DE69829379D1 - Herstellung von oxymorphon, oxycodon und derivaten davon - Google Patents
Herstellung von oxymorphon, oxycodon und derivaten davonInfo
- Publication number
- DE69829379D1 DE69829379D1 DE69829379T DE69829379T DE69829379D1 DE 69829379 D1 DE69829379 D1 DE 69829379D1 DE 69829379 T DE69829379 T DE 69829379T DE 69829379 T DE69829379 T DE 69829379T DE 69829379 D1 DE69829379 D1 DE 69829379D1
- Authority
- DE
- Germany
- Prior art keywords
- synthesis
- oxymorphone
- oxycodone
- derivatives
- preparation
- 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 - Lifetime
Links
- 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 title 1
- 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 title 1
- 229960002085 oxycodone Drugs 0.000 title 1
- 229960005118 oxymorphone Drugs 0.000 title 1
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 abstract 4
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 abstract 4
- 230000015572 biosynthetic process Effects 0.000 abstract 3
- 238000003786 synthesis reaction Methods 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 229960004126 codeine Drugs 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 abstract 2
- 229960005181 morphine Drugs 0.000 abstract 2
- VARGTNDMWUVZHW-OHRMOMTBSA-N 1-[(4r,4ar,7s,7ar,12bs)-7-hydroxy-9-methoxy-3-methyl-1,2,4,4a,7a,13-hexahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-7-yl]ethanone;hydrochloride Chemical compound Cl.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@@](O)(C(C)=O)[C@@H]1OC1=C2C3=CC=C1OC VARGTNDMWUVZHW-OHRMOMTBSA-N 0.000 abstract 1
- MFXFQKMUCYHPFQ-BKRJIHRRSA-N 6-monoacetylcodeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](OC(C)=O)[C@@H]1OC1=C2C3=CC=C1OC MFXFQKMUCYHPFQ-BKRJIHRRSA-N 0.000 abstract 1
- HLMSIZPQBSYUNL-IPOQPSJVSA-N Noroxymorphone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(O)C2=C5[C@@]13CCN4 HLMSIZPQBSYUNL-IPOQPSJVSA-N 0.000 abstract 1
- 238000006859 Swern oxidation reaction Methods 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- -1 cyclopropylmethyl halide Chemical class 0.000 abstract 1
- 229960002921 methylnaltrexone Drugs 0.000 abstract 1
- 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 abstract 1
- 229960003086 naltrexone Drugs 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pain & Pain Management (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/893,464 US5869669A (en) | 1996-07-26 | 1997-07-11 | Preparation of 14-hydroxynormorphinones from normorphinone dienol acylates |
| PCT/US1998/013592 WO1999002529A1 (en) | 1997-07-11 | 1998-07-10 | Preparation of oxymorphone, oxycodone and derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE69829379D1 true DE69829379D1 (de) | 2005-04-21 |
Family
ID=25401603
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69829379T Expired - Lifetime DE69829379D1 (de) | 1997-07-11 | 1998-07-10 | Herstellung von oxymorphon, oxycodon und derivaten davon |
Country Status (19)
| Country | Link |
|---|---|
| US (7) | US5869669A (en:Method) |
| EP (1) | EP1000065B1 (en:Method) |
| JP (1) | JP2001518444A (en:Method) |
| KR (1) | KR100363486B1 (en:Method) |
| CN (1) | CN1152880C (en:Method) |
| AT (1) | ATE291023T1 (en:Method) |
| AU (1) | AU740822B2 (en:Method) |
| CA (1) | CA2296035C (en:Method) |
| DE (1) | DE69829379D1 (en:Method) |
| HU (1) | HUP0003918A3 (en:Method) |
| IL (1) | IL133792A0 (en:Method) |
| IN (1) | IN1998KO01500A (en:Method) |
| NO (1) | NO20000111L (en:Method) |
| RU (1) | RU2183636C2 (en:Method) |
| SK (1) | SK102000A3 (en:Method) |
| TR (1) | TR200000033T2 (en:Method) |
| TW (1) | TW505648B (en:Method) |
| WO (1) | WO1999002529A1 (en:Method) |
| ZA (1) | ZA986144B (en:Method) |
Families Citing this family (93)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5912347A (en) * | 1996-09-30 | 1999-06-15 | Mallinckrodt Inc. | Process for preparing a morphinan derivative |
| WO2000066588A1 (en) * | 1999-05-05 | 2000-11-09 | The Government Of The United States Of America, Represented By The Secretary, Departmentof Health A Nd Human Services | Direct c-14 oxidation of opioids |
| US6177567B1 (en) | 1999-10-15 | 2001-01-23 | Boehringer Ingelheim Chemicals, Inc. | Method for preparing oxycodone |
| WO2003018588A2 (en) * | 2001-08-23 | 2003-03-06 | Akzo Nobel N.V. | Process for the preparation of a 14-hydroxynormorphinone derivative |
| JP3961796B2 (ja) * | 2001-08-27 | 2007-08-22 | ソニー株式会社 | 情報提供システム、情報処理装置および方法、情報提供装置および方法、記録媒体、並びにプログラム |
| DE10161963A1 (de) * | 2001-12-17 | 2003-07-03 | Johannes Schuetz | 6-Aminomorphinanderivate, Herstellungsverfahren dafür und deren Verwendung |
| US20040001889A1 (en) | 2002-06-25 | 2004-01-01 | Guohua Chen | Short duration depot formulations |
| US20040058946A1 (en) * | 2002-07-05 | 2004-03-25 | Buchwald Stephen L. | Abuse-resistant prodrugs of oxycodone and other pharmaceuticals |
| RU2236412C2 (ru) * | 2002-07-18 | 2004-09-20 | Власов Михаил Иванович | Способ получения производных морфинона, способ получения производных 14-гидроксиморфинона, и способ получения производных оксиморфона |
| RU2215741C1 (ru) * | 2002-11-05 | 2003-11-10 | Открытое Акционерное Общество "Международная Научно-Технологическая Корпорация" | Сложные эфиры n-замещенных 14-гидроксиморфинанов и способ их получения |
| RU2215742C1 (ru) * | 2002-11-05 | 2003-11-10 | Открытое Акционерное Общество "Международная Научно-Технологическая Корпорация" | Способ получения сложных эфиров n-замещенных 14-гидроксиморфинанов |
| DE60329520D1 (de) * | 2002-11-08 | 2009-11-12 | Mallinckrodt Inc | Verfahren zur herstellung von quaternäre n-alkyl morphinan alkaloid salzen |
| SI1575569T1 (sl) | 2002-12-13 | 2010-12-31 | Durect Corp | Oralni sistem dostave zdravila, ki obsega visokoviskozne tekoče nosilne materiale |
| US6864370B1 (en) | 2003-06-05 | 2005-03-08 | Zhaiwei Lin | Process for manufacturing oxycodone |
| US6790959B1 (en) | 2003-06-05 | 2004-09-14 | Halsey Drug Company, Inc. | Process for manufacturing thebaine |
| US7875718B2 (en) * | 2003-09-22 | 2011-01-25 | Johnson Matthey Public Limited Company | Process for the synthesis of morphinane compounds and intermediates thereof |
| ES2627995T3 (es) | 2003-09-22 | 2017-08-01 | Glaxosmithkline Australia Pty Ltd | Procedimiento para la síntesis de compuestos de morfinano y productos intermedios de los mismos |
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| TWI483944B (zh) | 2004-03-30 | 2015-05-11 | Euro Celtique Sa | 含有小於25ppm14-羥可待因酮之羥可酮鹽酸鹽組成物、醫藥劑型、延遲釋出口服劑型及醫藥上可以接受的包裝 |
| SK286047B6 (sk) * | 2004-04-13 | 2008-01-07 | Zentiva, A. S. | Spôsob prípravy derivátov 4,5alfa-epoxy-6-oxomorfínanu |
| US6946556B1 (en) * | 2004-05-21 | 2005-09-20 | Acura Pharmaceuticals, Inc. | Preparation of opioid analgesics by a one-pot process |
| CN1964976A (zh) * | 2004-06-08 | 2007-05-16 | 马林克罗特公司 | 从鸦片中提取生物碱 |
| LT1765292T (lt) | 2004-06-12 | 2018-01-10 | Collegium Pharmaceutical, Inc. | Nuo piktnaudžiavimo apsaugotos vaistų formos |
| LT2767292T (lt) | 2004-09-17 | 2016-12-12 | Durect Corporation | Palaikomosios vietinės anestezijos mišinys su saib |
| GB0421149D0 (en) * | 2004-09-23 | 2004-10-27 | Johnson Matthey Plc | Preparation of oxycodone |
| GB0421687D0 (en) * | 2004-09-30 | 2004-11-03 | Johnson Matthey Plc | Preparation of opiate analgesics |
| WO2006084389A1 (de) * | 2005-02-11 | 2006-08-17 | Cilag Ltd. | Verfahren zur reinigung von noroxymorphon-verbindungen |
| CN101133062B (zh) * | 2005-03-04 | 2014-08-06 | 欧洲凯尔特公司 | 减少阿片样物质组合物中α,β-不饱和酮的方法 |
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| CN115666621A (zh) | 2020-01-13 | 2023-01-31 | 度勒科特公司 | 具有减少的杂质的持续释放药物递送系统及相关方法 |
| CN114621239A (zh) * | 2020-12-10 | 2022-06-14 | 鲁南制药集团股份有限公司 | 一种纳曲酮的制备方法 |
| CA3200832A1 (en) * | 2020-12-28 | 2022-07-07 | Navin Saxena Research & Technology Pvt. Ltd. | Novel process for the synthesis of noroxymorphone from morphine |
| JP2024503402A (ja) | 2021-01-12 | 2024-01-25 | デュレクト コーポレーション | 徐放性薬物送達システム及び関連の方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3819636A (en) * | 1970-09-15 | 1974-06-25 | American Home Prod | 4a,10-(methaniminomethano)phenanthrene derivatives |
| 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 |
| DE3581423D1 (de) * | 1984-03-27 | 1991-02-28 | Mallinckrodt Inc | Herstellung von noroxymorphon aus morphin. |
| US4639520A (en) * | 1984-03-27 | 1987-01-27 | Mallinckrodt, Inc. | Preparation of 14-hydroxy-N-ethoxy-carbonyl-norcodeinone |
| US5112975A (en) * | 1984-03-27 | 1992-05-12 | Mallinckrodt Specialty Chemicals Company | Preparation of noroxymorphone from morphine |
| US4668685A (en) * | 1984-07-05 | 1987-05-26 | E.I. Du Pont De Nemours And Company | Substituted benzoate ester prodrug derivatives of 3-hydroxymorphinans, which are analgesics or narcotic antagonists |
| US4912114A (en) * | 1988-03-18 | 1990-03-27 | Sandoz Ltd. | Morphinan derivatives |
-
1997
- 1997-07-11 US US08/893,464 patent/US5869669A/en not_active Expired - Fee Related
-
1998
- 1998-07-10 CA CA002296035A patent/CA2296035C/en not_active Expired - Fee Related
- 1998-07-10 AU AU83791/98A patent/AU740822B2/en not_active Ceased
- 1998-07-10 TR TR2000/00033T patent/TR200000033T2/xx unknown
- 1998-07-10 ZA ZA986144A patent/ZA986144B/xx unknown
- 1998-07-10 HU HU0003918A patent/HUP0003918A3/hu unknown
- 1998-07-10 KR KR20007000252A patent/KR100363486B1/ko not_active Expired - Fee Related
- 1998-07-10 DE DE69829379T patent/DE69829379D1/de not_active Expired - Lifetime
- 1998-07-10 IL IL13379298A patent/IL133792A0/xx unknown
- 1998-07-10 EP EP98934213A patent/EP1000065B1/en not_active Revoked
- 1998-07-10 WO PCT/US1998/013592 patent/WO1999002529A1/en not_active Application Discontinuation
- 1998-07-10 JP JP2000502051A patent/JP2001518444A/ja active Pending
- 1998-07-10 RU RU2000100062/04A patent/RU2183636C2/ru not_active IP Right Cessation
- 1998-07-10 AT AT98934213T patent/ATE291023T1/de not_active IP Right Cessation
- 1998-07-10 CN CNB988088169A patent/CN1152880C/zh not_active Expired - Fee Related
- 1998-07-10 SK SK10-2000A patent/SK102000A3/sk unknown
- 1998-07-16 US US09/116,284 patent/US5922876A/en not_active Expired - Fee Related
- 1998-07-16 US US09/116,285 patent/US6008354A/en not_active Expired - Fee Related
- 1998-07-16 US US09/116,286 patent/US5952495A/en not_active Expired - Fee Related
- 1998-07-16 US US09/116,283 patent/US6008355A/en not_active Expired - Fee Related
- 1998-07-16 US US09/116,282 patent/US6013796A/en not_active Expired - Fee Related
- 1998-07-17 US US09/118,577 patent/US5948788A/en not_active Expired - Fee Related
- 1998-08-21 IN IN1500KO1998 patent/IN1998KO01500A/en unknown
- 1998-09-29 TW TW087116132A patent/TW505648B/zh not_active IP Right Cessation
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2000
- 2000-01-10 NO NO20000111A patent/NO20000111L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| RU2183636C2 (ru) | 2002-06-20 |
| EP1000065A4 (en) | 2001-09-12 |
| CA2296035C (en) | 2004-04-13 |
| US6013796A (en) | 2000-01-11 |
| CA2296035A1 (en) | 1999-01-21 |
| ZA986144B (en) | 1999-05-19 |
| US6008355A (en) | 1999-12-28 |
| HUP0003918A3 (en) | 2003-04-28 |
| US5952495A (en) | 1999-09-14 |
| KR100363486B1 (ko) | 2002-12-16 |
| AU740822B2 (en) | 2001-11-15 |
| US5922876A (en) | 1999-07-13 |
| NO20000111L (no) | 2000-02-25 |
| US5948788A (en) | 1999-09-07 |
| CN1272845A (zh) | 2000-11-08 |
| ATE291023T1 (de) | 2005-04-15 |
| WO1999002529A1 (en) | 1999-01-21 |
| US5869669A (en) | 1999-02-09 |
| TR200000033T2 (tr) | 2000-12-21 |
| CN1152880C (zh) | 2004-06-09 |
| EP1000065A1 (en) | 2000-05-17 |
| NO20000111D0 (no) | 2000-01-10 |
| SK102000A3 (en) | 2000-07-11 |
| JP2001518444A (ja) | 2001-10-16 |
| KR20010021693A (ko) | 2001-03-15 |
| HUP0003918A2 (hu) | 2001-07-30 |
| TW505648B (en) | 2002-10-11 |
| EP1000065B1 (en) | 2005-03-16 |
| IN1998KO01500A (en:Method) | 2005-03-11 |
| IL133792A0 (en) | 2001-04-30 |
| US6008354A (en) | 1999-12-28 |
| HK1028025A1 (en) | 2001-02-02 |
| AU8379198A (en) | 1999-02-08 |
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