-05-20 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2630703A Expired - Fee Related CA2630703C (en) | 2005-11-22 | 2006-11-22 | Processes for reducing contaminating michael acceptor levels in oxycodone and other compositions |
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| Country | Link |
|---|---|
| US (4) | US7875623B2 (https=) |
| EP (2) | EP2402346A1 (https=) |
| JP (2) | JP5415075B2 (https=) |
| KR (3) | KR101561760B1 (https=) |
| CN (2) | CN101346384B (https=) |
| CA (1) | CA2630703C (https=) |
| MX (2) | MX2008006710A (https=) |
| WO (1) | WO2007062184A2 (https=) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3175780A1 (en) | 2003-12-18 | 2017-06-07 | Metronom Health, Inc. | Implantable biosensor and methods of use thereof |
| TWI365880B (en) | 2004-03-30 | 2012-06-11 | Euro Celtique Sa | Process for preparing oxycodone hydrochloride having less than 25 ppm 14-hydroxycodeinone and oxycodone hydrochloride composition,pharmaceutical dosage form,sustained release oeal dosage form and pharmaceutically acceptable package having less than 25 pp |
| CN101346384B (zh) | 2005-11-22 | 2012-07-04 | 控制化学品公司 | 用于降低羟考酮和其它组分中杂质迈克尔受体水平的方法 |
| MX2008010921A (es) * | 2006-03-02 | 2008-09-03 | Mallinckrodt Inc | Procesos para preparar productos de morfinan-6-ona con bajos niveles de compuestos de cetona alfa, beta-insaturados. |
| US7875719B2 (en) * | 2006-12-04 | 2011-01-25 | Cox D Phillip | Process for reducing impurities in oxycodone base |
| JP2010511726A (ja) * | 2006-12-04 | 2010-04-15 | ノランコ・インコーポレーテツド | １４−ヒドロキシコデイノンの濃度が低いオキシコドンの製造方法 |
| FR2923484B1 (fr) | 2007-11-09 | 2012-11-09 | Sanofi Aventis | Procede de preparation de composes morphiniques |
| WO2012003468A1 (en) | 2010-07-02 | 2012-01-05 | Johnson Matthey Public Limited Company | Process for the synthesis and purification of oxycodone |
| RS58427B1 (sr) | 2012-08-03 | 2019-04-30 | Johnson Matthey Plc | Postupak za pripremu oksikodona |
| US9062062B1 (en) | 2013-12-18 | 2015-06-23 | Cody Laboratories, Inc. | Synthesis of oxycodone hydrochloride |
| US8846923B1 (en) | 2013-12-18 | 2014-09-30 | Cody Laboratories, Inc. | Preparation of 14-hydroxycodeinone sulfate |
| US10227354B2 (en) | 2013-12-18 | 2019-03-12 | Cody Laboratories, Inc. | Conversion of oxycodone base to oxycodone hydrochloride |
| CA2954600A1 (en) | 2014-07-09 | 2016-01-14 | Rhodes Technologies | Reduction of alpha, beta-unsaturated ketone levels in morphinan derivative compositions |
| US10695000B2 (en) | 2015-09-02 | 2020-06-30 | Metronom Health, Inc. | Systems and methods for continuous health monitoring using an opto-enzymatic analyte sensor |
| CN109725065A (zh) * | 2017-10-31 | 2019-05-07 | 中国石油化工股份有限公司 | 一种轻质油中硫醇类化合物的分析方法 |
| CN113237988B (zh) * | 2021-04-30 | 2021-12-31 | 北京济圣康泰国际医药科技有限公司 | 一种羟考酮液体制剂中降解杂质羟醛二聚体含量的检测方法 |
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| US6552170B1 (en) * | 1990-04-06 | 2003-04-22 | Amgen Inc. | PEGylation reagents and compounds formed therewith |
| JP2001505558A (ja) | 1996-11-15 | 2001-04-24 | シンソーブ バイオテック，インコーポレイテッド | 炭化水素ライブラリーのコンビナトリアル合成 |
| US6177567B1 (en) * | 1999-10-15 | 2001-01-23 | Boehringer Ingelheim Chemicals, Inc. | Method for preparing oxycodone |
| EP1456214A2 (en) * | 2001-12-14 | 2004-09-15 | Charterhouse Therapeutics Limited | Improvements in pharmaceutical compositions |
| TWI365880B (en) * | 2004-03-30 | 2012-06-11 | Euro Celtique Sa | Process for preparing oxycodone hydrochloride having less than 25 ppm 14-hydroxycodeinone and oxycodone hydrochloride composition,pharmaceutical dosage form,sustained release oeal dosage form and pharmaceutically acceptable package having less than 25 pp |
| CN101346384B (zh) * | 2005-11-22 | 2012-07-04 | 控制化学品公司 | 用于降低羟考酮和其它组分中杂质迈克尔受体水平的方法 |
| MX2008010921A (es) * | 2006-03-02 | 2008-09-03 | Mallinckrodt Inc | Procesos para preparar productos de morfinan-6-ona con bajos niveles de compuestos de cetona alfa, beta-insaturados. |
| EP2322926A1 (en) | 2009-11-11 | 2011-05-18 | Zedira GmbH | Stabilized open form transglutaminase as a diagnostic indicator for autoimmune diseases |
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2006
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- 2006-11-22 JP JP2008542458A patent/JP5415075B2/ja not_active Expired - Fee Related
- 2006-11-22 EP EP20110154924 patent/EP2402346A1/en not_active Withdrawn
- 2006-11-22 CN CN201210142283.4A patent/CN102816167B/zh not_active Expired - Fee Related
- 2006-11-22 KR KR1020137031487A patent/KR101561760B1/ko not_active Expired - Fee Related
- 2006-11-22 WO PCT/US2006/045316 patent/WO2007062184A2/en not_active Ceased
- 2006-11-22 MX MX2008006710A patent/MX2008006710A/es active IP Right Grant
- 2006-11-22 US US11/603,956 patent/US7875623B2/en not_active Expired - Fee Related
- 2006-11-22 EP EP06838339A patent/EP1971607A2/en not_active Ceased
- 2006-11-22 KR KR1020157007999A patent/KR20150041176A/ko not_active Ceased
- 2006-11-22 CA CA2630703A patent/CA2630703C/en not_active Expired - Fee Related
- 2006-11-22 KR KR1020087015013A patent/KR101417135B1/ko not_active Expired - Fee Related
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2008
- 2008-05-22 MX MX2012006612A patent/MX345055B/es unknown
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2010
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2013
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2014
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2016
- 2016-08-01 US US15/225,699 patent/US10201174B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN101346384B (zh) | 2012-07-04 |
| MX345055B (es) | 2017-01-13 |
| JP2013079279A (ja) | 2013-05-02 |
| EP2402346A1 (en) | 2012-01-04 |
| US10201174B2 (en) | 2019-02-12 |
| CN102816167A (zh) | 2012-12-12 |
| CN102816167B (zh) | 2016-01-06 |
| JP5415075B2 (ja) | 2014-02-12 |
| CA2630703A1 (en) | 2007-05-31 |
| KR20150041176A (ko) | 2015-04-15 |
| US20070149559A1 (en) | 2007-06-28 |
| US20170027199A1 (en) | 2017-02-02 |
| JP2009516750A (ja) | 2009-04-23 |
| WO2007062184A2 (en) | 2007-05-31 |
| US9034893B2 (en) | 2015-05-19 |
| US20150148537A1 (en) | 2015-05-28 |
| CN101346384A (zh) | 2009-01-14 |
| US7875623B2 (en) | 2011-01-25 |
| US20110136849A1 (en) | 2011-06-09 |
| KR101561760B1 (ko) | 2015-10-20 |
| US9403838B2 (en) | 2016-08-02 |
| KR20140002807A (ko) | 2014-01-08 |
| KR20080096750A (ko) | 2008-11-03 |
| AU2006318445A1 (en) | 2007-05-31 |
| KR101417135B1 (ko) | 2014-07-08 |
| MX2008006710A (es) | 2008-12-16 |
| WO2007062184A3 (en) | 2007-07-26 |
| EP1971607A2 (en) | 2008-09-24 |
| HK1179622A1 (zh) | 2013-10-04 |
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