GB815217A - 1-o-chlorophenyl-1-phenyl-3-(dimethylamino)-propan-1-ol and its salts and therapeuticcompositions containing them - Google Patents
1-o-chlorophenyl-1-phenyl-3-(dimethylamino)-propan-1-ol and its salts and therapeuticcompositions containing themInfo
- Publication number
- GB815217A GB815217A GB37690/57A GB3769057A GB815217A GB 815217 A GB815217 A GB 815217A GB 37690/57 A GB37690/57 A GB 37690/57A GB 3769057 A GB3769057 A GB 3769057A GB 815217 A GB815217 A GB 815217A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chlorophenyl
- phenyl
- propan
- dimethylamino
- acid addition
- 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
- WRCHFMBCVFFYEQ-UHFFFAOYSA-N Clofedanol Chemical compound C=1C=CC=C(Cl)C=1C(O)(CCN(C)C)C1=CC=CC=C1 WRCHFMBCVFFYEQ-UHFFFAOYSA-N 0.000 title abstract 4
- 150000003839 salts Chemical class 0.000 title abstract 4
- 239000011780 sodium chloride Substances 0.000 title abstract 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 4
- 206010011224 Cough Diseases 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 235000020357 syrup Nutrition 0.000 abstract 3
- 239000006188 syrup Substances 0.000 abstract 3
- VMHYWKBKHMYRNF-UHFFFAOYSA-N (2-chlorophenyl)-phenylmethanone Chemical compound ClC1=CC=CC=C1C(=O)C1=CC=CC=C1 VMHYWKBKHMYRNF-UHFFFAOYSA-N 0.000 abstract 2
- MWOOGOJBHIARFG-UHFFFAOYSA-N Vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 abstract 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000000829 suppository Substances 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- XYGSFNHCFFAJPO-UHFFFAOYSA-N 1-(2-chlorophenyl)-3-(dimethylamino)-1-phenylpropan-1-ol;hydron;chloride Chemical compound Cl.C=1C=CC=C(Cl)C=1C(O)(CCN(C)C)C1=CC=CC=C1 XYGSFNHCFFAJPO-UHFFFAOYSA-N 0.000 abstract 1
- RFCSOSSACJNSDT-UHFFFAOYSA-N 3-amino-1-(2-chlorophenyl)-1-phenylpropan-1-ol Chemical compound C=1C=CC=C(Cl)C=1C(O)(CCN)C1=CC=CC=C1 RFCSOSSACJNSDT-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- 240000007651 Rubus glaucus Species 0.000 abstract 1
- 235000011034 Rubus glaucus Nutrition 0.000 abstract 1
- 235000009122 Rubus idaeus Nutrition 0.000 abstract 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N Sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 abstract 1
- 230000000954 anitussive Effects 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 235000020426 cherry syrup Nutrition 0.000 abstract 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 1
- 229910052803 cobalt Inorganic materials 0.000 abstract 1
- 239000010941 cobalt Substances 0.000 abstract 1
- 229940110456 cocoa butter Drugs 0.000 abstract 1
- 235000019868 cocoa butter Nutrition 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000000470 constituent Substances 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 235000019441 ethanol Nutrition 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 1
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 150000003141 primary amines Chemical class 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
- 230000001225 therapeutic Effects 0.000 abstract 1
- 229940117960 vanillin Drugs 0.000 abstract 1
- 235000012141 vanillin Nutrition 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/02—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton
- C07C225/14—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated
- C07C225/16—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Abstract
The invention comprises 1-o-chlorophenyl-1-phenyl - 3 - (dimethylamino) - propan - 1 - ol, its acid addition salts, and its preparation by reacting o-chloro-benzophenone with acetonitrile in the presence of a strongly basic condensing agent, hydrogenating the resulting b -hydroxy - b - o - chlorophenyl - b - phenyl - propionitrile, and dimethylating the primary amine so formed. The invention also comprises therapeutic compositions in which the tertiary base or its acid addition salts form the active constituent (see Group VI). In an example, o-chlorobenzophenone is reacted with acetonitrile in the presence of sodamide to form b -hydroxy - b - o - chlorophenyl - b - phenyl - pro - pionitrile which is hydrogenated under pressure in the presence of Raney cobalt. The resulting 1 - o - chlorophenyl - 1 - phenyl - 3 - aminopropan-1-ol is dimethylated with methanolic formaldehyde in the presence of Raney nickel to 1-o-chlorophenyl - 1 - phenyl - 3 - (dimethylamino)-propan-1-ol, the hydrochloride of which is also described.ALSO:Antitussive compositions containing 1-o-chlorophenyl - 1 - phenyl - 3 - (dimethylamino) - propan-1-ol and an acid addition salt thereof with a liquid or solid pharmaceutical carrier are prepared in the form of tablets, capsules, powders, solutions, syrups, troches or suppositories. In examples, 1-o-chlorophenyl-1-phenyl-3-(dimethylamino)-propan-1-ol hydrochloride is combined with (1) glycerol, ethanol and water to produce a cough medicine; (2) glycerol and rubi idaci (raspberry) syrup to form a cough syrup; (3) ethanol, vanillin, cherry syrup and water to form a cough elixir. The same compound is also (4) blended with cocoa butter to form suppositories and (5) mixed with conventional excipients and tabletted. The results of pharmacological tests are also supplied.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB815217A true GB815217A (en) | 1959-06-17 |
Family
ID=1745009
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB37690/57A Expired GB815217A (en) | 1957-12-03 | 1-o-chlorophenyl-1-phenyl-3-(dimethylamino)-propan-1-ol and its salts and therapeuticcompositions containing them |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB815217A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3190920A (en) * | 1961-05-19 | 1965-06-22 | Smith Kline French Lab | 1-ortho-lower alkyl-phenyl-1-phenyl-2 lower alkyl-3-diloweralkylamino-1-propanols |
| US3275510A (en) * | 1966-09-27 | Topical antitussive preparations | ||
| CZ299556B6 (en) * | 1999-04-07 | 2008-09-03 | Grünenthal GmbH | Derivatives of 3-amino-3-arylpropan-1-ol, process of their preparation, medicaments in which these substances are comprised and their use |
-
1957
- 1957-12-03 GB GB37690/57A patent/GB815217A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3275510A (en) * | 1966-09-27 | Topical antitussive preparations | ||
| US3190920A (en) * | 1961-05-19 | 1965-06-22 | Smith Kline French Lab | 1-ortho-lower alkyl-phenyl-1-phenyl-2 lower alkyl-3-diloweralkylamino-1-propanols |
| CZ299556B6 (en) * | 1999-04-07 | 2008-09-03 | Grünenthal GmbH | Derivatives of 3-amino-3-arylpropan-1-ol, process of their preparation, medicaments in which these substances are comprised and their use |
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