DE1293782B - 1-(4-Hydroxyphenyl)-2-[2-(4-hydroxyphenyl)-aethylamino]-propanol, dessen physiologisch vertraeglichen Salze und Verfahren zu deren Herstellung - Google Patents
1-(4-Hydroxyphenyl)-2-[2-(4-hydroxyphenyl)-aethylamino]-propanol, dessen physiologisch vertraeglichen Salze und Verfahren zu deren HerstellungInfo
- Publication number
- DE1293782B DE1293782B DEN26270A DEN0026270A DE1293782B DE 1293782 B DE1293782 B DE 1293782B DE N26270 A DEN26270 A DE N26270A DE N0026270 A DEN0026270 A DE N0026270A DE 1293782 B DE1293782 B DE 1293782B
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- formula
- hydroxyphenyl
- amine
- salts
- 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.)
- Pending
Links
- 150000003839 salts Chemical class 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 3
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims 3
- 150000001875 compounds Chemical class 0.000 claims description 27
- 150000001412 amines Chemical class 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 150000004820 halides Chemical class 0.000 claims description 7
- 230000002829 reductive effect Effects 0.000 claims description 6
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 150000003335 secondary amines Chemical class 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 239000000243 solution Substances 0.000 description 18
- 230000000694 effects Effects 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 239000000047 product Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 238000006722 reduction reaction Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- -1 benzyloxy, diphenylmethoxy Chemical group 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- IOVGROKTTNBUGK-UHFFFAOYSA-N 4-[2-[[1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]phenol Chemical compound C=1C=C(O)C=CC=1C(O)C(C)NCCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-UHFFFAOYSA-N 0.000 description 5
- 230000003276 anti-hypertensive effect Effects 0.000 description 5
- 239000002585 base Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- JLTCWSBVQSZVLT-CDIPANDDSA-N (2s)-n-[(2s)-6-amino-1-[(2-amino-2-oxoethyl)amino]-1-oxohexan-2-yl]-1-[(4r,7s,10s,13s,16s,19r)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-benzyl-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosan Chemical compound NCCCC[C@@H](C(=O)NCC(N)=O)NC(=O)[C@@H]1CCCN1C(=O)[C@H]1NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@H](CC=2C=CC(O)=CC=2)NC(=O)[C@@H](N)CSSC1.C([C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@@H](C(N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N1)=O)N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(N)=O)C1=CC=CC=C1 JLTCWSBVQSZVLT-CDIPANDDSA-N 0.000 description 2
- LSQLSCUJBXFBRB-UHFFFAOYSA-N 2-bromo-1-(4-phenylmethoxyphenyl)propan-1-one Chemical compound C1=CC(C(=O)C(Br)C)=CC=C1OCC1=CC=CC=C1 LSQLSCUJBXFBRB-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- LTPVSOCPYWDIFU-UHFFFAOYSA-N 4-methoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1 LTPVSOCPYWDIFU-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 229910010082 LiAlH Inorganic materials 0.000 description 2
- 206010029350 Neurotoxicity Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 102000005320 Posterior Pituitary Hormones Human genes 0.000 description 2
- 108010070873 Posterior Pituitary Hormones Proteins 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 206010044221 Toxic encephalopathy Diseases 0.000 description 2
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 2
- 229960004373 acetylcholine Drugs 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 230000001813 broncholytic effect Effects 0.000 description 2
- 230000000572 bronchospasmolytic effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052987 metal hydride Inorganic materials 0.000 description 2
- 150000004681 metal hydrides Chemical class 0.000 description 2
- 231100000228 neurotoxicity Toxicity 0.000 description 2
- 230000007135 neurotoxicity Effects 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
- 238000005932 reductive alkylation reaction Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- WNCXDNZVUJLFPD-UHFFFAOYSA-N 1-(4-hydroxyphenyl)-2-[2-(4-hydroxyphenyl)ethylamino]propan-1-one Chemical compound C=1C=C(O)C=CC=1C(=O)C(C)NCCC1=CC=C(O)C=C1 WNCXDNZVUJLFPD-UHFFFAOYSA-N 0.000 description 1
- MKKMZZXGIORPMU-UHFFFAOYSA-N 2-(4-phenylmethoxyphenyl)ethanamine Chemical compound C1=CC(CCN)=CC=C1OCC1=CC=CC=C1 MKKMZZXGIORPMU-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- BMUKKTUHUDJSNZ-UHFFFAOYSA-N 4-[1-hydroxy-2-(1-phenoxypropan-2-ylamino)propyl]phenol Chemical compound C=1C=C(O)C=CC=1C(O)C(C)NC(C)COC1=CC=CC=C1 BMUKKTUHUDJSNZ-UHFFFAOYSA-N 0.000 description 1
- 229910000761 Aluminium amalgam Inorganic materials 0.000 description 1
- 101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 208000005171 Dysmenorrhea Diseases 0.000 description 1
- 206010013935 Dysmenorrhoea Diseases 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- CLJHABUMMDMAFA-UHFFFAOYSA-N Nylidrin hydrochloride Chemical compound [Cl-].C=1C=C(O)C=CC=1C(O)C(C)[NH2+]C(C)CCC1=CC=CC=C1 CLJHABUMMDMAFA-UHFFFAOYSA-N 0.000 description 1
- HXGGQRWKMAIQJK-UHFFFAOYSA-N OC1=CC=C(C=C1)C(C(C)NCCC1=CC=C(C=C1)OC)=O Chemical compound OC1=CC=C(C=C1)C(C(C)NCCC1=CC=C(C=C1)OC)=O HXGGQRWKMAIQJK-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 206010000210 abortion Diseases 0.000 description 1
- 231100000176 abortion Toxicity 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 229940124630 bronchodilator Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 229960004819 isoxsuprine Drugs 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 230000002101 lytic effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 231100000189 neurotoxic Toxicity 0.000 description 1
- 230000002887 neurotoxic effect Effects 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003506 spasmogen Substances 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/10—Mercury compounds
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL6401871A NL6401871A (hu) | 1964-02-27 | 1964-02-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1293782B true DE1293782B (de) | 1969-04-30 |
Family
ID=19789406
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEN26270A Pending DE1293782B (de) | 1964-02-27 | 1965-02-24 | 1-(4-Hydroxyphenyl)-2-[2-(4-hydroxyphenyl)-aethylamino]-propanol, dessen physiologisch vertraeglichen Salze und Verfahren zu deren Herstellung |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3410944A (hu) |
| AT (4) | AT261590B (hu) |
| BE (1) | BE660244A (hu) |
| BR (1) | BR6567446D0 (hu) |
| CH (3) | CH503692A (hu) |
| DE (1) | DE1293782B (hu) |
| DK (2) | DK118827B (hu) |
| ES (1) | ES309809A1 (hu) |
| FR (2) | FR1483718A (hu) |
| GB (1) | GB1111451A (hu) |
| NL (1) | NL6401871A (hu) |
| SE (1) | SE339481B (hu) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1962497C3 (de) * | 1969-12-12 | 1979-09-20 | C.H. Boehringer Sohn, 6507 Ingelheim | Naphthylalkyl- a -hydroxyphenäthyl-amine, ihre Herstellung und diese enthaltende Arzneimittel |
| US4704407A (en) * | 1984-12-20 | 1987-11-03 | Eli Lilly And Company | Soluble dobutamine salts |
| MY126489A (en) | 1998-07-08 | 2006-10-31 | Kissei Pharmaceutical | Phenoxyacetic acid derivatives and medicinal compositions containing the same |
| CN102060716A (zh) * | 2009-11-15 | 2011-05-18 | 海南中化联合制药工业股份有限公司 | 一种盐酸利托君的制备方法 |
| IT1399912B1 (it) | 2010-04-29 | 2013-05-09 | Lundbeck Pharmaceuticals Italy S Pa | Processo di preparazione di ritodrina cloridrato. |
| CN102976959B (zh) * | 2012-12-07 | 2014-06-04 | 许学农 | 利托君的制备方法 |
| WO2014108449A1 (en) | 2013-01-08 | 2014-07-17 | Atrogi Ab | A screening method, a kit, a method of treatment and a compound for use in a method of treatment |
| GB201714745D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
| GB201714734D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
| GB201714740D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
| GB201714736D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
| GB202205895D0 (en) | 2022-04-22 | 2022-06-08 | Atrogi Ab | New medical uses |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE612995A (fr) * | 1961-01-23 | 1962-07-23 | Philips Nv | Procédé de préparation d'un nouveau composé à activité optique |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL86359C (hu) * | ||||
| CA623286A (en) * | 1961-07-04 | N.V. Philips Gloeilampenfabrieken | Production of optically active 1-(3',4'-dihydroxyphenyl)-2-amino ethanols | |
| US2661373A (en) * | 1953-03-02 | 1953-12-01 | Kulz Ida | Certain amino alcohols and ketones |
| AT228786B (de) * | 1961-01-23 | 1963-08-12 | Philips Nv | Verfahren zur Herstellung des neuen (-)-Enantiomeren des 1-(p-Hydroxyphenyl)-2-(α-methyl- γ-phenyl-propylamino)-propanols-(1) und seiner Säureadditionssalze |
| US3250803A (en) * | 1961-07-06 | 1966-05-10 | Philips Corp | Method of manufacturing the individual racemates of n-(p-hydroxyphenylisopropyl) arterenol and products |
| NL302260A (hu) * | 1963-01-24 | 1900-01-01 |
-
1964
- 1964-02-27 NL NL6401871A patent/NL6401871A/xx unknown
-
1965
- 1965-02-24 AT AT161165A patent/AT261590B/de active
- 1965-02-24 BR BR167446/65A patent/BR6567446D0/pt unknown
- 1965-02-24 DE DEN26270A patent/DE1293782B/de active Pending
- 1965-02-24 CH CH1410368A patent/CH503692A/de not_active IP Right Cessation
- 1965-02-24 AT AT783867A patent/AT268252B/de active
- 1965-02-24 AT AT922766A patent/AT270618B/de active
- 1965-02-24 CH CH1410468A patent/CH539604A/de not_active IP Right Cessation
- 1965-02-24 DK DK95865AA patent/DK118827B/da unknown
- 1965-02-24 CH CH249665A patent/CH472368A/de not_active IP Right Cessation
- 1965-02-24 AT AT783767A patent/AT264502B/de active
- 1965-02-24 SE SE02385/65A patent/SE339481B/xx unknown
- 1965-02-25 BE BE660244A patent/BE660244A/xx unknown
- 1965-02-25 US US435344A patent/US3410944A/en not_active Expired - Lifetime
- 1965-02-25 GB GB8153/65A patent/GB1111451A/en not_active Expired
- 1965-02-25 ES ES0309809A patent/ES309809A1/es not_active Expired
- 1965-02-26 FR FR7240A patent/FR1483718A/fr not_active Expired
- 1965-05-24 FR FR18183A patent/FR4404M/fr not_active Expired
-
1966
- 1966-11-30 DK DK619266AA patent/DK116740B/da unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE612995A (fr) * | 1961-01-23 | 1962-07-23 | Philips Nv | Procédé de préparation d'un nouveau composé à activité optique |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1483718A (fr) | 1967-06-09 |
| CH539604A (de) | 1973-07-31 |
| AT264502B (de) | 1968-09-10 |
| BR6567446D0 (pt) | 1973-08-02 |
| AT268252B (de) | 1969-02-10 |
| GB1111451A (en) | 1968-04-24 |
| DK118827B (da) | 1970-10-12 |
| US3410944A (en) | 1968-11-12 |
| NL6401871A (hu) | 1965-08-30 |
| FR4404M (hu) | 1966-10-10 |
| ES309809A1 (es) | 1965-07-01 |
| AT261590B (de) | 1968-05-10 |
| CH472368A (de) | 1969-05-15 |
| BE660244A (hu) | 1965-08-25 |
| DK116740B (da) | 1970-02-09 |
| AT270618B (de) | 1969-05-12 |
| CH503692A (de) | 1971-02-28 |
| SE339481B (hu) | 1971-10-11 |
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