GB1012956A - Improvements in or related to n-cyanomorphinan derivatives and their preparation - Google Patents

Improvements in or related to n-cyanomorphinan derivatives and their preparation

Info

Publication number
GB1012956A
GB1012956A GB42093/64A GB4209364A GB1012956A GB 1012956 A GB1012956 A GB 1012956A GB 42093/64 A GB42093/64 A GB 42093/64A GB 4209364 A GB4209364 A GB 4209364A GB 1012956 A GB1012956 A GB 1012956A
Authority
GB
United Kingdom
Prior art keywords
group
hydroxy
preparation
morphinan
phenyloxy
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
GB42093/64A
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 GB1012956A publication Critical patent/GB1012956A/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)
  • Other In-Based Heterocyclic Compounds (AREA)

Abstract

The invention comprises compounds of the formula <FORM:1012956/C2/1> wherein R represents an alkyl group of not more than 5 carbon atoms, R1 represents a hydrogen atom or an aryloxy group, R11 represents a methylene or carbonyl group and X represents a hydrogen atom or a hydroxyl or acyloxy group, and the preparation thereof by reaction of a compound of the formula <FORM:1012956/C2/2> with a cyanogen halide. The reaction may be carried out at room temperature, but is preferably performed in an inert organic solvent under reflux. (-) - 3 - Methoxy - 6 - oxo - 14 - hydroxy - N - methyl-morphinan (cis) is prepared from the-baine by oxidation to produce the 6-keto derivative, conversion to the oxime, and hydrogenation to give (-)-3-methoxy-4-hydroxy-6-oxo -14-hydroxy-N-methyl-morphinan which is is converted to the 6-phenyloxy-derivative, ketalated, treated with sodium and ammonia to remove the 6-phenyloxy-group and finally deketalated.
GB42093/64A 1962-04-06 1963-04-04 Improvements in or related to n-cyanomorphinan derivatives and their preparation Expired GB1012956A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP1406262 1962-04-06

Publications (1)

Publication Number Publication Date
GB1012956A true GB1012956A (en) 1965-12-15

Family

ID=11850588

Family Applications (2)

Application Number Title Priority Date Filing Date
GB13486/63A Expired GB1012955A (en) 1962-04-06 1963-04-04 Improvements in or related to morphinan derivatives and their preparation
GB42093/64A Expired GB1012956A (en) 1962-04-06 1963-04-04 Improvements in or related to n-cyanomorphinan derivatives and their preparation

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB13486/63A Expired GB1012955A (en) 1962-04-06 1963-04-04 Improvements in or related to morphinan derivatives and their preparation

Country Status (2)

Country Link
CH (1) CH438349A (en)
GB (2) GB1012955A (en)

Also Published As

Publication number Publication date
CH438349A (en) 1967-06-30
GB1012955A (en) 1965-12-15

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