DD146749A3 - Verfahren zur herstellung von phenoxyalkanolamin-derivaten - Google Patents
Verfahren zur herstellung von phenoxyalkanolamin-derivaten Download PDFInfo
- Publication number
- DD146749A3 DD146749A3 DD77202331A DD20233177A DD146749A3 DD 146749 A3 DD146749 A3 DD 146749A3 DD 77202331 A DD77202331 A DD 77202331A DD 20233177 A DD20233177 A DD 20233177A DD 146749 A3 DD146749 A3 DD 146749A3
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- general formula
- radicals
- groups
- amino
- compounds
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 52
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 11
- 239000002253 acid Substances 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 7
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 5
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 4
- 150000007524 organic acids Chemical class 0.000 claims abstract description 4
- 235000005985 organic acids Nutrition 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 2
- 125000003277 amino group Chemical group 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 12
- 125000006239 protecting group Chemical group 0.000 claims description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- PARZURDQOGMVKY-UHFFFAOYSA-N 2,3-dibromopropoxybenzene Chemical compound BrCC(Br)COC1=CC=CC=C1 PARZURDQOGMVKY-UHFFFAOYSA-N 0.000 claims description 3
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims description 3
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 3
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 150000004985 diamines Chemical class 0.000 claims description 3
- JZEHWMUIAKALDN-UHFFFAOYSA-N 1-amino-3-phenoxypropan-2-ol Chemical compound NCC(O)COC1=CC=CC=C1 JZEHWMUIAKALDN-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 150000001541 aziridines Chemical class 0.000 claims description 2
- 125000004069 aziridinyl group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- KGYYLUNYOCBBME-UHFFFAOYSA-M 4-fluoro-2-phenyl-4-(4-propylcyclohexyl)cyclohexa-1,5-diene-1-carboxylate Chemical compound C1CC(CCC)CCC1C1(F)C=CC(C([O-])=O)=C(C=2C=CC=CC=2)C1 KGYYLUNYOCBBME-UHFFFAOYSA-M 0.000 abstract description 13
- 239000000150 Sympathomimetic Substances 0.000 abstract description 11
- 230000001975 sympathomimetic effect Effects 0.000 abstract description 8
- 229940064707 sympathomimetics Drugs 0.000 abstract description 8
- 239000005557 antagonist Substances 0.000 abstract description 3
- 239000000496 cardiotonic agent Substances 0.000 abstract description 2
- 230000003177 cardiotonic effect Effects 0.000 abstract description 2
- OCIDXARMXNJACB-UHFFFAOYSA-N n'-phenylethane-1,2-diamine Chemical class NCCNC1=CC=CC=C1 OCIDXARMXNJACB-UHFFFAOYSA-N 0.000 abstract description 2
- 101100072620 Streptomyces griseus ind2 gene Proteins 0.000 abstract 4
- 206010007556 Cardiac failure acute Diseases 0.000 abstract 1
- 206010007558 Cardiac failure chronic Diseases 0.000 abstract 1
- 230000001154 acute effect Effects 0.000 abstract 1
- 230000003389 potentiating effect Effects 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 28
- 238000002844 melting Methods 0.000 description 26
- 230000008018 melting Effects 0.000 description 26
- -1 alkyl radicals Chemical group 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 13
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- 239000000047 product Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 230000000747 cardiac effect Effects 0.000 description 5
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 230000003042 antagnostic effect Effects 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 4
- 229960001317 isoprenaline Drugs 0.000 description 4
- AFDBKKUOCNDDSN-UHFFFAOYSA-N 1-amino-1-phenoxypropan-2-ol Chemical compound CC(O)C(N)OC1=CC=CC=C1 AFDBKKUOCNDDSN-UHFFFAOYSA-N 0.000 description 3
- 241000700199 Cavia porcellus Species 0.000 description 3
- 230000001746 atrial effect Effects 0.000 description 3
- 230000001451 cardiotoxic effect Effects 0.000 description 3
- DSNYFFJTZPIKFZ-UHFFFAOYSA-N propoxybenzene Chemical compound CCCOC1=CC=CC=C1 DSNYFFJTZPIKFZ-UHFFFAOYSA-N 0.000 description 3
- 229960003712 propranolol Drugs 0.000 description 3
- 102000005962 receptors Human genes 0.000 description 3
- 108020003175 receptors Proteins 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 229940127230 sympathomimetic drug Drugs 0.000 description 3
- IEGUQOIJCDWHSG-UHFFFAOYSA-N 1-phenoxypropan-1-ol hydrochloride Chemical compound O(C1=CC=CC=C1)C(CC)O.Cl IEGUQOIJCDWHSG-UHFFFAOYSA-N 0.000 description 2
- SKQDKFOTIPJUSV-UHFFFAOYSA-N 4-[2-[[2-hydroxy-3-(2-methylphenoxy)propyl]amino]ethoxy]benzamide Chemical compound CC1=CC=CC=C1OCC(O)CNCCOC1=CC=C(C(N)=O)C=C1 SKQDKFOTIPJUSV-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- JRWZLRBJNMZMFE-UHFFFAOYSA-N Dobutamine Chemical compound C=1C=C(O)C(O)=CC=1CCNC(C)CCC1=CC=C(O)C=C1 JRWZLRBJNMZMFE-UHFFFAOYSA-N 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
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- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
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- 230000000903 blocking effect Effects 0.000 description 2
- 150000003943 catecholamines Chemical class 0.000 description 2
- 230000001186 cumulative effect Effects 0.000 description 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
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- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
- SZGKYGWSRRHUEA-UHFFFAOYSA-N 1-(aziridin-1-yl)-3-phenoxypropan-2-ol Chemical compound C1CN1CC(O)COC1=CC=CC=C1 SZGKYGWSRRHUEA-UHFFFAOYSA-N 0.000 description 1
- HCTDRZMGZRHFJV-UHFFFAOYSA-N 1-chloro-3-phenoxypropan-2-ol Chemical compound ClCC(O)COC1=CC=CC=C1 HCTDRZMGZRHFJV-UHFFFAOYSA-N 0.000 description 1
- YZZQBOZMOZKTGQ-UHFFFAOYSA-N 2,6-dichloro-n-(2-chloroethyl)aniline Chemical compound ClCCNC1=C(Cl)C=CC=C1Cl YZZQBOZMOZKTGQ-UHFFFAOYSA-N 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- JMUPNNYLJGSMPK-JPJJPTBZSA-N 3-[[(1r,2s)-1-hydroxy-1-phenylpropan-2-yl]amino]-1-(3-methoxyphenyl)propan-1-one;hydrochloride Chemical compound Cl.COC1=CC=CC(C(=O)CCN[C@@H](C)[C@H](O)C=2C=CC=CC=2)=C1 JMUPNNYLJGSMPK-JPJJPTBZSA-N 0.000 description 1
- HQARDVLSJLCFBA-UHFFFAOYSA-N 4-[(4-aminophenyl)carbamoyl]-1h-imidazole-5-carboxylic acid Chemical compound C1=CC(N)=CC=C1NC(=O)C1=C(C(O)=O)NC=N1 HQARDVLSJLCFBA-UHFFFAOYSA-N 0.000 description 1
- WUORSSYNZWHFQY-UHFFFAOYSA-N 4-[2-(methylamino)propyl]phenol;sulfuric acid Chemical compound OS(O)(=O)=O.CNC(C)CC1=CC=C(O)C=C1.CNC(C)CC1=CC=C(O)C=C1 WUORSSYNZWHFQY-UHFFFAOYSA-N 0.000 description 1
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- BALXUFOVQVENIU-GNAZCLTHSA-N Ephedrine hydrochloride Chemical compound Cl.CN[C@@H](C)[C@H](O)C1=CC=CC=C1 BALXUFOVQVENIU-GNAZCLTHSA-N 0.000 description 1
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- BYXYCUABYHCYLY-UHFFFAOYSA-N isoindole-1,3-dione;potassium Chemical compound [K].C1=CC=C2C(=O)NC(=O)C2=C1 BYXYCUABYHCYLY-UHFFFAOYSA-N 0.000 description 1
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- 238000003199 nucleic acid amplification method Methods 0.000 description 1
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- LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 description 1
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- 230000036581 peripheral resistance Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- 230000009090 positive inotropic effect Effects 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- POSICDHOUBKJKP-UHFFFAOYSA-N prop-2-enoxybenzene Chemical compound C=CCOC1=CC=CC=C1 POSICDHOUBKJKP-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- CXNGXKYCRQIQNZ-UHFFFAOYSA-N propoxybenzene hydrochloride Chemical compound Cl.O(CCC)C1=CC=CC=C1 CXNGXKYCRQIQNZ-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 230000002861 ventricular Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (19)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD77202331A DD146749A3 (de) | 1977-12-01 | 1977-12-01 | Verfahren zur herstellung von phenoxyalkanolamin-derivaten |
| AT730878A AT361904B (de) | 1977-12-01 | 1978-10-11 | Verfahren zur herstellung von neuen 3-anilino- aethylamino-2-hydroxy-1-phenoxypropanen sowie deren saeureadditionssalzen |
| DE2844497A DE2844497C2 (de) | 1977-12-01 | 1978-10-12 | Phenoxyalkanolamin-Derivate und Verfahren zu deren Herstellung |
| NL7810891A NL7810891A (nl) | 1977-12-01 | 1978-11-01 | Fenoxyalkanolaminederivaten en werkwijze ter bereiding daarvan. |
| BG7841339A BG33952A1 (en) | 1977-12-01 | 1978-11-09 | A method of obtaining derivatives of phenoxalkanolamine |
| GB7844545A GB2010261B (en) | 1977-12-01 | 1978-11-15 | Phenoxyalkanolamine derivatives the preparation thereof and pharmaceutical compositions containing them |
| DK520178A DK520178A (da) | 1977-12-01 | 1978-11-22 | Fremgangsmaade til fremstilling af phenoxyalkanolamin-derivater |
| RO7895753A RO76867A (fr) | 1977-12-01 | 1978-11-25 | Procede pour la preparation des derives de phenoxyalcanolamine |
| IT7852072A IT7852072A0 (it) | 1977-12-01 | 1978-11-27 | Procedimenti per la produzione di derivati della fenossialcanolamina |
| FR7833577A FR2410640A1 (fr) | 1977-12-01 | 1978-11-28 | Derives de phenoxyalcanolamines, leur preparation et leurs utilisations therapeutiques |
| BE191990A BE872342A (fr) | 1977-12-01 | 1978-11-28 | Phenoxy-alcanol-amines sympathicomimetiques et procedes pour leur preparation |
| PL1978211328A PL120540B1 (en) | 1977-12-01 | 1978-11-29 | Process for preparing novel derivatives of phenoxyalkanoloaminena |
| FI783655A FI783655A (fi) | 1977-12-01 | 1978-11-29 | Foerfarande foer framstaellning av fenoxialkanolaminderivat |
| SE7812371A SE7812371L (sv) | 1977-12-01 | 1978-11-30 | Forfarande for framstellning av fenoxialkanolaminderivat |
| ES475596A ES475596A1 (es) | 1977-12-01 | 1978-11-30 | Procedimiento para la preparacion de derivados de fenoxial- canolaminas |
| JP14896878A JPS5484540A (en) | 1977-12-01 | 1978-12-01 | Phenoxy alkanol amine derivatives and their manufacture |
| CA317,219A CA1095934A (fr) | 1977-12-01 | 1978-12-01 | Procede de production de derives de la phenoxy- alkanol-amine |
| AT0059280A AT368485B (de) | 1977-12-01 | 1980-02-04 | Verfahren zur herstellung von neuen 3-anilinoaethylamino-2-hydroxy-1-phenoxypropanen sowie deren saeureadditionssalzen |
| US06/133,128 US4356322A (en) | 1977-12-01 | 1980-03-24 | Phenoxyalkanolamine derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD77202331A DD146749A3 (de) | 1977-12-01 | 1977-12-01 | Verfahren zur herstellung von phenoxyalkanolamin-derivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD146749A3 true DD146749A3 (de) | 1981-03-04 |
Family
ID=5510642
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD77202331A DD146749A3 (de) | 1977-12-01 | 1977-12-01 | Verfahren zur herstellung von phenoxyalkanolamin-derivaten |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4356322A (fr) |
| JP (1) | JPS5484540A (fr) |
| AT (1) | AT361904B (fr) |
| BE (1) | BE872342A (fr) |
| BG (1) | BG33952A1 (fr) |
| CA (1) | CA1095934A (fr) |
| DD (1) | DD146749A3 (fr) |
| DE (1) | DE2844497C2 (fr) |
| DK (1) | DK520178A (fr) |
| ES (1) | ES475596A1 (fr) |
| FI (1) | FI783655A (fr) |
| FR (1) | FR2410640A1 (fr) |
| GB (1) | GB2010261B (fr) |
| IT (1) | IT7852072A0 (fr) |
| NL (1) | NL7810891A (fr) |
| PL (1) | PL120540B1 (fr) |
| RO (1) | RO76867A (fr) |
| SE (1) | SE7812371L (fr) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3023369A1 (de) * | 1980-06-23 | 1982-01-14 | Boehringer Mannheim Gmbh, 6800 Mannheim | Aryloxypropanolamine, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE3048487A1 (de) * | 1980-12-22 | 1982-07-29 | Cassella Ag, 6000 Frankfurt | Basisch substituierte pyridazine, ihre herstellung und ihre verwendung |
| DE3131146A1 (de) * | 1981-08-06 | 1983-02-24 | Boehringer Mannheim Gmbh, 6800 Mannheim | Neue heteroaryloxypropanolamine, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| US4556668A (en) * | 1983-07-15 | 1985-12-03 | American Hospital Supply Corporation | Ethylenediamine derivatives of aryloxypropanolamine aryl esters having various medicinal properties |
| DE3428525A1 (de) * | 1984-08-02 | 1986-02-13 | Boehringer Mannheim Gmbh, 6800 Mannheim | Verwendung von alkylendiamin-derivaten zur behandlung von durchblutungsstoerungen sowie arzneimittel, die diese verbindung enthalten |
| HUP9702411A2 (hu) * | 1997-12-11 | 2000-03-28 | Gyógyszerkutató Intézet Kft. | Fenoxi-alkil-amin-származékok és a vegyületeket tartalmazó antiaritmiás hatású gyógyszerkészítmények |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2817675A (en) * | 1951-12-07 | 1957-12-24 | Saul & Co | Basic condensation products containing nitrogen |
| US3637852A (en) * | 1963-08-26 | 1972-01-25 | Boehringer Sohn Ingelheim | 1-phenoxy-2-hydroxy-3-isopropylamino-propanes and salts thereof |
| CA957364A (en) * | 1968-11-18 | 1974-11-05 | Pfizer Corporation | Preparation of polar-substituted phenyl propanolamines |
| GB1395156A (en) * | 1971-07-28 | 1975-05-21 | Ici Ltd | Aldehyde derivatives |
| DE2339396C2 (de) * | 1973-08-03 | 1984-06-28 | Boehringer Mannheim Gmbh, 6800 Mannheim | N-substituierte 1-Amino-3-phenoxypropan-2-ole, deren Salze, Verfahren zu deren Herstellung sowie Arzneimittel, die diese Verbindungen enthalten |
| JPS5059339A (fr) * | 1973-09-28 | 1975-05-22 | ||
| US4041075A (en) * | 1973-12-12 | 1977-08-09 | Imperial Chemical Industries Limited | Phenoxy-alkanolamine derivatives |
-
1977
- 1977-12-01 DD DD77202331A patent/DD146749A3/de unknown
-
1978
- 1978-10-11 AT AT730878A patent/AT361904B/de not_active IP Right Cessation
- 1978-10-12 DE DE2844497A patent/DE2844497C2/de not_active Expired
- 1978-11-01 NL NL7810891A patent/NL7810891A/xx not_active Application Discontinuation
- 1978-11-09 BG BG7841339A patent/BG33952A1/xx unknown
- 1978-11-15 GB GB7844545A patent/GB2010261B/en not_active Expired
- 1978-11-22 DK DK520178A patent/DK520178A/da unknown
- 1978-11-25 RO RO7895753A patent/RO76867A/fr unknown
- 1978-11-27 IT IT7852072A patent/IT7852072A0/it unknown
- 1978-11-28 BE BE191990A patent/BE872342A/fr unknown
- 1978-11-28 FR FR7833577A patent/FR2410640A1/fr active Granted
- 1978-11-29 PL PL1978211328A patent/PL120540B1/pl unknown
- 1978-11-29 FI FI783655A patent/FI783655A/fi unknown
- 1978-11-30 SE SE7812371A patent/SE7812371L/xx unknown
- 1978-11-30 ES ES475596A patent/ES475596A1/es not_active Expired
- 1978-12-01 CA CA317,219A patent/CA1095934A/fr not_active Expired
- 1978-12-01 JP JP14896878A patent/JPS5484540A/ja active Pending
-
1980
- 1980-03-24 US US06/133,128 patent/US4356322A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE2844497C2 (de) | 1982-12-02 |
| US4356322A (en) | 1982-10-26 |
| DE2844497A1 (de) | 1979-06-07 |
| ATA730878A (de) | 1980-09-15 |
| RO76867A (fr) | 1981-08-30 |
| AT361904B (de) | 1981-04-10 |
| CA1095934A (fr) | 1981-02-17 |
| JPS5484540A (en) | 1979-07-05 |
| PL211328A1 (pl) | 1979-08-13 |
| IT7852072A0 (it) | 1978-11-27 |
| NL7810891A (nl) | 1979-06-06 |
| FR2410640B1 (fr) | 1980-08-29 |
| BE872342A (fr) | 1979-05-28 |
| BG33952A1 (en) | 1983-06-15 |
| GB2010261B (en) | 1982-02-17 |
| DK520178A (da) | 1979-06-02 |
| PL120540B1 (en) | 1982-03-31 |
| GB2010261A (en) | 1979-06-27 |
| FI783655A (fi) | 1979-06-02 |
| SE7812371L (sv) | 1979-06-02 |
| FR2410640A1 (fr) | 1979-06-29 |
| ES475596A1 (es) | 1979-12-01 |
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