CS208486B2 - Method of making the new derivatives of the alcanolamines - Google Patents
Method of making the new derivatives of the alcanolamines Download PDFInfo
- Publication number
- CS208486B2 CS208486B2 CS79886A CS88679A CS208486B2 CS 208486 B2 CS208486 B2 CS 208486B2 CS 79886 A CS79886 A CS 79886A CS 88679 A CS88679 A CS 88679A CS 208486 B2 CS208486 B2 CS 208486B2
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- Czechoslovakia
- Prior art keywords
- methyl
- compound
- threo
- mixture
- solution
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- 238000000034 method Methods 0.000 claims abstract description 19
- 239000002253 acid Substances 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 239000012458 free base Substances 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
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- 125000004429 atom Chemical group 0.000 claims 1
- 235000013522 vodka Nutrition 0.000 claims 1
- 230000000903 blocking effect Effects 0.000 abstract description 14
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 3
- QIQKBOLIZIVUOV-UHFFFAOYSA-N 3-amino-1-(1,2,3,4-tetrahydronaphthalen-1-yloxy)butan-2-ol Chemical class C1=CC=C2C(OCC(O)C(N)C)CCCC2=C1 QIQKBOLIZIVUOV-UHFFFAOYSA-N 0.000 abstract 1
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- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- BTSIZIIPFNVMHF-UHFFFAOYSA-N nor-leaf alcohol Natural products CCC=CCO BTSIZIIPFNVMHF-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229960005489 paracetamol Drugs 0.000 description 1
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- 229960002695 phenobarbital Drugs 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- DURULFYMVIFBIR-UHFFFAOYSA-N practolol Chemical compound CC(C)NCC(O)COC1=CC=C(NC(C)=O)C=C1 DURULFYMVIFBIR-UHFFFAOYSA-N 0.000 description 1
- 229960001749 practolol Drugs 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical group CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 150000003335 secondary amines Chemical group 0.000 description 1
- 231100000161 signs of toxicity Toxicity 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- C07D303/08—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB504278 | 1978-02-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS208486B2 true CS208486B2 (en) | 1981-09-15 |
Family
ID=9788658
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS79886A CS208486B2 (en) | 1978-02-08 | 1979-02-08 | Method of making the new derivatives of the alcanolamines |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4275058A (en, 2012) |
| EP (1) | EP0003664B1 (en, 2012) |
| JP (1) | JPS54115359A (en, 2012) |
| AU (1) | AU527044B2 (en, 2012) |
| CA (1) | CA1123458A (en, 2012) |
| CS (1) | CS208486B2 (en, 2012) |
| DE (1) | DE2962112D1 (en, 2012) |
| DK (1) | DK53079A (en, 2012) |
| ES (1) | ES477562A1 (en, 2012) |
| GR (1) | GR71462B (en, 2012) |
| HK (1) | HK45385A (en, 2012) |
| IE (1) | IE48065B1 (en, 2012) |
| IL (1) | IL56702A (en, 2012) |
| IN (1) | IN150570B (en, 2012) |
| IT (1) | IT1110540B (en, 2012) |
| NO (1) | NO146356C (en, 2012) |
| NZ (1) | NZ189603A (en, 2012) |
| PT (1) | PT69201A (en, 2012) |
| ZA (1) | ZA79508B (en, 2012) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4463190A (en) * | 1977-07-05 | 1984-07-31 | A. H. Robins Company, Inc. | 1-Aryloxy-4-amino-2-butanols |
| US4469706A (en) * | 1980-11-07 | 1984-09-04 | Massachusetts General Hospital | Selective beta-2 adrenergic antagonists for the treatment of glaucoma |
| FR2507181A1 (fr) | 1981-06-05 | 1982-12-10 | Sanofi Sa | Nouveaux ethers de phenol actifs sur le systeme cardiovasculaire, leur procede de preparation et leur utilisation dans des medicaments |
| US4455317A (en) * | 1981-06-23 | 1984-06-19 | American Hospital Supply Corporation | Method for treating glaucoma by the topical administration of selectively metabolized beta-blocking agents |
| US4402974A (en) * | 1981-06-23 | 1983-09-06 | American Hospital Supply Corporation | Method for treating glaucoma by the topical administration of selectively metabolized beta-blocking agents |
| US4454154A (en) * | 1981-06-23 | 1984-06-12 | American Hospital Supply Corporation | Method for treating glaucoma by the topical administration of selectively metabolized beta-blocking agents |
| DE3248835A1 (de) * | 1981-06-23 | 1983-06-30 | American Hospital Supply Corp | Zusammensetzungen fuer die behandlung von glaukom |
| US4559359A (en) * | 1981-06-23 | 1985-12-17 | American Hospital Supply Corporation | Method for treating glaucoma by the topical administration of selectively metabolized beta-blocking agents |
| US4501912A (en) * | 1981-06-23 | 1985-02-26 | American Hospital Supply Corporation | Method for treating glaucoma by the topical administration of selectively metabolized beta-blocking agents |
| US4578403A (en) * | 1981-06-23 | 1986-03-25 | American Hospital Supply Corporation | Method for treating glaucoma by the topical administration of selectively metabolized beta-blocking agents |
| GB8419357D0 (en) * | 1984-07-30 | 1984-09-05 | Ici Plc | Alkanolamine derivatives |
| GB202217505D0 (en) | 2022-11-23 | 2023-01-04 | Trio Medicines Ltd | Selective beta2-adrencoceptor antagonist |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL300886A (en, 2012) * | 1962-11-23 | |||
| NL301580A (en, 2012) * | 1962-12-11 | |||
| GB1023214A (en) * | 1962-12-17 | 1966-03-23 | Ici Ltd | Carbocyclic hydroxyamines |
| ES330705A1 (es) * | 1965-09-01 | 1967-10-01 | Boehringer Sohn Ingelheim | Procedimiento para la preparacion de nuevos ariloxi-2-hidroxi-3-aminopropanos sustituidos |
| US3534085A (en) * | 1968-10-16 | 1970-10-13 | Squibb & Sons Inc | 5,8-dihydronaphthloxy-aminopropanols and related compounds |
| DE1955229C3 (de) * | 1968-11-12 | 1978-12-21 | Yamanouchi Pharmaceutical Co., Ltd., Tokio | 1 -(Indenyl-7-oxy)-3-alkyIamino-2propanole, deren Herstellungsverfahren und Arzneimittel auf deren Basis |
| US4127675A (en) * | 1968-11-12 | 1978-11-28 | Yamanouchi Pharmaceutical Co., Ltd. | 4-(Alkylamino-2-hydroxypropoxy)-indenes and method of use |
| US3646066A (en) * | 1970-03-25 | 1972-02-29 | Squibb & Sons Inc | Adamantylamino-tetrahydronaphthyl-oxypropanols and ester derivatives |
| US4029676A (en) * | 1971-12-01 | 1977-06-14 | E. R. Squibb & Sons, Inc. | Esters of tetrahydronaphthyloxy-aminopropanols |
| DE2333846A1 (de) * | 1972-07-03 | 1974-01-24 | Squibb & Sons Inc | Aminopropanolderivate, ihre salze, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| CA994351A (en) * | 1973-01-11 | 1976-08-03 | E.R. Squibb And Sons | Tetrahydronaphthyloxy-amines and related compounds |
| JPS5134915B2 (en, 2012) * | 1974-07-27 | 1976-09-29 | ||
| US4048231A (en) * | 1976-02-09 | 1977-09-13 | E. R. Squibb & Sons, Inc. | 4-[3-(Substituted amino)-2-hydroxypropoxy]-5,6,7,8-tetrahydro-1,6,7-naphthalenetriols |
| US4017085A (en) * | 1976-02-27 | 1977-04-12 | Charles Stephen Maxwell | Golf game |
-
1979
- 1979-02-02 EP EP79300169A patent/EP0003664B1/en not_active Expired
- 1979-02-02 DE DE7979300169T patent/DE2962112D1/de not_active Expired
- 1979-02-05 US US06/009,362 patent/US4275058A/en not_active Expired - Lifetime
- 1979-02-06 ZA ZA79508A patent/ZA79508B/xx unknown
- 1979-02-06 IE IE219/79A patent/IE48065B1/en unknown
- 1979-02-07 GR GR58289A patent/GR71462B/el unknown
- 1979-02-07 IN IN88/DEL/79A patent/IN150570B/en unknown
- 1979-02-07 NO NO790394A patent/NO146356C/no unknown
- 1979-02-08 PT PT7969201A patent/PT69201A/pt unknown
- 1979-02-08 CA CA321,086A patent/CA1123458A/en not_active Expired
- 1979-02-08 AU AU44093/79A patent/AU527044B2/en not_active Ceased
- 1979-02-08 IT IT20030/79A patent/IT1110540B/it active
- 1979-02-08 ES ES477562A patent/ES477562A1/es not_active Expired
- 1979-02-08 JP JP1283879A patent/JPS54115359A/ja active Granted
- 1979-02-08 DK DK53079A patent/DK53079A/da not_active Application Discontinuation
- 1979-02-08 NZ NZ189603A patent/NZ189603A/en unknown
- 1979-02-08 CS CS79886A patent/CS208486B2/cs unknown
- 1979-02-20 IL IL56702A patent/IL56702A/xx unknown
-
1985
- 1985-06-13 HK HK453/85A patent/HK45385A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU4409379A (en) | 1979-08-16 |
| IE790219L (en) | 1979-08-08 |
| IN150570B (en, 2012) | 1982-11-13 |
| GR71462B (en, 2012) | 1983-05-30 |
| JPS6326099B2 (en, 2012) | 1988-05-27 |
| JPS54115359A (en) | 1979-09-07 |
| NO790394L (no) | 1979-08-09 |
| DE2962112D1 (en) | 1982-03-25 |
| IL56702A (en) | 1982-12-31 |
| EP0003664B1 (en) | 1982-02-17 |
| AU527044B2 (en) | 1983-02-10 |
| HK45385A (en) | 1985-06-21 |
| IE48065B1 (en) | 1984-09-19 |
| IL56702A0 (en) | 1979-05-31 |
| EP0003664A1 (en) | 1979-08-22 |
| IT1110540B (it) | 1985-12-23 |
| NO146356C (no) | 1982-09-15 |
| NZ189603A (en) | 1984-07-06 |
| NO146356B (no) | 1982-06-07 |
| ES477562A1 (es) | 1979-10-16 |
| CA1123458A (en) | 1982-05-11 |
| ZA79508B (en) | 1980-02-27 |
| US4275058A (en) | 1981-06-23 |
| DK53079A (da) | 1979-08-09 |
| PT69201A (en) | 1979-03-01 |
| IT7920030A0 (it) | 1979-02-08 |
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