KR20150041176A - 옥시코돈 및 다른 조성물에서 오염물질인 마이클 수용체 수준을 감소시키는 방법 - Google Patents
옥시코돈 및 다른 조성물에서 오염물질인 마이클 수용체 수준을 감소시키는 방법 Download PDFInfo
- Publication number
- KR20150041176A KR20150041176A KR1020157007999A KR20157007999A KR20150041176A KR 20150041176 A KR20150041176 A KR 20150041176A KR 1020157007999 A KR1020157007999 A KR 1020157007999A KR 20157007999 A KR20157007999 A KR 20157007999A KR 20150041176 A KR20150041176 A KR 20150041176A
- Authority
- KR
- South Korea
- Prior art keywords
- oxycodone
- thiol
- hydroxycodeinone
- michael
- composition
- 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.)
- Ceased
Links
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- 238000000034 method Methods 0.000 title abstract description 68
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- 229960002085 oxycodone Drugs 0.000 title description 172
- 230000008569 process Effects 0.000 title description 10
- 150000003839 salts Chemical class 0.000 claims description 18
- 150000003573 thiols Chemical class 0.000 abstract description 93
- 150000001875 compounds Chemical class 0.000 abstract description 46
- 239000002243 precursor Substances 0.000 abstract description 12
- 238000011002 quantification Methods 0.000 abstract description 5
- YYCRAERBSFHMPL-XFKAJCMBSA-N (4r,4as,7ar,12bs)-4a-hydroxy-9-methoxy-3-methyl-2,4,7a,13-tetrahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one Chemical compound O=C([C@@H]1O2)C=C[C@@]3(O)[C@]4([H])N(C)CC[C@]13C1=C2C(OC)=CC=C1C4 YYCRAERBSFHMPL-XFKAJCMBSA-N 0.000 description 129
- YYCRAERBSFHMPL-UHFFFAOYSA-N 14beta-Hydroxycodeinone Natural products O1C2C(=O)C=CC3(O)C4CC5=CC=C(OC)C1=C5C23CCN4C YYCRAERBSFHMPL-UHFFFAOYSA-N 0.000 description 128
- 239000000243 solution Substances 0.000 description 113
- 239000000370 acceptor Substances 0.000 description 101
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 82
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- 229940046307 sodium thioglycolate Drugs 0.000 description 31
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- DQCKKXVULJGBQN-XFWGSAIBSA-N naltrexone Chemical compound N1([C@@H]2CC3=CC=C(C=4O[C@@H]5[C@](C3=4)([C@]2(CCC5=O)O)CC1)O)CC1CC1 DQCKKXVULJGBQN-XFWGSAIBSA-N 0.000 description 20
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- 238000002835 absorbance Methods 0.000 description 17
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- YPZPXTZKBNWUTF-UHFFFAOYSA-N 14beta-Hydroxy-codein Natural products O1C2C(O)C=CC3(O)C4CC5=CC=C(OC)C1=C5C23CCN4C YPZPXTZKBNWUTF-UHFFFAOYSA-N 0.000 description 10
- 239000000356 contaminant Substances 0.000 description 10
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- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 9
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- GANZODCWZFAEGN-UHFFFAOYSA-N 5-mercapto-2-nitro-benzoic acid Chemical compound OC(=O)C1=CC(S)=CC=C1[N+]([O-])=O GANZODCWZFAEGN-UHFFFAOYSA-N 0.000 description 5
- 108010024636 Glutathione Proteins 0.000 description 5
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 description 5
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- YTLQUSFUTUNUQM-KFIKYVJASA-N (4r,4as,7ar,12bs)-4a-hydroxy-9-methoxy-3-methyl-2,4,5,6,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one;(4r,4as,7ar,12bs)-4a-hydroxy-9-methoxy-3-methyl-2,4,7a,13-tetrahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(OC)C2=C5[C@@]13CCN4C.O=C([C@@H]1O2)C=C[C@@]3(O)[C@H]4CC5=CC=C(OC)C2=C5[C@@]13CCN4C YTLQUSFUTUNUQM-KFIKYVJASA-N 0.000 description 4
- BQNSLJQRJAJITR-UHFFFAOYSA-N 1,1,2-trichloro-1,2-difluoroethane Chemical compound FC(Cl)C(F)(Cl)Cl BQNSLJQRJAJITR-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical group COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
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- 239000012223 aqueous fraction Substances 0.000 description 4
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- 239000005711 Benzoic acid Substances 0.000 description 3
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Classifications
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
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- 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
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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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- 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
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- 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
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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
- G01N30/62—Detectors specially adapted therefor
- G01N30/74—Optical detectors
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- G—PHYSICS
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- 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
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- 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
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- 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
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- 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)
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- Emergency Medicine (AREA)
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- Biomedical Technology (AREA)
- Pain & Pain Management (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)
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| 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 |
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| KR1020137031487A Division KR101561760B1 (ko) | 2005-11-22 | 2006-11-22 | 옥시코돈 및 다른 조성물에서 오염물질인 마이클 수용체 수준을 감소시키는 방법 |
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| KR20150041176A true KR20150041176A (ko) | 2015-04-15 |
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| KR1020137031487A Expired - Fee Related KR101561760B1 (ko) | 2005-11-22 | 2006-11-22 | 옥시코돈 및 다른 조성물에서 오염물질인 마이클 수용체 수준을 감소시키는 방법 |
| KR1020087015013A Expired - Fee Related KR101417135B1 (ko) | 2005-11-22 | 2006-11-22 | 옥시코돈 및 다른 조성물에서 오염물질인 마이클 수용체수준을 감소시키는 방법 |
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| KR1020137031487A Expired - Fee Related KR101561760B1 (ko) | 2005-11-22 | 2006-11-22 | 옥시코돈 및 다른 조성물에서 오염물질인 마이클 수용체 수준을 감소시키는 방법 |
| KR1020087015013A Expired - Fee Related KR101417135B1 (ko) | 2005-11-22 | 2006-11-22 | 옥시코돈 및 다른 조성물에서 오염물질인 마이클 수용체수준을 감소시키는 방법 |
Country Status (8)
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| EP (2) | EP2402346A1 (https=) |
| JP (2) | JP5415075B2 (https=) |
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| CA (1) | CA2630703C (https=) |
| MX (2) | MX2008006710A (https=) |
| WO (1) | WO2007062184A2 (https=) |
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| EP2659831B1 (en) | 2003-12-18 | 2016-11-30 | Metronom Health, Inc. | Stabilized oxygen transport matrix |
| TW201509943A (zh) | 2004-03-30 | 2015-03-16 | Euro Celtique Sa | 含有小於２５ｐｐｍ１４-羥可待因酮之羥可酮鹽酸鹽之組成物、醫藥劑型、延遲釋出口服劑型及醫藥上可以接受的包裝 |
| CA2630703C (en) * | 2005-11-22 | 2014-05-20 | Controlled Chemicals, Inc. | Processes for reducing contaminating michael acceptor levels in oxycodone and other compositions |
| CN101395159A (zh) * | 2006-03-02 | 2009-03-25 | 马林克罗特公司 | 制备含有低含量α,β-不饱和酮化合物的吗啡烷-6-酮产物的方法 |
| WO2008070656A2 (en) | 2006-12-04 | 2008-06-12 | Noramco, Inc | Process for reducing impurities in oxycodone base |
| ES2393221T3 (es) | 2006-12-04 | 2012-12-19 | Noramco, Inc. | Procedimiento de preparación de oxicodona con niveles reducidos de 14-hidroxicodeinona |
| FR2923484B1 (fr) * | 2007-11-09 | 2012-11-09 | Sanofi Aventis | Procede de preparation de composes morphiniques |
| PL2588481T3 (pl) * | 2010-07-02 | 2018-05-30 | Johnson Matthey Public Limited Company | Sposób syntezy i oczyszczania oksykodonu |
| PL2880037T3 (pl) | 2012-08-03 | 2019-07-31 | Johnson Matthey Public Limited Company | Sposób wytwarzania oksykodonu |
| US9062062B1 (en) | 2013-12-18 | 2015-06-23 | Cody Laboratories, Inc. | Synthesis of oxycodone hydrochloride |
| US10227354B2 (en) | 2013-12-18 | 2019-03-12 | Cody Laboratories, Inc. | Conversion of oxycodone base to oxycodone hydrochloride |
| US8846923B1 (en) | 2013-12-18 | 2014-09-30 | Cody Laboratories, Inc. | Preparation of 14-hydroxycodeinone sulfate |
| MA40332A (fr) | 2014-07-09 | 2021-04-28 | Rhodes Tech | Réduction des niveaux de cétone alpha, beta-insaturée dans des compositions de dérivés de morphinane |
| CN108135929B (zh) | 2015-09-02 | 2021-10-12 | 梅特罗诺姆中国Ip控股公司 | 使用光-酶分析物传感器进行连续健康监测的系统和方法 |
| 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 |
| AU736031B2 (en) | 1996-11-15 | 2001-07-26 | Synsorb Biotech Inc. | Combinatorial synthesis of carbohydrate libraries |
| US6177567B1 (en) | 1999-10-15 | 2001-01-23 | Boehringer Ingelheim Chemicals, Inc. | Method for preparing oxycodone |
| AU2002352402A1 (en) * | 2001-12-14 | 2003-06-30 | Charterhouse Therapeutics Limited | Improvements in pharmaceutical compositions |
| TW201509943A (zh) * | 2004-03-30 | 2015-03-16 | Euro Celtique Sa | 含有小於２５ｐｐｍ１４-羥可待因酮之羥可酮鹽酸鹽之組成物、醫藥劑型、延遲釋出口服劑型及醫藥上可以接受的包裝 |
| CA2630703C (en) * | 2005-11-22 | 2014-05-20 | Controlled Chemicals, Inc. | Processes for reducing contaminating michael acceptor levels in oxycodone and other compositions |
| CN101395159A (zh) * | 2006-03-02 | 2009-03-25 | 马林克罗特公司 | 制备含有低含量α,β-不饱和酮化合物的吗啡烷-6-酮产物的方法 |
| 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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Also Published As
| Publication number | Publication date |
|---|---|
| US9403838B2 (en) | 2016-08-02 |
| MX2008006710A (es) | 2008-12-16 |
| US7875623B2 (en) | 2011-01-25 |
| KR20140002807A (ko) | 2014-01-08 |
| HK1179622A1 (zh) | 2013-10-04 |
| MX345055B (es) | 2017-01-13 |
| WO2007062184A2 (en) | 2007-05-31 |
| AU2006318445A1 (en) | 2007-05-31 |
| CA2630703A1 (en) | 2007-05-31 |
| US10201174B2 (en) | 2019-02-12 |
| KR101417135B1 (ko) | 2014-07-08 |
| EP2402346A1 (en) | 2012-01-04 |
| US20110136849A1 (en) | 2011-06-09 |
| CA2630703C (en) | 2014-05-20 |
| KR101561760B1 (ko) | 2015-10-20 |
| JP5415075B2 (ja) | 2014-02-12 |
| CN101346384B (zh) | 2012-07-04 |
| CN102816167A (zh) | 2012-12-12 |
| EP1971607A2 (en) | 2008-09-24 |
| US20170027199A1 (en) | 2017-02-02 |
| US9034893B2 (en) | 2015-05-19 |
| WO2007062184A3 (en) | 2007-07-26 |
| US20070149559A1 (en) | 2007-06-28 |
| US20150148537A1 (en) | 2015-05-28 |
| JP2009516750A (ja) | 2009-04-23 |
| CN101346384A (zh) | 2009-01-14 |
| JP2013079279A (ja) | 2013-05-02 |
| KR20080096750A (ko) | 2008-11-03 |
| CN102816167B (zh) | 2016-01-06 |
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