ES411826A1 - Process for preparing pharmacologically active 1-aryloxy-2- propanolamines - Google Patents
Process for preparing pharmacologically active 1-aryloxy-2- propanolaminesInfo
- Publication number
- ES411826A1 ES411826A1 ES411826A ES411826A ES411826A1 ES 411826 A1 ES411826 A1 ES 411826A1 ES 411826 A ES411826 A ES 411826A ES 411826 A ES411826 A ES 411826A ES 411826 A1 ES411826 A1 ES 411826A1
- Authority
- ES
- Spain
- Prior art keywords
- propanolamines
- aryloxy
- pharmacologically active
- chloroform
- radicals
- 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
- 238000004519 manufacturing process Methods 0.000 title 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Procedure for obtaining pharmacologically active 1-aryloxy-2-propanolamines, which respond to the formula: ** (See formula) ** in which the radicals R1 and R2 that are attached to the aromatic ring can be respectively and at the same time (see graph) And as for the radicals R'and R''bound to nitrogen in each of the compounds respectively and at the same time: (see graph) whose procedure is characterized in that a phenol is reacted with epichlorohydrin, in the presence of catalysts at a temperature ranging from 70-100º for a time that can vary between 10-20 hours, the reaction mixture is treated with a hydroxide solution sodium for 24 hours; it is extracted with chloroform, the chloroform is removed in vacuo and the residue is distilled under reduced pressure and because in the second phase of the reaction the amine is dissolved in the glycidyl ether obtained in the first phase, dissolved in ethanol or tetrahydrofuran. corresponding to each case. (Machine-translation by Google Translate, not legally binding)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES411826A ES411826A1 (en) | 1973-02-20 | 1973-02-20 | Process for preparing pharmacologically active 1-aryloxy-2- propanolamines |
| GB5057373A GB1441976A (en) | 1973-02-20 | 1973-10-31 | Process for preparing pharmacologically active 1-aryloxy-2- propanolamines |
| FR7342192A FR2218094B1 (en) | 1973-02-20 | 1973-11-27 | |
| BE138389A BE808066A (en) | 1973-02-20 | 1973-11-30 | 1-ARYLOXY-2-PROPANOLAMINES |
| DE2359926A DE2359926C3 (en) | 1973-02-20 | 1973-12-01 | 1-Phenoxy-2-propanolamines, processes for their preparation and pharmaceuticals containing them |
| NL7317220A NL7317220A (en) | 1973-02-20 | 1973-12-14 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES411826A ES411826A1 (en) | 1973-02-20 | 1973-02-20 | Process for preparing pharmacologically active 1-aryloxy-2- propanolamines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES411826A1 true ES411826A1 (en) | 1976-01-01 |
Family
ID=8463472
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES411826A Expired ES411826A1 (en) | 1973-02-20 | 1973-02-20 | Process for preparing pharmacologically active 1-aryloxy-2- propanolamines |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE808066A (en) |
| DE (1) | DE2359926C3 (en) |
| ES (1) | ES411826A1 (en) |
| FR (1) | FR2218094B1 (en) |
| GB (1) | GB1441976A (en) |
| NL (1) | NL7317220A (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2623314C2 (en) * | 1976-05-25 | 1984-08-02 | Hoechst Ag, 6230 Frankfurt | 1-aryloxy-2-hydroxy-3-aminopropanes, processes for their preparation and pharmaceuticals containing them |
| DE2824764A1 (en) * | 1978-06-06 | 1979-12-20 | Hoechst Ag | NEW PYRIDYL PIPERAZINE DERIVATIVES AND PROCESS FOR THEIR PRODUCTION |
| EP0252007A3 (en) * | 1986-06-28 | 1989-07-05 | Ciba-Geigy Ag | 2-propanol derivatives as corrosion inhibitors |
| JP6196551B2 (en) * | 2010-04-12 | 2017-09-13 | スパーナス ファーマシューティカルズ インコーポレイテッド | Process for producing viloxazine salts and novel polymorphs thereof |
| FR3030514A1 (en) * | 2014-12-18 | 2016-06-24 | Centre De Coop Int En Rech Agronomique Pour Le Dev (Cirad) | POLYAROMATIC DIMERS |
| CZ309081B6 (en) * | 2019-11-21 | 2022-01-19 | Fakultní nemocnice Hradec Králové | 1-Aryloxy-3- (4- (2-hydroxyethyl) piperazin-1-yl) propan-2-oly, preparation process and use |
| CZ310541B6 (en) * | 2024-05-30 | 2025-11-05 | Fakultní nemocnice Hradec Králové | Derivatives of 1-(4-(2-hydroxyethyl)piperazin-1-yl)-3-phenoxypropan-2-ol, method of their preparation and their use |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3524851A (en) * | 1966-10-21 | 1970-08-18 | Merck & Co Inc | 1-phenoxy-3-morpholino alkylamino-2-propanols |
-
1973
- 1973-02-20 ES ES411826A patent/ES411826A1/en not_active Expired
- 1973-10-31 GB GB5057373A patent/GB1441976A/en not_active Expired
- 1973-11-27 FR FR7342192A patent/FR2218094B1/fr not_active Expired
- 1973-11-30 BE BE138389A patent/BE808066A/en unknown
- 1973-12-01 DE DE2359926A patent/DE2359926C3/en not_active Expired
- 1973-12-14 NL NL7317220A patent/NL7317220A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2359926C3 (en) | 1980-05-22 |
| FR2218094A1 (en) | 1974-09-13 |
| BE808066A (en) | 1974-03-15 |
| NL7317220A (en) | 1974-08-22 |
| DE2359926B2 (en) | 1979-08-23 |
| FR2218094B1 (en) | 1977-07-01 |
| GB1441976A (en) | 1976-07-07 |
| DE2359926A1 (en) | 1974-08-29 |
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