FR2189403A1 - Norcodeine prepn - by reduction of 1-halo-norcodeinones, novel intermedi-ates for narcotic antagonists - Google Patents
Norcodeine prepn - by reduction of 1-halo-norcodeinones, novel intermedi-ates for narcotic antagonistsInfo
- Publication number
- FR2189403A1 FR2189403A1 FR7321915A FR7321915A FR2189403A1 FR 2189403 A1 FR2189403 A1 FR 2189403A1 FR 7321915 A FR7321915 A FR 7321915A FR 7321915 A FR7321915 A FR 7321915A FR 2189403 A1 FR2189403 A1 FR 2189403A1
- Authority
- FR
- France
- Prior art keywords
- prepn
- norcodeinones
- norcodeine
- halo
- intermedi
- 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.)
- Withdrawn
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:
- C07D489/02—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
Prepn. of norcodeins by reaction of 1-halo-norcodeinones of formula: where X is Cl or Br; and Y is CHO, -CO2Me or -CO2Et with a suitable reagent to give a cpd. of formula: which in turn is reduced to norcodeins (III): Cpds. are new. Removal of the protecting gp. Y requires mild conditions to avoid possible rearrangement of the mol. When Y = -CHO this is performed with H2O2, or aq. or alcoholic HCl or HBr. When Y is CO2Me or CO2Et alkaline hydrolysis in an inert atmos. is prefd. Norcodeine is an inter. in the prepn. of narcotic antagonists such as nalorphine or normorphine.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US26308372A | 1972-06-15 | 1972-06-15 |
Publications (1)
Publication Number | Publication Date |
---|---|
FR2189403A1 true FR2189403A1 (en) | 1974-01-25 |
Family
ID=23000311
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FR7321915A Withdrawn FR2189403A1 (en) | 1972-06-15 | 1973-06-15 | Norcodeine prepn - by reduction of 1-halo-norcodeinones, novel intermedi-ates for narcotic antagonists |
Country Status (1)
Country | Link |
---|---|
FR (1) | FR2189403A1 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2009078987A1 (en) * | 2007-12-17 | 2009-06-25 | Mallinckrodt Inc. | Process and compounds for the production of (+) opiates |
US8624031B2 (en) | 2011-09-08 | 2014-01-07 | Mallinckrodt Llc | Production of alkaloids without the isolation of intermediates |
-
1973
- 1973-06-15 FR FR7321915A patent/FR2189403A1/en not_active Withdrawn
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2009078987A1 (en) * | 2007-12-17 | 2009-06-25 | Mallinckrodt Inc. | Process and compounds for the production of (+) opiates |
US8252808B2 (en) | 2007-12-17 | 2012-08-28 | Mallinckrodt Llc | Process and compounds for the production of (+)opiates |
US8624031B2 (en) | 2011-09-08 | 2014-01-07 | Mallinckrodt Llc | Production of alkaloids without the isolation of intermediates |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
ST | Notification of lapse |