CH515885A - 1-phenoxy-2-hydroxy-3-alkylamino propanes adrenolytic - Google Patents
1-phenoxy-2-hydroxy-3-alkylamino propanes adrenolyticInfo
- Publication number
- CH515885A CH515885A CH848371A CH848371A CH515885A CH 515885 A CH515885 A CH 515885A CH 848371 A CH848371 A CH 848371A CH 848371 A CH848371 A CH 848371A CH 515885 A CH515885 A CH 515885A
- Authority
- CH
- Switzerland
- Prior art keywords
- alkyl
- formula
- group
- carbon atoms
- hydroxy
- Prior art date
Links
- 230000002908 adrenolytic effect Effects 0.000 title 1
- 235000013849 propane Nutrition 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- -1 3,4-methylenedioxy residue Chemical group 0.000 claims abstract description 6
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
- 125000004429 atom Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 238000001640 fractional crystallisation Methods 0.000 claims 1
- 125000002560 nitrile group Chemical group 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 abstract 3
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000003282 alkyl amino group Chemical group 0.000 abstract 2
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 abstract 1
- 208000001953 Hypotension Diseases 0.000 abstract 1
- 125000006193 alkinyl group Chemical group 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 208000021822 hypotensive Diseases 0.000 abstract 1
- 230000001077 hypotensive effect Effects 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- MFEDKMBNKNOUPA-UHFFFAOYSA-N (2-bromo-4,7-dimethyl-3-oxo-7-bicyclo[2.2.1]heptanyl)methanesulfonic acid Chemical compound C1CC2(C)C(=O)C(Br)C1C2(CS(O)(=O)=O)C MFEDKMBNKNOUPA-UHFFFAOYSA-N 0.000 description 1
- YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 description 1
- QXMVQMLDKDSOLR-UHFFFAOYSA-N 3-amino-1-phenoxypropan-1-ol Chemical class NCCC(O)OC1=CC=CC=C1 QXMVQMLDKDSOLR-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- YIUIVFFUEVPRIU-UHFFFAOYSA-N 8-chlorotheophylline Chemical compound O=C1N(C)C(=O)N(C)C2=NC(Cl)=N[C]21 YIUIVFFUEVPRIU-UHFFFAOYSA-N 0.000 description 1
- DIZDWVWKKIRGNW-UHFFFAOYSA-N CCCC(C)(C)CC(C(N)OC1=CC(N)=CC=C1)O Chemical compound CCCC(C)(C)CC(C(N)OC1=CC(N)=CC=C1)O DIZDWVWKKIRGNW-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 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
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 239000000150 Sympathomimetic Substances 0.000 description 1
- 208000001871 Tachycardia 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
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 125000002648 azanetriyl group Chemical group *N(*)* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000003218 coronary vasodilator agent Substances 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000000314 lubricant 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
- 239000011976 maleic acid Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000001975 sympathomimetic effect Effects 0.000 description 1
- 229940064707 sympathomimetics Drugs 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
-
- 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
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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)
Abstract
(A) Cmpds. of general formula (I) - R = (5-8C) alkyl contng. at least one quat. C atom, the latter being linked directly or via a (1-4C) alkylene chain to the N atom. - R1=CN, CO2H, OH, NH2, NO2, or CF3, alkyl opt. subst. by (di)alkylamino, OH, Oalkyl, or CN, alkenyl, alkinyl, O-alkenyl, O-alkinyl, CO2 alkyl, CO2 (alkylamino), S-alkyl, acyl, O acyl, or NH acyl, all having (1-5C) atoms, hal, or (1-5C) Oalkyl, m- or p-to the propanolamino side chain. - R2 = H, hal, CN, (1-4C) alkyl, (1-4C) O alkyl, or (1-4C) alkenyl - R3 = H, hal, (1-4C) alkyl, or (1-4C) O alkyl, or - R2 + R3 = a 3,4-methylenedioxy residue with the proviso that if R = 1, 1-diethylbutyl, and R2 = R3 = H, then R1 is not = 2-bromo. - (B) Salts of I. - beta-Adrenolytics and hypotensives. Dose 1-300 mg.
Description
Verfahren zur Herstellung von neuen 1-Phenoxy-2-hydroxy-3-alkylaminopropanen Die Erfindung betrifft ein Verfahren zur Herstellung von neuen racemischen oder optisch aktiven 1-Phenoxy- 2-hydroxy-3-alkylaminopropanen der Formel I
EMI0001.0002
und von deren Säureadditionssalzen.
In dieser Formel bedeuten: R eine Alkylgruppe mit 5 bis 8 Kohlenstoffatomen, die mindestens ein direkt oder über eine Alkylenkette von 1 bis 4 Kohlenstoffatomen an die Aminogruppe ge bundenes quartäres Kohlenstoffatom enthält, R1 Wasserstoff, ein Halogenatom, eine Nitrilo- gruppe oder eine Alkyl- oder Alkoxygruppe mit 1 bis 4 C-Atomen und R2 Wasserstoff, ein Halogenatom, eine Alkyl- oder Alkoxygruppe mit 1 bis 4 C-Atomen oder zusammen mit R1 eine 3,4-Methylendioxygruppe.
Das erfindungsgemässe Verfahren zur Herstellung der Verbindungen der Formel I ist dadurch gekenn zeichnet, dass man eine Verbindung der Formel II
EMI0001.0005
reduziert. Das für die Durchführung des erfindungsgemässen Verfahrens benötigte Ausgangsmaterial ist zum Teil bereits bekannt, zum Teil kann es nach üblichen Ver fahren gewonnen werden. Die Verbindung der Formel II kann beispielsweise ausgehend von einem Phenol bzw.
Phenolat der Formel III 2
EMI0001.0007
worin Kt Wasserstoff oder ein Kation, beispielsweise ein Alkalimetallkation, bedeutet, erhalten werden, in dem man die Verbindung der Formel III mit Epi- chlorhydrin in ein Epoxyd der Formel IV
EMI0001.0010
überführt und dieses mit einem Alkylamin der Formel V NH2-R V umsetzt.
Die erfindungsgemäss erhältlichen Verbindungen be sitzen ein asymmetrisches C-Atom und kommen daher als Racemat wie auch in Form der optischen Antipo den vor. Letztere können ausser durch Racematentren- nung mit üblichen Hilfssäuren wie Dibenzoyl-D-Wein- säure oder D-3-Bromcampher-8-sulfonsäure auch durch Einsetzen von optisch aktivem Ausgangsmaterial erhal ten werden. Die erfindungsgemäss erhältlichen 1-Phen- oxy-3-aminopropanole der Formel I können in üblicher Weise in ihre physiologisch verträglichen Säureaddi tionssalze überführt werden.
Geeignete Säuren sind beispielsweise Salzsäure, Bromwasserstoffsäure, Schwe felsäure, Methansulfonsäure, Maleinsäure, Essigsäure, Oxalsäure, Milchsäure, Weinsäure oder 8-Chlortheo- phyllin.
Die Verbindungen der Formel 1 bzw. deren physio logisch verträglichen Säureadditionssalze haben im Tier versuch an Meerschweinchen wertvolle therapeutische, insbesondere ss-adrenolytische Eigenschaften gezeigt und können daher beispielsweise zur Behandlung oder Pro phylaxe von Erkrankungen der Herzkranzgefässe und zur Behandlung von Herzarrhythmien, insbesondere von Tachycardien, in der Humanmedizin eingesetzt wer den. Auch die blutdrucksenkenden Eigenschaften der Verbindungen sind therapeutisch interessant.
Die Einzeldosis der erfindungsgemäss hergestellten Substanzen liegt bei 1-300 mg; vorzugsweise 5-100 mg (oral) bzw. 1-20 mg (parenteral).
Die galenische Verarbeitung der erfindungsgemäss erhaltenen Verbindungen zu den üblichen Anwendungs formen wie Lösungen, Emulsionen, Tabletten, Dragees oder Depotformen kann in bekannter Weise unter Heranziehung der dafür gebräuchlichen galenischen Hilfs-, Träger-, Spreng-, Binde-, Überzugs- oder Schmiermittel, Geschmacksstoffe, Süssungsmittel, Mit tel zur Erzielung einer Depotwirkung oder Lösungs vermittler geschehen. Die erfindungsgemäss erhaltenen Verbindungen sind auch für die Kombination mit ande ren pharmakodynamisch wirksamen Stoffen wie Coro- nardilatatoren oder Sympathicomimetica geeignet.
Das folgende Beispiel dient zur näheren Erläute rung der Erfindung. <I>Beispiel</I> 1-(3'-Aminophenoxy)-2-hydroxy-3-(1,1-dimethylbutyl)- aminopropan - 2 HCl 7,1 g (0,024 Mol) 1-(3'-Nitrophenoxy)-2-hydroxy- 3-(1,1-dimethylbutylamino)-propan werden in 50 ml Methanol über Raney-Nickel bei 20 C hydriert. Nach Aufnahme der theoretischen Wasserstoffmenge wird der Katalysator abgetrennt, das Methanol abdestilliert und der Rückstand nach Lösen in wenig Äthanol mit äthe rischer HCl versetzt. Das kristallin ausfallende Hydro- chlorid wird aus Äthanol unter Zugabe von etwas Äther umkristallisiert.
Ausbeute: 5,1 g, Fp.: 173-174 C.
Process for the preparation of new 1-phenoxy-2-hydroxy-3-alkylaminopropanes The invention relates to a process for the preparation of new racemic or optically active 1-phenoxy-2-hydroxy-3-alkylaminopropanes of the formula I
EMI0001.0002
and their acid addition salts.
In this formula: R denotes an alkyl group with 5 to 8 carbon atoms which contains at least one quaternary carbon atom bonded directly or via an alkylene chain of 1 to 4 carbon atoms to the amino group, R1 hydrogen, a halogen atom, a nitrilo group or an alkyl or an alkoxy group with 1 to 4 carbon atoms and R2 hydrogen, a halogen atom, an alkyl or alkoxy group with 1 to 4 carbon atoms or, together with R1, a 3,4-methylenedioxy group.
The process according to the invention for the preparation of the compounds of the formula I is characterized in that a compound of the formula II
EMI0001.0005
reduced. Some of the starting material required for carrying out the process according to the invention is already known, and some can be obtained by conventional methods. The compound of the formula II can, for example, starting from a phenol or
Phenolate of the formula III 2
EMI0001.0007
wherein Kt is hydrogen or a cation, for example an alkali metal cation, can be obtained by converting the compound of the formula III with epichlorohydrin into an epoxide of the formula IV
EMI0001.0010
transferred and this with an alkylamine of the formula V NH2-R V is reacted.
The compounds obtainable according to the invention have an asymmetric carbon atom and therefore occur as a racemate as well as in the form of the optical antipodes. The latter can be obtained not only by resolution of the racemates with customary auxiliary acids such as dibenzoyl-D-tartaric acid or D-3-bromocamphor-8-sulfonic acid but also by using optically active starting material. The 1-phenoxy-3-aminopropanols of the formula I obtainable according to the invention can be converted into their physiologically tolerated acid addition salts in the customary manner.
Suitable acids are, for example, hydrochloric acid, hydrobromic acid, sulfuric acid, methanesulphonic acid, maleic acid, acetic acid, oxalic acid, lactic acid, tartaric acid or 8-chlorotheophylline.
The compounds of formula 1 and their physiologically tolerable acid addition salts have shown valuable therapeutic, in particular ss-adrenolytic properties in animal experiments on guinea pigs and can therefore be used, for example, for the treatment or prophylaxis of diseases of the coronary arteries and for the treatment of cardiac arrhythmias, especially tachycardias, used in human medicine. The antihypertensive properties of the compounds are also of therapeutic interest.
The single dose of the substances prepared according to the invention is 1-300 mg; preferably 5-100 mg (oral) or 1-20 mg (parenteral).
The pharmaceutical processing of the compounds obtained according to the invention into the customary application forms such as solutions, emulsions, tablets, coated tablets or depot forms can be carried out in a known manner using the pharmaceutical auxiliaries, carriers, disintegrants, binders, coatings or lubricants, flavorings, which are customary for this , Sweeteners, means to achieve a depot effect or solubilizers happen. The compounds obtained according to the invention are also suitable for combination with other pharmacodynamically active substances such as coronary dilators or sympathomimetics.
The following example serves to explain the invention in more detail. <I> Example </I> 1- (3'-aminophenoxy) -2-hydroxy-3- (1,1-dimethylbutyl) - aminopropane - 2 HCl 7.1 g (0.024 mol) 1- (3'-nitrophenoxy ) -2-hydroxy-3- (1,1-dimethylbutylamino) propane are hydrogenated in 50 ml of methanol over Raney nickel at 20.degree. After the theoretical amount of hydrogen has been absorbed, the catalyst is separated off, the methanol is distilled off and, after dissolving in a little ethanol, the residue is treated with ethereal HCl. The hydrochloride which precipitates in crystalline form is recrystallized from ethanol with the addition of a little ether.
Yield: 5.1 g, m.p .: 173-174 C.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1643262A DE1643262C3 (en) | 1967-12-13 | 1967-12-13 | i-Phenoxy ^ -hydroxy-S-alklyaminopropane, process for their preparation and medicaments containing these compounds |
| CH1843568A CH532015A (en) | 1967-12-13 | 1968-12-10 | Process for the preparation of new 1-phenoxy-2-hydroxy-3-alkylaminopropanes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH515885A true CH515885A (en) | 1971-11-30 |
Family
ID=25721019
Family Applications (9)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH848171A CH530955A (en) | 1967-12-13 | 1968-12-10 | Process for the preparation of new 1-phenoxy-2-hydroxy-3-alkylaminopropanes |
| CH848371A CH515885A (en) | 1967-12-13 | 1968-12-10 | 1-phenoxy-2-hydroxy-3-alkylamino propanes adrenolytic |
| CH847871A CH532018A (en) | 1967-12-13 | 1968-12-10 | Process for the preparation of new 1-phenoxy-2-hydroxy-3-alkylaminopropanes |
| CH848571A CH530957A (en) | 1967-12-13 | 1968-12-10 | Process for the preparation of new 1-phenoxy-2-hydroxy-3-alkylaminopropanes |
| CH848271A CH530956A (en) | 1967-12-13 | 1968-12-10 | Process for the preparation of new 1-phenoxy-2-hydroxy-3-alkylaminopropanes |
| CH847771A CH532017A (en) | 1967-12-13 | 1968-12-10 | Process for the preparation of new 1-phenoxy-2-hydroxy-3-alkylaminopropanes |
| CH848071A CH530954A (en) | 1967-12-13 | 1968-12-10 | Process for the preparation of new 1-phenoxy-2-hydroxy-3-alkylaminopropanes |
| CH847671A CH532016A (en) | 1967-12-13 | 1968-12-10 | Process for the preparation of new 1-phenoxy-2-hydroxy-3-alkylaminopropanes |
| CH847971A CH532019A (en) | 1967-12-13 | 1968-12-10 | Process for the preparation of new 1-phenoxy-2-hydroxy-3-alkylaminopropanes |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH848171A CH530955A (en) | 1967-12-13 | 1968-12-10 | Process for the preparation of new 1-phenoxy-2-hydroxy-3-alkylaminopropanes |
Family Applications After (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH847871A CH532018A (en) | 1967-12-13 | 1968-12-10 | Process for the preparation of new 1-phenoxy-2-hydroxy-3-alkylaminopropanes |
| CH848571A CH530957A (en) | 1967-12-13 | 1968-12-10 | Process for the preparation of new 1-phenoxy-2-hydroxy-3-alkylaminopropanes |
| CH848271A CH530956A (en) | 1967-12-13 | 1968-12-10 | Process for the preparation of new 1-phenoxy-2-hydroxy-3-alkylaminopropanes |
| CH847771A CH532017A (en) | 1967-12-13 | 1968-12-10 | Process for the preparation of new 1-phenoxy-2-hydroxy-3-alkylaminopropanes |
| CH848071A CH530954A (en) | 1967-12-13 | 1968-12-10 | Process for the preparation of new 1-phenoxy-2-hydroxy-3-alkylaminopropanes |
| CH847671A CH532016A (en) | 1967-12-13 | 1968-12-10 | Process for the preparation of new 1-phenoxy-2-hydroxy-3-alkylaminopropanes |
| CH847971A CH532019A (en) | 1967-12-13 | 1968-12-10 | Process for the preparation of new 1-phenoxy-2-hydroxy-3-alkylaminopropanes |
Country Status (1)
| Country | Link |
|---|---|
| CH (9) | CH530955A (en) |
-
1968
- 1968-12-10 CH CH848171A patent/CH530955A/en not_active IP Right Cessation
- 1968-12-10 CH CH848371A patent/CH515885A/en not_active IP Right Cessation
- 1968-12-10 CH CH847871A patent/CH532018A/en not_active IP Right Cessation
- 1968-12-10 CH CH848571A patent/CH530957A/en not_active IP Right Cessation
- 1968-12-10 CH CH848271A patent/CH530956A/en not_active IP Right Cessation
- 1968-12-10 CH CH847771A patent/CH532017A/en not_active IP Right Cessation
- 1968-12-10 CH CH848071A patent/CH530954A/en not_active IP Right Cessation
- 1968-12-10 CH CH847671A patent/CH532016A/en not_active IP Right Cessation
- 1968-12-10 CH CH847971A patent/CH532019A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH532019A (en) | 1972-12-31 |
| CH532016A (en) | 1972-12-31 |
| CH530957A (en) | 1972-11-30 |
| CH530955A (en) | 1972-11-30 |
| CH532018A (en) | 1972-12-31 |
| CH530956A (en) | 1972-11-30 |
| CH532017A (en) | 1972-12-31 |
| CH530954A (en) | 1972-11-30 |
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| PL | Patent ceased |