CN102459275A - 制备吗啡烷和吗啡酮化合物的方法 - Google Patents
制备吗啡烷和吗啡酮化合物的方法 Download PDFInfo
- Publication number
- CN102459275A CN102459275A CN2010800284272A CN201080028427A CN102459275A CN 102459275 A CN102459275 A CN 102459275A CN 2010800284272 A CN2010800284272 A CN 2010800284272A CN 201080028427 A CN201080028427 A CN 201080028427A CN 102459275 A CN102459275 A CN 102459275A
- Authority
- CN
- China
- Prior art keywords
- compound
- formula
- alkylene
- alkyl
- conditions
- 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.)
- Pending
Links
- 0 COC1=CC=C(C(Cc2ccc3O)N(*)CC4)[C@]44c2c3O[C@@]14 Chemical compound COC1=CC=C(C(Cc2ccc3O)N(*)CC4)[C@]44c2c3O[C@@]14 0.000 description 14
- RCFARRHVNAOXDU-AMPXAFIBSA-N CCC(CC1)(C(C2)N(CC3CC3)CC3)[C@]33c4c2ccc(OC(OCC)=O)c4O[C@H]3C1OC Chemical compound CCC(CC1)(C(C2)N(CC3CC3)CC3)[C@]33c4c2ccc(OC(OCC)=O)c4O[C@H]3C1OC RCFARRHVNAOXDU-AMPXAFIBSA-N 0.000 description 1
- RYIUYZDCRFQFCY-YABFIEQMSA-N CCC(CC1C(C)(C(C)(C)C)O)(C(Cc2ccc3OC(OCC)=O)N(CC4CC4)CC4)[C@]44c2c3O[C@H]4C1OC Chemical compound CCC(CC1C(C)(C(C)(C)C)O)(C(Cc2ccc3OC(OCC)=O)N(CC4CC4)CC4)[C@]44c2c3O[C@H]4C1OC RYIUYZDCRFQFCY-YABFIEQMSA-N 0.000 description 1
- ZKLXUUYLEHCAMF-MIIWOSQWSA-N CN(CC[C@]12c(c(C3)ccc4O)c4O[C@H]11)C3C2=CC=C1OC Chemical compound CN(CC[C@]12c(c(C3)ccc4O)c4O[C@H]11)C3C2=CC=C1OC ZKLXUUYLEHCAMF-MIIWOSQWSA-N 0.000 description 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:
- C07D489/09—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: containing 4aH-8, 9 c-Iminoethano- phenanthro [4, 5-b, c, d] furan ring systems condensed with carbocyclic rings or ring systems
- C07D489/10—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: containing 4aH-8, 9 c-Iminoethano- phenanthro [4, 5-b, c, d] furan ring systems condensed with carbocyclic rings or ring systems with a bridge between positions 6 and 14
- C07D489/12—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: containing 4aH-8, 9 c-Iminoethano- phenanthro [4, 5-b, c, d] furan ring systems condensed with carbocyclic rings or ring systems with a bridge between positions 6 and 14 the bridge containing only two carbon atoms
-
- 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
- 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
-
- 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
- C07D489/04—Salts; Organic complexes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17252109P | 2009-04-24 | 2009-04-24 | |
| US61/172,521 | 2009-04-24 | ||
| PCT/CA2010/000587 WO2010121369A1 (en) | 2009-04-24 | 2010-04-22 | Processes for the preparation of morphinane and morphinone compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102459275A true CN102459275A (zh) | 2012-05-16 |
Family
ID=43010633
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2010800284272A Pending CN102459275A (zh) | 2009-04-24 | 2010-04-22 | 制备吗啡烷和吗啡酮化合物的方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8853401B2 (https=) |
| EP (1) | EP2421868A4 (https=) |
| JP (1) | JP5824448B2 (https=) |
| KR (1) | KR20120088537A (https=) |
| CN (1) | CN102459275A (https=) |
| AU (1) | AU2010239059B2 (https=) |
| CA (1) | CA2758231A1 (https=) |
| IL (1) | IL215553A (https=) |
| MX (1) | MX2011011245A (https=) |
| NZ (1) | NZ595591A (https=) |
| WO (1) | WO2010121369A1 (https=) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105777765A (zh) * | 2014-12-15 | 2016-07-20 | 北大方正集团有限公司 | 一种乙酰化溴甲纳曲酮及其制备方法 |
| CN105777767A (zh) * | 2014-12-15 | 2016-07-20 | 北大方正集团有限公司 | 一种乙酰化Delta-7溴甲纳曲酮及其制备方法 |
| CN111777617A (zh) * | 2020-07-10 | 2020-10-16 | 华润三九医药股份有限公司 | 一种溴甲纳曲酮的精制方法 |
| CN114502560A (zh) * | 2020-12-18 | 2022-05-13 | 四川大学 | 一种新型中间体及其制备方法和应用 |
| WO2022127321A1 (zh) * | 2020-12-18 | 2022-06-23 | 四川大学 | 一种新型中间体及其制备方法和应用 |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010017573A1 (en) * | 2008-08-11 | 2010-02-18 | Tasmanian Alkaloids Pty Limited | PROCESS FOR MAKING MORPHINAN-6α-OLS |
| CN102558188B (zh) * | 2010-12-17 | 2014-07-23 | 北大方正集团有限公司 | 一种溴甲纳曲酮的制备方法 |
| CN102558189B (zh) * | 2010-12-17 | 2014-09-03 | 北大方正集团有限公司 | 溴甲纳曲酮的精制方法 |
| CA2833283A1 (en) * | 2011-05-02 | 2012-11-08 | Brock University | Processes and intermediates in the preparation of morphine analogs via n-demethylation of n-oxides using cyclodehydration reagents |
| AU2012253188B2 (en) * | 2011-05-06 | 2016-12-22 | Brock University | Process for the preparation of morphine analogs via metal catalyzed N-demethylation/functionalization and intramolecular group transfer |
| US8981098B2 (en) | 2012-02-03 | 2015-03-17 | Brock University | Process for the preparation of morphine analogs via the reaction of organometallic reagents with an oxazolidine derived from morphinans |
| US9701688B2 (en) | 2014-05-05 | 2017-07-11 | Noramco, Inc. | Process for the preparation of opioid compounds |
| US9701687B2 (en) | 2014-05-05 | 2017-07-11 | Noramco, Inc. | Process for the preparation of opioid compounds |
| EP3023427A1 (en) * | 2014-11-19 | 2016-05-25 | Siegfried AG | Improved method of manufacturing buprenorphine and analogues thereof from oripavine |
| WO2018211331A1 (en) * | 2017-05-19 | 2018-11-22 | Evolva Sa | Preparation of buprenorphine |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2671518A1 (en) * | 2006-12-04 | 2008-06-12 | Noramco, Inc. | Process for preparing oxycodone having reduced levels of 14-hydroxycodeinone |
| CN101570539A (zh) * | 2009-06-01 | 2009-11-04 | 漆又毛 | 一种吗啡酮季铵盐衍生物及其制备方法 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1136214A (en) | 1965-06-15 | 1968-12-11 | Reckitt & Sons Ltd | Thebaine and oripavine derivatives |
| US3474101A (en) | 1960-09-05 | 1969-10-21 | Reckitt & Sons Ltd | Thebaine and oripavine derivatives |
| US4176186A (en) | 1978-07-28 | 1979-11-27 | Boehringer Ingelheim Gmbh | Quaternary derivatives of noroxymorphone which relieve intestinal immobility |
| ES2127532T3 (es) | 1994-05-31 | 1999-04-16 | Mallinckrodt Chemical Inc | Preparacion de nalbufina con niveles bajos del epimero beta. |
| KR100204659B1 (ko) | 1996-05-28 | 1999-06-15 | 강재헌 | 신규한 부프레노핀계 진통제용 화합물 |
| AU6934400A (en) * | 1999-08-25 | 2001-03-19 | Barrett R. Cooper | Compositions and methods for treating opiate intolerance |
| US7119100B2 (en) | 2001-09-14 | 2006-10-10 | Institute Of Pharmacology And Toxicology Academy Of Military Medical Sciences, P.L.A. China | Oripavine derivatives and their uses as pharmaceuticals |
| DE10229842A1 (de) | 2002-07-03 | 2004-02-05 | Helmut Prof. Dr. Schmidhammer | Morphinanderivate und deren quartäre Ammoniumsalze substituiert in Position 14, Herstellungsverfahren und Verwendung |
| ATE444295T1 (de) | 2002-11-08 | 2009-10-15 | Mallinckrodt Inc | Verfahren zur herstellung von quaternäre n-alkyl morphinan alkaloid salzen |
| AR057035A1 (es) * | 2005-05-25 | 2007-11-14 | Progenics Pharm Inc | SíNTESIS DE (R)-N-METILNALTREXONA, COMPOSICIONES FARMACÉUTICAS Y USOS |
| ES2329296T3 (es) | 2006-01-05 | 2009-11-24 | Mallinckrodt, Inc. | El uso de oripavina como material de partida para buprenorfina. |
| KR101421747B1 (ko) | 2006-04-21 | 2014-07-30 | 넥타르 테라퓨틱스 | 모르피논의 입체선택적 환원 |
| FR2906252B1 (fr) | 2006-09-21 | 2008-11-28 | Sanofi Aventis Sa | Procede de preparation d'halogenures de n-aklyl naltrexone |
| US20080125592A1 (en) | 2006-10-17 | 2008-05-29 | Penick Corporation | Process for preparing oxymorphone, naltrexone, and buprenorphine |
| KR100791555B1 (ko) | 2007-02-02 | 2008-01-03 | 주식회사 선진화학 | 초미립자 무기금속산화물 수분산체 및 이의 제조방법 |
| EP2132443B1 (de) | 2007-03-06 | 2011-05-18 | ixetic Bad Homburg GmbH | Pumpe mit einem magnetisch angesteuerten schaltventil zur saugdrosselung |
| NZ579469A (en) | 2007-03-06 | 2011-02-25 | Mallinckrodt Inc | Process for the preparation of quaternary n-alkyl morphinan alkaloid salts |
| WO2008138383A1 (de) | 2007-05-16 | 2008-11-20 | Cilag Ag | Verfahren zur herstellung von n-methylnaltrexonbromid |
| US7999104B2 (en) * | 2007-06-29 | 2011-08-16 | Brock University | Methods for one-pot N-demethylation/N-acylation of morphine and tropane alkaloids |
| GB2450691A (en) | 2007-07-02 | 2009-01-07 | Alpharma Aps | One-pot preparation of oxycodone from thebaine |
-
2010
- 2010-04-22 KR KR1020117025806A patent/KR20120088537A/ko not_active Withdrawn
- 2010-04-22 MX MX2011011245A patent/MX2011011245A/es active IP Right Grant
- 2010-04-22 CA CA2758231A patent/CA2758231A1/en not_active Abandoned
- 2010-04-22 JP JP2012506298A patent/JP5824448B2/ja not_active Expired - Fee Related
- 2010-04-22 NZ NZ595591A patent/NZ595591A/xx not_active IP Right Cessation
- 2010-04-22 US US13/264,182 patent/US8853401B2/en not_active Expired - Fee Related
- 2010-04-22 CN CN2010800284272A patent/CN102459275A/zh active Pending
- 2010-04-22 EP EP10766555A patent/EP2421868A4/en not_active Withdrawn
- 2010-04-22 AU AU2010239059A patent/AU2010239059B2/en not_active Ceased
- 2010-04-22 WO PCT/CA2010/000587 patent/WO2010121369A1/en not_active Ceased
-
2011
- 2011-10-05 IL IL215553A patent/IL215553A/en not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2671518A1 (en) * | 2006-12-04 | 2008-06-12 | Noramco, Inc. | Process for preparing oxycodone having reduced levels of 14-hydroxycodeinone |
| CN101570539A (zh) * | 2009-06-01 | 2009-11-04 | 漆又毛 | 一种吗啡酮季铵盐衍生物及其制备方法 |
Non-Patent Citations (4)
| Title |
|---|
| DOLORES LOPEZ ET AL.: "Photooxidation of Thebaine. A Route to 14-Hydroxymorphinones and Hydrodibenzofuran Analogs of Methadone.", 《TETRAHEDRON LETTERS》 * |
| REZSO BOGNAR ET AL.: "Selective quaternerization in the morphine series", 《TETRAHEARON LETTERS》 * |
| ST MANOHARAN ET AL.: "Stereoselectivity in quaternization of thebaine: 270 MHz PMR spectroscopic studies", 《INDIAN JOURNAL OF CHEMISTRY》 * |
| THOMAS SAMUEL MANOHARAN ET AL.: "A convenient method for replacing the N-methyl Group of Morphine,Codeine,and Thebaine by other alkyl groups", 《SYNTHESIS》 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105777765A (zh) * | 2014-12-15 | 2016-07-20 | 北大方正集团有限公司 | 一种乙酰化溴甲纳曲酮及其制备方法 |
| CN105777767A (zh) * | 2014-12-15 | 2016-07-20 | 北大方正集团有限公司 | 一种乙酰化Delta-7溴甲纳曲酮及其制备方法 |
| CN111777617A (zh) * | 2020-07-10 | 2020-10-16 | 华润三九医药股份有限公司 | 一种溴甲纳曲酮的精制方法 |
| CN114502560A (zh) * | 2020-12-18 | 2022-05-13 | 四川大学 | 一种新型中间体及其制备方法和应用 |
| WO2022127321A1 (zh) * | 2020-12-18 | 2022-06-23 | 四川大学 | 一种新型中间体及其制备方法和应用 |
| WO2022127320A1 (zh) * | 2020-12-18 | 2022-06-23 | 四川大学 | 一种中间体及其制备方法和应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| IL215553A0 (en) | 2011-12-29 |
| CA2758231A1 (en) | 2010-10-28 |
| NZ595591A (en) | 2013-11-29 |
| MX2011011245A (es) | 2012-04-11 |
| JP2012524726A (ja) | 2012-10-18 |
| AU2010239059B2 (en) | 2016-06-09 |
| US8853401B2 (en) | 2014-10-07 |
| EP2421868A4 (en) | 2012-08-01 |
| WO2010121369A1 (en) | 2010-10-28 |
| US20120046465A1 (en) | 2012-02-23 |
| EP2421868A1 (en) | 2012-02-29 |
| KR20120088537A (ko) | 2012-08-08 |
| AU2010239059A1 (en) | 2011-10-27 |
| IL215553A (en) | 2015-01-29 |
| JP5824448B2 (ja) | 2015-11-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20120516 |