JP2009516750A5 - - Google Patents
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- Publication number
- JP2009516750A5 JP2009516750A5 JP2008542458A JP2008542458A JP2009516750A5 JP 2009516750 A5 JP2009516750 A5 JP 2009516750A5 JP 2008542458 A JP2008542458 A JP 2008542458A JP 2008542458 A JP2008542458 A JP 2008542458A JP 2009516750 A5 JP2009516750 A5 JP 2009516750A5
- Authority
- JP
- Japan
- Prior art keywords
- ppm
- less
- thiol
- composition
- michael
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 claims 41
- 150000003839 salts Chemical class 0.000 claims 17
- 239000000203 mixture Substances 0.000 claims 16
- 150000003573 thiols Chemical class 0.000 claims 8
- BRUQQQPBMZOVGD-XFKAJCMBSA-N Oxycodone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(OC)C2=C5[C@@]13CCN4C BRUQQQPBMZOVGD-XFKAJCMBSA-N 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 6
- 229960002085 oxycodone Drugs 0.000 claims 6
- 239000000825 pharmaceutical preparation Substances 0.000 claims 6
- 229940127557 pharmaceutical product Drugs 0.000 claims 6
- 239000011541 reaction mixture Substances 0.000 claims 6
- 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 claims 5
- 229960003086 naltrexone Drugs 0.000 claims 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 claims 4
- YYCRAERBSFHMPL-UHFFFAOYSA-N 14beta-Hydroxycodeinone Natural products O1C2C(=O)C=CC3(O)C4CC5=CC=C(OC)C1=C5C23CCN4C YYCRAERBSFHMPL-UHFFFAOYSA-N 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 239000003960 organic solvent Substances 0.000 claims 3
- SVFULCKGJOWFGT-UQIOWFBZSA-N COc1ccc2C[C@H]3N(C)CC[C@@]45[C@@H](Oc1c24)C(=O)CC(O)[C@@]35O Chemical compound COc1ccc2C[C@H]3N(C)CC[C@@]45[C@@H](Oc1c24)C(=O)CC(O)[C@@]35O SVFULCKGJOWFGT-UQIOWFBZSA-N 0.000 claims 2
- UQCNKQCJZOAFTQ-ISWURRPUSA-N Oxymorphone Chemical compound O([C@H]1C(CC[C@]23O)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O UQCNKQCJZOAFTQ-ISWURRPUSA-N 0.000 claims 2
- 229930013930 alkaloid Natural products 0.000 claims 2
- XYYVYLMBEZUESM-UHFFFAOYSA-N dihydrocodeine Natural products C1C(N(CCC234)C)C2C=CC(=O)C3OC2=C4C1=CC=C2OC XYYVYLMBEZUESM-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 229960000240 hydrocodone Drugs 0.000 claims 2
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 claims 2
- WVLOADHCBXTIJK-YNHQPCIGSA-N hydromorphone Chemical compound O([C@H]1C(CC[C@H]23)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O WVLOADHCBXTIJK-YNHQPCIGSA-N 0.000 claims 2
- 229960001410 hydromorphone Drugs 0.000 claims 2
- UZHSEJADLWPNLE-GRGSLBFTSA-N naloxone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(O)C2=C5[C@@]13CCN4CC=C UZHSEJADLWPNLE-GRGSLBFTSA-N 0.000 claims 2
- 229960004127 naloxone Drugs 0.000 claims 2
- 229960005118 oxymorphone Drugs 0.000 claims 2
- 239000002243 precursor Substances 0.000 claims 2
- LLPOLZWFYMWNKH-UHFFFAOYSA-N trans-dihydrocodeinone Natural products C1C(N(CCC234)C)C2CCC(=O)C3OC2=C4C1=CC=C2OC LLPOLZWFYMWNKH-UHFFFAOYSA-N 0.000 claims 2
- 229940006193 2-mercaptoethanesulfonic acid Drugs 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 1
- VLSOAXRVHARBEQ-UHFFFAOYSA-N [4-fluoro-2-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=C(F)C=C1CO VLSOAXRVHARBEQ-UHFFFAOYSA-N 0.000 claims 1
- ZNEWHQLOPFWXOF-UHFFFAOYSA-N coenzyme M Chemical compound OS(=O)(=O)CCS ZNEWHQLOPFWXOF-UHFFFAOYSA-N 0.000 claims 1
- 239000000356 contaminant Substances 0.000 claims 1
- 239000008177 pharmaceutical agent Substances 0.000 claims 1
- 238000011002 quantification Methods 0.000 claims 1
- 239000000741 silica gel Substances 0.000 claims 1
- 229910002027 silica gel Inorganic materials 0.000 claims 1
- GNBVPFITFYNRCN-UHFFFAOYSA-M sodium thioglycolate Chemical compound [Na+].[O-]C(=O)CS GNBVPFITFYNRCN-UHFFFAOYSA-M 0.000 claims 1
- 229940046307 sodium thioglycolate Drugs 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- -1 thiol compound Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
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 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013001763A Division JP2013079279A (ja) | 2005-11-22 | 2013-01-09 | オキシコドン及び他の組成物中の混入しているマイケル受容体レベルを低減させる方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009516750A JP2009516750A (ja) | 2009-04-23 |
| JP2009516750A5 true JP2009516750A5 (https=) | 2010-01-21 |
| JP5415075B2 JP5415075B2 (ja) | 2014-02-12 |
Family
ID=38042645
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008542458A Expired - Fee Related JP5415075B2 (ja) | 2005-11-22 | 2006-11-22 | オキシコドン及び他の組成物中の混入しているマイケル受容体レベルを低減させる方法 |
| JP2013001763A Pending JP2013079279A (ja) | 2005-11-22 | 2013-01-09 | オキシコドン及び他の組成物中の混入しているマイケル受容体レベルを低減させる方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013001763A Pending JP2013079279A (ja) | 2005-11-22 | 2013-01-09 | オキシコドン及び他の組成物中の混入しているマイケル受容体レベルを低減させる方法 |
Country Status (8)
| 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 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
-
2006
- 2006-11-22 CN CN2006800494626A patent/CN101346384B/zh not_active Expired - Fee Related
- 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
-
2008
- 2008-05-22 MX MX2012006612A patent/MX345055B/es unknown
-
2010
- 2010-12-06 US US12/960,991 patent/US9034893B2/en not_active Expired - Fee Related
-
2013
- 2013-01-09 JP JP2013001763A patent/JP2013079279A/ja active Pending
-
2014
- 2014-12-30 US US14/586,239 patent/US9403838B2/en not_active Expired - Fee Related
-
2016
- 2016-08-01 US US15/225,699 patent/US10201174B2/en not_active Expired - Fee Related
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