DE865315C - Process for the preparation of 3,5-Dioxyphenylaethanolaminen - Google Patents
Process for the preparation of 3,5-DioxyphenylaethanolaminenInfo
- Publication number
- DE865315C DE865315C DEC1020D DEC0001020D DE865315C DE 865315 C DE865315 C DE 865315C DE C1020 D DEC1020 D DE C1020D DE C0001020 D DEC0001020 D DE C0001020D DE 865315 C DE865315 C DE 865315C
- Authority
- DE
- Germany
- Prior art keywords
- hydrogen
- hydrogenation
- ether
- preparation
- resacetophenone
- 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
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 238000005984 hydrogenation reaction Methods 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 230000001476 alcoholic effect Effects 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 3
- -1 halogen ketones Chemical class 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- UIAFKZKHHVMJGS-UHFFFAOYSA-N 2,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1O UIAFKZKHHVMJGS-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 229940126601 medicinal product Drugs 0.000 description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000003916 acid precipitation Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229940114055 beta-resorcylic acid Drugs 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000010792 warming 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
- 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
-
- 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
- C07C213/08—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 not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von 3, 5-Dioxyphenyläthanolaminen Es wurde gefunden, daß man das bisher unbekannte 3, 5-Dioxyphenyläthanolamin oder seine Abkömmlinge der allgemeinen Formel worin R Wasserstoff oder Alkyl und R1 sowie R2 Wasserstoff oder aliphatische oder cycloaliphatische Kohlenwasserstoffreste bedeuten, nach für Synthesen des Adrenalins oder ähnlich gebauter Aminoalkohole bekannten Methoden, ausgehend von a-Halogenketonen der allgemeinen Formel worin X Wasserstoff oder einen leicht abspaltbaren Rest, wie Acyl oder Benzyl, und R Wasserstoff oder Alkyl bedeuten, herstellen kann. Diese noch unbekannten Halogenketone können beispielsweise nach einem im journ. of the American Chem. Soc., Bd. 46, S. a551ff. (19a4) beschriebenen Verfahren dargestellt werden. In an sich bekannter Weise können sie mit Aminen umgesetzt oder auch unmittelbar zusammen mit Aminen reduziert werden. Eine besonders elegante Überführung der angegebenen Halogenketone in die Norverbindungen (R1 und R2 = H) besteht in ihrer Umsetzung mit anorganischen Ariden und Reduktion der so erhaltenen Azidketone beispielsweise durch katalytische Hydrierung in Gegenwart von Säuren.Process for the preparation of 3,5-Dioxyphenyläthanolaminen It has been found that you can use the previously unknown 3, 5-Dioxyphenyläthanolamin or its derivatives of the general formula where R is hydrogen or alkyl and R1 and R2 are hydrogen or aliphatic or cycloaliphatic hydrocarbon radicals, according to methods known for syntheses of adrenaline or similarly constructed amino alcohols, starting from α-haloketones of the general formula wherein X is hydrogen or an easily cleavable radical, such as acyl or benzyl, and R is hydrogen or alkyl, can produce. These still unknown halogen ketones can, for example, after an im journ. of the American Chem. Soc., vol. 46, pp. a551ff. (19a4). In a manner known per se, they can be reacted with amines or else reduced directly together with amines. A particularly elegant conversion of the specified halogen ketones into the normal compounds (R1 and R2 = H) consists in their reaction with inorganic arides and reduction of the azide ketones thus obtained, for example by catalytic hydrogenation in the presence of acids.
.Die.- so. erhaltenen 3, 5-Dioxyphenyläthanolamine unterscheiden sich von dem bekannten Hormon Adrenalin und einer Anzahl ähnlich gebauter Aminoalkohole durch die Stellung der Oxygruppen im Phenylkern. Sie zeichnen sich bei gleichsinniger physiologischer Aktivität durch wesentlich höhere Beständigkeit aus. Während beispielsweise die außerordentliche Unbeständigkeit des Adrenalins für seine allgemeine Anwendbarkeit große technische Schwierigkeiten bereitet, es sehr rasch oxydativ zersetzt wird; nicht kochfest und auch peroral nicht wirksam ist, fallen diese Nachteile beim erfindungsgemäß hergestellten 3, 5-Dioxyphenyläthanoldimethylamin fort. Dessen größere Beständigkeit macht sich auch im Wirkungsverlauf innerhalb des Organismus vorteilhaft geltend..The.- so. 3, 5-Dioxyphenyläthanolamine obtained differ from the well-known hormone adrenaline and a number of similarly constructed amino alcohols by the position of the oxy groups in the phenyl nucleus. They stand out at like-minded physiological activity is characterized by significantly higher resistance. While for example the extraordinary volatility of adrenaline for its general applicability causes great technical difficulties, it is oxidatively decomposed very quickly; is not boil-proof and also not effective orally, these disadvantages fall with the invention produced 3, 5-Dioxyphenyläthanoldimethylamin continued. Its greater persistence is also beneficial in the course of action within the organism.
Die nach dem erfindungsgemäßen Verfahren hergestellten 3, 5-Dioxyphenyläthanolamine sollen als Heilmittel oder als Zwischenprodukte für die Herstellung von Heilmitteln, Farbstoffen oder Schädlingsbekämpfungsmitteln Verwendung finden.The 3, 5-dioxyphenylethanolamines prepared by the process according to the invention are intended as medicinal products or as intermediate products for the manufacture of medicinal products, Find dyes or pesticides use.
Beispiele i. 18,6 g o-)-Chlor-a-resacetophenon (Chlorrnethyl-3, 5-dioxyphenylketon), dargestellt aus dem Chlorid des a-Resorcylsäurediacetats nach dem im journ. Am. Soc. Bd. 46, S. 255iff. (i924) für ß-Resorcylsäure beschriebenen Verfahren vom Schmp. 1i7° werden in etwa 300 ccm Äther gelöst und mit 5o ccm etwa 25%igem ätherischem Dimethylamin versetzt. Es fällt sofort ein gelbes 01 aus, die Reaktionsmischung wird über Nacht bei gewöhnlicher Temperatur oder besser einige Tage im Eisschrank y aufbewahrt und der nach Abtrennen des Äthers verbleibende ölige Rückstand durch Verreiben mit Wasser und Absaugen als Kristallbrei gewonnen. Nach dem Trocknen wird er in Methanol gelöst, mit der berechneten Menge alkoholischer Salzsäure versetzt und mit Äther gefällt. Das so gewonnene Hydrochlorid läßt sich aus Methanol und Äther umkristallisieren und zeigt den Schmp.2io°. Die Base selbst ist schwer löslich in Wasser und organischen Lösungsmitteln und zeigt den Schmp.216 bis 2i8°. Eine Lösung von 23,i5 g des erhaltenen Hydrochlorids in Methanol wird in Gegenwart eines Palladium-Kohle-Katalysators bis zur Aufnahme von 1/1o Mol Wasserstoff hydriert. Das Filtrat wird im Vakuum zur Trockne gebracht, und das als Rückstand gewonneneN-Dimethylaminomethyl-3, 5-dioxyphenylcarbinol zeigt nach Umkristallisieren aus Methanol und Äther oder Chloroform den Schmp. i72 bis i73°.Examples i. 18.6 g of o -) - chloro-a-resacetophenone (chloromethyl-3, 5-dioxyphenyl ketone), prepared from the chloride of a-resorcyl acid diacetate according to the im journ. At the. Soc. Vol. 46, p. 255iff. (1924) processes described for β-resorcylic acid with a melting point of 17 ° are dissolved in about 300 cc of ether and 50 cc of about 25% ethereal dimethylamine are added. A yellow oil precipitated immediately, the reaction mixture was stored overnight at normal temperature or, better, for a few days in the refrigerator and the oily residue remaining after the ether had been separated off was obtained as a slurry of crystals by trituration with water and suction. After drying, it is dissolved in methanol, mixed with the calculated amount of alcoholic hydrochloric acid and precipitated with ether. The hydrochloride obtained in this way can be recrystallized from methanol and ether and has a melting point of 2io °. The base itself is sparingly soluble in water and organic solvents and has a melting point of 216 to 218 °. A solution of 23.15 g of the hydrochloride obtained in methanol is hydrogenated in the presence of a palladium-carbon catalyst until 1/10 mol of hydrogen is absorbed. The filtrate is brought to dryness in vacuo, and the N-dimethylaminomethyl-3, 5-dioxyphenylcarbinol obtained as residue has a melting point of 172 ° to 173 ° after recrystallization from methanol and ether or chloroform.
Das gleiche Endprodukt erhält man bei gleichartiger Umsetzung von co-Chloraceto-a-resacetophenondiacetat.The same end product is obtained with a similar implementation of co-chloroaceto-a-resacetophenone diacetate.
2. 18,6 g co-Chlor-a-resacetophexlon werden in etwa 40 bis 50 cm3 absolutem Alkohol gelöst und mit einem Überschuß von Methylamin in absolutem Alkohol vermischt. Nach mehrstündigem Stehen erhält man durch Behandeln der rotbraunen alkoholischen Lösung mit Äther und Einleiten von Kohlensäure zur Fällung des überschüssigen Methylamins mittels ätherischer Salzsäure das Hydrochlorid des w-Methylamino-a-resacetophenons, dessen Menge durch Aufarbeiten der Kohlensäurefällung noch vermehrt werden kann und das nach dem Umkristallisieren aus Methanol und Äther bei 235 bis 237° schmilzt. Durch Hydrierung entsprechend dem Beispiel i bis zur Aufnahme von i Mol Wasserstoff wird N-Methylaminomethyl-3, 5-dioxyphenylcarbinol erhalten, dessen Hydrochlorid nach Umkristallisieren aus Methanol und Chloroform den Schmp. 145 bis i46° zeigt.2. 18.6 g of co-chloro-a-resacetophexlone are dissolved in about 40 to 50 cm3 of absolute alcohol and mixed with an excess of methylamine in absolute alcohol. After standing for several hours, treating the red-brown alcoholic solution with ether and introducing carbonic acid to precipitate the excess methylamine by means of ethereal hydrochloric acid gives the hydrochloride of w-methylamino-a-resacetophenone, the amount of which can be increased by working up the carbonic acid precipitation and that after Recrystallization from methanol and ether at 235 to 237 ° melts. By hydrogenation according to Example i until i mole of hydrogen is absorbed, N-methylaminomethyl-3,5-dioxyphenylcarbinol is obtained, the hydrochloride of which, after recrystallization from methanol and chloroform, has a melting point of 145 ° to 146 °.
3. Durch Umsetzung von a)-Chlor-a-resacetophenon mit Methylbenzylamin in der im Beispiel 2 angegebenen Weise und Hydrierung des erhaltenen N-Benzyl-N-methylamino-a-resacetophenons, dessen Hydrochlorid den Schmp.225° (unter Zersetzung) zeigt, in alkoholischer Lösung bis zur Aufnahme von 2 Mol Wasserstoff, entsteht N-Benzyl-N-methylaminomethyl-3, 5-dioxyphenylcarbinol.3. By reacting a) -chloro-a-resacetophenone with methylbenzylamine in the manner indicated in Example 2 and hydrogenation of the N-benzyl-N-methylamino-a-resacetophenone obtained, the hydrochloride of which has a melting point of 225 ° (with decomposition) in alcoholic solution until 2 moles of hydrogen are absorbed, N-benzyl-N-methylaminomethyl-3 is formed, 5-dioxyphenylcarbinol.
4. Durch Umsetzung von oo-Halogen-a-resacetophenon in wäßrig-methanolischer Lösung mit Natriumazid erhält man a)-Azido-a-resacetophenon vom Schmp. 84 bis 85°. 19,3 g (1/1o Mol) davon werden in alkoholischer Lösung in Gegenwart eines Palladium-Kohle- oder Platinoxyd-Katalysators etwa 1/2 Stunde mit Wasserstoff behandelt. Es tritt sogleich eine merkbare Erwärmung ein. Die Hydrierung wird nach Verbrauch von 2 Mol Wasserstoff beendet, das Filtrat vom Katalysator im Vakuum zur Trockne gebracht und der Rückstand, der Aminomethyl-3, 5-dioxyphenylcarbinol darstellt, aus Alkohol und Äther umkristallisiert. Bricht man die Hydrierung ab, sobald eine meßbare Wasserstoffaufnahme einzutreten beginnt, so erhält man durch Fällung des Filtrates vom Katalysator nach Zugabe von etwa 1/loMol absolut alkoholischer Salzsäure mit Äther in nahezu quantitativer Ausbeute co-Amino-a-resacetophenon als Hydrochlorid vom Schmp. 2q.6 bis 248°, dessen Hydrierung ebenfalls das angegebene Carbinol liefert. In einer geschlossenen Apparatur ist der für die Hydrierung zu dem Aminoketon aufgenommene Wasserstoff nicht mehr meßbar, weil gleichzeitig i Mol Stickstoff frei wird. Erst nach dieser Reduktion tritt durch Verbrauch zur Hydrierung der dann einsetzenden CO-Gruppenreduktion zu C H O H ein meßbarer Verbrauch ein.4. By converting oo-halogen-a-resacetophenone in aqueous methanolic A solution with sodium azide gives a) -azido-a-resacetophenone with a melting point of 84 ° to 85 °. 19.3 g (1 / 1o mol) of it are in alcoholic solution in the presence of a palladium-carbon or platinum oxide catalyst treated with hydrogen for about 1/2 hour. It kicks immediately a noticeable warming. The hydrogenation is after consumption of 2 mol Hydrogen terminated, the filtrate brought to dryness from the catalyst in vacuo and the residue, which is aminomethyl-3, 5-dioxyphenylcarbinol, from alcohol and ether recrystallized. If the hydrogenation is stopped as soon as there is measurable hydrogen uptake begins to occur, it is obtained by precipitation of the filtrate from the catalyst Addition of about 1/10 mol of absolutely alcoholic hydrochloric acid with ether in an almost quantitative manner Yield of co-amino-a-resacetophenone as hydrochloride with a melting point of 2q.6 to 248 °, its Hydrogenation also provides the specified carbinol. In a closed apparatus the hydrogen taken up for the hydrogenation to the aminoketone is no longer measurable because at the same time 1 mole of nitrogen is released. Only after this reduction occurs through consumption for hydrogenation of the then onset of CO group reduction C H O H a measurable consumption.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC1020D DE865315C (en) | 1943-07-27 | 1943-07-27 | Process for the preparation of 3,5-Dioxyphenylaethanolaminen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC1020D DE865315C (en) | 1943-07-27 | 1943-07-27 | Process for the preparation of 3,5-Dioxyphenylaethanolaminen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE865315C true DE865315C (en) | 1953-02-02 |
Family
ID=7012487
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC1020D Expired DE865315C (en) | 1943-07-27 | 1943-07-27 | Process for the preparation of 3,5-Dioxyphenylaethanolaminen |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE865315C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3341594A (en) * | 1960-02-15 | 1967-09-12 | Boehringer Sohn Ingelheim | 1-(3, 5-dihydroxy-phenyl)-1-hydroxy-2-isopropylamino-ethane and salts thereof |
| FR2038102A1 (en) * | 1969-04-01 | 1971-01-08 | Draco Ab |
-
1943
- 1943-07-27 DE DEC1020D patent/DE865315C/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3341594A (en) * | 1960-02-15 | 1967-09-12 | Boehringer Sohn Ingelheim | 1-(3, 5-dihydroxy-phenyl)-1-hydroxy-2-isopropylamino-ethane and salts thereof |
| DE1275069B (en) * | 1960-02-15 | 1968-08-14 | Boehringer Sohn Ingelheim | 1- (3 ', 5'-dihydroxyphenyl) -1-hydroxy-2-isopropylaminoalkanes and processes for their preparation |
| US3422196A (en) * | 1960-02-15 | 1969-01-14 | Boehringer Sohn Ingelheim | Utilizing 1 - (3,5 - dihydroxyphenyl)-1-hydroxy - 2 - isopropylaminoethane and salts thereof in the treatment of bronchial spasms |
| FR2038102A1 (en) * | 1969-04-01 | 1971-01-08 | Draco Ab |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DD297806A5 (en) | PROCESS FOR PREPARING N-METHYL-3- (P-TRIFLUOROMETHYLPHENOXY) -3-PHENYLPROPYLAMINE | |
| DE1194418B (en) | Process for the production of new dihalogenamino-benzylamines or their acid addition salts with physiologically compatible acids | |
| DE1568277A1 (en) | Process for the preparation of new, optically active phenylisopylamine derivatives | |
| CH542201A (en) | Indoline derivs derived from dopa - having hypotensive antipyretic and antiparkinson properties | |
| DE865315C (en) | Process for the preparation of 3,5-Dioxyphenylaethanolaminen | |
| DE1300955B (en) | p-Chlorophenoxyacetic acid (beta-dimethylaminoaethyl) ester, its hydrochloride and process for their preparation | |
| DE1056139B (en) | Process for the preparation of alpha-amino-beta-oxy-carboxylic acid anilides | |
| DE964057C (en) | Process for the preparation of ª ‰ -oxybutyric acid-p-phenetidide | |
| DE1793693C3 (en) | ||
| DE1493960C3 (en) | 2- (3'-tert-Butyl-4'-hydroxy-5'methyl-phenyl) -2-hydroxy-ethylamine, its physiologically acceptable acid addition salts and process for their preparation | |
| DE946058C (en) | Process for the preparation of 3-aminoindanes | |
| DE900699C (en) | Process for the preparation of N-alkyl- and N-aralkyl-1- (p-oxyphenyl) -2-aminobutanol-1 | |
| DE568759C (en) | Process for the preparation of 2-methyl-5-oxypiperidine | |
| DE954155C (en) | Process for the preparation of 4-aminochromans | |
| DE963517C (en) | Process for the preparation of antipyretic and analgesic effective, basic substituted phenyldimethylpyrazolone derivatives | |
| DE588880C (en) | Process for the preparation of 1-phenyl-2-aminopropanolen- (1) in racemic form | |
| DE653259C (en) | Process for the preparation of nitro-1,2-diaminobenzenes | |
| DE925474C (en) | Process for the preparation of aminoacetal | |
| DE670968C (en) | Process for the preparation of 2-alkylhexahydrobenzothiazoles and 2-alkylhexahydrobenzoselenazoles | |
| DE951628C (en) | Process for the preparation of 3-aminoindanes | |
| DE945244C (en) | Process for the preparation of N-alkyl- and N-aralkyl-1- (m-oxyphenyl) -2-aminobutanols-1 | |
| AT142359B (en) | Process for the production of hydrogenation products of the follicular hormones obtained from animal or vegetable material or synthetically. | |
| DE555240C (en) | Process for the preparation of pyridine and piperidine alkines | |
| DE942513C (en) | Process for the preparation of therapeutically active 1- (3 ', 4'-dioxyphenyl) -1-oxo- or -1-oxy-2-aralkylaminopropanes | |
| DE494508C (en) | Process for the preparation of a condensation product from m-cresol and acetone |