GB1441976A - Process for preparing pharmacologically active 1-aryloxy-2- propanolamines - Google Patents
Process for preparing pharmacologically active 1-aryloxy-2- propanolaminesInfo
- Publication number
- GB1441976A GB1441976A GB5057373A GB5057373A GB1441976A GB 1441976 A GB1441976 A GB 1441976A GB 5057373 A GB5057373 A GB 5057373A GB 5057373 A GB5057373 A GB 5057373A GB 1441976 A GB1441976 A GB 1441976A
- Authority
- GB
- United Kingdom
- Prior art keywords
- reacting
- hours
- propanolamines
- aryloxy
- pharmacologically active
- 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- 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
- 150000001875 compounds Chemical class 0.000 abstract 2
- JZEHWMUIAKALDN-UHFFFAOYSA-N 1-amino-3-phenoxypropan-2-ol Chemical class NCC(O)COC1=CC=CC=C1 JZEHWMUIAKALDN-UHFFFAOYSA-N 0.000 abstract 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 abstract 1
- 239000000674 adrenergic antagonist Substances 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group 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
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 150000003839 salts Chemical class 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
1441976 Aryloxypropanolamines LABORATORIOS LIADE SA 31 Oct 1973 [20 Feb 1973] 50573/73 Heading C2C 3 - Phenoxy - 2 - hydroxypropylamine salts in which the benzene ring and amino group may be mono- or disubstituted (including compounds in which the nitrogen atom forms part of a heterocyclic group) are prepared by reacting the appropriate phenol with epichlorohydrin in the presence of a catalyst at 70-100‹ C. for 10-20 hours, treating the reaction mixture with sodium hydroxide solution for 24 hours, extracting with chloroform, isolating the phenoxymethyloxirane and reacting it with ammonia or the appropriate amine in ethanol or tetrahydrofuran, followed by salt formation. These compounds are (3-adrenergic blocking agents.
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 |
|---|---|
| GB1441976A true GB1441976A (en) | 1976-07-07 |
Family
ID=8463472
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5057373A Expired GB1441976A (en) | 1973-02-20 | 1973-10-31 | 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) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4892671A (en) * | 1986-06-28 | 1990-01-09 | Ciba-Geigy Corporation | 2-Propanol derivatives as corrosion inhibitors |
| 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 |
Families Citing this family (4)
| 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 |
| CA2992219A1 (en) * | 2010-04-12 | 2011-10-20 | Supernus Pharmaceuticals Inc. | Methods 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 |
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
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4892671A (en) * | 1986-06-28 | 1990-01-09 | Ciba-Geigy Corporation | 2-Propanol derivatives as corrosion inhibitors |
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2359926B2 (en) | 1979-08-23 |
| DE2359926C3 (en) | 1980-05-22 |
| ES411826A1 (en) | 1976-01-01 |
| FR2218094A1 (en) | 1974-09-13 |
| NL7317220A (en) | 1974-08-22 |
| FR2218094B1 (en) | 1977-07-01 |
| BE808066A (en) | 1974-03-15 |
| DE2359926A1 (en) | 1974-08-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |