MX2009010931A - Reduccion novedosa de opiaceos utilizando la reaccion de transferencia catalitica de hidrogeno. - Google Patents
Reduccion novedosa de opiaceos utilizando la reaccion de transferencia catalitica de hidrogeno.Info
- Publication number
- MX2009010931A MX2009010931A MX2009010931A MX2009010931A MX2009010931A MX 2009010931 A MX2009010931 A MX 2009010931A MX 2009010931 A MX2009010931 A MX 2009010931A MX 2009010931 A MX2009010931 A MX 2009010931A MX 2009010931 A MX2009010931 A MX 2009010931A
- Authority
- MX
- Mexico
- Prior art keywords
- hydrogen transfer
- oxycodone
- oripavine
- transfer reaction
- catalytic hydrogen
- Prior art date
Links
- 229910052739 hydrogen Inorganic materials 0.000 title abstract 2
- 239000001257 hydrogen Substances 0.000 title abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 title abstract 2
- 229940127240 opiate Drugs 0.000 title abstract 2
- 230000003197 catalytic effect Effects 0.000 title 1
- 238000006276 transfer reaction Methods 0.000 title 1
- ZKLXUUYLEHCAMF-UUWFMWQGSA-N Oripavine Chemical compound C([C@@H](N(CC1)C)C2=CC=C3OC)C4=CC=C(O)C5=C4[C@@]21[C@H]3O5 ZKLXUUYLEHCAMF-UUWFMWQGSA-N 0.000 abstract 4
- 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 abstract 4
- ZKLXUUYLEHCAMF-UHFFFAOYSA-N Oripavine Natural products COC1=CC=C2C(N(CC3)C)CC4=CC=C(O)C5=C4C23C1O5 ZKLXUUYLEHCAMF-UHFFFAOYSA-N 0.000 abstract 2
- 229940051808 oripavine derivative analgesics Drugs 0.000 abstract 2
- 229960002085 oxycodone Drugs 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 238000010952 in-situ formation Methods 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 238000005580 one pot reaction Methods 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
Classifications
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
Se proporciona un esquema de síntesis mejorado de compuestos opiáceos. Un mejoramiento a la oxidación de oripavina y derivados de oripavina comprende la formación in situ de los peroxiácidos requeridos para oxidar la oripavina y derivados de oripavina para formar un intermediario. Un mejoramiento a la reducción del intermediario para formar una oxicodona y derivados de oxicodona comprende la reducción utilizando un reactivo de transferencia de hidrógeno. Estos mejoramientos permiten la producción de oxicodona y derivados de oxicodona sin el aislamiento del intermediario, proporcionando un método de síntesis en un crisol.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US91195007P | 2007-04-16 | 2007-04-16 | |
| PCT/US2008/004869 WO2008130553A1 (en) | 2007-04-16 | 2008-04-15 | Novel opiate reduction utilizing catalytic hydrogen transfer reaction |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2009010931A true MX2009010931A (es) | 2009-10-29 |
Family
ID=39560869
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2009010931A MX2009010931A (es) | 2007-04-16 | 2008-04-15 | Reduccion novedosa de opiaceos utilizando la reaccion de transferencia catalitica de hidrogeno. |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8309727B2 (es) |
| EP (1) | EP2137190B1 (es) |
| JP (2) | JP5373764B2 (es) |
| AU (1) | AU2008241528B2 (es) |
| CA (1) | CA2684458A1 (es) |
| ES (1) | ES2423180T3 (es) |
| MX (1) | MX2009010931A (es) |
| WO (1) | WO2008130553A1 (es) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5923827B2 (ja) * | 1981-12-16 | 1984-06-05 | フエザ−安全剃刀株式会社 | 安全かみそり刃 |
| EP2377866B1 (en) * | 2010-03-23 | 2014-02-26 | Siegfried AG | Preparation of low impurity opiates in a continuous flow reactor |
| WO2011154827A2 (en) | 2010-06-11 | 2011-12-15 | Rhodes Technologies | Transition metal-catalyzed processes for the preparation of n-allyl compounds and use thereof |
| JP2013529595A (ja) | 2010-06-11 | 2013-07-22 | ローズ テクノロジーズ | 第3級アミンのn−脱アルキル化方法 |
| WO2012003468A1 (en) | 2010-07-02 | 2012-01-05 | Johnson Matthey Public Limited Company | Process for the synthesis and purification of oxycodone |
| EP2420503A1 (en) * | 2010-07-27 | 2012-02-22 | Universität Innsbruck | Process for the synthesis of 14-oxygenated morphinan-6-ones |
| EP2812336B1 (en) | 2012-02-08 | 2017-02-01 | Mallinckrodt LLC | One pot process for producing 6-hydroxyl nal-opiate |
| CA2870056C (en) | 2012-06-11 | 2021-01-19 | Siegfried Ag | Improved method of preparing oxymorphone |
| EP2877473B1 (en) | 2012-07-16 | 2017-06-14 | Rhodes Technologies | Process for improved opioid synthesis |
| KR101946103B1 (ko) * | 2012-07-16 | 2019-02-08 | 로드스 테크놀로지즈 | 개선된 오피오이드 합성을 위한 방법 |
| AU2014346883B2 (en) * | 2013-11-07 | 2018-07-19 | SpecGx LLC | Production of 6-hydroxy morphinans without the isolation of intermediates |
| 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 |
| MX374394B (es) | 2014-01-15 | 2025-03-06 | Rhodes Tech | Proceso para la sintesis mejorada de oxicodona. |
| AU2015207734B2 (en) | 2014-01-15 | 2017-02-23 | Rhodes Technologies | Process for improved oxymorphone synthesis |
| US20160052932A1 (en) * | 2014-08-25 | 2016-02-25 | Johnson Matthey Public Limited Company | Processes for Making Opioids Including 14-Hydroxycodeinone and 14-hydroxymorphinone |
| SG11201704523WA (en) * | 2014-12-12 | 2017-07-28 | H Lundbeck As | A process for the manufacture of idalopirdine |
| US20160340362A1 (en) * | 2015-05-20 | 2016-11-24 | Noramco, Inc. | Process For The Preparation Of Oxymorphone Freebase |
| ES2701855T3 (es) | 2016-05-31 | 2019-02-26 | Alcaliber Investig Desarrollo E Innovacion Slu | Proceso para la obtención de 3,14-diacetiloximorfona a partir de oripavina |
| EP3495371A1 (en) * | 2017-12-05 | 2019-06-12 | Siegfried AG | Synthesis of noroxymorphone |
| CN111205296B (zh) * | 2018-11-22 | 2022-10-04 | 中国科学院上海有机化学研究所 | 羟考酮类化合物及其中间体和制备方法 |
| CN114573508B (zh) * | 2020-12-01 | 2024-07-23 | 绍兴赜军生物医药科技有限公司 | 羟考酮类化合物、其中间体及制备方法 |
Family Cites Families (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2772270A (en) * | 1954-10-21 | 1956-11-27 | M J Lewenstein | 14-hydroxymorphinone and 8, 14-dihydroxydihydromorphinone |
| GB939287A (en) * | 1961-03-14 | 1963-10-09 | Sankyo Co | New morphinone and codeinone derivatives and process for preparing the same |
| BE638369A (es) * | 1962-10-10 | |||
| IL26896A (en) * | 1966-01-19 | 1970-11-30 | Endo Lab | 14 - Hydroxynormorphinins and 14 - Hydroxynormorphinones |
| GB1123768A (en) * | 1966-07-29 | 1968-08-14 | Smith Kline French Lab | New thebaine and oripavine derivatives and processes for preparing the same |
| US3905981A (en) * | 1973-10-12 | 1975-09-16 | Research Corp | N-dealkylation of tertiary amines |
| US4277604A (en) * | 1980-01-25 | 1981-07-07 | The United States Of America As Represented By The Department Of Health And Human Services | Facile synthesis of codeine precursors from thebaine |
| US4472253A (en) * | 1981-08-17 | 1984-09-18 | The Florida Board Of Regents On Behalf Of The Florida State University | Process for the preparation of an N-substituted 3-O-alkyl-14-hydroxynormorphinone derivative |
| US4795813A (en) * | 1981-08-17 | 1989-01-03 | The Florida Board Of Regents On Behalf Of The Florida State University | Synthesis of derivatives of codeine and other 3-O-alkylmorphines |
| US5112975A (en) * | 1984-03-27 | 1992-05-12 | Mallinckrodt Specialty Chemicals Company | Preparation of noroxymorphone from morphine |
| US4639520A (en) * | 1984-03-27 | 1987-01-27 | Mallinckrodt, Inc. | Preparation of 14-hydroxy-N-ethoxy-carbonyl-norcodeinone |
| US5668285A (en) * | 1986-10-31 | 1997-09-16 | The United States Of America As Represented By The Department Of Health And Human Services | Total synthesis of northebaine, normophine, noroxymorphone enantiomers and derivatives via N-Nor intermediates |
| FR2636330B1 (fr) * | 1988-09-13 | 1990-11-30 | Sanofi Sa | Procede de preparation de derives de morphinane |
| US6067749A (en) * | 1996-07-11 | 2000-05-30 | Tasmanian Alkaloids Pty. Ltd. | Papaver somniferum strain with high concentration of thebaine and oripavine |
| US5869669A (en) * | 1996-07-26 | 1999-02-09 | Penick Corporation | Preparation of 14-hydroxynormorphinones from normorphinone dienol acylates |
| US7202261B2 (en) * | 1996-12-03 | 2007-04-10 | Nps Pharmaceuticals, Inc. | Calcilytic compounds |
| GB9713703D0 (en) * | 1997-06-30 | 1997-09-03 | Johnson Matthey Plc | Preparation of opiates |
| US6177567B1 (en) * | 1999-10-15 | 2001-01-23 | Boehringer Ingelheim Chemicals, Inc. | Method for preparing oxycodone |
| AUPQ968300A0 (en) * | 2000-08-25 | 2000-09-21 | Glaxo Wellcome Australia Ltd | Chemical methods |
| IL160193A0 (en) | 2001-08-23 | 2004-07-25 | Akzo Nobel Nv | Process for the preparation of a 14-hydroxynormorphinone derivative |
| US6904126B2 (en) * | 2002-06-19 | 2005-06-07 | Canon Kabushiki Kaisha | Radiological imaging apparatus and method |
| US6864370B1 (en) * | 2003-06-05 | 2005-03-08 | Zhaiwei Lin | Process for manufacturing oxycodone |
| JP4879740B2 (ja) | 2003-09-22 | 2012-02-22 | ジョンソン、マッセイ、パブリック、リミテッド、カンパニー | モルヒナン化合物およびその中間体の合成法 |
| 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 |
| WO2006084389A1 (de) * | 2005-02-11 | 2006-08-17 | Cilag Ltd. | Verfahren zur reinigung von noroxymorphon-verbindungen |
| CA2595689C (en) * | 2005-02-25 | 2013-04-23 | Fina Technology, Inc. | Treatment of alkylation catalyst poisons with dehydrogenation |
| SI1861405T1 (sl) * | 2005-03-04 | 2009-10-31 | Euro Celtique Sa | Postopek za zmanjšanje alfa,beta-nenasičenih ketonov v opioidnih sestavkih |
| EP2073636B1 (en) | 2006-10-17 | 2012-09-05 | Penick Corporation | Process for preparing oxymorphone |
| GB0624880D0 (en) * | 2006-12-14 | 2007-01-24 | Johnson Matthey Plc | Improved method for making analgesics |
-
2008
- 2008-04-15 CA CA002684458A patent/CA2684458A1/en not_active Abandoned
- 2008-04-15 ES ES08742920T patent/ES2423180T3/es active Active
- 2008-04-15 JP JP2010504070A patent/JP5373764B2/ja not_active Expired - Fee Related
- 2008-04-15 EP EP08742920.5A patent/EP2137190B1/en not_active Not-in-force
- 2008-04-15 US US12/595,519 patent/US8309727B2/en active Active
- 2008-04-15 MX MX2009010931A patent/MX2009010931A/es unknown
- 2008-04-15 WO PCT/US2008/004869 patent/WO2008130553A1/en not_active Ceased
- 2008-04-15 AU AU2008241528A patent/AU2008241528B2/en not_active Ceased
-
2013
- 2013-07-26 JP JP2013155260A patent/JP2013216696A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP2010524938A (ja) | 2010-07-22 |
| JP2013216696A (ja) | 2013-10-24 |
| JP5373764B2 (ja) | 2013-12-18 |
| AU2008241528B2 (en) | 2013-07-04 |
| CA2684458A1 (en) | 2008-10-30 |
| ES2423180T3 (es) | 2013-09-18 |
| WO2008130553A1 (en) | 2008-10-30 |
| AU2008241528A1 (en) | 2008-10-30 |
| EP2137190A1 (en) | 2009-12-30 |
| US8309727B2 (en) | 2012-11-13 |
| US20100048905A1 (en) | 2010-02-25 |
| EP2137190B1 (en) | 2013-06-12 |
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