GB1031364A - Improvements in or relating to 6-hydroxymorphinan derivatives and their production - Google Patents

Improvements in or relating to 6-hydroxymorphinan derivatives and their production

Info

Publication number
GB1031364A
GB1031364A GB13478/63A GB1347863A GB1031364A GB 1031364 A GB1031364 A GB 1031364A GB 13478/63 A GB13478/63 A GB 13478/63A GB 1347863 A GB1347863 A GB 1347863A GB 1031364 A GB1031364 A GB 1031364A
Authority
GB
United Kingdom
Prior art keywords
oxo
cis
prepared
morphinan
methyl
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
Application number
GB13478/63A
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.)
Shionogi and Co Ltd
Original Assignee
Shionogi and Co Ltd
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 Shionogi and Co Ltd filed Critical Shionogi and Co Ltd
Publication of GB1031364A publication Critical patent/GB1031364A/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
    • 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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

6 - Hydroxy - morphinans of the Formula I wherein R represents a hydrogen atom, an alkyl group of not more than 5 carbon atoms, or an alkanoyl group of not more than 6 carbon atoms, R1 represents a hydrogen atom or an aryloxy group, R11 represents a hydrogen or a hydroxyl group, and a double bond may exist between the 7 - and 8 - carbon atoms are prepared by reduction of 6-oxo-morphinans of the Formula II <FORM:1031364/C2/1> <FORM:1031364/C2/2> wherein R111 represents a hydrogen atom, an alkyl group of not more than 5 carbon atoms or an alkanoyl group having not more than 6 carbon atoms and a double bond can exist between the 7- and 8-positions, the reduction being carried out by electrolysis, catalytic hydrogenation, alkali metals in alkanols, amalgams, metal hydrides or the Meerweim-Ponndorf method. Where the a - and b -isomers are both produced they may be isolated by conventional separation techniques. (-) - 3 - hydroxy - 6 - oxo - N - methylmorphinan (cis) is prepared by the action of hydrobromic acid on the corresponding 3-methoxy compound. (-) - 3 - Methoxy - 6 - oxo - N - methyl - D 7-morphinan (cis) is prepared by the action of acetic acid on (-)-3,6-dimethoxy-N-methyl-D 5 8-morphinan (cis). (-) - 3 - Methoxy - 6 - oxo - 14 - hydroxy - N - methylmorphinan (cis) is prepared from thebaine by oxidation to give the 6-oxo-14-hydroxy derivative which is converted to its oxime which on reduction gives 3-methoxy-4,14-dihydroxy - 6 - oxo - N - methyl morphinan. This is etherified to its 4-phenoxy-derivative which is converted to the 6,6-diethyleneoxy-derivative. The 4-phenoxy group is eliminated and the product deketalated to give the desired compound. (-) - 3,14 - Dihydroxy - 6 - oxo - N - methylmorphinan (cis) is prepared by the action of hydrobromic acid on the corresponding 3-methoxy compound. (-) - 3 - Methoxy - 6 - oxo - N - methylmorphinan (trans) is prepared from (-)-3,6-dimethoxy-N-methyl-D 5,8-morphinan by treatment with hydrochloric acid followed by reduction using palladium on carbon. (-) - 3 - Acetyloxy - 6 - oxo - N - methyl - D 7-morphinan (cis) is prepared from (-)-3-methoxy-6 - oxo - N - methyl - D 7 - morphinan (cis) b treatment with aluminium bromide and acetylation with acetic-anhydride and pyridine. (-) - 3 - Acetyloxy - 6 - oxo - N - methyl-morphinan (cis) is prepared by acetylation of the corresponding 3-hydroxy compound.
GB13478/63A 1962-04-09 1963-04-04 Improvements in or relating to 6-hydroxymorphinan derivatives and their production Expired GB1031364A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP1425062 1962-04-09

Publications (1)

Publication Number Publication Date
GB1031364A true GB1031364A (en) 1966-06-02

Family

ID=11855826

Family Applications (1)

Application Number Title Priority Date Filing Date
GB13478/63A Expired GB1031364A (en) 1962-04-09 1963-04-04 Improvements in or relating to 6-hydroxymorphinan derivatives and their production

Country Status (2)

Country Link
CH (1) CH438350A (en)
GB (1) GB1031364A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8937084B2 (en) 2012-12-14 2015-01-20 Purdue Pharma L.P. Nitrogen containing morphinan derivatives and the use thereof
US8946255B2 (en) 2012-12-28 2015-02-03 Purdue Pharma L.P. Substituted morphinans and the use thereof
US8957084B2 (en) 2012-12-28 2015-02-17 Purdue Pharma L.P. 7,8-cyclicmorphinan analogs
US8980906B2 (en) 2012-12-14 2015-03-17 Purdue Pharma L.P. Pyridonemorphinan analogs and biological activity on opioid receptors
US9340542B2 (en) 2013-12-26 2016-05-17 Purdue Pharma L.P. Propellane-based compounds and the use thereof

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8937084B2 (en) 2012-12-14 2015-01-20 Purdue Pharma L.P. Nitrogen containing morphinan derivatives and the use thereof
US8980906B2 (en) 2012-12-14 2015-03-17 Purdue Pharma L.P. Pyridonemorphinan analogs and biological activity on opioid receptors
US9403824B2 (en) 2012-12-14 2016-08-02 Purdue Pharma L.P. Pyridonemorphinan analogs and biological activity on opioid receptors
US8946255B2 (en) 2012-12-28 2015-02-03 Purdue Pharma L.P. Substituted morphinans and the use thereof
US8957084B2 (en) 2012-12-28 2015-02-17 Purdue Pharma L.P. 7,8-cyclicmorphinan analogs
US9388162B2 (en) 2012-12-28 2016-07-12 Purdue Pharma L.P. Substituted morphinans and the use thereof
US9340542B2 (en) 2013-12-26 2016-05-17 Purdue Pharma L.P. Propellane-based compounds and the use thereof

Also Published As

Publication number Publication date
CH438350A (en) 1967-06-30

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