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
- 239000003434 antitussive agent Substances 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- JAQUASYNZVUNQP-USXIJHARSA-N Levorphanol Chemical compound C1C2=CC=C(O)C=C2[C@]23CCN(C)[C@H]1[C@@H]2CCCC3 JAQUASYNZVUNQP-USXIJHARSA-N 0.000 abstract 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 150000002170 ethers Chemical class 0.000 abstract 2
- -1 (+)-3-propyloxy ether Chemical compound 0.000 abstract 1
- DIWAJQNYTVAWMY-QXAKKESOSA-N (1R,9R,10R)-4-ethoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene Chemical compound C1CCC[C@H]2[C@]3([H])N(C)CC[C@@]21C1=CC(OCC)=CC=C1C3 DIWAJQNYTVAWMY-QXAKKESOSA-N 0.000 abstract 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 1
- 229910019142 PO4 Inorganic materials 0.000 abstract 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 150000004703 alkoxides Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000001033 ether group Chemical group 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- KHFHZPIORFUMFT-UHFFFAOYSA-N methanolate;triethyl(phenyl)azanium Chemical compound [O-]C.CC[N+](CC)(CC)C1=CC=CC=C1 KHFHZPIORFUMFT-UHFFFAOYSA-N 0.000 abstract 1
- 150000003810 morphinanes Chemical class 0.000 abstract 1
- BEVGWNKCJKXLQC-UHFFFAOYSA-N n-methylmethanamine;hydrate Chemical compound [OH-].C[NH2+]C BEVGWNKCJKXLQC-UHFFFAOYSA-N 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 1
- 239000010452 phosphate Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 229940095064 tartrate Drugs 0.000 abstract 1
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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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 | ||
| EP2397158A2 (en) | 2008-10-30 | 2011-12-21 | Concert Pharmaceuticals, Inc. | Combination of morphinan compounds and antidepressant for the treatment of pseudobulbar affect |
| 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 |
| 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 (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3085091A (en) * | 1963-04-09 | Novel pkocess fos elimination of | ||
| 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 |
| US12319954B2 (en) | 2007-05-01 | 2025-06-03 | Concert Pharmaceuticals, Inc. | Morphinan compounds |
| US11473123B2 (en) | 2007-05-01 | 2022-10-18 | 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 |
| US9072711B2 (en) | 2007-05-01 | 2015-07-07 | Concert Pharmaceuticals, Inc. | Morphinan compounds |
| EP3248978A1 (en) | 2008-09-19 | 2017-11-29 | Concert Pharmaceuticals Inc. | Deuterated morphinan compounds |
| EP2634187A1 (en) | 2008-09-19 | 2013-09-04 | Concert Pharmaceuticals Inc. | Deuterated morphinane compounds |
| EP2418211A1 (en) | 2008-09-19 | 2012-02-15 | Concert Pharmaceuticals Inc. | Deuterated morphinane compounds |
| 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 |
| 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 |
| WO2017020002A1 (en) | 2015-07-30 | 2017-02-02 | Concert Pharmaceuticals, Inc. | Deuterated morphinan compounds for use in treating agitation |
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