GB2000137A - 7,8-Dihydro-14-hydroxy-normorphine - Google Patents

7,8-Dihydro-14-hydroxy-normorphine

Info

Publication number
GB2000137A
GB2000137A GB7827483A GB7827483A GB2000137A GB 2000137 A GB2000137 A GB 2000137A GB 7827483 A GB7827483 A GB 7827483A GB 7827483 A GB7827483 A GB 7827483A GB 2000137 A GB2000137 A GB 2000137A
Authority
GB
United Kingdom
Prior art keywords
normorphine
dihydro
hydroxy
converted
compound
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.)
Granted
Application number
GB7827483A
Other versions
GB2000137B (en
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.)
Warner Lambert Co LLC
Original Assignee
Warner Lambert Co LLC
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 Warner Lambert Co LLC filed Critical Warner Lambert Co LLC
Publication of GB2000137A publication Critical patent/GB2000137A/en
Application granted granted Critical
Publication of GB2000137B publication Critical patent/GB2000137B/en
Expired legal-status Critical Current

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:
    • C07D489/06—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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The present invention provides a process for the preparation of 7,8-dihydro-14-hydroxy-normorphine, wherein an oxymorphone compound is converted into the corresponding 17-(2,2,2-trichloroethoxycarbonyl) compound by reaction with a 4 to 6 fold excess of 2,2,2-trichloroethyl chloroformate in the presence of 1,2-dichloroethane at a temperature of from 25 to 170 DEG C., whereafter, if necessary, substituents present in the 3- and/or 14-positions are converted into hydroxyl groups and the 2,2,2-trichloroethoxycarbonyl radical in the 17-position is removed.
GB7827483A 1977-06-21 1978-06-21 Process for the preparation of 7,8-dihydro-14-hydroxynormorphine Expired GB2000137B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19772727805 DE2727805A1 (en) 1977-06-21 1977-06-21 METHOD FOR PRODUCING OXYNORMORPHONE

Publications (2)

Publication Number Publication Date
GB2000137A true GB2000137A (en) 1979-01-04
GB2000137B GB2000137B (en) 1982-01-06

Family

ID=6011952

Family Applications (1)

Application Number Title Priority Date Filing Date
GB7827483A Expired GB2000137B (en) 1977-06-21 1978-06-21 Process for the preparation of 7,8-dihydro-14-hydroxynormorphine

Country Status (7)

Country Link
JP (1) JPS549300A (en)
DE (1) DE2727805A1 (en)
FI (1) FI781962A (en)
FR (1) FR2395269A1 (en)
GB (1) GB2000137B (en)
HU (1) HU177923B (en)
NL (1) NL7806658A (en)

Cited By (7)

* 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
GB2438400A (en) * 2006-05-25 2007-11-28 Alpharma Aps N-Demethylation of 14-hydroxy morphinans with alpha-chloroethyl chloroformate
GB2438401A (en) * 2006-05-25 2007-11-28 Alpharma Aps Preparation of morphinan derivatives comprising N-demethylation, reductive amination and O-demethylation steps
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
US8946214B2 (en) 2011-05-06 2015-02-03 Brock University Process for the preparation of morphine analogs via metal catalyzed N-demethylation/functionalization and intramolecular group transfer
US9624232B2 (en) 2010-06-11 2017-04-18 Rhodes Technologies Transition metal-catalyzed processes for the preparation of N-allyl compounds and use thereof
US11845759B2 (en) 2018-02-23 2023-12-19 Rhodes Technologies Opioid compounds and uses thereof

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2562072B1 (en) * 1984-03-27 1989-07-07 Mallinckrodt Inc PROCESS FOR THE PREPARATION OF NOROXYMORPHONE FROM MORPHINE, AND INTERMEDIATE COMPOUNDS USED IN THIS PROCESS
FR2564838B1 (en) * 1984-05-25 1986-11-07 Sanofi Sa PROCESS FOR DEALKYLATION OF ALKALOIDS AND INTERMEDIATES
HU197750B (en) * 1984-07-17 1989-05-29 Alkaloida Vegyeszeti Gyar Process for n-demethylation of morphine alkaloids
WO2006084389A1 (en) 2005-02-11 2006-08-17 Cilag Ltd. Method for purifying noroxymorphone compounds
ES2537610T3 (en) 2010-06-11 2015-06-10 Rhodes Technologies Process for the N-desalkylation of tertiary amines
ES2701855T3 (en) 2016-05-31 2019-02-26 Alcaliber Investig Desarrollo E Innovacion Slu Process for obtaining 3,14-diacetyloxymorphona from oripavine

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3905981A (en) * 1973-10-12 1975-09-16 Research Corp N-dealkylation of tertiary amines

Cited By (16)

* 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
GB2471802B (en) * 2006-05-25 2011-02-16 Alpharma Chemical process
GB2471801B (en) * 2006-05-25 2011-02-16 Alpharma Process useful in the preparation of morphine antagonists
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
GB2471802A (en) * 2006-05-25 2011-01-12 Alpharma N-Demethylation of 14-hydroxy morphinans with a-chloroethyl c oroformate
GB2471801A (en) * 2006-05-25 2011-01-12 Alpharma Preparation of morphinan derivatives comprising N-demethylation, reductive amination and O-demethylation steps
GB2471803A (en) * 2006-05-25 2011-01-12 Alpharma 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
GB2438400A (en) * 2006-05-25 2007-11-28 Alpharma Aps N-Demethylation of 14-hydroxy morphinans with alpha-chloroethyl chloroformate
GB2471803B (en) * 2006-05-25 2011-02-16 Alpharma Chemical process
US9624232B2 (en) 2010-06-11 2017-04-18 Rhodes Technologies Transition metal-catalyzed processes for the preparation of N-allyl compounds and use thereof
US9657030B2 (en) 2010-06-11 2017-05-23 Rhodes Technologies Transition metal-catalyzed processes for the preparation of N-allyl compounds and use thereof
US8946214B2 (en) 2011-05-06 2015-02-03 Brock University Process for the preparation of morphine analogs via metal catalyzed N-demethylation/functionalization and intramolecular group transfer
US9108967B2 (en) 2011-05-06 2015-08-18 Brock University Process for the preparation of morphine analogs via metal catalyzed N-demethylation/functionalization and intramolecular group transfer
US9533993B2 (en) 2011-05-06 2017-01-03 Brock University Process for the preparation of morphine analogs via metal catalyzed N-demethylation/functionalization and intramolecular group transfer
US11845759B2 (en) 2018-02-23 2023-12-19 Rhodes Technologies Opioid compounds and uses thereof

Also Published As

Publication number Publication date
FR2395269A1 (en) 1979-01-19
GB2000137B (en) 1982-01-06
HU177923B (en) 1982-01-28
NL7806658A (en) 1978-12-27
FI781962A (en) 1978-12-22
JPS549300A (en) 1979-01-24
FR2395269B1 (en) 1983-06-10
DE2727805A1 (en) 1979-01-04

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Legal Events

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PCNP Patent ceased through non-payment of renewal fee