AU2010239059B2 - Processes for the preparation of morphinane and morphinone compounds - Google Patents

Processes for the preparation of morphinane and morphinone compounds Download PDF

Info

Publication number
AU2010239059B2
AU2010239059B2 AU2010239059A AU2010239059A AU2010239059B2 AU 2010239059 B2 AU2010239059 B2 AU 2010239059B2 AU 2010239059 A AU2010239059 A AU 2010239059A AU 2010239059 A AU2010239059 A AU 2010239059A AU 2010239059 B2 AU2010239059 B2 AU 2010239059B2
Authority
AU
Australia
Prior art keywords
formula
compound
process according
compounds
mixture
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
Application number
AU2010239059A
Other languages
English (en)
Other versions
AU2010239059A1 (en
Inventor
David R. Adams
Robert Carroll
Tomas Hudlicky
Hannes Leisch
Ales Machara
Lukas Werner
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Brock University
Original Assignee
Brock University
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Brock University filed Critical Brock University
Publication of AU2010239059A1 publication Critical patent/AU2010239059A1/en
Application granted granted Critical
Publication of AU2010239059B2 publication Critical patent/AU2010239059B2/en
Ceased legal-status Critical Current
Anticipated expiration legal-status Critical

Links

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)
AU2010239059A 2009-04-24 2010-04-22 Processes for the preparation of morphinane and morphinone compounds Ceased AU2010239059B2 (en)

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 (2)

Publication Number Publication Date
AU2010239059A1 AU2010239059A1 (en) 2011-10-27
AU2010239059B2 true AU2010239059B2 (en) 2016-06-09

Family

ID=43010633

Family Applications (1)

Application Number Title Priority Date Filing Date
AU2010239059A Ceased AU2010239059B2 (en) 2009-04-24 2010-04-22 Processes for the preparation of morphinane and morphinone compounds

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=)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
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
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
WO2018211331A1 (en) * 2017-05-19 2018-11-22 Evolva Sa Preparation of buprenorphine
CN111777617B (zh) * 2020-07-10 2025-06-06 华润三九医药股份有限公司 一种溴甲纳曲酮的精制方法
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
CN114502560B (zh) * 2020-12-18 2023-06-30 四川大学 一种中间体及其制备方法和应用

Citations (2)

* Cited by examiner, † Cited by third party
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
WO2009004491A2 (en) * 2007-07-02 2009-01-08 Alpharma (Bermuda) Investments Ltd. Preparation of oxycodone

Family Cites Families (20)

* Cited by examiner, † Cited by third party
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
CN101570539B (zh) * 2009-06-01 2012-01-11 漆又毛 一种吗啡酮季铵盐衍生物及其制备方法

Patent Citations (2)

* Cited by examiner, † Cited by third party
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
WO2009004491A2 (en) * 2007-07-02 2009-01-08 Alpharma (Bermuda) Investments Ltd. Preparation of oxycodone

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
BOGNAR, R. et al., 'Selective quaternerization in the morphine series', Tetrahedron Letters, 1964, No. 39, pages 2867-2871. *
LOPEZ, D. et al., 'The [4+2] Addition of Singlet Oxygen to Thebaine: New Access to Highly Functionalized Morphine Derivatives via Opioid Endoperoxides', J. Org. Chem, 2000, No. 65, pages 4671-4678. *
MANOHARAN et al, 'A Convenient Method for Replacing the N-Methyl Group of Morphine, Codeine, and Thebaine by Other Alkyl Groups', Synthesis, 1983, pages 809-812. *
MANOHARAN et al, 'Stereoselectivity in Quarternization of Thebaine: 270 MHz PMR Spectroscopic Studies', Indian Journal of Chemistry, 1987, Vol 26B, pages 140-142. *

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
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
CN102459275A (zh) 2012-05-16
JP5824448B2 (ja) 2015-11-25

Similar Documents

Publication Publication Date Title
AU2010239059B2 (en) Processes for the preparation of morphinane and morphinone compounds
AU725396B2 (en) Preparation of opiates, intermediates and uses of salts
JP2025096506A (ja) （Ｓ）－（２Ｒ，３Ｒ，１１ｂＲ）－３－イソブチル－９，１０－ジメトキシ－２，３，４，６，７，１１ｂ－ヘキサヒドロ－１Ｈ－ピリド［２，１－ａ］イソキノリン－２－イル２－アミノ－３－メチルブタノエートジ（４－メチルベンゼンスルホネート）の調製のための合成方法
NZ575417A (en) Process for preparing n-alkyl naltrexone halides
AU2009233315A1 (en) An improved process for the preparation of morphinane analogues
AU2018268173B2 (en) Preparation of buprenorphine
CA3159951A1 (en) Processes and intermediates for preparing mcl1 inhibitors
JP6127040B2 (ja) Ｎ−アリル化合物の調製のための遷移金属触媒プロセスおよびその使用
EP0496830A4 (en) Total synthesis of northebaine, normorphine, noroxymorphone enantiomers and derivatives via n-nor intermediates
WO2011037854A2 (en) Methods for producing hydrocodone, hydromorphone or a derivative thereof
EP2705040B1 (en) Process for the preparation of morphine analogs via metal catalyzed n-demethylation/functionalization and intramolecular group transfer
CN113754666A (zh) 一种苯并吡嗪类化合物及其合成方法
RU2236412C2 (ru) Способ получения производных морфинона, способ получения производных 14-гидроксиморфинона, и способ получения производных оксиморфона
AU6112800A (en) Method for making debromohymenialdisine and analogs thereof
CN104520302A (zh) 通过有机金属试剂与衍生自吗啡烷的噁唑烷的反应制备吗啡类似物的方法
CN116768898B (zh) 长春质碱的不对称全合成方法
CN102267973B (zh) 青蒿素中间体、合成方法和用途
Deschamps Investigations into naloxone-based degradation products in Suboxone® sublingual film
KR100574435B1 (ko) 후퍼진 ｂ 유도체와 이의 제조방법
CN101646675A (zh) 季n-烷基吗啡喃生物碱盐的制备方法
CZ2005795A3 (cs) Zpusob výroby (2S,7´R)-2-[17´-(cyklopropylmethyl)-3´-hydroxy-4´,5´-epoxy-6´-methoxy-6´,14´-endoethanomorfinan-7´-yl]-3,3-dimethylbutan-2-olu
CA2881229A1 (en) Methods for the preparation of hydromorphone
Yan-fen et al. Total Synthesis of Anisodine
Fleischhacker et al. Novel Ring Systems in Morphinoides II [1]: C8, 17-Ethano-Bridged 4, 5-Epoxyhasubanans

Legal Events

Date Code Title Description
FGA Letters patent sealed or granted (standard patent)
MK14 Patent ceased section 143(a) (annual fees not paid) or expired