GB981046A - Hexahydro-4ah-8,9c-iminoethano phenanthro-[4,5-b,c,d]-furan derivatives - Google Patents
Hexahydro-4ah-8,9c-iminoethano phenanthro-[4,5-b,c,d]-furan derivativesInfo
- Publication number
- GB981046A GB981046A GB2527862A GB2527862A GB981046A GB 981046 A GB981046 A GB 981046A GB 2527862 A GB2527862 A GB 2527862A GB 2527862 A GB2527862 A GB 2527862A GB 981046 A GB981046 A GB 981046A
- Authority
- GB
- United Kingdom
- Prior art keywords
- general formula
- hydroxy
- alkyl
- compounds
- 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.)
- Expired
Links
Abstract
The invention comprises compounds of general formula <FORM:0981046/C2/1> wherein R is hydrogen, alkyl, hydroxyalkyl or alkoxyalkyl, R1 is hydroxy, halogen or O.CO-alkyl, R11 is hydrogen, alkyl or C.OOH (alkyl groups contain from 1 to 6 carbon atoms), and X=X1 and is oxygen or sulphur or X is NH and X1 is S and n is 0 or 1, and the preparation thereof by reacting a compound of general formula <FORM:0981046/C2/2> wherein R and R1 have the above meanings with a compound of formula HX.CHR11.(CH2)n.CHR11.X1H, where X, X1, R11 and n have the above meanings, in the presence of an acid catalyst, for example, toluene-p-sulphonic acid, boron trifluoride etherate, or in the case of cysteine hydrochloride no additional acid catalyst is added. The compounds of general Formula I in which R1 is halogen may be formed from those in which R1 is hydroxy by treatment with the appropriate phosphoryl halide in 1,2-dichloroethane and dimethylformamide and heating at 65 DEG to 75 DEG C. for several hours. In addition, in an example a b -hydroxyethoxy group is formed at the 3-position by treating the corresponding 3-hydroxy compound of the first general formula above with ethylene carbonate. Pharmaceutical compositions having analgesic activity contain as the active ingredient the compounds of the first general formula above. The compositions may be in the form of tablets, lozenges, or injectable preparations. 5,6,7,7a,8,9 - Hexahydro - 7a - acetoxy (or propionoxy) - 3 - methoxy - 12 - methyl - 5 - oxo - 4aH-8, 9c - iminoethanophenanthro - [4,5-b, c, d] furan is prepared by treating the 7a-hydroxy compound with acetic or propionic anhydride at 100 DEG C. for 5 hours. 5,6,7,7a,8,9 - Hexahydro - 3 - ethoxy - 7a - hydroxy - 12 - methyl - 5 - oxo - 4aH - 8,9C - iminoethanophenanthro - [4,5-b, c, d] - furan is prepared by treating the corresponding 3-hydroxy compound with ethyl iodide and sodium hydroxide. The Provisional Specification also refers to compounds of the first general formula above wherein R11 represents COO-Alkyl.
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2527862A GB981046A (en) | 1962-07-02 | 1962-07-02 | Hexahydro-4ah-8,9c-iminoethano phenanthro-[4,5-b,c,d]-furan derivatives |
DK312863A DK107749C (en) | 1962-07-02 | 1963-07-01 | Process for the preparation of 5,6,7,7a, 8,9-hexahydro-12-methyl-4aH-8,9c-iminoethanephenanthro- [4,5-b, c, d] -furan derivatives. |
BE634402A BE634402A (en) | 1962-07-02 | 1963-07-02 | Hydrophenanthrene derivatives and processes for their preparation |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2527862A GB981046A (en) | 1962-07-02 | 1962-07-02 | Hexahydro-4ah-8,9c-iminoethano phenanthro-[4,5-b,c,d]-furan derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
GB981046A true GB981046A (en) | 1965-01-20 |
Family
ID=10225124
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2527862A Expired GB981046A (en) | 1962-07-02 | 1962-07-02 | Hexahydro-4ah-8,9c-iminoethano phenanthro-[4,5-b,c,d]-furan derivatives |
Country Status (2)
Country | Link |
---|---|
DK (1) | DK107749C (en) |
GB (1) | GB981046A (en) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2051532A1 (en) * | 1969-05-16 | 1971-04-09 | Organon Lab | |
WO1984003627A1 (en) * | 1983-03-21 | 1984-09-27 | Key Pharma | NOVEL 4,5alphaEPOXYMORPHINAN-6-SPIRO-2'-(4'-CARBOXY,1',3'-THIAZOLIDINE) DERIVATIVES |
WO2009152776A1 (en) * | 2008-06-20 | 2009-12-23 | 重庆医药工业研究院有限责任公司 | Morphinan derivatives and their preparation method |
WO2014188266A1 (en) | 2013-05-24 | 2014-11-27 | Rhodes Technologies | Opioid ketal compounds and uses thereof |
US9126977B2 (en) | 2010-08-23 | 2015-09-08 | Alkermes Pharma Ireland Limited | Methods for treating antipsychotic-induced weight gain |
US9211293B2 (en) | 2011-12-15 | 2015-12-15 | Alkermes Pharma Ireland Limited | Opioid agonist antagonist combinations |
JP2017521373A (en) * | 2014-05-27 | 2017-08-03 | パーデュー、ファーマ、リミテッド、パートナーシップ | Spiro ring morphinans and uses thereof |
US10005790B2 (en) | 2010-07-08 | 2018-06-26 | Alkermes Pharma Ireland Limited | Process for the synthesis of substituted morphinans |
US11707466B2 (en) | 2020-11-12 | 2023-07-25 | Alkermes Pharma Ireland Limited | Immediate release multilayer tablet |
-
1962
- 1962-07-02 GB GB2527862A patent/GB981046A/en not_active Expired
-
1963
- 1963-07-01 DK DK312863A patent/DK107749C/en active
Cited By (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2051532A1 (en) * | 1969-05-16 | 1971-04-09 | Organon Lab | |
WO1984003627A1 (en) * | 1983-03-21 | 1984-09-27 | Key Pharma | NOVEL 4,5alphaEPOXYMORPHINAN-6-SPIRO-2'-(4'-CARBOXY,1',3'-THIAZOLIDINE) DERIVATIVES |
US4496570A (en) * | 1983-03-21 | 1985-01-29 | Key Pharmaceuticals, Inc. | 4,5αEpoxymorphinan-6-spiro-2'-(4'-carboxy,1',3'-thiazolidine)derivatives |
JPS60500912A (en) * | 1983-03-21 | 1985-06-20 | キイ・フア−マシユ−テイカルズ・インコ−ポレイテツド | Novel 4,5α epoxymorphinane-6-spiro-2'-(4'-carboxy,1',3'-thiazolidine) derivative |
WO2009152776A1 (en) * | 2008-06-20 | 2009-12-23 | 重庆医药工业研究院有限责任公司 | Morphinan derivatives and their preparation method |
US8563721B2 (en) | 2008-06-20 | 2013-10-22 | Chongqing Pharmaceutical Research Institute Co., Ltd. | Morphinan derivatives and preparation methods thereof |
US10005790B2 (en) | 2010-07-08 | 2018-06-26 | Alkermes Pharma Ireland Limited | Process for the synthesis of substituted morphinans |
US9126977B2 (en) | 2010-08-23 | 2015-09-08 | Alkermes Pharma Ireland Limited | Methods for treating antipsychotic-induced weight gain |
US9211293B2 (en) | 2011-12-15 | 2015-12-15 | Alkermes Pharma Ireland Limited | Opioid agonist antagonist combinations |
US20160264589A1 (en) * | 2013-05-24 | 2016-09-15 | Rhodes Technologies | Opioid ketal compounds and uses thereof |
CN105246897B (en) * | 2013-05-24 | 2017-12-26 | 罗德科技公司 | Opium sample ketal compound and its purposes |
US20160244459A1 (en) * | 2013-05-24 | 2016-08-25 | Rhodes Technologies | Opioid ketal compounds and uses thereof |
CN105246897A (en) * | 2013-05-24 | 2016-01-13 | 罗德科技公司 | Opioid ketal compounds and uses thereof |
AU2014270109B2 (en) * | 2013-05-24 | 2017-05-25 | Rhodes Technologies | Opioid ketal compounds and uses thereof |
US11773107B2 (en) | 2013-05-24 | 2023-10-03 | Rhodes Technologies | Opioid ketal compounds and uses thereof |
US11731979B2 (en) | 2013-05-24 | 2023-08-22 | Rhodes Technologies | Opioid ketal compounds and uses thereof |
JP2016518459A (en) * | 2013-05-24 | 2016-06-23 | ローズ テクノロジーズ | Opioid ketal compounds and uses thereof |
WO2014188266A1 (en) | 2013-05-24 | 2014-11-27 | Rhodes Technologies | Opioid ketal compounds and uses thereof |
US10988480B2 (en) * | 2013-05-24 | 2021-04-27 | Rhodes Technologies | Opioid ketal compounds and uses thereof |
US11091496B2 (en) * | 2013-05-24 | 2021-08-17 | Rhodes Technologies | Opioid ketal compounds and uses thereof |
US11130765B2 (en) | 2013-05-24 | 2021-09-28 | Rhodes Technologies | Opioid ketal compounds and uses thereof |
EP3148535A4 (en) * | 2014-05-27 | 2017-11-29 | Purdue Pharma LP | Spirocyclic morphinans and use thereof |
JP2017521373A (en) * | 2014-05-27 | 2017-08-03 | パーデュー、ファーマ、リミテッド、パートナーシップ | Spiro ring morphinans and uses thereof |
US11707466B2 (en) | 2020-11-12 | 2023-07-25 | Alkermes Pharma Ireland Limited | Immediate release multilayer tablet |
US11951111B2 (en) | 2020-11-12 | 2024-04-09 | Alkermes Pharma Ireland Limited | Immediate release multilayer tablet |
Also Published As
Publication number | Publication date |
---|---|
DK107749C (en) | 1967-07-03 |
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