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 derivatives

Info

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
Application number
GB2527862A
Inventor
Michael George Lester V Petrow
Oliver Stephenson
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.)
BDH Chemicals Ltd
Original Assignee
BDH Chemicals 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 BDH Chemicals Ltd filed Critical BDH Chemicals Ltd
Priority to GB2527862A priority Critical patent/GB981046A/en
Priority to DK312863A priority patent/DK107749C/en
Priority to BE634402A priority patent/BE634402A/en
Publication of GB981046A publication Critical patent/GB981046A/en
Expired legal-status Critical Current

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.
GB2527862A 1962-07-02 1962-07-02 Hexahydro-4ah-8,9c-iminoethano phenanthro-[4,5-b,c,d]-furan derivatives Expired GB981046A (en)

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)

* Cited by examiner, † Cited by third party
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

Cited By (25)

* Cited by examiner, † Cited by third party
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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