DK227685A - PROCEDURE FOR DEALKYLING OF 14-HYDROXY MORPHINALALKALOIDS AND INTERMEDIATES FOR USING THE PROCEDURE - Google Patents

PROCEDURE FOR DEALKYLING OF 14-HYDROXY MORPHINALALKALOIDS AND INTERMEDIATES FOR USING THE PROCEDURE Download PDF

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Publication number
DK227685A
DK227685A DK227685A DK227685A DK227685A DK 227685 A DK227685 A DK 227685A DK 227685 A DK227685 A DK 227685A DK 227685 A DK227685 A DK 227685A DK 227685 A DK227685 A DK 227685A
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DK
Denmark
Prior art keywords
procedure
hydroxy
formula
morphinalalkaloids
dealkyling
Prior art date
Application number
DK227685A
Other languages
Danish (da)
Other versions
DK160048B (en
DK227685D0 (en
DK160048C (en
Inventor
Christian Hoff
Christian Vergely
Original Assignee
Sanofi Sa
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 Sanofi Sa filed Critical Sanofi Sa
Publication of DK227685D0 publication Critical patent/DK227685D0/en
Publication of DK227685A publication Critical patent/DK227685A/en
Publication of DK160048B publication Critical patent/DK160048B/en
Application granted granted Critical
Publication of DK160048C publication Critical patent/DK160048C/en

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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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Steroid Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)

Abstract

1. A process for the dealkylation of 14-hydroxymorphinan alkaloids, characterized in that it consists in : 1) reacting the 14-hydroxy derivative of the formula : see diagramm : EP0164290,P5,F6 in which R' is CH3 or COCH3 , with excess ethyl chloroformate, in the presence of potassium carbonate and in a solvent, 2) subjecting the resulting carbamate of the formula : see diagramm : EP0164290,P5,F2 in which R' is CH3 or COCH3 , to hydrolysis in a strong acid medium to give the corresponding dealkylated derivative of the formula : see diagramm : EP0164290,P5,F3 in which R is CH3 or hydrogen.
DK227685A 1984-05-25 1985-05-22 PROCEDURE FOR DEALKYLING OF 14-HYDROXY MORPHINANALKALOIDS DK160048C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR8408273A FR2564838B1 (en) 1984-05-25 1984-05-25 PROCESS FOR DEALKYLATION OF ALKALOIDS AND INTERMEDIATES
FR8408273 1984-05-25

Publications (4)

Publication Number Publication Date
DK227685D0 DK227685D0 (en) 1985-05-22
DK227685A true DK227685A (en) 1985-11-26
DK160048B DK160048B (en) 1991-01-21
DK160048C DK160048C (en) 1991-06-17

Family

ID=9304425

Family Applications (1)

Application Number Title Priority Date Filing Date
DK227685A DK160048C (en) 1984-05-25 1985-05-22 PROCEDURE FOR DEALKYLING OF 14-HYDROXY MORPHINANALKALOIDS

Country Status (12)

Country Link
EP (1) EP0164290B1 (en)
JP (1) JPS60258183A (en)
AT (1) ATE46163T1 (en)
AU (1) AU577379B2 (en)
CA (1) CA1244825A (en)
DE (1) DE3572819D1 (en)
DK (1) DK160048C (en)
ES (1) ES8603893A1 (en)
FR (1) FR2564838B1 (en)
NO (1) NO164981C (en)
NZ (1) NZ212193A (en)
PT (1) PT80519B (en)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
US6067749A (en) * 1996-07-11 2000-05-30 Tasmanian Alkaloids Pty. Ltd. Papaver somniferum strain with high concentration of thebaine and oripavine
GB2438400A (en) * 2006-05-25 2007-11-28 Alpharma Aps N-Demethylation of 14-hydroxy morphinans with alpha-chloroethyl chloroformate
GB2444052A (en) * 2006-05-25 2008-05-28 Alpharma Aps Processes of preparing morphinan derivatives such as naltrexone and naloxone comprising O- and N-demethylation and reductive alkylation steps
GB2438401A (en) * 2006-05-25 2007-11-28 Alpharma Aps Preparation of morphinan derivatives comprising N-demethylation, reductive amination and O-demethylation steps
US7999104B2 (en) * 2007-06-29 2011-08-16 Brock University Methods for one-pot N-demethylation/N-acylation of morphine and tropane alkaloids
US8962841B2 (en) 2007-06-29 2015-02-24 Brock University Methods for one-pot N-demethylation/N-functionalization of morphine and tropane alkaloids
US8101757B2 (en) * 2007-12-17 2012-01-24 Mallinckrodt Llc Processes for the preparation of normorphinan salts
US9131649B2 (en) 2008-03-07 2015-09-15 Tasmanian Alkaloids Pty. Ltd Papaver somniferum strain with high concentration of thebaine
AU2009233315B2 (en) * 2008-03-31 2013-08-29 Sun Pharmaceutical Industries Ltd. An improved process for the preparation of morphinane analogues
CA2936749C (en) 2010-06-11 2019-07-09 Joshua R. Giguere Transition metal-catalyzed processes for the preparation of n-allyl compounds and use thereof
EP2580218B1 (en) 2010-06-11 2015-02-25 Rhodes Technologies Process for n-dealkylation of tertiary amines
WO2012151669A1 (en) * 2011-05-06 2012-11-15 Brock University Process for the preparation of morphine analogs via metal catalyzed n-demethylation/functionalization and intramolecular group transfer

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4141807A (en) * 1977-03-01 1979-02-27 Stauffer Chemical Company Photopolymerizable composition stabilized with nitrogen-containing aromatic compounds
DE2727805A1 (en) * 1977-06-21 1979-01-04 Goedecke Ag METHOD FOR PRODUCING OXYNORMORPHONE
US4390699A (en) * 1981-07-16 1983-06-28 The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services 6-Keto-morphinans belonging to the 14-hydroxy-series
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
FR2533561B1 (en) * 1982-09-24 1986-07-25 Poudres & Explosifs Ste Nale PROCESS FOR THE PREPARATION OF VINYL CARBAMATES AND NOVEL VINYL CARBAMATES

Also Published As

Publication number Publication date
AU4284385A (en) 1985-11-28
DK160048B (en) 1991-01-21
CA1244825A (en) 1988-11-15
ES543338A0 (en) 1986-01-01
ES8603893A1 (en) 1986-01-01
FR2564838B1 (en) 1986-11-07
JPS60258183A (en) 1985-12-20
PT80519B (en) 1988-01-22
DE3572819D1 (en) 1989-10-12
ATE46163T1 (en) 1989-09-15
NZ212193A (en) 1988-10-28
NO164981C (en) 1990-12-05
PT80519A (en) 1985-06-01
DK227685D0 (en) 1985-05-22
AU577379B2 (en) 1988-09-22
NO164981B (en) 1990-08-27
NO852091L (en) 1985-11-26
EP0164290A1 (en) 1985-12-11
EP0164290B1 (en) 1989-09-06
FR2564838A1 (en) 1985-11-29
DK160048C (en) 1991-06-17

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