GB713146A - Anti-cough agents comprising (ú½)-3-hydroxy-n-methyl-morphinane ethers and process for the manufacture thereof - Google Patents
Anti-cough agents comprising (ú½)-3-hydroxy-n-methyl-morphinane ethers and process for the manufacture thereofInfo
- Publication number
- GB713146A GB713146A GB25960/52A GB2596052A GB713146A GB 713146 A GB713146 A GB 713146A GB 25960/52 A GB25960/52 A GB 25960/52A GB 2596052 A GB2596052 A GB 2596052A GB 713146 A GB713146 A GB 713146A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methylmorphinane
- hydroxy
- ethers
- ether
- morphinane
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
Abstract
The invention comprises ethers of (+)-3-hydroxy-N-methylmorphinane, the ether groups of which are alkyl or alkenyl containing more than one carbon atom, and acid addition salts thereof. The ethers are prepared by treating (+)-3-hydroxy-N-methylmorphinane with an etherifying agent, particularly a compound of general formula <FORM:0713146/IV (b)/1> wherein R1, R2 and R3 represent lower alky or alkenyl radicals of which at least one contains more than one carbon atom, or an alkoxide thereof. An unsaturated morphinane ether may be hydrogenated to the corresponding saturated derivative. In examples: (1) phenyl triethyl ammonium methoxide and (+)-3-hydroxy-N-methylmorphinane are refluxed in toluene, and the product distilled in vacuo to yield (+)-3-ethoxy-N-methylmorphinane, which may be then converted to its acid phosphate; (2) (+)-3-hydroxy-N-methylmorphinane is treated with phenyl allyl dimethyl ammonium hydroxide to yield (+)-3-allyloxy-N-methylmorphinane, and subsequently its hydrobromide; (3) hydrogenation of the 3-allyloxy compound using palladium charcoal produces the corresponding (+)-3-propyloxy ether, which is converted to its tartrate.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH713146X | 1951-10-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB713146A true GB713146A (en) | 1954-08-04 |
Family
ID=4530915
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB25960/52A Expired GB713146A (en) | 1951-10-18 | 1952-10-16 | Anti-cough agents comprising (ú½)-3-hydroxy-n-methyl-morphinane ethers and process for the manufacture thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB713146A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3085091A (en) * | 1963-04-09 | Novel pkocess fos elimination of | ||
| EP2397159A2 (en) | 2008-10-30 | 2011-12-21 | Concert Pharmaceuticals, Inc. | Combination of morphinan compounds and antidepressant for the treatment of intractable and chronic pain |
| EP2397158A2 (en) | 2008-10-30 | 2011-12-21 | Concert Pharmaceuticals, Inc. | Combination of morphinan compounds and antidepressant for the treatment of pseudobulbar affect |
| EP2418211A1 (en) | 2008-09-19 | 2012-02-15 | Concert Pharmaceuticals Inc. | Deuterated morphinane compounds |
| US8541436B2 (en) | 2007-05-01 | 2013-09-24 | Concert Pharmaceuticals Inc. | Morphinan compounds |
| US9314440B2 (en) | 2007-05-01 | 2016-04-19 | Concert Pharmaceuticals, Inc. | Morphinan compounds |
| WO2017020002A1 (en) | 2015-07-30 | 2017-02-02 | Concert Pharmaceuticals, Inc. | Deuterated morphinan compounds for use in treating agitation |
-
1952
- 1952-10-16 GB GB25960/52A patent/GB713146A/en not_active Expired
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3085091A (en) * | 1963-04-09 | Novel pkocess fos elimination of | ||
| US9072711B2 (en) | 2007-05-01 | 2015-07-07 | Concert Pharmaceuticals, Inc. | Morphinan compounds |
| US11473123B2 (en) | 2007-05-01 | 2022-10-18 | Concert Pharmaceuticals, Inc. | Morphinan compounds |
| US9868976B2 (en) | 2007-05-01 | 2018-01-16 | Concert Pharmaceuticals, Inc. | Morphinan compounds |
| US9314440B2 (en) | 2007-05-01 | 2016-04-19 | Concert Pharmaceuticals, Inc. | Morphinan compounds |
| US8541436B2 (en) | 2007-05-01 | 2013-09-24 | Concert Pharmaceuticals Inc. | Morphinan compounds |
| US8748450B2 (en) | 2007-05-01 | 2014-06-10 | Concert Pharmaceuticals, Inc. | Morphinan compounds |
| EP2418211A1 (en) | 2008-09-19 | 2012-02-15 | Concert Pharmaceuticals Inc. | Deuterated morphinane compounds |
| EP2634187A1 (en) | 2008-09-19 | 2013-09-04 | Concert Pharmaceuticals Inc. | Deuterated morphinane compounds |
| EP3248978A1 (en) | 2008-09-19 | 2017-11-29 | Concert Pharmaceuticals Inc. | Deuterated morphinan compounds |
| EP3090760A1 (en) | 2008-10-30 | 2016-11-09 | Concert Pharmaceuticals, Inc. | Combination of morphinan compounds and antidepressant for the treatment of pseudobulbar affect, neurological diseases, intractable and chronic pain and brain injury |
| EP2397158A2 (en) | 2008-10-30 | 2011-12-21 | Concert Pharmaceuticals, Inc. | Combination of morphinan compounds and antidepressant for the treatment of pseudobulbar affect |
| EP3603674A1 (en) | 2008-10-30 | 2020-02-05 | Concert Pharmaceuticals, Inc. | Combination of morphinan compounds and antidepressant for the treatment of intractable and chronic pain |
| EP2397159A2 (en) | 2008-10-30 | 2011-12-21 | Concert Pharmaceuticals, Inc. | Combination of morphinan compounds and antidepressant for the treatment of intractable and chronic pain |
| WO2017020002A1 (en) | 2015-07-30 | 2017-02-02 | Concert Pharmaceuticals, Inc. | Deuterated morphinan compounds for use in treating agitation |
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