CH475191A - Process for the production of new unsaturated amines - Google Patents
Process for the production of new unsaturated aminesInfo
- Publication number
- CH475191A CH475191A CH170668A CH170668A CH475191A CH 475191 A CH475191 A CH 475191A CH 170668 A CH170668 A CH 170668A CH 170668 A CH170668 A CH 170668A CH 475191 A CH475191 A CH 475191A
- Authority
- CH
- Switzerland
- Prior art keywords
- alk
- isopropylamino
- radical
- salts
- phenoxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- 150000001412 amines Chemical class 0.000 title description 2
- 150000003839 salts Chemical class 0.000 claims description 14
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000001294 propane Substances 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 230000001419 dependent effect Effects 0.000 claims 4
- -1 alkylene radical Chemical class 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- UWYVPFMHMJIBHE-OWOJBTEDSA-N (e)-2-hydroxybut-2-enedioic acid Chemical compound OC(=O)\C=C(\O)C(O)=O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
- QXQAPNSHUJORMC-UHFFFAOYSA-N 1-chloro-4-propylbenzene Chemical compound CCCC1=CC=C(Cl)C=C1 QXQAPNSHUJORMC-UHFFFAOYSA-N 0.000 description 1
- FZKCAHQKNJXICB-UHFFFAOYSA-N 2,1-benzoxazole Chemical compound C1=CC=CC2=CON=C21 FZKCAHQKNJXICB-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229960004909 aminosalicylic acid Drugs 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- WXBLLCUINBKULX-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 WXBLLCUINBKULX-UHFFFAOYSA-N 0.000 description 1
- 102000012740 beta Adrenergic Receptors Human genes 0.000 description 1
- 108010079452 beta Adrenergic Receptors Proteins 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000005586 carbonic acid group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 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
- C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur HersteJlung neuer ungesättigter Amine
Gegenstand der Erfindung ist ein Verfahren zur Herstellung von 1 -Isopropylamino-2-hydroxy-3-[o-(R- alk-O)-phenoxyj-propanen der Formel
EMI1.1
worin alk einen Alkylenrest und R einen ungesättigten aliphatischen Kohlenwasserstoffrest darstellt, wobei alk und R zusammen mindestens 4 C-Atome besitzen, oder ihren Salzen.
Der Alkylenrest ist insbesondere ein Niederalkylenrest mit 1-3 C-Atomen.
Der Rest R ist vor allem ein in beliebiger Stellung verbundener Propenyl- oder gerader oder verzweigter Butenyl-, Pentenyl- oder Hexenylrest oder ein entsprechender Rest mit Dreifachbindung.
Die neuen Verbindungen besitzen wertvolle pharmakologische Eigenschaften. Insbesondere bewirken sie eine Hemmung adrenergischer ss-Rezeptoren. Sie können dementsprechend bei Herz- und Kreislauferkrankungen als Medikament angewendet werden.
Besonders wertvoll ist das 1-Isopropylamino-2 hydroxy-3-(o-methallyloxy-phenoxy)-propan der Formel
EMI1.2
Das erfindungsgemässe Verfahren zur Herstellung der neuen Verbindungen ist dadurch gekennzeichnet, dass man aus einem gegebenenfalls in Salzform vorliegenden 1-Isopropylamino-2-oxy-3-[o-(R-alk-O)-phenoxy]-propan, worin alk und R die oben gegebenen Bedeutungen haben, das am Stickstoffatom und an der 2-Oxygruppe je einen einwertigen oder zusammen einen zweiwertigen, durch Hydrolyse abspaltbaren Rest aufweist, diese Reste abspaltet. Einwertige derartige Reste sind z. B. Acylreste von Carbonsäuren, wie niedere Alkanoylreste, z. B. der Acetylrest, oder der einwertige Kohlensäurerest, der auch in Form seines Halbesters, z. B. als Benzyloxycarbonylrest oder tert.-Butoxycarbonylrest, vorliegen kann.
Zweiwertige derartige Reste sind insbesondere der zweiwertige Kohlensäurerest, wie dies z. B. im 5-[o-(R-alk-O)-Phenoxy]-3-isopropyl-oxa- zolidon-2 der Fall ist. Die Hydrolyse wird in üblicher Weise ausgeführt.
Die Ausgangsstoffe sind bekannt oder können nach an sich bekannten Methoden gewonnen werden.
Die Salze der Endstoffe können in an sich bekannter Weise, z. B. mit Alkalien oder Ionenaustauschern, in die freien Basen übergeführt werden. Von der letzteren lassen sich durch Umsetzung mit organischen oder anorganischen Säuren, insbesondere solchen, die zur Bildung von therapeutisch verwendbaren Salzen geeignet sind, Salze gewinnen.
Als solche Säuren seien beispielsweise genannt: Halogenwasserstoffsäuren, Schwefelsäuren, Phosphorsäuren, Salpetersäure, Perchlorsäure, aliphatische, alicyclische, aromatische oder heterocyclische Carbon- oder Sulfonsäuren, wie Ameisen-, Essig-, Propion-, Bernstein-, Glykol-, Milch-, Apfel-, Wein-, Zitronen-, Ascorbin-, Malein-, Hydroxymalein- oder Brenztraubensäure; Phenylessig-, Benzoe-, p-Aminobenzoe-, Anthranil-, p-Hydroxy-benzoe-, Salicyl- oder p-Aminosalicylsäure, Embonsäure, Methansulfon-, Athansulfon-, Hydroxyäthansulfon-, Athylensulfonsäure; Halogenbenzolsulfon-, Toluolsulfon-, Naphthalinsulfonsäure oder Sulfanilsäure; Methionin, Tryptophan, Lysin oder Arginin.
Diese oder andere Salze der neuen Verbindungen, wie z. B. die Pikrate, können auch zur Reinigung der erhaltenen freien Basen dienen, indem man die freien Basen in Salz überführt, diese abtrennt und aus den Salzen wiederum die Basen freimacht. Infolge der engen Beziehungen zwischen den neuen Verbindungen in freier Form und in Form ihrer Salze sind im vorausgegangenen und nachfolgend unter den freien Basen sinn- und zweckmässig gegebenenfalls auch die entsprechenden Salze zu verstehen.
Die Ausgangsstoffe können auch unter den Reaktionsbedingungen gebildet werden.
Die neuen Verbindungen können als Racemate oder in Form der Antipoden vorliegen. Die Racemate können in üblicher Weise in die Antipoden zerlegt werden.
Die neuen Verbindungen können z. B. in Form pharmazeutischer Präparate Verwendung finden, welche sie in freier Form oder gegebenenfalls in Form ihrer Salze in Mischung mit einem für die enterale oder parenterale Applikation geeigneten pharmazeutischen organischen oder anorganischen, festen oder flüssigen Trägermaterial enthalten.
In den folgenden Beispielen sind die Temperaturen in Celsiusgraden angegeben.
Beispiel I
10,0 g 3-Isopropyl-5-(o-methallyloxy-phenoxy-me- thyl)-oxazolidon-(2) werden mit 50 ml 10-n Natronlauge während 15 Minuten unter gutem Rühren auf 1200 erhitzt. Hierauf gibt man 200 ml Wasser zu und extrahiert mit Äther. Die Äther-Schicht wird abgetrennt, getrocknet und im Wasserstrahlvakuum eingedampft. Es verbleibt das 1-Isopropylamino-2-hydroxy-3-(o-methal- lyloxy-phenoxy)-propan der Formel
EMI2.1
dessen Hydrochlorid bei 88 bis 90" schmilzt.
Beispiel 2
1 g 1-(N-Acetyl-isopropylamino)-2-acetoxy-3-(o-methallyloxy-phenoxy)-propan wird in 7 ml absolutem Alkohol und 3,5 ml 5-n. Natronlauge während 7 Stunden am Rückfluss gekocht. Die Reaktionslösung wird im Vakuum eingeengt. Den Eindampfrückstand versetzt man mit Wasser und schüttelt mit Äther aus. Nach Eindampfen der getrockneten Ätherlösung erhält man als Rückstand das 1-Isopropylamino-2-hydroxy-3-(o-me- thallyloxyphenoxy)-propan der Formel
EMI2.2
dessen Hydrochlorid bei 88 bis 900 schmilzt.
Beispiel 3
Zu einer Lösung von 5,0 g 3-Isopropyl-5-(o-methal lyloxy-phenoxymethyl)-oxazolidin in 50 ml Äthanol gibt man 25 ml 2-n Salzsäure und erwärmt eine Stunde auf 70". Anschliessend wird der Alkohol abdestilliert und den Rückstand versetzt man mit 75 ml 2-n Natronlauge.
Es scheidet sich ein öl ab, das mit Äther extrahiert wird. Nach dem Trocknen und Eindampfen des Äthers bleibt das 1-Isopropylamino-2-hydroxy-3-(o-methallyloxy-phenoxy)-propan der Formel
EMI2.3
dessen Hydrochlorid bei 89 bis 91" schmilzt, zurück.
Process for the preparation of new unsaturated amines
The invention relates to a process for the preparation of 1-isopropylamino-2-hydroxy-3- [o- (R-alk-O) -phenoxyj-propanes of the formula
EMI1.1
wherein alk is an alkylene radical and R is an unsaturated aliphatic hydrocarbon radical, where alk and R together have at least 4 carbon atoms, or their salts.
The alkylene radical is in particular a lower alkylene radical with 1-3 carbon atoms.
The radical R is above all a propenyl radical or straight or branched butenyl, pentenyl or hexenyl radical or a corresponding radical with a triple bond.
The new compounds have valuable pharmacological properties. In particular, they cause an inhibition of adrenergic ß-receptors. Accordingly, they can be used as medication for heart and circulatory diseases.
1-Isopropylamino-2 hydroxy-3- (o-methallyloxyphenoxy) propane of the formula is particularly valuable
EMI1.2
The process according to the invention for the preparation of the new compounds is characterized in that 1-isopropylamino-2-oxy-3- [o- (R-alk-O) -phenoxy] -propane, where alk and R have the meanings given above, that on the nitrogen atom and on the 2-oxy group each have a monovalent or together a bivalent radical which can be split off by hydrolysis, these radicals split off. Such monovalent residues are e.g. B. acyl radicals of carboxylic acids, such as lower alkanoyl radicals, e.g. B. the acetyl radical, or the monovalent carbonic acid radical, which is also in the form of its half ester, e.g. B. as benzyloxycarbonyl radical or tert-butoxycarbonyl radical.
Bivalent residues of this type are in particular the divalent carbonic acid residue, as is the case with e.g. B. in 5- [o- (R-alk-O) -Phenoxy] -3-isopropyl-oxazolidon-2 is the case. The hydrolysis is carried out in the usual way.
The starting materials are known or can be obtained by methods known per se.
The salts of the end products can in a conventional manner, for. B. with alkalis or ion exchangers, are converted into the free bases. Salts can be obtained from the latter by reaction with organic or inorganic acids, in particular those which are suitable for the formation of therapeutically useful salts.
Examples of such acids are: hydrohalic acids, sulfuric acids, phosphoric acids, nitric acid, perchloric acid, aliphatic, alicyclic, aromatic or heterocyclic carboxylic or sulfonic acids, such as formic, acetic, propionic, succinic, glycolic, lactic, apple- , Tartaric, citric, ascorbic, maleic, hydroxymaleic or pyruvic acid; Phenylacetic, benzoic, p-aminobenzoic, anthranil, p-hydroxy-benzoic, salicylic or p-aminosalicylic acid, emboxylic acid, methanesulphonic, ethanesulphonic, hydroxyethanesulphonic, ethylene sulphonic acid; Halobenzenesulfonic, toluenesulfonic, naphthalenesulfonic acid or sulfanilic acid; Methionine, tryptophan, lysine or arginine.
These or other salts of the new compounds, such as. B. the picrates can also be used to purify the free bases obtained by converting the free bases into salt, separating them and in turn frees the bases from the salts. As a result of the close relationships between the new compounds in free form and in the form of their salts, in the preceding and in the following the free bases are meaningfully and appropriately also the corresponding salts.
The starting materials can also be formed under the reaction conditions.
The new compounds can exist as racemates or in the form of the antipodes. The racemates can be broken down into the antipodes in the usual way.
The new connections can e.g. B. in the form of pharmaceutical preparations are used which they contain in free form or optionally in the form of their salts in a mixture with a pharmaceutical organic or inorganic, solid or liquid carrier material suitable for enteral or parenteral administration.
In the following examples the temperatures are given in degrees Celsius.
Example I.
10.0 g of 3-isopropyl-5- (o-methallyloxy-phenoxy-methyl) -oxazolidone- (2) are heated to 1200 with 50 ml of 10N sodium hydroxide solution for 15 minutes with thorough stirring. 200 ml of water are then added and the mixture is extracted with ether. The ether layer is separated off, dried and evaporated in a water jet vacuum. What remains is the 1-isopropylamino-2-hydroxy-3- (o-methallyloxy-phenoxy) propane of the formula
EMI2.1
its hydrochloride melts at 88 to 90 ".
Example 2
1 g of 1- (N-acetyl-isopropylamino) -2-acetoxy-3- (o-methallyloxy-phenoxy) -propane is dissolved in 7 ml of absolute alcohol and 3.5 ml of 5-n. Sodium hydroxide solution boiled under reflux for 7 hours. The reaction solution is concentrated in vacuo. The evaporation residue is mixed with water and extracted with ether. After evaporating the dried ether solution, the residue obtained is 1-isopropylamino-2-hydroxy-3- (o-methallyloxyphenoxy) propane of the formula
EMI2.2
its hydrochloride melts at 88 to 900.
Example 3
25 ml of 2N hydrochloric acid are added to a solution of 5.0 g of 3-isopropyl-5- (o-methal lyloxy-phenoxymethyl) -oxazolidine in 50 ml of ethanol and the mixture is heated to 70 "for one hour. The alcohol is then distilled off and 75 ml of 2N sodium hydroxide solution are added to the residue.
An oil separates, which is extracted with ether. After drying and evaporation of the ether, the 1-isopropylamino-2-hydroxy-3- (o-methallyloxy-phenoxy) -propane of the formula remains
EMI2.3
its hydrochloride melts at 89 to 91 ".
Claims (1)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH56369A CH476679A (en) | 1965-06-11 | 1965-06-11 | Process for the production of new unsaturated amines |
| CH170668A CH475191A (en) | 1965-06-11 | 1965-06-11 | Process for the production of new unsaturated amines |
| CH56269A CH476678A (en) | 1965-06-11 | 1965-06-11 | Process for the production of new unsaturated amines |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH170668A CH475191A (en) | 1965-06-11 | 1965-06-11 | Process for the production of new unsaturated amines |
| CH819365A CH465586A (en) | 1965-06-11 | 1965-06-11 | Process for the production of new unsaturated amines |
| CH397366 | 1966-03-18 | ||
| CH505866 | 1966-04-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH475191A true CH475191A (en) | 1969-07-15 |
Family
ID=27428264
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH170668A CH475191A (en) | 1965-06-11 | 1965-06-11 | Process for the production of new unsaturated amines |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH475191A (en) |
-
1965
- 1965-06-11 CH CH170668A patent/CH475191A/en not_active IP Right Cessation
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