GB975601A - Derivatives of 14-hydroxynorcodeine and their production - Google Patents
Derivatives of 14-hydroxynorcodeine and their productionInfo
- Publication number
- GB975601A GB975601A GB4245861A GB4245861A GB975601A GB 975601 A GB975601 A GB 975601A GB 4245861 A GB4245861 A GB 4245861A GB 4245861 A GB4245861 A GB 4245861A GB 975601 A GB975601 A GB 975601A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxy
- ethylnorcodeine
- acetate
- hydroxynorcodeine
- acetoxy
- 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
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The invention comprises compounds of formula <FORM:0975601/C1/1> wherein R is a hydrogen atom, a cyano-group, an alkyl group having at least two carbon atoms, or a saturated aliphatic carboxylic acid radical, and R1 and R2 are hydrogen atoms or saturated aliphatic carboxylic acid radicals, and their preparation by (a) reaction of 14-acetoxycodeine acetate or 14-acetoxy -N- ethylnorcodeine acetate with cyanogen bromide to give 14-acetoxy -N- cyanonorcodeine, which may be converted by heating in aqueous acetic acid or by hydrogenation over platinum in acetic acid to 14-hydroxy -N-acetylnorcodeine acetate, or which on treatment with lithium aluminium hydride gives 14-hydroxynorcodeine,(b) reducing 14-acetoxy -N-cyanonorcodeinone with lithium aluminium hydride to 14-hydroxynorcodeine, or reducing 14-hydroxy-N-ethylnorcodeinone with sodium borohydride to 14-hydroxy -N- ethylnorcodeine, (c) acetylating 14-hydroxynorcodeine under mild conditions to give 14-hydroxy -N- acetylnorcodeine acetate, or which may in turn be acetylated to 14-acetoxy -N- acetylnorcodeine acetate, also obtained by acetylating 14-hydroxynorcodeine under vigorous conditions, both of which acetylation products may be reduced by lithium aluminium hydride to 14-hydroxy-N ethylnorcodeine, and (d) acetylating 14-hydroxy-N-ethylnorcodeine under mild conditions to 14 hydroxy-N-ethylnorcodeine acetate, which may in turn be acetylated to 14-acetoxy-N-ethylnorcodeine acetate, also obtained by acetylating 14-hydroxy -N- ethylnorcoedine under vigorous conditions; both acetylations of 14-hydroxy-N-ethylnorcodeine may be reversed by hydrolysis using alkali. 14-Hydroxynorcodeine and 14-hydroxy -N- ethylnorcodeine may be oxidised by manganese dioxide to the corresponding norcodeine derivatives as described in Specification 975,602. The compounds of the invention have analgesic activity. The Provisional Specification also discloses the 7, 8-dihydroderivatives of the compounds of the above general formula, and compounds wherein R is an allyl, aryl, aralkyl or heterocyclyl radical, including an alkyl radical having a benzoyl substituent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4245861A GB975601A (en) | 1961-11-28 | 1961-11-28 | Derivatives of 14-hydroxynorcodeine and their production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4245861A GB975601A (en) | 1961-11-28 | 1961-11-28 | Derivatives of 14-hydroxynorcodeine and their production |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB975601A true GB975601A (en) | 1964-11-18 |
Family
ID=10424523
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4245861A Expired GB975601A (en) | 1961-11-28 | 1961-11-28 | Derivatives of 14-hydroxynorcodeine and their production |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB975601A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2062896A1 (en) | 2007-11-26 | 2009-05-27 | Siegfried Ltd. | Demethylation of 14-hydroxy substituted alkaloid derivatives |
| 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 |
-
1961
- 1961-11-28 GB GB4245861A patent/GB975601A/en not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2062896A1 (en) | 2007-11-26 | 2009-05-27 | Siegfried Ltd. | Demethylation of 14-hydroxy substituted alkaloid derivatives |
| 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 |
| CN103619847A (en) * | 2011-05-06 | 2014-03-05 | 布鲁克大学 | Process for the preparation of morphine analogs via metal catalyzed N-demethylation/functionalization and intramolecular group transfer |
| JP2014514339A (en) * | 2011-05-06 | 2014-06-19 | ブロック ユニバーシティ | Process for the preparation of morphine analogues by metal-catalyzed N-demethylation / functionalization and intramolecular group transfer |
| 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 |
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